A Girl I Met On AOL Chat Broke My Heart



What’s your gender? Man
How old are you? 41
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Muncie
Highest education received: High school diploma
What’s your occupation? Operator/Laborer
What’s your current relationship status? Dating casually
Religious affiliation: Agnostic
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)? 15
How many hookup stories have you here posted before? two

A Girl I Met On AOL Chat Broke My Heart

How long ago did this hookup happen? 20 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? For less than a month

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? In the late ’90s, when dial-up internet was prevalent, I had AOL for my ISP as many people did, which came with a chat messaging client. Sometimes random people would see your profile and start a conversation. In one instance, a girl did and we had a nice convo where we then decided to exchange pics. She most closely resembles the current young actress Alexandra Daddario and had green eyes and brown hair.

We chatted online over a period of about two weeks. She told me that she went to the local university and was 19 years old. Beyond that, I did get the feeling that she was just working me like she would seemingly have all of the same likes and dislikes that I did, which I found to be too coincidental. Then one day, she made a move and wanted to exchange nude pics. So we did, and I instantly fell head over heels for her. She was very attractive physically and us having so much in common seemed too good to be true.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? After the exchange of pictures, she began talking a lot about sex. For some reason, the topic of nicknames for our private parts came up, and after I told her I named my penis “wet willy,” she said she would like to “give willy a warm place to cum,” as she put it.

I was in awe of her beauty and ignored any common sense. She gave me her address and wanted me to come over at a specific time that day. So I hurried with a shower and drove some 25 minutes to her house.

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? She was even sexier in person than in her picture. She greeted me wearing tight shorts and a sports bra. Her breasts were quite large for her body, and I wondered to myself if they were fake or not. To my surprise, they weren’t, or at least they didn’t feel like they were. I was making conversation, but she acted as if she was just amusing me. She came off to me as seeming like she was in a hurry as she tried to lure me to follow her into her bedroom.

As I was talking, she sat down on her bed and quickly took off her clothes then spread her legs before me, making it clear that she wanted to fuck right away. Her body was very well toned, and I got hard just looking at her. I pulled down my pants and got on top as she guided my dick in telling me to push. I was pretty much just a slave to her looks at this point and not using any common sense.

Her pussy was like a rubber band; I went in easy and it snapped shut snuggly around my dick. The amount of friction was perfect. She was not too wet, not too dry, and I could feel every contour of her inside. As I pounded her, she was panting loudly and when she told me she was going to cum, it acted as a trigger and prompted me to cum sooner than I wanted to. So, I asked her where she wanted me to cum, and she just told me to stay inside. Normally, I would have anxieties about doing so, but I was dumbstruck by her looks and did as she asked.

We stopped momentarily as we caught our breaths. For some reason that I don’t understand to this day and will never forget, she took that opportunity to drop an unexpected bombshell on me. “Hey, just so you know, I have a boyfriend, but I want you to cum inside me again. Can you keep going?”

I felt a bit hurt and didn’t really understand why she waited until now to say this. She had her legs and arms gripped around me, not letting me go and continued provoking me to keep going by saying, “Come on. It’s okay.” So in the position I was already in, I gave it a shot even though my dick was now very sensitive to movement, but I guess my cum acted as a lubricant and helped.

I endured the discomfort for about another 10 or so minutes all the while thinking about why she even bothered to tell me that she was in another relationship. I can only guess that perhaps she only said it so that I wouldn’t get attached to her or think that she really liked me or anything. So she got what she wanted and was probably used to that, so I kept pounding away and it seemed like there was no end to it. She would get really loud at the point of orgasm, tensing up inside, arching her back, and pushing her hips into me making my dick even more uncomfortable than it already was while telling me to “fuck me harder,” as she put it. Finally, after quite a while, it started to feel really good again. It seemed as if a couple of hours had passed, though I’m sure it couldn’t have been near that long, and I was wondering the whole time if she was about done. Finally, she started repeating the words “cum for me” in my ear every few seconds, and finally, I was able to cum again. I immediately felt bad for her boyfriend the second I did that, especially thinking that he probably had no idea what kind of girl she really was.

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 I finished the second time, she finally released her legs around my waist and let me up. I felt a little awkward still thinking about what she said and again feeling very bad for whoever her boyfriend was, hoping it was no one I’ll ever meet. She kept her legs spread and sat up, watching my stuff ooze out of her, and she took her finger and began playing with it for a moment and rubbing the excess over her vagina. In hindsight, I’m guessing that maybe she had a cum or breeding fetish.

I got dressed, and she looked at me telling me I needed to get going before her parents got home. She put her clothes back on without even wiping off and basically rushed me out the door.

Despite that I developed feelings for her and maybe still had some hope that perhaps she was in the process of breaking up with her boyfriend or something, a couple of days later I tried to message her on chat. She would blow me off saying that she was doing homework or whatever until I finally stopped bothering her.

I felt hurt, and it broke my heart. But, if you ever read my previous story, then I suppose it was karma. I guess I deserved it.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, I don’t know if my partner was on any (other) method

What were your motives for this hookup? Attraction to partner(s), Emotional intimacy, closeness, connection, Hoping or expecting it would lead to something more

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? I don’t recall mentioning it to anyone.

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? Very

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

Do you regret this hookup? A little bit

Why do you regret this hookup? She was playing me and used me for a one-time thing. She waited until it was too late to tell me that she had a serious boyfriend.

What was the BEST thing about this hookup? The sex itself was a great experience, and she was very attractive.

What was the WORST thing about this hookup? That she waited until I finished before telling me she was in a relationship, leaving me to conclude that everything she told me was probably a lie and just wanted to lure me into a one night stand without making herself feel like a slut.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It has made me realize that people will avoid being upfront and honest just so they don’t feel like they are being too promiscuous.

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

All things considered, how NEGATIVE was this experience? Somewhat negative

Anything else you want to add about this hookup? I don’t mind a “notch in the belt” type of encounter, but I fell too hard and fast for a girl I didn’t really know and ignored the warning signs.

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? Same as my last story.

What do you think about the Casual Sex Project? Same as my last story.

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