Best Sex I’ve Ever Had

by Jane

What’s your gender? Woman
How old are you? 62
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? USA
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? education
What’s your current relationship status? Single
Religious affiliation: I was raised Christian but have developed a broader viewpoint. I now consider myself spiritual but not religious
How religious are you? A little
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? no
How many sexual partners have you had in your life (including oral sex)? about 10
How many hookup stories have you here posted before? 0

Best Sex I’ve Ever Had

How long ago did this hookup happen? 5 months

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? For less than a year

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? Tall, black, athletic, 20 years younger than me. I met him when I began a new job where he worked. I was instantly attracted to him. We work closely together in the same department. When we first met and got together or emailed or texted to talk about work stuff, all i could think about was having sex with him. I was smitten. I had broken up with my ex 15 years prior and after dating a few guys off and on after my break-up, I gave up on dating. I hadn’t had sex or even a date in over a decade. I didn’t even think about sex any more. I figured, OK, I’m old, that part of my life is over. But this guy turned me on like crazy! We got to know each other better over the next few months; he fixed my car and helped me out with some things at my house, we had drinks at his house, we made dinners together, I hung out with him and his kids (he’s divorced). He was dating several different women and we talked about his experiences. I gave him advice on getting back a girl who’d left him, etc. He knew how I felt about him, but he didn’t want to go there – mainly because we work together. I was surprised by the way I felt, after all those years of numbness, and also intrigued by my powerful attraction to him. I had never dated a black man before him.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? He had a Superbowl party and I made all the food for the party. We drank a lot, and everyone was pretty smashed by the end of the evening. Some were snorting too. A group of his friends were sitting around in his bedroom talking and i was lying on the bed, both drunk and tired. He was sitting next to me and I was scratching his back and flirting with him (I don’t remember that part, but that’s what he told me later). He told his friends he was taking me downstairs to have a nap on the couch in the basement so I could sober up. (I was more inebriated than the rest of them, apparently.)

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? When the two of us got to the basement alone, he told me to pull down my jeans and bend over. I happily obliged (I do remember that part). His cock was so hard and he tried to penetrate me, but he couldn’t, I was too tight and too hairy. He went back upstairs. When his friends left, he came down and brought me up to his bedroom, where I then took off all my clothes. I still remember how it took his breath away when he saw my naked ass for the first time. We were both so turned on! We kissed a lot and rolled around on his bed, enjoying skin-on-skin. He told me how soft my skin felt, which made me feel good, being so much older than him. But my pussy was still so tight and hairy that he couldn’t penetrate me, so we cuddled, naked, until the wee hours, then I went home before his roommate woke up.

Our second encounter happened at my house. He came home with me to spend the night. We made dinner and tried to watch a movie, but couldn’t concentrate – we wanted to fuck so bad. So we went to bed. I had removed all my pubic hair, so my pussy was wet and hairless, which turned him on. He immediately put his big, hard dick in me and it felt so incredibly wonderful! I had wanted him for so long, and this was like heaven! He was on top of me, fucking me hard, I was so wet and so into him, and he came. When he pulled out, there was a huge (I mean huge) pool of blood on my bed. But there had been no discomfort or pain during sex, so I was still so happy. I got a big towel and put it over the bloody area. We would have kept going, I think, if not for the blood. We rinsed off in the shower together then went to sleep. Neither of us was bothered by all the blood.

Our third time was also at my house, when he again came home with me to spend the night. We made dinner together then went to bed. I had gone to my gynecologist after the bloody incident. She said I had had too long a dry spell and his penis tore the wall of my vagina. She prescribed some vaginal cream to toughen up my vagina. I had healed up by this time. We had incredible sex – him on top, me on top, both of us came, we drifted off to sleep. But he rolled over to the far side of the bed and didn’t want to cuddle with me the rest of the night. I tried to put my arm around him but he ignored that gesture. I didn’t know what he was feeling; in hindsight I wish I had asked him to open up and talk to me. But I didn’t want to seem like I was complaining, so I just went to sleep. In the morning we got up and got ready for work and were both happy. We heard a song on the radio that seemed to be just about us and our relationship, and he kept humming the chorus all day long at work. It was so sweet!

