An Exciting Ride
(late 1990s)

I don’t remember if we were planning to go for a bike ride when we left the house, or if we were just out randomly looking for something to do that day, but Brandon and I ended up renting bikes and exploring some trails around a small town outside of Orlando. We liked to find such activities to spend our days off together. Towns like Clermont and Winter Garden, West of Orlando, were often our destination for lunch or antiquing, etc. We rented bikes at a kiosk along a very nice paved trail that went on for miles. I have recently tried to find this location on Google Earth, but there seems to have been quite a few changes. The trails extend for many miles farther than they did in those days. I am no longer sure where we were. But I know we rode East from the rental kiosk for several miles.

Whenever we went out on these day trips, I liked to dress sexy. Usually something sheer, or otherwise attention grabbing. But on this day, I didn’t take that too far. I wore my favorite skit and a nice tight blue top. As usual, I was not wearing underwear, except I did wear a bra this time because I thought it made my boobs look better in this top. I enjoyed riding the bike in my skirt with no panties. The wind felt so good, as did the thrills I got from the possibilities of being noticed by passing bikers. But I wasn't really planning any exhibitionist escapades. We were just enjoying a lovely ride on a perfect day, passing various parks, lakes, neighborhoods, open fields, and across bridges over swamps and roadways.

Eventually, we came to the end of the trail. It was a circle turnaround (like a cul-de-sac with no houses) in the woods just before a highway. I guessed they ran out of money to extend it with a bridge or tunnel to continue past the highway. As we were turning to ride back, Brandon stopped and made a common request, “Take off your shirt.”

He usually wants me to undress everywhere, so I didn’t think much of it. Knowing it would be fun, and that he would enjoy it, I complied. In one move, I pulled my top and bra off over my head and hung the garments over my handlebars. Then I squeezed my boobs together in a way I know he likes, while I teased him with the suggestion that I should ride back like this. As I said it, neither of us knew if I was joking. But then I recognized the look in his eyes, and I knew this was happening.

I was excited by the idea of riding topless down the bike trail. The thought of being caught I found thrilling, but equally concerning. Depending how far I went, I would pass houses and roads, but the real risk of being caught would be if someone came down the bike trail. When we started out from the kiosk, we encountered a lot of people through the first half of our ride, but almost no one for the last half. I knew if anyone was coming, they were still far away, and could only come from the one direction. So, I told Brandon that I would ride like this until we encountered people, if he would ride far enough ahead of me that he could ride back in time to warn me if someone was coming.

Brandon agreed right as I remembered that not far back we had passed along the backyards of houses, one of which was undergoing some serious landscaping. Several workers were using machines to dig up the yard. I thought maybe they were putting in a pool. So, I asked Brandon if he wanted me to ride past the workers with my boobs out. He smiled mischievously and snatched my clothes from my handlebars. I reached for them with no success as he raced off shouting for me to give him a good head start.

I shrieked and covered up with my arms as my nerves got the best of me. I had expected to remain in control of my top. Now this was very different. I was completely at his mercy. What if he never came back? This added another level of excitement, but frighteningly so. Again, I was experiencing those conflicting emotions and sensations trying to balance the titillation with the fear. And at that moment, the fear was dominate. I thought to use my skirt in some way to cover all of me, but it was too short - not long enough to cover everything - and I had no panties. I looked along the tree line, thinking to fashion something out of leaves. But identifying this as a ridiculous but possible solution helped me realize I really did want to follow through with the plan to ride back topless. My courage hit an upswing, and I started pedaling back down the trail. As I got up to speed and could fully appreciate the wind on by breasts and the phenomenal sense of freedom, my apprehension turned to euphoria. I began to think I could ride all the way back like this. Who cares what anybody thinks! I could turn some mild play with my boyfriend into an experience I would never forget. I imagined his surprise if I sped right past him, and everyone else, and rode right up to the kiosk.

But very soon I was approaching the landscapers, and my courage again waned. I debated making myself small, keeping my eyes ahead, and speeding past - or could I sit up, look them in the eyes, and wave as I slowly cruised by?

As I came around the bend to the straight away that would pass the landscapers, I could see Brandon stopped far ahead, out of sight of the workers, but looking back to watch. I now felt confident that I would be bold and wave at the men. The bike trail was raised, a few feet higher than the yards. There was a small slope covered in dense foliage down to the chain-link fence of the yard. I felt this was a safe barrier between me and my audience. But as I approached the yard, and saw one of the guys looking my way, and I felt my nerves again. I looked straight ahead and pedaled faster. Everything was happening quickly, and I kept waffling. One second, I was scared and wished for my shirt – the next, I was elated and really wanted to make a show of it. Watching Brandon watching me, I decided to go for it. I slowed the bike just a bit, turned toward the guys with my shoulders back and chest out, gave a big smile, and waved as I passed. There were at least 5 workers I could see, and they saw me. They said nothing while I waved, but as I rode away, I heard them calling after me. There was some whistling and shouted requests for me to come back.

