Scratching the Itch



What’s your gender? Man
How old are you? 62
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, Boston
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Business Consultant
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)? 90+/-
How many hookup stories have you here posted before? 0

Scratching the Itch

How long ago did this hookup happen? 3 Days

What was your relationship status at the time? Same as current status

How would you best classify this hookup? Paid sex

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 had seen pictures of V on her web page the last time I looked for a paid encounter and was attracted to her profile, though the logistics didn’t work out the first time. We continued to e-mail occasionally and her return to my city corresponded with a meeting in the area so we made plans to get together first thing that morning. She is attractive, of average height, fit, slender, smallish breasts, short dark hair and a pleasant face. She has a few tattoos, but not anything garish or distracting. V is half my age,which made me hesitate, and she is married which seemed very hot. I fantasized about her several times while having sex with others before our encounter. When we met for our date it had been about 2 1/2 weeks since I had had sex and I was ready.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We set the time to meet at her hotel by e-mail and didn’t speak until we actually met when she opened the door. Her voice was different than I expected, but she was definitely the girl in the pictures. She was fresh out of the shower and wore a short wrap (with nothing else underneath I learned). When I came in she kissed me lightly on the cheek and we started to chat to get acquainted.

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? Gradually I undressed as we talked and began caressing her back, hips, legs and moved to her breasts and nipples, which she seemed to enjoy. Her hands were on me and soon I was aroused. She was on top of me and started to grind her bare pussy against my cock. All this time there was no kissing and no moves to give or want to receive oral sex, which I thought was unusual. In my experience a paid encounter usually progresses to a blowjob and mutual oral very quickly, which I love, but here I felt it was out of the question. V paused the action and put a condom on me and then started to ride cowgirl. Our rhythm wasn’t quite right and I popped out so she asked me to be on top. She was on her back with her legs wide open in welcome and she put one leg over my shoulder so I could have the deepest penetration. Her pussy was very wet and felt small and tight and I lasted maybe 6 or 7 minutes before shooting off in the condom. We kept looking at each other while fucking and she seemed to be enjoying it.

I took the condom off and cleaned myself off in the bathroom and returned to the bed where we chatted and cuddled some more. It was unspoken, but there was going to be a round two. V purred when I touched her body and seemed to like the contact. Her hands moved to my cock, she had me hard and put another condom on, and rolled onto her back with her legs spread again. She smiled and took me in and it felt as good as the first time. We fucked for much longer this time, varying pace, depth, angle but staying in man-on-top position. V smiled and bit her lip and was very responsive, but again it was clear that nothing else was on the menu.

One of my goals for these encounters is to affirm my ability to perform and cumming twice in an hour is one measure. V brought me to the point of no return and I shot my second load into the condom. Again taking the condom off and cleaning up were left to me, which is different from the usual practice of the provider bringing a warm towel to clean my cock. When I came back she had slipped her wrap back on and our time was up.

As I dressed we chatted, then another kiss on the cheek, thank yous and it was over.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? No

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? I went about my business and caught up with the day. Oral sex is my favorite and I wished that had been on the menu – getting it is one of the main drivers for seeking paid encounters. V was nice, but we didn’t click at the emotional level. Some of it is the age difference, I’m sure, but with older providers there is more in common. I was also disappointed that I didn’t bring her to orgasm, but that usually requires oral attention to vagina and clit that wasn’t on the menu. I don’t think I will see her again.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

What were your motives for this hookup? Fun, pleasure, horniness, To feel better about myself

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? No one

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? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Sex with someone new. Two strong orgasms

What was the WORST thing about this hookup? No oral sex

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Nope, I still look forward to new encounters

All things considered, how POSITIVE was this experience? Very positive

All things considered, how NEGATIVE was this experience? Not at all negative

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 like being with different people. Married sex is good, but I wish my wife was more open to encounters with others. Monogamy isn’t natural and I wonder if half the women I meet aren’t repressing desires.

What do you think about the Casual Sex Project? It’s great and fills a real need. I like the opportunity to be reflective somewhere other than on an escort review site.

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