Juggling My Desires
(mid 1990s)

While going through the divorce from my first husband, I was using an office as my apartment, thanks to the kindness of business partners, Mark and Brandon. After a couple of months, I had grown quite close to both of them, and I was really enjoying the freedom from my marriage. But I began to wonder at what point I would be overstaying my welcome. Just as I was having these thoughts of what would be next for me, I learned of an opportunity to get paid to tour the mid-West for about 6 weeks.

One evening, I overheard a call Brandon received from what I came to understand was an old friend. Jackson was a professional juggler/magician/comedian. He was calling because he had contracted a tour performing at schools across the mid-West. I learned that Brandon had worked with him on similar tours before. He would help Jackson with his staging, audio, and a few other matters related to the tour. But Brandon now had better work, so he was not interested in going on the tour.

I had never met Jackson, but this sounded like a fun adventure, so I volunteered. Brandon thought I really wouldn’t want the job. He warned me that Jackson was cheap. Not only would the work not pay well, but he also wanted to share hotel rooms to save money. That didn’t bother me. I was excited to travel and thought that sharing hotel rooms for 6 weeks, with a guy I had never met before, only added to the adventure.

From the way Brandon was warning me, I wondered if he didn’t want me to go. Just coming out of a restrictive marriage, I was really starting to cut loose. I had returned to indulging my exhibitionist urges. In part as a reciprocal gesture for the kindness of my landlords, but mostly for my own thrills. I had begun hanging around the office/apartment often half-dressed and sometimes naked, in the presence of my friends, and I surprised them with a sexy video. The guys were enjoying this too, and Brandon had even begun videotaping some of my antics. We were not a couple. There was no sex. We were just having a lot of fun together and becoming very good friends.

But as it seemed that Brandon was making an effort to talk me out of the tour, I wondered if he was concerned about me sharing a room with Jackson. In these conversations, I learned that Brandon and Jackson grew up together and trusted each other. This made me feel safe, and I expressed that to Brandon. After he understood I was not concerned with the low pay or rooming situation, he had Jackson call me to discuss the job. Although in that call Jackson did explain what my responsibilities would be, it was less of an interview and more just me also convincing Jackson that I was fine with the conditions.

I spent the weeks before the trip asking Brandon about Jackson and the work. He told me a few funny stories about their adventures together, which made me even more excited for touring the mid-West in such a fun way. But what I did not know at the time, Brandon was also telling Jackson about me.

A few weeks later, Jackson picked me up in his truck full of equipment and we started off on our long road trip. I found him to be handsome and very charismatic. His whole job was performing for people. Whether telling jokes while juggling in front of a large crowd, or doing close-up magic with a more intimate group, he was always putting on a charming show. Even in private, he seemed to never turn this off. It made the time spent with Jackson a lot of fun, but exhausting at the same time. I came to learn that you could not get too close to him. He never seemed to be real with anyone, always the performer. But this was a good dynamic for our time together on this tour.

Most of the time we would be driving just a few hours between cities and towns in the mid-West, putting on shows in school theaters or gymnasiums, spending only a night or two in each town. But this first drive together was a long one as we traveled from Florida to Ohio. We got to know each other on this drive. I could already tell Jackson and I were going to get along very well.

As an exhibitionist just coming out of a stuffy marriage, I had been having a great time teasing Mark and Brandon. And in the weeks before the trip, I had been thinking about what fun I could have with Jackson. I didn’t want anything sexual. I like to be daring and surprise people with my antics. It is different to show off in front of a stranger, co-worker, or roommate than a boyfriend or lover. I knew that Jackson was straight and did not have a girlfriend. So, I thought sharing a room with him was going to be exciting for me, and hopefully him. I tried to gauge this during our long drive to Ohio.

It started with what I was wearing – a short skirt and tight tank top. I thought I looked good in this, but it also gave me the ability to escalate, if things went well. Even though it was Fall, my outfit was fine for Florida. But as we got closer to Ohio, this would not be suitable attire. So, my outfit provided an excuse to change clothes during the drive.

