My First Dress

Just over a week ago I bought my first dress.  I have been wearing my wife's cloths since before we were married.  First, her shoes but later, panties, nylons, slips, dresses, etc...  Only in the last couple of years have I begun to really get clothes for myself.  First, panties and nylons, then shoes.  This past September I bought my first bra in a lingerie store as well as a couple of camisoles in a dress shop.  My shopping experiences have for the most part been great.  One of my favorites was standing in the Macy's in downtown Chicago, being asked for help by another customer (she thought I worked there) and the whole time I was wearing a beautiful pair of black patent pumps (which I had to buy after that experience).  That was a great rush.  

This most recent adventure began Tuesday a little over a week ago.  I was heading into Denver, which is a few hours from home, for a few days.  I wore a pair of pink panties that day with black nylons and a black body shaper underneath my regular dress pants, socks, t-shirt, and dress shirt.  While driving I wore a comfortable pair of patent women's shoes which I would take off for the less "fun" stops.  After running a few errands, I decided to do some shopping.  First, I padded the bra part of the body shaper to give me about "B" sized breasts.  Small enough not to be too obvious under my coat, but noticealbe if I took it off or anyone took a close look.  Second, I put on a pair of black patent women's loafers.  Again not too obvious, but definitely women's shoes for a discerning eye.  

First, there were the walks around the thrift store and the Ross: Dress for Less.  A little nerve racking but fun just the same.  Then, I stopped at a Dress Barn women's store at a outlet mall.  It was 6:00 on a cold wintry evening so not any customers.  Still it was both exciting and scary.  There were two sales clerks.  One gave me suspicious, funny looks; the other seemed more willing to help out.  After checking out what was on sale, (I am crossdresser on a tight budget.) I decided to try on three different dresses.  They were all about knee length, black with some sort beading, sequins or such.  Each had a short sleeved mini coat to cover up my not so feminine shoulders.  It was fun trying them on thinking about the sales clerks out in the shop.  Unfortunately or maybe fortunately, they didn't really fit.  I needed a smaller size and they did not have any.  I really liked one dress in particular so I knew I needed to check out some other dress barns.  After a few other stops, trying on shoes, walking around an open air mall, and trying on some women's slacks (also too big), I called it a night.

Wednesday, I started my day skiing, wearing nylons and panties under my long underwear, of course.  After getting back to the hotel, I gave a quick call home to the wife and got clean up, and then it was time to shop.  My excitement and determination was higher.  I had black nylons, white panties and my white bra on.  I stuffed the bra cups to give me breasts like the previous day.  I put a camisole on over the bra and dress pants, shirt and socks over everything.  First stop a shoes store and then to the mall.  I was wearing my black patent loafers again as I walked from dress shop to dress shop at the mall.  A lot of beautiful dresses, but a little out of my price range. 

In JCPenneys, I grabbed some black women's dress pants to try on as well as a black and white,  nylon dress.  I went to one of the sales ladies in the women's department to see if I could try on the clothes there rather than walk to the opposite corner of the store to the men's department.  I thought that since it was not too crowded, that she might let me.  No, such luck. 

The dress was nice but not something I was really thrilled about.  I found a pair of pants that fit perfect.  Black women's slacks (my first pair).  These were a little long for my loafers, but that is the style anyway.  I kept them on, taking off the tags and carrying my men's slacks I headed to the cash register. 

Once I was back in my car I decided to try two more women's stores before heading to a Dress Barn to find my dress.  At the first store, a Catherine's, I decided to take my outfit up another notch, by putting on a pair of black patent pumps with bows and gold ornaments on the toes.  The heels weren't high (1-2"), but higher than the black patent loafers.  As I walked into the store, the sales lady offered her assistance.  I told her that I was looking for a dress.  She asked how big was the person I was buying it for.  I said it was for me.  She was nice enough, showing me what they had in stock.  I walked around a little, dressed in my feminine attire except for my shirt, belt and coat.  Sometimes I even forgot about my stuffed bra.  It was a rush, but nothing caught my interest.  After a similar experience in another store, I headed to the nearest Dress Barn. 

Located in an indoor outlet mall on the west side of town, I parked at the nearest door to the store.  It was still quite a walk through the parking lot on this snowy, cold evening in my pumps.  Inside the mall I was very conscious of my shoes as I stomped the snow off my feet in front of a woman waiting at the door.  It was a relatively short and uneventful walk past a half-a-dozen stores to the dress store. 

Once inside the store I immediately began looking for my new dress.  I found one hanging on the wall, not marked as a discount, but I figured it was just a mistake.  A quick glance at the label and I saw it was the size I was looking for.  As a I removed it from the wall, the sales clerk who had greeted me when I arrived, asked if I needed help.  I asked if she would check the price.  She said I was right and that it was 32 dollars.  My heart leaped and did a couple of back flips.  I asked if I could try it on.  She said sure and led me to a changing cubicle.  I ******** down to my bra, panties, and nylons and pulled my new dress over my head. It fit perfect.  The dress was covered in black chiffon with shirmmering sparkles in various patterns.  Under the chiffon was a bronze colored nylon liner.  The shoulder straps and mini coat were black velvet.  I felt aroused and excited, feminine and girlie, beautiful and sexy.  My padded bra added to the look.  It was wonderful. 

After taking the dress off I wanted to do a little more shopping at the store.  I had my dress but I wanted to leave with a blouse on and may be even dressier shoes.  I found a pair of black heels (2-3"), after trying on a couple of different sizes I picked the 9's and just wore them as I continued around the store.  My coat was in the changing room so my "breasts" were obvious now.  As it was a cold, snowy night, I wasn't worried about running into anyone I knew and I did not care what the odd stranger thought.  The sales clerk commented on my ability to wear pointed toed shoes as I walked the store.  I found an ivory, ribbed blouse that buttoned up only part way showing off the camisole underneath.

After a little bit more looking I found two more dresses which I decided to try on.  One did not fit at all.  The other was okay, so I asked the sales clerk for her opinion.  There I was standing in the dressing area in front of one of those three-way-angled mirrors.  The heels made my legs look so sexy coming out the bottom of that dress.  I wanted it, but it just did not fit right and the clerk agreed.  She looked for another possible dress for me but no such luck.  I just had to settle for the one dress. 

Back into the changing room one more time, I put my camisole, blouse, and dress slacks back on.  I was completely wearing women's clothing except for my belt and my coat.  Too bad I hadn't wore the black patent belt that was in my hotel room then my outfit would have been complete minus the coat. 

The sales clerk was very gracious, encouraging me to come back any time and mentioned that they held private shopping parties with discounts if I wanted to bring friends with me some time.  She mentioned that she had a male friend who also liked to shop at that store when he was in town.

I left the mall wearing my new heels and the rest of my new cloths minus the dress of course.  Too cold to wear a dress.  I wished that it wasn't so late at this point, otherwise I would have walked around the mall for the thrill of it while I still had the courage and to see how many people would notice.



htr60 htr60
46-50, M
6 Responses Jan 16, 2010

I know how you felt it feels so wonderful to be able to show off your femininity. I've been in your shoes before. I love going in to the stores and having the cosmetic women do my makeup now that's a super thrill. Show what you feel, women except it, and some love to help. Dress On!!

Nice story thanks

Wonderful story....a little past my courage level but maybe soon...LOL.
Glad to hear that you did not have any problems.

II bought my first dress on EBay and it just arrived. It was used an American Indian pattern brown and white. It is very pretty and feminine. I put it on and looked in the mirror and OMG I was so full of happiness.

Great story

i think the story is good. dress barn is real good.