[M]y first [m]otel experience, or any experience... | 2016

So after a failed relationship with yet another woman, I finally one night decided to indulge all the curiosities I'd ever had. Going on Craigslist, I messaged guy after guy and found either flakiness or bots, but there was one guy who was in a nearby motel, an Asian guy who seemed interested. Of course he demanded pics, and I sent some body and genital shots I'd done with one of the first generation blurry webcams (this was many years ago).

I seemed to have passed the test because we agreed to meet up in the parking lot of the motel, to be smuggled in the side entrance.

When I got there and he stepped out he was slightly older than I expected, and a bit "rougher", but that was fine by me. He nodded, and I followed him through the door, entering an elevator. I felt two things, the hammering of my heart and imagining the soundtrack to "Mission Impossible".

We went into his room, he closed and locked the door, and then he turned and we stared at each other for about four seconds, until he whipped his shirt off and dropped his pants to the floor in two swift movements, revealing a swimmer's body with a beautiful, hard cock.

I didn't get undressed quite so suavely but did so, and he reached for my dick and kissed me. His was slightly larger than mine, I noted with some jealousy. I pushed his hand gently away because I was really, really excited and wanted to prolong this as much as possible. He shrugged, and lay on the bed, inviting me to suck his penis.

I got down alongside him and took it into my mouth, feeling one in my mouth for the first time. It was like a hard, textured core with a softer, slightly movable surface. It tasted slightly salty and musky, and I started to shake.

After a few minutes of this, I realized I needed to make my move or I was going to chicken out, but also this was making me unbelievably horny. It was everything I dreamed of and more. He was a top, as he said, and unbelievably masculine - and being in a submissive state of sorts was starting to really turn me on.

He gave me a condom to put on him and I put it on, awkwardly. I'd heard it was easier to slip someone into you "on top" because you could control the penetration, but even though I'd put lube on him and me, I couldn't get the angle right, and the bedsprings kept shifting my position. I was starting to feel like a failure, though him rubbing against my anus as he tried was tantalizing.

Finally he said "let me."

He stood up, went over to the bathroom and got a towel, which he lay on the bed. "Lie down" he said, not an order, but firmly, and so I lay facedown with my ass in the air. "No, not like that" he said, turning me over. "If you do this" - and with it he brought my knees up to my chest and spread my legs "it opens you up more and makes it easier. First time?" I nodded.

He was putting on another condom, centering my ass over the towel, and lubing up. Then he put his penis against my anus, me almost shaking with excitement and fear, and then he pushed his dick all the way in.

At first I felt an unfamiliar stretch, which wasn't all that unpleasant, but then a slight burning and certainly some pain, and I went into a bridge, arching my back. "Are you okay?" he asked, and I shook my head, saying "give me a second to adjust". He waited, his hard cock still prising my bruised sphincters open. After a second or two it subsided, and I nodded. "Okay".

He started slowly fucking me, sliding back and forth inside my tight virgin asshole. I never knew being entered felt so good. That and the combination of him spreading my thighs open and pinning me down with his big dick were a total, total turn on. As I relaxed into it, eagerly feeling him slide deliciously inside me, he started fucking me harder.

I alternated between watching this handsome man's muscles strain as he pushed deeper and harder into my asshole, and feeling being fucked, having submitted completely to his dick and relishing every stroke.

This went on for a wonderful five minutes, a five minutes in which I wish this wasn't going to be the only time. I fantasized about him spanking me, I wanted to taste his cock again... until I realized I wasn't going to make it. I wasn't used to being fucked and it was starting to go from hot and pleasurable to being almost something to endure.

"Are you going to come soon?" I asked hopefully, scared and slightly turned on at the thought of having to endure more of this. To my delight he said "oh yes" and took one hand off one thigh. He reached in between us and grabbed my dick, massaging it perfectly with his hand. The combination of his head bumping my prostate and his lubricated hand jerking me off was bringing me close, so very close to coming.

"I want to watch it. I want to see you come" I begged him, and he nodded, smiling slightly. He was pounding harder and faster and I was getting close too, when suddenly he pulled right out of me with a pop that drove me over the edge. I started to spasm just as he ripped off his condom and I looked down to see both our cocks shooting hot ropes of come all over my stomach and chest. It was the strongest, hardest orgasm I'd ever had, and I was quivering with the intensity of it. He got off me, towelled himself off with a nearby towel, and thoughtfully put one on me so I could clean our fluids off me.

I stood up, the blood rushing to my head, disorientated by that and the flickering of the fluorescent lights. I went to the bathroom to wipe off the lube and saw a slight tinge of red to it. He followed me in having seen it on the condom, put his arm around me and said "you're bleeding. Are you OK?" I nodded yes, and he kissed the back of my neck.

This was goodbye. We both knew it. He had a meeting in the morning and I had work, and it was already 2 a.m. He was leaving town tomorrow, and I'd never see him again. I dressed hastily, thanking him, and left.

I thought about him again as I took an unnecessary AIDS test six months later, better 1000% safe than forever wondering. It was negative. So all I got to take from it was my happy memories and a certain sadness that I'll never be fucked like that again.