I would also plant topics in the conversation that would invite his thoughts on related matters. In my excitement for such a road trip, I re-read Jack Kerouac’s ‘On the Road’. And it gave me a way to bring up a fun idea. When the conversation slowed, I offered to read aloud from my book. Jackson agreed, so I kicked off my shoes, put my feet up on the dash, and settled back to read. Pretending to pick up where I had left off, I really just went right to a chapter I could use to test him. It was the part in the book when they are driving across Texas and Dean convinces the car’s occupants to disburden themselves of their clothes.

As I read this part to Jackson, I paused to joke that if we get bored with all the driving, we should disburden ourselves in the same way. He turned his head toward me with his eyes focused on my legs. Believing these to be my best feature, I had them elevated, and well displayed in the sunlight, as my bare feet caressed on the dash. This was causing my skirt to slip, revealing just a little more than a good girl should. Jackson was taking this in as he answered, “I will if you will.”

This gave me the tingles. I was already having too much fun. But I was relieved to now be sure that we were going to have a great time together. Mind you, if I had known then that Brandon had already told him certain things about me, I would not have been this flirty so early on the trip. This was too much, but at the time I thought I was just testing him with a little sexiness and a few jokes.

My not knowing what he knew affected another concern for me, but in a different way. I had been debating if I would keep with my habit of sleeping in the nude. If I knew he was practically expecting me to already, I would have gone for it. But fearing I might be shocking this guy who didn’t know what he was in for when he hired me, I was really torn on the topic. I planned to use what I learned about him on this drive to decide how far I could go. But I already knew that if I was going to sleep naked while he was in the room, it would have to be from the beginning. I couldn’t sleep in my clothes for a while then suddenly go naked one night. He might take this as an invitation. But if I established that I always slept in the nude, this would just be how it was. This decision depended on his attitude and the tone of our relationship that we were building this first day together.

By the time we crossed into Kentucky, the sun was down, and the temperature had dropped. When we stopped for food and gas, I grabbed some warm clothes from my suitcase in the back of the truck. I had decided to go through with my idea to change in front of Jackson. Standing at the back of the truck, while he was pumping gas, I thought about changing right there while we talked, even though it was cold. But before I worked up enough courage to change under the gas station lights, where others were likely to see, Jackson finished pumping. So, I brought my clothes with me into the truck. As we got in, he commented that I must be freezing. This was my opening. I agreed that I was not dressed for this weather and asked if he would mind if I changed. Jackson started driving as he told me to go for it and added that he wouldn’t look. I reminded him that we would be living together for the next month and a half, so we would have to get used to each other.

Aside from the occasional passing light, it was pretty dark in the truck. I took off my top and skirt, now just wearing panties but no bra, I fumbled with my pants and sweater longer than necessary to give plenty of time for me to catch Jackson peeking. I know he gave me the side eye a couple of times, but never really looked. However, he made constant jokes while I was changing. I don’t remember most of them, but one stuck with me. He said it was nice to see that I was not so clothes-minded. He kept me laughing the whole time I was changing. I could tell he enjoyed my reactions to his jokes. We were getting along well. This helped with a big decision. I would be sleeping naked at the hotel.

We finally stopped for the night just South of Cincinnati. Brandon was not kidding when he said Jackson was cheap. Even though I never had much money, I was used to hotels, not motels as he chose for most of this trip. The door to our room opened right into the parking lot. He had me duck down in the truck while he checked in, to avoid the fee for an extra person. Then I had to sneak into the room. It felt wrong, but in some ways, it added to the adventure, and set the tone for the illicit things to come.

I was relieved to find that the room had two beds. I feared that his checking in as a single person would put us in a room with only one bed. I knew it would be too much for me to flirt with him as I did on the drive, then slide naked into his bed. But having my own bed, I was excited to go through with my plan. We were both very tired. After taking a quick shower, I wrapped myself in a towel and took a few minutes in the bathroom to build up my courage. I was thinking about another time I made the decision to sleep naked in a hotel room with friends. It was a cheerleading trip, and when the girls realized I was naked, they tossed me out into the hallway. I knew Jackson would not do this. Although, I could not help but picture being locked out naked in the motel parking lot.

