PG 13 I Dress~up With Penny
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[INDENT]It was suggested to me that I should post this in Sissy Kiss Story Time.

This is a love story of sorts. It is a combination of my true experiences as well as my fantasies. I hope that you enjoy reading it as much as I did writing all about it....



I loved to visit my cousin because, well, she was a girl. And I was more at home with my cousin, Penny, than my guy friends back then in the mid-fifties. You might of thought that she was my best friend at the time.

She was about nine, a year younger than me. Her Mom always got her the prettiest dresses and things. And I'd love to go over when she got something really pretty and frilly to show me. You see, Penny was all girl, not a shred of tomboy in her. I guess she could tell that I had that special look when she would show or wear her latest party dress or other frillies. That look said, "I wish I could wear that pretty dress". And so, this latest visit was going to turn out to be different, but I just didn't know it yet.

Now Penny's Mom was the nicest lady you could ever meet, and she loved to have Penny and I play together, especially when we played non-violent girl's games like jacks or hopscotch. So when Penny asked her if we could play "dress-up", it was a done thing, as long as we did it quietly inside. Penny led me by the hand into her bedroom, which, to me, was little girl heaven. Everything was in shades of soft pink pastel and white, including the ruffled organdy curtains and satin bed sham and pillow cases. I felt all of a sudden an aura of femininity in such a satiny, lacey world, a little un-nerving for a boy that was the best hitter on his little league team.

Penny changed out of her yellow jumper and low cut sneakers of the day, and selected a beautiful poufy white party dress and what I later found out was called a white bouffant petticoat slip from her closet. She changed her cotton panties inside the closet, where I couldn't see, for a pink satin pair of panties with rows of lace ruffles on the bum she said were called rhumba panties. They even had frilly lace around the leg openings and a small dainty white satiny bow above the frilly rows of lace. She pulled the slip over her head and shook the skirts out, and with a pretty twirl, asked if I would like one like it to wear for dress-up. Now, I was speechless. I just nodded not knowing why I did. In spite of being a year older than Penny, I was thin as could be, so we knew fitting into her pretties would be no problem for me. But I was starting to have a problem because my little man was starting to stir. She retrieved a pair of pink satin rhumba panties from her panty drawer, and handed them to me saying, "the ruffles go in the back, Ricky". I was shaking and stood there looking at these panties just dripping with feminine frills. I suppose my face was super flushed too because she said, " hey, you're blushing"! No kidding Sherlock. I went into her closet as directed and took off my jeans and briefs where I couldn't be seen. I didn't know if I could do this! I mean, yeah, I had thought about this, but actually putting on girl's panties. And slippery satin ones at that!

"What's keeping you, Ricky" she said with impatience. " Do you need some help?".

" Mom, Ricky needs help with his panties". That did it! I quickly stepped into the slippery confection and pulled them up my legs. Oops, the ruffles go in the rear! This was getting critical. Penny's calling for her Mom to help me, my little man is not cooperating, and here I am fumbling around with little girls panties like a drunken fly!

Having got the panties on before reinforcements arrived, I rejoined Penny to find her holding up the pale pink bouffant petticoat slip to me, saying, "This should do nicely, they match your panties. Hold out your arms!" Now, looking at the slip, my arms feel like they weigh a ton each! " Come on, it won't bite you". She worked the slip over my arms, then my head, and pulled it down to settle over my hips to just above my knees. She fluffed it out and fixed the tiny ribbon straps properly over my shoulders. And I thought to myself, "thank goodness, she can't see my little man under this slip acting up now." I rubbed my hands over what she told me was the nylon tricot bodice, noting delicate lace trim at the top of the bodice with a pretty little pink bow in the middle. " Oh, if the guys on my team ever saw me now, I'd be dog meat for sure". Penny broke into my thoughts explaining that the underskirt was something called taffeta or paper something or other, and the outer layer was called tiered nylon net, and did I like how it felt. Well, It stood out so far from my waist that no way was I going to see my feet! None of my boys’ clothes ever felt this nice and slippery. I noticed that the taffeta and the stiff net seemed to rustle when I rubbed it against my thighs. And OMG. What a feeling! Now, between the panties and slip, my little man was really going out of his mind!

