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? Adventurous. Experienced.
How many sexual partners have you had in your life (including oral sex)? 350+
How many hookup stories have you here posted before? 10

Does Age Really Matter?

How long ago did this hookup happen? 3/15/2016

What was your relationship status at the time? Widowed

How would you best classify this hookup? Fuck-buddies / Booty call

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? A. is a short (about 4’8½”) Latina lady who weighs about 120 lbs., has short, somewhat curly hair, and has a nervous laugh that happens easily. The crazy part about A.’s and my hookup is that she is 80 years old. I have known A. for about 5 years. I met her shortly after I moved in next door to her while outside shoveling snow in the shared driveway. She let her dog out to do its dooty in the backyard, and came out to talk after I said hello. While we talked for about 10 minutes I realized that she had sweet, flirty eyes, and an allure that seems to be natural in many Latinas. I liked her right away but didn’t really think of her sexually other than recognizing her charming manner and size (I’ve always been partial to shorter women).

Over the next year A. and I became more acquainted and developed a good friendship. I helped her around yard several times in a number of different ways. On some occasions she would invite me inside for coffee and conversation, especially after I would do some special favor for her in her yard. We talked about many things; about her sister who lives in South America, and her adult children, and my family and work, and sometimes about her late husband.

Sometime in late summer of 2012, when I was over visiting, we were sitting at her dining table chatting when she mentioned that she had a massage therapist friend who would come to her house each month and give her a massage. I told her that I could give her a massage and wouldn’t charge for it. I teased her about giving her that massage for a few minutes, telling her that she could even keep her clothes on, IF she wanted to. We laughed about it for a few minutes and changed the subject. Nearly every time I visited I would ask her if she was ready for that massage. She would laugh and tell me that I didn’t have to do that for her.

I moved about 40 miles away early in the autumn of 2012, but business brought me back to that area at least once each week, so I would stop in and visit most Friday mornings. One Friday, when I was there for a visit, it happened to be the anniversary of her late husband’s death. She talked about him and their relationship for nearly an hour before I said anything. At some point while she was telling me about how he died, she put her hand out and started rubbing the back of my hand, saying that she always loved her husband’s hands, and that mine reminded her of his because of my long fingers and big knuckles. That started what quickly became somewhat of a tradition for us on my visits, where we would hold hands. Eventually, in early 2013, when I was there on a Friday morning visit, she got up from the table and walked past me to the other end of the room. On her way back I gently but firmly grabbed her hand and suggested that she sit on my knee for a minute. When she did, she took my hand in both of hers and started rubbing the back of it. This led to some light kissing, which then led, in short order, to making out. We made out nearly every time I visited after that, sometimes with roaming hands, other times not. We would sometimes fondle each other, sometimes through our clothing, other times she would pull me out of my fly and I would take her top off, and put a hand inside her panties, one time finger fucking her to an explosive orgasm while she stood in the kitchen before I left.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I had started seeing a lady in late 2012, whom A. knew about but wasn’t concerned. I eventually married this lady, but was married for just 18 months before she passed away. I hadn’t been up to visit with A. since about 2 months before I got married but she heard that my wife was very sick, so she called me one day to encourage me and let me know that she was thinking of us (they had met one time before we got married).

After my wife died A. asked if I would like to come visit her. I was planning on being in her area the following week anyway, so I scheduled the afternoon off for our visit. When I arrived she let me in the back door to her house, from which there are three steps going up into the kitchen. When she was on the second step I took her hand and turned her around. She looked me in the eyes and said, “It’s been a long time. (pregnant pause) For both of us.” (I wondered if she was referring just to seeing each other or if she was talking about sex.) At which time I stepped up and gave her a hug. To my surprise she turned her face toward mine and kissed me. It was just as it had been more than 20 months earlier. She is a very good kisser and uses her tongue expertly while kissing.

We went to her dining table and talked over coffee for about a couple of hours when I asked if she still had her massage table. She laughed and said she did but that her massage therapist friend hadn’t been there in almost a year. I told her all she had to do was ask and I would be happy to be of service. While still holding my hand she stood up, stepped in front of me, put her hand on my cheek, leaned over and kissed me. I had told her several times over the past several years that I wanted to be inside her and that I also wanted to taste her. (She has always had a naturally fresh aroma.) After we had kissed for several minutes I told her again that I wanted to taste her and be inside her. I was somewhat surprised when she said, “I have thought many times what it would be like to have you too. Are you sure you want a woman old enough to be your mother? Don’t you think I’m too old for sex?”

