Date: Mon, 4 Jul 2011 14:20:59 -0700 (PDT) From: Smith Smithy <smithsmith2332 (at) yahoo (dot) com> Subject: Meeting with Master (M/teen cd/tg, BDSM) So it's been a while since I wrote a story... I've started a few but haven't been able to finish them, but for some reason I just had to get this one done and written. It features graphic sex between an adult and a minor, as well as BDSM, and a wonderful transgendered narrator. If you're bothered by these things, your more than likely a prude and why the hell are you even here to begin with? Also, it shouldn't have to be said, but just in case: this is fiction, the only place where everyone really is safe, sane, and disease free, so please don't meet with strangers from Craigslist. Very little good can come from that. Also, please don't steal my story. It's mine and I like it very much and I wouldn't be happy if you took it. I love, love, love hearing from my readers: smithsmith2332 [at] yahoo.com Please send me love, hate, feedback, criticism, comments, or whatever you feel like. In the end, I just like knowing that people read my story. Alright, I'll shut up now, so unzip your pants, grab a tissue, and let's begin. Kisses, Sara Meeting with Master Master finished rubbing baby powder onto my right legs as I was finishing the lacing of the black thigh-high rubber boot on my left leg. As I started on the right boot, he left to grab the rest of my ensemble for the night: a black rubber top with long sleeves that ended in gloves and a bottom that tapered into four garter clips, which I attached onto the tops of the boots. A pair of false breasts under the top rounded my shape out, giving me a cute little pair of B-cups, made more exaggerated by the red and black rubber corset that Master then tied me into. The outfit left things open for a pair of panties, but Master had other ideas for tonight. He secured my wrists behind my back with a pair of leather cuffs before opening a box and revealing the last three items: a blindfold, a ball gag, and a chastity cage. He had shone it to me once before, telling me then that he had plans for it and me, but until now I'd never worn it. Needless to say, I was pretty excited from the sexy outfit that I was wearing, so he wisely had a pair of ice cubes ready to cool me down. He slid my now limp sissy cock into the cage and locked it shut. I was nervous about this, but by this point I trusted Master and knew he would keep his sissy plaything safe. He ran his finger around the edge of the cage to make sure it was tight but not pinching me before looking right into my eyes and kissing me softly on the mouth. "Thank you, daddy," I said as he pulled away. "You're very welcome, Jessica," he said with a grin that promised a fun night to come. --- I met Master through a Craigslist ad, of all places. He posted it, looking for a special sissy just like me. The title of the ad read: "Looking to explore your sissy side? Need a little discipline in your life?" It went on to discribe everything he was looking for: a submissive boi who was curious about being a sissy slut for a master/daddy, BDSM, nipple play, CBT, piss play, diapers, rubber, plastic, leather, heels, toys, and anal play. To name a few. "Chubby or skinny, blonde or redhead, young or old, it doesn't matter, so long as you want to have fun and explore your limits." I shot off a reply e-mail right away. I was nervous, of course, especially because I was only 16 at the time. My mom knew and supported my crossdressing, ever since she caught me trying on my old sister's panties when I was eleven. We had even talked about how I wanted to live my life and we decided that it would be the best for everyone if I transitioned into a full time girl before going to college. Despite all her love, I didn't think she would be as supportive about me hooking up with a random dom that I met online—still, this was something I needed to try, to submit myself to someone, to give up control and become a toy of mutual pleasure. And it's not like I wasn't careful about it: we corresponded for almost a month, sharing fantasies, ideas, and eventually photos of ourselves, before agreeing to meet at a coffee shop in a mutual side of town. At sixteen, I knew people would try to take advantage of me. So I was very careful to find one that would do it the way I wanted. He was tall, at least six-two, around 50, with chestnut brown hair, a thin little goatee, and just a little bit of gut. He wasn't the most attractive guy in the world, but I wasn't going to him for his looks—besides, I wasn't any beauty either. Five-six, short for a guy but tall for a girl, chubby with red hair. We chatted for a bit over our drinks, keeping our voices low in a corner booth. After about fifteen minutes, he said he was going to the bathroom and that I should follow in the next five minutes if I wanted to prove my desire to be trained. I was all I could do not to jump up and run in right then. The bathroom was a single unisex room, so I waited a few minutes, and luckily the place was pretty empty, so no one saw me slide in with him still in there. He locked the door and taught me the first rule when playing with him: any time he kissed me on the lips, I would reply "Thank you, daddy," otherwise I would refer to him as Master and address him as Sir. He then sat down on the closed toilet, pulled the bag he had with him close and motioned for me to drop my pants and lay across his lap. As I said