Penny was not one to linger. Approaching me with her pink confection of a party dress that, she informed me, was nylon organdy over satin. "Arms up", she demanded. and up my arms and over my head it went, swishing and rustling the whole time. My head popped through as Penny pulled the dress down adjusting the skirts and short puff sleeves as she went. Now, the sleeves felt funny because they had little elastics that that closed softly but firmly on my upper arms- another new feeling I was to note is not in the boys world. Penny buttoned me up in the back and tied a wide pink satin sash around my waist in the back into a large bow. "She's making me into a girl, well, into what I look like a girl!", I thought. A mixture of emotions raced through me- I’m not a girl, but I feel like a girl!

"Penny, I don't know about this...", I said, having second thoughts about entering into this 'sissy' world.

" Oh, you look very pretty, Ricky. Don't you feel pretty? ", she commented as she primped here and there on my dress, and then on hers. She asked me if I would button up her dress like she did for me, and tie her sash into a bow too. Every time I went to move, my skirts would swish making this delightful sound. The skirts of both the dress and petticoat slip were so stiff that the dress stood way out to my sides. I wondered how I could sit in this dress without displaying my frills to all around me.

"Come look in the mirror", Penny suggested, pulling me in the direction of a full length mirror located on her closet door.

" I've turned into a little girl like Penny", I thought. There in front of me was a little girl, but with my face! I liked it, but felt terrified at the same time. I swished from side to side and twirled looking at how the skirts went out. There are my panties! I can see my panties when I twirl, just like the girls at the playground.

"You look so pretty, Ricky”, Penny commented. " Mom, come look at Ricky! He's really pretty in my pink party dress and slip!".

"So this is what girls call dress-up. Secretly", I thought to myself, " I could possibly get to enjoy this! What am I saying! I’m a boy!” Confusion started to set in. Boys aren't suppose to think like this!

Again, Penny broke into my thoughts by telling me that " we're not finished yet". Leading me over and sitting me on the edge of her bed, she started to pull off my socks and pull some others on my feet. But these had some dainty lace around the tops of them when she turned them down! Penny said they were pretty white anklets with pink lace ruffles to match my pink party dress. She said it was what all the girls wore when they dressed up for something special, like church or parties. They certainly looked girlish to me, I thought to myself. I had to hold my skirts down in order to get a good look at them. She was right, they certainly were pretty! While I was still immersed in thought, Penny produced a shiny black pair of shoes for little girls. She called them Mary Janes, and said they were made from something called patent leather. Our feet must have been about the same size because she slipped them on my feet rather easily and fastened a strap with a shiny buckle over the tops of my feet. Penny jolted me with, " Wouldn't you like to go to school tomorrow in this pretty outfit, Ricky?" Now, the thought of this just terrified me! I couldn’t think of what to say for a moment, and I’m not usually one to be at a loss for words!

"Yeah right", I said, “I suppose you think I'll fit right in with the rest of the girls!"

"They would think you look so cute", Penny continued to rib me.

"Yeah, if I don't get beaten to a pulp by the jocks", I said.

" Here, let me get a picture of you", as she started for the camera.

"NO WAY!", I said, starting to panic at the thought that she might actually do it!

“Then, at least let's show Mom how you look."

" Um, I don't know. I feel kind of foolish dressed like this, Penny", semi-pleading for her to reconsider.

But it was too late. "Mom! Mom!", she called twice. I ducked into penny's closet to hide and think.

"Come on out of there, Ricky. Mom, wait 'till you see him, Mom." Penny giggled almost uncontrollably. Frozen in place, penny grabbed my wrist and pulled me from the safety of her closet. Her Mom, standing there, her jaw dropped with surprise and then turned slowly into a smile.

" Oh my gosh, Ricky. You are just so adorable! Penny has done a nice job for your dress-up." She had to turn away for a quick moment to stifle a giggle coming on.

" Thank you, Auntie," I said not being able to think of anything else to say.

Penny broke in with, "Want to try on another outfit, Ricky?"

