Jake is a young man living at home with his parents and his sisters. He seems perfectly normal but there are kinky sexual desires that live inside him. He likes girls and he’s even had sex a few times but he can’t stop himself from thinking about what it would feel like to be wearing the lingerie his girlfriends are always wearing when they sleep together. The last girl he had sex with, Cindy, put on a super soft and sexy red satin slip and red stockings and when she was on top of him riding his cock he was running his hands up and down her torso to feel the softness of the lingerie. That turned him on more than anything, including her incredible moans of pleasure as her pussy filled with his dick.
It was that experience with Cindy that got him thinking about trying something new, sexually speaking. He had dreamed of wearing women’s clothing – lingerie, specifically – before but he had never indulged in it because it seemed too weird. What would people think of him if they saw him prancing around in a camisole and a little skirt or a thong? Would they think he was gay? He didn’t feel gay because he wasn’t attracted to men. He just loved the feeling of something soft against his skin and women are the only ones that get to wear clothes like that.
His sister happened to have a whole lot of lingerie and soft clothing in her closet and Jake decided that the next time she left the house for an extended period of time he would explore her room and find something perfect for him. When she left a week later on a trip to the amusement park and his parents were at work he knew he had all day to himself. No one would barge in and disturb him as he became a crossdresser for the first time in his life.
Jake had been reading crossdressing stories on the internet because they turned him on so much. It was becoming an obsession of sorts and he hadn’t masturbated to anything but a crossdressing fantasy in a long time. Now he was going to become one himself, even if he was just going to be a man in his sister’s soft lingerie. Either way, it was going to be exceptionally exciting and he could feel something stirring in his balls as he made his way down the hallway towards her room.
Opening the closet Jake couldn’t help but get excited. “My sister has such beautiful clothes!” He said, pawing through the sexy skirts and beautiful dresses and tight tops. He didn’t know what to pick because it was all so beautiful and feminine. When he dreamed of being a cross-dressing sissy Jake always thought he’d wear something pink because it was the most feminine colour. Lucky for him there was a beautiful skirt and tank top staring him in the face as soon as he opened the door. He looked at everything else but the original is always the best and he pulled the outfit out and got ready to try it on.
Slowly he pulled the soft pink tank top over his head, letting it caress his back and chest as it fell over his shoulders. His nipples got hard instantly – not a reaction he was expecting – and his dick was throbbing. He grabbed a pair of his sister’s panties from her dresser and slid those up his legs as well. They too were soft and beautiful and once again he could feel a stirring reaction in his crotch. The pink skirt with the ruffled bottom was the final touch and it was perfect. He looked in the mirror and was thrilled with what he saw and more importantly with what he felt.
“I feel like such a girl! Who knew that being a crossdresser would be so much fun,” he remarked as his hand slid down to his new panties and began rubbing his dick.
He was getting awfully hard and it was the exact reaction he was hoping for. He wasn’t sure that he would have enjoyed the crossdressing experience so much but this was amazing. He was stroking his dick furiously as he dreamed of dressing in his sister’s clothing all the time when he heard the door behind him open. He froze instantly and turned around hoping against hope that it wouldn’t be his sister or parents. He could probably handle someone else finding him as a crossdressing boy but not a family member. That’s why he let out a soft sigh of relief when he saw Tiffany and Jennifer standing in the doorway with their mouths agape.
“Oh my God Jake! What are you doing,” Tiffany screamed when she saw him standing there with his rock-hard dick in his hand.
The girls had always been hot and Jake had spent more than a few nights dreaming about what it would be like to wear their clothes and fuck them. They both had big tits and brown hair, although Tiffany’s had a little bit of an auburn tint to it and he had always really liked her because of that.
Jake stammered “I:I can explain, I swear. I was just in my sister’s room and I saw the outfit in her closet it looked interesting so I thought I would try it on. I wasn’t going to make a mess or anything, I promise. Please don’t tell my sister you found me like this.”
“Your dick looks like it’s pretty close to exploding so I think you probably were going to make a mess Jake. You were going to make a mess all over your sister’s pretty clothes and then you were going to try to hide them. What a little sissy bitch you are,” Jennifer said with a menacing tone that sent a chill through Jake’s body.
The girls looked at each other and at the same time a big smiles spread across their faces. They had come to the same conclusion: they were going to fuck Jake’s ass with a dildo to show him what being a girl really felt like.
