Topped a 20-Something



What’s your gender? Man
How old are you? 43
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Australia
What country and/or city do you live in? Melbourne
Highest education received: College degree (eg., BA, BS)
What’s your occupation? IT Manager
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Agnostic
How religious are you? Not at all
What’s your sexual orientation? Mostly heterosexual
Any other term(s) that describe your sexuality or sexual identity? Acting out in a loving but sexless marriage. Couple encounters, unexplored curiosity lead to several gay sex encounters.
How many sexual partners have you had in your life (including oral sex)? 40-50
How many hookup stories have you here posted before? 0

Topped a 20-Something

How long ago did this hookup happen? 2 weeks

What was your relationship status at the time? In a relationship (monogamous)

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

How long did you know the person before this hookup? Just met that day

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? Guy in his mid-20s I contacted on a dating site online who was putting himself out there to be fucked (particularly by an older guy). Had a mostly smooth body, smallish penis and average looks. No attraction going in but there never really is – just fixate on cock/ass pics. Messaging replies were short and blunt which should have been a warning sign.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It was arranged through a handful of messages on that day. I was feeling horny and had an opportunity. I arranged to meet him at his flat a short time after chatting.

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? I let myself in and he was waiting clothed. I was on the back-foot from the start when he started frantically french-kissing me.  I avoid kissing males and generally don’t enjoy it. I didn’t enjoy it this time either – the feel of stubble on my face and the probing of his tongue. After some brief rubbing of crotches we stripped and he started blowing me. We moved to a more comfortable location and 69ed for a bit. His cock didn’t seem to get very hard in my mouth. His blowjob was enthusiastic and wet but I was struggling a bit mentally to get into it. After a time I put on a condom and fucked him doggy. I had an out-of-body experience asking myself why the fuck I was doing this, given that it gave me no pleasure and was sure to create a lot of guilt and shame. I continued fucking him, moving to him on top. He jerked himself to an orgasm and sprayed an impressive amount of cum on my chest. He passed me a cloth and I mopped it off. He took off the condom and he continued to blow me for sometime – I was hard but I wasn’t into it. We stopped and started a few times and eventually he offered to use a toy on me while he blew me. I borrowed a small cock-shaped dildo that he washed off in the bathroom, put a condom on it, lubed it up and inserted it in my ass. He worked it a bit while I stroked myself to an orgasm. I had to close my eyes and imagine a hot woman crouching over me and grazing my face with her fleshy wet pussy lips to reach orgasm. I felt awkward and wanted to leave. Conversation was polite but difficult between us. I cleaned up in his shower, washed the toy etc, dressed and said goodbye. I felt confused at my actions, numb and sad.

How sexually satisfying was this hookup? Not at all

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 terrible after the hookup (and still do). Although safe sex precautions were used for fucking I was/am anxious about HIV infection and now wish we had discussed our STI history. I’m most worried that some of his cum may have got on the condom-wrapped toy when I applied lube to it and inserted it. The risk from our behaviour seems low but its hard to suppress the fear and guilt. I resolved to message the other guy to offer some form of apology and to confirm STI status but he has blocked me from contacting him.

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, To feel better about myself, To feel more desirable, To cheer myself up, I was feeling lonely, Boredom, It was easy / convenient

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

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

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

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

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

To whom did you talk about the hookup? How did they react? No-one. It would be a terrible shock to anyone I know.

Did you get emotionally hurt as a result of this hookup? Somewhat

Do you regret this hookup? Very much

Why do you regret this hookup? I’m confused and dismayed at myself for pursuing this encounter when it poses such a risk to my health, undermines my significant relationship with my spouse, induced shame and fear AND provided no real pleasure.

What was the BEST thing about this hookup? It has made clear my instincts regarding my sexuality clear – I am straight (previously curious) and opened my eyes to the stupidity and self-destructive beliefs underlying my behaviour.

What was the WORST thing about this hookup? The anxiety of not knowing my STI status for several more weeks and the regret and shame of having followed through with it. The anxiety of encountering the other guy again while out with my spouse and/or children.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It has prompted me to get a full STI check-up in a couple of weeks so I can know one way or the other whether I have payed dearly for the encounter. The fear of infection has caused me to confront my actions honestly and make clear decisions for either outcome. If I test positive for HIV I will make arrangements to leave my spouse and children and confess my activity to her. If negative, I will consider myself lucky one last time and never again pursue casual sex and dedicate all my energy to trying to repair my relationship to a healthy sexual state. If I check-out healthy I may get counseling but its very unlikely I will disclose any of this behaviour to my spouse. As shitty as this sounds, I don’t want to lose what I have and I want to continue to provide and care for my children and spouse.

All things considered, how POSITIVE was this experience? Not at all positive

All things considered, how NEGATIVE was this experience? Very negative

Anything else you want to add about this hookup? I think my attitude to gay sex has been one of glorified masturbation and a naive belief (self-delusion) that its an acceptable form of seeking sex outside my marriage because there is no real attraction or emotional attachment involved so it feels less dishonest.

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? Outside this experience, it has its place. It allows people to experiment and identify their sexuality, wants and needs. The issues of successfully resolving sexual need in a sexless but otherwise loving and supportive relationship is a real one and would benefit from some open discussion given that technology and changing social attitudes makes finding anonymous sex discreetly so much easier now and the moral and cultural inhibitions to same-sex encounters widens the pool of opportunity.

As things stand for me, I feel that it is currently a willfully destructive behaviour and not a positive course of action.

What do you think about the Casual Sex Project? It has the potential to provide a useful insight into the range of psychological and sexual motivations that lead people to pursue casual sex encounters. It helps open debate and discussion about individual and social morality, self-acceptance, human sexuality and hopefully leads to better life choices and more tolerance and support of others.

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