Date: Thu, 28 Dec 2006 14:51:40 -0800 (PST) From: bill bobber Subject: Getting Started - 7 Getting Started - 7 TG - Young friends Cross-dressing, Oral, Anal, Masturbation This story deals contains sexualy explicit scenes. Do not read if you are not over 18. Otherwise, enjoy. I knew that I had to wait for my first chance to dress up. I wanted to do this right and that meant my mom needed to be at work. She's a nurse and works nights sometimes. That wouldn't happen for another four days, but in the meantime I could get ready. So the next day after school I told mom that I'd gotten muddy playing football at school and needed to take a shower. After locking the door I stripped and just enjoyed the feeling of being naked for a moment. I love that feeling and would be naked all the time if I could. One day I'll have a place of my own and then I will be naked all the time, unless I'm wearing some sexy lingerie or perhaps a French-maid outfit (giggle!) After admiring my smooth young body in the mirror and checking out my pert teen butt (I know it sounds conceited but I do have a nice round little ass and I like the idea that men might find it sexy and want to get into it) I got mom's razor out of the vanity. I'd never shaved myself before but one good thing was that I didn't have a lot of body hair. Never-the-less, I wanted it all gone. So I began, slowly, carefully, enjoying the experience of preparing my body for a man to make love to. As I made my body more feminine looking I imagined that I was Jim's girlfriend and that we lived together. He would be home from work soon and I wanted to look my best for him. I would be waiting, all smooth and clean, wearing the sexy clothing he had left for me. Ready and eagerly anticipating the sweet love we would soon be making. I imagined him coming in and the happy look on his face as he sees me standing there in my heels looking like a hot slut. I would walk over to him, the way that walking in 4" heels makes you walk, and kiss him. Then, I would drop to my knees and free his beautiful cock from where it has been kept waiting all day for me. Looking up into Jim's eyes I would smile lasciviously before engulfing his long, thick cock in my hungry mouth. Then, I would please my man, who had been working hard all day and needed some relief. I had loved sucking Jim's cock and knew that I would not hesitate to taste him in my mouth again. In my imagination, after a vigorous blow job, I would taste my man's thick cum spurting into my mouth and down my throat. I wanted Jim to be my boyfriend so I couldn't imagine doing anything other that swallowing his seed. I wanted him to love me and I wanted to satisfy his needs completely. To do that I knew I needed to be the best cock-sucker I could, and to savour every drop of sperm that came out the end of my man's cock. It also meant, I was pretty sure, that Jim would be wanting to fuck me, maybe a lot. I was a little scared thinking about that, Jim did have a big penis. But there was no denying the fact that I was also excited. Jim had been gentle with me as he had shown me how to please him with my mouth. I knew that I could trust him to be gentle with me if he wanted to fucked me. And as I stood in the bathroom looking at my slender and now hairless young body, I knew I wanted him to fuck me. I wanted to do everything in my abilities to satisfy him. I wanted to be Jim's girlfriend and that meant giving Jim not only oral love, but also free access to my tight young ass. Two days later, mom worked a night shift. One of my older sisters had moved out by now to college and the other was out on a date and I knew she would be very late. I was going to be alone. I did my best to look calm and un-excited during dinner as mom reminded my for the millionth time to do my homework. "Oh yeah, I have some extra special homework to do tonight mom." Finally, the door closed and I was free to do, and look, as I pleased. I ran upstairs and took down the bag from the back of the closet shelf. I was naked in seconds. As I looked down at the wonderful outfit laying on the bed before me I felt my penis rise. I was so excited! First it was the stockings. It took some practise and patience getting them on but I didn't mind because it felt so wonderfully girly pulling on stockings. Next was the garter - it was easier, once I figured out which way was the front. I fastened the snaps and smoothed out the stockings. I already felt fantastically feminine and so sexy. I just stood in my room and fondled my penis for a few moments overwhelmed by the erotic sensation of transforming myself into a girl. Next was the bra. It was padded so it looked like I had breasts. Getting the fastener to work was tricky at first, but I soon got it. I