An Outlaw Biker Gang And A Sissy

Years ago, during the middle of a hot summer day with a clear cloudless blue sky, all of a sudden the roar of thunder was filling the air. Early teenage me was out, was hanging out with his friends when it happened. While we kept on doing our what we were doing, the roaring sound got louder and louder, came closer and closer.

It didn’t took long and our parents began to call for us. There was some genuine worry in their voices, most of my friends left the little park we were in, but I decided to ignore my mothers calls. I went into hiding, because curios me wanted to see what exactly was rolling into town.

My hiding place was a simple one. A fence gave me cover from getting seen from the street, a hedge gave me cover from my mothers hawk like eyes. Once I was at my spot – it actually wasn’t the first time of me using the exact same place – it didn’t took long and the roaring thunder entered the small town I had been living in.

Lots of heavy big motorcycles slowly drove down main street. The bikers were in no hurry at all, and they occupied the whole street. All the other vehicles previously on the street – not that there was much traffic to speak off – drove into a side street or into a drive way. Even the sheriff made sure to get out of way so that the of the motorcycle club could roll into town without anything or anyone standing in it’s way.

I was more than fascinated by those wild big men on their big loud machines. Watching them riding into the small town I was living in, straight towards the town’s only gas station on an empty street, because everyone had gotten out of their way, it made me more than curious about what was going on, it made me wanting to be one of them.

Then the bikers lined up in front of the gas station. One motorcycle after the other got fueled, and then, then my mother found me and dragged me back into our house. She was a little bit mad about me not obeying her, but she mostly was worried, because all kind of things could happen when there was a biker gang in town.

During the following weeks and months still barely teenage me tried to find out as much about the motorcycle club that had rolled into town as anyhow possible. I searched the internet, I looked through books in our tiny small town library and I tried to get a glimpse on everything regarding biker gangs on TV. All that I was talking about were motorcycle clubs, motorbikes and things that were close to the topic.

My parents weren’t pleased with my new hobby. But they let me have my fun, while secretly hoping that it just was a phase that would go by. That their only son would come back to his senses, focus on school, get a university degree and become a lawyer, a doctor or a higher ranking public official.

A few years later, regarding my parents wishes for me I was a minor disappointment, I didn’t had made it to university. After high school I ended up working as an accountant – I really liked that job – in a bigger city, spending my workdays in an average office wearing some business outfit and crunching numbers. While still dreaming about becoming a motorcycle club member and spending a part of my free time in some nice female panties, maybe even lingerie while fucking myself or getting fucked into oblivion.

Yes, you read right, I had discovered my feminine side when I was around twenty. As soon as I moved into my own place, I got myself some lingerie, I began to shave my body – not that I had much body hair to begin with, or even a beard – and I began to fuck myself with some toys. I just was drawn to those kind of things, I more and more began to embrace my sissy side. It was my hot secret. My guilty pleasure that slowly but steadily more and more took over my life and replaced male me.

But there still was my other, maybe even bigger dream. I was roughly twenty two years old when I had enough disposable income to buy myself my first motorbike. It wasn’t the biggest, and the most expensive machine, because I was everything but a tall strong men – I just didn’t grew tall, and my body resisted to put on huge muscles or fat – so handling a huge bike was not really doable for me and getting an awesome custom made bike, I hadn’t had that much money on my hands.

I spent the following weekends learning to ride my bike. I even got a motorbike driving license. My sissy side, it had to wait for the time being, but it never fully went away. Once I had reached a level where I wasn’t afraid on riding my motorbike out on the streets anymore, where I trusted myself enough to be able to handle an hours long ride, I got myself some biker clothes, lots of leather, and then I headed out, exploring the countryside that surrounded the city I was living in and visiting a few biker hot spots while doing so.

About a year later I had made a few biker friends. We went out on trips together, we even were thinking about founding our own little club, but that never happened. What happened was that we were hanging out in biker bars, places that were also frequented by actual motorcycle club members, and there, over some cold beverages, I gradually connected with some “real” bikers.

Again, roughly another year went by and about twenty four year old me became a supporter – people not members of the club, but hanging out at events and generally supporting the club from time to time – of the biggest motorcycle club the city I was living in had to offer. It gave me a first taste off how it actually would be to be part of a club, and I more than liked it. I liked the social community aspect of it, and I also liked that people treated you with respect when you showed up. Or they just were afraid of you, it didn’t really made a difference for me back then.

And nope, no one did knew that I mostly always was wearing some cute very feminine panties beneath my heavy leather biker outfit. My sissy side still was my secret, something that I embraced on my rare home alone time, and mostly only shared with like minded random strangers all over the internet, and an occasional hook up from time to time. When playing with myself, I was getting off a lot to the fantasy of some rock hard biker dick penetrating my holes until I would be an orgasm filled leaking shivering mess.

