What’s your gender? Man
How old are you? 53
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Ojai, California
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Postal Service
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Christian
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 6
How many hookup stories have you here posted before? None

Drunk 50 Year Old Woman Took My Virginity At 20

How long ago did this hookup happen? 33 Years Ago

What was your relationship status at the time? Single

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? I was a 20 year old airman in the US Air Force stationed in England at RAF Lakenheath. I was also a virgin. I was driving home when I saw a woman flagging me down on the roadway. She looked distressed so I stopped and she asked for a lift. I agreed and she asked me to drive her to the other nearby base in Mildenhall to the NCO club. She was a mess. She was 50 (she told me) and was dressed in a mini skirt, but she was actually very ugly looking. She was very small and skinny. She looked like a worn out hag. Plus, she was a bit drunk.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Being a virgin with no experience in woman, I didn’t think of bedding her at first. Not to be bragging here, but I was a pretty good looking guy at 20. I was also very shy and inexperienced in the ways of the world. But I was also a very horny kid and when she put her hand onto my knee and smiled, that was it for me. My lust got the better of me and I invited her to my home (I lived off base by myself) and she accepted. In my mind, I was telling myself that I was only going to give her a place to spend the night safely and that would be it.

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 got to my home and since it was about midnight, I showed her my bedroom and told her she could go to sleep and I wouldn’t bother her. She went to the bed, took of her dress and panties and kept her top on and got into bed. I turned out the light and was about to leave when she told me she wanted me to sleep with her. Up until that moment I’d been fighting with myself to steer clear of her. But hearing her say that and patting the spot next to her was too much for me. I sat on the bed and she reached out for me trying to take off my shirt.

I then stripped off and got underneath the covers with her. I could see her clearly since the propane heating furnace was on. From then on I went into automatic mode. I’d seen porn and Rated R movies, so I sort of knew what to do. I wanted to kiss her (I’d never even kissed a girl before) but she was so damn ugly I just couldn’t do it. But I did want to see and such her breasts but she had her shirt on. I tried taking it off but she got angry and started yelling at me to leave it on. She then spread her legs and told me to get on top of her.

I obeyed, and once I was in position I had no earthly idea what to do. I even told her that I didn’t know what to do next, and then she reached down, took my penis into her hand, guided me to her entrance and let go. I was greeted with an extremely wet spot between her legs. I thought she was bleeding and pulled back which angered her again. She asked me if I wanted it, and I mumbled that I did. She got me into position and once again I felt her wet spot. She told me to push in, and I did and I suddenly realized that I was now inside her.

I started moving between her legs and I looked at her very ugly face and I suddenly caught a whiff of something that smelled very bad coming from her. I remembered looking down at her face at that moment and saw that she was smiling at me. She told me that I looked so handsome and began running her fingers in my hair.

I suppose had this been with a beautiful woman I’d have probably come in a matter of moments. But I was with an ugly, smelly old hag that revolted me. Only because of my youthful lust was I able to remain very hard inside her. As a result, I was able to stay inside of her for probably five minutes of hard thrusting and she seemed to enjoy every moment of it. When I told her I was about to come she wrapped her legs around my waste and held onto me tightly as I flooded her with my sperm. Stupidly, I didn’t use a condom.

When I was done she looked at me and told me that she felt me come.

I was disgusted and revolted by my actions. I got out of bed and cleaned myself off and then told her to go to sleep. She told me she wanted me to sleep next to her but I told her I’d join her later. I then sat by the fire the entire night repenting of my actions. I had to stay in the room because it was the only heated room in the house.

Early next morning she woke up sober and l was still awake. She looked around confused for a moment and the say me and smiled. She looked at her blouse she was wearing and took it off. She apologized for not taking it off last night but was concerned that I would see that she had small breasts and wouldn’t want her.

As soon as she took off her blouse and exposed her breasts to me I got hard again. She asked me to come back to bed and without hesitation I stripped off my clothing and got back underneath the covers with her.

We did some fondling and I got to suck on a woman’s breast for the first time. She obviously had a hang over and didn’t really want to do this now, but I think she felt obligated to do so since I let her spend the night. I couldn’t kiss her on the lips though because she was so ugly in the morning light. The smell coming from her was even worse after she came back from going to the bathroom. She asked me to give her oral sex but I almost threw up just thinking of putting my face near her bottom where the smell was coming from.

I decided to go ahead and get this over with so I asked her if I could enter her. She told me it was fine and I did a repeat from last night. But this time she wasn’t wet between the legs and I couldn’t enter her. I asked her for help and she put some spit onto her fingers and smeared it between her legs and told me to try again. It worked and I soon was back inside of her.

The sex was awful for the both of us. Had I been older, there is no way I could have maintained an erection as long as I did. I actually lasted maybe fifteen minutes inside of her but I had to turn away from her face to keep myself stimulated.

When I finally came inside of her there was relief on both of our faces now that I was done.

She got up and took a bath (how I wish she had done that first). She asked me to come rub her back with water and I did with some revoltion. Though I’d been intimate with her and hadn’t really seen her nude, and believe me she wasn’t any better looking naked than with clothing.

After she got dressed I took her to a bus station and though I didn’t have to I gave her twenty pounds (about 45 dollars or so) and she gave me a kiss on the cheek, and that was it.

How sexually satisfying was this hookup? Not at all

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? No

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 came back home and wanted to cry. I was also scared that I’d caught an STD. Luckily, that didn’t happen.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

What were your motives for this hookup? I didn’t want it but was unable to stop it.

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? A little tipsy/high

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? A little bit

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.

Did you get emotionally hurt as a result of this hookup? Very

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? Very much

Why do you regret this hookup? I lost my virginity to a smelly, fifty something old hag.

What was the BEST thing about this hookup? Not a damn thing.

What was the WORST thing about this hookup? The smell coming from her.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Don’t screw drunk, old hags.

All things considered, how POSITIVE was this experience? Not at all positive

Anything else you want to add about this hookup? A time machine to go back and warn myself.

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