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."