reached up under the bra and squeezed one of my nipples which sent shivers up and sown my spine. Now the shoes. I had been looking forward to these perhaps most of all, but I was also kind of afraid of them. They were very exciting with such high heels and the straps that wound around my leg, but I had no idea of how to walk in them. I almost collapsed the first time I tried walking. This was hard! I felt all wobbly like I was going to fall over at any moment. How did women walk in these things I wondered. I stood in the middle of my room and teetered from side to side as I tried to figure it out. I soon found that if I held my arms out like I was walking a tight-rope that it was a bit easier. So I practised like this for a long time - walking as back and forth across the room, arms straight out to the sides, trying to walk as much like a woman as possible. Soon, I began to see the upside of high heels. First, they made my legs look really long and my calf muscles were tight which looked good. They also did something to my ass which was really thrilling. I don't know what happens back there when you've got heels on but it seemed to make my ass really look like a girl's, all round and pear shaped. I spent quite a bit of time fondling my smooth butt cheeks while imagining it was Jim that was feeling me up. What a little tart! Finally, heels made me walk sexy. Not graceful, but totally feminine. As I watched myself in the mirror, transformed into a young slutty-looking girl, I was perhaps most excited by the way I walked. Or strutted, I should say. It took a lot of practise, but I was enjoying every second of it. Learning to swing my hips, swivel my ass, how to balance on my toes while I walked so all this motion looked coordinated and sexy. Quite a bit of practise. The last piece of the outfit was the wig. Long and blond, the hair hung down past my shoulders. It didn't smell very good, but not gross, just not pleasant. The effect on the image I saw in the mirror was remarkable. Instead of a young man dressed like a young woman, I now saw only a woman. Sure, a tarty looking young woman who was still wobbly in her heels, but there was nothing masculine left. I posed and twirled like a slutty showgirl in front of the mirror imagining I was putting on a show for Jim. I was also getting more and more aroused and needed to do something about that little thing sticking out from where my pussy would be if I were a woman. I knew it was time to play with the other items that Jim had given me. The two dildos and the lubricant were hidden under my bed. I know, not very original, but I had been playing with them at night before I went to bed. I enjoyed sucking on the smaller of the two because it was sculpted to look and feel very much like the real thing. I would stroke my cock as I imagined that Jim had come in my bedroom window and needed to have his balls drained by my eager young mouth. I would orgasm imagining that the pulses of cum erupting from my cock were really shooting from Jim's big dick into the back of my mouth while I slurped and slobbered on the lucky dildo. The bigger one was more firm and had a fat head that led to an almost equally fat shaft, that had to be at least 10" long. I hadn't done much more with this one other than kiss and lick it. It was too big to comfortably suck on. This one, "Big Daddy," I had been saving for tonight. It would be deep in my ass before the night was through, I vowed. I needed to be ready when Jim wanted to fuck me and this monster was going to be the one to get me prepared. Or I would just fuck myself silly; either way it was win-win. I moved the mirror so that I could see myself on the bed, then, with my two latex lovers and the tube of lube I lay back against the pillows and spread my legs. I began by inserting a finger into my rectum. Mmmmmm. I had been craving the feeling of something right there. Something in me. Something in my bum. Ohhh! It might only be a finger but it felt so good! So right! I was sure that I wanted Jim to fuck me and I wanted it to be wonderful. With one hand stroking my rigid cock I began finger-fucking my horny hole. I felt so incredibly slutty! Dressed like a young hooker, finger up my ass, a young man crazed with lust as he imagines being used by an older man for his sexual satisfaction. Shameless! Yup, I felt no remorse. Only a growing need to be used completely by Jim. To be fucked and fucked until I was filled with his cum. Oh! I was so horny. It was time for the lube. I took my time coating the tight opening of my anus with the slippery stuff because I was getting a little overheated. I wanted this to last and if I kept up that kind of pace I would cum too soon. I gently eased two fingers into my love hole. I