Ian was on the bus because it was the cheapest way to travel. He was in college and paying for it himself with loans and all the work he could find so he was trying to live as cheaply as possible. That meant when he wanted to go on vacation that he would have to take the bus. As it turned out this bus ride was better than any he had ever been on because he spent the entire time flirting with a beautiful girl named Sandy. She had short red hair, big tits and a wicked tight body that she didn’t have any trouble showing off based on her cropped top and her tight pants. They ended up sitting next to each other and spent almost the entire ride gabbing about anything and everything.
When the lengthy bus ride ended he grabbed his case and that of his lovely lady friend Naomi. He was being polite because he wanted to make a good impression on her in case they ever met again. He didn’t quite have the balls to ask her out for a drink or dinner so he just passed her the case and wished her good luck. On the way to his hotel room, he scolded himself for being such a wimp. He should have just asked her out!
There was something about Naomi that made him feel a way he’d never really felt before. He couldn’t quite place it but he was experiencing feelings unlike any he’d had. When he thought about it a little more he realized that those were feelings of jealousy. He was jealous of Naomi’s beauty her sensuality and her big tits. He was jealous that she was a woman. What? How could a man be jealous of something like that? It didn’t make any sense but the more he thought about it the more it struck him that he wanted to be Naomi even more than he wanted to be with her.
His head was buzzing as he opened the door to his hotel room and pulled his suitcase in behind him. He threw the case onto the bed and popped it open to start unpacking. That’s when fate intervened. The clothing inside was all female. He had switched cases with the lovely Naomi and now he had all of her clothes and she had all of his. Was this some guiding force telling him that it was okay to dress as a woman, to become a crossdresser? Because he had already spent so much time thinking about being a crossdressing boy and being a woman he decided that’s exactly what fate (or God or whatever) wanted.
The fact that her suitcase was filled with exceedingly sexy items turned him on even more. She had stocked it with lingerie and frilly bra and panty sets and stockings and sexy dresses and some fairly slutty outfits. Clearly, she was planning on doing a whole lot of partying on her vacation. That would be pretty difficult now since all her clothing was sitting in his room. Instead, Ian would have to take on the mantle of the party girl, something he was more than prepared to do after daydreaming about being a woman for the better part of three hours. Could he actually take the next step and become a crossdresser?
When he found a pink satin bra and panty set he felt like it was calling his name, “This is beautiful. I have to put this on.”
He knew the satin would feel good again his body, caressing his skin so soft and making him feel like a woman. He had always been fairly hairless so he wouldn’t look completely ridiculous like some hairy monster putting on girls’ clothes. It would just be a little ridiculous. The first thing he did was slide her pink satin panties up his legs. It was the very first step in his becoming a sissy crossdresser and it felt so good. His body actually shivered as the soft material went over his knees and groped his thighs and finally came to rest against his balls.
His dick was instantly hard, a sure sign that this was something he was meant to be doing. He stroked his shaft and it was more pleasurable than it had ever been before. Was he becoming a sissy boy this quickly? Was it possible his body was responding to the cross-dressing pleasures even more than he thought it would? It certainly seemed that way.
The bra went on next and he found some tissue to stuff it a little so he didn’t look totally flat. It was way more interesting when he was sporting a nice pair of titties like a college girl instead of a flat chest like a college boy. It didn’t even occur to him but Ian was totally acting as an experienced crossdressing boy would. He was trying to look as feminine as possible, presumably because he wanted people to notice him and at the very least because he actually wanted to be a girl.
He found a pair of black lace top stockings and his hands practically trembled as he went to pull them up his legs. Slowly but surely they rose towards his crotch, making everything tingle along the way. Who knew that something so simple as putting on a pair of nylon stockings could make this sexy crossdresser so aroused? After putting on just one of them his dick was raging and precum was dripping all over. He had always been a heavy precum producer but this was ridiculous. Clearly, his body was responding strongly to him becoming a crossdressing slut.
After putting on the second stocking he looked in the mirror and he loved what he saw looking back at him. It was a woman or at least a fairly close representation of one. Obviously, he wasn’t going to turn into a completely passable sissy crossdresser in the span of one session but Ian knew that this was going to be his life going forth. He would wear boy clothes when he had to go out into the wide world but he would spend most of his private time dressed as a woman. This felt too good to pass up.
