47 comments/ 155790 views/ 268 favorites My Used-To-Be-Tomboy Sister, Tommi By: FitNerd I'm not exactly sure how I wound up in my current situation. The worst part is that I still can't make up my mind about it. On one hand, I had the most, the... most, incredible sexual encounter of my entire life. On the other hand... well, we'll come around to the other side of that soon enough. I mean come on, let's not rush things. If I could do it all again, I wish I had had the option of taking my time. Maybe I wouldn't have made such bad decisions. Or, then again, maybe it would have happened in exactly the same way. You're probably wondering how I could be so "on the fence" about the most amazing sexual experience of my life. Well, maybe if you knew it involved my sister Tommi, then you'd understand. I know, it's wrong, but I didn't exactly have a choice in the matter. Well, not after it started at least. Let me explain. It's probably important that you understand some things about my family. I have a great family. I laugh and joke with my family just as much as I do with my friends. We all respect each other. Nobody would expect, and God do I hope nobody finds out, that anybody in my family would be involved in such debauchery as what I've experienced. My dad is one of those fit and funny types. He likes sports and I've overheard them enough to know that he and my mom definitely have no problems in the bedroom area. After all, who could with a mom who looks like mine does. At least, that's the impression I get from my friends. They're always joking about how hot my mom is and I guess they're right but I never really thought of her that way. Like I said, we are, were... anyways, just a normal family. I had recently come back from college having finished my degree in computer science when this all sort of started. My sister graduated high school a few months before I returned from school. She's quite a few years younger than me and I didn't really expect her to be so... grown up, I guess is the right way to describe it. She was always kind of thin and tom boyish when we were growing up and I never felt guilt about shortening her name to Tom during our sibling banter. So, with a sister I playfully called Tom, you can imagine that I didn't expect to come back to such a beautiful sister. I can say with one-hundred percent honesty that she is a very hot woman. Even before all of this happened, I would have said so. I never had any dirty thoughts about her though. Like I said, I'm a normal guy with a normal family. Everyone knows that puberty is a powerful thing. It definitely did my sister wonders, especially because she was so plain before. Right around when she turned 18, her boyishness completely faded. She wore a D cup bra. I know because my mom always playfully gave her shit for one-upping her in that department and she was a C cup. She had shoulder length red hair and was oddly enough the only red head in the family. Her pale complexion was slightly freckled and her green eyes were breathtaking. Yes, I knew that if any of them had the chance, my friends would chop of their own dick if it meant they could have sex with her. I had never seen her body in less than a hoodie and sweat pants up until this point, though. Needless to say, I wasn't ready. I was working out in our home gym and I was really hitting the weights hard. I had worked up quite a sweat before she came to join me. This wasn't unusual but it had been quite a few years since we worked out together. Maybe it was the heat, maybe it was the oxygen debt, but as soon as she turned away from me to get on the stair master, I felt a jolt go straight to my cock as I laid eyes upon the nicest shaped ass I'd seen in my life. The college girls at the gym that I had gotten used to seeing didn't even phase me but for some reason, my body was instantly aroused by her. I sat there trying to catch my breath and losing that game horribly as I felt the heat across my forehead and the redness across my cheeks and noticed that I was blushing in time to her hips swaying from side to side. Her ass stretching her green spandex pants to the max and my mouth was watering as I unconsciously took a mental bite out of her left ass cheek. I closed my eyes as soon as I realized what I was looking at. I was watching my own sister's ass, my blood was pumping in the worst way and pretty soon I was going to have problems. I "finished up my workout" as quickly as I could, which basically consisted of me grabbing a towel and hanging it in front of my crotch as I pretend to wipe my sweat away as I walked toward the door. I couldn't help but glance back as I went through the door. Sweat had begun to form on the top of her big soft breasts as she climbed one excruciating step after the other. She had headphones in and was focused on her workout. Her green eyes pierced me as she glanced at me on my way out the door. "Holy shit," I thought as I finally got out of the room. It finally felt like I could breathe. What, the fuck, just happened. After I cooled down a bit I realized I had my hand on my dick. I immediately moved it away and decided I should just relax. It was normal to react physical to something as physically perfect as her amazing ass and tits. Whatever. I'd get over it. At least she didn't notice my perversion. That was that until a few days later when we were having our annual labor day party. My family always celebrated by throwing a big pool party and inviting all of our friends. Once again, I was taken by surprise at what I saw. I was sitting in the hot tub by the pool. The party was going pretty steady. There was music and almost everyone I remembered from growing up was there. I turned away from a conversation with the next door neighbors when I saw my red headed sister walking out of the house. She was wearing a white string bikini. Her hair flowed down to her shoulders. She was simply stunning. I was speechless as I watched her tits bounce with each step, seemingly in slow motion. Her hips moved in such an exaggerated pattern that I couldn't help but think sexual thoughts about her. I felt that familiar jolt as my dick started to harden. I knew I wouldn't be able to get out of the