A Poem: Don't Be Ashamed, Dear Sissy

 A Poem: Don't Be Ashamed, Dear Sissy

My dear, sweet sissy
I know why you cry
It won't go away
So don't even try
You do it in secret
So nobody knows
You feel so guilty
As you toss all your clothes

Your mind is tormented
You feel such shame
You know you can't fight it
You're caught in the game
Here comes the package
There's more lingerie
You think that it's sexy
Does that make you gay

Pink satin, lace panties
They'll make you feel pretty
Excitement is building
You notice your clitty
You put on your panties
You think you look hot
Now, don't make a mess
You see your wet spot

The pink lacey bra
You slip on with a smile
Just look at that sissy
She has quite a style
You grab your pink nightie
Your mind has gone numb
You play with your clitty
Til you make it cum

Gone is the thrill
As the guilt settles in
Again with the battle
Will you ever win
You hide all your clothes
Will you throw them away
And regret that decision
When you want to play

You say to yourself
As you look in the mirror
"Hey, I know that person
Such a cute, sissy queer"
New words come to mind,
As you say them out loud
"I know I'm a sissy,
And, today I am proud."
 

The Poker Game

 The Poker Game

Steve and his friends were enjoying a game of poker. His wife was out of town, so he invited his best friend Jeff and the guys for a little drinking and gambling. The stakes could get high in their games, and he was hoping to take advantage of that.

Steve wanted to take his wife Cheryl to a special spa retreat for a vacation get away, and he lost a couple hands to his friends. The pot was getting rich, and he knew this was his hand to win. He was confident as they threw more chips in the pot.

He admired his cards, trying to keep an expressionless face. The 3,4,5,6 and 7 of clubs. He had this one. But, there was a problem. He was down to $100 and didn't know what to bet.

"The bet is two, Steve-o. You're short a bill, " Jeff had a grin on his face. "But I know that look. You think you have us beat."

"I'm beat, " said Jim as he threw his cards on the table. "I'm getting a beer. Anybody want one?"

Scott downed half a beer. "Yeah, sure. I'm on empty here."

"Well, I can offer up my..."

Jeff shook his head. "Nope. You don't have anything I want, bro. Just admit you lost."

He reached out for the chips as Steve stopped him. "Wait. I have a proposal."

Jeff arched an eye brow with a curious expression. "I'm listening."

"The wife is gone for the night, so if you win, I'll serve the four of you refreshments and snacks in her red dress."

Scott took a beer from Jim and burst into laughter. "Are you serious? What are you, gay?"

Steve looked at Jeff. "Remember that time in college when I was pledging the frat and I had to serve you guys all day at the frat party. How you were all laughing at me. I just thought..."

Jeff smiled. "Okay, I'll allow it."

The other three guys were surprised. "What? Are you serious?"

"Relax guys. Were about to have a serving wench for the rest of the night."

Steve shook his head. "Don't be so sure about that, Jeff."

"Show me, Steve."

Steve proudly lay his cards on the table one at a time. A straight. Read 'em and weep."

Jim shook his head. "The fucker set you up."

Jeff grinned. "Well, that wins just about anywhere but in my kingdom. Perhaps you've heard of them, the 10, the jack of all trades, her royal highness, the king himself and his ace in the hole."

Steve stared at the royal flush in shock. "No fucking way."

"Oh, yes way. Better get that red dress and get your hot little ass in here, Steve, or is that Stephanie?. The boys are thirsty, and I think you can fix us up a little snack too."

Steve had considered this might happen when he made the bet, but he was confident he would win. He got up from the chair. "Okay, let me get ready."

"He's doing it, " said Scott as he took a drink. "Oh my God. I don't believe it."

"Of course he's doing it, " Jeff replied. "He's a man of his word. Now, deal us in, Ben. I feel lucky tonight."

Steve went to the room and stripped down, admiring his smooth body in the full length mirror. His cock strained against his chastity cage. He had no way out of that as Cheryl held the key. He quickly slipped into a red bra and panties and the knee length red dress his wife bought him.

It was all he could do to fight the urge to get one of his butt plugs to try and calm down as his cock fought an unsuccessful battle with his cage. He carefully applied foundation, blush and eye makeup. He had the perfect brown haired wig and put dangling hoop ear rings in his pieced ears.

"Hurry up, Stephanie. The guys are thirsty, " came Jeff's voice from the room.

He meticulously put on his red lip stick, lip liner and gloss. He admired them in the mirror before reaching for a pair of four inch red open toe heels. "Perfect." He looked in the full length mirror again. "Well, here goes nothing."

When Steve returned to the dining room, the guys were floored by how much he had transformed. "Are those... breast forms, " Jim asked as he admired the D Cup falsies that gave Steve an attractive bust line?

"Well, I figured a bet is a bet, " he replied in his feminine voice.

"Dude, you only had to wear a dress." Jeff looked his friend up and down. "Come over here, turn around for me."

Steve complied and felt a slap on his ass. "Damn, that ass looks nice in the dress."

"Dude, that's gay, " said Scott.

"So, you're telling me if you didn't know this was Steve you wouldn't think about fucking that ass, " Jeff's erection was hidden from view? "If I met Stephanie at the bar..."

Steve blushed. "Okay, I think they get it. What do you guys want?"

"More beer, " said Jim.

"And how about some pizza, " Ben added. "I know you have the good stuff."

Steve went to work, listening to the conversation as his chastity cage wasn't getting any looser. He sat some more beers on the table and went to the oven.

Scott wouldn't let it go. "Are you serious, Jeff? Are you telling me you'd fuck Steve?"

He grinned. "Look, all I'm saying is if I met him at the bar and didn't know it, I'd be totally turned on."

"I see his point, " Ben added. "Any cards, Jeff?"

He looked at his cards and put two on the table. "Yeah, two. Come on, Scott. Look at Stephanie's lips. Are you telling me they wouldn't look good on your cock?"

Steve was blushing as he put two pizzas in the oven. He said nothing and tried to pretend he wasn't listening.

"I'm saying that's gay, " Scott replied.

Jim laughed "Not if you aren't being fucked or sucking her."

"See, Jim gets it. Imagine her sucking your cock while I take her from behind. Tag team style bro, just like Vegas."

Jim high-fived Jeff. "You know it. That night was so awesome. You know, I still get e-mails from Renee."

As the game went on, Steve served them pizza and several beers, and the guys were getting hornier. They kept referring to him as Stephanie. He wasn't discouraging that as he spoke in a feminine tone.

Jeff was the lucky one, winning close to $5,000, but he had an idea brewing as he looked lustfully at Steve. Steve sat down. "What? I know that look. What are you thinking?"

Jeff held the deck of cards. "Are you up for a game of chance?"

Steve would never admit to this, but he hoped that the night would take a sexy turn. That was his intent all along, but he played coy with the guys. "What are the stakes?"

"I'll bet my winnings, " he replied with a grin. "All of it."

Steve needed that money for his vacation plans. "And what if I lose?"

Jeff shuffled the cards. "I think you know the answer to that, Stephanie. Me and the boys here will have a night with you that will make Renee from Vegas blush."

"No way, " Scott protested.

Ben laughed. "Oh, shut up, Scott. We've all been watching you rub your pants under the table when she walks away."

Scott shook his head "That's a he, dude."

"Not tonight, " said Jim as he high fived Ben.

Jeff looked intently at Steve. "So, how about it Stephanie? Are you in?"

Never had Steve felt the pain of the chastity as he did in this moment. "What's the game?"

Jeff sat the deck on the table. "I don't have all day. High card wins."

Steve looked at the deck for a long time before grabbing a card. "Fine, I'll do it."

Jeff grinned. "No turning back now, Stephanie. We won't be leaving until we are all satisfied."

"Damn right, " said Jim as he took his drink and headed for the couch.

Jeff drew his card and lay it on the table without looking at it. "You first, darling. What do you have?"

Steve smiled. "King of Hearts. "

"Oh fuck, dude, " Ben said with a laugh. "You blew it."

Jeff kept his hand over the card and didn't lose eye contact with Steve. "You know what I've always liked about you, Steve? You love taking chances. You love taking risks. That's why you have the business you have now, a hot wife, this nice home. You never play it safe when you have a hunch."

Steve took a sip of beer. "I could say the same about you, Jeff. We're a lot alike. I think that's why we've been friends all our lives."

"This money would be nice. I had my eyes on a really nice ring for Helen, but here's the thing. Ever since you walked in here looking like that, I wanted to fuck you. I wanted to fuck you hard and show you how it feels to be my woman. What do you think about that?"

Steve didn't say a word, but his red face told the story. "Show the damn card, Jeff."

He turned the card over and revealed an Ace of Diamonds. "What do you think of it now, Stephanie? Because it's about to happen."

Jim sat on the couch with his cock in his hand. "Mind if I have first crack at her mouth, Jeff?"

Jeff laughed. "Be my guest Jim. Shall we all adjourn to the living room?"

"I can't believe I'm doing this, " said Steve.

As Ben and Scott sat next to Jim and dropped their shorts, Jeff led Steve to Jim. "That's bullshit, Stephanie. This is exactly what you wanted. You put far too much effort into this. I think you wanted to be fucked like a dirty little whore, and you're about ready to get it."

"Jeff, I..."

Jeff led Steve to his knees in front of Jim. "It's not polite to talk with your mouth full, and his cock isn't gonna drain itself, Stephanie."

Steve looked at Jim's hard cock, which stood an an impressive seven inches and was not very well trimmed. He started kissing and licking it as the guys roared their approval. "Suck it, Stephanie."

Steve welcome Jim's cock inside his eager mouth, bobbing up and down and licking the shaft. He was deep throating it and doing a good job. "Holy shit, " said Jim as he enjoyed the sensation.

I'm next, "Scott called out."

Jeff rubbed Steve's ass. "Fine with me. I told you her ass was mine."

As Jeff caressed his ass, Steve was sucking Jim's cock like a greedy little slut, thinking about Scott's cock. Jeff reached underneath Steve's dress and came into contact with the chastity cage. "What the hell is that?"

A sound came ftpm the front door as a key entered the lock. Steve's beautiful blonde wife Cheryl was home in a tight and skimpy blue cocktail dress. "Honey, I'm home early, " she said with a smile.

Scott got up in a panic, but Steve continued sucking Jim's cock. Jeff was looking at Cheryl with a confused expression on his face. Cheryl stopped Scott. "Not so fast, Scott. I know you've been telling Steve how you want to fuck me, and I say tonight's your lucky night."

Steve kept sucking Jim, who was enjoying the sensation while watching the crazy scene play out in front of him. "What the hell is going on here, " asked Jeff?

"Well, Stephanie said she was gonna have a gang bang here with you guys while I was gone, and I said not without me. She said I'd better get home then. Honestly, I had my doubts, but there you are."

She sat down on the chair, pulling her dress up to reveal no panties. "Well, go on Jeff. Fuck her. She's been going on and on about it for days now." She looked at Scott. "Um, Scott, my pussy isn't gonna eat itself, dear. You've got to lick it, if you want to stick it."

Jeff grinned and lifted up Steve's dress. "Fuck it."

Steve pulled up off of Jim's cock as he tasted the pre cum. He looked back at Jeff in his feminine voice. "I wish you would."

As Cheryl sat with her legs spread and Scott's mouth buried in her pussy, Ben went to the edge of the chair and shoved his massive eight inch cock in her face. She giggled as she took his cock in her mouth. "I see why they call you Big Ben."

"I've never had any complaints, " he boasted.

It took little effort for Jeff to penetrate Steve's ass. "Oh, fuck yeah. You have a nice tight little pussy, Stephanie."

"Hmm " was all he managed as he felt like Jim was about to burst inside his mouth. He didn't want to waste a drop.

"I don't know how Helen would like this, but what she doesn't know won't hurt her, " Jeff remarked.

Cheryl got up from her chair and had Ben sit down. "You'd be surprised, Jeff. If the way she eats pussy is any indication, she might love it."

"Oh fuck, " Jeff groaned as he was loving the feeling of Steve's ass on his cock "I think I could get used to banging your sweet ass, Stephenie. What do you think of that."

Jim smiled. "She's a little too preoccupied right now, bro. Just keep sucking. I'm about ready to pop."

Cheryl sat down on Ben's massive cock, taking it in her ass as she reclined in the chair and looked at Scott. "Well, come on baby. Mama has another hole that's available."

Scott slid his cock into her wet pussy as he and Ben used Cheryl as their personal fuck toy. "Why didn't you tell us you were such a slut?"

She pulled him in for a kiss. "Now you know, sweetie."

As Steve sucked on Jim's cock, he felt the first spurt hit the back of his throat. "Oh, fuck yes, " Jim proudly proclaimed. "Take it, Stephanie. Swallow my cum."

Steve had sucked cock many times for Cheryl. He was always told that it was impolite not to swallow a load, and he wasn't about to stop here. He kept his mouth on Jim's cock as he continued to cum.