"Well, maybe Ricky has had enough for one day, Penny", as her Mom saved me from having my face catch fire from the super blush I could feel from the heat coming from my face. Penny and I finally played hopscotch in her back yard for a while, making sure that it was sheltered sufficiently from the street and neighbors by high hedges. Later, I undressed, with the help of her Mom, after realizing that I couldn't reach all the buttons on the back of the dress. I left Penny's home wondering about the experience I just had into the world of little girls, and how her Mom just coo'ed over us. It was a good feeling. Boys didn't get that kind of attention, I thought. And my little man desperately needed a rest.

There would be other "dress-up" times that I would have with Penny. But, as nice as they were, they would never be as special as that first time with my cousin.

To my knowledge, no one else ever knew of our dress-up play together outside of her Mom and her baby sister. We'd talk about it now and then when we were alone. We eventually went our separate ways going through school, college, then marriage and children. We would keep in touch, especially through the Holidays, and share the latest developments in our immediate families. And occasionally, we would talk about our secret dress-up sessions as kids.


Penny passed away last year after a long bout with Cancer. I miss her very much. I know that we shared something special for those few years when we were just little kids. But I'm thankful for the special memories we forged together in our party dresses back in an age of innocence, and how, as a young boy, she presented to me an opportunity to feel a side of the fairer gender that few males get to experience. Thank you, Penny. I love you….

[/INDENT]
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mya
thaks fur the store
 Princess are kind, brave, beautiful and determined they can do or be anything 
                                  
even change the world.  

 All girls are princess what you see in the Mirrors doesn't define you.
 
It doesn’t meter if you weren't born a girl. As long as your one at heart you too
are a princess 

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HarperMaybel
Very cute story
If you want a sun shower, you'll have to put up with the rain.
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eleventhdr


 
[INDENT]It was suggested to me that I should post this in Sissy Kiss Story Time.

This is a love story of sorts. It is a combination of my true experiences as well as my fantasies. I hope that you enjoy reading it as much as I did writing all about it....



I loved to visit my cousin because, well, she was a girl. And I was more at home with my cousin, Penny, than my guy friends back then in the mid-fifties. You might of thought that she was my best friend at the time.

She was about nine, a year younger than me. Her Mom always got her the prettiest dresses and things. And I'd love to go over when she got something really pretty and frilly to show me. You see, Penny was all girl, not a shred of tomboy in her. I guess she could tell that I had that special look when she would show or wear her latest party dress or other frillies. That look said, "I wish I could wear that pretty dress". And so, this latest visit was going to turn out to be different, but I just didn't know it yet.

Now Penny's Mom was the nicest lady you could ever meet, and she loved to have Penny and I play together, especially when we played non-violent girl's games like jacks or hopscotch. So when Penny asked her if we could play "dress-up", it was a done thing, as long as we did it quietly inside. Penny led me by the hand into her bedroom, which, to me, was little girl heaven. Everything was in shades of soft pink pastel and white, including the ruffled organdy curtains and satin bed sham and pillow cases. I felt all of a sudden an aura of femininity in such a satiny, lacey world, a little un-nerving for a boy that was the best hitter on his little league team.

Penny changed out of her yellow jumper and low cut sneakers of the day, and selected a beautiful poufy white party dress and what I later found out was called a white bouffant petticoat slip from her closet. She changed her cotton panties inside the closet, where I couldn't see, for a pink satin pair of panties with rows of lace ruffles on the bum she said were called rhumba panties. They even had frilly lace around the leg openings and a small dainty white satiny bow above the frilly rows of lace. She pulled the slip over her head and shook the skirts out, and with a pretty twirl, asked if I would like one like it to wear for dress-up. Now, I was speechless. I just nodded not knowing why I did. In spite of being a year older than Penny, I was thin as could be, so we knew fitting into her pretties would be no problem for me. But I was starting to have a problem because my little man was starting to stir. She retrieved a pair of pink satin rhumba panties from her panty drawer, and handed them to me saying, "the ruffles go in the back, Ricky". I was shaking and stood there looking at these panties just dripping with feminine frills. I suppose my face was super flushed too because she said, " hey, you're blushing"! No kidding Sherlock. I went into her closet as directed and took off my jeans and briefs where I couldn't be seen. I didn't know if I could do this! I mean, yeah, I had thought about this, but actually putting on girl's panties. And slippery satin ones at that!

