Introspection

And as he went on with these kinds of fetishes, he found that they were beginning to consume his addiction. All of his other diverse interests began to gravitate towards these fetishes. And he slowly began to convince himself that it wasn't gay, of course not. He wasn't interested in the penises, only the feminine features and feminization aspects of it. Of course. He couldn't be gay. But if he was, did it matter? It's not like anyone in this town knew him, and when he started school this upcoming year what would it matter?

Thoughts and questions like those buzzed in his head like a wasps nest. The thoughts of these fetishes and his sexuality began to creep into his regular time during the day. When he didn't have something important to think about, he was usually fantasizing about tranny porn and wondering if he was still straight. Day after day he found himself more and more dedicated to them. And day after day he found out more about them, more actresses, even more specific and refined fetishes within the larger whole. Things like futanari, femdom, and gender reversal opened up more unique options to him. But the biggest that he found was something called 'Sissification' or the act of turning a boy into a feminine ladyboy. At least, that's what he assumed it was. As he began to look into it, he began to understand that it was so much more than that.

The porn unraveled in layers after layers. First trans porn, then the weirder specific things like sissification, then the even more refined brands of that fourth level fetish like sissy hypnosis, sissy trainers, sissy captions, sissy videos, and more. The list went on and on, and as he explored them he discovered that sissies weren't just lady boys. They were supposed to be mindless fuck sluts. Loyal to men, specifically black men. They never second guessed their masters, and were always craving satisfaction. A chastity cage was common, and women's clothes was a must. Things like sex toys, butt plugs, makeup, wigs, shaving, lotion, anything to make them as feminine as possible seemed common. And all of it seemed to get Jimmy's rocks off more than anything he had found before. Something about sissification, how both feminine and not it was. In some ways, the stripping of masculinity from a boy and enforcing feminine character onto them through pure and total domination was just too arousing.

Slowly Jimmy's porn folder became dedicated to sissy porn. He became well versed in all minor specifics of the genre. And as the summer entered it's third and final month, Jimmy was beginning to stagnate. He had dug as deep as he could, found all that there was to find, and beat his six inch dick off to everything in his folder and seemingly everything online. The only source of new content was the drip feeding of individual sissies and traps posting photos of themselves online every once in a while. Jimmy began to idolize these 'girls', following every photo they posted and commenting anywhere he could. He loved their lives, loved their spirits, and adored their character. His favorite one, a cute skinny blonde sissy that posted every few days onto their tumblr, was his main inspiration. One day he commented, and swiftly got a response from her.

"You're so hot, I wish I could be like you!" He posted.

"What's stopping you?" She replied within five minutes, followed by a winking emoji.

He began to type a response before he paused and leaned back. He was trying to think of what to say, but was coming up short. He had no idea what was stopping him. He had around ten hours every day where he was alone in his house, added on top of that the whole of the night. He thought of something, leaned back in and began to type.

"I don't have the things I would ne-" But he stopped and shot out of his chair.

He rushed over to his closet and swung the door open dropping to his knees by the corner. He tossed the small things aside and dragged the boxes out once more. It had slipped his mind for this whole time, but just then he remembered the boxes of his mothers things. He dragged them out to his bed and began to pry them open. Both were stuffed with clothes. The box on his left seemed to be filled with smaller things, such as panties, bras, socks, stockings, leggings, etc. While the one on the left had all the shirts, dresses, skirts, pants, and... And a weird bag at the bottom of it. Jimmy spotted the bag and was a little confused. He dragged it out, spilling a few articles of clothing over onto the floor, and tossed the bag onto his bed. It didn't strike his as clothes really as it had a different weight and feel. It was a light grey pull string bag almost the length of his arm. He grabbed it and pulled open the top. But he didn't see what it was at first.

On the top was a mound of blonde hair. He grabbed it and pulled it out before realizing it was a long blonde wig. Underneath it was a short, brunette, bob cut wig as well. He was totally confused. He grabbed the wigs and tossed them aside before looking back in. The next thing in the bag was a couple pairs of skimpy lingerie, things like panties with a part on the crotch. He wasn't as interested and tossed all of those aside as well. Now as he looked in, his face burned red. There was a 7" purple dildo shaped to match a humans, a 10" black dildo with a strange shape and end to it that resembled some kind of animal's, a small metal butt plug, a vibrator, and multiple small bottles of lube.

