Long Term Fuck-Buddy


This post is sponsored by The T Bar.


What’s your gender? Man
How old are you? 46
What’s your race/ethnicity? Southeast Asian
What continent do you live on? North America
What country and/or city do you live in? Toronto
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Business profesisonal
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? Wish the numbers were less and the quality was higher
How many hookup stories have you here posted before? Zero

Long term fuck buddy

How long ago did this hookup happen? 2010

What was your relationship status at the time? Single

How would you best classify this hookup? Fuck-buddies / Booty call

How long did you know the person before this hookup? For 1 to 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 “Liz” at a speed dating event. She was 40 and I was 38 at the time, in 2008. She was a senior exec in sales at a brand name company. She was super intelligent, out-going, had a well-organized life, 5 foot 8 inches with short blond hair and physically fit from working out. She was a type-A with a typical MBA grad personality. This was just my type. The only problem was that she was older than what I was seeking, and she was not that attractive. I’d say a 5/10.

We had a short first date over coffee, during which she laid out that this was who she is and if I was interested, I can follow up. It sounded like her intimidating high powered position kept her single all this time. I could sense that we could be in a FWB relationship. So after that coffee date, I reached out and lined up a real date which led to sex. We indeed started a FWB relationship. When either of us were dateless on a weekend, we’d go out for dinners and follow up with sex. We went to a film festival together followed up with sex. We went skiing together, which ended up with sex. If either of us were horny some night, I’d go over to her place for sex. She lived only 15 minutes from me by car, door-to-door, which was super convenient. We even took a short vacation together which included sex.

We did try a relationship once, for about 3 months. But there was little romance and we found out that our life priorities were different. That experience was good because we figured out that we were not meant to be, but we got along well as friends. From there, we went back to a FWB relationship and then the passion just took off. Things got kinky and rough as well as romantic and gentle as suited our emotions. We hooked up two or three times a month for almost two years while we were each seeking to find someone long term. We commiserated over our poor luck at dating, and fucked each other to provide emotional support.

Two years later, in early 2010, she got into a long term relationship with someone, so I lost track of her.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I hadn’t heard from her in about four months. Then one Friday morning, she emailed me asking how I was. I replied that I was okay and still single. Her reply was “I broke up with my ex-boyfriend last week. I need a good fuck tonight.” I had an instant hard-on reading that. I asked if she wanted to meet for dinner after work. That was how we usually started our Friday night hook-ups. But her reply was “No, just come over after work and fuck me.” I told her I would see her at 7 pm.

I showed up at her place exactly at 7 pm. When she opened the door, she was holding a glass of wine. She was still dressed in her business jacket, knee-length skirt and 2 inch heels from work. She knew that turned me on. We knew each other enough that I knew what she wanted. This was going to be the professional business woman by day and whore in the bedroom by night fantasy.

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? I said I’ve been hungry for her all day. We both chugged a glass of wine while looking each other in the eyes. I pushed her against the wall and started kissing her and biting her lip and neck. I pulled off her jacket and tore off her shirt. We made out like that for a few minutes then went to her living room. As she kicked off her heels, I tore off her skirt, and then we started tearing off the rest of each other’s clothes. We were kissing and biting and licking each other with intensity. She was already wet when I started licking and sucking her pussy. Then I had two fingers inside her and was finger fucking her to get her off.

Meanwhile, I slid on a cock ring. We didn’t use these often, but this was going to be one of those sessions where it would be needed for some intense screwing. She had an orgasm from my fingering and then I just slid into her. We never used condoms when we fucked. We knew each other’s sexual history, and while I didn’t know about her last partner, at this point, I just wanted to fuck her.

I told her you “you are a bitch for dating that loser. I should be fucking you and I’m going to give it to you now.” She said, “yes, give it to me.” “Yes” was her code word that she liked it. She was lying on her back while I held her ankles over her head as I fucked her aggressively. The sweat was dripping off my forehead onto her face. When I came, I pulled out and ejaculated on her neck and face.

I was still hard with the cock ring around my penis. I immediately inserted my cock back into her vagina. I rested her calves on my shoulders so I could grab her throat, and then I started pounding into her again like a jackhammer to ensure the intensity would maintain an erection.

I said “you are a whore.” She replied “yes I am. I need a man who understands me.” At that point, she had an intense orgasm. I kept pounding away while she was screaming, and then I felt a second orgasm come from me.

I flipped her around. She was on all fours and I fucked her doggy style. I squeezed her hips firmly with my hands as I thrust into her. When she rested her head onto her arms, her shapely ass pointed higher and I started spanking her. “Are you going to go back to that loser?” She said “I want your cock inside me now. Yes, fuck me more.” So I kept going, I started pulling her hair, and then she came again.

We took a break, and then she rode me. She was riding back and forth very aggressively which brought forth another orgasm from her. I left her place around midnight. We agreed that it was best to take a break before hooking up again.

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? We resumed our FWB about a month later. We hooked up about once a month, then it got less and less.

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

What were your motives for this hookup? Fun, pleasure, horniness, I was feeling lonely, She contacted me up for a hook-up

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

What substances did you consume? Alcohol

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

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? I didn’t tell anyone.

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? I don’t know / I’m not sure

Do you regret this hookup? A little bit

Why do you regret this hookup? I should have moved on and focused on looking for the right person for a relationship.

What was the BEST thing about this hookup? I had a dry spell, I was not feeling good about it, and this came at the right time to pick me up.

What was the WORST thing about this hookup? I don’t know.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? My relationship with “Liz” taught me that sex and LTR do not necessarily work together. For most people, it does. In my case, I was looking too long to find the “right” person. I am married now. While my wife is loving and a good person, she does not have the sex drive I need, and she does not turn me on the way Liz and other women have. Its as if I need non monogamous sex to be turned on, which is different from a monogamous relationship. I won’t cheat on my wife now, but I still wish I could go out and have random hookups and fuck FWBs from my past like Liz.

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

All things considered, how NEGATIVE was this experience? Somewhat negative

Anything else you want to add about this hookup? After it ended, I just went home, then picked up with the rest of my weekend. It was exciting when it happened and to get off, but it was just the rush of orgasm and sexual communication. I could have just as easily got off in different ways, by getting drunk, getting a high from a hard run, or playing sports with my friends. It made me realize that sex is like just another dopamine rush.

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 wish I could have just settled down much earlier with a family and then I wouldn’t have been running around trying to get pussy, but focus on building a better career and life for me and my family.

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