Constructive criticism is appreciated. Enough positive reviews I might do a sequel.
Let me start out with a little bit about who I am. My name is Chris and I'm sixteen. I look like your average sixteen year old with brown hair, brown eyes. The only thing that isn't average about me is my height, I'm not even six foot. In fact, I'm only about 4'9 which is really short for my age. I weigh 100 lbs, which is about the weight you would expect someone to be at my height.
Since this involves my sister Olivia I'm going to describe her too. My sister Olivia is twenty-one, five years older than me. Despite this great age difference there isn't much of a difference in our body sizes. We were both short and skinny, except she was 5'0 even. Olivia has brown hair and eyes just like I do, except she is not average looking like I am. Even as her brother I can tell she is attractive, and the fact that all my friends talk about how hot she is.
The twist to this story and my eventual downfall is that my sister is in fact a lesbian. She came out when she was 18 and my parents said they were okay with it as long as she didn't change anything drastic about the way she looked, which she agreed. Good thing too, because she would have been kicked out on her butt.
When my sister came out it made me question my own sexuality. Did our family have some sort of gay gene, and did I have it? I decided the only way I could know for sure was to dabble a little bit in the life of a female, or as close as I could get to it. I had the perfect night planned out and everything.
It was Friday, and my parents had went out dancing as usual. They left at 5:00 and weren't expected back until late hours of the night, later than I would need. My sister was gone, I didn't know where, and nor did I care. She was always gone on the weekends, staying out at her friends, so I was in the clear for her too.
I took a long, hot shower. I sat in the shower for 20 minutes, going over the plans in my head again and again. After the entire bathroom was good and steamy I grabbed the shaving cream and proceeded to shave all the hair off my legs. I wasn't sure how to do it so I shaved all the hair, even my pubic hair and between my butt cheeks. I didn't know if there was any hair there anyway but it felt so good I just did it. I lastly shaved my arm pits smoothe, and started washing my hair and doing the usual things you do in the shower.
I jumped out and dried myself off. I sat on the edge of the bathtub and ran my hands up and down my legs to see if I missed any spots, which it appeared I didn't. I wasn't sure how I liked this yet, but my legs sure did feel smoothe. So did the rest of my body.
When I was confident there wasn't any strips of unmissed hair, I started sifting through my mom and sister's makeup drawer. Between the two of them they had everything I needed. My sister provided the nail polish. I chose hot pink because I thought it was the girliest. I applied it pretty well, or so I thought, and moved on to makeup. This was a little bit harder, but I managed to get the eyeliner around my eyes which I thought did the most. Then I applied some blush, a little eyeshadow and called it good. I looked at the mirror and saw what I expected, a girl.
I got dressed and walked out of the bathroom with a towel over my head, just in case someone had come home I had an excuse to cover my face. No one was home. I made a pitstop into the third story attick to find an old wig we had up there. I don't know why we had it but I knew we did, and it wasn't hard to find. It was on the head of a manakin. It was a medium length, curly brunette wig, which was perfect because I had brown hair.
I grabbed it and nearly floated into my sister's room. At this point I was getting excited. I locked her door behind me without turning the light on. I clicked on the bulb and turned the dial down to a very dim light. I started searching through her drawers. She had all sorts of thongs, underwear, bras, even a couple pairs of handcuffs, the fluffy kind you get at a sex thrift store. I started to wonder just what types of things my sister was into when something caught my eye. They were big, pink ruffle underwear. They were thong or anything, which usually were the kind I liked, but the bright pink and the ruffles looked appealing to me. I decided to try them on.
I stripped completely naked, throwing my clothes and the towel in the corner of her room. I stepped into my sister's pink ruffle undies and slid them up my freshly shaven legs. As I slid them into their proper place it sent shivers through my body like never before.
I decided that since I didn't have any boobs, I wouldn't be needing a bra. I walked over to her closet and started rummaging through her clothes with complete disregard for her privacy. I was hoping the same thing would happen that happened with the underwear, and something would just catch my eye. I searched from left to right, taking a look at each dress, shirt, and skirt and started getting disheartened, for none of the things had stood out to me the way the pink ruffle underwear had.
As cliche as it may be, the very last thing on the rack was the one that I wanted. I didn't even know what it was. The word "girdle" and the word "corset" came to mine, but this thing looked like them both combined. It was black with white ribbon like material sewn vertically into it. There was black lace on the top and bottom, which reminded me of the ruffle on the underwear.
