by First Time Bad Boy
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? Detroit
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Sales
What’s your current relationship status? Single
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
Met At A Library
How long ago did this hookup happen? 13 Years
What was your relationship status at the time? Same as current status
How would you best classify this hookup? Short fling
How long did you know the person before this hookup? For less than a week
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 recently sold a business and was looking for a job to begin moving forward with my life. I would spend each afternoon at the local library (I didn’t have home internet at that time) doing job searches. One late Thursday afternoon in mid-July, I was doing a job search and saw a pretty 30-something woman coming down the stairs. I thought she was one of the hot moms that were often there with their kids. I could see she didn’t have any kids with her and that she was wearing professional work clothes. She was in her mid-30’s with dark curly hair, dark eyes, and a mischievous smile. She was about 5’5″, with an hourglass figure, B-cup boobs, and a booty to match. Her dress pants perfectly hugged and showed off her butt.
A few minutes later, she came over to me and we started talking. After 15-20 minutes, she gave me her number and asked me to call her for a date sometime. Instead, I asked her if she was busy that evening and we agreed to meet for coffee a couple of hours later. We talked for a few hours and then got ready to head home. Since I didn’t have a job at that time, she asked what I was going to do when I got home. I told her I was going to go for a swim in the lake by my house and then head to bed. She said that should would love to, but he had to be at work early the next day and would take a raincheck for that swim. We had already agreed that she would come over to my place that Saturday night for dinner.
On Saturday morning, I was driving back from the grocery store when she called me and asked if she needed to bring anything for dinner. She then told me that she wanted to take me up on that rain check for the swim and wanted to know whether or not she needed to bring a bikini or if we would be swimming European style. Almost driving off the road, I was able to calmly reply that there was no need for her to bring a bikini, as we were both adults. The rest of that day, I wondered if she was serious about going skinny dipping or if she was just joking with me.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? When she arrived on Saturday evening, she was wearing a lovely yellow sundress with lilies on it. It showed off her cleavage very nicely. We sat and watched the sunset from the bluff near my house and then had dinner together. We had a marvelous conversation during dinner, but I was distracted by the thought of seeing her naked. As we finished dessert, she looked over at me and asked, “So, are we going for that swim or not?” I ran upstairs to grab a couple of towels and we were off to the beach.
We got to the private beach in my neighborhood. It was dark and no one else was around. We proceeded to get undressed, laughing how we were seeing each other naked after just meeting two days before. We swam around for about 10-15 minutes under the moonlight and talked. Soon, she said she wanted to go where we could stand up. After we got to where the water was at my chest and her shoulders, She put her arms around my neck and we started to kiss. The kissing got heavier and she started to give me a hand job while I sucked on her nipples. After a minute, I was really hard and started to try and go inside her. She stopped me and said that she didn’t want to do it in the water, but we could go back to my place. We got out of the water and quickly got dressed. Just as we were leaving, a group of teenagers was coming to the beach to probably do the same thing as us.
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? When we got inside, we quickly went upstairs and undressed. She went down to her bra and panties, and I to my boxer briefs. We started to make out in front of my mirror and then made our way to the bed, I climbed on top of her and started to make my way down kissing her. Of course, I went right for her nipples again. To save me the trouble of working around her bra, she told me to just take it off and we kept going from there. After a couple of minutes, I had made my way down to her navel and asked if she wanted me to go down on her. She replied “No. I want you inside me.”
With that, I took off her underwear and started to take off mine. Less than half a second after they came off, I was somehow on my back with her doing oral sex on me. After a few minutes, she stopped and said she didn’t want to waste a good erection on oral sex and that she wanted me inside of her now. I could barely get the condom on before she had pulled me down to her. We spent the next hour and a half going at it in a few different positions. She came twice during that time, but I hadn’t come yet. Then, she said she wanted me to come in her from behind (vaginally) and as we started doing it, the condom started to come off. When I went to adjust it, she said to just take it off as she hated using condoms. When she saw the surprised look on my face, she said she was on the pill and she had recently gotten a clean STI test. Since I had never had unprotected sex, she knew I was clean as well.
With that, I threw away the condom and we went back at it harder than before. Being inside her with nothing on, I realized why my buddies complained about using condoms. I couldn’t believe how much the bare skin accentuated the experience. We continued to go at it for another 30-40 minutes before I finally came (she came again as well). After that, we were both exhausted and incredibly satisfied.
She had to go home right after that to let her dogs out. We talked the next day and happily recounted the experience. Over the next month and a half, we continued to have sex about once a week. It was always a marathon session and always raw (I loved not having to worry about taking condoms on a date or taking the time to put one on). Then, one night, she suddenly called me up and said she had met another guy that was better “marriage material” and that we were done. Apparently, I had just been a boy toy for her until she found someone she wanted to marry.
Ironically, I ran into her about a year later a few days before she was going to get married. I told her congratulations and she confirmed that it was the same guy for whom she dumped me. When we talked about our time together the previous year, she wistfully said “Oh, I’ll never have sex that good again”. I told her that if she wanted to experience that one more time, she wasn’t married yet. She seriously thought about it and realized that her schedule was completely booked until she got married. Last I saw of her several years later, she had two kids and was still married.
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? I felt excited the next day and kind of surreal, like “did this really happen?” After she and I talked about it (she was much more sexually experienced even though we were the same age), I felt much better about it and was even more glad it happened.
What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Birth control pill / patch / ring / injection / implant, Discussed STI testing history
What were your motives for this hookup? Attraction to partner(s), Learning new things, experimenting, Emotional intimacy, closeness, connection, Thought it was an important experience to have
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’ve told a few male friends about it. They all high fived me and thought it was the best sex story they had ever heard, like something out of a porn movie.
How would you best summarize people’s reactions about this hookup? Relatively positive
Did you get emotionally hurt as a result of this hookup? A little bit
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? Getting to enjoy condom-less sex for the first time.
What was the WORST thing about this hookup? Getting dumped out of nowhere just as I was getting used to having regular sex.
Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I realized after this that you didn’t have to be in a serious relationship to have sex with someone you found attractive. As long as both partners agreed on their status, you could just take sex as the pure, natural experience unto itself.
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 is ok for two people to experience together, as long as they are both in agreement as to what it means or doesn’t mean. However, I think that if you have too much casual sex, then some of the specialness that sex provides to us is lost.
What do you think about the Casual Sex Project? Great way for people to express their thoughts on a somewhat taboo subject.
You have a hookup story to share? Submit it here!