by Crazy Canuck
What’s your gender? Man
How old are you? 47
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Bay Area
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Executive
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Agnostic
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 19
How many hookup stories have you here posted before? 3
African American Long-Term FWB
How long ago did this hookup happen? Just over two years ago, but ongoing
What was your relationship status at the time? Same as current status
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? African American woman, 57 years old at the time (about 13 yrs older than me). She’s a tall 5’11”, full AA braids, and had a BBW body type.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I am away from my wife long-term due to work, so I was looking for some action on Craigslist. I came across this post from an AA woman looking for a FWB relationship. She was pretty clear what she was looking for, and I responded with a thoughtful and long response. She responded and we arranged to meet one Sunday for brunch at a restaurant just before the Xmas break in 2014. Despite the socio-economic differences, we had a good time.
Because of the Xmas break and work commitments, it was over a month before I reached out to her again. She responded promptly and had had a medical emergency that left her slightly handicap and in need of a wheelchair for extended mobility. She was in the hospital for over a month, when she got home I arranged to go over to her place to provide company since she lived alone.
Because of her disability, she spends most of her time in her bedroom where she has a 50″ TV. I sat on the bed to watch TV with her as we chatted. As it was early spring and she kept the heat in the house down, I was starting to get chilly and I asked her if she minded if I removed my pants to get under the covers with her. This was by no means a suggestive move by me, but rather motivated by my dislike of wearing pants under covers because of the friction between the pants and the covers when you moved. Being somewhat inexperienced (my wife of 15 years, a one week fling with another man, a Vegas one-night stand, a two evening non-intercourse play date with a nurse, and giving oral to another woman) I did not realize that my request may have been interpreted as a sign.
We continued to watch TV until just after 9 pm, at which point I had to catch the train home as it was a 70-75 minute journey. I got dressed and went to the front door to put on my shoes. I returned to the bedroom doorway to say goodbye and she responded “Do I get a kiss?” I was a little taken a back by this but thought there was no hard with a little peck on the cheek.
I approached the bed and leaned over to give her a peck on the cheek, but she suddenly shocked me by turning her head and kissed me lips-to-lips. I was shocked but could not pull away as I was leaned over and she had secured my head in what seemed like a tight wrestling grip. After a few seconds, I thought “wtf” and started to fondle her breast, first outside her pajama top and then slipping my hand underneath. Eventually, she stopped and decided that since she initiated the heavy kiss, that was a green light to get naked and bang.
So I pulled away, undid and removed my shoes, and then proceeded to get undressed. Given my lack of sexual experience with different women, I decided I would “notch the bedpost” with this lady.
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? After I disrobed I had her slide down the bed and spread her legs. I mounted her in the missionary position and slide my rock hard cock into her, bare as a baby’s butt. We obviously had not discussed STIs, but I have had a vasectomy and given she was a fair bit older than me I assumed she had hit menopause. I could not believe how wet she was – by far the wettest woman I had ever had (not saying much) and certainly the wettest woman I have had since then (saying more).
Her accident has caused a significant strength loss in her legs, so we maybe lasted ten minutes before she through in the towel. During that time, she had at least one and I think two vocal orgasms. Given she was so wet and I’m not exactly hung like a porn star, I could not generate sufficient friction to cum. Eventually, we had to stop due to her legs getting weak, and I just rolled off her and laid beside her as my erection subsided. We chatted for 10-20 minutes and then went for round two, with her again having 1-2 orgasms and myself none. But it was still a notch on my bedpost so I was satisfied, and when I got home I jerked off to release the built-up tension.
How sexually satisfying was this hookup? Somewhat
Did you have an orgasm? No, not even close
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? Given my lack of experience with very few women, I was happy despite not cumming. The socioeconomic differences mean we will never be a pair, but over two years later we continue to have casual sex on a regular (2-4x/month) basis.
I finally nutted in her during our fifth get-together, and now that she has built-up a long more strength in her legs we are able to go longer and in doggy and now I blow my load in her every time. I like how she just lays back and lets my cum leak out of her pussy after taking my cum in her pussy. My wife could never cum through intercourse and whenever I nutted in her, she had trained me to rush to get a Kleenex for her to rid herself of my sweet nectar of love.
What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Sterilization
What were your motives for this hookup? Fun, pleasure, horniness, Learning new things, experimenting, Making new friends, Didn’t want to disappoint my partner
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? A little bit
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 have a couple of female friends in the Bay Area that I share my sexual exploits with. They were very supportive, but cautioned me about unprotected casual sex due to my inexperience with casual sex.
How would you best summarize people’s reactions about this hookup? Relatively positive
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? Made a friend. We’re in a true FWB relationship which we both know will be nothing more. She knows I won’t leave my spouse for her.
What was the WORST thing about this hookup? Her pussy isn’t the best smelling. I won’t do oral on her because of that.
Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yes – it gave me confidence that I could actually find women on Craigslist that are interested in causal sex.
All things considered, how POSITIVE was this experience? Very positive
All things considered, how NEGATIVE was this experience? Not at all negative
What do you think about the Casual Sex Project? Awesome idea! I visit almost daily!
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