before, my mom is quite supportive of me being transgendered and encouraged me to dress and be a girl after school and on the weekends when I was at home. Out and around town like today, however, I didn't risk it and was wearing boy jeans, which worked great to hide the panties I was wearing. I'd been wearing panties full time since my last stint of required gym class—and though my body hair was pretty light, I'd also been shaved from the neck down since then as well. I wore a bra fill with false breasts at home as well, hoping to get a real set of my own boobs once I started taking hormones in my senior year. Master complimented me on my pretty yellow panties, hipsters with a cute bow above the crotch and a little seam up the back that cupped my ass. I lay down over his legs and he caressed my ass gently, complimenting its roundness and saying how he was so excited that a bigger girl answered his ad. He pulled a decent sized butt plug out of his bag and rubbed a little lube onto it. I wasn't any stranger to playing with my ass: mom knew that my sister and I were young, horny girls and that we would need a way to relieve our selves, which is why we each got a ten-inch waterproof vibrator for our fifteenth birthday. That toy was in me at least three times a week, often more. Mom didn't get involved or anything, but she was happy that I was happy and exploring my sexuality. Still, despite my experience with my toy at home, it still hurt a bit when he started to press the plug in. A girly squeak escaped my mouth, followed by a breathless moan as the plug slide home. Master stood me up, pulled my panties and jeans up, giving my now hard sissy clit a little squeeze, then kissed me hard on the mouth. "Thank you, daddy," smiling as I said it. "You're welcome, Jessica. You said you were free on Saturday, correct?" I nodded an affirmative. "Good, I want you to meet me at my home at 8 PM on Saturday. You'll be spending the night, so make sure that's okay with your mother. Until then, you'll leave this plug in except when you need to use the bathroom. You will clean it and reinsert it immediately once you're done. Remember, this is not only a show of servitude to me, but also a test for yourself. You're on the honor system, and it's up to you whether you want to really experience this life for yourself. Do you understand?" he asked as he handed me a piece of paper with his home address on it. "I understand, Sir," I said as I nodded meekly. My ass was stuffed with the plug, my sissy cock was rock hard in my lacy panties, and I knew I wasn't going to mess this experience up. --- My cock was already straining against the chastity cage as Master placed the ball gag in my mouth and the blindfold over my eyes. He led me over to the wall of the dungeon and quickly unlocked my wrists, brought them up and locked them into the hanging chains. A small push on my legs had them spread and soon I was chained spread eagle against the padded dungeon wall. "I'll be right back, my sweet," he said as he left me blind, mute, and restrained. I guessed about ten minutes passed before he was back, but I was already drooling around the gag, enjoying the tight corset and rubber against my body. If I could have, I would have been rock hard and leaking like a faucet already. I heard him enter the room, his rubber suit squeaking lightly as he moved. He reached up and grabbed the back of my head, released the gag, and roughly pushing me into him—right into his armpit, I quickly realized. He didn't even need to tell me what to do as I began licking deeply, inhaling his deep manly stench. It was intense, and I could only assume he hadn't showered for a day or two. My clitty was straining in it's cage. I serviced both his armpits, then his rock hard nipples. He slowly lowered me to the floor by releasing some slack in the arm chains. Flipping me over, I serviced his feet and legs next. I knew where this was going and I couldn't wait—my mouth and tongue worked up the back of his leg to his glorious hole. He was fairly hair all over, but he kept his asshole and his crotch shaved. I lapped egerly at his hole, glad I had a Master considerate enough to clean himself well with an enema. He smelled flower fresh and tasted great. Through the rubber I could feel his balls resting lightly on my chest, twitching ever so slightly. I'm sure he was loving this as much as I was, a thought that was confirmed as he started moaning softly. Less than a minute later, "Oh baby, I'm gonna cum all over your pretty rubber encased tits, oh baby!" He began to spasm, and I could only guess how many spurts of hot jizz he shot all over my chest. He rolled off of me to the side, both of us panting heavily but with big smiles on our faces. He released my arms and legs and helped me stand up before finally removing my blindfold. I was standing in front of the mirror when he did, giving me a good lock at my self: my long hair was all messed up, my face was red and sweaty, and my chest was covered in cum. Master grinned next to me, wearing a rubber suit that went from his feet up into a tank top. The crotch was zippered and he had just re-zipped it. Master gently placed his arm around me and said "Who is that beautiful sissy slut in the mirror?" "Me, sir." "And who does that sissy slut belong to? Who does she love and need?" "You, sir, my Master". He carefully scooped his cum off the rubber and fed it to me by hand. As he did, he told me that that