Rebound For My Rebound’s Mom



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? Atlanta, GA, United States
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Data Scientist
What’s your current relationship status? Dating casually
Religious affiliation: Agnostic
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)? 14
How many hookup stories have you here posted before? 0

Rebound For My Rebound’s Mom

How long ago did this hookup happen? Ongoing

What was your relationship status at the time? Dating casually

How would you best classify this hookup? Short fling

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? A female friend, married, who is my age, “arranged” for me to be a rebound for her younger cousin. Cousin only had one partner and just got out of a 10 year relationship with her ex that started back in HS. It ended up continuing for over three months, but I knew the end was near. In the interim, her mom started flirting with me. She was unexpectedly widowed late in 2017, and did not have any activity since.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? My dad told me the biggest compliment a woman can give you is to introduce you to her friends. In this case, my rebound’s cousin’s perspective means a lot – she was highly coveted when single. Her cousin clearly took to me physically and emotionally, but as things started to die-down, her mom threw out some softballs to start flirting with her. I definitely took the bait. My former hookup is quite attractive, and it’s clear where she got her looks from, her mother. Daughter is eight years younger than me, mother is 16 years older.

The flirting became more aggressive and direct, less euphemisms. I said my only boundary was things had to be over with her daughter. It was clear we weren’t in it for the relational aspect.

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 mother had to work two Fridays ago, but was supposed to meet her kids camping at their cabin the next day. I texted her if she wanted company that night, which she was receptive too. We briefly spoke and I told her there’s no sense in delaying something happening, if her daughter found out regardless, it would be bad. Plus, I said the only expectation was I was going to sleep there, even if it was on the couch.

I knew we had a lot to cover about our histories, etc. She had only been with two men previously and was faithful to her former husband for 30 years – didn’t even kiss another man since then. Despite my higher body count, she was a progressive thinker knowing I was unmarried. When I was her daughter’s age, my body count was 3. I learned from one or two one-night stands I need to have a connection with somebody, which I had with her. I was as nervous as she was because I wanted it to be worthwhile for her since she probably never fathomed having another man even one year ago.

At first we were in her pool (secluded area, no threat of neighbors). As we wrapped up our historical sex discussion, we kissed for the first time. She suggested transitioning to her whirlpool tub in the master bathroom. There we kissed and undressed each other before getting in. She’s very well built for a 51 year old woman, but wasn’t used to seeing a muscular guy like me for a long time. Plus she remarked I was bigger than anybody previously.

It seemed to progress naturally. Some foreplay, some talking, some laughing, etc. It got to the point where she said, “I want you to fuck me,” then we proceeded to her bed. It was just missionary for the first time, but very sensual. She was fully engaged, very passionate with kissing, she was moaning loud for the majority of it. I told her to let me know when she was going to cum. She did twice during the normal course of sex, then came again when I came.

She never had three orgasms in sex in 35 years of being active. She said she could count on two hands the amount of times she came twice, and it usually involved oral sex as a prelude. It was the most powerful sexual experience I had, which I told her.

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 didn’t get much sleep and both performed oral sex on each other later, followed by another round of sex, where she was more assertive. She called her kids the next morning saying she got called into work but would be up on Sunday. We spent the day and night together, but managed to not be sexual during the day after we crashed for a few hours.

We have to pick our spots, but we’ve had two more encounters since then.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Her tubes were tied.

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Emotional intimacy, closeness, connection, Thought it was an important experience to have, Intoxication

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

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 didn’t give a clear ‘yes’, but I didn’t give a ‘no’

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? Nobody due to risk of it becoming public.

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? I don’t know / I’m not sure

Did your partner get emotionally hurt as a result of this hookup? I don’t know / I’m not sure

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Being totally uninhibited with somebody who shares same value of you, that you see in them.

What was the WORST thing about this hookup? It’s going to have to end.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It meant a lot to see a widow experience passionate sex again. I was glad I could be her “first” after her husband passed away since it was equally as meaningful for me.

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

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

Anything else you want to add about this hookup? Too many women my age are not as open sexually I’ve found. Being with a woman who is completely confident in her sexuality is powerful.

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? I would like to see more women be liberated.

What do you think about the Casual Sex Project? Amazing.

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