What’s your gender? Man
How old are you? 58
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, USA
Highest education received: Some college (not currently in college)
What’s your occupation? Sales
What’s your current relationship status? Single
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Free & Easy
How many sexual partners have you had in your life (including oral sex)? 350+
How many hookup stories have you here posted before? 0

Old Lady’s 1st MFM

How long ago did this hookup happen? May 2019

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

How would you best classify this hookup? Group Sex

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? (Names changed for privacy.)

Haze is 80 years old and is a natural blond who has her hair dyed its original color. She is about 5’3″ tall, weighs about 170 lbs., and was widowed a little more than a year ago.

I knew Haze and her husband, Phil, for more than 20 years. She always seemed to be the goodie-two-shoes, holier-than-thou type; rather judgmental regarding “immorality,” and always has something “authoritative” to say about nearly any topic that comes up. Other than that, she really is a kind person who would rather do something for somebody else than not. Read: rather giving of her time and talents.

She confided in me a few years ago, after her husband’s health started to decline, that she had 3 affairs while her husband was working when she was in her early twenties. She also told me about two of her uncles flirting with her, starting when she was 11. She thought it was fun and flirted back. She started having sex with each of them at separate times when she was 12 and says that she enjoyed it enough to “play with” a few other men before she met Phil at 16 years of age.

After telling me some of these things over the course of a couple of months, she tried to flirt with me, but I was not interested at the time for two reasons: 1) Phil was a very good friend and, in some ways, a mentor, and 2) she was not attractive to me. I liked her as a friend and as Phil’s wife but was not attracted to her.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? A few months before I had to move away for work, Haze started coming onto me again but this time she was very bold and would grab my crotch from behind, or sometimes, when we would hug upon my arrival or departure, she would rub my cock through my pants. I told her several times that I was not interested in going down that road with her, especially while Phil was still alive. She would usually just say, “We’ll see about that,” before giving my cock another gentle squeeze.

After Phil died, I started traveling to her home, which was over 2 hours away, every couple of weeks. I did things around the property to help her out. On one of my visits, when it was time for dinner, which she always insisted on feeding me (this was something she always did for everybody who visited), she mentioned that she wanted to try something she had never done before. I jokingly asked if she was going skydiving. She chuckled and said that she had never sucked a cock before and that she wanted to suck my cock that evening before I left. Well, it just so happened that it had been several months since I had sex, and I happened to be thinking while working that afternoon that I should probably call up a friend on my way home and stop off for a good fuck. So, when my dick twitched when she said that, instead of saying anything I just stood up and pulled my cock out while walking around the table toward her. I told her that she was about to have her first mouthful of cum. She was a natural, which surprised me. It took about 15 minutes of her slobbering and sucking on my dick to fill her mouth and give her her first taste of semen. She said that she liked it and wants to have more.

After that first blowjob, we repeated the deed every time I went to her place for the next several months, and she finally convinced me to fuck her. I introduced her to porn while we were fucking one night. She didn’t really get into it but wasn’t turned off by it either. I began showing her MFM and gangbang videos, especially with older women, but she told me that she was done watching porn and didn’t want me to show her anymore. I agreed but told her that I wanted to watch her suck another man’s cock while I fucked her. She said that she didn’t think she could do that because of her beliefs, but I continued telling her what I wanted to watch her do, which included watching her fuck and suck strangers while I watched before joining in. When I would say those things to her while we were fucking, she would become more active, breathing harder, and would bite her upper lip and have a strong orgasm rather quickly.

I knew I had found and activated her imagination station, but she continued to insist that she “didn’t think she could do that.” So, I had to figure out a way to help her get over her fears. I called an old buddy of mine, Carl, who used to share his wife with me for about 8 years until she got sick and died about ten years ago. I explained the situation, and we came up with a plan. We would both drive up to her town in separate cars on the following weekend. I would tell her that, instead of her making dinner that we were going to order pizza to be delivered. I would call him, he would be at the local pizza shop, get the pizza and deliver it. When he arrived he would look at Haze and give her a compliment with a mild sexual innuendo. And I would make the suggestion.

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? The plan was in place. I intentionally got to Haze’s place later than usual, which meant that I didn’t have enough daylight to work on the lawn. When she said that she would start dinner I told her that I was going to have pizza delivered, and called Carl. Carl arrived with the pizza about 25 minutes later and, as planned, stepped into the house. When he saw Haze, he said he liked her dress and that it reminded him that he was, “ahem, hungry,” as he looked her up and down. I looked at Haze and said, I think we’ve found your first threesome. She snapped her head back in surprise and said, “YOU’VE GOT TO BE KIDDING! I never said I would have a threesome!”

