Date: Mon, 13 May 2013 17:10:03 -0400 From: John Smith Subject: Wicked Stepsister - Chapter Two TG Beyond asking me to pass one of the side dishes to her at meal time, Renee pretty much ignored me until the weekend. She didn't even say anything to me when we got off the bus Friday afternoon. It's strange, but I was really happy to see that her mom's car wasn't parked at the house. I was under the impression, despite all the evidence to the contrary, that one of these days I could do everything right and make Renee so happy with me that she'd finally let me fuck her... make a man out of me and all that. I was never too bright about some things. It was my turn to wash the dishes, but it didn't take very long. When I went into my bedroom, I saw that the pair of panties had been laid out on my bed. I never left them out like that, so I knew that Renee had taken them out of my hiding place and put them there as a message. I quickly stripped out of my school clothes and pulled the pink underwear up my legs. It was only me second time putting them on, but they already felt just as natural as the rest of my clothes. I ran down the hallway, but made sure to slow down before I hit Renee's door. I decided it would probably be a good idea to show respect, so I knocked and, as politely as I could, asked if I could come in. "Enter, slut," Renee responded after a nice long pause. I did as I was told and opened the door. Renee was sitting at her computer and didn't even look up to acknowledge me. She was wearing what looked like a pair of basketball shorts and a slim fitted t-shirt. I stood patiently and waited for her attention. Being a little nervous, I did find myself picking at the waistband of the panties a couple of times. Just when I figured she intended to make me stand there the whole night while she ignored me, she asked me a question. "Have you been a good girl, slut?" "Yes, Renee," I replied, meekly. "You haven't been touching your dick have you?" She asked. "No," I answered quickly, then had to correct myself, "Not jacking off, I mean. I have to touch it when I wash in the shower." "That's okay," she explained, "Now come here." I obediently padded over to Renee. She swiveled around in her chair to face me. I could see she had been video chatting with someone, but must have closed the connection. "Turn around, slut," she demanded, "I want to get a better look at what I'm working with." I jumped a little when she squeezed my right butt cheek. Just from the touch of her skin against mine, I could feel my dick started to stir. There was nothing I could do about it, I just had to hope it wouldn't upset her. "You have a really nice ass," she observed, openly palming and groping my backside the way I'd seen some of the football players do with the cheerleaders after pep rallies. "It is so cute and girly," she added, right before the slap landed. I was probably more surprised by how loud it sounded than by the sting. I was surprised again when I felt her hands playing over my inner and outer thigh. I was certain she knew she was torturing me, the way her hands kept creeping higher and higher only to fall away at the last moment. "Did you shave your legs, slut?" she asked. "No, Renee," I said, after clearing my throat, "It's a family thing or something, we don't get a lot of body hair." "You're like the perfect slut," she remarked before giving me ass another slap, this time on the left cheek, "I'm going to buy you some g-strings. It wont be long before you'll have something up your ass, twenty four seven." When Renee used the words "up your ass", I felt a nervous flutter in my stomach. It was kind of insane, letting her have so much power over me. I could have jacked off at school or something and she would have never known, but I actually liked doing what she told me during our first session. It was something I'd been curious about, but would have never attempted on my own. Maybe that is why I was so willing to go along with her, she'd give me an excuse to find out what really worked for me...or maybe I was just so desperate to cum that I would have agreed to anything. Growing up, I dreaded long family trips or any activity that meant I couldn't slip away if I needed to. If something got me worked up and I couldn't get off fast enough, my brain started coming up with all these weird things to up the ante. "In the right clothes, I bet nobody would even guess you used to be a boy." Renee observed. "I don't have any tits," I said, sheepishly over my shoulder. Renee rewarded me with another bracing slap on the ass. I was tenting the panties again. "Some guys like androgynous girls," she said, "Lets do an experiment. I want to see what you look like when you're dressed for your role. Follow me." I trailed behind Renee as she made her way to her closet. We were amazingly close to the same size, as my experience with her panties had proven. She pulled out tops and mini-skirts and made me hold them up to my body. She finally settled on what appeared to be a schoolgirl outfit. Plaid, pleated skirt and all. "Go put these on in my bathroom," Renee said, after adding a pair of stockings and a bra to the jumble of clothes in my arms, "I have to go get something for you." Even though it felt like I was getting further and further away from being allowed to cum, I was actually excited to see what I would look like in the new outfit. It took me a little effort, but soon enough everything was on and in place. Looking down at my body, I felt like a completely different person. I'd left the top buttons open so I could look down my own shirt. Renee's bra was probably the tightest thing I was wearing. The strong little black garment was doing the best it could to make my pecs look like boobs. I found myself kind of obsessing over my chest, pushing what I could together, or up, to see how it looked in the mirror. I wondered what was taking Renee so long. I was really anxious to see what she thought of the outfit. I actually had my cock, which was pretty much perpetually half hard or better through the whole fitting experience, tucked under and my dress hiked up so I could see how it would look when I saw her coming up behind me in the mirror. "You're such a slut," she smiled. It turned out she'd been looking through old boxes of her mother's things to find a wig for me. It was black, so it looked like a pretty natural fit for my complexion. Even before Renee finished putting the makeup on me, I was amazed at how completely my boy self had vanished into my slut self. I looked like a totally different person. "Not bad," Renee said, appraising her work, "Lets go see how good of an actress you are." Renee made me bring in a chair from the