tagTransgender & CrossdressersSissy Shopping Adventure

Sissy Shopping Adventure


This story involves pure public humiliation and not any sex. So if this is your thing read on but if you're looking for a sex story... well there are plenty of those on this site but this isn't one of them.

This is based on an actual experience that happened to me. In past stories, I've gotten comments from readers that they seemed far fetched and maybe they were. Not this time.

Hope you enjoy!


I have been addicted to phone sex for a long time. My favorite type of calls is where the girl loves to feminize sissies. I have one girl in particular who is my Mistress and she loves to play. One day I saw an email from her. She likes to do mass pay per view emails which can be annoying but I got one that looked intriguing. It was a "sissy shopping assignment" which involved going to a Merle Norman or Ulta store for a makeover, followed by a trip to a retail store for clothes. She had a list of items to get and an obviously the idea was to go there and humiliate myself.

I decided to take it to a whole new level by creating a note to the employee. The message would involve telling them that I am a sissy who is shy but would like to get some help. This would allow them to not get into trouble with the management and hopefully have some fun. My Mistress wanted to do the call with me at the store. She was very supportive and told me to write out a note that would include basic instructions for each place. One note was for the makeover place and another one for the clothes store. She had me send her the notes via email beforehand so she could review and edit them. She added pink hearts around the notes and changed the font to a girly one. Naturally the font was pink.

She told me to start at the makeup store to ramp up the humiliation, since I couldn't cover up it up. Then it would be off to shop for clothes. At the time there was a store called "Deb" that carried styles for larger girls. I printed out the two notes in color and headed out.

I began the phone sex call from outside the mall; she gave me a little pep talk before going in.

"Sherry this is going to be so much fun! Make sure you are nice to the employees; they will catch on quickly and while it may be uncomfortable at first, it'll be great. Now let's go and just do as you're told."

I walked into the Merle Norman store and was very nervous. A young and attractive girl welcomed me into the store. She had a name tag on that said "Amy." When she asked me how she could help me I just handed her the following note:


I am a sissy who would love to get a makeover. I am new at this and I'm asking for your help. Here are the items I'd like but if you have any ideas that might help please feel free to let me know.

- Liquid foundation

- Blush

- Eyeliner

- Mascara

- Eyeshadow

- lipstick

I would also like help thinning out my eyebrows a bit. I'd like to leave here feeling and looking as feminine as possible.

I have a friend on the phone with me who is encouraging me along. You can talk with her if it's okay to do so.

If you can talk with my friend just reach out your hand.

Thank you so much and please let me know if it's ok. I like to be called Sherry."

To my surprise she gave me the back the note and reached out her hand. I handed her my phone. They seemed like they were talking forever; finally Amy handed me the phone back and smiled.

"Hi Sherry. Of course we can help you. That's why we're here. Now your friend said that you want to have long lasting makeup applied today. You're in luck. We have an opening with one of our best makeup artists who just had a cancellation. Her name is Nadia; let me call her up."

In a few minutes I saw a woman come out who made my heart skip a beat.

Nadia was tall and very pretty; she reminded me a bit of a younger Angelia Jolie; a stunning brunette with beautiful eyes and a very athletic figure. She had full lips and a fantastic smile.

"Hi I'm Nadia and I understand you're here for a makeover?"

I stammered a short reply and handed her the note. I saw a smile come across her face. Like Amy, she reached her hand after she was done reading the note. I gave her the phone. As they talked I saw a huge smile come to her and she giggled. Nadia mostly listened and at one point her face lit up.

"OK let's get started Sherry. My instructions are to make you look as sexy as possible and to use waterproof makeup. Your friend has a big day planned for you. One thing though she wants the results to a surprise so she wants me to turn you away from the mirror. And she said she's in charge of this and to follow her instructions and not yours."

