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Strip Poker

by Jennifer White

 

Drew thought he was a pretty good card player. He always won money when he played poker at the casino, and he could routinely beat his friends. So when he heard that his new girlfriend Jean told him that she played poker with her friends every other weekend, he wanted to get in on it.

"I'll ask them, but it's a chick thing" she said. "I don't know if they'll like having a guy there."

"It can't hurt to ask" he said.

"All right, I'll try. I'll let you know what they say" she replied, hanging up the phone. She then called Ellen, who's turn it was to host the party this time, and proposed bringing Drew with her.

 

After a long talk and much debate, Ellen was convinced. What Jean was asking her to do sounded fun. She called the other girls, and made preparations. It wasn't all that hard to stack the cards...

 

* * *

 

On the appointed Saturday, Ellen's place was all set up for cards. There was a table full of snacks set up, as well as bottles of wine, and strong margaritas. When Drew and Jean arrived, Ellen was quick to put a full glass in his hand, which he of course quickly drank. All through the evening, as the other girls started to arrive, she made sure to keep his glass full.

Annette was the next to show up. She was looking good in her tight black pants, and her matching halter top. She played with her long black hair as she talked to Jean. Drew could not help but to check out her butt. Nice.

The final arrival was Libby, who was a cute short blond. She wore a pink skirt and a white sleeveless top with a few pink stripes. It made her look even more perky. She was hot too. Not that Jean wasn't great looking, but all of her friends were really hot. Ellen was wearing a green plaid skirt, which made him think of school girl uniforms.

They all talked some more, while Drew put away a couple more drinks. Now it was time to play cards.

"Today" announced Ellen, "since it is my turn to host, I get to name the game. And that game is: strip poker."

"Not again" said Annette. "You know what happened last time we did that!"

"No, it's my call" said Ellen.

"I'm up for it" said Drew, butting in.

What guy wouldn't be up for playing strip poker with four hot babes? He'd rob them blind, and get to check out their tits. Maybe he'd lose a hand, so they could see his bare chest, and get turned on by him. They'd all want him. Who knows what they'd end up doing? He smiled. This was going to be fun.

 

"Okay, house rule. Shoes and socks off now. Those don't count. Clothes only."

The girls whined, but Drew was quick to jump in to support Ellen. Less things to take off would mean that he'd see more skin faster. Cool.

"And only the low hand loses. That keeps it more interesting" said Ellen.

Drew didn't like that rule as much, but oh well, he'd be winning, so some chick would be stripping.

 

Ellen dealt first. Drew looked at his cards. Nothing. He kept the Jack of spades and the Queen of diamonds, but he drew a 2, 5 and 9. Nothing.

Jean won the hand with two pair. When everyone showed their cards, he was the lowest hand. All the others had at least one pair. So he had to go first, and take something off. He chose his shirt, hoping that Annette would lose the next hand, since she wasn't wearing a bra under her halter top. You could tell by how the nipples showed through the thin fabric.

 

The next hand was even worse for Drew. Not even one face card! Libby had three tens to win the hand. Again, the others had at least a pair, so Drew had to strip. Off came the pants. Now he was worried. He was down to just his boxers, and none of the girls had taken off *anything* yet.

But his luck would change. It had to. The third hand went a little better. Jean lost, and she took off her top, revealing her bra underneath. But he saw that all the time. He wanted to see the *other* girls undress. Variety is the spice of life, after all.

But on the 4th hand, Drew again had nothing! He held a 2, 3, 6, 7 and 9, with all four suits represented in his hand. He lost, and he had to bite the bullet, and take off his boxers. Now naked, he had nothing to go. He turned red in embarrassment.

"Game over" said Ellen.

"No. One more hand. I am going to win" said Drew.

"But honey, you're already naked. What if you lose another hand?"

"That's not going to happen. I'm due for some luck."

"Well I'm not playing if you don't have any more risks to take" said Annette.

