What’s your gender? Man
How old are you? 30
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: College degree (eg., BA, BS)
What’s your occupation? Audio Engineer
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Christian
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)? 30
How many hookup stories have you here posted before? 1
Online Girlfriend and the Rogue Sickness: Part 1
How long ago did this hookup happen? 15 Years Ago
What was your relationship status at the time? In a relationship (monogamous)
How would you best classify this hookup? One-night stand
How long did you know the person before this hookup? For 1 to 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? She was a toned brunette with an incredibly hot body and a unique look to her. She looked like Britney Spears with a slight bit of Asian heritage somewhere in the mix. We knew each other ‘well’ but we had only known each other online. Being that this was in the earlier days of the Internet, she was my ‘online girlfriend’ before we actually met up for maybe about a year. We had met through a mutual friend I also played video games with, and for the most part we gamed a lot together. We talked a lot and generally enjoyed each other’s company, and even though I had never seen her in person I had some pictures of her and loved what I saw. I also liked her personality a lot, thinking that this would actually lead somewhere in the future.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We were both still in high school at the time and I drove to her parent’s house which was many hours from mine. She lived in a huge house, I would almost call it a mansion, and when I arrived I met her and her family which was a little awkward. Afterwards we went into her room and we started chatting about whatever, but within 5 minutes of being there she got up and got changed right in front of me. I didn’t know what to do at the time, as this turned me on to an unbelievable level, so I got up when she was just in her pants and underwear and pulled her to me, complimenting her body and kissing her briefly.
For the rest of the day/night until I left we hung out watching TV on her couch and held each other. Eventually it was time for me to find a hotel room, so I left but it was dark and I had absolutely no idea where I was at at the time, so instead of finding a hotel I simply pulled over to a secluded area and slept in the back of my car. Unfortunately it was extremely cold and the blanket I had was anything but adequate, so it was a pretty rough night of sleep.
The next morning I woke up to her knocking on my car window, as I had told her where I had gone to sleep. She told me to follow her back to her house so I did, and when I got there I immediately noticed we had the whole house to ourselves.
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? After hanging out a little bit we went back up to her bedroom and started making out aggressively. I was inexperienced at the time to know how to take it to the next level, so I just grinded my dick on her pussy through my clothes for a long while. I finally couldn’t take it anymore and started stripping her clothes off, but when it came time to have sex, I realized I had left the condom in my car. So I got up to get my clothes on and that’s when I first got extremely nauseous.
I went down to the car and got it, and got back upstairs where she was laying in bed rubbing herself. We started making out again, and I quickly took my clothes off, shoving my cock in her mouth to get my dick hard. She sucked my dick pretty good and it didn’t take long until I was ready to fuck her brains out. I pulled the condom out and wrapped it on, getting in between her legs in missionary position and slid my dick inside of her. I was more than ready to fuck, but as soon as I started thrusting in and out of her, my stomach started getting nauseous again, providing the ultimate biological cock block.
This, in turn, caused me to get super distracted and slightly lose my erection, which then caused the ring around my cock to squeeze way too hard making the whole situation extremely uncomfortable. To make up for this, I started fucking her harder, which she seemed to really get into not having any idea how much of a bind I was in. But I had dated this girl online for a year, I wasn’t about to let the first time we met go unfulfilled, so I just kept fucking her hard until I felt too sick to thrust, then I’d slow down until my dick would start losing its erection and get uncomfortably squeezed by the condom on the base of my cock, then start pounding her again.
After some time I got her up on all fours and started fucking her doggy style. Knowing I wouldn’t be able to cum like this I went to adjust the condom for the hundredth time, but this time I said fuck it, took the condom off and slid back inside of her. I knew this was a terrible idea but it worked, I was fully hard and this time the feeling of my nauseous stomach didn’t distract from the feeling of her pussy around my bare cock.
I had never had sex without a condom at this point in my life, so it took me only a couple minutes before I was ready to cum. I was pounding her deep, and at the angle we were at I couldn’t get out of her pussy before I shot a stream of cum inside of her, but pulled out immediately acting like I pulled the condom off and shot the rest of my load on her ass and lower back. I was super nervous that she would know what happened, but alas she had no idea and we laid in bed together basking in the afterglow a bit. I got a bit of anxiety because I knew she wasn’t on birth control and had no idea what had just happened, and I immediately regretted my decisions up to that point.
