Conflicted but Content

This post is sponsored by Trust Massage Oil.

by Lucky Guy

What’s your gender? Man
How old are you? 55
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? USA/Georgia
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Self employed
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 30?
How many hookup stories have you here posted before? 0

Conflicted but Content

How long ago did this hookup happen? 15 years

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? 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? I was attending an industry conference and was at the bar after the first day. We bumped into each other racing to the bar for a drink. She was not an conference attendee. She was visiting the city and staying at the hotel with her elderly mother. She had a very happy, smiley face; very pleasing to look at. It was the face of a smart, confident woman (turnout she had a Phd in sociology). I knew I wanted to get to know her better and I definitely discovered that she wanted to know me a little more too.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? By the end of that 1st night at the bar, there was no doubt how the evening would culminate…in my room. We made out the whole way up the elevator. She was the 1st woman I had kissed besides my wife in over 15 years. So you can imagine that I was a bit conflicted by what I was doing. But I got over it. Or subdued it. Or compartmentalized it. I dunno. Somehow I rationalized it. And to the sack we went! (BTW: She was about 5 years older than me. Never married and no kids. She lived in Georgia too, about 90 miles away in Atlanta)

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? The sex that night was awe inspiring. Having been married for 15 years, blowjobs were a distant memory and even doggie style had gotten a bit too unconventional for my wife. This night was ‘no holds (or holes) barred’. A lot of fluids were exchanged. She was an excellent partner. She had to leave around 3 am to sneak back in her room with her mother but we agreed to go bar hopping the next night, too. And enjoy whatever that led to later.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than 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? After she left that night, guilt ran thru my mind again, but asshole that I am, I pushed it back into a further recess in my brain and locked it away. We resumed in my room again that night after a lot more drinking. The sex was just as enjoyable but not as prolonged. We were too intoxicated and WAY too tired from the previous 24-36 hours.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Birth control pill / patch / ring / injection / implant

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Intoxication, Making new friends, It was easy / convenient

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? A little tipsy/high

What substances did your partner(s) consume? Alcohol

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? Nobody! You guys are the first!

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? I don’t know / I’m not sure

Do you regret this hookup? A little bit

Why do you regret this hookup? Well, it’s over. We met a lot over the next 8-10 years. I always had reason to be in Atlanta and she was always willing to make her condo available or visit me at my hotel. We liked each other quite a bit. She understood my situation, tho: married, father of two. I wasn’t going to leave that. But she didn’t seem to have any more interest in having me around more than I was anyway. But we did end it. I regret that I don’t have the chance to see her any more. I enjoyed our conversations very much.

What was the BEST thing about this hookup? The other avenue for great conversation that I had because of it. (I did tell you she was smart; a very interesting person)

What was the WORST thing about this hookup? The lies I had to come up with to make it work on my end at home.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Not really. I like the idea of casual sex. Funny tho, I would NEVER dream of having a relationship with any one I know IRL. This hookup worked (for me) because we were anonymous to each other when we met.

All things considered, how POSITIVE was this experience? A little positive

All things considered, how NEGATIVE was this experience? A little negative

Anything else you want to add about this hookup? I think I’d do it again. Not sure tho. My sex drive isn’t quite what it used to be (I hate to say).

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 have no reservations about casual sex as long as all parties involved are in consent and understanding of any boundaries.

What do you think about the Casual Sex Project? Just now linking to it from the New Yorker story today. I’ll keep up with you.

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