Jeff continued to fuck his best friend hard, and he was amazed at how he could still focus on sucking a cock. "Cheryl isn't the only slut in this house. I think Stephanie gives her a run for the money."

With a mouth full of cum, Steve held out his tongue to show Jim and then swallowed the load before rubbing his wet cock all over his face and kissing it. "You know, this changes the way we see you, Stephanie. You're a sissy slut to us now."

He grinned. "I've always known that. Now you guys do too."

"Oh, here it comes baby, " proclaimed Jeff as he was about to cum. Steve surprised him by pushing back to take his cock as far in as he could. Jeff unloaded spurt after spurt into his sissy best friend's pussy hole.

He leaned forward and kissed him on the back of the neck with his cock still inside him. "You're mine now. You know, I'm gonna want you again after this."

He turned around to kiss him. "I'm counting on it, baby."

Cheryl had reached her first orgasm before Scott unloaded inside her pussy. As he pulled out, she bent over the arm of the chair to have Ben fuck her from behind in the ass. Steve kissed his wife. "Oh baby, you have to try Ben's cock. It's the best."

Ben was pounding Cheryl's ass like a jack hammer for several minutes before he exploded inside her. The guys all watched in amazement as Steve cleaned Ben's cock and then started cleaning his wife's two well used holes.

Cheryl smiled. "Just so you boys know, she's my sissy. But if you let me into your poker games, I think we can all have some fun together."             

The Secretary's Secret

Monica had a bit of a dilemma. She was a happily married woman in a special relationship with her husband, Brian. Brian ran a successful publishing company. He had been married to Monica for 15 years. They had two children in the marriage, and Brian worked hard to make sure they were provided for. Though Monica helped Brian start the company, she settled into the role of home maker after their second child was born.

She was starting to get bored with her life and was searching for something more. About a year ago, Brian dropped a bombshell on her. He had been secretly dressing up in women's clothing behind her back. He had been dressing up since he was a kid, but he stopped when the two of them got married. He started again not long after Monica became a home maker.

Monica had the talk with him about what it all meant. He said it was a turn on to him to wear lingerie. He also said he often wondered what it was like to be a woman and had started playing with toys. He showed her his lingerie collection, which included some sexier things than she had. She had to process all of this, and at first she felt betrayed by him and considered leaving him. But, she knew he loved her. She loved him too.

Monica was an attractive woman. She had black hair and hazel eyes. She was always getting her hair and nails done. She did keep herself in shape with exercises and walking the treadmill they had at home. Though she had nice breasts, she would probably say her best feature was her shapely ass. She prided herself in keeping it in shape. Monica was also a writer and wrote the first romance novels the company published.

She read up on the whole sissy culture to try to understand her husband. She had already found that he was letting her make many of the decisions at home and suspected he had a strong submissive side. However, she wasn't really the hard core Domme type. She saw herself as more of a sensual Domme who liked to use tease and denial to get him to comply. Two things changed from that point on.

First of all, she began dressing her husband, which meant whatever lingerie she picked out for him would be worn underneath his clothes when he left home. It was usually frilly panties and a camisole. Sometimes a sports bra or an even sexier bra. She sprayed him with perfume and disallowed cologne. She had his toe nails painted and his body shaved. Occasionally, she ordered him to wear things that had him on edge all day, fearing that he would be caught, but he always did what he was asked to do.

In the bedroom, he wasn't performing sexually the way he had. Brian wasn't particularly well endowed, but he had been adequate before these revelations. He improved greatly in the oral department, but he wasn't really getting it done otherwise. He tried, and it caused him anxiety when he failed. Her teasing probably didn't help as she was calling him Brenda, her lesbian lover and joking that she needed to find a real man to satisfy her. Privately, she wondered if he might really have gender identity issues, but they hadn't had that discussion.

She was conflicted. She really wanted a lover who could satisfy her sexually, but it felt like cheating on Brian if she did it. Brian never told her not to seek a lover when she teased him. He just got quiet. She thought about this every day, but the solution eventually presented itself. It was not something she expected, but when it happened, she was hooked.

Brian needed a new secretary to help keep him organized and focused. Edna had been with him since he opened the business, but the older woman decided to retire. That's when Stacy entered the picture. She was a knock out. Beautiful blond hair and blue eyes. She had the most shapely round ass, and Brian was a man who enjoyed looking at a beautiful woman's ass. Her breasts filled out her bras nicely. Stacy dressed provocatively, but when she smiled, he was putty in her hands. The only other woman who had that effect on him was his wife.

When Stacy entered his office for the interview, she was the 12th person he had seen. None of them sounded right, and she certainly sent off warning lights in his head that day. Any pervert of a boss would have hired her to play with, but he needed somebody who could handle anything. She would be practically running part of the business, or basically executing parts of his agenda for him while he was working on negotiating a buyout of a rival company.

For some reason, Stacy chose a tight red dress that barely contained her breasts, and she wore the prettiest shade of red lipstick. He found it difficult to look at her resume when she was staring at him with those adorable blue eyes. "So, um, " he nervously cleared his throat. "It says here that you have no college education, no experience as a secretary and..." He looked at her. "I'm sorry, but why should I hire you? You do realize this job will be demanding?"

"I can type really well, " she smiled, and he found himself tenting in the pink panties his wife had dressed him in under his suit.

"I see, but..."

"Mr. Griffin, I can do this, " she interrupted. "I can do this. I know you need somebody who has managerial skills. I practically ran my home for my mother and raised my four brothers and sisters with her. I'm creative and can think under pressure. I can even write..."

He shook his head. "Still, I don't think I can hire you, " he looked at her and noticed a tear in her eye. "It's just that you..."

"Please, just give me a chance, " she pleaded desperately. "I need this. I need the money, and I know I'll do good if you give me a chance. Just give me a week. If I'm not good, you can fire me."

He looked at her resume again, knowing that nothing on it suggested that she was right for this job. However, her tears and her beautiful face overrode logic. He smiled. "Okay, I'll give you a chance. Be here tomorrow at 6 a.m. Edna will be here to show you what she's been doing. That will be a start, but I'm telling you there will be more than that."

Stacy turned out to be a big surprise. She showed up at 5:30, waiting for Edna. Again, she dressed provocatively, but her attitude towards work was professional. When Brian arrived, she brought him coffee and a doughnut and breezed through the documents she was expected to type. Brian put her on the new erotica department that the company was establishing. She surprised him by coming up with a better plan for marketing the books.

Brian wouldn't have believed it, but Stacy was perfect for the company. At the end of the week, he informed her that she was hired full time. She smiled. "That's great sweetie, but I'm gonna need another $2.00 an hour for this, maybe more."

Sweetie? $2.00? Who does she think she is? He looked at her and those blue eyes got to him again. "Okay, we'll do it, but don't think this is gonna be easy, Stacy. It's just the beginning."

She shook his hand. "I hope so. I'm always up for a challenge."

Things seemed to be going better for Brian and Monica at home, but Brian was always praising the new secretary. She's amazing. She did this and that. She saved us money. The erotica department is taking off. Monica began to wonder if there was something going on between the two. But, Brian was every bit as attentive to Monica's needs as ever.

Monica walked into the room in a red robe as Brian sat on the bed. "So, are you fucking her, " she asked?

"Sweetie, you know you're the only woman for me, " he replied.

She shook her head. "That's not an answer, dear. Are you fucking her?"

"No, I'm not fucking her."

She stood in front of him, smiling seductively. "But, you want to fuck her, don't you?"

Was she jealous of his secretary, playing a game or both? "Sweetie. No, I only want you."

She giggled. "Oh, who am I kidding. That little thing can't satisfy me. She'd probably laugh you out of the room once you pulled down your panties." She looked him in the eyes. "Does she know you wear panties every day under your fancy suits?"

He went read in embarrassment. "No. Of course not."

She walked to the door and turned around. "Maybe somebody should tell her that her boss is really just a panty wearing sissy."

He stood up. "Sweetie, you aren't seriously thinking about telling her, are you?"

"Well, I don't know, " she replied with an evil grin. "We do have the office party on Friday, and I think it's time I finally met this woman."

Brian was hoping she was just teasing him again as he approached her with a hug. "You know I love you. You're the only woman I want to be with in any way. " He felt something poke him as he hugged her. "What the.."

"I see you felt my surprise for you, " she laughed as she disrobed to reveal her red lingerie set and a modest six-inch strap on cock. "Do you like it?"

He backed up. "Sweetie, a strap on? I don't think I can handle that."

She stepped up to him and took his hand. "Nonsense. You can handle it. Besides, I'll be gentle." She gave him the look that always made him melt, "You did say you wanted to be with me in any way, right?"

"But I..."

She squeezed his hand. "I want you in this way, baby. I want to fuck you like a woman." She laughed. "I want to make you my bitch. I think it's time, don't you?"

The tent in is baby blue panties revealed how turned on he was. "Baby, I don't..."

She reached over to the dresser for a tube of red lipstick and handed it to him. "Here sweetie. Put this on."

"Why?"

She flashed her hazel eyes with an innocent look. "To suck my cock so you can get it ready for that tight little ass of yours, silly."

He started putting the lipstick on, but she stopped him. "Do it like I taught you, Brenda."

"My name is Brian, " he protested as he turned to the mirror to carefully apply the lipstick as he had been taught.

She shook her head. "You have to be Brenda, sweetie. A real man wouldn't wear panties and make his lips all pretty to suck my cock." She looked at his lips. "Oh, that's just just perfect. Now, smear that lipstick all over my cock. Show it some love."

He tentatively got on his knees in front of her and kissed her cock, leaving a nice lip print. "Aren't you the one who used to talk about lipstick on your cock, " she teased? "Well that's a good start. Show me how it's done."

She had never done this with him until now. His sucking adventures had been in private with his own dildo, and he was turned on by this turn of events. The fact that Monica seemed really into it made it better. "I knew you were a cock sucker. Look at that lipstick all over my cock, and pretty far down too. You are a little slut, aren't you Brenda?"

He looked up at her. "I love you."

"I know you do, " she replied with a laugh. "We'll see how much you love me when I have this deep in your ass. I guess now you'll be expecting my cock, won't you? Begging for it?"

He barely took his mouth off of it to answer. She knew she had him where she wanted him. "You'll have to make me happy and earn that honor first, but I do want you ready. You never know when I might have you serving a real cock, since yours is so inadequate. I've been so good to you, but maybe I should lock it up."

"Another cock, " he wondered to himself. Was she seeing a guy? He didn't like the thought of being locked up. "Please, no chastity."

"You don't get a vote in that, " she replied. He seemed to be getting into sucking her cock, and she privately wondered what it would be like to see him suck a real cock for her. She could see him gagging as he tried to take it deep. "Okay, that's enough foreplay, princess. On your hands and knees at the end of the bed. You know what's coming next."

He nervously took his position on his hands and knees and looked back at her. "Sweetie, I don't know if I can do this."

She rubbed her hands on his ass and teasingly poked at it with her fake cock. "Nonsense. You've had dildos in your ass before, or did you forget you mentioned that to me before?"

"But that was different."

She pouted as she grabbed some lube and began probing his tight hole with her fingers. "Don't you trust me, Brenda? I thought you trusted me."

"I do trust you, " he replied.

She was pushing her cock head against his tight opening. "And I trust you. I know you have been faithful to me. Not that your secretary would have use for your little wee wee anyway. Plus, you'd tell me first, wouldn't you."

"I would never be with another... Aww, God, " he yelled as she pushed into his ass and it gave way.

"Shhh, don't yell. It will wake up the kids," she giggled. "Want them to see me fucking you in the ass?"

He grabbed a pillow and yelled into it as he was still feeling discomfort. Her rubber impaler was easing into his well lubed hole, but it still hurt. He hadn't played with his toys since telling her the truth. Secretly, this is what he was hoping for, but he didn't want to push her. He wanted her to embrace this, and he felt lucky that she seemed to be opening up to it.

She felt empowered as her husband screamed into a pillow with her plowing his ass. She wasn't sure how she would like this, but it was turning her on reversing the roles in the bedroom. "Good girl. Just relax. You'll get used to it. Isn't that what you told me when I let you have my ass the first time?"

It was starting to feel better as he looked behind at her with tears in his eyes. "I love you, Monica. You are my Goddess."

She shoved it in deep and he groaned in pain. "Your Goddess demands access to every inch of your body for her pleasure. Can you handle that?"

He was pushing back to take the cock deep. "Yes, my Goddess."

"Even if it means I'm the only one allowed to cum?"

He whimpered. "Yes. I belong to you."

"Good girl, " she replied as she held it in deep. "And for the record, I will let you know when I decide I need a big cock."

He looked back at her with a hint of sadness in his eyes, and she knew what that was all about. "Oh, for crying out loud, I'll let you watch."

She grabbed his hips and began thrusting in and out at a steady pace. "You certainly are sensitive little bitch, aren't you? It turns you on at the thought of watching a big cock fuck me hard, doesn't it?"

