OccasionallyJamie
11-02-2014, 06:31 PM
This is my first posting so I’ll apologize in advance if it is a little disorganized. For quite some time I’ve been discreetly cross-dressing as time and life allow. Recently I have been able to be more adventurous in my activities. I’m not “out” and don’t know if I ever will be. But this Halloween I (finally!) went out in more than ambiguous women’s clothes (that is, in more than girl jeans, neutral color top, etc).
I went late night shopping wearing a dress, hose, heels, bra with breast forms and padded girdle. I had no illusions of “passing”. I don’t have a decent wig, and my breast forms and a padded girdle gave only a little (very little) feminine shape, so I was definitely “a dude in a dress”. I drove around for quite a while and eventually drove to a 24-hour drug store (one of the big chain stores). After I parked it took a while but I finally got up the courage to go in and do some shopping.
Since it was very late, after 2 AM, the store was practically empty. I spent a few minutes picking out some lipstick, nail polish and pantyhose and then checked out. Surprisingly, the young lady at the register didn’t comment on how I was dressed and, as far as I could tell, didn’t even bat an eyelash at my appearance. As I was paying the store manager, a guy who’d guess in his late 20’s, came over and laughingly asked “Halloween costume? What are you?” I answered "yes", and a “guy in a dress”. He said that when normally looks at people from a distance he generally looks at them from the shoes up, and when he first saw me from down the aisle he noticed my heels, hose, dress and thought “a woman”. Then he got to my head (with no wig and short hair) and thought “what the … that’s a guy”. He then came over to check things out. We chatted for a few minutes. At one point he asked if was hard to walk in the heels since he couldn’t imagine how women were able to walk in them. I told him it wasn’t too hard (they were only 2-3/4 inch and I had practiced in them before) but the worst thing was the clip-on earrings. I said I had continuously felt the pinch from the clips from the minute I put them on.
I had a small camera in my purse and asked him if he would take my picture, which he did without hesitation. (I’ll have to the edit the picture to reduce the file size and figure out how to upload it). I’d guess I was in only the store for 15 minutes, but it seemed a lot longer.
It was a fun and somewhat liberating evening. I know that a man dressing in women’s clothing at Halloween is generally socially acceptable, so that my venturing out was not a huge risk. But for me it was a positive, albeit small, step in my CD’ing.
I went late night shopping wearing a dress, hose, heels, bra with breast forms and padded girdle. I had no illusions of “passing”. I don’t have a decent wig, and my breast forms and a padded girdle gave only a little (very little) feminine shape, so I was definitely “a dude in a dress”. I drove around for quite a while and eventually drove to a 24-hour drug store (one of the big chain stores). After I parked it took a while but I finally got up the courage to go in and do some shopping.
Since it was very late, after 2 AM, the store was practically empty. I spent a few minutes picking out some lipstick, nail polish and pantyhose and then checked out. Surprisingly, the young lady at the register didn’t comment on how I was dressed and, as far as I could tell, didn’t even bat an eyelash at my appearance. As I was paying the store manager, a guy who’d guess in his late 20’s, came over and laughingly asked “Halloween costume? What are you?” I answered "yes", and a “guy in a dress”. He said that when normally looks at people from a distance he generally looks at them from the shoes up, and when he first saw me from down the aisle he noticed my heels, hose, dress and thought “a woman”. Then he got to my head (with no wig and short hair) and thought “what the … that’s a guy”. He then came over to check things out. We chatted for a few minutes. At one point he asked if was hard to walk in the heels since he couldn’t imagine how women were able to walk in them. I told him it wasn’t too hard (they were only 2-3/4 inch and I had practiced in them before) but the worst thing was the clip-on earrings. I said I had continuously felt the pinch from the clips from the minute I put them on.
I had a small camera in my purse and asked him if he would take my picture, which he did without hesitation. (I’ll have to the edit the picture to reduce the file size and figure out how to upload it). I’d guess I was in only the store for 15 minutes, but it seemed a lot longer.
It was a fun and somewhat liberating evening. I know that a man dressing in women’s clothing at Halloween is generally socially acceptable, so that my venturing out was not a huge risk. But for me it was a positive, albeit small, step in my CD’ing.