Love & Sex

Everyone I’ve Ever Had Sex With: Female, 26, New York City

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The Ginger didn't really have a soul, but he was good in bed.

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It was New Years and I had just turned 17. In my back pocket I had Apple Pucker in a flask and in my hand I was holding a book of CD's from my car. I changed the music to Mandy Moore – Candy and immediately made eye contact with Tony. We bonded over our love for Mandy and started making out in a corner, we moved to a walk in closet where I lied about my age, virginity and pretended to know what to do with an uncircumcised penis. At some point I realized another couple entered the closet as I was standing against the wall and getting fucked. We never talked again after that night.


My shortest "relationship" if you could even call it that. I was 17 and he was a 21 year old drug dealer in a band. The first night I stayed at his house, we watched Finding Nemo and fell asleep. I woke up to him trying to finger me, we fucked until I couldn't stay awake anymore and had round two in the morning. The most memorable part of our relationship was taking Mushrooms and fucking for what seemed like days. We dated for two weeks until he ended up in the hospital and broke up with me.


I spent nearly 5 years with Ian, it was a very domestic relationship with a sex life that always felt like something was missing. Although he wasn't my first, we had a lot of firsts together. I remember the day he first made me squirt and I was a blushing teen, the night we tried anal and later learned we were clearly doing it wrong and then all the nights where I tried to just blow him and he wanted to simply play World of Warcraft instead. In the end, our sex life completely ran it's course and I fell out of love with him.


This is the first boy I let sleep over my house when I was still living with my parents. We dated for a few months and for some reason he always wanted to just mutually masturbate. I would spend 20 minutes pretending to rub myself off until I could just give him a blow job and finish him. When we fucked, it was glorious and I don't understand why we didn't do it more often. Later that year, my dad embarrassingly said "I know what you're doing in there" and I never had sex in my parents house again.


I barely remember this drunken night, because I had one goal and it was to fuck Matt. It was a hate fuck, with a middle finger pointed directly at my ex-bf. After a mediocre session of missionary and doggy style, He finally came on my tits and fell asleep.


How we ended up fucking, I still have no idea. He was older than me and was still living with his parents, I came over late one night and discovered he had a mirrored ceiling. I pretended to really enjoy it when he was fingering me and ended up sitting on his face to make him shut up. We fucked for five minutes and I jerked him off so he could watch himself get off in the aforementioned mirrors. 


Continuing with the "older than me" phase I was currently in, Dave was much older and owned a home. For some reason his room was in the basement of his house and we ended up only fucking in positions where he could look at my ass. He always smelled strongly of dial soap and I broke things off after a few sleepovers.


A long time friend. Way before losing my virginity, he was the first boy to try to finger me and made my leg twitch uncontrollably. He said that meant I was orgasming and he was hitting the right spot. Fast forward, he picked me up from the airport one night and I slept over his house. He must have practiced a lot over the years, because I have never had so many orgasms in a night from hands alone. I craved his touch for weeks afterwords, but it never happened again.

My Second "Long Term" Boyfriend

I drove hours to meet him to spend Valentine's day with him and in later weeks found out he was in a relationship and still lived with her. We spent about an hour on the couch talking about sports before we had hours of sex. He desired the most taboo things in sex and he was the first person I ever puked on, and it wasn't an accident. We ended up dating for over two years and it ended terribly. I now have a restraining order against him.

Missed Connection

A co-worker pointed out a missed connection for me on Craigslist and although I was still in a relationship- I answered it. We became strictly platonic and he was very aware of my soon-to-be ending relationship. After things ended, I made him swoon me. He was probably the skinniest man I have ever had sex with and I probably cannot count the amount of bruises I got from his hip bones. We stopped talking for a while, slept together again when we were both lonely and recently got in contact again.


Thank's again Craigslist. I was trying to sell something and instead had a very aggressive man messaging me to send pictures. I was feeling bored and played along, he worked in fashion and after a few emails and texts I figured he was normal. I visited him a month later and within five minutes in the door he had thrown me on the floor to spit on me and fuck me. It was the wildest experience of my life and during my "no fucks given" phase. I think we fucked one time after this and I realized how insane he was and had to end it. We are still friends on FB.


I swear this man modeled in those domestic "Porn for Women" coffee table books. We were roommates and he was always cleaning shirtless around the house, he was basically asking for it to happen. I didn't have AC at the time, so I asked to sleep in his room and well- one thing led to another. It happened twice and luckily it never got awkward.


I deeply regret breaking this boy's heart. He worked at a restaurant next to my job and would visit me often. We would hang out and listen to records, watch movies and after a few weeks we slept together. I remember him being very well endowed. We lost touch after a while and slept together this past year, he wasn't as well endowed as I remembered.


