This post is sponsored by Trust Massage Oil.
What’s your gender? Man
How old are you? 64
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Cleveland, Ohio
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? happily retired
What’s your current relationship status? I have a submissive who I allow to serve me four or so days a week and a married mistress who is in a sexless but otherwise loving marriage,
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? I am a dominant with spanking, corset, and leather fetishes
How many sexual partners have you had in your life (including oral sex)? I would guess between 60 and 80, perhaps. Perhaps slightly more. Less than 100, surely. I don’t know for sure, I don’t “keep score”.
How many hookup stories have you here posted before? 4
What Comes After G?
How long ago did this hookup happen? 4 months
What was your relationship status at the time? In a relationship (open)
How would you best classify this hookup? Sex with an ex
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? G is my submissive. She’s 45, quite shapely due to the corset she’s been trained to as well as her fine tits and ass. Excellent legs as well. She had been in my service for about a year at that point. Becca was my ex-wife, we’ve been divorced for over a decade but are still friendly and in fact have been friends with benefits off and on since. Becca is 63 but you’d never guess she over 50. She’s about 5’8″ and quite lovely, a shapely figure for the most part but I always tease her its time she was trained to a corset because she’s getting a little thick in the middle. She’s thick compared to G. in her corset (but who isn’t) and is still pretty good compared to most women and certainly compared to women of her age. G. is my pet and my baby, Becca is my dear friend and confidante.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? When we were married, Becca and I had a b&d leather relationship we each and both found it very satisfying. Becca was a switch, however, and fantasized about dominating other women. Becca’s fantasy was sharing another woman with me with Becca wearing a big strap-on. But we never lived that fantasy during our marriage. Becca always chickened out when push came to shove, so to speak. I’ve been training G. for the past year or so in a submissive lifestyle. I have regularly sent pictures of G. being bound, being punished, and being used hard anally, orally, and vaginally to Becca. Becca was in a much more vanilla relationship with another man. They live together. Becca and I communicate back and forth on email fairly regularly on a host of subjects but I never comment on the pictures of G. I send to Becca, nor does Becca respond about them to me. No comments but no complaints, either. When Becca finally split with her guy and maybe 6 weeks had passed, Becca commented on one of G’s pictures, saying she was pretty. G was pretty in the picture. She was bound spread-eagle on our bed with a vibrator up her vagina and my cum on her face. I told Becca it was about time she lived her fantasy. Becca didn’t respond at first, then finally agreed it might be nice.
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? It was interesting. G is quite hetero and had never been with a woman before. Becca had fantasized about being dominant toward another woman but had never been with another woman either. Becca had never worn a strap-on. G was reluctant at first but she’s my very good girl who always does what she’s told. (Yes, I’m proud of her.) So Becca showed up and she and G met for the first time. The girls were apprehensive, I was amused. G had been prepared and was in her corset, her plump ripe shaved pussy shining, breasts held like soft boiled eggs by the corset half-cups, nipples exposed. Becca was a little nervous and it showed. Becca had also brought a corset (she knew my predilections) and a lilac strap-on with silver sparkles. I laughed when I saw it and even G smiled. Basically, we tied G. down in a lying position on the bed with her hips held up in the air by a foam wedge. G couldn’t move. I started Becca with a flail and then switched her to a slapper. Becca had been on the receiving ends of those implements before but never the giving side of things and was a little reticent to swing too hard in her inexperience. I had to step in and punish G more firmly, as G herself expected and enjoyed, and when G’s ass was cherry red, I invited Becca to use her strap-on. At first Becca was tentative, then she got into the motion and began enjoying herself. The sparkly lilac dildo was decidedly larger than my cock, which I think was a surprise to G at first and eventually kind of a turn on. G was twisting and moaning under the pounding in a way I knew said she was enjoying it. The dildo vibrated as well and I think both G and Becca were enjoying that aspect. I think both came and maybe more than once. I had only coached and watched, mostly watching my girls get it on. But eventually both of the girls got tired or were post orgasmic or both and Becca rolled off G. I released G from her bonds and she rolled over, too. The girls were both lying there, kind of enjoying the moment, drifting and happy. I unfastened Becca’s dildo and it fell to the floor. I mounted Becca and she just looked up to me, a little surprised but not resisting, and I fucked her hard until we both came. I had that delicious post-ejaculation lassitude but I resisted it and grabbed G. by her hair. G had been lying quietly next to us while I fucked Becca, watching. I pulled G over and pressed her face into Becca’s pussy, telling her to suck all my cum out of Becca, which she at first reluctantly and then more enthusiastically did. After a few minutes of this attention, Becca came again. I got a warm wash cloth and washed my sweet G’s face off, and then her crotch, softly and caringly. Then I washed Becca’s crotch just as caringly. You have to take care of the things you love if you want them to last. They are both such fine women. I turned out the lights and we all dozed in the bed for an hour or so, at which point Becca got up and got dressed and left. G and I slept until morning. I kissed my G and pampered her in the morning and made gentle love to her the way she liked, no pain or punishment, only sweet reward. I told her how proud she always made me.
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? To be clear, I had an orgasm with Becca the night before and then with G in the morning. G had at least one orgasm the night before. I don’t know if she had an orgasm in the morning but I know she loved the care and attention. Becca had multiple orgasms before she left. When Becca has orgasms she is very demonstrative and its exciting for her partners as well. After the hook-up both Becca and G went to work, me, happily retired, I went back to bed. I think all of us had a good time but I doubt it will ever happen again. Becca is still my good friend who has now checked off one more thing on her bucket list, G is still my sweet and loving submissive.
What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Sterilization
What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, It was loving on so many levels.
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? Very
Did your partner(s) consent to this hookup? To be clear on the previous question, Becca was apprehensive but anxious to try this, G was less enthusiastic but she understood her role. I doubt Becca will do anything like this again, I think G will be much more enthusiastic if I decide we will do something like this again with someone else.
To whom did you talk about the hookup? How did they react? I talked a little with Becca, but she seems almost ashamed to talk about it. She says she liked it, she is happy we did it but doesn’t want to talk about it any more than that. G and I talked about it at length and she is fine with what happened and would definitely do it again if I told her to. I haven’t talked about it with anyone else. I doubt Becca has. I know G has talked about it with one of her young friends at work G has occasionally brought home for me to have sex with. G had watched us have sex before but I suspect if her friend and I have sex again, G will make it a threesome. (I only have sex with other partners in our bed with G watching. It’s our form of fidelity.)
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? I think it was sharing all this with these two particular women, both of whom I like and care about, both of whom are truly wonderful people.
What was the WORST thing about this hookup? Nothing was bad about it.
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? Not really. It was nice cumming inside Becca again, it was nice to see G once again so good and so submissive. She always turns out to be better than I had expected.
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’m very pro casual sex, which has been pretty important in my life.
What do you think about the Casual Sex Project? I hope it helps change attitudes.
You have a hookup story to share? Submit it here!