Another year later I made it. After hanging out in the clubhouse a lot, attending plenty of wild parties, connecting with the members of the motorcycle club, unfortunately not sucking off their hard dicks, the sergeant at arms – he was the one responsible that meetings in the club were held in an orderly, proper way, definitely a higher ranking member of the club – approached me one day and asked me if I wanted to become a prospect, a member on trial. His words put a huge smile on my face: “I’d love to.”

At the next official event at the club house about twenty five year old me got his prospect patch that I immediately sewed on onto my cut off denim jacket. It had been one of the best days in my life so far, it was the day when the biggest dream of mine began to turn into reality. In three years, the prospect time the club I had joined was three years, I eventually would become a member, and then, then who knows where I would end up inside the club’s own hierarchy.

Now nearly all of my time off work was dedicated to the club. I put my sissy side aside, I just had no time for it anymore, and took over the so called minor tasks that had to be done to keep the motorcycle club up and running: Cleaning the clubhouse, making sure that the fridge in the club house was stocked, serving drinks and food at parties, buying all sorts of things for full members – they paid for the things I bought, I just was sent out to get them – and sometimes even cleaning the motorbikes that were standing in the backyard of the clubhouse.

Because that was the place where the members kept their more expensive rides, because someone always was on guard, or at least present in the clubhouse all around the clock. And yes, I was on guard duty too. On the weekend only, because they club somewhat looked after me and made sure that I was able to continue my regular job. Because as I later found out, they didn’t made an account a prospect with out some strategic thinking behind it.

At work they were not that pleased that my hair was getting a little bit longer, but I was good enough at cooking books that I got away with me caring a little bit less about the office dress code. And no, I wasn’t showing up in full biker gear. I always wore a suit, I just went to went to work without a tie and as mentioned above, I let my hair grew out a little bit.

I had been a prospect for roughly a year when it once more was my turn to look after the clubhouse over the weekend. More or less the whole club would leave town until Sunday afternoon, visiting a befriended club in the next bigger city. They were ridding there on their bikes, and honestly, I was a little bit disappointed when it got told that I wasn’t allowed to ride with them.

But that disappointment quickly went away when I realized that it meant that it would be one night on my own, a night more or less home alone in the clubhouse, one of the few nights rally free nights on my own since I had become a prospect, and I decided to use my time wise.

I decided to embrace my feminine side in the club house. To make myself pretty and to fuck myself into oblivion by using my favorite toys. I was more than turned on by those thoughts, and so I began to count the days until I would have to look after the clubhouse.

Then that one Friday afternoon came along. After work I quickly went into my apartment, I got out of my work clothes and put on my biker clothes, then I grabbed my backpack that I had already packed on the evening before and got over to the clubhouse. Most of the club was already present, there was some chit chat going on, then there were a few goodbyes said and then the gang started their bikes and rode out of town.

I looked after them riding down the street, and when they had disappeared behind a corner, I went inside the clubhouse. Where I made sure that all the curtains were drawn, and I also made sure that all the doors were closed from the inside. Not that anyone with a key would have theoretically been able to open up the doors from the outside, but that didn’t matter, because everyone that had a key was either out of town or caught up elsewhere. Or at least I thought so.

After making an additional round through the clubhouse to make sure that I really was on my own, it was time to put my plan into action. It was time to put on some nice lingerie, to do my hair in a feminine way, to apply some makeup, then to prepare my backdoor for some serious penetration and then fucking my more than needy smooth body elsewhere.

Once I was done preparing myself I admired female me in the mirror for some time, I took a selfie and posted it online, not with my real name, and then I left the bathroom with my backpack and my male biker clothes in my hands.

Then horny me roamed through the other people free building for some time, looking for a place to have some nice high quality alone time. I ended up getting comfy on the conference table of the small conference room. The room where the innermost circle and the heads of the club met to talk business. So far I only had heard of those meetings, I had prepared the room beforehand and cleaned it up afterwards, but I never had been present during one. And it should take some time until I would be.

After entering the room, and once more making sure that all the windows were fully blocked – they had some pretty heavy curtains and even some heavy blinds installed in that room, because the meetings in here normally were top secret – I got comfy on the desk. I put a blanket on it, then I climbed on top of it, then I pulled my favorite dildo out of my backpack and began to suck on it.

While wrapping my lips around that plastic dick in my hands I imagined it was the rock hard dick of one of my fellow club members going in and out of my mouth, and slowly but steadily heading down deeper and deeper into my throat.

The toy going in and out of my mouth, it felt so good, it felt so right, and it made my asshole feel all tingly inside while my rock hard dick – I know, not very lady like, but things just were like that back then – leaked more than just some pre cum. I would have moaned out loud if there would have been no plastic dick sliding deeper and deeper down my throat.

