(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 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 seem to have been quite a few changes. The trails extend much farther than they did in those days. I am no longer sure exactly where we were, but we rode 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 skirt, khaki and pleated, with a nice tight blue top. 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 nice, as did the thrills I got from the possibilities of being noticed while on my bike. But I wasn’t really planning any serious exhibitionist escapades. We were just enjoying a lovely ride on a perfect day, passing various parks, lakes, neighborhoods, 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 on my handlebars. Then I squeezed my boobs together in a way I know he likes, while I teased him with a suggestion.
“Maybe I should ride back like this?”
As I said it, neither of us knew if I was joking. But then I caught that familiar 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 on how far I went, I could pass many houses, roads, businesses, and dozens of people, if not hundreds. But on my bike, I could speed away and soon be far from anyone who might see me. I thought this would be wonderfully fun and stimulating. There was also the risk of being caught up close if someone came down the bike trail. Although exciting to imagine, I knew that could lead to the kind of trouble I might not be able to escape.
That morning, when we started out from the kiosk, we encountered a lot of people through the first half of our ride, but no one for the last half. I considered this now as I stood topless over my bike on the trail, trying to build my courage. I supposed the path would be clear out here for a while. If anyone were coming toward us now 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. Then I reminded him of something (although I knew he probably hadn’t forgotten). Not far back we 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.
“You want me to ride past those construction workers with my boobs out?” I put as a question, but it was more of a statement. I knew what he wanted.
Brandon smiled mischievously as he snatched my top and bra 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.
Brandon looked back at me just as he rounded the corner out of sight. Seeing the look of joy on his face helped my courage, and I started pedaling. As I got up to speed and could fully appreciate the wind on my 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 we would never forget. I imagined his surprise if I sped right past him, and everyone else, and rode right up to the kiosk in just my skirt with boots on and boobs out.
But as I was approaching the landscapers, my courage again waned. I thought to make myself small, keep my eyes ahead, and speed past. Then I heard my little voice ordering me to sit up, slow down, look them in the eyes and wave with a big smile.
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, I felt my nerves again. Looking straight ahead, I pedaled faster. Everything was happening quickly. 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.
I rode on as my thoughts returned to doubting Brandon would come back to me if someone came riding up the trail. I knew he would love to have me ride half-naked past everyone – all the way back to the kiosk. Remembering the many roads and populated areas I would be passing before I was likely to catch up to him, I became lightheaded. With everything swirling in my mind, a wave of intense arousal and anxiety hit me as I accepted that Brandon, with my top and bra, was definitely gone. The only chance I had of seeing him again was if he stopped to watch.
As much as I fantasize about scenarios like this, the experience is different when made real. And in that moment, fear was taking over. 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. (I did this once for a jungle-themed party at college. A story for another time.) Thinking of the failures from the last time I made a costume of leaves, I knew it would not be easy. This idea seemed a ridiculous solution, although possible. As I came to believe that I could find a way to cover myself for the ride back, another feeling came over me – disappointment. I knew I really did want to follow through with the plan to ride back topless.
Most of the ride so far was under a canopy of trees, and those few backyards. But as I continued and the trail opened to a large field, the sun and wind hit my bare skin with wonderful warmth, and I was simultaneously refreshed by the open air. The amazing sensations distracted me from my fears and I gained terrific confidence. Feeling wonderfully displayed, I noticed how nicely my breasts swayed with the rhythm of my pedaling. I intentionally exaggerated this movement, gratified by these sensations and the liberating 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.
As I neared 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.
As I drew close, 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 near the crossing 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 as I rode away. This confirmed that I was not going to make it to my top without committing to ride closely by people, most likely very many people. The incident with the car was nerve-wracking. 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 top. 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. 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 smiled at them as we passed on the trail. I knew from experience that when people see a naked girl in public, they often first assume she is in trouble. So, I try to always smile to let them know I am okay. I think this helps everyone relax and reduces the likelihood of anyone calling the authorities.
The couple glanced at me as we passed, but they mostly kept their eyes ahead and continued down the trail. I felt something like pride for keeping it together. But I had to figure out what to do next. I felt ready for my interaction with the workmen, but 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 while I worried that others would come along at any moment. It was also now proven that Brandon was not going to return if anyone came down the trail.
