Just Look at Me Now Ch. 07

As my first six months of guided feminization drew to a close, I entered negotiations on a contract for my first full year of submission to Jude and Becky. Our discussion proceeded over the course of a couple of weeks, in person and by email, and was punctuated by my trip to Melinda's lingerie boutique to buy new bras. I'll tell you a bit about the contract before I describe my shopping adventure.

When you consider that Jude and Becky's opening negotiating position was essentially that they could make me do anything they wanted, I managed to eke out a few concessions that made me comfortable signing a document that I considered as binding as any legal filing. As I look back now at the contract and recall the experiences to which it led, I feel like I got snookered to just about the right degree for everyone's enjoyment.

It was important to me that we preserve my anonymity, though I would risk going to SF Pride en femme and would undertake a number of challenging shopping trips for lingerie, cosmetics, sex toys, and so on. Becky and Jude had no problem with my privacy concerns, or with my proposed prohibitions against lasting marks, urine, and scat, so these matters were quickly settled.

My main worry was over something that they had hinted at on Halloween—that my sissification would not be complete until I had sucked a man's cock the way Melinda had sucked mine after the Halloween party. For me cock sucking was the ultimate humiliation, and while I was willing to try it I was not willing to blow some random guy at a party. To accommodate my concerns, the contract required prior notice for me, STD screening of the man, and a maximum of four blow jobs for the year, always with just one man present. If you think these logistics might make the cock sucking unmanageable, don't be too sure!

The other item that caused me the most apprehension was the section on Anal Training that made my getting pegged a specific goal. My worries here, though, were purely those of safety and physical ability. Would it really be possible to gradually stretch my little anus sufficiently to take even a smallish dildo? That frankly seemed unlikely at the time, but emotionally and erotically I was eager. I had already been bound to the spanking bench with a finger up my ass and a strap-on in my mouth, so the thrill of being used fore and aft at once was a known and much-craved experience. We would just be taking it to a new level once my body was prepped.

The other items in the contract—the hypnosis, the slush fund, my sissy diary, and so on—prompted nervous and exciting anticipation, not real fear.

As I mentioned, my in-person shopping for bras occurred in the middle of our negotiations. I met Jude and Becky at their apartment about an hour before my 11 a.m. appointment. They gave me a few final instructions—for example that I must not rush the shopping—but mostly they were supportive and encouraging. They knew that being seen by strangers while crossdressed was a huge step for me, and they genuinely admired my willingness to take this risk.

I changed into a relatively safe outfit for our five-minute walk to the boutique. I wore women's jeans that were almost indistinguishable from men's; my light gray blouse, though it buttoned the wrong way, was not strikingly different from a men's dress shirt. Despite the slightly chilly air on a sunny December morning, we all walked the two blocks without jackets, which would only get in the way while shopping. Beneath my jeans were panties, of course, and beneath the blouse I wore my best fitting bra that didn't require breast forms.

I carried a Lululemon bag with a few key items: a wig, a pair of women's flats, and my two sets of breast forms, the D size I had originally purchased plus my brand new, heavy, seriously large GG pair. I had shopped for these online with Becky and Jude early in November as we began shaping my contract. Melinda had warned that anything bigger than F cups might make me top-heavy, but Jude insisted we go big. "This way we can call your boobs 'Gigi,'" she joked. We also opted for attachable forms with—who knew?—a choice of nipple shapes. Of course I ended up with the most prominent nips. So I had this bag of goodies, and Becky carried a small garment bag with more clothes for me—two skirts and three additional blouses.

As you know, I'd seen the shop from the outside previously—standing with Melinda and Sandy, admiring the lingerie through the shop window, and wondering how long it would take for the key to my cock cage to reach me in the mail. As I was about to enter I felt the way I do when a rollercoaster is reaching the highest point of its slow climb—excited, a bit scared, and intensely aware that a wild ride is about to begin.

Becky held the door open and Jude gestured for me to enter first. Reminding myself not to rush, I walked past a couple of shoppers to the cashier's counter, swallowed hard, and announced in a reasonably calm voice, "Good morning. I'm Nick. I'm here for my bra fitting appointment, 11 o'clock. These are my friends Jude and Becky."

