tagTranssexuals & CrossdressersWhoring for freedom

Whoring for freedom

byTrinni69©

It is four o'clock on a Friday afternoon and I have been driving for almost two hours on my way to a cabin in the middle of nowhere. According to the instructions my Mistress gave me, I still have about an hour to go. I have the air conditioner on because it is a very hot day and I have to make sure my make-up is perfect and I smell pretty when I arrive. I can't believe I'm so stupid I got myself into this situation. My Mistress ordered me to dress up like a slut and drive to this cabin so I can be sex slave for some male friends of hers.

When I met my Mistress over a year ago, I had no idea she was going to be my Mistress and I would become her slave. She was a beautiful girl I met at a bar and I had no idea she was so conniving. I think she picked me because I was a thin guy and with long hair and I had very little body and facial hair.

I was sitting at the bar and she sat down next to me and ordered a drink. We started talking right away and we really hit it off. We laughed and danced together late into the night before we returned to my place. During that evening she said in a joking manner that I was weak and she could have me dressed up like a girl and having sex with men. I figured it was just a joke and no way in hell that would or could ever happen. I just laughed it off and forgot about it. What a big mistake that was.

After that night we were inseparable. It seemed like we had everything in common and she was and excellent girlfriend. For the first few months the excellent sex but nothing kinky or out of the norm. But after that she started slowly introducing me into bondage. She would tie me up and would tease my cock until I would cum harder than ever before. I started really getting into it when she took it to a new level.

One night while I was tied up she put a male chastity belt on me. It was only for a short time but when she teased me while I was wearing the belt, it was the wildest sensation I had ever had. No matter how horny I was, the device would keep me from getting hard. I would get a little spacey and my head would feel hot. Then she would take it off and make me cum harder than ever before. Over time she would increase the time I had to wear it. Since I work from home on my computer and rarely ever have to see anyone in person, she took great advantage of that and would make me wear it for days at a time.

That was until about eight months ago when she put it on and has not let me cum since. That is when she went from my girlfriend to becoming my full time Mistress. The only time she takes it off it to wash my cock area. Every time she does that I am tied up so I can't relieve myself or stop her from putting it back on. I have tried to remove the device but the only way is to cut it off and that scares the hell out of me. In these past eight months she has trained me in the finer art of acting like a girl, applying make-up and sucking her strap-on. I have never been with a man but she has taught me how to please multiple men at the same time. At first I completely resisted but as time went on she broke me down.

She has even filmed me in many humiliating situations and made me stand at attention while she shows the films to her friends. Then she and her friends use me to practice S&M and B&D techniques. I have teased, humiliated and used for so long, I can't take it anymore. Now I am willing to do anything to get this off my cock and be able to cum. I just want to go back to being a regular guy again. Now I don't know what to except when I get to the cabin. I just know I'm not leaving until everyone of her friends is fully satisfied. I don't have a clue on many guys are going to be there or how long I will have to be their slave. The other problem is this cabin is so far away from anyone or anything, even without this chastity belt I will be completely at their mercy. I'm just praying that when I'm done in the cabin she will finally let me be me again.

I finally pull up to the final turn which leads me to the cabin. I slowly drive up the drive way which seems to be almost a mile long and my heart starts to pound. I see a large two story wood cabin with a large front porch. On the left side of the porch is a large gravel parking lot with about ten cars parked in it. On the right side I see a lake with a large gazebo in it with an arched walking bridge leading over the water to it. I park in the lot, I look around to see if I see anyone and there is no one in sight.

As I was ordered, I check my make-up to make sure it is perfect before I step out of the car. I step out and feel the gravel under my white high heel shoe. I have to steady myself as I get out and I immediately pull the bottom hem of my short white thigh high dress down. It is so tight it rides up with almost any movement and shows off everything I have. This includes the fact I have fake breast which my Mistress had adhered to my chest before I left with no bra or panties on under the dress and the chastity belt which is on my cock. If the dress was not so tight which made it obvious I had a cock in a chastity device, I would easily pass as a girl.

