My name isn’t Thomas, but it was when I flew on a plane for the first time headed to New York City. I had never been on a plane before, nor have I been to New York, nor have I ever had sex. I didn’t have a detailed plan for my trip and I was not entirely sure what I would be doing during my stay in this unfamiliar city. I knew I would have a good time, but I had no clue that I would end up having sex with 4 different women in a span of 5 days.

This is not a love story, this is not a Tinder advertisement, this is not supposed to be a shitty erotic novel, this is a quick and straightforward overview of how I lost my virginity followed by having sex with multiple women in less than a week’s timespan. I went from virgin, to a low budget Hugh Hefner overnight and I’m not sure if it was supposed to be as easy as it was. This is a true story.

Before I came into being “Thomas” in NYC, I was a lonely Asian tech nerd working a full-time developer job in Los Angeles, California. My dating life was scarce of women and I spent most of my days and weekends looking at JavaScript code. Although I was making decent money, I was living with my parents because I was planning on moving out of state at the time, but looking for a developer position in Nevada was a bit difficult. Months went by as I was a full-time developer working 50+ hour work weeks on top of a 3 hour combined daily commute. I was becoming unhealthy, stressed out, cranky, social skills were plummeting, and I didn’t have anytime to work on myself or my other passions. It was absolute hell and everyone thought I had it all together because of my paycheck, but in reality I was miserable and the money didn’t mean anything to me.

Then came the day when I realized I could no longer continue commuting 3 hours on top of staring at a computer screen for another 8 to 10 hours a day. I was sitting in traffic and I realized that I’d rather make a lot less money and do something less detrimental to my life and happiness. I’d rather risk my life chasing something I love doing than to accept that life is just a 9 to 5 job until retirement.

What made things worst was that after a long day of work, I didn’t come home to a girlfriend or a loving wife. I came home to my parents and I didn’t have much space of my own. I was going insane. In only 6 months into my full-time developer job, I quit my job and a few weeks later I booked a trip to NYC for 7 days not knowing what the hell I was going to do there. I knew that I wanted to have at least one date since I didn’t know anyone in the city and I had the bright idea of downloading Tinder a week before and start swiping girls who lived in Manhattan. I had never used online dating because I always and still prefer to meet women in real life such as coffee shops, clubs, libraries, malls, etc. However, for this trip, I gave myself an exception and I had no idea what I was in for.

Once I landed in Manhattan and stepped within my small and aesthetically contemporary Airbnb, I was for once living on my own in a city I’ve never been in. I could do anything I wanted. I had several Tinder dates lined up for the week and I had no clue how it was going to turn out…

Tinder Date #1 — The 29 Year Old Data Analyst

My first tinder date was a 29 year old white girl that worked in I.T and her personality backed up that fact. She was a bit on the heavier side, wore glasses, and she spoke with a very logical tone. She was like me in many ways besides the part about being heavy; I worked out often and I kept myself in shape, so I was pretty fit for this trip.

On Tinder, our conversation was pretty straightforward and it was clear that she we were going to have casual sex. She was to come over at around 8pm and I would have beer and wine ready. About an hour prior before her visit, I walked down the street into a liquor store, bought a huge bottle of Jack Daniels, red wine, a bottle of Guinness beer, and some other IPA beer. I went back up to my apartment, poured myself a glass of Jack and started drinking waiting for my first sexual partner to show up.

Once 8pm struck the clock, my iPhone dinged. It was a message from her letting me know that she was outside. I went downstairs to get her and walked her up to my apartment door, once she was in we sat on the couch and I offered her the IPA. She took it and started drinking. The conversation was pretty boring, platonic, and as I remembered, awkward as fuck. I knew I needed to transition into a more sexual vibe so I said “I think we’re a bit too tense and we should probably break some barriers.” Whatever the fuck that meant, I’m not even sure. I was just trying to sexualize the mood before she left due to boredom and the awkwardness.

It worked pretty well, I leaned in to make out with her face and so did she. Our clothes came off pretty quick after that and she started giving me oral. I got hard and I took her up to the bedroom where I put on a condom and started penetrating missionary position. Her ass was really big and my penis is only average size. It was difficult and I kept slipping out. My dick felt small, but I didn’t care. Eventually, I got tired and decided to start eating her out. I didn’t think twice whether she was clean or not at this time, I just completely lost sense of responsibility at this point. She was really turned on and told me to get back to fucking her, so I did. For some reason, I kept getting limp. I’m not sure if it was because of whiskey dick or because of performance anxiety. Maybe it was a little bit of both, but in the moment I said “You’re ass is too big…” and I gave out a chuckle. I told her that she was the biggest ass I’ve ever had and she said “really?” I said “Yeah, it is.” I wasn’t lying, but I also left out the part where it was literally my first ass ever.

