by Handsome Exec

What’s your gender? Man
How old are you? 47
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Virginia
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Senior VP
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 139
How many hookup stories have you here posted before? 8

The Horny Principal

How long ago did this hookup happen? Last weekend

What was your relationship status at the time? Same as current status

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

How long did you know the person before this hookup? For less than 6 months

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? D is the quintessential soccer mom MILF. I got to know her over the course of the season when our sons played on the same soccer team. She’s a local school principal but not in the same district as the soccer league. We usually just chatted casually and often spoke about the aftermath of divorce. She knew I was married (having been divorced in the past). She’s a petite redhead, early 40s, not heavy but a bit thick in the middle but with nice legs and ass. I often caught myself staring at her ample bust. After the last game of the season, D asked if I wanted to grab lunch at a local place. I said sure. We talked some more and the discussion turned to affection and sex. She said she hadn’t been laid in months. After lunch she invited me over to her place (she had just moved in) but I said I was busy. How about later that afternoon?

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We agreed to meet later in the day. She opened the door wearing nothing but a robe — it was clear what her intent was. We sat down on the couch and she immediately began kissing me. We embraced for a while, kissing more passionately. I ran my hands up her smooth, strong legs and untangled the strings of her robe. My hands went up to cup her massive DD tits. In a moment she was completely naked — and I still had clothes on. We kissed some more and she led me to her bedroom.

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? The candlelight was flickering when we arrived in her bedroom. She started stroking my jeans to find my cock standing at attention. She slowly undressed me, clearly satisfied by having a man in her bedroom, the first since she moved in alone following a divorce. Once my clothes were off, we frolicked in the bed to give each other more attention. I went down on her large clitoris. In no less than 30 seconds of my tongue action she recoiled in delight. Orgasm number one — the first of many for her. We did 69 and enjoyed each other’s bodies. Eventually we couldn’t take it anymore and I slid my cock (covered) inside her. Wow, off to the races — many positions and I took the time in between to go down on her, eliciting even more vocal responses. After 30 minutes of passionate love-making we were spent!

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, multiple

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? We laid in bed a while and talked. I eventually left and texted her how much I enjoyed our visit. I’m married (I know, I know), so I can’t promise her I’d see her again.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

What were your motives for this hookup? Fun, pleasure, horniness, Didn’t want to disappoint my partner, Just happened, I don’t know why, just went along with it

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Not at all (no alcohol or drugs)

How wanted was this hookup for you at the time? Somewhat

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? Very

Did your partner(s) consent to this hookup? They gave enthusiastic consent

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

Did you get emotionally hurt as a result of this hookup? Not at all

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Acting on the impulse of fucking a soccer mom.

What was the WORST thing about this hookup? I’m married, so there’s that.

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

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

You have a hookup story to share? Submit it here!

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