Latest Encounter with My Friend



What’s your gender? Man
How old are you? 48
What’s your race/ethnicity? Mixed / Multiracial
What continent do you live on? Australia
What country and/or city do you live in? Sydney
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Transport
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Agnostic
How religious are you? Not at all
What’s your sexual orientation? Bisexual
Any other term(s) that describe your sexuality or sexual identity? Enthusiastic
How many sexual partners have you had in your life (including oral sex)? Over 50
How many hookup stories have you here posted before? About seven, can’t remember exactly

Latest Encounter with My Friend

How long ago did this hookup happen? Two weeks ago

What was your relationship status at the time? Same as current status

How would you best classify this hookup? Friends-with-benefits

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? Tom is my long-standing friend with benefits. He’s a handsome guy, same age as me. I’ve known him for over 20 years. We haven’t been having sex for all that time – I knew him first as a friend, and we tried for a relationship about three years after we met but it didn’t work out for various reasons (both of us too immature if truth be told). That’s when we first had sex. After that, we left each other alone physically for about ten years. Then we started having sex again. What sparked off our renewed sexual relationship (about thirteen years ago) was his plan to move away and I suddenly couldn’t stand the idea of never being close to him again. We went to the pub and had a couple of farewell drinks and when we walked out to go back to our respective homes. As we were alone, I grabbed him and kissed him, and things went from there. I should say that I really love Tom, but we are not in a romantic relationship as such. We are both in committed relationships with other people and have sex about three or four times a year maximum so you couldn’t even really call what we have an affair. Though, both of us are drawn to each other.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Planning is always involved with our hookups. Shortly after his birthday, he invited me to his house to help with a bit of garden work when his partner was at work and he was on a day off. Before I went over I found a piece of purple gift wrap ribbon and tied it on my wrist. I went over and helped out for a bit but I honestly couldn’t take my eyes off him. He’s well built and fit (unlike me). I kept running my hands over his arms and across his shoulders. He stopped to kiss me a number of times, and I felt his cock hardening in his pants. I told him that it was time for him to unwrap his birthday present and held out my wrist with the ribbon tied around it (corny I know, but he’s so masculine and dominant that somehow I always feel like a giggly schoolgirl around him). He pulled it off and I told him that we could do whatever he wanted. We finished the work and took a shower together, then he led me to the guest room.

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? We lay naked together hugging and kissing. Tom grabbed my cock and rubbed it gently and I did the same to him. I put him on his back and kissed down his body, taking his cock in my mouth. God his cock is beautiful. I love sucking on it. He seemed to love it too! Eventually, we ended up in this position where I was lying on my back with my head over the side of the bed, looking straight into a full-length mirror. He stood over me, legs apart and pushed his dick into my mouth. I took it all the way – I loved seeing myself in the mirror with his balls pushing right up against my lips. Then he bent over and took my dick in his mouth. His blowjobs are the best! He always says he doesn’t like giving head and hardly ever does to his partner, but he always does to me. I don’t know why that is, but it does make me feel special. We 69ed like that for a while then he pulled out and asked if he could fuck me.

Now I definitely enjoy anal but it can be quite painful for me so I was a little hesitant, but I had promised Tom anything so I said yes. Tom laid me on my side and I lubed up my arse while he lubed up his cock. Then he lay behind me and I felt the head of his dick against my hole. I guided him in and pushed back. For the first time, I didn’t feel the slightest bit of pain. Just that wonderful feeling of fullness you can only get from having a hard cock in your arse. He fucked me slowly like that for a bit, feeling my nipples while he fucked me. Then he pulled out, turned me onto my back and put my calves against his shoulders and slid into me. “Your arse is so tight,” he whispered as he started to fuck me harder. He pushed my legs apart and bent down and we kissed passionately. Then he returned to slamming his dick into me. “God I’m close,” he said, and I saw the questioning look in his eye. I just nodded and he unloaded into me. I love seeing his o-face, it’s like he’s in absolute ecstasy…so much it’s almost painful. I love knowing I can get him like that, and I love him to stay in me until he’s so soft he just slides out. I love that feeling of us being connected.

After he pulled out he took me in his arms and kissed me while he wanked me to an amazing orgasm. I came all over his hand and my belly. It took about ten tissues to completely clean up.

Afterward, I sat on the toilet letting his cum leak out of me then we showered again and I took him out for a birthday lunch.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, one

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? I felt like I was on a high for the next two days. My expectations for the future with Tom are generally more of the same. We both recognize our partners are our first priority, though, so it’s always possible that each time together may be our last. I love Tom, and he and his partner are good for each other and there is no way I’d want to ruin that for him. We had our chance years ago and blew it, so now I’m just grateful that we can still be as close as we are, emotionally and physically. Although when he’s deep inside me I can never get rid of that nagging thought that goes something like, “you idiot, if you hadn’t messed up back then, you could have this every night… “

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Discussed STI testing history, Exchanged recent STI test results

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection

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

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

How wanted was this hookup for you at the time? Very

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? Only your website

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

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? Not at all

What was the BEST thing about this hookup? Everything. It was perfect and I wouldn’t change a thing.

What was the WORST thing about this hookup? Nothing – see above.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No

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

All things considered, how NEGATIVE was this experience? Not at all negative

Anything else you want to add about this hookup? I think I’ve said it all.

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? As I’ve said before, it plays a huge role in my life and I just wish I could be more open about that with my partner.

What do you think about the Casual Sex Project? Wonderful. I think it will be an important archive of our times for future researchers. Also, it’s quite a turn on to read others’ stories and imagine others reading mine.

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