My whole life I’ve considered myself straight and have had girlfriends. The only experience I’ve had with another guy was a few drunk make outs. This past semester I decided to live by myself.
The last few girls I’ve gotten with, I wasn’t as turned on and had troubles staying hard. It made me curious about being with another guy. I always get turned on watching gay porn and surfing gay Reddit pages. I decided to give Tinder a shot to maybe find a guy to hookup with.
My experiences on Tinder weren’t great at first. I had a few conversations and flirted a little but was always too afraid to actually meet up. I matched with a much older guy in his 40s who messaged me right away with a long paragraph about just wanting a friends with benefits. It was Sunday afternoon and I was pretty horny so I told him sure and said I could host. I told him to bring condoms and lube since I didn’t have any.
I was extremely nervous waiting for him to arrive but I already gave him my address so I was committed. I went down to get him when he arrived and he looked just like his pictures. Fit muscular guy in his 40s, pretty attractive. We had some small talk walking back up to my apartment and we didn’t waste any time going to the bedroom.
I didn’t tell him this was my first time because I didn’t want to seem inexperienced. He laid on the bed and I started to take his pants off. He had a really nice cock. Like 6.5/7 inches but thick. He was already somewhat hard before I started to suck him. I’ve never sucked a dick but it’s sort of felt natural and I don’t know if I was any good but he seemed to really enjoy it. He took charge of the whole situation which I really liked.
After I was done sucking him, he told me to lay on my back. He put a condom on and lubed up his dick and put a few fingers in my ass with lube. His cock was thick and had trouble getting it in while laying on my back. We tried with me laying on my side and that still didn’t work. He added more lube and we tried doggy and he finally got it all in. He started slow but it still hurt so bad… I didn’t expect that much pain but I tried to tough it out. He started to pick up the pace and it definitely started to feel better but still hurt a little. The pain wasn’t as bad when I was stroking my own cock and actually felt really good.
At this point, he’s balls deep pounding my ass from behind and I was moaning uncontrollably. He was slapping my ass pretty hard which hurt but made the sex feel better. I told him I wanted him to cum inside me. (Not sure why but it was in the moment and felt so slutty) He took the condom off and spit on his dick before putting it back in. I could tell he enjoyed it more without a condom then he finally came, I didn’t even feel the cum inside of me like I thought I would. I came a few seconds after he did.
After he was done, he got dressed and told me he was down to do it again next weekend. While I enjoyed it at times, it was more pain than I thought it would be. I read online about anal desensitizers and butt plugs that could potentially help. I definitely think I want to try it again, any advice?
Source: reddit.com/r/gonewildstories/comments/jy18ud/21m_first_gay_experience