Author: Maid Jennifer
Summary: The day I was caught by my best friend and what he did to me. Then being caught by his mom while he was using me and what she did.
It all started when I was eighteeen and my best friend caught me doing something I should not of been doing. You see I have some fetishes that get me into trouble sometimes, one is cross-dressing and the other is exhibitionism. It really all started when I was really young playing dress up with my sisters and their friends, they seem always had me dress as a girl. I also really liked the feeling of their panties, bra and stockings on me. So I began sneaking my sisters clothes and wearing them under my clothes. One day I was feeling really naughty so I put on my sisters bra, panties, garters and stockings then stuffed the bra, then my own clothes and went for a walk. I ended up at a schoolyard near my house on the swings swinging, when I got more daring and removed my clothes leaving me just in my sister's clothes. I was swinging and rubbing my cock when it happened I was CAUGHT.
My best friend was watching until he decided to make his presence know by saying OH MY you like to dress up as a girl and a naughty one at that. I jumped up and started to run for my clothes but he tackled me and pinned me down. He was sitting on top of me with my cock pinned in his crotch, which was getting me really excited, making me hard and he knew it. Then he said if I did not do as he says everyone would know, I agreed and he got up.
Then he ordered me to crawl to him and remove his cock and suck him. I crawled to him and started sucking his cock enjoying the taste of his manhood and pre-cum. It took me 10 minutes before he started to cum with me swallowing the best I could, then before he finished Cumming he pulled out of my mouth and shot the rest all over my face and chest. He ordered me too suck him clean and make him hard again so he could use my pussy/asshole. He had me pull my panties down to my knees then bend over so he could fuck me and he did until he shot a big load in my pussy/asshole. He then ordered me to kneel in front of him dripping of cum and told that from now on that I was to do as I am told when ever and where ever I was, with no hesitation or I would be punished. He also said that I was to call him Master James at all times and to always answer him with yes master or no master, no matter where we were. He then gathered up my clothes and started to leave. As he left he ordered me to stay just like I am and wait for him to return, Yes Master James. He left and returned in about an hour just before dark. I don't know why I just stayed there kneeling waiting for him to return, but I did. He came up and said look at the slut dog then produce a collar with a tag that read Master James slut dog. He ordered me to remove the rest of my clothing because dogs don't wear clothes and he put the collar around my neck. He then put my clothes in a bag and hooked a leash to the collar and lead me to his house with the bag in my mouth and me on all fours with the dried cum on my face and chest. On the way we ran into a friend from school. She was out walking her dog and when she saw me her jaw dropped open in shock, then started laughing. When she stop Master James and her started talking while her dog started sniffing around my ass and licking which made my cock hard. They noticed me and started laughing again saying look your dog is a faggot dog he gets excited by a male dog licking him. Her dog had is cock coming out of it's sheath and they made me lick and suck on it. She then pulled us apart and said we will let them play tomorrow and she left.
My master and I made it the rest of they to his house with no further incident. When we got their he took me to his back yard and bathed me and gave me a cold enema using the hose. When he was finished and I expelled all the water he had me suck him until he was hard. Then he fucked my pussy/ass filling me with his cum and piss, when he finished he quickly pulled out and replaced his cock with a plug that he could lock in position and I could not remove. He then led me over to a dog kennel that was barely big enough for me and put me in it for the night still full of his piss and cum and left. There I was full of cum and piss, in a cage wishing I could release the liquid that was in my ass and relieve the cramping that I was feeling. It took a while but I finally fell asleep.
The next morning I was awaken by a warm fluid hitting me in the face and when I opened my eyes it was Master James peeing on me, when he saw I was awake he ordered me to open my mouth and drink the rest of his piss. He then pulled me from my cage and released the straps holding the butt plug in; he then pulled the plug out and let the fluid flow out of me. Next he cleaned me up and told he had a special day planned for me, just then the gate opened and in walked the girl and her dog from yesterday. She asked if she was she was ready and Master James said yes she is the girl then brought the dog over to me and ordered me to lick the dogs cock and balls until he was excited then get ready for a good fucking.
