What’s your gender? Man
How old are you? 50
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? United States
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Small Business Owner 250 million dollar company
What’s your current relationship status? Engaged/Married (open)
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Horny
How many sexual partners have you had in your life (including oral sex)? 9
How many hookup stories have you here posted before? 3
How long ago did this hookup happen? This past weekend
What was your relationship status at the time? Same as current status
How would you best classify this hookup? One-night stand
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? Ellie is 5’7″ tall, dark black hair down to her waist with green eyes. She is slender, 26 years old and working as she completes grad school. She is the night clerk at the Marriott I stayed out this weekend. She checked us in the first night, and was there the next two nights, since she works Friday, Saturday and Sunday.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? On Saturday morning, I woke up around 1 a.m. and needed to get some water and go for a quick walk. I usually walk when I wake up at 1 a.m. as I find it relaxes me and allows me to sleep better. I got on my sweat pants, a shirt and shoes, and went for my walk. At 1:30a.m. I headed back into the hotel and went to the front desk, getting a bottle of water. Ellie was there, asked me for my room and my last name which I gave to her and said “Thanks gorgeous.” Ellie stopped me, and said “Why did you say gorgeous?” “I always say that to a beautiful woman which you are.” I replied. “What makes me beautiful?” she asked.
At this point I paused, and looked her over and inquired “Do you really want me to say?” “Yeah, or I wouldn’t have asked.” was her reply. ‘Okay, I love your long, black hair that goes to your waist and if I was 20 years younger I would want to have it draped around me. Your green eyes are piercing and show signs of high intelligence. Your cheeks compliment your facial structure perfectly and your lips, are full and again, if I was younger I would long to kiss them, to feel them press against mine, and to feel our tongues dance inside of each other’s mouth. Your smile is captivating, disarming and inviting, friendly. You are truly beautiful.”
I continued. “You have a long neck, one that is perfect to kiss and explore. Your breasts are perfectly round, large, firm and your dress shows your self-confidence. Your slender waist is attractive and I bet you look great in a bikini. You have a small, tight ass, and I won’t mention it would be great to squeeze it while making love with you. Also, your long legs are not only attractive, they would be wonderful to wrap around your lover as you make love together.. So yes Miss Ellie, you are indeed a beautiful woman physically and intellectually.”
With that I grabbed my water hoping she enjoyed the compliment from a 50 year old man, and as I grabbed the water bottle, her hand closed around mine. “Damn, that was beautiful” Ellie said. She smiled, went to the back room for a moment, came out with her assistant, who was smiling, and Ellie asked if I would come with her. “For what?” I asked. She smiled, taking me by the hand and leading me down the hall to the first guest room. Her key unlocked the door, we entered and she shut the door.
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? Now Ellie stood there and took me by the hand and led me to the bedroom. There she put her arms around my neck, and said “I wish more men said shit like that to me.” With that she kissed me, her lush lips pushing on mine, her tongue dancing into my mouth greeting my tongue. I kissed her back and then paused. She stopped and asked “What?” “Age?” I asked. I was literally old enough to be her father. “I don’t give a damn.” Ellie said. “Look, you turned me on, a lot. I know your married, I don’t care. I am not looking to marry you. I just want to fuck you for a couple of nights, enjoy it, and you go your way and I’ll go mine. No one will know, ever. So shut up and make love to me.”
With that Ellie began making out with me again, and we undressed each other. Sure enough, she was beautiful. Her breasts were firm, young, full and perfectly round. Her pubic hair was present but trimmed nicely. We moved to the bed, laying side by side and Ellie touched my balls and dick, I sucked and licked her breasts and nipples. I felt her pussy and she was soaked. Ellie put her leg over me and I moved myself into position, my hard dick eagerly seeking the warmth and wetness of her cunt.
I brought my penis up to her pussy hole and Ellie took my dick and guided it right inside. Slowly, I thrust my dick completely inside her causing her to moan. Slowly I withdrew about 2/3 of the way and then slowly thrust it back inside completely. I did that for about 5 minutes, slowly in, slowly 2/3 of the way out, slowly back in. Ellie moaned as she paused kissing me saying “Yeah, hell yeah.” We kept up this deliberate and slow pace, sometimes Ellie would pause and stop me when I was completely in her. She looked at me and said “John, your awesome.” “Why?” I asked continuing now to thrust and withdraw. “I’ve been with three men, and all three were done by now. You’re really turning me on.” She smiled and said “Change.”