While we laid together I started slowly realizing that I didn’t feel much towards her other than physical attraction, and felt the same way about her to me. Sure we had things in common but given that the entire experience up to that point was awkward and overall really strange I wasn’t quite sure what to think of it. For the rest of the day we hung out laying together doing pretty much nothing, and at one point we took a shower together and I fingered her to orgasm. She loved it, but when I asked if I could fuck her again (I didn’t have another condom) she told me no she just sucked my dick in the shower, to which I didn’t orgasm. At the end of the day before her parents came home I got my things together and left to drive back home, somewhat satisfied with the time I’d had given that I had such little to compare it to at the time.
How sexually satisfying was this hookup? Somewhat
Did you have an orgasm? Yes, one
Did your partner have an orgasm? Yes, one
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 the hookup I made the hours long trip back home and continued as normal, but noticed immediately that she was acting different towards me. Honestly, she was way out of my league at the time and I was pretty lucky to get to have sex with her in the first place. It wasn’t but a week later that she called me up with some news, which was that she had been cheating on me almost the entire time we had been ‘dating’ each other. I was shocked at first and a bit upset, but the next few days I thought about it a bit and even I had been looking for someone else during that period of time, but I had planned to break it off with her had any relationship looked promising. It didn’t take me but a week or two to be completely over her and move on, and honestly I forgot quickly about the possibility of her being pregnant given that I knew it wouldn’t lead back to me at that point.
Needless to say I didn’t feel bad about pulling the condom off when we fucked anymore, and even though she wanted to keep me as a friend, shortly after I stopped calling her and answering her calls. We did, however, find each other on Facebook many years later and I unloaded my leftover upset feelings in her pussy while I passed through her town on a trip, but that is a story for a soon-to-follow part 2.
What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Withdrawal, Condoms
What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, Thought it was an important experience to have
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? Somewhat
Did your partner(s) consent to this hookup? They didn’t give a clear ‘yes’, but didn’t give a ‘no’
To whom did you talk about the hookup? How did they react? I told a few friends about the basics of the encounter and the subsequent breakup and most people told me they thought she was bad news long before she and I had met up. This helped me rapidly get over it and move on.
How would you best summarize people’s reactions about this hookup? Relatively negative
Did you get emotionally hurt as a result of this hookup? Somewhat
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? Fucking a super hot girl who I had a decent connection with. Also this was the first time I ever had condomless sex, even if that part was only for a couple minutes. She was also super comfortable being naked around me unlike my previous partners, so I got to explore her whole toned body.
What was the WORST thing about this hookup? Pretty much everything else. Being sick while having sex is absolutely terrible, and having only a small amount of time to do the deed complicated things that much more. Having a half erect cock with the condom squeezing the hell out of my dick was terrible too. Not to mention she cheated on me the whole time, and afterwards I worried about STDs, pregnancy and my self-confidence for quite a while. Honestly, every part of it except just the act of having sex with someone who I was insanely physically attracted to was pretty bad.
Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Definitely. First off, don’t ‘date’ girls online. Second, be prepared in all respects, as not securing a hotel room and getting sick was what screwed me over the most. Also, be prepared and have a condom that fits with me no matter what. Finally, don’t get too emotionally attached to someone unless you know they’re mutually emotionally attached to you.
All things considered, how POSITIVE was this experience? A little positive
All things considered, how NEGATIVE was this experience? Fairly negative
Anything else you want to add about this hookup? Part 2 is a LOT better.
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? Even though we were ‘together’ for a year beforehand, I still consider this a casual sex encounter. What we had is basically what people have together with people on Tinder, just over a longer period of time.
The only thing I feel about casual sex now is to ensure both parties going into it know what the deal is, so neither person expects something more in the end.
What do you think about the Casual Sex Project? I’ve been able to remember some of my best times having sex as a result of reading some of these stories, even some that I had completely forgotten about.
You have a hookup story to share? Submit it here!