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I started a fiction short story over 10 years ago, but never finished it. It’s G rated and features the type of ultra-feminine clothing from the 1950’s that I love.
*****
HIGH SCHOOL SENIOR BOY BECOMES PROM GIRL By Sheila Tampa
Randy Lassiter is a 17 year-old high school senior. He is 5’6” tall and quite slim. He has a very attractive ”pretty boy” face and longish yellow blonde hair. Although extremely good-looking, he is also very shy, and he has no date for the senior prom, which is just two days away.
Keith Mandarole is Randy’s best friend. Keith is the president of the student council. He had a date for the prom, but he and his date had an argument this afternoon, and now he has no date. With only a week left until the big event, and virtually all girls accounted for, Keith fears he will have to attend alone, which would be very embarrassing for the student council president.
Keith’s 21 year old sister, Amy, when hearing of Keith’s predicament, has a brilliant idea! Randy has no date for the prom, is small and “pretty”, and as Keith’s best friend, should help him out by becoming his date for the prom as a girl. . Keith realizes this is the only way he can attend the prom with a beautiful “girl”. Amy and Keith invite Randy over to their house, and they spring their plan on him. Randy is shocked and upset at their idea, and firmly shouts, “No way”! However, after Amy and Keith lay a “guilt trip” on Randy if he does not help save his best friend from the embarrassment of not having a date for the prom, he relents and agrees to become a girl for the prom. Amy tells Randy to come back Saturday morning, and she will have everything Randy will need to become a beautiful girl.
Saturday morning, Randy dutifully arrives for his first “transformation” . Amy tells Keith to wait in the living room while she supervises Randy’s first time in becoming a girl. Amy tells Randy that he will now undergo a complete 100% image transformation from boy to girl. She explains that she will not be dressing him for the prom this time, but she wants him to feel how other girls’ outfits will feel before she dresses him in a prom gown. The prom gown will be pink, and will be worn over 2 or 3 soft flaring ruffled petticoats. Amy wants Randy to feel how it is to wear a cocktail dress over more standard, non-petticoated lingerie.. After Randy takes a delightfully scented bubble bath, Amy helps him shave his legs, arms, and underarms. Next she hands him a pink gaff, which is a garment to hide any trace of masculinity. Randy starts to feel real trepidation as he snugs himself into this dainty garment which hides any trace of masculine anatomy in the “privates” area.
Next, Amy hands Randy a pair of pink, lace-trimmed, wispy nylon tricot panties. Randy protests, ”Why can’t I just wear my male jockey shorts?”. Amy insists that any male undershorts would be took bulky, and he will have to wear all lingerie under his outerwear to give the proper feminine appearance. “Besides”, she says with a sly smile, “I think you will grow to love knowing that you have gorgeous girly lingerie under your outerwear”. So, with great embarrassment, Randy steps into the girlie panties and slowly pulls them up his legs and snugly into place.
Next, Amy tells Randy to put on the sweet matching pink nylon tricot bra with luscious lace trim. She helps him into the dainty garment, and fastens the hooks on the back. Amy hands Randy a pair of breast forms, which she borrowed from her female impersonator friend, Nadine. She had gotten the pink gaff from Nadine also. Randy starts to feel an odd, but pleasant, tingle as he glances at his girlish image in the mirror in his pretty bra and panties. Amy gives Randy a lacy pink garter belt with 6 dangling straps. A pair of shiny taupe nylons are next. Inwardly, Randy is really starting to enjoy becoming a girl. Amy supervises him carefully pulling up his nylons, and attaching each stocking to the 3 garter straps for each leg. Amy says, “Randy, this is fun, isn’t it? Now you know why we girls are so into our marvelous feminine clothing and lingerie”. Randy is surprised to realize that he is secretly enjoying this, but he lies, “No, I am only doing this for Keith, and I find this to be very embarrassing”.
Randy sees the next wonderful garment he will put on. It is an absolutely luscious pink nylon tricot full slip, with lots of wispy lace at the bodice, and a 2 inch high lace trimmed hem with a dainty flower pattern. The gorgeous satiny slip matches his bra and panties. He blushes and he slowly dons this beautiful and ultra feminine garment. He takes a few steps, and can’t believe how wonderful the slip feels as it swishes on his legs and caresses his panties. He starts to inwardly swell with emotion, and realizes, “I just adore this”.
