A Disaster of a Night



What’s your gender? Woman
How old are you? 52
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 (California)
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Attorney
What’s your current relationship status? Getting divorced after spouse suffered brain injury 3 years ago
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Figuring it out as I go
How many sexual partners have you had in your life (including oral sex)? 10ish
How many hookup stories have you here posted before? 3

A disaster of a night

How long ago did this hookup happen? A month ago

What was your relationship status at the time? Same as current status

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? He was tall, balding, fairly slim. Dressed nicely in casual business attire. I hardly knew him. In retrospect, I think he was MUCH older than he let on. Like mid-60’s or older. I don’t even remember his name! I was going to Chicago for a few days and would be working there on my way to another city. I thought it would be hilarious to meet a couple of people before I got there to go to dinner with, or hang out with or possibly more. I read an ad on Craigslist the month before I went that sounded interesting. I responded and explained my situation, and that I really was looking for a more innocent encounter. Dinner and drinks. Or so I thought. I keep surprising myself anymore with what I want from the men I have met. He was very well educated. Liked what I do and what I said, and we hit it off in an email. He called me once before I traveled to Chicago. We decided to meet in my hotel bar after work and then go out to dinner. I met him for the first time that evening in the bar and we had a nice hour-long chat over drinks, and both decided we wanted to have dinner together. He was pretty clear that he doesn’t go out to dinner with everyone he meets on CL because you could get stuck in an awkward situation of not wanting to spend several hours with someone you don’t know. I had to agree with that, but I was away from home, by myself, no kids, and he was interesting and easy to talk to. I thought dinner would be fun and harmless.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? After drinks, we wandered down the riverfront to a really good steak restaurant where somehow by luck we got the last table out on the deck and ate dinner looking up at the Chicago skyline all lit up on a gloriously beautiful warm evening with a cool breeze blowing. We both had had several drinks at dinner by then, not including the drinks at the bar before dinner. We stopped at the bar in the restaurant on the way out and had a last drink and watched the end of a Cubs game.

He walked me back to my hotel and on the walk we got somewhat flirty. I told him he was cute and fun to talk to. I had no idea what I was doing but started thinking it would be nice to invite him upstairs at my hotel. I have never done that before, but it seemed right with that guy. We got back to my hotel and he got in the elevator with me to take me up to the lobby. I kissed him goodnight on the lips and whispered that he could come upstairs with me if he wanted. He literally leaped back onto the elevator to go up to my room.

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? Passionate kissing in the hallway ensued. Someone at one point opened their door to see what the commotion up against their wall was! We made it down to my room at the end of the hall. The door flung open, there was more wild passionate kissing, I lost all of my clothes and … he was not hard at all. Not even slightly hard. Not anything. He apologized. Said he didn’t have his Viagra, but too bad for me because he was spending the night. Before I knew it his clothes were off, he was in bed with me under my covers and I actually felt a drop of drool land on my shoulder as he started to snore! I couldn’t believe it. By now it was well past midnight. I had to get up early for work the next morning. I was still on California time so didn’t fall asleep for a while. But who could sleep anyway with a total stranger in their bed snoring and drooling on them? It was the most uncomfortable, excruciating night of my life. At one point in the night with me lying there uncomfortably he woke up and announced he was going down on me. He kept saying “Tell me you like it. How much do you like it?” I hated it. He was rough. There was nothing sensual about it. No build up. I didn’t want him in my bed. I wanted him gone. By the morning I got up and showered and he sheepishly got dressed and left. I still don’t know what to make of all of it. It was awful. I really took a risk inviting him upstairs. I thought it would be fun and wonderful. A spontaneous decision to have fun with a man I connected with over dinner. But it was one of the worst sexual experiences of my life. I wrote him an email a few days later just saying thanks, because hey, the guy did drop everything to come to Chicago and take me out to dinner. But it was horrible. I will luckily never have to see him again.

How sexually satisfying was this hookup? Not at all

Did you have an orgasm? No, not even close

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? In the morning, he had to use my cell phone and laptop to make a call about some appointment he had because his phone died. I just wanted him gone. Gone gone gone. I should have stood my ground the night before and said “no fucking way bud. I need sleep. You have to go.” Next time I will be braver and say that — if there ever is a next time with someone so clueless and out of it and just all around yuck. I will be much better about vetting potential candidates for coming back to my room in strange cities.

The guy actually said he wanted to come back the next night with his Viagra and show me a good time. HAHAHA! I politely declined and said I had plans. And as it turned out I randomly met a Chicago cop who after work picked me up and drove me all around the city in a lightening storm for BBQ, and to sight see and for an amazing hot dog and mac ‘n cheese experience in the middle of the night. Completely platonic, just a good guy who wanted to show a strange woman his city. That was a blast. Lots of fun. And I did not even once feel like inviting him back to my room! I kept looking over my shoulder for the old guy though in case he was hiding out around a corner waiting to jump out at me with his Viagra! Never again. I read all these stories here about people who have these incredible hook ups randomly at conferences or on business trips or from Craigslist. Not me! I met Mr. Viagra on my first venture out into the land of hotel sex with a stranger. It can only get better from here I guess.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, No penetrative sex happened

What were your motives for this hookup? Fun, pleasure, horniness, Learning new things, experimenting, Intoxication

How intoxicated were you? Drunk/high but not wasted

What substances did you consume? Alcohol

How intoxicated was your partner? Drunk/high but not wasted

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? Somewhat

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 mentioned it to one other person I think. A man I have been talking to and meeting with for about a year. We have not started seeing each other but he really wants to. He’s married and I’m trying to stay away from relationships that are difficult for me or I probably would start fucking him. He thought the story was hilarious.

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

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? A little bit

Do you regret this hookup? Very much

Why do you regret this hookup? It was just a stupid waste of my time with someone who was a complete weirdo.

What was the BEST thing about this hookup? Nothing. Ok, the dinner beforehand was very nice. I liked him a lot at dinner. He was a different person in my room.

What was the WORST thing about this hookup? The guy. And his penis that didn’t work. But in retrospect I’m glad it didn’t work. I had to lie there all night with him but at least he couldn’t fuck me!

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I need to be a little more selective next time if I’m going to do something spur of the moment like that.

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

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

Anything else you want to add about this hookup? I think I have said it all. It makes my skin crawl just to think about it. I was totally trapped by this guy. Entangled all night with a weirdo stranger, I couldn’t sleep, and I was a wreck the whole next day at work. I wanted to punch him to get him out of my room, but I didn’t. I remained polite. Next time I will not be polite. But there won’t be a next time because I won’t let that happen again.

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 love casual sex. I’m trying to get better at it. Practicing! But I have a long way to go obviously. I felt it was important to post this story because the overall sexual experience was so terrible. Not every story is about the best sex someone ever had. Some of them are about pretty awful fucked up experiences. I have to laugh at myself. I’m trying to be slutty! But not yet succeeding entirely.

What do you think about the Casual Sex Project? Love it. It’s a great resource.

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