All the Times I Had Crappy Sex

Adventures of times I wish I stayed home.

I can’t truthfully say these are “all” the times I had crappy sex. I’m sure I’ll think of more in a week, at 2 am, and then desperately try to forget again.

Many of these escapades started from Craigslist. You know, the site you went to if you wanted to roll the dice on getting murdered. Some were a result of hookups by mutual friends; I’m not sure what heinous act I did to them to warrant these connections.

The common theme is my horrific sense of self-worth that allowed these to even happen.

The guy who called me “Baby”

I was about 28. I would guess he was 40. Well, 40 going on 50, I think he was a heavy smoker.

We agreed to meet in a seedy hotel but I wanted to back out. I have this weird sense of commitment that even if I don’t want to have sex with someone, I must honor my word if we agree to it. No one taught me that agreeing to sex isn’t an RSVP to a wedding. I didn’t listen to the gut instinct that told me it wasn’t right for me.

I don’t think I’m a prom queen but I was way out of his league. His pictures didn’t match his appearance. And he knew it. He immediately became a nervous wreck. He tried to sit down and impress me with conversation; I jumped straight to the action. The sooner his dick went in, the sooner it would be out and I could leave.

The most unnerving part was his repeated use of calling me “baby”. No one else had ever called me that. It seemed like a term of endearment for two people who knew each other well. I don’t think I even knew his name (why know the name of your potential Craigslist murderer?).

There he was, on top of me, just repeating “baby” every other second. As soon as he came, I jumped up and bailed out. It took me years before I could get over hearing “baby” again.

The guy who bragged about his ex

I met Rob through a mutual friend. He was the epitome of tall, dark, and handsome. There was chemistry, enough to call for movie dates and sex. Every time we saw each other, I drove. That should be a red flag in a state that is car-centric. His truck was conveniently broken every time.

With paranoid fervor, he constantly reiterated that he wanted to stay as friends with benefits. You only gotta say it once gentlemen. When you repeat it over and over, it sends the message that you really, really don’t like the girl and want her to know it. I was 23 and too insecure to tell him, “yeah I get it asshole. Shut the fuck up already.”

Sex was fine except as soon as he came (while still pulling the condom off), he would tell me all about his ex-girlfriend. Specifically, the ex-girlfriend who was a model. Why…WHY? Why would a guy babble about his hot ex-girlfriend to the girl he just fucked? Why would he do it every time?

More importantly, why did I keep having sex with him? It wasn’t doing anything for my self-esteem. Eventually, I started dating someone else and had the biggest thrill of turning him down, multiple times, when he pestered me for sex again.

The guy with the rough blanket

Another Craigslist gem. We enjoyed grabbing drinks beforehand but he wasn’t my type. He was quite overweight and kept griping about his ex-wife. No woman wants to hear about “my bitch ex-wife” all evening. A few of his coworkers happened to arrive and saw him; I became the trophy date he showed off.

I drank too much. I’m hoping the average guy would see a girl who is barely standing upright and either sit with her until she sobers up or call her a taxi (in a pre-Uber era). I’m responsible for my actions so I don’t fault him. I just wish he looked past the needs of his cock.

He half carried me to his SUV and layed out a scratchy, dirty, awful plaid wool blanket in the back after putting the seats down. I couldn’t even string a single, coherent sentence from my drunkenness. I try to be somewhat of an active participant during sex but this is the one time I have ever, ever just laid there like a statue. My only thought was, “don’t throw up” on loop. When he finished I stumbled out, threw up in the parking lot, and got into my car. I drove home when I should have sobered up but I was so mortified and wanted to crawl into bed.

While he kept calling me for months after for more sex, I threw one excuse after another. He refused to give up when I told him it just wasn’t going to happen. I even lied and told him I was pregnant with someone else’s child; it didn’t deter him.

The icing on this vomit-filled cake was that one coworker we met that night ended up, coincidentally, dating a close friend of mine. Thankfully, he never once brought up that we had met before.

The guy who took the condom off

While I may have fucked a lot of random guys, I’m very insistent on condoms. My girly parts are pristine and I’d like to keep them that way.

I met Mike through a friend; he saw my pictures on her Facebook page and harassed her to introduce us.

We met for drinks. He was hot as fuuuuuuuuuuck. He had the charm to match the looks and knew how to use them. After drinks, we parked nearby and boned in the back of his SUV.

When he came, I was confused because there was…goo in me. He told me he took the condom off halfway. At the time, I didn’t know this was a form of rape. I didn’t want to be the uncool, freakout chick so I just sat there somewhat stunned and engaged in his post-coital small talk. With his good looks and charm, he knew how to get what he wanted from a woman. After fifteen minutes he was ready for round two, sans condom of course. I had no logical argument for “no, really, I want a condom” when he had already cum in me once before. Since we were in his SUV in a dark parking lot away from my car, I didn’t want to upset him.

In hindsight, I wish I had flipped my shit on him. I wish I had clocked him in the teeth. Instead, I thanked him for the lovely evening when he finished the second time and drove me to my car.

