[M]y First Time with a [M]an Turned Into a Threeso[M]e | 2016

As a teenager on into my young adulthood, I had always considered myself sexually submissive to women, and loved the idea of a strong woman being my Domme, tying me up and fucking me with a strap-on. I still do, and had a great Domme for a year in my late 20s who did just that, but by the time I reached the age of 24, I couldn't deny it any longer - I also wanted some dick. I had fantasized about it a lot, usually passable trans girls or just a woman with a dick - sucking, getting fucked, always bottoming, always submissive. Sadly, passable trans women are rare in the real world (and, it turns out, usually want you to ignore their dicks), and women with actual, large, working dicks even rarer, and I slowly realized that the best way to satisfy my need for a cock in my mouth would be to find a man who wanted to fuck me.

Luckily, I live in a fairly large city (don't laugh, Kansas City is big), and I knew where the gay bars were (gee, I wonder why?). Once I'd made up my mind finally, I was eager to get started, so I put on my tight jeans and my snap-up shirt and headed out. It was a Friday, luckily, so around 7 pm I went to the first gay bar I thought of - Buddies. I stepped in the door, looked around, and meandered over to the bar, where I ordered a gin and tonic. There was an older gentleman to my right, in his mid-40s, who looked me up and down appreciatively, and I smiled at him. As I turned around on the stool to survey the floor, his hand brushed my thigh. I looked over to him again, smiled again, and thought, Well, what the hell. I turned back, brushed his knee with my knee.

He told me his name (can't remember, so I'll call him Richard... wait, I think it was Richard. Naaahhh, that's too pat), I told him mine. We talked a little bit about this and that, and then a short Hispanic guy walked up and put his hand on Richard's shoulder. "This is my partner, Esteban. He doesn't speak very much English."

Damn, I thought. Oh, well, night's still young, I can be polite and then see about hitting on someone else. They leaned close together and whispered a little. I sipped my gin and tonic.

Richard leaned close to me and said, "What are you looking for?" He raised an eyebrow.

I played it coy. I didn't know how gay bar etiquette worked, but I assumed it was like straight bar etiquette and you didn't just tell someone you were looking to get fucked. "Just, y'know... a fun night out."

I was wrong about gay bar etiquette, apparently. "Do you want to come back to our place?" Esteban smiled at me.

I gaped for a second, but feeling the courage of the gin and the horniness of young age, I nodded. Richard settled his tab, then we left and drove up to the Northland, suburban KC, me following his car.

We got to his house and without preamble he turned on the TV and put on some gay porn. They must have been cruising for someone exactly like me, because the VCR was cued up to a scene where a young man was on his knees in front of two older guys, blowing them alternately, looking up at them for their approval. I moaned a little bit. Richard smiled. "Is that what you want?" I nodded. He unbuckled his belt, then said, "Well, go ahead." They stood in front of me in their living room, Richard 6-foot-tall or so, lanky, with salt-and-pepper hair and a thin mustache. Esteban must have been 5'8" or 5'9", because although he looked short next to Richard, he still stood taller than my 5-foot-7 frame. I sank to my knees and unbuttoned and unzipped his pants. I pulled his hardening cock from his jeans, stared at it eagerly for a second, and then turned to Esteban and did the same. They stood proudly side-by-side, and I stared at their cocks, reached my hands up and grasped them. Richard's was about 7 inches long, not very thick. His pubes were trimmed short, salt-and-peppery like his hair and mustache. Esteban's cock was shorter, at about 6 inches, but it was thicker and felt heavier in my hand.

Richard put his hand at the back of my head, getting impatient. He pulled me gently towards him. I opened my mouth and placed it around the warm, spongy head. He moaned. I sucked gently, remember from my dildo practice to watch my teeth, and slowly sucked his whole cock into my mouth, down into my throat. I gagged as the head of his dick hit my throat, backed off, and began to rhythmically bob up and down, doing my best to suck as I did it. At the same time, my right hand stroked Esteban's cock, and he and Richard were caressing each other and kissing.

