The People I Slept With.


Category: sex stories


by ThePeopleISleptWith

I moved to Florida landing a job at a gas station. A guy who would pull up on his Harley and fill up once a week, and as glamorous as spinning the hotdogs on the broken heat rack may sound, his weekly visits became my high points. Now I couldn’t understand this guy for shit because he had such a deep WV accent, but it didn’t matter. I was tired of the deadass Tim’s loving NY boys and was looking forward to a geographical dick change as well.

About a month after riding around pretending I understood everything he was saying, it was time. I was finally alone In my brothers bedroom, with this Marlboro smoking, Harley riding, momma lovin southern boy. We were getting frisky when blurted – “spit in my mouth it’ll be sexy”. My mouth dry as can be as if I rode the entire way to the house with my mouth open on the back of his bike…I panicked. Not wanting to loose the moment, I hocked back and a grand ole loogie came forward and I spit it with force into his mouth, figuring this was the nasty he was into.

It was not in fact his type of nasty, the look on his face will haunt me forever as he looked at me with horror and swallowed. Good ole southern boys don’t waste an opportunity though-and we continued on-and for that, I thank his momma raised him right.

**submitted post**

That’s What She Said

by ThePeopleISleptWith

Five months ago he didn’t respond to a text I sent so I blocked his number. But now I’m lonely, horny and the only hot guy I met on Tinder tried to buy me a butt plug before our first date. So I texted him asking to buy some weed- which was ridiculous because his weed sucked and he charged too much…. Yes, I was willing to pay $50.00 to possibly get laid.

He came over and immediately started playing the Office them song on my roommates piano.

“Do you want to make out?” He asked. I sat there pretending to contemplate the decision as if it wasn’t my plan all along. We started making out and then he reached down my pants.

” I have my period,” I warned him. I didn’t think he would stop but he did. DON’T JUST GIVE HIM HEAD I told myself as he clearly motioned for me to suck his dick. So I let him put it in my butt and spent the remainder of the night chain smoking cigarettes trying to figure out why I am so bad at life. He ghosted me and I basically paid him to stick it in my ass.. great.

Hip to Be Square

by ThePeopleISleptWith

My first attempt to lose my virginity was cock-blocked by Huey Lewis from Huey Lewis and The News. How you ask?

My parents were spending the night in Manhattan to see Huey Lewis and The News and were leaving me alone for the first time overnight. This was a BIG DEAL. I did what any teenager would do and invited a few friends over so we could drink my parents alcohol and hook up. There was a bottle of vodka that had been in the fridge since I could remember. But after five years of stealing some and filling it back up with water.. I guess it was safe to assume it was just water at that point.

I invited two couple friends over. One of the couples were currently doing a lot of anal, and proudly discussing it in the cafeteria every day. I clearly needed something captivating to talk about as well so I invited Mark. Mark was very cute but most importantly Mark was from a different school. He had been looking at me during shows and flirting with me on AIM. But when he commented ” ❤ “on my Myspace picture a week prior I knew the deal had been sealed.

About an hour into my get-together we were finally alone in my room. We were sitting on my bed when I reached across him to turn my CD player and he kissed me. It was my very first REAL kiss and all I remember thinking was does there really have to be so much tongue? I wiped his salvia from my face. My phone rang. Mark moved to the end of the bed.

“Hello,” It was a man’s voice I didn’t recognize. “Who is this?” ” It’s Huey, Huey Lewis.” I didn’t know what to say, unfortunately this took place years before I began to fully appreciate Huey Lewis and The News and I was kind-of in the middle of something. ” I’m here with your mom and dad,” he told me. “Okay.” It was clear I had disappointed Huey with my unenthusiastic reaction. Mark stood up. Huey handed the phone back to my mom.

“That was really Huey.” ” I know.” My mother went on as Mark shuffled around my room awkwardly inspecting my sponge painted walls. My carefully organized plan was failing in front of my face. My mother continued to ramble and eventually Mark left my room. The moment was over. The mood had been killed. After saying a quick goodbye to Huey my mom eventually hung up and I joined my friends in the kitchen as they pretended to be drunk off orange juice and a dash of watery vodka.

The Twisted Tea Diary:

by ThePeopleISleptWith

We met at a house party. He was cute and I was drunk. I sipped on my tall can as we discussed the appropriate ways to use the word C-word. A few weeks later I went to a party with every intention of getting to know him. But when I struggled to grab his attention off the bat I resorted to an old handy move of mine – A move with a zero percent success rate but nevertheless I proceeded …

I avoid the target and spend most the night talking to one of his friends; appearing chill, funny, and desirable from a distance.

Unfortunately the move often results in charming one of his friends and like at least three times before waking up in the wrong bed. So once again thanks to a lack of self control combined with the emotional capacity of George Costanza I woke up in the wrong bed.

“Want to get dinner tomorrow?” He asked.

I didn’t know how to tell him that while I was totally fine sleeping next to him topless I wasn’t interested in eating a meal with him.. even if it was free. I left, dodged his kiss as my friends watched with horror, drove back to Brooklyn and slept for thirteen hours.

Five days and I kid you not SEVENTEEN unanswered texts later he texted me (#18) to tell me he found out about this blog and HE was over it. Fifteen days and a six pack of Twisted Tea later I signed a lease for a beach house with three friends and him.

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.

Kegel’s and Tequila

by ThePeopleISleptWith

Shortly after turning 23 I forced my college roommate to join me on a five hour road-trip to party with some friends…. and not at all to hook up with a professional skateboarder who had just turned 18. I had met him back a few years ago when I would have ended up in jail for acting on my crush. In my defense our mutual friends were my age and he was kind-of famous. So yes I, a 23 year old sort-of professional woman crossed state lines for dick.

After the party we went back to his mom’s house. A few unnecessary Tequila shots later we made our way to his waterbed. I had played the scenario out several times in my head the weeks prior but surprise, surprise things were not going as planned. He seemed to be enjoying himself but I felt nothing. A wave of panic consumed me. I can’t feel him inside me, how big is my vagina? I started doing kegel exercises underneath him frustrated with my apparently huge vagina.

Just as I had accepted my fate I looked down and noticed something odd. He was not inside me. His body was just laying on top of me, dick just kinda flapping over my stomach like a fish out of water. Relief.

“You’re not inside me,” I said politely tapping his shoulder.

” Can I at least nut?” he slurred, eyes glazed over. I got right out of bed and spent the night in the bathroom tub.

Fast forward seven years. I’m a 30 year old professional woman who sleeps with men her own age. Out of curiosity while telling my co workers about my traumatic experience as a cougar I looked him up. First thing that showed up on goggle was his date of birth. 10/20/1995. He had just turned 17 not 18. I quickly looked up the age of consent for the state we were in and to my relief I’m not technically a felon.