Different Kinds of Cramming!

Paul is a cute, slightly feminine blonde college freshman and he loves the theatre. The people there have always been accepting of him whereas the jocks in high school would always pick on him for being kind of girly. He can’t help how his body developed so he never understood why they picked on him so much. He would get shoved around all the time and it wasn’t uncommon to get beaten on pretty well by the bullies. That’s why he was thrilled to go to a liberal arts college where they were far more likely to embrace anyone that walked through the doors. He really couldn’t wait.

When he showed up on campus in the fall of his freshman year it turned out to be almost everything he had been hoping for. The people were indeed really nice and there was a great theatre program that would allow him to pursue his ultimate dream of acting.

He wanted to be a performer and when he went in for his first audition they praised his performance. He did a monologue from Hamlet – perhaps he was aiming a little too high for his first audition – but they seemed to think he nailed it so he walked away satisfied.

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When the cast list went up he was delighted to see his name but he was a little surprised too. They had cast him in the part of the ing? nue. He was to play a pretty young woman and that’s not exactly something he had done before. What surprised him even more than seeing his name up there, though, was the feeling of excitement he had when he read it. He was actually looking forward to putting on women’s clothing and getting on stage in a dress and underwear and all that good stuff. It seemed such an odd thing but perhaps the director saw that in him during the audition and decided he was going to make the best of it.

The costume fitting was three days later and they had everything laid out for him in a private dressing room. There was a lovely red dress with a beautiful ruffled skirt that flared out, a curly brown wig, black stockings, red high heels and a pair of blue panties to keep his dick in place. They also gave him a makeup set and instructions on how to apply everything. The director didn’t want him to have to dress in front of anyone else for fear of embarrassing him before he even got underway with the part so he was left on his own in the dressing room to figure out his costume and put it on so he looked his best.

As it turns out Paul was something of a natural at dressing like a woman because he put it all together very well. When he was done he looked like a college girl all dressed up to go to a fraternity formal. The dress fit his body perfectly and the long puffy skirt made him feel and look so feminine. He swished when he walked and there was nothing more girly. He could feel the encroaching girliness all over his body in fact. He was a crossdresser now and although he didn’t know it yet it would become something that he loved with every fibre of his being.


He did his makeup very well, going with dark pink lipstick and just a light covering on the face to keep it simple and youthful. A little eye shadow and just like that he was ready to make his debut as a crossdressing boy. He stepped out into the hallway and felt his thighs brush together as he walked and the dress caressing every inch of his skin was enough to generate some serious action down in his crotch. He was unbelievably aroused and it was then that he began to think that this cross-dressing thing might be more than something for his costume. Perhaps he was going to be indulging in wearing women’s clothing quite a bit more often.

Just as he was thinking all those pretty thoughts in his little crossdresser head his math professor came down the hall. Somehow he recognized Paul in the girly outfit and told him that they needed to talk in his office. He didn’t seem fazed by the female clothing; if anything he was more interested in Paul than usual. At the time that didn’t strike Paul as unusual but he would certainly think about it later.

“Paul,” he said gruffly, “you’re failing my class. You scored a 55 on the last test and it’s obvious that you haven’t been studying.”

Paul, with panic in his breath, pleaded with Mr Thomas, “Sir, I’m sorry I’ve been studying really hard. Math is just a really difficult subject for me and I need help. I will get a tutor and come to your office during hours and do extra credit. If I fail this they’ll take my scholarship away and I won’t be able to come back to school next semester. That would be a disaster sir. Please, you have to help me.”

At that point, Mr Thomas sat back in his chair and rubbed his chin like a villain from an old James Bond movie. Paul should have recognized that as the first sign of trouble but he was so panicky and still a little caught up in the delight of being dressed like a pretty woman that he didn’t even blink an eye.

“How long have you been a crossdressing boy, Paul?”

“This is my first-time sir. I got a role in the school play. I’m not really sure why they cast me as a girl but I really want to act so I decided to take the part and at least give the costume a shot. How does it look?”

Mr Thomas looked Paul up and down like a butcher appraising a cut of meat. “You look fantastic. In fact, you look so good that I think I have a deal for you.”

That’s when Paul got nervous. He could see the lascivious look in Mr Thomas’ eyes and he knew that sexual hunger was behind it. He had experienced that same feeling for some of his female classmates and it was bizarre to be on the other end of it. Who knew that dressing up as a sissy would make him into a sexual object for his grey-haired math professor?