Amy says that now that he has finished donning his lingerie, it’s time to apply his makeup. She wants Randy to learn how to apply his own makeup, so she supervises in detail, as she has Randy apply foundation, blue eye shadow, eye liner, mascara, use an eyebrow pencil to shape his brows into a beautiful feminine shape, and ruby red lipstick. Amy has borrowed a long blonde wig from Nadine, and she carefully puts it on Randy. Randy looks in the mirror at the stunningly beautiful, ultra-feminine teenage girl staring back at him. He turns his away from Amy for a minute, to hide the fact that is overcome with emotion and just barely keeps himself from crying. Here he is, a 17 year old boy, made up as a beautiful girl, and wearing the most delightful lingerie. He can’t believe how gorgeous he looks and feels in his lovely full slip, bra, and panties.
Shiny classic black patent leather pumps with 3” spike heels are gently fitted onto his feet. He loves how it feels as the nylons are inserted into the strange feeling woman’s shoes. The open toed pumps display his nylon clad toes peeking out, and there is a dainty bow on each toe. Amy suggests that Randy put on all his jewelry before he puts on his dress. So, he slowly puts on silver dangly clip-on earrings, a beautiful pearl necklace, a dainty ladies watch, and a beautiful ring with a large bluish stone. Next, Amy lovingly paints Randy’s fingernails in a red that matches his lipstick. The final step is to slowly step into a wispy powder blue satin chiffon cocktail dress with a flaring skirt, and a sequined bodice. The dress ends about 2 inches below his knees. The skirt of the dress swishes delightfully against his legs as he moves, and he is thrilled that he can actually feel his pretty slip swishing against his pretty pink panties, and his dress lovingly caressing the slip. “God, no wonder girls love being girls – this is fantastic”, he thinks to himself.
Amy takes Randy’s hand, and slowly leads him into the living room where Keith is waiting. Right before they step into Keith’s view, Amy whispers affectionately to Randy, “Girl, you are simply gorgeous, and I know you are loving this, but that will just be our little secret. “Well, Keith”, Amy bubbles, “isn’t SHE gorgeous”. Randy secretly loves that he is being referred to as SHE. Keith almost falls off his chair in disbelief at how unbelievably gorgeous and feminine his best buddy is.
SECOND DRESSING SCENE
Keith joins Amy and Randy to witness the entire transformation from guy to girl. Randy comes out of the bathroom wearing only the pink gaff. Amy hands him a pair of the sweetest, girliest nylon tricot yellow ruffled “sissy” panties. As Randy slowly pulls the shimmering, satiny panties up his legs, he secretly loves the feeling, and the way the panties look on his body. Seeing his buddy smoothing the ruffled panties into place, Keith starts doubting his friend’s masculinity.
Next, Amy helps Randy fasten his white nylon tricot bra, and place inserts into the cups to give a beautiful womanly shape. A white lace garter belt is next, and the 4 straps are gingerly pulled under the sissy panties. Randy slowly and lovingly pulls up both his light coffee-colored nylon stockings and attaches them to the garter straps. Keith is starting to get secretly turned on, since he always did watching his girl friends in their lingerie, and Randy is turning into a very pretty girl wearing very pretty lingerie.
Next, Amy hands Randy a very beautiful white lace-trimmed nylon tricot camisole. Randy just adores the image in the mirror of him in his cami, panties, and nylons. Amy tells the guys that she now has a surprise. She leaves the room for a minute, and comes back with an armful of yellow ruffles. They turn out to be 2 incredibly soft, nylon tricot yellow ruffled flaring petticoats. Randy can hardly contain himself as Amy helps him step into not one, but both of the girlie petticoats. The two together flare very widely from his legs, and the sensation of the petticoats shifting against his legs and ruffled panties is incredible!
“Now for the ‘piece de resistance’”, states Amy. She hands Randy the most frilly, girlie, sweet yellow satin chiffon prom dress with puffed shoulders and “little girl” bow in the back. He has to fight the powerful wave of emotion that nearly overcomes him, as he steps into the stunning gown. The satin chiffon skirt flares way out, showing just the very bottom of the ruffles of his girlie petticoats. The feeling of moving in this adorable clothing is indescribable in Randy’s mind. He just ADORES it!
*****
That’s all I wrote, and probably will never finish it, but this is the type of CD fiction I love to read.
Hi Girls,
There are a few typos in my story … sorry about that, but I think you’ll know how to read through those typos. Also, there’s a “continuity” mistake … the beginning of the story says the prom is just 2 days away, but later it appears the prom is farther in the future.
