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? California
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Legal field
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Straight and normal; love sex, especially bareback
How many sexual partners have you had in your life (including oral sex)? 20
How many hookup stories have you here posted before? 3
How long ago did this hookup happen? 2.5 yrs ago
What was your relationship status at the time? Same as current status
How would you best classify this hookup? Friends-with-benefits
How long did you know the person before this hookup? For less than a month
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? She was an 57-yr old African American, 5’11”, curvy, hair in braids. She posted on Craigslist for a FWB and I responded. We had brunch together in December, 2014 and then when I reached out to her again in February or so she was in the hospital suffering from a kidney stone. The infliction ended up limiting her mobility and she ended up in a wheelchair.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I reached out to her approximately 2-3 months after our first brunch. We texted while she was in hospital, and one Saturday after she returned home I offered to come by to keep her company and do stuff around the house for her that was more difficult since she was now walker/wheelchair bound. She wanted me to just come over and watch some TV, so I brought my laptop over to stream a hockey game.
Ends up her TV is in her bedroom, so we ended up on the bed watching the game and some stuff after the game ended. During the game, I was a bit cool and wanted to get under the covers, but find sitting under covers with jeans on very uncomfortable. So I asked her if I can take my jeans off to get under the covers. Given her condition and the fact that she was still weak after the surgeries I wasn’t looking for any sex that day, but I guess I was a bit naive in what my request signaled.
When it was time for me to go home, I got out of the bed, put my jeans back on and went to the entry way and put on my shoes. I yelled “bye” to her from the entry way, expecting to leave. After I yelled “Bye”, her response was “Do I get a goodbye kiss?”
I thought this was a bit weird given we barely knew each other, but thought “WTF – she’s disabled after going through a very difficult time, so what’s a kiss going to hurt?” So I went back to the bedroom and leaned over the bed to give her a kiss. As I leaned in, she suddenly grabs my face/body with both hands and plants a big, juicy, passionate kiss on my lips using her big, juicy, passionate lips! At first I was shocked at her forwardness, but then thought, “WTF, she initiated it. Why not try to grab some tit?”
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? At this point, I reached under her light pajama top with my left hand and grabbed a mitt full of black boob on her right side as I leaned over her laying on the bed. She didn’t bat an eyelash at it so I continued to massage it before flipping it out latching on to the erect nipple like a baby on her mother’s teat! After a minute of two of sucking and massaging the tit and listening to her moan, I decide she’s down to fuck so I back off and undo and remove my shoes, followed by my pants, underwear, and shirt.
By this time she’s leaning back against the headboard supported by pillows. I climb on the bed, spread her legs and begin to enter her bareback. At this point I didn’t know her age, but was fairly confident that she was old enough to no longer be fertile. We hadn’t discussed sexual health issues at all, but the opportunity to fuck a strange woman bareback and cum in her wet pussy overcame any concern over STIs.
We had sex in the missionary position for maybe 5-15 minutes, and she came at least once. I usually take a while to cum, and a 5’11” chick has a loose pussy for my average-sized dick, so her weakened legs gave out before I came. We rested for about 10 minutes before I decided I wanted to try to nut again, so I gabbed another mitt full of black boob and started sucking on it again. She immediately started moaning and throwing her head back so I positioned myself and got into position to fuck her missionary again. I again pumped her for 5-15 minutes before her stamina gave way again. She came for at least the second time, but again I did not.
About 45 minutes after I was first going to leave, I was again dressed and leaving, this time with aching blue balls.
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? When I got home I sat on my sofa and beat off like a rabid monkey to release the sexual tension I was experiencing. I texted her so as well.
It is now about 2.5 years later and we’re still hooking up about once a week. She’s not sexually attractive at all, but she’s a good person, gives me discounts through her company’s “Friends & Family” discount program, and has an insatiable appetite for sex! In fact, I just nutted in her two hours ago!
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, Emotional intimacy, closeness, connection, It was easy / convenient
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 didn’t give a clear ‘yes’, but I didn’t give a ‘no’
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 two female friends that I am very open about my sex life with. They were happy for me and know that the relationship continues as we speak. I have also told others about her as well with no adverse reaction.
How would you best summarize people’s reactions about this hookup? Neutral
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? Bareback first time with a new partner and the spontaneity of the sex
What was the WORST thing about this hookup? Not being able to cum in her the first time I had sex with her. Also, her pussy doesn’t smell that good.
Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It’s opened my eyes to the fact that you can have a sexual relationship with a person and be friends with them at the same time. I would actually like to have the same relationship with another woman or two, but obviously you can’t have too many of them or you can’t meet their needs!
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? A couple of times I have wanted to end the relationship, but being newly handicapped at her age for someone who has always been independent has thrown her into some depressive states. I realize how much our relationship means to her and fear me walking away will throw her into a depression which might result in job loss, house loss, and the ruin of her life, so I just keep going on with it in the absence of a real reason to break it off.
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 women wouldn’t be judged so harshly for engaging in casual sex. It’s such an outdated and unsupportable accusation which just serves to perpetuate the stereotype that women are inferior.
What do you think about the Casual Sex Project? Interesting concept!
You have a hookup story to share? Submit it here!