Hey! It’s been a while since I’ve posted a story, so I thought I’d pull this from when I first started having sex. With the first girl I ever had sex with.
I’d known this girl since middle school when I was dating this bitch who cheated on me and she passed me a note in class.
*”Hey… so I saw (my girlfriend at the time) kissing (some fuck) yesterday…”*
Honestly, I’d expected this because of how much a cunt she was anyway, but I didn’t believe it. This though started a friendship between, we’ll call her, DeeDee and myself. It was simple middle friend/crush stuff, passing notes in class, and me teasing her when I passed by her. Then one summer she told me, she had a crush on me, and I celebrated that fact.
Nothing happened between us, through middle school or high school.
I went through my hoe phase in high school, but her and I never hooked up. Till it was the end of our senior year and we both had this afterschool activity together. We sat next to each other, we’d chat, flirt, and then after school text. Soon the texts became more and more flirty and then turned sexual. At the time, I just ended this relationship with another girl who’d, surprise surprise, cheated on me. She would send me texts to cheer me up and then, one text she sent me a picture of her pulling down her tank top and showing off her pink push-up bra.
*”I wish you were here to take this off… ;)”*
Instantly, turned on and we started sexting. Which is pretty ironic as I had never had sex and was virgin up until then. So we texted back and forth and she sent more texts with pictures of herself.
****DISCLAIMER: WE WERE BOTH 18 AT THE TIME****
This was also the time that my aunt was the general manager of the hotel, I would eventually start working out a couple years in the future! So I texted her asking her if she wanted to hang out and she said yes. So, I told my mom I was going to hang out with a friend and I’d be back later. I picked her up at her house and then we went to hotel. My aunt let me use a room, so I could use the wifi there since the connection at home was shit. We went into the room, I locked the door, and like an inexperienced idiot. I didn’t know what to do. We sat on the bed awkwardly and talked, and then I’d tease her and she’d shoot back and then it turned to tickling till we were laying on the bed and we started kissing. Slowly at first, my lips gently pressing against hers. My heart racing, and my mind racing at a hundred miles an hour at what would happen. As we kissed more and more, it became more passionate. Our breathing got heavier, her hand reached up and gripped the sleeve of my shirt as if she wanted me to go further. I followed this up with sliding my tongue inside her mouth, french kissing her, her hot breath hit my lips. Her hips squirmed and she grabbed my hand and pulled it between her legs. So now I was kissing her and rubbing her pussy over her pants. I unbutton her pants with my hand slowly, and then unzipped them slowly. Sliding my hand under her pants and between her legs. She wore white lace panties and she was already wet. I played with her pussy a little, stroking my hand up and down soaking her panties more and more. Then I’d occasionally play with her clit and she’d let out a little moan everytime.
This foreplay continued on a for a few more minutes till I got off the bed and started to undress. Taking off my shirt and tossing it on the floor. She sat up and smiled and giggled. She took off her shirt as well, tossed it on the floor. She stood up and took off her pants and kicked them on the floor. She stood in front of me wearing a matching white lace bra and panties.
DeeDee stood about 5’4″, she had a little chunk on her, but that didn’t bother me at all. She had DD cup tits and a cute tight little ass. She had long brown hair and she teased it like all the girls were doing back in the late 2000s.
I fully undressed and stood there in front of her. I stand at 5’11”, at the time I was still skinny as I was in high school, had very little hair on my body. She looked up and down and bit her lip. I walked over closer to her and she started to look down at my cock. She looked back up and me as she reached her hand out and grabbed it. She let out small giggle as her eyes looked up at me and widened. Stroking my cock up and down, letting the precum ooze on her hand. I looked down at her and leaned forward and kissed her slowly, but passionately. She started stroking my cock faster as we kissed. My hands reached behind her back and unclasped her bra slowly. I slowly slide each strap off her shoulders and then let her bra fall to the floor. Next, I gently pushed her back till she was sitting on the bed. She laid back and lifted her butt up a little as I slid down her panties and laid them next to her head. Before I got ahead of myself, I reached down and grabbed my pants and searched my pockets for the condom I’d brought with me. I put it on and it was apparent I had no real idea how, but I got it on. I walked back over to her and spread her legs slowly. I press the tip of my cock against her and started to gently push inside her. She let out soft moans and she grabbed my wrist tight.
“Are you okay?”, I stopped and asked her. She nodded and said in a soft voice, “*I… I’m ready…”*
So I continued to push inside her and I let out soft groans as each inch of myself was gripped by her, she was tight and wet. Finally, I went in as far I could and I pulled back out slowly. She was letting out soft moans as she bit her lip. I told her I was going to go a little faster and she looked back up and me and nodded. I started to thrust inside her faster and this started her to moan louder.
I leaned down and thrusted in and out of her. Kissing her as her arms reached around my neck and pulled me in for passionate kiss. This caused me to push inside her deep, her legs kicked up and pulled me in. She let out a loud moan and so did I. Finally, I decided there to say fuck it and I started pumping into her harder and faster. She kept her arms locked around behind my neck and her legs wrapped around my waist. My balls slapped against as I fucked her hard and fast. She moaned louder and louder. Until, I could feel her pussy grip my cock even tighter and she let out a loud squeal. As she gripped tighter and tighter, I came closer to cumming myself. Within seconds of her, squealing I came. I collapsed on top of her out of breath as my balls emptied into the condom.
Finally, I stood up and took the condom off. I tied it up and tossed it in the trash can in the room. Smiled and laid next to her. We cuddle for about half an hour, laid there and just chatted. Then we got dressed, I took her home and then that started my first real friends with benefit relationship. Also, that was the first time I fucked in that motel and it certainly wouldn’t be that last. ;)
Thank you for reading! I hope you enjoyed! I’ll try and post more when I get a chance and if I think of more stories I’ll be sure to post right away! Have a good week, take care of yourself, wear your mask, and don’t forget to wear condoms!
Source: reddit.com/r/gonewildstories/comments/mapdw6/how_i_m_lost_my_virginity_to_my_friend
A good story. Still in touch with her?