[23M] How I lost my virginity [MF]

Now before we get on with the story, everyone mentioned is 18+

I have been very hesitant about sharing this story, but the people who for some reason follow me on Reddit wanted it! I really wish I could say that I lasted super long, well, I mean, I kind of did, if you count cumming multiple times lasting long. Anyways, it was very, awkward, to say the least.

(Skip to “$$$$$“ to get to the actual sex part)

October 31st, Halloween 2015. I had just turned 18, four days ago on October 27th. I decided to go to a Halloween party instead of Trick or Treating because I’m not a little kid anymore, even though I dressed up as Naruto like the little nerd that I am. I went with 4 other friends who also dressed up as Naruto characters: Sasuke, Rock Lee, Kakashi, and Shikamaru. Ok I’ll stop nerding out now. We all arrived at the party and we got a ton of looks, both good and bad, but mostly good. We were all getting compliments on our outfits the whole night and I had a couple girls flirt with me but I shrugged them off as compliments, because I was 18 and stupid. But there was this one girl, she was in a Zelda (specifically Twilight Princess Zelda) costume that looked amazing. Being the giant nerd that I am, I started to drift towards her. I “accidentally” bumped into her and started talking with her.

She was beautiful, light brown hair (it was really black but she dyed it for the costume), bright green eyes, pale skin, some [nice tits](https://imgur.com/a/FtPNqRq), [small round ass with long legs](https://imgur.com/a/UE8qa0o), and around 5’7. We both had similar interests: video games, anime, cosplay, and a ton of other stuff. Mid conversation, my friends ran up to me and told me there was a girl in a Hinata (the girl Naruto ends up getting with in the anime) costume and dragged me over to her, luckily I got the other girls number. (I actually have a story with her that is pretty cool, so if you think I should share that, tell me!)

I got over to the Hinata girl and, holy mother of god, she was meant for the cosplay. She was shy, long black hair, contacts that looked like her eyes in the anime, and most importantly, [HUGE tits](https://imgur.com/a/Sd3TyXj), she had a nice ass too (couldn’t find a reference that looked like it). When I walked over, I saw her notice me and I could tell she was thrilled. She nervously started to inch her way over to me and I for some reason started to get nervous. I guess she got too nervous and went back to the spot she was at before. I mustered up the courage and walked over to her. She was sitting on a couch and I sat next to her but like a couple inches away not to make it weird. I looked over and she looked like she was going to faint. I asked if she was ok and she said she was fine in a high pitched voice, lower than the anime (she has like an extremely high pitched voice) but it was still pretty high pitched.

I asked if I could get her some fruit punch or a snack and she said she would love that. I got up and when I was out of vision of her I started walking as fast as I could over to the food table. I saw my friends over there and I was asked a ton of questions but shut all of them down and told them I was in a hurry. I grabbed two drinks and two ghost shaped sugar cookies for her. I walked back over to her and saw some guy in a vampire costume sat very close to her very obviously creeping on her. I looked at her and she was very uncomfortable so I sat down next to her and she very quickly said to that guy that I was her boyfriend, which very much shocked me and I almost spent my drink out but that made the guy quickly walk away from her. I looked at her and before I could say anything she thanked me and gave me a hug which made us sit right next to each other.

I asked if she knew that guy and she had no clue who it was, and told me that he sat next to her as soon as I left. I also asked her why she said boyfriend instead of just a friend, she replied with “well since were are in a couples outfit it would make it more believable.” Fair enough. I asked how old she was and she said 19, and told me she wasn’t a virgin and winked. That caught me way off guard but me being the virgin I just nervously laughed and continued conversation with her.

$$$$$$$$$$$$$$$$$$$$$$

We sat there talking for hours, most of the people had left the party, except for about 10 people (there was like, 150 people at that party, it was a big house), 4 of which were my friends. At this point we were both flirting like crazy with each other. Like almost every other sentence was a flirty remark to the other. I did the cliché yawn and put my arm around her and she started giggling. She brought her legs up onto the couch so she raised herself up and kissed my check and quickly looked away.

I started blushing so hard and in response I kissed her cheek. I heard her gasp and she hugged me. I hugged her back we were soon kissing. My hands explored her body and landed on her tits. She pulled away and said “you’re a pretty good kisser for a virgin!” (was mentioned in an earlier conversation that I was a virgin and had never kissed a girl before) I was flattered and told her to follow me. I walked around with her arm around my waist the entire time trying to find the host of the party.

I finally found him after 3 minutes of having no clue where I was in the giant house. I asked him if there was an open bedroom that we could use. He had the look on his face that said he had been asked this question quite a few times. He walked us past a couple of bedrooms, one of which I heard moaning coming from, and opened the door to this small bedroom that only had a bed and a nightstand next to it and told us to have fun. I shut the door and locked it and turned around to see her take her top off and squeeze her tits together.

