by

What’s your gender? Woman
How old are you? 43
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Pennsylvania
Highest education received: High school diploma
What’s your occupation? Currently Unemployed
What’s your current relationship status? Married but with an understanding
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 8
How many hookup stories have you here posted before? None but am thinking of sharing somemore

My introduction to Casual Sex

How long ago did this hookup happen? 24 years

What was your relationship status at the time? Engaged/Married (monogamous)

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

How long did you know the person before this hookup? For more than 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? He was extremely attractive with long, brown shoulder-length hair. He was well-muscled with an athletic build, but on the slim side. He was also taller than me. I only came up to his chest.
I knew him from high school, back then we talked on many occasions during school, but ran different social circles so I didn’t see him much outside school. I knew he was shy back then, and I thought that it was odd that he dated freshmen.
We had never hooked up, but my girlfriends and I thought that he was a hottie.
He had a typing class with me, and I used to catch him staring at me and my girlfriends. We would innocently bend over so he get a glimpse of our breasts, or cross and uncross our legs so he could see our panties. It was our little joke and we always wondered why he never approached us.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it?  I got married the end of my senior year, and once I graduated we moved to the other coast. For my 25th birthday, must husband arranged for me to have a vacation and go home to visit my family. He wasn’t able to accompany me due to commitments, so I was happy to go but a bit disappointed too that he would not be able to make the trip.
Anyway, I ran into him one night when I was out with my sister. He too had moved away and was home because he had just finished law school, and was home to relax and visit his family before he started on his career. We shared some small talk and then he told me that a few of our classmates were getting together that weekend for an impromptu reunion and that I should come.
I went because I thought that some of the people that I ran around with would be there. I couldn’t have been more wrong as they were all of the preppy snobs. I guess that caused me to drink more than I should have. They were boring in high school, and they were boring now, too. I think that he sensed that and maybe because he had invited me, he started paying attention to me and brought me into the conversation. It wasn’t long before we sat together and just talked to each other about our lives and reminiscing about old times.
As the evening drew to a close he offered to give me a ride home as I had told him that my sister dropped me off. I had actually started enjoying myself and his company, I thought what the hell and called my sister and told her that I had other plans.
In his car we continued talking about old times and while I wasn’t drunk, I was at that tipsy point where I get open and honest so I told him what we did at typing class and asked why he didn’t flirt back. He laughed and said that we scared him. Then he admitted that I had always turned him on, but he was intimated by how mature I acted. I don’t know why, but I was entertained by the ease of our conversation, it made me feel comfortable and relaxed that I moved a little closer and rested my hand on his thigh and told him that it was a shame that he never told me that back then. There was sort of a silence and then he said that he needed to stop by his motel to talk some more.
I like to say that it was spontaneous. We didn’t plan it and it was mutually instigated, but I think that we both knew what was going to happen if I went into his motel room.

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?  We sat down, continued talking, the way he was listening, the way he displayed interest in everything I was saying, how he charmed me on sharing my thoughts. It felt liberating, but there was a beginning of a sexual tension that I hadn’t felt in years…
He leaned in towards me when he spoke, innocently brushing against me, and it felt electric. I began do a little physical flirting and positioned myself so he could catch a glimpse of my boobs. I could feel his eyes going all over my body almost like he was devouring me. It was stimulating, exciting, and the anticipation was delectable. In the back of my mind I wondered if he was going to make a move. It all made me feel young, alive and tingly.
I mistook him leaning towards me so I leaned into him and kissed him. I think that he was a bit surprised but he kissed back, his tongue parted my lips, I was lost in that moment. He held my head and we kissed so passionately, and that’s when I knew that I wanted him. We rolled back in his bed, making out like a couple of teenagers.
He must have gotten a lot of experience in college as he was an extremely accomplished and confident lover. He set the pace, slow and sensuous, no rushing, just savoring every moment. Slowly undressing each other, exploring, nibbling, and sharing passionate kisses. Of course I have had fantasies about having sex with a stranger and the scenario was always ripping each other clothes off and getting a fast and furious fuck, but this was so much more different. There was an authentic passion, and it generated a real heat.
He started to give me the most exquisite oral, instinctively I wiggled and pushed and he buried his face into my pussy. Frankly, I am not much for giving oral but we sort of ended up in 69 so I reciprocated, his penis was a little above average, but much thicker than I was used to. He had a lovely dark brown uncircumcised penis, so rock hard. It began to ooze after I played with it, the taste was neutral but sweet and surprising on how much it turned me on
He gave me an orgasm and then moved around to mount me. I was so aroused and wet that neither one of us had to guide his penis — it slide inside me like it belonged there. It all felt so natural, how in touch were with each other’s needs. He was very vocal, asking me how it felt, urging me to let go. I’ve never been very talkative during sex, but found it kinky and motivating and soon was voicing my desires to him.