It’s been years but I still feel very upset over that night. On the plus side, after I told my friend what happened, she verbally raped him back for his atrocious actions.

The lunchtime blowjob

I agreed to meet this guy for lunch. He kept prattling about how his wife refused to have sex with him. I didn’t blame her; I didn’t want to have sex with him either. He was whiny and complained about everything. I was grateful I only had one hour off work.

After lunch, I had every intention of just walking back to my car. He got all mopey and sad. I should have said, “sorry, not in the mood”. Instead, I gave him a pity blowjob. Ironically, it took putting his dick in my mouth to shut him up.

The one-pump-chump guy

I met this guy off Craigslist, but not for sex. He bought my tennis racket which I gleefully sold as a middle finger to the ex-boyfriend who gave it to me (ask me how many times I’ve ever played tennis. The answer starts with a Z.) We hit it off so much while chatting over coordinating the sale that he asked me out on a date. My eavesdropping coworker remarked, “did…did he just ask you out? What was that?!”

There was no pretense. He was temporarily in the country on an internship. We had a blast emailing up until our date. Our romantic evening began at Macaroni Grill and ended in his bedroom.

We got naked and I ran my hands along his body. My twenty-something self had never been with a guy who had shoulder hair before. I couldn’t stop fixating on it. I can still imagine the feel of it under my fingers.

He rolled the condom on, slid right in and…that’s it. It was over. I don’t know if he’s a one-pump-chump when there was no actual pump.

Fortunately, I have the ultimate game face and can smile through any awkwardness. I made it seem like we just had fantastic sex for hours.

Thankfully he left back to his home country when his internship ended and I never had to risk awkward sex with him again.

The guy who became a rapist

My college boyfriend and I were “on a break” à la Ross and Rachel. His frenemy Matty, who lived above my boyfriend’s apartment, told him he was going to ask me out. I was a pawn in their years-long battle against each other.

We watched a movie on the couch (I fell asleep and still don’t know what happens in Goodfellas). He led me to the bedroom and my mental Stranger Danger alarm went off. He wore tear-away track pants like all the cool, hip kids of the 90s. He ripped them off and proudly displayed his erect cock.

I didn’t want to have sex. I also had a feeling this guy wasn’t going to say no. He was a hockey player three times my size and overly aggressive in his manhandling of me. I did what the only thing a female can do to truly disarm a guy with a hard cock: I gave him a blowjob. He had shaved his entire pubic area but it was growing back and the stubble scratched my face. Matty finished and I bailed out.

Eventually, my college boyfriend and I reunited. Shortly after, we heard Matty bragging about how a girl passed out in his bathtub and he had sex with her. I dodged a bullet.

The threesome guy

In my younger years, I didn’t know anything about threesomes except what I learned from Sex and the City. I wasn’t the type who would be okay with another woman in bed with her and her boyfriend. It seemed to easy for jealousy and to wonder if my nonexistent boyfriend would always wish he was with her instead.

To partake in this fantasy, I realized I could be the third. I wouldn’t have to deal with the aftermath and I wouldn’t have to see them when it was over. I think this made me a “unicorn”; a young, cute female who wanted to experience threesomes with other couples.

I chatted up with a couple that I cherry-picked online. They were roughly twenty years older but very attractive and nice. The husband said he wanted to meet first to make sure we would be cool with each other.

All dolled up, I met him in a Mexican restaurant for drinks. His wife was out of town; the plan was to just meet and make sure we felt comfortable with each other. I underestimate how adorable I was in my twenties (Sigh. Why did I think I was hideous?). He begged me to go back to his place and hang out in his hot tub. Naked.

I agreed since it all seemed kosher until this point. He tilted his patio umbrella so the neighbors wouldn’t see us naked in his backyard spa. He told me he wanted to have sex with me and in the absence of anything else to do (clearly I have a theme of having sex when I’m not interested because I don’t want to be rude and say “no”), I followed him to his bedroom.

This dude didn’t mess around when it came to sex. Mirrors covered his ceiling. He slapped on a condom and got to town. From what I remember, he was the thickest guy I have ever been with. As in, more girth than length. Take your soda can, turn it sideways, and that was his cock. Not even sure how he got a condom on that thing.

Staring up at my reflection in the ceiling mirror, I wasn’t very impressed with myself. Something didn’t seem right, aside from his horrible taste in room decor.

When he finished, he tried to cover up his deceit. “So, my wife and I have threesomes all the time,” he said, “but I’ve never met them on my own. Let’s not tell her that we did this without her, okay?”

His wife returned from her trip. I never joined him in their bedroom. I lost my appetite for threesomes.

Considering how many people I’ve slept with, thankfully my experiences have been more positive than negative. The rest of the ones that weren’t stellar were along the lines of unmemorable car trysts.

Aside from the prick who took off the condom (I’m still not fully over that, almost two decades later), I put myself in these situations and could have backed out. I don’t begrudge these men; I didn’t tell them I didn’t want sex anymore. Fear of confrontation and awkwardness leads me to make poor decisions on behalf of guys instead of myself.

Hmm, I should maybe work on saying “no” to unwanted sex…right?