A New FWB Date



What’s your gender? Man
How old are you? 60s
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? USA
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
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)? >50
How many hookup stories have you here posted before? Two

A New FWB Date

How long ago did this hookup happen? 2 months 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? Just met that day

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? “G” is an attractive, blond-haired 40 yr woman, with average build, around 5’5 and 150 lbs. Pretty face. She is a busy divorced mother, working in the medical professions. We had not met prior, having just introduced ourselves through an NSA/FWB type site where we corresponded before switching to other channels. I was scheduled to visit her city, searching for companionship, and asked if she would like to meet for dinner; she agreed. I was excited to have found an interesting date with someone I had never met.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We met at a restaurant of her choice and had a nice dinner with a drink or two. We spent the time chatting and getting to know each other better. The conversation flowed pretty naturally, although it tended toward the serious rather than the light-hearted. She told me about her work, and about her fairly recent divorce, and I told about my life in return. It turned out that she had been married fairly young and had hadn’t dated that much before or since. I was relieved to find that she was the person she had represented—not always the case in my experience!—and she appeared to be likewise reassured. After dinner, I asked if she would like to come to my place to continue the conversation, and she said yes.

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 had prepared the place in the event I could entice her back with me, with music at the ready and the necessaries by the bedside, in case we should wind up there. We began on the sofa and continued the conversation as before for a while, until I moved a little closer after fetching refreshments, reaching over to stroke her back, and then into a kiss. Expected to things move slowly under the circumstances, if at all, but she responded positively. Within a minute or two, before I made any further moves—she moved her hand up my leg and began rubbing my crotch. Taking this as a positive sign, I soon asked if she would like to move to the bedroom, but she responded that she did not want to have intercourse. I said, “ok that’s fine, I understand;” she didn’t stop rubbing my cock, though…I’m sure my erection was obvious. After another couple of minutes, she said something along the lines of, “This is what I miss about having a man around! Is there anything else I can do?” Before I could blurt a response, she was unzipping me and fishing around to pull my dick out. “Oh you have such a nice cock, I really want to suck it! I love giving blow jobs!”

Her sudden transition from mild mannered medical professional was a surprise, but I didn’t argue. I unbuckled and pulled down my pants, but before I could even get them off, she was between my legs and enthusiastically demonstrating that she meant it. I was a bit in shock at how quickly things had progressed, but I was enjoying every second! She kept stopping to say how much she loved sucking cock. “Sometimes I can come from this! This is more enjoyable for me than sex” she said. Meanwhile, I was moaning, trying not to cum too soon, and reaching down her blouse for her breasts. She stopped just long enough to say again how much she was loving what she was doing, how much she missed it, and to undo her bra for me. Her breasts, though not especially large, were very nice in the hand, with firm, erect nipples that I would have loved sucking if she had given me the chance. I made a half-hearted attempt to reach into her pants, telling her I wanted to reciprocate, but the angle was impossible and she didn’t move to make it possible. At some point, I reached behind her head but trying not be a jerk about it. “Yes, grab my hair!” she said. I grabbed it and started gently directing her, not that she needed it! By now, I felt myself beginning to lose control of my orgasm and warned her that I was going to cum soon if she didn’t let up. “Yes!” she said and started deep-throating me hard. Then, more urgently, “I’m going to cum!”, but she went all in, and I lost it and jizzed and jizzed, all the way down her throat, as she gagged and kept going even beyond that sensitive instant when all you can do is cry out and laugh at yourself. She swallowed most and spit the rest on my cock, which she grabbed with her hand to rub over her lips and face, then rubbing her slobbery face all over my cock and balls. She was such a turn on! I was spent and could only slump back against the couch for a minute. It wasn’t the most sensual blow job I’ve ever experienced, but certainly one of the sexiest and most enthusiastic. It was a great moment!

Afterward, I told her that I was feeling guilty for not reciprocating and giving her a turn. She said, no I had given her exactly what she wanted. After a few minutes of cuddling on the couch, she excused herself to clean up and then was business-like again, saying her baby sitter expected her soon. I walked her to her car, gave her a peck goodbye, and waved as she drove away.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? No

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 continued messaging. She wanted to meet again before I left, but I wasn’t able to. We still communicate. She likes dirty talk and gets straight to the point. She wants to blow me again. She has also suggested we should fuck next time.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, No penetrative sex happened

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting

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 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? No one

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? Great blow job!

What was the WORST thing about this hookup? I could not reciprocate. Would have liked to spend a few hours in bed with her…

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No

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

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

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? It has been important to my emotional health for the past 15 years or so.

What do you think about the Casual Sex Project? Love it. See my earlier posts for comments

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