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Pinky's First Shopping Assignment

Disclaimer: All my stories are pure fiction, unless otherwise noted. Any similar events that may have occurred are purely coincidental.

*****

I just got home late at night from a rough day of work. I tossed my jacket on the kitchen chair, kicked off my shoes, got a beer from the fridge, and decided to sit down at my computer to check my messages before turning in to bed.

I did get a few messages. One of them was from a woman that I do general housecleaning for. You see, I'm a 49 year old male that does housecleaning while wearing a sissy maid uniform. And this woman loves sissy cross dressers and takes great pleasure in humiliating them.

Back to the message, it said:

"Pinky, tomorrow you are going shopping for a bra and panties. I've made arrangements with a good friend of mine who works at an intimate apparel store. She will be assisting you with your shopping. You are to report to her when you get there.

I'll e-mail you further details in the morning. The shopping assignment is to be in the afternoon. This should give you plenty of notice to make yourself pretty. Remove your body hair, paint your nails, etc.

Text me when you get this message.

Mary"

So I'm being sent to an unknown store to purchase a bra and panties for myself. This should be interesting. I texted Mary to let her know that I got her e-mail. She replied that she will contact me in the morning with additional details and to be ready to go when I get her instructions tomorrow. I ate, checked my other messages, and went to bed.

The next morning, I woke up to find another message in my inbox. It said:

"Pinky, you are to report to the shop at 1pm. Your contact's name is Sue. I'll text you the address when you leave. It's about 2 hours from your apartment, so be ready to leave at about 11am. Be sure your body hair have been removed, your nails are painted, you smell feminine, etc. And wear those pretty pink lace panties that you wore last time you cleaned for me as well as that black lace cami.

Mary"

I got into the shower right away and removed my body hair. It was easy because I had little body hair to begin with. I then used feminine body wash to cleanse myself with and got out of the shower.

After drying myself off, I sat down and clipped my fingernails and toenails. I then painted my nails a bright pink color. I didn't put any make up on though because I'm still inexperienced in the makeup department and Mary knows that or she would have told me to use makeup as well.

I put on my pink lace panties and a black lace cami top. I then selected a pair of Gloria Vanderbilt jeans to wear because they feel nice and girly, but can pass for male jeans if an observer doesn't look too hard. I put on a male t-shirt and shoes. I wasn't instructed to dress feminine or I would have selected feminine clothes instead. I had no idea where I was going, so I decided to be safe in dressing in male clothes for my shopping assignment.

It's almost 11am and I get the text message with the address on it. I go to my vehicle and got in and started it up. I mount my phone on the dashboard and input the address on a navigation app and off I go.

2 hours later, I pull in the parking lot of the intimate apparel store. I get out of my vehicle and do a deep breath. I then enter the store. It's full of bras, panties, pantyhose, etc. all on display. The store is not too busy. There's only a couple customers milling about. A pretty young woman came up to me. She couldn't be any older than 25.

"Hello. My name is Misty. How can I help you?" she said to me.

"Um, I'm supposed to meet a woman named Sue that works here," I said with a bit of hesitation in my voice.

"I'll go get her. Wait here a moment," said the girl.

I watched as the woman walked off to another part of the store. I saw her approach another woman, who was hanging bras on a display. The first woman pointed in my direction and the second woman nodded in acknowledgment, stopped what she was doing, and walked towards me. We shook hands. This woman appears to be in her early 30's.

"So you are Pinky, right?" said the woman.

"Yes, Ma'am," I replied.

"My name is Sue. Nice to meet you," she said as she was looking at my jeans. "Those are Gloria Vanderbilt jeans, right?"

Busted.

"Yes, Ma'am," I said.

Sue smiled a wicked smile and gestured in a general direction.

"Come this way please," she said, walking towards what appears to be a fitting room area.

She takes out a key from her pocket and opens the fitting room door and beckons me inside. She joins me in the fitting room and grabs a tape measure hanging on the wall.

"Take off your shirt please. I need to measure your chest," said Sue.

I hesitate a moment because if I remove my shirt, she'll see the black lace cami that I'm wearing underneath my shirt. Sue notices my hesitation.

"Pinky, take off your shirt - now," she said.

I comply and remove my shirt to reveal the black lace cami that I am wearing underneath the shirt. Sue smiles and tells me I can leave the cami on. She takes the tape measure and wraps it around my chest. After getting the measurement, she puts the tape measure away.

"Stay here. I'll be right back," she said as she left the fitting room.

I wait a moment and then I hear two voices talking to each other as they approach the fitting room. I'm like, oh no. Is Sue bringing her coworker Misty back with her? The door opens and sure enough, both Sue and Misty are standing in the doorway. Misty smiles.

