Sheery in her favorite Victorias Secret teddy

My first love has always been pantyhose since I was a kid. Yet as I grew up through my weird pubescent years I grew a fondness for lingerie way back when there were paper catalogs that had lingerie sections which I collected, my comic books of sorts I guess. I would fantasize and obsess while gawking through those pages, not at the typical ladies in bras and panties, but the more sultry garments. You know, anything with garters or all lace or “push-up” but what really caught my eye were the teddies. I fell in love with how they were basically a bathing suit but far sexier.

Then there was that time when I was still in high school, I had just got my drivers license and started working in a shitty fast food job earning minimum wage but my own fun money basically. So what did I do with that first paycheck? I drove right down to the mall, gave into my urge to try lingerie that wasn’t stolen, and bought a sexy camisole set. Wearing it later that night, with pantyhose of course, was at the time probably the most erotic and sensual experience I ever had.

Of course, being able to shop and afford things myself, my lingerie purchases didn’t stop there. With my fascination with teddies, I remember ordering a hot pink lace teddy with underwiring and a very high leg cut from a Sears catalog. Then I excitedly picked it up a few days later, rushed home and slipped it on, again, over my pantyhose. It was another sexy, sensual moment in the books but this teddy was something that truly felt amazing having on. I wouldn’t say it was a very feminine feeling but more like a sexual excitement and of course shortly after came the gratification (pun intended).

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Sheery posing in Wolford pantyhose

As I sit here right in my living room, I have just slipped on a pair of black Wolford Neon 40’s and then had thought that really made me stop and wonder. This beautifully sexy, silky garment is pretty much the basis for my entire life. Obviously it is something you know (I know you too!) but it is quite surprising to think of how it made me who I am.

I can remember vividly how it all started at five years old by falling in love with Mrs Rainwater and her navy blue pantyhose that she would wear with sandals. I think the real life shaping event, however, happened when my sister actually had a pair of navy blue knee highs at the time, which I stole from her that first time then eagerly wore them dreaming of “being” Mrs Rainwater. Little did I know the seed that this planted growing up!

Funny, though, I actually never really got into pantyhose until I was around 11 years old having worn knee highs up until then. But one day, I don’t know what got into me, but I was in a Circle K market and saw the rack of Legg’s pantyhose and just grabbed a pair of Sheer Energy in an Off Black color (yes, I do remember that first pair well) then brought it to the counter to buy. I remember the cashier saying “Don’t you hate it when your mom makes you buy these?” and I nodded in agreement (and reflief). Then I rushed home to get these on my legs. That would be the point where I never looked back.

My teenage years took a slight deviation, having to try out lingerie to accompany my legwear. This was probably the time where my crossdressing was in its infancy since I needed something more than pantyhose to satisfy me, yet while still enjoying them. I suppose there was a growing need to feel more girly and lingerie made me feel “better.” However, I only found it more as a compliment to pantyhose since I would never wore bras, pantys or other lingerie alone. In fact I exclusively wore lingerie with pantyhose but then I would wear pantyhose at any time, under pants or whenever and get myself off without anyone noticing.

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Edith Body teddy over Filodoro pantyhose

I’ve been devoting quite some space here to pantyhose lately, almost seeming to forget their other silky (and just as sexy) counterparts… lingerie. The real reason for it’s omission is I haven’t really found anything in a while that I like and I rely on slipping into an older piece usually bought from a lucky whim. It’s primarily due to my issues with the typical lingerie found these days, not just from the point of view from a crossdresser, but I’ll go out on a limb and say for women too (OK, maybe some):

  • It is cheaply made from only nylon and/or fishnet and in the same black, red and white colors. Not to mention pricey for the tacky styles and low quality.
  • Or you find something you can just picture draped elegantly over you. Then the price tag let’s that dream die hard.

So, it usually means an undies purchase for the femme me is in the form of pantyhose, pantyhose and more pantyhose. Well, that is until I randomly came across a sexy teddy that caught my eye, overpriced of course. However, after a little digging in Google, I reached the ultimate candy store for crossdressers, SeksownaForYou.pl, from Poland.

This site appears to be the umbrella shop of Polish brands of lingerie, Avanua, Casmir and Passion which, to tell the truth, I had never heard of until I found the website. Yet, the selection of silky threads was amazing and now I’m extremely elated after tearing into that unmarked package that I received this past week.

First of all, while browsing the website, I was quite content to find lingerie styles that looked like fashion made actually made for this season. In other words, none of that run-of-the-mill fishnet bullshit you would see at your local sex shop. No, I could see there was the possibility of some quality in that stretch satin visible in many of their pieces. At least enough so where I absolutely had to try them out.

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Sheery the Crossdresser

Dear Mrs. Rainwater,

I’ve always been very curious when recalling my path leading up to becoming a crossdresser (and likely a future transvestite roaming the streets). It all seems to trace back to you as my teacher in my very first year of school when I was just five years old at the time. Actually those memories of you are still quite vivid in my mind.

I remember you would always wear those blue tights with sandals that would let those glorious hosed feet show. On those days, I would obsess over those gorgeous blue legs adding to the innocent boyhood crush I had on you. Of course, how could I forget, there was that one day where you lined up me and all of the other students and gave each one of us a big kiss on the cheek in appreciation of having us as students.

I’m sure you’re aware that doing that today would send you right to jail. However, I took it for what you intended it to be: reaffirming that crush I had on you was the real thing, even though I was five.

Since then, I wanted to be just like you, starting with the tights.

