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.