I felt a burst of energy and was so delighted and frenzied by the short experience that I was tittering to tears. I no longer wanted to catch up to my clothes. I wanted to turn around and ride past them again. I loved that they enjoyed me. I don’t always get such immediate and enthusiastic feedback. I could still hear them calling to me as I watched Brandon continue away and out of sight around a bend. I returned to doubting his coming back to me if someone came up the trail. I was now really remembering the many roads and populated areas I would be passing before I was likely to catch up to him. As all settled in my mind, a wave of intense arousal and anxiety hit me as I realized he was definitely gone. I knew he would love to have me ride half naked all the way back to the kiosk. The only chance I had of seeing him again was if he stopped to watch.

Most of the ride so far was under a canopy of trees, and those few backyards, but as the trail opened to a large field, I gained terrific confidence. The sun hit me, and I felt wonderfully displayed as my breasts swayed nicely with the rhythm of my pedaling. I intentionally exaggerated this movement, gratified by these sensations and the vast exposure as I cruised down the path through the open field. It was exhilarating. There were busy roads in the distance, but they were so far that I thought no one could see me well. However, I remembered that I would soon have to cross a road, and then ride alongside it for a while. This was not a busy road, but there would certainly be some traffic. I wasn't sure my confidence would sustain to carry me through this part.

Reaching a point where I could see this road ahead, I slowed and looked for cars. From my position, I could see both ways for some distance. After one car passed, I started pedaling fast toward the crossing, hoping to cross before another car came. I didn’t know what I would do when riding alongside the road. Maybe just be wildly audacious and immerse myself in what was sure to be a sensational experience - or dive into the bushes, if I must. Then a car turned onto the road. It seemed we may arrive at the crossing at the same time. No doubt they had already seen me. I was very close now but would have to stop to let them pass. So, I quickly turned around and rode back the way I had come. The car came to a stop and beeped at me, but now my back was to them. Riding away, I realized I was not going to make it to my top without committing to ride closely by people, perhaps dozens of them. The incident with the car was nerve-racking. Exciting for sure, but not like the fun I had with the landscapers. I felt stuck and needed a new plan.

I had noticed that a few of the landscapers were working with their shirts off, and at least one shirt was hanging on the fence. I rode back to the cover of trees while considering if I could sneak up and steal a shirt. I decided against it, but thought it might be thrilling, and solve my problem, if I approached them and asked for a shirt. In some ways that seemed crazy, but the more I thought about this, the more I liked the idea. Even if they refused, such provocative interaction would be wildly stimulating. And I knew there was no getting out of this without encountering more people, so it may as well be with the landscapers who apparently enjoyed my show so far.

Although I liked this idea, I still had trouble committing. Riding closer to the men, I grew increasingly anxious. I noticed a place to pull off the trail where I could hide behind some bushes, and took advantage of this while I thought through my plan to approach the workmen. I felt safe in the bushes and figured even if Brandon went all the way to the car, if I just waited here, he would eventually come back. I could just stay and watch for him to pass on the trail. But I was only there a few minutes before I got bored and decided to keep things interesting by going to ask the landscapers for a shirt.

Riding toward the men, I remembered something that got my heart beating even faster. With no pockets, I had put my money in my bra. It was probably now somewhere along the trail, and most likely on the ground where I took off my top. I decided to just ride past the workers and assess the situation on the way to check for my money. If I didn’t think I could stop and ask for a shirt, this would at least give me an excuse to ride by them a couple more times. If all went well, I would find my money and then stop to ask the men for help.

Coming within sight of the landscapers, I could feel the pressure building. I didn’t make a show of it this time as they were not looking toward me. Riding past, I noticed that a shirt was still hanging on the fence, but the foliage was too thick and sharp for me to try to reach it. I heard some loud talking just after I moved out of sight from the yard, but I wasn’t sure if they had seen me.

