It started with curiosity. It was the early 2010s, I was a grad student who spent most of his time on the internet and I just learned about this dating app that seemed popular abroad. Emboldened by a movie I just saw, I decided to give it a go.

It didn’t take long for me to realize that Grindr was really just a hook up app, but I was hopeful. I had declined offers from guys knowing they only wanted one thing, and I had been rejected by a lot for not being too masculine. I had already gotten over it after a few weeks of trying and decided to give it one last go. I decided to message a few guys and said to myself that if none of them would respond favorably, I was gonna quit and get rid of the app for good.

After a few hours & a few pointless conversations, one of the guys responded & we got to talking. He seemed pretty decent & there was no mention of sex the entire time. When he asked me if I wanted to hang out, I thought “wow, finally, someone who just wants to hang out”.

We agreed to hang out at his studio apartment because apparently he made too much mac & cheese. We talked, ate, and watched TV—it all seemed like a legit hangout until he noticed that I maintained proper distance the entire time. He motioned me to join him on his bed while we watch TV because the chair I was sitting on definitely wasn’t very comfortable (no backrest). He then held my hand and told me they felt cold. I said it was probably because I was nervous to be alone in a room with a guy I just met. Then he said we can go out & get coffee if I wanted to, but I said we didn’t have to. We could just have coffee at his place instead if he had some. He laughed & said I was cute. Embarrassed, I looked down & said thanks.

He got up to check if he did have enough coffee & told me to make myself comfortable, but I stayed frozen on my spot. He walked back to prop a pillow down on my side of the bed & said I should lie down while he makes coffee. I laughed nervously. He noticed the tone of my laugh & asked if I was still nervous around him. I said I was a little. Then very bluntly he asked if he could kiss me. I was stunned and asked why, and he responded that maybe it would help me feel more at ease. I told him I’ve never kissed anyone before, and then he held my face. I didn’t know what to do then because it felt nice. He asked again if he could, and I just nodded. Then he went in for a short, sweet kiss.

Stunned & enchanted, I told him that it felt good & he can kiss me again if he wanted to. And he did. This time, deeper & with more gusto. I tried to match him & I could tell he liked it. It lasted much longer than the first kiss and when we broke it off, he held my hand & kissed it. I thought it was sweet & he didn’t let go. However, he strategically placed it on his leg, close enough for me to feel the tip of his hard member. I was flustered, but didn’t move my hand.

“Do you want me to make the coffee?”, I offered. He smiled and said, “Don’t you want something else instead?” He moved to kiss me again and I let him, and this time I could feel more than just the tip. He let go of my hand and pulled me closer. I ended up on top of him, and we kept kissing for about 5 minutes.

I decided to acknowledge the elephant in the room and mentioned how hard he was. We laughed and got to talking again. He said he hadn’t had sex in a while, and I said that I hadn’t had sex at all. Then he began playing coy & asked if I’d ever have sex with him, and I said maybe after date #3. He laughed and teased me putting my hand on his crotch. He said, “Are you really going to wait until then?” I don’t know what came over me, but suddenly my hand slid down his shorts & grabbed his rock-hard cock. He let out a moan, and then that was it. I lost it completely.

I pulled down his shorts & took his entire length in my mouth. I had never done it before, but somehow my hands & my mouth knew what they were doing. A few moments later I had my first taste of precum and I was going crazy. He had his hands on my hair & pushed my head down while he thrusted his hips up. I was choking on his thick dick & my eyes were tearing up. That’s when he asked me if I wanted him to fuck me.

I had always been the romantic type. I didn’t want to hook up with anyone because I wanted my first kiss, my first time, to be special. I had refused meeting up with guys before because I didn’t want to be fooling around with someone I wasn’t in a relationship with. But just a few minutes earlier, I let a hot guy I just met kiss me, and soon after I had his fat cock in my mouth. I couldn’t see why I shouldn’t just let him fuck me too. So I looked up at him with a mouth full of dick and nodded.

Both naked &very horny, he laid me down on my back & put my legs over his shoulders. He spat on his dick and slowly teased my hole. This was it, I thought. I was finally gonna lose my virginity & have my hole wrecked. I was gonna get fucked. Or so I hoped.

He tried to slide his cock in, but I was very tight. Or he was very thick. But I think it might have been both? Anyway, he tried several times but it hurt every single time. And it hurt a lot! We tried different positions, and he even tried to finger me, but even that couldn’t get in. My ass wasn’t having it! It was closed for the day. It just wasn’t happening.

Both gravely disappointed, we settled with another round of blowjob and him finishing in my mouth. By then it was too late for coffee and I had to get home. He said thanks & I said sorry, then we said our goodbyes. And while I was waiting for my train, I was hit with the realization that things were never going to be the same for me again.