Pippy; Entered In A Sissy Pageant

Normally being a part of a large family is beneficial, or at least somewhat helpful. I was one of the six children that our parents had, four boys and two girls. Mom was methodical in her bearing of children, having two sons each a year apart. Then two girls next, each one of them also a year apart. Then things went haywire and her next visit to the hospital bore twins, identical twin boys. Maybe because she skipped a couple of years before she had us, her timing might have been thrown off. There were complications my brother was wedged in the wrong way blocking the birth canal. They had to do a cesarean to get things untangled and eventually we both emerged.

My brother was a few minutes older since he appeared first, but that was not the only problem my mother faced that day. While getting us out the doctor inadvertently damaged her womb, so as soon as we were out he had to repair the damage. Five hours later Mom was taken back to her room, two scrawny hungry babies wanting to be fed. Over the next few days Mom decided that was it for children, telling my father to get a vasectomy or she would cut it off herself. With a house full, Dad took the hint and soon we were to be the last of the brood.

Dad hired a nanny to help Mom, especially with two of us it was greatly appreciated by all concerned. Later in life, according to my other brothers and sisters, there was considerable frustration with us, we were always hungry, grouchy and often a pain in the ass for Mom and Nanny. This was told to us and anybody who was interested when asked about our upbringing. Once Mom recouped from her child bearing years, she went back to her career as a bank manager. That left the two of us for Nanny to be raised and cared for. I never thought Mom didn’t care about us, it was just the appeal of a position with authority. A one word definition would be power, power to be someone who is admired and respected something she did not feel she had as a Mother with six children.

I guess we were more than enough to handle when young, the nanny took to dressing us as girls quite often, since our sister’s clothing was still functional and we seemed to be quieter when dressed that way. Of course, when school started the clothes were taken away and the rough boys clothing had to be endured. I managed to do better than my brother, he threw a fit when not in his female clothes, even once stripping off his male clothes at school and refusing to put them back on. That caused all kinds of ruckus as both of our parents were called to come and pick him up. I was taken home too, them not wanting to make a second trip later for me. It was a chilly ride, with Mom and my brother going at it verbally.

In the weeks to come Nanny managed to bribe him to wearing the more unisex female clothing to school, but once home he was out of them and into dresses as soon as he made it into the house. He was bullied some at school, myself and several teachers bailing him out of a beating more than once in his grade school years. I was teased some by association, since I was the freaks twin brother. There were lots of names used when addressing my brother, none of them favorable. Freak or tranny the most widely used of those names.

For high school, my parents and Nanny finally gave in and sent him to a private girl’s school. No more trouble, he fit in well and was happy in his dresses and makeup. He was an excellent student, earning straight A’s all during his school years. Of course his grades made my life miserable, I was not as focused as he was, so a B or two and mainly C’s was the best that I could accomplish. My parents pointed to my report card every six weeks, wanting to know why I couldn’t do as well as my brother. I had no answer, we even tested with the same IQ, so a lack of intelligence could not be blamed for my shortfalls.

Our older sisters welcomed him to their girls club, more fun shopping, and talking about boys that way. He fit in perfectly often knowing more than his sisters about fashion and makeup. Then Mom heard about a pageant for sissy boys, of course she was interested, finding all about it and when the pageant was to be held. Our sisters never wanted to do pageants with Mom, although she tried often to get them interested. They steadfastly refused to participate, so Mom kept with her career, but now a possible pageant with her sissy son to look forward to.

I would often find her in her office late at night when I was on my way to bed, glued to the computer with pamphlets strewn all over the desk. On occasion she would not pick them up and put them away, the next day I would enter the office, anxious to see what she was so concerned with. That was my introduction to what was in store for brother. I am sure it would be perfect, a way for her to be the sissy she truly wanted to be. It never bothered her to be called a sissy, she viewed it more like a title or honor. In fact I often teased her about being the girliest sissy I knew. We got along, but it was not the close bonding of an identical twin, more like a girl and boy friendship.

Participating in a pageant, that was quite a different story for my brother. They went to the first one, and Pippy, her female name, won easily. Thus started her path into the sissy pageant circuit. Mom and her were off most weekends, traveling all across the U.S, hitting as many pageants as they could. Some were simple pageants, offering a trophy and a sash for the winner. Others were major affairs, having talent and bathing suit competitions along with the standard beauty pageant tropes. Some of the contests had substantial prize money, Pippy winning enough to pay all their expenses and put a little aside for later. Since this was a lifelong wish of Mother, a life on the pageant circuit, she quit her bank job and became a full time pageant Mother. Of course, Pippy was thrilled, she getting to indulge in her dresses and all things female now whenever she wanted.

