This post is sponsored by The T-Bar.
by Ian O’Rourke
What’s your gender? Man
How old are you? 57
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? US
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Educator
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Agnostic
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? rampantly horny
How many sexual partners have you had in your life (including oral sex)? dozens
How many hookup stories have you here posted before? 2
Very Happy Ending
How long ago did this hookup happen? 6 weeks
What was your relationship status at the time? Engaged/Married (monogamous)
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? A is a gorgeous 52 year old redhead of Italian heritage with beautiful olive skin. She is tall and strongly built, a massage therapist by profession. I met her about 6 years ago while attending a conference in her city, which is about 2 hours from where I live and work. I needed a massage, and a colleague recommended the school of massage therapy that A owns and directs in town. I stopped in without an appointment, and all her students were busy, but she offered to massage me herself. It was probably the best therapeutic massage I ever had. Every year, when I attended this same conference, I would schedule a massage with A while I was in town. We struck up a friendship, and after the second or third massage, went out for drinks afterward. She was married, I was married, but we were very simpatico and enjoyed drinking together with our mutual friend, the colleague who referred me to her massage school. It was completely platonic for years.
Then, about 2 years ago, our mutual friend got married, and we were both invited to the wedding. We, and our spouses, were seated together at the reception, and A and I danced a couple of times, including a slow dance with some mild grinding on both our parts. Alcohol will do that to you. There was some sexual tension developing. The four of us went back to their hotel room to get high. We traded partners to exchange foot rubs, but nothing else happened. She definitely had my attention, however.
I should mention, shortly after this, she and her husband separated and later divorced.
The last time I was in town for my conference, about 5 months ago, we went out for our customary drinks after my massage. She actually brought up the issue of our mutual attraction, which led me to share the stories of a couple of my previous exploits (described elsewhere on this site). She was intrigued, I guess, because we started texting to explore the possibility of getting together. It took her a while to get comfortable with the idea, and to establish some ground-rules to keep things on a FWB basis, then we set a date and made plans.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Just to put a little spark in it, we planned a little role-play at a bar near her house. She and her sister-in-law were attending a memorial service and stopping at the bar afterward. I was to already be there. She and I would pretend we didn’t already know each other, and I was to try to pick her up, right in front of her sister-in-law. This account is already too long, but just the scene in the bar would be worth re-telling in detail. To summarize, however, I was successful, and we ditched her sister-in-law and went back to her house.
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? When we got back to her house, it was only mid-afternoon, and the tenant who rents an apartment over here garage and his girlfriend were waiting to talk to her about something. We ended up inviting them in and having a couple of drinks. The sexual tension was killing both of us, and I maneuvered us both into the kitchen a couple of times to steal some quick but very wet first kisses. The other couple eventually left, and A and I started making out in earnest in the kitchen, with lots of groping and grinding. At one point, she hiked up her dress, squatted on her 4-inch heels, took out my cock and started blowing me in the middle of the kitchen. We moved upstairs to the bedroom, peeling off our clothes as we went, and ended up in her bed. We fucked in every position we could think of, most of it pretty conventional. Because of the alcohol we’d been drinking and the Viagra I popped as soon as we got back to her house, we were able to keep going for a couple of hours. We were well-matched in our appetites and preferences, and it was very comfortable and easy. No first-time jitters. Our long-standing friendship certainly contributed to that level of comfort and familiarity. It was more like, we should have done this years ago!
After a couple of hours of nonstop fucking, we took a break, and went over to her brother’s for something to eat and hang out for a while. The look on her sister-in-law’s face was priceless when we walked in, because she could easily figure out what we’d been doing since we ditched her in the bar.
After hanging out to eat pizza and play cards, we went back to A’s house, fucked some more and fell asleep. I was spending the night, so there was no rush. I love overnighters. Fuck some, sleep some, fuck some more, sleep again, fuck some more, sleep some more. We probably fucked 4 or 5 times during the night.
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? She had to meet her grown daughters early the next morning, so we pretty much woke up early, dressed, and both left without a lot of interaction. It was very natural and comfortable, however, and there was no doubt there would be a next time.
We’ve hooked up once more since then, and it was even better than the first time. As we communicate needs, wants, preferences, and expectations, we’re both better prepared to please ourselves and each other.
We are adhering to three rules: 1. Family first. Obligations to family take priority over our play-time. 2. No falling in love. Neither one of us is changing our respective relationship statuses, and we are friends first and lovers second. 3. It’s over when either one of us says it’s over. No whining, no expectation of anything more.
What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Sterilization, Discussed STI testing history
What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s)
How intoxicated were you? Drunk/high but not wasted
What substances did you consume? Alcohol
How intoxicated was your partner? Drunk/high but not wasted
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? A former lover of mine. She and I are close friends and swap hook-up stories when we have something worth sharing.
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? Finding out that an old friend and I were mutually attracted, sexually compatible, and comfortable with this new aspect of our friendship.
What was the WORST thing about this hookup? That she lives two hours away, and it won’t be easy to find alibis to visit and spend the night as often as we would like.
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? No.
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? It dawned on me after about 20 years of marriage that it is unrealistic to expect one person in the world to meet ALL of one’s needs in life. Sex is one of the most basic and fundamental pleasures in life, and we should enjoy it wherever we can find it. Monogamy is a social construct, not a natural inclination. We are not meant to share ourselves with only one person for the rest of our lives. Unfortunately, polyamory is not universally appreciated or accepted, so deceit is sometimes necessary.
What do you think about the Casual Sex Project? It’s wonderful to be able to share these experiences in this forum.
You have a hookup story to share? Submit it here!
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