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A Day at the Mall

How I Learned to be Proud of My Breasts

Background: The Trainer

I hate men, passionately. They're hairy, ugly, and all too often, dirty. I can't stand the feel of their stupid faces against my skin. They're either unshaven, therefore tickle, or poorly shaven, therefore scratch. Their bodies are hairy and ugly and misshapen, too. They have no soft places to kiss and caress, unless they are disgustingly fat and wobble when they walk. Their sex organs are downright ugly, slightly reminiscent of crocket mallets waiting to pound on something. Their scrota resemble those stress-exercise balls used to firm up one's grip. That actually is one pleasant image, grasping their balls in one hand and squeezing, squeezing, squeezing as hard as possible.

However, I am a romantic, and a somewhat attractive woman, though I do wear “a few extra pounds” here and there. I enjoy sex, even if only at the behest of a vibrator. I try to limit orgasms to one per day, though I have occasionally exceeded this goal. Every time, I do imagine the feel of a man inside me, filling me, stimulating me.

Since my early twenties, I've presented myself as a male. I wear my hair short, not a buzz cut but about an inch long. This leaves me with no hassles involving tangles or combs or brushes. Ten seconds is enough to ensure my hair is completely in place. I do not wear makeup. I hate makeup. It's gooey and smelly and never goes in the right places, based on the few times I tried it as a teenager. I do not wear nail polish. It's even smellier, and loves to climb onto my cuticles and skin. I do not wear jewelry, except for one garnet necklace given to me by a close friend. I especially do not wear earrings, for the thought of poking holes in my body gives me the shivers. I dress in sweatshirts and hoodies one size too large, along with plain old denims and tennis shoes, to hide my curves as well as I can. I do wear bras, usually sports bras one size too small so they compress my admittedly generous breasts against my chest. And my panties are as plain as can be, gray cotton things. I do find my monthly maintenance chores to be annoying, but push through them as quickly as possible.

So, in short, I make believe I am a man, trapped in a woman's body. Though my given name is Margaret, I accept, gladly, the nickname of Bobbie. I've been doing this for twenty years, and I am happy. I have no desire to change.

This has led to some stress at work and with family. Men, against all reason, ask me out for dates. “No way” is the most polite answer I offer, when I'm in a good mood. Women wonder if I'm gay, and glance at me when they think I'm not looking. Maybe I am, I sometimes think, then banish the thought. My siblings often ask annoying questions about my love life, and get nothing but a glare in return.

At one office holiday party, I did get a wee bit drunk. I'm sure I could have stood up if I really tried, but I didn't want to try. One of my co-workers, I forget who, got into a discussion of gender-bending stuff, like “should boys who feel like girls be allowed to use girls' bathrooms at school?” I didn't pay much attention, for the whole topic seemed silly (boys are boys, just see if anything's hanging between their legs) and I had a hard time following the discussion. But I do recall someone mentioning “The Trainer”, as a friendly expert on gender stuff.

A few nights later, with nothing else to do, I got to thinking about my gender preferences. It dawned on me that maybe not everything was aligned as well as it could be. Up came Google, with a search for “The Trainer”. After the inevitable movies and plays and other garbage, I did find a reference to a woman in my area whose web site offered “private consultations about one's role in the modern sexual marketplace”. I know, this is not impressive, but I did give in to an unexpected urge to make contact. I sent an email from a semi-anonymous account to The Trainer. It contained a variation of the summary I've presented here, along with my pointed question of the form “So what can you do for me?”

She responded quickly and very politely. She admitted that she'd need to meet me to properly answer my question. She added some detail, stating that her goal was to help people find comfort in themselves, acknowledging reality and shedding pretense. Her preferred method was role-playing. She'd meet with a client, work out a way to experiment, with an emphasis on emotional safety, with different presentations. She was clear that she is not prescriptive and she is non-judgmental. Her only goal is to find the most comfortable self-image for her students.

Normally I avoid feel-good advisors who only feel good when they receive a check from me. But The Trainer seemed more sincere, and more humble, than other quacks I've encountered. I decided to give her a chance, just one.

I made an appointment to visit her the next Wednesday, from noon to 5PM.

