Losing my virginity – New Sex Story 2018
So the story of how I lost my virginity is actually a very interesting one now that I write about it, and it had a very happy ending (Get it?). So this started in 2014 when I was in high school, the school year was over and I was working on becoming more ” open” and have fun. I wanted to talk more with my friends, have fun, meet girls, so I decided to throw a “school’s out pool party” at my house and I invited many people, I made sure to invite plenty of single girls, one day I was at my house getting everything set up for the party the next day when my friend “Gary” came thinking the party was on this day and he brought a girl with him. This girl I thought was very pretty, and she wasn’t I guess you’d say “slut sexy”, she was kind of chubby, she was wearing a tanktop with some very revealing tit’s. Her name was “Kim” and she had a great smile and after telling them the party wasn’t until tomorrow they decided to stay and help with getting everything together for the party. Once she went to the bathroom, Gary and I started talking and he explained that they were just friends with benefits, and I brought up the fact that I thought she was pretty but at the time I had a huge crush on another girl that was coming to the party, so I figured if I said anything else about liking Kim, if my crush found out she would think I was a “player” and wouldn’t go out with me, so I kept it to myself for the rest of the day.
At one point Gary went to his car and me and Kim were talking about how they met through Facebook and she was very open about the two of them sleeping together and I didn’t really react a lot besides saying “Nice” or “Cool” but I said it with a confident and cool headed voice that she seemed to like, and throughout the night I kept talking like that and when Gary asked me about it I said “I want to be more confident for the party tomorrow” and he said to me “Oh I get it, you’re trying to get laid tomorrow, well I’ve got you covered dude” and he reached in his pocket and handed me like four condoms. I looked at him and said “Why are you just carrying these around?” and he whispered to me “Me and Kim are going to her house to fuck” and I laughed and gave him a fist bump and said “Nice dude” and I walked them out, I shook Kim’s hand goodnight and she asked if I had Facebook and I said “Yes”. That night I got on Facebook and saw she had sent a friend request and after accepting she quickly messaged me and we talked for a little bit about the party and school and after I said goodnight she said goodnight with a cute photo of herself and my cock got hard immediately and I jerked off looking at her and I fell asleep ready for the party tomorrow night.
The next day getting the party all set up everyone started showing up, and I was very surprised how many people came and as I was expecting everyone to be bored within like half an hour, everyone was fired up from the word “go”. We didn’t even have beer since my parents were home (And because I didn’t want it there, yes, I’m that guy lol). We had burgers and hot dogs, we had a DJ playing music, a fire pit with marshmallows, and the pool were everyone was having fun, I was even more comfortable showing off my somewhat big body, compared to the other guys there with six packs I had more of a “Milk jug” stomach, but as the party was going my crush finally showed up but informed me she could only stay for a little bit and couldn’t swim because she had to babysit her siblings since her parents were going to the movies.
Even when she was there I couldn’t get her into the party that much, I didn’t really want to dance, she didn’t want to eat anything, she just seemed bummed out until I took a big leap of uncertainty and started a dance off, and being as shy as I was this was weird for me but I got everyone in on it, even my crush and at one point, me and Kim started just side booty bumping and having fun and before my crush left I got her a burger and some chips and we talked for a little bit before she had to leave and she recommended I throw another party right before school starts so she could come and I quickly said “That’s an amazing idea!” and I got up on a table and said “Everyone you can thank (My crush) for this idea but should I throw another party before school comes back? Say YEAH!” and everyone yelled “YEAH!” and it was awesome to hear that, as the night started getting darker and some people started leaving, me, Gary, Kim, and a few more of my friends were hanging around the campfire eating marshmallows and Gary said “We should play truth or dare” and everyone surprisingly agreed so we went on for a little bit, nothing to crazy and I left for a second to go to the bathroom and when I came back out everyone was laughing out loud and saying “Oh my God” and I was confused about what happened.