There developed something between the two, even when home Mom and her would be doing things together, typically Mother and daughter things. My sisters were jealous of the two, they wanted nothing to do with the pageants, but would have loved to do the shopping, cooking and socials that Pippy got to enjoy with Mom. Dad stayed detached, knowing that any intervention with Mom about his son might raise her full ire.

I was just there, entering my sophomore year at high school. My grades never improved that much, I was bored most of the time. I tried out for sport teams, but was just as uncoordinated at them as I was at getting better grades. Maybe I was just not motivated enough to do well. My older brothers did things with Dad, my sisters had found a network of female friends to do things with leaving me the odd one out. I just didn’t fit in with any of them, too many years difference between my older brothers and me, too little interest in what my sisters did.

Mom and Pippy had been shopping for weeks now getting new clothes for the upcoming pageant season. Like school the pageants took a few weeks break in August before starting again the first week of September. Pippy did have a couple of friends that she met at some of the pageants that lived locally. It was on one of those sleepovers with one of her friends that she was exposed to measles. Of course, it was inevitable that she came down with a bad case of them, the doctor confining her to bed for several weeks. Well that threw a monkey wrench in the pageant thing, according to the doctor Pippy would miss at least three pageants before she would be well enough to travel and participate again.

Nanny took care of the infected child, since no one else had ever had measles including Mom and Dad. The two were sequestered in the apartment above the garage, where they had everything they needed to exist. In fact it was Nanny that had taken Pippy to the doctor to be diagnosed. Mom was beside herself for several days, her entrant in all the pageants out of commission for several weeks. Then one morning she noticed me eating my breakfast cereal alone in the kitchen. If I had been aware of how she was eyeing me up I should have run as fast as my legs could carry me to somewhere safe.

Mom once she decided something is a force of nature, making plans and always getting her way. I was grabbed after putting my dishes away and taken to her room. As soon as were arrived I was undressed, as she surveyed my naked body. Unfortunately my twin and I were exact look a likes even down to birth marks and body structure. Since I never was able to do much sport wise my body never developed much muscle, hence I looked pretty much like Pippy, only having shorter hair.

One of Pippy’s dresses was slipped over my head and I came to the realization of what she was planning. I panicked, tried to get out of her grasp then broke down in tears. Mom held me for the longest time, it felt so good, something I had been denied since early in grade school. The tears did eventually dry up, but I savored the embrace even snuggling a little closer to her body. It was almost an hour later when Mom made her pitch to me.

“I need to have someone fill in for Pippy in the pageants. You would be perfect in that role. Please consider doing this for me. I know I have ignored you as a child, maybe we can connect on some level while you fill in for your sister. I know you have protected her often at school, risking your own well being while doing so. Let’s face it I have been a lousy Mother, letting the Nanny do what I should have been doing most of my life. Can you give it a try for me, if after we get you all dolled up you don’t want to do the pageants I will not force you. I know I am asking the world of you, but it would mean so much to me. Pleaseeeee.”

Of course, I was so unaccustomed to the different ways that a female can get the opposite sex to do her bidding I fell for it and in less than thirty minutes we were off to her salon. Still in the dress, with a pair of frilly panties slid up underneath it. The silky panties almost doing me in as she pulled them up my legs. The only thing saving me from massive eruptions was when she pulled my thingy back hard as she pulled the panties snugly in place to hold it there. In a nano second it shrunk, almost to oblivion at her rough handling of my crown jewels.

I reluctantly got out of the car at the beauty salon, but then was grabbed by my hand and led in to my demise. At least to me it seemed to be my demise, the salon so girly that even walking down the aisle I felt I was on my last few moments on this planet. I was introduced to another lady, she seemed nice and friendly. Mom exited leaving me with the lady not knowing what was going to be done to me. I didn’t miss Mom leaving with the dress I was wearing in her hands. The lady introduced herself to me, her name was Tricia and she would be seeing to my transformation today. She took time to explain what she was going to do, and how it would be done. Nothing she was going to do today was permanent, a few things taking a couple of days to return to a masculine appearance. Piercing my ears would be one of the things lasting longer, but if I didn’t wear earrings in them the holes would eventually heal up.

