Another Sissy Shopping Adventure

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Another sissy shopping assignment from a young mistress.
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In my last story, I related a story about a mistress who gave me a sissy assignment several years ago. This involved going to a mall and getting a makeover and getting girly clothes.

Like the other story in this topic, there's no sex just some good old fashioned humiliation.

This is the latest adventure and I hope you enjoy it!

*********************

I have been doing some serious bonding with a young, hot mistress who knows exactly how to push my buttons. She has totally latched onto and embraced my sissyhood. I met her doing phone sex; she is 20 and hot as hell! Her pictures are fabulous and she claims it is her. The pictures look genuine enough as they are not airbrushed like so many others. Even if it's not her, I fantasize about her constantly. Especially as she dominates me so easily.

I know I have to do everything she tells me to do. She has pictures of me sucking BBC, getting fucked and dressing up; I do a lot of stuff on Skype and she takes alot of pictures. So she tells me to be a "good girl" and things will be okay.

She has set up a session for me where I will be on cam and will have to perform for a bunch of her friends. They will be on vacation, likely having consumed alcohol and will be ready for major humiliation of me. I paid her hundreds of dollars for the privilege and also provided her with a list of things I will have to do for them. As I am writing this story, I haven't had this session yet (maybe that will be the next story!) but this is about the preparation for this session.

She ordered me to get a pink nightie, a dildo, makeup and nair to get ready for the session with her friends. I made up an excuse to get out of the house and made my way to the local adult store. I agreed to start the call with her, put the phone in my pocket in speakerphone mode so she could hear everything. Then I went into the store.

There was a 20 something woman at the counter who greeted me as I walked in. She had pink hair and a nose ring.

"Welcome sir! How can I help you?" She asked.

"I'm looking for a nightie... something in a 3x." I said.

She showed me the rack of nighties and i glances through them. I was looking for an opening to tell her it would be for me. My mistress insisted on it.

"Well I don't know... I always have trouble getting them to fit me." I said.

"Oh, it's for you? You know you can try on the top but we have a policy against trying in the panties." said the clerk.

I then did as I was instructed by my mistress and handed the phone to the salesclerk. They chatted for a while and I could see a smile come across the sales clerks face. She told me my "friend" on the phone insisted I try on the nightie.

I decided to do it. I took one the largest pink nighties in the rack and went to the changing room. As I took off my shorts I recalled I had been wearing swim trunks from earlier in the day. So I would not have anything to cover up my little dick (or "clit") as my mistress instructed me to call it. After taking off all my clothes I put in the nightie and walked into the store. The clerk was right there.

"It looks very cute on you." She said.

I walked girlishly around, swaying my hips.

"I'll take it!" I said.

"Ok, anything else?" She asked.

"I also need a dildo" I said and we walked over to the section in the store. I still had the nightie on. While we walked I apologized for not having anything on under the nightie.

"That's ok, I didn't look." She said.

I doubted that but I told her "there's not much to cover up down there." She smiles an evil type of smile.

We picked out a nice fat dildo and the clerk commented on the size. I licked my lips and said how hot the guy on the front of the package is. She agreed!

I went back into the changing room and noticed I had a little stiffy and the clerk hadnt even noticed! I got dressed and went to the counter. I paid for the purchases and left.

I still need to go to a drugstore to get the makeup and the nair. My mistress has insisted I get all my body hair off before the big cam show. She will also want me to put on makeup. I can't let her down or disappoint her so I'll do that soon.

My mistress was very proud of me that I didn't chicken out at the store. She has plans for me to go shopping in a more conventional mall in the very near future.

***

So my readers, if you have any suggestions that you would like me to do in an upcoming adventure, here's your chance to make suggestions. My mistress will have the link to this story and would love to hear from you!

Love and sissy kisses

Sissy Sherry

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5 Comments
AnonymousAnonymous6 months ago

What a sad, pathetic little wimp.

AnonymousAnonymousover 5 years ago

Maybe for the mall trip, the little sissy should have a vibrator in her. And definitely should wear panties. Though she should wear them 24/7 like a good girl.

AnonymousAnonymousover 5 years ago
love it

As a closet sissy this is exactly the kind of thing I love. Maybe for another assignment you can visit a gloryhole and take some cute pics? <3

AnonymousAnonymousover 5 years ago
Was boring

Barely any humiliation and no action. Could have read this in Readers Digest. Need to push limits and spice things up

sissysherry2sissysherry2over 5 years agoAuthor
You help write the next chapter!

My mistress has big plans for me. She will be sending me to the mall soon and you can help write the next chapter by leaving comments here! Please feel free to do it!

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