A True Story of Transformation

by: Walt Williams

 

When still quite young, around twelve as I recall, there was one Halloween when my parents had planned on spending the evening out so as not to be bothered with the whole trick or treat thing. I was the youngest of four, and of us kids, my two sisters were the oldest, my brother next, and then myself. Oddly enough, my oldest sister and myself more closely had mom’s face and complexion, including fair skin and flame red hair while my other sister and my brother had for the most part, dads features, with dark hair and dark complexion. We were an interesting mishmash of our gene pool.

As the evening approached, my parents readied themselves to escape the endless doorbell ringing and candy giving, and checked on our plans for the evening. My two sisters were having their boyfriends over to help with the trick or treaters, and that was ok with mom and dad, as they knew them and trusted they would be gentlemen, and my brother was going out with his buddies to a movie. That left me and I wanted to go out with my friends to collect candy. Mom agreed to everyone’s plan, though she assigned me a curfew, and gave the task of putting together my costume to my sisters, then mom and dad left. That was fine with me, because with my sisters having their boyfriends over, they wouldn’t enforce the curfew. In fact, the longer I stayed out, the better they would like it.

Next was the problem of a costume. We never had store bought costumes, but our outfits were always very creative. Especially when my sisters were in charge. This time though, they were a bit agitated that they had to spend valuable primping time on me, and took out their agitation by taking me to mom’s room and began by selecting some underwear for me to put on. I complained, but they said they had no time to argue, and if I wanted to go out, I would do as they said. I harrummphed a bit but finally, I did as they said and pulled on mom’s all-in-one open bottom girdle with garters, and the frilly panties that were my sister Js’ idea and contribution. A drawback for me (or plus, depending on your point of view.) was that I was right about moms’ height and measurements, considering she was the shortest member of the family, and I was a bit pudgy, with baby fat breasts that caused me great embarrassment when swimming or doing anything that required me to be topless. It was really so bad that I avoided these types of activities, and one time, when home alone, I had tried on one of moms’ bras, and not only did it fit, but I nearly filled the c cup, just as I did this evening. Then they came back into the room and helped with everything else. There was mom’s lacy white full slip, and a pair of beige stockings that were expertly clipped to my garters. Next came a pair of black low heel pumps (which, by the way, gave me very shapely legs), a string of faux pearls, some clip on earrings, and a very nice light blue sheath type dress. I was beginning to look almost exactly like mom, and my sisters were as shocked by the resemblance as I was, but we all found it fascinating. So much so that I forgot totally about my earlier reticence about the whole "dressing" thing.

Upon discovering this uncanny resemblance, they put more effort into the transformation, going so far as to expertly apply my makeup, and then styling my somewhat longish hair. After a sprits or two of moms’ expensive perfume, they took me to her mirror and the three of us stood there in awe. They were no longer being spiteful or giggling, and I was no longer complaining about the female persona they had given me. The three of us stood there dumbstruck. There were my two sisters flanking a younger (though not terribly so, as the makeup and hairstyle seemed to have aged me to near 16 or 17 years at a guess) version of our mother. All three with mouths open, but no one saying anything.

Of course, I filled out moms’ corset very effectively, and it in turn shaped my baby fat body into the feminine form that held us riveted to the mirror. It was almost magical, and it was some moments before they agreed it was a done deal, and scooted me off downstairs with mom’s light pink sweater to finish off the costume. They gave me a quick once over, and showed me how to smooth my dress as I sat if that became necessary, then handed me a bag and scooted me out the door so they could freshen up for their boyfriends impending arrival.

Well, I stood on the porch in the fading light of day considering my new self, and, to my surprise, feeling quite flush about the whole adventure. I loved the way all the silky underwear slid on my smooth skin as I walked, and even began to relish the tightness of the corset. It was all so new to me and yet so enthralling. I LIKED BEING DRESSED!