I honestly had no idea what his name was when I invited him to my house. We had been hitting it off all night and I really needed to have sex. It was terrible. I made up an excuse that I had to go to work early and made him leave. Years later I found out he is now in jail for killing his girlfriend. I'm still speechless.


We were friends for a while and ended up closing out a bar together. It was in walking distance to his house and we wanted to drink more. The thought of sleeping with him never crossed my mind, until he was down to his American Apparel underwear and standing in front of me. It was terrible, I don't think he even came and he kept trying to drunkenly fuck over and over again.


My friend was staying me at the time and invited her friends to crash at my house. Somehow we had split into two groups and as it seems, I am always trying to just go to sleep. Some flirting happened and soon I reached down to discover how well endowed he was. We were spooning and fucking for a bit until we ran to the bathroom down the hall, He tried to fuck my ass but there was no way he was able to succeed. Hands down the largest cock in length and girth I have ever encountered.


I remember hanging out with Tristan for a few weeks during the summer and being unable to wear shorts. Why couldn't I wear shorts? Well, Tristan somehow managed to be so aggressive in bed that my upper thighs were constantly in a state of black, blue and yellow. He also managed to bite my inner calf so hard I had the most ridiculous bruise from it. I didn't enjoy my pants-wearing summer, but it could have been worse.


Wasted at a house party, this sober "angel" let me sleep in his bed. His roommates were a couple who tried to get me to have a threesome with them, I tried to pass out and instead gave a pathetic performance in bed and wished it never happened.


My first multi-partner experience. I made jokes at the bar about an orgy and a close friend of mine was determined to fuck me with her strap on later that night. She called her boyfriend over and I called over the most recent boy I fucked. Before I even made it in my door, I tried to call it off because I was so drunk. Not a second later, we were leaning against my house and she had her fingers down my throat to make me puke. It worked until I realized how comfortable my bed was and I just wanted to sleep. She had no problem keeping me awake though after she started fucking me. Finally the boys came over and it was a lot of stimulation going on, and for some reason mainly on me. The boy I invited over got really overwhelmed and I ended up taking him to another room to finish him off. If anything, I think I just did this for the story.


While in town visiting, I mentioned to my friend that I jokingly wanted to be set up on a date. She took this seriously and in an hour, I had a handsome prison guard show up to her door. She had left for the evening and said I could do whatever I wanted to in her room. We hung out on the bed and decided to just have sex, after a few pumps we both started laughing and realized we couldn't do this. We were both attracted to each other but the whole situation was so ridiculous- it really killed our mood.


I love working in restaurants and making friends with the cooks. It would always result in delicious snacks and eye candy. Matt and I had a great work relationship for a while that escalated to outside of work hang outs. This situation made me realize how oblivious I am to my surroundings that are the opposite (or sometimes same) sex. At this point, you'd think I would understand what it means when someone says I can sleep at their house instead of trek home. But no, I never got it. We slept together and after him pressing me to hang out again, my delicious treats and eye candy turned into hungry work shifts and side eye.

OkCupid Round One

Mike messaged me on OkCupid saying he was new in town and wanted to hang out with someone like me. I didn't understand what that meant, but went with it. He made me meet him really south of the city and escort him to a restaurant of my choice. I should have known the date was going terrible when we split the bill and the server ran the wrong bill on my card. Instead, I went back to his house for some coffee and decided to stay over. He was very forward once in his room and immediately stripped both of us down. After we had sex, we were looking up images on his computer when I noticed he had photos of me saved to his desktop. I made my exit after thirty minutes and never spoke to him again.

OkCupid Round Two

This photo-hipster messaged me asking if I wanted to make last minute plans. We exchanged a few messages, flirty texts and met up for a drink the next night. He invited me back to his schoolhouse turned loft apartment and wanted to make it clear he doesn't sleep with people on first dates but that I could sleep over. After getting into bed, we fucked for two hours. I had work in the morning and slipped out of bed quietly. He recently added me on Instagram, so I don't think there were hard feelings.


He took me on an amazing dinner date and to the casino. During the night, he asked me if he could photograph me with his bikes in different positions for him to hang up in his bathroom. We started making out while I was playing Kitty Glitter and decided to leave immediately. Without speaking, we bolted for his front door and left piles of clothing throughout his apartment. The night immediately halted when he said he only wanted to fuck me in the spooning position and it lasted for less than 6 pumps. We never went on a date again but he recently was in town and begged me to visit him in his hotel. I declined his offer.