"I just want you to be happy, " he moaned as he was really getting into the pounding he was taking.

Monica was quite aroused herself as she continued to deflower her husband with her newly purchased cock. "You'd suck his cock for me, wouldn't you?" He said nothing. "You'd let him fuck you if I ordered you to, wouldn't you?"

He said nothing, but the way he was riding her cock told the story. She started to finger her wetness and noticed him staring to stroke his cock. "Oh no. You don't cum until I tell you you can."

She pulled out of him and removed the strap on as she took a position on her back in bed. "Eat me baby. Right now. Put your tongue in my pussy."

He didn't have to be ordered to do that. Many times, he begged for it. He worshipped her pussy. He knew all the right places to drive her wild, and it gave him confidence knowing nobody could make her feel this way with their oral skills but him. Plus, he craved her taste. This was the woman he wanted to spend the rest of his life with.

It was in these moments that her honesty came out. He could make her feel like nobody else could, and she couldn't imagine herself with another man, even one with a big cock. "Right there, baby. Yeah, oh yeah. God, right there baby. I'm gonna cum, yeah. Oh God. Baby, I love you."

She had just enjoyed a big orgasm when she allowed him on top of her to cum inside of her wet pussy. He knew he couldn't last long, but he kissed her passionately as he released his seed inside of her. As frequently occurred in this situation, she had him clean her pussy once again. Moments like this made him feel like the luckiest man alive.

She kissed him. "Sweetie, that was wonderful. Could you go get me a drink?"

He reached for his pink babydoll nightie and panties. Most nights, she selected the lingerie he would wear to bed, and this night was no different. He went to the kitchen for a drink. He returned to find her asleep, so he put the drink on the nightstand, crawled into bed beside her and drifted off to sleep.

Monica may have talked about having other men, but she really wasn't serious about it. This felt like betrayal to her, and she loved Brian too much to even entertain the idea. Sometimes, solutions to problems happen when you least expect them. This one happened at the office party. The occasion was the company's acquisition of their rival. Brian had successfully landed the deal.

Up until then, she had only heard of Stacy, but she never met the woman. Monica didn't like to go to the office because, truth be told, she missed being a part of it all and this would make he want it more. He missed that, but she also loved being a good mother to her children. She couldn't help but notice Stacy, who was wearing a pink French Maid's outfit despite the fact that it wasn't a costume party. She said she was protesting the fact that Brian overruled her idea for the party.

It was easy to see what Brian and everybody in the office liked about the younger lady. She was easy to get along with. She was flirtatious and friendly. This lady was in many ways running the office. Brian still called the shots in what needed to be done, but some decisions were made by Stacy. Plus, she was the one who motivated the employees to make it happen. It wasn't so much that she ordered people around. They wanted to do it to make her happy.

Stacy seemed to make time during the party to have one on one conversations with everybody except Monica, who noticed that fact. She finally approached Stacy. "Have you been avoiding me Stacy?"

She smiled that same smile that had everybody melting, and Monica felt a tingle. "Not at all. I figured I'd get everybody else out of the way first and save the best for last."

Monica blushed. "Oh, I'm sure you don't mean that."

Stacy took her hand. "Can I be honest?"

"I wish you would."

"Well, your husband is always going on and on about you and how much he loves you and he's building this company up to make sure you and the kids have everything you need."

Monica was surprised by the revelation. "Really?"

"Absolutely, " she replied as she squeezed her hand gently and gave her a look of genuine adoration. "And, I must confess, you are even more beautiful in person than the pictures."

Monica couldn't help but blush from the flattery. "Oh, but I'm sure you don't mean that. The way my husband goes on about you, I thought you two were having an affair."

Stacy smiled and wiped some of her blond hair out of her eyes. "Your husband is a sweet man and very attractive, but there's somebody else I'm interested in."

Monica smiled at the gorgeous woman in front of her. "I'm sure he's a lucky man to have the attention of you."

Stacy again grabbed her hand with both hands this time and squeezed it. "It's not a man I'm after, sweetie."

Monica blushed and panicked in that moment. "Oh, I um... Could you excuse me."

Monica went walking to the ladies room and into a stall. Moments later, Stacy entered the room and locked the door. She stood in front of Monica. "I hope I didn't alarm you, but I wanted to tell you. You seem so sweet, and I feel like I can tell you anything. I feel like I need you tell somebody, but I can't."

Monica smiled nervously. "Well, you’re standing in front of me in a bathroom stall, so you might as well tell me."

Stacy reached under her dress and pulled something out of her panties. "Perhaps I need to show you."

She revealed a rather large eight-inch penis. Monica looked into her eyes in astonishment and saw the lady's vulnerability. "You're a..."

"A transsexual."

Monica was speechless. "I don't get it. Why are you telling me?"

"I don't know. I kind of wanted to tell Brian, but I was nervous about it. Then I started thinking about you and what he says about how caring and understanding you are. I just thought I could tell you." Stacy stared at her, but she got no response. "I shouldn't have done this, should I? God I'm gonna get fired."

Monica thought about how this gorgeous woman revealed her most intimate secret to her. Nobody at the office knew it, but Stacy trusted her. She also thought about how she would like to experience sex with a big cock inside of her, and there was one pointing in her face. If she didn't act now, this lady might walk out of their lives forever, filled with shame for being rejected.

Monica leaned into the cock in front of her and took it inside her mouth. It was quite a bit bigger than her husband's and attached to a feminine body. It was at once confusing and arousing to her. "Oh my God, I was hoping you would like me, " said Stacy as she gently ran a hand through Monica's hair. "I've been thinking some dirty thoughts about you."

Monica was savoring the taste of her magnificent she cock as she sucked the tip. "Like what?"

Stacy smiled seductively. For one thing, burying this thing deep inside your pussy. I bet I can hit you in places he can't."

"Oh my, " she was blushing again as she kept sucking. "I thought transsexuals liked men."

She pulled out of Monica's mouth and guided her to the sink counter to have a seat on the edge. "Not all of us." She kissed Monica. "I'm not against a good cock, but I prefer pussy. More specifically, your pussy."

Monica removed her already wet panties. "Well, then take it. I want you inside of me."

Stacy gently entered Monica and felt the warm embrace of her womanhood. This was truthfully something she wished she was born with. She'd even considered surgery, but she worried about not feeling anything during sex. Her cock still gave her pleasure, and she found that women enjoyed it inside them. Since she could feel that pleasure and still look like a woman to the outside world, she resolved to keep it that way for now.

With her cock inside Monica, she embraced her in a passionate kiss. Their hands explored each other's backs. The feeling of their breasts pressed up against each other was a unique sensation to Monica, but she was very turned on by the contradictions. She squeezed Stacy's girlie love stick inside of her as Stacy continued her gentle thrusts. Despite this being their first actual meeting, this was more of a love making session than a fuck.

The love making went on for a few moments before Monica felt something she hadn't felt with Brian in a long time. As she began to have an orgasm, Stacy came inside of her. They climaxed together and kissed deeply as their tongues engaged in a sensual dance. Monica came out of the sexual haze first and started to worry. "Oh my God. What do I tell Brian?"

Stacy seemed unphased by all of this as she kissed Monica again before pulling out of her. "Do you trust me?"

Monica looked into her beautiful blue eyes. "Yes."

"Good, then lets gets back out to the party. I'll handle Brian at work on Monday." Stacy exited the ladies room first as if nothing had happened. She went right back to flirting with everybody.

Monica couldn't get the memory of being fucked by Stacy's big cock out of her mind, and she carried a bit of her inside of her. When she and Brian arrived home that night, she ordered Brian to eat her out again. He was very thorough. Whether or not he could taste Stacy on her pussy, he didn't say.

At the office on Monday, Brian noticed Stacy staring at him most of the day. What was it, he wondered? Could she tell he was wearing a pink thong? The way it rode up his crack was a constant reminder that he was wearing it. Could she make out his pink bra? He didn't think it looked detectable, but he was starting to have doubts. Stacy chose to wear a much more secretarial looking black skirt suit, while also keeping her blond hair tied back in a bun.

It was when the last employee left that Stacy entered his office. "Will there be anything else, Brian? Do you need any dictation done?" She emphasized dick in dictation.

He squirmed in his chair. He just wanted to get out of there without being noticed. He was sure she knew something. "No. I'm fine. You can go."

She walked to his side of the desk and leaned on his desk. "Well, maybe I have some dictation for you to take."

He looked at her face and knew something was going on in her mind. What was she up to? "What's on your mind, Stacy?

"The erotica line of books."

He sighed. "This again? Stacy, I think you've done a great job of getting that started, but I just don't know."

She smiled at him to try to set him at ease. "Brian, you do know that it's not just people who are in vanilla relationships that read this stuff, right? The gay community reads it. There's potential in the BDSM market. There's the transgender community. And, of course, sissies read it, and they love to read a hot story."

There was something in the way she looked at him when she said sissy that had him squirming. In fact, he became even more nervous. "I just don't know if we're the right publishing company for that."

"I think it would be a hit. It's a niche market, but we can test the waters." She grabbed a pen on his desk and started moving it between her fingers as he watched her perfectly manicured red fingernails move. "Besides, we received an inquiry from an author writing a story about a sissy and his Mistress. It's really quite good, and I bet you'd love it."

He did not like where this was going at all, and he shifted uncomfortably in his chair as his penis betrayed him. "Oh really. And who would write such a story?"

She stood up and walked around the room, delighting in teasing him. "There's this author that you published some 15 years ago. She had a knack for romance novels. It's been a while, but she has a really good idea about a sissy who needs to be put in his place. It's cute actually. The sissy goes out in public dressed as a woman and looks somewhat convincing."

Brian's face went white as he realized who she was talking about. "I don't know, Stacy. Maybe we could give it a shot to test the market."

She walked towards him and leaned over the other side of the desk, giving him a good view of her cleavage. "Tell me something Brian. Have you ever thought of going out as a woman in public?"

He blushed. "What would ever give you that idea?"

She smiled and stood up. "It's just a question. I'm curious." She walked to his side of the desk and stood there. "Tell me, are the panties riding up your ass crack today, sweetie?"

She giggled. "I've known for a while dear. I don't think the people here can tell, but I know the signs. She really picks out a nice lipstick for you when you have your lipstick days. Very subtle. But, Channel 5 is kind of pushing it, I mean, you want them thinking you are a man, right?" She winked.

He was caught, and yet he tried to deny it. "I don't know what you're talking about."

"I tell you what, " she bargained. "Show me you aren't wearing panties or a bra and I'll leave this job and you won't see me again. Show me you are, and we'll try my erotica idea."

He shook his head. "No. I can't."

She sighed. "Sometimes, confession is good for the soul, Brian. You show me the truth, and I'll tell you a secret that I've only shared with one other person. In fact, you may fire me after that."

He reached for her hand. "Stacy, no. Don't even joke with me about that. I need you here. You've meant the world to this company, to me."

"So, strip for me, Missy. Show me."

He was still unsure about this. "You... You won't think I'm some sort of freak or something and quit on me?"

She giggled. "Who said being a freak was necessarily a bad thing? Besides, I kind of like the idea that you are a panty wearing sissy who fantasizes about being a woman."

Gradually, he removed his clothes to reveal the pink thong and matching bra. With his shoes and socks off, his hot pink toe nails were exposed. "Oh my God, I love those toes, " she said with a smile.

"Show her the tattoo on your ass, " came a female voice from the door. It was Monica.

"Oh my God, you have a tattoo? Show me."

He blushed. "Monica!"

She glared at him. "Oh, stop crying and show it to her, sissy."

He turned around and bent over to reveal a pink heart that read Sissy For Life. Above it in red was the word Monica's. "Aww, how sweet." Stacy smiled at him. "That is adorable. I knew you loved her, but to proclaim yourself Her sissy? That's sweet."

He was about to put his clothes back on when Monica spoke again. "Sit down. We're not done here yet."

He immediately sat in his chair. "We're not?"

Monica walked over to Stacy and kissed her on the lips. "No, we're not. I made a promise to you that I intend to keep. I told you I would tell you when I found another cock out there. Well I did."

He was surprised. "You... You did?"

Stacy giggled. "She did."

"Oh, " he replied, trying not to sound too sad.

"Well, " Monica continued. "I feel bad about it, because I kind of got laid before I told you. It happened so suddenly that I had no time to think about it."

"It's true, " Stacy nodded. Brian looked over at Stacy, wondering how she knew about his wife's tryst with another man.

Monica smiled flirtatiously at Stacy. "Anyway, it occurs to me that the best way to make it right is to have you please the cock of my new lover too. That way, we've both shared a similar experience."

Brian shook his head. "That's okay, sweetie. I don't need to do this. I'm okay with it."

She walked over to him and kissed him. "Well, maybe I don't want you to just be okay with it." She walked over to Stacy and kissed her sensually. "Maybe he needs to know how it felt to please such a beautiful cock."

Brian was confused. "I don't get it."

