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? 2

MILF Mistress

How long ago did this hookup happen? 4 years to present

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…)? Friends with benefits

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? “Martha” is a tall, athletic beauty. She was helping a client of mine and was part of a meeting with a client. Even though I was engaged at the time, I could not take my eyes off her. Dark, beautiful eyes and hair, slim figure (my favorite), ample breasts and a sweet, intelligent disposition. She was single and a few years older than me. A definite, sexy MILF. She was wearing a sundress that showed off an incredible body. I didn’t think a lot of her after the meeting, but we had to meet a few times for business and we got friendly. After a few minutes, we went on a brief hike together, where we kissed. She knew my situation (engaged) but she didn’t care. She rubbed my hard cock on the hike! And I explored her body with my hands.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? A few days later we made arrangements for me to come to her house over lunchtime. She invited me for lunch but the intent was clear. After a delightful lunch and great conversation we kissed more and without hesitation she grabbed my hand and led me upstairs flirtatiously. Once in her bedroom, we quickly disrobed. She revealed what I suspected — the most gorgeous figure! She was better built at 51 than most 25-year-olds I’ve slept with. Her strong legs and firm ass were a turn-on but it was her breasts with the biggest erect nipples I’ve ever seen that really got me started.

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? In a whirl we were both naked. I was giving oral and she started to moan so loudly I thought the street would hear it. She reciprocated with a divine blow job that was one only an experienced woman can provide. She then positioned me so that I entered her wet pussy (wait, no comdom?) The sex was out of this world. Full of passion and feeling. We tried a few positions. I lasted surprisingly long. She then begged me to come inside her and I did, leaving us breathless and wanting more.

Did you have an orgasm? Did your partner(s)? We both did and in fact she had multiple orgasms during oral and vaginal sex.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? None. She was approaching menopause and is a health freak. But we didn’t discuss anything. We probably should have given that, combined, we’ve slept with a couple of hundred people.

What were your REASONS for having this hookup? Attraction. Instantly. No other way to describe it. Even though I was engaged it was not a barrier.

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’ve been making love on and off for four years now. Above all, she’s a good friend and confidant. She’s seen other men and during that time we refrained. But she always comes back complaining how her other conquests are not as good as when we’re together. We try to see each other once in a while.

To whom did you talk about the hookup? How did they react? None for me given that I’m married. She’s mentioned it to close friends.

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

Do you regret this hookup? If so, why? Sometimes I do feel guilty. I love my wife and would never leave her. But she is so bland in bed I need Martha to get me fired up and feel loved.

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? The friendship and closeness that accompanies the sex. We haven’t crossed the line to love. The worst is that I am cheating on my wife regularly.

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

All things considered, how NEGATIVE was this experience? A little negative

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