My Terrible Friend’s Ex-Boyfriend

by Creep

Gender: Female
Age: 27
Race/ethnicity: White
Location: Evansville, IN, USA
Highest education received: Some college (currently in college)
Occupation: Customer Service
Religious affiliation: Humanist
How religious are you? Not at all
Sexual orientation: Heterosexual
How many hookup stories have you here posted before? 0

My Terrible Friend’s Ex-Boyfriend

How long ago did this hookup happen? 8 months ago

How would you best classify this hookup? Fuck-buddies

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 my partner– we’ll call him Stan– at the birthday party of a mutual friend. We actually went to high school together but did not know one another and when he walked into the party that afternoon, he looked NOTHING like he did in high school. When he walked up, I was sitting with a friend of mine who was actually a REALLY bad friend. I had been trying to shake her for awhile but we had a lot of mutual friends and it just felt really awkward. A few months before she had been telling me about this guy, “Stan,” that she had been seeing, and she was complaining that he was going to be at the party. Mysteriously enough, I had never seen a photo of him or her out with him so I had no idea what he looked like. Anyhow, when he walked up to the picnic area where the party was being held, he immediately caught my attention. He was tall and solid– he looked like a MAN. He had a giant beard and wild hair, he was wearing a black shirt and black jeans with a giant tear in the knee and I. Was. Captivated. I immediately said, “Oh my goooood, Terrible Friend, who IS that?” She replied with, “That’s my ex-boyfriend, Stan.”

OF COURSE IT IS. FML. [Fuck My Life]

We didn’t talk at the party… I could feel him eyeballing me as I mingled and talked with everyone else, but he didn’t say anything to me at all. I left several hours later without having breathed a word to him. I regretted not saying anything but figured at some point I’d run into him when she wasn’t around.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it?: The next morning, I woke up and saw I had a friend request on Facebook. From Stan. My heart started racing and I immediately accepted it. He didn’t message me at first. Later that day, I logged into OKCupid and saw he’d messaged me there. We talked a bit, I asked him very bluntly how recently he had been tested for STIs, he told me it had been a few weeks and sent me a photo of his receipt from the clinic he used with the date on it. I invited him over that night.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? Did you have an orgasm? Did your partner(s)? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? Stan came over, we drank some wine and watched a movie. He was kind of shy, which surprised me, but conversation came very naturally. He jokingly said he’d sleep on my couch because he was “too drunk to drive,” and I made it very clear if he was sleeping in my house it would be in my bed. He pulled me into the bedroom and stripped down. We crawled into bed together and started kissing and exploring one another’s bodies. It started with him giving me oral which led to several orgasms for me, then PIV intercourse which led to several more. He was very attentive and clearly knew what he was doing. We fucked for what felt like hours. It had been awhile for me and he definitely took his time breaking me back in. He talked a LOT, and told me over and over again how beautiful my body was. When we finally finished, the sun was coming up. We slept for a very short time, then he got up and left so I could go to work, and I high-fived him, thanked him for the good time, and planned to never see him again. Luckily, he called me a few times after that and we had mind-blowing sex on several more occasions.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We did not use protection, but we did discuss STI history and the fact that I am surgically sterile, and I got tested once during our time together and then after him and before my current partner.

What were your REASONS for having this hookup? I had filed for divorce earlier that year. It had been a VERY long time since I had any sexual interaction with my ex-husband and I had been hesitant to hook up with anyone else, even after a year of abstinence. But when I saw Stan I knew I would regret it if I didn’t try because I was so intensely attracted to him.

Were alcohol or drugs involved? If so, how much? We each had a few glasses of wine before but we both made our intentions very clear before the wine. When we met initially at the party, neither of us were drinking.

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? After we stopped hooking up (my decision) I wrote him a lengthy email letting him know how much I appreciated the experience and him easing me back into a normal, healthy sex life. My expectations at this point are that if we see one another at another party, we’ll high five and be glad to see one another. I do not want to hook up with him anymore– neither of us wanted a relationship at that time, and I lucked into a man who makes me very, very happy very shortly after cutting Stan off. There were absolutely no hard feelings, we ended things on good terms, but we weren’t friends before and we did not carry on pretending we were after. He’s a very sweet guy, but a little unsettled in life for my situation.

During the course of our hookups, I finally cut ties with the Terrible Friend. I didn’t let her know about my interactions with Stan, I didn’t want to crush her, only to ease her out of my life. It was fine.

To whom did you talk about the hookup? How did they react? I told my very best friend about the hookup. She was also friends with the Terrible Friend and she was not at all surprised. She did want details. She got them all.

Was this a consensual and/or wanted experience for you? For your partner? It was absolutely consensual and wanted on both our parts.

Do you regret this hookup? If so, why? No regrets ever. He made me feel good about myself again and gave me a LOT of orgasms, haha. I like to think I did the same for him.

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? The best thing about the hookup was the lack of inhibition. We were both very straightforward and had no expectations beyond great sex. The worst thing was having to keep it a secret because of Terrible Friend, but ultimately that was a good thing, too. It absolutely changed the way I thought about casual sex– I never would have had sex outside of a committed relationship before, but when I let that hang-up go, I had a very satisfying sexual relationship with no obligations outside the bedroom.

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

All things considered, how NEGATIVE was this experience? Not at all negative

What did you think about this story? Tell us in the comments!

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