Nevertheless, I hope you enjoy!
2016_poets corner: Sheila Tampa original post:
I started a fiction short story over 10 years ago, but never finished it. It’s G rated and features the type of ultra-feminine clothing from the 1950’s that I love.
*****
HIGH SCHOOL SENIOR BOY BECOMES PROM GIRL By Sheila Tampa
Randy Lassiter is a 17 year-old high school senior. He is 5’6” tall and quite slim. He has a very attractive ”pretty boy” face and longish yellow blonde hair. Although extremely good-looking, he is also very shy, and he has no date for the senior prom, which is just two days away.
Keith Mandarole is Randy’s best friend. Keith is the president of the student council. He had a date for the prom, but he and his date had an argument this afternoon, and now he has no date. With only a week left until the big event, and virtually all girls accounted for, Keith fears he will have to attend alone, which would be very embarrassing for the student council president.
Keith’s 21 year old sister, Amy, when hearing of Keith’s predicament, has a brilliant idea! Randy has no date for the prom, is small and “pretty”, and as Keith’s best friend, should help him out by becoming his date for the prom as a girl. . Keith realizes this is the only way he can attend the prom with a beautiful “girl”. Amy and Keith invite Randy over to their house, and they spring their plan on him. Randy is shocked and upset at their idea, and firmly shouts, “No way”! However, after Amy and Keith lay a “guilt trip” on Randy if he does not help save his best friend from the embarrassment of not having a date for the prom, he relents and agrees to become a girl for the prom. Amy tells Randy to come back Saturday morning, and she will have everything Randy will need to become a beautiful girl.
Saturday morning, Randy dutifully arrives for his first “transformation” . Amy tells Keith to wait in the living room while she supervises Randy’s first time in becoming a girl. Amy tells Randy that he will now undergo a complete 100% image transformation from boy to girl. She explains that she will not be dressing him for the prom this time, but she wants him to feel how other girls’ outfits will feel before she dresses him in a prom gown. The prom gown will be pink, and will be worn over 2 or 3 soft flaring ruffled petticoats. Amy wants Randy to feel how it is to wear a cocktail dress over more standard, non-petticoated lingerie.. After Randy takes a delightfully scented bubble bath, Amy helps him shave his legs, arms, and underarms. Next she hands him a pink gaff, which is a garment to hide any trace of masculinity. Randy starts to feel real trepidation as he snugs himself into this dainty garment which hides any trace of masculine anatomy in the “privates” area.
Next, Amy hands Randy a pair of pink, lace-trimmed, wispy nylon tricot panties. Randy protests, ”Why can’t I just wear my male jockey shorts?”. Amy insists that any male undershorts would be took bulky, and he will have to wear all lingerie under his outerwear to give the proper feminine appearance. “Besides”, she says with a sly smile, “I think you will grow to love knowing that you have gorgeous girly lingerie under your outerwear”. So, with great embarrassment, Randy steps into the girlie panties and slowly pulls them up his legs and snugly into place.
Next, Amy tells Randy to put on the sweet matching pink nylon tricot bra with luscious lace trim. She helps him into the dainty garment, and fastens the hooks on the back. Amy hands Randy a pair of breast forms, which she borrowed from her female impersonator friend, Nadine. She had gotten the pink gaff from Nadine also. Randy starts to feel an odd, but pleasant, tingle as he glances at his girlish image in the mirror in his pretty bra and panties. Amy gives Randy a lacy pink garter belt with 6 dangling straps. A pair of shiny taupe nylons are next. Inwardly, Randy is really starting to enjoy becoming a girl. Amy supervises him carefully pulling up his nylons, and attaching each stocking to the 3 garter straps for each leg. Amy says, “Randy, this is fun, isn’t it? Now you know why we girls are so into our marvelous feminine clothing and lingerie”. Randy is surprised to realize that he is secretly enjoying this, but he lies, “No, I am only doing this for Keith, and I find this to be very embarrassing”.
Randy sees the next wonderful garment he will put on. It is an absolutely luscious pink nylon tricot full slip, with lots of wispy lace at the bodice, and a 2 inch high lace trimmed hem with a dainty flower pattern. The gorgeous satiny slip matches his bra and panties. He blushes and he slowly dons this beautiful and ultra feminine garment. He takes a few steps, and can’t believe how wonderful the slip feels as it swishes on his legs and caresses his panties. He starts to inwardly swell with emotion, and realizes, “I just adore this”.
