How Girls Clothes Changed Me

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An 18-year-old boy tries on girls clothes for the first time.
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(A true story about me.)

As a teenager I got a job working as a handy boy/janitor for a local ladies dress shop. They liked me and I certainly enjoyed working there. Even at such a young age I quickly could tell what needed to be done and soon was working without much supervision -- much to the shop owner's delight. All through high school it was a great job for me since my savings would allow me to get my first used car soon.

In such a situation I'd often see interesting feminine garments and loved how they felt and looked. I would even got an erection sometimes just staring at the lingerie there.

However, working in that store I would often hear comments about how wonderful this or that garment felt to wear. Often the women and girls were referring to a piece of lingerie. Naturally, I began to wonder anew about what it must be like to wear panties, etc. Somehow these thoughts didn't kick in until I was 18 and my hormones were working on me.

One day, while working to repair a floor mounted electrical outlet under the center of a circular skirt rack, two of my female classmates entered the store. I didn't realize they were there until I overheard their voices and recognized who they were. They were the two prettiest girls in my senior class in high school and only days older than me.

Before I could utter a "Hello" from inside the skirt display they launched into a commentary about how this or that skirt would flatter their legs or make their asses look even sexier to the guys. I didn't dare speak up now! However, I quit my working on the outlet and began to get an earful about how and why girls selected certain skirts.

Just then a clerk arrived and inquired if she could help the two girls. They went on to tell her they had come in to buy a box of nylon stockings each (I'm dating myself here) and the one girl needed a new panty girdle. The stockings counter was just about five feet off to the side from the skirt rack and behind it were shelves of different styles and sizes of nylon stockings.

The girls oohhed and aahhed about how silky and lovely this or that pair of flat knit nylons would feel on the legs. Eventually, they both made their selections of style and color (reinforced heel and toe seamless silky dress sheer flat knits were their choices) and then the one girl looked at panty girdles.

She chose a Jantzen "Postage Stamp" panty girdle in her size and then the clerk went to the rear of the store to ring up the purchases and bag them. After she departed the one girl laughed about how good panty girdles were at fending off boys wandering hands and the other quickly joined her giggling.

While waiting, the two wandered to the table displaying panties just steps away. A bit further, from me, but still within earshot. They sorted through the panties while

commenting about how wonderful this or that pair would feel to wear. By now I had a hard on and was really intrigued about what girls were able to wear all the time.

That day, and from then on, after the two girls left, I would "accidently" brush against a silky nightgown hanging along the wall, or touch the panties when no one could see me.

About a month later the owner of the store asked if I would be willing to work Sunday afternoon washing and waxing the linoleum areas of the store. They weren't open on Sundays, so it was a good time for such maintenance work. I'd done this before, with the owner and his wife in the office in the back doing bookwork and I expected the same.

Then I was informed they would be out of town that day but could give me a key so I could let myself in and lock up. Instantly I accepted the chance to earn some extra cash but also had another reason.

That Sunday I arrived right after lunch and parked my bike behind the store. Letting myself in I locked the back door and made sure the front sunshades were still down.

Right away I set to work in earnest scrubbing the flooring and then applying a coat of wax and buffing it to a nice high shine. I think I set an efficiency record that day!

Once finished I put the tools away and then set about on my own agenda.

First was a trip to the front of the store to the foundations counter. I chose a Playtex all rubber open bottom girdle. Reason for this was the sizes were printed on the outside of the cardboard tube the girdle came in. It was a delightful shade of light pink and had four garters attached to the hem.

Next I chose a box of Claussner brand RHT seamless dress sheer nylon stockings in a dark cinnamon brown shade. Following that I was off to the brassiere display where I picked up a pink satin bra, guessing at the size.

At the panties display table I picked out a pair of silky ultra-sheer light pink flare leg panties with just a hint of lace along the leg openings. Next came a pink nylon full slip and I was off to the fitting rooms in the back of the store out of sight from the street.

In the carpeted area, where the fitting rooms were, I entered the first room and placed my choices on the end of the light green velvet bench in the fitting room. A full-length mirror on the facing wall would help me determine how things fit and looked on me.

Stripping nude, I slipped the girdle out of the tube and stepped inside it. The fragrance was wonderful and I began to get an erection which caused me to smile. However, putting on that girdle was a huge struggle!!

I must have pulled and tugged for 5 minutes before I had it up in place and was able to hook the hooks and eyes together so I could zip up the zipper on the left side. At just 18 I would have a girlfriend who would show me how to put on my Playtex girdle much easier (she also got me into wearing a garter belt). She showed me that girls would roll the girdle inside out half way down after powdering the inside with talcum.

