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High School Tease

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This is a true story recounting experiences from my high school days.


During my last two years of high school I had a girlfriend who enjoyed teasing me sexually. When we made out in my car or in the TV room in the basement of her parents' house, she would come up with clever ways of touching and stroking that kept me on the edge of orgasm for extended periods. I remember clearly the first time she touched me, when I was seventeen and she was sixteen. We had been kissing passionately for a long time and I had been excitedly massaging her breasts, when she gradually began to insert her hand down the front of my pants. She was very tentative, as if she feared that I might be shocked by what she was doing. She had a reputation as being a nice girl (this was the late 50s).

Needless to say I didn't stop her and when she finally made contact with my erect cock she moaned and melted into my arms, working her tongue eagerly into my mouth. Quickly getting my belt and zipper undone (I helped, I admit), she proceeded to caress and explore me with both hands, experimentally touching and stroking, delighted by my helpless reactions. All the while she continued to kiss me gently, running the tip of her tongue over my lips. I was delirious with pleasure!

A couple of weeks after that we parked in a local lovers' lane, where we soon started kissing and caressing each other. She had worked my pants down over my hips and was starting to go to work on my erection. Instead of the straightforward stroking she had employed on the two or three dates we'd had since the first time she touched me, she proceeded to brush her fingertips very lightly all over my genitals. She barely touched the surface and tantalized me into a frenzy. I was whimpering with a mixture of pleasure and frustration, but I managed to whisper, 'You're teasing me so much!'

She answered, 'But don't you like to be teased?', never stopping the maddening feathering with her fingertips. At this point I completely surrendered, realizing that I did indeed like to be teased; in fact I had instantly come to desperately crave it!

After this, she became devilish in the delight she took in subjecting me to sexual frustration. She enjoyed leading me on, as on one occasion when she made me believe that she was going to treat me to a complete hand job. She started by stroking with her fingertips to get my cock hard and then took it in her curled fingers and started the slow up and down motion that was sure to get me off. She held my cock captive and taut with her left hand, while the right lightly stroked up and down, slowly and gently. Occasionally when her hand reached the head on the up-stroke she paused and gave it a squeeze with a little twist and then proceeded stroking again. She repeated this about ten times and then on a down-stroke paused, squeezed and abruptly let go. Leaving my devastated member twitching and abandoned. This was repeated several times that night, and each time I was coaxed into believing that I was finally going to get relief and each time my hopes were dashed.

As time went on she developed other teasing tricks. She had very quickly learned about the little sweet spot on a man's penis. The underside just below the head that is so sexually sensitive. One night after getting my genitals completely exposed, she began a little manipulative action with two or three fingertips, brushing and flicking as if she were sprinkling salt. She started under my scrotum and proceeded slowly up the ridge of the shaft, causing me to hold my breath in anticipation. Then, just before reaching that wonderful little pleasure point, her fingers stopped and reversed direction back down the ridge. She repeated this several times, causing me to moan in frustration. Then, finally, she didn't stop and instead her fingers parted as they reached the sweet spot, thumb on one side and index finger on the other, missing it completely! To make sure I knew that she was tormenting me on purpose she made rapid little circles around where I needed to be touched most, around but not touching. She giggled and sighed contentedly to see the effect all this was having on me. Finally she gave me what I craved, placing her entire palm just below the head and moving it in slow, luxurious circles, massaging me to ecstasy.

Perhaps the oddest thing about all of this is that never did she bring me to orgasm, nor did we ever have intercourse. Perhaps our up-bringing had made us too shy, perhaps it was the repressive guilt of the times (I've never understood why people are nostalgic for the fifties). At the end of our make-out sessions I invariably went home unrelieved, although needless to say I took care of matters myself soon after arriving back! Now, many years later, I think of her often and sometimes wonder if she is responsible for what is still a hopeless addiction to tease. I rather doubt it; she probably just struck a responsive chord in my psyche. In any event, I've never regretted the excitement, pleasure and even the frustration I received at her hands.



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