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What’s your gender? Man
How old are you? 60
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Nashville, Tennessee, USA
Highest education received: Some college (not currently in college)
What’s your occupation? Retired
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Not sure
How religious are you? A little
What’s your sexual orientation? Mostly heterosexual
Any other term(s) that describe your sexuality or sexual identity? Got a hardon when I was 14 from a cousin(male) who spent the night with me and I woke up with his hand in my underwear. At 15 another male friend wanted to get naked and try sucking each other to see if we liked it; I was very hard.
How many sexual partners have you had in your life (including oral sex)? 100 or more
How many hookup stories have you here posted before? 1

One And Only Time Fucking A Friend

How long ago did this hookup happen? About 10 years

What was your relationship status at the time? Engaged/Married (monogamous)

How would you best classify this hookup? One-night stand

How long did you know the person before this hookup? For more than 3 years

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? We had been friends since we were 16 years old and this happened when we were in our early twenty’s. We went out drinking and went back to his mom’s house to crash. His stepfather woke us up and said we should be ashamed and get dressed. We were completely naked and sleeping on the pullout sofa in the living room. We were both young, and in great shape, and I remember getting dressed and both of us sitting next to each other and staring at each other’s dicks. I specifically remember thinking I really wanted to feel his dick and I started getting aroused. Then he said: “man I’ve always wanted to see your dick and I said I always wondered what yours looks like, and now I want to touch it.” We decided to do that some other time.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? There was no planning and I instigated it. It was 25 years later. I went back to visit him and we were sitting around talking and I was feeling horny. I told him to break out the porn and he tells me he doesn’t have any, but I kept asking. He finally got up and came back into the living room with a DVD. He says, “before I put it in, I’ve been into Tranny porn for several years and I use butt plugs and dildos while watching.” I tell him I’m ready to watch some Trannys, so he starts the movie and within 10 minutes I’m hard as a rock. I stand up and I start getting naked and when I’m standing there in my Birthday suit with a hardon I say, “I hope you don’t care,” and he brings up that time we woke up naked together. I told him I remembered both of us staring at each other’s dick and getting hard and both saying we wanted to touch each other. By this point, he’s staring at my dick sticking straight out and I pointed out that he was still dressed. He gets up and starts getting naked and I walk over to him when he’s done. Now we were standing with our dicks almost touching and I knew something was going to happen. He reminded me about the video, and we sit on the couch together so close that our legs are touching. I’m feeling the electricity between us and we try watching the movie, but really can’t stop looking at our cocks. So I got up and got a drink, and as I’m walking back to the couch, he stands up and says, “I know you’re aroused. We both want to touch each other, so would you like to fuck me in the ass right now?” I almost passed out from too much stimulation. I told him to lead the way.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? He reached out and wrapped his hand around my cock and gently pulled me towards the bedroom. I was in heaven thinking about what was going to take place. He pushed me back on his bed and told me he’d only had toys in his ass and asked me to go slow. I told him I would. He grabbed some anal lube and spread it all over my cock. I was sure I was going to cum just from him stroking me. He then lubed his asshole and told me he was going to straddle me so he could control how much went in. I was just watching as he grabbed my cock and guided it to his well-lubed asshole. When the head of my cock touched his asshole I told him I thought I was going to cum before he even got it in. He squeezed my cock until the feeling stopped and sunk down on it about 2 inches. We looked at each other and I told him he felt tight. He then slid down another couple of inches and stopped and then he slowly lowered himself all the way until he was sitting on me. He told me he’d never felt so full and asked me if I liked what I was feeling. I said yes and he raised up until just the head was still in, before he went all the way down again. I told him he’s tighter than any woman I’ve been with and he went all the way up and then slammed all of his man pussy back down and told me to fuck him like a woman. I started pounding his man pussy like we were teenagers and after a couple of minutes, we turned until he was on his back. I got his legs on my shoulders and I fucked him for all I was worth. He started moaning and squirming and I could feel the cum building. I told him I was gonna cum and he said, “cum deep in me.” Without any stimulation on his very nice cock, he started coming; 4 or 5 big ropes of cum hitting me on my chest and stomach. That was all it took, and I plunged into his man pussy with the best orgasm I’ve ever experienced almost passed out. My ears were ringing and he told me he’s never been fucked like that from a dildo and that he knows he’s loving life as a man pussy. I told him that was the best sex I’d ever had. My cock deflated and gently slipped out of that asshole and I was mesmerized as my cum started leaking out of his man pussy. We laid there talking about what just happened and decided, before I left the next day, that we would fuck as much as we can.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, multiple

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? Well, we fucked 4 more times and the next day as I was leaving, I felt some regret for cheating on my wife! We didn’t talk about getting together again and both agreed it was awesome. We are still friends, and every now and then we message each other and send dick pics and talk about our first gay experience!

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

What were your motives for this hookup? Fun, pleasure, horniness, Learning new things, experimenting, Just happened, I don’t know why, just went along with it

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Not at all (no alcohol or drugs)

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? Very

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? I told my wife’s sister about it because she told me about her experience trying lesbian sex.

How would you best summarize people’s reactions about this hookup? Neutral

Did you get emotionally hurt as a result of this hookup? Not at all

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? Somewhat

Why do you regret this hookup? That I’ve been married for 30 plus years and cheated on my wife with a man.

What was the BEST thing about this hookup? One of the best orgasms ever

What was the WORST thing about this hookup? Guilty pleasure

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It has; why label if it feels right.

All things considered, how POSITIVE was this experience? Somewhat positive

All things considered, how NEGATIVE was this experience? A little negative

Anything else you want to add about this hookup? It made me realize that being safe sexually and telling my wife everything was the right thing to do. She actually said it turned her on and asked would I fuck him again so she could watch and he said anytime.

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? Men fucking a lot of women makes him a stud and a woman a whore and that’s just wrong.

What do you think about the Casual Sex Project? Great experiences need to be brought out to the public.

You have a hookup story to share? Submit it here!