by

What’s your gender? Man
How old are you? 32
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? South Florida, USA
Highest education received: College degree (eg., BA, BS)
What’s your occupation? IT
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 50, 55-60 if counting oral
How many hookup stories have you here posted before? Lots

Taking Turns on a Police Officer

How long ago did this hookup happen? 8 or 9 years ago

What was your relationship status at the time? Single

How would you best classify this hookup? Group sex

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? Well, to be perfectly honest, “Carla” was ugly. Really ugly. Out of everyone I’ve ever hooked up with, she’s the only one that embarrasses me (from a physical perspective).

She was of Hispanic descent, but everyone thought she was Asian because of her eyes. She was very fair skinned, very thin, had dark brown hair, brown eyes, a patch of prominent freckles over her nose and across her cheeks, thick glasses, and not a bit of ass. Her tits, thankfully, were at least a small handful. Her teeth were too small for her mouth, her personality was dorky, and she didn’t have a bit of self-confidence. Oh, and she was a police officer. I never asked her about her profession, but something tells me she was more likely to be handing out speeding tickets than pursuing hardened criminals.

I met Ugly Carla through my friend “Matt” and his fianceé “Allie.” Allie and Carla were best friends and rather inseparable.

After college, I went through a long period of mild depression. I had lived the life of fucking every girl I met, but I was starting to wonder how I was going to ever find a potential wife now that I had moved back home. Everyone in my circle of friends was either married or engaged; I was single and we weren’t the type of people to go out to clubs or bars anymore. Basically, I felt like it was going to be very difficult to meet anyone.

Having not met any “new” girls in a long time, I began to open up to the idea of sleeping with Ugly Carla out of desperation. I knew she had a crush on me, but she knew I wasn’t remotely interested. She saw the kind of girls I used to sleep with and knew she wasn’t in their league. But after going through a dry spell of almost 3 or 4 months without getting laid, I was getting pretty depressed and desperate.

Long story short, I told Ugly Carla we could be friends with benefits…and we fucked. I refused to kiss her, which made sex sort of awkward, but I didn’t care. She knew I was using her body for sex and I guess she somehow rationalized it to herself. When we fucked, I was rather uncaring and rude toward her. I would let her blow me, never returned the favor, fucked her until I came, and then paid her no attention. I don’t know why she put up with me. She must have been lonely, too. I’d never heard her talk about a guy in her life before.

The sex was fulfilling on a “at least I had an orgasm” sort of way. Her bod wasn’t terrible. If you didn’t look at her face, it was actually not too bad…just plain.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Matt wasn’t entirely in love with his fiance Allie. He felt like she was the best he was going to be able to get in life and pretty much asked her to marry him out of obligation and guilt. Because of this, he was always eyeing other girls and had a thing for Ugly Carla. He wasn’t a bad looking guy, but he had a non-visible disability that kept him from having any type of confidence whatsoever. As it was, he constantly told me how he had the hots for Ugly Carla and wanted her…partly because he was attracted to her nerdy personality and partly because it was his fiance’s best friend.

Having a lot of persuasion power with Ugly Carla, I told Matt I would see if I could arrange something with her for him. After talking to her, I found out that she was bisexual and would be more than willing to join Matt and Allie for a threesome. Only problem: Allie wasn’t bisexual. The mere mention of having a threesome with her best friend and Matt would have made her leave Matt for good. So Matt, Ugly Carla, and myself made a new plan. Quite simply, our plan was to get Allie good and drunk. We figured if she got wasted, she could either be coerced into having a threesome with her fiancé and best friend, or she would pass out as things got heated up and Matt could hook up with Ugly Carla without her knowing.

The next time we all got together, we got out the Jägermeister. If anything was going to work, it would be Jäger. I got hammered. Matt got hammered. Ugly Carla got hammered. Allie got hammered. When Matt and I started pushing the girls to get romantic with each other “for fun,” Allie laughed it off and refused. But then when Ugly Carla started to get in on teasing her and telling her it wasn’t a big deal, Allie became a bit more receptive. With enough Jäger and peer pressure from the three of us, Allie eventually gave in and made out with her best friend. Pretty soon, we got them to take their tops off and massage one another’s tits. Ugly Carla told Matt to take pictures with his digital camera because this was something she didn’t want to forget. It was one thing that Allie got drunk enough to fool around with her best friend. It was another thing all together that she was drunk enough to go topless and make out with Carla in front of me, her fiancé’s best friend. I knew we were headed to a good place.

We convinced Allie to have a three-way make-out session with Matt and Carla. Matt was ecstatic. We weren’t sure if Allie was going to be drunk enough to agree to a threesome, so we all kept pouring the shots. We got Allie and Carla to scissor each other on the floor (with their pajamas kept on). But when Allie let a moan sneak out, she quickly covered her mouth and exclaimed in shock “that felt good! what the fuck!” as if she was surprised she wasn’t immune to her pussy being rubbed affectionately. But we had finally pushed her too far. When she realized that she was getting sexually aroused by rubbing her pussy into her best friend, she promptly got up and said she was going to go to bed.