"You're right. He is such a sissy," said Misty.

I blush at the comment and it is then I notice both women are each carrying a bra. Sue is carrying a pink bra and Misty has a red bra in hand. At that moment, a customer calls out for assistance. Misty hands the red bra to Sue.

"Have fun. Let me know how it goes," said Misty, walking off to help the customer.

Sue comes in the fitting room, shuts the door behind her and hangs up the red bra.

"All right, take off the cami. I want to put this bra on you to see how it fits," said Sue.

I take off the cami and hang it up. Sue puts the bra on me and adjusts it. She steps back to take a look and smiles. She takes her phone out of her pocket and snaps a picture of me wearing the bra before I could say anything.

"Don't worry. I'm sending this to Mary," said Sue. "Let's take off the bra and try on the other one."

I still feel embarrassed having my picture taken like that as Sue removes the red bra and puts on the pink one. She snaps a picture of me wearing that too and sends the picture.

"That pink bra really looks nice on you," Sue said.

I blush and at that moment Sue's phone chirps, indicating an incoming text message. She looks at it and smiles.

"Looks like Mary agrees. She likes the pink bra too," said Sue. "Let's take off the bra and get dressed. Mary wants you to go look for some pretty panties with the bra."

Sue helps me remove the bra and leaves the room as I put on my cami and t-shirt. I exit the fitting room to see Sue talking to Misty. Sue has her phone in her hand and appears to be showing Misty the pictures. Misty smiles and looks at me.

"I agree. I like the pink one better too. It looks good on you," said Misty.

I blush as Misty walks away to assist another customer. Sue hands me the pink bra.

"Hold that while I help you look for panties to match that bra," said Sue, leading me to the panties section. She looks through the selection of panties, finds a pink pair of briefs with a lace trim and holds it right in front of my waist to see how it would size up on me. I look around and thankfully, there is only one other customer in the shop. But I do see Misty coming towards us again.

"That would look cute on him too," said Misty.

"I agree," said Sue. "Let's see if we can find other pairs."

Sue hands me the panties and tells me to hold it while she and Misty look at other panties. Misty shouts out, "How about this one?"

Misty is holding up a pair of pink panties with ruffles on the back.

"Turn around," said Sue.

I comply, turning around with my back to Sue. Sue holds the panties in front of my butt with the ruffle side facing out.

"That would look cute on him too," said Misty.

"I agree," said Sue. "Ready to check out?"

I'm eager to leave as I'm embarrassed enough already, but I didn't show it.

"Yes, Ma'am," I said to Sue.

"Good. Misty will check you out," said Sue.

"Come this way," said Misty, leading me to the cash register at the front of the store. She rings up the two panties and the bra.

I look over at Sue still over in the panties section. I see she is talking on the phone, probably with Mary, no doubt. Misty rings up the transaction and tells me how much it is. I take out my wallet and take out the cash and give it to Misty. At that moment, a customer comes by the register, ready and waiting to purchase her own merchandise. The customer is a young woman about 25 or so herself. Misty puts the bra and panties in a bag, then she puts the receipt in the bag and hands the bag to me.

"Enjoy your bra and panties - sissy!" said Missy.

The customer looks at me and grins. I blush. At that moment, Sue walks up.

"Can you come with me a minute?" said Sue.

"Um, yeah, sure," I said.

I follow Sue back to the fitting room. She opens the door and looks at me.

"Mary wants you to put on the panties with the ruffles on it. And put on the bra too," said Sue. "Give me a shout when you have done so."

I go in the fitting room and shut the door. I put on the bra and panties and look at myself in the mirror. I then shout out, "Ok, I'm ready."

Sue opens the door to see me wearing the bra and panties. She smiles a very wicked smile.

"Misty, come here! look at him!" said Sue.

Misty arrives quickly and sees me in the bra and panties.

"Damn, they look cute on you," said Misty.

Sue takes out her phone and snaps another picture. She tells me to get dressed and shut the door. I can hear Sue and Misty giggling outside the fitting room. I put the lace panties that I was wearing earlier in the bag and then I exit the fitting room. I see Sue talking to Misty as I leave the fitting room carrying the shopping bag. Sue looks at me and smiles.

"Thanks for coming. I had fun," said Sue. "Be sure to come back again."

"Yes, Ma'am, I sure will," I said, leaving the store. I walk to my vehicle and open the door. I turn around and look back at the store. There is Misty and Sue standing in front of the window. They are looking at Sue's phone and appear to be giggling. I blush and get into my vehicle and drive away for the 2 hour trip back home.Disclaimer: All my stories are pure fiction, unless otherwise noted. Any similar events that may have occurred are purely coincidental.