was one of the best orgasms he had ever had, that he had cum without touching himself, and that I was an excellent sissy ass licker. I blushed furiously, his cum still in my mouth, knowing that he hadn't given me permission to swallow yet. He turned towards me and kissed me deeply, sharing his seed between us. "Thank you, daddy," I said obediently after he pulled away. He sent me into the bathroom to give us a minute to catch our breaths and also so I could fix my hair and make up. I quickly braided it into two pigtails and reapplied my lip-gloss. I've always looked young, but the effect of the pigtails made me look almost like a pre-teen—I knew Master would love that. I walked out of the bathroom to find Master next to his leather padded saw horse. I immediately lay forward on it, letting him lock my arms and legs onto the posts. The support in the middle pushed me boobs apart, and with all the layers I wore it almost seemed as if as if they were actually real and attached to me. He circled around me once, grinning as he playfully tugged my pigtails before he finally walked over to the wall and pulled down a simply black riding crop. He wasn't into this fake punishment junk that other doms did, inventing mistakes that I needed to be punished for—he spanked, whipped, and paddled me because we both loved it. The hot sting that the riding crop gave me made me feel alive, while the grunts and moans that I produced helped his impressive cock recover. The crop was set aside after a good number of strokes, only to be replaced by a flogger, which in turn was replaced by master's hand. He caressed my now bright red cheeks slowly before suddenly launching into a hard spank. He did this again and again, until the tears were flowing and I was screaming loudly with every hit. Finally the onslaught stopped, and Master walked around front, talking in a soothing voice like he was trying to calm a screaming baby. Which actually was almost exactly what I was by that point. "Dry those tears, honey, daddy loves you. Did you enjoy your spankings, sissy Jessica?" The tears had stopped but I was still blotchy and red as I nodded. "Good girl, I'm glad you enjoyed it. I bet your little clitty is just begging to get out of its cage, isn't it?" "Yes sir, I'm close to cumming and I want to play with my sissy clit." "Patience, my sweet. I'm going to check you, and if you're a good girl, we'll make sure you cum hard." I was a good girl: he reached down to my sissy pussy and immediately felt the plug nestled within me. This had become our tradition: every Wednesday we would meet at the same coffee shop that we first met at. We would talk about our play sessions for a bit and eventually make our way into the bathroom, where he would do two things: first, every week he would give me a gift of a new pair of panties. Every color and variety you could imagine—sexy red lacy thongs to girly patterned hipsters. Once he even gave me a pair of super tight beige granny panties—we both laughed at it, but I loved wearing them for him anyways. Secondly, just like our first meeting, he would plug me and order me to wear it until we got together to play on Saturday. I'd always spend the evening and the night at his house. Mom thought I had an overnight job, which I told her all the money went to buying panties. I hated lying to her, but I wasn't ready to tell her the truth just yet, so the lie would have to stand. The latest plug he had given me was a step up in size than what I was used to. It was quite difficult sitting through school without fidgeting from either the plug or my nearly constant hardness. Master grasped the base of the plug and slowly pulled it out, pumping it back and forth as he went and making me moan. It finally popped out and I could feel my sissy pussy gaping as it slowing shrank closed. He unlocked me from the horse and gently carried me over to the bed in the corner. He sat on the edge of the bed while I knelt over his lap. One hand was reaching around spreading lube on my already stretched hole while the other lovingly fondled my tits through the corset and top. Finally we were ready, and I grasped him at the base while slowly lowing myself onto his rock hard seven inches. The breath escaped my mouth in a slow moan as I impaled myself on his cock, pushing until I felt his balls on my still sore cheeks. I began slowly, pumping myself up and down on him, my chastity cage rubbing lightly across his belly. My arms were around his neck and our eyes were locked together as I rode him harder and harder. Since he was an older man and he had just cum recently, I knew it was going to be a while before he came again. I closed my eyes and flung my head back, enjoying the ecstasy that was being fucked by my Master. My cock was pinched hard in its cage when suddenly it fell off in two pieces. I didn't slow a beat as he showed me the quick release key that he had been wearing on a chain around his neck. We were both almost ready to blow, my sissy clit rubbing hard against his belly and his cock deep inside my pussy. Finally, I hit the wall and with a loud moan shot four great big loads all over his chest. That was all it took to send him over the edge and he pushed me down on the shoulders as hard as he could before emptying his cum deep inside me. We were both breathless as we came down off of our orgasms. I looked him straight in the eye before leaning in and kissing him passionately. "Thank you, daddy."