Jimmy didn't know what to do. He only dropped the bag and stepped back to take the whole scene in. In front of him was his sissy dream come to life. He could already see the image in his head before he had come to terms with what he was about to do next. He rushed back to his computer and only responded with, "Thank you." Before switching over to new tabs.

He began pulling up every sissy guide, tips, how-to, and advice page he had found. After he had found enough, he rushed out of his room. He ran for his bathroom, and flicked the light on. He jumped out of his clothes and grabbed for his razor. He had read multiple things online about what to try and what to avoid with shaving. He got some wet towels, then decided to just run the shower. He stepped in and got to work. It took him some time, and there were definitely some challenge areas that he had to get creative with. But stepping back out of the shower twenty minutes later and he was almost completely hairless. He felt himself up and down, admiring the smooth feeling. Then, he grabbed the for the bottle of lotion and began to spread it all over his now smooth body.

He walked back into his room and went back for the boxes. He dug around again in the right one until he found another smaller box that was in the corner under the string bag. This box was mostly transparent with small metal edges. He grabbed it and went back to his computer. He grabbed the laptop, and took both back to the bathroom. He set the laptop down and tabbed over to his makeup tutorials and advice pages. Then he set down the box, unclasped the metal hook, and opened it up to reveal his mother's old makeup kit. He read over the instructions and set about his work.

It was a tricky thing doing makeup. There were so many details, and so many steps. One mistake and he could ruin it all. And there were many, many small mistakes. But he braved through it and managed until the end. He had followed the instructions, which had been specified as a light makeup casual look. There was a bit of concealer, a dash of color on his cheeks, a little color above his eyes, and some straightened eyelashes with short cat-eye lines drawn in. Of course, he had to add the firetruck red lipstick that he found in the makeup kit. Though the guide recommended not using a bright color, he wanted to feel it. Once he was done, he looked back in the mirror to the lady boy standing there. His (her?) transformation was nearly complete.

He went back to his room and began searching through the box of clothes. He found the things that he liked the most, being a pair of pink lace panties and bra, a short black skirt, a pair of black stockings, a white V-neck Tee shirt, and to top it off the short bob wig. He was about to start getting dressed before he looked back at the bag and began to wonder. He dug in it for two things: The butt plug and the bottle of lube. He pulled them out, popped open the bottle, and applied a healthy layer all over the cool metal. He tossed the bottle aside and brought the piece of metal around to his rear. He lined it up and winced at the wet, cool metal against his bare smooth cheeks. When it began to praud against his hole, he once again shivered. He paused for a few moments, worried about what he was about to do. But gritting his teeth and sucking in a breath, he pushed it down. At first, there was only pain as it bore its way into his ass. But it slipped in smoothly, and after it was all the way down, the pain quickly began to subside. It didn't become pleasure, only a strange bulge of pressure.

He leaned back and took a step, and that's when the strange feeling began to resemble pleasure as the pressure rubbed against his insides. It sent shivers up his spine and down his legs, slightly buckling his knees. He took a few more steps to adjust to the feeling. And as soon as he did, he was jumping for his clothes. He slipped into them cleanly and smoothly, and soon the soft fabrics clung to his body. Once all the articles were on, he grabbed the wig and tucked it over all of his hair. And with that, he walked back to the bathroom to look in the mirror. Staring back was not just a lady boy, but a sissy. A beautiful, sexy sissy. And her name would be Jenny.

Jenny spent that night in drag taking photos and masturbating with the plug in her ass. Something about it all made things a thousand times better. She responded to the comments made earlier, thanking for the boost of confidence. As the conversation thread continued, a few people requested that she post pictures of herself. It took her a few moments of thinking, but the heat of the moment overpowered her common sense and she posted them. Immediately the love and affection began to roll in. She read and replied to each comment on her pictures, and felt her cock press more and more against the fabrics with each comment she read. She ended up coming three times that night.

