Introspection

"Alright then, shall we?" Caitlin said as she opened the door next to them and pulled Jenny through.

"What are we doing?" Jenny whispered into Caitlin's ear.

"I'm going to give you your first taste of dick, girl." Caitlin whispered back.

Jenny was about to say something when Caitlin grabbed Jenny's white dress and pulled it up to reveal her smooth butt and panties.

"Alright boys, you already know about my friend's little secret. Which one of you is man enough to claim her cute ass?" Caitlin said while Jenny was frozen in embarrassment.

"Oh I'm all game." Mark said confidently.

"Alright then. James, you're my ride for the night then. You guys both have protection?"

The boys both nodded and began to pull out their wallets. Jenny didn't even get a chance to say anything before Caitlin pulled her back in for another kiss. Jenny melted once more into Caitlin's arms as they made out, and she didn't notice what the boys were doing. But suddenly, Jenny saw James come around behind Caitlin, and she felt Mark's hands on her ass. But the girls kept making out until the boys pulled them apart. Mark spun Jenny around in his arms and pulled her into a kiss. This is when Jenny realized that he was naked except for a pair of boxers with an obvious tent being pitched. Jenny couldn't help herself from melting into his arms as well, and his kiss was fiery and sloppy like Kyle's.

Jenny lost track of what the others were doing while she made out with Mark. She began to feel his member press against her thighs, and her sissy instincts began to kick in. She began to do what Caitlin had done to her, slowly crouching down and running her hands all down his chest. When she got down to the right level, his member was pressing through his boxers right in front of her face. She could smell booze and musk on him, but in some ways it only turned her on more. She pulled at his boxers and tore them down, letting his member spring free. It was big, about eight inches, and her hands instantly began to rub it. Before long, she was kissing the head of it, dying for a taste.

When he placed his hands on her head and began to lightly push her down, she took his member between her lips and started. It tasted exactly how she expected, musky, a bit like booze, and the subtle warmth of pre-come. It was warm on her tongue and slid down through her mouth. She moved slowly, trying to avoid scraping it with her teeth. She failed a few times and scraped a bit, but he didn't seem to care. She could feel his pulse on her tongue, and it only made her more aware of her own thumping heart. She got about half way down before it began to poke into the back of her mouth. She gagged and pulled almost all the way out.

"Don't worry about it, you don't need to push yourself any further. I know it's your first time." He cooed her softly.

She took his advise and stuck with how far she had managed. She tried to move like Caitlin had, and how she assumed she was moving right now, but it proved to be difficult and exhausting to be so diligent in her movements. But she managed to move back and forth slowly, beginning to improve at avoiding teeth. But just as she was getting the hang of it, Mark grabbed her head and pulled her off. He reached down and grabbed her ass, practically lifting her off the ground by it. He picked her up and spun her around once more so her ass was pressed against his bare cock. She yelped at the sudden excitement, and could now see what the others were doing. Caitlin had already blown James and they had moved to the bed. Caitlin was on all fours at the far end of the bed with James positioned behind her. They were both looking at them now.

Mark began to move Jenny towards the bed. Jenny got the hint as he lightly pushed her onto the bed, and Jenny positioned herself on all fours as well in front of Caitlin. Caitlin leaned in and whispered, "Are you ready, baby?"

Jenny once again didn't get to respond as she felt Mark's hands traversing her ass. He pulled up her dress, rubbed her bare cheeks, then pulled down her panties. Her mostly hard seven inch dick hung down between her spread legs, and all of the sudden the same embarrassment rushed back. Her ass was on display for another man. She felt her panties fall to her knees, and Mark's hands began to rub all around her now bare cheeks. He spread them, squeezed them, and even tugged at her dick which made her moan. Finally, James and Mark nodded at each other, and Mark began to move into position.

Suddenly, Jenny felt Mark's cock place on top of her ass. She was beginning to panic while she saw James push his into Caitlin's pussy. Caitlin moaned in joy and her eyes rolled back a little. Jenny spoke up and said, "Please be gentle!"

That's when she heard Mark open some kind of bottle, and he rubbed lube onto his cock. He responded, "Don't worry baby, I don't want to split you on your first try."

