A Little Experimentation



What’s your gender? Man
How old are you? 50
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Indiana, USA
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Programmer
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Atheist
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? Curious
How many sexual partners have you had in your life (including oral sex)? 20-ish
How many hookup stories have you here posted before? 0

A Little Experimentation

How long ago did this hookup happen? 6 years

What was your relationship status at the time? Single

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? Ron (not his real name) was 5’7″ or so, good looking, in very good shape, somewhat muscular. He was Asian (I believe he was from Malaysia) and worked as a medical professional; very intelligent and friendly. He was in a committed but open relationship; he and his boyfriend seemed to fairly regularly play with outsiders, both together and separately.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I had just gotten divorced about six months before. I had always been curious about exploring with another man, and stumbled across Ron’s ad on Craigslist. The ad mentioned the possibility of hooking up with just him, or with him and his boyfriend. I responded, not really expecting things to go anywhere, but Ron replied to my response almost immediately and we began first exchanging emails and then texting.

Ron told me that his boyfriend was busy that evening, but that he was interested if I was. It being my first time, it seemed like maybe a little one-on-one would be preferable. He asked me what I was interested in, and I told him that I was into experimenting a little, that I had always been curious, and that I would just be down for some oral playing, which he was fine with. We exchanged pictures (the first and only time I’ve sent a picture of my penis to anyone, male or female) and after some back and forth I agreed to drive the 45 minutes or so to his house to hang out.

When I arrived, he offered me a beer and we hung out and talked for twenty minutes or so. He was, as his pictures had indicated, very good looking, and was dressed casually in a t-shirt (which nicely showed off his pecs) and sweat pants. We discussed his relationship (the openness of it and all that) and my recent divorce and the fact that I had never been with a man before. He told me about his first time, with a friend years and years ago, and how he had been in a relationship with a woman for several years before deciding that he was fully interested in men. Eventually, he asked if I wanted to see his house; I said yes and he walked me through the upstairs, ending up in his bedroom.

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? Ron and I sat on his bed; he asked me if I was into kissing, and I told him definitely yes. So we started making out for a while. At first we were just sitting on the edge of the bed, but eventually we kind of laid back and we were running our hands over each others bodies. He took my shirt off, and then I took his shirt off. He had me stand up and unbuckled my belt and we both slid my jeans off and I stepped out of them. At this point, I was super nervous (despite the fact that Ron had done a great job of trying to help me relax), and I had to pee, so I stepped into the bathroom (which adjoined the master bedroom).

When I came out, Ron was lying back on the bed, his head and chest somewhat propped up by several pillows. Like I said, he was in great shape, with nice pecs and a six-pack and all of that. Even though I was nervous, I was very turned on, and I climbed on the bed and crawled on top of him and began making out. I think he was a bit (pleasantly) surprised by my initiative. We made out like this for a few minutes, and then I started kissing my way down his chest and abs until I got to the waistband of his sweats; now or never, I told myself. So I started pulling down his sweats down until I freed his cock, which was beautiful and uncut and somewhat thick; maybe 6 inches or so (I’m a little longer, maybe 7”, but not quite as thick and I’m cut). I ran my fingers over his gorgeous cock, and then started kissing up the length of his shaft until I got to the head. I ran my tongue over the head, which he really seemed to enjoy, and began moving my hand up and down his shaft while taking his head in my mouth. I got my first taste of another man’s precum (I’ve tasted my own before many times), and was in absolute heaven.

At this point, Ron was moaning and seemed very into the attention I was giving him. We took his sweats the rest of the way off, and he pushed me down and got on top of me while removing my boxer briefs; I’m not sure I’ve ever been harder in my life. He stroked me and then went down on me for a few minutes, then came back up and we kissed for a while longer. I noticed that he was stroking himself at one point, and told him that I wanted him to come in my mouth; he seemed a bit surprised that I was so insistent, it being my first time and all.

We played around for a while longer. We got into a 69 (which was somewhat awkward, as it often is), and then he climbed on top of me and sucked my cock while cramming his entire cock down my throat until I almost gagged, which was both uncomfortable and a turn-on (I liked the forcefulness of it).

After 15 or so more minutes of making out, of kissing and licking and sucking, he straddled my chest and started to stroke his beautiful penis while I opened my mouth and kissed the head and ran my tongue over him. He told me he was close to coming and I told him please; he asked if I still wanted him to come in my mouth and I told him please again. He fucked my mouth for a couple of minutes (an incredible turn-on), then started stroking himself again and moaning more and more loudly. I could feel him tensing up; I ran my hands over his tight ass while my tongue licked and flicked him. I looked him in the eyes, clearly desiring him, and the eye contact sent him over the edge. As he came, I made sure to open my mouth and swirl my tongue around the tip of his penis so he could see his cum filling my mouth. It was amazing, pleasuring him like this, and I swallowed eagerly.

Eventually, I straddled his chest and came in his mouth, too (he commented happily on how much cum there was), by which time he was rock hard again. He made some comment about his state of arousal, so I told him that he could cum for me again if he wanted. I went down on him, and after a few minutes he came again while I held his gaze, begging him to come in my mouth.

By this time, it was late. So I got up and started to get dressed for the drive home. He commented on how beautiful my ass was, and told me he thought I would really enjoy fucking. He was standing behind me, and I pulled him close to me and turned my head to kiss him; I could feel his cock pressed up against my ass, which was another huge turn on. I told him maybe next time, and we kissed some more before I got dressed and drove home.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, 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? We stayed in contact for a while, and we discussed the possibility of a return visit. He wanted me to meet and play with his boyfriend, too. While I was very into the idea, I entered into a committed relationship with a woman shortly after and we never did hook up again.

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

What were your motives for this hookup? Learning new things, experimenting

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

What substances did you consume? Alcohol

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

What substances did your partner(s) consume? Alcohol

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? I have never told anyone. I live in a fairly small town, and have kids, and just don’t have anyone in my life that I’m close to in such a way as to share something like this.

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? The sex was amazing. The vibe was amazing. Being that desired was incredible. I loved being naked, lying next to Ron, making out.

What was the WORST thing about this hookup? Nothing at all.

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

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 would like to be in a position where I experimented a bit more. I am currently in a relationship that is on again/off again, and it seems to be wrapping up. I’d like to play around some more, try some new things.

What do you think about the Casual Sex Project? Incredibly sexy.

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