Then, girls would step inside their rubber Playtex girdles and easier slide them up with the aid of the talcum powder. Once the bottom hem was in place they simply unrolled them the rest of the way to then hook the hooks and eyes together and zip it closed.

Anyway, I didn't know this at the time and wondered how girls ever got to school on time! I was a bit winded, but managed to open the box of nylon stockings and then sit on the velvet bench and put them on as I'd seen my mother do when she didn't know I was around. It was easy and, like the girdle, the stockings fit perfect!

It was amazing, to me, to suddenly be exposed to the feeling of a thousand silken fingers caressing my legs all the way from my toes to almost the girdle. It was wonderful and I knew girls were soooooo lucky to be able to wear such things.

The panties had slipped off the stack, on the bench, so I retrieved them from the floor and stepped inside and slithered them up my nyloned legs. This was almost too much for me and I had to sit down to catch my breath.

As I sat on the bench, looking at the mirror, I was astonished to see this young flat chested girl with with a boy's haircut looking back at me. It was amazing the transformation just these few garments were making on me!!

Unwittingly, I crossed one silken clad leg over the other. I was totally unprepared for the feelings this would create! One nylon clad leg sliding over the other was incredible, and the whistling sound nylons always made when you did that only added to the sensations! My 7.5 inch clitty was hard and sticking proudly out the leg opening of my sheer pink panties. Just then I suddenly erupted into an orgasm, without even playing with my penis, and shot hot white cum all over my nylon stockings!!

The orgasm was more intense than when I would jack off and I nearly fainted and almost fell off the bench in the fitting room!! It took me several minutes to recover from what had just happened to me. I'm sure I sat there shaking for several minutes.

I quickly removed the nylons and rinsed them out in the janitor's sink just a few steps away. Then, once I'd cleaned and dried myself off (the panties were okay), I donned another pair of silky nylon stockings.

All the while I was thinking, "If this is how it feels to dress like a girl I will always do it!!" Well, I still am and wear panties daily often with garter belt and silky nylons.

Once I had settled down I tried on the bra and slip only to find they were too small. A quick trip to the front of the store, hiding behind counters, I managed to find the right sized pink satin bra and a pink nylon full slip.

The rest of the afternoon was spent trying on various dresses and skirts and blouses. My penny loafers looked fine with the skirts and blouses but not dressy enough for dresses. High heels were still a few months away for me (thanks to my girlfriend's mother -- but that's another story).

I finally had to stop and slip my panties down and jack off before changing back into my boy's outer clothing.

When leaving the store, that day, I wore the girdle, panties, and nylon stockings home. My undershorts and socks were in a bag in my bike basket that contained the rest of the box of stockings and a light blue semi-sheer ankle length nylon nightgown.

I even was thrilled at how my jeans slid against my nylon stockings as I pedaled my bike home and my cockette got hard all over again.

The store had an arrangement where the employees got a discount on their purchases. We would merely write down the item number on a sheet in our time box and the owners would deduct the cost of that garment from our pay. My items: they thought were for my mother.

At home I reveled in what I was wearing. At bed time I donned the nightgown, since my bedroom was upstairs and my parents were downstairs. My other siblings were all grown, so I had the upstairs to myself.

As I lay in bed I had to jack off to one more terrific cum and knew I'd always want to be a sissy.

During the night, at about 2 o'clock, I began to dream I was a girl on a date with her boyfriend. We were at a drive in movie and were in the back seat of his car. We were necking up a storm and he was feeling up my breasts as I stroked his cock which I'd managed to retrieve from his slacks. Soon he had me sucking his cock and I was loving doing that. Then, he slipped my panties down my nylons and began fucking me. That is when I experienced a wonderful wet dream (the first of my life) and further convinced myself I'd always be a sissy and began to look at boys differently from then on.

Sincerely in panties,

sissy erica

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luvtodoitluvtodoitabout 3 years ago

A lovely story. Thanks for the memories.

pantycladladpantycladladover 8 years agoAuthor
Who Girls Clothes Changed Me

Dear Reader,

Yes, it may seem a bit flat. However, this was my very first attempt to write anything. Also, it really, really, really is a true story. What I describe as happening in that ladies store that Sunday afternoon is what really occurred. Even the wet dream I had that night, my first night sleeping in a nightgown, is also true.

Sincerely,

sissy erica

AnonymousAnonymousover 8 years ago
S/he does NOT "sick really bad".

This story was a bit flat compared to many on Lit. But I know from reading your other works you get MUCH better. This should be listed as a prequel to the Alice series

DaveXX80DaveXX80almost 9 years ago
Nice!

I enjoyed reading!

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