Fun Under Plaid

Caitlyn had been seeing me for about 2 weeks when that fateful night happened. I was 19 years old, and new in town. She was a local prep school girl at Episcopal High, young, but mature in form. That night was the first night we had spent in privacy at her place watching a movie while her mom was out of town. She called me up that afternoon and told me she'd be late from school, but to just come over at 7 pm.

When I showed up she had just arrived and was still in her cute little uniform, with white blouse and plaid skirt which was a bit too short past regulations. We quickly settled down on the couch to watch a movie we had both already seen when she shifted towards me in a manner that put my forearm in contact with her chest. You see, before this we had only engaged in kissing and I hadn't been so forward with this young girl as to try anything with her beyond that. I let my arm stay in that position when suddenly she looked at me with apprehension and I froze, not wanting to scare her off. But she said, "Why don't you take off those jeans and be more comfortable, since we're squeezed on this couch?" Of course I lazily got up and went to the bathroom to remove the jeans.

My hands were shaking from the excitement and I was worried that she would take note of my obvious arousal. When I got back she was leaning on her back with a slight grin on her face. Could this be the prim girl I had been seeing for 2 weeks?

"Caitlyn, move over so I can fit on the couch," I said and she reluctantly acquiesced, turning her face towards the cushion, with her skirt riding up even more to expose her upper thighs. I lay down next to her, spooning her and let my hands drift up where I wouldn't have normally dared, only I was so excited. She took my left hand and placed it on her breast as I shuddered, since I felt that she was wearing no bra. I leaned over and saw it lying on the floor and mentioned it to her. She replied that she was "uncomfortable" in it and decided to undo a few buttons of her shirt as well. I tried very hard to maintain my composure as my crotch began to tighten against her nice bottom.

"Um Brit, what is it that you're doing?" I asked.

"Nothing, just getting comfortable," she replied and shifted again so that my hand was partially inside her shirt. I began rubbing her chest, working my hand down to her soft bosom, wondering if this was right, when I felt her hand working it's way down my stomach. I involuntarily squeezed her breast as her hand hit my crotch and she responded by squeezing my dick in kind.

I groaned. "Caitlyn, what are you doing?"

"Making you more comfortable, my little boy." With this she turned over, pressing her chest into me and proceeded to unzip my pants and pull them down to my knees. "I can't expose myself to you, your mom would kill me!"

"She's not here, and anyway, I'll hide you under my skirt." With this she took my penis and pushed it under her skirt, and draped her plaid pleated skirt over my lower body. Oh, was I in heaven. She was mewing and kissing me softly and running her fingers through my hair. Movie forgotten we started moving rhythmically and I slid my hands under her skirt. She lifted a bit to give me access and I had a momentary doubt. This she soon allayed as she put my hand to her panties in the middle and I felt how wet she was. My my I said to myself as I slipped my thumbs through the sides of her bikini briefs. "What a good girl you are!" and I pulled her panties down to her ankles while she lowered her warm wetness onto me.

"Mmmmmm...." She began kissing me all the more as our flesh was in contact under the blue pleats of her uniform. My hands were drifting across her bottom and my dick was pushed against her warm cunt. I pulled her shirt back so that her breasts could press upon me as she ground me into the sofa. By this point I was so turned on that I couldn't move except to kiss her and meet her hips. She slid back a bit to come up against me again and though we had said we wouldn't have sex, the position offered penetration that I couldn't refuse. So she came forward and my dick sprang up into her and she gasped.

She bit my lip so hard I thought I was bleeding, but I was in so much pleasure I couldn't feel the pain. With that she pushed down onto me all the way thrusting me into her. I was pinned to the couch with her skirt all the way up between us and her shirt hanging loosely around her shoulders when she started to cry out. I was worried that she was upset about what was happening but she started thrusting harder and faster. This was the best situation I had ever been in and I couldn't hold it any longer. She started to say something when I interrupted, "Oh Brit, I'm cuminnnnggg... please let me cum!"

"Nggggghhhhhh" and she drove herself down on me. Well that was it. I shot hard and gripped her so tightly I left marks. She bit my shoulder and squeezed her legs against me and came hard with me. After we lay there, her hands playing around me, lazily stroking me while I kissed her and removed the rest of her soiled uniform. Things went quite well after that night.