As I left the porch, and stepped rather demurely onto the sidewalk (I was still getting used to heels), I noticed something at once strange and exciting. No one was noticing me. There were no looks of appreciation of my costume, and no teasing from any of the neighbors. Nothing. Just a pretty young girl walking down the street, who happened to be carrying one of those cloth shopping bags with handles that must easily have been mistaken for my purse, and I’ll tell you why I know it was in a little bit.

I walked the five blocks to where my friends and I were to all meet, and became mesmerized by the swivel in my hips, and the rhythmic gentle roll of my too well shaped breasts. I even began to feel strange urges, like wanting to find some older man and tease him. I knew of sex but not about it. I mean I knew it existed and was supposed to be pleasurable, and I suppose I might even have known a little of the mechanics of it (a rather unromantic description, I know, but the best way I can describe my grasp of the subject at the time.) but I had no experience beyond looking up a girls dress when I had the chance. Now I didn’t have to though, did I? I knew what secrets they hid because I was hiding the very same secrets myself.

Without realizing how dangerous a game the teasing could have been, and I surely could have made that happen as I received several honks and whistles as I strolled to my rendezvous with my friends, the danger passed for the moment as I came upon the group of costumed clowns, pirates, spacemen and Napoleon Solo’s who were my trick or treating partners.

No one recognized me and I was forced to explain myself to boys who knew me well, and still I drew open mouthed stares. It was a few moments before they accepted that fact that it was me, and then they started lifting my dress and laughing and ooohing and ahhing until, just like a girl, I pulled my dress down and told them to stop. They laughed it off, as did I though I was a bit embarrassed that they had all seen my slip and even my panties, but I couldn’t let them know this. It would only cause further teasing.

After some boyish bonding and a brief discussion of our trick or treat "plan of attack" which was in essence, the routes we would take to obtain the most and best candy, we set off in a direction even further from our own neighborhood than I had already walked. Like I said, though, I was enjoying all these new sensations, and didn’t mind the extra walking. In fact, I was getting quite nimble in my heels.

Well, here’s the part where I explain the reason I know people thought my trick or treat bag was a pocketbook. At the majority of houses we visited, all my friends were offered candy while I often had the door closed in my face. At first I didn’t understand this hurtful behavior, and I was too shy to knock on the doors again, so I just walked away, stunned and hurt. I kept trying, and to be honest, I did get some candy because I started getting in front of the boys (yes, I noticed I referred to my friends as "the boys" too.) and so was first in line to receive the goodies. Sometimes the candy came with strange looks which I didn’t understand either, but at least I was getting candy. Finally, it was all made clear to me when a little old lady gave candy to the boys, then instead of offering me candy, she said how sweet I was to take the younger kids around trick or treating.

"You know young lady, it’s very nice of you to help out your mother with the younger kids. Are they all your brother’s?" she asked, probably grateful for the chance at adult conversation after the string of cute children and mischievous boys she must have had. I decided to play my part.

"Oh dear me, no ma’am. Just the one boy dressed like the clown. The rest are his friends but I told their mothers that since they I had to watch Tommy, I would watch them as well if they wanted me too. They were grateful for the break. " I said, ending with a smile. I was enjoying this deception more than the collecting of free candy.

"That’s nice. Mother’s can use all the help they can get, especially today what with all the trouble youngsters seem to be getting into. God knows what it will be like when your ready to have kids." She offered, raising her eyes to the sky as if whispering a prayer for my future motherhood. On another day, I might have joined my friends in teasing and taunting this little old lady, but tonight, I liked her, and I liked her thinking me a future young mother. It was weird. Even to me.

I noticed my friends moving on to the second house away from where I stood, and thought I’d better end this and catch up.

"Well, better catch up to the little trouble makers before they get too far ahead. It was nice talking to you. " I said, showing my devotion to my responsibilities, and bringing an end to the conversation at the same time, but it had an unexpected side effect as well.

"What’s your name young lady?" the lady asked as I started to turn away. I turned back to her and said the first girl name that came into my head.

"Sylvia ma’am." I said, still playing the game.

