Craigslist Hookup on Holiday

by Starman

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? Quite a few

Craigslist Hookup on Holiday

How long ago did this hookup happen? Eight months ago

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

How would you best classify this hookup? Paid sex

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? He was a young guy, said he was 18 but might have been slightly (but not much) older. I’ll call him Joe. He was nicely built, not especially buff, with a round face, dark hair and a nice smile. I found him on Craigslist while on holiday in America. His ad caught my eye – said something like, “18 yo would like to meet an older man for mutual sucking and perhaps anal if things work out.” I’ve never had great luck with Craigslist, but I enjoy arguing with the scammers via email, so I emailed him. I was surprised to get a reply so soon – he said upfront that he was having trouble paying the rent and could I help out, which I agreed to. Then he sent me a couple of pics (face, body, dick) all of which looked good to me. So he gave me his address (about 20 blocks from where I was staying), and I showered and went to meet him.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I met Joe on the street outside his building. He seemed nervous but glad to see me. He told me bluntly that he’d often get to this point and walk away if the person looked like a creep. Then he said, “I’m not gay, I just do this when I’m short on cash.” We went inside and talked a little more. He seemed like an interesting guy and to be honest he reminded me of guys I knew when I was his age. Guys who swore they were heterosexual but would come to me for sex. He seemed confused in that way because while he insisted this was just business for him and didn’t really turn him on, he kept mentioning we could meet for sex on an ongoing basis and he wouldn’t always be asking for money. I had no wish to take advantage of someone in that situation, so I told him, “Look, I like sex with people who want it. You seem down on your luck, so take the money, and I’ll go.” But he almost begged me to stay.

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? Joe said he couldn’t just take the money without doing something for me. “Let’s trade blowjobs,” he said. I assured him that would be fine and I wasn’t all that into anal anyway, and he looked relieved. He put some porn (lesbian! I remember thinking how incongruous this all was) on his tv and we sat together on the couch. I really wanted to kiss him – he had soft, sensuous lips – but I thought that might be a bridge too far for him. We both pulled our pants off, and he started to suck my still flaccid cock. I love oral, and he seemed exceptionally good at it for one so young. His mouth was warm and wet, and his lips and tongue put just the right amount of pressure on me. I became hard almost instantly but pulled him off me before I got too close to cumming and sucked his already hard dick into my mouth. His dick tasted nice and clean, and after sucking around the head, I went down all the way and took him into my throat. From the noises he made I think he enjoyed it. When I came up for air, he pushed me back and went down on me again. I usually take ages to cum, but it was only a few minutes before I tapped him on the shoulder and said, “I’m cumming.” He pulled off, and I spurted all over my belly. While I wiped up with a paper towel and came down from the rush, Joe finished himself off by hand. Pity because I would have sucked him to completion and swallowed his cream if I wasn’t wallowing in bliss from my own orgasm. After that, we both cleaned up and went our separate ways – I to do touristy things and him to pay the rent which was overdue.

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?

e to pay any more,” which made me even more confident he’s one of those confused guys. He looked downcast so I asked what was wrong and he said he didn’t want to be a whore. I told him I was from Australia and in our society prostitution was legal and generally not seen in such harsh terms as in the US. He seemed to brighten up at that and asked again if we could meet later in the week. I did try to hook up once more, but I didn’t have much time, and when I was free, his flatmate was home so there would’ve been no privacy.

The day after this hookup I was still coming down from that wonderful blowjob and orgasm, and jerking myself off to the memory of his mouth and cock. Wish I could see him again but doubt it will ever happen since we’re worlds apart both literally and metaphorically.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Thought it was an important experience to have, It was easy/convenient

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? I don’t know/I’m not sure

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

To whom did you talk about the hookup? How did they react? My fwb back home but not in great detail – only that it happened. He was pleased as he always feels bad he and I can’t meet as often as we’d like.

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

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? I don’t know / I’m not sure

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? His wonderful blowjob – one of the best. And he was a nice guy.

What was the WORST thing about this hookup? Not sucking him to completion and not getting to taste and swallow his cum.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Not really though I’m glad when it got to the point where I felt I was forcing Joe into a position he didn’t want to be in I was willing to give him the money and go. I’m glad my dick does not entirely rule me to the point where I’d force myself on a young guy who’s down on his luck.

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? Generally, I avoid guys that are confused about their sexuality. Way back when I was 18 till I was 21 I had an ongoing fuckbuddy/friend with benefits who would come to my bed, have wonderful sex, then afterwards say he was heterosexual (not even bi). It made me feel like I was nothing. I never wanted to be in that situation again. But somehow Joe was a bit different. I think he’ll be able to be more honest with himself and partners in future.

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? I love it. It’s a significant part of my life. Just wish I didn’t have to sneak around behind my partner’s back.

What do you think about the Casual Sex Project? Great!

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