The People I Slept With.


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.


by ThePeopleISleptWith

1) He tipped in change. 50 cents to be exact.

2) He said “he already ate” when I mentioned being hungry.

3) He suggested a threesome with a friend I saw at the bar… four times.

4) When the bartender handed me the wrong drink he said, ” She’ll just drink that.”

5) He only complimented my butt.

6) He ordered the exact amount of beers that I said would get me drunk.

7) He wore the wrong size condom.

8) He asked me if I came. If you have to ask the answer is no.

—-> Instagram


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.


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.

Forbidden Fruit

by ThePeopleISleptWith

My orthodox Jewish boyfriend took me on a date to the Museum of Natural History. Things were going great as we walked hand in hand admiring each exhibit. When we arrived at the dinosaur exhibit he dropped a bombshell on me. He told me that he did not believe in dinosaurs. Then went on for 20 minutes stating with utter certainty that fossils were planted by people to trick dumb people. I laughed it off praying he was just making a very bad joke.

A week later he came to my apartment, in an area of Brooklyn he most likely never stepped foot in. I spent the night prior scrubbing and reorganizing my apartment in order to create the illusion that I was a mature adult woman but my efforts went unnoticed. Plastic furniture, shark posters and dinosaur toys just aren’t for adults. He walked in and sat right on my bed, that laid on the floor without a box spring.

We started making out then he looked me in the eyes slowly removed his yamaka and made his way down my body. He started going down on me and I never felt so powerful. I looked at the yamaka upside down on my floor, back at him and smiled at the God I don’t believe in.

After we had sex as I laid in his arms he brought up dinosaurs again. My ceiling were covered in glow in the dark prehistoric creatures so I can see where the thought came from. Turns out he wasn’t joking he seriously didn’t believe in dinosaurs. I spent the night trying to prove him wrong.. unsuccessfully. I could get behind not pushing buttons on Saturday but no dinosaurs.. no way.

Our short relationship ended when I was unable to expand his mind and he was unable to close mine. There was no way I could continuing dating someone who doesn’t believe in dinosaurs.


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.”


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.


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. 



by ThePeopleISleptWith

Recently I came across an article about the fun shapes one can shave their pubic hair into. I was intrigued and very bored so I attempted “The Martini Glass.” Turns out it’s much harder than it looks. I was off to a rough start and things just went down hill from there. I won’t lie… It wasn’t good. To my credit it did slightly resemble a martini glass but no I wasn’t about to show it off and quit my day job.

I forgot about my short-lived career as a pubic hair stylist and went about my day. That night I unexpectedly ran into my friend with benefits. I had completely forgot about the deformed Martini glass until he took off my underwear. He inspected it. “It’s a Martini Glass…” I shrugged. He laughed and high-fived me. I think I fell in love a little.