I told her in a little pathetic voice I was trying this for Mom, not sure if I would actually participate in the pageants yet. It all scares me, being dressed as a sissy and parading around on a stage in front of lots of people. I got a hug from Tricia, then let’s get started, one beautiful sissy coming up.

All kinds of treatments were performed on me over the next few hours. Each look in the mirror showing a little more of the male in me vanishing. I kind of liked the look, not exactly like Pippy but very close. The earrings were fascinating, I especially like the dangle earrings in the bottom holes as they swung against my neck sending little shivers all through my body. That was until she glued some breast forms to my chest. Once she released them and they pulled down some on my chest, all thoughts of the earrings ceased to exist.

Then she moved to my groin, explaining that my male thingy needed to be glued back and hidden under a silicone vagina, to keep my appearance feminine at all times. She made sure I understood he will still be there, just not visible to others. I was kind of in favor of that, fearing that if I got excited I might embarrass myself something awful in a dress. It felt funny looking down there and seeing a slit. I knew what a female’s sex looked like, having classes in human sexuality my first year of high school. Never saw one in person, girls still scared me, all seemed so self-assured and driven, while I was content to do as I was told and ride things out to an eventual end.

My nails were done somewhere in this time period, extensions were added making them long and quite feminine. Once the bright pink polish was added, there was little doubt they belonged to a female or a sissy. I got a permanent, a smelly treatment of the hair that made my hair into little rings of curls, assuring my hairdo would last for weeks. I gave her a funny look, as she smiled at me “It can be undone if necessary, but will keep your hair just perfect for a would be sissy.” Not exactly reassuring but too late to avoid that particular treatment. It did make my hair super curly, changing how I looked quite a bit. All of my male essence seemed gone now, nothing but this sissy want a be now sitting in the salon chair.

Makeup next after my hair was set in curlers, larger this time to help shape the finished hairstyle. I just shrugged my shoulders, at this point it was all downhill from here on out. The roller coaster pulled out from the start, gaining in speed as I attempted to stand up wanting to get off. By the time it entered the first turn it was too late, the lap rail was in place holding me secure to the seat as the roller coaster climbed for the first of many downhill runs. I was in the seat and a sissy was the only thing to emerge, so I took a deep breath and screamed in my head as the sissy coaster did its job.

When I managed to come back to the here and now I was mesmerized at my image in the mirror. My hair was out of the curlers, a cute curly hairdo empathizing my feminine looks. The makeup erased any doubts of the gender of this sissy, my newly shaped eyebrows screamed female, not model like female but super girly sissy.

I was helped out of the salon chair, still a little unsteady after being in it for hours. I looked at the accompanying table at the clothes picked out for me and nearly fainted. It started with a brief pantie with tons of lace on the fanny portion of the garment. Then a bra to hold my little boobies secure in its embrace. Of course it matched in color to the panties, also trimmed in matching lace. Then a corset held up to me, Tricia telling me that my waist was not very lady like and this would handle the problem. It was secured around me and tightened quite a bit. Tomorrow after sleeping in it, it could be tightened some more giving me the figure I desired. Then some stockings silky and secured to the corset garter tabs. I was glad that my thing was hid away, the feel of the stockings did all kinds of things to my body, I am sure if he was out it would have been embarrassing.

Then the dress, my mouth was open all the way as soon as I caught a glimpse of it. Pink and pale lavender in color with huge flowing skirts with sewn in petticoats underneath the dresses skirt. Trimmed in contrasting lace it was so frilly, even though I had seen Pippy several times in her sissy dresses this one outdid them all. I was left alone for a few minutes, standing in front of the mirror and examining the reflected image. I was almost identical to Pippy, maybe a little cuter in my opinion. Yes I said cuter, somehow this had all been processed by my mind, realizing that replacing her for a while was going to be fun. Fun, but also scary weird since what I will become is far from anything normal for a male.

Mom came to get me shortly thereafter, took one look at me and squealed. I have never heard Mom squeal like a teenager before, causing me to giggle at her actions. I was hugged, kissed and hugged some more. She paid the bill thanking Tricia for her services. I was taken to the car and driven home. Mom calling Nanny to take a look at me. Again the hugging and kissing, apparently everybody pleased at how feminine I turned out.