"Me too" said Libby.

"Okay, what do you want from me?" asked Drew.

"Since he can't strip, what if we get to dress him if he loses again" said Ellen.

"What do you mean?" asked Drew.

"We'll dress you in *girl's* clothes. If you lose the next hand, you'll put on panties. Then a bra. Stuff like that."

It didn't sound very appealing to Drew, but he knew that his run of bad luck had to end soon. He was due for some good cards. He just *had* to see them strip. He was determined to win. It was a bad penalty to pay if he lost again, but that wasn't going to happen.

"Okay, I'm in" he said, full of macho confidence.

 

That confidence was shaken the next hand, when unbelievably he lost again. This time, he had a pair of fives. But Jean had a straight, Annette had a pair of aces, and Libby had a pair of tens. He was low man again! Even with a pair, he still lost. This was just incredible.

Ellen went to her bedroom, and returned with a pile of clothes. She handed a pair of panties over to Drew, so he could pay up for losing the last hand. He took a deep breath, and for the first time in his life, he put on panties. They were pink and silky. He had to admit the felt nice against his skin. But he wasn't about to tell *them*!

The next hand was a disaster, with no scoring for Drew. Libby's hand had nothing too, but her high card was a King, which beat out Drew's Jack. Now he had to put on a bra. It felt so constricting that it was almost hard to breath at first. He was completely intimidated by it, and just kept staring at his chest in disbelief.

 

Most people who gamble know when it is time to cash in and walk away. However, there are always some who just can't conceive that they will lose, and they keep betting, even when they are sinking further and further into a hold. Drew was in this category. Instead of quitting how, he kept going.

When Annette won the next hand, with Libby losing, it gave him more hope. She took off her top, exposing her dainty little bra underneath. Drew got very aroused seeing her. Now this was more like it. He kept playing. He looked at the cards he was dealt. Nothing!

His face went pale when he saw the cards he picked up to replace his discards with. Nothing. Now he had to put something else on: a sundress. He felt so embarrassed putting it on. The girls were all giggling at him, but he scowled. He would show them! He never lost!

But the next hand was no better. Since he was already wearing a bra, panties, and a dress, they decided to stuff his bra for losing. And when the following hand was also a complete disaster, they decided that they would put him in makeup.

He just sat there, and let them work on him. They applied foundation, lipstick, blush, mascara, eyeshadow, perfume, and even some sparkling glitter on the cheeks. He needed another drink. He downed yet another margarita, and was now starting to feel the effects of so much tequila in his system.

The next hand was yet another loss. Now the girls decided to paint his nails. He held his hands out limply as they applied a pink color to his fingernails, and a bright red to his toenails. He had to win next time. He just had to!

 

Drew held his breath as he looked at the cards. Nine of hearts. Ten of hearts. Ten of clubs. Queen of hearts. King of hearts. Almost a great hand! He just needed the Jack of hearts, and he would win the hand. He asked for one card, and nervously waited to see what it would be.

Ellen slid it over. He was heartbroken when it was the three of clubs. He had a nothing hand. And now, he had lost yet *again*. What would they do to him now?

"Well, we can't dress him up much more. What did he lost this time?"

"How about his name?"

"Yeah! We'll use a girl's name for him now."

"You mean *her*."

"Yeah, her."

"How about 'Sharon'? That's a good name for a girl."

"Good idea."

"Okay Drew" said Annette. "You lost your maleness. You are Sharon now. You are a chick."

"You're one of us now" said Libby. "A girl."

"You're wearing makeup. You've got a bra on. You're wearing a dress" said Ellen.

"Sounds like a girl to me!"

"My Sharon, you are pretty."

"Yes Sharon. You're a very sexy girl."

What had he gotten himself into now? This was terrible. Terrible. They were all calling him a girl now. He *was* all dressed up like a girl. And he was wearing makeup. How could he ever live this down? It was terrible. He looked up, in time to see Jean with her digital camera. Flash! She had taken a picture.