They helped the dog get his cock in me then sat back to watch the show. The dog was going at it for about twelve minutes when I felt him swell and release his cum in me burning my sore asshole. When he was done he tried to get off of me but his knot was wedged inside of me so he could not pull out of me. There I was being pulled around the yard by this dog while Master James and the girl were rolling around on the ground laughing, just then a car pulled into the drive way. It was my best friends mother, the look on her face went from shock from seeing me attached to the dogs cock to anger of what was going on in her yard. She said WHAT IN THE HELL IS GOING ON HERE!!!!!!!! Her son started to explain when the dog finally slipped out along with some cum. Her son finished the whole story and I begged her not to tell my mom, she said she would think about it. She told her son and the girl to strip naked and clean me up. When done all three of you come into the house where I will be waiting.
So they gave me a bath just like a dog and dried me off, master James then put the collar back on me then the leash. He then surprised me by producing another leash and collar; he then put it on the girl and led us both into the house to where his mom was waiting for us. She immediately told James how bad he was for doing the things he did and said you need punishing but first your friend's names so I can call their mothers. The girl and I immediately started to begging her not to call our moms saying we would do anything she wanted no matter what it was, she said anything with a evil grin on her face. She order her son over her lap with his cock clamped between her legs, then began spanking his butt with a riding crop leaving red welts. She kept it up until he shot his load on her legs, all the while asking us questions. She asked me to tell her all that had happened since she had left the day before, I recounted every moment for her in detail. She then pushed her son to the floor and told him to get on his hands and knees with his butt in the air. Now for you two aim now Mistress Wendy and you Carl will be slave Jennifer since you like being in women's clothes, and you Amy will be slave Amy. She then ordered us to lick her sons cum from her legs, slave Amy and I took one leg each and started licking all the cum off and working are way up to her pussy which was very hairy and smelled of urine and sweat but we kept licking until she order me to stop and go fuck her son. I immediately stopped and went to her son and shoved my cock in his ass. I started slowly at first then began to pick up speed while watching slave Amy licking Mistress Wendy's cunt. Mistress Wendy and I came at the same time she coating the face of slave Amy and me filling her sons ass with my cum. She then ordered slave Amy to go get the butt plug and me to also pee in his ass. When slave Amy returned she had me pull out and then slave Amy put the plug in and lock it into position. She then ordered slave James to clean the house while we went shopping, but first she had slave to go to the bathroom. We licked her clean and she was satisfied that we did a good job she threw us two t-shirts and two pair of shorts to wear. My shorts were way too small and show my bulge off very well, slave Amy's clothes were the same way and showed her breasts and dark bush under her shorts and t-shirt quite well. She then said lets go to Amy and I, then ordering slave James to have the house cleaned by the time we get back. We went out and got in the car and we were off.
First stop was the beauty salon, when we walked in all eyes were on us for the way we were dressed and that Mistress Wendy basically announced why we were there. She said he needs to have his entire body waxed, then his eyebrows plucked, nails done, and then taught how to put make up on. Then she said Amy needs waxing, nails, hair and make up. The beauty shop owner called two of her girls up and instructed them on what needs to be done. They said follow us and we did to the back of the shop then we were told to strip naked, we hesitated so two other girls came over and did it for us and for not obeying our mistress let each of the four girls give us five swats each in plain view of all the women in the shop.
After the swats they proceeded with the waxing not even closing the curtain to prevent everyone from seeing us being waxed. When we were done they took us to the massage chairs for a pedicure and nails. At the same time they plucked my eyebrows to look more like a female. Then my girl took to her chair and showed me the proper way to put on make up. So now that we were all done and made up they gave us back our shorts put not our shirts instead they gave us two blouses with no buttons so all we could do is tie them at the bottom. Then we were off to the next stop Victoria's Secret.