I decided to finger her and make out until she came, which she did very loudly. We then decided to go back downstairs to the living room and take a rest and hopefully I could fuck her right this time. I tried, but for some reason I could not cum. She started giving me head until she got tired and decided to start getting dressed and go home.

I really didn’t want her to leave because I wanted to satisfy her and I also wanted to cum. So I smoothed talked her as she getting dressed and continued to make out. She said she was really hungry and I told her that we could go eat for a bit and come back. She said “If you’re treating, sure.” I replied “yeah, sure.”

I’m pretty intoxicated at this point because we’ve both drinking throughout the whole night since meeting so I let her find a place where she wants to eat. We find this fancy restaurant and sit down. We order food, I get a cocktail, she gets an IPA. We talk for a bit, this time it’s a lot more comfortable and nothing like how we just first met. Maybe it’s because we were fucking each other for about an hour and we’re intoxicated. Whatever the reason, there was no longer any awkwardness between us. We talked a little about ourselves, why I flew to NYC, how long we’ve been on tinder, if she had any tinder crushes, etc. She asked for feedback on her Tinder profile and I told her that her first cover photo should be changed to the 3rd one she has which was a picture of her face with good lighting and the angle was good. In which, she did listen and changed. She gave me feedback which I didn’t ask for, but was appreciative of anyways. She told me that I was a bit naive during sex because as she was sucking my dick, I pushed down on her head and she didn’t like that. I nodded my head, and took a mental note. My bad.

Once we finish eating, I paid the $80 food bill and we went back to my apartment. We started fucking again for a few hours. I made her cum and I came inside her. I asked if she was clean and she told me that she got tested recently. I took her word for it and so did she with me. She slept over and left in the morning. Tinder date #1 was a wrap and that morning when I woke up I was no longer a virgin. I was satisfied with my trip so far, but had no idea what was cumming for the next few days.

Tinder Date #2 — The Adorable International Indian Student

I assumed that most Tinder dates were just regular dates and that girls looking for one night stands were just a small percentage of the demographic. Damn, I am naive as fuck.

This date took place the very next day after Tinder Date #1.We matched a few days prior to me landing in NYC and I asked if she was busy this day. She said she wasn’t and agreed to meet for food at around 6pm. We met at a relatively close ramen spot near central park. She was about 15 minutes late and while I was waiting outside the establishment, I was sure this would be the first time a girl flaked on me for a date. As I stood there in the cold, I just kept thinking to myself, “Well, there is a first time for everything and I guess this is the first time I get stood up. It’s not a big deal.” But she did arrive and she was much more cute and adorable than what her Tinder pictures showed. As she walked towards me, I greeted her by her name. “Thomas?” She asked. “Hey, Your name is really cute. I like it”, I said. “Thanks.”, she replied. We sit down and order food. She has the cutest accent and it compliments her petite 5’3 body very well. We start getting to know each other. She talks about her upbringing in India and how she came to NYC to study in school. I tell her about my experience in NYC so far and all the little quirks that differ from L.A. We talk a little about the food, the city, what we like to do. So far it’s a good normal date and in my head I’m convinced that this adorable 19 year old girl is only using Tinder to meet cute guys to talk to and not the type to fuck on the first date. Again, I am naive as fuck.

I finish my bowl of ramen a lot quicker than she does. I guess she likes taking her time. At one point, I’m just waiting for her and she gives me a slight shit test and says “You can leave if I’m taking to long, I’ll just finish my food” as she laughs. “No, it’s fine, I like watching you eat and I’m not in a rush” I reply. I try to order a beer which is on the menu but the waitress says they don’t serve beer anymore. So I begin asking her what sort of alcohol she likes which is a good topic, because alcohol is associated with partying and sex. Turns out she is quite the underage drinker and she like to party. Then I begin to wonder if, in fact, she does want to have sex.