Stacy began removing her clothes. "Remember when I said I had a secret?" She removed her top and bra to reveal a nice set of DD Breasts. Then came her skirt and panties, leaving a semi erect eight-inch penis. It was smoothly shaved. "I'm a transsexual woman."

He stared transfixed at the beautiful woman with the big cock, unsure of what to say. She was still beautiful to him. He knew he still needed her there. "Why didn't you tell me?"

She laughed. "Yeah right. I have no experience, no formal education and I'm a tranny. Would you have hired me?"

He was speechless as she approached him. "Thank you for not lying to me just now."

He looked into her eyes, those blue eyes that played such a big part in his decision to hire this determined and intelligent woman. "You really mean a lot to me and my company. I can't imagine maintaining things without you."

"There is one way you can thank her, Brenda."

Stacy stood in front of him, looking down at him for his response. "Suck her cock for me, " Monica ordered. "Trust me, sweetie, it tastes great."

Stacy turned her head to say thank you as she was greeted by Monica's kiss. In that moment, Brian was sucking his first cock. Not the cock of some hairy man, but a beautiful, feminine transsexual woman. He had already established a friendship and good working relationship with her, and he hoped this wouldn't jeopardize it.

As he was licking on her beautiful cock head and tasting his first traces of her pre release, Monica was stripping naked and took a seat in the other chair by the desk, fingering herself. Brian let Stacy's moans be his guide as he worked his tongue around her sensitive areas and bobbed up and down. "That's it baby. Are you ready for my new lover to feed you her cum?"

He didn't answer as he the stronger taste let him know that she was getting close. "I think she wants my cum, " she said with a look of pure pleasure in her eyes. "Oh yeah. Here it comes baby. Swallow it all."

When he finished sucking her clean, he collapsed in his chair, but Stacy looked over at Monica. "Are you just gonna let your wife sit over there fingering herself, or are you gonna show her what a good pussy licker you are?"

Soon, he was on the floor in front of the chair with his face buried in his wife's neatly trimmed pussy Stacy was kissing her and fondling her breasts. "I could get used to this, " Monica proclaimed.

"Me too, " Stacy replied between kisses.

As Monica had a mini orgasm delivered by Brian's talented tongue, Stacy's cock was alive again and inside Monica's mouth. Monica was in ecstasy when she got up and walked to the desk and bent over it. "Brenda, dear, guide our sexy lover's cock inside of me." On his hands knees by the desk, Brian kissed Stacy's cock and positioned it in front of Monica's quivering pussy.

Brian was incredibly turned on at the sight of his gorgeous secretary's shaft disappearing inside of his wife. He had no idea until today that Stacy was transsexual, and it made no difference to him on a professional level. On a personal level, he knew that he and his wife had found a lover who seemed all too eager to join them in their sexual adventures. He couldn't be happier.

By the sounds of his wife's moans and the way she was breathing, he could tell she was enjoying a big orgasm. As Stacy continued to plow her, Monica stopped her. "Stacy, honey. I'm gonna get over here so my sissy can lick me. I think your next load should be for him, don't you?"

Stacy pulled out and pushed his head onto her shaft. "Clean it sissy, " she instructed as Monica moved across the desk. "Are you saying you want me to make him my pussy boy?"

"Unless you don't want to."

She looked at Monica and then Brian. "The thought has crossed my mind more than once, to be honest with you. And, I know panty boys like him crave it. Okay, bend over the desk sissy."

Brian offered no resistance this time. He wanted it. "Oh shoot. I don't have any lube, " Stacy admitted.

Check my purse, " Monica replied as her husband's tongue was probing her pussy again. "I had a feeling we'd need some today."

Stacy laughed. "I'm sure you did." She lubed his hole up well and was soon pushing her monster cock into his tight hole. With each inch came some pain as Brian got used to it. From Stacy's perspective, it was pure pleasure. She preferred to give it, but occasionally it was nice to receive it. "Does my pussy boy like his secretary’s cock up his ass?"

Brian kept licking his wife's sweet love box until she ordered him to answer. "Brenda, it's impolite not to answer. Don't be rude."

"Mm, I love it, " he replied before going back to work on his wife.

Stacy looked Monica in the eye and had a satisfied smile on her face. "That's what I thought. He has a nice tight butt. I could get used to fucking this hole."

"Well, if he gets too uppity from now on, you know what to do, " Monica replied with a wink.

The pleasure continued to build for Stacy as the sissy's violated hole felt good around her hardness. She could tell the way Brian was moving his ass that he was into it, but she was pleased with herself when his ass started to spasm, indicating that he was in the midst of an anal orgasm. "Oh my God, Monica. Your sissy is cumming. I think he likes it."

Monica's head was leaning all the way back with her eyes glazed over in pleasure. "Oh God.... He's not the only one." Monica was having her third orgasm of the day.

Soon, Stacy joined them as she unloaded her seed inside of her boss's ass. She leaned in to kiss him on the back of the neck. "I know you are my boss, but now this makes you my bitch, Brian. You're my pussy boy."

The three composed themselves and were later sitting on the couch in the lobby, still naked. "Of course, you know that Stacy has the real cock in this relationship now, right sweetie, " she asked her husband as she kissed him?

He thought about how Stacy made him cum by fucking him without him touching himself. "I do."

"You were amazing, Brian, " She kissed him deeply. "You are a natural bottom. You've never done this before?"

"No, never."

Monica giggled. "I have a feeling Stacy has a voracious appetite for sex."

Stacy nodded. "I do. I love to fuck."

Monica kissed Stacy passionately. "So, we need to be ready for her when she needs release inside one of our holes."

"Even here at the office, " Brian asked, noticing Stacy getting aroused again?

"Especially here at the office, " Stacy replied with a grin. "I build up a lot of tension here and need release."

"But..."

"Sweetie, you love me, and you've already chosen to submit to my desires. " she said with another kiss on her husband's lips. " I say we have to submit to the real cock in our relationship, and that's Stacy."

He kissed his wife, "Yes dear."

Stacy grinned. "Good. Now that that's settled, how about you suck my cock some more. I want to see how good your wife's ass feels."

The three enjoyed another couple of hours of passion at the office. True to her sexual appetite, Stacy would sometimes show up to visit Monica during the day for an afternoon lovemaking session, or even at night, She did take Brian's ass when she wanted it, and he never resisted. There were lots of exciting times between the three of them, including Stacy's insistence on having monthly office costume parties and dressing Brian up as Brenda, completely femme in public. Of course, these are stories for another time.            

Tyrone's New Cell Mate

Tyrone sat on a bench out in the yard with his best friend JD. His sissy cell mate of the past five years was finally released. Their relationship was a process of building up trust. Tyrone was a tall and muscular black man. He was the biggest man in this prison, and nobody messed with him if they knew what was good for them

When Chrissy, Chris at the time, was thrown into prison, it was a process of building up trust. He could just rape him if he wanted to, but what was the point of that? He had time to spare, and it wasn't like he was getting out any time soon. Killing a police officer is not something they let you off for, even if he was acting in self defense. The judge didn't want to hear any of that.

He had raped a few new fish, but it just wasn't for him. He wanted somebody who actually wanted to please him, so he changed his approach. Chrissy was his biggest success story. He had lingerie smuggled in for her, makeup and even hormones. Chrisy had a cute pair of breasts and her brown hair grew nice and long.

By the time she got out, she was riding his big black cock like a naughty little slut and begging for more. She actually cried the day she was released She promised to stay in touch, but of course it didn't happen. Tyrone wasn't hurt by that. He knew how it went. The last thing you wanted to do when you got out of here was come back.

He'd had a couple of short term cell mates, but they were gone before he could work his magic on them. Today was the day a new cell mate would be coming. He wondered who it would be this time. "So, what you gonna do, " JD asked? "You've been moping around for too long. The little faggot is gone."

Tyrone turned and gave his friend a threatening look. "Don't be talking about Chrissy like that."

"Alright, alright. I feel you. But you know he ain't coming back to see you, right? What you need to do is find some fresh meat and make him yo bitch." JD grinned and pointed to the short black haired white guy walking along the fence. "Like that one over there."

Tyrone laughed. "You mean the one you fucked?"

"I'm telling you, that one knows how to suck my cock just right, and he's got a nice tight, fuckable ass."

Tyrone shook his head. "JD, I don't want your bitch."

JD grinned. "I'm just saying, gimme that carton of menthols you got coming and he's yours."

"I got my own system, bro. I'm gon get me a new sissy cell mate, you just watch." Tyrone got up and walked over to a couple of black guys who were in a serious discussion. These were two of his associates who helped him get the things he needed.

Back in his cell, Tyrone lay on his bed when the prison guard led a slender, blonde headed guy into the cell. He had no facial hair, blue eyes and his hair was in a pony tail. The guard looked at Tyrone. "Be nice, Tyrone. This kid ain't like you guys. The judge threw the book at him."

Tyrone grinned. "I'm always nice, " he replied as the guard slammed the door shut.

The blonde man sat next to the bars with his arms wrapped around his legs and started crying. Tyrone shook his head as he looked him over He looked to be all of 20 years old. "You got a name?"

"It's Danny, " he sobbed.

Tyrone smiled. "I knew a girl named Dani. Danielle actually. Prettiest thing. You remind me of her. I think it's your eyes. So what did you do to get in here?"

Danny rubbed his eyes. "Pot. I sold pot in my neighborhood. Fucking judge gave me 20 years, and I've never been in trouble before. I just needed the money."

Tyrone looked the small, effeminate man over. "Yeah, don't we all. And don't even get me started about judges. Mother fuckers don't care about justice. You know, if you like to blow smoke, I have some here we could share."

Danny perked up. "Really? I'd like that." He paused "Wait, then I'll owe you."

Tyrone lit a joint. "Girl, relax. I just think you could use this, and I look out for my fiends."

"We don't even know each other, " said the new cell mate.

The muscular black man handed him the joint. "You have an honest face, almost like that girl I used to know. I think we gon be good friends, if you know what I mean."

Danny nervously took a hit off the joint and tried to relax. "So, what are you in here for?"

"Life, " he said with a frown.

Danny handed him back the joint. "Life? For what?"

"I killed a cop, " he replied casually as he took a big hit.

"A cop?"

He blew out a big cloud. "Yeah. Mother fucker tried to set me and a friend up and then threatened us. He shot my friend and I grabbed the gun and killed his ass. Him or me. I chose me."

Danny gasped. "Oh my god, that's terrible. I'm so sorry you had to go through that. " He received the joint and took another hit, feeling a very nice buzz.

The two talked casually and realized they had a few things in common. Both liked to read and enjoyed science fiction. Both enjoyed soul and rap music, even though Danny liked rock & roll too. Both even shared similar political views.

Tyrone surprised his effeminate cell mate. He reached into a box and pulled out a red baby doll nightie and panties. "Do you like this lingerie, Dani?"

Danny blushed. "I've seen the girls on TV wear that. It looks so pretty on them."

He set it on the bed next to him and grabbed some lube. "I bet it would look good on you."

"But I... I'm not gay, Tyrone. Please don't..."

Tyrone laughed. "Relax, babe. I'm not gonna make you do anything you don't want to do, but I'm feeling horny as a mother fucker right now. Pot always does that to me. Do you mind?"

Tyrone pulled down his pants and revealed a thick eight inch cock. He applied lube to it. "I feel like I'm about to burst."

Danny blushed and looked away. Tyrone laughed. "No need to get so nervous. We in here for a long time, baby. We all have urges. Feel free to play with yo little thing too if you want."

Something in the way he said "little thing" made Danny nervous, but he said nothing, He watched as Tyrone came. There seemed to be a lot of it too. "Damn, I needed that. Just a shame I didn't have somebody special to share that with, you know what I mean?"

Danny blushed, and Tyrone noticed. "I got this one," he thought to himself. "Say, Dani, could you hand me that towel by the sink. I made a mess here."


In the shower the next day, Tyrone got a good look at his cellmate's slender and anything but masculine body. He was practically hairless, and had a small cock that couldn't have been bigger than four inches. His own cock started to stir when he noticed one of the black men approach Danny. "Hey bitch. Why don't you get down there and suck my cock."

Tyrone grabbed his arm. "Don't you fuck with Dani over here, understand." He looked around the shower. "That goes for all of you. Hand's off. She's my friend."

Danny felt safe and yet nervous. He loved having protection, but did Tyrone just refer to him as she? The guys laughed. "Uh oh, Tyrone got another girlfriend. She gon be prancing around here shaking her ass in no time, just like sissy Chrissy." They all laughed.

"Stop it guys, you're embarrassing her." He patted his cell mate on the back. "Pay no attention, babe. They just jealous."

The masturbation scene played out in the cell for the next few nights, all the time Danny just watched. Tyrone took it up a notch on the third night as he pulled out some pink lipstick a bra and a pink t-shirt. "I hope you don't mind, but these belonged to somebody I used to know."

Danny watched him stroke his cock again as he talked. "What was her name?"

