What’s your gender? Woman
How old are you? 31
What’s your race/ethnicity? Mixed / Multiracial
What continent do you live on? North America
What country and/or city do you live in? USA
Highest education received: Post-graduate degree (currently pursuing)
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
How many sexual partners have you had in your life (including oral sex)? 3
How many hookup stories have you here posted before? 0

Twice My Age

How long ago did this hookup happen? 8 months

What was your relationship status at the time? Single

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? For less than 6 months

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? He was a shortish, intellectual man in his late 50s, bald, with thick black-rimmed glasses and a square jaw. I had known him for a while through work and liked him, and then contracted his work services for a while, and became friends. When I left my long-term boyfriend and was left with nothing, including no place to go, he put me up in his large house and offered me the master bedroom. We had strong chemistry, and I correctly guessed where this would end up going, despite (more probably because, since he was a safe choice) his age. He turned me on, not at all physically, but because he seemed like an aware, sensual, kind man of the world. He seemed like he would be good in bed.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We flirted in our shared home for a few weeks, before we were watching a movie one night, sitting on a blanket on the floor, and ended up embracing, rolling around on the floor together, pushing our torsos together, and entwining our legs. I wasn’t ready for much more yet, so when he kissed me lightly on the mouth I excused myself and went to my room.

A few days later the same thing happened, and this time he pulled my yoga pants down around my ankles, and ran one experienced hand down to my clit. Just that touch was like fire; I was already so wet from the forbidden, unlikely nature of the situation. I excused myself again but was so wet for hours; I masturbated in my room, thinking of him, coming powerfully several times.

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? Over the next couple weeks we would go further and further, mostly him eating me out enthusiastically until every cell of my body was singing with joy and exhaustion, and I would always tell myself that this was a bad idea, not to do it. I’ve never been one for casual sex; it’s a pretty big part of my self-concept that I don’t go in for casual sex. But at that point I was already 30 and had only been with one man in my life, and ran out of reasons why I shouldn’t ride this guy’s cock and have screaming orgasms with him. I knew it was a time-limited situation and I really, really wanted it.

We had several sessions of oral before trying penetration, and he was so nervous because of his age. What if he couldn’t get it up? That’s what happened the first time, with a condom; he got hard for maybe 15 seconds, but that was plenty of time to enter me. He actually felt amazing, semi-erect, because he had a gorgeous huge cock and the friction/suction was even better than it would be if he were totally hard. His problems with his erections went away before long; he knew that he satisfied me, and in fact, was the only man that could make me come with his 8″ cock alone. One time he was sleeping in his bed, and I went to spoon with him. He got hard, and since I had been wet just thinking about that no-strings-attached cock, I arched my hips up and backed myself onto it, letting him enter me smoothly. I have never had an orgasm like that in my life. 7 or 8 gentle, languid thrusts from him and no attention to my clit whatsoever, and I came hard. He would always hold me after sex. He said that my pussy tasted like the sweetest honey. I have never known anyone who loved the female body and female sex as much.

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? Unfortunately he was unable to handle the fling-like nonmonogamous terms of the relationship, and would get extremely jealous (yelling, throwing things) and attempt to be controlling, which I would not abide. I had just gotten out of a long-term relationship with a man to whom I lost my virginity, and the next year would enter another long-term monogamous relationship. I did love this man very much, and grew very bonded to him, but was unwilling to continue the relationship when it was clear that it was hurting him. He ended up engaging in some pretty crazy behavior – driving up to my new town and pounding on my door, jealously ranting outisde – so I no longer speak to him.

I worry that I will never have sex as good as the sex I had with this man. I’m sure it sounds gross to others, but a much older lover that was motivated to please me and secure in his skills, along with a really really great penis that seemed to have been tailor-made for me, was a once-in-a-lifetime experience for me. I still dream about it.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Withdrawal, Fertility awareness (days counting, temperature), Discussed STI testing history

What were your motives for this hookup? Fun, pleasure, horniness, Learning new things, experimenting, Emotional intimacy, closeness, connection, To feel better about myself, It was easy / convenient

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 ex, when he wanted to get back with me (reacted with disgust and anger, condemnation)
My best friend (reacted with neutrality/happiness if I was happy)
My dad (he was alarmed but let me make my own choices)

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? Somewhat

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? The NSA nature of it, his oral skills, his perfect cock, the convenience of having him in the other room; I could pop right in and pop on him when I was horny

What was the WORST thing about this hookup? Jealousy and controlling nature on his part

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yes. I am proud of myself; because I have a low number of partners in general, I’m happy I had something other than “monogamous relationship leading to marriage” to put on my roster. I feel that it makes me a more well-rounded person, and someone who knows more about her sexuality.

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? I still fantasize about finding an older well-hung man to hook up with again. Something about their probable skills in the bedroom, having lived and loved a lot more and not grown up in the age of internet porn and Tinder, and the fact that they’d consider having sex with me, an attractive 30-something, to be a gift.

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 don’t judge anyone for anything they do. I wish that my own mores, personally, let me “live” and hook up a little more, and enjoy it!

I do wish that it weren’t so very cool to pretend not to care about those you have sex with. “Catching feelings” is not a disease or an illness. The fact that “catching feelings” is a saying, to me, means that our approach to casual sex needs to be evaluated.

What do you think about the Casual Sex Project? I think it’s wonderful. Shared, real, anonymous experiences.

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