I waited there on my bike until the couple passed by again. I acknowledged them with an even bigger smile and a wave, which may have been a mistake, as the girl stopped and asked if I was okay. I told her I was fine, but she kept staring at me. I think she wanted an explanation, but I offered only the smile. Eventually, she nodded and continued down the trail toward her boyfriend, who slowed and kept looking back but 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 then 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 a sexy 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 the guys 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 the only reason 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 one was still insisting on the trade for my skirt. So, just before I mounted my bike, I turned away from them and flipped up the back of my skirt. This clearly thrilled them, and their excited vocal reaction thrilled me in turn. Their deep enthusiastic calls 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 almost regretted not trading them my skirt. But reality slowly sank in and I knew I could not ride back to the kiosk bottomless any more than I could topless.
When I reached the open field, 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 arousing and salacious way.
I was riding across the field when 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, to which I said, “That’s what he gets for abandoning me.”
At first, Brandon did not think I should bother with returning the shirt, but I felt I should. He went along only because he could then catch the second act of my little show, or so I thought. He 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. At that point, 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 believed I wasn’t going to again lose control of my top.
Brandon gave me my top but kept my bra, and I gave him my money to hold. Then he waited and watched as I approached the landscapers. They were pleased, and I think a bit surprised, to see me again. I straddled my bike on the path above their yard and waited while they gathered at the fence. I looked down the trail at Brandon, grabbed the bottom of the sweaty shirt and pulled it off over my head. Making the most of it, I took my time, teasing as I scanned the eyes of my admirers and the windows of the houses while slowly working the borrowed shirt into a ball that I could toss. When I finally made this effort, the shirt hardly went a few feet, landing in the brush at the edge of the path. The guy had to come retrieve it again.
Believing Brandon was enjoying my little show as much as me, I stayed there for a bit. Still straddling my bike, with my new friend standing next to me, I chatted with the men 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 own shirt now, and wasn’t putting it on.
Energized by the success of my teasing, I started pushing things further. I was slightly rubbing and enjoying the stimulation of the bar of the bike between my legs, as I playfully asked questions and listened to their compliments of my boobs. This was most flirtatious fun. But now a couple of them were insisting that I reneged on the trading 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.
Stepping off the bike, I handed my top to my new friend, 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 at 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 boots. But that is not exactly what happened.
I let my skirt fall. The men cheered, although everything was somewhat muted to me as I was numbed by the overwhelming sensations. Stepping out of my skirt, I picked it up and handed it to my new friend still standing next to me. I felt wonderfully alluring, striking various poses I thought were sexy when I practiced in the mirror at home – pretending to be Marilyn Monroe. But I soon realized this may be too much now, as a couple of the other men climbed the fence and started up the hill toward me.
I knew I should get out of there, as I was about to be surrounded by a group of strange men, but I couldn’t stop myself. I loved everything about this, Brandon watching me pose naked (but for my boots), while feeling the humid Florida air and gaze of the men on my body. This was the kind of thing I fantasized about. But as the men made their way through the brush, I saw the neighbor’s back door open. Panic struck, I thought to run but hesitated, half wanting to see who would emerge. I quickly looked to Brandon – and another surprise. I guy was cycling down the path toward me.
‘What am I doing?!’ I thought to myself as it now seemed like people were everywhere while I stood on the public bike path completely naked in my little boots. I snatched my clothes back from my new friend and clumsily gathered myself onto the bike and started to rush back toward Brandon. As I passed the cyclist, I instinctively smiled, but I am sure it was more of a wince. No doubt a guilty look that confessed my feelings of having been caught. The cyclist returned my grimace, wide-eyed, smiling, with a nod of approval. That, and seeing Brandon laughing, calmed me such to better appreciate what was happening.
Now up to speed on my bike, my emotions were swirling from being so exposed and admired. This mixed with the caresses of the wind on my body and the feeling of complete freedom. I was elated and inspired.
With the landscapers watching from behind me on the path as I rode away, I looked back and blew a kiss. But it was not the charming and sexy maneuver I had planned. It was a graceless effort while struggling to maintain control of my bike and clothes. But I like to think they found me adorable anyway.
