A Friend Of My Buddy’s Date

by Ivory

What’s your gender? Man
How old are you? 69
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: College degree (eg., BA, BS)
What’s your occupation? retired
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Atheist
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)? 16
How many hookup stories have you here posted before? 0

A Friend Of My Buddy’s Date

How long ago did this hookup happen? 5

What was your relationship status at the time? Same as current status

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? Just met that day

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? Judy, not her real name, was in her mid 50’s, had an attractive fit figure with ample breasts. Her hair was light brown, straight and somewhat long. Overall I found her attractive. I met her at her friends place in Florida where she had gone to vacation for a few days. My buddy, Fred, was also visiting her friend and encouraged me to drive down and meet Judy; he thought we could all party and ultimately, I could fuck Judy.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The first evening we all partied a bit at her friend’s place as Judy and I got to know each other. It was a bit awkward, because Judy was reserved and not a great conversationalist. Nevertheless, when bed time came, I lobbied for her to allow me to sleep with her. She was reluctant, but agreed under the condition we did not engage in sex.

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 first evening we slept together, wearing only our underwear; I convinced to remove her bra. We kissed and touched and fondled. We did not have sex, but she was so turned on she was ready to explode. I felt certain she would be ready the following night and she was. She slipped under the covers and sucked my cock and then mounted me cowgirl style with her tits in my hands. After I climaxed, she immediately put her panties back thereby holding all of my cum inside her pussy. We had intercourse again after we awoke in the morning – it was a sloppy fuck because her pussy was still full from the previous load of cum I injected. I didn’t really care for the experience and it didn’t smell too great. The third night was a similar scenario, with her becoming slightly more aggressive, which was ok.

How sexually satisfying was this hookup? Somewhat

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? She starting becoming more attached and hoped for a future – I meanwhile was trying to distance myself. The sex was pretty good, but it was her personality and increasing attachment to me that I did not like. She was not very bright and she held strong views about various social issues that were not subject to open discussion. I do not wish to repeat the experience.

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), Learning new things, experimenting

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? My friend/buddy who was there at the time.

How would you best summarize people’s reactions about this hookup? Relatively positive

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? Somewhat

Do you regret this hookup? Somewhat

Why do you regret this hookup? See my comments above.

What was the BEST thing about this hookup? The sexual experience

What was the WORST thing about this hookup? The better I got to know her, the less I enjoyed her company.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yes, get to know the person. I learned something!

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

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

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 wish casual sex was more openly accepted and practiced.

What do you think about the Casual Sex Project? good to share

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