Kelly's Diary 041 - My First Time With a Virgin - Cover

Kelly's Diary 041 - My First Time With a Virgin

Copyright© 2024 by Kelly85

Chapter 2: Movie Date With Randy

Coming of Age Sex Story: Chapter 2: Movie Date With Randy - I can't even begin to say how many times I've heard guys dream about sex with a virgin. Well, why wouldn't the same apply to a girl?

Caution: This Coming of Age Sex Story contains strong sexual content, including mt/ft   True Story   First   Oral Sex  

That Friday evening I got ready for my date with Randy. During my shower I shaved my legs and crotch. While I was never one for a lot of makeup, a little blush, a dab of eye shadow and a light coating of lipstick never hurt. Rummaging though my closet I picked out a cute blue plaid skirt and a white lace blouse. The blouse was semi-sheer and buttoned down the front while my skirt came less than halfway down my thighs. Together with my heels my legs would show off at their best.

Normally I’m not a big fan of underwear but there are times when it can be more sexy to wear it than not. This time knowing my audience I selected on a pair of standard white cotton panties and decided for fun to wear a bra. All-in-all a pretty conservative outfit for me but I had a feeling Randy would be scared off if I wore one of my more typical dating outfits, especially the cute little skirt and halter set my dad referred to as “Kelly’s high school slut outfit” (but actually it was his favorite!)

Standing straight in my bare feet, I checked myself out in a full-length mirror, imagining a pair of nervous hands running over me. Closing my eyes, I slowly traced the backs of my fingers down the sides of my neck and then down to my breasts. My hands cupped my breasts through the bra and I pressed them tightly to me, then squeezed them gently and pinched my nipples. A shiver ran down my legs as I dreamed of being gently caressed and fondled. My hands slowly ran down my flat stomach and I lifted up my skirt, allowing my hands to run up the inside my thighs, tickling me and making me tingle when they met in my crotch. With my hands pressed tightly against my pussy I could feel the warmth even through the cotton panties. As my fingers began to rub my pussy through my panties I dreamed of Randy exploring me, playing with me, touching me.

Just as I was at the point of moving my panties aside so I could do some serious fingering I heard a car in the driveway and knew it was Randy. Reluctantly I straightened out my skirt and blouse and went downstairs to meet him. My parents were out for dinner so there was no need to make him get out and go through the “meet the parents” routine so I just went out through the front door to greet him. As I approached him I saw that his car certainly left a bit to be desired as it looked to be older than I was and not in very good shape. The one good thing I noted was the front seat, an old-style bench seat instead of the typical bucket seats found in most cars today. We exchanged hellos and I took a seat on the passenger side as he drove to the theater. On the way we just talked about school and church, nothing memorable. Hoping to get started on the right foot, I didn’t bother pulling my skirt down when I got in so it was riding up pretty high, not quite exposing my ass but pretty close! I noticed he couldn’t help but look over at me at times, taking in a few eyefuls of my legs and I was hoping that he was thinking about what was under my skirt as well.

When we got to the movie theater it was very crowded so Randy had to find a parking space out behind the theater along with a number of other moviegoers. Randy was a perfect gentleman the whole time, opening the car door for me and paid for everything, including some drinks and snacks. I don’t think he had a lot of money and for him to spend this much must have been hard for him. Then again, I pretty much expected a guy to pick up the tab on a date. It wasn’t like I wasn’t going to do my part in return.

Finding seats towards the back of the theater, we relaxed and watched the movie. After half the movie went by without so much as a touch I put my hand on the armrest between us but he never even touched me the entire movie. Now I love dates in movie theaters and not because of the delicious popcorn so for me it was a bit strange to actually watch an entire movie! I’d given my first blowjob in a theater like this one and even been fucked more than once in similar ones so to just sit and watch was a new experience for me. Fortunately it was a good movie and the evening went along fine. Even so, I was more than a bit disappointed that he didn’t make one move towards me. I wondered if he knew what a unique date this was for me.

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