The "i Dare You" Bicycle Ride.

A couple of days before what I’m about to tell you, I was having a clear out of my garage. This garage had a load of junk in it when I moved in so it was time it was dumped. As I went through it I came across a woman’s bicycle, it was in quite good condition and this gave me an idea.
The next day I went out and got some lights for it and fitted them. That evening I was going out for my first ride as a female.
I went through my clothes and decided on a black knee length skirt with black stockings underneath, my panties were white and lacy and I also wore a pair of black suede knee high boots with a two inch heel. The weather was raining a bit so on top I had a white long sleeved turtle neck sweater with a white padded out bra underneath and a waist length rain proof coat. As it was raining a bit I chose my short blond wig and only did minimal make-up.
I walked out of my flat and down two flights of stairs to the garage compound, as I walked across the concrete my boots made that loud clicking sound that we all love. I opened the garage door and got the bicycle out. I got on it, the way a woman should and not like a guy by throwing your leg over the seat. I rode through the garage compound and down to the road, I turned right and took the next left, this took me to the local park. Once at the park I rode round the park a couple of times, but there was nobody in there. Then I decided to ride to the entrance on the opposite side to the park to where I came in, this led from the park to a busy road. This busy road led to town and about a quarter of a mile along this road was another entrance to this very park. I sat on the bicycle for a moment thinking “should I go for it, should I ride along the busy road and re-enter the park by the other entrance?” Sadly I found myself saying in my mind, “I dare you”. So I took a deep breath and away I went.
The road curved round in a long S bend as I approached the first bend there was a group of lads walking on the sidewalk, I just looked to the opposite side of the road and casually rode past. As I passed I heard the comment, “look at the legs on that”, I looked down to see my skirt had ridden up and my stocking tops were on show for all to see. At that moment a car approached from the opposite way and the driver loudly blew the horn. I got to the next entrance of the park and rode through the gate, I rode up to a bench, got off the bicycle and sat down, took a deep breath and lit up a cigarette. As I sat there I realized that what I had just done was such a buzz and I began to think of other places to ride the bicycle and what other clothes to wear, should I dare myself to wear a shorter skirt, should I wear plain color pantyhose so my legs look naked, things like that.
Oh well, until next time.
Katy X
51-55, M
3 Responses Jan 19, 2013

I definitely dare you to wear a shorter skirt - it would be awesome if your panties accidentally showed while you were riding your bike

I have worn a shorter skirt, but my panties were on show more than just accidental.

Which was probably an awesome experience, part embarrasing, part exciting

A little embarrassing and very exciting, almost a high.

I know, how do you think my shorts eventually got so short

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Great adventure

Thank you.

Good for you, Katy! I wouldn't wear a shorter skirt if I was you since the one you wore you already showed the top of your stockings. But pantyhose, that I would ...

Thank you Lee for taking the time to read my experiance.
Sadly I have been out on the bicycle in a shorter skirt and with plain pantyhose since this time almost got me into a spot of bother as the skirt rode up so high my panties were on show and i couldnt pull it down while riding the bike.
I have worn the same short skirt with black pantyhose out on one of my walks and even that i had a bit of bother at a bus stop. But thats for another day.

You're welcome Katy. Yes I would love to hear about the situation you had at a bus stop ... that is when you have the time to write and share it.

I would be happy to share it with you and others as long as you are all over 21.

Oh too see 21 again, knowing what I know now! ;-) I am afraid that was a long time ago now.
But what you post, Katy, if my memory is right there is a button at the bottom that you can click that will preclude someone who is under 18 from reading it. Now if when they registered they checked that there age as being 18 or over, effectively lying, well what can I say ...

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