by

What’s your gender? Man
How old are you? 54
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: College degree (eg., BA, BS)
What’s your occupation? Sales executive
What’s your current relationship status? Dating casually
Religious affiliation: Christian
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)? 7
How many hookup stories have you here posted before? 0

From Casual Friend To FWB

How long ago did this hookup happen? 3 months

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 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’ve known her since our university days, through friends. That was 25 years ago! She is two and a half years older than me. She’s English and German. Back then, she was built like an European tennis star. In other words, a very hot body. There was some talk that she was sexually experimental: not slutty, but was very comfortable about her sexuality. We went on a date once back then, but since she was older than me, I had my eyes set on younger girls. I always knew she was single. She worked to travel and to participate in marathons in different cities. She lived a very independent lifestyle.
Fast forward to today, my dating life has been going nowhere, and nothing has been working. I haven’t had sex in years. So I reached out to her. We went on a date. Her body is still amazing from her running, swimming, and cycling: 5′ 8″, short sassy hair, toned legs for days, slim athletic body, tight stomach, and breasts that were surprisingly firm.
The date was good. She made is clear that at this point in her life (she is 56 now), a relationship did not fit her lifestyle and routine, but she also talked about all her single female friends who yearned for an emotional connection with a man. I figured she was interested in the same.
Following that date, we later agreed on a weekend trip to Boston over the Memorial Day weekend.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? In Boston, we shared a hotel room with two double beds. The day we arrived, it was very relaxed. We saw an art gallery, walked around some streets, and there was plenty of body contact and touching. Over dinner, the topic of dating and relationships came up again. I said my life also had its routine and I haven’t been able to fit a relationship into it. We gazed in each others eyes a lot, waiting for something to take things to the next level, and that’s when I said I always found her interesting and attractive and sexy. She expressed the same about me. That’s when a feeling of excitement and anticipation came over us as we shared a desert then made our way back to the hotel.

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 started kissing as soon as we got into our room. This went on for a while. I took off her clothes. I hadn’t had sex in years, but I was in no rush to just fuck. I took in the smell of her body and she was aroused by my interest in her body. She told me that her breasts were bigger since menopause. That comment caught me by surprise. I grabbed her breasts and they felt quite firm to me. This led to me massaging her body and eventually her pussy. She told me that her vagina was quite dry since menopause. Again, her candidness surprised me, but I took it upon myself to rub her clit, which led to me giving her oral sex and fingering her. Her pussy was actually quite wet, and she was surprised, because she said she didn’t know she can get so wet!

Her candidness also made me reveal to her that my cock is not as hard as it was when I was younger. To that, she started giving me oral sex. Then she started tickling the back of my balls! She gave me this massive erection. She laid back onto the bed, and I penetrated her. She rested the back of her legs on my shoulders while I held her thighs and we fucked like that for a while. Then she did something awesome. She clenched her calves tight around my neck and then did kegel type exercises with her vagina. Her pussy felt so tight and it actually felt like her vagina was pulling my cock in! It was the most sensational feeling, but that was just the beginning. We moved to doggy style and that’s when she orgasmed. We went back to the first missionary position that I enjoyed so much. We also did another position where she was standing with her legs spread, bent over with her hands holding her ankles, and I penetrated her from behind while grabbing her hips. She also rode me, and that led to her second orgasm. We alternated in those positions a few times and did some variations of those. We had really good sexual chemistry. Each move into another position was purposeful, and the penetration felt tantric, like she was worshiping my cock and I was worshiping her pussy. There was a communication and connection in our rhythm of fucking. The way she used her pussy around my cock gave me a strong, hard, powerful and sustained erection. I was able to pleasure her very wet pussy to orgasm four times. The sex lasted about an hour before I orgasmed, shooting pulses of my cum into her.

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? We slept together. When I woke up with a morning erection, I fingered her pussy. That woke her up and then I penetrated her. We had morning sex in missionary position. We both enjoyed the pleasure of being wrapped around a naked body in bed, as both of us had not had sex in years. We continued to have amazing, fulfilling sex for the next two nights of our vacation. When we went back, we agreed to maintain a Friends With Benefits relationship. We’ve been having sex once a week since then.

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

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 did not tell anyone. She told me that she told two of her close friends that we are in a FWB relationship. She told me that her friends were very happy and supportive of it.

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? Not at all

What was the BEST thing about this hookup? She never thought she could get so wet, and I did not think I could still get such strong erections. We both realized that we were turning each other on and our good sexual response is all about arousal. Also, sex without condoms felt awesome. She is past menopause and we both know we are clean.

What was the WORST thing about this hookup? We’ve been in a FWB relationship for the last three months. We’ve been getting together and having sex once a week. I’d personally like more frequent sex, and I think she does too, but I worry about whether this may get emotional and lead to a LTR. We both agreed, at least for now, that we both don’t want any committed relationship, as we have different habits and life interests that are not compatible. We get along fine on short dates, and we have good sexual comparability.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I wish we could have got into this arrangement earlier. It works well and we are both happy to have sex back into our lives.

All things considered, how POSITIVE was this experience? Not at all positive

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

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