"Hi everyone, I'm Jasmine," the saleswoman replied. "I see you on the schedule here. Melinda, our store manager, is expecting you. I'll let her know you're here."

As predicted, the boutique was somewhat crowded with the holiday sale just beginning. Although the storefront was not very wide, the boutique was surprisingly spacious—with a long shopping area in the front leading to a set of seven dressing rooms in the back. The walls of the show room were packed with thousands of bras—more than a dozen brands, scores of styles from each manufacturer, and a full range of band and cup sizes. Cabinets beneath the racks of bras held additional sizes and, I learned later, matching panties when available.

I had a few moments to take all this in as well as to note how the other shoppers were reacting to me. I encountered many a curious glance followed by clear efforts to be discrete; no one stared or commented, but they had all heard my voice. I assumed my presence was making a few of them uncomfortable, but considering how uncomfortable I was it seemed like a fair trade-off.

Melinda soon emerged from the dressing room area, accompanied by a young salesclerk. "Good morning, Nick," Melinda said. "It's great to see you. I'm going to make sure you walk out with better-fitting and more luxurious bras than you've ever imagined, and at sale prices!"

"I hope you can help me out a bit, too," she continued. "This is my sales associate Beth (5-way introductions all around here). Beth is a relatively new hire. She's extremely capable but hasn't had a chance yet to work with any of our trans or crossdressing clients. If you don't mind I'd like her to do your bra fitting along with me and then help out with your selections as well. Is that OK?"

"Yes, that's fine," I replied, not only because Jude would likely have required my cooperation, but because I honestly didn't mind. After all, half a dozen women had already seen me, and more would do so shortly.

"Great," said Melinda. "Your dressing room is ready. Just follow me."

So the five of us walked to the back section of the store and entered a spacious dressing room with two chairs, a full-length mirror, loads of hooks, and a large curtain at the doorway. Jude and Becky were given the chairs while Melinda, Beth and I stood. Tight quarters for five people, but manageable. I had noticed that we were in the middle of a row of five rooms with two more across the aisle; all of their curtains were closed, but I could hear quiet conversations from a couple of them, and some bras were hanging on hooks at the doorway, presumably to be handed to clients sequentially.

"Let's begin with a measurement," said Beth as she grabbed a tape measure from a hook. "Are you wearing a bra right now?"

"Yes," I answered. "Melinda recommended that I wear my best-fitting bra." I was acutely aware that any of the women I had heard could hear me too, but I tried to maintain a normal voice.

"Perfect," said Beth. "If you don't mind removing your blouse that will let me get the most accurate measurement, but I can measure over your blouse if you prefer."

"I don't mind taking it off," I replied as I began unbuttoning it. "And as you can see we've brought a couple of other outfits, so I'll be changing clothes as well as bras."

"I'll hang that here for you," said Beth when I had the blouse off. "That's a very pretty bra you have, though I can see it gaps a little bit in the cups."

The measurement took less than a minute, with my role being primarily to stand up straight and keep my arms out of the way. Beth measured me at the band level and then across the bra at the largest circumference of my chest.

"I make your technical fit a 40 AA," she said. "If you want comfort more than support you could go to a 42 AAA, a size you won't find in just any old store. Melinda, would you like to double-check it?"

So Melinda measured me as well. "Spot on," she announced. "Of course every brand and style of bra varies slightly, but this will give us a great starting point. Remember as you try things on that you'll want to use the loosest set of hooks when the bra is brand new, then move to tighter ones as the bra stretches slightly over time."

"Beth and I will bring you some options, both underwire and wire-free, and you can begin to narrow things down—unless you want to buy them all! Oh, and Beth, you should know that Nick will be trying on larger sizes a bit later—I believe he brought along his breast forms. That's why I blocked out this room for two hours. Nick, remind me of the other cups sizes you want to shop."

I had mentally prepared for such a moment, but it was still a little hard to get the words out: "I want to try on bras with a D cup and also a double-G cup."

"Good to know," said Beth. "We can work our way from small to large, beginning with our IBTC collection."

