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Shopping for a new sissy..
He slowly walked around the mall casually glancing at the store windows and eventually stopped and looked in the window of a women's clothing store called "Maria's". The store had stylish dresses, skirts, tops and pants in the window which he admired while trying to control the feminine urge that was taking hold of him. After a few minutes he moved on continuing to glance at other stores.
Before he realized it he was again standing in front of "Maria's" drawn to the lovely clothes within. He tried to be nonchalant and subtly bit on his lower lip as his sense of femininity welled up inside of him. The store owner had seen him earlier but hadn't paid much attention, however, as he continued to stare at the clothes she walked outside and asked "Can't make up your mind?" "Excuse me?" he answered. She smiled and said, "You seem to be interested, why not come inside and take a closer look I have other clothes as well." He didn't answer just gave a shy look and followed her in. "Is there something in particular you have in mind?" she inquired. "I'm not sure, may I browse?" he asked. "Take your time and let me know if I can help?" she responded. He causally looked around occasionally stopping to look closer at an item and feel the fabrics which excited him.
After awhile she approached smiling and asked "So, is there anything that you think she might like?" "Possibly," he sheepishly replied. "What size does she wear?" she asked. This time he hesitated in responding afraid to tell her the truth. She sensed his nervousness and softly said "May I ask, are you shopping for yourself?" His face quickly blushed giving her the unstated answer. "It's okay, "she reassured him, adding "Let's pick some things out for you." As he stood mortified before her she asked "Have you bought any women's clothes for yourself before? Do you know your size?" "This is the first time," he meekly replied and added "Are you sure this is okay?" "It's fine sweetie," she replied. She looked him over and said "I'm thinking we should try either a size 10 or 12, but once you try something on we'll know for sure." "Try them on!" he exclaimed anxiously. "Well of course, otherwise you may be disappointed when you get them home," she stated and added, "If this really is your first time you'll not know how they should look and fit." "But what if some women come in the store?" he nervously asked. "Don't worry, its not the first time I've had a male shop for himself," she responded.
"Now what shall we look for, dresses, skirts, tops, pants, or all of them?" she asked smiling. Still nervous he replied "dresses." "Alright! Now one thing I need to know, will you be stuffing your bra cups? You will be wearing a bra correct?" His face was bright red as he was utterly mortified and responded softly, "Yes." She asked, "Do you have bras already?" "No, I have nothing," he replied sheepishly, and with his embarrassment growing said, "Maybe I should go." "I'll have none of that." she stated and added, " I need to know how large your boobs will be so I can appraise how your dresses will look with them." "I'm sorry I have no idea. What do you think?" he responded. "Well, I think boobs should make a statement, so a C cup," she said laughingly. His face reddened again, but he remained silent. "Okay now that your bra cup size is settled let's pick you out some pretty dresses." she said adding, "I think pretty floral, pink, and white summer dresses will do the trick. How does that sound?" "I guess that would be okay." he answered. She just smiled and selected the dresses from the racks. "Do you like these?" she asked. "They are very pretty." he said. Still smiling she said, "Good! Now go try one on and let me know if you need any help. Once you have it on come out so I can see how it fits and how you look." He took a deep breath and went into the fitting room. He slowly took off his clothes and selected the pink and baby blue floral dress which he slipped into and zipped up the back. He stood for a moment looking at himself in the mirror his excitement growing. "Do you have a dress on sweetie?" she called out. "Yes," he replied. "Don't be shy come out and show me." she said. He expected her to be outside of the room when he opened the door but she was not. He tentatively stood by the fitting room entrance as she stood in the center of the store. "Come on sweetie, come show me how you look," she told him. He nervously did as she told him and as he approached her she said, "Oh my, that dress suits you perfectly. Turn for me slowly, hmm, very pretty, very pretty on you. Once you get some pumps, nylons, bras, panties and make-up you'll look all the prettier. Now go try on the next one and come back out."
After trying on all of the dresses she asked, " So what do you think, one or all of them?" "All of them." he responded. "Excellent!" she exclaimed. As he was about to leave after paying and thanking her she asked, "Do you have any idea what shoes will go best with the dresses, or for that matter what bras and panties, and make-up?" Again blushing with shame he responded, "No, I will have to try to figure that out." "Hmm, I think it best if you had a female to help get you started." she replied. "I'm afraid I don't know anyone who'd be interested." he meekly replied. "Saturday is my day off, meet me at the main mall entrance at 10 o'clock," she said. He stood looking at her, and before he could speak she said, "Do you like the clothes I sell?" "Yes." he replied. "Well, if you want to keep shopping here you're to meet me promptly at 10 o'clock this Saturday so I can take you shopping for the other things you need. If you don't show up don't ever come by here again. Understood?" her tone more authoritative. "Yes, "he replied. "10 o'clock sharp." she pointedly repeated. With that he left the store and headed home.