Sex for Four Hours Non-Stop

by Dan

What’s your gender? Man
How old are you? 50
What’s your race/ethnicity? East Asian
What continent do you live on? North America
What country and/or city do you live in? Canada
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Business development
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Late bloomer to casual sex
How many sexual partners have you had in your life (including oral sex)? 10
How many hookup stories have you here posted before? 4

Sex for Four Hours Non-Stop

How long ago did this hookup happen? 2009

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 month

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? I met Kate through an online dating site. She was a 32 year old school teacher, 5’5″ with long blond hair and a slim build. Her online photos showed that she was “girly” and attractive. Since she was off work for the summer, I decided to take her to lunch on a week day at a celebrity chef restaurant for our first date. It featured local food which was a hip trend at the time. I could tell from her profile that she would like a fancy date like that. I picked her up at her apartment. She wore an elegant summer dress and high heels. She was much more attractive than her online photos. She could easily pass for a beauty pageant contestant. Seeing her sexy heels gave me hard on. Our lunch was relaxed and very pleasant. We had a second date soon after that. I forget what we did for the second date, but we ended up back at my apartment. While we sat on the sofa, I reached out to kiss her and she turned her head away to present her cheek. I asked if this was because she was not interested. She seemed shy and was being coy. She didn’t give a straight answer, but something came out about other guys being more aggressive. With that, I reached in again, held her by the chin so she couldn’t turn away again, and kissed her on the lips. This led quickly to a heavy make out session. I took her upstairs to my bedroom where we continued making out on my bed. Then our clothes came off and we had sex for the first time. It was very enjoyable for both of us. As I was about to take her home, she said “that was very good” with a happy and satisfied smile. I was 43 at the time and elated that I was with a younger woman who was strikingly beautiful, sexy, and seemed to be interested in me. I could see a relationship happening leading to long term marriage and family.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I also forgot where we went on our third date. I remember that it was a Friday night, and we ended up back at my place again. We headed straight for my bedroom. I put on a CD and we started making out. The last time we had sex, I felt the tip of my cock hitting something as I thrusted in deep. Maybe she had a short vaginal canal. I asked her about this, and whether it hurt. She said other guys have asked her that before. She sounded a bit embarrassed, and then she said she squirts. I was excited to hear that. I asked if hitting whatever it was caused her to squirt. She didn’t have an answer. She just said she squirts. She said she enjoys it, and it feels like a release. With that, I was ready to have sex.

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 continued kissing. I started stroking her pussy. As soon as she got wet, I inserted two fingers and started stroking and rubbing her insides, feeling for her G spot. After a good amount of moaning from her, we moved to missionary style sex. Even though my first time sex with Kate went very well, I remembered my premature ejaculation with Susan (see an earlier post), so I wanted to avoid this with Kate tonight. I told Kate, “I am going to pace myself.” I started with slow steady thrusts, and concentrated on kissing Kate passionately, massaging her body, and embracing her. This went on for a long time, until my cock was used to the pleasure of Kate’s pussy wrapped around it. I then started fucking Kate a little faster. This felt great for both of us, and Kate started moaning now. As soon as I felt an orgasm starting to rise, I stopped thrusting. I stayed penetrated deep inside Kate, but not wanting to remain still, I started vibrating and shaking my hips and ass intensely. This brought waves of moans from Kate. I must have been stimulating her clitoris by doing this, because she was coming. Meanwhile, by not thrusting, I was calming down from an impending ejaculation. I continued like this, alternatively thrusting in and out of Kate for a few minutes, followed by vibrating my hips and ass as I pushed my cock to rest deeply inserted inside Kate. She was moaning loudly every time I did this vibrating move. Finally, I noticed the CD had finished playing. I knew the play length of this CD meant that we had been fucking for at least a good 50 minutes. It was probably about 1 am now. Since this was working, I didn’t change anything. I kept fucking Kate like this. Since the pressure was off and I lasted for so long, my thrusting became faster. Kate asked, “how can you last so long, did you take a pill or something?” I said “no, I am just pacing myself, and you are so hot and sexy that I want to keep going.” She liked that reply. She said “thank you” and continued moaning. Without the music playing, we could hear ourselves having sex. After a while, Kate said “I wonder what the neighbors are thinking.” I replied “I don’t care what they think!” With that her moans got even louder. This went on for what seemed forever. But by now, I couldn’t have an orgasm after holding it back for so long. Believe me, I tried. I tried thrusting hard and faster but nothing came. Eventually, I just pulled out. It was well after 4 am now. It was amazing: my cock was inside Kate for over 4 hours. We were about to go to sleep, but we noticed the bed sheets were soaked. The wet spot was a foot and half circle under where her pussy was. The mattress under that was soaked wet. We had to lay towels over the mattress and change the bed sheet. She said she was sorry, but I said it’s not a problem at all. The next morning, when Kate woke up, she got of all fours over me. Her pussy was wet. I could feel two drips of her wetness dripping onto my groin. She said, “I want your cock inside me.” As much as I wanted to fuck again, the intensity of the four hours of non-stop sex the night before was too much. I couldn’t achieve an erection.

