Pleased To Meet Ya

[TransBear-]

*This is a work of fiction.*

I arrived at the hotel at around 6pm. It was already growing dark, and my stomach was full of butterflies. I'd been quiet the whole ride over, other than the faint wet sounds between my legs whenever I'd shifted position. He'd told me to be ready when I arrived, and I sure as hell made sure that I was.

I'd met him, Daniel, online. We'd connected instantly, bouncing off of one another with ease. We felt good talking to each other, so when we agreed to meet up for coffee we were both excited. Thankfully, our chemistry was just as good in real life as it was online, and we had a blast with every meet up since then. And then we'd broached the real reason why we'd started talking in the first place; sex. Kink. Our limits aligned, as did our likes and dislikes. He was the dominant type. He liked his partners chunky, fat, fluffy, however you wanted to put it. He wasn't straight. He was into body hair. Absolutely perfect. We'd chatted about everything at length and finally decided to go for it. We set up a date, gave each other plenty of opportunities to back out if we wanted.

I looked up at the building as I slid out of the car, feeling my stomach somersaulting more. I was very excited, and, as promised, extremely aroused. I had to wear a heavy overcoat to make sure I was fully covered, as I was wearing very little underneath. Daniel had taken an overnight bag for us both which would have everything I would need to be comfortable afterwards. It was quite a swanky looking hotel, with balconies and high ceilings. Much more than I used to. I thanked the taxi driver, then walked into the building, spoke to the receptionist, and was on my way to the 17th floor. I took off my shoes at the door and left them outside, then let myself into the room.