“Okay Jake, we promise we won’t tell your sister as long as you agree to do something for us,” Tiffany said with a naughty smile on her face.
“I’ll do anything as long as you keep my little secret,” he said with relief in his voice.
“Then we have an agreement. Jennifer and I are going to fuck your ass with a dildo to show you what it’s like to be a girl. You need to know how it feels to receive the deep penetration of a thick cock so you can decide if you want to become a real sissy that gets fucked all the time. Do you think you’d like being a crossdressing slut that spreads her legs to get fucked whenever someone asks, Jake?”
He looked at the ground and mumbled something unintelligible as his answer. He was feeling a burning shame and a little bit of embarrassment at the prospect of getting fucked up the butt by a dildo. At least it wasn’t a strap-on cock; that would have been the ultimate shame! The ladies went into his sister’s closet and pulled out a huge blue dildo that he had no idea even existed. His sister was a naughty girl!
Jennifer spoke next, saying, “You don’t have a pussy to fuck Jake but your tight virgin asshole will be just as good. You can find out what it’s like to get pumped full of cock just like a girl does when a man takes her cherry. It’s going to hurt at first but I’ll be gentle with you.”
While Jennifer was getting ready to plug the crossdresser’s ass with her toy Tiffany was playing with her tits and fingering her pussy. She was so turned on watching him get fucked like a sissy bitch that her pussy was dripping wet.
“How does it feel to be a girl?” Jennifer asked him as she started fucking his ass deep with that big toy.
She was really thrusting it deep into him, making him into the sissy slut that he knew he would eventually become when he put on his sister’s clothing. It was inevitable that wearing women’s clothing would turn him on to the things that women like to do in the bedroom but it happened so much faster than he could have anticipated. Here he was on his knees getting rammed hard from behind by an incredibly thick plastic dick. There were two girls getting turned on by the fucking too; clearly, Jennifer and Tiffany were kinky gals in their own right.
With the skirt bunched around his waist, Jake was made to get on his knees on the floor facing the couch so he could eat Tiffany’s pussy while Jennifer continued working on his ass. She was fucking that big toy in there hard and moving the other end into her pussy. It was a double-ended crossdresser-girl fuck and he was getting more and more turned on. At first, it hurt to get penetrated by the big toy but now he was enthralled. He was in heaven getting taken so deeply and as he was eating Tiffany’s wet box he realized that he was living out one of the fantasies he had experienced while reading crossdresser stories online.
The girls moved him onto the couch and had him sit with his legs spread so he could be taken in a simulated missionary-style type position. The big blue dildo split his asshole again but by now the crossdressing slut was plenty loose so it slid right in and filled him up good. He moaned and Tiffany lowered her pussy onto his face to shut him up.
“Quiet down and eat my pussy you crossdressing sissy. We’re going to use you anytime we want from now on. We like to have fun with a sexy sissy slut sometimes and since you clearly want to be that for us then we’re going to call you anytime we’re in the mood. You’ll come over, we’ll give you something pretty to wear and then we’ll fuck your ass hard. We each have strap-on cocks so maybe someday will double penetrate you to really make you feel like a bitch. Don’t worry, you’re going to love being our little toy. Now eat my pussy good and make me cum you bitch!”
Tiffany was getting ready to cum hard and Jennifer was watching in excitement and playing with her pussy. They were turning Jake into a man that loved crossdressing sex more than any other kind and he was never going to be able to go back to regular fucking. The look on his face was one of pure pleasure as the dildo pushed in deep and rubbed his prostate and he was clearly looking forward to the pleasure of shooting his big load.
Jennifer said, “It’s time for you to cum Jake. I know you have a big load built up in those heavy balls of yours and we want to see it come out. We want you to lose your load and confirm that you’re a sissy crossdresser and that you’ll only want to wear women’s clothing when you orgasm from now on. Go ahead and stroke your meat and shoot it all over me. Confirm that you’re a sissy by cumming on my titties and my pretty face.”
Jake loved everything she was saying. He felt like a sissy crossdresser and if these two were promising him a life of cross-dressing sex he was not going to turn it down. It would be more arousing than any kind of sex he’d ever had before and he could feel his balls boiling. The cum rushed up his shaft and it was the most powerful orgasm he’d ever had. Shot after shot of hot jizz splashed on Jennifer’s body and she smiled up at him while Tiffany ran her finger over his asshole and told him what a good girl he was. It was the start of a very new life for the young man.
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