I’ve explained further in another subreddit, but essentially I was in the middle of a divorce process going a bit crazy. I’ve never been with a guy before, but it was officially out that I was bisexual. During the meantime, my now ex-wife was taunting me with the stuff she was doing with new men. I don’t blame her, she was going through a lot too and she didn’t know how to process it. With that being said, it started pushing me to finally take the plunge.
I started chatting casually with a couple online. They were probably 10-15 years older than me but they were nice. I explained my situation, and they explained theirs. After a few hours of chatting I was driving over to their house with my heart thumping hard and fast. I kept thinking to myself “am I really going to do this?” Before I knew it, I pulled up to the street by their house. It was honestly huge, and looked expensive. It took me a lot of courage to step out of the car and to knock on the door.
I was greeted to the older of the 2. He was Italian, on the bigger side, but with a friendly smile. He gave me his name, though I believe I mentally blocked it of my head for one reason or another, so let’s just call him Adam to make it easier. I was let in and asked to take a seat in the living room. Adam chatted with me about his experiences, and how he wanted me to feel safe and in control if I didn’t like how things were going. His husband, let’s call him Bill, took about 5 minutes before he arrived at the place too. He was Asian, and quite a bit shorter, and thinner. We introduced ourselves and made some small talk
Before I knew it, I was being asked if I wanted to go into the bedroom. I nodded my head, not even sure if I wanted to but thinking I was already this far, I shouldn’t turn back now. I went into the bedroom and was greeted by the site of a very wide bed. Before I knew it, they both completely stripped and laid on the bed. There was a space in between them in the bed, and it was pretty obvious what they wanted me to do.
I tried to avoid eyesite as I followed suit taking off my clothes, not wanting it to look as if I was staring and judging. They were staring at me though, and as I relieved my package, they both gave me compliments.
I was quite a bit larger than them both down there, and they had a good amount to say about it. I was beckoned over to get in between them and I almost panicked and ran out… but I found myself slowly approaching the bed. Before I knew it, I was in between them. Adam placed his arm under my neck while Bill was slowly touching my chest. They were both staring at my dick…
Bill asked me “may I?” I nodded my head. I thought he was going to just touch it. Before I knew it, he engulfed 75% of the length of my cock, which was more than I ever had my wife take before, at least that way. I audibly gasped, while Adam placed my hand on his cock. It was weird touching another man at first, but I knew what would probably feel good for him so I stroked it the way I liked to be stroked. He seemed to enjoy it, but it didn’t take long before he wanted more.
“Do you want to suck it?” I honestly didn’t know how to answer that. I was still deciding on what I even wanted to do with men. I figured this was my chance to explore though… so I said “sure.”
He guided my to lay stomach down in between his legs. I hesitated for a moment, but internally said “fuck it” and took it in my mouth. It was harder than I expected to stretch open my mouth as much as I needed to to accommodate him. He wasn’t very long though, so I could get pretty much most of it in.
Bill was watching, and stroking. After a couple minutes I could hear him shuffling behind me. I remember thinking “fuck! Is this happening? Should I stop him?” I felt him touching my asshole… I lifted up my back end to accommodate. Before I knew it, I felt a cold gel hit my asshole. Adam was giving me tips as this was happening. I heard a condom wrapper rip open. Once again, I almost booked it, but I felt myself frozen in place. Then I felt it. It was slowly pushed in over the course of a minute or 2, while I focused on bobbing my head up and down.
It hurt a bit, but Adam was talking me through it. It honestly didn’t feel good though after the pain went away, it just felt tolerable. I haven’t done it since so maybe that was just not for me, but it didn’t take long for Adam to tell me that he was close. I was already in deep enough, so I figured I’d let him cum in my mouth. I didn’t expect him to push my head down as he did. I swallowed.
I was flipped over, and Bill was quickly on top of me. He asked “may I?” and I nodded again. He offered me a condom, but I opted to use the ones I bought instead since they felt a bit more comfortable around the bad area. he placed a lot of live on it and he then lowered himself onto my cock slowly. He moaned quite a lot as he did it. It felt pretty good, definitely tighter than what I was used to. My ex never let me fuck her ass before, just play with it. It probably took me about 5 minutes of this before I was close. I came in him… or at least in the condom I suppose. Before I knew it, he was jacking himself off onto my chest, as Adam was just watching and being supportive.
I was offered a towel to clean up, and was out the door within 5 minutes. My legs were shaking like crazy.
I never met up with them again, since COVID quickly became a thing afterwards. I’m taking care of myself, accepting who I am and figuring out what I like
Source: reddit.com/r/gonewildstories/comments/ns7vae/my_m_first_time_with_a_guy_was_an_all_male
Awesome story. Good luck on figuring things out.
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