Propositioned While Crossdressed
As I explain on my crossdressing history page, I moved to a big city after graduating from college. I threw away my stash before my move, but it was only a matter of months before I began building a new crossdressing stash up. As part of my new life as a working member of society, I joined a fitness club at the urging of a co-worker who wanted someone to play
As part of my new health kick, I also bought a mountain bike and began riding it everywhere including using it to commute back and forth from work. When I would go to the gym after work to play
racquetball, I would inevitably ride my bike to the gym and then ride it back to my apartment about three miles away when I was finished.
On one occasion, I safely made it to the gym on my bike after work, but when I finished my workout and went to ride my bike home, I noticed that the front tire was flat. I was in a hurry, so I hopped in a cab and headed for home leaving my bike behind.
This was a on a Friday, so I began to think about how I could go retrieve my bike and repair the flat tire before work on Monday. The idea came to me that it might be an opportunity for me to dress up like a girl and walk to the gym late at night to retrieve my bike.
At the time I was still in my mid-twenties and terrified of crossdressing outside unless the area was
completely deserted or it was night time. My adventures while crossdressed were limited to late night walks to the park or short walks through the neighborhood. I didn't even have a wig back then, so when I say I was crossdressed for these walks, I usually wore a white t-shirt with a bra underneath if it was warm or a sweater and a bra if it was cold. On my lower half, I would wear a pair of shorts with suntan pantyhose and unisex-looking sandals. I'd walk to someplace with a bench and then sit down for about 10 minutes crossing my legs this way and that admiring my legs in pantyhose.
On this occasion, however, I determined to wear a dress and put on some makeup and then go for a three-mile walk to pick up my bike. I was still experiencing with makeup at the time. I remember seeing a cheap makeup kit in an ad from the supermarket, so I bought it along with other food items that I needed. I also wore my bangs quite long, so if I combed them straight forward, I could get them wet and then curl them around a comb and blow dry them to give them a truly feminine look.
Since it was either October or November and chilly outside, I figured that I could wear a unisex jacket with a hood over a denim one-piece dress and not have it appear too strange. On that Saturday night, I wore my denim dress with bra, panties, and pantyhose for most of the evening, and then about 10 PM I began to apply my makeup and curl my bangs. When I was finished with my make-up and hair, I put on the jacket and pulled the hood over my head to cover my boyish haircut so that only the feminine-looking bangs would show throw. I was satisfied with the look since I would only be outside at night, so I donned a pair of brown leather sandals purchased in
Tijuana of all places and headed out the door for my long walk.
It was an absolutely thrilling experience to be walking outside like that dressed as a woman, and I didn't care that I had to walk several miles. As I got closer to the gym, there was more and more foot traffic on the streets, but I stayed in the shadows the best I could and didn't have any negative reactions from anyone even though I must have encountered several dozen people. I finally reached my bicycle, unlocked it, and began walking it towards home, but I had scarcely walked for a minute when a car approaching from the other direction began to slow down. I anxiously watched the car as there was no other reason it would need to slow down, and I saw that two guys dressed in business suits were riding in the front seat. When the car reached me, to my horror it stopped, and the driver looking right at me, rolled down his window, and said with a coy look on his face, "are you going home so soon?"
The playful tone of his voice made his intentions clear, and I was so shocked I wasn't quite sure how to react. There was enough distance between me and the car that I don't think he suspected I
was a man crossdressed, and I certainly wasn't wearing anything that would give the appearance of a streetwalker as my denim dress ended well below my knees. There was also no way he could have known I had a flat tire, so with my bike it was obvious that I didn't need a ride anywhere. I honestly think he was trying to pick me up. I just turned away from the car and began wheeling my bike the opposite direction a little faster, but the adrenaline started to flow about five seconds in, so I hopped on the bike flat tire,
denim dress and all and started pedaling away from the car as fast as I could. Thankfully, the car didn't turn around and come after me, but I was so shocked by the event that I couldn't stop pedaling until I reached my apartment.
Once I got home, I was able to laugh about the incident. I went inside, took off my jacket, and plopped myself down on my couch putting my feet up on the coffee table reviewing the night's events in my mind. I don't know what made me smile more...the thought of actually passing to the extent that a guy would proposition me, or the sight of my riding a boys bike with a flat tire through town while wearing a long denim dress. As for my female ego, I was thrilled for several weeks after at the thought that someone from society thought I was a woman. All in all, it was a fun crossdressing
adventure for me and one that I can't forget
A Visit to Victoria's Secret
Celebrating the 4th of July as a girl
Attending the musical Wicked as a girl
21 straight days as Lisa
Les Miserables en femme
A night at the opera
Near-miss with the boss
My wife's reminder
Tights in Tokyo
My first photos in public
Errands and a picnic
Shopping for bras en femme