Preparation: Making the Plan

I showed up at The Trainer's apartment precisely at noon. She let me in, and immediately offered me a seat and a cup of tea. She was a mature and rather dowdy woman, but clearly energetic and intelligent. Her apartment was small, containing a single living/dining room and a hall leading to a bathroom and, I assumed, a bedroom. Two cats lounged on the floor, but seemed quite elderly, as they barely moved when I entered.

We talked about innocuous things as we got to know one another. We both hate sports, and the men they attract. We both enjoy history and music, though I'm more into engineering, and she into art. It was easy to open up to her, for she was quite open with me.

Then we got down to business. She clearly understood that I visualize myself as a man, biology notwithstanding, and am happy with that. She was very supportive of this, emphasizing that one should find a role in which one feels comfortable, and stick with it, regardless of outside opinion. She even asserted that I was handsome, though I wrote this off as the kind of pandering that comes with professional client relations.

The crux came when she asked me what alternative roles I had considered. I blushed. I do have a secret fantasy. So secret it's known only to me. I thought long and hard about whether I should reveal it to her. She waited, silently, knowing that I was struggling internally. She was patient. She seemed sincerely interested in my thoughts. I gave in.

“I do sometimes wonder what it would be like to live life as a real woman, provided we could get rid of all the men”, was my current thought. “I don't think I want to be a lesbian, but I do sometimes wonder what it would be like to be Cinderella – without Prince Charming.”

She was silent. I was silent. We looked at each other, and she smiled a bit and nodded slightly. “I know exactly what you mean” she spoke, softly. I believed her.

“Would you be interested in a simple experiment to help clarify your feelings?” she asked.

“What kind of experiment?” I wondered. I liked her, but was not about to yield control to her.

“Let's just go for a ride. Go to a mall, perhaps. Let's find a place not far from here, but where you won't be known. In the process, let's do some simple role-playing. Let's just fix you up to be a bit more feminine, and see how you feel about it.”

“What do you mean by fixing me up?” I had to know.

“I suggest we keep things simple. I can put some light makeup on you. I can loan you a simple wig, not big and long, but something down to your shoulders, perhaps. I have some discrete jewelry. But mostly, let's show off your breasts a bit more.”

I was seriously taken aback, especially by her final clause. Repeat: I don't like makeup. Repeat: I don't like long hair. Repeat: I don't like jewelry. Repeat: I don't want other people staring at my breasts. But I do like having breasts, and sometimes, late at night, I stand in front of a mirror and…whatever.

However, I did feel a surge of interest, maybe even excitement. A warm feeling grew in my crotch. Something sexually significant began. I became modestly aroused, and this does not happen outside my bedroom.

“Think about it for a few minutes”, said The Trainer.

I did. I imagined walking down the aisle of one of the nearby malls. I imagined wearing those self-forbidden items: makeup, earrings, bracelets, and wig. I especially imagined allowing my breasts to show. The warmth spread. Arousal grew. I went further, and imagined adopting the arched-back posture used by exotic women, pulling my shoulders back and pushing my breasts forward. My breath caught in my throat. I wanted to do this, to let myself go, to appear as a woman, sensual, erotic. Damn the men. I formed the idea of competing with other women: “Mine are bigger than yours, now what do you say?”

To this day, I don't know what I desired more at that instant: a climax, or to go on with The Trainer's expedition. I was so aroused that judgment failed me. I acceded to her suggestion.

But then cold feet set in. I wondered why I should bother at all with this silly idea. I was sure no good would come of it, and the next day I would simply revert to my normal, comfortable life. Why take any risk at all? I still didn't know The Trainer very well, though I was beginning to like her. Besides, I'm happy being male, at least in concept.

Fortunately, it was winter. I could contemplate a compromise: I could wear my winter coat, which I had left in my car. This would hide my breasts, to some extent, if things became to embarrassing. I did not want men to be glaring at me, under any circumstances.

