tagTranssexuals & CrossdressersHotel Room Cocksucker

Hotel Room Cocksucker


Larry leans back in his chair by the desk with his legs spread and his stiff cock pointing at the ceiling. I'm stripped down to my black bra, matching panties, thigh-high stockings and stiletto heels. My cock presses hard against the silky panties as I fall to my knees. Larry glares down at me. I wrap my lips around his throbbing dickhead.

My head starts to bob. At first, I take half of his meat pole into my mouth. But I swallow more each time I go down. Our eyes are locked together in an intense lust stare. I'm careful to keep my teeth off his sensitive skin so that all he will feel is my warm wetness. His prick hits the back of my throat. I don't think I can take anymore. But then he puts hand on the back of my head and pushes hard, burying my nose in his curly hairs.

I gag. He lets me up for air. I take a breath, and we begin to develop a rhythm. Larry is making me take all 10 inches of his cock into my gullet. He still has the hungry-lion glare fixed on me as he begins to tremble. I can tell he is trying to hold back, but it's no use.

Larry grunts as he shoots his wad. I can't believe how much cum he blasts. It fills my mouth, spilling out the corners. His jizz drips down my chin as he pushes me away. I tilt back my head and show Larry the salty mess he has deposited in my mouth. He smirks. I close and swallow.

I'm not Larry's first hook-up. He knows the deal. He doesn't have to make conversation while he puts on his khaki pants and blue button-down shirt. Larry dresses in silence while I savor the aftertaste of his cum. He says "thanks" and walks out of the hotel room without another word.

I'm a secret cross-dresser. Something about putting on slutty lingerie makes me want to suck dick and get fucked up the ass. But I'm too embarrassed to be "out" about my sexual preferences. I live as a straight guy with a girlfriend and a job selling office furniture to corporate clients. But whenever I get the chance, I dress like a porn star and post a personal ad on craigslist seeking playmates.

I've been cross-dressing for years. But Larry was my first hook-up in what was probably the greatest sexual adventure of my life. I had arrived in Chicago a day early for a meeting. I checked into my hotel and drove the rental car to a mall about a mile away. I set myself up with a complete outfit, starting with the bra, panties and stockings at Victoria's Secret. Then I swung through Fredrick's of Hollywood for a tight, black club dress and then on to Payless for the high heels. On my way out of the mall, I hit Claire's for a fake pearl necklace, matching clip-on earrings and cat-eye sunglasses. I picked up make-up and cheap perfume from a Walgreen's before heading back to the hotel.

When I opened up the laptop on my bed, I already had several responses to my personal ad in my email inbox. Larry went first because he was looking for a quickie and was available immediately. He made it clear that he he wanted a blow-and-go. He wasn't interested in reciprocating. That was fine with me. I normally would have jacked myself off while sucking his cock, but I decided to save my spunk and channel my sexual energy into another hook-up.

It didn't take long to find one. His name was Josh.

Josh is behind me. He wraps his arms around me and cups his hands over my tits. His stiff cock presses into my ass. He plants his lips on my neck. Goosebumps pop on my arms. I know I'm not supposed to be gay, but his touch is too gentle to resist..

"I want you, baby," he whispers into my ear.

"I want you, too," I say.

He turns me around, pulling my hips into his. I drape my arms around his neck. We gaze longingly into each other's eyes. Up this close, I can see how much younger he is. I'm 35. He's not even 20. But age doesn't matter in this moment.

"You're the sexiest woman I've ever seen," he says.

I press my lips against his. Our mouths open. Our tongues play. He squeezes me tighter. Our stiff cocks rub together. Josh suddenly pulls his head back.

"I won't hurt you," he says.

"You can if you want," I say with a smirk.

Josh pushes me. I fall back on the bed. He's smiling as he drops to his knees between my spread legs. He starts kissing my thigh, making his way from my knee to my pulsating cock. He puts his mouth on the head and blows his warm breath through the silk panties. Then he pulls back and starts working on the other leg in the same pattern. When he gets to my crotch, he licks the crease between my leg and my ball sack. It's unexpected. I almost cum but manage to hold back. He starts to peel back my panties. I stop him. He looks up, surprised.

"No," I say. "Tonight is all about you-- your pleasure."

"You're so sweet," he says.

"Just get me ready for your cock," I say.

"Take off your panties," he says.

After I slip them off, Josh has me get in the doggy-style position on the bed. He spreads my ass cheeks and dives in head first, slipping his tongue directly onto my bung hole. He licks hard and fast. The passion he puts into it lets me know how badly he wants me. I'm beginning to think about what it will feel like to have him inside me. Josh reaches up and gently strokes my ball sack. The teasing becomes unbearable. I try to scream, but all that comes out is a hoarse whisper.

"Do me, Josh," I say. "Do me now."

