Losing My Gay Virginity

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***This is a real true story of my first gay sex about 10 years ago, I did not use a condom because I was young and stupid, please always practice safe sex****


I was in my 3rd year of college and home for the summer. I went to school out of state and thus could not out with new friends, and I hadn’t bothered to keep in touch with people from High school. My younger brother had an internship and friends of his own so most of time I was home alone, bored, and incredibly horny.

I have never thought of myself as gay, and still don’t, though for some reason people have a hard time truly believing a person can be bisexual (but that is what I would say I most closely identify with). I would watch all kinds of porn, straight, gay, transsexual, it all turned me on depending on my mood.

To describe myself I’m nothing special. A 7-8 on the attractive scale. I’m mixed white and Japanese but look mostly white except for my eyes which are slanted – gives me a slightly more ‘exotic’ look. I’m 5’10 140lbs and athletic so I had a slender, swimmers build.

As the days of summer went by and my boredom grew, porn could only hold my attention for so long. I wasn’t seeing anyone, I had broken up with my girlfriend a few months prior and wasn’t pursuing anything at the time. Eventually I started browsing Craigslist personal ADs – what for I wasn’t sure, maybe for something different, maybe for something more ‘real’, and maybe I would find a girl who was just as bored and horny as I was (hey a guy can dream right?)

Eventually I learned that any posts that were woman seeking man were either scams or bots. I kept browsing though, and became intrigued at the amount of male for male posts, the open/willingness to post pictures and say exactly what they were looking for. My curiosity and horniness bested me, I started contacting a few of these men. Knowing full well I wasn’t going to meet up with them, but the act of exchanging emails was enough to satisfy my thirst for now. After a few hours of back and forth talk of what we would do for/to each other they all realized I wasn’t going to meet with them and they stopped messaging me. So with that my boldness grew, I posted my own AD. It read something like this:

“21m seeking older man for casual time”

In a short paragraph I talked about wanting an experienced man to make me his lover and how I wanted to be bottomed. Attached was a seductive picture of myself in my boxers. I didn’t mention anything about how it would be my first time or how I would probably never go through with anything – but I think even at this point a growing part of me desperately wanted to.

In came the flood of responses. Most were spam or guys I could never find attractive. But then one caught and held my attention. He was older than me, 38, said he was into younger guys and sent a picture of himself. He was cute with a genuine smile. Not overweight, not skinny, but looked like he had a gym membership and took care of himself – oh and the picture he sent of his dick was very alluring too. We started emailing back and forth, I revealed that I had never done this and it would be my first time. He reacted in the best way possible Çankaya Escort and said that there was no pressure at all, I could just come over and hang out and if I wasn’t comfortable I could leave. He kept the conversation away from sex and talked about regular things, his job, hobbies, etc. everything about this made me feel a bit more relaxed and confident in myself that I maybe could go through with this. With my heart pounding and throat closing up, I messaged him back, letting him know I was going to come over and that I’d be there in a bit. I hopped in the shower and shaved everything as best I could with a shaking hand. I got dressed and got in my car…I was on my way.

The drive to his house was about 35 minuets, which was perfect because I needed time to still talk myself into this. I texted him when I was halfway there saying I was having second thoughts. He urged me to still come to hang out, he said he was on his way to the store to get some beers for us to relax with, I continued on.

When I got to his address I must have circled the block four times looking for ‘danger’ (hey, I was horny as hell and on a sexual adventure but I was about to have sex with a stranger from the internet, I still had some sense). I parked across the street and walked to his house. I held my breath and knocked…nothing. Was I at the wrong house? Did I get scammed? Should I leave? All of these thoughts and more were racing through my mind. Then I heard the footsteps, I held my breath again and the door opened. There he was, smiling in a fitted tank top and shorts.

“Hey! So glad you made it! Come on in.”

I walked in and frantically scanned for signs of ‘danger’ but found nothing. Only signs that his house was a home, there was recycling to go out, mail on the counter and dishes in the sink. I remember that this put me a bit more at ease. He handed me a beer and I gladly took it, I still hadn’t said anything. The beer tasted wonderful, cold, crisp and relaxing. My first sip must have been long because he chuckled. I put the bottle down.

“Yeah, I’m nervous.” I admitted.

He waved it off and sat down motioning for me to as well. Then he frankly asked,

“So what are you looking to do?”

I lied, “I don’t know.”

Even though inside I knew I wanted to be fucked, I wanted to feel the other, submissive side of sex, and to pleasure a man. He suggested that we just sit and have a few beers and chat, I gladly agreed.

After we each had 3-4 beers he said let’s take a tour of the house. His house was modern, clean and cool – I still remember it to this day. When we got to the master bedroom I was in awe, his king sized bed was against a wall of glass overlooking the lake. While looking around I absentmindedly picked up a bottle of massage oil.

“Great idea!” He said, “Let me give you a massage to help relax you.”

I was already more relaxed from the beers and I felt safe so I agreed. I took my shirt off and hesitated,

“Should I take my pants off?” I asked timidly.

“Only if you’re comfortable. Do you mind if I take my clothes off?” He replied.

I paused, Keçiören Escort “No…that’s fine.” I eventually said.

