Transvestite gets blackmailed

I was just a girl cruising the tinder for her master. Well I wasn’t a girl at all; I was a guy in drag… I advertised on the Internet as a novice TV looking for a master. I got much more than I ever bargained for.

I have been cross-dressing since puberty. My friends and I lived near a college, and one day we found a pair of panties on the ground near a dormitory. My friends tossed them around and made up stories about how they got there. The stories they made up had my young mind on fire with fantasies. Later that evening, I returned to where we had left the panties, I pretended to walk along and I casually picked them up and put them in my pocket. I was terrified that someone would see me touching a woman’s panties. When I got home I was overwhelmed by the desire to examine them. When I pulled them out I realized that they had a distinct smell to them. As I touched them I was overwhelmed by how soft and smooth they were. I was overwhelmed by the desire to feel what a girl felt when she was wearing panties.

I undressed and slowly pulled the panties upward… As I stood there wearing the panties I looked into the mirror, my little penis got hard as I stared at my self in the mirror. The panties were a silky yellow nylon, and they felt incredible. I started touching my cock through the silk and I felt a strange sensation. I lay down on the bed and kept touching myself; a weird feeling was coming over me. I had never felt this way before, as I touched myself, I thought that I might pee myself. I didn’t care if I would pee; I just wanted to keep doing this. I suddenly let loose with what I would soon realize was my first orgasm!

I had always liked girls; I was completely humiliated to realize that I had my first orgasm dressed like one. As I reflected on this situation, I wondered what it would be like if someone caught me dressed like this. What would my friends do if they found me all dressed like a girl, getting off on it? Perhaps they would just see me as a slut needing what a slut needs. Perhaps they would make me be like a girl, holding me down, pushing their cocks in my mouth…

I had a lot of fantasies like this. I began trying to steal girls’ underwear. Once when I was staying the night at a friend’s house, I idly looked in his hamper. Right on top I found his sisters underwear. But it was different than anything I had seen before. Most girls our age wore white cotton briefs and bras. My friends’ sister however, was older by five or six years. What I found in the hamper were definitely sex clothes. I found a black bra and bikini panties, along with a garter belt and stockings!

I decided to steal the panties, but I just had to put all the clothes on. I was shaking from excitement and fear. My friends’ sister was a tall athletic woman, and her clothing fit me snugly as they went on. I smoothed the stockings up my legs first, followed by the garter belt. Then came the panties, I thought I would pass out as I pulled them up. As I put on the brassiere, I looked in the mirror; once again I was extremely excited to see a slutty girl. I took some socks out of the hamper to complete the transformation.

I don’t know how much time transpired, but suddenly someone was hammering on the door! “C’mon dumbass I need to go”! Shouted my friend. Oh my God, I was caught, I realized that I was standing in my friends’ bathroom in woman’s underwear. I freaked out as I tried to pull everything off at once. The panties were fouling everything up by being on the outside. I yelled to my friend to hang on, as I tried to get my clothes on. My friend must have heard my struggles, as I tried to switch my clothes he said, “what are you doing jerking off”? I finally finished dressing and opened the door. Luckily, he did have to go bad and didn’t notice my mortification. I did notice his sisters’ underwear hanging out of the hamper though.

As my friend pissed, I realized that I wasn’t wearing my underwear at all, I was still wearing panties! In my haste to unhook the garter belt, I had left the panties on! My friend finished and joined me in the hall, teasing me about my red face, certain that I had been jerking off. I was freaking out in my head wondering where my underwear had gone. I decided I would wait an hour to go back to the bathroom. After an hour I went and retrieved my underwear. I changed very quickly so that my friend would not come looking for me. I was afraid he would see the small lump that his sisters’ panties made in my pocket…

I was very careful for a long while after this. My brother knew I dressed but didn’t ever bring the subject up. One day he got a baby-sitting job down the street. I was sitting home when he called me to come over. When I got there, he told me he wanted to show me something after the kids went to bed. He called me from the upstairs several minutes later. When I got upstairs, he motioned me into the master bedroom. He had been snooping and found a whole collection of marital aids in the underwear drawer of the kids mother. He pulled one big rubber cock out and said, “this is what you want, right up the ass”. I just stared; a he had never made reference to this before. I was stunned, but he had a big grin on his face, and I realized that he was joking with me. I held up a bra to myself and said, “yeah, I want to be your sex slave”. We busted out laughing and put the stuff away.

Two weeks later my brother was again baby-sitting for the same family; He told me to stop by if I was bored. When I got there another friend of his was already sitting on the couch. We watched a movie for awhile, until I said I needed to pee. I went upstairs and decided to detour to the bedroom. I went right for the under wear drawer. As I stuffed a pair of panties in my pants I heard the door open… “PUT THOSE BACK RIGHT NOW”!! Said a voice. It was my brother and his friend standing at the door. I almost peed my pants. My brother and his friend were laughing their asses off at me. I got really pissed and left to walk home, my brothers’ friend decided to come with me. As I walked I began to cry, I told my friend that no one knew about this, and he was nice about it and said that he wouldn’t tell anyone.

