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What’s your gender? Man
How old are you? 54
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Michigan
Highest education received: Some college (not currently in college)
What’s your occupation? Executive
What’s your current relationship status? Widowed
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Hungry. Very hungry.
How many sexual partners have you had in your life (including oral sex)? 350+
How many hookup stories have you here posted before? 11

The Boss’s Girlfriend

How long ago did this hookup happen? June 1986

What was your relationship status at the time? Single

How would you best classify this hookup? Dangerous

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? J. was a beautiful, 19 year brunette with a full body. She had average sized but perfectly shaped breasts; stood 5 feet 7 inches; carried about 160 firmly packed, fit lbs.; and had a sweet giggle and a perfectly gorgeous smile that came easily during any conversation. I liked J. from the first time we met, she was sweet and just slightly demure. While we always dressed casually for work, her attire seemed to be a bit more thought out or planned than any of the other girls who worked there, which caused her to appear to be a bit more sophisticated than the others but, because of her natural humility she never acted like she was better than them, and everybody liked her (except one girl who wanted to take B. from her. LOL.)

J. and I met because her boyfriend (we’ll call him B., a late-40s mob type guy, who was married and had a reputation of being a real hard ass) bought the arcade that I worked at part time as my 2nd job. B. fired some of the employees after he bought the place but decided to keep me on because he said I seemed like the kind of guy who would protect his girlfriend. J. and I had a lot of time to chat while working together, especially during the week, and we quickly learned that both of us enjoyed smoking marijuana and that we both almost always had some with us. So, we often looked for opportunities to smoke together. Sometimes we would sneak away from the desk when nobody was around or the place was dead, and go out back for a quick toke; other times we would meet early before work or stay late. After several months of this I asked her if she would like to take a ride with me after work so we could get high in a less risky place. She agreed but said that she would have to meet me somewhere else because B. often would go back to the arcade after hours to check things out and do the books for the day.

Smoking together off-site, we were considerably more relaxed and took time to talk more personally. After our first couple of relaxed smokes together we started doing shotguns, which naturally led to light embraces during the hits, which eventually led to getting our lips closer and closer. Obviously with this growing liberty between us came increased sexual energy, which was almost palpable at times. But because of B. we never let it go beyond some light brushing of her breasts and ass, or sometimes she would “accidentally” put her hand on my crotch, when she would feign embarrassment, and offer a mock apology. Most often we would just laugh and take some more hits of the joint.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Early one Tuesday evening, about a year after B. bought the business, his wife showed up at the arcade with their two children. (She was just as stunning to look at as J. [more on her another time]) After she and B. talked for a while, he came to the desk and told J. and me that they were going to take off and would be gone all night. After telling us this, B. looked at me and said something along the lines of, “Don’t let any of the guys flirt with her. If they try, tell them that I will make them wish they never worked here.”

Of course, I agreed to his command and told him that I would protect her. Funny thing about that is that J. had gone to the other side of the window to take care of a customer real quick and, while B. was still standing there she reached under the desk and brushed my cock on purpose while reaching for something that was in front of me. I nearly shit my pants! Fortunately he had just started turning around when she did that, so he didn’t see my face instantly go flushed.

After B. and his family left, J. and I chatted about several things and planned to go out and smoke a few joints after we closed the place for the night. Instead of going to some of the places we were both familiar with I told her I was going to take her someplace new. She asked if she needed protection, to which I answered, “That depends. Are you on the pill?” We laughed a little and got back to our jobs, knowing that kind of talk could get us in some real trouble.

After we left and met at a parking lot a couple miles away, she got into my car and said, “Yes.” I asked her what she said that for, to which she replied, “Yes. I am on the pill. Do you think I need any other protection?” I just smiled, put the car in drive and took off down the road while I handed her a joint to light. We smoked and joked as we traveled to a lake with a beach about a 1/2 hour away. When we got to the beach she asked me, “Why here?”

I replied, “Skinny dipping seemed to be the easiest way to see you naked without trying to fuck you.” She gave a big laugh and said, “Let’s go!”