He stripped his tank top off and slide his shorts down. And there he was, with a shaped chest and his muscles flexing under his creamy skin, his 4 in soft cock right below a neatly groomed patch of hair. I was starring but he didn’t mind. He was…he was…hott. I slid my shorts off but left my boxers on and laid face down on the bed. I tensed when I heard him climb on the bed behind me and open the bottle of oil. He straddled my thighs, his cock resting at the base of my ass.

The massage felt good, his strong masculine hands going every inch of my arms, shoulders and back. Ever creeping lower, after a couple of minutes his fingers were prying under the waistband of my boxers, signaling what he wanted. I arched my back and lifted my hips, signaling back that it was okay. He went to pull on my boxers but they got caught on my growing erection. I went to adjust myself when he stopped my arm. He reached around and in a non overly sexual way grabbed my cock and removed the boxers with his other hand. He gave me a light squeeze and tug before returning to the massage. I gasped at the sensation of a mans hand on my dick, and continued to let out soft moans as he massaged my ass and the backs of my legs. Each pass moving closer to my hole. It was at this point I could feel him, his full sized dick now sitting between my cheeks. I rotated my ass against his cock and he responded, he pushed against me, gliding his cock between my ass cheeks. I reached my hands around and spread them for him, with one hand he pushed his dick down, thrusting between my cheeks. He paused and leaned over me,

“Want to flip over now?”

All I could get out was a vague nod before his hands were on my hips and he was flipping me over. There I was, dick hard and completely exposed to this sexy older man as he was looking me up and down. Nothing had made me feel more sexy in my life.

He put his head down and I lost my breath. His mouth around my cock and toungue encircling me. I ran my fingers through is hair and moaned. I felt a slight pressure at my hole, I looked at him, I nodded, indicating that it was okay. He easily slid one finger inside me (I would frequently finger myself while masturbating, but never more than 2 fingers). He pulled out and pushed 2 inside me, it stung a little but still went in with relative ease. Panting harder now from him both sucking me off and fingering my hole, I was able to silently mouth the word ‘more’. He pulled his face away and sat up. He poured some more oil and spread it all over my ass. He lined up three fingers and pushed gently. I clenched and made a face, trying to stay relaxed. He grabbed My hand – my eyes lingered on this. We hadn’t kissed, nor did I think we were going to. But this handhold…this was intimate. He pushed a bit more and got then in, working his fingers around he was stretching me out, he started slowing stroking me, knowing that the more turned on I was the easier this would be. After a minute of stretching and when I was relaxed I said to him

“I Etimesgut Escort want you to try.”

He got himself into position and I could feel his cock at my entrance. He slowly pushed into me and in an instant I could tell that he was much bigger and much different than a couple of fingers. After my tight hole made it past the head of his cock and clenched, I took a deep breath. I felt full, but knew there was a lot more to go. I started to worry, what if I couldn’t get him in? Then this would all be for nothing.

He grabbed my hand again and gently said, “You’re doing great.”

That relaxed me a bit and he pushed further. It was painful, but not enough to make me want to stop, he was going slow and I loved him for it. After a few minutes he was all the way in. We both breathed a sigh of relief and just rested there. The fear of not being able to take him faded and pain turned to pleasure. He started thrusting, slow and shallow at first but each one touching parts inside me I didn’t know I had. As his thrusts quickened and deepend my eyes rolled back and I was in ecstasy. This felt amazing, and I felt so sexy for turning him on and being an object for his sexual satisfaction. I reached my hand for my now semi hard cock and that was a mistake. Even only partially hard, the sensation of touch was about to make me cum, I quickly stopped.

With one last pump he forced himself all the way into me and leaned in,

“I want you to be on top, I think you’ll like it.”

He pulled out of me and laid down on his back. I faced him and straddled him, reaching my hand around I found his oiled cock and guided it to my hole. It went back in surprisingly easy and It felt like like it was suppose to be there. I rocked my hips back and forth, getting used to this position and how it felt. When I started raising and lowering myself on him is when I felt it, the sensation from the inside on my g-spot, and how it made my dick ooze. I was loving it, bouncing my body up and down on his cock, feeling every texture, every vein, every inch in my ass. My semi hard cock flopping between my stomach and his. It didn’t take long like this when he suddenly grabbed hold of my ass,

“I’m going to cum” he said in an almost whisper.

“Cum for me, cum in me.” I urged him.

He matched my movements and in only a few moments I felt it. The tenseness of his cock getting bigger and harder beyond normal, then the warmness inside me all over, and the pulsing as each load was shot into me. He grabbed my dick and started beating it feverishly. That, combined with the satisfaction of him cumming inside me sent me over the edge and in a few quick stokes I was cumming all over his chest.

We remained there for a minute, speechless, panting. His cock softening in my ass, and mine in his hand as he slowly tugged it. I felt awkward making eye contact, so he turned my head to him and fed himself and me a fingertip of my cum. I graciously took it, wanting to communicate to him that I would do anything for him. He lifted Me off of him and brought me under his arm. As I laid there in his embrace he asked,

“Did you enjoy that?”

“More so than I ever thought I could,” I said back to him. He smiled and held me.

I had just had my first sex with another man and I felt fulfilled, satisfied and changed. I knew instantly that this needed to happen again.


***Thank you for reading! Comments and suggestions are encouraged and welcome! Just trying to get my foot in the door in the community.

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