“So…you want to get naked?” My first true gay experience [MM] [Long]

Hey there! This is my first attempt in writing about my sexual experiences. Hope I do well!

So this is a story about my second ever sexual encounter with another person. A little backstory first. It happened during my final year of college a few years ago, a time where I was discovering my sexuality, hooking up with others, and putting myself more out there. For my entire life up until 2015 I considered myself a straight male, having happily dated a couple girls in the past, but a trend of letting the occasional gay thoughts wander led me to discover that I’m in fact bisexual. My first encounter was with a trans girl and didn’t involve much, but it was my second encounter with a full-on man that still remains one of the best experiences I’ve had so far.

Anyways, I would browse the personals on Craigslist a lot, mostly due to how new and shy I was about bringing up sex and exploring my sexuality with anyone I knew. Finally had the courage to post an ad myself one day; I was 21 at the time and am relatively small compared to other guys my age, being about 5’5″ tall with a twink build. Despite my usual straight side with women, my gay interests were mainly on the submissive side. You can imagine how many bad replies I got because of all that, but luckily I was always extremely picky when it came to guys. I needed them to be attractive, not too old, and able to form complete sentences. Responses came in and I kept ignoring them until I got a message from the lucky winner.

As I was making myself dinner that night, I got a nicely-worded text (I wasn’t very smart including my phone number in the ad) from an interested 26-year-old who we’ll call James. He sent a picture of himself in sexy underwear, revealing his great, toned body and attractive face. “I hit the jackpot,” I thought to myself, as we talked more about what we’d want to do and scheduled to meet at his house (again, not a very smart move) in a couple hours. It was hard to contain my excitement as I ate dinner and took a shower afterwards. Even though I got a really genuine vibe about him, I realized how risky of a thing it was to meet a stranger at his house for sex, so I actually ended up writing an “If I’m not back by tomorrow night,” note that I left in my room for my roommates. It was a little silly going that far in retrospect, but hey, I was still new to hookup culture and it was unused in the end anyway.

James lived about ten minutes away from me, so I took a nice, quiet drive on over and got there around 9 pm. We coordinated through text where I would park, which ended up being a tiny bit away from the front of his house to avoid any possible suspicion. He was at the door and let me in as I walked up.

Wearing a white t-shirt and gym shorts, he welcomed me in. His dog excitedly greeted me as I stepped inside too, followed by interested looks from his two cats. I took off my shoes and coat and went over to the two different couches in the corner of his living room. We sat down and chatted about each other for a little bit, and that combined with the presence of his pets made me feel really comfortable. It was a nice moment to calm my nerves but it was obvious that our sexual tension was off the charts.

“So…you want to get naked?” he asked when the small talk came to an end. I said yes and he led me to his room, closing the door before his dog could get in too. It was clear that he prepared the room for us; it was spacious, the bed was made, and the lights were dim. We stood face-to-face and started feeling each others’ bodies. I looked up at him (he was decently taller than I was) and we went in for a kiss that quickly turned into making out. It was my first time ever kissing another guy, and I couldn’t have asked for a better kisser to do it with. Knowing that I was still new to everything, James took the lead and eased me into things. His hands went up my shirt and down my pants, grabbing my ass, to which I did the same to him. Once our hands met each others’ bare torsos, our shirts came off and he pulled me so that our bodies themselves made contact. Still kissing, it wasn’t long until he unbuckled my pants and pulled them down, revealing my hardening cock against my already-soaked briefs. I took his shorts off and started rubbing his cock through his underwear as well.

Our clothes were off in no more than two minutes of starting, and he led me over to lay against the pillows of his king-sized bed. I sat back with my legs apart and he began going down on me. He instantly set a new standard for giving the best blowjob I’ve had, and all I could do was lean my head backwards with small sighs of pleasure. With this he also dove his tongue into my asshole, something I never thought I would love so much, he was so good at rimming. After a little bit of that we swapped places and I laid stomach-down, head between his legs, with my lips wrapped around his cock. I think he noted how well I was doing despite having little to no experience giving head and was impressed, which made me happy to hear. I blew him some more and and pulled myself up onto him, grinding our wet cocks against each others’ while we made out some more.

He swung me around so that his head was between my legs and my face met his cock, and we started sucking each other some more in a 69 position. This was definitely one of the many highlights of this encounter, as 69ing was something I always found really hot. I really felt the size difference between us when doing that. He wasn’t that much bigger than I was, but his overall body type was a lot more masculine compared to my twinkish physique, and laying myself onto him like that appealed to all of my sexual sweet spots.

We continued to do this for a while, slowly turning on our sides. I flipped myself back around and kissed him some more as he rubbed our cocks against each others’ again. At this point I was almost completely wrapped around him, he opened me all the way up and I felt like I could do anything with him. “Your dick is bigger than mine,” he noted while stroking both at the same time. I chuckled and agreed. I was about 6 and a half inches hard, while his was about an inch shorter. We joked about how the younger twink sported the bigger package.

After a little bit more naked cuddling and humping, he got himself over me and in a missionary position. Now, when we first started texting each other we talked about how I’ve never had anything in me before and I probably wouldn’t want to try penetration. Instead of actually putting his dick inside me, he grinded his shaft against my spread ass and cock, teasing my asshole by sliding his cock against it. He made all the movements and sounds of fucking me without actually going in. I was so turned on by it, and it was obvious that he really wanted it too. The experience was going so well and I was so hard for him that I changed my mind and asked if he could try fucking me for real. James got up and walked over to get a condom and some lube, and I took the moment to stand up and stretch. As he put his condom on, I sat on the side of his bed and then laid down so he could lube up my asshole. He told me that he’d go slowly, and if anything started to hurt too much I’d let him know. I agreed and lifted my legs over his shoulders as he began to poke my asshole with the tip of his cock. I could already feel how tight it really was, but even with how little was going in it felt so good. As the head of his cock made its way in, things kind of took a turn as he tried pushing the shaft in. My hole couldn’t take much more widening, so I sadly had to stop there. We were bummed by it, but made up for it by sucking each other off some more.

I laid on my back again and he sucked and jerked me off, and I was trying so hard to cum for him. No matter how much we tried, though, I wasn’t able to, probably because of some leftover nerves still holding me back. When we were both out of breath, the experience came to an end. Lights came on, we cleaned up, and we talked some more about each other and our lives, me sitting at the foot of his bed with him standing in front of me. We both knew that we had to get moving eventually, so he told me he wanted to get a shower before bed, which was my cue to head on out myself (I secretly wished I could’ve joined him though). As he walked me out, he said to keep in touch if we’re ever up for it again.

The next morning, I texted him to thank him for the really nice time, and that I was glad he was so gentle with me. He said he enjoyed himself a lot as well, but wasn’t really interested in doing any more hookups at that point in time. A little disappointed, I understood what he wanted and didn’t try to change his mind. We still stayed loosely in contact with each other for the next couple years, though. I always wanted to do something with him again, as I still hold that experience in very high regard. Talking to him again recently, it seems like we may get back together again soon, though, and if anything does happen I’ll definitely make an update if you guys are interested :)

Source: reddit.com/r/gonewildstories/comments/8erxn7/soyou_want_to_get_naked_my_first_true_gay