School’s Out

by Duke

Gender: Male
Age: 45
Race/ethnicity: White
Current location: New Jersey
Highest education received: College degree (eg., BA, BS)
Occupation: Business Executive
Relationship status: Married
How religious are you? Not at all
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 60ish
How many hookup stories have you here posted before? One

School’s Out

How long ago did this hookup happen? Two Months

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…)? Sex with an Ex

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? Perry had been my son’s second grade teacher.  She has pale skin, currently shoulder length black hair and is in her early thirties.  She tends to dress conservatively and wears glasses.  She is quiet and shy until you get to know her.  The term mousey comes to mind.  However she is very different than she comes across.  She is quite inked up, with tattoos on her arms, shoulders, chest, back, stomach and thighs that are usually hidden by her clothes.  I knew her pretty well, we had dated for a little more than a year, my first relationship after my wife and I had decided on an open marriage.  She has certain sexual proclivities and liked to be fucked in public places where there is a risk of getting caught.  I did get the impression I wasn’t the first Dad she had hooked up with.  I had liked her and been very attracted to her.  We had split up more than three years ago, Perry had been looking for a real relationship and someone to start a family with.  At times though I still thought about her.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I am married, but as I said I have an open marriage and my wife and I are free to pursue and date other people, it’s an arrangement we have had for about five years.  There have been two women I have spent enough time with that I would consider girlfriends during this time and Perry was one of them.
It was a chance meeting that brought me and Perry back together.  I live more than an hour from where I work, a choice about where my wife and I wanted to raise our kids.  Because of this I keep an apartment in town that I also use as a bit of a fuck pad since my wife and I have a rule that I don’t bring anyone home.
I bumped into Perry at a bookstore, not an odd place to find her.  She was dressed in a tank top and short shorts, different than I had seen her dress before.  We started talking, and decided to grab coffee.  Coffee led to flirting and she was quickly asking me back to her place.

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 didn’t make it to her place, and barely to the car.  We started kissing and groping each other and decided to find someplace private as quickly as we could.  That would end up being the back office of a nearby business I owned part of.  I bent Perry over a desk, pulled her shorts down and my pants and stuck my cock in her.  She was facing away from me and I grabbed her by the hips and fucked her.  It took me about ten minutes to cum and Perry moaned a little.  She was eager and enthusiastic before and during but afterwards pulled her shorts on quickly and left, I think she was a little embarrassed.

Did you have an orgasm? Did your partner(s)? I did and Perry did not

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? None which looking back was foolish and I did finish inside her. I had recently tested clean and Perry was fine

What were your REASONS for having this hookup? I really wanted Perry and also had been a bit since I had sex

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? Being in an open marriage complicates things, I don’t hide it but I usually don’t volunteer it with new partners right away. I still love my wife and have no plans on leaving her, she is just unavailable sexually.  Most women don’t get it and are unwilling to peruse anything so the past five years have mostly been one night stands or short flings.
Now Perry and I have hooked up a few times since and the sex has been great. We have discussed it and I am considering resuming my old relationship with her,  but the reasons we split up are still there.  Perry still wants a family and I am still married and as I said I have no plans on leaving my wife.

To whom did you talk about the hookup? How did they react? Nobody, unless my wife asks I am not to tell her and she has also asked that I don’t brag or tell people

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

Do you regret this hookup? If so, why? No

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? I would say it was some fun with someone I once really cared about as for the worst part, I would say how complicated I have learned sex with an ex is and when your in an open marriage how that complicates things.

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

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

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