This post is sponsored by The T Bar.
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? Virginia
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Sr VP
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)? 150
How many hookup stories have you here posted before? 12
Redhead in my bed
How long ago did this hookup happen? This week
How would you best classify this hookup? One-night stand
How long did you know the person before this hookup? For less than a month
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 travel a bit and I’ve tried before to post ads online to the effect of ‘handsome executive in town to please you.’ It’s just for fun — there’s never any serious response. Until now. “Rebecca” responded to an ad I posted a few weeks ago during my last visit to her city. She couldn’t meet then but in the meantime we traded emails to stay in touch. When I had to go back to her city a couple of weeks later I asked if she could get together. She could, and we made plans to hook up. In the process of emailing her I learned she’s in a relationship and wanted to keep this hush-hush. We traded photos so I had a good sense of what she looked like. The day came to meet in my hotel bar to see where things go. She was just as beautiful as her photos — a wonderful smile, long and flowing reddish-blonde hair, fit and trim. She’s a professional and very smart too, which is a turn on to me. With blue eyes, that dashing smile, beautiful face and a body to die for,well, I knew it would be a fun evening. The ultimate MILF.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We hugged in the lobby and proceeded to take a booth in the bar. We talked a lot since we established we had some things in common through the earlier email exchanges. We conversed for more than an hour over a glass of wine, each time making great eye contact. I eventually started to hold her hand and she was very comfortable with that. With her limited for time that evening I think we both came to the same conclusion. Time for a nightcap in my hotel room upstairs.
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? We kissed in the elevator before strolling toward my room. Once inside it wasn’t fireworks right away. We sat on the couch and talked some more before I leaned in to kiss her. She quickly reciprocated. It was off to the races. I ran my hands around her fit, muscular body. She ran her hands all over me. A few minutes later I changed position so that I was kneeling on the ground while she was sitting on the couch. She started unbuttoning my shirt and then undoing my belt. I was hard and she quickly grabbed my raging cock. At this point she got up and stripped naked, revealing a tight, fit body that belies her over-40 years. I lifted her up and carried her toward the bed. We made out passionately and I eventually grabbed a condom. We exchanged oral for quite some time, and I was sure to make her orgasm first. She was very sensitive and came several times. Eventually she grabbed my cock and put it inside her. She rode me for a while and I flipped her missionary, which she really enjoyed. We also tried doggie and a few other positions. She got dry due to the condom and we eventually stopped. So she went back to work my cock with her mouth. It didn’t take long and eventually I came into her mouth.
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? We cleaned up and got back in bed to snuggle. She seemed nervous and explained that she had to get back home. She clearly enjoyed it but also recognized that she was cheating on her boyfriend. I offered to stay in touch next time I’m in town but she said not to. She assured me I was a good lover — as was she — but it was clear she just wanted to get laid.
What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms
How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it
What substances did you consume? Alcohol
How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it
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? No one.
Did you get emotionally hurt as a result of this hookup? A little bit
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? That you can find a beautiful woman online for a casual hookup.
What was the WORST thing about this hookup? That she had to run and doesn’t want to stay in touch.
Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It’s not just men who want quick sex. She wasn’t the first who just wanted to get laid.
All things considered, how POSITIVE was this experience? A little positive
All things considered, how NEGATIVE was this experience? A little negative
What do you think about the Casual Sex Project? Keep up the good work, and thanks for running my profile interview!
You have a hookup story to share? Submit it here!