Hey everyone! Sorry for the delay, getting back into the swing of class while everything covid related is leaving schools in total uncertainty plus Emily really gearing into indoor season has really left me in a bit of a writers block mood, but I’ve persevered and today you have my story of my first time. If you’ve read my Q&As you know what answer I’ve given for when this event happened, but for the purposes of reddit terms of service, all persons in this story are 18 and it is written as such. I hope you guys enjoy, and plan on getting another Chapter in in the next few days now that I’m back in my writing mood again! As always, feel free to drop a message in our DMs or leave something in the comments! We try to respond to everyone! And if you have something specifically for me or Emily, just say so and we’ll be sure to get to you! ♡ Jen
So how did I lose my virginity? I was 18, in my senior year of highschool, about to go to college. I was still fairly petite, with an athletic build and C cup breasts. I was always tan from playing on the soccer team and I wore my dark brown hair to about the middle of my back. It was prom night. Stereotypical I know. Bare with me, I think my story is still fun.
So I had been dating Kevin, an exchange student from South Korea for a few months, since he had asked me to be his homecoming date back in the fall. He was maybe 5’6, slim with short black hair and a fairly nerdy but cute overall style. He was a huge fan of League of Legends and I actually thought he was super cute.
So Kevin picked me up at home in a dashing black tux, with a peach bowtie and vest that matched my dress, which was floor length, flowing with a toga style cross of fabric, crisscrossing my chest with an open back. I wore my hair down, slightly curled as it hung down my back.
We had your average night of dancing and hanging out with our friends, taking lots of pictures and overall having a good time. Kevin was an absolute gentleman, except he let his hands wander down my butt as we slow danced at the end of the night. I thought it was so scandalous and loved that we were getting away with something in front of the chaperones…let’s be real, no one was getting away with anything, just no one cared to comment.
Now this isn’t to say Kevin and I were a totally chaste couple, we had had our fair share of steamy makeouts and we had even touched eachother before…and scandalously enough I had given him maybe like three blowjobs out on dates we’d had the past few weeks…at his house, in my totally awesome soccer mom mini van, and even once behind the gym way late after school.. We had talked about going further, but we both wanted our first time to be special. We had talked about maybe going all the way at prom, and I said I’d try if Kevin figured out a plan.
So back to prom night, the dance was at this fancy hotel. As the night was winding down, we were thinking of heading out to my friend Kelly’s house for a house party her parents were letting her throw. But Kevin said he had other plans. He had booked us a room at the hotel the dance was at. So instead of heading out with our friends, he pulled out a room key and walked me upstairs. My parents were okay with me going to Kelly’s so “that’s where we went”, and quite frankly, Kevin’s host family kinda just let him run wild if he wanted, so no worries, just go have fun.
As Kevin opened our room, I was blown away. To 18 year old me, it was a stunning, top class room. Looking back, it was an average king bed room at a 3 star hotel, but to me it was perfect. As soon as we were inside, we pretty much immediately started making out beside the bed. As things heated up, Kevin slipped out of his tux and was in an undershirt and some cute blue plaid boxer briefs. I still hadn’t done anything with my dress when Kevin asked if he could undo the top of my dress between kisses on my neck.
I reached back and undid the clasp he was struggling with and let the drapes of flowing peach fabric that were holding my C cup breasts fall away, exposing my braless look for a wide eyed Kevin who had never seen me totally topless except in dirty snapchats I’d sent him before.
I pushed my dress below my hips and to the floor, revealing a purple lace thong I’d worn to prevent any pantielines under my dress…and I thought it’d be cute if we got this far tonight. As my dress fell away, leaving me in just a thong, I suddenly felt slightly embarrassed, being this exposed to a guy for the first time. Kevin pulled his shirt off “so we could match” and I laughed, the awkwardness breaking away as we started to kiss again and he eased me back onto the bed, positing his body between my legs as we continued to make out.
I reached into Kevin’s boxerbriefs and grasped him in my hand. He was a little small, maybe 5 inches but he was rock hard and it was a huge turn on to feel him that excited for me. He slipped his briefs off and reached into my thong as he continued to kiss me. His fingers awkwardly traced their way between my lips, sometimes brushing up against my clit and sending shivers down my spine as I nervously waited to see how this would go.
He sat back on his heels between my legs and he pulled off my thong and we were suddenly naked together for the first time. His dick looked so much bigger than the hair brush handle I would use alone in my room and he could tell I was nervous. He was nervous too, this was a big first for both of us. He slipped a finger slower inside me, my walls relaxing slightly as I got wetter in anticipation. He leaned down and kissed me passionately as he continued to work his finger in and out of me, and I rocked my hips in time with his movements.
This continued on until he pulled away again and asked if I wanted to go further. I nodded yes and asked him to take it super slow. I could feel the tip of his hard cock bumping around between my legs, trying to find my entrance. He slightly was embarrassed and asked if I could help him. I giggled and reached up to kiss him as I reached between our legs, grabbed his shaft and placed his head against my vagina. He gasped slightly as his head slipped in and I pressed against his hips to keep him from going in deeper.
I let out a slight squeal as he suddenly pushed inside me for the first time and I grabbed his hips, easing him all the way inside me as I stretched out to take him. It hurt slightly but nothing crazy. It was a dull ache between my legs as he slowly started to move in and out of me in an awkward rhythm.
He kissed me again and again as he picked up speed little by little. I moaned into his mouth in a mix of ache and pleasure as I stretched out all the way to take him, in one breath feeling the ache between my legs and in the next, the mix of pure pleasure that lead me to know I would enjoy the feeling of being with someone once my body relaxed. After maybe 2 or 3 minutes he said he was close and honestly, I was too. I pulled him out of me and he quickly jerked himself off, splattering my pubic bone and stomach with ropes of cum as my fingers found their way to my clit, furiously rubbing my way over the last hurdle and achieving an aching climax as my freshly stretched walls clenched in orgasm as I lay there covered in Kevin’s release. We kissed a little more before moving to the shower to clean up…my first time taking a shower with a guy. We didn’t do anything else sexual that night but spent an intimate night together, all because Kevin made the effort to go all out for me before he went back home to South Korea after graduation. My parents never found out and I was happily a virgin no more!
Thank you all for reading! I hope this was an enjoyable one for you, even if it was a little quick (first times usually are). As always, I’d love to get your feedback in the comments or DMs! ♡Jen
Source: reddit.com/r/eroticliterature/comments/s4461k/jens_university_chronicles_part_17flashback_to_my
Love reading these , hope you are well