Teaching Heather

by De Von

Copyright© 2011 by De Von

True Sex Story: A teen finally realizes her secret crush fantasies, as she gives up her virginity to her friend's older brother

Caution: This True Sex Story contains strong sexual content, including mt/ft   Romantic   Heterosexual   True Story   First   .

Here's one from the past ... twenty years goes by so fast!

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I first met Heather when she was 12. We were in Leo club together. She was just a skinny little short kid then, nothing like the beautiful young lady she would later become. We were friends but nothing more. I was 15 then, and Leo club got boring after I got my license, and I left it and Heather behind.

Fast forward three years, and my little sister, who's now 12, keeps talking about her friend Heather, who's in the grade ahead of her, but a couple of years older. I didn't think anything of it, probably just another kid. Then one afternoon I came home to Mom telling me, "Sis's friend Heather is spending the night."

"Great", I thought, "another kid to put up with." Then in walked this HOT girl! As I was thinking she looked familiar, she grinned that devilish smile of hers and ran over to give me a big hug. Only then did I connect her with the short little kid from Leo's. Heather had obviously grown up quite a lot in the last couple of years. She was a good foot taller now, and all of it seemed to have came from her legs, which made a perfect ass of themselves! Her breasts were nicely sized, just enough to accent her frame.

Over the next few months Heather and my sister spent more and more time together, and I began to notice her smiling and watching me more and more as well. I began to realize she had a crush on me. At first I thought it was cute, but then began to see her less as a little kid and more as a possible girlfriend. She was 3 years younger than me, but at our ages it didn't seem to matter much. I began to hang out more with the girls, taking them to the movies, the mall, and other places they might want to go. My little sister thought it was great, as she got to run and go, and Mom trusted me to watch after her and Heather.

One fateful night in August, Heather was spending the night again. She and I and my sister ended up watching movies in our living room until late into the night. I dozed on the floor for a while, and woke to find Heather lying next to me, watching the current movie. "Top Gun" again, I think it was. They LOVED Tom Cruise back then.

My sister was asleep on the couch, and Heather and I were quietly talking and flirting with each other. As we heard soft snoring from the couch, I leaned forward and gently kissed her. Heather's soft lips met my kiss, and returned it, ever so softly. We lay there and kissed for quite some time, simply making out and not really doing more. Eventually I allowed one hand to slowly begin to migrate from her waist, where it had been resting, to slowly caress her side, moving closer to her breast. I could feel her breathing speed up as I did so.

I kept kissing her as I gently cupped her breast in my hand, feeling her gasp as I did so. Her responses were eager, yet reserved. I sensed it was more that she didn't really know what to do, rather than any reluctance. I slowly explored her body with one hand, but carefully avoided directly contacting her center. At one point, as my hand softly caressed from her knee up the outside of her thigh, I paused and broke our kiss, pulling back a bit. As she looked at me with a somewhat puzzled look, I quietly asked her, "Are you sure you want to go ahead with this?"

"Yes!", she responded immediately. "Let's move, then" I told her. She nodded as I slipped one hand under her knees, and the other behind her shoulders and then picked her up. She wrapped her arms around my neck and laid her head against my chest. Still holding Heather in my arms, I stood and quietly walked to the front door, managing to open it with the hand under her legs, and slip out into the warm summer air. Heather pulled the door closed behind us, ever so slowly to keep from waking up my sister.

I walked to the side of the porch, out from in front of the door, and slowly knelt, and then lowered Heather to the smooth boards of the porch deck. She had a look of love and admiration on her face as I leaned in and kissed her again, resuming my exploration of her body with my hands.

Heather was wearing a short, pink, one-piece jumper and now I reached for the knot where it was tied behind her neck. She leaned forward a bit, giving me room to untie it. As I pulled the two pieces of string apart, I tugged gently on them, pulling the top of her jumper down to her waist, exposing her delicious young breasts to the night air. I kissed her again as I caressed her breasts with my right hand, enjoying my exploration of her body. After a bit I broke the kiss again and sat up some, tugging on the sides of her jumper. She lifted her bottom off the deck and allowed me to pull the jumper down her legs and off. I laid it carefully to one side and then turned my attention back to Heather's luscious body.

As I resumed my caresses, I slowly worked toward her soft, secret center, passing over her downy hair and finding her slit already moist. As my fingers caressed her outer lips, I continued to kiss her, slowly exploring her mouth with my tongue at the same time as my fingers explored her ever wettening pussy. I had removed my shirt earlier, and now felt her fingers on my pants, tugging at the button of my jeans. Using both hands, she got the button free and pulled the zipper down. I felt her small, warm hand slip inside the waistband of my briefs and then her fingers wrapped around my hard cock. We continued like that for a few minutes, until she tugged softly on my jeans. I paused my attention to her body long enough to remove my jeans and briefs, then lay next to her, both of us now naked. She reached and gently wrapped her fingers on my cock again.

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