Dating my platoon leader Part 8…flashback to my first time [MF]

Hey guys, this one took a little time but I’m happy with the end result. Basically Matt has been following along with my story on here and loves it so far…and he asked if I’d write a chapter about how I lost my virginity. I’ve agreed to indulge him on this one, I hope you don’t mind the slight deviation from our regularly scheduled Avery+Matt sexcapades. More of those will return in part 9.

As always, feel free to message me with feedback and critiques! Disclaimer, everyone is 18+ in this chapter. ♡Avery

So how did I lose my virginity? I was 18, in my senior year of highschool, about to go out and join the Army. I was still petite, with an athletic build and B 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.

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 three blowjobs out on dates we’d had the past few weeks. 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 letting me spread my wings before leaving for the army, and quite frankly, Kevin’s host family kinda just let him run wild if he wanted.

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 started making out on 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 b 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. I moaned into his mouth in a mix of ache and pleasure as I stretched out all the way to take him. After maybe 2 or 3 minutes he said he was close. I pulled him out of me and he quickly jerked himself off, splattering my pubic bone and stomach with ropes of cum. I thought it was kinda hot…a little like some of the porn I watched alone in my room some nights. 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.

I hope you all enjoyed this story! We’ll be back to more of Matt and I in part 9 I promise (:
Thank you all for your feedback! I look forward to any critiques you want to message me with! ♡Avery

Source: reddit.com/r/gonewildstories/comments/i7z5wz/dating_my_platoon_leader_part_8flashback_to_my