Sissy Shopping Adventure

by sissysherry2

I have been addicted to phone sex for a long time. My favorite type of call 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 obviously the idea was to go there and humiliate me.

I decided to take it to a whole new level by creating a note for 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 of 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:

“Hi! 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 a 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 fits 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 as a girl. I got a ton of stares, and a lot of people laughed at me. It was humiliating but very exhilarating!

The End.


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