He grabs the lube off the nightstand and squirts some onto his fingers. I reach back and spread open my cheeks so that he can grease me up. He starts by smearing the gel on the outside of my asshole. It's cool. The goosebumps return to my arms. He massages the outside of the hole, making tiny circles with the tips of his fingers. Then he slips one finger inside me, not far, probably up to the first knuckle. My ass hungrily accepts. He begins pumping his finger, slowly going deeper. I don't know if Josh has done this before, but he is good. Very good.

My hole is completely relaxed, totally prepared for him. Josh can feel it. He pulls out his finger and takes off his pants, flinging them into the corner. Josh kneels behind me. I'm still holding open my cheeks for him. He puts the head of his cock against my lubed hole without pushing it in. He starts rocking back and forth, tapping the hole. Teasing me. Just when I don't think I can take it anymore, he shoves the head inside me. A sudden mix of pain and pleasure shoots through my body. "Uh!" I say. His cock is much thicker than it looked through his pants. He begins fucking me the same way he warmed me up-- slowly and progressively deeper. His hands are squeezing my hips. My hands have instinctively balled up into fists. I suddenly realize I'm moaning. Josh picks up the pace. His balls are slapping against my ass. He is penetrating at the perfect depth. Any more would be too painful. Any less wouldn't be intense enough. He starts to grunt. I can tell he is losing control. He is about to cum. "Pump it inside me," I say. I've sent him over the edge. He takes one last stroke, and he cums with a shudder, collapsing on my back.

Josh pulls out. I start to turn over. He holds me in place.

"Not yet," he said.

Josh spreads open my ass cheeks and starts licking up his own jizz as it drips out of my asshole. I wand so badly to reach down and jack myself off, but I know. There is more fun coming later d later. When Josh finishes cleaning my butthole, he turns me over and gives me a long, deep kiss. I taste his salty spunk on his tongue.

He gets up and starts putting on his jeans.

"Baby," I say. "You can do me like that anytime you want."

"When can I see you again?" he asks.

"I'll be back in town next month."

"So it's a date?"

"It's a date."

He walks out of the hotel room with a smile on his face.

After Josh left, I went back to my computer to look for another hook-up. My hard-on was raging. I needed a grand finale. Boy, did I ever find one. The email came from a man named Don.

I'm laying on the bed with my legs in the air. Don thrusts his cock into my lubed asshole. He looks angry, but I know he's not. He's just far gone in a lust haze.

Don's pumps start slow and shallow, but he doesn't need much time to warm up. He is soon burying his whole cock inside me on each stroke. His thrusts become fast and hard, but he never loses control. Every push forward is done deliberately. I can tell he is an experienced butt-fucker. He knows exactly how to deliver the right mix of pleasure and pain. He grunts. I moan. We're staring hard into each others' eyes.

"Fuck me," I say.

He wraps his hand around my throat and squeezes just hard enough to cut off the air. I tray to gasp. Nothing comes. I feel my self start to fade. I'm blacking out. I don't struggle because I know I am totally in Don's control. But just before I go under, he releases my throat. Air fills my lungs. Adrenaline surges through my body. My heart is pumping. Goosebumps pop on my arms. It is the most amazing sexual thrill I've ever felt. Don chokes me again, this time taking me even closer to passing out. When he lets go, I almost cum, even though he hasn't touched my dick. But I manage to hold back. I want to keep the experience going.

Don suddenly pulls out of me and leaps across the bed to his wife, who has been naked and dildoing herself next to me. He aims his prick at her face and starts to shoot. She is dripping with jizz from her hair to her chin by the time Don shakes the last drop and backs away.

"You wanna fuck her?" he asks.

I look her over. She has long, blond hair, big, natural tits and a hairy, early-1980s-style bush. Her pussy lips are glistening. I nod my head.

"Then eat my cum," he says.

I'm still wearing my bra as I slide my hips between her thighs and look down at her messy face. She moans as I pumped my cock inside her. Don's wife feels up my titties over the bra as I begin slowly licking the cum off her face. I swallow every salty bit of it.

I'm trying hard not to cum, but it's no use. I blasted hard into her pussy and rolled off of her.

"You're not done yet," Don says. "If you're going to use my wife's twat, you're going to have clean it up when you're finished."

My jizz is already beginning to ooze out of her labia. I lay on my stomach between her legs and get to work, starting with the streams of cum on her thighs. Then I work my way to the pussy lips and finally thrust my tongue inside her. She grabs the back of my head and won't let go. Her pelvis bucks against my face.

"Oh, oh, OH!" she says. She cums hard. Her juices run down my chin.

Don and his wife dress quickly and head toward the door.

"Call us next time you're in Chicago," he says.

"I will," I say.

They leave and door slams shut, leaving me with the taste of cum in my mouth and a bra on my chest. I feel like a piece of shit. I've spent $192 on women's clothing I will throw in the trash. I promise myself I will never fuck another guy in my life, but I know it's a promise I'll never keep.

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by Anonymous

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by cdCindy101/15/18

I love hotels too

I too become a sissy slutty CD when I go out of town on business. I love meeting new anonymous men, sucking their cocks and getting fucked. I love your stories and I can't wait to read more of them.

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