The Vegas Hat Trick + 1

I guess what happens in Vegas, doesn't stay there. In under 24 hours, I managed to wake up in someone's bed, make my way to another, fall asleep in a third and invite someone to my room the next morning. I think we should leave some mystery to these four however, the overall experience was memorable and nothing I ever desire to do again. Vegas, baby.


I flew out to Los Angeles with the promise of a Disneyland on the horizon. We had been talking for months prior and time was really on my side with this one. I arrived and we immediately had a 3-day relationship, with unlimited amounts of PDA and sex. I finally got my Disneyland with my pretend Boyfriend and when I got out of his car to go to the airport, it was a mutual understanding that this is where the magic stopped. We still talk every few months, I wouldn't change what we had for anything.


If you've ever accidentally dated someone without realizing it, you'll understand what happened here. We hung out 3-4 times a week when I was new to New York City and he was my adopted tour guide. Little did I know, we were going on dates and when I let him sleep at my house one night- I found out the hard way. He made an advance and by that time everything came together, how did I not figure it out sooner?! I slept with him and while he was inside of me, explained that we could never be more than friends. He claimed to be okay with this, but I lost my tour guide after this night.

Ian (2)

I think we met on an online forum, where we discussed being pen-pals and living extremely close. We talked online for weeks and I found out he had a baby and with that- a baby's mama. There was mutual sexual attraction and we ended up sleeping together while he was at work one night. Things got complicated with the baby's mama and I had to exit the situation.

OkCupid Round Three

Before I moved to NYC, this person messaged me on OkCupid with hopes of going on dates in the future. Somehow we exchanged messages and texts over the course of a year before I even made it to NYC. When I finally got settled in, I met him for a few drinks at a terrible beer and pizza bar in Brooklyn. He asked me if I wanted to come over and I agreed, we finally made up lost time and had sex after he made me listen to terrible synthesizer music he made. He still texts me two years later to come over and play. I don't see this happening again.


I would marry Kent, if he asked me to. He is an ideal husband who works hard, studies hard and knows basically everything about me. We used to live in the same city for years and after my terrible "Second Long Term Relationship", wanted to date me. I wasn't ready for it and we remained close friends. After moving away, I was in town for the night visiting and stopped by his house. We were both single at the time and he started kissing my neck. He took a video of me giving him a blow job and decided to fuck me. The night was ruined when he pulled his dick out and realized he was covered in blood, which didn't come from me. There was a lot of confusion and we decided the timing just wasn't on our side. We still talk and have a pact to get married in our 30's if we are both single and lonely.


I admired Tom for weeks before making any sort of advancement towards him. Had I known how easy he was, I would have definitely made a move early on. The first night we slept together was after hours at the club he managed, in the women's bathroom while I was bent over the sink. We slept together over the course of the next two years and had the best fuck buddy situation I have ever been in. It was always strictly business. We are still friends.


We were set up on a "blind" date through a mutual friend of ours. We both shared a love for Rom-Com's and bikes. We met at a really shitty Brooklyn bar and had small talk for a while, then he decided to kiss me. We made out for a longer than appropriate time in public and decided to head to his house. Now, I think of shower sex as something you do in a relationship but for some reason- this was a regular non-relationship thing we did every time we fucked. He was obsessed with my tits and I didn't hate his dick inside of me. It worked for a while until he freaked out that we were becoming too "domestic".


We talked for a long time before actually meeting, although he was close friends with everyone else I knew. He visited me and thus began a summer of heart break. I fell into a complete downward spiral that summer, putting him in front of everything else I did. We had amazing sex and it only got better with time, especially when I found out that he wanted me to fuck his ass and treat him like a slut. One night he lied to me and basically begged for my forgiveness, I only considered it after I fucked him and felt really dominant in the situation. It ended on terrible terms.


I met Richard after work one night, while out with co-workers. He made a few comments throughout the night that made me think he was interested. Soon, it was four in the morning and last call had already passed. We split a cab to my house and without talking immediately got undressed. He commented that I was different than anyone else he had ever slept with and I told him he was the only Asian I had been with. The sex wasn't memorable, it never happened again.

Mike from Home

We flirted online and through texts for a couple of weeks before I visited home and he promised to take me on a date. I met up with him at our mutually favorite sushi spot and the night immediately turned into a roller coaster. After drinking my weight in every alcohol imaginable – we took a cab to his house and got into bed. After heavy petting and making out, the layers eventually shed and he whispered in my ear "My only rule is that we can't fuck". Not letting this ruin anything, I continue on kissing him and pawing at him. Within 5 minutes, he whispered "Fuck it, I have to be inside of you". When all was said and done, I went to use the bathroom and immediately projectile vomited all over his Hello Kitty shower curtain. I haven't talked to him since we said goodbye.