I kept on going until the dildo was all inside my mouth and down my throat. I shed a few tears of joys, I even gagged a little bit, but all together, my favorite dildo stretching out my throat, filling out my mouth, it was exactly what I needed. And doing it on the table of the small meeting room in the clubhouse of the motorcycle gang I was a prospect off, it made things even hotter, even more interesting.

As the plastic dick kept on going back and forth, in and out of my mouth I drifted off deeper and deeper. My brain began to turn off, my inner horny animal had taken full control of me and my acting. That horny animal living inside me told me that it was time for something else, that it was time to stop sucking on my dildo and to shove that meanwhile more than well lubed thing up my ass.

To be on the safe side of things I drowned the saliva covered dildo in lube, I applied more than plenty of lube on my butt hole and then the dildo went up my ass. I took my time sliding the toy in, I enjoyed every second of it, the plastic dick stretching out my asshole, it felt more than good.

Once the toy was all in, all up my more than well prepared ass, I took a break. While getting used to the more than pleasant sensation of having something up my butt I let my imagination run wild: It all was about me being on the same table with the heads of the club and the members that belonged to the inner circle taking turns on me, and making sure that I was airtight all the time. One rock hard dick up my ass, and another one down my throat. And one cum shot after the other landing on my smooth feminine body.

I was still imagining the things mentioned above when I began to fuck myself. When I gave myself one gentle but deep thrust after the other. It shouldn’t take long and my moaning was filling the room as the plastic dick kept on going in and out of my ass. It didn’t took long and I was fully lost in the act. I lost track of time, track of my surrounding, track of everything but the more than pleasant sensation of fucking myself up my ass.

My eyes were already running in circles, I was moaning out like a woman when my inner horny animal decided that it was time for more, decided that it was time to get the dildo with the suction cup out of my backpack. I mounted the thing onto the table, I lubed it, I got on my knees above it, then I lowered myself down and then I rode the well lubed toy more than hard. My meanwhile totally limp but still pre cum leaking dick, my balls, they were bouncing up and down every time I bounced up on my suction cup dildo.

My moaning for sure was filling the room while I kept on riding the suction cup dildo. Sweat was running down my body, an intense inner heat built up and it was then, that all of a sudden the following words came to my ear: “Are you enjoying yourself, prospect?”

I got a minor heart attack. I had got caught in the act, I got caught riding a suction cup dildo while being dressed up like a woman. And the one who caught me in the act was the roughly forty year old sergeant at arms who had come back to the clubhouse to pick up the present for the club they were visiting.

Because they had forgotten to take it with them when they left the club house earlier that day. It was the sergeant at arms that came back, and not a prospect, to get the gift because he was the fastest and most ruthless motorbike rider who didn’t let out any opportunity to go full speed ahead on his heavy machine.

And it was the sergeant at arms that was now standing in the same room with me, looking at me with a lust filled expression on his face, watching my reaction onto him catching me in the act. Licking his lips while carefully checking me out from tip to toe. And yes, the bulge between his legs was growing.

I calmed down, our eyes met. Our lust filled eyes met. We both agreed on whatever would happen next without exchanging a single word. We agreed on doing whatever our inner horny animals would make us do. It didn’t took long and the sergeant at arms was naked and standing next to the table in the center of the meeting room who’s walls were filled with insignia of the motorcycle club he and me were a part off.

Yes, I knew that he had a wife and a family, judge me for it if you like, but more than horny cock hungry me didn’t care, and neither did he, who was known to fuck everything within in reach. With the consent of the one he fucked, and his wife too. Because she on her side, she was no angel either.

From now on it was him calling the shots. The roughly forty year old bulky not too tall but also not small sergeant at arms stood next to the table, his dick above the table top, looked at me and said the following words: “Suck on it. Take it all in.”

I moaned out a “yes, sir” before I crawled over to him, went down and began to suck on his almost rock hard dick. At first I only took his glans in his mouth, and I sucked on it like there was no tomorrow. My doing, it made him moan out a little bit, and me, I enjoyed the taste of his dick in his mouth. It had been a while, since before I became a prospect, that I had some real cock inside my mouth.

Then I gradually took him deeper and deeper. The sergeant at arm’s dick stretching out my throat, it felt so good, and then he began to fuck me. The about fifteen years older man used my face to cure his horny urges. Now his moaning was filling the room as his rock hard dick kept on going back and forth, in and out of my mouth and down my throat. My dick got hard again and was leaking a lot of pre cum while my asshole began to feel all tingly inside.

I was more than happy with his dick down my throat, the sergeant at arms clearly enjoyed it too, but while he was holding on to my head and practically using me as a living flesh light, I began to crave more, I began to crave something else: I wanted his dick up my ass. I wanted him to fuck me hard and fill my butt hole with his sticky cum.