When I sat down no one would tell me what happened until I asked Gary “Truth or Dare” and when he picked “Truth” I said “tell me what happened when I left” and he paused and looked at Kim and he said “Kim got dared to flash her boob’s at everyone” and as everyone started laughing again I laughed a little bit looking at Kim and gave a cute little thumbs up and she smiled at me, at that point my cock once again got really hard. The game kept going with some craziness where a guy was dared to run down the street and back naked which was funny until someone hid his swim trunks so I jumped back into the pool. Thankfully we found them and as I went into the house to answer my mom who was woken up by the loud noises outside, Kim walked up to me and said “Hey, I need to get changed out of my swim suit, which bathroom could I use?” and I answered “You’ll have to use the bathroom in the basement, my mom doesn’t want water dripping throughout the house” and she said “OK, can you show me? I don’t really like basements”. And I said “Yeah, just let me tell my mom something and I’ll show you” and I calmed down my mom and she said she was going back to sleep and I went back downstairs to Kim and I showed her downstairs telling her “You don’t have to be worried about this basement, it’s completely finished, my bedroom is down here too” and she answered “Really? That would be weird sleeping in a basement” and I said “Well I made it look really cool, check this out”.
And I walked her into my room next to the bathroom and as she looked around at the room I got really turned on and I thought “Man I really want to see those tit’s” so I decided to set up a way to get her to show them to me. She looked on the ceiling and noticed my blacklight and I said “Here let me turn it on” as I hit the light switch and then the room became bathed in purple light and she smiled and said “wow this is really cool ! I would love to have these in my room” and I said “yeah sometimes I’ll just fall asleep with them on, it’s very peaceful”. and she smiled at me and said “I’ll bet” it a very cute ton and as we looked at each other I said “hey, before you go, lemme ask you something” and she giggled and said playingly “uh oh haha, what’s that?” and I said “Truth or Dare?” and she giggled again and said “Ok, truth” and my cock started popping up in my trunks but the netting held it down as I gave her a little look of me saying “C’mon, pick the other one” and she noticed and giggled more and said “mmmmh ok, Dare” and I choked up a little bit because this could go very wrong, but I looked at her and said ” ok, so since I wasn’t outside, how about….I dare you to flash me” and she thankfully didn’t get mad, she actually laughed and said ” I really shouldn’t, it was kinda weird doing it before, I just did it to be fun before” and I leaned close to her and held her hand and said “C’mon…I’ll tell you what….” and my face got really red looking at her amazing face and said “I’ll flash you if you flash me” and she giggled and thought for a second and she raised her eyebrow slightly and said ” Alright”.
And my cock began getting even harder so I took a step back and she began to undo the top of her swimsuit and she revealed two amazing double d boob’s as they were bathed in the blacklight she smiled at me and I said in my confident and almost jock sounded voice “wow, you look so sexy right now” and she giggled and said “Really…awe thank you” and I walked up to her and said “Can I feel them?” She said “Yes, you can” and I felt them first with one hand, them with both, they were so smooth and as I squeezed them slightly she let out a slight gasped and I looked at her face and we looked each other in the eye’s, and as I looked back at her breast’s her nipples were very hard. I took my hands off and said “Those feel really amazing and…” I thought about what I wanted to say and I dropped the jock part of the voice and became really confident and continued saying ” Ever since I saw you I’ve thought you were extremely sexy, even knowing you and Gary aren’t dating makes me like you even”. She looked at me and smiled and said “I like you too, I think you’re very sweet, you’re handsome, and a lot of fun” and I thanked her and as she started to pull up her top again I grabbed her arm and said “Wait…..” and I put my other hand on my swim trunks and said ” My turn” and her eyes widened as I pulled my trunks down enough to the point that my stiff cock popped up and stuck out like a diving board.
She looked down and I saw her take a deep breath and she looked back up at me and said with a smile “Wow…you have a very nice dick”. And at that point I noticed her pinching her lip a little bit and by this point my shyness was completely gone and I said “Feel it” and as we looked each other in the eye’s I felt her hand slowly grab onto my cock, she smiled and whispered to me “You are really hard!” and I laughed and said “That’s just how much your body turns me on baby” and she smiled and said “Do I turn you on? Really?” and I responded and said “My cock get’s this hard every time I’ve looked at you tonight….” and I choked up a little but I put my hands on her waist and whispered to her “…I want you baby” and she whispered “I want you too, but we need to get back to the party” and in a moment I thought up an excuse and said “We won’t be gone that long, no one will notice we’ve been go to long” and she started to take her hand off my cock but before she said anything I leaned in and kissed her, I could feel her hold her breath and with our eyes open looking at each other, her eyelids slowly shut and she began to moan.
