First Hook-up With FWB



What’s your gender? Man
How old are you? 45
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? LA
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Finance
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Jewish
How religious are you? A little
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 150+
How many hookup stories have you here posted before? Zero

First Hook-up With FWB

How long ago did this hookup happen? Four years ago

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

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

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? I had known Haley for about 3-4 years, but not very well. She was a friend of my sisters, and lived in my neighborhood, but we never had a chance to get to know each other. But I did notice her distinct look. Black hair and athletic body and beautiful smile. We got reacquainted when our kids were in Sunday school together. She was collecting money for a teacher gift, and we began to text. Innocuous at first, and then the texts became flirty. I was very interested. Even though I love my wife, my sex drive is way above hers and I miss the adventure and passion. It had been a long time since I was with someone else.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? After several months, I went to her apartment lobby to drop off a magazine with an article that I thought she should read. On the way to leave, she told me she was ready to cross the line, and moved closer to me. I pulled her in close for a deep kiss. It was amazing. We made out for about 2-3 minutes (in the mailroom at her apartment complex) and then left. We made out 2-3 more times before the big hook-up.

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 made plans to meet at a friends apartment in her complex. Her friend was out of town and we would have time to relax and be alone. I got there expecting a make out session on the couch and maybe some clothes off, but she had other plans. We started to make out when I got in the door. Long, deep kisses. My hands on her face as we made out. Hers right around me. I reached around her and pulled her pelvis in close to me. What a hello! She could feel how excited I was and led me to a bedroom. She laid down on the bed and we continued to make out feverishly. Exploring each other’s bodies and enjoying the amazing chemistry. I took her top off and unhooked her bra. Her full round breasts were amazing for a 40 year old. She told me she had a reduction after her second child and they shaped and lifted them. Amazing. I took my shirt off and she reached down to feel me hard inside my pants. We continued making out and I reached inside her pants and could feel how wet they were. She wriggled out of her pants and smiled at me as my eyes explored every inch of her body. She looked amazing. Athletic body, not perfect—but perfect to me. She unbuckled by pants and I pulled them off. She grabbed my hard seven inches and started to stroke me. She then took me in her mouth—and it was amazing seeing her down on me and felt perfect. Then what she did next really surprised me—she laid back and spread her legs and asked if I had a condom. I said no, that I didn’t expect to need one. She smiled and said just don’t cum inside me. I was shocked, but didn’t hesitate to position my cock at her open wet pussy and slowly slide inside her. She took all of me inside and we kissed deeply. The kisses becoming more intense and deep and long as I slid inside her slowly at first—to savor the moment—and then faster. I wish I could say I lasted a long time, but I didn’t as I was so excited. She can’t cum from intercourse, so I fingered her and played with her clit while kissing her deeply while she came. It was an amazing experience.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, one

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? We laid there holding each other and kissing and then cleaned up, as I came on her stomach. We both agreed that we would see each other again and have stayed in touch for years—off and on. More stories to come about that. 🙂

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Withdrawal

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

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? 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? 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? The sex was great, but the intimacy with this person that I have feelings about was amazing.

What was the WORST thing about this hookup? Deception and sneaking around.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It fulfills a need for me for passion and intimacy.

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

All things considered, how NEGATIVE was this experience? A little negative

Anything else you want to add about this hookup? It was amazing and we still meet up on occasion.

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 love casual sex so long as you control the circumstance and can handle the complexities especially when married. I feel that it fulfills many desires, and that monogamy is unrealistic.

What do you think about the Casual Sex Project? This is an amazing site. Finding others in similar circumstances is amazing. Thank you!!

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