Without asking my permission she spun me around and started working. The whole process took forever as she worked her way around my face. She plucked my eyebrows which really hurt, applied makeup as she went down to my eyes, cheeks and of course my lips. During the call I left my phone on speaker so we could talk. My Mistress told me to tell Nadia I had a date with a new guy that evening. We talked about girl stuff and I really started enjoying it.

Finally, Nadia spun me around and I couldn't believe what I saw in the mirror. I truly looked feminine; it was a dream come true! Nadia took a picture with my phone and one with hers. I then handed her my credit card and she left. A few minutes later she came back.

"Sherry you look stunning! I've gotta admit this is one of my best jobs ever. Your friend told me I could decide what my tip will be so I made it $100. Sign here."

I signed the credit card slip and stood up. I didn't realize it but my little dick was hard. Nadia laughed.

"Your friend predicted that would happen. She told me about your "little problem." Don't worry you can't really tell. I can't wait to show my friends these pictures!"

I then left the Merle Norman store in full makeup. Since it was waterproof makeup I couldn't wash it off so I walked through the mall to a lot of stares and snickers. The next stop was for clothes. I still had my Mistress on the phone.

I walked into the local Deb store and went right to the counter. The woman there happened to be the store manager who was named Raquel. I handed her a different note which was also in the girly and pink font. It read as follows:


I am a sissy who needs help getting clothes and I am hoping you can help me. I need a new outfit for a date I have coming up. I'd like something feminine like a skirt and blouse. I also need bra (size 40B) and panties. If it would be possible to try them in and show you I would appreciate it but would understand if you didn't allow that. I like to be called Sherry. I have a friend on the phone who would like to help. If you would like to talk with her just reach out your hand.

Thank you!"

Raquel then reached out her hand and started talking with my Mistress. After a few minutes she motioned me over to their large size spring collection. There were skirts of all colors; I was hoping for something like a jeans skirt but Raquel handed me a couple of flowery girly skirts and a couple of blouses. I carried them over to the area where they had bras and panties. Raquel picked out some and handed them to me.

"Sherry, you need to try them on. Go into the last booth on the side there. Put it all on and come out so we can see. Here's a bra extender to use so you can get it on."

I did as instructed; I went into the dressing room, leaving my male clothes in the corner. I put the lingerie on first; it fit well and I felt great. Then I put on the skirt and twirled around. Finally the blouse went on. I came out of the dressing room and Raquel and one of the clerks were there.

"Wow Sherry you look great!" Raquel said. "Walk around a bit to see if it is comfortable."

I walked around the store and I admit it felt great. The store was quite busy and a lot of girls saw me. They were actually quite supportive and told me they liked my outfits. I tried on several outfits. My Mistress and Raquel chose the most feminine one for me.

"OK Sherry, it's time to check out. Your friend told me to bag up your man clothes so you can wear your new ones out of here. First though we want to get some pictures!"

Raquel took pictures of me posing on her phone and on mine. So did the clerk.

So I walked out of the mall dressed up like a girl. I got a ton of stares and a lot of people laughed at me. It was humiliating but very exhilarating!

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by Anonymous

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by sissysherry211/09/18

Yes Mistresses

I can’t wait for more fun times!!! It was soooo much fun. Next adventure will be the real sissy shopping adventure. Sorry for interrupting your fun

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by Anonymous11/05/18

soo cute, cept youre a bad girl!!

sherry, youre such a bad girl! you need to be punished because you never shut up and your interrupt our playtime with your worthless babbling. mandi and caitlyn own you

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by sissysherry207/03/18

Yes My Mistress

I can’t wait! I’ll write another story when it’s done

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by Anonymous07/03/18

Mistress Caitlyn

Oh Sissy Sherry, My good little Sissy Bitch.You always look so pretty all dolled up. I think it's time we get you out again where more people can see you and show it all off. Don't worry, I'll make suremore...

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by Brian7005/21/18


Great transformation, fun read. Xoxo, Brie

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