How sexually satisfying was this hookup? Very

Did you have an orgasm? No, but I was 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? I took her out for breakfast. As Kate was getting dressed, she was happy with her tousled hair, looking like she just had sex. She said her hair always looks like this after sex. She didn’t make any effort to change this look as we went to a neighborhood restaurant. We talked about the night before. She said she also enjoys the cow girl position and her best sex position was being pushed against the wall. It sounded like she had a lot of partners, despite how shy and conservative she appeared. For fun, I asked her how often do you want sex? She replied three times a day. I asked her do you want to try that? She said sure. So we made plans for me to stay over at her place for half the week. The first night, we had sex in the butterfly position before going to sleep. The next morning, I fucked her missionary style. I arrived at work fully satisfied to start the day with sex. All day long at work, I was semi-hard thinking about sex again when I got home. When I arrived back at Kate’s apartment that night, I forced her against the wall and nailed her the way she said she liked. I could feel her wetness running down my leg as I fucked her standing up. That night before bed time, she rode me hard in the cow girl position. I found that the more sex, the more I wanted it, and the better I was at lasting longer. I was in a zone of performance that I did not thought possible. Kate and I started looking up different positions on Cosmopolitan magazine to try. This went on for almost a week, until it was taking up too much of our time. I also wanted a long term relationship leading to marriage and was serious about this path and so was Kate. At 43, I was looking for this for a long time. However, things unraveled very quickly. Within a few weeks, I was getting annoyed that I was always paying for everything. She never lifted a finger. He response to this was that I should be treating her as the man. If I didn’t want to do this, there were plenty of other guys that would. We also had different interests outside of sex. She was also chronically late for everything. She was beautiful and loved to wear heels and dresses. She even showed up at the beach with bikini and heels, and turned every guy’s head. But she wanted constant complements about how beautiful and sexy she looked. Once I did not compliment her, she got livid. She finally told me it was over after three weeks of dating. I did see her on dating sites after that. I even saw her at two speed dating events in the years later. When we spoke, we were always pleasant and friendly. I even sent her some excellent wine for her birthday because she loved red wine. Last I checked, she is still on the dating site where we met. She’s 40 now, and gained a lot of weight, and is not as attractive as she once was. But I still remember the great sex we had. It was the best.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Hoping or expecting it would lead to something more

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? 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? 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? The great sex, leading to more great sex after this hookup.

What was the WORST thing about this hookup? I could not reach orgasm.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Casual sex is a great way to start a relationship. Just do it and see where it goes.

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? No

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 replied to this in an earlier post.

What do you think about the Casual Sex Project? I replied to this in an earlier post.

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