Standard disclaimers apply.
I'm Madison, Chapter 2. The Shopping Trip
It had been six months since I had made my decision to transform myself into Madison, but so far, I still dressed and looked like a man. Despite that, the changes were starting to show. In six months, I had completely changed my eating habits. It took a while, and there were some set-backs, but I was now completely eating as Madison. Breakfast was an egg-white omelet or bowl of whole grain cereal. Lunch each day was a light salad. Supper was usually a piece of grilled chicken and a vegetable. Not much variety, I know, but I wanted to look good in a swimsuit! The diet had helped a lot. My weight had dropped a good 30 pounds. I was no longer technically overweight. I still wasn't as slender as I hoped to be, but with the diet, I was getting close. I started doing aerobics to tone my body. I stayed away from weights. I didn't want to bulk up at all!
So my body was coming along nicely, but I was starting to really want some women's clothes. As I didn't fit my old clothes anymore, now seemed the right time to go shopping. The only problem was that women's clothes fit tighter than men's, and I knew I'd be shrinking. I'm employed and not in debt, but didn't want to spend money on an all-new wardrobe twice in a year. I finally decided that the time was not yet right to buy public clothes. I worked at home, and rarely went out. I had some older clothes that I had grown out of years before. I could wear those on the rare occasions I left the house, but I really wanted...you know...the panties. I got excited just thinking about it. I spent a whole day on the Internet looking up women's sizes. This was not going to be easy. In fact, shopping seemed terrifying. I could order my clothes online, but was afraid they wouldn't fit. I couldn't go into any store and ask if they had any clothes for a 6'4" 210 pound "woman". I might get laughed out of the store. I knew I told myself I wouldn't be afraid anymore, but damn! Being unafraid was hard, maybe impossible. At least right now.
After spending hours doing searches on "Women's Plus Sizes", I finally searched for "Cross Dresser Store". There were so many! The search even led to chat sites and message boards. I had been to chat sites before, but only for cyber sex. Never to actually find information. Learning from the store websites, I started to find what I was looking for, but I still wanted to actually go into a store, confront my fears, and buy what I wanted. In the boards, I found threads talking about local stores that catered to "special clientele". There didn't seem to be any in my town, but there were more than one in a major city just one state away. In fact, I'd always wanted to live there. I decided to visit the city and buy what I wanted. I would drive, so I wouldn't chance any embarrassing moments at the airport. And I would stay the weekend.
The drive was uneventful, and I checked into a hotel not far from the store. I found it quickly, and went inside. To any observer, it was a women's clothing store like any other. The selection sizes went from small to large. I walked around browsing, starting to get worried. I didn't see anything that could fit me!
After a few minutes, an associate greeted me. She was small and pretty, and most importantly, smiling openly.
"Hi, can I help you?" Her smile was so inviting. My heart was beating a mile a minute in my chest, though.
"Yes, I'm doing some shopping today." There, a nice, neutral answer.
"I see. For a wife, or girlfriend?" There it was. A way out. I could say it was for girlfriend, buy something small, and get out.
But that's not what this trip was about! Come on, be Madison! Be strong! Take a chance!
"No," I whispered, "for me."
I felt my heart stop. There it was. My secret desire. Out there in the open. It was only one girl in one store in a city and state I didn't even live in, but God this was terrifying!
She seemed to sense my fear and placed her hand on my arm.
"It's OK, we do have a wider selection of clothing sizes than we display. Would you like to see them?"
It was OK! It was really OK! I exhaled loudly in relief!
"Yes, please!" I almost laughed in relief.
She still smiled. "It's really OK here. Is this your first time shopping for clothes?"
"Yes"
"I see. Have you bought anything on line?"
"No. I didn't want to buy anything that wouldn't fit."
"Good choice. Lot's of girls make that mistake their first time." I was confused when she said girls. Wouldn't she want to stress the word with air quotes, like "girls" or something. She seemed so relaxed! Much more comfortable than me! Of course, she did this all the time. It's not every day you shop for your first pair of panties.
"I'm Becky by the way. What's your name?"