Tyrone smiled. "Chrissy. She was the cutest little thing, just like you baby. I got her nice things to wear, makeup, even got her hormones."

Danny was confused. "Hormones?"

"Yeah, baby. Female hormones." He felt himself about ready to cum but waited. "See, girls like Chrissy really want to have the body, a pair of tits, a nice ass. I got her hormones. Still have some here too in case I find somebody who needs them."

"So, Chrissy was a guy like me, and he... She... Did she do things with you like..."

Tyrone started cumming. "Suck my dick and swallow my cum? Yeah, she did. That and a few other things. She was real sweet."

Danny was mesmerized by the amount of cum his friend had. He blushed as he thought about swallowing Tyrone's cum. Tyrone grinned. "Relax, babe. I'm not making you do anything you don't want to. But if you ever want to..."

Danny had strange erotic dreams that night. Perhaps it was because he went to bed high, but more likely because of what he had witnessed. In the dream, he was wearing the red panties and nightie and kneeling in front of Tyrone, sucking his cock. He came on Danny's face in a big load. The image in his mind resulted in a very wet dream.

He was almost robotic in the mess hall, just sitting next to Tyrone, listening to the guys talk business. He started to notice there were effeminate men, mostly white, wearing some makeup and clothes in a feminine style.  How could those boys let them dress them up like that?

Were they forced too? He knew what went on in prison. Did the bigger black men rape them and make them dress this way? Tyrone seemed to like the idea too, but why didn't he force him to do it for him? He was so nice to him, protected him, shared his pot with him. He seemed to like the idea of having Danny dress in lingerie for him. Would that be so bad, he wondered?

Tyrone had gone out to the weight room to work out when Danny returned to the cell. He went straight to the box and pulled out a red lacy bra. It felt nice to the touch, so he removed his shirt and put the bra on. His cock started getting hard at the sensation as he looked in the mirror over the sink. He put a shirt on over it. He untied his blonde hair and let it flow

He held the satin red panties in his hands. How would they feel over his cock, which was hard as a rock, all four inches of it. He removed his pants and underwear and slipped into the panties. He was on overload as he put the pants back on. What kind of man would do such a thing and get turned on by it? Maybe he wasn't a man at at. What did the black guys here say? Maybe he was a sissy.


Tyrone and JD sat on the bench in the yard, chit chatting about the ball game. "Yeah, but he still should have caught the pass, " said Tyrone. "It was right to him."

JD caught a glimpse of Danny walking into the yard. "Don't look now, but here comes yo bitch. So, you fuck her yet?"

Tyrone noticed that his hair was down and he liked it. He grinned. "These things take time, bro."

JD shook his head. "No, man. You gonna get a bad reputation if you don't tap that sissy's ass. If word gets out that you haven't..."

"Are you gonna say anything?"

"Come on man, you know I'm not. I'm just saying..."

"Don't worry about it. I got this, " he said with a s mile. "By the time I'm through, Dani over there is gonna be riding up and down on my dick and calling me daddy."

As Danny walked towards Tyrone, the panties were showing ever so slightly above his pants. One of the skinheads noticed it and grabbed him. "Hey faggot. I got something you can suck right here."

Danny pulled his arm away. "Leave me alone."

He shoved the sissy to the ground. "Don't you take an attitude with me, bitch."

Tyrone was there in an instant and laid out the man in one punch. "Lay off, she's mine." He reached out and pulled Danny up. "You okay baby?"

Danny felt a tingle. "Yes, thank you. I don't know what I would have done if you hadn't..."

"Don't worry about it. Come sit with my and JD, " he led Danny to the bench. "By the way, I like what you did with your hair."

Danny blushed. and smiled "Thank you."


In the cell, Tyrone pulled out another joint, and they relaxed. He pulled down his pants and reached for the box. Danny stopped him "Tyrone, I have a confession to make."

He pulled down his pants and removed his shirt to reveal the red bra and panties. "I'm sorry. I just couldn't..."

Tyrone stood up and hugged his sissy. "Relax, baby. I wanted you to wear them. Those are your clothes. My girl wears sexy things for me."

He reached into the box and pulled out the satin baby doll nightie. "Would you wear this for me, please?"

Danielle blushed, but did as asked as Tyrone handed her a tube of red lipstick. "And this too, please."

Daniele looked into the mirror and tried to get it just right. Nervously she turned around. "How do I look?"

Tyrone took her into his arms and kissed her. "Does this answer your question, baby?"

She melted into his kiss as she felt his bulge pressed up against her. He sat down and pulled his pants down. "Baby, I've been dying for you to do something for me. Would you?"

"Do we... Do we need a condom for this?"

Tyrone laughed. "Baby, it's just you and me. You ain't sucking any cock behind my back, are you baby?"

She blushed. "Of course not. It's just..."

"Baby, we gon be together a long time. Might as well get used to my cum. I got a lot of it for you. Now, put those pretty red lips on yo daddy's cock."

Danielle knelt between his legs and kissed the tip of his cock. Having never done this before, she could only guess what needed to be done as she licked his hard shaft and then started slowly sucking it. She felt it twitch as she slowly glided her tongue underneath his head. "Yeah, baby, that's perfect."

She gave him a slow and sensual suck as his taste became stronger. She recalled her dream of a couple nights earlier, but she wanted his cum in her month. In moments, she got her wish as he let his manly fluids loose. He smiled as he watched her. "That's it, baby. Swallow daddy's load. It's all for you."

When she was done, they cuddled in the small bottom bed and kissed. "Tyrone. Do you think I should take hormones like your old girlfriend?"

He kissed her. "That's up to you do decide, baby. The hormones will be in the box if you want them. I guarantee you gon be a hot babe if you take them."

They spooned in bed and fell asleep with him holding her in his arms from behind. It was a couple hours later when she got the surprise of her life. Tyrone was hard as a rock and pressing his cock up against her tight sissy hole. She had never been penetrated before. "Tyrone, what are you doing?"

He reached into his box for the lube. "It's time, baby. I need to make you mine."

"But, you're too big, " she protested.

"No babe, you just too tight is all." He spread some lube on her hole and entered it with a finger and then two. "How does that feel?"

"I don't know. It doesn't hurt too bad."

He lay her on her stomach and pressed his cock against her hole. She started to moan. "Bury your face into the pillow, baby. We can't be making too much noise now."

It hurt as the first couple inches of his cock pushed their was past her tight entry way, and she felt a tear in her eye as he kept pushing in. He was determined to get it all inside. He kissed the back of her neck. "You doing fine, baby. Almost in. Just relax. A little more."

Danielle felt like she would be split in half as Tyrone had it all the way in. "There it is baby. How does it feel?"

"Still hurts a little, " she moaned.

"Feels real good to me baby, " he said as he kissed her neck. "Just relax and let daddy take control."

He began to slowly thrust in and out, and the pain was still there as she felt empty and them full with each slow thrust. Was this going to be her life in prison? Was she ready for it? So many thoughts and emotions ran through her mind as he slowly fucked her virgin ass.

Was this so bad? She knew she would probably get raped in prison. Everybody warned her about it. But, Tyrone wasn't bad at all. He was good to her. And, she kind of liked him too. Was it to much to ask to let him have her ass for all the good things he did for her?

"Oh God, I'm gonna love pounding this fine ass baby, " said Tyrone as he continued to thrust inside of his sissy's loosening ass. "How does it feel now, Dani?"

"Kind of nice Tyrone, " she confessed.

He picked up the pace. "It's gonna get even better. Let me know where it feels good and I'll show you. I know how to make girls like you feel good."

She relaxed and started to realize there was a place inside her hat felt really nice when he hit it. She started working on it. "Yeah, right there."

"You like daddy's big cock in yo ass baby?"

"Mmm, yeah, gimme your cock, daddy."

He kept fucking her deep. "I know a few places around here we can fuck. Me and Chrissy used to have a good time. We gon have fun together, Dani. Just you and me."

She was pushing her ass against him as he trust in. "Fuck me anytime. I'm yours. I think I'm gonna cum."

He kissed her neck. "You cum when you feel it. Daddy won't be far behind you."

The pleasure both felt was amazing. Tyrone hadn't had a tight sissy ass in a while. He felt her ass squeeze his cock and knew he as making her cum from the pleasure he gave her. It was a slow and steady cum that felt unlike anything Danielle ever felt before. She could get used to it.

It wasn't long before Tyrone grunted and tensed up. He began filling his sissy's no longer virgin hole. He lay on top of her with his cock still inside her. She felt oddly secure and safe underneath her man. He kissed her on the neck again. "Baby, how long did you say you in for?"

"20 years."

"Well, don't take this the wrong way, but I'm glad."

He pulled off of her and they lay face to face. She felt his warm cum inside her ass, and it felt nice to her. "Why is that, " she asked?

He kissed her deeply. "Because, you and I can have a lot of fun together. The way I see it, as long as we in here together, we're married. You mine, " He kissed her again. "You take care of me, and I'm gon take care of you."

Danielle felt goose bumps, and she smiled. "I think I'm gonna like being your wife."

She melted into his kiss. Prison was not where she wanted to be. But, if she had to be, at least she was in a situation in which she felt safe and secure.            

Sissy Breanna's New Daddy

Sissy Breanna's New Daddy

Billy was a young college student looking for ways to make money. He did what he could do and managed to get by okay. He also had a secret that people didn't know. He loved to dress up in private and always felt that he was more of a girl than a boy on the inside. He was also very guarded about his personal business and had a fear of talking to the therapist he would need to speak with to get started on his transition.

Like many others, that led to self medication, which he had done off and on for a few years. His already slender frame had taken a more feminine softness, and he managed to grow B Cup breasts before stopping for fear that his feminine appearance might hurt him in the job department. This left him very conflicted, and he struggled at times. His dorm room wasn't a safe place to dress up, and it had been a while since he had a few moments of time for his feminine side.

Ken Jones was a successful business man in his 40's. He had slightly greying black hair and kept himself in pretty good shape. He ran a hardware chain, and at times that left him out of town for several days or even a week at a time. Ken threw himself into his work when his wife of 20 years died suddenly a year earlier. Though he was lonely, he hadn't so much as dated since then.

Ken decided to hire a house sitter to keep things in order. This involved some cleaning of the house and swimming pool in the back, washing the cars and feeding the cats and dogs. He immediately liked Billy and hired him during his first interview. He thought the young man was intelligent and dependable, albeit a bit shy and guarded.

It was on the first weekend on the job that Billy found the clothes. They belonged to Ken's wife Margaret, and they were in boxes in one of the other bedrooms. There was also a makeup desk with makeup still there. Billy looked through the boxes and found countless lingerie items, dresses, skirts, and casual wear, and was excited when he found that they fit. Wanting to make sure he got everything done, he did the chores before he dove into the clothing.

Billy could barely maintain his focus as he went through all of the routine before returning to the boxes. He stripped down immediately, and was disgusted by the site of the body hair he had. He went through Margaret's boxes and fond some disposable razors. He drew a bath with some of her finest bath oils and meticulously shaved all of his body hair, including around his crotch. He preferred to be smooth.

When he got out of the tub, he admired his work in the full length mirror. His small cock of about four inches stood at attention as he gazed at his reflection. He went back to the boxes and found a hair drier and a curling iron before attempting to do something feminine with his medium length brown hair. Satisfied with his work, he went back to the room and found a sexy red lace teddy and matching panties.

The job wasn't complete. He sat down at the makeup table. There was some foundation which seemed close enough to his shade. There were a couple of shades of lipstick, and fortunately ruby red was one of them. There was also lip gloss and lip liner, and he was meticulous in having the perfect lips. He went through the mascara and a light blue shade of eye shadow.

Billy looked at himself in the mirror and smiled. "There she is , " he thought. His feminine self, Breanna. He started fondling his breasts through the nightie. It had been a while since he'd had any hormones, but they were still very sensitive to the touch. Breanna was turned on in this moment as she went to the boxes. "I wonder, " she thought.

Before long, she found the answer. In a box within one of the boxes were three very distinct toys. There was a small vibrator and a regular sized vibrator. She turned it on and the batteries still worked. The dildo in the box was flesh colored and looked to be at least eight inches long. She took the working vibrator and the dildo into the master bedroom.

The bedroom was still decorated with a woman's touch. There were lots of pink and red. The bed had satin sheets. On the dresser was a picture of Ken and Margaret, standing by the water in their swim suits. She wore a pink one piece with a floral pattern on it. Her bust looked to be at least DD cup, and her ass filled the bottom of her swim suit quite nicely.

Breanna stared at Margaret for a long while. She had beautiful long blond hair and pretty blue eyes. What a gorgeous woman, she thought. Those thoughts turned to jealousy of that beautiful body, and then she looked at the picture of Ken. There was a noticeable bulge in front of his tight swim suit. Thoughts turned to what it must have been like for Margaret to please her husband. She set the picture down on the dresser and took a seat on the bed.

