Dear Auntie Helga,
Jenny, my wife, (Ms Jennifer to me) keeps me on my submissive sissy toes by taking me on regular lingerie shopping trips to humiliate me. This time she outdid herself. She has a friend, Wendy, who manages a women's clothing dept at a large department store. She gave her a call to cook up a night that I would never forget.
Jenny had me prepare for my shopping humiliation by getting dressed in the outfit she laid out for me. On the bed was a black bra, black lace panties, stockings, garter belt, white ladies slacks (that zip in back, without pockets or belt) and a sleeveless, pink, silk blouse that buttoned-up-the-back. I was in a panic. I knew that the black panties and garter belt would show through the white slacks and the black bra would be clearly visible thru the sheer pink blouse... I would have trouble even keeping the bra straps from showing since the blouse was sleeveless and showed lots of shoulder.
I dressed and looked at myself in the mirror. Just as I thought, the sheer blouse showed every stitch on my bra like it wasn't there and the panties and garters were clearly visible through the slacks. I wore ladies penny loafers and, of course, no socks, so my stockings showed even when I stood due to my slacks being a little short. I lifted the short blouse a bit and saw my garter belt around my waist, well above the low riding slacks. If I so much as leaned forward everyone would get a nice show of my lace garter belt. I had to push the bra straps in to keep them from showing. I began to cry at the thought of the humiliation I was about to endure. Jenny calmed me down by handing me a black sweater to cover the sheer, feminine blouse and limit the risk of my garter belt being exposed. I was so relieved. I dropped to my knees and gave her bottom a kiss, as she requires when I thank her.
Jenny's shopping buddies, Melanie and Kim, (Miss Melanie and Miss Kim to me) arrived. Kim is Jenny's niece. They loved my feminine look and commented on my sexy black panties and sheer stockings. They loved joining in the fun of Jenny's teasing and humiliation. They also love my submission to dominate females. I am required to obey all females without hesitation and they take full advantage by barking demanding commands and embarrassing rules. Whenever Miss Kim is present, for instance, she requires me to curtsy when a female enters the room, very humiliating. She loves to observe my curtsy technique and correct me if it does not meet her standards.
We all jumped in the car and headed out. Kim sat next to me. She put her arm around me and played with my bra strap. After a bit she said, Sissy Bobbi, take that hot sweater off. I saw Jenny smile as Miss Kim helped me take it off exposing my feminine blouse and black bra. Kim gasped at my humiliating attire and told Jenny what a great job she did picking out my outfit. "Very sexy and hot". When we arrived at the small shop Jenny told me I could put the sweater back on. I could have kissed her. I felt so fortunate that only my panties and stockings were visible.
I knew I would be here for a while. Jenny immediately introduced me to Miss Wendy, her friend and the shop manager. I couldn't believe it, my attire was identical to all the sales ladies, white slacks and sheer pink blouses but none were wearing black lingerie. Jenny then explained, "Wendy, as we discussed, Sissy Bobbi is here to work for you. The girls and I will be shopping for several hours so Sissy is at your disposal to do with as you please." I was flabbergasted! Jenny was about to leave me there for hours to work in a lingerie dept. This was my most humiliating fantasy.
Miss Wendy then took control. She pinned an official name tag on my blouse that read "Sissy Bobbi", then told me in no uncertain terms that sweaters were not allowed by the employee dress code and I would have to take it off. Miss Jenny and the girls giggled as they waved goodbye and walked away. She helped me out of the sweater to reveal the sheer pink blouse showing my black lacy bra. Miss Wendy adjusted my bra straps so they didn't show from under my sleeveless blouse and warned me to make sure that they did not show for the rest of the evening or else.
Miss Wendy took me over to table brimming with hundreds of panties in a big pile. She introduced me to a sales associate, Kirsten, who looked like she was half my age. Kirsten would train me on how to sort and hang each of the panties on racks by size, style and color and then verify my work quality. I was to obey her every command.