To which I replied, “Last I recall you got very wet down there, and you seem to be quite moist now.” As I reached between her legs and up her skirt. She almost came at my touch.

She then said, “Let’s go to my bed before I change my mind. I want you inside me too.”

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 walked quickly into her bedroom where she immediately sat down on the edge of her bed and started stripping. I followed suit, then laid her down as she scooted back onto the bed. I then got down on my knees and dived face first into her already soaked pussy. She had three quick orgasms as I ate her out. After her third one she breathlessly said, “Put it in. Put it in. Put it in me now.” So I stood up, pulled my pants down the rest of the way and mounted her in the missionary position. She has easily the loosest pussy I’ve ever slid into, but it was hot and moist, and it had been several months since I last had sex with my wife before she got sick, and I shot my load deep inside her within five minutes. I was rather embarrassed because I normally can last for nearly an hour or more before being ready to cum. She said that it was okay, that she didn’t think she could handle it that long anyway.

How sexually satisfying was this hookup? Somewhat

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? After we were done fucking we laid on the bed and held each other talking about what we had just done, what we liked best about it, how we would like to do it differently if there is a next time, whether there would be a next time or not. We agreed that I would come for a visit about once a month, and that we would definitely have sex again at some point. She said she was never into giving head because her late husband wouldn’t bathe before sex every time, and that the odor of his crotch turned her off. She said that at least I was always clean and that she might try it next time, but no promises. I told her I would love to feel her mouth on my cock, and would love to see her take me into her mouth. She asked why that was such a turn on to guys, to which I replied, “Have you ever watched a porno video?” She said she hadn’t. I told her that I might bring a DVD next time I visit. She said that she would watch one with me if I brought it. We talked for about another ½ hour, then got up and got dressed before I had to leave.

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, Attraction to partner(s), Learning new things, experimenting, Emotional intimacy, closeness, connection, Thought it was an important experience to have, To cheer myself up, Just happened, I don’t know why, just went along with it, It was easy / convenient

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? Somewhat

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? Nobody

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? Somewhat

Why do you regret this hookup? My wife had been dead only 10 days when A. and I got together. I think it would probably have been a good thing to wait at least a couple of months in order to “catch my breath” and get some of the mourning out.

What was the BEST thing about this hookup? We were each other’s first sex after losing our spouses. For both of us the sex was rather therapeutic, maybe even cathartic. We each had a first experience: for her I was only the second man she had ever touched sexually, despite being 80 years old; and for me, she was considerably older than any other woman I had ever been with.

What was the WORST thing about this hookup? Each of us felt some guilt over getting together so quickly after my wife died (10 days). Also, that I was unable to last more than five minutes.

I violated one of my own rules: Never have sex to cheer myself up.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Only in that even geriatrics desire sex now and then; so why not enjoy it now and then?

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

All things considered, how NEGATIVE was this experience? A little 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? I have enjoyed casual sex for over four (4) decades, except for the few times that I have been in a monogamous relationship. I feel that CS (Casual Sex) is one of the most underrated methods of social interaction, while at the same time being one of the most, if not the most, overrated ways people use to try to improve their self assessment/esteem. It is possible to go from casual hookup to serious relationship, but this is uncommon and an unrealistic expectation. That being said, for the most part I would rather have several fairly regular sex partners who are trusted, loving friends than a monogamous relationship. The reason being is that there is less emotional baggage with CS partners, even though the intensity of the relationships can potentially be as deeply intimate, so long as the ground rules are clearly understood by both/all, and an attitude of mutual respect and responsibility for each other’s safety is maintained.

What do you think about the Casual Sex Project? I enjoy reading the stories more for the relational aspect rather than those that are simply porn writings. Some seem to be contrived, while the ones where the author talks about his/her thoughts, feelings and perceptions tend to feel more authentic. That being said, I do enjoy a good raw romping story now and then.

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