by Wilhelmina

Gender: Female
Age: 39
Race/ethnicity: Caucasian
Location: Iowa
Highest education received: College degree (eg., BA, BS)
Relationship status: Committed
Religious affiliation: Atheist
How religious are you? Not at all
Sexual orientation: Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 25-30
How many hookup stories have you here posted before? None

“I don’t like kissing very much.”

How long ago did this hookup happen? 2 years ago

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? One-night stand

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 met “Brad” on OKCupid, and we didn’t exactly get off to a promising start. He was a decade younger than me, hadn’t finished college yet, and worked in retail. It was pretty clear, reading between the lines, that he still lived at home. Bottom line, I knew there might be some maturity issues there, but he was kind of cute, and his profile was pretty funny, and funny goes a long way with me.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Here is what happened. I had met another man (let’s call him “Kieran”) about three weeks before my fateful date with Brad, and we’d had around five dates at that point. I really liked Kieran, but things weren’t yet serious or defined between the two of us. I asked him if he wanted to get together the next Friday night, and he made some vague excuse about already having plans with friends, so I knew he probably had a date with another woman. I was a little disappointed, but I thought the best thing would be to get a date with someone else myself.
And that’s when I remembered Brad, the guy with whom I’d had some reasonably fun online chats but had dismissed the moment I met Kieran. I contacted him through OKCupid, apologized for disappearing on him, and asked him if he’d like to go out that Friday. I said it would be my treat since I knew he probably couldn’t afford it otherwise. He said cool. I didn’t actually plan it to be a hookup, just a way to avoid spending the evening moping around about Kieran.
He lived about half an hour from me, but I agreed to meet him at a popular restaurant close to his house. We had to wait awhile to be seated. He was very quiet and didn’t make eye contact. Luckily I had brought along my list of fun getting-to-know-you questions that I like to bring along on iffy first dates in case of awkward silence. I whipped out my list and asked him a question at random.
“Tell me about a book that made an impact on you somehow,” I said.
“Huh?” he said.
“A book that made a difference in your life.” I realized I sounded a little Oprah-like there, so I added, “Or a book you just really liked.”
“Um…Cloudy with a Chance of Meatballs,” he said.
“Oh, isn’t that a children’s book?” I asked.

“Oh. Well, what did you like about it?”
“It was just a good story.”
“What’s it about?” I asked.
He told me and then was silent. I realized my list of questions probably wasn’t going to work on him. I noticed he was wearing a Superman t-shirt, so I asked him if he liked comic books. I don’t remember what he said. Eventually we got called to our table. I was relieved–at least we could talk about the food!
“Get whatever you want,” I said. “Remember, it’s my treat.” I then read my menu several times and pretended to think long and hard about what to order while he ate all the bread in the complimentary bread basket.
The waiter came over to take our orders, and I ordered the biggest steak on the menu. He turned to Brad.
“Um, can I just get some fries?” he asked.
“Just a side order of french fries?”
“Maybe two side orders of French fries? But on one plate?”
The waiter looked a bit confused but quickly pulled it together and acted like this was a normal thing for an adult to order at a steakhouse. He asked if we wanted more bread, and Brad said yes.
Eventually I found a topic of discussion that wasn’t completely painful–the videogame he was currently playing. I had played an earlier game in the series and was able to ask reasonably intelligent questions about how it differed from the version I had played, and he actually seemed to enjoy talking about it. I ate my steak and broccoli, and he ate his big plate of fries and then a third bread basket.
After dinner, I was trying to think of a nice way to say goodbye in the parking lot, but he beat me to it. He said, “It’s still early. Can we head over to your place?”
I was utterly unprepared for such a direct question. I almost said no, but then I had a vision of Kieran out having fun on his date. Kieran certainly wasn’t heading home alone at this early hour. I thought, hey, we could watch a movie or play a videogame. We wouldn’t have to talk. It might be okay.
“Um, sure. Do you want to follow me in your car?” I asked.
“I can’t really afford the gas to get to your town and back.”
“Oh. Well I guess I can drive you and then bring you back here to this parking lot again.”
“Great!” He hopped in my car. We didn’t speak a word during the entire thirty-minute drive. I played music. I thought about asking him if the music was okay, but then I realized I didn’t really care.
We pulled into my garage and I began walking up the stairs to my living room. He grabbed my ass right there on the staircase. I turned around and kissed him. That went on for several minutes. I tried to pretend it was Kieran, but that was impossible–Kieran was a really great kisser and Brad was not. Then Brad kind of pushed me away.
“I don’t like kissing very much,” he said.
“Oh okay,” I said. “Well we don’t have to do that.” I was about to suggest that he take a look at my DVD library when he started removing his clothes, right there in my living room.
I realized then that it would be easier and less awkward to just have sex with him than it would be to say no and drive him back to his car. I told him I needed a few minutes to put in my diaphragm and went into the bathroom to do that.