I took this item off the hanger and slipped it around me. I slid the thin black straps over my shoulders. The corset-girdle only came down to just above my butt, so a small part of my back was exposed between it and my underwear. I tried pulling it down but it seemed too short. I tried pulling the two front flaps together and clasping them, but at first it didn't seem like it would fit. I sucked in my stomache and held it while I slid the bottom clasp in, then the second, then the third. There were 15 in total that stopped just below where the boobs were supposed to go, in the middle it came down in a U shape. I tried to breathe and found that I was extremely restricted, but to my suprise I found this extremely arousing. In fact, never had I been more aroused in my entire sixteen year old life.
The bottom of the corset-girdle had two pieces of fabric that extended down each leg, and I knew instantly what they were for. I started rummaging through my sister's drawers again until I found what I wanted: stockings. She had a ton of them. Some were different colors, some fisnhet, but the ones I wanted were neither. The ones I wanted were black or dark blue and made of a thick material that you couldn't see through, almost like a leg warmer but not quite. I slipped my left leg in first for good luck, and pulled the stocking up my leg and clasped it into the girdle. I let go of it and could tell that without the girdle, the stocking would in fact slide down. I did the same with the right.
I walked around my sister's room on my tippy-toes feeling like a little princess. I realized there was something missing in this equation. I walked into her closet for a third time but this time I looked down towards the floor. She easily had 20 pairs of shoes paired up, from nike running shoes to stilettos. I grabbed a pair of shiny black leather stilettos. They looked to be my size, maybe a little small. I went to put my left foot in and found it gave a little resistance, so I pushed a little bit harder and the stockings allowed my foot to slide in firmly, and the right foot went the same way. I now stood at a towering 5'2. I started walking around the room, adjusting to my new height and just feeling very horny in general.
I wanted to look in the mirror, but before I did I walked over to Olivia's bed, with a little difficulty, and grabbed the wig. I slid it over my head, felt the elastic band still doing it's just and clinging firmly around my head. I walked over beside the door and stared at myself through my sister's mirror. I looked sexy, felt sexy, and felt just amazing. I stepped back a few feet and fell onto my sister's bed.
I started wishing I could do this all the time. Then I started thinking, why not? I could sneak in here every chance I can get, my sister is always gone and my parents never check on her room. I could just... "Whoa" I thought to myself suddenly. I almost drifted off there for a second. Suddenly I was very aware of how late it was. I had only been in here for a matter of minutes but it felt like an eternity all of a sudden.
I felt a sharp pain in my back and cried out, "Ouuchh." I was laying on my stomache and my back was arched forward. It only took me a matter of seconds for my heart to start beating fast and for me to start realizing what was going on. My arms were thrown back behind me and I could feel something fastened securely around my wrists. As if both my hands being restrained wasn't enough, so were my legs. I could feel the same device closed tightly around both of my ankles.
I took a second to think, and I guessed that I was indeed handcuffed. It took me a few more second of thinking to realize that my left wrist was handcuffed to my left leg, and vice versa.
"Christopher," I heard a familiar voice speak softly through the darkness. Even though my sister spoke quietly and calmly, I knew I was in big trouble.
I didn't say anything, but she continued anyway, "Christopher, I'm not mad at you." My heart continued to pound. I thought my heard was going to explode right there. "I'm not mad at you, Chris, but I am going to teach you a lesson. It's either this, or I can bring Dad in here and let him take care of you. What's your decision?"
I continued to sit there in silence, not wanting to say anything. I was completely humiliated. Luckily, she took my silence as consent.
"Alright then," she said, and started moving across the room. I couldn't tell where she was at first but when she started walking I realized she was right in front of me. It was so dark in her room my eyes still hadn't adjusted. She walked close to my face. At first I thought she was going to slap me, and after a few seconds she did.
She smacked me on my right cheek, but it didn't make a slap sound, it kind of flopped instead. In fact, what I got hit with wasn't even flat. "Open your mouth," I heard her command. She didn't sound like she was kidding. I wanted to open my mouth and speak for the first time, protest her demands, but before I could I felt something press against my lips. It felt rubbery, almost the same consistency as a rubber bouncy-ball.
I closed my eyes in suprise and as I opened them my eyes started catching up with things. I could see my sister's black shirt, her blue jeans, but the important thing is what she was holding onto. I had never seen a dildo in my teenage lift, but now one was pressed against my lips. It looked to be black, even in the darkness, and therefore I couldn't make out any details about it. I could see that she was wearing some sort of harness that the dildo poked through, apparently holding it firmly in place.
With one hand my sister held onto the dildo with determination, pressing it against my lips that were covered in her lipstick. Things were so backwards it made my head spin. I kept my lips sealed even though she started prodding them with the dildo, mashing them against my teeth.