Also, I wanted an escape path. I didn't want to give The Trainer more control than necessary, but I did think her presence could give me confidence. I asked her for a piece of paper and pen, and scribbled out the following caveats:

1. I wear the entire setup, including my winter coat, as we leave your home, and I drive us to the Mall

2. We walk into the Mall, and promenade around it, with my coat buttoned, window-shopping, as I adjust to the wig, makeup and jewelry

3. You signal me to unbutton my coat, revealing the shape of my breasts, and we continue walking

4. We find a seat in the Food Court, and you signal me to remove my coat entirely, exposing the shape of my breasts to all who would look

5. After some time, we resume our walk, with me carrying my coat on my arm, again window-shopping, breasts clearly on display

6. If the weather permits, we return to the car, you unlock it and tell me to put my coat in it, then we return to the mall, removing the psychological safety net that the coat had provided

7. We continue our promenade, and as we pass each store, you ask me to identify an item we might examine in each one

8. You select one store for us to enter and contemplate a purchase, where I must talk with a sales person (preferably female), my breasts directly in front of her.

The Trainer took no issue with these suggestions. We had a plan.

Transformation: From Bobbie to Maggie

The Trainer took charge. “Stay here, I'll be right back”. Sure enough, a few minutes later she returned, arms full of stuff.

“Let's start with the basics. Take off your sweatshirt, please.” This gave me no pause, as my sports bra is a very utilitarian thing, not likely to excite anyone, especially The Trainer.

“Thank you. Now, here's a more appealing bra. Put it on. Would you like me to leave while you do so?” This was an interesting combination of authority and sensitivity. Again, I gave in.

“No, you may stay, of course.” I examined the bra she had given me. It was lacy, but well constructed, as the back panel included four clasps. It also had an underwire, the purpose of which I had long forgotten. I put it on, and almost gasped. I discovered the reason for the underwire, as it rounded my breasts. Being of the proper size, the cups forced them to protrude more than I'd ever experienced. The lace was semi-transparent, and my nipples showed clearly, both in color and in shape. I looked bustier than I ever had. I did not enjoy the concept. I do not show off my breasts. Yet here, I did. Something again stirred between my legs.

The Trainer said nothing. She handed me a turquoise knit sweater, obviously wishing me to put it on. I did. It covered the bra, and hid the color of my nipples, but not their shape. I protruded. They protruded. I felt as though an alien had overtaken my body. Unconsciously, I arched my back, slightly. I protruded more. I became more aroused. My nipples protruded more. This was not me! But it was fun.

She handed me a wig. I somehow figured out how to pull it over my short-cropped hair. It fit snuggly. As promised, it was not too long, not quite coming down to my shoulders, with bangs almost reaching my eyebrows. She pulled out a comb, combed the wig quickly, and then stepped back.

“Go into the bathroom, and take a look at yourself.” I did. I gasped, for real. For that was not me in the mirror. It was a busty woman, with simple yet feminine hair. Was I that woman? “Put these on”, she said, handing me a pair of dangly, somewhat tacky, earrings. The pressure of the clips on my ear lobes was quite surprising. “Turn and look at me” was her next instruction. I did, and she deftly dabbed eye shadow, eyebrow pencil, and lipstick on me. “Look again.” I did, and could not believe the transformation. At least from the waist up, I was no longer my own comfortable tomboy. I was a full-fledged woman. It made me very, very uncomfortable, for this was an entirely unfamiliar concept. It was arousing, though, for inexplicable reasons. “Tell me what you see.”

“I see a woman, a real woman. She is not me. I would be embarrassed to be seen like this in any other circumstances. I am embarrassed now. I do not want to be this woman. She defies major parts of my personal self-image. Let's stop.”

“Can we compromise, and just take a break? Please, come take a seat in the living room?” She led the way, and I followed. Somehow I had fallen into a subservient role, accepting her suggestions, though still feeling free to offer my own opinions. She offered, and produced, another cup of tea. It was Earl Gray, I think.

“This is just a role-playing experiment. I'm not trying to change you at all. You will be the same person tomorrow morning as you were when you woke up this morning. The only thing that will change is your experience. Please, stay with me, let's do this, so you can go home knowing, in more detail, what you've chosen not to include in your self-image, yet.”

I remained silent. She had a good point. Her offer was to try something new, like bocce or skydiving. I would not change. Or if I did change, it would be my choice to do so. I would be embarrassed in the process, just as if I were to take up bocce, having no skill in it. I would learn something, though, and I do appreciate the value of learning. “Ok.”

We left her apartment, and walked to my car. Nobody was in the hallway, so nobody saw me. We got to the car, opened it, and I immediately put on my winter coat. I almost never wear it, because it has a somewhat feminine cut and fur collar, but now it served as a savior. Buttoned tightly, it effectively hid my breasts. I again felt comfortable. I didn't even think about the other parts of my transformation. I relaxed.

