The People I Slept With.

I WOULD LIKE TO APOLOGIZE TO BUT MOSTLY THANK THE GUYS MY FRIENDS AND I HAVE BEEN INVOLVED WITH BECAUSE ALL OF THE FOLLOWING STORIES ARE TRUE. Only names, dates and locations were changed to protect the fragile male ego.

Tag: sex stories

MY “FRIEND” WITH BENEFITS

by ThePeopleISleptWith

He texted me at 2:09am to hang out. “Just come do it real quick.” SPOKEN LIKE A TRUE GENTLEMEN. If you’re trying to sleep with someone, “real quick ” may not be the best way to persuade them. Yeah, lemme get out of my cozy bed for this quickie.

“Don’t be difficult, ” he replied. I wasn’t trying to be difficult or play hard to get. I never asked for anything. For him, I was never hard to get. For whatever reason, he was under the impression that I was on-call. A few disrespectful texts later, it was clear that we weren’t friends. It no longer mattered how good the sex was, I couldn’t be a hole to stick his dick in “real quick” anymore.

WINNING

by ThePeopleISleptWith

We had been together for four months and for the first time in our relationship, the sex lasted longer than two minutes. Although I was pleasantly surprised, he seemed quite obviously annoyed. Sweat dripped off his forehead as he aggressively stabbed my insides with his penis.

Not long after he finished, he looked at me and proclaimed “I win.” ARE YOU ACTUALLY PROUD THAT YOU ARE UNABLE TO MAKE ME ORGASM? The first person to reach an orgasm doesn’t “win.” I don’t know if he was a moron or an asshole BUT I dated him for three more months – and I lost every single time.

“IT DOESN’T FIT”

by ThePeopleISleptWith

I kneeled on all fours as he “made love” to me in the back of my Jeep, parked next to a dumpster. This would have been fine if he wasn’t using the jack-hammering technique (often used by first timers or high-school boyfriends). “It doesn’t fit” he said, simultaneously lighting a cigarette and a joint. I had no idea what he was talking about.

“From behind, it doesn’t fit. I can tell -you were fidgeting a lot” he said, proud of his apparently massive penis. I explained that it was fine. “It was just too fast. It didn’t feel good.” He refused to believe me and went on to brag to his friends about how his penis would not fit inside of me from behind. It wasn’t the size… just the rapid jack-hammering motion of the ocean.

SWEAT, TEARS AND VOMIT

by ThePeopleISleptWith

It was Thanksgiving Eve I was on my fifth game of beer pong when a boy I had been having casual sex with over the summer walked through the door. Our “relationship” fizzled out when he left for college and after four unanswered texts I had given up on him and clearly my dignity. I had planned to leave the party and met up with some dude who sent me a series of unsolicited but impressive dick pictures the night prior. But there is was… hand full of whisky, belly full of pills, looking real good. He looked directly at me and I knew that moment I wasn’t going anywhere besides his car in the parking lot.

Two shots of Vodka later we were outside alone. He didn’t say anything. He just kissed me. And before I knew it we were ripping off each-others clothes in the back of his Jetta with our friends smoking cigarettes barely six feat away.

I began going down on him when i heard his stomach rumble. He started to dry heave, opened the car door -turning on the interior lights and threw up. Half on the street, half on the car. Our friends stared blankly with a perfect view of our naked bodies. I wanted to comfort him but not as much as I wanted to hide. He was sitting on top my clothing crying so I tried rubbing his shoulder to console him as I yanked my clothing out from underneath him and ran inside.

“He has a girlfriend at college. Did you know that?” A friend asked as he passed me a joint only moments after my run of shame. I took a hit but on the inside I was screaming. I exhaled.

“No, I obviously I did not know that.” I zoned out, starring at the Christmas lights prematurely hung on the wall. He texted me that he made it home safe and planned to “make it up,” to me… I planned to punch him in the face.

SURPRISE!

by ThePeopleISleptWith

After a night of drinking my boyfriend and I went back to his apartment to hook up. While I was going on him he was trying to tell me something but I couldn’t decode his slurred-drunken speech. He sounded like he was enjoying what I was doing so I kept going.

Not long after he mumbled again, but this time is sounded like a question. I naively nodded …. I wasn’t about to take his dick out of my mouth and ask him to repeat himself. A second later he pulled out and came all over my face and hair. I stood there in shock, covered in semen. Apparently he was asking me if he could cum on my face.

LESSON LEARNED: KNOW WHAT YOU’RE SAYING YES TO. 

The Fishbowl Effect

by ThePeopleISleptWith

We hooked up one afternoon after a bottle of Mango Mimosas. He was my roommate’s friend and I was convinced I had Vaginal Depression thanks to a Womens Health article. Our afternoon bone-sesh lasted a total of two minutes and cost me a fair amount of dignity and there really wasn’t much there to begin with.