I wrapped my hands more around her waist and she put her arms around my shoulders and we began making out, I pulled her in and my cock began poking her right on her pussy and she stopped kissing me and looked down and said “Do you want me?” and I slipped my hand down to her ass and said “I want you so bad, Gary will never know” and she cupped my head and kissed me again before she began stroking my cock and I slid my trunks all the way off, and as I removed her top off completely she feel back onto my bed and I feel on top of her we began making out more and she whispered to me “Do you have a condom?” I thought for a second and grabbed one that Gary gave me out of my nightstand and I put the packaging in my mouth and began pulling her bottoms off. I took the condom out of the packaging as she stroked my cock more and more and she said to me “Have you ever had your cock sucked?” and I said “No” I stopped myself from saying I was a virgin and she said “I’ve never given one before, I kinda want too” but I said to her “That’s alright, it’s better you don’t, that way we can just keep making out with each other”. She smiled and as she laid back on the bed she moaned and said “Stick your cock in me….please !”.
I rolled the condom onto my cock and as I started sticking my cock inside her the sensation felt very stranger with it being my first time I was wondering if I was doing good but my worry was put at ease when I heard her start to moan. We started making out again as I kept thrusting deep inside of her, kissing her neck and feeling up her breasts she began to moan more and more, she stuck her tongue out and I stuck mine out as we played with each others tongues she wrapped her legs around me as we locked our hands together. As we got more into it I pulled her on top of me and she road my cock, I watched her rack bounce in the blacklight she worked my cock so much but I kept from cumming until we switched to the doggy position. As I kept fucking her I would hear her moaning things like “It feels so good” and ” faster baby”. We kept going until I could start to hear someone outside call my name. Kim didn’t hear it but I knew I had to finish quickly. I flipped her onto her back and I pulled my cock out and took off the condom. She asked “What Are you doing?” I whispered to her “I’m gonna tittyfuck you baby, and cum on your chest”.
She smiled and moaned as she said “mmmmh baby I’ve never been tit fucked before, not even Gary has done that”. I stuck my cock in between her boob’s and pressed them together as I asked “So does that make me better than him” as I began to thrust she moaned and said “You’re so much better than him baby” and as soon as she said that I could feel my cum rush to the tip of my dick and I moaned out and said “I’m gonna cum baby” I took my cock in my hand and stroked it as she looked me in the eye’s and moaned “Cum on me baby” and I blasted my cum all over her tit’s as she moaned and smiled at me and said “That was so fucking fun!”.
I got off of her and quickly threw away the condom as she got up and said “Ok, I’ve gotta get cleaned off and changed” as I looked over she was going into the bathroom to get changed I ran over to her and said “Wait” and she looked to me and I kissed her one more time and she smiled and said “Here” as she handed me her underwear which was hot red and I said “Fuck your underwear is even sexy” and she said with a smile “Some other time you’ll see me in it” as she shut the door I laughingly thought “I can’t wait to see you out of them again”.I took the panties and stuck them and the rest of the condoms under my mattress, after she changed we went back up to the party where everyone was wondering where I was and I said I was talking to my mom and Kim was changing. No one questioned it and the party continued for a little longer and as everyone was leaving I walked Gary and Kim out and I asked Gary if he wanted to hang out tomorrow but he said he had to work. I told him maybe some other time then and as they walked away I waved goodbye and Kim turned back and waved and said ” Goodnight, Thanks for the fun party”.
Later that night after I got everything cleaned up I got on Facebook and Kim sent me a message, I opened it up and it said “Do you want me to come over tomorrow?” My heart started beating faster as I sat on my bed I messages her back and said “I would love that”. The next day we were swimming and I brought up the idea of us being fuck buddies and she loved it, we fucked several times that summer and I almost convinced her into anal but she said she didn’t want to get hurt so I dropped the idea. After a while her and Gary drifted apart and she started dating someone so I told her it would be best if we stopped fucking. She agreed and I told her about how I was a virgin that night and she said she couldn’t even tell the difference, which made me happy. I went into the new school year with tons of confidence and with my new sexual experience I was ready for more high school sexual experience, but I’ll always remember my first time, I’m still friends with Kim, we haven’t fucked since I broke off the agreement but after writing this, I think I’ll talk to her tomorrow….see if she want to hang out