When I came out of the bathroom, Jackson was already in bed, but not yet asleep. My mind was buzzing. I could feel the pressure of my blood pumping as I grew more excited. I was about to drop my towel in front of my boss, who I just met today. The lamp on the table between the beds was on, so I moved to turn it off, but stopped myself as I thought better to leave it on. Now standing inches from him, I turned my back to him and prepared my bed. He wished me a good night. Without looking back at him, I said, “Good night,” removed my towel, and hopped into bed. All was quiet for a minute or so, then he asked, “Do you want this on?”

Not expecting this question, I answered, “I don’t want anything on.”

Then I realized what he meant as he turned off the lamp. I pulled my head under the covers and cringed at my stupid answer as I heard him say, “I noticed.”

As tired as I was, I had worked myself up too much to sleep. I heard his last comment over and over in my head for at least an hour before I finally fell asleep. In the morning, I woke to Jackson talking on the phone. He was fully dressed, sitting on his bed, and facing me as he was reviewing some schedule changes with his booking agent. When he noticed I was awake, he told me we needed to get moving. We had a few more hours to drive before arriving at our first show that afternoon. This was before most people had cell phones, so he was using the phone on the nightstand. I knew he would be sitting there until he was off the phone. So, I had to decide how best to get out of bed. I had laid my towel on the bed, but it was gone. I looked around at the floor, as much as I could from under the covers, but no luck. He knew I was naked, but should I stand up out of bed just inches in front of him? Would it be more awkward if I shimmied across to get out from the other side of the bed and scurried to the bathroom? I decided to get up and pull the covers with me, but they were tucked in tight. I was able to stand, but now I was stuck standing in from of him, wrapped in a sheet, and unable to move. Still on the phone, he laughed at me while I tugged as hard as I could at the bedding. He gestured for me to hurry. What I had planned as a graceful display had turned quite pathetic. Frustrated, I gave up and untangled myself from the sheets, almost falling as I came free, and stumbled naked to the bathroom. There I found my towel. He had hung it up. I wondered if he thought he was being helpful, or if he had set me up. I figured the latter. But I knew he was at least amused by me so far. Before hanging up with the agent, I heard him say that the trip was already off to a great start.

As we drove toward the first school, I didn’t want to bring up what happened at the motel. I was hoping he would, but he didn’t. We talked more about the show, and what I would do when we got there. My job was easy. Sometimes he would need his PA system set up, but most of the schools would already have one for him. I would help unload and stage his props and equipment, then put it all back after the show. He would usually do all the talking with the staff and kids. It became obvious to me that I was hardly needed. I realized that he just didn’t want to be alone on the road for so long. I was really more of a paid companion. Even with the low pay, I thought this was a great job for me.

We only had one show that first day, so when it was over, we took some time for him to teach me a few things about his equipment and what more I could do to help. We had to be in another town by the next morning, where we were scheduled for three shows at three different schools that day. This was pretty much how it worked. One to three shows each day, and a drive to a new town that evening. We would do sightseeing on the weekends, which we had off.

As we pulled into another motel that evening, Jackson asked me again to duck down so we could avoid the fee for an extra person. I told him that if we keep doing that, we may end up with only one bed. I could not tell if this was just something he had not considered, or if it was his plan. But he thought hard about this without responding. I added that I was fine with sharing a room, but I wanted my own bed. He nodded and asked me to hide anyway, saying that he would make sure I got my own bed.