The Ginger

The Ginger really didn't have a soul, but he was really good in bed. We had some of the greatest sex imaginable and craved each others touch. Every time we slept together, we had a minimum of three rounds. I have never had a partner who came as much as he did, as many times as he did. I was obsessed with everything about it. Reality hit at some point though and we realized we didn't even like each other aside from using each other for sex. We no longer talk, but I would use him again.


Nothing tastes better than forbidden fruit, right? I actually feel terrible that this happened. I'd like to erase this one off my list and never talk about it again.


I was a rebound for then Ex-Girlfriend, he hit on me harder than anyone I have ever encountered. He took me to his gorgeous waterfront apartment in Manhattan and he really wined and dined me. Over the next few weeks, we consistently saw each other. The only memorable time we had sex, was in his kitchen where I spent half of the time reading the back of a Nutella jar while his face was buried into my clit and I stood above him. We stopped talking and he's back together with his Girlfriend.


I was in Europe for work and spent most of my afternoons at the pub with foreign co-workers. The company only put up employees if they lived a certain distance from our meeting, Mat happened to be one that lived too close. I offered him a place to stay for the night and when we got back to the hotel, he immediately undressed down to his boxer briefs and laid in the center of the bed. I awkwardly got in and realized he was already rubbing his cock. We fucked for a while that night and I even let him fuck my ass. He came while saying "I love American slut's". The next day at the meeting we didn't make eye contact.


We met in another state while I was traveling for work and realized we were both from New York. We ended up becoming close friends pretty fast and I spent the initial weekend denying his affection. When we were both back in New York, we hung out daily. I slept at his house multiple times, where no sex happened at all. One day we stopped over to pick something up between plans and it just happened, I was on top of him riding him and at some point just spit in his face. He came immediately and we realized we were already late to dinner. We had sex one time after that and still remain friends. He recently told me he had a dream that we took mushrooms and had sex, I'll let him keep that as a dream though.


After I sobered up from a long winter of drinking, I was given a ride home with Connor and friends. Apparently their idea of giving me a ride home however, including dropping Connor off at my place. We had flirted in the past but I never thought much of it, until I was put in this weird position. He started pawing at my tits and I really was not in the mood at all, we had a pathetic one night stand and I lied about having a meeting in the morning to kick him out.


I can honestly say, I never expected to sleep with this person. We were friends and he had a reputation among a certain area of Brooklyn that I really had no interest in becoming a part of. One night I was hanging out at his house and it got late, he invited me to stay and I accepted. There was no cuddling, no flirting at all and I fell asleep. At some point, I woke up to his arms around me and a boner on my ass. He started flirting and I did my best in my half awake state to go along with it, there was no fore-play or kissing at all. He just went for a really intense 2 minute session before getting off. I had no idea what to think of it and we never really talked about it again.

Irish guy

Well, this was a bad idea. Thanks to loads of alcohol and being in a foreign country, I ended up going home with someone from the bar I was at and just let things happen. I was in bed sipping on some terrible wine when he went to the bathroom and came back to the room reeking of some kind of foreign Axe body spray. I tried to give him a blowjob but I swear he was using that spray as spermicide or really did not want me to go near his penis. I told him I wanted to watch him jerk off before I let anything else happen and fell asleep right after he came.


It's boy's like this one that make me appreciate the other sex as a whole. He is a beautiful man who knows exactly what to say. I actually turned him down for months and months, because I knew his type pretty well. I called him out on playing the innocent card when he was the complete opposite and finally invited him to stay over when he was in town. I knew what he wanted and he wouldn't accept that I didn't care, I finally gave in and made the first move after I realized he wouldn't do anything about his raging boner pressing against my ass by himself. We've slept together multiple times and he's great at boosting my ego and telling me that he jerks off constantly thinking about blow jobs from me.


One of the most beautiful women I have ever encountered. Somehow, we ended up flirting extremely hard and I realized that I had to make a move. I took her back to my house and she only wanted to please me, she told me she didn't deserve to get off. She played up the submissive girl act extremely well and I didn't hate sitting on her face for an hour while wave after wave of orgasms hit. Unfortunately, she also came with a side of crazy and we no longer speak.


My most recent relationship. We dated for three months and I don't think I touched my vibrator during any point of it. I don't know who taught him where a clitoris was, but I would like to shake their hand. He was extremely handy and knew what he was doing and did it over and over again. When we broke up, I realized that finding a toy to replace him would be impossible.