"Well Sylvia, I have been looking for a young lady to help out around the house on Saturdays with cleaning and such, and you seem very responsible. I would pay $5.00 an hour for probably 3 or 4 hours on Saturdays. (That by the way, was a fortune back in the early sixties.) Would you be interested?" she asked.

I was flabbergasted. I quickly calculated in my head and all I saw was $15.00 or even $20.00 for a few hours work, and answered without thinking.

"Yes ma’am. I would. " I said excitedly.

"Good. Come see me next Saturday morning, and we’ll talk. " she said grasping my hand softly, then retreating inside and closing the door.

I didn’t even think about the implications of her hiring "Sylvia" at first. The very first thing I thought of was how soft her skin was to the touch, even at her age. And how gentle it was. More like someone wrapping your hand with a big cotton ball than holding it in their hand. How wonderful it must be to be a woman all the time and have such silky soft skin. And wear such soft and pretty underthings all the time, I thought. Then I remembered my friends and wanted to tell them what happened, but looking down the street, they were nowhere to be seen. They had left me, and I was probably near 15 blocks from home. Oh boy.

I wasn’t really worried though it was completely dark now, and I seemed to have lost my interest in trick or treating anyway. I had fallen deeper and deeper into the Sylvia persona my sisters had created and as I walked slowly toward home, the only thing I thought about was how I could lay claim to that nice little old ladies offer of a Saturday job.

There was still the occasional trick or treater but they became fewer and farther between as I meandered on my way, often turning down streets I had not been on before just so I could extend my walk a bit more.

The remainder of my stroll through the night as Sylvia was practically uneventful, except…

I was maybe 8 blocks from home now when I saw a group of teenage boys, probably around my brothers’ age, coming toward me on the same sidewalk. They weren’t particularly menacing or anything like that, but it did appear they were a little tipsy. It was fairly common around this time for the older teens, especially the boys, to finagle themselves some beer or other alcoholic drink and get drunk. I hadn’t tried that yet but I knew my brother had several times, so I was aware of it, and not really worried about these boys. I guess I had forgotten for the moment that I was Sylvia.

As they approached, they too were fooled by the magic my sisters had worked because they started to whistle and say things like "Hey Baby. Where you goin?" and "Wanna come have a drink with us?" and though the thought of being accosted was totally foreign to me, I did feel this odd indignation and an urge to turn my pretty powdered nose up at them. In fact, I did just that as I tried to walk past them on the inside of the sidewalk.

"Oh, don’t be like that. What’s your name, Babydoll?" said the boldest of them as he pinned me against some hedges and put his arm around my waist, drawing me too him.

"None of your business, now let go of me!" I demanded as his other arm came around my waist as well, and he pulled me very close to him, to the point where my pointy breasts were pressed against his chest, and his face was inches from mine. I struggled a bit, but I still wasn’t thinking about being violated, so my struggles were minimal, as if against some minor annoyance, and he easily held me fast.

"Awww, c’mon babydoll. I’m just trying to be friends. Give me a little kiss, huh?" he said, his lips coming less than an inch from mine, and his hands sliding up and down the back of my dress. I know he was enjoying the sensation of soft skin beneath layers of nylon because I was too.

I wasn’t aware that he had worked my dress and slip up my thighs slowly till I felt the coolness of the October night air on my thighs above the stocking tops, and realized his hands were cupping my prettily pantied bottom while his fingers played with the lace ruffles. I was mortified, and now started to be scared.

All at once, I was aware of everything. This boy who had me exposed and trapped. His friends who watched hungrily, but silently. The empty darkness of the street. Everything. I was totally incapable of reaction. My mind was outside my body, and it too was watching in silence. I saw myself groped and pinched, cupped and caressed, and one of the silent watchers even approached to feel my breasts’.

I was frightened but actually enjoyed my predicament as much as they did. That was part of what frightened me so much, I guess. I know I liked the feel of hands all over me, and even to a point, the sensation of helplessness.

