Some experiments that didn't work out so well when cross-dressing
Over the years, I have both actively experimented wearing women's clothing, and not actively (meaning I was just wearing a women's sweater for the sake of the fetish, not cross-dressing). I have to say that the majority of the time went very well - no cynical comments, nothing hostile, etc. Even back in the high school and college days, when things weren't so "free", it was pretty quiet. There have been a few stories of things that weren't so quiet, and I figured I would share them here in an effort to move on from them and embrace everything I like about women's clothing mixed with men's clothing:
The story I spoke about from college when I had bought an Anne Klein fuzzy kid mohair sweater with a fall leaf design, and the store clerk snickered when she and a co-worked saw me wearing it.
I only had one other incident in college - that Express Fuzzy Mohair Turtleneck that I bought from a stranger - well I had bought a new one of my own and was enjoying just comfortable wearing it one night in my college dorm. I was watching TV on a Friday or a Saturday, while my room mate was out with his friend (who happened to be a joint female friend) and they weren't supposed to be back for the night. Well - that was wrong, and they BURST into the room. LUCKILY (at the time), my roommate was drunk, and noticed nothing, but my friend noticed but didn't say anything and asked if I wanted to come out with them. She tried to drag me off the bed where I was lying down watching TV and I said no. I was SO EMBARRASSED - dressed in whatever men's pants, but a big, long tunic length women's mohair sweater. I thought at the time that all was well when they left, and only later in that year did she approach the topic. We actually had become good good friends, close friends (not sexually) and we were talking one night about honesty or some other topic like that and she dropped it - "why haven't you told me you like to wear girl's sweaters?" I must have turned purple and she said it was OK and to not be embarrassed. Of course I asked why she asked me and she referenced that night - she KNEW where the sweater came from and wanted me to try to go "out" with it on to make me more comfortable. She also said that it was obvious from then on when I would wear my own (men's sweaters) and how fuzzy and possibly feminine they were. We talked for HOURS that night. I learned a lot about myself, and a lot about tolerance and being open minded. She came out to me as a lesbian that night, and it was eye-opening how "normal" that kind of thing was. She was not judgmental, and neither was I. We remain good friends to this day, and although I don't get to see her more than once every couple of years, when I do she actively forces me to bring the clothes I want, and to wear what I want.
Back when I was right out of college, and had one of my first jobs, I was enjoying the freedom of being single and alone (moved away from home and parents), I got bold and it was a little too early to be so I guess. Since it was release in the late eighties, there was a sweater called "The Bubble" that I LOVED - it was a Perry Ellis design, and as it was well past the time of the sweaters being available, I had one made for me in an amazing green mohair yarn. The sweater was supposed to be huge, so I had the knitter upscale the sweater to fit me like it would fit a woman. It was like a dress really, dropping to just above my knees. The yarn is SUPER fuzzy, and the overall design is unique in my opinion. Well because I was being "brave" I wore it out grocery shopping after work one night. I got a LOT of looks from people, but the one more hostile one came from 2 teenagers, and they proceeded to walk up to me and call me a f%ggot. At the time is didn't hit me, but a bit later in the night I realized how mean spirited it was, and really - who cares what I have on? I thought about that word too and how harmful it can be - and will call out ANYONE that uses it around me about anybody else. So many people are focused on others - who cares?
Right when I started to wear women's skinny jeans (not even jeggings), I was dresssed in a pair of Lane Bryant skinny jeans and a fuzzy mohair turtleneck sweater and I was shopping in a Target store. This was perhaps 4 years ago, and a woman approached me and said "you are wearing women's jeans". I was in the right kind of mood, so I retorted "wow - so are you!" She gave me a dirty look, and I said, funny - I am also wearing a women's sweater - do you like it? She said nothing and walked away from me. This was the beginning of me being more brave with the general public - because again - who cares what I am doing - people would do so much more to mind their business and take care of themselves. Perhaps open one's mind and one might learn of something "interesting" that they like and embrace it!
The Anne Klein sweater I still enjoy wearing today...
An example of the Perry Ellis Bubble sweater. Mine is green and custom knit to be this size on my larger frame.