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What’s your gender? Woman
How old are you? 18
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
Highest education received: High school diploma
What’s your occupation? Waitress
What’s your current relationship status? Dating casually
Religious affiliation: Christian
How religious are you? Very
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 5
How many hookup stories have you here posted before? 0

BFF’s Dad

How long ago did this hookup happen? 3 weeks ago

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? For more than 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? Mr. J is my BFF Melissa’s Dad. Melissa and I became friends when we were in the 5th grade and I’ve known her Dad since then. I used to sleep over at her house and go on vacation with them. Melissa was a late in life surprise. She’s the only girl and the baby of the family. She is a spoiled daddy’s girl. There is a nine-year difference between Melissa and her older brothers, and I’ve heard her parents tell people they both had surgery after she was born so there would be no more surprises. Mr. J is in his early 60s and not a bad looking man for his age. He’s tall with an average build, has blue eyes and salt & pepper hair. He recently retired, but his job required him to wear a suit and tie which I always found to be attractive.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Melissa and I just graduated and as a gift, she wanted to get away to the mountains. Her parents rented a cabin in the Poconos for a month. One morning, Melissa and her mom left to go shopping and I stayed to take a run on the 12-mile trail around the lake. I got back and decided to rinse off in the outside shower.

I turned off the water and I heard Mr. J outside. In just a towel, I walked out and he was sitting on a bench trying to put on a pair of waders for fly fishing. I noticed he was only wearing boxers. He looked at me with his blue eyes and I kept staring at his crotch. I noticed movement down there so I pounced.

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? No words were spoken as I dropped the towel and went straight for his cock. He was slightly groomed. I took him in my hand and gave him a blowjob. He sat me on the bench, got on his knees, spread my legs and returned the favor. He spent a long time down there and I was thankful because his oral skills were amazing. He stood up and positioned his cock to my shaven entrance. With my hand, I guided him closer before he plunged it inside me fast and hard. I was being submissive and he took charge by holding one leg in the air and fucked me hard. It didn’t take long before his rhythm had sent me into an orgasm. The bench was not comfortable so I stood and bent over. He fucked me from behind until he got off. He pushed himself deep and I could feel each pulse of his warm cum hit me. The warm feeling felt great! He kept his cock inside me until he went soft.

How sexually satisfying was this hookup? Very

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? I could tell he was shocked when we finished. He started to apologize but I cut him off. I reassured him by saying, “If it makes you feel any better, I’m not very innocent and I did initiate this. I promise I will never tell anyone.” I could tell that made him feel better as I gave him a kiss on the lips. I told him I’ve only been with guys my age but I’m attracted to older men. I fed his ego with a few comments on cock size, stamina, technique and I thanked him for the experience. Being very flirty, I looked into his eyes and said, “You are so good, You can fuck me anytime.” He squeezed my butt and we kissed longer. I felt him get hard again so we had sex one more time. After that, we never talked about it and continued like nothing ever happened. We haven’t had sex since.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Sterilization

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Submission / Relinquishing power, Just happened, I don’t know why just went along with it, 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? I don’t know / I’m not sure

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 don’t plan to tell anyone because Melissa is a good friend and I don’t think Mr. J has ever done anything like that in his life. Melissa’s mom has treated me like a daughter over the years. My intentions were never to wreck a marriage. I just wanted to have sex with Mr. J. I would feel bad if Mrs. J found out.

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? 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? Having sex with an older man. My only experiences have been with guys my age and they don’t have the skill or appreciation for pleasuring a girl. Mr. J’s oral skills were off the wall and I’m so jealous of Mrs. J. Mr. J is the first guy I’ve had unprotected sex with. I knew he couldn’t get me pregnant so I was excited when he came inside me.

What was the WORST thing about this hookup? That he felt bad at first but I quickly reassured him I wanted it. Knowing that might be the only time we ever hook up.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I’ve always been curious about being with an older man. It was an amazing experience and I hope we can continue.

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

All things considered, how NEGATIVE was this experience? Not at all 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? Society puts stigma that sex is wrong and dirty unless it’s between two married individuals. I think sex should be something two consenting adults should enjoy no matter the age, race or marital status as long as there is no emotional connection or intent to steal away the person. Over the years, I’ve had great conversations with Mr. J. What’s the difference in having an innocent conversation and taking it a step further to having consensual sex? Why does society look down on a girl (an 18-year-old adult) that decides, on her own, to have casual sex with an older man? Why does society think it’s bad for a married person to have consensual sex with someone that’s not married as long as the only intent is sex?

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