The Delicious Night That Everything Changed



What’s your gender? Man
How old are you? 52
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Vancouver
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Designer
What’s your current relationship status? Engaged/Married (open)
Religious affiliation: Jewish
How religious are you? A little
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 11
How many hookup stories have you here posted before? 0

The delicious night that everything changed

How long ago did this hookup happen? 3 months

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

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? For less than a year

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? Melissa and I had first crossed paths at a local sex-positive event a couple of months prior. In a room full of fun, attractive and sexy folks, she made an impression with her geeky-in-the-best-sense vibe (those glasses, yum!), tightly curled shoulder-length hair, and vulnerable smile. But we only spoke briefly and had just a little playful interaction during the sexy icebreaking “games” the host put on, to help people relax and get in the spirit of things.

At a subsequent event, again attending with my wife, I “helped” Melissa, at her request, along with one other man, by stroking and caressing her as she enjoyed a rideable sex toy. Though having attended these kind of events several times, along with my wife, by this point, this was my first true sexual interaction with someone other than my wife. While she rode, and became more heated and vocal in her reaction to the stimulation, I sucked her nipple, then nibbled it quite firmly. She moaned with pleasure. I rubbed her back. I stroked her feet. It was intense and so sexy, as she crescendoed to a loud and wet finish. Afterward, she had a slightly dazed, satisfied smile on her face and a reddish tinge on her upper chest.

In the days afterward, my wife and I had some good conversations about how we might in theory involve another partner or couple in our sex life in some way. But it was just theoretical. Then, ironically enough, on my birthday as we were enjoying dinner at a retro diner, I received a Facebook message… from Melissa. She had so enjoyed our encounter and wanted to thank me… and asked if I would be open to further explorations, next time we found ourselves together.

It was the beginning of some amazing things to come (pun intended).

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Melissa and I had traded FB messages back and forth. The arrival of each new block of text in that little window made my heart leap a little, not least because, due no doubt to the vagaries of schedules and availability, there was a random amount of time between my response and her reply.

This was in late June, and the next opportunity to see her at a play party wouldn’t be until September. In the meantime, my wife and I discussed what our boundaries would be and what she would be comfortable doing. Initially, she said she wanted to be present for any play between Melissa and me, and that if that occured, penetration was to be “off the table”. I was willing to accept this, but it’s interesting how feelings can change and rules can turn out not to be so firm. After thinking about it, she eventually said, “it seems unfair of me to deny you two the main thing Melissa wants!” She knew that my “appealing cock”, along with my smile and positive energy, were what had drawn Melisss to contact me. As well, my wife explained that she really does feel that sex should be able to be something people do purely for the fun and enjoyment of it, without it needing to require any deeper commitment or exclusivity. Naturally, I feel the same way and was grateful to hear that – at least in theory – we shared this attitude.

So, I anticipated that September event, and the first chance I’d have to be with Melissa again. The anticipation was intense, and as the big evening approached, was almost impossible to bear.

Then the big night finally arrived.

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? My wife and I were approaching the entrance to the venue and we saw Melissa and her husband, Jim, approaching. We chatted pleasantly at the entrance hall, but before long we like all the guests were ensconced in the sexy environment and enjoying some of the icebreaker games – though this time there was really no ice left to break! We also engaged in some lengthy, passionate kisses.

Finally, somehow, we arranged to move to a more secluded area with a little cot. My wife had earlier said she’d wanted to be present for any play, but now she said she preferred not to be right there. She wished us well and relocated to another part of the venue.

Then it was just Melissa and I, alone at last.

I remember caressing her lean body, sucking and licking her from her shoulders, to her breasts, and down. Now I was tonguing her petite pussy lips, and was in absolute heaven. She writhed on the little cot and emitted cries of enjoyment.

Finally, it felt that the time for me to enter her had arrived. Somehow – I can’t even remember how – Melissa retrieved a condom from the supply she’d brought. And as I rolled it on, I noticed that I felt a little like a fumbling teenager again – anxious but excited, just as in those moments I’d experienced years before when I was less experienced, and the impending moment of delight, so long anticipated, loomed before me.

Now I gently laid myself onto Melissa, feeling her warm, soft skin all along my body. It was very easy to slide into her moist, welcoming wetness.

From there, we rocked back and forth in a tandem dance of thrusting passion, the tempo increasing, until at last, unable to hold back, I came explosively, crying out in uncontrollable spasms of pleasure.

At the risk of appearing less than the perfect lover, I have to admit that I’m unsure if Melissa truly orgasmed during our encounter. But my best sense of the rhythm and flow of her reactions assured me that she was deriving great pleasure from the experience.

We lay together in the dim light of our little nook, as my heart gradually slowed down to something like a normal pace.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? I don’t know

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? It felt like my world had been transformed, in that I had been able to make love to a lovely and appealing woman, enjoy an intense and satisfying experience, and then return to my lovely wife and transfer that sexual energy back into our relationship. Call it sex-positivity, polyamory, open relationship, or just a little good old fashioned fun – regardless of what we were doing, there was no guilt and no regrets.

I knew I was going to want to meet up with Melissa again at the next monthly event, but I also knew that there was no threat to my relationship with my wife. This was someone who could be in my life in this particular way and it would be OK. My connection with my generous, progressive, sexy and wonderful wife would only be strengthened. And so far, it seems that it has been.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms, Sterilization, Discussed STI testing history

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

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? My wife was supportive of my having the experience and wanted it to be a good one.

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? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? I’m a fairly confident guy and feel I have good self-esteem, but this experience, from the initial expression of attraction right through to the culmination of our mutual attraction, made me feel even more confident and happy than I’d ever been. It was a dream come true.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? As I say, it made me feel incredibly confident. I literally felt that I could be more direct and engaged with the world at large and with everyone I met, and this feeling remains, even long after the initial rush has inevitably faded.

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’m truly grateful to Melissa for reaching out to me – it turns out this was something she’d never done before! – and adding something very special to my life.

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 feel that society forces a disingenuous double standard on us in making non monogamy something unacceptable to the mainstream even as the high rate of breakups, cheating and divorce make it clear that “one partner only for life” is simply not a realistic reflection of our true desires and natures. I’d like to see media, drama, fiction – the ways we reflect our attitudes about what’s OK and how we should behave – reflect a more open and accepting attitude and to even acknowledge approaches like polyamory, open relationships, etc. as viable.

What do you think about the Casual Sex Project? It’s great to have an online venue for sharing my story and thoughts about this topic, and in particular one that is intentionally very reputable, responsible and non-exploitative in its approach.

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