17 comments/ 224393 views/ 63 favorites Sissified by My Sister By: GreenGale I will never forget that night. The night I discovered how I truly am. My true self. Its an unforgivable night. And I never thought my little sister would be the one to help uncover this part of me. I was a young, average 19 year old, my sister and I were home from college for winter break. I had short, blond hair and my sister had brown hair cut about at her shoulders. Both very petite and feminine bodies. We both had fair skin and a blush was nearly always present. I feel like my sister Olivia and I have always had a strong bond. It was a cold night in January. I was watching television and getting a little bit horny browsing porn on my iPod while the TV was running. It was getting a little stormy and the TV cut off. The power must've gone out from the storm. I knew my sister was probably up even though it was 1 AM because she always watched TV until 2 in the morning most of the time, it helped her sleep. But since the power cut out she used to come into my room because she gets scared in the dark. I continued to look at porn on my iPod, now no longer distracted from the TV. I looked at a wide range of porn, softly jerking my cock. As soon as I started to speed up, I heard Olivia start to walk towards my room. I stuffed my dick into my pants and Olivia knocked on the door. "Come in" I whispered and Olivia stepped into my bedroom. "Hey, Dan, you're still awake?" my sister whispered. "Yeah, you?" I said stupidly, panicking. "Haha of course I am! You must be tired. Do you mind if I sleep in here? I cant sleep without the TV so I thought I'd keep you company" she said in the cutest damn voice. I couldn't resist. "Yeah sure thing!" I sat up and hid my iPod. "What have you been up to tonight?" she said "Oh, ya know... just watching TV" I started getting nervous because she was climbing into my bed with me. "Oh... okay, well I'm gonna try to get some shuteye. Goodnight brother!" she said with a wink. "Hah, okay goodnight" I say After a couple of minutes, I see her eyes are shut, I open up my iPod. I know it was probably a bad idea in hindsight, but I was just so horny. And having a girl in my bed didn't help, even if she was my sister. I was looking at my iPod, stroking my cock, when I felt a presence over my shoulder. I turned over and I saw my sister staring at me. She looked a little scared. I say "Oh gosh I'm so sorry Olivia. I don't know what I was thinking!" I would never forget what she said. "I think I know what you were thinking..." It was then I would never forget what happened next. She suddenly looked at me with her beautiful blue eyes and kissed me on the lips. I didn't know what exactly to think. But my boner did, I felt so turned on I grabbed her intently and pressed my boner in between her legs. Our tongues continued to dance together and I felt her hand brush my rock hard dick. Her soft hands fondled me. She pulled back and said "I've always wanted you, Dan" She stopped and said "Wow... this isn't right. I'll be right back." She ran out of my room and came back a few minutes later. She threw something under my bed and climbed back into the bed. She said "sorry about that Daniel. I didn't mean to interrupt anything. So you were watching porn?" "...y-y-yes" I studdered and she grabbed my iPod. "You wanna keep watching? I'll watch it with you" She said, opening up the porn website I had up. "This isn't weird, is it?" she said. "It is very weird." I said, she look mortified. "But I love it." We watched a whole video together and softly stroked each other. We went from video to video slowly fondling each other. Finally Olivia said "How about I pick the video?" she says. "Sure thing, sis" I say. The words felt weird coming out of my mouth. She clicked on the 'sissy' category of the porn site. She opened a video of a boy getting pounded by a dildo. A classic pegging video. At the time, I have never seen pegging. It was so strange to me. It turned me on. It turned Olivia on, too. I felt how wet she was. I knew she had a pegging fetish. "You like this stuff?" I asked. "Yeah.... ooohhh yeah!" Olivia whispered, fingering her pussy. "Do you wanna make me really happy? Reach under the bed." Under the bed was exactly what I feared. It was a pleated red skirt and a red bra and panties and a blue tank top. She asked me to put it on and I complied. I got to a mirror, and I gotta admit I looked really cute in it. The skirt and the tank top showed off my girlish figure just enough for it to trick me into thinking I was a girl when I looked in the mirror. "Haha, you look like a dyke!" Olivia said. Seeing my short blonde hair in the mirror made me agree. I felt like a woman. She kissed me gingerly and I loved feeling her long, wet tongue shoot down my throat. I wanted something more filling though. Never did I expect her to fulfill that wish. She pulled a strapon from under my bed, a pink 6 inch dildo of hers she brought in with my clothes. She slid the strapon on and she looked so sexy. Her short brown hair, her hips, her smile. It made me go crazy. I just wanted her to pin me to the wall and fuck me all night. It was so strange to have a thought like that. I never saw myself in the dominated position, but I loved it. She guided me to her sexy strapon. I started to suck on it and get it wet. I looked up at her lovingly and she looked so domineering. I wanted her to fuck me. I turned around and she started to stroke my cock like she was milking me. She squeezed my balls and I felt so defenseless. I wanted her to just fuck me already. "You ready for this, Dee?" Olivia lustfully groaned. "Oh hehe, I like that name. Dee. Does it suit me? Am I a good girl?" I say. She leans up next to me and