by crazedude70

Gender: Male
Age: 44
Race/ethnicity: Caucasian
Current location: Ohio
Highest education received: College degree (eg., BA, BS)
Occupation: Insurance
Relationship status: Married
Religious affiliation: Catholic
How religious are you? Somewhat
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 20ish
How many hookup stories have you here posted before? 1

After School Special

How long ago did this hookup happen? 3 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…)? 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? Her name is Stephanie. At the time I was 40 she was 32. She is about 5’7″. Nice hourglass figure black hair blue eyes.  Before the hook up we had known each other for about two years our kids are in school together. I always thought she was pretty and had fantasized her a few times.  She had just split from her husband.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We had a parent meeting at our kids school. The meeting was scheduled for two hours. Someone in her building was watching our kids.  My wife was working and I offered to drive stephanie to the meeting.   The meeting was over in about 10 minutes. As we were leaving she asked if there was anything we could do for the next couple of hours. I looked at her in the car acted like I was thinking about her question and said, “we can go to your place and fuck.”. I figured she would take it as sarcasim.  To my complete surprise she said, in a very casual way, ” OK sounds good”. Now I wasn’t sure if she was being sarcastic.

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? While driving I reached over and felt her boobs. I rubbed over her shirt, when she didn’t resist I reached under her shirt and played with them under her shirt but over her bra. The were firm and full I would guess a full C.  We hit a stop light and I reached over and un button and un zipped her jeans. I reached between her legs and played with her lips and clit. She was giving some moans that I could tell she was enjoying the attention.  We were getting close to her apt and I slid two fingers into her, she was wet.  I pulled my wet fingers out slowly as we were parking and when she looked at me I put my fingers in my mouth to taste her.

We could not get to apartment quick enough.  Once we enter her place our lips met for the first time.  After some animalistic kissing and stripping I kneeled between her legs as she sat on her couch. I did take my time breathing heavy and gently kissing her pussy.  She did cum while I was performing oral on her.  She moaned ” I want to feel you in me “. Without hesitation I pulled away she laid on the couch and I position my self with a knee on the coach foot on the floor and entered her. There was nothing slow, patient or romantic about it. I was so turned on and she had cum I entered her and I fucked her. There is no other word to describe the passion and heat of what we were doing, we were fucking.   I did cum, inside of her. There was no complaint on her part.  My orgasim was one of the most amazing I ever had.  She knew when I was shooting and she would keigle extracting every drop I had.

We did have some more time, and we fucked again with her on top and again keigling as I was Cummings in her.

Did you have an orgasm? Did your partner(s)? Yes multiple for both

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? None

What were your REASONS for having this hookup? It just happened

Were alcohol or drugs involved? If so, how much? No alcohol or drugs

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? Nothing we are still friends, but since her divorce  she has gotten in a bad relationship, which I wish she would get out of.

To whom did you talk about the hookup? How did they react? Wife, she was surprised but loved the details

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

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? Best thing –  best orgasims of my life.

Can’t think of anything bad.

First time I had extra marital sex with “permission” from the wife. Realized sex is just an act and doesn’t have to be emotional

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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