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What’s your gender? Man
How old are you? 35
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? USA-Midwest
Highest education received: Some college (not currently in college)
What’s your occupation? Self Employed
What’s your current relationship status? Single
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
How many hookup stories have you here posted before? 0

Mom’s Best Friend

How long ago did this hookup happen? 13 yrs ago & still happening

What was your relationship status at the time? Single

How would you best classify this hookup? Friends-with-benefits

How long did you know the person before this hookup? For more than 3 years

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? She is my mom’s best friend. Our families are close and I have known her my entire life. I have always had a crush on her. She is sexy, 5’4″, 125lbs, is a 34c, a brunette, and she has an amazing body.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It started at a wedding reception when Judy sat next to me on a small bench. The champagne was flowing and as we were visiting she started talking about her husband and the affairs he had. I told her that she was the most beautiful woman that I know and I couldn’t believe he would cheat on her. I told her to remember that no matter where she was that she was always the most beautiful woman in the room. She started rubbing my leg and whispering in my ear that she wanted me to come visit her when her husband wasn’t home.

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? I went to visit her about a week after the wedding reception. She answered the door and we locked into a passionate kiss and then made our way to the bedroom. I undressed her and kissed my way down her body. I licked her clit and inserted two fingers in her pussy and my little finger in her ass. She had a massive squirting orgasm. We made love for hours. Afterward, we held each other and talked, and decided it wasn’t going to be a one-time thing. We have been hooking up for the past 13 yrs.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than 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 continue to hook up and we both have no regrets. We will continue to see each other as we both love each other.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

What substances did you consume? Alcohol

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

What substances did your partner(s) consume? Alcohol

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

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.

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

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? Sex with an amazing woman.

What was the WORST thing about this hookup? Nothing.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No.

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

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

Anything else you want to add about this hookup? Every young guy should have sex with an older woman.

What do you think about the Casual Sex Project? It’s great!

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