"What was that for?" said Drew.

"To make sure that you understand now that you have to do exactly as we say" she replied.

"Because otherwise, we'll email the picture to all your buddies, and they'll see that you're a girl now."

"Do you think they'll want to still hang out with you, once they know that you're a chick?"

"Do guys like pretty babes like you Sharon?"

"What do you want from me?" said Drew, confused and upset. Why was Jean helping with this? Why wasn't she being more supportive?

"We want to turn you into a girl" said Jean.

"But why?"

"Because you need to be. You hit on my friends! You stare at their boobs! Do you realize how much that embarrasses me? Do you realize how that makes me feel?"
"I guess not" said Ellen.

"Well, once she's been a girl for a few days, and had some guys checking *her* out, then she'll learn. Maybe" said Jean.

"I'm not going to do this for days! And I'm not going to let any guys see me like this!"

"Yes you are" said Jean. "You see Sharon, you will do everything we tell you, because we have your photo. Now here is what you are going to do: you will go with me to the bedroom, where I will fit you for your wig. Then you will go to the tub, and shave your legs. By the time you put on your pantyhose, the guys will be here for the party. You will come out, join us, and act like a girl all night. You will flirt with the guys. You will let them check you out. You will act like a girl all night, or else we let *everyone* know all about you."

"You can't do that!" said Drew.

"I will" said Jean. "Now are you going to put your wig on, or do I need to get my email sent out?"

Defeated, Drew put his head down, and followed her into the bedroom.

"Tell me you're a girl. Tell me that your name is Sharon now" she said, as they walked off.

 

* * *

 

When Drew emerged from the bedroom as 'Sharon', there were already a few people who had arrived for the party. There were a couple more women there who he didn't recognize, and there were several guys. Drew was extremely conscious of the fact that he was dressed up like a girl, from head to toe.

He was wearing a wig of long brown hair, which was full and had little curls in it. His face was covered with a thick layer of makeup. They had plucked his eyebrows back, attached clip-ons to his ear lobes, stuffed his bra full, and put him into a very pretty outfit. The top was black, and the tight skirt wrapped around him was a leopard skin print. The girdle underneath made it look like he had curves.

Immediately, and guy came over to him.

"Hi, I'm John. Nice to meet you" he said.

"I'm...Sharon" said Drew, extending his hand, with his new long press on fingernails, painted a delicate pink color, which matched the color on his toes, which showed through the open-toe high heel shoes he wore.

"Can I get you a drink?" asked John.

Drew really needed a drink. Badly.

"Sure" he said, smiling through is lips, which were a dark crimson color, from the lipstick he was wearing.

He shifted his weight, uncomfortable in the heels. He purse over his shoulder, with it's long thin strap, was hard to get used to. But he was told he had to keep it with him, all night.

John returned with two glasses of margaritas. He took a bit slug of the cool green liquid, but Drew just took a dainty sip, like they had told him to. With all the pictures they had taken during his transformation in the back room, he had to be very careful to do exactly what they said.

Suddenly, there was a noise coming from his purse! A cell phone was in there, with a ring programed to the theme from 'Cats'.

"I get it. Cats" said John. "You must love cats, with the leopard skirt and all. I love pussies too."

He smiled and winked at Drew, as he opened the purse to get out the cell phone, and make it stop ringing! He unzipped the top, and reached in. Immediately, a couple of while cylindrical objects fell out. He bent his knees, lowering himself to get them, but John did the gentlemanly thing, and grabbed them before Drew could.

Drew looked down in his hand, as John handed them back. Tampons. Oh no. John would think that he was carrying tampons, so he must be on his period. In fact, that made John seem to lose interest in him right away. What guy wants a girl at 'that time of the month'?

So it was a good thing for Drew, and a bad thing. The good was that it scared this guy away, and he didn't have to be embarrassed anymore by being flirted with, by a guy. But the bad part was that John now firmly believed that he was a girl. He would talk to others. Everyone there, except for the original poker players would think he really was a girl. And that was bad. Very bad.