dining room and set it next to hers in front of the computer. She had a random video chat program open, and was ready to hit the connect button. "Put your hands in your lap," she directed, "and try to look cute." The first person she connected to was a an olive skinned dude with really hairy arms who was already masturbating for the camera. Renee frowned and clicked the "next" button before the guy could peel his hands away long enough to type a greeting. It took about twenty clicks before a guy popped up that Renee approved of enough to communicate with. He was fairly normal looking, claimed to be eighteen, and had a nice smile. I waited for instruction as Renee started typing. She told him that I was her cousin and that I was a little insecure after a breakup. The guy typed back that I didn't have anything to be insecure about. He typed that I was hot and my ex boyfriend was an idiot. I smiled and blew a kiss to the camera. I guess I should have been offended that he couldn't tell I was a boy, but I didn't really care. That was more validation than I'd had in my normal life in years. He started typing flirty things and asking me about music and what kind of stuff I liked doing. Renee shoved the keyboard over so I could type. I told as much truth as I could and made up the rest. I felt a little weird about manipulating him and lying, but I was really loving the positive attention. Growing up as a boy, you never really want to hear that you're pretty, but you I guess you can get used to it in a hurry. Eventually he asked me where I lived, if it was anywhere near him. He was three states away, and kind of bummed that I wasn't planning on taking a trip anytime soon. He said he had to go, probably looking for someone close enough to actually hook up with. I waved to the camera and Renee hit next. Over the next half hour, Renee taught me how to be a tease and how to flirt. Guys liked my pouty face, but they really seemed to enjoy it when I squeezed my pec tits and licked my lips. It was just benign fun, and we didn't see another cock until the last guy we connected to. He was a handsome blonde with really nice abs. It seemed like he was just waiting for an excuse, or for permission, to whip it out. The flirting escalated pretty quick, and he evidently didn't care that we were on opposite ends of the country. He claimed he was lonely cause he just broke up with his girl. I typed back asking why, and he responded that she didn't giving him blowjobs. I typed back that she's crazy, blowjobs are so much fun. It went pretty quick from there, and for a while he seemed perfectly content just to stroke his rod for me as we narrated sex acts back and forth in the chat window. Then he typed out an almost sheepish sounding: Can I see your ass, baby? I looked over at Renee, and she nodded. We stood up and she adjusted the camera placement a little so it tracked my ass. She guided me into leaning forward and supporting myself against the chair's back. I kept my legs together, doing kind of a reverse tuck to try and make sure nothing gave away the fact I had boy parts. Renee assisted me by flipping the back of my skirt up. She pulled the seat of the panties in from the sides, creating like a makeshift g-string and putting my ass completely on display. Straining to look back at the screen over my shoulder, I could see the words our friend had typed: beautiful ass! Tits please? Renee had something else in mind. She delivered her strongest slap yet, actually rocking me forward. I was sure she'd left a handprint that time. Our friend was really enjoying the show, stroking his big dick furiously. That was when Renee decided to turn up the heat. She leaned in and covered my lips with hers, thrusting her tongue into my mouth. We alternated between tongue kissing and spanking. It wasn't long before our friend managed to type out a feeble "Im gonna cum". By the time he finished blowing his lovely load, my ass felt raw, and I was so hard from making out with Renee that the swat team could have used my dick as a battering ram. I'd seen guys get off in porn before, but it was different knowing that it was for me. It made me feel so sexy and horny. I was all set to blow another kiss to the screen and say goodbye when Renee grabbed my shoulders and spun me around to face the camera. She made sure to lift the front of the skirt up, putting the way my cock stuck out above the panties on display for our friend. Judging by the look on his face, and the mad scramble for the disconnect button, he wasn't a fan. I wasn't sure what was going to happen, if she was going to punish me for getting in to it so much, or if the reveal was the punishment, but I knew better than to ask. She closed out the program and kissed me again as she grabbed my shoulders. I tried not to smile as she forced me back onto the bed, but to my surprise, she commanded me to roll over. Once I was face down, she spanked me again for taking too long. Renee was panting like an animal, and I wasn't sure what she had planned for me, but I got an idea when I felt her weight press down on me. The girl was urgently grinding against my ass, pretending I was taking an imaginary cock in or something. The strong rocking motion felt wonderful, with my own cock trapped between my abdomen and the bed as Renee humped me as hard as she could. It was starting to smell like girl in the room again, even stronger this time than when she'd been thumbing her clit during the hairbrush blowjob. I found myself picturing her with a cock of her own, maybe like the nice one our friend from the chat had. I wondered what it would feel like to have Renee's dick inside of me. Finally, between the fantasy and the friction, I started to come. I felt the warmth spurt out along my abdomen, instantly getting smeared around as Renee's assault continued. With the sensory overload, and everything that lead up to it, I came harder than I ever had before. It felt like I was about to pass out. A couple minutes later, after thoroughly grinding my softening cock, and a good bit of my new outfit, into the sticky mess I'd made, Renee must have come as well. She shrieked and thrashed around before rolling off of me. "Not bad, Slut." She said, patting me gently on the butt. It was all I could do to roll over without losing consciousness. I looked up in time to see Renee get up from the bed and strip. She tossed her top and sodden shorts onto me and headed toward the shower. "I want everything clean and the sheets back on my bed before dinner," she commanded over her shoulder, "But don't start the washing machine until I'm out of the shower unless you want to wear your uniform to school on Monday." "Yes, Renee," I said, dreamily.