We did have two beds this time, as well. Because it was not yet late, we walked down the road to get some food and ended up bringing some beer back to the room. As we hung out drinking and talking, I decided to change into something more comfortable. I knew I could go into the bathroom to change, but I thought it would be fun to just change at my suitcase beside my bed. I put my back to him as he continued his story. We talked while I took off my shirt, pants, and bra. I enjoyed hearing the changes in his voice while he tried to pretend all was normal. Leaving on my panties, I pulled my t-shirt over my head and joined him back at the little table across the room. It was obvious that I was having the effect on Jackson that I wanted. I felt bold and sexy.

We talked for a couple of hours over a few beers before I could tell he was fighting to stay awake. So, I went into the bathroom to get ready for bed. Teasing Jackson was turning out to be more fun than I had hoped. I wanted to keep taking things further. So, with a little help from the beer, I left the bathroom door open as I took my shower. He could not see me unless he came up to the door, but I still got a thrill from leaving it open. Afterward, I wrapped myself in a towel and walked out to see that Jackson looked to already be asleep. I dropped my towel on my bed and climbed in. Then I reached up and turned out the light. I heard him say, “I see you still don’t want anything on.”

I covered my face in embarrassment for an instant before my arousal took the lead. I first thought to not respond, but I just had to ask, “Why did you take my towel?”

At first, he didn’t know what I meant, so I reminded him of that morning when I got out of bed. He said that he found the towel on the floor and hung it up.

“How chivalrous,” I stated with sarcasm.

I don’t remember his exact words, but he went on, in an inebriated stammer, to say that Brandon had told him that I was quite liberated. He knew I walked around naked in front of the guys. I was shocked. But my feelings were a confused mixture of mortification and elation. I demanded he tell me what else he had heard about me. He added that he knew I went skinny dipping with some friends at Brandon’s apartment complex, and photocopied my boobs at work, spreading hundreds of the copies around our circle of friends. (I did copy my boobs, but other people spread the copies.)

Without confirming or denying, I pushed him for more of what Brandon had told. He added a little about my being naked around the apartment, then insisted that was all. I decided to say nothing more and just get some sleep. But I laid there trying to decide how I felt about Brandon telling all of this to Jackson. At least a full minute passed before Jackson (unsolicited) blurted out, “Okay! I also saw some videos. A lot of videos. Good night.”

When he said, “A lot of videos,” I knew Brandon must have shown him everything, because there were not a lot. There was one where I did a little fashion show, and Brandon had recently caught me in the kitchen cooking naked, recorded me in a bubble bath, and I spent an afternoon posing on the sofa. I had not yet seen most of these videos, but I remembered that I pleasured myself on the sofa and in the tub. Again, my anger quickly turned to arousal. When making the videos, it turned me on to think they could show up anywhere, anytime. This is what was happening. It was what I wanted, but still surprising and hard to process what I really thought about it. I knew we had to be up early tomorrow, so I said nothing else to Jackson, and tried to fall asleep. Eventually, I did.

The next morning, I woke up before Jackson. Just like every morning, I was feeling randy. But even more so now with all these thoughts in my head, and after not having touched myself for two days. I usually pleasure myself every morning, and often several more times before the day is done. I have been a chronic self-stimulator all my life. I knew this trip with Jackson was going to be interesting. I figured that I would have to curtail my habit, or spend more time in the bathroom, but I like to enjoy myself in bed when I am in that groggy state of waking. So, seeing that Jackson was still sleeping, I found this to be a good time. I tried to be discreet, staying quiet and under the covers. I like to lay face down and use both hands to put pressure where it counts as I make quick and random gyrations with my hips. Unlikely I would wake anyone not in my bed, but if someone were watching, what I was doing would be obvious. Two days is practically a record for me, and I was revved up by all that was going on. So, I wasn’t able to fully hold back my moaning through the first orgasm. And just as I was considering a second round, Jackson stood up and walked to the bathroom. My face, already red, must have turned purple as I felt the realization hit me that he may have not really been sleeping that whole time. Just like most of my would-be humiliating moments, I could not reconcile if I were more embarrassed than aroused.