She’s almost done with her ramen, finally, and I ask her if she’d like to walk around for a bit and maybe she could guide a tourist like myself to show me some places. She agrees. She leads us to an isolated part of town near a river. We lean against a railing and as a look down at the body of water I tell her a story of how I fell into a lake back at home and I almost drowned, but my friends pulled me out. True story. she laughed. We take a few pictures near this huge bottle house art piece. As we’re exploring this place together she’s talking about how she envies weird people that are able to have happy relationships. I guess it was a subtle way of her hinting that she was seeking affection. It’s getting cold and I realize that I need to get this girl in a nicely dim bar or cafe so I can set the mood and get her back to my apartment and fuck her. Because at this point, she’s given me enough subtle hints to let me know that she’s down. I find the nearest bar on Yelp and we both think it’s a great idea to go to it. She’s not yet the legal drinking age, but for some reason, I had a feeling we could get away with ordering drinks with no issue.

As we walk to our destination, she begins talking about her personality, life of partying, and all the things she is trying to “suppress” while she’s a student in NYC. I ask her more about it and she starts giving more hints that she’s a wild party animal. At this point, I get the message and I am eager to get to this fucking bar, but it’s hidden and we’re lost. I tell myself that there is no way I could fuck this up, I really need to find this stupid bar right this second. I finally walk into this random building and ask the guy at the front desk if he knows where the bar that I show on my phone is located at. He gives me directions. Luckily, it was right next to the building we were currently in.

Finally, we enter the bar, it’s a very fancy hotel bar with a high ceiling. The atmosphere is perfect. Lights are dim, there are candles, the seating is nice and comfy. It’s romantic and it’s the exact mood I was looking for and it’s what she wanted too. As we’re waiting, we have small talk and our connection is pretty good and I actually like the company of her. At this moment, I enjoy the date and I don’t care whether I have sex or not. I love connecting with other women and this girl had a great personality.

The waitress comes over to take our order of drinks. She looks at my date and the first thing she says is “How old are you?” I would have been a lot more surprised if she didn’t ask that. “I’m 23” she says. I’m impressed about how confident that came out of her. “Uhm, do you have an I.D?” The waitress asks. “I’m actually an international student, can I show you my passport on my phone?” My date says. “I’ll see if that works” the waitress says. I show her my I.D and say “Can I order my drink until just for now?” “Sure” she says. I tell her the drink I want and she charmingly tells me that I shouldn’t get that one because it’s not that great and recommends a better drink. I smile and say “Sure, I’ll take that one.” As I chuckle. She looks at my date and says “and you’ll have this one?” My date nods. She never showed a single piece of I.D. We did it. We successfully ordered our drinks. Thanks cool waitress lady.

We drink. We talk. We laugh. We get closer. I get the check. Pay the bill. We’re outside. It’s time to get her back to my apartment. I’ve built rapport, we’re both comfortable with each other. Let’s do this. I touch her arm and lean in closer, “Hey, do you wanna drink at my place?” I asked while being straightforward and smooth at the same time. “okay” she says. Fuck. Is this really happening? We’re going to have sex. To think, just a few hours ago that I thought it was just going to be a ramen date and that was going to be the end of it. I request a Lyft and now we’re headed to my place.

We enter the apartment. She observes the place and says it’s cute. I offer her wine, she accepts. I pour wine in the same two glasses that were used in my previous date the day before. I make sure to wash it of course. We begin drinking and we sit down on the couch to watch Netflix. We start watching the FYRE documentary. This is the first time I’m watching it and her commentary is hilarious. We have a great vibe going on and after about an hour into the documentary I realize that it’s about that time we should start having sex. I lean in and we start making out. It was natural and I think we were both waiting for it to happen. In the middle of making out she pulls back and asks “Are you a Trump supporter?”. “hahaha, No I’m not. What the fuck.” I say with a smile. She explains that she just wants re-assurance that I’m not part of a problem. I’m not. We continue.

“Babe, take your shirt off” I say in a seductive voice. She nods, “okay”. We’re naked and fucking on the bed. This time I use a condom because she’s strict and I want to be responsible. It also turns out she’s a totally aggressive sex freak and she is biting the fuck out of my neck like some vampire. Not the vampires in Twighlight either, more like the vampires from Blade. She’s going buck wild on my dick and I tell her to slow down, but she’s not listening. She continues to fuck me until I feel her cum, then she stops riding. “It’s getting late, I should get going” she says. Damnit, I didn’t even cum yet and she’s leaving already.

She starts getting dressed. I really like this girl and I don’t wanna spend a night alone because the Airbnb makes weird noises at night. So I begin convincing her to stay.

“Baby, don’t go” I say.

“It’s really getting late, I should get going.” She says.