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? When I emerged from the bathroom having successfully put in my diaphragm, Brad was completely naked, lying on his back on my bed. His erect penis was the second- or third-smallest one I’d ever seen (and I’ve seen quite a few)–I’d estimate it was 3.5 inches. Now I am not a size queen by any stretch of the imagination, but I’ll be honest–I did not take it as a good sign.
I disrobed and climbed on top of him. I just kind of sensed that grabbing my ass had been his idea of foreplay and that I shouldn’t expect any more of it, though by that point my goal was really to just get it over with as quickly as possible. I could barely feel him inside me. I didn’t moan or sigh or fake pleasure in any way. I didn’t really care about his ego at this point. I just grinded my hips against him until he let out a tiny little sigh, letting me know he had reached orgasm. I climbed off. It had been about as physical and about as sexy as doing my laundry.
“If you give me a little while, I can probably go again,” he said.
I decided to get him out of my house before he was ready to go again. I was willing to fuck him once to be polite and to potentially even the score with Kieran, but twice would have been beyond the pale.

What were your REASONS for having this hookup? As I said earlier, it was really all about Kieran. He was the first man I’d dated after the end of a six-year relationship. I had found myself developing feelings for him, even imagining a future with him, and though I was confident I was better than any other woman Kieran could possibly be dating, I still realized it would be smart to play the field a bit, at least until I had more evidence of Kieran’s feelings for me.
I later found out that Kieran was not on a date with another woman on this particular night–he was at a bar with some buddies. I vaguely regretted Brad then.
However, after three months of twice-weekly dates, Kieran told me he’d started seeing someone else and that he thought he might be in love with her. He did not even turn off the soccer match he was watching on TV at the time to tell me that. In fact, he interrupted his own breakup speech at one point to jump up off the sofa and cheer when his team scored a goal. And then I did not regret Brad at all.

Were alcohol or drugs involved? If so, how much? Brad and I were both stone-cold sober. Alcohol might have helped.

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? I chatted with Brad for a little while after the sex, and then I told him that I needed to take him back to the restaurant parking lot because I had an hour-long round trip ahead of me and was getting tired.
I drove him back to the parking lot. When we got there, I actually found myself saying very cheerfully, “Well this was fun! We should do it again sometime! Text me.”
He said, “Okay, I will.”
He never did.
A couple of days later, I realized he’d given me a yeast infection.

To whom did you talk about the hookup? How did they react? I told a few close friends. They laughed at me. A lot. They even gave him a nickname–“Bad-Date Brad.”

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? You know, life is all about having experiences. I don’t believe sex between two or more consenting adults is morally wrong in just about any circumstances, and I’ve also never believed that I’m like some delicate flower that wilts a little bit every time a man puts his penis into me. But some experiences are more worthwhile than others.
I don’t always orgasm easily (though my fiance would disagree with that–lucky me!), and when I do, I tend to scream, loudly, and there is often a lot of female ejaculating. It’s loud and it’s messy, and unless there is some level of trust and intimacy between myself and my partner, I just can’t–it’s too embarrassing. I’ve tried the experiment quite a few times, and I don’t think I’ve ever reached orgasm in a one-night stand situation. I can sometimes enjoy a friends-with-benefits situation, but ultimately, one-night stands just aren’t worth the risk for me. After Bad-Date Brad, enough was enough!

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


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