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What’s your gender? Man
How old are you? 50
What’s your race/ethnicity? East Asian
What continent do you live on? North America
What country and/or city do you live in? Canada
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Business development
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Sexually inexperienced until later in life
How many sexual partners have you had in your life (including oral sex)? 10
How many hookup stories have you here posted before? 1

Fuck buddy for sexual workouts

How long ago did this hookup happen? 18 years ago

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 less than 6 months

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 a small town where it was hard to find singles to date. A colleague at work, Bill, was divorced for about a year. He was 40 at the time. I was 32. We became friends and acted as wing men for each other at clubs. One night at a bar, I was chatting up a group of women. One of the women I was speaking with started coming on to Bill.

Afterwards, Bill told me her name was Heather. We both thought she was with the group of women talking to me, but it turned out she was there at the club by herself. I was impressed that Heather had the confidence to walk into a club alone and approach men of interest to her. Bill and Heather started dating soon after that. He told me she was also recently divorced for about a year, and she had a five year old son whom she shared custody with her ex-husband. She had a good job as a regional sales manager.

Heather was quite attractive, positive and friendly. She was 35 with brown shoulder length hair. She was very fit and athletic. Bill told me that she worked out at the same gym as him, but he never noticed her until now. She did triathalons and recently started sail boarding. I could see that Bill was smitten.

For the next month, all Bill talked about was Heather. As a humblebrag, he even mentioned that he needed to buy more condoms. Then I heard Bill start to complain that he was just a “dildo with eyes” to Heather. Before long, she broke up with him. He wanted a relationship, and apparently Heather did not.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The next time I was back in the club, I saw Heather, hanging there alone and apparently looking again. I was standing alone in the club for a little too long looking to start a conversation with someone, so I approached her. I didn’t let on that I knew much about what went on between her and Bill. To my surprise, she took quite an interest in me. She wasn’t drinking, but she sure came on to me in an unexpectedly forward manner. She was even telling me that she liked the feel of my muscles. I have a slim build, but I started weight lifting intensively at the gym at the time. So this was a nice compliment. At that point, I realized she was simply a horny woman looking to enjoy her singleness after marriage with some casual flings. I was willing to oblige. I was horny, I hadn’t been laid in a long time, and I didn’t see how this would affect my friendship with Bill.

Heather and I had dinner the following evening. The conversation was good. It ranged from talk about our work and our interest in business, about family, our different sports adventures, and even light hearted funny. There was no sexual innuendo, but deep down, I could feel sexual anticipation between us. My cock was hard most of the evening, and I could feel precum oozing from the tip. We went back to her home. Her son was with her ex for the weekend.

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? She doesn’t drink, so when we settled into her living room, there was no preliminary small talk. We spontaneously started kissing. This led to fondling while we peeled off each other’s clothes. She was wearing black lacy thong panties underneath. My cock got harder seeing what she was wearing and knowing that she was prepared for this evening from the very start. The feeling of not wanting to let her down brought out my sexual confidence in ways I had not expected. I was saying and doing things I never did before with anyone.

We enjoyed feeling up each other’s fit bodies. Rather than peeling off her sexy thong panties, I took my time enjoying the sight as I licked her body and traced the outline of her thong with my tongue. I could feel the wetness in her crotch area. I told her she smelled so sweet down there. She responded by squeezing her thighs around my head, pressing my face against the wet thong that stood between my mouth and her pussy. The foreplay lasted for another half hour until I said, “let’s go to bed.” She held my hand and led me to her bedroom. I find the first time being led to a woman’s bedroom is most arousing, particularly being led now by a woman slightly older than me and apparently more sexually experienced. I was whispering into her ear how sexy she was and how hot I found her body. She liked hearing that and returned my compliments. I slipped off her panties and started giving her oral sex. I am not normally into oral sex, but her wetness was fueling my lust. I was licking her juices, enjoying the taste, and looking for ways to get more. I told her to tell me what moves get her more wet. She guided me by saying “oh yeah, oh yeah” and “right there, right there.” I proceeded to finger her. I found that pushing up and rubbing vigorously got her moaning loudly. I combined this with rapid tonguing of her clitoris. I don’t know where I got the idea to do all these things. It was crazy spontaneous and she was going over the edge with some very loud moans and the occasional scream.