"What's keeping you, Ricky" she said with impatience. " Do you need some help?".

" Mom, Ricky needs help with his panties". That did it! I quickly stepped into the slippery confection and pulled them up my legs. Oops, the ruffles go in the rear! This was getting critical. Penny's calling for her Mom to help me, my little man is not cooperating, and here I am fumbling around with little girls panties like a drunken fly!

Having got the panties on before reinforcements arrived, I rejoined Penny to find her holding up the pale pink bouffant petticoat slip to me, saying, "This should do nicely, they match your panties. Hold out your arms!" Now, looking at the slip, my arms feel like they weigh a ton each! " Come on, it won't bite you". She worked the slip over my arms, then my head, and pulled it down to settle over my hips to just above my knees. She fluffed it out and fixed the tiny ribbon straps properly over my shoulders. And I thought to myself, "thank goodness, she can't see my little man under this slip acting up now." I rubbed my hands over what she told me was the nylon tricot bodice, noting delicate lace trim at the top of the bodice with a pretty little pink bow in the middle. " Oh, if the guys on my team ever saw me now, I'd be dog meat for sure". Penny broke into my thoughts explaining that the underskirt was something called taffeta or paper something or other, and the outer layer was called tiered nylon net, and did I like how it felt. Well, It stood out so far from my waist that no way was I going to see my feet! None of my boys’ clothes ever felt this nice and slippery. I noticed that the taffeta and the stiff net seemed to rustle when I rubbed it against my thighs. And OMG. What a feeling! Now, between the panties and slip, my little man was really going out of his mind!

Penny was not one to linger. Approaching me with her pink confection of a party dress that, she informed me, was nylon organdy over satin. "Arms up", she demanded. and up my arms and over my head it went, swishing and rustling the whole time. My head popped through as Penny pulled the dress down adjusting the skirts and short puff sleeves as she went. Now, the sleeves felt funny because they had little elastics that that closed softly but firmly on my upper arms- another new feeling I was to note is not in the boys world. Penny buttoned me up in the back and tied a wide pink satin sash around my waist in the back into a large bow. "She's making me into a girl, well, into what I look like a girl!", I thought. A mixture of emotions raced through me- I’m not a girl, but I feel like a girl!

"Penny, I don't know about this...", I said, having second thoughts about entering into this 'sissy' world.

" Oh, you look very pretty, Ricky. Don't you feel pretty? ", she commented as she primped here and there on my dress, and then on hers. She asked me if I would button up her dress like she did for me, and tie her sash into a bow too. Every time I went to move, my skirts would swish making this delightful sound. The skirts of both the dress and petticoat slip were so stiff that the dress stood way out to my sides. I wondered how I could sit in this dress without displaying my frills to all around me.

"Come look in the mirror", Penny suggested, pulling me in the direction of a full length mirror located on her closet door.

" I've turned into a little girl like Penny", I thought. There in front of me was a little girl, but with my face! I liked it, but felt terrified at the same time. I swished from side to side and twirled looking at how the skirts went out. There are my panties! I can see my panties when I twirl, just like the girls at the playground.

"You look so pretty, Ricky”, Penny commented. " Mom, come look at Ricky! He's really pretty in my pink party dress and slip!".

"So this is what girls call dress-up. Secretly", I thought to myself, " I could possibly get to enjoy this! What am I saying! I’m a boy!” Confusion started to set in. Boys aren't suppose to think like this!