As five in the morning bagan to roll around, she jumped out of her chair and went to undress. She tucked everything back in their boxes and pushed the boxes back into the closet. She went to her bathroom and cleaned the makeup off, stowing it away in the cabinets. She then finally went back to her room and fell asleep. The next day, Alex knew nothing, Sarah knew nothing, and Jimmy had gotten away with it. He was beginning to think that Jenny would be making a lot of appearances going into the future.

And as the final month of summer melted away, Jimmy's guess was right. Nearly every night Jenny would get herself prepared, trying out different combos, testing makeup, playing with toys, and practicing being a girl. Every night she would take photos and post them online to reap the rewarding comments. And every passing night Jimmy grew more and more attached to his new alter-ego. The comments grew nicer and more abundant, while the photos grew skimpier and sexier. Jenny's skills began to refine as she continued studying up on all the tips and tricks of cross dressing. It was all going so well, until school started.

School was the big thorn in Jimmy's side that had only been growing larger as it approached. He had been a decent student, mostly A's and B's, and had established a small close group of friends from his old town that he would hang around during school. He liked his old school, liked his teachers, liked the smaller school feeling, and it's outdoor design. Now, Alex had sorted him out in the main high school for his new town. As the town was substantially bigger, so too was the school. The school was about three times larger, and as it makes sense for larger schools it was mostly in doors. Gone were Jimmy's days of sitting out on the grass in outdoor quads during breaks with his friends, and in came the days of standing under bright LED lights in crowded hallways by the lockers. But the school itself was the least of Jimmy's worries.

He had no friends, knew none of the teachers, and for that matter knew no one at all. Walking into school his first day, he was assigned a student to help show him around but even they seemed uninterested in being friends with Jimmy. Plus, starting at a new school is already a hard time but doing it your senior year just made it worse. Jimmy felt unmotivated to meet people because he would be leaving after that year. And that lack of motivation leaked into his school work as he found himself sitting in his classes with no drive to try in them. To him, it didn't matter what happened anyway. He hadn't ever had a plan for after high school. When his mother was around, she would tell him how important it was to go to college and find a career. But after she passed, his father would go on and on about how college was for suckers willing to dish out wads of cash for nothing in return. With all the mixed messages, Jimmy just never put much thought into it, leaving him here in his senior year without any kind of idea where his future was heading. All he knew for sure was that every night he would go home and dress up as a sissy.

As homework began to be passed out in classes, and his grades were already suffering he found the struggle for time between following his fetish and doing his work. But after a few weeks in, Alex sat Jimmy down and talked to him. Alex explained that they were happy to look after him, take care of him, and get him into college if he wanted but that meant Jimmy had to try in school. The way Alex said it wasn't harsh, or even very demanding. It was sweet, more like a recommendation for everyone's mutual best interests. It only made Jimmy feel worse, reminding him that he was indebted to Alex. He owed it to Alex to do well in school. So Jimmy started doing his homework again and studied for tests. His grades steadily rose once more. In exchange for that, Jimmy had to give up on dressing up every night and instead chose to do it only Fridays, Saturdays, and Sundays. It would be his weekend treat.

But Jimmy still felt no need to make friends. He attended his classes, took notes, did homework, and didn't participate in anything else at the school. He sat in the back of most of his classes, and during lunch periods he sat alone. Jimmy didn't mind the silence, but he didn't need to because Caitlin would do it for him. Caitlin was a girl that had his physics class and math class. She was a really sweet little thing that only stood at about 5'6" with long curly blonde hair. She was extremely attractive, with a large round rear and a surprising amount of bust for such a small girl. She first introduced herself to Jimmy in their math class and mentioned that she felt bad for him being all alone. He would tell her it was nothing to worry about, but she insisted. And one day during lunch, she brought two of her close girl friends to come sit with him. She introduced them to him, and they began chatting.