I ran to my room to get a closer look at my body and face, passing Dad on the stairs. All I heard was Pippy you should not be in the house, you will give one of us the measles if you stay. I finished running to my room and entered locking the door behind me, let Mom tell Dad I am not Pippy but his youngest son. I did hear some yelling a little while later, apparently Dad not happy loosing another son to the sissy world. I knew it would not change anything Mom ruled the roost and has always done so, her word the last word.

I stood in front of my mirror staring at my image, a cute sissy is such a feminine dress, white stockings and a matching lavender kitten heel. Makeup and my head in tight little girl curls completed the image. I remembered Pippy in a similar hairdo, only she had ribbons woven in among the curls to match her dress. I rubbed my lips over my lipstick savoring the taste and feel. I held up my hands looking at the longer fingernails now all painted in a matching pink color to my dress and lipstick. Even though I was in high school now I looked much younger maybe ten or twelve years of age. I stood there turning back and forth to see all sides of my appearance. That is where Mom found me after I unlocked the bedroom door.

She had made several calls, the main thing was that I will now be attending the girls school alongside Pippy. In fact Mom decided I would take over Pippy’s identity and name, the old Pippy now becoming Tippy, a name my sister preferred all along. Thus when she recovered we both would be entered in the sissy pageants, as twins Pippy and Tippy. She had already made entry in several more pageants to coincide with the expected time of Tippy’s recovery.

I realized that my trial period had vanished, now I was to be a sissy for the foreseeable future. Nanny would start training me in the feminine ways and movements as she had done for Tippy. That would be done in the house so she could keep an eye on Tippy in between my training. I would be checked out of my present school and after a couple of weeks of training start at the girl’s school along with Tippy.

After receiving some basic training as a wanna be sissy and several more visits to the salon I was anxiously awaiting attending my first sissy pageant. Mom and I drove the three hundred miles to the pageant, while I reminiscenced about the last few weeks. I did win the first pageant, my enthusiasm for doing this suddenly through the roof. Now I was looking ahead. To the next pageant and beyond.

Originally I was dead set against it, to dress like an immature female and prance around seemed like a death sentence. Day by day the disguise seemed to affect me. lowering my resistance to the things I was doing. The clothes felt wonderful, not like my old male clothing. I think the deciding factor was my image. When I looked in the mirror I saw a young attractive sissy, dressed in her feminine finery and smiling. The smiling never done much when I was a male. My previous experience as a male was not bad, but lacked anything exciting or unusual. I had a few friends, we did things together but looking back they were just something to do, not really things I enjoyed or would want to do again later in life. The friends part was just a word, for they meant nothing to me and I am sure I meant very little to them.

Already I could tell a difference in my thinking, what would have been a definite no-no in the past, now openly embraced. When this all ends will the male me re-appear or will he be lost and trapped in frilly dresses and girly actions. The dresses, the makeup and acting girly I was actually looking forward to it. So much for my years as a male, all of that trashed in an instant as soon as I got a look at my image in the mirror. But will it be for the short term, or will it be for the rest of my life? I sincerely hope the latter.

Tippy joined me a few weeks later on the pageant circuit, where we won almost every pageant we were entered in. At home we excelled in our studies at the girl’s school, where I finally found a niche that suited me. We both had a lot of female friends, the girls loved our clothes, even though a little young for most of them, they were jealous of all the clothes we got to wear, our makeup and the jewelry we wore all the time.

When we reached the ripe old age of eighteen, we could no longer participate in the pageants, Mom finding us jobs as models for a manufacturer of young girl’s clothing, most of what would be classified as sissy wear. The job paid well, and we were featured in most of the young female magazines, now recognized wherever we appeared in public. We did end up back at a lot of the pageants, as spoke persons for the clothing company, doing impromptu modeling shows featuring all of the new designs available for the young sissies.

In a way I was thankful Tippy caught the measles, allowing me to take her place. Otherwise I would have missed a special part of my life, becoming a sissy and taking part in all of the pageants. Regrets, no way. Give me a sissy dress, some makeup and a curly hair style and I am in heaven. Entered in that first pageant, the path to my future became evident. A future I still look forward to every day.

Story Complete For Now

© 2016 thru 2021 Fran Cesca Walker

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