hot tub for quite some time. She started walking over the hot tub just as I was drawn out of the spell I was under. The sound of the party came roaring back to normal as I realized that I had sort of drowned it out as she was walking around the pool. I was lucky I had been wearing sunglasses because that could have been pretty embarrassing had someone seen me ogling my own sister. I regained my composure as she sauntered up to the hot tub. She leaned over and put her hands on the side of it and started talking to one of our neighbors. "Hey Mr. Jones! How's the Missus?" She said jovially as her tits hung forward, making them look even bigger than they already did. At this point, I decided to use my tried and true calming method so that I didn't blow this whole thing out of proportion in my head. I have always been a believer that if you indulge your thoughts about something, you could experience it in your mind, no harm done. This is the main idea behind meditation, to allow yourself to think and feel whatever it is you are feeling. This way, I could objectively get over the feelings I was having without things getting too far out of my control. I sat back and watched her, listening quietly from the sidelines while I allowed myself to feel a little bit of the lust that desperately wanted to boil over and out of me... "Kind of boring," she responded shyly after he asked her how life was after high school. "I kind of just sit around all day and read or workout lately, between looking for a job that is, haha!" Her laugh sent shivers down my spine as I realized that my cock was suddenly rock hard. Images of her red hair wrapped around my fingers as I pumped my cock in and out of her mouth flashed through my mind as I stifled a groan that nearly escaped. That's when I started to second guess my decision. This wasn't helping at all. Maybe it was the heat once again, this time from the hot tub, or maybe it was the warm slick feeling of her soft breasts wrapped around my dick as she fucked me with her chest, those gorgeous green eyes daring me to come on her tits. Well, that's what she was doing to me in my head when I realized that I needed to stop this right away. I was not prepared to masturbate to my sister and that was the clear ending to this line of "meditation" if you could call it that. I couldn't let myself do that. That was a line that I didn't feel right crossing. I willed my engorged shaft to go down but my libido was on fire. The sexual energy coursing through my veins was a freight train dead set on smashing into my dignity as soon as someone found out that in my head, my very own sister was bent over the kitchen counter taking the full length of my cock deep in her pussy with every sweet, slow stroke. Luckily the bubbles in the hot tub were hiding my massive erection. I feigned comfort as I laid back, pretending to be enjoying the hot tub, even though my fear was definitely at the forefront of my thoughts. Every time I closed my eyes it was another dirty image. She was licking my balls and telling me how badly she wanted me inside her one second and then just a blink later, she was riding me whispering the dirtiest of things in my ear while biting my ear, begging me to fuck her harder. I had lost this game and I was resigned to whatever my fate would be at this point. Just a few seconds later, much to my relief, I was saved by the lunch bell. A general increase in chatter and movement signaled that lunch was served as everyone began to head in that direction. In just a few moments, everyone was headed off to the other side of the pool where the food waited. I looked up as my sister lagged behind the rest and boy did she look nice lagging behind. Her ass was magnificent. She was wearing one of those white bikini bottoms that basically grips each cheek individually. I could both of her globes as she walked, causing me to sigh in frustration. Just then, I found myself saddened as that amazing ass turned out of view. It dawned on me just a bit too late that she was now standing half-sideways and she had stopped walking. "Hey! I said, are you coming for lunch?" Oh man if only she knew about whether or not I was coming. My voice cracked just a bit as I responded. "Oh, yeah I'll uh, be right there! Just enjoying the water." as I smiled. A pensive look flashed across her freckled face for a half second before she responded with a playful smile. "You're such a nerd!" She said, just like she always did as we grew up. I was always into video games and she always made fun of me for it in jest, even though I knew she didn't actually mean it negatively. I responded as I usually did. "Why don't you go lift more weights, I think your arms are getting bigger than mine. Are you sure that isn't some chest hair I see growing in?" I had always jabbed back at her, making fun of her tom-boyishness. She turned fully around and put her hands on her hips as she gave me her best "that really hurt" expression. I swear she just had to know what she did to me. After a moment, she wiped away her saddened look and started to walk toward me. I was immediately silent as it seemed like she approached in slow motion, the sway of her hips had me enthralled. She stopped at the opposite end of the hot tub and bent at the waist, leaning as far forward as she possibly could. Her tits looked amazing from this view, thank God for sunglasses. I could almost see into her top, seeking out her nipples with my gaze as she said with a smirk and one cocked eyebrow, "Maybe if you spent more time learning how to play with women instead of your video games, you wouldn't have to jack off to internet porn all day." She lazily hung her head sideways as she waited for me to respond, her face sending shivers down my spine. I panicked. The first thing that I could think of was to burst out in song to hide my fear. For some reason, the first relevant song I could think of cropped into my head and it was probably the worst possible song to sing, considering the circumstances. I took a big breath and broke out into song and dance to divert her attention. "I touch myself! When I... think about you!" (Yes, by the Divinyls and yes, I know I'm terrible with song lyrics, why