"Madison" That was much easier.
"So, Madison, what exactly are you looking for? A dress, an outfit, some lingerie?"
I whispered again, I couldn't help it, "Lingerie. I'm not quite ready for outside clothes yet."
"I see, well I'll lay out some choices close to your size. We don't see a lot of girls with your height, but we do on occasion. I think you'll be happy with our selection, and if you find something you like that's not in your size, we can special order."
She led me to the back of the store where most clients don't go. There wasn't a dressing room, but an employee restroom that I could use for trying things on. There were also some slips of paper to protect the panties from...well...my excitement.
I nodded my thanks and started browsing. Soon, I had a number of things to try. I spent 3 hours in the back of the store trying on various panties, chemises, slips, bustiers, camisoles, bras, and gowns. I quickly learned that, one, thongs and g-strings were not for me. My cock kept slipping out. A bikini cut panty was my best choice for sexy while keeping it tucked away. I also learned that without boobs, a lot of the other outfits didn't really look good or feel good on me. I decided against buying breast forms or stuffing my bras or anything like that, so migrated away from outfits that had definite cup sizes built in. That still left me with a wide selection of gown, chemises, camis, bustiers, and some baby dolls. I also found some thigh highs to wear.
I went to the front of the store with my selection, and stood in line. A couple of women in front of me smiled. One woman, however, saw what I was carrying and asked who it was for.
I tried to ignore the question, assuming the air of a guy in a lingerie store. You know, slightly turned on, and slightly embarrassed by being there. The lady didn't take the hint, though.
"Hi - I asked you, why are buying so much lingerie?" Pushy bitch!
I looked her in the eye and said, very clearly and in a normal tone of voice, "They're for me."
She looked shocked. The 2 other women in line were biting their lips to keep from laughing. The pushy bitch laid her things on the counter and walked out of the store without another word.
I blushed now as the 2 women and the shop girl smiled and laughed with me. I apologized for losing her sale, but she said I was buying more than that lady anyway. I laughed and paid my bill, and started to leave.
As I turned away, Becky stopped me, "Madison, are you new in town?"
"Just visiting, actually."
"Well, just remember that there will always be people like that old broad, but there are also a bunch of people here that will support you. You were very brave today."
"Thank you," I said, feeling better every second about coming here.
"You know. There's a club I've heard of a few blocks away for people who live alternative lifestyles. Would you like directions?"
Directions. So she wasn't asking me out. Well, I wasn't ready to date anyone yet. And I was still pretty sure I wanted my next date to be with a man anyway. I politely declined, and went back to the hotel. I couldn't wait to try on my things again.
Once there, I wasted no time. I tried on everything twice. I thought I'd really love sleeping in a gown from now on, and really liked the panties that matched the 2 gowns I bought. But I wasn't ready for sleep. I picked a black bustier set that included the panties and garters to attach to the thigh highs. It was black, and all lace. I could see my skin underneath it. It fit so well! Looking in the mirror, I knew I didn't look like a woman, but I started to feel like one, or at least what I thought they'd feel like. Exposed, but covered, and so sexy.
I grabbed my bag by the bedside and took out my newest dildo, a purple silicone dong, around 6", erect but soft, and not very thick at all. I put it in my mouth and sucked it, imaging it belonging to a very horny man who was removing my panties as I blew him.
I slid it between my lips as I lowered my panties, then lubed it and spread my legs. I slowly pushed it inside me. It hurt a little, but I'd being doing this for months now, and could relax as it entered me.
I fucked myself with one hand while the other lowered the bustier straps from my shoulders. I pushed it down around my waist while I fondled my nipples.
Finally I started jacking off with one hand while fucking my ass with the dildo with the other.
In a few minutes I had cum on my hand, very slowly, my body tingling. I smiled and brought my own cum up to mouth. I licked and sucked it off my fingers, savoring it, while wishing it was someone else's.
As I lay there, my bustier around my waist, my legs still spread and my ass still enjoying the fullness of the dildo in my ass, I knew it wouldn't be long now.
I was on my path.
I was Madison.
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