She imagined Margaret taking her husband's cock in her mouth and soon had the dildo in her face. She kissed the tip, leaving a trace of red lipstick on it. She giggled to herself as she licked it off and opened her mouth wider to take it inside. She ran her tongue along the underside and moaned a little as she imagined Ken's wife going down on him. Before long, she was testing her gag reflex, which got her excited as she got on her back on the bed.

She reached over into the night stand drawer and found a jar of Vaseline among the contents. She pulled down her panties and inserted two fingers into her tight hole. She held the dildo in her hand and continued sucking while fingering herself for a moment. She then replaced her fingers with the vibrator, which she turned on high. In no time, she had the vibrator deep inside her while continuing to suck the dildo.

She felt like a genetic woman in that moment, pleasing two guys at once. Up until that moment, she hadn't even touched her clitty, and the vibrator was hitting her in places that made her feel like she might explode. But the pleasure built up and subsided a few times before she gave in. She put the dildo down and started slowly stroking her clitty while working the vibrator inside her. In moments, she had an immense orgasm as spurts got away from her and landed on the bed spread.

She lay there catching her breath before feelings of guilt started to enter her mind. This was wrong. She took off the lingerie and took the spread and blankets to the washer. She cleaned the toys and put them up, telling herself she couldn't do it again. “I'm Billy. Nobody would understand. Knock it off Billy.” Billy gathered his senses and headed to the living room.

There was a baseball game on, and he remembered Ken telling him he could help himself to the beer in the fridge. Within a couple of beers, he was loosened up as he went to the bathroom. He realized he hadn't even taken off the makeup. He still looked very feminine. He found a nude bra and panty set, a pair of cute shorts and a purple top and put them on. Then, he noticed some hot pink nail polish on the makeup stand. He took it and returned to the living room.

After grabbing another beer, he painted his toe nails. He barely paid attention to the game as he tried to get the polish to dry. He considered painting his finger nails, but thought it wasn't a smart move. Upon admiring his painted toe nails, the feminine feelings were returning. Then, came the realization that the dogs needed to be walked and the car needed a wash. Not wanting to change clothes, it was Breanna who left the house with the dogs.

Breanna walked the two dogs to the park, looking around to see if anybody noticed her. There were people in the park and the roads were somewhat busy. However, nobody seemed to notice her. It was on the way back when a group of guys drove by and yelled out the window. "Hey baby. Nice ass."

Empowered by her walk, Breanna decided to stay dressed this way to wash the car. It felt liberating to be completely feminine and in public. She longed for this to be a permanent thing, but she knew that it would end with the weekend. She was grateful for the time she had here and excited about the possibility that it would continue when she was called back to watch the house again.

When Ken returned, he had a look around at the house and the car He was pleased with what he saw. "You did a good job Billy, " he said as he offered him a beer. "I'm gonna tip you 20 bucks, and next time you can wash the other two cars. Do you know anything about shampooing the carpets?"

Billy took a big drink. "No Mr. Jones, but I can learn if you want me to."

Ken smiled. "Good. I like somebody who can adapt when the situation calls for it. I'll rent the shampoo machine next weekend."

Billy shook his hand. "Sounds good. I really appreciate you giving me this opportunity, Mr. Jones. I needed the extra money. If there's anything you need, I'll be more than happy to do it for you."

Ken saw Billy to the door and set his laptop computer on the kitchen table. It booted up with the same picture from the room as his wall paper. He ran his finger gently on the screen over Margaret's face. "I miss you so much, baby."

He accessed the surveillance program, which enabled him to view the cameras around the house. He wasn't planning to view any in the house, but he wanted to make sure there was nobody creeping around outside. He viewed it backwards from that moment. Then, it came to the car washing scene.

There was a pretty brunette washing his car, and she wore a pair of shorts that looked familiar. The woman looked familiar as well. "That's odd, " he said out loud. "Billy never mentioned his sister stopping by to help."

He focused on a clear shot of the woman's face and was shocked at what he saw. "That's Billy. It has to be. What the hell is going on in here?"

He accessed the recordings of the living room and saw the woman doing her toe nails. There was no mistaking that this was Billy now. Ken was familiar with transgender people. His wife did volunteer work at a homeless shelter and had brought a few of these ladies home to stay with them from time to time.

He focused on the room with his wife's clothes in it and started the recording from when Billy arrived. He watched in amazement as Billy rummaged through her lingerie and watched intently when he returned to the room smooth shaven and in the lingerie as he did his makeup. He felt a stirring in his pants as he was becoming aroused by what he saw, and he was even more curious when Billy took the two toys with him out of the room.

He took note of the time stamp and started the camera recording from the master bedroom at that point. He watched intently as Billy grabbed the picture and looked at it. When Billy grabbed the dildo and started sucking it, Ken undid his pants and released a rather large eight-inch cock. He couldn't help but imagine Billy's red lips wrapped around his man meat.

Soon, Billy was on the bed with a dildo in his mouth and a vibrator in his ass. Ken couldn't take his eyes off of the image as he stroked his rock-hard cock. He imagined what it would be like with his cock in Billy's ass. He had no way of knowing at the time that Billy was a virgin. The scene was too much for Ken, who shot his load moments before the video showed Billy stoking his clitty to an orgasm of his own.

Ken had conflicting thoughts going through his mind. He liked this young man, and he felt that he could very well be transgender or at least a transvestite. The small breasts indicated that Billy had at least begun transition. If that was the case, he had more than enough money to help. At the same time, thoughts of burying his massive cock deep inside of Billy's ass were over powering, and he felt himself getting harder just thinking about it. He also knew he had a problem.

If he brought this up in the wrong way, Billy was liable to leave and not come back. He wanted Billy to stay. He could tell he had a kind heart, but that he didn't like to talk about himself. He was definitely geared towards pleasing others, which is something he had in common with Margaret. Margaret was always helping other people, and she was very giving in the bedroom.

An idea came to Ken in that moment. He went down to the bedroom with the clothes and started going through the boxes. He took a note pad and started writing down items he recalled his wife wearing that were no longer in the boxes. This would include corsets, stockings and garters, five inch stiletto heels in various colors. Then, there were toys. He resolved to help Billy get ready for his cock by buying a butt plug set as well as a couple more dildos. One was a high dollar suction dildo.

He looked at the makeup desk and decided to add more makeup products, but he knew he needed to rush this stuff in before the weekend. He called Margaret's closest friend Dee, who sold Mary Kay Makeup products and held the occasional pleasure parties for women. He explained what he was looking for over the phone to Dee. "Good for you sweetie, " she said. "I'm glad you are getting back on the scene with another woman. If I wasn't married, I'd scoop you up myself. Let me grab my catalogs and come right over."

There was a knock on the door in 15 minutes and he answered. A short brunette woman carrying a bag came in. "I got here as soon as I could. So, who's the lucky lady?"

He led her to the couch. "I need discretion in this matter if you don't mind."

She took a seat. "Understood."

"And, " he added as he expected a negative reaction. "I need it all by Thursday."

She shook her head. "Ken, I can’t do..."

"I will pay you triple what it costs if you do this, and I will be eternally grateful."

She paused for a moment and picked up her cell phone. "Sweetie, do you still have any of that red wine we used to have when Maggie used to cohost the parties with me, and can I get some? I need to make a call?"

He smiled. "Of course. I'll bring the bottle." He ventured down to the wine cellar and grabbed a nice vintage after taking a few moments to figure out which one. He returned to the kitchen for glasses and brought them to the coffee table. He poured two glasses and handed one to Dee.

"So, you can then? Great. Let me get back to you in a about 30 minutes. Thanks, you're an angel." She hung up the cell phone and took a sip of wine. "Well, good news. Glenda can fulfil the order in that time."

He handed her the list he made. "That would be great. I made a list and I think I got the names right on the things. Plus, I want you to order every makeup item Maggie ever bought from you that you still have."

That last drink almost went down the wrong pipe after what Dee heard. "You're kidding? All of that?"

"Absolutely."

"She must be a special lady for you to spend that much." She poured herself another drink.

He smiled. "Put it this way, I want this lady to feel a special as she is."

Dee looked at the list. "Butt plugs. Stiletto heels, corsets."

He took a drink. "Oh, better add some of that special lube oil and the scented body oil. Maggie always knew the ones..."

She took his hand for a moment and looked him in the eye. "Sweetie, is there something you want to tell me? Are these things for you? You can tell me anything..."

His face went red for a moment. "No. Nothing like that, Dee. I'm all man, and I love women. It's just..." He finished a drink and poured another one. He knew her well enough to know she wouldn't let go of it until she got answers. "Look, you have keep this hush hush for now. It's not that I'm ashamed, but I have my reasons for now. Promise?"

"Ken, of course I'll keep it a secret." Her pink campaign lipstick got on the glass as she took a sip. "I have to do that for some of my clientele. You'd be surprised how many sissies and cross dressers I sell to."

"Well, I'm thinking this one may be transgender and needs guidance. And, I'd like to help her."

A mischievous grin spread cross Dee's face. "Sweetie, a man doesn't spend this kind of money on a woman for nothing. You want to fuck her, don't you?"

He spit his drink out of his mouth at that last comment. "No. It's not like that. I mean, I want to... Um... I want to be with her, but I want to help her too. I think she needs guidance to understand who she really is, and..."

She took his hand. "Sweetie, how long has it been since you've been with a woman?"

"Since Maggie."

"Oh my God, " she said as she took a drink."

He looked at her and her poker face was blank. He knew she was thinking something. "What?"

She started giggling, "You're gonna split that poor girl in half."

"Dee!"

She took another drink. "I'm just saying, Maggie told me about you."

He smiled as a look of pride crossed his face. "Well, that's why I'm getting the butt plugs and the dildos."

She poured another drink as the alcohol was already making her feel good. "So, who is this would-be cock rider?"

He remained silent, but she wouldn't let go of it. "Come on, Ken. Spill it."

"You just don't give up, do you?"

She shook her head. "Tell me."

"It's my house sitter, Billy."

She gasped. "The college student? The shy kid you were telling me about? Ken, he's half your age, you perv."

"Yeah, well check this out Dee." He stood up and grabbed his laptop from the kitchen table. He had the four videos open. "There's this one, " he started with Billy washing the car in his wife's shorts and top.

"Okay, so, those are your wife's old clothes?" He nodded and showed the video of Billy painting his nails and doing his makeup. "Oh my. Are those.... Is he growing breasts?"

He nodded. "Yeah, so you see..."

"What's the other video, if you don't mind me asking?"

He shook his head. "You don't need to see that. I think this pretty much..."

"Show me Ken, " she insisted. "Something has you worked up to spend the kind of money you're about to spend."

He hit play as the scene unfolded from Billy looking at the picture to sucking the dildo and taking the vibrator up is ass. She gasped. "Oh my. Well, that explains it. Okay, let me send this order to Glenda, and we'll get it started."

He stood up and went to the kitchen table. "I'll get my card."

After ordering, she stared at him for a moment. "You know, you should be careful not to play with Billy's emotions too much. Transgender women have to deal with a lot."

He nodded. "I know. Remember, Maggie and I helped a few. I think I understand. It's just that Billy seems to be living in denial right now, and I think I can help."

She burst out in laughter. "By fucking his brains out."

He chuckled. "It's not like that, Dee. Are you sure you're okay to drive? I can call you a cab."

She poured another drink. "That would probably be best." She took a drink. "Unless you want to take me for a ride on that monster."

"Uh huh, and what would Dave say about that?" I'll call you a cab.

On Thursday, everything arrived on schedule, and Ken began removing the tags from all the items. He added them to the various boxes thinking that Billy wouldn't notice they were new. He found a smaller box, put the dildos inside it and then put that box inside one of the bigger boxes. Then, he put the makeup in the bottom drawer of the makeup desk. At some point, knew Billy would investigate things further.

On Friday, Ken found himself feeling so horny that he had to jerk off three times before Billy got there. "Okay, Billy, the shampoo machine is here and it's pretty simple to use. I want you to do the living room and the guest bedroom. Keep things clean here, wash the cars, take care of the animals and feel free to help yourself to whatever is in the fridge."

"Got it. You can count on me, Mr. Jones"

The older man shook his head and smiled. "And none of that Mr. Jones stuff. Call me Ken."

Ken drove to the airport thinking about what Billy would be doing next. More importantly. How could he take this to the next stage? He reasoned that until he figured that out, he would let Billy explore his feminine side with whatever was available in the house. He would watch the scenes unfold on his surveillance recordings. He decided it best to wait until after he got home for that or he might not get any work done.

Billy watched the car pull out of the drive way and headed to the room with the boxes with stripped naked. He felt his skin and decided a bath and a body shave might be needed first. He dreamed of a day when he could afford hair removal. After the bath, he started looking more carefully through the boxes. Was there more this time or had he not paid close attention? He spotted a pink teddy with matching panties that said, "Dirty Girl" on the back. There were stockings and garters, and he decided to go all out. A corner box marked shoes revealed more shoes than he had dreamed of. Within the box was a pair of pink open toed five-inch stiletto heels.