When we arrived there the salesgirls looked at me and started laughing, saying what is he suppose to be a girl or a faggot.
Then my mistress went up and talked to them. She then ordered me to do anything they say and left with Amy. The head sales girl then ordered me to the back of the store to where the 3-way mirror was and strip naked for them. There I was standing naked in front of the mirror being inspected by the girls. I was then ordered to stroke my big clit, so there was jerking off in front of that mirror for all to see while the girls watched. It was actually exciting me standing there in front of the mirror and them jerking my cock that I shot my load rather quickly. They then went and got me some things to put on. They brought back black seamed stockings, garter, bra and matching panties. I put them on; just then a nice looking black man walked into the store and saw me. He acted as if he did not see me but kept looking my way, one of the sales girls asked him if she could help him and he said yes. He was looking for something for his girlfriend but kept looking at sizes that would fit him. So they figured it out and let him know it was all right and that they noticed him eyeing me in the back. Then they asked him if he would like to use me, he said yes and followed them back to where I was.
He then ordered me to my knees and pulled out his cock, it was huge at least 11'' and 3'' across. He order me to start sucking it I did slowly at first the faster and as much as I could get in my mouth. I was sucking him for about 10 minutes when he shot his load down my throat and in my mouth, I had no choice but to swallow all of it. The girls said look at that cock sucking whore and then the first girl ordered me to eat her so I started to and the other two were getting the man hard again. Soon as he was hard I felt him shove his cock in my ass. It hurt like hell but no one could hear me scream because my mouth was on the first girl pussy. I ate her pussy until she orgasm then the next one took her place all the while he was fucking me in the ass, then third girl took her place and they came together just as my mistress walked in the store with slave Amy. I turned and greeted Mistress Wendy still kneeling on the floor. She then hand me a maids uniform for me to put it on, I started to reach for my panties but she said no panties whores don't wear panties. Then slave Amy dressed and she gave us both 6'' stiletto heels to wear. She paid and thanked everyone then we left. It was hard walking in the heels but some how I managed to make it clear across the mall and out to her car. When we got there she informed me that she could not have me getting cum that was dripping out my ass and down my legs on her car seats so I would have to walk home.
On the way home from the shopping trip
As you remember I was left at the mall parking lot to walk two miles home to my mistresses house, So there was nothing left to do but start walking. Whistling, rude comments and verbal abuse greeted walking across I. Finally I reach the street and started toward my mistress's house too much of the same. I had cum dripping from my ass and down my legs. I had gone a few blocks when this big black limo pulled up and rolled down the window, then this beautiful black female chauffer asked me how much I told her I am not for sale ad she pulled away, but to return at the next block to ask me again. But this time the phone rang and the chauffer answered it and said it was for you, I took the phone and answered it, it was Mistress Wendy, she told me to do what the chauffer says and to tell her 10,000 dollars. The chauffer said ok and hung up the phone.
