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What’s your gender? Man
How old are you? 49
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 occupation? retired (teacher)
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
How many sexual partners have you had in your life (including oral sex)? 60ish
How many hookup stories have you here posted before? 2

Different Worlds

How long ago did this hookup happen? 23 year ago

What was your relationship status at the time? Single

How would you best classify this hookup? One-night stand

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? I had just moved to a new larger city for a job, coming from a small town where I had few dating opportunities. Among the things, I now tried were the phone lines where women could call for free, men for a minute-based charge, and each got to cycle through the introductions of anyone online to see if they wanted to talk directly. The few half hours or so was free so I tried this a few times and pretty quickly exchanged numbers with Sheri and Jana. Sheri invited me to her place fairly quickly, explaining that she had two young kids, both under 10, and couldn’t easily go out on a date. She was a few miles away, in a more run-down part of town; a large vacant block was across the street from the row of tiny bungalows.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? She let me in wearing only a thin nightgown and shushed back her kids, who seemed very curious to see me. The house had cheap wood paneling inside, and she had disheveled brown hair. She wasn’t ugly but wasn’t beautiful either. She led me into a square side room separated from the main living room only by a curtain, which her kids occasionally tried to peek through. She put on some music and we talked for a while, but once as she was looking at records she bent over, perhaps even kneeling on the floor in front of me, and I could see her ample breasts and even nipples very clearly through the gap in her gown. I felt embarrassed, and totally lacked the confidence to do what in later years I might have done: stroke her shoulder and ask for a blowjob. As it turns out, she certainly would have given me one right there only minutes after we met, but I didn’t know that (although honestly I was also worried her children might see, so perhaps it was best that we waited). After a while, she put her kids to bed and led me into her back bedroom. It was a hot night, and hers was the only room with AC, so that was the given excuse. We talked about our lives; my limited dating experience contrasted with hers with terrible men, many of whom were abusive. She smoked, including marijuana, and offered some which I declined. Her mother had recently died of cancer, and she was just above water financially, while I was just starting a professional job and had bought my first house. All in all, I felt we were coming from different worlds and had little in common except loneliness.

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 expressed some embarrassment about this and said something about not wanting to take advantage of her, and then she got fairly blunt, saying she didn’t invite me over just to talk but needed a man. So in short order, we were kissing and fondling. Her body felt wonderful through and under the nightgown, I could finally stroke those breasts she had been teasing me with. Before long she had my clothes off and was stroking my hard cock while I was playing with her breasts, straddling her chest and tit-fucking her. Then her cell phone rang, and she started chatting with a friend but kept pulling on my cock as I stayed as quiet as possible; she looked up smiling now and then at our mutual wickedness. Finally, she got off the phone and kept stroking me steadily. After a bit more of this, I said I would love to cum on her face if possible, but felt embarrassed asking since I had never done this before. She said nothing but kept stroking me fast and strong. Another couple of minutes and I said I was going to cum. Suddenly she pulled her head up and pulled me toward her, swallowing my cock and sucking strongly with her wet mouth. My god, I was in heaven feeling her do this. I had actually only been sucked by two women before, one of whom let me cum in her mouth. I had no idea that Sheri was ok with this, but without asking she pumped her head back and forth during my minute of ecstasy and suddenly I started squirting my cum through my cock into her mouth as she lay under me and continued sucking me fast and furiously, using her hand to enhance the pumping. She swallowed all my cum and finally let up as I thanked her profusely.

I slept there that night, spooning her all through the night without waking once. In the morning, we cuddled and fondled again a bit, and this time I was a little more assertive, straddling her and fucking her tits again, then saying I wanted to cum again but this time on her face. She said nothing but watched as I stroked myself inches from her face, and finally grunting as I squirted several spurts of cum directly under her mouth so it stuck between her chin and lip. I made it clear how much I enjoyed looking at that, and how fun it was–I had never done that before so she was my first. She got up to start gathering her clothes for the day and stood to look at me for a bit, cum still stuck to her chin. That moment was powerful and vivid, as she neither invited nor disapproved of what I had done, it seemed completely neutral to her, but she gave me what I asked for and a bit more. Finally, she got cleaned and dressed.

How sexually satisfying was this hookup? Somewhat

Did you have an orgasm? Yes, more than 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 got together a week later, after my first date with Jana, who I seemed a little more compatible with. I was immediately honest that I was dating someone else, though in retrospect I perhaps shouldn’t have rushed into Jana’s arms, as we weren’t ultimately compatible either, and she wasn’t quite as good sexually (more on that in another story). But I said I still found Sheri very attractive, and she didn’t kick me out. She said she wanted intercourse this time, but I found I couldn’t hold an erection very long in a condom so that only lasted a minute or two. We talked about other kinds of sex but she said she would never do anal, and while I wanted another blowjob she wasn’t going to do that again on this visit. I slept there again, not as well, and gave her a ride to do an errand in the morning. She said she was concerned about a check-up for possible cancerous signs, and I called later to see if she was ok, and she confirmed that she was healthy so the cancer scare was off. But we never saw each other again.

On the second visit more than the first, I noticed her being abusive to her kids, yelling at and hitting them to get them to do what she wanted. They asked in the morning if I had stayed over, and she gave a transparent lie: “I don’t have men overnight, so he wasn’t here overnight”–suggesting that I had left last evening, then came back in the morning, which was obviously not true. They seemed very nice, just curious. But she explained that they were trying at times to have sex with each other after an ex-boyfriend had sexually abused the daughter. This made me feel terrible, and at a loss on how to evaluate the situation or help her. I felt I was completely out of my depth, and coming from a completely different world where nothing like this could happen. I felt sorry for her kids, and knowing her for such a short time, didn’t feel it was my place to say anything more about her parenting. But it felt dishonest to stick around only for the sex, as good as it was.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms, No penetrative sex happened

What were your motives for this hookup? Learning new things, experimenting, Hoping or expecting it would lead to something more, To feel better about myself, To feel more desirable, To feel more confident, To cheer myself up, I was feeling lonely

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

What substances did your partner(s) consume? Marijuana, hashish

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? 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? A little bit

Why do you regret this hookup? Because I knew so little about her, and her family life was so obviously troubled, in ways I was powerless to affect for the good.

What was the BEST thing about this hookup? The most excellent blowjob, followed by a beautiful night’s sleep next to her smooth body.

What was the WORST thing about this hookup? Feeling so out of place. Feeling somewhat desperate for having chosen it.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? A little more aware that people’s lives are complicated, and there’s a lot going on behind the surface, which you may or may not want to delve into.

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

All things considered, how NEGATIVE was this experience? Somewhat negative

What do you think about the Casual Sex Project? It’s great.

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

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