With her free hand she grabbed a handful of wig and whipped my head backwards. I didn't think my sister had that much strength in her. She must have nearly broken my neck. I opened my mouth in a silent scream. "That's it," she said, whipping my head back like it was before, "Keep your mouth open little girl."
Now I was getting scared. I had never seen my sister this furious. She had never placed her hands on me in her life, but here she was whipping my head around like a volleyball. With these things in mind I kept my mouth open wide.
I felt the dildo enter my mouth. It didn't feel like smoothe rubber, it felt like it was made to be "skin-like" but I couldn't have been sure. All I could do was estimate it's size. It felt larger than a golf ball around. It felt like my lips had to stretch to get around it. She pushed it in further with my lips locked tightly around it. My lips ran over some sort of hump that I guessed to be the head of the dildo.
"Suck on it," my sister said, sounding angrier than ever. I locked my lips around tightly and started sucking, or trying to. It was like one of those real big jawbreakers that you get, that you could never suck on cuz they were so big. Despite this, I sucked. I swallowed all of my saliva with some effort. I wasn't used to swallowing with my mouth open, let alone with objects in it.
She let go of her dildo and used that hand as a second set of grippers for my wig. She started moving my head up and down. The thing is no more really went into my mouth. She was more just shaking my head in place. I was forced to breathe through my nose, which I rarely did, so I started losing my breath and breathing heavily. The room was silent except for this sound.
Her hands were still gripping my head firmly, as if being hogtied on my stomache wasn't enough, she pulled her hips back pulling the dildo from my mouth with a pop. It was like taking a bottle from a baby. I closed my mouth and swallowed hard.
"Open your mouth," she said, and just as I did she impaled my face with it once again, only this time she jammed it hard. She jammed it so hard I thought she was going to crush my tonsils. I made a weird duck sound as I gasped for air. I closed my lips around it, swallowed her and without missing a beat my sister said, "Keep your mouth open," she emphasized the word with an extra thrust, "Chris... Christy. Keep your fucking mouth open, Christy."
My face burned in the darkness of my sister's room. This was the most humiliating thing that has ever happened to me, I started thinking to myself. I opened my mouth wide in fear of further humiliation. She started thrusting it into my mouth, ramming it against the back of my mouth. I tried to relax my throat but with every thrust my throat would tense up and I thought I was going to puke. I prayed that I didn't.
"Suck on the balls, Christy, you're my little slave now," my sister hissed. She didn't even sound like my sister anymore, I didn't even know who she was. She took one hand from my wig and pulled the dildo from my mouth again, but this time without a baby-bottle pop. She leaned forward and thrusted her pelvis in my face. I didn't know if I felt more uncomfortable about being so close to my sister's vagina or the rubber testicles I was about to suck on.
I kept my mouth wide. They hit my mouth and I wrapped my lips around them and sucked. At this point I was not asking questions. I just wanted to avoid further humiliation.
"Yeah, that's it," she said. The thing that scared me the moast is that I knew she couldn't really be getting pleasure from this. Regardless, I sucked on the balls like I meant it. I wanted her to think I really did mean it. I sucked on both of them into my mouth as far as I could, then started moving them in and out of my mouth.
She popped them out of my mouth, then turned around and walked to her dresser. I heard one of the drawers open, some shuffling, then the drawer closed. She walked back over to me. "You've been pretty good so far, if not a little slow, Christy. Now, mouth wide."
I closed my eyes and opened my mouth again, expecting more tonsil ramming. What I closed my lips around was not a dildo. At first I thought it was, but it was so big that I couldn't fit my mouth around it, it just opened my mouth until my jaw nearly unhinged. I had half a second to retaliate before I felt some sort of belt around my head. "Oommmm," I moaned in protest, but my sister fastened it tightly around my head.
"OOOMMM," I screamed, but the gag muffled my cry. It was no louder than someone talking at a normal voice. It felt like the entire front of my face was one big cramp. I moaned a few more times in pain.
My sister completely ignored in me. In fact, she was not in front of me anymore. She had moved around to the side of the bed. I couldn't see her, but I could hear her. I felt the bed move and before I knew it she had each of my ankles in her hands. She spread them apart and climbed between my legs. She climbed all the way up to my back, straddling me, an arm tied to a leg on either side of her. I felt her messing with one of the handcuffs and to my suprise, one of them clicked open. I thought about running, but then I realized that I had nowhere to run, and that my sister would likely tell on me.
