Shopping for a bra can be a marvelous experience if you go to the right store.

What started as a wild idea had become an obsession. It all started when I was window shopping at the mall last year on Black Friday, the start of the Christmas shopping season, and had walked into a Victoria's Secret store for the first time. The place had long fascinated me, but unlike boys my age who looked at the window posters with lust, I my emotion was always envy. That day I could see from outside that the store was crowded with shoppers including couples of all ages where a guy had been dragged in to be given 'hints.' I figured that the presence of other males and the excuse of holiday shopping would provide me cover. I wandered around for a while admiring the sexualized feminine displays and imagined how wonderful it would be to wear something like that. After a few minutes I sensed that one of the women working in the store was approaching me.

"Can I help you with something?"

"Just looking," I said nervously. She gave me a curious look, and I quickly left, thankfully without further incident.

For as long as I could remember I had wished I had been born a girl, but could never bring myself to talk openly about this. Growing up I had never fit in with the guys, but had a lot of social friends among the girls. Being good with art and music and being one of only two boys in the high school dance company certainly helped me in that regard. I knew I wasn't gay like the other boy in the dance company, but wasn't sure what gender terms applied to me. My constant fantasy was being transformed into a girl and growing up to be a woman. I figured my family would disown me, or worse, if they knew, so I just kept my secret to myself year after year.

Like many boys I had 'experimented' with Mom's clothes. Later, when I was in Middle School I had salvaged some unknown girl's bra from the school trash when the custodians were cleaning out the gym lockers at the end of the year. The fit was terrible, but I treasured it. After a few weeks I decided the bra was too dangerous to keep hidden in my room and it went into the dumpster behind a convenience store.

Now, that first Victoria's Secret visit started me in a new fantasy direction -- shopping openly for feminine clothes became something I would think about lying in bed at night. As time went on this fantasy became more and more a part of my thoughts and I began to think about really doing it. At first I thought about using the crossdressers well-worn 'gift for a friend' excuse. I would rehearse my lines until I had a credible story and had my presentation down like a good actor. Time and again I would go to the mall, walk past Victoria's Secret, then chicken out. I was afraid of a lot of things: being recognized by someone who knew me or my family; disapproval from people in the store; or just losing my self control and ending up looking like a fool.

Meanwhile, I was becoming more and more convinced that I needed to do something dramatic to test my own commitment to femininity. I figured that if I could come out to a stranger it would help me develop the courage to share my secret with my family.

As usually happens, I kept raising the ante in my fantasy.
My dreams evolved from just buying a bra to making it totally clear who the bra was for. About this time I came across a web site discussing whether Victoria's Secret allowed men into the changing rooms. Like most chat rooms the answers were poorly written and ranged from 'I don't know' to 'it depends,' but the idea sent me into another new direction. That night I imagined not only openly shopping for a bra but also trying it on to be sure it fit before paying. This fantasy was becoming more and more unrealistic. I live in a small town and our family is well known so how was I going to manage this charade without encountering someone who knew me? What if the store clerk was shocked by my request and kicked me out of the store. Worse, I could imagine a woman calling mall security about some pervert in the changing rooms. Of course, this sense of danger only increased the fascination.

I suppose my male hormones that I detested so much were still enough to give me that love of danger that makes young men into risk-takers. At my age there is an incredible thrill to doing something that has potentially terrible consequences and proving that you can get away with it. Most guys my age drive fast, drink excessively, get involved in fights, join the Army. I just wanted to go back to Victoria's Secret and shop as though I was a girl.

My break came when I got an email asking me to schedule an interview for a summer job at a fine arts camp in the southern part of the state. The trip there would take me though a distant city where I would be unlikely to be recognized, and I quickly verified that the city had mall with a Victoria's Secret shop. What major mall doesn't? I accepted the interview invitation and specifically requested a Monday afternoon. If I left early and drove the speed limit I would have plenty of time to shop before the interview. I knew that Monday mornings were the slowest time of the week. That was important since the lack of customers would make the clerk anxious to make a sale, and reduce the risk of any encounters with other customers. I continued to plan: have plenty of cash, wear something gender-neutral or better yet a bit flamboyant, have my hair neat. If I was going to do this crazy thing I wanted to make a real statement about my identity. I had been slowly accumulating some clothes and accessories that were not strictly masculine. Mom sometimes rolled her eyes, but let me spend my money as I wanted.

On the big morning I dressed in a pair of no-fly briefs (sold as men's fashion high-cut, but at least not baggy boxers), a smooth light blue shirt, and a pair of skinny jeans with a hint of embroidery on the back pockets.

"You're up early, dear. I guess you are excited about the interview."

As I sat down to breakfast Mom was clearly checking me out.

"That's quite a pair of pants. I guess a fine arts camp is used to men who dress like that, but for a job interview ..."

"Got to go, bye," I mumbled as I headed out to my old but serviceable car. It was a big expense on my after school job income, but wheels gave me independence. I cruised down the street heading toward the freeway on ramp. I was full of anticipation, but tried to think about other things. I knew if I thought too much about what I was going to do I would never go through with it. Being relaxed was the key. After a few hours I finally arrived at Red Desert Mall, and parked in the nearly empty lot. "Good so far, " I thought.