That went on for almost an hour. By the time I penetrated her, she let out a satisfying “oh yes.” I was worried I was going to ejaculate after all that excitement. I started with slow thrusts. She was tightening her vagina muscles around me. It was an awesome feeling. I told her she felt great and to use my cock to exercise her pussy. She loved my creative talk about athletic sex and reciprocated by saying I am a great sexual workout buddy. We got into a rhythm where I thrusted in, and she would squeeze her vagina tight as I pulled out. It was hypnotic. After about a half hour of that, my cock felt conditioned to hold back from exploding. I was able to thrust hard and fast at a consistent pace. This brought Heather over the edge again. By then, I found it hard to orgasm. I was pounding away, to Heather’s satisfaction, but trying to find a sensation that would make me orgasm. When I started thrusting with some hip movements, I felt a wonderful new sensation from the slight twisting at the base of my hard cock. That was enough for me to let go. I never felt an orgasm like that. There was ejaculation, but I kept thrusting. I felt my cock was throbbing, and then I felt a second extremely satisfying long gush of warm semen.

I was so turned on after that orgasm that I couldn’t sleep. Heather and I continued to caress, and fondle, and lick each other. I was hard again after 45 minutes or so. We started to have sex again. I used up my only condom. We dithered about unprotected sex, but just for a little while. I was a bit nervous about this, but I was super horny and our lustiness in the moment made the spontaneous choice that much more exciting. The feeling of the warmth, and wetness and tightness was awesome. We had sex a third time, again unprotected, when we woke up the next morning.

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? I felt great. She also felt the same. We had breakfast, and then she got ready for her ex to return her son later in the day. We continued to hook up every other weekend. I never made Bill’s mistake of bringing up a relationship to drive her away. She seemed happy to date an intelligent guy that took her out for dinners and movies, or to go biking or running with, and have good conversations, and always ending with great sex. A few months later, I left that city for a job in another city. The job change was planned before Heather and I hooked up the first time. We didn’t talk much after I moved away as I was busy with my new job. About two months after I was in my new city, she called me up to tell me she was in town for a business meeting. We met for dinner at her hotel, and then we went to her hotel room to fuck. I didn’t sleep over, since we both had an early work day the following morning. As she said, and I would agree, we were good sexual workout fuck buddies.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Condoms, Discussed STI testing history

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Emotional intimacy, closeness, connection, Thought it was an important experience to have, To feel better about myself

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 never talked to anyone. Neither did she, as far as I know.

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? I learned things to say and do and how to get my body moving in ways to better turn me and my partner on. I sometimes play over in my head the sex Heather and I had together because our sexual experiences together taught me about how to have good sex. I’d say she was the one of the top two best sex partners I ever had.

What was the WORST thing about this hookup? Not much. I wish we could have used each other as fuck buddies for much longer.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Having had a some poor relationship experiences in my high school years and facing some traumatic romantic rejections in my twenties, this experience greatly increased my sexual self confidence. I came to see casual sex as being a very positive experience. In fact, as it becomes harder as we get older to find a long term relationship leading to marriage, I found casual sex with a willing partner to be very enjoyable. This fuck buddy relationship showed me how.

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

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

Anything else you want to add about this hookup? At the time, she was not looking for a relationship, and I was not looking to settle down with a single parent who was 35 while I was 32. So this casual relationship worked for both of us. I heard she never did get married again and is still single. Looking back at what I know now about the relationship options to come later, I think we could have had a serious long term relationship. It was timing and thinking the future would be better for both of us, but the sex… ah, the sex was unbeatable.

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 can be more exciting than relationship sex. If only there were more convenient ways to find it.

What do you think about the Casual Sex Project? Worthwhile. My experience was too satisfying to keep to myself.

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

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