Just a Game Ch. 01byDark_Rose90©
Stan Johnson is just you're average twenty year old guy. At least he used to be. But before we get into that, let's look at his background.
Stan grew up like any other guy. He played a few sports. Mostly baseball. He developed one bad habit during this time though. He would bet on things all the time and play games with interesting twists. Tonight, he would be playing one of those games. But this game's twist is unlike anything he could ever have expected.
Stan's girlfriend, Jen, was out of town this weekend. She was visiting her parents on the other side of the country and wouldn't fly back in until Sunday night. It is currently Thursday morning. Stan loves Jen but he could never convince her to go "all the way" when they spent nights together.
Upon checking his messages, he realizes he's got to be at Mark's in about 4 hours for their game of poker. As a slender, 5'8 guy, Mark used to pick on him a lot. Also being a swimmer, Stan's body is completely hairless, with the exception of his head. Which is why he was hoping for some luck in tonight's strip poker game. He headed upstairs and figured he'd get ready to go. Upon opening his underwear drawer, he found what should have been the first sign that something was wrong.
"Man, Jen's such a tease." He thought out loud examining the black and pink lacy thong and bra he found stuck in his drawer. He also discovered matching stockings with pink bows.In his shirt drawer he discovered a black baby-doll with a pink bow in the middle of the cups and pink lace trim on the bottom. "What I wouldn't give to see her in these." He thinks more quietly. Upon opening his closet to find his shoes he discovered a pair of black stilettos and a long silky black robe hanging on the back of the door. "Okay, maybe she has a surprise planned."
About 30 minutes later, Stan knocks on the door at Mark's place.
"Come on in, Stan. Oh by the way, did I mention tonight's game has a special twist?"
"No. But I've handled you're 'twists' before so it shouldn't be too bad."
"Oh you'll see when we get there." Mark smiled evilly behind Stan's back as they walked to the table.
A few hands later, It seemed Stan had the upper hand as he only had his socks and shoes off, whereas Mark was in his boxers. However, Stan's luck soon turned sour. Before he knew it, he was sitting in his boxers as well.
"Well, it seems we're even now Stan."
"I'll be right back. I've got to grab what we need for round 2." Mark came back down with two piles of lingerie. "Round two," he explained, "involves putting clothes back on. Just not the ones you came in. As you lose a hand, now you'll be putting on the lingerie and one of these wigs. You'll lose entirely when you're completely dressed as a woman."
"Doesn't sound too bad I guess. If it's just for the short time until the games over." Mark smiled that same evil grin. The next hand, Stan lost, forced to take off his boxers. The next hand Mark lost, removing his. However, the next few hands involved Mark winning and Stan pulling the silken white panties up his hairless legs, snapping the matching bra across his chest, and slipping stockings up his legs. The next hand, Stan had lost again, putting his feet in to a pair of white pumps. Eventually, with Mark still on a winning streak, Stan pulled the red wig over his head and fixed it so the hair fell over his shoulders, contrasting with the white sheer robe. Stan had lost.
"Looks like I win, Stan."
"Yep now if you don't mind, I wanna change and head home."
"You're not going home yet. You didn't let me mention the other rule. The loser, dressed as a woman, has to BE a woman for the next four hours. Doing whatever womanly things I ask you to do."
"And why should I?"
"Because, you pull of the female look pretty damn well. Might even make Jen jealous. Now the first thing I want you to do, is go upstairs to the bathroom. I'm going to help you put some makeup on that face of yours." Before Stan knew it, he was looking in the mirror at a pretty redhead in white. He found the white ironic, since he was still a virgin. And then what was about to happen next dawned on him. He was about to lose his virginity... as a woman instead of to one.
"Okay, Stacy. That will be your name for the next three and a half hours. This is round three of the game. It starts with going to my bedroom. You are to get on your knees and do as I tell you. Or pictures might find their way to Jen..." Not wanting his girl to see him like this, Stan complied. And now, here he was dressed as a woman, kneeling in front of a naked man, with a semi-erect dick, much larger than his own. It had to be at least 8 inches long and 3 thick. The next thing he knew, that 8 inch cock was being pushed through his glossed lips. "Open up, Stacy. This is what I want you to do first. Be a good girl, and this will be very nice for both of us."
Before she knew it, Stacy was taking six inches in her mouth and bobbing her head up and down, as she had often seen women do in the porn she would watch for entertainment. If she didn't know any better, she'd think she was rather enjoying herself. Wait, she thought, why did my pronouns suddenly change?
"Good girl, Stacy. If i didn't know any better I'd say you've done this before. You sure are good at it. But now, it's time for you to lose those panties." Stacy dropped her panties exposing her cock and ass. Stan knew that he was soon to be lost forever, as Stacy was beginning to enjoy herself. Mark grabbed a bottle and began applying lubricant to her hole and with the other hand placed a condom over his fully hard, 8 inch cock. The next thing Stacy knew, she was on her back. Mark held her legs apart and slowly began sliding his cock into her ass. Stacy felt like she was being torn apart, until suddenly, it started to feel... good. She began to make sounds so feminine, she even began to doubt she had been a man. After about an hour and a half, Mark pushed his dick as far into her as he could and it began to twitch. A hole had torn in the tip of the condom and suddenly Stacy felt hot, sticky jets being pumped into her ass. Her whole body began to shake as her own jets of semen leaked out onto her stomach. She had just experienced her first orgasm and it was just too enjoyable.
"Wow. That was... great, Stacy." Stan became aware of himself at this point and began to cry as he realized he just lost his virginity to man and that his ass was filled with cum.
"I've gotta get out of here." He ran down the stairs, grabbed his keys, and drove home the way he was. I'll get rid of this when I get home he thought. "Oh my god. At least Jen won't have to know about this. I don't want to think about how she'd react if she found out her boyfriend was just dressed up like a slutty redhead and fucked senseless by another man." Stan got out of his car, running into his house as quickly as he could in white pumps, and ran upstairs to his room, passing a camera set up unbeknownst to him. He threw himself on his bed and began to cry. He had no clue what had just happened, and how it had made him or her feel. Just who was s/he? As he reconsidered the nights events, the way he felt, and how naturally good she was at what she had done, she may have found his answer for him. Stacy was becoming a reality.
*** ~The Next Day~
"She took right to it. The progress was stunning." Mark said into the receiver.
"Good." The mysterious voice replied. "How was she?"
"Oh you're going to love her. She was a natural. I've never had a convert take to it like that. It's like she was born to become a woman."
"I'm so glad she picked red. I just love slutty little redheads. I can't wait to get back and get my hands on her. Thanks for the help, Mark."
"No problemo, boss." DING-DONG. "I've got to go. Someone's at the door."
"Keep me posted on her progress. I have the camera in place for you already."
"Will do. Thanks again, boss."
Mark opened the door to reveal Stacy, fully made-up, red wig straight and wearing all of the black lacy things she had found in her drawers and closet the day before. She left the robe open to reveal her shaved, stocking covered legs and sexy baby-doll. She got up on her tiptoes and kissed his neck be fore whispering in his ear.
"Hi, Mark." She said to him, "I want to play again tonight. But this time, let's just skip to round three." And she kissed him passionately, nearly forcing him upstairs to the bedroom.