Sweet Transvestite

"I still can't believe you talked me into this," Rob said as he tried to slip the black fishnet stockings over his freshly shaved legs.

"I know," his girlfriend called out from the fitting room behind him, "But it was such short notice. And besides, you were the only other guy I could think of who could pull off Dr. Frank N. Furter."

"Yeah," he said, "But did I really have to shave my legs for this? I mean, what do you think the other guys will think if they see this."

"Oh relax," she shouted back at him, "It just wouldn't look right if you had stubly legs down there. And it's only for a couple of nights anyway. Do you remember the lines?"

"Yeah," he said, "I've seen the movie enough times."

Rob's girlfriend Natalie was an aspiring actress, which meant that she always had some theatre thing going on. This month it was the Rocky Horror Picture Show, which was actually pretty awesome, until one of their star actors broke his leg. Quite literally. He was in a car accident and was going to be stuck in a cast for a couple nights. Of course, Rob only found out about this after he got a phone call at 10 P.M. that night. Reluctantly, he agreed to do it.

Now, he found himself in full drag, staring at the mirror as he tried to put on his lipstick and make-up. Puckering his lips together, he struggled to get the right look going. It wasn't quite Tim Curry, but it was still a pretty decent approximation. He adjusted his corset and fishnets and struck a pose, trying not to seem too flamboyant.

He didn't see Natalie coming up behind him, already in full costume. She was playing Columbia in this production, and her costume only accentuated her full, busty figure. Her normally long red hair had been cut short, but it actually made her look a couple years younger when it was styled that way. And her tight little halter top pressed her ample bosom together, accentuating her cleavage. In fact, Rob couldn't help but stare when he first saw her in costume.

"Wow," his girlfriend said as he looked in the mirror, "Somebody is really pulling off a good Dr. Frank N. Furter!"

Rob spun around quickly, no small feat in those high heels.

"Well," he chuckled, "Just for a couple of nights anyway."

"Oh rubbish," Natalie said as she walked over and hugged him, "I think you would be a good permanent Frank N. Furter. In fact, can I let you in on a little secret?"

"What's that," Rob asked, trying not to stare too obviously at his girlfriend's massive chest.

Natalie looked up at him and smiled, her dark, doe-like eyes lined with dark mascara. It made her look like a tramp, but Rob liked it. It was kind of sexy!

"I've always thought it was hot when I saw a man dressed in women's clothing," she said.

Natalie slowly dragged her fingers across his crotch, literally rubbing his raging hard erection through the thin satin fabric of his panties. Rob could simply grunt in pleasure as he dripped a small stain of semen.

"Oooh," he said as he tried to maintain something of his composure, "I see..."

"Oh my God," she exclaimed eagerly, "I just had a really dirty idea! Why don't we have sex!"

"What," Rob exclaimed in disbelief, "You mean... you mean right here!?!? Right now?!?"

"Why not," Natalie purred as she pushed her boobs together and shoved them in her boyfriend's face.

"Don't you find me sexy," she cooed, "Especially in this tight little costume..."

Rob's throbbing erection -- still all too visible through the black satin panties he was wearing -- betrayed his true feelings.

"No," he exclaimed hesitantly, "It's not that... it's just... well what if someone catches us in the act?"

"Oh come on now hon," Natalie said as she dropped to her knees and pulled down her boyfriend's lingerie, "We're pretty much the only one's back here. It's not like anyone is going to catch us... and besides, that's part of what makes this so sexy in the first place..."

Rob offered no protest as his girlfriend wrapped her lips around his massive cock and began to suck. He simply stood there, still in full drag, and closed his eyes as she brought him towards the heights of ecstasy. Natalie was definitely a pro when it came to giving head. Without even thinking about it, Rob began to buck his hips, thrusting his manhood deeper and deeper into his girlfriend's waiting throat. A slight trail of saliva escaped from her mouth as Natalie tried valiantly not to choke.

For her part, Natalie pulled down her shorts and began to finger her cunt. She gave out a few muffled cries of pleasure, but Rob's cock filled her mouth, preventing him from hearing what she was saying. Not that he really cared right then, of course. Natalie was surprisingly wet, her own panties literally soaked from their quick romp of taboo sex. She brought herself to earth-shaking ecstasy as Rob dragged his fingers through her short red hair.

As she felt that familiar tempo start to build in her boyfriend's thrusts, Natalie stopped and let his still hard cock slip out of her mouth. A trail of jizz and saliva trailed down from her lips, pooling down her neck and into her beautiful cleavage.

"I think you deserve a special treat," she said as she smiled up at her boyfriend.

Slowly, Natalie pulled down her gold-sequined top, exposing her huge melons. Almost without thinking, as if taken over by an animalistic instinct, Rob reached down and groped his girlfriend's enormous breast. Ever so gently, he pinched her swollen nipple. Natalie shivered as a wave of erotic sensation tingled through her body.

"Oooh," she said, "That feels sooo good. Go ahead hon, I want you to fuck my tits! Fuck my big, juicy tits"

Rob hardly needed any encouragement. Straddling over his girlfriend's generously-proportioned chest, Rob positioned his cock between her breasts. Squeezing them together, he slowly began to thrust in and out, as if he were actually penetrating her. Fortunately, the mixture of semen, sweat and drool which now coated her body provided excellent lubrication for this very sort of activity.

The pleasure of having her already sensitive melons squeezed together proved to be too much even for horny Natalie, and he writhed in pleasure beneath her boyfriend as he thrust his member between her cleavage. After only a few more thrusts, Rob shot his load and drenched her face, neck and chest with his seed. He even managed to get a few drops in her hair. Natalie would have to wash that out before the show tonight.

"Wow," he said, wiping his forehead of sweat.

"That was amazing," Natalie said, her eyes drifting down his stubly, fishnet-clad legs, "Think we've got time for one more?"

"Why not? It's not every day you get to live out your fantasy of having sex with a guy while he's in full drag, now is it?"

It certainly wasn't, but Natalie was more than happy that her boyfriend would oblige her that wish tonight. Maybe next week she could talk him into wearing a sexy little sun dress...