Her First Time Sober



What’s your gender? Man
How old are you? 56
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? Engineer
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? Horny old man
How many sexual partners have you had in your life (including oral sex)? 11
How many hookup stories have you here posted before? 1

Her First Time Sober

How long ago did this hookup happen? 17 years ago

What was your relationship status at the time? Same as current status

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? For less than 6 months

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? She was a somewhat average, yet attractive younger woman. Ten years younger than me. I’d say she was about 5’4” and maybe about 150 lbs or so. Medium long brown hair with C cups. Unusual since I usually am more attracted to older women. She was a single mother with two younger children.

We had met about three months earlier when I was up her way for hunting season. We had been introduced by a mutual acquaintance and seemed to hit it off right away. By the end of the week I had her in the back seat of my pickup at a pullover on a back road. Both of us we very uninhibited having drank quite a bit of beer. This hookup was much better though as I’ll explain.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We stayed in touch in spite of me having to be very discrete. I had found a reason to return to our cabin about 10-12 weeks after our first meeting. We had arranged to meet at the little bar up in the mountains again that Saturday evening. This was in January in the mountains of north central PA. Yes it was bitter cold with blowing snow, but I was on a mission.

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 walked into the bar and found her talking with a few women at the bar. I approached and she introduced me as her date for the evening. It soon became clear she had been sharing her plans for the evening with them. A somewhat awkward, but intriguing experience. The women knew that Miss H planned on getting laid that night.

I ordered a beer and sat with them. H finished hers and declined my offer to get her another one. She seemed a little anxious and suggested we go. It seemed almost too easy. I thought I’d have to wine and dine (at least wine) her for a while before I would get her to go for the ride. The other women wished her luck, wink wink, and told her to be safe.

We left and jumped in my crew cab pickup and headed in the direction we took a few weeks earlier. As we crossed a field and headed towards the forest it became evident what the sign that said no winter maintenance meant. The state forest road was blown shut with a deep drift. Since there was little chance of any other traffic coming by I backed into the driveway of an empty cabin and turned the lights out.

Since the truck was just warming up, we began to make out in the front seat, eagerly moving our hands underneath the heavy winter wear while passionately kissing. In about five minutes the truck was quite toasty. We moved to the huge back seat that I had made sure was emptied out earlier that day. If you ever have the pleasure to do it in the back seat of Ford Super Duty crew cab, try it. With the front captains chairs moved all the way forward Its like an adult playpen back there.

The winter boots came off first, then the jackets. Soon we we both comfortably naked and all over each other. I knew from the last outing that she wouldn’t let me go down on her so I didn’t bother trying. But oh my was she wet! After fingering her a few minutes she had a very satisfying orgasm. She then proceeded to return the favor after letting me know she didn’t want me to cum in her mouth. She obviously wasn’t well versed in giving a BJ, but none the less it still felt good.

She did manage to get me real close after about ten minutes of working my dick. I could tell she about had enough so I pulled her up and continuted kissing and fondling her. I unpacked a condom and unrolled it over my shaft. I gently pushed her onto her back and onto a soft blanket I had positioned behind her head, up against the door. I grasped her ankles and raised her legs to the roof. I slid into her slopping wet pussy and slowly picked up speed until I was fucking her hard and she was moaning. After a few minutes I pulled out and sat in the middle of the back seat. I pulled her up onto me with her wrapping her legs around my waist. I sat on the edge of the seat with my legs spread so she could slide her ass down between my thighs getting me deep into her pussy. In this position she could lean back against the front seats and I could play with her breasts and finger her while we fucked. It wasn’t long before we both came hard. I thought I was going to launch her through the moonroof. We collapsed against each other and savored the moment.

It was then that she told me that was the first time she fucked sober and that she was always so uncomfortable with other guys she always got drunk first. I took that as a compliment.

We cleaned up and I got rid of the filled condom and wrapper. Couldn’t accidentally leave that laying around in the truck. We wrestled our winter clothes back on and returned to the bar. To my favor the other women had already left and we could enjoy some time together.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, 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? I felt great, and from her reactions I think she felt good about it too. Since I was (am) married I had to be very cautious about contacting her on a regular basis. I didn’t return to the cabin until later in the spring. I found out she had found a steady boyfriend so I didn’t pursue looking her up.

I saw her a few years later at a different bar and she was alone. I was with a new long term FWB that night and I couldn’t talk with her. I did notice her checking me out though, but neither of us let on like we knew each other. I still keep an eye out hoping to see her again, but I have no clue if she’s still around.

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

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, To feel more desirable, To feel more confident, Making new friends, It was easy / convenient

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

What substances did you consume? Alcohol

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

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? The guys at camp. Got the ol high five. Back in the day, they’re 20 years older, they had quite a time in hunting season with the locals.

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? I don’t know / I’m not sure

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Very good sex with a very enthusiastic partner.

What was the WORST thing about this hookup? That we never hooked up again. Would have liked to have been able to take her to the cabin in nice weather and use a real bed.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No. I’ve always enjoyed casual sex with the right partner. They’re just to far and few between.

All things considered, how POSITIVE was this experience? Very positive

All things considered, how NEGATIVE was this experience? Not at all 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 casual sex between consenting adults is fantastic. Good way to relieve tension and explore yourself. Great confidence booster.

What do you think about the Casual Sex Project? Like checking in daily for my fix.

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