He didn't know if that was worse than being flirted with or not. But he didn't have time to sort it all out right now. It just flashed through his mind as he picked up the cell phone.

"Hello?" said Drew.

"Hi, its Ellen. I'm calling from the back room. I see how you've been flirting with a guy. Cool. I'm glad to see that you're really getting into being a chick."

"Um..." said Drew, not sure what she wanted.

"Now listen. I'll be calling you every so often, and giving you an instruction. You need to do exactly what I say. Do you understand?"

"Yes" said Drew.

"Excellent. You make a wonderful chick, Sharon. Now here is what you are going to do next."

Drew held his breath. Whatever it was, it couldn't be good.

"Over against the wall on your left is a guy in a black T-shirt. Go talk to him, and tell him you heard he likes basketball."

"What?" said Drew.

"Just tell him *Sharon*."

"Okay" said Drew, hanging up. He walked over to the guy in the black shirt. He had short hair, almost military looking.

"Ellen tells me that you like basketball" said Drew.

The guy's face lit up, with an expression of surprise and anticipation.

"I sure do. You like b-ball too?"

"Yes" replied Drew truthfully. It was his favorite sport.

"I'm Bill" he said.

"Sharon" replied Drew.

Before he knew it, he and Bill were deep in a conversation on the ball game. They both preferred college basketball to the pro game, because of its purity. Before Drew knew it, the time slipped away, and most of the guests had left.

"I guess I should head home too" said Bill.

"Yeah, me too" said Drew.

"Listen Sharon, I had a wonderful time tonight. I'd really like to get a chance to see you again. Can I have your phone number?"

"Aw, I don't think so" said Drew taken aback. He was just talking about basketball with the guy, not flirting. But the guy was interested in him! This was terrible.

"Then take mine. Call me some time" said Bill with a smile on his face. He winked and waved good-bye as he walked out the door.

 

"I am *so* glad that is over" said Drew, as the last of the guests left, and it was just him, Jean and Libby.

"Help me clean up as we talk" said Jean, who was moving empty glasses from all around the house, over to the sink. Drew was still all dressed up, so it looked like three women cleaning and talking.

"I am *never* playing poker with you again" said Drew.

Jean and Libby giggled.

"We stacked the deck against you" said Libby.

"What!!?" said Drew.

"Look Drew, you're always thinking that because I'm a woman, that you're superior. You don't listen to me. You don't take me seriously. You think that you should control everything, and you keep trying more and more to take over control of our relationship. I did this tonight, so you could see things from my viewpoint. I hope you learned your lesson."

"I sure did" said Drew.

"Good. I'll never bring up tonight again. I'll never tease you about it. As far as I'm concerned, it is all over."

"I'll try better to treat you right" said Drew.

 

Libby went home, and Drew went with Jean to the bathroom to undress and take off his makeup....

 

* * *

 

A month went by, and Drew's night as 'Sharon' was never mentioned again. He improved dramatically in his relationship with her at first, but over time, he started to slip back into his old bad habits. Jean got more and more frustrated as the lessons of Strip Poker Night slipped away from his mind.

She was at the point of considering the possibility of dropping him, and moving on. He wouldn't change. He was never going to become the man she hoped he would be. But then one day, she got The Call.

 

"Drew!" said Jean, after she got off The Call.

"What?" he replied as he continued to read his newspaper. He didn't even bother giving her his full attention as he talked to her. That made her feel like she was less important to him than some stupid story in the sports section.

"Drew, how would you like front row tickets to the game on Friday?"

"What, the basketball game?"

The local college team was in the playoffs, and now they were one win from going to the "sweet sixteen" playoff round. Drew wanted to go, but it was sold out, and the scalpers were asking five hundred dollars for tickets. He couldn't afford it, so he was going to just watch it on TV.

