What’s your gender? Man
How old are you? 46
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 Orem UT
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Vice President Sales/Co-Owner $250 million dollar company
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? None
How many sexual partners have you had in your life (including oral sex)? 4
How many hookup stories have you here posted before? 2
How long ago did this hookup happen? Yesterday Jan 28th
What was your relationship status at the time? Same as current status
How would you best classify this hookup? Friends-with-benefits
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? Linda is 51 years old, married, and is five foot six inches tall. She has short black hair that has blonde highlights to hide the very little gray she has. She has striking and piercing green eyes, an elongated nose that is adorable, size 38D boobs, and she is plump but not fat, just a couple of nice love handles. She is extremely smart and was our Controller/Accountant until she left for another company. I saw her and talked with her daily, and we had developed an excellent friendship. I am really attracted to Linda and have wanted to fuck around with her for a while now.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Linda left our company before I had the balls to tell her that I was attracted to her and wanted to make love with her. So after she left, I typed up a letter and sent it to her the old fashion way, in an envelope to her new work. I didn’t reveal myself to her, but I did tell her how I felt about her as a person and how I longed to be part of her life, how I wanted to make love to her, and how I imagined that experience to go the first time. I asked her to take a selfie of herself in a green top and post it on her Facebook account if she was interested and then the following Monday at 4 pm, reserve a room at a Fairfield Inn and post an image with the room number in the post.
Well, Linda took the bait out of curiosity I am sure and last Thursday, two days after she would have received the letter, she posted a selfie of herself wearing a green blouse. Yesterday at 4:05 pm local time, Linda posted a clever image of a license plate that read 122, telling me she was in room 122. I had left work at 3:45 pm so when I saw the post of 122, I sped up and by 4:20 pm I was at the Fairfield Inn. All the way I was getting more and more horny, harder and harder. I parked my car, went to the front desk, and retrieved my key. I went up to the room, unlocked the door and entered.
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? Linda was exactly where in the letter I had asked her to be. She was naked, lying on top of the bed. When I walked in, she smiled and said, “I knew it was you.” I lifted off my shirt and then moved to undo my pants, but Linda by now was standing next to me. “No way, I get to do that,” Linda said as both her hands moved to unbutton and unzip my pants. As her hands moved swiftly, her lips brushed mine once, twice and three times as we kissed quickly. By now, Linda had my pants down to my knees and my boxers down revealing my hardening dick.
I removed my pants and stood there naked with her. “It’s been six years Jess, so make it great!” Linda said. I knew she was in a sexless marriage with her husband by her choice, and six years ago she had ended a four-year affair with a man who wanted more than just an affair; he wanted to marry her. I would give Linda whatever she wanted just as long as we were together.
I looked at her, and we then held each other, our skin touching and rubbing each other as we made out for the first time. Her tongue hardened as it entered my mouth, then relaxed. Linda and I made out for a good five minutes. She then led me to the bed, and we laid down side by side. I fingered her and sucked her tits as she stroked my dick. My dick is large, 8 inches long and probably 8 inches in diameter, and Lynda enjoyed stroking it.
Without hesitation, after 20 minutes of foreplay, Linda pushed me on my back and mounted me. She rubbed her pussy against my dick five or six times and said to me, “I love a real man with a huge dick.” She rubbed my dick against her pussy again two more times and then using her pussy, she drove my dick inside of her vagina.
I entered her, and Linda was soaking wet. My penetration felt so good to both of us. Linda drove my dick about half way in and then out until just my dick’s head was inside of her. She then drove my dick slowly all the way inside of her and then back out again, with just the dick’s head in and then slowly back in all the way. It felt damn good, and by now, I knew that Linda was in charge of this fuck and that turned me on even more.
Linda kept screwing me like this for a good five minutes and then she leaned forward and kissed me, her tongue again darting inside my mouth, but this time she drove my dick deep in her and moaned, “Uhm.” I moved my dick in and just slightly back in her cunt now as we made out and fucked each other slowly. After a good ten minutes of this, Linda sat back up and leaned forward, with her tits bouncing in front of my face. I had to use my hands to hold one and suck it as Linda increased the pace of our fucking.
As I kept sucking her boob, I could see her turn flush in her chest and boobs and watched that spread up her chest to her neck, then to her cheeks and face. Linda started fucking me really hard now, thrusting in and out rapidly and moaning, “Oh yeah” and “So damn good.” Her green eyes connected with mine and in that instance, we became one: one sexually, one physically, one emotionally, simply one and nothing else mattered. Time stopped, and the grind of daily life didn’t exist; our commitments were gone except for the one to pleasure each other, to enjoy each other, and it was beautiful. It was the sex that two middle age people are totally capable of when they want it and the need to feel alive so bad.
I felt the cum rising in my dick and knew I couldn’t hold back and Linda felt my dick starting to throb inside her vagina. Faster she went and Linda said, “Cum in me, shoot your shit in me!” Her body exploded at that moment as orgasms erupted in her, and she collapsed on my chest. I began ejaculating, shooting my cum deep inside her and Linda used her kegel muscles to squeeze and milk my dick. “Give me all of it,” she said turning me on and enhancing my own orgasm.
Afterward, we kissed and slowly began to talk. My dick though partially soft now staying inside her. Linda, after a good 40 minutes, had let my dick fall out and had begun to play with it as I sucked her boobs and rubbed her clit. An hour later, I moved Linda on her back, supported by pillows to help her back and putting my weight on my knees I entered Linda again in a modified missionary position. This time it only took 35 minutes for me to make her orgasm, but I wasn’t ready to ejaculate. So we moved to a spooning position and made love for over an hour before Linda had her third series of orgasms and I released my sperm and cum deep inside of her again.
We showered about 45 minutes later and made love with me standing behind Linda in the shower and Linda putting her right foot on a small step in the shower. That was incredible and for her fourth time Linda experienced multiple orgasms, and I spread my delicious cream of cum deep inside of her.
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? After we finished at about 10:00 pm, we agreed to meet the next Monday and repeat the experience. Linda was glad she took the chance, and we agreed to be lovers and to just enjoy ourselves each Monday and forget the world, the grind, and our commitments for the five or six hours we fuck and make love. Linda wants that, and it works for me. I probably am more emotionally connected than Linda, but that is okay. Linda is in menopause and I only fuck my wife who is faithful. Linda has had no partner for six years so we use no protection as Linda likes her dick hard, strong, and raw.
What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None
What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, Hoping or expecting it would lead to something more, I was feeling lonely, Submission / Relinquishing power
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? To feel connected to a woman who knows exactly what she wants from a man, who goes for it, and gets what she wants while ensuring my needs are also taken care of. The emotional, physical, and mental connection between us is incredible, and the sex is the best I’ve had.
What was the WORST thing about this hookup? Nothing. Maybe cost of the room.
Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I have had 1 affair about 11 years ago for about 2 months, and the woman felt guilty fucking her husband, me, and her brother-in-law, so we ended it. This one is like a total release from responsibility and cares, and it is just fun to fuck someone I care about without a commitment.
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? We text each other, and Linda leaves cute hidden messages to me on her Facebook page that only I would get.
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? There are times you need something more than what a 24-year-old marriage or a 32-year-old marriage offers. You don’t want to end the marriage but having someone else to share and fuck with is incredible and wonderful.
What do you think about the Casual Sex Project? Interesting stories and a variety of them at that.
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