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 3: The Theater Parking Lot

Coming of Age Sex Story: Chapter 3: The Theater Parking Lot - 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  

Once the movie was over we went back to his car. The crowds must have been seeing another movie and left as the area where his car was parked was now empty except for his car. As we walked to the car I started planning a few ways to spice the night up a bit so when we got in the car I turned in my seat to him.

“Thank you Randy for the movie and stuff. I really appreciated it.”

“You’re welcome Kelly, I’ve never been on a real date before and I was so afraid of doing something wrong.”

“Well Randy, you were a perfect gentleman. Here, let me thank you in a more personal way.”

Before he truly realized what was happened, I scooted over in the seat until I was up next to him. I put my arms around his neck and kissed him. Just a short kiss with my mouth closed but I could feel him tense up as I did. I’d never had to be the aggressor before on a date. Indeed, in most cases I was the one fighting off the attack although admittedly it’s not like I actually resist all that much! Tonight, though, I knew if anything was going to happen it would be up to me to get things started. I pulled back just a bit from him and looked him in the eyes.

“So Randy, have you ever been kissed by a girl before?” I asked sweetly.

“NNNNNooo Kelly,” he stammered, his face turning so beet red I cold se it in the dim light of the parking lot lights.

Just the answer I was hoping for! I’d never been with a boy on his first date before and it excited me to think I’d just given him his first kiss! Licking my lips just a bit I Leandras over and kissed him again. This time he wasn’t so shocked and after a short while he was obviously getting into it more. After we had gone on this way for a while I opened my lips slightly, just enough to let my tongue slip out and touch his lips. Randy’s eyes opened wide and he pulled back a bit. Not wanting to backtrack, I tried to make him feel at ease.

“It’s OK Randy, it’s called French kissing. Just relax and try it. I promise you’ll love it.”

Before he cols say anything I kissed him again and this time Randy followed my lead and our tongues met. He FINALLY put his arms around me and we kept kissing for the longest time. It seemed to be up to me to take the initiate so I took one of his hands and pulled it to my breast. He was stiff at first but as he felt my soft bosom his hands instinctively began to fondle me. He was a bit clumsy at first but that just made it all the hotter for me knowing that he’d never done anything like this before and that he was learning with me.

After a while I sat back in the seat and gave him a coy look. “So tell me Randy, have you ever seen a girl before? I mean REALLY seen her? I’m not talking about your father’s Playboy or anything like that. Haven’t you always wanted to see what a girl really looks like?”

Randy’s face was flushed and he was biting his lip nervously as he looked at me. Since I’d made no effort to pull down my skirt after I had moved around it was riding up nice and high, just as I intended. With my legs up on the seat I knew he was getting a good view of my crotch, even though my panties were covering everything of interest.

Once again it was looking like Randy was too scared to make the next move so I did it for him. Reaching down I started to rub my crotch through my panties. My hand was moving very slowly and deliberately, not really meaning to turn me on but to turn him on instead.

“Mmmmmmm, do you like to see me doing this Randy?” I softly teased him.

“Damn Kelly, I can’t believe this is really happening. God you look so hot! I don’t even know what to say.”

“Don’t say anything Randy, just watch me. I love it when a boy watches me touch myself.”

Leaning back against the passenger door, I pulled my skirt up to my waist and then pulled my panties down until they were at my ankles. By spreading my legs wide apart I gave him a perfect view of my crotch. Back then I wasn’t shaving it completely but instead trimming it and keeping it cleaned it up enough so I could wear a sexy thong bikini. Randy was just staring at me, or I should really say my pussy, as I took my hands and spread my pussy lips apart to allow him to see me even better.

“Mmmmmmm, I love the way you’re looking at my pussy Randy. See here? This is my clit and it loves to be touched and teased.”

When I touched my clit I gasped as a deep shiver ran through me. While I love to masturbate, it especially thrills me when someone watches me do it.

“You know Randy, sometimes at home I like to watch myself in the mirror when I touch myself like this. Will you be my mirror tonight?”

OK, so I plagiarized the line from one of my dad’s porn movies but Randy didn’t know that. The look on his face was priceless. Running a finger up and down my pussy crack, I dipped it just enough inside to get my finger wet and then back up to my clit where I teased myself and caressed it. Randy watched my every move in total silence, not even hardly even blinking. Then I slipped off my panties from around my ankles and handed them to him. He took them so gingerly I was ready to bet that he’d never held a girl’s panties before, especially a pair that was still wet in the crotch from her excited pussy! I put my finger inside of me again and he stared like a deer caught in the headlights.

“What’s the matter Randy, don’t you know how girls masturbate? When I do this I imagine a guy being inside of me. Do you imagine being inside of a girl when you jerk off?”

He looked a bit shocked when I said that. I was sure no girl had ever talked to him like this and as much as I loved touching myself, I was getting off more watching his reactions.

“Don’t be embarrassed Randy, all guys jerk off. Well, in case you didn’t know, so do girls. But I like it even better when a guy touches me.”

As I spoke to him I kept stroking my finger in and out of me, dreaming it was Randy fucking me instead with that hard cock I could see outlined in his pants! I moaned as the pleasure I felt started to overtake me. Having Randy watching me with those wide eyes and open mouth only intensified the feelings. As I massaged my boob and masturbated, my breathing was getting more labored and my moans were louder and longer. God I was going to cum already! My orgasm started to rise in my like a volcano erupting. My pussy was on fire as I thrust my fingers into me as fast as I could with my palm rubbing over my clit at the same time. I gasped and looked at Randy as he stared at me with a look of wonder on his face.

