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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? 2

Online Girlfriend and the Rogue Sickness: Part 2

How long ago did this hookup happen? 5 Years Ago

What was your relationship status at the time? In a relationship (monogamous)

How would you best classify this hookup? Sex with an ex

How long did you know the person before this hookup? For more than 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 brunette with a somewhat toned body, at this point with a little extra weight on her but still extremely attractive. She still looked like Britney Spears with a little Asian heritage in the mix, with decent sized breasts and an amazing ass. I had dated her online many years prior which is described in part 1, but lost contact with her for many years after we met in person and soon after split up.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? When I first saw her friend request on Facebook I contemplated just ignoring it given that I knew what kind of a person she was from when we dated before, but I figured it wouldn’t hurt or matter so I accepted it. At the time I was in a very unhappy relationship, and one night the perfect storm hit.

She messaged me when I was super horny and intoxicated, and we started catching up after all that time of not speaking. I explored her Facebook page a bit and it looked like she had not made some of the best decisions since then, which I sort of expected. Time hadn’t exactly treated her well, but despite that, I still found her very attractive, and during our pleasant conversation I remembered a little bit as to why I liked her and her personality in the first place. She was also in an unhappy relationship at the time and we both talked about our situations. For the first time in years I felt like I was able to relate to someone else in a completely real way, and that seemed to give both of us some genuine comfort that allowed us to relax and just have fun chatting.

That’s when things started to get sexual. At first it was just an innocent inquiry about my then-girlfriend and I’s sexual relationship. I explained that we had sex often but how I felt it was boring and just an expected habit more than something I actually enjoyed, which was the truth. Then she went into this long explanation about how her current boyfriend wants to have sex all the time but wasn’t good at it, was an everyday expectation and never had passion. She didn’t know it at the time but she described the exact situation I was in too, and in that way I felt my compassion for her situation bridge into some slight feelings that I was surprised I felt.

At the time I didn’t think anything of it, but I mentioned her town was on my way when I went to visit my family back home, and also mentioned in another part of the conversation that I’d be visiting home in the next few weeks. I still can’t tell if she had planned all of this or if it really was the perfect storm, but a few weeks later a couple days before I was going to leave she asked if I wanted to meet up with her for lunch on my trip down. I hesitated at first because I was still a little apprehensive about her, but since it was just lunch I told her I would and she gave me her number.

Unfortunately, I got a little sick before leaving for the trip that morning, but not near as bad as the first time. I think I was a little nervous about meeting up with an ex that I had met a total of once and had an awkward sexual experience with, but when we met up at the restaurant and gave each other hugs, my anxiety went away pretty quickly. At first, we just chatted about normal bullshit, but somewhere the conversation turned to our previous relationship. She told me she was sorry for ‘cheating’ on me but I also told her that I didn’t really see it that way, given that we were pretty much just dating online anyway. We then talked about meeting up at her parent’s house then, and I told her the story almost exactly how I wrote in Part 1, all details intact. We laughed about it for quite a while, but I could also tell she was getting turned on a little bit over my intentional irresponsibility with her when we were young, as was I. She kept asking me about certain parts of the story, having trouble believing some of it but thinking it was hilarious, and we laughed about it together a lot. At some point in this conversation she bumped my leg under the table, but instead of moving away left them touching until lunch was over.

When we were leaving the restaurant we gave each other hugs, and when we pulled away she asked me if I wanted to have a do over. I told her I would in a heartbeat but I had a girlfriend, to which she replied that she was going to be splitting with her boyfriend soon and it sounded the same for me, and there is a hotel right across the street. We moved our cars over to the parking lot and rented a room with a king sized bed.

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 teased each other and laughed as we walked to the hotel room, but as soon as we entered it was time to fuck. We started stripping our clothes off and as soon as we were to our underwear I couldn’t stand it anymore and started making out with her, leading her to the bed as we aggressively stuck our tongues down each other’s throats. My hands explored her perfectly curvy body as we exchanged saliva, pushing my dick up against her pussy through our underwear as if I was fucking her already. After a while, I moved down to sucking on her tits, and slid her panties to the side to start finger fucking her as aggressively as I could.

