by Ry

Gender: Male

Age: 28
Race/ethnicity: White
Location: Massachusetts
Highest education received: College degree (eg., BA, BS)
Occupation: Retail Manager
Religious affiliation: None
How religious are you? Not at all
Sexual orientation: Heterosexual
How many hookup stories have you here posted before? 0

Hot & Heavy in a Hotel

How long ago did this hookup happen? One year ago

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 at a going away party for a friend. I’ve had a tendency to hook up with her friends, and pretty much went into the evening with intentions of having sex with one girl with whom I’d already fooled around a couple of times. That didn’t pan out as everyone at the party found themselves on the dance floor, and she started making out with another guy right there. That mixed with alcohol had me pretty bummed out.

But another of her friends appeared. Chelsea. We’d flirted a bit earlier in the night, but she seemed way too out of my league for me to think anything of it. And while the first girl was doing her thing, Chelsea was also on the dance floor, trying to get frisky with another woman. I, along with every other guy in the area, enjoyed the scene.

It wasn’t long after this that the venue closed and the night came to an end. I still don’t really know what led to it, but recognizing that we were both still a bit too buzzed to drive, Chelsea invited me to come hang out in her car for a bit.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Once in her car, we just chatted. Maybe she recognized my discouragement with the other girl, but we got to talking about my lack of confidence. I remember her telling me that I had to be more forward to get what I want. And with that, I reached up her dress. It was a bold move, and it paid off. She provided zero resistance here, and we instantly began making out quite heavily and passionately.
Neither of our cars nor our living situations were suitable for what we both wanted. Still too drunk to be on the road, we drove around looking for a hotel. The whole experience was out of character for me, but I had no problem throwing down the money for a room to make this happen. It was probably 3 am at this point, and I’m sure it was no secret to the attendant at the front desk what was happening. Pretty sure my hand was still up her dress as I was swiping my credit card.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? Did you have an orgasm? Did your partner(s)? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? The anticipation of getting from the bar’s parking lot to the bed had us both dizzy.
Her dress came off, and my eyes fell out of my head. Chelsea is beautiful. Korean and Italian, ~5’3″, maybe a size zero waist, perfect C-cups, and FIT.
It had been a long time since I was this attracted to a partner, so that did even more for my sex drive.
As badly as I wanted to fuck her, I knew I needed to taste her first. She was soaked and delicious.
The ensuing sex was simply unreal. We fucked. And fucked. And fucked. And kept fucking. I fucked her from every angle, and she got in positions I couldn’t even fathom. It was unreal. And as small as she is, she had no trouble taking every inch of me.
At one point exhaustion hit us, and we both just kind of fell to our backs and drifted to sleep. Slumber lasted no more than 45 minutes, and we were right back at it, fucking straight into the morning light.
We had to be out of the room by 11 am, and I don’t think we left until 10:58. As many times as we tried to leave, we couldn’t help ourselves. Once she put her dress back on, she just looked too fucking good not to take again.

This was the second time in recent history that I ended up having sex in a hotel room, and there is something almost entirely uninhibiting about the experience. In that situation, I am extremely confident, and this time, it helped to provide the hands-down best sex of my life.

The one downside here was that I never came. I always seem to have a hard time finishing when I’m with a partner for the first time. As hard as we each tried, I was just never quite able to get there, and ended up with the worst blue balls. I could barely walk. But to be fair, neither could she.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We didn’t use anything. It wasn’t until later discussion that we covered our history.

What were your REASONS for having this hookup? Do I need to describe her again?

Were alcohol or drugs involved? If so, how much? Again, we were both pretty drunk going into this, but we certainly sobered up as we fucked.

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? It was one of those things where it was just SO good that we couldn’t get our minds off of each other. We quickly began dating, but I think we both confused deep physical attraction and incredible sex for something more. It only lasted about another month, but golly, that was a fun month. Things ended rather awkwardly, and we really haven’t spoken since. I’ve considered contacting her but just haven’t been able to pull the trigger.

To whom did you talk about the hookup? How did they react? I told EVERYONE give or take a few details haha. I was a bit distracted by the whole experience to notice, but my friends seemed to pick up on a few red flags as I told them about her. The most glaring, being her best friend- the one whose party we met at- and her less-than-stellar reaction to the whole thing.

Was this a consensual and/or wanted experience for you? For your partner? Yes. Yes. Yes. Yes. Yes.

Do you regret this hookup? If so, why? Again, best sex of my life. I’m rock hard as I write this.

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? The experience did a lot for the confidence that we chatted about in her car that night. But it also had a pretty significant impact on me. I dove headfirst into treating this as a relationship, as I have always had a habit of doing. My time with Chelsea made me realize how dangerous that can be, and since then, I have been far more casual in my dating. I have a better sense of casual sex being just that, and I try not to get caught up in treating it as more.

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

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

Anything else you want to add about this hookup or anything else? I’m just bummed out that we never got to follow through on that 3-way she teased me with.

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