Best Friend’s Sometime Girlfriend, Oral Sex

by Pilot2B

What’s your gender? Man
How old are you? 60
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Louisiana
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Senior Technology Manager
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Non-Practicing Catholic
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? High Sex Drive Heterosexual
How many sexual partners have you had in your life (including oral sex)? 50
How many hookup stories have you here posted before? 3

Best Friend’s Sometime Girlfriend, Oral Sex

How long ago did this hookup happen? 40 Years Ago

What was your relationship status at the time? Single

How would you best classify this hookup? Friends-with-benefits

How long did you know the person before this hookup? For 1 to 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? This happened 40 years ago when I was single, going to college, and living in the Northeast U.S. Her name was Rachel, and she was my best friend’s girlfriend. Rachel was from our hometown and my best friend was not being faithful to her while in college. She had an average face and a “Rocking Body”. I was 20 and she was 2 years younger than me. She was about 5’4” with 36C breasts with nice dollar size nipples and a nice round bottom. She was a brunette with olive skin. My friend would spend summers at his family’s beach house and Rachel and I stayed and worked near our homes. We were friends but had not pushed things any further.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I knew that she was sexually active with my friend and liked sex. One Friday night I guess we were both lonely and horny. We went to a secluded place in a park near her home and brought a blanket and some beer.

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? After a few beers we started kissing and I got no resistance when I reached under her shirt to remove her bra. That was the first time I had seen her breasts in all of their naked glory. I started kissing and sucking on her big nipples. Rachel was loving it and so was I. I was able to reach down the front of her jeans to feel her furry bush. Next, I tried to unsnap her jeans to get them off. She stopped me and said that she was on her period and could not have sex. I was pretty sure that was being truthful as we had gotten this far and I knew that she liked sex. I undid my belt and unbuttoned my pants to free my raging hard-on. I then moved her hand to me and she jacked me up and down as we continued to kiss and I continued to suckle her breasts. I asked her if she would take me orally and she agreed. I am sure she was not that experienced but I was hard as a rock, horny, and it felt great. It did not take too long before I blew a huge load in her mouth. She tried swallowing most of it, but there was so much it dribbled out of her mouth. Afterward, I kissed and thanked her. We had to pack up and leave as it was getting late.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? No

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? This was late in the summer and I went back to college soon after. We stayed good friends but never had the opportunity to have full intercourse. She admitted that she wanted to have full sex with me if we got the chance, as she was intrigued by my size, as I was bigger than my friend. Every time I saw her after that she was with my friend and I did not want to cause a problem with their relationship, even though my friend admitted to me that he was just using her for sex.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) No penetrative sex happened

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), I was feeling lonely, It was easy / convenient

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? The only person that found out was my future girlfriend, who was friends with Rachel, and Rachel told her before we started dating.

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

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? Enjoying intimacy with a beautiful young woman and friend.

What was the WORST thing about this hookup? We never had the opportunity to have full sex.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No

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

All things considered, how NEGATIVE was this experience? Not at all negative

Anything else you want to add about this hookup? No

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 participated in casual sex before I was married, while married, and after I was divorced.

What do you think about the Casual Sex Project? Pretty cool. I like the stories.

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