I walk through the parking lot and up the walkway to the front porch. On the porch I see a chain bolted to the floor and an open pair of hand cuffs. As ordered I get on my knees, connect the chain to my white collar and place the lock on it securing me to the porch. Then I place the cuff on my left wrist and bring both of my hands behind my back securing the right wrist into the other cuff. Straighten up my back but lower my head to show my obedience. I hold myself in that position of over an hour which makes my knees hurt and my back start to get tired. I have held this position for a long time for my Mistress but after the drive and the anxiety of my immediate future was taking its toll.

The sweat is rolling down my face and into my eyes which makes them sting. I realize I left my purse with my make-up in the car and there is nothing I can do about it.

I hear the sound of many men walking and talking behind me. As I have been trained, I don't move a muscle. I'm guessing someone finally noticed me because I start to hear guys whistling at me and stating how much fun it was going to be to humiliate me and fuck the shit out of me. Knowing I was about to be used by multiple men, it took everything I had not to cry or let it show. I got to love the bondage part when I wasn't being treated like a girl or humiliated. However, I never have had the desire to be with a guy much less some guys bitch.

The footsteps get louder and I can tell someone is now standing right behind me. I feel my dress get pulled up exposing my ass to everyone and cheers and laughter bellow behind me. My head gets push forward to the floor and I feel a pair of hands reach between my thighs forcing me to spread my legs. I spread them out just past shoulder width. The hands the spread my ass cheeks and someone shouts out how it looks like I have a tight pussy ready to be fucked. My ass cheeks are released and I feel a hard slap on across my ass.

I hear the person who slapped my ass say, "Everyone, let me have your attention. Our little slut is dressed in a white because she is a virgin and has never touched a real cock. Stay just like that slut until we are ready for you. I hope for your sake you flushed that thing out because if anyone of us gets shit on our dick, you are licking it off and getting punished for it too."

I don't move at all as the men walk inside the house. I feel a slight breeze brush across my ass as I wait for the inevitable. I hear everyone inside the house and try to figure how many men there are. It sounds like there has to be somewhere between fifteen to twenty guys and I hope they won't be too brutal with me.

I hear a single set of foot steps walking towards me. Suddenly I am grabbed by my long brown hair and get my head pulled up. I see a handsome looking man in his mid twenties starting at me.

"Hell, you have been sweating so much out here you already look like we have pulled a train on you. That's not work for me or the boys. We want you to look fresh. Didn't Jan tell you that bitch? I'm going to un-hook you from the porch so you can touch up your make-up. Where is it?"

I tell him I forgot my purse in the car and that is where I keep my make-up.

He shouts, "Guess what gang, the slut forgot her purse in the car. Come outside so we can teach her a lesson and make sure she doesn't forget anything else."

Just then I hear all of the guys walk out onto the porch. Still holding my hair, the guy starts to turn around as I stay on my knees. Once I'm turned around and facing the crowd I see I was right about how many men there were. My dress has risen up over my chastity device and most of the men start to point and laugh at my secured cock. A medium butt plug which has a long chain connected to the base is thrown on the ground in front of me as well as a tube of lube. I'm ordered to lie on my back and insert the plug giving everyone a show. I pick up the plug and start to lube it up. I lie back and spread my legs wide. The lube feels cold on my ass as I start to insert it. As ordered I take my time slowly fucking myself with the plug as I work it into my ass. I'm feeling completely humiliated as I get called names like sissy, slut and bitch while I'm doing this. Once I have it all of the way in, the guy next to me releases the chain on my collar but picks up the end of the chain connected to the plug.

He advises me that under no circumstances should the plug come out unless it is approved. Then he starts to walk towards the crowd. I awkwardly start to slide myself on my back following him so it doesn't pull out and everyone burst into laughter. He stops and tells me to get on my knees. I get on my knees and start to pull my dress down. My hand gets slapped by another guy as he tells me to pull it back so everyone can get a good look at what use to be my cock. I'm ordered to tilt my head back, open my mouth and keep it open. I'm also told I my not allowed to swallow anything until I'm given permission. Just then everyone pulls their cocks and start to jerk off. One of the guys told me my punishment for forgetting my make-up in the car was some extra humiliation. I keep looking up at the men jerking off when one guy steps forward and points his cock towards my mouth and shoots his cum into it. The next guy steps up and also shots his load into my mouth. It takes a few minutes before anyone else cums. I hold the cum under my tongue so I don't accidentally swallow it. The cum has a different taste from my cum but does not taste bad. I stay there as guy take turns stepping up and cumming in my mouth. I have a hard time keeping it all in without swallowing because of it mixing with my saliva. When the last guy cums in my mouth I am ordered to gargle the cum for a minute then swallow it down it one big gulp. Once I get it all down I have to open my mouth to prove I swallowed it all.