While Jackson was in the bathroom, I looked for my towel. It was nowhere around my bed. I knew now that he really was messing with me. That got me excited, but I decided to get dressed before he came out of the shower. I had to calm down. This was only day three and I was about to explode.

Over a fast-food breakfast on our way to the first school of the day, I brought up what was most on my mind. “So, Brandon told you all about me?”

Jackson blew me off by saying something like, “Not really,” and turned the topic to our schedule for the day. I learned that he was just as interested in our little games as I was, but that would have to wait until after work. He wanted to, or had to, focus on the shows during the day. We were dealing with dramatically different worlds – working with kids all day, and sexy games at night.

As the day went on, I decided I would not ask Jackson more about what he had learned of me. I wanted to keep some mystery around our play. And I didn’t want to spoil my feeling that I could still surprise him. I had also thought about calling Brandon, but for the same reasons, decided not to address the topic with him either. At least not yet.

That evening we had a long drive and arrived in the next town very late. So, when we walked into the room to find only one bed, we were both too tired to find another room. Jackson said he would sleep on the floor, but I told him it was fine. We could share. When I said that, I thought to myself that I would sleep in a t-shirt. I had already established that I slept in the nude, so I could get away with that when I wanted. But tonight, he would know why I slept in a shirt. I took a quick shower and came out in a towel to get dressed at my suitcase. I could feel Jackson watching me as I changed into my t-shirt and panties. I felt the urges building in me. As tired as I was, I still wanted to play. I noticed he was climbing into bed in a t-shirt and boxer shorts. I walked over to my side of the bed and pulled back the covers. He gave me a hard look and reached up to the lamp asking, “You want something on this time?”

Already on the edge, the opportunity to offer a clever retort was all I needed to commit. I answered with a simple, “No,” pulled my t-shirt over my head, slid my panties off, and got into bed while adding, “No funny business.”

The lamp went out and we didn’t say another word all night. I knew he was shocked. I was giddy with delight.

In the morning, I woke to feel that my bottom was pushed up against Jackson. I thought I should move, but was enjoying the sensation. I was so much in the mood for my morning routine, although doubting I could get away with it. I slid my hand between my legs but could only tease myself a little without being too obvious. When Jackson began to stir, I moved away. Now we were each lying on our backs, and I noticed he was no longer wearing a shirt. He opened his eyes to see me staring at him.

“Are you naked?” I asked.

He answered, “No, are you?”

I rolled my eyes and complained that he had slept in his underwear every night until I was in his bed. But he insisted that he was wearing underwear. I was just having fun with him, but I stuck to my shtick.

“Show me,” I ordered.

He hesitated.

“I knew it!” I exclaimed.

But again, he insisted he was not naked. When I was pushed up against him, I could tell it was not his bare skin. So, I felt pretty sure he was telling the truth, but I enjoyed watching him squirm.

“You need to show me right now.” I demanded.

He started to explain what happens to many guys in the mornings. I stopped him as I already knew about this, and could relate. Nevertheless, I asked if it happens every morning, or if it is happening because I am naked lying next to him. He finally caught on to me and mumbled a profanity as he got out of bed, still in his boxer shorts, and covered his erection as he made his way to the bathroom.

I gave it a few seconds before a final jab, “Whatcha doin’ in there?”

He replied, but I couldn’t understand him. I wondered if he was commenting on what I had been doing the morning prior. I didn’t matter. At this point, I was hoping he did catch me. Either way, I was teasing Jackson on so many levels, and I knew we were really enjoying each other.

When I first learned about this trip, I was mostly excited for the travel. But so far, we had only seen rundown elementary schools, in small industrial towns, between nights in dirty motels. But I was still having a great time.

The next few days and nights played out much like the previous, except that we did not have shows on the weekend. We were in Northern Ohio when we reached the first Friday night. Not appreciating how long it takes to get to Niagara Falls, we decided to spend the weekend there. Neither of us had been before, and we both wanted to do some sightseeing. We didn’t think this through very well. A quick glance at the map and it seemed not too far. But a few hours of driving after a late evening start, we decided to stop and get a room for the night.

