When Jon awoke, the sun was shining brightly through the picture window in his new bedroom. The accommodations that Girl World had provided were spectacular; a king sized bed, walk-in closet, and a view of the beach that he could die for.
He stood up, ignoring that he was still only in his bra and panties, and walked over to the window to stretch. The next building over Jon could see a young man on his balcony staring at him, his hand down his pants. Jon smiled and waved. It was so nice to have good neighbours, even if the man seemed to have some sort of medical condition causing him to itch. Briefly Jon wondered if the man had a rash, as he watched him rub his hand up and down in the front of his pants. Maybe Jon should stop by later with a cream or ointment to help the man out...
Not wanting to waste the morning, Jon turned around, leaving his back to the window and bent straight down, touching his toes. Jon had never been the athletic type, but beginning his day with a good stretch just seemed like such a good idea. He didn't know yoga, but he could improvise. He held the pose, he rear end in the air, feeling the sun on his panty-clad behind, and let his mind wander back to the night before.
He had sure gotten carried away the night before! Not that Jon minded the hundreds of dollars in tips he'd collected, but he'd been so engrossed in his job, it was almost as if he had taken on a new personality, one that was made to wait tables! It had all been too easy, as if the men, and crossdressers, Jon had served had been eager to tip him. Well, the crossdressers hadn't been big spenders, but the other men, the one in men's clothes, they pracically threw money at him. And all it had taken was a little bit of friendly hospitality.
Jon stood up slowly from his bent pose, then slid his feet to each side, slowly lowering himself to the ground doing the splits. He'd never done the splits before, Jon didn't know he could be so flexible, but as he sat on floor spread out before the window, he felt great. No wonder so many people were taking this up as a hobby!
Even after Kelli and he had finished up, after last call, Jon had had a difficult time turning off his new attitude. Maybe it was the buzz of the evening, maybe it was all the success that he'd had, but he was positively giddy. He'd even taken to performing a European cheek kiss to the bartender to say goodbye, a courtesy that he'd also extended to his cross-dressing roommate, Kelli, before he'd gone to bed.
Maybe the kiss had been the reason he'd had the dreams...
They had mostly featured himself and Kelli, only they weren't exactly Jon and Kelli. Jon was himself, mostly, but when the dream allowed it, and he could examine himself, his body had changed, adjusted. His chest, Jon had discovered, was much more masculine, so much so that it had ballooned outward, filling up his bra, bikini top, blouse, whatever each dream had dressed him in. His face, a rugged, tough looking face, with big puffy red lips, smokey eyes, long blonde hair. His stomach was thin, finally loosing those extra pounds he'd wanted to drop, but his rear end meant business. It was a macho looking bubble, always clad in something skin tight, except for the couple occasions where he had been completely naked.
Those naked dreams had given him the revelation of how far his transformation had gone. His penis was huge. Twice the size it was normally, hanging low between his legs.
It was like he'd been given his dream body. A true vision of beefcake, something that belonged on a poster.
Kelli, too, had undergone a transformation. Much of Kelli's body matched Jon's (maybe they'd been going to the same dream gym, Jon thought), but never did Kelli's penis become evident. Probably tucked behind his legs, the young man thought, which was good. The last thing Jon wanted to see was another man's penis.
The dreams took place in a variety of locations, always with Jon and Kelli as best friends, but they always ended the same way. The pair began, as if each had something to prove, to wrestle. Jon always got the upper hand, but in the process both men, now visions of masculinity, found themselves ripping the clothes from each other's bodies, dresses, skirts, lingerie, all discarded, revealing their hardy physiques beneath. Once naked, the dream would end, and another would begin.
Jon leaned forward until his bra-clad chest was on the ground, then slid his legs behind him until they were shoulder width apart. Then, pushing himself backward while keeping his chest on the ground, he bent at the knees and pushed his behind in the air, once again enjoying the warmth of the sun on his ass.
While Jon didn't relish the idea of spending time with a cross-dresser in Girl World (he was afraid that it would cramp his style), Kelli seemed to be a genuinely nice person. Maybe Jon would give him a day, allow his roommate the chance to become friends. Who knows, if Jon spent enough time with him, maybe Kelli would pick up a thing or two, maybe he'd stop being so girlie, and pick up on Jon's more masculine fashion habits.
Satisfied that his workout was enough, Jon stood to his feet. He turned toward the window again, adjusting his bra straps that had slid down his shoulders, and looked across to his friendly neighbour. The man's face was bright red, as if he'd just had a workout himself. He'd taken his hand from his pants, which Jon assessed as a good sign, but now he had a large wet stain on the front of his pants! Oh no! He must have spilled a drink on himself while he was scratching, a purely miserable experience, Jon was sure.
Giving one more wiggle of his fingers, followed by a friendly wink and a blown kiss (Jon was turning more European all the time!), Jon turned away from the window and walked out of the room, excited for another day of island living.
