Friend Of A Friend

by The Bad Guy

What’s your gender? Man
How old are you? 40
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? STL
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Office Manager
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Easy?
How many sexual partners have you had in your life (including oral sex)? Not sure, 15-25?
How many hookup stories have you here posted before? None

Friend Of A Friend

How long ago did this hookup happen? Around 18 years ago

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? 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? She was around 20 years old, and was reasonably attractive. She had long curly blonde hair, was caucasian, 5’5 ish, and was slightly curvy with larger breasts. I met her “that day” in that it was within 24 hours. I met her at a party late the night before. Then she came over and we hooked up earlier the next night. My friend was trying to date her, but they weren’t exactly a couple. He brought her to a party at my place, and my girlfriend was also there. Within an hour we had found ourselves alone for a moment and started to make out.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? She got my number after we made out for a few minutes, but before we returned to friends. Early the next day, she texted and asked if we could hang out. I invited her over again that night. We both knew what we were interested in.

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? I was in college and lived at home. It was a Saturday and my family was gone. She came over and we went directly to my room. We turned something on TV to “watch”, but within ten minutes we were making out. In very short order she reached down and had her and on my cock, registering how hard it was and making it harder. 30 minutes after she walked in my door I was sliding my jeans off and she had her mouth on me. As I watched her blow I asked if she wanted to go further. It was “that” time and she said she was self conscious, so we’d just play with me tonight and that I could finish in her mouth, so I did. It was fun, but not mind blowing. She’d switch techniques and was best when using her hand and mouth together. After we got a snack and cuddled to actually watch what we turned on, it was around 8. She stayed until 2 am and went down on me 3 more times. Each was a little different.

The first time I had her top off, and it stayed off until she left. Her breasts were larger, but fit her frame, and she had pointy, pokey nipples. The second time, I stood and she used her hand with her mouth the whole time. It was quick and she stroked me off on her chest, cleaning off in my bathroom after. The third started when a parent knocked on my door. I talked to them through the locked door and she came over and started as the conversation was going on. When the conversation was over I got a little aggressive, taking her by a pony tail of hair to try and fuck her face. She didn’t have a lot of deepthroat experience so it went only so well. Her makeup ran so I decided to finish on her face, which ended up a mess. After taking a while cleaning up, I thought that may be the end of the night, and I guessed it was rougher than she’d experienced, but she stayed. After midnight I started suggesting is was time to go. After a while of ignoring me, she softly started a forth time. It went forever, and I was worn by that point. It was soft and leisurely and it was a surprise when I actually finished again, which she swallowed. I could tell she wanted to spend the night, but I was firm and soon after she left.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than 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? I felt very guilty the next day as I spent the early afternoon with my girlfriend. I also felt satisfied, something akin to scratching an itch. I wanted the whole thing to be done and forgotten. The hook up didn’t, she tried to come over the next night. I told her she should spend more time with my friend, he’d appreciate it. She did not appreciate that. I didn’t see her again until oddly recently I came across her on social media. We’ve both far moved on and chatted on good terms.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, No penetrative sex happened

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), To feel better about myself, To feel more desirable, To feel more confident, Power / Dominance, Boredom, It was easy / convenient

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Not at all (no alcohol or drugs)

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? No one. I betrayed a girlfriend and a friend.

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? Somewhat

Do you regret this hookup? Somewhat

Why do you regret this hookup? Betraying two people I care about. There was nothing to gain except a little sex, but a lot to lose.

What was the BEST thing about this hookup? I mean, 4 blowjobs over 7 hours. I didn’t think it was possible.

What was the WORST thing about this hookup? Guilt, the fact that the hook up wanted more.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yes and no. Reminded me of guilt and reinforced that I think it’s bad. Has not stopped me from doing more.

All things considered, how POSITIVE was this experience? A little positive

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

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