I pulled her close and replied, “But every time I say something about you fucking or sucking another man while were having sex you start into a climax. I say the idea of it gets you excited,” as I grabbed a handful of breast. She started to pull away when I took her hand and put it on my crotch, and said, “just imagine, you can have two of these things tonight instead of waiting another few weeks for me to come back.” I asked Carl, “Well, old friend, what are you waiting for?” “Old friend?!?!” Haze asked in surprise.

“Haze, do you really think that I would trust just anybody to treat you right for your first time? Carl and I have talked about this for the past week or so. I’ve told him all about you and how you cum almost instantly when I mention that I am looking forward to watching you with another man. If you are really against it, Carl will be glad to leave now but, if you are as curious as I think you are,” as I stepped away and nudged her toward him, “I promise, you will really enjoy us tonight.”

Carl stepped toward her, took her in his arms, and kissed her as she nearly melted, instantly beginning to breathe shallow, rapid breaths as she grabbed his growing cock through his pants. I sat down on the stool while they began to make out, kissing, touching, caressing. Then Carl took her by the hand and led her into the bedroom (I had given him the layout of the house earlier), where he laid her down on the bed as he lifted her dress before going down on her. After Haze had several loud orgasms, I decided to strip and go in with them. Carl was still eating her pussy as I climbed onto the bed and offered her my cock, which she quickly took into her mouth.

After eating her cunt for well over 15 minutes, giving her many orgasms, Carl stood up, dropped his pants and slid easily into her cunt. She continued having countless orgasms while she had, for the first time in her 80 years, two men servicing her at the same time. We switched positions several times before I told Carl to lay down on the bed, and Haze to get on top in the reverse cowgirl position. When they were in position, I got between their legs and slid my cock into her pussy next to Carl’s, and we dp’d her for several minutes before we both emptied our loads into her pussy, him first, then me just seconds later.

We all collapsed onto the bed laughing while catching our breaths.

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? Haze was surprised that she let go of her inhibitions so easily and said that she wanted to do it again. Carl was game for that, of course, and I suggested that he come back up with me in a couple of weeks, to which Haze quickly agreed.

Carl stayed the night with us, Haze sleeping between us. (Fortunately, she has a king size bed.) I was glad to be the one to help Haze get past at least one inhibition and to introduce her to something that she later told me that she had dreamed about for many decades but couldn’t get over the idea that she would be stigmatized. Carl has been back up twice since then, one time without me. We also introduced her to a young, 22 year old guy, and she fucked and sucked all of us, especially because he gave her such large doses of cum in both her pussy and her mouth.

We have talked about getting a stranger for a one-time bang. She is not altogether against it but says she will have to work into that. I have high hopes for her new found drive to have new sexual experiences. We have even talked about having someone video her while having a small gangbang but, again, she says she will take it one experience at a time. We have been watching porn nearly every time we get together. She is intrigued with girls eating pussy but is hesitant about bringing in another woman. She is naturally and understandably nervous that long time friends will find out about her new found hobby, and that they will abandon her. But there is one woman she has talked about, a friend in her mid 60s, who has indicated many times over their years of friendship that she can be promiscuous. She is considering how she might be able to broach the subject with her.

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, Learning new things, experimenting, To help an old friend overcome fears and inhibitions

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? Other than the 22 year old gentleman, I haven’t talked about this particular hookup with anyone else until now.

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? Besides the obvious sexual pleasure, helping a friend to overcome her fears and inhibitions, and to open her eyes to more of what is possible when we let go of “traditional” limits.

What was the WORST thing about this hookup? There was some deception involved in setting it up. I really don’t like to deceive others but I thought this was the only safe way to help her break the ice in this area.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Not really.

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? Haze couldn’t believe how amazing it was, or how many orgasms she was able to have in one evening. I only wish that I had as much semen available to give as I did 20 or 30 years ago. LOL.

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 lived for casual sex for several decades. I enjoy sex with all types of women. I prefer smaller women; not necessarily tiny but smaller, around 5’3″ to 5’7″, and less than 130 lbs. Smaller women have always been more attractive to me, but I recognize the beauty and sexuality in all reasonably healthy women.

What do you think about the Casual Sex Project? Great forum! I will be back.

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