Our fourth and final time together took place at his house. I was frustrated about something and called him to talk about it. He told me to come over, he was just making dinner. I was so happy to be with him again that I forgot all about my frustration. I wasn’t thinking beyond dinner, but when we were finished he asked me if I was thinking about fucking, I told him that any time I was anywhere near him I was thinking about fucking. So we went upstairs and I had the most incredible sex of my life! I don’t know what specifically made if so wonderful, since we didn’t do anything out of the ordinary. But our initial nervousness after our first times together was gone, and everything just felt so right. I gave him head, then got on top of him. He was so hard! I rode him like crazy. I came, then he got on top of me and fucked me like no one else had ever done. He came and then we fell asleep for a while, cuddling. Then I woke up and started stroking his dick, which got him hard, and then I sat on top of him and rode him until I was in a complete state of bliss and then I came. I collapsed next to him and we cuddled again. I remember looking out at the cloud formations moving in the sky, and listening to the blustering wind, and the wildness of the weather felt so right.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than 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? We weren’t done, I wanted to suck him and make him come again, and we wanted to do it doggy style. But his roommate came home unexpectedly so we jumped up and got dressed. We started making dinner together, but he was restless. He said he had to get out of there, so he called a friend and left in her car. At the time, I thought it was because his roommate caught us in the act. But later, several months later, I finally realized that what he needed to get away from was me. The overwhelming emotional and spiritual connection that we both experienced was too much for him to deal with, I think. He wouldn’t talk to me for several days after that. I was hurt and upset, and I really needed to talk with him, but he wouldn’t answer my calls or texts.

He distanced himself from me at work. We still laughed and joked around about work stuff, but he wouldn’t talk to me about what he was feeling or what was going on with him. I knew he was dating other women, which at first was hard for me to deal with, but I had reconciled myself with that before our final time together. But this emotional distance really cut like a knife. He has since moved in with one of the other women he was dating. He’s very secretive about her; I think he’s afraid I will be jealous/angry or do something to hurt him. He’s trying to protect himself. I have gone through a whole range of emotions, including anger, but I still love him and the bottom line is that I want him to be happy. He needs time to be sure of that; to be sure I won’t turn on him, I guess. He had a very unhappy marriage and his ex caused him a lot of pain.

We will talk about this some day, when he is ready. We’re still friends, and we still work closely together.

How I’m feeling now: I still feel the pain of loss and it makes me sad. But more importantly, I am extremely grateful to this man for waking me up from my state of numbness. I didn’t know how badly I still needed intimacy in my life, but now I am acutely aware of this. I am a different person because of him; a more real and authentic version of myself. I feel rejuvenated; I have more confidence in my attractiveness and sexual appeal. I’m actively participating in several online dating sites. Nothing has developed yet, but it will, given time.

As for our history together, who knows! I am optimistic that whatever happens will be for the good. Al I can say for sure is that I have never felt as strongly about anyone before in my life, and I know he felt it too. Perhaps our story is not completely written yet.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

What were your motives for this hookup? Attraction to partner(s), Emotional intimacy, closeness, connection, Hoping or expecting it would lead to something more, To feel more desirable

How intoxicated were you? Drunk/high but not wasted

What substances did you consume? Alcohol

How intoxicated was your partner? Drunk/high but not wasted

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? no one

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

Did you get emotionally hurt as a result of this hookup? Somewhat

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? It woke me up from a decade-long state of numbness to realize that I still crave sex and intimacy in my life, and that I’m still attractive and have a lot to offer. It made me feel young again.

What was the WORST thing about this hookup? It created distance between me and my friend. He will no longer share much about his personal life, particularly his relationships with other women. He’s become cautious and reserved with me. No more drunk phone calls in the middle of the night from him. I miss the fun, carefree part of our former relationship very much!

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It made me realize that there are many kinds of relationships that can be good and healthy. I’m less of a prude and more open to casual relationships and/or dating someone when it’s not an exclusive relationship. And I feel younger now! I was starting to feel old and dried up, but I’ve been rejuvenated! All in all, this relationship was just what I needed.

All things considered, how POSITIVE was this experience? Very 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 think that our society needs to be more open-minded about sex, period. As I read in the New Yorker article where I found the link to this site, people have been having all sorts of sexual relationships for many years, but are hesitant to talk about them. Sex is a normal, healthy part of being human, and we need to stop being ashamed of it and/or afraid to talk about it.

What do you think about the Casual Sex Project? It’s a great idea! I don’t see it as a scientific endeavor per se, but it fills a void, a psychological need. I read a few stories before writing my own and I look forward to reading more of them. The more I learn about other people, the better I understand myself. I’m sure that goes for most people.

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