“I’m about to get into a serious relationship, but if I weren’t we would make a good couple, right?” he asked handing me my sock so I could clean myself off. I wiped off his off-spring avoiding eye contact. To be honest I had mixed emotions. On one hand it was kind of perfect because no one would ever have to know. It won’t happen again. No drama. No awkward moments. On the other hand….. who does he think he is? I did the only thing I could think to do and kept drinking until I passed out at 6pm.

The next morning shorty after setting sail on a charter boat for a fishing trip with my roommates… and just as the sea sickness began to kick in I was informed my secret had been leaked. The regret, the sea, the jokes, the Mango Mimosas, the smelly fish… it was all too much. I spent the three hour trip throwing up into a bucket.

On land after a blunt, a beer and a Big Mac later things appeared to be looking up. That was until he walked in with his new girlfriend. I could sense the eyes on me looking for a reaction. I watched her kiss his lips knowing all too well where they were not even 24 hours ago. I didn’t realize “about to” meant that night. All the sudden I was back on the boat. I went to the bathroom and threw up again.

AN ODE TO THE UNCIRCUMCISED

by ThePeopleISleptWith

I pretended to be much more intoxicated than I was when I asked him for a ride home. He drove to my house, parked and invited me to the back seat. My plan was to kiss him, hopefully making him want more and then go straight to bed. But my lack of self control prevailed and I joined him in the backseat.

That’s when I saw my first uncut penis…. It was like a hermit crab coming out of its shell. A bald head popping threw a turtle neck. Was it attractive? No. But I’ve yet to see a dick that is. Most importantly it felt good. Fifteen minutes later I was fully satisfied and an advocate of the Uncircumcised Penis.

Lindsay Bluth, Arrested Development, said it best “It’s a Doberman, let it have its ears.”

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OH BABY I LIKE IT RAW

by ThePeopleISleptWith

Shortly after consuming three rolls of Sushi and four Sake Bombs I pulled my date into his bedroom. I had recently learned a new move – the “Gluck Gluck 9000” and I was ready to try it out. I began giving it my all… a pathetic attempt to make this mediocre man obsessed with me. Things seemed to be going according to plan when suddenly I felt queasy. At first I tried push through knowing I was only moments away from a triumph finish.

Please cum before I vomit I prayed, sweat dripping from my forehead as I performed the “Gluck Gluck” like a professional. I wasn’t about to walk away… all that hard work for nothing…no way. I had a job to finish so I kept going. Each second he was closer to cumming and I was closer to vomiting privately in the comfort of the bathroom. Just as I saw the light at the end of this nauseating tunnel I lost control. He came as I waited for him to notice the small but noticeable amount of regurgitated Sushi on his dick. Luckily for me he had no idea.. that or he’s pretending that it never happened, either way lesson learned. 

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SEX, DRUGS, THEN PLEASE LEAVE.

by ThePeopleISleptWith

“Want to see my Beat Laboratory?”

…You had me at the Step Brothers reference. I followed you in giving you my usual rant about not being a relationship person – See it’s best to sabotage any chance for feelings ASAP. This way you’ll never even have to know if they liked you enough to date you. It’s all about creating the illusion that you’re control while you spend your nights drinking alone.

Maybe it was your Bob Dylan impression, LOST obsession, cute butt, the free weed or genuine love for Twisted Tea but we fucked on your unmade bed. Then again at my place. During the second time around you came in my mouth and I grabbed a glass of lemon water I had sitting on my nightstand. It wasn’t until I took a large gulp that I realized the lemon in the water had rotted. I was now drinking one of my infamous science experiments.

{ Lemon + Water + Leave for 2+ days } I swallowed.

After, you got dressed you told me you weren’t looking for anything serious. I paused. Just what you want to hear before you’ve fully digested someone’s cum. The taste still lingered in my mouth. You left. I got high on your weed and deleted your number.

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THE PERSON I THINK I SLEPT WITH

by ThePeopleISleptWith

My contacts were stuck to my eyes. I could feel his beer breath on the back of my neck. I had underwear and a wife beater on… but no bra. His hands moved slowly from my waist to my ass… did I sleep with him? The night prior was a blur. It wasn’t until I saw the bottle of Jagermeister on the night stand, next to the White Castle bag, that I realized.. I probably did. He sat up, afraid I hid most of my face underneath the covers, as if that could magically make him go away. I felt a warm kiss on my forehead then he left the room. I should of asked him what happened but I’m not sure I wanted to know. I got dressed quickly and walked out of his room. Disheveled and disoriented I walked right into the living room where four of his friends were hanging out. After 10 of the most awkward seconds of my life he followed me to the door. ” I had fun,” he said but before he could lean in for a kiss I gave him a high-five. I guess I’ll never know.