It was my left leg she uncuffed first. I thought maybe for a second she was just going to let me go, but I was wrong. She cuffed my left wrist to my right, police-style. Then she uncuffed my right leg and arm, freeing the extra pair of cuffs. I thought she was going to cuff my ankles together, but she didn't. She slid down to my knees, still straddling me, and placed one hand on my ass.
I jumped so hard she nearly was flung off the bed, but she didn't even take notice. She placed a second hand on my ass, one on each cheek, and started massaging and squeezing them. "You got a cute ass, little girl," my sister said. Every time she spoke it was like she slapped me. I couldn't believe this was even happening and my sister seemed to be provoking things.
"I'm gonna fuck your little ass," I flinched as my sister spoke. Every word was venomous. "But first, I'm gonna stretch you out." I felt her hook her fingers into the band of my pink ruffle underwear and pull them down, exposing my butt.
She let go of my underwear and placed her hands on my bare ass and squeezed. "Nice fingernails," she said, "Now,I'm gonna put a butt plug in you. Be a good girl for me and spread your ass wide, both hands. "
Since my hands were already cuffed behind my back, I only had to move them a small distance. I placed one hand on each cheek, making sure I got a good grip, and spread my cheeks. I felt some sort of warm liquid being poured between my cheeks, then something hard and cold slid up and down my crack. I knew immediately what it was.
My sister slid the buttplug up and down my ass crack a couple times brushing over my anus, but it was when it stopped directly on it that I started panicking again. The combination of the lube and the smoothe texture of the buttplug made it impossible to tell exactly when the buttplug entered me, but I knew when it was in. It felt like I was relieving myself in reverse. My butthole continued to expland around the buttplug until it was stretched to it's limit. My sister applied a tiny bit more pressure and it felt like my ass was going to split.
"Mmmmmhhhhh-uuuhhh," I managed to moan, less audible than a whisper.
"Just a little..." she pushed harder, "bit..." I felt my ass being stretched to it's limit. I thought I was going to cry it hurt so bad and my sister was not letting up. I was relieved when the buttplug slid completely into me and my anus locked around the base. The base wasn't the thickest part but it felt like nothing compared to before.
She started pulling the buttplug out. I squeezed my cheeks together tightly but the buttplug popped out of my ass with great pain and resistance. Once out, she started fucking the tip into my asshole before inserting it again, and again pulling it out. God I wanted to cry. She continued to do this for the next couple minutes. Then she pulled out the big guns.
When she dropped the buttplug beside me on the bed I knew what was next, and she knew I knew, because she had no warning for me. I felt her place the tip of the dildo up to my loose asshole and push. I squeezed my cheeks together to try and stop it, but I could feel my asshole stretching.
"MMMmmmmmmm" I moaned again, but this time I was nearly screaming. My asshole was being stretched more than before. The buttplug felt like little games compared to this.
"It's just got a big head," my sister assured me, "once it's inside you, you'll loosen up quite nicely." She said it as-a-matter-of-factly, and pushed harder. I spread my ass cheeks so hard with my hands. I figured the wider I spread my ass the easier it would enter me. I kept repeating this in my head over and over and after a little encouragement I felt my anus contract around the shaft of the dildo and I knew the head was in. She was right, the shaft was a lot skinner than the head.
She thrust her hips forward and the dildo grinding into me made me moan again. I felt my sister place her hands on mine, spreading my ass with me. It's hard to explain but it was almost romantic. As she did this she retracted her hips, then thrusted them, then retraced them. My sister was officially fucking me in the ass. I was thankful she didn't try to drive it deep into me. Her dildo was so big I was sure it would reach all the way up to my rib cage.
"You like your ass being stretched," my sister asked? "Answer me you little slut."
I felt her fumbling with the gag until it unclasped and fell down around my neck.
"Yes!" I squealed, hoping she would stop all this. Unfortunately, she didn't. Not right away, at least. She fucked me for a couple more minutes before she spoke again.
"You wanna suck it little girl? You wanna suck it don't you?" my sister tauned.
"Yes," I shreaked, "let me suck it." I said it before the true horror of what was happening sunk in. Was the talking about sucking on it after it was up my ass? I hoped it wasn't true, but it was. She slowly pulled the massive dildo from my ass. It popped out and my butthole instantly puckered up, but before it did I could feel just exactly how much she had stretched me. It felt like I could fit a can of tennis balls into me with ease. Olivia rubbed the dildo up and down my ass crack a couple times before getting off the bed and walking around in front of me.
"Roll over on your back, Christy. Fucking your little ass isn't the only thing I'm going to do to you tonight that you're not going to like." Not knowing what she was talking about I rolled over onto my back. My shoulders started hurting instantly because of the awkward way my arms were cuffed behing my back. My sister hooked her hands into my arm pits and pulled me towards her until my head hung off the bed.