Mr Thomas stood up and walked over to Paul, “I have a special attraction to boys like you Paul. I like cross-dressing sex. I like to see a young boy like yourself dressed up like a girl and waiting to service my cock. Pardon me for being blunt but I’d like to fuck your asshole, Paul. I’d like to fill you with dick and then make you drink my cum. I think you’re a gorgeous sissy slut and that you should have your cherry popped so you can know what it’s like to be a real woman. You couldn’t possibly have dressed up like that without knowing the effect you would have on men. Do you know how beautiful your dress is, how sexy your stockings look?”

Paul swallowed hard and looked into Mr Thomas’ eyes. “So you’re saying that if I have crossdresser sex with you that you’ll give me an A in class?”

Mr Thomas smirked because he knew he was going to get to fuck the sissy’s asshole.

“It’s very easy to take an eraser to my grade book Paul. All I have to do is change the grades from F to A and all of a sudden you’re one of my best students. All you have to do is give up that hot virgin mouth and that tight virgin asshole of yours. Are you willing to do that?”

With a quiver in his voice, Paul said, “Yes, Mr Thomas.”

With that, he had given himself over to the pleasures of crossdressing sex and his asshole was going to be owned by his math professor for at least one night. He would become a fuck slut and the next day he would wake up a completely changed young man. Things are never the same after you’ve been screwed in the rear by your teacher.

Mr Thomas started by groping Paul’s hot ass through the soft material of his dress. He groaned about what a hot sissy slut the young man was and then he began lifting the skirt. There was a whole lot of material so it took him some time but all the while he was caressing the crossdresser’s legs and groping his ass and Paul was getting more and more turned on. Earlier that day he had never worn a piece of women’s clothing and now here he was bent over about to get fucked like a sissy slut. It was a change of pace he would never have seen coming.

When Mr Thomas had the skirt pulled up around Paul’s waist he yanked his panties off quickly and began fingering the sissy asshole that his cock would soon be entering.

“Your asshole is nice and tight, just like a virgins should be. Are you looking forward to getting fucked for the first time, sissy slut?” he asked.

Paul looked back at him with big innocent eyes and said, “Yes sir I’m looking forward to getting fucked. I want to feel your big cock in my asshole. I want you to fuck me hard.”

By the time he finished asking to get fucked he actually meant it. He wanted to know what it felt like to have a man hump his asshole and he was ready to be taken by this old teacher. After the fingering to loosen up the virgin sissy ass Mr Thomas drove his cock inside roughly. He wanted to tear open that tight butthole and at that point, there wasn’t anything Paul could do. He was bent over the desk like a sissy whore and even though it hurt he couldn’t help but moan. He was so deep in the mindset of the crossdressing slut that he just wanted to make his lover happy. He wanted to make sure that Mr Thomas got all that he desired from his sissy slut boy.

The crossdressing sex started to feel good after just a few minutes because his asshole was loosening up. The more the hard senior cock thrust into his sissy butt the better it felt. He was getting rammed like a slutty crossdresser and he was starting to moan for real. He was being loud and he meant every groan. He was in love with being used as a sissy slut and he knew at that moment that putting on the dress was the greatest thing that had ever happened to his sex life. Now he was going to be a crossdresser whore for anyone with a big dick.

Mr Thomas flipped Paul over onto his back and started pumping away at his butt missionary style. Thrust after thrust he hit that hot ass and when his dick started rubbing against Paul’s prostate the pleasure went to another level. It was far better than any masturbation he had ever done and it was making his sissy cock leak like crazy. He was looking into Mr Thomas’ sexually crazed eyes and understanding exactly how a sissy boy could fall in love with a man if this kind of sexual pleasure was involved.

The last thing Mr Thomas wanted to do was feel Paul’s virgin mouth around his cock. After fucking his ass hard with his big dick he pulled out and made the crossdressing slut boy get on his knees and suck. Paul did so dutifully, always delighted to pleasure his man in any way possible. The sacking led to a big load of cum that splashed onto his face and down his throat. He ate it all dutifully and then thanked his new lover. The crossdresser walked out of the office delighted with himself and knowing that he would be back again soon to get nailed once more.

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