A Lady With Gray Hair


What’s your gender? Man
How old are you? 31
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Maryland
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Engineering Consultant
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Catholic
How religious are you? A little
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? >70
How many hookup stories have you here posted before? 0

A Lady With Gray Hair

How long ago did this hookup happen? 2 months ago

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? Jane is in her early 60s, slightly under 5 feet tall, thin petite body, blue eyes, and has very short gray hair with a modern style. Generally, I like long hair on women but Jane can pull that look off perfectly and with class. She looks amazing for her age.

I was on travel having lunch at a small coffee shop near my hotel. From the corner of my eye, I noticed a pink high heel connected to a sexy leg sticking out of a tiny table. I took a second glance and noticed those legs belonged to a lady with short gray hair sitting alone looking at her phone. She was wearing a pink sleeveless dress that showed off her toned arms. The dress fit tight on top and flared at the bottom. It was a conservative but sexy outfit. By her appearance alone, I could tell she had professional occupation.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I usually use a popular online app to find a hook-up but something was tempting me to try my luck with this lady first. The worst thing that could happen would be to get rejected.

My coffee and sandwich was ready so I walked over to her table and asked if I could join her. My excuse was no other places to sit. BTW: There were plenty of empty tables. She looked around the dining area, smiled and gave me a witty reply, “Is that the best you’ve got? You can have a seat ONLY if you plan to ‘hit on’ me.” I smiled and said, “Now the awkward first impression is out of the way……” I sat down and began to flirt. I could see in her eyes she loved the attention and kept rocking her leg up and down as I poured on the charm.

During our brief ‘getting to know you’ conversation, I found out that she’s a lawyer, works around the corner from the coffee shop, and is also married. She was wearing a wedding ring set with a huge diamond. I told her I was in town on business and she leaned in interrupted and whispered, “And you’re looking for companionship tonight?” I put my hand on hers and said, “I would love to enjoy your company tonight.” She asked where I was staying and I told her the hotel across the street. We exchanged numbers and I sent her a text with my room number.

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? I got back to my room that evening around 6pm. I got a text from her soon after. She was leaving work now and on the way. Within fifteen minutes, I heard a soft pecking on the door. I let her in and we wasted no time removing our clothes. Her body was fit with smooth skin and she had a well trimmed landing strip. I offered oral but she told me she came here for sex. I was hard and she insisted to start on top. Her pussy was wet and felt tight as she lowered onto me. I grabbed her smooth firm ass with both hands. She rode me till we both got off. She asked to cuddle a little so we did. Her hands felt soft as she placed them on my cheeks as we kissed. Her skin felt like silk as I was using my hands on her body. We were kissing with tongue and she lowered her hands to massage my cock until I was hard again. I put on another condom and guided it back inside her. We kissed and had passionate sex. We took turns rolling over on top of each other and having slow sex until we were both spent. She laid on my chest, put her soft hands on my cheeks, and we kissed until she decided it was time to leave.

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? She sent me a text the next day offering to hook-up again the next time I’m in town.

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

What were your motives for this hookup? Learning new things, experimenting, 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? 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? A few co-workers. We all share hook-up stories. They thought this was hot story and impressed she’s willing to hook-up again. I’m friends with her on a social media account. I showed them a photo of her and they thought I made a good decision.

How would you best summarize people’s reactions about this hookup? Relatively positive

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? When I first seen her at the coffee shop, I never thought she would agree to a hook-up. I assumed I would get rejected so I took the ‘all in’ approach. She loved it and we both had a good time.

What was the WORST thing about this hookup? I can’t think of anything. It was all good.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I’ve been married for 6 years. I started traveling with my work 3 years ago and began hooking-up soon after. I never thought I would cheat, but after hearing stories from my co-workers, I was curious. They helped me load an app and gave me advise on a few details to keep things anonymous. After I got my first experience out of the way, it has become regular for me when I’m away from home. It’s easy to find someone to randomly hook-up for sex.

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? With what little time I had with Jane, I came to the conclusion that she was a powerful and professional woman that’s direct but not pushy or dominating, knows what she wants but not demanding, and likes to have a good time but with a little passion.

All of my past hook-ups have been a ‘one-time’ thing because it keeps emotions out of the situation. Jane is the oldest person I’ve had sex with and the experience was amazing and thought this story was worth sharing.
I keep reading Jane’s text with the offer to hook-up when I’m in town again and I’m seriously considering.

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? Within my circle of friends/co-workers, casual sex while traveling is common. With technology and social media, it’s become easy and confidential too. People are having casual sex, but it’s not talked about openly. My wife is unaware. The wives of my co-workers are unaware. The way society evolves, there may be a day it becomes common for married couples to incorporate casual sex in a marriage.

I think the next issue society will have will be that casual sex will become so common, people will stop dating and having relationships.
I know loads of men and women in their 20s and they constantly complain about the pressures of dating and that it’s easier to arrange a casual sex hook-up than find a nice person to go on date with.

What do you think about the Casual Sex Project? It’s a great idea. Glad it’s out here for people to read and share.

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