This was back in the days of chat rooms. I was in my late 20s and starting to get that itch to explore some bi feelings. I had only been with a handful of women, married to a woman now but had that familiar urge. I eventually wound up befriending a guy who lived in the city, about a half hour away. He was older, mid 50s, we’d chat online, eventually show off for each other. This went on for months. He had invited me to hang a few times but I was nervous. He was persistent but never pushy. We had built a pretty solid trust and I finally caved. I was going to be in the city anyway and took the plunge.

We had discussed the idea of exchanging massages alot. It was something he was really into and I felt like it was low risk enough that I’d be ok trying it. The day arrived and I walked up to his apartment a bundle of nerves. He buzzed me in and welcomed me at the door.

He was much shorter than I expected, I’m 5’8. He was about 5’5. Pleasant enough face and slightly more effeminate in person. I had been at work all day so I told him I’d love to rinse off before we gave each other massages. He showed me to the bathroom and got me towel, turned on the shower. He left the bathroom but kept the doir open. I undressed and hopped in. We made small talk. He eventually came back to the bathroom and asked if it was ok for him to watch. I was so turned on by that point I told him of course he could. He stood there for a few minutes staring and making conversation. It was such a turn on to be on display like that. I was almost done when he asked if he could join me. Again I said yes. It was all so hot but still a little awkward. I had never done anything like this

He started undressing, I’ll never forget him standing there in his tighty whities slowly pulling them down. Now I had seen his cock online, I knew it was big but attached to his short frame it looked massive. Thick. Decent length. Longer than my uncut 5.5 inches. I didn’t feel inadequate as much as i was impressed by his size.

He jumped in the shower with me and my nerves got the best of me. I told him I was done rinsing and he rolled with it. Touched my chest a little bit but could see I was nervous. He offered to towel me off and led me to his bed. He suggested that maybe to loosen up, he’d massage me first. I needed that. I laid on my stomach, completely nude and he stood over me. The moment his hand touched my back it was electric. He took his time, kneeling over me, I could tell he was just admiring the view. He’d rub my back and shoulders. Work his way down to my ass. I could feel his big cock graze my body as he leaned over me. I turned my head so I could look at it. It really was a good looking cock. He massaged my cheeks and thighs. Lightly between my legs. He asked if I was ready to turn over, I was rock hard and ready. It was nice to be fully exposed with him. To be completely nude with another man. I laid there looking at him while he rubbed my body. It felt incredible. But nothing could beat the moment he grabbed my cock. I shook. He was so gentle and patient with me. Slowly rubbing and jerking. Touching my balls. Really drinking it all in. I was in heaven. We didn’t want me to cum before I could massage him so he stopped

We switched positions, him laying on his stomach and I did my awkward best to rub him down. He seemed to enjoy it. It was the first time I had ever felt another man’s ass. I liked it. It wasn’t the nicest but felt so good to squeeze. He flipped over and it felt like he was just presenting me his big dick. I didn’t touch it right away but the urge was too strong. I grabbed it and he smiled at me. Asked if I liked it. Of course I did. It was truly a beautiful penis. I stroked him for a bit. He reached over and started stroking me. It was so intense. We picked up the pace, jerking each other and I was on the verge of exploding. He sat up and said he’d like to rub our cocks together and patted his lap. Told me “why don’t you lay across my lap”. Again an absolute bundle of nerves. I laid so our cocks were touching and he started massaging me again. This time really focused on my ass. He complimented it as he rubbed my cheeks and gently spread them. I squirmed, grinding our cocks together. He kept spreading my ass and studying my hole. Told me he really like it. He never attempted a finger inside but gently grazed a few times. It felt so good. I felt so vulnerable but also so secure with him. We very naturally fell back and laid side to side and jerked ourselves. He wanted to watch how I do it. I wanted to see how his big dick looked while he stroked. We watched each other for a bit but he soon took over. He was ready to make me cum. He was so skilled. Stroked my cock, played with my foreskin, rubbed my balls. I told him I was close and he said he wanted me to cum on my stomach. I exploded rope after rope. All over my chest and neck. I was fully drained and covered in my cum. It was too much for him and he immediately rolled oh his back and jerked himself off. His cum dribbled out all over his stomach. I couldn’t get enough. It was so hot to see another man cum.

He got us a towel and a glass of water. We laid there nude for a few minutes but that post nut clarity hit hard. I was ready to go. He told it was well worth the wait and to come back anytime. We hung out twice after that. Almost the same situation, swap massages, jerked and even a little more. We lost touch but it was the perfect first time for me