Then I am pulled up to my feet and I'm led out to my car getting slapped on the ass by everyone I pass. I open the door and lean in to grab my purse off of the passenger seat. I feel a tug on the plug and quickly get back out of the car. I do it so quickly I almost hit my head on the way out. Once again everyone laughs. As I'm led back to the house and inside I get more slaps on the ass.

Inside there was a large dinning room on my left and a large living room on my right. The living room is full of chairs and couches facing a large screen TV. I'm led past a set of stairs to a back room of the kitchen. The chain is let go and I'm told to fix my make-up but not to take too long. I closed the door and look at myself in the mirror and want to start to cry. Not because I'm sweaty and my make-up looks terrible but because of what I had just gone through and knowing this is just the beginning. I get all fixed up and open the door to have someone reach between my legs and grab the chain connected to the plug. I'm led out to the living room and ordered to stand next to the TV so I can not see the screen and but facing everyone.

All of the guys are now facing me and the TV sitting comfortably in just a pair of shorts and nothing else. The TV comes on and all of the guys start to smile. I have no idea what they see on the screen. I stand at attention and listen trying to figure out what it is. It does not take but a few seconds to realize they are watching a video my Mistress made of me being humiliated. I could not help but to bow my head once I realized. I was ordered to keep my head up because the humiliation on my face just made the video that much better. Some of the guys started rubbing there crotch through there short while the video went on. I could tell they were really getting into it and could not wait to get to me. One guy pulled his medium size hard cock out and told me to crawl over to him. As I get on my knees and crawl between his legs people comments about the video of me and saying how I look like a natural cocksucker.

"I can't take it anymore. I need your hot lips to wrap around my cock and suck me off."

I reach up and grab my first real cock. I'm glad it is not too big for my first one. I kiss the head and I'm surprised how soft it is compared to this hard shaft. None of the dildos captured this feeling. I swirl my tongue around the head and take it into my mouth. It taste a little salty and musky but not too bad. I tease the cock in my mouth for a few minutes then swallow all of it. I give some suction as I start to bob up and down his shaft. Within a couple of minutes I feel his legs tense up around me as he shoots his load into my mouth. His cum hits the back of my throat and I almost start to gage. I quickly regain my composure and jerk him off with his cock in my mouth until he is done.

"Go ahead a swallow it Bitch. They're right you are real good at giving blowjobs but the job ain't done yet, swallow Bitch."

I swallow it and another guy shouts out I'm next. I crawl to the next guy with his hard cock in hand and this one is bigger than the last cock, but not as big as some of the dildos I have been trained on. I start to caress his balls as I start to swallow his cock. I waste no time sliding my lips all the way down his hard shaft to his balls. I hold my nose against his pubic hair for a second then I quickly pick up the pace working his cock and balls. He starts to moan as I suck him off. He also can't last long and shoots his load into my mouth. I hold my position on the head until he stops then I pull off and swallowed his cum which was much more salty.

Figuring I was blowing everyone in the room I looked up to see who was next and notice by now all of the guys are naked and some are lightly stroking themselves. I felt a tug on the chain from my left so I backed up being led by the chain. I until I came in contact with the next guy. I turned around to see a much larger cock that I think might be a challenge to swallow it all. As I reach for his cock he tells me to take my time because he wants to last longer than the last two guys.

