Shoe shopping for a sissy in training | Erotic sissy story |  Mistress Andrea

 

Not wanting to keep Maria waiting, he rose early on Saturday so that he could give himself enough time to get to the mall before10 o'clock. He loved his new dresses and had seen some skirts in her store that he would like to have so he heeded her warning.  He waited outside the main mall entrance and saw her step out of her car at exactly 10. He had noticed the other day how attractive she was, but it struck him even more so as she approached. Maria was dressed in leggings, a tight fitting  sweater and spiked heels. "Good morning," he said "Thank you for meeting me." "Glad that you listened to what I told you." she responded. "By the way what is your name?" "Michael." he said. "Hmm, well once you get femmed you'll need to decide if it should be Michele, or another girl name." she replied. They entered the mall and she said "I think we'll shop first for some pantyhose, and bras and panties."  "Where do you think will be best to do that?" he asked. "For the style dresses you are wearing I think we'll go to the department store, they carry some pretty bras and panties. Also, a woman who shops in my store works in that department so we can get you measured for your bra."  His face blushed with anxiety as he asked  "Will this be out in the open?"  "I would guess so." she answered and added "If you want me to help you dress properly as a woman you need to do everything I decide. Understand?" "Yes, I'm  just scared and embarrassed." he answered. "I can understand your embarrassment, but you just need to endure it and listen to me," she replied an air of authority in her tone. 

 

He followed her quietly as they made their way to the lingerie department of the store. "Hi Brenda!" exclaimed Maria. "Hi Maria, how are you?" she replied, adding  "Your turn to shop today?" "Out shopping yes, but not for me." replied Maria. "This is Michael. He purchased three sundresses from me this week, pink and blue floral, pink and white, (she hesitated purposefully for a moment)  for himself. The dresses are all that he presently has in his wardrobe so  I offered to help him find some bras and panties, pantyhose, pumps, and make-up to go with the dresses. I'm  hoping you have  have some pretty pink, white and possibly baby blue bra and panty sets that would be nice matches with his dresses." Michael stood there horribly embarrassed as Brenda gave him a smirk. "I'm sure Maria that we can select some for him." replied Brenda. She then turned to Michael and asked  "What size bra do you wear?" Michael stood there for a second expecting that Maria would tell her that he didn't know but she didn't say a word. "I am not sure, I have not tried to purchase any until now." he meekly replied. "Okay let me get the tape so we can  measure you. Please take off your sweater while I go get it." said Brenda. Michael slowly took off his sweater and stood blushing and biting his lip waiting for Brenda to return.  With the tape in hand Brenda instructed him to raise his arms up and took his measurements. "Hmmm, 40, " she announced out loud "and a B cup."  "Let's make it a C cup." interjected Maria. "Wow, a full figured girl!" exclaimed Brenda which caused both she and Maria to breakout laughing. Michael grabbed his sweater and was about to run off when Maria said "Remember what I told you about shopping at my store." That held him in his tracks, and Brenda said "Follow me." which he did.   

 

Michael stood nervously looking on as Maria and Brenda discussed what style bra and panty they should select for him. "I really think silk and lace, or maybe all lace with the panty being French hi cut would be most appropriate for him given the sundresses that he'll be wearing." said Maria.  "Yes, I think you're right." replied Brenda who then turned to Michael and asked "Are you intending on buying skirts and blouses as well?"  "I think so," he answered. "Are you intending on staying with more feminine girlish styles like your dresses?" asked Brenda. Before he could respond Maria interjected "Yes, I think that will be best for you." "If you think so." Michael meekly replied. Brenda went "Hmmm" as she smiled at Maria sensing there was more going on than she expected.