I switched off, now focusing on Esteban's smaller member and stroking Richard's. Esteban's cock fit easily into my mouth, and the joy I got from being able to have a mouth FULL of cock solidified my feelings that this was the right thing to do.

As I sucked them, I slipped my jeans off and pulled off my shirt. I did it slowly, concentrating more on the cocks in my mouth than getting naked, so this took about ten minutes. As soon as I was naked, Richard pulled me up and grabbed my dick, rock hard and straining. He whistled a little at my own 7-inch cock. "You've got a big dick for a little guy." I smiled, blushing at the compliment. Esteban nodded. "Do you want to take this to the bedroom?" I bit my lip, then nodded.

We walked to the bedroom, where I immediately climbed on the bed. Esteban directed me to lie on my back with my legs up, holding my knees. Then he placed his cock in my mouth and gently fucked my face. Richard, meanwhile, had pulled on a glove and was lubing and fingering my asshole. It hurt a little bit, but even that hurt felt great, and he stroked my cock while he upped the number of fingers and twirled and spun them around inside me more. Even though I was really nervous about having something larger than a butt plug up there, I also couldn't wait, and wasn't about to tell him to be gentler or slow down. I needed this.

Finally, he stopped, threw away the glove, and slipped on a condom. He pressed the tip of his cock to my opening, pressed. I moaned or groaned, even I couldn't tell, and Esteban's cock in my mouth stifled the noise anyway. Richard pushed harder, and pop! He was inside me. The rest of his dick slid effortlessly into my ass, and by the time he was all the way in me, I felt full and a peculiar stretching pain. I also felt like I had to go poo, which I've learned is normal, but it freaked me out a lot. Luckily, this story doesn't turn down that road.

As soon as he had rested inside me for a moment, he began fucking me in earnest. He used deep, powerful strokes, and hit something every time he buried himself to the hilt, so that I was yelping as I sucked, and tried desperately not to bite down on, Esteban's dick.

Richard pulled out, and he and Esteban switched places. Richard pulled the condom off and slid his dick into my mouth, and I eagerly sucked it clean of the condom lube (mainly to get rid of the taste of it). Esteban was even quicker, his thick cock stretching me out more than Richard's had, but without the pain of him bottoming out. He fucked me like that for five or six minutes, then he pulled out, tossed his condom away, and scrambled up to the head of the bed. Richard told me to flip over, so I did, and he positioned me so that my head was right in Esteban's lap. Not being stupid, I immediately sucked him into my mouth, and Richard climbed on top of me, put the head of his newly-condomed dick against my asshole, and drove it deep in one thrust. Then he lay on top of me fully, legs pressed against legs and his stomach against my back, his cock deep in my ass, his lips right by my ear. I loved this position so much that I've requested or begged everyone who has since fucked my ass to do me this way.

After lying there a moment, letting me feel the full weight of him, he began thrusting in earnest, pulling his dick almost all the way out and slamming it home every time. This actually hurt, and I moaned and squealed around Esteban's cock. Richard paused a moment and said, "I'm going to cum soon, do you need to stop?" Well, gee, when you put it like that - I moaned, "Mm-mm, mm-mm", shook my head the tiniest bit. Richard resumed, and suddenly the pain felt bearable, pleasurable. After another minute or two, he tightened up, thrust deep inside me, then kind of gave a bunch of micro-thrusts. Gasping, he lay down more on top of me, whispering in my ear, "Keep sucking, boy, he likes it. He probably won't cum, but keep going." Then he lay there, watching me suck his partner's cock while his cock softened and slowly pulled itself out of my sore ass.

After another few moments, he got up off of me. Esteban got up, too, and I figured the night was over. Just as well - I was exhausted. I shakily washed up in their bathroom, put my clothes back on, hugged them and took their phone number, and drove home. I masturbated to what had just happened, then fell asleep.