However, I could not escape the realization that I was no longer Bobbie. I was back to being Margaret, or perhaps Maggie.

Experience: At the Mall

We headed to the mall, and I concentrated on driving, nothing else. I focused my attention on traffic, signals, and other wild and dangerous drivers. She chatted about her cats, the decorations in her apartment, and her enthusiasm for medieval English history. No thoughts of the coming activity complicated our thinking.

We arrived at the mall, and I parked somewhat near one of the main entrances. Feigning nonchalance, I got out, sure that the coat was completely buttoned. I helped The Trainer out of her side, locked the car, and we proceeded to the mall entrance.

Somewhere between the car and the entrance, it hit me. I was now a different person. I had long hair. I was wearing makeup. I was wearing earrings. And despite my self-delusion, my breast-mounds clearly filled out my coat in a way I'd not experienced in many, many years. I was Maggie. I was exhibiting femininity, not hiding it. The Trainer was silent at my side, inscrutable, letting me come to grips with the new reality.

As we approached the door, two or three scruffy men stood outside. They were smoking, and they were gaping. They weren't gaping at The Teacher, since she was dressed very conventionally, and comported herself with a deliberately lackluster demeanor. No, they were gaping at me. To them, I was a well-made-up busty woman, despite the jeans and sneakers, and they barely restrained their leers. Embarrassed though I was, I held their eyes, knowing that this would increase their interest, but refusing to be intimidated by them.

We got to the door, and went inside. We entered on the second floor. A short way ahead of us was an escalator down to the first floor. We were in a light, airy lobby, and I felt as though I had just stepped on stage. Everyone in the lobby could see Maggie, even though I was not really Maggie.

At the base of the escalator, two mall handcart vendors accosted us. “Hello, ladies, would you like some mumbledygook?”. I didn't even pay attention to what they were selling. I instinctively don't like being called a lady, for I am Bobbie, and I am a male. Except then, I was not Bobbie, I was Maggie, and I was female. I became very confused.

The Trainer led us into a gem shop. It was very nicely set up, with sales staff that clearly valued customers. One saleswoman came over to me, and asked about what I was interested. At any other time, this would have been a pleasant experience. But now, The Teacher had brought us directly to the 8th step of the 8 step way I had insisted upon, and I became severely disoriented.

Here I was, big-busted woman with breasts enhanced by an underwire bra, wearing makeup, earrings, and long hair. This image was far from the masculine Bobbie to which I was accustomed. I put my hands deep into my pockets. I hunched over to hide my breasts. I shifted my shoulders up so that my coat collar would cover my neck. I tried to hide. The Trainer ignored me, pleasantly gabbing about this and that. I left the store, found a corner in which to stand, and pretended to be invisible.

Eventually The Trainer emerged from the shop. She immediately recognized my distress. She led me over to a set of chairs in the lobby through which we had entered, and gestured to me to sit down. “What's wrong?” she asked, kindly.

“I wanted to ease into this situation. I provided you with a list of incremental steps by which we could do this. You took us right to the end of the list. I am feeling extremely uncomfortable. I simply do not know how to comport myself when I'm in this position.” Those were the nice words. The less nice thoughts included no small amount of anger, for I felt she had violated the implicit compact we had made when she accepted my amendment to her plan.

“You are absolutely right. I got carried away. I am so sorry. Would you like to go home now, or figure out a way to proceed?” Such compassion and humility surprised me. Anger fled. Now that I was in her scene, I did want to go forward. But I wanted to slow down.

“There's a food court in front of us. Can we find someplace to sit, as far out of sight as possible?” I asked.

“Sure, that's a good idea”, she said. “Lead the way.”

I led us to a half-booth near the ground floor entrance. She offered to get us slices of pizza and soft drinks. I acceded, and she went off to do so. Left alone, I thought about my situation. The good news was that I was in a position where I really could try on a new personality. The bad news was that it was one with which I was completely unfamiliar, and therefore completely lacking in self-confidence. An interesting element of fun remained, however. I was a new person, Maggie. I could project a distinctly feminine image. And with The Trainer's support, I could readily avoid normal irritations. I resolved to try, but at my own pace.

Updated: December 19, 2016 — 5:17 am
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