He began to position his cock between her cheeks. She felt his now lubed and protected cock press against her asshole. She sucked in her breath as he began to push. She hadn't ever told Caitlin or anyone that a part of being a sissy was playing with sex toys. Caitlin thought this would be Jenny's first time being penetrated, but really Jenny had played with her toys enough that her ass readily accepted Mark's cock. It was still tight, and both Mark and Jenny moaned in unison, but there was no pain for Jenny. Only extreme joy flushing her mind.

Once again his warm member bore its way into her ass, and she could feel every pulse and every movement he made. Her eyes rolled back and her arms began to waver as he began to pound her sissy ass. He grabbed her cheeks and used them as leverage to pump her. She was moaning like Caitlin now, and the two girls were being dominated together. Jenny was reminded of Caitlin's presence when her soft hand touched Jenny's cheek. Jenny looked back down to see Caitlin leaning in to keep kissing. Jenny embraced her girl friend, and they were moaning into each others mouths. The boys grunted and heaved as they pounded the girls. Jenny was losing her mind in the ecstasy, and every now and again Mark would slap Jenny's ass.

Jenny was too lost in the ecstasy, and reached one hand down between her legs to began beating her own cock. Her senses were completely overloaded, from Mark's cock and Caitlin's kiss she couldn't think straight. She began to jerk her dick, and within a minute or two she was coming. Her whole body convulsed and shivered as she spurt a few ropes of come onto the bed. Something about this seemed to send everyone into a tizzy, as Caitlin moaned louder into Jenny's mouth, and the boys picked up the pace and grunted heavier. Jenny had begun the end, and suddenly the girls were torn away from each other. James grabbed Caitlin's hair and pulled her back as he completely dominated her pussy, while Mark pushed Jenny down into the sheets as he pounded away at her ass.

Jenny was moaning and panting like a dog before she felt Mark begin to tense up. James came first, followed immediately by Caitlin. As they were coming down, Mark came too, and Jenny felt the condom fill with his jizz in her ass. Suddenly she desperately wanted the condom to be gone, to feel his sperm fill her ass. They sat like that for a few moments, in a pile of sweaty and panting sex. But finally mark and James pulled out of their respective girls, allowing the girls to collapse forward. They crawled next to each other and began to catch their breath. Jenny heard the boys say something, then after a moment she saw Mark holding something over her. It was his condom, filled to the brim with his come. Jennie's eyes lit up as she opened her mouth.

Mark laughed at how pathetic and sexy it was, then began to pour his come out of the condom onto her face. He intentionally missed her mouth mostly, instead pouring it all over her face and wig. Once again Jenny's senses were overwhelmed by the musky man juices now covering her face. And as she looked over she could see that James did the same to Caitlin. As the boys stepped back and began to redress, Jenny leaned up and flopped over on top of Caitlin. Caitlin was at first surprised, but when Jenny took Caitlin back in for one more kiss, they shared their prizes together. They sat like that for fifteen minutes, feeling and licking come off each other. Once they stood up and began to get ready, the boys had already left. They found their girl friends and left the party after that.

Of course, they left for one of their houses. Jenny found herself at her friend Sally's house, sitting around Sally's couches, talking about how everyone knew that Jenny and Caitlin were boned together. Apparently, news spread fast at parties like those, and not even five minutes after the boys left the room the entire party knew exactly who and what went down in that room. Jenny and Caitlin had some explaining to do with their girl friends, starting with Jenny. The questions were as you might expect, interrogating her if she was gay, bi, pan, or whatever. When she couldn't muster a real answer for them, Caitlin took charge. Caitlin began to explain her interpretation of Jimmy's condition, "Jimmy is as he describes a sissy. They're boys when they want to be boys, but girls when it comes to the fun parts. When they're girls, they're the cutest, most obedient little things I've ever seen. Jenny here spent most of the night with me, and she was the best part of it all."

Most of the girls seemed to ponder this idea for a few moments. Then, they all rang off one by one about how supportive they were of it, and how excited they were not to have a gay best friend, but a sissy best friend. And so the next half hour was spent talking about the other girls' endeavors that night. Almost all of them were about making out, sex, or boys hitting on them. The circle made it's way around multiple times, and Jenny had to share each experience she had, with Kyle, Caitlin, and the boys.