Matt told me to go after her and see if I could seduce her. He told me he didn’t care if I fucked his fianceé if it gave him a chance to fuck his long-standing crush. Allie wasn’t great looking (she had nice tits, as I had just seen), but I wasn’t about to push that boundary. Instead, I left the room and closed the door on my way out so Matt and Ugly Carla could have some privacy.

After no more than 5 minutes, Matt comes awkwardly walking out of the room holding the crotch of his pants way out in front of him. Before I could even ask him if he got laid, he tells me, “We started making out. She got on top of me…she started grinding into me…and I came my pants.” His face was a combination of amusement, conquest, and disappointment. I’m sure he was happy that Carla made him blow his load, but clearly he was hoping to last long enough to actually fuck her.

When he went across the apartment to clean himself up, I decided to go check on Ugly Carla. She was sitting on her knees on a futon and looked like a dog in heat. You didn’t need to see any more than her body positioning to know she was extremely fucking horny.

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? Not one to pass up an easy opportunity, I sat on the futon beside her. Without asking, she straddled me and started grinding in to me in the same way I have to imagine she was just grinding into my friend. She put her face close to mine, but I turned my head to the side, avoiding any possibility of kissing. Gross. She buried her face into my neck and continued grinding into me.

After a few minutes of grinding, she said something like, “I knew you wouldn’t be as easy to make cum.” I gave her a look like “no shit” and pushed her off of me. I told her that if she was going to make me cum, she’s going to have to let me fuck her.

Without hesitation, Ugly Carla dropped her pajama pants and panties, and sat on the futon. I walked up to her, took out my dick, and guided her face toward it. She sucked enthusiastically, massaged my balls, and stroked my shaft. When my cock was plenty wet from her saliva, I pushed her back, mounted her, and started fucking her. As with each time we had sex, I didn’t pay the least bit attention to her needs or body cues. I just kept trying to position myself in the best way to make myself cum as quickly as possible. Sex with Ugly Carla wasn’t ever something I was proud of; I just wanted to blow my load and be done with it.

After fucking her for maybe 10 minutes- who really knows- I realized that she had begun to cry. I immediately stopped. I didn’t care about this girl at all. In fact, I was sort of annoyed. But I new right away that I was just going to pull out and go home. I didn’t want any drama (too late!). The moment I slid my dick out of Ugly Carla, she realized that her crying wasn’t as muffled as she thought, immediately apologized, and told me to keep going; she wanted to make me cum. I told her absolutely not, the mood (however flimsy it was to begin with) had already been ruined.

How sexually satisfying was this hookup? A little

Did you have an orgasm? No, not even close

Did your partner have an orgasm? Yes, one

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? When I left the room, Matt was on the couch watching TV. He had a look on his face that screamed “We did it!” I told him I was going home and that Ugly Carla was crying in the other room. He looked puzzled, but not too concerned.

In the future, we all still hung out, but neither Matt (that I know of) nor I had any sexual contact with Ugly Carla again. I was done fucking her; I didn’t want the emotional baggage. She acted normally around us, too. It was as if nothing ever happened.

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, Intoxication, To feel better about myself, To cheer myself up, I was feeling lonely, Power / Dominance, Boredom, It was easy / convenient

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? A little bit

Did you consent to this hookup at the time? I didn’t give a clear ‘yes’, but I didn’t give a ‘no’

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? Matt and I joked about it, but not too much. He was probably embarrassed that he blew his load before even whipping his dick out and I wasn’t very proud of fucking a chick I thought was really unattractive.

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? Somewhat

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? The only good part about fucking Carla was that I was so detached from her emotionally- and she was so accommodating to let me do whatever I wanted- that I was able to use her like a living, breathing sex toy. It was as if I was entirely freed from any societal norms that instructed me to take her feelings and desires into consideration. I guess it’s a fucked up thing to say, but it was really quite liberating to be able to use a girl for purely carnal pleasures and not worry about her needs in the slightest. I could bend her, use her, and fuck her however I wanted without even as so much kissing her or making her feel appreciated. I loved that aspect of it. And I felt like I didn’t even have to feel guilty about it, either, since she was understanding and okay with our unspoken arrangement. That is, until she got very drunk and emotional, at least.

What was the WORST thing about this hookup? In case I didn’t make the point clear enough: Carla was so ugly that I refused to kiss her. I wouldn’t have been seen with her publicly.

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

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

Anything else you want to add about this hookup? Matt and his fianceé wound up calling off the wedding. He realized she wasn’t really the one. He and I are also no longer friends. He prioritized a new girlfriend (who hated all of his friends) over all of his friends to the point that we never saw him anymore.

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

Comments