Not surprisingly, my reputation for being a lesser male preceded me among the girls in my grade.  I’m not sure who told them, but I sometimes saw the girls point at me and giggle behind their hands.  One time at lunch, Lana Roxbury even made the hand sign of her thumb and index finger barely an inch apart before laughing out loud.  That really irked me because I had a huge crush on Lana and never forgot the time on the playground in front of school when I wasn’t watching where I was walking and my face ran smack dab into her rather nice, full bosom.  I quickly apologized, but I don’t think she bought it when she saw me smiling in elation.  As I mentioned earlier,   I was one of the shorter males in our class so most girls towered over me and I began to think of all women as unattainable Amazons.

Luckily we had school dances and even short guys like me could dance close to the girls and pretend like they were with us.  I really worked on my moves and some girls did actually seem to enjoy my more nimble steps than some of the real popular guys.  I even got some slow dances and I was in Heaven with my head resting below a girl’s chin and on top of her protruding feminine charms.  I would press my leg against a girl’s and hope that she would feel the hardness of my prick as well.  However, at the end of the dances I would go home alone.

Freshman year, most guys were catching up to the giantesses that were our age.  The high school had other junior highs feeding into it so our class size trebled in size.  In gym class I was back in familiar place as I noticed that I was still the smallest boy in the shower.  There were 2 other white kids who approached my sexual stature, but they felt emboldened as they discovered someone even tinier than them.  I continued to get more than my share of towel snaps and other harmless fun from the “Jocks” that ruled our football minded school. 

Once Kenny Schenker grabbed my original jock strap from me (the one I purchased for 7th grade).  As his friend Gary Willis held my arms behind me, Kenny attempted to walk a mile in my shoes so to speak.  He finally got the belt to his waist.  His cock and balls were stuffed to the seams in the mesh of the strap.  At certain points, skin from his junk poked out of the insufficient material and he lifted his arms above his head and did a ballerina like tiptoe maneuver and cried out “Look at me!  I’m Ronnie Dempsey.  I have to wear such tiny little jockstraps.  They feel like panties!  I’m Ronnie Dempsey, I wear panties!”

John Huff pulled his jockstrap up on my legs and soon I found my sexual organs enveloped in what seemed to be a yard of material.  The front part hung down despondently due to the lack of familiar male organ volume.

The rest of the guys laughed uproariously as my face turned five shades of red.  Kenny then pulled the strap off and placed it over my head.  Somebody grabbed the elastic band and stretched it out.  They released it and the back of my head felt like someone had hit it with an industrial sized rubber band.  Some guys were laughing so hard that they were tearing up.  I snatched the jock off and ran to my locker and hurriedly changed to leave.  The next day, when I put the jock strap on, it felt uncommonly loose and I don’t think I was getting any hernia protection from it anymore.

When I got to my sophomore year and finally got my license, my dating opportunities did expand a bit.  The first girl I got really intimate with was a sweet transfer student by the name of Vicky Smart.  She was a cute little dishwater blond who was surprisingly more mature than me although she was a freshman.  We went to dances, a couple of movies and “made out” in front of her house a few times.  She was so sweet to me and she even taught me how to French kiss.

We went to a baseball field one night after a date at the pizza shop and started to get hot and heavy in my Dad’s Ford Fairmont.  I finally got to touch her breasts (they were not Lana Roxbury’s size, but they were plump enough to squeeze).  I was so happy to finally feel the hidden flesh of a girl.  She then guided my hand down to her jeans and she helped me work the button loose and pull down the zipper.  My fingers started to stroke her mound on top of her panties.  Her little bow at the top was something new to me.  She guided my fingers under the panty and I felt her pubic hair and a slippery wetness that I had never experienced.  I traced the fold of her labia and her eyes closed and a soft moan escaped her lips.

I felt her hand also creeping down my Levi’s and she expertly unzipped me in a deft flip of the wrist.  Her hand snaked through and I felt her fingers pry open my jockey short’s flap.  We kept kissing and my finger was nearly knuckle-deep into her womanhood and tickling her inside.  Her digits started to search for my penis.  She found my balls and worked her way up, up, and up.  I felt her mouth slacken a bit and my eyes opened and I saw a look of consternation in hers.  She finally found the bottom of my shaft and traced the fullness of my hard on.   The kiss was broken and she firmly grasped my head and fished me out of my underwear and jeans.

Since we were sitting instead of reclining and my pants were still on, the full magnificence of my erection could not be appreciated.  In the fading light of the dusk Vicky squinted at the pink strawberry between her finger and thumb and the ½ inch of shaft that was outside from the material of my clothes.  She tugged on it slowly but with increasing pressure as if she could stretch me out to a more agreeable size.  Feeling foreign fingertips on my manhood was amazing and suddenly droplets of white liquid dribbled down on Vicky’s phalanges.  Weirdly, my finger in her love cleft no longer felt as wet as it had a couple of minutes ago and I swear that her nether lips seemed to relax and shrink away.

Vicky cupped my junk in the palm of her hand and she looked up at me incredulously and said “I’ve never been able to play peek-a-boo with a boy’s cock before.  You are SO SMALL!”

Before her words could really register, a bright light came in through the driver side window and a deep voice rumbled “What are you two doing at the Kiwana’s ball field?  Please row down your window the rest of the way.”

My throat went to my mouth and I extricated my hand from Vicky’s panties with all alacrity.  I (and Vicky) felt my hard on shrivel back into the folds of my jeans and out of sight.  “N-n-nothing officer.  We were just getting ready to leave,” my teenage voice cracked irritably!

The officer gave a half smile and said “Nothing is probably right, huh boy?!”  Vicky snorted and laughed while buttoning up her disheveled blouse.  He asked for my ID and went back to his car.  Then after some agonizing minutes he came back.

“Take this nice young lady home and drive safe Mr. Dempsey.  I don’t want to catch either of you here again.”

We thanked him profusely for not calling our parents or running us in and I drove slowly back to Vicky’s house.  Instead of the normal lingering French kiss I expected, I just got a brief peck on the lips and a quick “Goodnight.”  For the next week, whenever I phoned Vicky she said she was busy.  At school she avoided me and I wondered what had happened.  The cop “busting” us was embarrassing, but I didn’t see why that would still be bothering her.

Finally I cornered her between classes after she had just left the girls room.  I asked “Vicky, why aren’t you talking to me?  Did I do something wrong?”

At first she looked annoyed and then a little sad and said “Really?!  You don’t know?!  Oh Ronnie, you didn’t do much wrong.  As a matter of fact you didn’t do much at all.  I just don’t think I can deal with a boy with your special…features.  I’m growing into a mature woman and you’re…you’re not growing!”

That was the end of my first high school romance.  Vicky started dating Eugene hot and heavy a few weeks later.  He was my friend so when she was with him, she was nice to me, but I could tell that she really didn’t want to spend too much time around me.  He knew that I had dated Vicky before him and he joked “It’s too bad her sister is only in sixth grade, we could go on double dates!”  Vicky said “Oh, I don’t think that would work…for her!” and laughed.  Eugene agreed saying “My brother Alex is more her size…err… age!”