An Ode To My First Grade Teacher

My first memories were blue

My first memories were blue (Flickr: Sumlin)

I’ll be so kind to admit it right now. I’m in my late thirties and, using my sharp math skills, have spent the better part of thirty years as a crossdresser. Even as a lot of time has passed since my first days across the border, I’ve always found myself trying to recall those first moments that would bend my gender the rest of the way.

No, I didn’t raid my mother’s drawer of bras and pantyhose. No, no one decided they would have some cruel fun, dress me all girly and proceed to laugh at me.

It actually can be traced back to first grade in grammar school and my beloved teacher, Mrs Rainwater. I can vaguely remember what she looked like. Things like her youthful face and short curly hair.

I remember one detail about her rather vividly and something that bonded me to her back then. She always wore blue knee-high socks on some days and on other days, blue pantyhose.

Now back then, I remember having socks that were somewhat girly (thanks mom) but out of those pairs was, you guessed it, a pair of blue knee-highs. Due to my infancy, I didn’t make an erotic connection with our common garments of choice, even on those days where we wore our knee-highs on the same day.

That is until the unthinkable happened. Ok, it was innocent but she lined up all the student in her class and proceeded to give each child a big kiss on the cheek, including me. Try that today and they are sure to slap handcuffs on you. I’ll chalk it up, though, to the post-hippie love present since it was the early 80’s.

The erotic line was now crossed and wearing blue knee-highs became the precursor to being like my teacher. The sexy young woman with blue legs.  I can remember rubbing myself on the bed (you know, infant masturbation) with a no-cum climax. The first of many to come.

I can characterize this first experience as the early days of my new-found fetish. I still had not yet liked pantyhose (we’ll get to when at a later date) but the girly socks had it’s effect. I didn’t feel like a girl but the knee-highs with a rub in the crotch was very satisfying.

Mrs Rainwater is probably retired by now. I’d just like to see her one last time, give her a real kiss and let here see how some modern, sexy blue pantyhose look on her former student crush.

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7 comments on “An Ode To My First Grade Teacher
  1. PaulaPlaytex says:

    I Later Found Out That My Cute History Was A Crossdresser Like Me…When The School Year Ended, We Spent A Lot Of “Girl Time Together” !!!

  2. my sister got me started by looking at me and my friend experiment to find out how to hump a girl and we would have our pants off and we would get it in between our ass cheeks and pump up and down to find out how it feels. her and her friends were able to see what was going on.

  3. I saw my sister in her room with her in nylons and underwear and I love to see what it feels like to have that on and I just wanted to do that again because it was so good for me.

  4. Sheestar99 says:

    My former sister-in-law really cemented my hosiery fetish and started my experiments with crossdressing. She worked at a Parklane Hosiery outlet and wore pantyhose all the time. I was already obsessed with a middle school teacher’s hosed legs so this was just hosiery heaven. When she came over, I would drop paper on the floor and casually touch her hosed feet while picking it up. She caught me looking at her pantyhose legs all the time.

    One Thanksgiving she showed up way overdressed; little black dress, strappy heels and sheer black pantyhose with a back seam and bow on the heel. Slightly embarrassed, she went into my bedroom and changed into more casual clothes. As soon as I could, I made a beeline for those pantyhose and locked myself in the bathroom. I was overcome with hormones and lust as I slipped them on and came almost instantly. I was carful not to run them and my heart raced smelling her perfume on the silky material. I put them back where I found them and tried to act like nothing happened.

    Later that year, I spent the summer at her house. When my brother and sister-in-law were working, I went through her lingerie drawers marveling at her slips, bustiers, garter belts, stockings and pantyhose. I would try them on and hump the bed in ecstasy. Well, one morning she confronted me about the cum stains on her pantyhose. I was a stuttering mess but I did own up to it and said I loved the way they feel. She said it was perfectly fine to experiment – she was a free spirited hippie lady – and after some questioning, gave me a couple pairs of sheer to waist pantyhose, a bra and that little black dress to enjoy as long as it remained our secret. She said the sheer to waist pantyhose would feel better against my cock. That summer, my hosiery fetish and crossdressing desires got hard wired into my brain. The sensations were out of this world.

  5. Sheery says:

    @Sheerstar99 I can’t count how many lingerie drawers I raided too, memories we have!

  6. Sheerstar99 says:

    We definitely share the same passions. That summer was so heavenly. She knew I was exploring her silky stockings and pantyhose, trying on the bustiers and bras, slipping into her skirts and blouses. She even put aside some makeup and let me watch her apply hers before going to work. I loved walking around the house fully dressed and made up with a little bit of perfume on my pulse points. Crossing and uncrossing my legs, feeling the wonderful sensations of hosiery and silk. She dressed so feminine and stylish and her hosed legs were almost always on display. I wanted to feel as femme and attractive as she looked to me.

    It took a while after leaving home before I met and moved in with a girlfriend who had a lingerie drawer that would compare to my sister in law’s. My girlfriend had a lot of stockings and pantyhose. She was into pantyhose sex but only grudgingly accepted my dressing. I loved dressing in her Donna Karan pantyhose with a bustier and leather miniskirt topped with a silky blouse and pearl choker. When she was visiting her mother out of town, I’d dress up and chat with other CDs and likeminded souls on AOL and Yahoo (yes, that long ago!). Heavenly.

  7. Sheery says:

    @Sheerstar99 We definitely do share the same passions and I used AOL too all glammed up!

    I think the first thing you have to do when at the friend or relative’s house (with a female living in it) is raid their closet when you get the chance. Fun times!

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