By complete submission and luck, Jimmy had fallen into a friend group. And somehow, he had fallen into the group of peppy and popular girls. There were about twelve of them, over half were cheerleaders, volleyball players, or softball stars. Almost all of them got good grades, and once again over half dated stars of the football team. Caitlin had been Jimmy's in, and after a week they all accepted him as their new 'gay best friend'. Of course, he didn't tell them that when they jokingly called him their 'gay best friend' it hit too close to home with his sissy fetish. But either way, they were fun, interesting, and people to talk to. So despite his defeatist attitude, he was happy where he landed. And began to fall into a rhythm.

Jimmy became pretty close with his new set of friends, but mostly with Caitlin. They would hang out at every break, every lunch, and after school whenever they could. She showed him around the town which he hadn't explored at all. She took him to movies, restaurants, bowling allies, anything they could do together they did. Jimmy was beginning to find that Caitlin was his closest friend he'd ever had. She was so sweet, thoughtful, and caring. None of his male friends from his old school ever cared as much about him as she did. The rest of their group cared too, and were all nice in their own right, but Caitlin was something special. He had become so close to her, he felt like he owed her something. He owed her his word. And he would always keep his word, and trust hers.

The first quarter of the year was over in a flash. After Jimmy had found his friends, found his groove in class, and worked out his situation at home he found that time was flying by. Going into their second quarter, it was approaching Halloween when things began to spice up for Jimmy. At lunch one day, he and his girl friends were sitting by their table discussing their Halloween plans. They had been invited to the quarterback's Halloween costume party, and they were sharing what they would wear. Jimmy had to stop himself from laughing at the cliche choices they were going with as they went down the line: Sexy cat, Nurse, black widow, etc. All of them were going as something skimpy. Eventually the line got to him.

"What about you Jimmy?"

"Huh? Oh, I'm invited too?"

"What?!" A few of them cried in astonishment, "Of course you are! We would never let them exclude you. You're with us." One of the girls said.

"Oh, hah thanks. Well I hadn't thought about it since I didn't know I was even going... I feel kinda awkward since, you know, all of you are going as these sexy costumes and I'll probably be there dressed like Dracula or something..."

The girls laughed at that, "Yeah you'll be with us but you'll stick out like a sore thumb."

"He should match with us!" One girl cheered out.

"Hell yeah!" Another girl exclaimed, while the rest began to chatter in agreement.

Jimmy was beginning to get nervous, "Yeah Jimmy, you gotta do it! It'd be the best thing ever if you dressed up in drag to match us!"

"Ehhhhhhh... Uhm..." Jimmy couldn't respond to that as his face burned red.

Caitlin pulled on his shoulder and looked at him with puppy dog eyes, "Come on Jimmy, you gotta!"

"Heh... I guess... I could do that..." He gave in and relented.

The crowd of girls roared in praise and agreement before moving back to talking about their costumes and the night. Jimmy sat quietly contemplating what he had agreed to. He was hoping they would all forget by the time it happened, but then he felt Caitlin tugging on his shoulder again. He looked over to see her proud smile.

"I'm so glad you agreed! It'll be really fun. I promise." She chirped.

"Yeah... It's no big deal."

"See Jimmy? This is why you're cool. Most guys would be too chicken to agree to something like that. But you're better than that."

"Heh... Thanks."

"So how are you gonna do it?"

"Do what?"

"Dress up as a girl, duh!"

"Oh I don't know..."

"Maybe you can get your uncle's girlfriend to do it for you!"

"What?! No... She couldn't do it, she's... too busy." He stammered, not wanting to risk having Sarah see him as a girl.

"Oh... Maybe I can do it!" She chirped again.

"Um... Sure?"

"Awesome! It's on friday, so I'll come by after school and we'll do it."

"Yeah, ok..." He heaved, sickened by what he had gotten himself into.

By Thursday, Jimmy had gone into a complete funk about the ordeal. One on hand, he didn't know how to feel about dressing as a girl in public, especially in front of other people from his school, but on the other hand he felt really excited by the idea and his sissy nature craved it. He was panicking by the end of the day and found Caitlin to explain to her that he wasn't going to go through with it. He found her by her car, and when he told her she didn't seem to respond. She only looked disappointed then offered him a ride home. He was unsure how to feel about her lack of a response, but not wanting to walk home either he accepted. She drove him back to his house and they both got out. They walked into Alex's home and he once again prodded her with his frustration.