It was as if the naked tattooed motorcycle club member was reading my mind. He pulled out of my throat and my mouth, he looked down at me and gave me another order: “Bend over the table, now.”

His words drove another more than welcome shiver through my body. I did as told, I also reached for the bottle of lube standing within reach and handed it too him. The sergeant at arms understood, he drowned his rock hard dick in lube while I went in position. Then his rock hard dick went up my ass. It felt much better than my plastic toys.

The man around forty didn’t hold back. He had seen me riding my suction cup dildo, so he knew that I already was warmed up properly. So he just went inside and fucked me slow, deep and hard. Then he fucked me faster, deeper and even harder. It didn’t took long and our moaning was filling the room, and most likely the whole clubhouse, because the theoretically soundproof door of the small conference room was open.

It didn’t took long and sweat was running down both of our bodies. My not that hard dick and my balls were bouncing back and forth with every thrust he gave me. His strong hands were holding on to my waist, while my hands were holding on to the table I was bent over. Fuck, he really knew how to fuck an asshole.

Two pair of eyes were most likely running in circles as we drifted off deeper and deeper. One hard thrust after the other melted our brains away. Our inner horny animals had a field day while our bodies were practically over heating.

Then there came one very hard, very deep thrust with his rock hard dick up my ass and boom, I came. My untouched balls unloaded themselves through my also untouched and meanwhile totally limp dick. I let out a few last very loud and intense moans while my body began to tremble.

It was me coming, me having an orgasm that pushed the sergeant at arms standing behind me over the edge too. He gave me a few more very hard and deep thrusts while he dumped his load. He shot his load as deep inside me as anyhow possible. Then the strong man collapsed onto me, and we both collapsed onto the table I was bend over.

Two heavy breathing, post orgasm sensation enjoying bodies kept on laying on the conference table inside the small meeting room of the clubhouse of a motorcycle club. Both of them were members of the club, one a prospect with a feminine sissy side, and the other one one the clubs sergeant at arms, one of the higher ranks inside the club. And they both just had fucked each others brains out.

But now they came back to their senses, their inner horny animals were locked into their cages again, and things got a little bit awkward between the sergeant at arms at me. We avoided to look at each other while collecting our belongings. Then we totally accidentally pumped into each other, our eyes met and we had to laugh out loud because of what ever reasons.

That laughing out loud luckily broke the ice, and the sergeant at arms and me began to talk. To talk about what just had been happening between the two of us. We decided to keep it a secret. To pretend that it never happened, because two members of the same motorcycle club ending up in bed together, it was on the same level like doing your coworker. And there are reasons why you don’t do your coworkers.

When we were done talking we both disappeared into the bathroom to fix up ourselves, and then a fully dressed sergeant at arms met up with mostly dressed me. It didn’t took long and we were exchanging horny views again. But this time the sergeant at arms pulled the plug. He got the present for the befriended motorcycle club out of the save in the corner of the small conference room, then he went towards the front door of the club house.

I tried to seduce him for a round two, but he ignored my doing and said the following words: “Maybe another day, I have to leave. The rest of the club is waiting for me. But well, maybe another day.”

Him telling me that we might fuck again, it made me feel all warm and fuzzy inside. I blushed a little bit, then he left the club house, and I knew, and he knew, that a next time might come one day, but when we would meet up again he would be the sergeant in arms and I would be the masculine – or as masculine as I could be – prospect again. So to get him fuck me again, I maybe would have to pull a string or two.

After the sergeant at arms had left the clubhouse I briefly thought about going for a round two, filling up my butt hole once more with my suction cup dildo, but my horny levels just weren’t quite there any more. So I decided to clean up the mess I had made and then head upstairs – there were a few small apartments of the second and the third floor of the clubhouse, mostly used to accommodate guests or members in need of a roof over their heads – to take a long and hot shower.

Once I was done cleaning up myself and getting dressed again, biker attire wearing male me found himself in the close to restaurant grade kitchen of the clubhouse – some real cooking was happening in there before and during bigger events – looking for snacks and some ice cold beverages. I found both and then got comfy in front of the TV in the sofa filled lounge room.

Yes, the clubhouse had it all. Back then I had no clue who and how the place was financed, because the members fee, and the fines that members had to pay on occasion when breaking the rules or fucking up something, they for sure weren’t enough to pay for a place like that.

But not knowing how the place was financed didn’t really bothered me, I just enjoyed that being alone in the clubhouse a little bit longer, until I fell asleep, on the sofa, in front of the TV, watching my favorite biker movie from the late 1960s.**An Outlaw Biker Gang And A Sissy \[F25/M40\]**