After 30 Years



What’s your gender? Man
How old are you? 55
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Alaska
Highest education received: Some college (not currently in college)
What’s your occupation? tech
What’s your current relationship status? Engaged/Married (open)
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Famished
How many sexual partners have you had in your life (including oral sex)? 60+
How many hookup stories have you here posted before? several

After 30 Years

How long ago did this hookup happen? A week ago

What was your relationship status at the time? Same as current status

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? Susy is a few years older than me. She is a native lady that has been a friend since the late 1980s. She moved out of town with her husband in the 90s, but we have always been very glad to see each other over the years. We used to get together as families in the past and had fun playing games and hanging out. It all began when I met her at a bank she was working at. We used to chat a lot and one time she invited me and my family to visit, and from that time it began.
As time passed I did develop an attraction to her. Often, when fucking my wife or jacking off, I would mix the thought of Susy in my fantasy and ejaculate with her on my mind. She was sweet, soft-spoken, and just pure and real.
Later I went through a divorce and remarried. A few years ago I saw her in town. I was astonished. She was looking great and we greeted each other with a prolonged hug. We talked and she came over for dinner. It was, as always, nice to see her. In the end, I ended up with her cell number and we started texting. She told me how her marriage was not a happy one. We talked a lot about many things, but I confessed how I had always had the hots for her, and she confessed she had felt that way too. I could sense her religious guilt was holding her back. I flat out urged her to come with me to make some intimate time, but she resisted. So, in the end, she went back home to the city life and I still stayed in touch with her until recently.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I kept flirting and telling her how I wanted to kiss her and be with her, and she kept telling me how miserable she was. She started telling me it could happen and I told her if I went to town I wanted to kidnap her. She said that sounded like fun and she agreed. Over time she expressed concern because I was married, so then we worked out an agreement. We would be friends with intimacy, but will not let it affect the life we live or our families. It was to be private and undercover, and if we saw each other in public we were just friends. When she thought this through, she agreed full heartedly. So it was arranged that I had to pick her up after church, take her to where I was staying in the big city, in a snowstorm, and then I had to return her at a decent time.

Sunday morning I drove out and waited for her. She walked out and got into the car, we smiled at each other, and I started driving. She asked me if I was sure if I wanted to do this, and I told her “absolutely.” I could tell she was feeling nervous, but I kept driving. As we neared the city she said she wasn’t sure if she could go through with it. I told her that was okay. We got to the place I was staying at. It was a nice townhouse in a suburb of Anchorage. We went and got settled in and I found some music. She was acting all silly and nervous, but she played a song she wanted to dance with me. I moved in and tried to hold her, but she was rigid and kept apologizing to me. We agreed, in the beginning, not to have alcohol as we wanted to be clear headed. I told her to come over and sit next to me on the couch and we kept talking. We talked about her sexual experiences and she asked if I was getting hard. I said yes and pressed my pants to show her where my hard cock was. I told her to touch it, guided her hand, and she started to rub it. I asked her if she wanted to see it and she said YES! So I removed my pants and as I stood in my boxers, I pulled out my hard cock and balls and she smiled. She stood up and I grabbed her hand and led her into the bedroom.

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 went into the room, she reminded me she only wanted sex, no touching her pussy, and that she didn’t want to handle or suck my cock. I told her that was okay, so she removed her skirt and down to her panties, but her blouse was still on top, so I was disappointed but rules are rules right?
She laid the bed very shyly, and I put on the condom. I grabbed her panties and quickly removed them to see her somewhat hairless pussy. I wanted to touch it, but she grabbed my hands away. So I climbed on the bed and crawled straight between her legs. I leaned close to her face and smiled at her and kissed her awkwardly. She was very self-conscious of her body, so I went ahead and covered her exposed body from her legs and up to her chin with the soft sheet of the bed only exposing her pussy. The only contact between us was our faces and where my cock was pushing into her pussy.
I told her she needed to guide my cock into her pussy. She reached down, held it and rubbed it around, and slowly, I pushed into her. It took some time because she had told me it had been 2 years since she had sex and she was early 60’s now, so I had to be careful. She was very tender so I would slowly move in and out. I wished I could have licked her to help her get wet. When I finally got all the way into her warm tight pussy, I lay still a little and she looked into my eyes and told me I was bigger than any dick she ever had. I started pushing slowly at first and going faster a little at a time. She slowly relaxed and eventually, she hooked our legs together and wrapped her arms around my neck and her body was grooving on my cock. She was feeling it and gave me warm tender moans that expressed her pleasure more than words could. I was feeling so aroused thinking about how so many years ago I had fantasized about this lovely woman and now she had opened the gates of her heavenly pussy and taken me into her.
I kept saying her name and telling her how good her pussy felt and she was fucking me back and our rhythm was slowly increasing. I recall feeling my balls slapping her ass cheeks and that sensation after 20 minutes started to stir the impending explosion of my sperm. I asked her if she wanted me to prolong it or if I should let it go out of me and she said to just finish it. My primal moan groaned out of my belly as I pounded her, looking into her eyes as my ejaculation filled the condom inside her, she smiled at me and kissed me. I laid inside her for a few moments and told her it was amazing and thanked her.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, one

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? She smiled and I pulled out. We got up and I fetched her tissue and brought her clothes to her. I stayed naked for a while as I was enjoying that she kept looking at my cock. She seemed happy.
After we got dressed, we went back to the kitchen and I gave her some snacks. I dropped her off and she said she had fun.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), 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? 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? Her and one close friend

How would you best summarize people’s reactions about this hookup? Relatively positive

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? After 30 years she is still attractive. She is lonely, and has always attracted my attention and lustful desire, and it has finally been fulfilled. It was not disappointing, in spite of the patience it required, and she has expressed the desire to have more.

What was the WORST thing about this hookup? That we only fucked one time and the 4 hours back and forth driving to get to her.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No, it has re confirmed that sex can be a part of your life any time and be fulfilling with the right partner who you agree with the terms of the interaction. Also that a wild romp with a stranger can be just as fulfilling, but this time it was a trusted woman who knew me well.

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? After I got home she admitted to me she regretted that she didnt stay longer she wished she gave me more freedom to do some of the things I told her I wanted like letting me lick her. She felt turned on more than she thought she would and that she came when we were doing it. She also told me she wants me to kidnap her again the next time I travel. I told her I would.

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 have always agreed that sex is a personal thing and that when opportunity reveals itself, it is up to the people involved as long as no one is hurt.
I also believe there are, in a positive experience, beneficial effects for the soul to charge each other and a bond is somewhat forged between the people involved. Whether they ever see each other or not, there is a memory and link between. I take each act of sex I commit to and consider the benefits and pleasures and risks. As for society, what I do with my body, in my space, is none of their business. Unless I am having sex in public, then I can expect the wrath of judgement, if I get caught.

What do you think about the Casual Sex Project? I love this site and read here regularly.

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