Kirsten told me to address her as Miss Kirsten and to listen closely since she didn't want to have to instruct me twice. She then showed me exactly how the panties were to be sorted and hung on hangers, she was very specific. She also described the different styles to be sorted and the order of the colors when placed on the racks. She explicitly instructed me to be sure that each panty hung naturally without wrinkles, which took some doing. My head was spinning. Here I was dressed as a sales girl with panties and bra showing for all to see, my name tag reading Sissy Bobbi and a huge pile of silky panties before me that I had to be hung, sorted and arranged to specifications which I could hardly remember. And to top it off, being bossed around by Miss Kirsten, a young woman who could pass for a teenager. I had never been so humiliated.
I started in, picking a hanger and clipping a pair of panties in place, silky, lace trimmed baby blue nylon briefs, size 7. I had to fuss with them to get them to hang nicely. So pretty and feminine and so embarrassing to have to fondle these ladies dainties as I stood in the middle of the shop where customers were milling about, fearful that one would come up and ask me a question. Then it happened, a customer came over and began looking through the panty pile. She turned to me and giggled as it was clear that I was a cross-dressed sissy. Sissy Bobbi, can you find me a size 5 in this style? Her question was a command to me so I nodded and began looking for the pink lace trimmed hipster style in the requested size. I eventually found the right pair and offered them to the customer. She asked me to put them on a hanger and then added, don't you wish you were wearing a pretty pair like these? I quickly clipped them to the hanger and handed them to the lady, who giggled some more as she walked away. So humiliating.
I had worked for 30 minutes when Miss Kirsten returned... and she was not happy. I had only arranged a few dozen pairs on the rack and I had the style and color order all wrong. She berated me for my incompetence right there on the floor as customers looked on. "I knew a sissy cross-dresser was not going to work out" she said. I felt so humiliated to be publicly shamed by this young woman as I stood there in my revealing blouse and slacks. She threw all the panties back on the pile and told me, "start over and this time it better be right or I will have to call Wendy over."
Miss Kirsten returned in about 20 minutes and noted little progress on the quality of my work. She smiled and told me that Wendy would need to decide what to do with me. "Maybe you should come over to my apartment and sort my panties and bras for me for practice, would you like that?" I didn't know what to say so I said, "I would like that Miss Kirsten." She smiled and said "maybe that could be arranged." Then she reached up and pulled my bra straps out from under my blouse so they could be seen.
Wendy walked up and asked how things were going. Miss Kristen explained that my work was very substandard and unacceptable. She stated that she had already made me start over once but she questioned if I was motivated properly. "And what would you recommend" asked Wendy. Sissies need to be disciplined, a spanking is in order and then some additional humiliation. "Agreed", said Wendy, "and maybe a spanking will help Sissy remember to keep those bra straps properly tucked away too. Bring Sissy to the back room and we will give her bottom the paddling it needs." I was speechless as Miss Kirsten grabbed my wrist and took me to the back room.
There Kirsten unzipped my slacks and pulled them down. Next she lowered my panties to expose my bottom and my chastity device. They both laughed at the device that controlled my sexual release and kept me from masturbating. "Jenny sure knows how to control a sissy" said Wendy. She then took a seat and commanded me to lay across her lap. My bottom was now exposed and ready. She gave me a dozen firm spanks with her bare hand. The pain increased with each swat and my cheeks turned bright red. She them demanded "should I continue or are you going to obey Miss Kirsten properly?" "I will obey her I pleaded, please stop." I was in total submission and humiliation. Kirsten stepped in and suggested that she should give the next dozen spanks to reinforce who was in charge. Wendy agreed and had me lay across Miss Kirsten's lap for another 12 swats. Here I was, helpless and laying across the beautiful legs of a young woman, being spanked like a child. I was crying like a baby when she finished.