Thankfully, my money was lying right where I had taken off my shirt. Keeping it in my hand, I gripped the handlebars and tried to work up the courage for what I was about to do. I took a deep breath and started back toward the workmen. But I had taken too long. Around the corner came a young couple on bikes. A man and woman who looked to be in their twenties. I was completely caught off guard as they were upon me suddenly. For a quick moment, I thought I would pass out. Then a calm washed over me as I accepted the situation. This has happened to me before. I relate it to a serious injury, or some kind of intense pain, when your body just releases adrenaline or something that just helps you survive. I was no longer afraid, and looked right at them as we passed on the trail. They glanced at me but mostly kept their eyes ahead as they continued around the bend and out of sight. I felt something like pride for not just collapsing with embarrassment. But I had to figure out what to do next. Now ready for my interaction with the workmen, I didn’t want to be in the middle of that while the couple rode back past us, which I knew they must because they were headed toward the dead end. So, I decided to stop and just wait there on the trail until the couple came back my way. This seemed to take forever as I wondered if anyone else would be coming along. It was also now proven that Brandon was not going to return if anyone came up the trail.

I waited there on my bike until the couple passed by again. I acknowledged them with a smile, which may have been a mistake, as the girl then stopped and asked if I was okay. I told her I was fine, but she stared at me, I think wanting an explanation. I just continued smiling. She nodded and continued down the trail toward her boyfriend, who never stopped. I was now feeling very bold and raring for some real fun with the landscapers.

One of the men saw me coming and began to wave me down. He rushed to the fence not knowing I already intended to stop. As I pulled up, his coworkers noticed and a couple more of them approached the fence. They were quite enthusiastic. The loudest of the group asked where I was going. I halfheartedly kept a hand over my boobs, trying to appear shy and helpless, as I told him that my boyfriend stole my shirt as a joke. I asked if he would give me his shirt. He just repeated my request back to me, probably stalling or not sure what to say. I thought about offering some of my money, which was still in my hand. But he offered to trade his shirt for my skirt. I was standing over my bike, which was a boy’s bike. So, even on my tiptoes, the bar was high between my legs, pushing my skirt up. Because I was uphill from the guys, I thought they might already see that I wasn’t wearing panties. Although, I still debated lifting my skirt as an erotic way of confessing the dilemma of surrendering it. Then another of the group removed his shirt, balled it up, and tossed it toward me. But, it caught the wind such that it stalled in the air and fell short, landing in the brush on the side of the hill.

I was aware that I could be seen from the house, and the neighboring houses. No one else was in the yards, but someone could be watching from the windows. I was so absorbed in the encounter that this didn’t bother me. I enjoyed the possibilities. I gave up on covering my boobs as I dismounted the bike and walked to the edge of the path considering how to reach the shirt. I really had no intention of going down the hill, but I was making the most of being half naked and helpless in front of these men who were considering what to do about me. A couple of them were admiring and complimenting me, and the others seemed genuinely concerned and were trying to help. The one who tossed his shirt toward me jumped the fence, retrieved it from the brush, and carried it up to me as the loud one insisted that I trade my skirt for it. I thanked the guy who gave me his shirt and told him I would return it when I found mine. I thought it would be cute if I kissed him on the cheek, but he stumbled back down the hill before I could. The shirt was wet with sweat, but that is not why I didn’t put it on immediately. I was having so much fun, and thought it would be more entertaining if I rode off without putting it on. The loud guy was still insisting on a trade. So, just before I mounted my bike, I turned away from them and flipped up the back of my skirt. This clearly thrilled them, but their vocalized reaction thrilled me more. Their deep and excited voices reverberated through me as I practically felt them appreciate my bare bottom. I got on my bike and again promised to return the shirt as I rode off. They kept calling to me until I was well out of sight.

Dizzy with excitement, I was motivated to intensify my naughtiness. A part of me wanted to totally lose control. But I just kept riding, not sure what to do. I was elated and enchanted by the experience so far, and was almost regretting not trading them my skirt. But reality slowly sunk in as I knew I could not ride back to the kiosk bottomless anymore than I could topless. I convinced myself to stop and put on the sweaty shirt. It was pretty gross, but in some ways it turned me on having this stranger’s now cold wet shirt against my skin. I felt truly dirty, in the most salacious way.

By the time I rode back to the open field, I saw Brandon heading my way. I stopped and waited for him to reach me. As he pulled up, I accused him of abandoning me, but he didn’t answer for that, only asking about my new shirt. I told him the story. He was shocked and expressed disappointment for missing that part of the show. I said that is what he gets for abandoning me, and we now must return the borrowed shirt. Brandon followed me back toward the landscapers but stopped just before we were in sight of them. I reached for my top, which was wrapped around his handlebars, but he backed away saying I had to return the borrowed shirt first, then he would give me mine. I knew he would ride off as soon as I was topless again, so I refused. We debated about this until I suggested that he give me my top, I would return the borrowed one, then ride back to him before getting dressed. He trusted me because he knew I would enjoy doing this. And I wasn't going to again lose control of my top.