"Yes dear, to the playoff game. In the front row."

"Wow! How did you pull that off Jean?"

"I didn't. Bill did."

"Bill? Who is that?"

"Remember Strip Poker Night?"

"How can I forget" he said, blushing. This was the first they had talked about it in a month.

"Bill was the guy you flirted with all night."

"I didn't flirt! We just talked b-ball."

"To a guy, you were flirting."

Drew just glared at her, with a steamed look in his eyes.

"He keeps calling me, asking for Sharon's phone number. But when he called today, he told me he has two front row tickets for the game, and asked me to tell Sharon, and see if she would go with him."

"There is no Sharon" said Drew.

"There could be" said Jean. "I know how much the game means to you. All you would have to do is dress up again as Sharon, and you could go to the game."

"But...I'd have to be a girl again."

"Not a girl. A woman. You're not ten years old."

"Whatever. How could I do that? I'd be out in public."

"I understand" said Jean. "I'll just call Bill back, and tell him that Sharon isn't interested in going to the game Friday."

She picked up the phone and dialed. As she held the phone, visions of being at the front row in the big game flashed before Drew's eyes. He could be there! All he had to do was to go as a *woman*. He was torn inside. What was more important to him, the big game or a little of his pride? He had already been Sharon once, and it hadn't hurt him. What harm could it be to do it again? All this flashed through his mind an a split second.

He reached over, and grabbed the phone from Jean.

"Hello?" said Bill.

"Bill! It's Sharon!" said Drew.

"Sharon, I'm *so* glad to hear from you. I've been thinking of you, and when I got ahold of the tickets, I knew who I wanted to be with at the game."

"I'd love to go" said Drew.

"Great! I'll pick you up at 5:00 for dinner. Where do you live?"

"Why don't you pick me up at Jean's place? You know where that is already."

"Sure. Sorry, but you caught me at a bad time. I need to run. But I am *so* glad you're coming with me Friday."

"I'll see you then" said Drew, hanging up.

"I'm going to the game!" he said, holding both arms up in the air, in triumph.

Jean smiled.

"I'm sure you'll have a great time" she said.

 

* * *

 

On Friday, Drew met up with Jean at 3:00, so he could begin his transformation. He needed to shave his legs and chest again to start with. And now this time, Jean had some more elaborate things to aid in his illusion. She had bought a realistic pair of fake breasts, which filled out his bra now. And she bought a special girdle with lots of padding in the right places, to make it look like he had curves. And then there was the 'gaff'. It was a device worn inside the panties, which helped tuck his manhood in, so that there was no bulge to be seen in his pants.

Now when it was time to put on women's clothes, he would look a lot more realistic. Jean decided that he should have a nice casual look for the game, so she started with khaki colored pants, that came down to just below his knees. She put an anklet on him, and painted his toenails, before putting him into a pair of open toed flats. She selected a black sleeveless top, that wasn't cut too low. It would hide the fact that his boobs were fake.

With the wig, the makeup, the rest of the jewelry, the purse and the long red nails (matching his toes of course), he looked a *lot* more like a woman than the previous time. He would be out in public, but he would fool all but the most discerning eye. They worked on how to walk and sit, until Bill showed up at the door.

They walked down to Bill's car after exchanging pleasantries. Bill opened the car door for 'Sharon', which felt so strange to him. And he treated 'her' like a lady all night. He paid for dinner. He always held the doors open. He ordered for her, after she told him what she wanted. He bought a flower for her from the girl going around with the tray.

All of that was hard for Drew to get used to. The wine was making him have to go pee. The words that Jean had told him echoed in his mind: "Don't forget to use the Ladies room!". He had to brave it, and go through a lot of trouble to get out of his girdle and his gaff before he could go. He promised himself not to drink much at the game, because this all took so long that he would miss too much of the action.

"You women sure take a long time" laughed Bill when Drew finally returned.