"Now for some humiliation to reinforce your lesson" said Miss Kirsten. Wendy asked, "what do you have in mind Kirsten?" I think we should have him model a nightgown in the display window for a while. Great idea, I'll pick one out. Wendy returned with a short, pink baby doll nightie. Let's get that blouse off and slip this on you. In a moment I felt like a bride on her honeymoon night, attired in a beautiful baby doll nightie that was so short in showed all of my lingerie. My panties and garter belt could be seen plainly no matter how hard I tugged to pull the nightie down and my black bra was visible through the sheer nylon layers. Wendy and Kirsten took me a small door and helped through. They then commanded me to remain perfectly still, like a mannequin until they returned. They shut the door of the display and pulled back the curtain.
I was now on display for the entire store to see. I struck a fixed mannequin pose as commanded. Ladies and men gathered to look at me and snicker. It was obvious that I was a sissy man, cross-dressed in baby doll finery and sexy lingerie pretending to be a mannequin. I stood there fixed and unflinching, eyes set forward, but my tears of humiliation giving me away. After what seemed like hours, Jenny and her friends approached the window. They gasped and laughed when they realized that the mannequin in the window was their Sissy Bobbi. I was so humiliated.
The curtain closed, the door opened and Wendy helped me out of the display to where Kirsten, Jenny and her friends were gathered. Miss Kim gave Kirsten a hug, apparently they had met at college and were best friends. I curtsied since Miss Kim was there, she barked "Do it again, deeper this time and hold it until I say you can rise." I curtsied again, deeply, and held the low position, my eyes lowered, my fingers holding the hem of my gown out, waiting for permission to rise. My muscles ached after a few minutes. Finally, when Miss Kim thought I had learned my lesson, she allowed me up. Jenny approached and felt the silky nylon of my gown. "You look so pretty in your new gown Bobbi, you will be wearing that to bed tonight with all your lingerie, just as you were dressed in the display window." They then discussed if I should be made to walk to the car in my pretty baby doll. Kim said that I looked so feminine and pretty that some big man might attack me, so it might be best to change.
Melanie offered to let me wear the new sundress she just bought. She pulled out the short spaghetti strapped dress, everyone agreed that it was the perfect outfit for my walk thru the mall to the car. "Hands up" they commanded as they slipped me out of my baby doll gown exposing all of my feminine lingerie. Melanie unzipped the dress and held it out for me to step into which I did. She then slipped it up over my arms and then slowly zipped it up the back as she told me what a pretty sissy I was. She turned me to look full in the mirror where I saw myself transformed into a sexy sissy. My bra straps showed and the short hem allowed my stocking tops and garters to be seen by all. "Let's get him into some pretty shoes" Melanie exclaimed as she slipped a pair of high heels on my feet. Now Sissy Bobbi is ready for his final humiliation walk for the night. They thanked Wendy and Kirsten profusely for their fine supervision of me to which they responded, having Sissy here has been a lot of fun and we are looking forward to his regular shifts on Tuesday and Thursday evenings. Bring him back anytime because he will be earning lots of credits for lingerie purchases as we agreed. I couldn't believe it, I now have regular hours working in a lingerie shop and my earnings could only be used to buy feminine lingerie.
Jenny turned to me and said "Kirsten asked if you could come over tomorrow night. She needs your help with something. I am busy but Miss Kim said she would take you over, won't that be fun?" I hoped that the fun would be limited to organizing Miss Kirsten's lingerie and curtsies to please Miss Kim, but I was afraid that it would be much more.
"Let's go" said Jenny. Tears welled up as Jenny and Kim took my hands to walk me out to the mall for all to see me in my new sundress and exposed lingerie; they steadied me as I stumbled a bit in my new heels. I had learned my lesson in obedience and submission thoroughly, my humiliation was also thorough and it was not over as I realized that tomorrow evening I would be at the mercy of Miss Kim and Miss Kirsten.
Thank you for your letter Sissy Bobbi. Your generous Mistress and her wonderful friends all appreciate the humiliation brought on by public exposure, you should be very thankful that this was a small shop and not a large store in the mall. Of course as most sissies know, this type of embarrassment brings a certain thrill that can't be denied. A most memorable occasion to be sure.