It wasn't dark inside, but the main lights weren't on. Candles, mood lighting, rose petals; the works. A bottle of champagne was chilling on ice in a bucket. Daniel was waiting over by the window. I could see across the city even from where I was standing by the door. He turned when he heard the door close, and he smiled at me.
"Good evening. Glad to see you arrived okay."
"I left with plenty of time."
He continued to smile at me as he crossed the room. "You did. I'm pleased."
His hands came up to the buttons of my overcoat and I breathed in deeply as he kissed me tenderly. He started slowly unfastening the buttons until they were all undone, then pushed the overcoat off of my shoulders. It fell around my feet, leaving me exposed.
"Mmm, perfect."
He took my hand and lead me across the room, then stood me by the window.
Goosebumps rose up on my skin, partially due to the sudden change in temperature, partially due to being this naked so close to a huge window. My nipples were erect, as they had been the whole ride over, clamped. All I had been wearing was a black lace thong, my largest butt plug already inserted.
"You follow instructions well. All prepped?" He asked, giving me the once over.
"Yes, sir."
I'd showered, groomed myself, obviously. Then I'd worked my holes. I'd stretched my asshole just enough to accommodate his cock, being sure to use a generous amount of lube before plugging myself. I'd edged myself for hours to make sure I was good and wet. Soaked, actually. I was surprised I hadn't left an obvious wet patch in the backseat of the taxi.
"Good boy."
He backed me up against the window, pressing me against it, then raised his hand to lightly grip my neck. "Good boys get rewarded, don't they?"
"Yes, sir."
He kissed me again, deeply, holding my throat with one hand, snaking the other around my waist to pull me close to him. I moaned into the kiss, amazed by him already. When we broke apart another small moan escaped my lips. I gazed up at him even as he gently pushed me down to my knees.
"Open your mouth."
I did so, licking my lips before opening them, still keeping my eyes up on his. He unzipped his trousers, releasing his cock, then offered the tip between my lips. I took it hungrily, sucking on it, swirling my tongue around it. He let out a low rumble of pleasure and I kept working the tip of his cock before slowly letting more and more of his length glide into my mouth. I sucked more the harder he got, working up a good pace and rhythm. He pressed a hand against the window as he gripped his cock, pushing it into my mouth, then pulling back. I looked up at him every time I could, even when his cock brushed the back of my throat and made my eyes water. Even when he thrusted into my mouth all the way, holding it there for a few moments, then pulled back. I gasped and caught my breath but still, eagerly, took his cock back into my mouth and kept sucking. He pressed both his hands onto the window as he pushed his cock deep into my throat, working his hips. His length was soon dripping with my drool as he fucked my throat. When I raised a hand to tap his thigh he pulled back, letting me cough and breathe.
"Such a good boy. Very good." He stroked my hair, then helped me to my feet. He gathered some of the drool that had fallen across my chest on his fingers, then pushed them into my mouth. I sucked on his fingers, moaning. "Good..." When his fingers inched back in my throat I looked up at him again, and before too long he was finger fucking my throat, working up a good load of drool that went dripping down my chest, running off my nipples. When I coughed, he stopped, taking a step back to slap my chest. I jumped and moaned, staying stood against the window. He slapped again, ensuring he hit my nipples in their clamps. It felt amazing, sending waves of pleasure through my body.
"Well behaved boys get slaps, don't they?"
"Yes, sir."
"Louder."
"Yes! Yes, sir! Thank you!"
"Good boy."
He pulled me into a very wet kiss again, our tongues rubbing together. I felt his cock twitch against my stomach. I broke the kiss.
"Please, sir. I need your cock."
"Oh, do you?"
"Yes, sir. Please."
"Turn around."
I did so, pressing my wet and sensitive nipples against the window. I kept my back arched, pushing my ass towards him.
"You have such a fantastic ass, little boy."
"Mm, yes sir."
"Let's see how good a job you did, shall we?"
He snatched my thong down my hips, letting it drop to the floor. He then spread my cheeks.
"Oh, wow. You're sopping wet."
"Just like you asked, sir."
"Mm, good..."
He buried his face between my legs, slurping up my juices, burying his tongue into my aching, wet hole. I cried out, arching my back more. His tongue flicked over my tdick before he started sucking on it, making my hips buck. I hadn't realised how close I was until that moment, and my legs started shaking.
"P-please, sir! I'm gonna c-cum!"
He stopped. I panted, relaxing slightly. He straightened up and gave me a firm slap on my ass.
"Do you want to cum? Hm?"
"Only around your cock, sir."
"Good answer."
He slapped my ass again, then held his hand against my skin before raising it to slap again. Each firm stroke made me whimper and writhe. Drips from my cunt rolled down my thighs.
"What hungry little holes you have. It would be cruel to deprive you any more, hm?"
"Yes, sir." I panted, looking over my shoulder. He smiled at me, planting a tender kiss between my shoulder blades before he positioned himself behind me and finally, slowly, deliciously, slid his cock inside me.
He started with the tip, pushing just enough inside me to make me moan before he pulled back. Toying with me, teasing my throbbing hole. He slowly added more, and more, until he came to rest fully inside me. He rolled his hips, grinding inside me, before he started fucking me properly. It was easy for him to fuck me, giving how wet I was. It felt amazing, his cock filling me entirely with every thrust.
"Oh, fuck! Yes! Yes!" My hands slid down the window, struggling to find purchase, as he fucked into me as hard as he could. "Unf, yes, daddy, yes!"
"Fuck...call me that again."
"Mm, daddy! Fuck me!"
He slapped my ass again, then gripped my hips. "Whose cunt is this?"
"Yours, daddy!"
"Whose fucking cunt is this?!"
"Yours, daddy! Yes!"
He kept fucking me, my moans and his grunts probably heard several rooms away. I held on as long as I could, but it was inevitable.
"Daddy! Please let me cum!"
"Mm, cum on this cock. Good boy."
Believe me, I did. I cried out loudly as I came, pushing back against him hard. My cunt gripped his cock tightly, pulsating around it, desperately trying to milk his load from him. He kept thrusting throughout my orgasm, making it nearly impossible for me to fully recover before I felt another wave.
"Daddy! I'm gonna cum ag-again!"
"Oh shit."
My hips bucked wildly as I came again, only this time it wasn't just me. I felt him tremble as he came, shooting his load deep inside me. He kept fucking, filling me entirely.
When I was sure he was finished, I pushed him back, then stepped forwards. His cock was still semi erect, soaking wet with our combined cum. I sank to the floor and took it back in my mouth, moaning at the taste of us both.
"Fu-fuck...you're...amazing..."
I giggled, flicking my tongue over the tip of his cock before sucking it down again, slurping it clean. I teased my tdick as I sucked, using his cum to keep things slick down there. Then I looked up at him, stroking his cock.
"Wanna fuck my asshole, daddy? It's all ready for you."
"Oh, definitely."
I got to my feet and lead him this time, taking him over to the bed. I pushed him down on it, then climbed onto it with him. I straddled him, being sure to give him another deep kiss as I got myself into position.
As I pulled back, I reached a hand between my legs, pulling out my plug. It made a wet sucking noise, and I made sure to position his cock against my hole before too much lube could dribble out.
"Ready, daddy?"
"Yes, baby."
I started guiding his cock into me, letting my ass adjust to the feeling of his tip stretching me open again before sinking further back, taking more and more of his cock. He felt amazing, sliding in to fill the space the plug had been taking up. Once he was fully inside me, I started working my hips, gliding up and down. He pulled me into a kiss, thrusting up to meet my movements. My tdick rubbed against him effortlessly with wetness from my cunt. He fucked into me deep, holding me close against him as we continuously kissed. I worked my hips hard, bouncing my ass on his cock. When I came again I broke the kiss, pushing myself up. I stayed in that position, my tits in his face. If his cock came out of me I quickly pushed it back inside, moaning loudly every time.
I pushed up fully, sitting on him, letting his cock bottom out against me with every sit. I worked my tdick, my fingers teasing my hungry hole.
"Mmm, I love your cock, daddy. You fill me up so good."
Soon enough, I felt the familiar pressure of an orgasm between my legs, and I worked my fingers into my cunt properly.
"Mmm, mmm, daddy! I'm gonna cum again! Your cock feels so good!"
"Mm, yes, good boy."
In a short series of very quick movements, Daniel had gripped me tightly and rolled us over so that I was lying against the bed, him above me. He fucked deep into my asshole as he came again, just as I did. The feeling of his cock pulsing inside me, filling my ass with his cum, was enough to make me cum a lot quicker than I'd expected.
As our orgasms passed, he all but collapsed against me, burying his head in my shoulder as he caught his breath. I closed my eyes, wrapping my arms (and legs) around him. He pulled out of me and I felt his thick load escaping shortly after. I let out a giggle.

Edited September 20 by TransBear-
spelling errors