Forbidden Pleasures

Author - Ami

Challenges Fulfilled - Easy Challenge #1 - Blair as a virgin. Easy Challenge #2 - Jim as a virgin to gay sex. Easy Challenge #17 - Blair has a secret - what is it?

Summary - Jim comes home one night to find a very different side of roommate.

Warnings - Cross-dressing.

*Author's Notes - I never intended to write a story for the Fest; at the time I started the Fest, I wasn't even writing. Then Peja asked for more cross-dressing fics, and put out the word challenge 'Forbidden Pleasure'. The rest is history.

Forbidden Pleasures

by Ami

He knew it was taboo, forbidden, illicit. But he couldn’t help himself. He supposed it all started when he was thirteen, and the bullies in school started calling him ‘pretty’ as an insult. It took a few years, but one day, when he was 17, worn-out from his first year at Rainier and wishing there was something he could do to be himself, when he didn’t even know who he was…he’d accidentally walked into Victoria’s Secret. All that satin and lace…and from then on, all he could think about was being pretty.

It wasn’t really that hard to be a cross-dresser. He started by growing his hair out. He might have told Jim that his hair was a babe magnet, and it was, but the real reason he wouldn’t cut it was because he couldn’t cross well without it. It made him look more feminine, especially after he put the sparkles and beads in it.

He didn’t do it that often, just when he needed a little pick-me-up. At first it was flattering, being hit on by all those guys. With Naomi for a mom, he’d been brought up to appreciate the male form, but since most of kids who bullied him were guys, he was kinda soured on them. But these guys didn’t think he was a geek, even when all he wore was jeans, a T-shirt, and his glasses. They thought he was ‘cute’. Of course, he looked female, but they still thought he was cute!

He sometimes thought briefly about taking one of them up on their offers to spend the night, but he knew once they found out he was male, they’d take off, or worse, beat him up. Then, he met Jim. Jim was a walking wet dream – a Sentinel, a handsome man – and unfortunately, totally straight. He’d occasionally thought about trying to get closer to him in his female guise, but he wanted Jim to want him, not Jasmine, his female persona.

When the longing got too much to bear, he’d get dressed up and go out. He only did it when he was sure that Jim was going to be gone for several hours, or even all night. It took him almost an hour to get ready, so he wanted to make sure Jim wouldn’t walk in on him. He didn’t know what Jim would do if he found out his roommate like to cross-dress, but he didn’t want to chance finding out.

This night, Jim was going to be on stakeout till the wee hours, so he decided to go all out – he waxed his legs, his chest, his arms, and everything else, washed, conditioned and blow-dried his hair, and dusted it with glitter powder. His makeup was light – lavender eye shadow and sheer lip-gloss were enough – and he put on the new satin and silk lace negligee he’d bought. It was white, and he’d bought baby blue thong panties to go under it.

The negligee was filmy, and hung from two satin straps on his shoulders, with the collar just above his breasts – or what looked like breasts. He wore a white silk corset with a pushup bra to make it seem like he was a B cup. The bottom of the negligee ended just above his knees was a lettuce-edged hem, and you could see the blue of his underwear through the sheer material.

He smoothed the skirt of the negligee down to the tops of his stockings, delighting in the feel of the silk against his now-hairless thighs. He thought he’d never looked sexier – not that he had any mental pictures of actual women to compare himself to. Once he’d started crossing, he realized that women didn’t turn him on half as much as men – and that he’d never have the nerve to approach a man. Since most girls didn’t even notice him till he was 19, two years after he’d started crossing, he was still a virgin.

He knew Jim would tease him mercilessly if he knew that Blair was still a virgin, but he didn’t want to be that intimate with someone he couldn’t share his secret life with. He thought about telling Jim, but he waffled between the opposite feelings on the matter – Jim would understand, because his Sentinel senses made him feel out of control, and his crossing was a way to purposely go out of control, or Jim wouldn’t understand, because he’d always thought Blair was straight, and while he wasn’t homophobic, living with a man who has the hots for you is an entirely different thing.

Which is why he was completely terrified when he heard Jim’s key turn in the lock, and saw Jim come through the door.

***

Jim blinked. He knew he’d heard Sandburg’s heartbeat, and only Sandburg’s heartbeat, so why was there a woman in his living room? A woman in a short white negligee and baby blue underwear, if he was seeing things right. And then he realized that Blair’s heartbeat had speeded up…and was coming from the young woman in the living room.