He was focused on giving me another orgasm. He rubbed my clitoris as he pumped into me. I started moaning, and he said “Just moan, baby, if you like it, moan louder if you want it deeper. Moan quicker if you want it faster.” Hearing those words, I wrapped my legs around him and pulled him deep inside of me. He grunted and gave me deep, deep thrusts, and we orgasmed together.

He lay on top of me, still very erect and firm. I was laughing, it had all felt so wonderful. We made love in several more positions, each time he finished inside me, and by that time my clitoris was so sensitive that it felt like one long orgasm. We ended up exhausted, intertwined, and sweaty.
When I woke up in the morning, he was spooning me. Arms around me, cupping my breasts, his semi erect penis between my legs. I was sort of afraid to move because I didn’t want to wake or disturb him. It all felt so sublime. Still, as I snuggled closed and he woke, and kissed the back of my neck, massaged my breasts and whispered in my ear how lovely I was. It started a fantastic session of morning sex

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?  I spent the morning with him. We showered together, and I would had liked to have had sex one more time, but he joked how I wore his little man out. At breakfast, we were both ravenous and talked about what had happened, how we felt and then about our significant others. We both felt a bit strange that we had enjoyed each other so easily and it just didn’t feel like sex, but something more. We both came to the conclusion that it was a special time we’d both treasure, on but that there was no future for us together. He was engaged I was married.
I have run into him a few times since then, at class reunions, now a very successful lawyer he was a featured speaker at an alumni function, we talked, but our spouses were with us and there wasn’t any mention of our special time, but I could tell by the looks that he gave me that I was on his mind. I have him as a friend on FB now and I have occasionally looked at his page, and we message each other the best on holidays and birthdays. I have become mature enough to realize that time could not be duplicated.

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, Just happened, I don’t know why, just went along with it

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 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?  My best friend and I talked about it later that week. At first she just wanted to hear about the juicy details, then she asked me some serious questions like did we use birth control, did I still feel the same way about my husband, things that you don’t think about in the heat of the moment. Then she gave me some good advice about how that experience was a private thing, to treasure it but put it in a private place. Especially if I knew it wasn’t going anyplace and certainly if I still loved my husband.

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? A little bit

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? Besides the sex, I think that all of the introspection it caused me to do, and how it made me think about my marriage, fidelity and commitment.

What was the WORST thing about this hookup? Youth, inexperience, heat of passion, whatever I wasn’t thinking. It wasn’t till I was late for my period did I even think about letting him come inside me. I was quite confused had a lot of mixed feelings and some very silly young girlish fantasies when I thought he might have gotten me pregnant, but fortunately it was only late.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general?  Yes it changed the whole way that I looked at sex and marriage. I had always believed that sex and marriage were inclusive. I had gotten to that point where I felt that I was my husband property and that I had disappeared. I stopped feeling that way, and know that my life is not defined by being a wife and mother, I am still an individual. While it may sound arrogant and selfish of me, I realized that I could love my husband deeply but can sometimes satisfy my physical needs elsewhere.

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?  My husband is 2 years older than I am and I also knew him in HS, he was much more experienced than I was when we met. He was and still is a very attractive and outgoing man. He is a much more liberal thinking person now. While I have never told him about any of my prior escapades, we have had that serious discussion about marriage, and the exclusivity of sex. We both understand that our love and marriage is based on more that monogamous sex. We are partners and while he is very content with just having sex with me, he realizes that because he feels that way I shouldn’t have to.

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 think that not all marriages should be define as a monogamous relationship. That type of thinking does not encourage communication between partners.

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

Comments