So consumed with the pleasures of the encounter, I impulsively rode past Brandon without stopping. Holding my clothes against the handlebars, I just had to keep going. I felt like I could ride nude forever, past everyone and everything. If you have ever ridden a bike naked in the daylight for all to see, you know how blissfully liberating this is. I was completely consumed with pleasure and joy.
Pedaling fast, with Brandon pursuing, I came to the open field. I now fully committed and dropped my clothes for Brandon to gather as I sped out into the open, across the field toward the road ahead. Although my confidence was peaking, I somewhat came back to reality seeing a considerable amount of traffic on the road. I slowed to look back at Brandon who was watching while collecting my clothes. I loved that he was amazed by me and had no idea what I would do next. I didn’t either, but knew it was a bad idea to keep going, no matter how much I wanted to do just that.
I turned around and pedaled back toward Brandon, who now stood over his bike on the trail, waiting to see what I would do. I cruised up close to him but couldn’t bring myself to quit. Just as he thought I was going to stop, I quickly turned around and raced back across the field. I just wanted to keep playing and tease that I may continue past all the traffic and busier areas. But Brandon must have known I was only teasing as he did not follow. I circled back and forth a few times with my actions and expressions bouncing between my contradictory intentions. Smirking at Brandon as I rode toward him to surrender, then abruptly turning back toward the traffic, suggesting I was going for it.
Although I was pretty sure I could be seen, I had kept some distance from the road, always turning back before I got too close. But on my last lap, knowing I was going to stop soon, I rode quickly all the way up to the crossing, hoping to convenience Brandon I was really committing to continue across the road and along with the traffic. Several cars slowed, but just before the crossing, I turned around to finally get back to my clothes. I was still too far to yet see the look on Brandon’s face, but I knew he was shocked, as were a few of the drivers. One car pulled over. I looked back for a quick glimpse of the car before speeding up to escape.
When I reached Brandon, still standing at the opening of the field holding my clothes, I could see he was thrilled.
“Oh my God! That was so fun!” I exclaimed. “But, I might be in trouble.”
I looked back at the car at the side of the road just before I realized the cyclist was riding up from behind Brandon. Again, I felt the rush of momentary panic, but quickly settled myself, remembering his positive reaction from before. I smiled at the cyclist, thinking he would pass, but he stopped right beside me. I reach for my top and started to dress.
“What are you guys up to?” He asked.
“Just having a little fun,” I answered, always feeling better when just owning the situation.
The cyclist went on with a few more questions, clearly baffled by my display. I finished dressing as we talked. He wanted to know if we rode there often. He was all made up in professional gear, so I knew he either competed or was a real enthusiast. I wanted to ask, but he kept on with how wild and sexy I was. Although I enjoyed this, it was obvious he was hitting on me, and with the car still watching from the side of the road, I thought it was time to go and best not to encourage more conversation. We excused ourselves as I led Brandon back down the path toward the trees. I didn’t want to ride along with the cyclist, or go past the car. We waited out of sight until the car left, then continued back toward the bike kiosk. However, our adventure was not quite over.
My bra was still hooked around Brandon’s handlebars, and as we moved into more populated areas, I was entertained by the idea that people may notice and wonder. The whole adventure of this day really got me going. I was thinking 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 recently passed several people on the bike path, 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 above the oncoming traffic 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 a bit, I started feeling silly, and got the giggles. After a while with no reaction from the traffic below, 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 put my top back on, 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 a little ridiculous as the girls passed. But, even this was still fun.
“Just flashin’ the truckers,” I confessed.
“Okay.” One of them answered as they moved on.
Although I have gotten myself into much more daring and exciting situations, this was one of my favorites. I think because it was completely unplanned. We were just out to enjoy a nice day off with no real plans for a sexy adventure. But I found myself in several stimulating, if not outright thrilling, encounters. When I think about all that happened, I find it odd that through this whole adventure the only time I truly felt embarrassed was at the very end. When we returned the bikes, I was distracted and forgot that my bra was still on Brandon’s handlebars. I did not think about it until after we were back at the car. (Later, Brandon 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 two teenage boys who worked there. I had to ask them for my bra.