Ellie now moved from being side to side, to getting on all fours and telling me to do her from behind. I did that, keeping up a steady rhythm and brought Ellie to her first orgasms. She collapsed on the bed, and my hard dick fell out of her. She rolled over and brought me down on top of her, those long legs wrapping around my hips and ass, “Like this?” she smiled, referring to my comment of her wrapping her legs around her lover. “Yeah.” I said and she guided my hard dick back inside her still wet vagina. “Fuck, me John, really fuck me.” Ellie said. I did, I entered her and kept my dick in her pulling it almost completely out, before driving it all the way in. A quick, steady pace I kept up doing this as I kept my weight on my hands and made love to her.
I kept the pace up and my dick was rubbing her clit as I made love to her. Ellie started raising her ass up off the bed and moaning. I kept going and felt my dick get harder and Ellie’s eyes went larger and she moaned more. Faster and faster I went, feeling that sensation to cum arrive, holding it back. Suddenly Ellie squeezed me tight, her legs squeezing my hips and ass hard, and her body tensing as her ass and vagina went into multiple fast spasms of pleasure. I let my first load ejaculate deep inside of Ellie, and she screamed in pleasure and I moaned loudly. Again and again, she came and I shot my loads until we collapsed and began kissing.
“Are all older men so great?” Ellie asked. “It’s experience, knowing what a woman likes, putting off your own ejaculations until your lover is pleasured. Your pleasure will only bring more pleasure for me.” I said. “Okay, tomorrow night, 1:00a.m. again? ” Ellie asked? “Sure.” I replied. It was now almost 4:00a.m. We dressed, Ellie went back to work after explaining she had never done this at work, though her team mates had multiple times. I told her I had had a vasectomy so no worries about pregnancy. Ellie said no disease from here as she hadn’t had sex in 2 years and was clean. Same for me.
I went back to my room, my wife was still asleep, I got back into bed, thinking about making love to Ellie and slept until 9:00a.m.
The next night I went down at 1:00a.m. again, no walk, I wanted another workout. Ellie and her assistant was there and the assistant smiled at me. Ellie said “No, he’s mine.” Ellie took me to the same room, and there we undressed each other, made out, got on the bed, and made love. This night we did the missionary again, we did Ellie on top which was a first for her and which just made her wild and was the first time I came in her. We then kissed and made out a bunch, with a lot of foreplay until I got hard again and Ellie wet on her own again, and then we did the kneeling position, she loved that also, then the spoon position and finally Ellie finished on top. Ellie had three orgasms from each position the second time and I came in her multiple times with her on top.
Ellie fell on top of me, kissing me, said “Good thing you don’t live here or this would end up being an affair!” I looked at her, kissed her and said “I think I could handle that but oh well, we are 5 hour apart by car.” “Yeah, maybe next time you come down?” Ellie asked hungrily? “If your still working here.” I said. “Oh, I will for the next 2 or 3 years. How often do you come down here?” she inquired. Two to three times a year.” I said. “Well, you will have to return to our Marriott won’t you?” she said. Kissing her again I said “Especially if your still here.”
With that we began making out and got turned on one last time. We made love missionary style and each had an orgasm. It was now 5:00 a.m. and we got up afterwards, dressed, and I went to my room, back to bed, and Ellie on her way.
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 checked out Sunday morning and Ellie was there at the counter. She pulled me in the back, kissed me, gave me her number and email and said, “Keep in contact.” “I will, whenever I am down here.” “Promise?” Ellie said. “Yes.” I replied. I then pulled my luggage cart outside waiting for my wife to pull up. I loaded the car, caught Ellie watching me and I noticed why I was so attracted to her. She reminded me a little of my wife who has short black hair, hazel eyes and is the same height.
I drove away, finishing our business in this city and then we drove home. It was a memorable weekend.
What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Sterilization, Discussed STI testing history
What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Just happened, I don’t know why, just went along with it
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? Somewhat
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? I will with my wife. We have a semi open relationship. She prefers being sexless so I can cheat once every so often as long as I stay clean.
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? Not at all
Do you regret this hookup? Not at all
What was the BEST thing about this hookup? Sex was incredible. I haven’t had sex in 18 months so it was much wanted and enjoyable.
What was the WORST thing about this hookup? I felt bad in our age difference but Ellie didn’t care, still doesn’t care. She wasn’t sure at first but tried it and loved it. I still have a slight hang up on it, but got over it fast.
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? Great two night stand! Loved making love to Ellie, enjoying her and giving her pleasure and then receiving pleasure.
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? We need the emotion and physical pleasure sex brings. There is nothing like the human touch, to soothe, excite, pleasure and enjoy. Nothing. Each their own.
What do you think about the Casual Sex Project? I find it interesting that there are so many posts and views.
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