I was flying to Philadelphia for business and was looking to be a little adventurous in the big city. We had talked prior to meeting and exchanged pictures so I knew what I was getting into. I had expressed to him that I wanted to try to deepthroat him and just sort of submit to him and his desires, but he thought that since it was my first time, we should probably take it easy, which we did. We had worked out a few of the details beforehand, but for the most part the night progressed organically.
I had a nice hotel room (thanks work!) that he was going to come up to and I was going to be on my knees for him and slide the card under the door. My heart was pounding as I watched him walk down the hall. My room was the last door looking down the hall so I could see him from the second he turned the corner from the elevator; he looked a little nervous like he felt out of place, but he walked up and knocked on the door. Like we had discussed prior, I had taken my shirt off, slid the card under the door, and waited on my knees with my hands behind my back waiting for him to enter.
He opened the door, walked in, and looked at me. “Wow” he kind of laughed like he didn’t actually expect me to follow through on the whole dynamic thing. “Alright” he said mostly to himself grinning. He was a little shorter than me, but I was eye-level with his waist in this position. He stepped closer and said something like, “is this what you want?” grabbing his cock over his shorts. I was so nervous, all I could do was nod. He moved closer.
“Do you want to kiss it?” he said to me, staring at his shorts. Without saying anything, I leaned in and kissed the shaft of his cock through his gym shorts. “Now that’s the kind of greeting I like!” He laughed to himself. I untied and took off his shoes and asked him if he wanted to sit. “Not yet,” he said, “don’t you want to take my shorts off too?” I reached up to pull down his shorts but he stopped me. “You can do better than that, can’t you?”
Knowing what he was implying I should do, I bit the top of his shorts and began working them off with my mouth. My head brushed against his cock against his underwear, and I paused to take in the sensation. “You like the way it smells?” He asked, and I think I let out a moan because I really did like it. “It’s okay, take your time.” He said as he put one of his hands on my head. Not forcing anything, just letting me know he was there. With his other hand, he pulled his shorts the rest of the way down as I pressed my face further into his scent. I got the idea to lick his cock through his underwear, and when he noticed he said, “You’re eager, aren’t you? Here, let me help”. And he pulled his dick out for me to lick the real thing.
I had seen it in the pictures he sent beforehand, but I didn’t expect it to be as big as it actually was. When he was hard (and he wasn’t yet at this point) he was as long as my forearm (seriously, no joke) and pretty thick too. “Go ahead” he encouraged me, and I licked his cock from its base to its head. I did this a couple times, and the realization of my own submission got me very aroused. Here I was, kneeling before a man (he was only like 2 years older than me) I’ve never met before, licking his cock while he’s looking me in the eyes holding my head. It was at this moment I knew I belonged to him.
I tried to take him in my mouth, but all I could fit was the head and a little of his shaft. It was no where near what I wanted for my goal of “deepthroating”, but he reassured me that he like his head played with the most. I think he was just trying to make me feel better since it was my first time, which I appreciated. His reassurance did not stop me from choking on his dick a couple times trying to fit it in my throat. “Do you like that?” He asked genuinely. I told him I wasn’t sure and he clarified his question, “no I mean like to you have a vomit fetish? Do you want to throw up?” I told him no, I did not and that I was just trying to fit more of him in. “Don’t worry about it,” he said kindly, like how’d you’d expect an older sibling to ease your anxiety about something unimportant, “I’ll sit on the couch and you can give my balls some attention.”
I followed him to couch on my knees and started kissing his balls while he reclined back. “Go ahead and suck on them,” he told me. “You never want to forget about the balls!” He joked. So that what I did, one at a time I would lick and suck on his balls while he moaned in approval. After a little of this, I went back to licking his cock, which was now hard and laying up against his stomach. It went up past his belly button, and I savored every inch of it. I took him in my mouth a few more times, and eventually he leaned forward and saw that I was very erect.
“You’re really enjoying this, aren’t you?” He asked as he rubbed my dick with his hand. He grabbed it gently and kind of played with it. I told him I really was enjoying it, I just wish I could take more. “Do you want me to fuck you?” He asked. I told him I didn’t think that would be something I’d enjoy, but I’d never tried it before. “No worries,” he said moving right along. “Why don’t you lay up on the bed.” I went to the bed and layed on my back. He came up and swung his leg around my head; we were going to 69. I grabbed his dick and put it in my mouth and it block all of my air. I couldn’t breathe. He pulled my underwear back and put my dick in his mouth.
The combination of my excitement, my panic caused by a blocked airway, and him sucking me caused me to cum right away! So quick, no joke, I didn’t even feel it come on. I was mortified. He got up, wiped the cum off his lips, looked at me and went “what?” Sort of like “is everthing alright” mixed with “did that really just happen?” I’ve cum before with women, but this was by far the hottest thing I’ve ever been a part of, I had no idea what happened. I explained it to him, and he laughed and brushed it off. “I think I need a minute…” I told him. He was super cool about it, and we spent some time laying on the bed just talking.
He was a really smart dude, computer programmer, plays guitar/composes music, reads philosophy. We had a lot to talk about. After talking for maybe 10 minutes about all sorts of things, I asked him to further explain his thoughts on one of the philosophical topics we were discussing. As he elaborated, I made my way down his body and started playing with his cock in and around my mouth. He stopped talked, and I stopped playing. “Keep going,” I told him. “I actually want to hear your opinion on the matter.” I resumed when he did and we went on for a while longer.
He asked me again if I would let him fuck me, so we talked about it for a little bit, and I agreed on the condition that he take it easy with it being my first time (and I was afraid he’d pierce one of my lungs…). I asked him what I needed to do, and he told me to just stay where I was at the end of the bed and hang my legs off the side. I felt incredibly vulnerable when he approached me from behind, but he walked me through everything he was going to do before he did it. He started by licking my ass, which felt warm and I actually enjoyed it (would recommend). Then he stuck one finger in, he told me he was going to ease me into it.
He had one finger in for a while and we just continued our conversation from before, but with him inside of me. He laughed a couple times just because of how casual it was; I think it surprised him how laid back the whole thing was. Eventually he added a second finger, then a third, and after that, he grabbed a condom and the lube he brought with him and he eased himself into me.
Now this I didn’t really enjoy, honestly. It wasn’t bad, I didn’t dislike it, but it didn’t bring me any pleasure personally. Truthfully, it just felt like pooping. And maybe I didn’t enjoy it because I had already cum, I don’t know… I layed there and took it for a bit, and I even bounced on it for him. He came, but our night wasn’t over.
Afterward I sat on the couch, and he sat on the chair and we talked for another 3-4 hours. I was really connecting with this guy, he was very smart, we shared a lot of interests, and I feel like he cared about the things I had to say.
We said our goodbyes, he left, and I’ve never seen him again. But I think about it often.
Source: reddit.com/r/gonewildstories/comments/kb1r9y/my_first_mm_hookup