“Please, I really enjoy watching Netflix with you and I feel like we have a good connection” I say.

I begin making out with her and she’s not resisting.

“Okay, I’m down to just lay down and watch T.V with you.” She says.

“Yeah, okay” I say.

We lay down for a bit and eventually we go sleep upstairs. I’m too drunk to try and have sex again so we both fall asleep. The next morning, she wakes up, gets dressed, I say goodbye, she walks out the door and that would be the last time I ever see her again.

I wasn’t used to this. I had more women in my life than ever before, yet there was a sense of emptiness after these hookups. I guess I was experiencing what people called “casual meaningless sex”. It was okay, though. Tinder date #3 was showing up tonight.

Tinder Date #3 — The Filipina Nymphomaniac

After hooking up twice in a row, my mind was still focused on my last 2 previous dates. I almost forgot I even had a girl coming over this night until she sent me a text letting me know that she might get to me a bit earlier. Turns out that I was just watching Netflix and scrolling the inter webs so I told her to come over as soon as she’d like. She told me that she had been trying to “study” for about the last 4 hours and that she was eager to come over and have sex. I was flattered.

She comes over. I pour her Jack Daniels. We both sit on the couch and begin to drink while watching Conan Without Borders on Netflix — great fucking show. We start touching each other and eventually, I make out with her and she takes her clothes off and starts sucking my dick. We go to the bed upstairs and we start fucking. She’s super wet, more wet than the previous girls. I’m fucking her with a condom and she keeps asking if I always fuck with a condom, she was giving hints that she wanted me to go in raw. Eventually I take it off and I tell her that I just want to stick it in for a few seconds. Of course, I wanted to go in raw because she was super wet. I take the condom off and begin fucking her for a few seconds and take it out. “I’m not gonna fuck you” I tell her. I stick it back in and continue fucking her for a few more seconds and take it out. I put another condom on and we continue having sex. She cums again and again. Long story short, we go downstairs, she takes the condom off to suck my dick and I fuck her raw and cum inside a little before pulling out.

“Oh shit, I think I came inside”, I say.

“You did? That’s not funny”, she says.

“I’m sorry, I thought you were gonna get off on time. “ I say.

She licks some cum off my dick and says “Hmm, it taste good too”.

Damn, this girl is wild.

I asks if she could try and take the jizz out of her body. She goes in the restroom for a bit and comes back out. We lay on the couch together and I tell her that I’ll buy her Plan B and she has to promise to take it. I’m kissing her forehead and trying to keep the mood going because If I think that If I’m too demanding or straightforward, it would piss her off. She’s a little reluctant to allow me to buy Plan B because she explains that she doesn’t want to have a forced period. I’m freaking out inside and I’m trying to keep my cool. “I DON’T EVEN KNOW YOU, I DON’T WANT KIDS, AAWW SHIT I FUCKED UP, THIS GIRL IS CRAZY. FUUUUCKCKKKKKKK!” I think to myself while looking completely calm. “Baby, I could get you the pill, it’s not a big deal. I don’t want kids” I tell her in a controlled soothing voice. She giggling for some reason. “I’ll get checked in two weeks. Just let me take care of it” she says. After some back and forth discussion, I decide to let her do her thing. We’re both hungry after sex, so we decide to go out for some food. I look up the nearest restaurant that looks appetizing on Yelp. I try to show her my phone as she is laying on my lap and I drop my phone on her face. I laugh and apologize. I kiss her on the forehead. Shit was hilarious.

We go out to get food and it’s practically a date. We have a good time and we’re talking about random stuff. At this point, we’re having a normal date. After we finish our food. She offers to get me some Artichoke Pizza because it’s her favorite. I’m still hungry so I tell her it sounds like a great idea. We get to the pizza shop and she buys herself and I pizza. It’s huge and delicious. We could both barely finish ours and we get full before getting anywhere near finishing it. We throw it out and she leads me back home. We reach her train stop and I make out with her and say our goodbyes. I go home and lay on my bed. I take in the fact that I had just slept with 3 different women on back to back days since I’ve landed in this city. Life is great and I’m having fun.

Tinder Date #4 — The Gorgeous Short Haired Girl

I can’t tell the story of my 4th Tinder date without bringing up the previous girl — The Filipina Nymph, because she came back. A day after we hooked up, I got a scary text from her that read “Thomas, can we talk?” That shit nearly gave me a stroke. I was thinking to myself that she must’ve caught feelings after sharing that Artichoke pizza with me and decided that I was the man to have a child with. The text that followed gave me a huge relief — “Would you mind still getting the pill?” She asks. “I don’t mind.” I respond. She plans on coming over that afternoon so I could buy her Plan B and we’re also planning on having sex again.

