by Handsome Exec Virginia

Gender: Male
Age: 47
Race/ethnicity: White
Current location: Virginia
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Occupation: Sr VP
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)? 130+
How many hookup stories have you here posted before? 4

Banging the Apartment Manager

How long ago did this hookup happen? 4 years

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? Short fling

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 first met “Monica” during a very difficult time in my life — months after separating from my first wife. I had to move out of the house but to make it easy on my kids I looked at renting an apartment in a high-end complex near the marital home. “Monica” was the manager and I first talked to her on the phone and really liked her. I set an appointment. I waited in the lobby for her to get back from another meeting. When I heard her from a distance I knew it was her based on the phone call. Then I saw her — petite, slim (the way I like it!), blonde, friendly. And that skirt! Holy crap, a nice blouse and professional skirt that showed off her body and amazing looking ass and legs, honed by her years as a collegiate athlete. We toured the complex in a golf car. I couldn’t take my eyes off her legs, with the skirt lifted up a bit during the ride. I eventually found a unit and signed a lease. I thought that would be it. But we remained friendly, saying hi. She impressed me when she brought me a bag of toys for my boys knowing I was going through a tough time and had nothing.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? A few weeks later I asked her out to lunch but she said that wasn’t a good time. Eventually she was able to meet for dinner. We hit it off but she revealed that she was married and in the process of a divorce as well. Perhaps that’s why we got along so well.  It was a nice dinner, we hugged and went on our way. A few nights later we went to a vineyard overlooking my city and had a great time talking. She was lonely for sure but made it clear she can’t date residents of her apartment complex. I drove us back to the complex to drop her off at her car for her long ride home. But we kept talking in the car, then started kissing, first gently then passionately. About an hour later I asked her to  come back to my apartment. She gladly complied.

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 got into my unit and continued kissing passionately. She straddled me and I started to unbutton her blouse. I was stunned to find beautiful C cup breasts, which she was able to hide underneath her professional outfits. I enjoyed that view before carrying her into the bedroom. She immediately undressed me and started sucking my cock. She could not fit it into her small mouth. I went down on her and enjoyed her pussy. She gave a few moans of encouragement. After considerable foreplay, I reached for a condom but she stopped me, saying she doesn’t like them. So I went in bareback. That night we must have made love 8 times, with me always carefully pulling out. Her body was incredible. 8 years younger than me, she did not have one ounce of fat on her yet wasn’t too skinny. Just perfect. I could not get enough of her. We literally made love all night and in the morning I was spent and tired!

Did you have an orgasm? Did your partner(s)? Yes, both, many times

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? None. She wasn’t even on the pill but I pulled out. She was married but didn’t have much sex. We had no discussion of sexual history. If she only knew my scorecard! But I was clean and had no issues going bareback.

What were your REASONS for having this hookup? Loneliness mostly. Both married in dead-end relationships.

Were alcohol or drugs involved? If so, how much? None.

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? We dated and made love for quite some time after that. We’re still in touch.

To whom did you talk about the hookup? How did they react? No one.

Was this a consensual and/or wanted experience for you? For your partner? Very consensual. After our night together she said she wanted to bed me after our first dinner.

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

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? Best was recovering from a separation knowing I was wanted. It led to a number of NSA arrangements.

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

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

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