New Neighbor



What’s your gender? Man
How old are you? 66
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 West of Seattle
Highest education received: Some college (not currently in college)
What’s your occupation? carpenter
What’s your current relationship status? In a serious relationship (monogamous)
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)? 50 or so.
How many hookup stories have you here posted before? 0

New Neighbor

How long ago did this hookup happen? 17 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 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? She is still a neighbor. Small stature, very good looking. She walked up to my house to see who was moving in. We talked a little she seemed nice, a little too much of the little old lady thing going on. She was/is a bit prissy, a bit too worried. I liked her and was attracted to her size. I like smaller women. Not tiny but not big.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? She stopped by one afternoon and I asked her if she wanted to go for a drink. No planning. Just happened.

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? We had a couple of drinks. She might not have finished her second glass of wine. We went back to her house, and she was sitting on the floor next to me, and I put my hand down her shirt and felt her breast. I figured it would be ok and if it wasn’t, I would apologize. It was fine, she feigned some surprise, but I could see she wasn’t really. We proceeded to have some of the best sex I have ever had. She was passionate, responsive, active, aggressive, and came like a house on fire. She could cum in a way I have never seen before. If I squeezed a particular part of her, she could cum again. We had sex about 4 or 6 times, and she broke it off. We did not talk about much.

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? I was thrilled to finally find a sexual partner that was so into it and orgasmic. I found that this seemingly little old lady 50y/o was the best lover I had ever had. I learned a lesson. I hoped we could somehow keep going and have some fun.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Discussed STI testing history

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Thought it was an important experience to have

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? A little tipsy/high

What substances did your partner(s) consume? Alcohol

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? I don’t know / I’m not sure

Did your partner(s) consent to this hookup? They didn’t give a clear ‘yes’, but didn’t give a ‘no’

To whom did you talk about the hookup? How did they react? We live in a small town so I told 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? A little bit

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? Exciting Sex. Nothing fancy but it was very hot, at least for me.

What was the WORST thing about this hookup? It ended too soon.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? A little, it spoiled me for anything much less. But everything since is not as good. So I could say in the long run it was hurtful.

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

All things considered, how NEGATIVE was this experience? Somewhat negative

Anything else you want to add about this hookup? You never know what someone is going to be like during intimacy, you can’t judge a book by its cover.

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 am serially monogamous and am currently in a very solid relationship with a wonderful woman. I would not blow it for the world, but I wish I could have it both ways. At 66 that is far from realistic so I accept my old ways of casual sex as past and gone. I think casual sex is good and respectable.

What do you think about the Casual Sex Project? Good idea. I have had plenty and have some imagination so I probably won’t read much of it but keep it at it.

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