By this point, I had made it my habit to leave the bathroom door open when I showered. The design of most motel rooms allowed Jackson to either ignore me, or maybe catch a quick peek if he wanted. This was stimulating for me, and I think also for him. But the layout of this room was different, and it had a mirror covering all of the far wall, reflecting the bathroom to most of the motel room. When I got out of the shower, I caught Jackson watching me in the mirror as I was toweling off. At first, I pretended not to notice because I wanted him to watch. But when he realized that I knew, I joked that he should, "Take a picture, it will last longer."

Being the comedian that he was, he picked up his camera and took a picture. I laughed and expected that would be it, but he kept taking pictures. The more he took it seemed less like a joke and more like he really just wanted these pictures of me. Each time I heard the camera go off, I got more excited. I was a little nervous to come out of the bathroom, but I was enjoying the attention. So, instead of wrapping myself up in a towel, I just came out naked. He was no longer laughing or joking. He looked serious. But just as I thought to really start posing for him, the film ran out. He put the camera down. I was already too far gone. I couldn’t stop.

This was another occasion when we only had one bed. I laid down in the middle of our bed and stretched my arms above my head while turning my body just so and positioning my legs to complete what I hoped he would find to be an irresistibly sexy pose. He just stared at me and seemed to not know what to do.

So, I offered, “Is that it?”

“What would you like?” he asked.

I told him he could do as he likes… and he did.

We spent the next five weeks driving to the different towns, performing at the schools, and having intense sex every night. Maybe it is not accurate to call it sex. We were fucking. It was wild and uninhibited.

I don’t want to be too crass, but I would not be truly telling about this experience if I did not better detail just how intense our adventure became. My favorite part of sex is when a man ejaculates inside me. I love to feel his throbbing and exploding. Most guys want to move on right after they finish, but I want him to stay inside me for as long as possible because my contractions go on much longer. I want to feel the resistance of him inside me. I want him to feel me. So, when I am really into it, and I can tell he is getting close to climax, I will wrap my arms and legs around him tightly and repeatedly beg, "Cum inside me." I think this drives most guys as wild as it does me. I like to vocalize, but I am not usually a screamer. Although, I took advantage of these motels with Jackson to really cut loose. Sometimes he would try to quiet me, but I enjoyed that our neighbors could likely hear my sexual mantra as I begged him. We had loud and savage motel sex daily for the next five weeks.

This lessened my thrills of exposing myself to Jackson. But it was well worth it. It turned out that Jackson was a real horndog. I know my libido is far greater than most. I cannot express how wonderful it was for me to share a time with someone who also has an elevated sex drive. And we did find other ways to amuse ourselves. We even carried out my idea to disburden ourselves of our clothes on a long drive. I did this several times, but there was one time that Jackson joined me. The two of us driving naked together along Indiana and Michigan farmland is one of my favorite memories from this trip. I think of it as my Kerouac experience.

As soon as my relationship with Jackson turned sexual, I called Brandon and told him everything. Brandon expressed happiness for me. I think he knew what would happen. He knew Jackson well and had a pretty good idea of what I would do. I did not mention that I knew what he had told, and shown, Jackson about me. Brandon enjoyed the details of my stories from the trip. Every few days I would call him and update. I felt sure Jackson was doing the same thing. I would love to have known what they said about all of this, but I never asked.

Although Jackson and I had great fun together, I knew we were not really into each other. It was entirely sexual. But what I did with Jackson in those motel rooms across the mid-West was something that I think could only happen with a loose affiliation. It would have been different with someone I truly love. Nevertheless… it was fantastic!
-


I include a few videos that I mention in the story. And I have attached the pictures that Jackson took after I caught him watching me in the mirror. I came out of the bathroom and cleared some items from the bed before lying down and offering myself to him. And there is one picture I took of him. (A little secret, I got to know some of these juggling pins… intimately.)
Apologies that these pictures are old and mostly taken in the dark.