had to go very slowly because my sphincter was fighting to close. "Come on now," I tried to tell it. "You want to be part of Jim's girlfriend don't you? We want to be Jim's girlfriend. That means he's going to (hopefully) want to slide his big fat cock up inside you. You need to let that happen. Surrender, don't fight it. Let it in. Let him take you and fill you." It must have worked because it stopped hurting and I began to feel pleasure as I sawed two fingers in and out of my slippery rectum. I enjoyed doing this for several minutes before I felt I was ready for "Junior." This was the smaller of the two dildos. But it was still a lot bigger than two fingers. More lube, more pep talk, and then I was ready; pressing a cock shaped dildo against my poor little rosebud. My legs were pulled up against my chest, knees wide apart, ass cheeks spread open as I gently but firmly pushed the dildo up my ass. There was pain, but it didn't last long and it was a good kind of pain. Before long I had the entire length of the phallus inside me. I stroked my cock as the wonderful sensation of having something big in my ass washed over me. I almost came right there, but was careful to stay in control. I carefully got up off the bed and stood looking in the mirror. I loved what I saw. A sexy hot tramp who had a dildo in her ass. I looked at the garter, the long stockings, the very high heels, the padded bra, and the long blond hair and I nearly came again. I slowly began do do a sexy dance wishing that Jim could be watching me. I loved the way the dildo felt in me as I moved. I loved the feeling of being full. I turned so I could see my ass and the dildo sticking out of me. It looked so big! My ass looked good being fucked by the thick phallus, like a girls. I hoped Jim would think it looked sexy too. Now it was time for "Big Daddy." My anus had become used to "Junior" and it was time for more training. I climbed onto the bed on my hands and knees and slowly and gently pulled out "Junior." With a wet sounding "slurp" my latex lover left my ass feeling empty. But I wouldn't be for long. I had "Big Daddy" ready. And more lube. I placed the big dildo behind me with the huge tip against my already stretched anus. Pausing to admire the view in the mirror of a young horny boy/girl preparing to fuck herself I then began to lower my ass onto the dildo. I'll spare the details. It took some work and a bit of pain but I had lube and more importantly, the desire. And after only a few more minutes I had the biggest dildo I had ever seen deep in my ass. I leaned forward on one arm and with my other hand began to stroke myself. I was almost beyond the point of control now. The view in the mirror, the anal sensations, and the knowledge that I was being impaled by a monster cock was driving me crazy with lust. I loved how my ass felt and loved imagining Jim was behind me on the bed fucking me deep and strong. I bucked my hips back at my imaginary lover fucking myself against him letting him know I wanted it as much as he did. I loved feeling like a hot young slut crazy for men's cocks and cum. I loved how I looked all dressed up in order to please my man. I wished I had a man with me right then to teach me all night long how to fuck and swallow cum. I thought about how many men there probably were right now all over the country who would love to find a horny and willing boy to be their sexual plaything. How wonderful it would be to have one, or two, or even more, suddenly appear and be as happy to see me as I would be to see them. And then we would be able to make our fantasies come true. Mine, of being able to please a man (men?) sexually, and theirs, of finding and fucking a hot and horny young boy/girl. It was too much to handle. I came. Hard. Face down, ass in the air, monster dildo sticking straight up, cum all over the sheet below me, I shot and shot and shot until my release was finally complete. Afterwards, I didn't have the strength to move for quite a while. I just revelled in the "just been fucked" feeling, wishing it were a real cock that had fucked me. I reluctantly pulled "Big Daddy" out of my ass. I felt all wiggly and loose. But I was already beginning to feel horny again. My ass felt empty and I didn't like it. I wished for the millionth time that Jim really was with me. I would gently suck him until he was hard again and then ask him to fuck me again. And again. And again. To be continued.... Please let me know what you think. I write these stories for YOUR pleasure (and yes, mine too) so I love to hear that someone is paying attention. Thank you to all those who have taken the time to write me. Thank you, thank you; it's been great to hear your comments. I love to please! Love, Randylad(y)