Best Sex of My Life

by sweetmouth

What’s your gender? Man
How old are you? 60
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Santa Monica
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Tourist
What’s your current relationship status? Single
Religious affiliation: Agnostic
How religious are you? A little
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? A switch in D/s terms, s with women and D with men, tran fan in my past.,
How many sexual partners have you had in your life (including oral sex)? 50
How many hookup stories have you here posted before? 0

Best Sex of My Life

How long ago did this hookup happen? 30 yrs

What was your relationship status at the time? Single

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? Just met that day

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? When I was 25 years old, one summer before my second year of graduate school. I met N, a married woman, who was 37 year old at the time. She told me when she was 20 she married a 40 year old man and raised two kids with him. Now he was about 60 and just couldn’t perform, so they agreed she could take a lover under some conditions. He needs to be a college boy, as when he graduates he will move away, and that will provide a graceful ending to the fling. One horny evening, we went to an alternative/mainstream nightclub in this university town with 40,000 students. Mid-week, it was kind of quiet there. I noticed in the back this woman sitting on the bleachers, crying. I went over and asked, what are you crying about. She to me that no guys are paying any attention to her, and that she hadn’t been out in a while. At this point our fate was fixed. We were so turned on. It was on. But neither of us actually broke the ice verbally. We competed to see who could make up excuses to get closer to having sex. First, I said lets go outside to get fresh air. Her only reply to me the entire time I knew her was, “YES!” Next, she invited me to see her new car. I said YES, the only response I ever gave for our entire fling. Both of us scrambling for a plan. Anything to just move in the direction of a place to do it. As we walked to her car, I’m still trying to gather information on her, when I notice as she reached to unlock her car door, a rock on her hand that had to be at least worth 4x as much as this new Ford car. Somebody loved her.  She offered me a ride in her car. I said YES. She asked if it would be OK if she made a short stop to pick up something from a friend. I said YES. She parked in a secluded and dark spot. Returned in 5 minutes, said she got it. I never knew what it was. Then, a very long pregnant pause in the dark. She turns to me and says get your cock out, get over here, I’m going to play with it. I said YES and slid across that bench seat so fast I nearly got carpet burn. She just looked so hot to me. I was out of my mind for her. She was a real Mrs. Robinson, I was living the movie, The Graduate.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It began in my apartment about one mile from the club where we met. No planning was involved. She broke the ice, but to me the hookup began about 5 seconds after our eyes met. From there, it picked up steam on a quick pace. I’d have to say that we were mutual instigators. Imagine us both pulling hard in the same direction. We were on a rail to our destination.

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 entered my apartment, while still trying to latch the door, I felt shudders of good feelings enter my body. She already had my pants down and was blowing me. Did she know about surprise sex and how to employ it to circumvent a persons defenses? I didn’t have time to ask. I was in the cross hairs. We had vaginal sex, some intimate talk before sex, I tried to get her onto the Amazon position. She didn’t seem to understand, thought it might hurt my balls. But it is what I really needed. Mind you it was only ten minutes after we met that she came all over my cock. The bed got so wet, I had to throw it out into the yard. She said getting together with you so quickly is not a problem for me if I can just get answers to three questions. She had her stuff together. std’s, pregnancy and expectations. On the topic of pregnancy, she showed me her scars where she had her tubes tied. Our expectations matched and I believed her. Not like with women my age who said later to marriage and kids, but left me with feeling that they wanted kids sooner rather than later. Sex is ruined for me if it’s built on a feeling that I know is not right. In other words if her words do not truly match her feelings. That alerts me. I don’t like it that way. She expected to be my lover for the school year until I graduated and moved out of town.
That was very important to me. I like to please a woman very much in bed and after as well. To give her a total good experience that lasts in her memory as good and stands the test of time.

How sexually satisfying was this hookup? Very

Did you have an orgasm? No, not even close

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? On the same night, she laid out her plan. She scheduled to be with me every Thursday night starting at 7:30 PM, lasting until midnight. She expected to take me out and show me off. I looked much younger, probably about 20 yrs old. Some guys would just give me a wry wink. (Good for you, lucky bastard. knowing that a woman her age is at her prime, and she was). One lady threatened to call the cops. She accused N. of molesting an under age boy, and walking around a very busy night club area to show him off. N. just loved it. One night she took me to a play directed by her gay friend William. He gave me the up and down then whispered something into her ear. We were running late, so the only seats were in the center of the room. The chairs were open back so you could see thru. Late we definitely had that JBF look. We had just been fucking, so sweat was dripping off us as the play started. I just could not keep my hands off of her. I worked my thumb across and inside the waste band of her pants in the back. I knew others were watching. I just had to do it. It wasn’t much except that it told everything. I was proud to be seen with her.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms, Sterilization, Discussed STI testing history

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 feel better about myself, To feel more desirable, To feel more confident, To cheer myself up, I was feeling lonely, Submission / Relinquishing power, 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)

s 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? Nobody. I had already gotten enough grief from my class mates. Whenever we went out drink socializing, they would always complain . There he goes again, a room full of nice coeds and he is interested in that woman over there that is clearly old enough to be his mother. So, I did not tell them about N.

How would you best summarize people’s reactions about this hookup? Mixed (Some positive, some negative)

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? Not at all

What was the BEST thing about this hookup? We seemed to have a very strong match in our desires at the subconscious level. That is a match that neither of us could really talk about at the time. One clue was that she had me meet her two grown kids, a son and a daughter. The son was essentially my doppleganger. What could I say? “N. do you fantasize that I am your son when we have sex?” That seemed risky to me. I didn’t say a word. Seemed obvious to me. But we never talked about the thought police. What a shame, because if we had, I’m quite certain we both would have agreed that any words were allowed, any topics, to be as free with your mind as you are with your buck naked body. But we never disclosed any questionable action we might have had regrets about. It would take me years of therapy to discover repressed memories of incest between me and my mother. I lusted for N. as more of my mother right from the start and N. longed for incest with her son. We had complimentary deep fantasies. It was like our two subconscious minds hooked up. Normally this type of connection would take a lot of trust building steps and much intimate talk. Not between N. and me. It was full throttle from the get go.

What was the WORST thing about this hookup? I dearly miss seeing her and her touching me.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It was great. She became my sexual mentor. We had a good solid reason as to why we were having sex every time. We both agreed it was good for our mental health. I easily made the honor roll that year.

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? I wonder where she is now. Just give me a phone call. I think she went out for a little sex and got a bit more than she bargained for. She had married young and so probably didn’t have much experience with young guys. As they say we are all dick. That was me. All true.

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? Casual sex is wonderful and plays an important part in my sexuality. I like hookups or the opposite of a long term relationship. Not too much in between. The second time I have sex with the same partner can really be better than the first because all those compliments she gives you after first fuck must be true as she has returned with her body for round two. What she said was true.

What do you think about the Casual Sex Project? Wonderful to see a sex research project, to discuss the truth about sex. Possibly could help to reduce divorce rate, make people happier and move sex into the mainstream of discussion where it needs to be. I’m not talking about gross pornography but rather the truth about good sex and how it plays a huge role in a persons happiness. Nothing at all dirty or offensive about that. Just good clean fun to confirm our human nature. We are social animals and sex is the most social, if not complicated, and enjoyable act. So just be who we are. A social animal.

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