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What’s your gender? Man
How old are you? 41
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Muncie
Highest education received: High school diploma
What’s your occupation? Operator/Laborer
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)? 15
How many hookup stories have you here posted before? None

The Forbidden Fruit

How long ago did this hookup happen? 18 years ago

What was your relationship status at the time? Single

How would you best classify this hookup? Short fling

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 was my friend’s mother, and I knew her from hanging out with my friend and his brother for several years before this story took place. She’s approximately 5’1 and 110 lbs. She had straight, long dark hair, a dark complexion, an overall nice figure, and was attractive. But back then, I didn’t think anything particular of her, nor did we even talk much. To me, she was just my friend’s mom. At least, until this story took place.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? A few years after high school, my friend’s step-dad “Mr. H” was found to be cheating on “Mrs. H,” and when she found out, she left and shared the rent for an apartment with one of her sons but kept going back and forth. She would catch him cheating with the same woman again, get angry, then leave but only to end up going back to him after a period of time. This went on for a couple of years I do believe.

One night, I went to a local bar with another one of my friends and saw Mrs. H there, sitting at the bar, seemingly alone. I walked up just to say hey, and we talked for a few. This was probably the longest conversation I ever had with her, and she seemed as though she already had a few drinks. She started telling me how she had left Mr. H again because she knew he was out with that woman, except her words to describe this other woman were not so friendly. Long story short, she mentioned that she didn’t want to stay at her apartment because her son/roommate had a girl over, and she felt awkward to intrude. So without even thinking, I casually told her that she could crash at my place if she wanted. I was just being hospitable I thought. She turned it down, and I cordially parted to go back to hanging out with my friend and a few beers.

Before I left, she stopped me and said she changed her mind. So trying to think, since I only had 1 bedroom and a couch, I figured I’d be nice and let her take my bed and I would sleep on the couch. With that, she followed me to my place. It was now approximately 2 AM or so when we arrived, and I did my best to make her feel at home. She wandered around my small place, checking things out, then suddenly asked a question that started a topic I could never have prepared myself for.

She asked, “So how are we gonna do this?” I assumed maybe she didn’t agree with my idea for the sleeping arrangement. “What do you mean?” I queried. Her response caught me completely off guard, “So do you want to wear a rubber or just cum inside me or what?”

I felt like a wave of electricity just shot through me. I didn’t know what to say, but I felt awkward and baffled at the same time. Like I didn’t understand how she thought I brought her over for this when all I did was offer a place to crash at for the night. So I uttered out the only objective answer I could think of. “Well, I don’t think I have any condoms here.” She said, “That’s fine. I don’t like them anyways,” and with that, she got up and went into the bathroom. I got flush. I had to sit down, and I felt afraid to turn her down, thinking she might feel rejected, and plus, she was already bummed out about her whole situation. I realized then that she just wanted to use me as revenge against Mr. H to make herself feel better for him cheating on her.

She walked out of the bathroom completely naked without a care in the world. It was literally the first time I ever looked at her in any sort of sexual type of way, and I had to admit to myself that her body was quite pleasing to the eyes, especially for her age. It was apparent that she worked out more than I previously realized. Call It pre-internet era ignorance but back then, I had a preconceived notion that women her age didn’t shave their pubic hairs, but she apparently did.

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? Not wanting to rock the boat, I just played along and followed her into my room. She asked me which side of the bed I preferred. I don’t recall what I said but probably that I didn’t care. So I got undressed, down to my boxers, flipped the light switch and got into bed next to her. She put her hand on my chest and asked how many women I’d been with, and I don’t remember what else we discussed. But, I felt as though I never knew her and maybe in a way, I didn’t other than being a familiar face. I knew it was probably a bad idea but at the same time, it felt hot to have an intimate encounter with someone that I knew I should not have and found it quite arousing. Once we started kissing and groping each other, I was no longer in control of myself.

I started fingering her as we kissed, and she gently played with my penis until pulling me on top of her. I slid inside her slowly and pushed all the way in and just stayed there motionless for a moment. I probably had preconceived notions of older women with kids as being “loose.” I remember thinking that inside her felt just as tight as any of girls my age without kids did. So, it dispelled a myth for me I suppose.

I prefer slow sex, and she made it quickly known that she was the opposite and wanted me to go faster and harder. Before I knew it, I was having to pound her about as hard as I possibly could as her moans got louder the harder I pounded. I quickly was losing stamina and fortunate for me she started orgasming which allowed me to slow down and catch my breath.

Finally, she wanted to be on top. We managed to roll over holding each other without me having to pull out. She was grinding on me fast and seemed to be in the middle of another orgasm when I could no longer hold back my own. I told her was about to blow, but she acted as though she didn’t hear me, or she just didn’t care, and I ejaculated into her. Though it felt really good to do so, I felt guilty for it soon after.

How sexually satisfying was this hookup? Somewhat

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 fell asleep, and she woke up a few short hours later, got dressed, and then left. I’m not sure where she planned to go, but I know at some point, she went back to her husband. From then on, she used me for sex whenever she got mad at him and would randomly come over to my house to spend the night. This went on for about 7 or 8 months, but then, she left him for good and I never saw her again. I had no further expectations, I knew what she came around for and was using me, but the sex was good that I didn’t care.

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, Learning new things, experimenting

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol, Marijuana, hashish

How intoxicated was your partner? A little tipsy/high

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? I don’t know / I’m not sure

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? I don’t know / I’m not sure

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

To whom did you talk about the hookup? How did they react? I never told anyone. I couldn’t due to our relationship with each other, plus she was my friend’s mom.

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? The forbidden fruit. Being with someone that would be considered wrong.

What was the WORST thing about this hookup? The fact that she was using me to get revenge on her husband.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I don’t think so.

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? For years since then, I find myself recalling my memories of having sex with her and masturbate to it.

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? Mentally healthy

What do you think about the Casual Sex Project? Could be educational to see how society as a whole engages in sex.

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