Next, he turned to Naomi’s suitcase to find something sexy to wear. He was thinking that a dress would be perfect because it would make him feel the girliest. At the heart of all of this was his desire to be Naomi and he knew that a dress that allowed a breeze to blow up his skirt and gently caress his ass would be a perfect choice. She had quite a few choices but he ultimately went with a short red number. It was fairly low cut but not too slutty and it had long sleeves that billowed out at his wrists. It was a mixture of a hippy look with a slutty party girl look. As he held it up in front of him he could see his hands shaking just a little bit. The thought of putting it on made him so excited he couldn’t even hold still.
He knew that putting on the dress would mark one of the final steps to becoming the crossdresser he was clearly meant to be. If he cut it all off now he wouldn’t have to become a sissy for the rest of his life but if he put that dress over his head then he was making a decision, setting a direction for the rest of his days and it would be of huge importance. As big a decision as it was Ian didn’t even have to hesitate. He knew he wanted to be a sissy crossdresser and that putting on this dress was the thing that would take him there. With that, he pulled it over his head and let it fall slowly to settle on his shoulders. The soft material felt wondrous against his newly minted crossdressing skin and he sure did feel good.
The final step was putting on makeup and even though he didn’t have much experience with it applying lipstick, eye shadow, blush and foundation seemed to come naturally to the young man. It was just another thing that confirmed to Ian that he was meant to be a crossdressing boy.
After he had finished putting on the makeup and completed the outfit with a cute-looking hat of Naomi’s he heard a knock on the door. He experienced a moment of sheer terror that was soon replaced by curiosity. If he answered and it was the hotel manager or a maid what would they think of his new look? Would they think of him as a freak or would they think he was sexy? Would the manager want to fuck him? All of these things flashed through his brain as he opened the door and the last person he expected to see was Naomi, the woman whose clothing he was wearing.
“What the hell are you doing? Are you wearing my clothes you little sissy?” she practically screamed at him.
He could see genuine rage and a little bit of surprise in her eyes but it softened quickly when he explained why he was dressed like that, “I wanted to see what it felt like to be a woman.”
His demure voice and the way his eyes were cast down at the floor seemed to quiet her rage. A new idea popped into her head when she remembered that she had brought a big blue vibrator in her suitcase.
“If you really want to know what it’s like to be a woman then I’m going to show you, sissy boy,” she said with a distinct tone of menace in her voice.
She directed him to the bed and then she reached into her suitcase and found the toy. It was awfully large and it didn’t take Ian any time to know that she was going to fuck him with it. That was probably doing to hurt but he also knew that a true sissy crossdresser was able to take cock in his ass. If he was ever going to fulfil his new and powerful dream of becoming a crossdressing slut full-time then he would have to spread his legs and let her fuck him the way she wanted. It promised to hurt but he figured he could take the pain that she was going to be doling out.
She tied his hands behind his back to make sure that he didn’t try to get away and then lubed up his asshole using the KY she had brought. She wasn’t being gentle or easy with him. She wasn’t trying to give him a good time; she just wanted to fuck his asshole like a sissy bitch and punish him for being such a bitch and putting on her clothes.
“Now you’re going to have your cherry popped. You’re going to find out what it’s like when a girl loses her virginity. I can tell you that it usually doesn’t feel very good, especially when the dick first fucks into you.”
With that, she pushed it past his anal ring and started fucking him for real. He was taking cock like a little crossdressing bitch and it hurt. It felt like his asshole was on fire because that vibrator was so damn thick. She had turned it on before shoving it inside him so the vibrations were loosening him up quickly but he was sure that he would be bleeding like crazy when it was over.
“How does that feel sissy slut? Do you like having a big cock up your ass? Wouldn’t you love to have a man fucking you like a crossdressing bitch?”
All of those things rang true in Ian’s head and as much as he wanted to deny it he was having a great time. He liked getting fucked by Naomi and he liked that she was treating him like a slut. Was this what it meant to have crossdresser sex? Was this what being a sissy boy would be like? If so he was even more excited about his new life.
After fucking him in what was effectively the doggy style position Naomi had Ian sit up so she could give him a little missionary loving. That’s when she saw how big and hard his cock had gotten and she was impressed. She gave him a hot handjob while ass fucking him since she was clearly getting into it too. This was her first experience with a sissy but she was really enjoying it. She even licked his dick a little but she was not pleased when he ended up shooting his load all over her face.
“I didn’t say you could give me a facial you little bitch!” she screamed at him.
He didn’t say a word since he was lost in his own head. The pleasure of his first sissy orgasm was overwhelming and he could barely think, let alone speak. Naomi gathered her things but she didn’t bother to ask for the dress or lingerie that Ian was wearing back. She wanted him to keep that.
As she was walking out the door she turned around and spoke, “You should give that ass a try with some guys now sweetie!”
He was certain that he would be doing that very thing in no time at all.
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