*****

I just got home late at night from a rough day of work. I tossed my jacket on the kitchen chair, kicked off my shoes, got a beer from the fridge, and decided to sit down at my computer to check my messages before turning in to bed.

I did get a few messages. One of them was from a woman that I do general housecleaning for. You see, I'm a 49 year old male that does housecleaning while wearing a sissy maid uniform. And this woman loves sissy cross dressers and takes great pleasure in humiliating them.

Back to the message, it said:

"Pinky, tomorrow you are going shopping for a bra and panties. I've made arrangements with a good friend of mine who works at an intimate apparel store. She will be assisting you with your shopping. You are to report to her when you get there.

I'll e-mail you further details in the morning. The shopping assignment is to be in the afternoon. This should give you plenty of notice to make yourself pretty. Remove your body hair, paint your nails, etc.

Text me when you get this message.

Mary"

So I'm being sent to an unknown store to purchase a bra and panties for myself. This should be interesting. I texted Mary to let her know that I got her e-mail. She replied that she will contact me in the morning with additional details and to be ready to go when I get her instructions tomorrow. I ate, checked my other messages, and went to bed.

The next morning, I woke up to find another message in my inbox. It said:

"Pinky, you are to report to the shop at 1pm. Your contact's name is Sue. I'll text you the address when you leave. It's about 2 hours from your apartment, so be ready to leave at about 11am. Be sure your body hair have been removed, your nails are painted, you smell feminine, etc. And wear those pretty pink lace panties that you wore last time you cleaned for me as well as that black lace cami.

Mary"

I got into the shower right away and removed my body hair. It was easy because I had little body hair to begin with. I then used feminine body wash to cleanse myself with and got out of the shower.

After drying myself off, I sat down and clipped my fingernails and toenails. I then painted my nails a bright pink color. I didn't put any make up on though because I'm still inexperienced in the makeup department and Mary knows that or she would have told me to use makeup as well.

I put on my pink lace panties and a black lace cami top. I then selected a pair of Gloria Vanderbilt jeans to wear because they feel nice and girly, but can pass for male jeans if an observer doesn't look too hard. I put on a male t-shirt and shoes. I wasn't instructed to dress feminine or I would have selected feminine clothes instead. I had no idea where I was going, so I decided to be safe in dressing in male clothes for my shopping assignment.

It's almost 11am and I get the text message with the address on it. I go to my vehicle and got in and started it up. I mount my phone on the dashboard and input the address on a navigation app and off I go.

2 hours later, I pull in the parking lot of the intimate apparel store. I get out of my vehicle and do a deep breath. I then enter the store. It's full of bras, panties, pantyhose, etc. all on display. The store is not too busy. There's only a couple customers milling about. A pretty young woman came up to me. She couldn't be any older than 25.

"Hello. My name is Misty. How can I help you?" she said to me.

"Um, I'm supposed to meet a woman named Sue that works here," I said with a bit of hesitation in my voice.

"I'll go get her. Wait here a moment," said the girl.

I watched as the woman walked off to another part of the store. I saw her approach another woman, who was hanging bras on a display. The first woman pointed in my direction and the second woman nodded in acknowledgment, stopped what she was doing, and walked towards me. We shook hands. This woman appears to be in her early 30's.

"So you are Pinky, right?" said the woman.

"Yes, Ma'am," I replied.

"My name is Sue. Nice to meet you," she said as she was looking at my jeans. "Those are Gloria Vanderbilt jeans, right?"

Busted.

"Yes, Ma'am," I said.

Sue smiled a wicked smile and gestured in a general direction.

"Come this way please," she said, walking towards what appears to be a fitting room area.

She takes out a key from her pocket and opens the fitting room door and beckons me inside. She joins me in the fitting room and grabs a tape measure hanging on the wall.

"Take off your shirt please. I need to measure your chest," said Sue.

I hesitate a moment because if I remove my shirt, she'll see the black lace cami that I'm wearing underneath my shirt. Sue notices my hesitation.

"Pinky, take off your shirt - now," she said.

I comply and remove my shirt to reveal the black lace cami that I am wearing underneath the shirt. Sue smiles and tells me I can leave the cami on. She takes the tape measure and wraps it around my chest. After getting the measurement, she puts the tape measure away.

"Stay here. I'll be right back," she said as she left the fitting room.

I wait a moment and then I hear two voices talking to each other as they approach the fitting room. I'm like, oh no. Is Sue bringing her coworker Misty back with her? The door opens and sure enough, both Sue and Misty are standing in the doorway. Misty smiles.