"J-Jim," the young man (woman?) stuttered. "Um, I can explain," Blair started, wide, terrified eyes staring at the floor.

"Okay," Jim said simply; he wanted to know why his roomie was apparently a cross-dresser, and Blair was complying by agreeing to tell him – couldn’t get any simpler than that.

"Um, er," Blair started; he hadn’t actually expected Jim to take him up on his offer. "I, well…I cross-dress," he said finally, deciding to just plunge in.

"I can see that, Chief," Jim said wryly, giving Blair an appreciative once-over; he was a very handsome man, but he made a gorgeous woman. Jim had known about his attraction to Blair for months, but this was the first sign he had that Blair might swing that way – not that he thought all cross-dressers were gay, but he knew quite a percentage were at least bi.

Blair blushed. "I-I started doing it in college; I never seemed to fit in, and I was trying to find where I did, and I just sort of happened upon this."

"I see," Jim said softly, and he did. God knows he’d heard enough of the jerks down at the station say that Blair looked like a woman; Blair must have decided to be one to take control when other guys taunted him with it. "Do you have a different name when you’re…crossed?" he asked hesitantly, not sure exactly how this worked.

"Jasmine," Blair said softly. Jim seemed to be taking this well, but he wasn’t sure if the other man wasn’t just in shock.

"A beautiful name for a beautiful lady," Jim said, deciding to be bold. He walked around his Guide, looking at him from all angles; male or female, Blair was more erotic than anyone he’d ever seen. He inhaled deeply; and caught a whiff of exotic spices. Blair’s perfume was intoxicating.

"Jim?" Blair asked; it sounded like Jim was hitting on him, but that couldn’t be…could it? "Are you…okay with this?" he asked, deciding to get his immediate concern answered as soon as possible.

"I have no problem with you being a cross-dresser, Chief," Jim said seriously. "I just wish you felt you could’ve told me, instead of me having to find out like this," he finished quietly.

"I’ve never told anyone," Blair revealed. "And I wanted to tell you, I just wasn’t sure how you’d react. Why are you home now, anyway?" he asked, suddenly remembering Jim’s stakeout – which he was supposed to be on now.

"The guy confessed," Jim said bewilderedly. "We had nothing but hearsay on him, and he up and confessed. So the stakeout was called off."

"Oh," Blair said softly. He shifted nervously from foot to foot; he was wearing almost nothing, and what he was wearing was mostly see-through; he felt extremely exposed.

Jim took a deep breath and decided to go for it; he’d never get a better chance. He sighed and said, "This might come back to bite me on the ass, but…" He walked closer and sank his hands into Blair’s mahogany curls, brushing his thumbs down petal-soft cheeks. "I love you, Blair Sandburg," Jim said solemnly. "Male or female, cross-dresser or not, I love you…and I always will," he finished quietly.

Blair gasped in shock, wonder, and…happiness. He blinked tears from his eyes, glad he wasn’t wearing mascara, and smiled shyly. "I love you too, Big Guy," he said softy. "I have for a long time."

Jim let out the breath he’d been holding since he’d first said those three little words. "Would you come upstairs with me?" he asked shyly, knowing that if Blair would sleep in his arms tonight, and for the rest of his life, he would want for nothing else.

"Yes," Blair acquiesced softly.

Jim smiled and leaned in to kiss his mate, touching their lips together tentatively. Blair returned his advances hungrily, wrapping his arms around Jim’s neck and snaking his tongue out between his lips to play with Jim’s. They broke apart reluctantly, panting for breath.

"You wanna…maybe…do a little more than sleep when we get upstairs?" Jim asked hesitantly.

"O-Okay," Blair said, smiling uncertainly; he knew he wanted this, wanted Jim, but he was still a virgin, and he was nervous.

"We don’t have to do anything you don’t want, Sweet," Jim assured his soon-to-be lover.

"Oh, I want to," Blair said semi-boldly. "I just…I’ve never done this before," he mumbled.

"Been with a man?" Jim asked. "Neither have I, Baby."

"A man…or a woman," Blair said, heat staining his cheeks.

"You mean you’re a…virgin?" Jim asked unbelievingly.

"Yes," Blair said so softly, no one but Jim would have been able to hear him. "I never wanted to hide who I was while I was with someone, but I could never tell anyone that I crossed…until you."

