A Decade-Long Fuck Buddy

by Hippie

What’s your gender? Man
How old are you? 39
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: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Marketing
What’s your current relationship status? Single
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)? 29
How many hookup stories have you here posted before? 0

A Decade-Long Fuck Buddy

How long ago did this hookup happen? 2009

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 less than a week

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 was living in San Francisco and posted an ad on Craigslist for casual sex seeking a BBW. She responded. She was shorter and curvy with large breasts and a very slight space between her teeth, which I found amazingly sexy. Her features were an interesting mix of Irish and Mexican, and she had a fiery attitude. I was 30 and she was 36 at the time. She worked a couple blocks over from me downtown so we agreed to meet up for coffee. I had dreadlocks and a beard at the time, and she seemed very buttoned up, so I didn’t expect her to like me very much. Our conversation was very easy with lots of jokes and stories and laughing. She said she wanted to meet me again for a beer in my neighborhood.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We met up at this dive bar across the street from my apartment building to watch a bit of the Giants game. She and I had very different backgrounds but we were both enthusiastic Giants fans. After a few beers and a couple hours of joking around, I suggested we go back to my apartment. She was nervous but fine with the plan. In fact, we were both nervous. We’d both fucked off of Craigslist a few times but it’s never an easy or natural thing.

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 got up to my apartment and cracked a beer, while I told her how I’d originally moved there with my ex-girlfriend who bolted because I didn’t want children. She was wearing this blue dress with little white flowers. I remember kissing her and it was a struggle. She and I had very different approaches to intimacy and things were a bit off. We struggled through the foreplay and got naked. I licked and fingered her pussy for a good while since I love eating pussy and she had a surprisingly juicy pussy with thick lips and a nice exposed clit. Being younger and a fitness freak, I put on the condom and slid all the way inside of her. I began fucking her firmly and deeply as I had always done up to this point. I’m 6’2″ and she was about 5’2″ so the size difference was acute but I made a point of sucking and licking her large tits. She just kept saying “Oh fuck, oh fuck, oh fuck, oh fuck” as I pounded her. She said (then and prior at the bar) that she hadn’t had a lot of sex over the past 10 years, being in a sexless relationship. She hadn’t been fucked hard or deep in a long, long time and she was overwhelmed at first. Then we slipped into this amazing and deep rhythm, fucking in this amazing raw, intense way. Her legs and pussy opened more and more with every thrust, her juices soaked my sheets and mattress. We were safe and I wore a condom, but even with it, I could feel her entire body react to me. This quiet, almost shy woman was practically screaming and clawing at my back as she came and came and came. After nearly an hour, I finally came and could feel her pussy squeezing every drop of cum into the condom.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, 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 was quick to leave, as it was late and we both had to work in the morning, but I felt very relaxed and happy with the experience. She emailed me in the morning with a cute message saying she was a tad overwhelmed. Hence all the “oh fuck’s”, but had a great time and would like to hang out with me again. This began what has been the longest relationship I’ve had with a woman, as we’ve been friends and FUCK buddies for a decade now. Together, we’ve unlocked some amazing things in each other sexually while also developing a deep friendship. It became cumbersome when I met my ex-wife and when she found her current boyfriend.

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

What were your motives for this hookup? Fun, pleasure, horniness, Hoping or expecting it would lead to something more, I was feeling lonely

How intoxicated were you? Drunk/high but not wasted

What substances did you consume? Alcohol

How intoxicated was your partner? Drunk/high but not wasted

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? We keep our relationship secret for the most part.

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? Somewhat

Did your partner get emotionally hurt as a result of this hookup? Somewhat

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? We discovered the true depths of our sexuality and desires and were not afraid to experiment with each other. She went from a non-sexual person to a woman who would squirt while sucking my dick in an alley.

What was the WORST thing about this hookup? When I started dating my future ex-wife.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I wish it could continue on and I miss it.

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? Best sex of my life BY FAR. Her’s as well, we both miss each other.

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? Casual sex is good sex but has become far more trivial and base than it used to be with all the apps and bullshit.

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

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