She let go of me and grabbed her dildo, still fastened into it's harness. She started slapping my face with it. At first she slapped it softly, then she started slapping the gag that filled my mouth, but then she started slapping hard, and all over my face. My eyes, my nose, my lips, all were getting abused by this. I started shaking my head to make it stop.
"I'm gonna fuck your stupid, little throat," she said, with all seriousness. "And if you say a thing I'm going to march outside and go get Dad. Do not test me, little girl.
"Open your mouth and stick out your tongue," she said, and I did. I opened my mouth wide and stuck my tongue out. She started slapping the dildo on my tongue. She did this for about 10 seconds before sticking it in my mouth. She started "fucking my throat" just like she did before, ramming it against my tonsils.
My sister grabbed my throat. For a second I thought she might murder me, but immediately dismissed the idea. She bent my head down towards the ground. It felt like it was going to snap backwards. "Thaaat's it," she said sadistically, "a straight runway into your stomache." I felt very vulnerable with my sister gripping my throat firmly.
Olivia leaned forward with what must have been all of her weight, but it was unlike any of the previous times. The dildo jammed against the back of my throat, but she used her weight to jam it harder and harder. I felt the dildo bend into my actual throat, and I instantly dry heaved. My sister, feeling my dry heave, tightened her grip on my throat and pushed harder. I felt the bulbous head of the dildo grind down my throat. Before I was in fear of my tonsils getting bashed, now she was going to bash my vocal cords.
The dildo was 3-4 inches into my throat when my sister pulled it out. "Now, you're gonna take this thing to the balls once for every piece of clothing you stole from me. Take a deep breath."
"First, the corset," my sister said, leaning her weight forward and jamming the dildo into my mouth. It bent down into my throat a little easier than before but once again I dry heaved, my stomache lurching into the air. She held my throat firmly.
"Ooohhh," she said, once the entire dildo had beein jammed into my throat. I felt my lips touch the firm plastic harness and I thought I might pass out. I could no longer feel the head of the dildo expanding my throat, it must have been in my stomache. She pulled it out slowly and I found that thought to be true.
She retreated the dildo until just the head rested in my mouth. I sucked hard and swallowed all the extra saliva in my mouth.
"Pink ruffle undies," she said, once again plunging the dildo down my throat, scrubbing my vocal cords. And once again she pulled it out. "Nylons," she said, repeating the process. "And... my high heels." This time she gripped my throat so hard it choked me. I knew if I tried to talk my voice would come out a squeak. She jammed the dildo down my throat and this time started fucking my face. She pulled it out like before.
"Get off the bed and get on your knees, now."
I rolled over onto my stomache and stepped off the bed. My sister had turned to the side. I walked up to her and dropped to my knees.
"You're lucky this isn't a real penis or you'd be swallowing cum right now. But, you're gonna suck my dick like I am going to cum."
With this I leaned my head forward and opened my mouth. I plopped the head onto my tongue and sucked.
"I shouldn't have to help you get it in this time. All the way down."
I leaned forward and to my suprise the dildo slid down my throat with a decent amount of ease. I didn't dry heave. I think I had learned how to relax my throat better so I didn't gag. I fucked it in and out of my throat a couple times before she spoke. "Suck it like I'm cumming in your mouth," she said, and started moaning.
"Ohh, mmmm I'm cumming," my sister encouraged. I started fucking the dildo in and out of my mouth. I slid the head in and out of the entrance to my throat. Now that my throat had relaxed it felt kind of good.
"Ohh yeah," she moaned, "all in your throat." She pulled it out and started stroking it. "Open wide," she commanded. I opened my mouth and looked up at her. She leaned down and I thought she was going to kiss me, but she didn't. She spit a large wad of saliva onto my tongue. "Swallow," she commanded heartlessly, and I did. I swallowed hard and was glad that this was all over.
"What is today," she asked rhetorically. "I tell you what, Christy. Today is Friday the 16th. Next Friday the sixteenth at 8:00 sharp I want you on my bed, dressed to swallow some cum. Maybe real cum, if you're lucky. You understand me?"
I looked down at the ground. "Yes," I sulked in shame. My sister reached down and uncuffed both of my wrists.
"Now, get the fuck out of my sight."
"But, can't I at least get my..."
"GET... OUT..." she yelled, and all the hairs on my body stood up.
Still in my sister's corset, nylons covering my legs, ruffle undies riding up my butt and high heels on my feet, I opened her door and fled to my room, fastening the lock behind me.