After some foreplay I was ready, so I pulled her panties off, then my boxers, but then I remembered that I didn’t have a condom since not only was this unexpected but my then girlfriend and I didn’t use condoms. I told her I didn’t have one and for a split second she gets a worried look on her face, but then says something that turned me on more than anything I’ve heard a girl say to me before or since then. She said,”Well, you pulled the condom off before, right? And if anything happens, I’ll just blame it on my boyfriend, but you’re not about to stop now.” I slid my dick into her pussy as deep as I could and we both let out moans of relief for each thrust as we start fucking.

Lucky for me given how turned on I was she wasn’t super tight, so I quickly end up pounding her as hard as I could as I watched her titties bounce and explored her body with my eyes and hands. One thing I distinctly remember is I loved her natural scent, which made me want to taste every part of her body. We switched positions a few times, from missionary to doggy to cow girl to me standing on the side of the bed fucking her on her back as she rubbed her clit furiously. She could tell I was getting close to cumming and tells me to cum inside her, and it wasn’t but a few thrusts later that I was filling her pussy up with my cum. This turned her on tremendously and after I pulled out I sat on a chair behind me and watched my cum leak out of her onto the bed and floor as she rubbed her clit to an orgasm. She came, squirting everywhere which I had never seen before, and I laid on the bed next to her and pulled her up next to me as we both lay there exhausted after our near thirty minute fuck.

She then told me that she’d never had a guy cum inside her before, then corrected herself saying that actually the first time we had sex was technically the first time and we both laughed really hard. She went to use the bathroom and clean up a bit, and I turned on the TV while she did so, but when she came back out she told me she was ready and laid down on her back, spreading her legs.

For the rest of the day and night we fucked over and over again, every time I would finish we would take a break and watch some TV or go get something to eat, then come back and go at it again. We both were extremely comfortable and we got pretty kinky, I was sucking her toes, fucking in the shower, spitting in each other’s mouths, tied her up at one point with sheets and made it clear that we were there to use each other as much as we could for the night. We both had a lot of pent up sexual frustration and it all came pouring out that night all in and over each other. We even did anal, but without lube it didn’t last too long.

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? The next morning we woke up and had sex again, but unfortunately had to make it quicker given that our check out time was soon. After we checked out we hugged and agreed to do it again, which we did a couple more times much later. While I felt a little guilty that I had just cheated on my then girlfriend, the encounter also encouraged me to break it off with her sooner rather than later. At the time I had considered trying to pick up a relationship with her, but given that we lived so far apart and I was tied to my current location I couldn’t see any way it could possibly work. Plus, honestly, I barely knew her anyway. I did, however, worry for a while if I got her pregnant, but I never heard anything about it so after a couple months that anxiety subsided completely. From that point forward I always carried a condom hidden in my wallet.

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

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Emotional intimacy, closeness, connection, Thought it was an important experience to have, To cheer myself up, Revenge / Getting even, Boredom, It was easy / convenient

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? I don’t know / I’m not sure

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? Only some friends a long time later. I didn’t go into detail, so they didn’t think much of it but didn’t like that I had cheated. Though, given that I broke up with my then girlfriend right after it was forgivable.

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

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? Honestly, there’s a lot that contends for the spot of best in this encounter, but I would have to say that having my ‘ex’ seem to seduce me even after not having the best sexual experience from all those years before was pretty awesome. I guess there was more to our connection than physical attraction, and it was nice to be able to give a chance to make up for the first time.

What was the WORST thing about this hookup? Worrying afterwards about pregnancy and STDs. I straight up threw all caution to the wind, not a good idea for my subsequent mental health.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yes it did, I had casual sex with girls before, however, I never experienced an almost purely sexual desire from another female. Usually, it was paired with liking each other quite a bit, which to an extent this encounter had, but once it was time to have sex it was all about that. After I broke up with my then girlfriend and I had a couple experiences with friends of hers which were pretty similar.

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

All things considered, how NEGATIVE was this experience? A little negative

Anything else you want to add about this hookup? I had heard from a mutual friend of ours some time after this hookup that she heard she had gotten pregnant at some point in passing conversation. I have no idea about the timeline of this happening or if it was even true, but good god when I heard that my heart dropped.

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 even with casual sex there needs to be some type of emotional connection, even if it is shallow. In my experience, even with the slight connection this person and I had, it made the sex infinitely better than following experiences I’ve had with people I don’t share any sort of connection with. This is partially also why I am now completely monogamous and in a committed relationship.

What do you think about the Casual Sex Project? Pretty awesome!

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

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