Jim took a deep breath. "I hope I don’t disappoint you," he said quietly. "I want it to be good for you, but I’ve never been with a guy before, either."

"I’m sure anything we do together will be wonderful," Blair told his lover, confident that their love would see them through anything.

Jim smiled and guided his love up the stairs, only turning the dimmer switch on halfway so the light would not detract from Blair’s beauty.

"You’re so beautiful," Jim said in awe; he couldn’t believe that someone as wonderful as Blair wanted him, Jim Ellison, for his first lover.

Blair blushed. "I-I think you’re beautiful, too, Jim," he said lowly.

Jim slowly approached his lover, gathering him into his arms and just stood there, swaying for long moments.

"Mmmm, this is nice," Blair purred.

"Yes, it is," Jim returned softly, leaning down and brushing his lover’s lips with his own. They kissed for long moments, reveling in the connections of their mouths, finally as one, as their hearts had been for so long.

They broke apart slowly and stood swaying for a few minutes until Jim pulled away and guided Blair to the bed. "Are you sure, Chief?" he asked his lover.

"I’m sure, Jim. Make love to me," he beseeched.

"It might be easier if we took our clothes off," Jim said teasingly.

Blair’s face warmed. "It might," he agreed, starting to undo the buttons on Jim’s shirt. Jim shrugged the shirt off and undid his belt, while Blair unzipped his pants and peeled them down his legs. When Jim was in his boxers, Blair realized that it was his turn.

"You ready?" Jim asked, tracing the strap of his negligee between his fingers.

"Uh-huh," Blair said nervously, smoothing the other strap down his shoulder as Jim did the same, till they were both held up by his elbows. Jim reverently pushed the gown down his body, and laid it carefully on the bedside table; he wanted to see Blair in it again.

Jim’s breath caught as he saw what Blair was wearing – a white satin corset and light blue silk thong panties – with garters connected to his silver silk stockings. The underwear barely constrained Blair’s rampant erection, and the precum it was weeping had soaked through. Blair was the most ravishing sight he’d ever seen. His mouth watered when he saw that Blair had apparently shaved his whole body – his sex was as hairless as a baby’s.

He smoothed his hands down Blair’s thighs, running his thumbs over the patch of milky white skin bared between his panties and the tops of his stockings.

Blair moaned at the delicious feeling curling in his gut.

"Chief," Jim said softly. "I wanna taste you. Can I, Baby?" he asked.

"I wanna taste you too, Jim," Blair purred seductively. He shimmied out his panties, and tossed them on the floor. "Turn around."

Jim nodded and complied, lying on his side beside Blair’s body. He grinned and gave the head of Blair’s cock a tentative lick, savoring the taste.

Blair whimpered. "God, that’s good," he whispered.

"Why don’t you try it, Baby?" Jim suggested.

"Okay." Blair smiled and leaned in, slipping his tongue out for a hesitant taste. "Mmm… You taste good, Big Guy," Blair murmured. He sucked carefully on the cap of Jim’s penis, thrilling at the moans that issued forth from his lover.

Jim moaned and laved Blair’s cock, taking the first three inches into his mouth. He relaxed his throat and took him farther, but before he got past the fifth inch, he had to back off or choke. I guess that’ll take some practice, he thought ruefully.

Meanwhile, Blair was using his hand to pump Jim’s dick, using his mouth on the top few inches. Jim tasted better than almost anything he’d ever eaten, and he wanted more.

They caressed each other with their mouths for long minutes, pleasuring each other with teeth and tongue. They couldn’t last long – this was their first loving, and they didn’t have the means or inclination to keep themselves from cumming too fast. Blair came first, moaning around Jim’s cock and cumming down his lover’s throat. Jim milked Blair shaft with his throat as he came inside Blair’s mouth.

They lay there panting for long moments, reveling in the afterglow.

"That was…amazing," Blair gasped, sitting up and removing his corset – it might look sexy, but it wasn’t comfortable to sleep in.

"Yeah…it was," Jim agreed, sitting up himself and helping Blair remove the restraining silk. He gathered Blair into his arms and kissed his curl-covered head. "And it will get even better," he promised.

"Mmmm…it’ll never get better than this," Blair stated emphatically. He yawned. "Never better than with you," he mumbled as he drifted off to sleep.

END