by Handsome Exec Virginia



Gender: M
Age: 46
Race/ethnicity: White
Current location: Virginia
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Occupation: Executive
Relationship status: Married
Religious affiliation: None
How religious are you? Not at all
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 112
How many hookup stories have you here posted before? 0


Deflowering A 33-Year-Old Virgin


How long ago did this hookup happen? 3 years ago

How would you best classify this hookup? One-night stand

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 met a very beautiful woman who looked utterly stunning in a tight business suit. We were at a business breakfast. I introduced myself at this networking event and learned she was in the process of moving to our region. As someone who helps lots of people get connected I introduced her to a few people and encouraged her to call me for more information. She did. We had lunch, where I gave her some more contacts to help her get a job in our region. Other than being pretty, professional and “with it” I really didn’t think we’d end up in the sack.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was on my way to her city on business and e-mailed to see if she wanted to get together for dinner. Being a good cook, she recommended cooking us dinner at her house. I checked into a nearby hotel (I honestly didn’t think even at this point there would be much of a connection) and arrived at her house with a bottle of red wine, her favorite. We made dinner together and seeing her now — in a sundress, hair down, flirty — was a turn on. We had laughs over dinner, then walked her neighborhood, holding hands. Afterward she invited me in, and we sat up for a few hours talking. Then she revealed to me that she was a virgin. At 33. I was stunned as she was beautiful, had a fit, toned body from what I could see, had a great job and owned her own home. Said she just never met anyone she wanted to sleep with.

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? She said she wanted me to deflower her. I wasn’t prepared for that. When I agreed, she led me up the stairs to her bedroom. I slowly undressed her, revealing a stunning body with great legs, perky breasts and fantastic ass. Knowing she was a virgin, I took it slow and explained every step of the way. She was already a good kisser, so she had some experience there. It was very difficult to penetrate her. Between my size and her virginity, it took all night to loosen up through oral, touching, etc. We made love 8 times in 12 hours, but I never came. She told me I could come inside her since she was on birth control to manage her cycle. After a night in bed we took a shower and after the shower I lifted her onto the vanity and we did it again — this time I came deep inside her. She smiled, like it was mission accomplished.

Did you have an orgasm? Did your partner(s)? Yes, we both came. She multiple times and didn’t know what was going on.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? None. I was clean and she was virgin, and given the lack of planning talked it over ahead of time that bareback was OK.

What were your REASONS for having this hookup? For me, it was a surprise that I gladly accepted. For her — frankly, to finally get laid. I guess I was the one.

Were alcohol or drugs involved? If so, how much? Just a few glasses of wine. We were both sober.

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? I left the next morning to my business meeting. We e-mailed afterward and she said she enjoyed my visit. I wasn’t sure about anything long-term, and sure enough she eventually didn’t contact me. I’ve seen her a few times at business functions, but it’s always business-like around other people. We’ve never gotten together since.

To whom did you talk about the hookup? How did they react? None.

Was this a consensual and/or wanted experience for you? For your partner? Yes to both.

Do you regret this hookup? If so, why? Not at all.

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Being able to help a woman who obviously wanted to lose her virginity. The worst part was that it was dealing with the unknowns of a virgin who didn’t know what she liked. While I’ve had many partners, this experience emboldened me following a divorce.

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

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

Anything else you want to add about this hookup or anything else? I was probably used but then again we both enjoyed the experience.

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