Day On The Bike Trail

A couple of years ago I had to change shifts at work. Much as I hated it I went to tues through sat. The plus side was that I had mondays to myself. It was a day when I could dress the way I wanted and go where I wanted.
After everyone would go to work I'd take a shower, shave and put on a air of panties, panty hose and bra. Ususally I'd do my make up and then slip into a miniskirt and tank top. A pair of high heels and my long frosted wig.
That taken care of I'd get a sports bra and a pair of Haynes thigh firmers and a pair of sneekers before heading for my truck. I'd load my bike and head for the city where the bike trails were long, the girls were frequent and no one knew me.
Normally I'd get to the parking lot and unload my bike then put on my thigh slimmer as bike shorts, then remove my skirt and top before adding the sports bra. Then I'd ride for ten to fifteen miles before doing other things and heading home. About half way to the city I decided that I'd ride in my skirt and tank top. I needed to get a pair of shoes that were more femine so I stopped at a Payless shoe store. I walked in and chatted with the clerk awhile and she took me to my size shoes and I tried three pair on. She was looking at me the whole time and my 12" skirt showed all as I took them on and off. I decided on a pair made the purchase and went on my way. She told me to come back soon.
Back in my truck I headed for the bike trail and parked my truck and got my bike out. I changed my shoes and put my sportsbra in the bag along with my two water bottles.
This was the first time I'd ridden in my skirt and I was a little nervious. The short skirt didn't hide my panties crotch as I peddled along but know one seemed to pay attention. I rode west for about ten miles before the trail ended and I turned around. I stopped for a break and sat on a park bench drinking when a young lady came up and started talking to me. The subject of my clothes came up and she was very complimentary and commented on the color of my bra straps which showed because of the cut of my tank top. She asked if the bra was also "that pretty blue".
I told her that it was and that I'd thought of riding with the bra as a top and usually rode with a bra and a sportsbra over it. She told me that she thought that would be cool. then she said that she'd ride two miles with me if I' take my tank top off. I was really hesitant and drank the rest of my water before she told me she'd ride with just her bra as a top if I would. Without another word she peeled her top off revealing a beautiful black bra. I was in no place to argue and remove my top as well.
We rode the two miles and passed several guys and two girls.. We got several whistles and I wonder if they realized it was a guy and gal. At the end of the two miles I suggested that we switch bras for a mile. To my delight she agree and removed her bra showing her beautiful ****. We put each others bras on and rode the next mile. Then we exchanged again ond put on our own bras. Also we put our tops back on.
At her request I pulled my skirt up around my waist and she rode behind me for awhile. We came to an intersection and went into a convience store for a drink and talked some more before resuming our ride.
By the time I reached my truck I was really hot. I'd lost my riding mate with a date for the next week. I decided to ride three more miles and see if anyone was at the apt. swimming pool next to the trail. With luck there was apretty blonde tanning herself and no one else. Her top was undone and I asked if I could be her guest and cool off. She said I could as long as I kept my clothes on. I agreed and walked down the steps into the pool. It was only deep enough to cover my bra cups but the water turned my tank top transparent showing my blue bra plainly. I swam for a few minutes and thanked her then offered to buy her a soda. She accepted and we chatted while we drank. I was really surprised when she sat up and let her top fall down. I told her how beautiful she looked and she graciously accepted my comments.
It was getting late and I left riding another three miles before returning to my truck still damp from the pool. I loaded my bike and changed into my heels then went to BK for a burger. I went inside to eat and several people watched me but made no comment.
Back in my truck I headed for home and three truck drivers honked at me. I pulled my skirt up and took my tank top off for their pleasure. I don't think any of them realized I was a guy from their comments on the CB.
Love my days off. They are so relaxing.
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26-30
Sep 12, 2012