He stopped and went to the desk where there was nail polish and remover. A cute hot pink polish was begging to be used, so he removed his toe nail polish from a week before and added a new coat of pink. He got bold and painted his finger nails too. After allowing them time to dry, he applied makeup. He couldn't find a hot pink lipstick, but a search of the bottom drawer found the color in lipstick, lip liner and gloss. His lips looked immaculate, and he saw traces of Breanna again. It made him smile as he finished applying the eye shadow.

Breanna loved the image staring back at her in the mirror. For the first time in a while, she was thinking it might be possible to order more hormones. She started dancing around the room in her high heels. She knew she'd better get started on the floors, but she decided to get her toys ready for play time. As she looked inside one of the boxes for the smaller box, she discovered there was a plug set, and a suction cup dildo. She felt a tingle as she grabbed both items.

After retrieving the Vaseline from the master bedroom, she opened the plug set and grabbed the medium plug. She lubed her tight hole and shoved it in. She felt a bit uncomfortable at first, but somehow whole. As she got adjusted to it, she began leaking a bit into her panties. It was a constant state of arousal for her. She began rubbing her panties. "Dammit. I think I need a chastity cage, " she said aloud.

"Oh, to heck with it, " she said as she rubbed her panties for a moment. She felt herself ready to cum and pulled her clitty out to shoot on her hand in front of it. Without even thinking, she came on her hand and licked off every drop. She began to feel the remorse again, but instead of removing everything, she headed for the living room.

After briefly reading the instructions, she moved things out of the way and began slowly shampooing the room. The pleasure of the plug inside of her was again getting the better of her. When the room was done, she headed to the clothing room, grabbed the suction dildo and headed to the master bedroom. On the wall opposite closet mirror, she found a place and fastened the dildo. She rubbed her panties as she began sucking the dildo.

She imagined Margaret sucking her husband's cock in that very room. She guessed she probably did it hundreds of times. She wondered how big his cock was. She imagined herself kneeling in front of him and sucking it until he came in her mouth. She wondered how his cum tasted. That was it for her. She removed the plug and her panties. She slowly backed up on the dildo.

The thoughts in her mind were again of Ken, and she pushed back while looking at her reflection in the mirror in front of her. "Oh, Kenny, fuck me, " she caught herself saying. She kept a steady rhythm as the dildo slipped in and out of her well lubed sissy pussy hole. Her clitty dangled down untouched for a while as she focused on the fake cock in her ass. To her, it was Ken's cock in that moment. "Give it to me daddy, " she said as she turned to simulate Ken leaning down to kiss her.

The pleasure built as she kept the pace up, in and out. It was driving her over the edge as she began stroking her clitty again. "Mm, I'm cumming, daddy," she proclaimed as a few drops came out of her and onto the floor. Without hesitation, she turned around and cleaned the mess with her tongue. She felt like a dirty little slut, and she liked it. There wasn't as much shame this time as she knew this was right to her.

She also knew that the plug made it difficult to concentrate on her work, so she left it out for the time being as she shampooed the guest room. With the living room and bedroom floors drying off, she went back to the clothing room and switched into a pink shirt and shorts to go feed the dogs and cook something to eat. That night, in a black satin chemise and matching panties, she reinserted the plug and slept soundly in Ken's bed.

Her toy play continued the next day with another ride on the suction dildo. She ventured out of the house in a cute knee length purple dress. She again found some five-inch heels and a purse that matched them in black. She was meticulously made up and had the plug inserted as she went to the grocery store. She didn't really need anything, but she went just to go out.

At the store, she picked up some milk and cookies, and then had an idea to get a big take and bake pizza from next door for when Ken returned. She wouldn't be dressed up then, but she would have a meal waiting for him upon his arrival. When the day came, Billy was back in his shorts and shirt and no makeup. When Ken called to say he'd be back in 20 minutes, he put the pizza in the oven.

When Ken walked through the door, Billy greeted him with a beer. "Welcome back. Got a beer for you and pizza is almost done. How was the trip?"

The first thing Ken noticed was the hot pink nail polish that Billy forgot to remove. He looked at him with a smile. "Really? Did something happen that you need to tell me?"

Billy shook his head. "Oh, no sir. I was just at the store and bought a pizza yesterday. I thought you might like some after the trip."

Ken looked around the living room. "Floor looks spotless. Nicely done. I see you figured it out."

Billy felt the urge to kiss him for the compliment. "I got it all done, just the way you like it."

Ken had a curious look on his face. "I like it when you can do it just the way I like it."

Billy blushed and headed to the kitchen. "Let me get your dinner on the table."

Ken followed him. "Care to join me?"

Billy brought it to the table. "I wish I could, but I have to get back. I have a big test on Tuesday, so I need to study."

Ken gently rubbed his back, making the young college student tingle all over. "Well, I sure appreciate all you've done. I'm gonna give you another bonus. If you didn't have school, I'd bring you on full time as my personal maid."

Billy felt a stirring at that last comment and noticed the bulge in Ken's pants. He laughed nervously. "Too bad I'm not a maid."

"Well, I could always get you a nice maid's outfit if you want, " he replied with a grin.

Billy headed for the door. "Let me know when you need me again."

Ken accessed the videos from the program and watched the young man transform into a young woman and dance around the room in the pink high heels. "What was that, " he asked as he went back a moment in the video to hear what was said.

"Dammit. I think I need a chastity cage, " Billy remarked on the video.

Ken released his rock-hard cock from the confines of his pants as he accessed the video from his bedroom. Knowing that Billy was already plugged was one thing, but soon he saw the video of Billy sucking on the suction dildo. Soon, it was up his ass when Ken heard the next comment. "Oh, Kenny, fuck me."

He started to imagine his cock up Billy's ass, giving it to him deeply. There was no doubt in his mind that the college student was more girl than boy. He watched Billy look behind and simulate the kiss as he said, "Give it to me daddy."

Soon, Ken was shooting his load underneath the kitchen table. "I've got to get this one into my bed." He kept the video going when he saw Billy reinsert the plug and then slip into his bed. He knew he had to make it happen.

Ken took a chance by ordering a chastity cage sent to Billy's dorm room. He figured it would might look like he was leading him on if he suddenly found it at the house, and he could play it off as a joke if somebody saw it in the dorm. As luck would have it, nobody knew about the package but Billy. He took some razzing for the pink nail polish, but he played it off as spending time with his young niece, who painted his nails. He was floored to see a pink chastity cage in the box. He couldn't wait to try it on.

When he arrived a Ken's house a few weeks later, he had the cage on. He made use of all the clothing he could as he got more comfortable as Breanna. He excelled at doing the chores and taking care of things. He got more adventurous using the toys, including an outside cum session by the pool in one of Margaret's swim suits. Every weekend he found an excuse to leave the house in a dress and heels. He also let his hair grow longer. Watching Ken's house became the most important thing happening in Billy's life. He also continued the ritual of having dinner and a beer waiting for Ken when he returned home.

However, Ken knew he needed to take things to the next level. After careful research about transitioning from male to female, he ordered several things from a reputable online pharmacy and decided to invite Billy to his house for the weekend as a thank you.

Billy was nervous when he arrived with a bag. "You didn't have to do this, Ken."

He just smiled and pointed to the bedroom. "I think I did. Put your stuff in the guest bedroom and come join me in the living room."

Billy set his bag on the bed when he noticed a sexy pink babydoll, panties and bra set. "He walked into the living room, carrying the three things. Um, Ken, what is this?"

"Oh that, " he replied causally? "That's for you to sleep in, sweetie."

Billy blushed. "Ken, I..."

"I know what you've been doing here, young lady, and I must say..."

Billy's face went red. "Oh. Well, I guess I better get my stuff and go. I'm sorry."

Ken reached out and grabbed Billy by the arm. "No, sweetie. You didn't let me finish. I was gonna say, if you had told me up front, I might have helped you."

"To what, fuck me, " Billy blurted out?

Ken laughed. "Honey, if I wanted to take that ass by force, I could have had you weeks ago, and I doubt I would have needed to use force. But, that's not what I mean. I want to help if I can."

Billy was skeptical. "What, be my daddy?"

"Don't be ridiculous, " he replied with more laughter. "Daddy's end up having sex with their girls, and I'm not gonna force myself on you, Billy, You're too confused and vulnerable. I only want to help if I can."

"But, I'm not confused. " Billy had a look of certainty in his eyes. "I know I'm a girl inside."

"Regardless, there's no pressure from me, Billy. But, I would like to get a look at this girl you say you feel you are inside."

Billy thought about it for a moment. "I need to get freshened up."

Ken smiled. "You know where everything is. Take all the time you need, but I'd like to see you in that lingerie." Billy looked at him nervously. "Oh, don't give me that look, young lady. I just want to see how it looks on you."

The young sissy grabbed a razor from his room and drew a bath. He removed his chastity cage for the bath. As he shaved, he started to relax a bit. He admired his naked body afterwards with pride. After reattaching the chastity, he slipped into the silky pink panties and bra. He strained against the cage at the site of his reflection and began to fondle his small breasts through the bra cups.

Breanna was starting to emerge as she slipped into the soft and sexy, short babydoll. It practically melted into her skin, causing a wonderful sensation. She slipped into the clothing room for the curling iron and hair dryer and attempted to do something with her hair. She managed to curl it a little. "I really need a salon appointment, " she said to herself.

In the clothing room, she grabbed the pair of pink, five-inch stiletto heels. She considered stockings and garters, but opted for bare legs. After some mascara and eye liner, she applied a few shades of blue eye shadow and went for the smokey eye look. She admired her work in the mirror. "I'm getting better at this, " she thought.

She reached for the hot pink lipstick and lip liner, finishing it off with the pink gloss. "You about done in there princess, " she heard him call.

"Almost. Gimme a minute, " she replied nervously.

"No rush. Take your time. I'll have a glass of wine waiting here for you, so we can relax and watch a movie or something."

She started thinking about what he really wanted from her. Was he looking for sex? Could she really perform for him and how would his cock feel inside her? How did he know what she was up to before? That part bothered her a little bit. She admired her reflection and headed out of the room. "Ready or not, here I come."

As she walked into the room, she felt his eyes staring intently at her. She walked to the center of the room and did a twirl as gracefully as she could in the high heels. She turned around and shook her panty clad ass seductively. "Damn, sweetie. You shouldn't tease me like that. I'm trying to be honorable and respect your virtue."

She giggled. "So, what do you think?"

"Gorgeous, simply gorgeous." He patted the seat next to him. "Have a seat, sweetie. I know I can't call a pretty thing like you Billy anymore. So, what's your name?"

She sat next to him and grabbed the glass of wine for a big sip as she tried to relax. "It's Breanna, or Brea if you like." She took another bigger drink, leaving a trace of pink lipstick on the glass.

He touched her bare leg gently, sending goose bumps through her body. "Breanna. A beautiful name for a beautiful young lady."

She finished her drink. "So, how did you find out?"

He poured them both another drink. "By accident. It's kind of a long story. I hope you don't get upset with me."

"It depends, Ken. Just tell me."

He took a drink. Looking at the pretty young thing next to him was causing a strain in his jeans. "Well, I have an outdoor surveillance camera. I've had people prowling around, and I just try to keep an eye on things. The first time you watched my house, I noticed a young lady washing my car in a cute pair of shorts that hugged her ass as she dunked the rag in the bucket to soap my car up. Imagine my surprise when I recognized you."

She squirmed a little in her seat at being found out. "I see. Well, I was just..."

"Anyway, " he interrupted. "I have had cameras in every room of my house for several years and upgraded to the current system three years ago before my wife..."

"You what?"

He grinned. "Well, my wife and I liked to have fun from time to time, and we played in every room in the house. She really knew how to turn me on, and I've got to tell you, the things we did..." A tear came to his eyes as the loss of his beloved Margaret still hurt over a year later.

She rubbed his leg. "You really did love her, didn't you?"

He took a drink. "More than you know. She was one of a kind, had a heart of gold and she helped a lot of people. We even met a few women like you."

"Women like me?"

"Transsexual women, Breanna." He smiled at her. "You are transitioning, aren't you?"

"You could tell? I haven't been on hormones for a while, " she replied with a hint of sadness in her voice.

"Sweetie, I hope you don't mind me saying this. I think you have a cute pair of breasts developing, and I think you would be beautiful if you didn't hold back."

She shook her head. "It's not that easy. You don't understand."

He took her hand. "I'd like to, if you'd let me. I'm here for you if you need me."

Breanna was getting uncomfortable talking about this and deflected the attention. "Your wife was very beautiful. That body was amazing, and that hair. Oh my God, she was a Goddess."

He smiled. "She was. Do you mind me showing you something?"

"What?"

"It's, " he cleared his voice, "one of our videos from a few years ago. Chelsea was staying with us and..." He stood up and put a DVD in the player and a movie played. "This was one of those nights when..."