I first suck on his balls for a few seconds then run m y tongue all the way up his shaft to his head. I swirl my tongue around his head a bunch of times before I lightly kiss it. I play with his balls with my left hand as I grab the base of his shaft tightly with my right hand. I give a vibration motion with the hand I holding his cock with as I tease his head with my lips and tongue. By his sounds and the fact he puts his hand on the back of my head I'm guessing he can't take much more of what I am doing. He pushes my head down his shaft and I open my throat as much as I can. I surprise myself and everyone who is watching how I take all of is cock into my throat. I hold it for a few seconds before I slide back up his shaft. He lets go of my head and I go back to the teasing I did before. This time I jerk the bottom of his shaft and I alternate from teasing his head and working my mouth up and down. I let go of his cock with my hand and swallow him whole again. I start slowly sliding all of the way up his shaft giving a little tease at the top, then all the way back down. While my left hand caresses his balls I use one finger to tease his asshole. This starts to push him over the edge and I feel him tense up. I slide back up his shaft at jerk him off as go back to teasing his head with just my tongue. He shoots his load and some goes into my open mouth and some hits my face. I reposition my mouth to catch the rest for his cum. I milk the rest of his cum out with my hand onto my tongue before I swallow. Then I kiss his head and as I smile at the crowd I realize from my training and tasting my own cum for so long, not only was this not so bad, I'm actually licking it. I even notice I am getting the warm and spacey feeling I get when my Mistress teases my and makes me horny.

"Look at the smile on our little slut. I knew from the video she was a natural at sucking dick but it seems she really loves it too. Before you swallow my dick I want to see what those tits look like. "

I cross my arms and reach down to the hem of my dress which is half way up my waist by now. I grab and slowly pull the dress over my head and drop it on the floor. The fake breast my Mistress had adhered to my chest are real expensive and look pretty real. Everyone starts whistling and complimenting my boobs. The guy who asked me to show my tits walked up to me and so did another guy. Now I'm on my knees with two medium size cocks in front of my face. I grab both cocks and start to stroke them. I kiss the one to my right and then start to suck the one on my left. I work my lips down until it meets with my hand which is sliding up his cock. I jerk off the cock I'm not sucking and after a few minutes I switch cocks. Both guys are enjoying what I am doing to them, but I am starting to get into sucking these guys off. I didn't think it would be this way but there is a feeling of power controlling when a guy cums with your mouth. The guy to my left starts to cum while I'm sucking the guy to my left. His cum hits my cheek so I quickly switch cocks to finish him off with my mouth. He finishes cumming and steps away.

I go back to the cock on my right and another guy walks up to my left. At this pace I will finish all of them off in no time. I continue sucking two guys at a time for awhile. I now have cum on my face, in my hair and dripping onto my chest. I think I'm done until I see four guys with cocks that look like they are in the twelve inch range looking at me.

I'm ordered to crawl up to the first large cock. I grab the base and start to take my time by wrapping my lips around his head. I tease it for a minute and try to open up my mouth and throat as much as possible. I try to take as much as possible but I can only go but so far down his shaft. He grabs the back of my head and starts to take control sliding my head up and down as he slowly thrust his hips back and forth. He has complete control as he fucks my mouth. The feeling of power is gone and as he makes me gag, so is the enjoyment I was having. Everyone makes fun of me every time I gag and the humiliation is rushing back like a tidal wave. He does not go very fast but he makes his cock go further down my throat than any dildo I have taken. I'm pushed to my limit and he picks up the pace. In no time he is fucking the hell out of my throat and luckily he does last very long before he cums. He continues to fuck my mouth as he cums so his cum is running out of my mouth as he finishes.

He pulls out and he next big cock steps right in. I barley have time to catch my breath before the next cock is fucking away. I'm just praying these last three guys finish fast. I never thought a cock could go so far down my throat. This guy and the next guy do the same thing. Fuck my mouth quickly and deeply and cum hard. I take a quick breath and open up for the last guy. To my surprise he puts the head of his cock in my mouth and stops. He tells me to swallow as much as I can and if it is not enough, then he will make the other three guys seem like a party. I grab his ass, close my eyes, open my throat and pull him into my mouth as I force my face towards his balls. To my surprise my lips go very far down his cock. I guess the fucking I just took, got my throat use to being opened more than before. I worked him in and out taking as much as I could. I guess it was enough because he never took over control. I felt the control facture coming back and a bit of pride that I was swallowing so much cock. I picked up the pace and worked his cock like a pro until he started cumming. Just as he started, he pulled out and shot his load all over my face. When he stepped back I looked up to see there were no more cocks to suck. I sat on my feet and lowered my head.

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byTrinni69© 0 comments/ 75060 views/ 12 favorites

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