The Best Friend of All



What’s your gender? Woman
How old are you? 23
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: College degree (eg., BA, BS)
What’s your current relationship status? Single
Religious affiliation: Agnostic
How religious are you? A little
What’s your sexual orientation? Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? Many
How many hookup stories have you here posted before? 0

The Best Friend of All

How long ago did this hookup happen? About a year

What was your relationship status at the time? In a relationship (monogamous)

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 met James (not the real name, of course) because I used to go to the store his family owned. I was instantly attracted although I wouldn’t describe him as being a traditionally attractive person. He had the longest (I mean, super long. To the middle of his back just about.) dark brown-blonde hair and an unfortunate perpetual baby-face. He was built very burly, and very strong though. Definitely a man who looked like he had done some hard labor for a good part of his life. When we met we were both in monogamous relationships, but there was definitely mutual attraction.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? This was actually the second time we hooked up. The first involved large amounts of alcohol and was less than fulfilling. But the second time was different. We had been friends for about 3 years at this point, best friends even, and I had certainly loved him for a long time. One night we were cuddled up in a camper behind his family’s house after a family/friend party involving large amounts of alcohol on both our parts. There wasn’t any planning but he initiated and I reciprocated cuddling. Then he told me he loved me and we kissed.

The story kind of begins a little before that though. A year after our first hook up James and I took a canoeing trip together where we both had a few hits of LSD. Surprisingly, even under the influence of that much acid, I refused to have sex with him because I was in a relationship at the time (the same relationship I was in during our second hook up). Even though I wouldn’t have sex with him I did let him touch and fondle me. The effects of the drug made me feel like an absolute goddess. It was one of the best sexual experiences I’ve ever had. We hooked up about a month later, both saying how much we wished we had sex the night of our canoe trip.

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? The moment of the kiss in the camp initiated 2 – 3 days of a nonstop fooling around/fuck fest. I can’t even remember when either one of us slept. From the night of the kiss to the first early afternoon I still wouldn’t have sex with him. We fooled around for nearly 12 hours and it was one of the dirtiest and sexiest times I’ve had.

After kissing and fooling around in the camper, that next morning, when we had light to see by, we sat on opposite sides of the camper and watched each other masturbate for hours. I opened my legs wide and let him enjoy me slowly fingering and play with myself. Sometimes he’d give me orders like “open your legs wider”, “spread your pussy apart more”, or “suck on your wet fingers”, and I’d happily oblige. I watched him stroke his huge dick (8″ – 9″, maybe more and with a nice girth) in the early afternoon summer sun. He was absolutely gorgeous.

At one point, he asked me to get him a beer so I pulled one from the 6 pack on the camper table and rubbed the tip of it all over my wet pussy while he watched. I sauntered over to stand in front of him, opened the beer, took a drink, and watched as he finished the rest. When he finished, we shared some slow, sensual kisses after having shared the beer I rubbed between my legs. We watched each other masturbate awhile longer but eventually moved up to a private room in his mother’s house.

At this point, I’m still reluctant to have sex with him although we’ve done everything but. We find our way to a bed and lie down side by side, but eventually, the urge to fuck and be fucked was too overwhelming that I rolled over on top of him and rode him with everything I had. He picked me up from riding his dick and had me ride his face. Not only did his head feel good between my thighs, he definitely knew what he was doing with his tongue and mouth. He ate me out like a starving man. When the feeling became too intense I lifted myself off his face but he told me to “sit my ass back down” and I immediately obeyed, especially enjoying him kissing my ass as I came back down to sit on his face.

Eventually, we got around to fucking some more. This man put me in enough positions to fill an entire erotic novel. In fact, there wasn’t a position he couldn’t put me into or a way he couldn’t fuck me that I wouldn’t enjoy. It’s amazing what the body is capable of when the dick is so good. He had me every way he wanted to have me, but my favorite had to be when he was lying directly on top of me, pounding me with his huge cock and his big, callused hand wrapped tightly around my throat.

Unfortunately, the best sex of my life does not have a happy ending. After we both came I cried from the shame of myself and guilt of betraying my partner. Although James did comfort me, which helped immensely.

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? After the hook up I still felt horrible and ended up leaving my partner, never telling them the truth of what happened. I really had hoped something would become of James and I, especially since I thought we both loved each other. Later I learned he was just interested in sex, and it destroyed our friendship even though we still hang out from time to time. Looking back, I’m glad nothing became of us. It definitely would not have worked out.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Birth control pill / patch / ring / injection / implant, I don’t know if my partner was on any (other) method

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, Hoping or expecting it would lead to something more, Intoxication, To feel better about myself, To feel more desirable, To feel more confident, To cheer myself up, I was feeling lonely

How intoxicated were you? Drunk/high but not wasted

What substances did you consume? Alcohol, Marijuana, hashish

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

What substances did your partner(s) consume? Alcohol, Marijuana, hashish

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 talked to James’s brother and I also talked to my best friend at the time. They both had the same general “these things happen. Don’t be too hard on yourself.” answer.

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

Did you get emotionally hurt as a result of this hookup? Very

Did your partner get emotionally hurt as a result of this hookup? I don’t know / I’m not sure

Do you regret this hookup? Very much

Why do you regret this hookup? I was ashamed of myself and had guilt because I felt as though I betrayed my partner at the time.

What was the BEST thing about this hookup? The sex was hands down absolutely the BEST sex I’ve ever had, even to this day.

What was the WORST thing about this hookup? The feelings of shame and guilt.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Definitely. The hook up also felt like a grab for attention on my part. I didn’t feel my partner was meeting my sexual needs at the time. I’d hook up with someone again but not while in a relationship and not with a friend.

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

All things considered, how NEGATIVE was this experience? Fairly 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? Casual sex should be talked about more, especially cheating. It doesn’t make it okay to break a social contract but I was surprised by the number of people who seemed to be okay with my actions. I, on the other hand, had more or less condemned myself. I later found out that so many more people engage in this behavior than I previously thought.

What do you think about the Casual Sex Project? Great resource for people looking to discover the infinite ways humans experience sex and sexuality.

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