Every now and then Sam and I enjoy an early evening ride around a nearby lake on our bikes. Although we don't do this very often we've found that it's good exercise and quite relaxing, at least most of the time. If I can catch Sam when she's feeling a bit adventurous I'll encourage her to go for the ride without wearing a bra. Even though she has small tits that haven't sagged they are soft and pliable and bounce quite a bit while riding around the lake.
I find that she's most often willing when she's already braless, such as after an afternoon of housework or some such. I often try to get her to wear one of her sheerest shirts, or one of her loosest tank tops, but most of the time she doesn't since that would take a deliberate act of her having to go and change clothes.
If you've read some of the other stories you'll remember that she's doesn't like to expose herself, but only allows it if I'm exposing her, and then she'll go pretty far!
However, I still haven't figured out a way to take off her shirt while bicycling!
The best opportunity I ever had for showing her titties while on the bicycle happened a couple of years ago. We'd been out doing some clean up in the back yard and she was wearing a rather loose fitting tank top. When she would bend over to pick something up it would fall open and clearly show both of her breasts. After we finished the work, and had a couple of cold drinks I suggested that we go for a bike ride. She thought that was a good idea, and didn't think about changing her shirt as she knew I enjoyed seeing her breasts jiggle as we rode the bikes.
When we got to the garage one of the tires on her bike was flat, and had a hole in it. (I wonder how that happened?) Since we were already to go I suggested that she just take one of our daughters bikes instead. I should add here that her bike has the upright handle bars, while our girls bikes have the typical bent down handle bars. She gave me a questioning look, but when I started to beg she finally said ok.
We rode the mile or so up to the path around the lake without meeting anyone, but I could tell from the shaking inside her shirt that her breasts were indeed hanging loose and swinging freely. I finally got a chance to get along side of her and just as I passed her I looked back to see just how much she was showing. I must say that I was very pleased that both of her little white breasts were exposed all the way to her dark red nipples.
As soon as we got on the trail Sam began to attract attention. The one thing I like about this trail is that it's a one way only for bikes, but the runners and walkers can go either direction. It wasn't long before we'd met a few couples walking towards us. I could tell from the shocked look on the wife's faces, and the grins on the husband's faces that they were able to see her breasts. After meeting a couple of guys running, who actually stopped while she passed, Sam pedaled just a bit further and stopped under a tree in as empty spot in the grass.
We'd only made it about a third of the way around the lake by then, so I knew she wasn't tired, but I figured that she might be questioning the wisdom of what she was doing. I pulled up along side her and she immediately as "how much am I showing?" At this point I decided that truth was the best response so I told her she was showing it all. She chuckled a little bit, and blushed at the same time, and said that she thought she must be after the last two guys stopped in their tracks.