Melinda noticed the puzzled look on my face. "Oh, that's an acronym you definitely should know. It stands for the Itty-Bitty-Titty-Committee, and your natural AA/AAA cup qualifies you to be a card-carrying member! We'll be back in a few minutes—you'll have time to change clothes if you like, and we'll knock before we open the curtain.

It's of course polite to knock before entering, but a knock says nothing about who else might be passing by. I figured this out right away when Melinda pulled aside the curtain so that she and Beth could exit. Walking by as I stood in my bra and women's jeans was a well-trained sales associate who didn't so much as glance at me, but her client was not quite so discreet. She didn't exactly stare, but she took a careful look as if to be sure she was really seeing a man in a bra.

"Time for a skirt," said Jude as Beth swept the curtain shut. I changed quickly from the jeans into a solid navy skirt, knee length, that would go with any of the three blouses I'd brought along. I swapped shoes and then we briefly waited for Melinda and Beth to return. That's when the blizzard of bras began in earnest.

Melinda knocked, swept the curtain aside, complimented me on my skirt, and hung eight bras on a couple of hooks. "I suggest you try all these on, if only for fit," she said. Some come in more than one color, so if you like the style and fit you can choose a color later. I'm sure you've noticed our Yes-No-Maybe hooks. It really helps us if you use those so we can at least clear away the No's and not end up with fifty bras in here at once."

She again swept the curtain aside—no one outside this time—and Jude and Becky and I got down to work. It was immensely helpful to have their four hands busy handling the little hangers and, more importantly, fastening my bra hooks and helping adjust the straps. It would have taken me three times as long on my own. I had just removed my second bra (resulting in one No, one Maybe) when there was a knock, the curtain was swept aside, and Beth in the doorway with seven more bras. This was when I stopped counting. It was also the point at which Becky told Beth "you can just come in without knocking—Nick's not shy, and he'll be out on the floor shopping soon, so no worries about other customers seeing him."

sFor the next thirty minutes or so I stood pretty much like a mannequin as bras went on and off, Melinda and Beth came in and out, and the curtain opened and closed with saleswomen and clients occasionally getting a look at me. If my body was still, however, my voice was busy, as Jude in particular kept up a steady stream of observations and questions. So I was saying things like, "this feels a little tight" and "yes, the pink is prettier than the black," and "no, I haven't had a bra with detachable straps before."

My emotions were also busy. I was quickly becoming accustomed to my environment—the most markedly feminine setting I'd ever experienced—and when enough time passed with nothing hostile or mean-spirited having been said, I began to relax and, well, just shop for bras. And that was quite a challenge: even as we worked with just the small-cup bras, the fit and the quality of almost every single one was better than I'd ever managed to buy online.

Finally I narrowed the field to two Maybe's and countless No's—even at sale prices I couldn't afford to buy a dozen bras. My two favorites in this first round of shopping were attractive for different reasons. One was a simple wireless bra, in a solid sky-blue, that would be easy to conceal under almost any shirt and comfortable enough to wear all day. The second, with its underwire, was sexier: a royal purple background with elaborate black lace. It also provided a little lift and shape to my chest; when I looked at myself in the mirror and touched my nipples through its fabric, I felt like truly had my own titties, itty-bitty as they might be.

Now it was time for a tougher challenge—shopping for a D-cup bra. I had agreed to leave the relative safety of the dressing room to shop in the show room, assisted by Melinda and Beth. Jude and Becky would be out there too, picking out a few bras that they'd like to see me in.

Melinda brought me a simple full-figure bra, 40D, to check the fit. When I had it on, Jude said, "Well, Nick, let's have a look at your boobs!" And so I took the smaller set of breast forms from my Lululemon bag and the four women had a look at them. In fact they had a feel of them too, passing them around to assess their weight and density. "These are excellent quality," said Melinda, "and of course perfectly symmetrical, so we'll just have to find bras with enough structure to hold them in place. I like that floral blouse you brought... how about wearing that for now?"

Given the situation, one blouse was as good as another as far as I was concerned, so I positioned my breast forms in my bra and buttoned on the floral blouse. "Oh, these too," said Jude, pulling a pair of panty hose from her purse.