"Jenny you make such a good girl. No offense or anything honey, but you make a better girl than boy. You should consider completely transitioning!" A girl named Tristyn said.

Before Jenny could retaliate, all of the other girls except for Caitlin were pitching in about how good of an idea that was.

"N-No, I don't think so. I like how things are right now, and I'd like to keep them that way." She explained.

"Okay fine. But whenever we're going out together or hanging out apart from school, you should be Jenny instead of Jimmy." Another girl said, with the others agreeing.

"Okay... I guess." Jenny relented.

"Ooooh! This'll be so fun, Jen, we can all dress you up, show you how to be a pro at makeup, and hair, and around boys!"

They only spent a few more minutes together before Jenny had Caitlin driver her home. They got back far later than Alex would be awake, so Jenny could sneak back into her bathroom to take off her disguise (Or maybe to put back on her disguise) transforming back into Jimmy. Jimmy then put everything away, posted the photos of Jenny online, and went to sleep. It was hard for him to fall asleep that night. Too many things were buzzing in his head. He began to think back to his experience with Kyle, and the boys. He remembered the feeling of Mark's cock in Jenny's ass, or Kyle's tongue with hers. Jimmy began to get hard again, and he had to run to the bathroom to relieve himself. But it was weird, when he tried to look at photos of girls while jerking it, he couldn't finish. Only when he pulled back up the photos of Jenny and focused on those feelings from Mark's cock could he finally come. Back in bed, he was lost in his own head until he finally drifted asleep.

That party, and the events that transpired there and at Sally's house were only the beginning. Soon, aside from Jenny's usual dress up and photo shoots every other night, Jenny went out with her friends on the weekends. They would go to more parties, or each others houses, or down to go see movies. Jenny always had to get dressed and ready at one of her friend's houses, which was okay because that meant she got help from one of her friends on makeup, hair, clothes, etc. And in the coming months, she became an expert herself. And not just at those things either. Her girl friends recommended she worked out her girl voice, though it was alright it needed work. So she did, and soon she mastered that too, getting the high pitched little innocent girl voice down. She also learned how to walk, posture, pose, flirt, dance, and think like one of her girl friends. But the most exciting of them all, was she learned how to fuck like her friends.

Every party they went to, Jenny had sex at. Jenny began to grow a name for herself, outside of Jimmy, as all the boys and other girls who frequented parties began to get to know her. She became one of the girls that hung out with Caitlin's posse, but of course to guys she became just another target. And she was alright with that. Jenny would start party nights with shots, begin flirting, then slow down as she moved to regular beers. By the time she was truly tipsy, she was likely already making out with boys in the corner. For the first few months, the sex that would happen by the end of the party was usually oral or just a hand job. Jenny became pretty good at those, and it didn't jeopardize people finding out her true identity. But slowly, she began to hunger for more, and the boys always wanted to see how far they could get.

By the third quarter of the year, Jenny opened her doors to actual sex. At first, the boys were a little shocked to find out she had a penis. But because she was so hot, and they were all so drunk none of them were turned away. And by the time they came, they were completely sold and would be lining up for more the next party. Of course, with this came the inevitable. Not every jock at these parties were complete idiots, and a lot of the girls that would then hear the rumor that Jenny was actually a boy could also start putting two and two together. And soon, after Jenny had already won over most of the boys that might have bullied her for it, the whole school began to know who Jenny was. But because of high school, and how teens decided to act and pretend, they had to put on the same show as always. They would talk about what a faggot Jimmy was to each other, but to Jimmy's face everyone suddenly became so much nicer. Those same jocks would come up to him and casually chat about upcoming parties. They would invite Jimmy, full well knowing and hoping that Jenny would be the one coming. And their hopes were always met.

Jimmy began to lose his masculine side. The more he had sex, and the more he was Jenny, the less he cared about being a boy or a girl and the more he cared about having fun and having sex. It had changed his life, and changed his character. He would never be the same again, and who knows, even the thoughts of never being a 'he' again began to creep into his mind. Life was amazing at school, and Jimmy had never been so happy socially. But not everything was so peachy.