“Oh my God Randy! Watch me cum! Ohhhhhhhhh, it feels so wonderful, I love this soooooo much!”

My hand pulled up hard against my crotch, driving my fingers deep in me and pressing my palm against my clit as my orgasm reached its climax until it finally started to subside. God that let so good! I lay there breathing hard, bringing my wet fingers to my mouth and sucking my cum juices off of them.

“Mmmmmmm, I love the way I taste Randy. Did you like watching me cum for you. I know I did! Now it’s your turn to touch me.”

Randy seemed confused, almost like he couldn’t believe what he was hearing. Keeping things moving, I turned around and got up on his lap with my back to his door. I could feel his jeans under my bare ass and there was a definite bulge in his crotch that pressed against my butt. He put one hand behind my back and the other on my knee. I put my arms around his neck and we kissed again. As we kissed I moved my arm down and took his hand off my knee and moved it to my bare thigh. His courage grew and I could feel his hand slowly moving on my leg, touching me up and down and eventually moving upwards toward my crotch. I pulled back from our kiss just for a moment.

“It’s OK Randy, you can touch me. I told you that it was your turn and that meant that I wanted you to do it. Don’t worry, just explore me and see how I feel. You can touch me ANYWHERE you want. You won’t hurt me if you just be careful and don’t force anything.”

Gingerly his fingers began to touch and explore my pussy. From his fumbling it was obvious he really didn’t have a clue where to touch me so I took his hand and guided him to the places I like to be fondled. Finally I moved him to my pussy hole and pushed his finger inside of me. God it felt good! I felt his finger wiggle around inside of me, touching me as he obviously was trying to figure out what was in me. Oh yeah ... even though his technique needed a lot of work, the innocence of his explorations really turned me on. I was so wet from my earlier orgasm that he easily slid in and out of me and he rubbed the opening of my pussy. I took his hand and pulled it up to his mouth.

“Taste your fingers Randy, see how I taste on you.”

Randy hesitated for a second and then put his finger in his mouth. A smile came to his face.

“See? I knew you would like it. So tell me randy Randy, what do you think about your first taste of a girl’s pussy?”

Randy hesitated and then said slowly, “Different Kelly. I don’t even know what to compare it to. All I know is I like it!”

“That’s good Randy, now I want you to undress me.”

Randy took a deep breath and tried to unbutton my blouse. He obviously was not use to doing this because it took him for what seemed to be forever until it was open, exposing my little 34A bra. It was just one step above a training bra but I knew that Randy had never seen one up close and personal before so he wouldn’t mind. I reached behind me and unhooked it for him, allowing him to lift it up and off my small boobs. Looking at him I saw his eyes fixated on my little boobs and erect nipples.

“They’re not big but they’re VERY sensitive so be nice to them. Touch them Randy, it’s OK ... really you can touch them.”

Even though he wasn’t a big guy I was still so small that Randy’s hand was able to cup and cover my entire breast. Nope, I wasn’t teasing about them being sensitive! When I’m alone I love just running my fingers along them, just brushing up against the nipple. More than once I’ve had to catch myself in public like in class or even church when I would absent-mindedly start to run my fingers along them, forgetting for a moment where I was and what I was doing. Fortunately I’d never been caught as it would have been quite embarrassing!

Randy squeezed me softly, learning for the first time how a girl’s breast felt as he touched mine. I wondered what he was thinking as he caressed my breast while I sat bottomless on his lap? I loved watching him touch me as he moved from one to the other, sending ripples of pleasure through me as would take his whole hand and just squeeze me softly.

“Now I want you to suck my nipples Randy. Put them in your mouth and softly suck on them. They love to have a LOT of attention paid to them.”

Randy eagerly licked his lips and lowered his head to my bosom, softly sucking on one boob and then the other. God it felt so good! I held his head against my chest, running my fingers through his hair.

“Oh yes Randy, that’s it! Suck on it. Put as much in your mouth as you can and suck hard. Run your tongue over the nipple while you do that. Oh Randy ... you make me feel so good when you do that.”

Actually I wasn’t just building his ego, I WAS feeling good! Squirming in his lap I could feel his hard cock through his jeans, desperate to escape so it could to be with the pussy just above it. After allowing him suck me for a while I felt torn between the pleasure he was giving me and the desire to get a closer look at that bulge I was feeling under my ass, which was now even larger than before. Finally my desire for his cock overtook me so I pushed his head gently away from me. Quickly I moved off his lap and got on my knees on the seat next to him where I unbuckled and then unzipped his jeans. As I tried to pull his jeans and underwear off he raised his hips to make it easier for me. What I saw then made my mouth water. Talk about a nice surprise ... Randy had a nice sized cock and it was as stiff as a steel rod. Smiling, I looked up at Randy.

“Mmmmmmm, I love the sight of a hard dick waiting for me. OK Randy, get ready. I’m going to touch you now.”

Eagerly I reached out and put my hand around his shaft. Oh my was he hard! My fingers wrapped around his stiff shaft and he felt so warm in my hand. He shuddered as I started to stroke it so very slowly to start. Yes, it felt so hot knowing I was the first girl to touch it. Gripping him with the bottom of my hand at the base of his cock, a couple of inches still extended beyond my hand so I guessed him to be about six inches long or so. I could feel his pubic hair against my hand, so curly and dark. The musky smell of his desire was heavy in my nose.

“You have a beautiful cock Randy, did you know that? See how it fits perfectly in my hand which also means it would fit perfectly in my mouth. Will you let me suck you Randy?”

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