I became so obsessed with tights, that is, starting with the pairs I stole from my sister, who was catching on to my love for them. Then one day, I scrounged up my allowance money to buy my own pair of L’Eggs Sheer Energy pantyhose in an off-black color. My very own shiny, sensual, nylon-covered legs gave me such a thrill, almost as much as that smooch you laid on me years before.

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Platno Tana Bodysuit with CdR Rubino Pantyhose

I absolutely love wearing lingerie with my pantyhose yet, somehow, I usually end up buying way more pantyhose than lingerie. Chalk it up to my lingering pantyhose fetish but that’s just how it is. So when I do make a girly unmentionables purchase, it’s usually something special that I need to slip on my body right this second.

Naturally, I was surfing around for pantyhose on the Shapings website and came (literally) across something so simply sexy that I had to try it, the Platino Tana Bodysuit. And I mean simple, as in no lacy trim or shiny satin or embellishments of any kind. It’s just a regular bodysuit in a thong cut and in a brown color at that. Yet it turned out to be one of my sexiest pieces of lingerie that I now absolutely adore.

I’m already very familiar with Platino pantyhose and, given that those are a favorite of mine, it wasn’t a hard decision to give the Tana bodysuit a try. This is despite the fact that there really wasn’t even a clear image of what it was, only a picture of the packaging on the website. However, when I ripped into that little pantyhose-style package and hurried to slip into this, I was not let down at all.

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Black Club Dress

Part 3: “Hard” Lessons Learned

Part 2: All Dolled Up

Part 1: Fantasy Gone Horribly Wrong

* * *

Part 4: Punished, And Liking It

Rob was shocked by what he heard. There in front of him was what appeared to be the only other female in the club (besides his own mother) yet was another crossdresser, just like him, who was dressed just as sexy but in a black dress and also wearing black Wolford pantyhose, just like he was. “She,” however, appeared to be several years  older, much like the other college aged dudes in the club.

“Oh, well nice to meet you,” said Rob, “I really love that dress and are those Wolfords you have on?” he continued admiring the confident beauty in front of him.

“Thank you darling, I wouldn’t wear anything else just like you,” replied Sandy, the other crossdresser. “What brings you here?” she then asks.

Rob decided enough with the whole psychology project excuse and explained to Sandy the whole story right from the top. First the trip to the mall to buy sexy lingerie and pantyhose, then racing home to try them on, next getting caught by his mother and, finally, being “punished” by going out to a bar and club with his mother as his teenage crossdresser self.

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Flexees Decadence Slip

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Not too long ago, I discovered a long lost piece of lingerie from way back, a body shaping slip bought about twenty years ago. Yet ever since that moment of rediscovery and, let’s face it, somewhat sadly reliving my teenage crossdressing days, I’ve become obsessed with this particular piece of lovely lingerie.

Normally, I’m not really into shapewear. More often than not it is just a garment with all kinds of weird tight stretchy panels looking like a bathing suit your grandma once wore proudly. Nothing really sexy to them in my eyes anyway and, therefore, I never really kept up with the trends of shaping.

Yet the trends brought us to the age of Spanx, which really looks similar to those ultra modern swimsuits used in the Olympics. Still not something I’d go for when I want something sexy to throw on with my pantyhose to feel nice and girly (or cheap).

Throwing on that now-vintage Flexees shaping slip, however, changed my whole impression of shapewear for the time being.

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Legs Crossed in Black Pantyhose

Unfortunately, I’ve been a bit under the weather this past week. Nothing, however, beats the day that you wake up, sickness gone, and go about doing the things you had planned to do before the illness began.

Take today for example. I feel so good that the first thing on my mind is throwing on some of my girly wear to capture that silky feeling I love so much. But then I thought, “Why stop there?” Since I feel like this is a day that I can dedicate purely to crossdressing, I might as well document it all, right?

Of course it may reveal how absolutely boring I am but I don’t give a shit. I’ll have my fun (alone), then write…

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Black Dress and Wolford Tights

Part 2: All Dolled Up

Part 1: Fantasy Gone Horribly Wrong

* * *

Part 3: “Hard” Lessons Learned

Renee continued to eagerly suck on Rob’s member, or should we say blowing the Wolford pantyhose encasing it. Since it was his first blowjob, yet alone while transformed into a very sexy girl by his mother, he didn’t know what to do or what to expect, normal for a teenager. Yet he really didn’t have to as his erection did all the talking that was necessary.

Then came the point of climax a short while later as Renee kept to her task, not missing a slurp over the silky nylon covering his rod. “Ahhhhh,” Rob let out as he came with a pool of hot sticky love juice squirting out through his newly bought Wolfords. Renee was kind enough to lick it all off hungrily not wanting him to “stain” his pantyhose on his one night out as a woman.

“Did you like that?” Renee asked.

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Wolford Pantyhose and Lingerie

Part 1: Fantasy Gone Horribly Wrong

* * *

Part 2: All Dolled Up

Rob was still in deep embarrassment of having his mother walk in on what was the probably most exciting woman-to-be fantasy he had acted out yet. There he stood in with his new Wolford pantyhose gleaming over his legs, a Wonderbra fitting so perfectly giving his chest a womanly appeal and, let’s not forget, thong panties to match.

Then there was that red lipstick painted neatly over his lips as prime evidence he “borrowed” it from his mother. He knew he was at the mercy of whatever his mother’s reaction was but, when he heard her say she would take his car away, his thought quickly turned to losing his prized Christmas gift.

“We’re going to go out on a night in the town, you and me, and since you want to dress like me then you’ll go out that way too,” continued Wanda. Shaming him in public ought to teach him a lesson and will ultimately set him “straight” again, she thought to herself.

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