whispers "No. You're a very naughty girl. And you need to be taught a lesson." She slides my panties asides and guides the wet strapon into my ass. I've never had anything in my butt that wasn't supposed to be there. And I loved the feeling. It hurt a bit and I yelled out in pain. But it filled me up, I felt so sexy. She grabbed me by the hips and thrust into my ass. "You like that?" she says. "I LOVE THAT!" I grunt. She keeps thrusting away at my ass and I start to see stars. "You okay, Dee?" She says "N-n-nauu-..." I moan, and I lose consciousness. I blacked out with Olivia pounding me, it was so embarassing, but I guess it was to be expected. It was so much to take in, mentally and physically I just couldn't take it. I woke up in the bed with her, her hands draped around my cock under my skirt. She had a smile on her face even though her eyes were clothes. I hoped that one day very soon I can prove that I can take it from her. Sissified by My Sister Ch. 02 Well about a week past, and my sister continued to come into my room to bury that hard strap-on into my ass. It started to become routine. Actually I was just thinking it was starting to hurt less when Olivia came up to me in private, and said "Ohh, my pretty little Dee-bear, my boyfriend is coming up for the end of winter break, just letting you know~" And at that point I hadn't thought much of it. Later that night she did the usual. I started going to bed wearing the outfit that she lays out for me under the covers, and she sneaks into my room and "punishes me for being naughty." It's what I deserve for being such a sissy all my life. The day her boyfriend Casey came over, I assumed we would stop doing stuff every night. But I was dead wrong. I hopped into bed that night and I realized she left me a pair of striped blue and white panties, a light blue bra, a pleated black skirt, and a blue shirt. I reluctantly put them on and awaited the worst. I was so scared Casey would find out and beat me or her up! After a couple of minutes of waiting, Olivia came in and said "Ohhh is my Dee bear all cute for me, yet?" "y-y-yes.." I say, shakily. I don't know why exactly I was especially afraid this time, it must've been the thought of Casey bursting in. Olivia steps in the room, black bra and panties with a garter belt, and a dark blue 7 inch strap-on. She has a devilish smile on her face. "Liv, are you sure about this?" I mutter. "Of course I'm sure! Now shut your little mouth! You have no right to question me, you little slut!" She barks back. "Now let me show you whos boss!" She grabs my cock as hard as she can, and it seems like it gets hard as soon as she touches it. She starts giving me a handjob while she pulls a blindfold out from under the bed. She must have put it there when she put my clothes out. She puts the blindfold over my eyes and everything is completely dark. I can't see through it at all. She turns me over into doggystyle position on the floor and starts to rub her fingers along my asshole. "I have a special suprise for you tonight. But you're going to have to wait~" she says cheerily. I knew I was in for some shit. She starts to slide her 7 inch strap-on in my ass and I clench and form a bit of a grip on the dildo. "Wow. I forgot how tight you are!" she says. I feel her pull the strap-on out of my ass and then I hear her walk over to my face and I feel the heat of the strap-on after pumping my ass against my face. I open my mouth and I feel it just slide in towards my throat. I then feel the plastic dildo shove up my ass again. But its still in my mouth?! I start to panic when I realize that the dildo in my mouth is actually Casey's rock hard cock. "Haha, you just realized, didn't ya. Haha what a sissy." Casey said as he thrusts harder onto my face. "Oh... Dee, was it? Tell me if I hurt you. Hahaha" Casey and Olivia were having the time of their lives on me. I felt so used. So slutty. I loved it! Both of those rock hard cocks just pounding away at me, destroying my self-view. Turning me into a full sissy. I think what turned me on the most was that it was Olivia doing all this to me. We used to always play pretend but of course it was never like this. Casey pulled his cock out of my mouth, while Olivia followed suit. He pulled the blindfold off. Then something happened that I think even Olivia didn't expect. Casey brought his face closer to mine, we both locked eyes. He wrapped his hand behind my head and kissed me. Right on the lips. At first I resisted, but I let up and began to slip my tongue into his mouth, and our tongues dance together. It was like no other kiss. It must be what girls feel like when they're kissed. Olivia looked at Casey with a grin and she began kissed him, right after me. She looked at me and gave me a long kiss as well. Casey brought his dick back up and Olivia started to suck it. She was amazingly good at it. It felt weird watching her suck dick after her being so dominate to me. Even after all that happened I felt dirty watching my sister suck Casey's cock. She sucked hard on his dick until finally he came in her mouth. She didn't swallow yet, though. She moved over to me and kissed me, swapping the cum into my mouth. I've never had cum in my mouth. It felt so weird. It tasted warm, almost like mucus but slightly metallic. "Now swallow the cum like a good sissy!" Olivia said, demanding satisfaction. I smiled at both of them and thanked them for the good time. They both just laughed and Casey said "Maybe soon I can cum in your mouth, but I dunno... You may need to beg for it!" He laughed and left with my sister. It was a strange night, and it all happened so fast. But I think it helped my sexuality a lot. Tonight taught me things about myself that I had not expected.