The Hotel 02: Room 271

This is the second of the hotel series. Due to a request for male focus content, this is very different to my usual writing. If you're not into gay content, skip this one!

Jake closed the door as he returned to his room. He was pleasantly surprised by how good the hotel's gym was. It was as well equipped as the gym he used back home. He stripped off his clothes in preparation for his shower, looking at himself in the mirror. He flexed his muscles, proud of the progress he was making. He was tall and muscular, a typical looking gym bro. Turning away from the mirror, he made his way into the bathroom and showered.

Once finished, he returned to his room and paused in surprise. Sat on his bed were two items, a dildo and a chastity cage. He looked around the room confused and concerned, had someone been in while he was showering and left these for him? He checked the door, it was still bolted from the inside, so no-one had been in. How had these items been left here?

A second thought hit him, did someone know about his secret? Jake had never admitted it to anyone before, but he loved watching porn involving femboys. It wasn't that he wanted to fuck them, it was actually the opposite, he was intensely jealous of them. He got so turned on imagining how they felt, their smooth soft bodies, the sexy girly clothing and the intense pleasure they must be feeling as their tiny cocks sprayed through their chastity cages as they massaged their prostates with dildos and other toys.

Is that why someone had left these items here? Did they know about that? Jake looked at the chastity cage and felt a strong desire to put it on. It was small, far too small for his cock. He walked over and picked it up, bringing it down to his crotch to compare. Looking down, Jake realised his cock had shrunk by a lot. It was far smaller than it had been when he entered the shower. Now it was tiny, much like the little clitties of the femboys he watched.

Rather than being shocked or upset by the change, Jake felt glad it had shrunk, now it would fit inside the cage he was holding! He'd never put one on before, but knew straight away what to do as he snapped it closed over his cock. He turned to look at it in the mirror and this time he was shocked, but not unhappy, as he saw his appearance. He was shorter now, slimmer too, his muscles were gone and his arms and torso with thin and skinny. His hair had grown, it was now a cute pixie cut while the hair on his body had completely vanished.

There was no denying it, he was now a femboy.

Jake felt a rush of excitement, too caught up in what was happening to question any of it. Since he'd accidentally stumbled across the first video of a femboy having a prostate orgasm, he'd secretly wished he could try it. Part of his motivation of going to the gym was to try and get rid of those desires, to make himself look at manly as possible. Thinking about it now, Jake didn't know why he had fought his urges so much. He'd been ashamed, he could remember that, but right now he couldn't figure out why.

He pulled open a drawer on the dresser, finding an array of women's lingerie inside. His little clitty tingled in excitement as he selected a few items. First was a pair of fishnet stockings which he pulled up over his smooth legs. Next, he clipped a garter belt to the stockings and settled it on his hips. He then pulled on the panties he'd found. They were extra sexy, with two gaps in the material around his crotch and ass, meaning his little clitty was exposed, along with his tight pink asshole.

Finally, he pulled on a cute little crop top that only covered a small portion of his chest and barely reached down far enough to cover his nipples. Jake looked at himself in the mirror and felt a wave of emotion. He was so happy to see his reflection being that of a cute femboy. He turned around and turned his attention to the dildo on the bed. He picked it up and looked at it, it had a suction cup on the base.

Crouching down, Jake stuck it onto the tile floor. He felt his clitty pulse inside its cage as he crouched down. Leaning back on his hands, Jack lowered his hips until he felt the tip of the dildo press against his virgin asshole. It felt huge as he began to lower himself onto it. The slick head began to stretch his ass open and he groaned at the sensation. It felt incredible already and it hadn't even penetrated him yet.

He felt the thickest part of the tip stretching him open before it suddenly slipped inside. Jake let out a girlish moan as the toy slipped into him. He couldn't believe it was finally happening, it felt just as amazing as he thought it would and he wanted more. Growing more confident, he lowered himself faster, sinking deeper onto the dildo until its entire length was inside him.

"Oh shit," he moaned, pleasure flowing from his insides.

He picked himself up before lowering himself back down again, repeatedly impaling himself on the fake cock until he settled into a good rhythm. It was unlike anything he had ever felt, the sensation of it stretching his insides over and over, grinding along his prostate, Jake felt like he was going to cum any second.

He bounced up and down on the dildo, his clitty tingling inside its cage as Jake felt himself on the edge of cumming without even touching it. He was so close, but it wasn't enough, he needed something more. He didn't know what he needed until he heard the door close. He froze, the dildo buried deep inside him as he heard footsteps approach.

A man stepped around the corner, completely naked. He was tall and strong, not as muscular as Jake used to be, but definitely stronger than average. He was good looking, but what really caught Jake's attention was the long thick erection protruding from the man's crotch.

"So pretty," the man said, looking down at Jake. Jake couldn't take his eyes off the man's cock. He didn't resist as the man picked him up, the dildo sliding from his ass as the man placed Jake on the bed. Jake felt the man grab his hips, turning him over. He again didn't resist as he was manhandled onto his hands and knees. Something about the sensation of a stronger, bigger man handling him like that excited Jake.

Jake was on his hands and knees with the man behind him. He felt the man's hand running over his ass cheeks, gripping them and spreading them apart. Jake moaned as he suddenly felt the man's cock pressing against his ass. He pushed back gently as the man's cock slid into him. Pleasure flowed through Jake's insides as the man's cock slid into him.

The man began to fuck him firmly, not being rough, but using long, solid strokes. Jake moaned constantly, his cock rocking below him inside its cage. Precum dripped from the tip as Jake gripped the bedsheets. From the noises he was making, if someone had overheard their fucking, they'd definitely have assumed a woman was being fucked inside the room.

"Oh god, I'm gonna cum!" Jake moaned.

"Yes, cum for me! Cum like a good girl," the man urged. As the words left his mouth, Jake's clitty exploded. Pleasure flooded Jake's body and shot down his tiny clit. His whole body trembled and his legs shook as a river of cum flowed onto the bedsheets below. Jake was in heaven, he couldn't believe how good it felt to finally cum without having to touch his cock at all. He wanted to always cum this way, he never needed to touch his little clitty ever again.

The man continued to fuck him and Jake was happy for it. Unlike when he normally came from stimulating his cock, he still felt horny and ready to go again. He bucked back against the man, trying to do his share of the work which had the desire effect. The man groaned and picked up his pace as his orgasm approached.

Jake moaned loudly, the sudden extra stimulation pushing him over the edge again as another river of cum flowed from his cage. He couldn't believe he was cumming again already. It felt just as good as the first time. The man grunted and Jake felt his cock thrust deep into his ass before it twitched and began filling Jake with the man's own sticky fluids. Jake moaned at the sensation, he felt like a real femboy now and never wanted to go back.

As their orgasms faded, the man didn't say a word as he slid his cock out of Jake and got off the bed. He walked out of the room and left Jake on the bed, his ass still in the air. Jake rolled over, throwing the soiled sheets to one side. He felt asleep quickly, suddenly drained by what had just happened. He had strange dreams, but couldn't remember them in the morning. He looked in the mirror, fixing his hair and making sure his chastity cage was firmly in place before he got dressed into his favourite skirt and t-shirt. He packed his suitcase and checked out of the hotel. They returned his ID and he smiled as he saw his picture, he really was pretty.