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? As we got out of the car I challenged her to a race to see who could get into the water naked first. She said, “Let’s start on my count of three. 1. 3!” and she was running while stripping. What I didn’t realize is that she took her shoes and socks off while on the way there, so she had a bit of a head start already. She won the race, laughing all the way, and ran into the water and dived in. After I got in and caught up to her she said I cheated. Of course, I asked her how I cheated, reminding her that she had already removed her shoes and didn’t give a proper 3-count. She said, “You got to see me all the way naked but I was underwater and didn’t get to see you all the way naked.” Instead of answering I jumped up as high as I could, which exposed me, then went underwater and swam away. It was night time, so the only light was that of the 1/2 moon, so she couldn’t really see where I went. Fortunately, I have a very good sense of direction, as well as excellent hearing, so I found my way back to her rather easily. As I approached her I had my arm outstretched and put my arm right between her thighs. She let out a scream! Then I came up from behind her, grabbed her around the waist and lightly bit her on the shoulder. She almost melted in my arms, and turned around to look me in the eyes. I told her that she was more beautiful naked than with clothes on, then bent down and kissed her on the lips. She kissed back, and that started the mutual groping and pawing at each other’s body.

We made out standing in 4 feet of water, touching and fondling each other for about 10 minutes or so before she gestured that she wanted to put me inside her. I told her to follow me to deeper water. We went out to where the water was about 5-1/2 feet deep, causing her to walk on her tip toes and bounce slightly to keep her nose above the water. I turned around, lifted her up so she could straddle me and, without manual assistance from either of us my cock slipped inside her pussy for the first time. We fucked standing in 5-1/2 feet of water for probably 20 minutes or so before I released my first load into her. After my first orgasm I carried her up to the shore, still buried inside her twitching pussy, and laid her down in the water just off the beach so that the water was caressing her legs and just barely slapping at her vagina. Then I ate her out to her first orgasm of the night, which I later learned was the first orgasm of her life.

We fucked and swapped oral until about 5:00 in the morning in the water, on the picnic tables, on the lifeguard stand, and in the sand on the beach, taking a break every now and then to have a drink of water and a smoke. I lost count of how many times I came inside her that night, and how many orgasms she had. Suffice to say we were both well satiated. Also, that was the first time either of us had sex in the water, which was supremely enjoyable for both of us.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than 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? After our night of smoking and fucking, we went to breakfast at a little diner neither one of us had ever been to. We had been in the water so much that our skin was so wrinkly that it was beginning to hurt as it dried out. While having breakfast we talked about the night, what we enjoyed most about it and what we wanted to do the next time we got together. We joked with the waitress and each other, and had good general conversation for about 1-1/2 hours before going back to town and taking her to her car.

I was scheduled off that Wednesday night (fortunately), so it was easy for her to give an easy to believe explanation of why she was so tired (she also had another job during the day). We got together many times over the next year or so until she went to college out of state. Several years later, after she graduated from college, we ran into each other at a bar and hooked up a few more times. She told me several months later that she was pregnant with another man’s child. I asked if she was sure it wasn’t mine, to which she replied, “Yes, I had another period after our last time together.”

I have thought of J. many times over the years, wondering how she is, if she ever got married, and if she had more children, but most of all hoping she is doing well.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Birth control pill / patch / ring / injection / implant

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, Hoping or expecting it would lead to something more, Thought it was an important experience to have

How intoxicated were you? A little tipsy/high

What substances did you consume? Marijuana, hashish

How intoxicated was your partner? A little tipsy/high

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? Somewhat

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? This is the first I’ve ever said anything about it.

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? Having sex in the water with a woman I had fantasized about for nearly a year. And that it led to at least another 100 hookups with her over the next year or so. We even fucked on B.’s office desk and on the pool tables several times.

What was the WORST thing about this hookup? The danger that faced both of us if B. had found out about our escapades. He was a violent man and had spent several years in prison for killing a man 20+ years earlier for flirting with one of his girlfriends.

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

Anything else you want to add about this hookup? Sex in the water produces a whole different experience.

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? Casual sex can be both beneficial and risky behavior. I believe that when a person enjoys consensual sex with another person(s) that there is a positive effect not only in their body but in their mind as well, AS LONG As they don’t base their self-opinion on their ability to please another person sexually or think that it will make them feel better about themselves for more than a few hours. My experience is that when a person bases their opinion of themselves on their ability to seduce or get a sex partner or perform well, then they are really setting themselves up for regret. On the other hand, when it is for enjoyment, closeness/connection, or to expand one’s experience base, then it can be a very positive thing.

Social stigmas should be erased across the board concerning those who choose to enjoy sex without commitment.

What do you think about the Casual Sex Project? I enjoy reading the stories, especially the ones in which the author relates his/her thoughts and emotions regarding their partner(s), and about their experience.

I wish that comments could be made/read natively on this site because there are those of us who choose to not use mainline social media outlets.

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

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