"You're right. He is such a sissy," said Misty.

I blush at the comment and it is then I notice both women are each carrying a bra. Sue is carrying a pink bra and Misty has a red bra in hand. At that moment, a customer calls out for assistance. Misty hands the red bra to Sue.

"Have fun. Let me know how it goes," said Misty, walking off to help the customer.

Sue comes in the fitting room, shuts the door behind her and hangs up the red bra.

"All right, take off the cami. I want to put this bra on you to see how it fits," said Sue.

I take off the cami and hang it up. Sue puts the bra on me and adjusts it. She steps back to take a look and smiles. She takes her phone out of her pocket and snaps a picture of me wearing the bra before I could say anything.

"Don't worry. I'm sending this to Mary," said Sue. "Let's take off the bra and try on the other one."

I still feel embarrassed having my picture taken like that as Sue removes the red bra and puts on the pink one. She snaps a picture of me wearing that too and sends the picture.

"That pink bra really looks nice on you," Sue said.

I blush and at that moment Sue's phone chirps, indicating an incoming text message. She looks at it and smiles.

"Looks like Mary agrees. She likes the pink bra too," said Sue. "Let's take off the bra and get dressed. Mary wants you to go look for some pretty panties with the bra."

Sue helps me remove the bra and leaves the room as I put on my cami and t-shirt. I exit the fitting room to see Sue talking to Misty. Sue has her phone in her hand and appears to be showing Misty the pictures. Misty smiles and looks at me.

"I agree. I like the pink one better too. It looks good on you," said Misty.

I blush as Misty walks away to assist another customer. Sue hands me the pink bra.

"Hold that while I help you look for panties to match that bra," said Sue, leading me to the panties section. She looks through the selection of panties, finds a pink pair of briefs with a lace trim and holds it right in front of my waist to see how it would size up on me. I look around and thankfully, there is only one other customer in the shop. But I do see Misty coming towards us again.

"That would look cute on him too," said Misty.

"I agree," said Sue. "Let's see if we can find other pairs."

Sue hands me the panties and tells me to hold it while she and Misty look at other panties. Misty shouts out, "How about this one?"

Misty is holding up a pair of pink panties with ruffles on the back.

"Turn around," said Sue.

I comply, turning around with my back to Sue. Sue holds the panties in front of my butt with the ruffle side facing out.

"That would look cute on him too," said Misty.

"I agree," said Sue. "Ready to check out?"

I'm eager to leave as I'm embarrassed enough already, but I didn't show it.

"Yes, Ma'am," I said to Sue.

"Good. Misty will check you out," said Sue.

"Come this way," said Misty, leading me to the cash register at the front of the store. She rings up the two panties and the bra.

I look over at Sue still over in the panties section. I see she is talking on the phone, probably with Mary, no doubt. Misty rings up the transaction and tells me how much it is. I take out my wallet and take out the cash and give it to Misty. At that moment, a customer comes by the register, ready and waiting to purchase her own merchandise. The customer is a young woman about 25 or so herself. Misty puts the bra and panties in a bag, then she puts the receipt in the bag and hands the bag to me.

"Enjoy your bra and panties - sissy!" said Missy.

The customer looks at me and grins. I blush. At that moment, Sue walks up.

"Can you come with me a minute?" said Sue.

"Um, yeah, sure," I said.

I follow Sue back to the fitting room. She opens the door and looks at me.

"Mary wants you to put on the panties with the ruffles on it. And put on the bra too," said Sue. "Give me a shout when you have done so."

I go in the fitting room and shut the door. I put on the bra and panties and look at myself in the mirror. I then shout out, "Ok, I'm ready."

Sue opens the door to see me wearing the bra and panties. She smiles a very wicked smile.

"Misty, come here! look at him!" said Sue.

Misty arrives quickly and sees me in the bra and panties.

"Damn, they look cute on you," said Misty.

Sue takes out her phone and snaps another picture. She tells me to get dressed and shut the door. I can hear Sue and Misty giggling outside the fitting room. I put the lace panties that I was wearing earlier in the bag and then I exit the fitting room. I see Sue talking to Misty as I leave the fitting room carrying the shopping bag. Sue looks at me and smiles.

"Thanks for coming. I had fun," said Sue. "Be sure to come back again."

"Yes, Ma'am, I sure will," I said, leaving the store. I walk to my vehicle and open the door. I turn around and look back at the store. There is Misty and Sue standing in front of the window. They are looking at Sue's phone and appear to be giggling. I blush and get into my vehicle and drive away for the 2 hour trip back home.

shopping   pinky's   first   assignment  

Apr 24, 2018 in femdom

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