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Printed from https://www.writing.com/main/interactive-story/item_id/1745122-Stuck-in-Skirts/cid/2115430-Prom-dress
by Spooky Author IconMail Icon
Rated: GC · Interactive · Other · #1745122

My shot at a compilation about gender bending be it crossdressing, magic, sci fi, whatever

This choice: Prom dress  •  Go Back...
Chapter #35

Prom dress

    by: Unknown
Being laden with so many bags slows you all down considerably so by the time you have reached the formalwear store, all three of you are exhausted. As you enter you gaze around, marvelling at all the fine tailoring that has gone into create such beautiful dresses and you mentally take some notes that you could apply to your own school fashion project.

"Hello there ladies." A cheerful shop worker approaches you. "How can I assist you today?"

Your mom drops the bags and gestures to the woman that she needs a moment to get her breathe back. The woman waits patiently still smiling. " Sorry about that" your mom says finally. "Hello, um yes. We are here for my daughter Jessie here. Her school prom is next week as well as her birthday so I would like to treat to a very nice dress, shoes and set of lingerie."

It takes you a moment to realise that she is talking about you since she referred to you as a her but luckily you keep your mouth shut so as not to blow your cover.

"Very good and does the young lady have any idea of what kind of dress she would like?" The woman asks.

Your mom looks down at you and you shrug. You hadn't really given much thought into what type of dress you might want to wear since you had almost given up hope on going with no one asking you.

"Perhaps we could see what you recommend." Your mom says.

"Of course, if you can undress for me in that changing room for me, I will bring you some dresses that you can try on." She leads you to the changing room and hurries off back into the store to fetch your dresses.

When in the changing room you stip down to your bra and panties. With the wall to wall mirrors of the changing room you can appreciate your assets from all angles. There is no doubt, the woman will never in here wildest imagination consider you as a boy. Your small penis really works to your advantage as there is no bulge what so ever. When finished admiring yourself, you peak through the curtain. "Mom, I'm ready, should I come out?"

"Go ahead Jessie."

Taking a deep breathe, you step out into the world.

"Why aren't you a pretty thing" the woman says by a rack of dresses. "You've really come into your body haven't you." You blush at this and then feel your mom's hand on your shoulder.

"I'm really proud of you Jessie" she whispers and you fell great.

Your time in the shop is spent putting on and taking off multiple dresses, finding out what you think of it and then running it past the expert panned of Sam and your mom for approval. Your mom seems to like the more sexy looking dresses while Sam likes the cute and flirty ones but none they both agree on you seem to like. Finally there is a winner however in the form of a cream chiffon dress with pearl lining on the neck. You love it and it gets the important thumbs up from Sam and your mom and even the shop assistant says it is probably the best choice. Having settled on the dress, you reluctantly climb out of it and are then presented with a pair of nude 5 inch heels to try on. While not as comfy as the black pair you just bought, they are very nice and compliment your dress perfectly. After taking these off and handing them to the woman, you are led to the lingerie section.

"Mom, why do I have to get lingerie for the prom? I'm not complaining put isn't it just about the dress." You ask when waiting to be given a set to try on.

"It's about confidence honey. Knowing that you look gorgeous all the way through can be a great boost to self esteem. Also you do want to please your date right?" She gives you a wink and a nudge at this.

You are about to reply concerning the implications of your date seeing you only lingerie and possible progression from that point but the woman returns holding a sheer and lacy teddy the same colour as your dress.

"Here try this on. I guarantee that you won't be disappointed." She hands you the lingerie and ushers you into another changing room. You take off you panties causing your tiny cock to flop free and then tentatively take off your bra, shivering slightly as your hands caress them. You then dress yourself in the teddy, enjoying its soft material rubbing against your body. Looking in the mirror you gasp. You look like a woman straight out of a Victoria's Secret catalog. Hearing your gasp, your mom draws open the curtain.

"Jessie are you alight wow..." She is stopped in here tracks and stares at you. You turn to her and see tears welling in her eyes. "You've grown up." She says and rushes to embrace you, this time with more concern for your breasts.

"I told you that it wouldn't disappoint." The woman says. "Am I right to assume you would like the set?"

"Yes yes." Your mom says still hugging you.

"Very good. I will just get the matching stockings and take all your items to the counter so you may pay. Would be so kind to redress yourself in your clothes?"

Your mom very reluctantly lets go of you and allows you to redress in your skirt and jumper. When dressed you all go to the counter so your mom can pay. Though you fear the price for these beautiful clothes is very large, your mom doesn't even bat an eye lid producing her bank card and eagerly entering her pin.

"Thank you mom" you say.

"No Jessie thank you. I know these past few weeks haven't been exactly easy for you but you and your sister" she points to Sam "have made me so proud and happy, these clothes are the least I could do."

Your surprised how emotional your mom is getting about all this but you give her another hug anyway.

When all is paid for and you are now given more bags to carry, you mom checks the time.

"Well it's time to head home. I told Sarah and Ella to either meet us outside this store or back at the car. Let's hope they're just outside. I don't think I could make it with all these bags and you two can't carry too much."
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