 

Maria and Brenda selected two lovely pink, and two similarly lovely white bra and panty sets. "Unfortunately we don't seem to have anything similar in baby blue." said Brenda. "No problem, we can check elsewhere," stated Maria. She handed Michael the bra and panty sets and said "Hold these." She then asked Brenda where she might have similar cut floral panties. Brenda showed Maria where they were, and after looking them over Maria selected a panty that had pretty pink flowers over a white base. "I want you to get this panty also." said Maria as she handed the panty to Michael.

 

Maria turned to Brenda and said "I'll be back in a moment, I'm going across the floor to get his pantyhose. He'll pay for everything here." As Michael stood with Brenda she turned and said "Though you seem very nervous I bet you're excited about your new things." He blushed and smiled weakly in response. Maria returned and said "I selected pink, white and nude for you." " Thank you." he replied. As Brenda began to ring up his purchase she said "I bet you can't wait to try on your bra and panties." Once again he blushed and smiled meekly at her. As Brenda was packing the items into the bag Maria asked "Would it be possible for him to put on the floral panty and a pantyhose in the fitting room?" "Hmm, I think it would be better if he did it in the men's room at the end of this floor since I'm starting to get more customers." said Brenda. Maria turned to Michael and said "Take the bag down to the bathroom and put on the panty and nude pantyhose." "But why!" he anxiously exclaimed. "You need to have hose on to properly try on the pumps." responded Maria. "Maybe we should  shop for them another time then." he replied. "No, its our next stop!" Maria emphatically stated; adding. "But then again, maybe you don't want to shop in my store anymore."  "I'm scared!" he exclaimed. "Nonsense!" she sternly said, "decide now and don't waste my time." He looked imploringly at her but she just said "Decide!"  Michael sheepishly walked towards the bathroom and heard Maria say "Be quick about it." Once Michael was far enough away Brenda said "I get the sense that you are really enjoying this, and that you have even more in mind." Maria smiled and replied "Yes, and yes!" at which they both began to laugh. When Michael returned Maria asked  "Now that wasn't too bad was it? "  "I was so scared that I'm still shaking."  he timidly replied. "How do your panties feel on?" asked Brenda. "Very nice." he replied. "Mmm Hmm, enjoy!" she said.  

 

They both thanked Brenda and Maria turned to Michael and said "Let's go, there's a shoe store at the other end of the mall that I know has pumps that will go with your dresses. Once we finish with that we'll buy you some make-up." Michael didn't say a word as they walked towards the store,  he was getting excited by the wonderful feeling of the silk panty caressing him, and from the nylons on his legs. Maria noticed that he was carrying the bag close in front of him and said "Go in the restroom just ahead and tuck that thing between your legs." Mortified, Michael rushed ahead and did as she said.  Maria didn't say anything when he returned she just continued to lead him down the mall.

 

When they reached the store Michael exclaimed "Oh no, oh no!" as he saw the salesman. "Relax!" said Maria. "Oh no, isn't there somewhere else we can go?" he asked anxiously. "No! I like their shoes and we're going in. If you complain one more time I'm through with this."  His heart pounding Michael followed her into the store. As the salesman approached Maria said "We need a pair of white, pink and baby blue pumps, either with or without bows on the tops, and 2 or 3 inch heels. Oh, they're  for him!"  Michael's face reddened and he looked down as the man turned towards him. "What size do you wear?" asked the man. "9 and a half." replied Michael head still down. "Is that in men's or women's?" the man asked. "Men's."  Michael sheepishly replied. "Take a seat I'll see what we have."  stated the man. Michael sat nervously next to Maria as they waited. After several minutes the man approached with several boxes and Maria instructed Michael to take off his shoes and socks. Not paying any attention the man said "I'll get some peds." "No need, " replied Maria, " he has pantyhose on." The man just shook his head, placed the boxes in front of Michael and handed him a shoe horn. "Pick a pair, put both shoes on and try to walk so I can see how they fit and look." instructed Maria. This time Michael did not argue as he wanted to leave as quickly as possible. Maria, however, was enjoying his humiliation and made him retry on each pair. Finally, she said  "I think you'll take all of them."