It’s 5pm and she’s back at my place, we’re watching Conan Without Borders. I tell her I have a Tinder date in 3 hours and she’s cool with it. She says “We could fuck real quick and get the pill within 3 hours”. We start fore playing and making out. We get naked. Have sex. I cum in her twice. Fun times. She gets dressed and we’re ready to go down to the CVS around the corner to get Plan B. Before we leave I ask her if I should shower before seeing the other girl, she smells me and says I smell good and that a shower was not necessary. I don’t shower. We get the Plan B and I kiss her goodbye as she heads to her train stop.

By this point, I’ve fucked a girl twice, I’m munching on Jalepeno chips and I’m exhausted. I need to get ready to meet my 4th Tinder date in about an hour at a bar right across the street from my place. 8pm hits the clock. She texts me that she’s waiting outside the bar. I’m dressed, tipsy, tired, and ready to meet. I get a text from Tinder date #3 and she says she forgot her ring at my place and that she’ll come get it real quick tomorrow afternoon. Okay.

I head outside to meet tinder date #4. I arrive at the front of the bar and she’s waiting for me. I hug her and greet myself. She’s very pretty. She’s Caucasian, about 5’7, with a short hair that fits her and she’s wearing a dress. She actually looks kind of lesbian, but she’s cute.

We get seated in the bar. I ask her what would she like to drink and she wants a Heineken. I order a Heineken and I get myself whiskey while she waits for her fries.

We get our drinks and food and sit on a table across from each other. She says I look exhausted. She’s right. I just had sex right about an hour before and I’ve been drinking since 5pm. I didn’t tell her that. Not yet, at least. We talk about typical things people talk about on a date — our jobs, school work, common interests, etc. I compliment her hair and I begin making observations about her. I say she seems like a very observant person as she’s looking around the bar. I make a joke and say that if anything bad were to happen, she’d be prepared. Unlike me, someone that constantly spaces out, I would die in an emergency situation. The date continues. We talk more. I build rapport. We joke. Blah blah blah. Eventually, she asks for a tequila shot and I’m happy to get it for her. She takes it and says something like she doesn’t hook up and I tell her that It’s perfectly fine and that either way I’m happy regardless. Then I ask her if she wants to come watch Netflix across the street at my place. She agrees.

We reach the apartment and I she begins to observe the living space. We talk about the ridiculous rent prices in Manhattan and about where she lives. I pour a shot of Jack Daniels for both of us. We sit down on the couch and begin drinking and watching Conan Without Borders. After some time of talking and getting closer. I lean in for a kiss and she avoids it for a bit and calls me a fuck boy. She’s being playful and I laugh and back off. I wait a bit and move in for a kiss and she kisses back. We start making out. Clothes gets thrown off. We’re naked and we are fucking. I’m going at it on the couch with her and I orgasm. I have a condom on. I pull out and she takes the condom out and she says she wants to play with it. Sure, go for it.

I’m eating Jalepeno chips. She’s playing with my condom. Conan Without Borders is playing on the T.V. She wants to keep going. We hang out on the couch for a bit and she starts telling me an emotional story about being in love and about her ex. I’m kissing her and nodding my head. Then something bizarre happens. As I’m in the middle of kissing her I start chuckling and let out a loud laugh. I start laughing and it gets worse. As I’m giggling like some jackass, I get up and say “Sorry, I need to use the restroom”. I close the restroom door, turn on the fan, turn on the water, start biting on a towel and start laughing hysterically within the towel. I’m in there for about 3 minutes. I finally come out, sit next to her and apologize. Till this day, I still have no idea why I was laughing so hard. I try to explain myself. I tell her that I wasn’t prepared for the transition in topic and that she caught me off guard. I don’t remember what was said after, but we were back on track shortly.

Anyways, a few moments later, we go upstairs and start having sex again. I run out of condoms and I start going in without one. We have sex for the next hour and I can’t cum because I’ve had sex about 3 times with 2 different women within the last 3–4 hours. I am exhausted. She begins humping the pillow and cums. It was pretty damn hot. We lay together and talk. It gets pretty intimate. She says she needs to go because her parents are going to wonder where she was all night. I say it’s fine. She gets dressed, I make out with her, we say goodbye and she goes on her way.