It never occurred to me to tell them I was a boy. I’m sure I wasn’t even thinking like one at the moment. There was no repulsion at being groped by other boys, only at being groped. And even that wasn’t really repulsion. Had it been just one boy, I might not have been feeling the mixture of embarrassed pleasure and helpless fear that I was feeling. Only embarrassed pleasure, but as it was, there were just too many boys trying to get at me. I started to tremble a bit, and the boy holding me tightly became less rough, even gentle.

"Hey. We’re just playing babydoll. Don’t be frightened." He said softly, trying to calm me.

"Backoff!" he said to the other boys, who had witnessed the exchange, and had already begun to do so. I guess in fear that I might scream or something. They weren’t really a gang or anything. Just a group of teenage boys who were a little drunk, and very afraid of getting into trouble.

My dress was allowed to fall back down into place, though my slip was still bunched up around my bottom, and the boy holding me relaxed his grip. I was still nervous but no longer to the point where I was trembling and he smiled sweetly at me.

"See. I wouldn’t hurt a pretty little thing like you." He said trying to show me he was not a hoodlum.

"I just want to be friends. Now why don’t you give me a kiss and tell me your name? I’m Bill. " he offered, hoping telling me his name would induce me to tell him mine.

"No. I don’t want to give you a kiss. Your mean." I pouted. I didn’t mind the idea of giving him a kiss, but already I was learning to play the game.

"Awe, I’m sorry. I’ll behave myself. Just one little kiss, please?" he begged teasingly.

"Then will you let go of me?" I asked, stringing him on just a little.

"I promise. One little kiss, and your name, and I’ll let you go." He swore with his hand in the air like a Cub Scout. What could I do? I kissed him.

I tried to kiss his cheek but he was too fast and shifted so my lips met his perfectly and he again strengthened his grasp while he pushed his tongue past my lips and into my mouth. I struggled a bit, but only in surprise. As his tongue roamed in my mouth freely, I realized I was enjoying this, and gave myself to it.

His friends had strayed a few more steps away, but I was aware that thy watched with smiles of approval. Their friend Billy had scored as far as they were concerned. And he had scored with the girl in the lacy slip and panties. He was BMOC to them. After the kiss, which seemed to last 5 or 6 minutes, and maybe it did for that matter, Bill again asked my name, and all I could think to say was the name I had given the old lady.

"Sylvia." I whispered with my head down. I was just a little embarrassed by my surrender.

"That’s a pretty name. Can I see you again Sylvia? A movie maybe?" he asked, seriously wanting to see me again, but not really me. He wanted to see Sylvia. This was getting more and more complicated. Even more so because I would have liked to see him again. Without all his buddies.

"I’m going to be in this neighborhood next Saturday." I said to him with a shy smile, and I gave him the Little old Ladies address, and explained I would be helping her that day, though I had no idea how I was going to work this out. He grinned broadly and promised he would wait all day on her steps if need be. Then I became playfully stern with him and told him to turn around and stand between his friends and me so I could fix my slip. This he did, but I caught him peeking while my dress was once again raised, though I continued my adjustment anyway, and pretended to be cross with him.

"Now you stop it, or I won’t go to the movies with you." I said petulantly.

"OK! OK!" he said laughing a little at my "distress" and happy that I had accepted his movie invitation by default, as it were.

"Alright. You can turn around now." I said after lowering my dress back into place, which he did just as I turned to leave, but he gently caught my arm and turned me back to him and before I knew what he was up to, he stole another of my kisses. (hehehehe)

"See ya next Saturday, Sylvia." He said when he had satisfied his need to kiss me, and turned to join his friends.

"See ya next Saturday, Bill." I said with a faint wave to his receding back.

"I hope." I thought to myself as I too turned and headed for home.

This was going to be tricky, but I so wanted to make it happen. But how? I would study this problem day and night for the next few days.

 

 

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© 2001 by Walt Williams. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, compilation design) may printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without express written consent of the copyright holder.