The chauffer got out and came around to me, she said ok now remove your dress, I hesitated and she said it again with a stern voice this time that scared me so I did. There I was standing on the sidewalk in just garters, stockings and stuffed bra for all to see. She then opened the limo door and there was four men sitting inside all naked. I was told to get in and do whatever they said. So I climbed in and kneeled on the floor limo, one if them said look at the cunt already knows her place. Then one order me to start sucking, I did making it as good as I could while the other played with my ass and cock. Just as the first guy was Cumming in my mouth one of the others shoved his cock in my ass. This went on for a few hours until every guy had cum in my mouth and ass twice. Then a voice came over a speaker saying ride is over and slave remain in the center of the limo just as you are. The men dressed and the limo stopped and they exited. Ten minutes later two of the most beautiful black women entered the limo wearing the sexiest leather out fits ever. I just sat there staring at them and their lovely legs almost in a trance like state until one spoke saying "What are you looking at CUNT" I snapped out of my trance and started to apologize, but they cut me short as one of them pulled out a short riding crop. She then ordered me to show her my ass and proceed to whip my ass leaving nice red welts while she had me explaining what I was doing looking at them in that way until she was satisfied that I would not do it again. I was then ordered back to the center of the floor and that is when I notice the door of the limo was still open and a crowd had gathered, then one of the ladies ordered me to get out and show them their handy work. When I exited the limo I noticed two naked black men kneeling at the side of the limo, but before I could study the situation too long the limo driver grabbed me and spun me around then bent me over putting my head between her legs and clamping down tight. Then she had me spread my legs wide apart and proceeded to whip my ass and balls. The whip was flexible enough to lay right thigh my ass crack and hit my balls. She kept whipping my ass and balls until I actually shot a big load of cum on her shoes. She got mad and made me lick them clean right there on the sidewalk in front of everyone, she then put collar and leash on like the black men had on. Then we were led into limo first one black man, then me, then the other black man. I finally got a good look at them and man were they hung one was 10'' and 3'' across and the other was 12 '' and 2'' across. Then one of the ladies said look a Oreo cookie but there is one thing wrong with it and ordered spike to put is 12'' in my ass which he did with one swift push causing me to scream in pain. Then she ordered rex to put his 10'' in my mouth to keep me quiet as the crowd applauded. Then the door shut and we were off to who knows where while I was being fucked from both ends
It was about 15 minutes when first rex flooded my mouth with his cum and right after that spike filled my asshole. They then switched positions and filled me up again. When they were finished they were ordered to fill my ass with a Tabasco sauce enema, when it started flowing in, it burned like hell so I was screaming so the put a penis gag in my mouth. Once I was full they put in a 4 x 4 butt plug in to hold it in my ass. Then the lady's got on the phone and talked to the driver and a little while later the limo came to a stop. Then about 5 minutes later the door open and I was ordered out so I crawled out of the car to see that I was in an empty field over looking the city. There was also a blow up pool set up and I was ordered into it and the butt plug was removed, and then was allowed to expel the burning liquid from my ass into the pool. Then I was ordered to lie down in the pool and was tied spread eagle. The two ladies then inserted two enema tubes in their slaves Asses and proceeded to fill them up while they shit on me and pee in my mouth. When they were done they made me lick them clean of all the shit and pee. Then they had the two slaves stand over me facing each other and start peeing as they were doing that, they released their enemas all over me. Once they were done I had to clean them up too. Then the driver said it was time to take them back to the hotel and that she would be back for me soon and they all left with me lying there in the shit and piss. There was lying their exhausted form all the abuse unable to move until I finally fell asleep.
I don't know how long it was before I heard a car coming up the road but the sun was just starting to come up when it pulled up. It was the limo and the driver got out and untied me then helped me clean up. She then wrapped me in towel and helped me to the limo and laid me down on the floor and shut the door. Off we went and soon I was asleep again, I slept until the door open and she helped me out and into the huge house. We went straight to the bathroom where she had me shower while she filled a Jacuzzi tub with hot water. When I was done with the shower she told me to get in the tub and close my eyes. She then slides into the tub next to me and that is when I notice just how gorgeous this black lady was sitting next to me. When caressed each other and kissed. It felt so good that I was in heaven, I was really enjoying myself when I reached down and found a huge cock between her legs, my heart skipped a beat and she knew what I found and asked me if everything was alright? I said OH YES a dream has come true. She then asked me what was that, and I said to be a slave to gorgeous black women, man or as in your case a transsexual. She said so you like this, I said very much so. She said good because I am now your mistress and that 10,000 was to buy you from Mistress Wendy, but I want my slaves to stay here because they want too not because of being forced too. I responded by saying I would love to serve you MA'AM! She said well now lets get out and dry off and tonight you will sleep in my bed with me. Then tomorrow we will discuss the rules and contract you will have too sign, I responded bye saying yes Mistress. Off to bed we went falling asleep in each other arms and me feeling so safe knowing the she was going to take care of all my needs.