Sex With My Sister’s Old Boyfriend



What’s your gender? Woman
How old are you? 61
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
Highest education received: High school diploma
What’s your occupation? Housewife
What’s your current relationship status? Engaged/Married (open)
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? Enough
How many hookup stories have you here posted before? None

Sex With My Sister’s Old Boyfriend

How long ago did this hookup happen? Summer of ’74

What was your relationship status at the time? In a relationship (monogamous)

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

How long did you know the person before this hookup? For less than a month

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? Marty was your typical 70’s hippie type. He was a head taller than me, slim, and muscular with long curly brown hair that he wore in a ponytail.
My husband (then my boyfriend) lived in a house that was split into apartments. I had seen Marty there a few times, and I would classify him as a friend of a friend of my husband. He worked with them and attended college.
I thought that group of guys were cool as they were about 10 years older, and they just didn’t seem to have any cares except to ride their Harley’s and party.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We stopped by my H/BF apartment to pick something up and these guys wanted H/BF to go get some weed for them. They could always talk him into things so he agreed. I was okay with staying, as there were a few girls I knew and I wanted to have a few beers.
I was coming out of this common bathroom and Marty stopped me and asked me if I was so and so’s younger sister, I was. Then asked about her which I told him that I hadn’t seen her in a while. Then he asks if I want to share a joint. Now I was a naive 17-year-old, but I told him yes, so he takes me to his bedroom.
Well, we took a few hits and then he says let’s not waste it. He takes a deep drag on it and then puts both his hands on my head, brings our lips together, and as he exhales tells me to breathe in. I was sort of dumbfounded but did it. His lips were so soft, then he told me it was my turn and I was a bit more clumsy and pushed my lips on his more like a kiss. The next thing I know we were kissing and my halter top was off.

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? Once he got my top off, he caressed my boobs and kissed them. I thought ‘wow I shouldn’t be doing this’, but at the same time I was getting really aroused. It was sort of dreamlike as the next thing I knew my shorts and panties were down to my ankles and he was fingering me. He certainly knew what he was doing and now I wanted him.
He laid me on the bed and started giving me the greatest oral and didn’t stop till I had an orgasm. He got undressed and stood there, I assumed that he wanted me to suck his dick. I wasn’t that experienced in giving oral so I thought ‘well I’ll do it a little and then let him do me’. Surprised, it was my first uncircumcised dick so I guess that I was curious and enthusiastic.
Then I guess he wanted to do me before my guy got back, so he put his arms behind my knees opened me up and gently slid into me. It was great sex.
When he came, yes inside me, he told how great it was. Now the funny part was that I didn’t know that he had done my sister, but his last comment was on how hairy my pussy was, just like my sister’s.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, one

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? I got my clothes on, went back to the party and was drinking a beer when my guy got back. We left and went to the movies. It was funny as he wanted to feel me up while we were watching the movie and I wouldn’t let him as I had Marty’s stuff leaking out. (I hadn’t thought about that until it happened)

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, Intoxication, Didn’t want to disappoint my partner, Just happened, I don’t know why, just went along with it

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol, Marijuana, hashish

How intoxicated was your partner? I don’t know

What substances did your partner(s) consume? Alcohol, Marijuana, hashish

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

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? I have never told anyone.

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? A little bit

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

Do you regret this hookup? A little bit

Why do you regret this hookup? At first, I did. Then I thought what the heck.

What was the BEST thing about this hookup? After thinking about it I slowly introduced some new things to our sex as we were both very inexperienced. The combination of being high and not worrying about seeing him again sort of tossed all of my inhibitions out the window. I said that the sex with him was mind-blowingly great. Animalistic!

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It certainly did.

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

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

Anything else you want to add about this hookup? Why I share this now, is that I read in the paper that Marty passed away, and well I thought about how this one chance encounter changed how I looked at sex for the rest of my life.

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? Not enough time to tell you all that I think.

What do you think about the Casual Sex Project? It nice to read about others experiences, it makes you feel like you’re not alone.

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