I had not heard a word until a week later, when my brothers’ friend called me on the phone. He was baby-sitting (different house) and told me to stop by. When I got there I found out that he wasn’t baby-sitting, he was house-sitting. He had me in and started asking me questions about my sexual fantasies. He told me to answer all of his questions if I wanted him to keep my secret. After he questioned me for awhile, he told me that he wanted to see me dressed as a hooker. He told me to go up to the bedroom and find some clothes to wear. I was shaking as I climbed the stairs. When I reached the bedroom I found the dresser of the couple who owned the house. I opened the dresser and was dismayed to find that the fat woman that lived here had ugly underwear.

My new friend came up behind me and was angry to find me still dressed as a boy. He told me that I had better get some girl clothes on fast. I whined because the fat woman’s didn’t turn me on’ clothes, He told me he didn’t care because this was about him! He told me to be ready in five minutes. I was very scared but I quickly put some clothes on. My friend returned, coming up behind me and rubbing his crotch on my ass. He had an erection and was rubbing it on my ass. He asked me what I would do to keep my secret safe. I told him that I would be his sex slave and asked him what he wanted me to do. He turned me around and told me to undress him. As I helped him with his clothes I could feel his cock rubbing against me

As I pulled my new masters pants off, he grabbed me lightly by the neck, forcing me to my knees. He told me that a good slave needs to suck cock on her knees. He held me down and told me to start sucking his dick. I started licking his dick, but found that I didn’t like the taste of his cock. I told him that I didn’t like this and wanted to go home. He slapped me lightly and said that it was time to get on the bed or else.

He told me to get on the bed and grab the headboard with my hands. When I had done this he got on top of my chest and straddled me. He started slapping me with his erect cock. He told me to say that I loved being a hooker, and that I wanted to suck cock. He told me to beg for his cock. He then started feeding me his cock. He told me to suck it down to the root. I kept gagging but he kept pushing it into my mouth. He would pull it out and slap it on my face, then continue to fuck my mouth. He started to push faster and grabbed my head in his hands, starting to fuck my mouth harder

He then told me to take one hand and grab his balls. He pulled his cock out and started yanking it furiously. He told me, “lick my balls slave”. His hand was hitting my face on every downstroke, as I licked his balls. He slid forward and suddenly his ass was on my mouth. He said, “lick it bitch”. His ass came down and was cutting off my air; couldn’t push him off because I had no leverage. So I started licking his ass. I only licked for a minute when he slid back and slammed his cock back in my mouth. He continued to jerk off as I sucked the head into my mouth. Suddenly he pulled out and started shooting his jizz all over my face! He covered my face with cream and blinded me in the process.

He was shaking with his orgasm, and started laughing saying, “you are one ugly whore”. He told me that he wanted to see me shoot, and that he wouldn’t let me go until I had. He told me that I had one minute to jerk off or he would fuck my ass. I tried hard to jerk off, but my eyes were burning and I was nervous so I couldn’t get off. He told me that I would have to get off like a girl, while I was being fucked. He told me to grab the headboard again. He took some of the fat womans nylons and tied my hands to the corners. After that he got a rag and wiped my eyes. He told me he wanted me to see again. He took the rag covered in semen and pushed it in my mouth. He told me he would be right back.

When my brothers friend came back in the room I saw he was holding some things in his arms. He told me to close my eyes. When he told me to open my eyes, I saw that he had a polaroid camera in his hands. My new master laughed as he took the first picture. He told me to look at him or the next picture would be me with the dogs cock in my mouth. He next took a bottle of lotion and squirted it on my stomach area, and took a picture. He told me to pull my legs back up to the headboard. My master then took a big handful of lotion and put it all over my cock and ass.

As my master began to work the lotion into my ass, I popped a fresh boner. Soon he was pushing his finger into my ass. He told me I really was a girl, because I got off by being fucked. He pulled the gag out of my mouth, and told me to beg him to fuck me. He began fucking me with one hand and stroking my cock with the other. I had never felt anything like this, I was shaking with humiliation, fear, and lust. As I started to orgasm, my master took his hand off my cock and grabbed the camera. He shot two pictures of my own jizz hitting me in the face as his finger fucked me. It looked like I was coming from the finger fucking only! My master told me it was lucky he wasn’t a faggot or he would have fucked my ass with his cock. He then told me he was going to leave me tied up for the couple that owned the house.

My master returned a few minutes later, and untied me. He told me that if I ever said a word, he would show every one the pictures he took. He told me that if he ever wanted me again that I would do whatever he said. I lived in fear of him for several years, though he never made me do anything again.

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