Again, Penny broke into my thoughts by telling me that " we're not finished yet". Leading me over and sitting me on the edge of her bed, she started to pull off my socks and pull some others on my feet. But these had some dainty lace around the tops of them when she turned them down! Penny said they were pretty white anklets with pink lace ruffles to match my pink party dress. She said it was what all the girls wore when they dressed up for something special, like church or parties. They certainly looked girlish to me, I thought to myself. I had to hold my skirts down in order to get a good look at them. She was right, they certainly were pretty! While I was still immersed in thought, Penny produced a shiny black pair of shoes for little girls. She called them Mary Janes, and said they were made from something called patent leather. Our feet must have been about the same size because she slipped them on my feet rather easily and fastened a strap with a shiny buckle over the tops of my feet. Penny jolted me with, " Wouldn't you like to go to school tomorrow in this pretty outfit, Ricky?" Now, the thought of this just terrified me! I couldn’t think of what to say for a moment, and I’m not usually one to be at a loss for words!

"Yeah right", I said, “I suppose you think I'll fit right in with the rest of the girls!"

"They would think you look so cute", Penny continued to rib me.

"Yeah, if I don't get beaten to a pulp by the jocks", I said.

" Here, let me get a picture of you", as she started for the camera.

"NO WAY!", I said, starting to panic at the thought that she might actually do it!

“Then, at least let's show Mom how you look."

" Um, I don't know. I feel kind of foolish dressed like this, Penny", semi-pleading for her to reconsider.

But it was too late. "Mom! Mom!", she called twice. I ducked into penny's closet to hide and think.

"Come on out of there, Ricky. Mom, wait 'till you see him, Mom." Penny giggled almost uncontrollably. Frozen in place, penny grabbed my wrist and pulled me from the safety of her closet. Her Mom, standing there, her jaw dropped with surprise and then turned slowly into a smile.

" Oh my gosh, Ricky. You are just so adorable! Penny has done a nice job for your dress-up." She had to turn away for a quick moment to stifle a giggle coming on.

" Thank you, Auntie," I said not being able to think of anything else to say.

Penny broke in with, "Want to try on another outfit, Ricky?"

"Well, maybe Ricky has had enough for one day, Penny", as her Mom saved me from having my face catch fire from the super blush I could feel from the heat coming from my face. Penny and I finally played hopscotch in her back yard for a while, making sure that it was sheltered sufficiently from the street and neighbors by high hedges. Later, I undressed, with the help of her Mom, after realizing that I couldn't reach all the buttons on the back of the dress. I left Penny's home wondering about the experience I just had into the world of little girls, and how her Mom just coo'ed over us. It was a good feeling. Boys didn't get that kind of attention, I thought. And my little man desperately needed a rest.

There would be other "dress-up" times that I would have with Penny. But, as nice as they were, they would never be as special as that first time with my cousin.

To my knowledge, no one else ever knew of our dress-up play together outside of her Mom and her baby sister. We'd talk about it now and then when we were alone. We eventually went our separate ways going through school, college, then marriage and children. We would keep in touch, especially through the Holidays, and share the latest developments in our immediate families. And occasionally, we would talk about our secret dress-up sessions as kids.


Penny passed away last year after a long bout with Cancer. I miss her very much. I know that we shared something special for those few years when we were just little kids. But I'm thankful for the special memories we forged together in our party dresses back in an age of innocence, and how, as a young boy, she presented to me an opportunity to feel a side of the fairer gender that few males get to experience. Thank you, Penny. I love you….

[/INDENT]  






Yes it is a real pty that so many of us little boys never got this chance like you did how i to would ahve loved to ahve had an oppertuinty to at last get into little girls cloths and be all girly as often as i could ahve as i can still recall ow cute and pretty little girls used to dress vack in the late 1950's and early 1960's and how i had to keep quite of my own secret desires to be ion even thier regular day dresses when they used to come to school in pastel dresses i was so envious and wanted to be in them and to be girly to run and playin a dress instead of silly stupid boys cloths girls were so lucky back than they got to wear such cute pretty clpths whilke we boys were stick in yucky jeans and pants with little to no imagination at all little girls got to play thier gilry games and could be seen playing quietly and i wanted to join them and be a little girl at last in a cute dress and i still feel tis way even tod ay all this time later to go back and be one of those little girls yes i would chuck it all to be a little girly girl i nevrer had any sistgers but wished i had been a girl and a sisiter so i to could ahve been playing outside with all of the other little girls doing only what girls can do i still wish i were a little girl
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