The One Night Stand: Virgin Edition

The One Night Stand: Virgin Edition The One Night Stand: Virgin Edition

Status: Finished

Genre: Erotica


Status: Finished

Genre: Erotica


This is a short story about a very humorous sexual event that occurred in my life at the age of 18 based on a true story.


This is a short story about a very humorous sexual event that occurred in my life at the age of 18 based on a true story.


Submitted: November 16, 2015

A A A | A A A


Submitted: November 16, 2015



(Characters names in the story have been changed)

The One Night Stand

It was one week before my 19th birthday and all I could think about was how I was going to turn 19 and I am still a virgin. All my friends had lost their virginity while in highschool and I was going on two years after highschool being  a virgin. Of course, me wanting to be just like them, I lied about losing my virginity to a girl that lived in the next building from where I lived. There had been so many other intimate moments I had experienced that just never reached the "sex" part of the event, so I had managed to gain some experience in the foreplay area, which i believed I was pretty good at.

I was working at Dunkin Donuts at the time and my sister Kaylin invited me out to a hookah lounge with her friend Ashley. After work, we went straight there in my uniform, minus the apron, without showering or anything, So try to imagine me smelling like coffee in my white polo shirt and blue jeans. I found my sister's friend to be somewhat attractive. I thought to myself, 

“I just want to have sex tonight and I am going to try to sleep with Ashley tonight.” Later that night after the lounge, we headed back to my sister’s place where we were going to stay up all night watching TV and talking in Kaylin's room. Ashley kept giving me the eye almost as if she wanted something to happen between the both of us. Kaylin decided that she was going to talk on the phone with her boyfriend out in the living room, leaving Ashley and I with the room to ourselves. I told Ashley,

“You should sit closer to me because I want to be near you.” So she did. After a few minutes I then told Ashley,

“We should mess around while we’ve got the room to ourselves” Ashley and I started making out on the bed. I laid her down and got on top of her kissing her slowly. I kissed and licked her neck as my tongue made her head roll back. As I licked her neck, I took my right hand and started to crawl up her shirt, making my way underneath her bra and squeezing her left breast. My left hand was occupied behind her head pulling her hair so that her head would stay rolled back. With my right hand I was able to lift up her shirt completely. I took a break from licking her neck and I started to lick her body, starting from below her belly button to licking in between her breasts. I took my tongue and placed on the edge of her nipple and moved it in a circular motion and then licking the middle. I put her nipple in my mouth and began to suck on it while my left hand was playing with her right breast and I eventually switched. After arousing her with my tongue, I began to unbutton her pants and that is where she stopped me. Ashley said, 

“You won’t be going down there tonight.” 

"Aww come on! Not again" I said.

“If you stay the night with me without leaving then next week I will let you.” she said. 

"But next week may never happen and that we have the opportunity to do it now and we should take it." I said. 

“How do I know that after we do it you won’t just get up and leave when we finish?” said Ashley. I promised her that I wouldn’t go anywhere and that I would spend the night with her. Ashley continued to tell me that she did not want this to happen and promised me that there would be a next time and that it would happen. After three hours trying to convince her to sleep with me that night, I finally told her,

"Okay... the truth is that i'm a virgin. I've had so many opportunities to have sex in the past, but everytime I thought it was going to happen, the chance slipped away or the girl was also a virgin and wasn't ready to do it and here it is happening again." 

 I went on about how I was 18 and my birthday was in a week and I was going to be 19 and still haven’t had experienced sexual intercourse. She felt sorry for me and took my word that I wouldn’t leave after we finished. She began taking off her pants and I couldn’t believe that it was really happening. That I was going to finally lose my virginity and then Kaylin walked back inside the room. I could not believe that it was happening again, but I wasn’t going to let this chance slip away so I pulled Kaylin to the side and told her,

“Hey sis, I know this is really messed up, but could you let us use your room? We were just about to do it! Could you please stay out here until we are done?” Surprisingly enough, she agreed to let us use her room and I was happy because there was still a chance for this to happen. I get back inside the room and Ashley was waiting for me with her pants off in bed. I take off my pants and put on the condom that I had in my wallet for months and I got on top of her. She opened her legs, and I tried to put it in and I just could not find the hole. The lights were off and the only light we had came from the nightlight across the room. I told her,

"So.. I can't find the hole. Can you help me?" She grabbed my penis and guided it to her vagina.

"There. now push it in" She said.

As soon as I felt my penis inside of her vagina, I immediately started stroking fast. I thought of sports and math so that I wouldn’t ejaculate so fast. Counting up from one to ten in my head and doing multiplication to keep me from cumming. I imagined myself running on a football field, dodging tackles and getting a touchdown. These are tips that I had taken from friends and they worked pretty well in my opinion.  

“I thought you said you were a virgin? You are doing so good for your first time,” She said as she moaned, sinking her nails into my back leaving scratch marks and blood.

“Hell yea I’m a virgin!… well not anymore I’m not,” I replied as I was stroking. While breathing heavily, Ashley asked, 

"Are you sure that you're a virgin!?"

Sadly, I only lasted about two minutes, but I didn’t care for how long I lasted because when I finished, I felt so proud and accomplished. Being that it was my first time, I was scared when I pulled out and felt the condom wet. My thoughts immediately were that the condom broke and the wetness was my sperm so I ran into the bathroom and filled the condom with water from the sink to see if it was leaking and thankfully, my first time was not a disaster. However, there was blood on the condom. 

Finally, calming down and realizing that the condom did not break and that I was no longer a virgin, I went back into the room and put my pants back on and laid next to her in bed as I promised. I asked her,

"Are you by any chance on your period?" 

She denied being on her period, so I thought I might have “popped her cherry” which is what everyone described it as when you make a girl bleed vaginally, which forced me to ask the question,

"Well... then are you a virgin?"

"No, I'm not a virgin. Why?" She asked.

"I am just trying to find an explanation for all the blood there was on the condom." I replied. I spooned her and closed my eyes and when I heard Ashley say,

“Babe you’re on my hair,” my eyes opened so wide in fear that she wanted something more than a one-night stand. I did not want to be in a relationship with her. We finally fell asleep. At 6AM the next morning, I woke up, grabbed my things and left her asleep in bed. Ashley became a stalker and very needy after that night. She wouldn’t stop calling or texting me and argued with me for not texting her cute things. I had no choice but to change my number. Or maybe I could have been honest with her, but I never heard from Ashley again after that night. My intentions were not to leave her the way that I did, but her actions caused me to do so.


Please leave constructive criticism. 

If you'd like to read more short stories of my real life sexual experiences, I would be more than glad to share them all. I've got stories for days.

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