I was as hard as a diamond and it was very obvious too. She laughed and said “well someone’s excited!” I climbed onto the bed and she climbed on top of me and we started kissing again. She was grinding against my massive erection and unzipping my jacket. I unzipped her jacket and her took off her sports bra and her tits fell on top of my chest. She moved up and smothered my face with them and moved side to side, making them slap me. We both started laughing like idiots and my hard on had slightly softened. I grabbed her left tit and licked her nipple, massaging the other one with my hand. She let out soft moans and started rubbing her hands on my chest. She pulled back and asked if I was “ready for the appetizer?” I at first thought she was going to blow me, but after I said yes, she started undoing her pants. I realized that she meant I was going to eat her out.

She laid on her back and finger wagged me over to her. I sat up and got on all fours in front of her. I stared right into the eye of the storm and I had no clue what I was looking at. She laughed and said “you really are a virgin.” She told me to give her my hand and she guided it to where her clit was and said to rub that.

I started rubbing it and she let out a soft moan and told me to lick her lips. I thought that was a strange request and went over to her face to lick her mouth lips. She hit the top of my head and told me not these lips and laughed. I was confused and she said her pussy lips. I facepalmed and we both started laughing. So I went back down and started licking her pussy lips and place my thumb back on her clit. She tasted fucking amazing, I was already hooked. I flicked my tongue up and down and she moaned “fuck, Naruto” which caught me so off guard and I laughed. “So you want to roleplay?” I told her, and she was bright red. She said “I’m sorry I just got too into it and since we’re both in costume, it just felt right.” I responded with “if you want to say it, I’m completely fine with it, but you don’t have to.” She nodded and I continued on with my duties. I massaged her thigh with my free hand as I was licking her, now soaking wet pussy and rubbing her clit.

Her moans started to get more intense and louder and breathing heavier. She almost screamed she was going to cum and one hand gripped onto my hair while the other gripped onto the sheets. I stuck my tongue into her pussy and she came on my tongue. It tasted so good. I had just had my appetizer, and now it was time for hers.

She pushed me onto my back and took my pants off. She started kissing my cock through my underwear and I was having the time of my life. She finally took my underwear off and kissed the head of my cock which made it twitch. She started licking it up and down from the base to the head. I felt like I was in heaven with the way it felt. She started stroking it and sucking on my balls which made me go wild. Out of nowhere, she shoved the whole thing into her mouth. It was one of the best feelings I have ever had and I’ve never been able to replicate it. She blew me for 30 seconds before I came, and I felt so embarrassed.

When she was cleaning the cum off of my cock, I came again, which surprised us both. I was still hard so I offered if we had sex. She agreed and asked if I had a condom. Since I had just recently turned 18, I bought a condom and kept it in my wallet just to be safe. I rummaged around in my pants and found my wallet. I pulled it out and opened it. I put it on and she made sure it was tight on there and got on her back. I teased her and slowly stuck it in, this was the moment I had been waiting for. I stuck it in and it felt, ok. Like it was good but it did not feel as good as I thought it would. I started thrusting in and out and it made it feel a little better but, not as good as I hoped. About 2 minutes after I had stuck it in, I felt a bunch of tension release. I pulled my cock out and there was a giant tear around the tip of the condom. I said, “ummm, we have a slight problem. The condom broke.” I had apparently gotten a size too small and grew too hard to fit inside of it. She looked at me and smiled. “Just take it off and keep going.” I looked back at her and asked if she was sure.

She was 100% positive. I took it off and slid it back in. That felt fucking amazing. It felt way better than when I had the condom on. I thrusted into her and she moaned loud into the pillow she was on. I went on for two minutes and I felt like I was going to cum. I somehow managed to pull out just in time for me to shoot a load that hit her in the face. She squealed and giggled since she didn’t expect to get a facial. She looked at me and said, “Thank you, Naruto-kun.” (weeb shit don’t worry) I kissed her and then passed out completely next to her. I then woke up in a car with my costume on and the girl laying her head on my shoulder. We went home but before she got out, she gave me her number and blew me a kiss.

We started dating shortly after and the sex was pretty good, probably one of the three people I’ve ever slept with. We dated for a little over a year but then broke up because I moved across the country (West coast to East) and she didn’t want to do long distance. We’re still really good friends, I even visited my hometown in 2019 and I saw her as well as all of my other friends there. We didn’t do anything, unfortunately, because she was with someone at the time.

Source: reddit.com/r/gonewildstories/comments/ptpin9/23m_how_i_lost_my_virginity_mf