While Jimmy's social life at school began to take off because of Jenny, he also began to watch the fall of Alex's relationship. Since day one he knew that it was an unhealthy one, almost completely because Sarah was a flaming bitch about everything. Jimmy saw Alex's descent into madness and depression while Sarah only got more and more angry at him. Their usual small fights became loud bursts of screaming coming from down stairs. Their usual movie time became time to discuss why they hated each other. And every night after Sarah left, Alex seemed a little more defeated. But what always amazed Jimmy was that Alex never laid a hand on her, and never resorted to heavy drinking. He stayed cool, collect, and only drank as much as he ever did. Some things that Jimmy's real dad couldn't have even considered. But all the same, that's why it didn't come as a surprise to Jimmy when he came home one day and found Alex breaking that second rule while he sat at the dining table with an empty bottle of jack Daniels and obvious tear marks on his face after they had broken up.

Though it was an unhealthy relationship, it had been a long one. And Alex felt lost without Sarah. He would talk to Jimmy about finding a way to make it up to her. But Jimmy, who had begun hating Sarah a while ago, insisted that Alex didn't go back to her. Jimmy implored Alex to begin dating again, to find someone else, someone better. After a few days of convincing, Alex finally got back up on his feet and began searching. He dated online, went to bars, had plenty of dates, but every one only seemed to reinforce the hurt. Alex only got more and more sad, and that sadness infected Jimmy's life too. And Jimmy wanted to somehow help Alex.

One day, nearing the middle of their fourth quarter, Jimmy was venting about his home life issues with his girl friends. He explained Alex's issue, and how it was ruining both Alex's and Jimmy's spirits. The girls brought up the same advice that Jimmy had already tried, and the ideas that Alex had already gone through with and failed at. They had been talking about it for the entire lunch and turned up nothing. None of them could help Jimmy. And when that lunch bell rang, they all apologized to Jimmy and began to leave for their classes. All except for Caitlin and Jimmy. Caitlin grabbed Jimmy's shoulder and whispered something into his ear.

"Come to my car after school." She whispered, then walked away.

Jimmy realized that she had spoken up during the entire conversation. His suspicions were already piqued, but he loved Caitlin as his best friend ever and knew she was probably onto something. So he trudged through his final classes of the day until the final bell rang. He got up and grabbed his things, beginning to make his way to Caitlin's car. When he saw it, she was already in the driver's seat with the car running. He walked up to it, around, and got in the passenger side. The AC was already running, and music was playing lightly through the speakers.

"Jimmy, how much do you care about helping your uncle?"

"A lot, why?"

"Because I had an idea. But why do you care so much?"

"What? Because he's my uncle. And he's the first person who's ever treated me right since my mother was still alive."

"Alright I get that, but the way I see it there's only one real way to help him and it would be... A little out of your comfort zone."

"... Okay. Well what is it?"

"Seriously Jimmy, how much do you care for him? Are you just telling me that you care for him, or do you genuinely believe yourself?"

"For fucks sake, the man took me into his home from an abusive family and has showed me nothing but kindness, what more do I have to say? Yes I care for his happiness!"

"Okay, fine. So the way I see it, he needs someone committed to him the way that his girlfriend was. Though it was a terrible relationship, they had been committed so long that he's lacking that significant other, not someone else who works well with him. He's never had that, so he doesn't know what he's missing."

"Okay..."

"So what I'm saying is, he just needs someone who can skip the getting to know him part, skip the finding out how they work together part, skip the long dating part, and get right to the part where they're committed to him and his needs."

"I... Don't think I know what you're suggesting."

"For fucks sake Jimmy, I'm suggesting that you introduce him to Jenny and skip right to being that person for him!"

Jimmy was in a stunned silence, "...What...?"

"Think about it. I know it's weird, but you two already know each other pretty well. You're already close. And you're already committed to him and his happiness. If he met Jenny, and Jenny was there for that commitment and his needs, then maybe that could help him stay afloat while he actually finds someone else. You follow?"