I entered and found the store directory sign. As I looked for the Victoria's Secret location I realized my heart was already racing. I knew from drama workshops the importance of calming down and being in character. I found a drinking fountain then the (men's) restroom before walking down the corridor. I saw the Victoria's Secret ahead, slowed down, glanced in, then kept walking. I realized I was still too nervous. I walked a bit farther, paused in front of a few store windows, turned around, and went to the food court to sit down. I was just another customer in the mall, but I felt that everyone was looking at me as if they could read my mind. Impossible! How could the security guard, the janitor, the lady with kids in tow, the jewelry salesman at the kiosk, or anyone else know what I had in mind? Eventually I got my mental state back in control and was ready for another attempt.

This time I approached the Victoria's Secret and walked right in. I glanced around and saw that the store was empty except for one employee working on rearranging displays. She was about my age and quite attractive. I started wandering around looking at all the delightful merchandise. I wasn't familiar with all the bra options so I started to read signs and look carefully at the mannequins. I knew that before long the clerk would notice me, and I hoped I would remember what I planned to say.

"Good morning? Looking for anything special?"

Special, was that a code word? It was now or never. No lying about gifts for girl friends or anything else like that."

"I'm looking for a bra." I did it! No turning back now.

"Do you know what size and style you want?" I noticed that the clerk was not asking, "Do you know HER size?" She was acting like my request was perfectly normal.

My mouth was dry so I swallowed before answering. "I'm not sure, probably something with small cups but a large band." I had measured myself countless times but I let fantasy trump reality. "Maybe a 36 or 38 B?" She gave me a quick once-over with her eyes and smiled. My answers did not leave much doubt about whom the bra was for, and I clearly was not a B-cup.

Without hesitation she began sorting through the bras on the table display below a sign saying 'Sexy Teen Bras.' "I was expecting to find something nice right here, but it looks like we are out of the larger sizes. I think you will like something padded."

I nodded as she directed me to another section of the store, opened one of the drawers and continued sorting through the endless piles of bras. I was savoring the experience. Eventually pulled out a very pretty flesh-colored bra with lace trim and nicely formed foam-padded cups. "Maybe something like this will work? It's a Body by Victoria push-up. Lots of girls your age really like this style."

She handed it to me, and I turned it over and over admiring the shape and the fabric texture. I could hardly believe this was really happening. I decided to go for broke. "This sounds silly, but do you mind if I try this one on? I'm really not sure of my size."

"That's not a silly request. Of course."

I followed her back toward the changing rooms. I have no idea what I would have done if we had encountered another customer at that point. I was not prepared to explain why a boy was heading to the changing rooms carrying a bra. Fortunately, the store was still empty. She unlocked the white-and-pink door, and I went inside. Trying to keep calm I took off my shirt and undershirt, carefully hanging them up. I slipped my arms through the straps and of course struggled with the fastener. I knew how to do it, but was not skilled at connecting hooks and loops high behind my back. At least all the stretching exercises in dance class gave me more shoulder flexibility than typical for a boy.

"How does it fit?"

"OK, but a bit tight" Being in the Victoria's Secret changing rooms was awesome, and I had given an honest answer to what seemed a perfectly normal question.

"Let me get you another one."

A moment later I saw a hand drape another bra over the top of the door. "This one may have a bit more stretch. Let me see what else I can find for you."

Of course I had to try the second, then the third, on too.

"Is the problem that the band is too tight?"

"Yes."

"Unfortunately, we only stock larger band sizes in C and D cup, and I don't think that's what you are looking for. But, have you considered a bra extender?"

"What's that?" Another honest answer.

A moment later she came back and handed me a small package over the door. "These will add a couple of inches. Lots of my customers really like them."

I took out a two-hook flesh-colored extender, attached it to the bra, and tried again. This time the fit was perfect! I stood straight with my shoulder blades pulled back and admired myself in the mirror. I couldn't compete with figures of the girls in dance class, but the padding and push-up effect combined with my own chest fat to give a definite hint of boobs. The feeling of having my chest cradled in the cups and the fastener against my back was wonderful. Unlike the salvaged bra from the dumpster, the hooks were not straining to the bursting point, and nothing was digging into my armpits. After looking at my self front and sideways I readjusted the shoulder straps to get just the right height for the cups.

I decided I better not push my luck by lingering. I ran my hands over the cups a final time, changed back to my shirt, opened the changing room door, and calmly walked to the counter where the girl was waiting. "I'll get this one."

She smiled. "We have panties on sale right now. Would you like to get something pretty to wear with your new bra?"

I wasn't going to pass up that opportunity, but was worried about having enough cash if this shopping spree continued. I picked out three pairs guessing a size that would be a compromise between my overly thick waist and my less-than-ample hips. I paid cash (no credit card records) and watched her remove the security tags and put the bra, extender pack, and panties in the distinctive pink bag.

"I just wanted to thank you for being so understanding and helpful today."

"I love helping customers like you. We get more men in here than you might think. Have fun wearing your new things."

Walking out of the store I ignored the glances from the few people in the mall that early in the day. I had done something I had long dreamed about, and decided I was ready for my next step toward femininity.