Amy says that now that he has finished donning his lingerie, it’s time to apply his makeup. She wants Randy to learn how to apply his own makeup, so she supervises in detail, as she has Randy apply foundation, blue eye shadow, eye liner, mascara, use an eyebrow pencil to shape his brows into a beautiful feminine shape, and ruby red lipstick. Amy has borrowed a long blonde wig from Nadine, and she carefully puts it on Randy. Randy looks in the mirror at the stunningly beautiful, ultra-feminine teenage girl staring back at him. He turns his away from Amy for a minute, to hide the fact that is overcome with emotion and just barely keeps himself from crying. Here he is, a 17 year old boy, made up as a beautiful girl, and wearing the most delightful lingerie. He can’t believe how gorgeous he looks and feels in his lovely full slip, bra, and panties.
Shiny classic black patent leather pumps with 3” spike heels are gently fitted onto his feet. He loves how it feels as the nylons are inserted into the strange feeling woman’s shoes. The open toed pumps display his nylon clad toes peeking out, and there is a dainty bow on each toe. Amy suggests that Randy put on all his jewelry before he puts on his dress. So, he slowly puts on silver dangly clip-on earrings, a beautiful pearl necklace, a dainty ladies watch, and a beautiful ring with a large bluish stone. Next, Amy lovingly paints Randy’s fingernails in a red that matches his lipstick. The final step is to slowly step into a wispy powder blue satin chiffon cocktail dress with a flaring skirt, and a sequined bodice. The dress ends about 2 inches below his knees. The skirt of the dress swishes delightfully against his legs as he moves, and he is thrilled that he can actually feel his pretty slip swishing against his pretty pink panties, and his dress lovingly caressing the slip. “God, no wonder girls love being girls – this is fantastic”, he thinks to himself.
Amy takes Randy’s hand, and slowly leads him into the living room where Keith is waiting. Right before they step into Keith’s view, Amy whispers affectionately to Randy, “Girl, you are simply gorgeous, and I know you are loving this, but that will just be our little secret. “Well, Keith”, Amy bubbles, “isn’t SHE gorgeous”. Randy secretly loves that he is being referred to as SHE. Keith almost falls off his chair in disbelief at how unbelievably gorgeous and feminine his best buddy is.
SECOND DRESSING SCENE
Keith joins Amy and Randy to witness the entire transformation from guy to girl. Randy comes out of the bathroom wearing only the pink gaff. Amy hands him a pair of the sweetest, girliest nylon tricot yellow ruffled “sissy” panties. As Randy slowly pulls the shimmering, satiny panties up his legs, he secretly loves the feeling, and the way the panties look on his body. Seeing his buddy smoothing the ruffled panties into place, Keith starts doubting his friend’s masculinity.
Next, Amy helps Randy fasten his white nylon tricot bra, and place inserts into the cups to give a beautiful womanly shape. A white lace garter belt is next, and the 4 straps are gingerly pulled under the sissy panties. Randy slowly and lovingly pulls up both his light coffee-colored nylon stockings and attaches them to the garter straps. Keith is starting to get secretly turned on, since he always did watching his girl friends in their lingerie, and Randy is turning into a very pretty girl wearing very pretty lingerie.
Next, Amy hands Randy a very beautiful white lace-trimmed nylon tricot camisole. Randy just adores the image in the mirror of him in his cami, panties, and nylons. Amy tells the guys that she now has a surprise. She leaves the room for a minute, and comes back with an armful of yellow ruffles. They turn out to be 2 incredibly soft, nylon tricot yellow ruffled flaring petticoats. Randy can hardly contain himself as Amy helps him step into not one, but both of the girlie petticoats. The two together flare very widely from his legs, and the sensation of the petticoats shifting against his legs and ruffled panties is incredible!
“Now for the ‘piece de resistance’”, states Amy. She hands Randy the most frilly, girlie, sweet yellow satin chiffon prom dress with puffed shoulders and “little girl” bow in the back. He has to fight the powerful wave of emotion that nearly overcomes him, as he steps into the stunning gown. The satin chiffon skirt flares way out, showing just the very bottom of the ruffles of his girlie petticoats. The feeling of moving in this adorable clothing is indescribable in Randy’s mind. He just ADORES it!
*****
That’s all I wrote, and probably will never finish it, but this is the type of CD fiction I love to read.
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