Chelsea had her face buried between Margaret's legs and was going to town on her pussy as she stroked what looked to be a decent sized clitty. "You like the taste of my wife's pussy, " came Ken's voice from out of the picture?

Breanna was shocked that he would share this with her, but admittedly turned on. "Oh my God, she's eating your wife out."

Ken looked at her and smiled. "Jealous?"

She took a drink. "A little."

"My wife had the best pussy, and the tightest ass. Nothing was off limits and we did everything together." At that moment, Ken came into the picture, naked and stroking what looked to be a big eight-inch cock. "Give her a taste of what you give me daddy, " said Margaret in the most angelic voice.

He pushed that monster cock up against her tight hole and it surrendered to his hardness. Chelsea never lost focus as she kept her face in Margaret's pussy. Margaret seemed to be close to an orgasm as her husband's cock disappeared inside the t-girl's pussy.

Ken pulled his cock out of his pants, and it looked bigger in person as Breanna couldn't help but stare. "I hope you don't mind, but my pants kind of hurt."

Without even thinking, Breanna put her head over his crotch and started sucking Ken's cock. "Hmm... You don't have to do this, Breanna. I'm sorry if I implied that you... Oh, you know what you're doing."

She looked up at him with a smile. "I've had a lot of practice with toys."

He ran his hands through her hair. "This isn't a toy, dear. This one shoots lots of cum."

She continued sucking his cock and deep throated him a bit with some success. The strong taste that she could only surmise was his cum let her know he was about to burst. Sure enough, it happened. "Right there, " he said as he held her head on his cock. She gasped for air as he shot several spurts down her throat. She gagged a bit as some cum dripped out of her mouth."

Soon she came up for air. She looked at him with a hint of anger and lust in her eyes and his cum dripping off of her chin. He smiled. "You look good with my cum on your face."

She giggled as she took two fingers and wiped the cum from her chin. She put them in her mouth. "Good to the last drop, " she started to stand up, but he held her down.

"Wait a minute, " he instructed. "Check this out."

The video showed Chelsea bucking up against his big cock as he was thrusting in and out at a rapid pace. Suddenly, he slowed and tensed up and Breanna knew what was happening. Ken put a load of his manly seed inside the t-girl's pussy. When he pulled out, his cum leaked out. There was quite a bit. She looked at Ken. "Oh my."

"Next to my wife, the best piece of ass I ever had, " he admitted. "That girl knew how to work a cock, and she loved riding mine."

"You did it more than once?"

He nodded. "Maggie had a thing for t-girls, and it rubbed off on me. She helped a few girls and brought them back here. I tell you, we had some wild times."

She didn't know what to make of this. "So, these girls were just a piece of ass to you two?"

He shook his head. "What on earth gave you that idea, Brea? Maggie and I loved these girls. We gave them a place to stay and get back on their feet. Chelsea lived with us for a few months. We were gonna help her get the final surgery and she met the man she ended up marrying. We adored that girl like she was family."

"So, why am I here again? Did you want me to fuck me? Is that all I..."

He sighed and got up. She could tell she upset him. "Ken, I'm sorry." She got up to follow him to his room.

He went for a box on his bed. "I had something I was going to give you before you left, but now seems better. No strings."

"What is it?"

"Look."

The box had pills in it and a couple of syringes and what looked like were containers for injections. There were some papers in there explaining what it all was and what the proper doses were. She looked at him and back at the box. "Hormones?"

"A six-month supply, Brea. I just want you to get your blood work checked by a doctor that I know. Just to be safe. I think you should see a therapist..."

"I'm not letting anybody mess with my head, " she protested.

"That's not what it's about, " he tried to reassure her. "It's for your own good. They help you sort through things, and you need to go through the channels to get the surgery. You do want that, don't you?"

She nodded. "More than you know."

He looked Breanna in the eyes. "That's what Maggie and I did. We tried to get the girls the help they needed. You have no idea what some of them go through, sweetie. And, you are in college. You have a good future ahead of you, and you can be the woman you know you are inside."

She started to cry. "You think?"

Ken held her in his arms for a big hug. "I know. Breanna, I like you. I can help you if you let me, and there's no strings. That's why you have you own room here. Come on, let's go back to the living room." He took her hand and led her back to the couch.

"If there were no strings, why the lingerie?"

He laughed. "Sweetie, you’re a girl, and I know how girls are with lingerie. They like to feel sexy. My wife did, and don't forget I've seen you on video."

"Oh." She finished another drink. "Were you the one who sent me the chastity?"

He nodded. "I heard you say you needed it."

She giggled. "You have a dirty mind."

He finished another drink and laughed. "Hey, just be thankful I didn't demand the key."

She gave him an evil grin. "You have to earn that honor."

"Oh, is that so?" He picked up the phone. "I'm gonna order a pizza. Peperoni okay?"

"Sounds great."

The two enjoyed the pizza together and watched a ball game as they made idle chat. A few hours went by, and the two were enjoying each other's company. "Can I ask you something, Ken?"

"Anything."

"Do you ever get tired of flying to your other stores and taking all the business trips?"

He sighed. "Everyday. I hated leaving Maggie at home all the time. I always knew I'd come back to her, and then she died of that heart attack. She was in great shape too. It didn't make any sense."

"I'm sorry."

He shut off the TV. "As far as the hardware chain, I've been thinking of retiring. I can get $250 million at least, which is more than I'll ever need. I'd love to do that and enjoy my time with a special lady. Then, when we traveled it would be to Paris, Rome, Hawaii, any place nice."

Breanna put her hand in his. "She would be a lucky lady to have a man like you."

He squeezed her hand gently, and she felt a tingle. "I think a man would be lucky to have you, Brea."

"I don't know about that."

"I do." He looked into her hazel eyes. "You're smart, you're reliable. You are very creative. You can be anything you want to be in this world.

He stood up. "And, you are sexy as hell."

She blushed. "I don't know about that, but thank you."

"Anyway, I'm gonna go to bed. I want us to go someplace and do something tomorrow."

"Can I ask you something, Ken?"

"Anything, darling."

She stood up and followed him until she got to her door. "Why didn't you make a move on me?"

"Because, that's up to you, Brea. I want to help you, but I'm not going to take advantage of you."

"Oh." She smiled at him and kissed him on the cheek. "Goodnight Ken."

He felt his cock stir in his pants again. "Goodnight dear."

Breanna sat on her bed with her mind going a million thoughts a minute. She stood up to go to Ken's bedroom, then sat down again. Should she or shouldn't she? She finally got up and went to his room, opening the door without knocking. What she saw made her blush and lick her lips.

Ken was stroking his massive cock as he lay in bed. He smiled. "I wasn't expecting you, Brea, but you're welcome to join me if you want."

She crawled between his legs and licked his cock, but Ken had other thoughts. "Sweetie, that's not what I need right now. I need you to bend over for me."

She was still a bit nervous. This was a fantasy of hers, but it was about to become reality. She bent over, anticipating his hard cock. Instead, she felt something wet touching her tight pussy hole and realized he was licking her. She relaxed and pushed her ass towards his face.

Ken was skilled at licking t-girl pussy and enjoyed the experience as much as licking his wife's ass. He could tell she was relaxed enough. "Are you ready for me, baby?"

She looked back and licked her lips. "Uh huh. I'm ready."

"I'll be gentle," he assured her.

"As long as your cock is inside me, " she said with a smile.

"You little slut, " he said as he shoved his cock against her tight hole. It gave way and she felt herself being stretched, inch by inch. She expected it to hurt. It was uncomfortable at first, but she was taking it well. Soon, she was impaled on his massive cock with Ken leaning over and kissing her on the back of her neck.

The feeling was exquisite. Toys were no comparison to a real man's cock inside her sissy love hole. In that moment, Breanna found her calling. Her goal was to please her man and drain his cum inside her. She gently squeezed his cock inside her. "So, you like daddy's cock inside you, " he asked as he began slowly thrusting in and out?

She was already pushing back to meet his thrusts. "Mm, I love daddy's cock inside me."

He shoved in deep again. "That's good. With an ass like yours, daddy's gonna love giving you his cock."

A tear came down her cheek as Breanna realized what she had been missing and what she needed in her life. She needed a man to make her feel like the woman she always knew she was. She attempted to rub her clitty, but the cage was in the way. "Ah ah ah, " Ken admonished. "No touching that thing. In fact, I want your key. There's only one way for my girl to cum."

She pushed against him and took him deep as she let out a moan. "Your girl?"

He grinned as he steadily fucked her and could tell he was hitting her sweet spot. "Admit it, baby. Since you met me, you wanted to be daddy's girl."

She turned her head to say something, only to be met by his lips as he kissed her with his cock buried deep inside. "With my cock inside of you, I claim you as daddy's girl."

She whimpered as she could feel the pleasure building and wanted to rub it out of her. "Mm, fuck me daddy."

He reached under and grabbed her cage firmly as he continued to thrust in and out. "I'm gonna make you leak in your cage." He felt a little moisture at the tip of her cage and stuck his finger in her mouth. "You're already dripping baby. That's how much you love daddy's cock."

Breanna was angling her ass as she desperately wanted him to hit her in just the right place to make her cum. "That's it baby. Learn where it feels best. Hurry up. Daddy may cum before you."

"Please, " she begged. She could feel herself approaching the edge and then it happened. Her first girlie orgasm where she didn't touch herself. It was an amazing feeling that seemed to last a while.

Ken started thrusting more rapidly. "Now, beg daddy for his cum."

"Fill me up daddy, " she begged as she pushed back to meet his thrusts.

Ken's breathing became erratic as he tensed up and slowed down his thrusts. He unleashed a wave of cum, giving her a warm feeling inside. "Oh yeah, baby. You're mine now."

The two cuddled in bed together as Ken's cum was still inside her. She wanted it there and tried not to push it out. She kissed him. "Do you really mean that? Am I really your girl?"

"What do you think?" he kissed her passionately. "As far as I'm concerned, you're my girl. You can move in here and share my bed or have the other room. Whatever you want."

She started to worry about the age difference and people's reactions. "But what will your friends think? Or the people at my school?"

"We're both adults, so fuck what they think, " he kissed her again. "We have enough money to do whatever we want after I sell the business."

She took his cock in her hand and then went back between his legs. She started licking and sucking his cock. "Can I move in this week?"

"Sweetie, you keep doing that to me and you can do whatever you want." He was getting hard again.

The love making continued as Breanna sat on his hard cock and took him for a slow ride. She bottomed out and squeezed him as she grinned mischievously. "Looks like I'm on top now daddy."

"You little tease, " he said as she lay on top of him in a passionate kiss with his cock still inside her. "I never knew you were such a naughty little slut."

She went back to riding him. "Well, maybe I needed you to bring it out of me. Now, cum for me daddy."

Watching the budding young transsexual doll bouncing up and down on his cock was a beautiful site to Ken, and after several minutes, he released more cum inside her already seeded sissy pussy. She collapsed into his arms with his cock inside of her until it popped out.

Breanna couldn't imagine the turn her life had taken since meeting Ken, and now he was her boyfriend and daddy, the dream of many girls. The two kissed and cuddled for some time, and Ken seemed to take delight in playing with her breasts and her nipples.

It was Ken who woke up that morning to find her sleeping peacefully on her stomach with her ass exposed. He got up to go to the bathroom. When she appeared to still be sleeping, his cock got hard and he got the idea to wake her up with a good morning fuck. Her stretched hole offered little resistance as he was inside her and kissing her neck. "Good morning beautiful."

"Hmmm, morning you horny old man, " she moaned groggily.

He was slowly pushing in and out. "I should tell you that an exposed ass in my house is an invitation for my cock to come visit. And you have a nice inviting ass baby."

"Did your wife get woken up this way, " she asked in curiosity over the blond bombshell?

He was feeling his eruption coming to the surface. "Oh yeah... Mm, all the time baby. I think she would sleep that way on purpose."

"Ah, yeah, " she moaned. "Who could blame her? I think I'm gonna cum."

In moments, the two came together as she received her third load inside her well used sissy pussy hole. He lay on top of her, kissing her neck some more. "Baby, I'm hungry."

She giggled. "Well, let me up and I'll make us some breakfast,"

She walked to the door, naked except for the chastity cage. He laughed. "I still see an uncovered ass. Better watch yourself in the kitchen, sweetie."

"Be my guest, baby. I've always wanted to be fucked on the kitchen table." She winked at him and went to the kitchen. The two enjoyed a nice breakfast. Later, Ken took her out for a night of dinner and dancing with her in a beautiful blue dress. She did move in and began HRT. Ken talked her into getting therapy, and she was quickly diagnosed with Gender Dysphoria.

With his money, Ken made sure she got the best hair removal, breast augmentation and anything else she needed. Despite the age difference, the two fell madly in love. Ken impulsively asked her to marry him, and she said yes. He made an agreement that she could leave him in ten years if she felt the age difference was too much. Ten years later, they were still happy together. Breanna had GRS, and the two had every bit the adventurous sex life that he and his previous wife had. But that's for another story.