Hi again. I thought that I’d tell the story of the first time I was ever fucked. If you haven’t read my previous stories, you can find them on my profile. Some background first: this takes place during my freshman year of college, back in 2003. It was near the end of the year, and I’d been seeing Eliot for several months at that point. We were never officially boyfriends, as he tended to avoid those conversations. He was also deeply closeted, so our intimate time together was limited to where his roommate was out of town for the weekend, which was not very often, unfortunately.

After we’d had our first intimate night together, I’d sort of ghosted him for a couple of weeks. I know, I know—bad gay! Bad! But here’s the thing—I had never done anything sexual with anyone before, ever, so that night was both amazing and a bit outside my comfort zone. When we did run into each other again, I used the excuse that my classes had gotten more intense and I’d been focusing on my studies. I know, it was a really shitty thing to do, but I didn’t quite know how to deal with all of this new intimacy at that point. He seemed to accept my explanation, and we went back to business as usual: the occasional dinner or lunch together on campus, and the rare alone time in each other’s dorm rooms. We’d put on a movie, kiss, feel each other up, and exchange blowjobs (me giving way more than he did).

Toward the end of the year, he told me that his roommate had dropped out and was leaving, so we’d be able to spend more time together. I was excited at the possibility of getting to see him more, and of what other sorts of things we might do together. It took a couple of weeks, but we finally found a night that we were both free and I would be able to stay the night in his room.

By this time, I’d made a couple of friends in a one of my classes and they just happened to live in Eliot’s hall, so it wasn’t unusual for me to be there to see one of them and hang out. It was lucky for him, mostly, since I don’t know how well he’d be able to keep any rumors from spreading about me being there with him all the time.

Anyway, the big night came. I headed over later in the night, as we’d agreed. Unlike my hall, where everyone was friends and we all hung out together, getting up to mischief at all hours, Eliot’s hall wasn’t as friendly. I mean, people were friendly with each other, to be sure, but they weren’t as close as my hallmates and I were, and definitely not as boisterous. So when I get up to his floor, the hall is entirely empty and quiet, which made it easier for me to sneak in and out.

He met me at the hall door and we headed to his room. He was in his usual nighttime outfit: tank top and basketball shorts. I just had a t-shirt and some thin lounge pants. I was surprised as we entered his hall, since he grabbed my hand and held it all the way to his room. This was about as public as he was willing to be - no one around to see or comment on us being in any way intimate. A lot of red flags, I know, but in that moment I felt giddy at his touch.

As soon as we were through his door, he closed it quickly and embraced me, immediately going in for a kiss. We stood there for what seemed like hours, kissing and feeling each other up in the dark room, the only light coming from the lamps outside shining through his window. After several minutes, we finally came up for air. He took a step back, dropping his shorts and taking off his tank top, throwing it to the ground. He stood there before me, wearing only a pair of very tiny briefs that left nothing to the imagination. I followed suit, discarding my clothes as fast as I could, wearing only a pair of boxer briefs. He came back in close, and we started to kiss again, this time without all those clothes to get in the way of each other’s touch.

Another few minutes went by like that, until he stopped kissing me and took my hand, leading me over to his bed. There was no movie playing to distract us this time. He laid down, moving over so that I’d have enough room to lay next to him. As we continued kissing (what can I say, I’m a slut for kissing!), we felt each other more and more, our hands exploring each other for what felt like the first time. After a time, he suggested that we 69. We both took off our underwear and then I moved into position, and was immediately in heaven. I played with his dick and balls while he did the same to me. At some point, I felt his hands around my ass, and followed suit. After a few minutes, I started to feel a new sensation - his fingers exploring my hole.

At this point, I’d never done anything beyond kissing and blowjobs, so this was a very new sensation! It felt a bit weird at first, but I quickly got used to the feeling. Slowly, he started pressing his fingers in, then deeper and deeper, until he had 3 fingers going in and out slowly and gently. I tried to do the same to him, but he told me he didn’t like that, so I stopped. His fingers in my hole felt so good, so I didn’t complain about not being able to do the same to him.

After a few minutes of this, he pulled his fingers out completely, and asked if he could fuck me. I told him that I’d never done that before, but that I’d like to try. He directed me to grab lube and a condom from his dresser drawer, which I handed to him. I helped to put the condom on him, and then he directed me to lay face down on the bed. As I lay there, he slowly rubbed my ass, giving me a couple of slaps to each cheek, then started slapping his dick around my ass.

He started slowly, rubbing his dick between my cheeks, then teasing my hole with his tip. After an eternity of this, he started to enter me. He had a huge dick, about 8” in length and girthy, so it hurt a bit as he entered me. But he was slow going, getting me used to his size. It took him a while to get fully inside of me, my ass hurting like nothing I’d ever experienced before. But once he was fully in, he started going in and out slowly, then quickly picked up speed. After a while, the pain subsided and turned to pleasure. It was amazing, feeling him inside me. I got lost in the new sensations I was feeling.

As he started to pick up speed, he leaned forward, grabbing my hands and holding them behind my back as he fucked me hard. This, too, was new to me. I wasn’t sure how to feel at first, but was soon very turned on by this dominance he was showing.

We stayed like that for maybe 15 minutes - him fucking me while holding my hands behind my back. Then he started going even faster and his moans became louder. He told me he was about to cum, and he let go inside me not long after. I was thankful for the condom he was wearing, as I wasn’t sure at the time if I could have handled being barebacked during my first time.

It took him a few minutes to come down from his cum high, and he pulled out slowly, discarding the condom into the trash can by his bed. As he laid back down beside me, we began to kiss again while I jerked myself off. He still explored my body, sucking on my nipples and playing with my balls, but he was basically done for the night.

When I finally came, which wasn’t long after, we both got dressed again and laid in his bed. We held each other close as we drifted off to sleep. It was the first time I’d ever spent the night at his place, and it would be the last. I woke up early the next morning and let myself out, being as quiet as possible so I wouldn’t wake him.

When I finally saw him again a couple of weeks later, he told me that he couldn’t continue seeing me. He had invited me back to his room, and even tried to fuck me again, but as soon as those words were out of his mouth, I knew I was done. Done with the uncertainty of our relationship and done with all the hiding for him. I was angry and left, slamming his door. We didn’t talk again for almost 2 years, and only after a mutual friend had pointed out how disruptive Eliot and I had been during a group meeting at the LGBT center. We had lunch, talked, and made amends, but we were never close again after that. I still saw him around campus from time to time, and would be cordial to him, but any spark that had existed between us was gone.

Thanks for reading and I hope you’ve enjoyed this story. I wish it had a happier ending, but such is life and first relationships. Live and learn, I guess.