"Well, we have to fix our makeup, and gossip with the other girls" said Drew, not wanting to admit the real reason for taking so long. He had heard the real women talking about their boyfriends and relationships while they stood in line. So it wasn't quite a lie, it was what the *real* women in there had been doing.

 

After dinner, Bill drove them to the game. Drew was walking on air (in opened toed flats!) as he walked down the steps of the arena, further and further, until they got to the first row! He was so excited that he could barely contain himself.

"Wow, I can't believe this!" he said. "Front row!"

"I can't believe it either" said Bill. "I finally got you to come out on a date."

A date. He was on a *date*, with a guy. Drew blushed. But he didn't have to think about it very long, because the buzzer sounded, and the teams came out onto the floor. Soon the game started, and it held Drew's full attention. He didn't even protest as Bill held his hand.

"You have such nice soft skin" said Bill.

Drew pulled away to clap his hands.

"Come on, defense!" he yelled, trying to sound like a girl yelling. If Bill realized now that he was a guy, well nothing good could come of that. But he was unwilling to allow this touching to go on, nor was he willing to take any more compliments on how pretty he was, how soft his skin was, and so on.

But Bill seemed to pick up his uncomfortableness, and stopped trying to make advances. And the game was so good that it held Drew's full attention. The team won, and he felt absolutely giddy as they left. They were stuck in traffic a long time in the parking lot, but they talked about the game, and it wasn't too bad.

When they got back to Jean's, Drew was quick to get out of there, before Bill tried a good-night kiss or anything. He was relieved to duck into her apartment and shut the door. Whew. It was over.

 

* * *

 

"Bill wants to take you out to the hockey game on Tuesday" said Jean. Over the past month, Bill had taken out 'Sharon' to see four different games. He always bought 'her' dinner, treated 'her' like a lady, and had premium seats for them to sit in. Drew had even consented to talk to Bill a few times on the phone.

"Tell him I can make it, but I'm busy right now!" yelled Drew. He was busy trimming his eyebrows, so his face would look nicer that night, when Bill was taking him to the football game.

Jean smiled. Drew was going out with Bill just about as often as he was going out with her. He was doing things every day like shaving his legs, plucking his eyebrows, and using lotion to keep his skin nice. He was starting to act more and more like a woman, so he could be with Bill at the games.

He no longer thought anything about going out of the house in a skirt anymore. It was becoming more and more normal. It was like living a fantasy for him, seeing all the big games, and having a friend who knew sports like he did. Everything was going perfect for Jean's plan. Soon, he'd be spending more time with Bill, than with her. Soon, he would start falling in love with Bill. With the estrogen she was secretly dosing him with, his sense of attraction would change over time, and he would be more and more willing to be with Bill. He didn't realize just how far along the way he was to becoming a full time woman.

"Have fun tonight dear" she said, as 'Sharon' walked out the door.

"Don't wait up for me" he replied. "I think Bill wants to go out dancing after the game."

"No problem" replied Jean, as she waved good-bye.

Drew giggled. Giggled! He didn't even realize how far gone he was.

 

* * *

 

"So tonight's the big night?" said Jean.

"Yes. I think I'll finally get him to go to bed with me" replied Bill.

"I can't believe he made out with you like that last night" said Jean.

"He was wonderful" said Bill. "You're right. Those hormones you put him on made his skin very soft and smooth, like a girl's."

"I knew you'd like it" she said.

"I'm going to ask him to move in with me, full time" said Bill.

"Does he know that you know he's really a man?"

"I don't think he cares" said Bill. "It doesn't matter to me. All that matters is that we're in love now."

"Way to go!" said Jean.

"Thanks for setting it all up babe."

"No problem, babe. Have fun. Take care of him. I used to love him once."

"I will" said Bill. "Now that I've trained him out of his bad habits, I'll really take care of him."

  

  

  

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2004 by Jennifer White. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, and compilation design) may be printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without the express written consent of StorySite and the copyright holder.