Brandon gave me my top but kept my bra. I gave him my money to hold. Then he waited and watched as I approached the landscapers again. They were pleased, and I think a bit surprised, to see me again. I took off the borrowed shirt and tried to toss it back over the fence, but it hardly made it a few feet into the brush. The guy had to come retrieve it again. I could see Brandon up the trail enjoying my little show, so I stayed there for a bit. Standing over my bike, I chatted with them and found out they were not putting in a pool but working out some drainage problem. They knew I was having fun with them, because I was holding my shirt now, and wasn’t putting it on. Really enjoying the success of my teasing, I started pushing things further. I was slightly rubbing and enjoying the bar of the bike between my legs, as I playfully asked what they thought of my boobs. The guys were very complimentary. But a couple of them were insisting that I reneged on the trade of my skirt. I reminded them that I never agreed to that deal. But I was happy the subject had come up again. It was a fresh invitation to what I knew I wanted to do. I looked down the path to Brandon thinking of how shocked he would be if I dropped my skirt right there on the bike path. I loved finding ways to surprise him. And I rarely had such a terrific opportunity and enthusiastic audience. I stepped off of the bike, unbuttoned my skirt, and paused for encouragement. I knew I was going to do it, but it was so much fun to tease them with my mock hesitation. I looked to Brandon to be sure I had his attention. The guys were roaring for me to do it.

My plan was to let my skirt fall to the ground, strike a pose or two, appreciate everyone's reaction, gather my clothes, and blow the men a kiss as I ride off wearing only my socks and shoes. But that is not what happened.

Just as my skirt hit the ground, I saw the neighbor’s back door open. I panicked and quickly pulled up my skirt, and with it half on I clumsily gathered myself onto the bike and rushed back toward Brandon. I did still blow a kiss during my escape, but it was not the charming and sexy maneuver I had planned. It was a graceless end to the otherwise marvelous encounter. But I like to think they found me adorable anyway.

As much as I was startled by the neighbor, I was still so consumed with lascivious impulses, I just rode past Brandon without stopping, wanting to see how far I could convince myself to go this time. But when we came to the open field and saw the traffic ahead, I did stop to get dressed.

Our adventure was not quite over. My bra was still hooked around Brandon’s handlebars, and as we moved into areas around other people, I was entertained by the idea that people may notice and wonder. The whole adventure of this day really got me going. I was now looking for a place to pull Brandon off the bike path to have sex in the woods. But as we crossed a bridge back over a highway, which I think was the Florida Turnpike, Brandon stopped and dared me to flash the truckers. We had passed several people recently, but no one was on the bridge at the time. I don't know if that would have mattered. I was so revved up, and game for more fun. I rode up to the fence and pulled my top down.

It was common for us to make up rules for our little games, and Brandon now told me I had to keep going until one of the truckers honked. I accepted the rule, but after standing like this for only a short time, I started feeling silly, and got the giggles. After a while with no reaction, I decided I wasn’t obvious enough, so I pulled my shirt all the way off and waved it above my head. A car honked. I cheered for my success, but when I started to get dressed Brandon pointed out that it was a car, not a truck, that had honked. So, I dropped my top and faced the traffic again just as two girls on bikes came around the corner and onto the bridge. Brandon’s voice was high and panicked as he tried to warn me, but it was too late. We were caught. I held my boobs feeling ridiculous as they passed. I just went with it and said, “Just flashin’ the truckers.” To which one of them answered, “Okay,” as they moved on.

Out of this whole adventure, I think the most embarrassed I got was at the very end. After the girls caught us on the bridge, I was distracted and forgot that my bra was still on Brandon’s handlebars. I did not think about it until we were back at the car. (Later he told me that he remembered but was waiting for me to notice.) So, I had to go back to the kiosk, where the bikes had been put away by the 2 teenage boys who worked there, and I had to ask them for my bra.
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Pictures:

1: I am not sure if this was taken the same day, but this is the exact outfit I wore for the bike ride.

2: My bike trail outfit, except the shoes. (I was wearing tennis shoes on the trail.)

3: Taken a different day, but this is the skirt from the story, so how I was dressed when riding topless.

4: Always happy to show off… This is about how I looked when first flashing the highway traffic.