The Once and Future Queen



What’s your gender? Man
How old are you? 48
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
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Attorney
What’s your current relationship status? Divorcing
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 30ish
How many hookup stories have you here posted before? 0

The Once and Future Queen

How long ago did this hookup happen? Three months ago

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

How would you best classify this hookup? Sex with an ex

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 college girlfriend, and perhaps “the one.” And the personification of my type; dark brown hair, green eyes, curvaceous. I have loved her since the moment I first saw her, but I was a clueless fuck up when we were together a quarter of a century ago and I let her get away. We have had sporadic telephone or email contact over the years, but unhappily married other people and found ourselves on opposite coasts.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Early this year we connected on Facebook messenger and found each other technically married, but functionally single. Our banter quickly resumed as if it had never stopped and before long there was phone sex and regular daily contact, often concluding with us falling asleep together across a continent. I flew her to NYC for our first rendezvous, and subsequently met her in Vegas for a second.

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? In anticipation of NYC, we discussed the assumption that we would be having sex, but our interaction was awkward at first, causing me to get sullen at dinner. Later, back at the hotel, she pity fucked me as a way to break the ice, but only let me do her from behind, since she feared too much intimacy. Ultimately, however, we essentially spent the weekend in bed, reacquainting ourselves with each other and falling back into love. I went down on her repeatedly over the weekend, and we fucked at every opportunity. Our connection and sexual compatability had always been epic, and the years apart did nothing to change that.

Weeks later, in Vegas, was the same. Passionate, urgent sex. Making up for lost time, and fucking ourselves past the regret at what could have been. One drunken night, she asked me to fuck her ass as we looked out over the Strip from our hotel window.

How sexually satisfying was this hookup? Very

Did your partner have an orgasm? Yes, multiple

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), Emotional intimacy, closeness, connection, Hoping or expecting it would lead to something more, Intoxication, To feel more desirable

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? Only my therapist.

How would you best summarize people’s reactions about this hookup? Mixed (Some positive, some negative)

Did you get emotionally hurt as a result of this hookup? Somewhat

Did your partner get emotionally hurt as a result of this hookup? A little bit

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? The sex was amazing.

What was the WORST thing about this hookup? The emotional connection with this person has made our mutual desire for something more somewhat overwhelming, especially since we each have established lives on opposite coasts. She, in particular, couldn’t deal with it and ended it as a result

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? Fairly positive

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

Anything else you want to add about this hookup? Would not be surprised if it happens again.

What do you think about the Casual Sex Project? Enthusiastic support.

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