"Just come out whenever you're ready," said Melinda as she pulled the curtain aside and ushered Beth out of the dressing room. "We'll begin picking out a few different styles for you to consider." So I was spared wrestling on my pantyhose in front of Melinda and Beth. Soon I was fully dressed—panties, bra, hose, skirt, blouse, and flats—but was I ready? Could I roam around a room of women I'd never met while talking to Melinda about push-up bras and front-closure bras, about fabrics and colors, and about the availability of matching panties?

As I hesitated, Jude reminded me that nothing bad could happen—customers would look, but none of them would know me. Becky faced me, held my shoulders gently, and told me to take five deep breaths while I looked into her eyes. (The calming effect this had on me turned out to be a preview of her emerging talent for hypnotism. I'll tell you sometime about what it was like to see a video of myself performing naked jumping jacks with absolutely no memory of the experience.) "You can do this," she said. "Just have fun being a woman for a while."

Calmed at least somewhat by these reassurances, I drew the curtain back and walked down the short hallway to the salesroom. Again I thought of a roller coaster ride and beginning the plunge—now there was no going back. I spotted Melinda across the room, but though I knew I would feel safer by her side, I took my time and actually stopped and looked at some of the beautiful bras all around me. At first this was play-acting—I was just trying to look like I was shopping as I assessed the women around me and reminded myself to breathe.

Certainly I drew a lot of immediate attention. Some women saw me right away, and if they were alongside a friend or a sales associate, they invariably directed others' eyes to me with varying degrees of (un)subtlety. It was also clear that the dressing rooms were clearing out; the women who'd known a man was trying on bras now had a chance to add a visual to the soundtrack. I interpreted their reactions as mostly innocuous—some surprise, some amusement, and a tendency to look at me, then away, then at me again, as if to observe without ogling. In these first few minutes of my venturing out among the other shoppers, only one woman's expression was emphatically negative—apparent disgust with a tinge of anger, or at least that's what I imagined.

I gradually transitioned from fake shopping to real shopping, paying attention to what bras were most lovely as I strolled around the perimeter of the room. After a few minutes of looking around, it occurred to me that I hadn't actually touched any of the bras out on the sales floor, so I made a point of taking one down from its rack, checking its size and price, and looking to see if a D cup was in stock. After this warmup exercise I joined Melinda for her expert guidance.

Our Halloween encounter was of course fresh in my mind, and I liked to think of that night as a bit of adventurous role-playing—me as a sissy maid and Melinda as a cross-dressed young wizard who didn't mind sucking a cock when the stars aligned. Now we took on new roles—her familiar role as a sales associate and my unfamiliar one as an uncloseted lingerie enthusiast.

At first I performed like an understudy: unsure of my lines, my voice quavering at times, a slight tremor in my hands when examining a bra. Melinda, however, gave a polished, confident performance, treating me precisely as she would any other customer. Meanwhile Beth spent most of her time helping other shoppers, but occasionally stopping by with a bra or two I might want to try on.

I also had two very brief conversations with clients. When Melinda was showing me an intricate bra from a French manufacturer, a woman just to my left simply said, "That's gorgeous!" She was about my age, and I remember her very long brown hair, narrow face, and bright red lipstick.

"Yes," I agreed. "Melinda, if you have this in my size I'd like to try it on."

"Me too," said my fellow shopper. "It's just lovely. I'm a 34C."

Both sizes were in stock, so we had identical "Maybe" bras to try on. That was fun. The woman and I exchanged smiles but no further words, and I felt more at ease.

The second woman who spoke to me was much younger and not quite so tactful. Approaching me sheepishly, she said, "I'm sorry, I have to ask, um, are those your real boobs?" She apparently knew a lot more or a lot less about hormone therapies than I did.

"No, they're silicone breast forms," I replied.

"Oh. Sorry, I just, I mean I was curious. I didn't..." She was blushing and clearly embarrassed.

"What about yours?" I asked.

"What? Oh—they're real!" She gave them a little shake and we both laughed.

"No harm done," I said. "I know you don't meet someone like me every day. If you stick around for a while I'll show you my bigger boobs, also silicone." She did, and I did, but I get ahead of myself.