that song came into my head I'll never know) as I threw my arms up into the air and then pointed my finger very close to her face in an exaggerated mostly arms type of dance. Instantly, I realized what I had said and both of our faces turned serious and embarrassed. The silence seemed to last forever but was really only a few seconds. I didn't know what was going to happen but I was definitely able to speak, waiting for her to do something. I was immediately relieved when she broke her expression and immediately started laughing uncontrollably and started singing and dancing to the song. I joined in quickly and we both sang in chorus while laughing, "I don't want... aaaaaanybody else. When I think ab-ooooooout you I touch myself! Oh no, Oh NO, OH NO!" The laughter trailed off as we acknowledged a good laugh. My erection had completely subsided due to my nerves so I jumped out of the hot tub and gave her a noogie as I said, "Let's go get some food, Tom!" She responded by punching me in my stomach with a playful "Hey, fuck you man!" look on her face. I tensed up my abs just in time for impact and I made a show of flexing my manliness(I'm actually really fit for a nerd) before we walked over to get food with my dork swagger turned up to 11. I really felt like I had dodged a bullet that time but even as traumatizing as that experience had been, nothing could have prepared me for what happened a week later. Over the next week, I couldn't shake the thoughts of banging my sister. It didn't help that she was not only stunningly beautiful but was also an awesome person. She had a great way of engaging everyone she spoke to in conversation with a very warm and interested feeling with her genuine smile. Every time we ran into each other over the next few days, she would say something and open her mouth just wide enough that it would trigger the image of me slipping my hard cock between her lips as she sucked me dry. Or, she would bend over to pick up a dropped pencil and I would immediately imagine her doggy style on my bed fucking me hard as she looked back at me with her green fuck me eyes. I would imagine pulling her back by her red hair and pinning her to the bed as I fucked her even harder. In my head, she came on my dick before I realized I should really get a hold of myself. Every time an episode like this would happen it would get me flustered for at least 20 minutes. I would quickly find a reason to leave the room to cool down for 19 more excruciating, breathless minutes. It was really getting ridiculous. Luckily, I was doing a good job at keeping my lust hidden. As far as I could tell, she still thought I was her normal, dorky, older brother. In my head I was anything but that, though. I was a dirty sister fucker who couldn't get his dick out from between his sister's beautiful, sexy, dreamy tits. Anyways, it had been a few days since I had an episode. I was reading up on some jobs in town when I heard a knock on my door. I opened the door and it was my sister. She had a very serious look on her face. Instantly, I thought she knew. I felt like I was about an inch tall and normally, seeing my sister at all would have made me rock hard. However, that look on her face forced all thoughts of sex from my mind. She looked up and said seriously, "Can I talk to you about something?" "Um, sure, I guess... what's up?" I hoped she wasn't about to say what I thought she was going to say. "I really need your help, can we close the door real quick?" she said as she came into my room. I shut the door and turned around. She had a pleading look on her face. "Ok look. You know how I have been trying to find a job right?" I nodded. "Well, that isn't exactly true." She said with a worried look. "Wha- what do you mean?" I asked with a shrug. She was obviously skirting around the issue. "Well, I've been making money. Lots of money actually..." She trailed off and looked away twiddling her fingers. "What is it? Just spit it out already." I said with a mini-laugh. She blurted her response out rapidly, cutting me off. "I'vebeenmakingmoneyonacamsite!" She said with a relieved sigh. Her shoulders sunk in relaxation. I didn't think I had quite caught all the words. "A what?" "Cam... site. I've been making money online on one of those cam girl websites." She actually looked quite comfortable at this point, having finally gotten it out. "Ok so what does this have to do with me? I'm super confused." I said with a shrug and a laugh. She got serious and worried again, wiping the smile off my face. "Well, I need someone to help me and I thought maybe you could..." I saw where this was going and out of fear I responded quickly and harshly. "Woah, what?! Listen, I don't have time for..." She cut me off. "No, it's not what you think. Listen, please hear me out." I nodded, curious where this was going while putting on my best fake, impatient look. "So, the thing is, I haven't been getting naked or masturbating or anything like most cam girls do. It's not one of those regular cam sites." I was intrigued. "It's a BDSM site. I kind of accidentally came across it. I realized that I could just talk dirty to these guys and they would pay me money BECAUSE I didn't show them anything. It's like they get off on me staying in clothes. They wanted to be controlled and dominated and I'm pretty good at that apparently," she said matter-of-factly. "So, what's the problem? It seems like you've got it figured out to me." "Well, I made a mistake. I'm about to lose my fans. You see, I don't have a ton of fans. It's more like I have a few fans that pay me lots of money so if I lose their interest, I'll lose my income. I kinda goofed up and told them that I had a slave. It really turned them on and I started getting tons of money. It lasted for a while, but now they just keep questioning whether or not I actually have a slave. I was forced to defend myself because I didn't want them to think that I had lied to them." She was looking extremely hopeful and pleading and... desperate, at this point. She kept going. "Listen bro, I know I'm too manly for you and all that and I know I'm your sister and you'd never do anything sexual with me but that's actually why you're perfect for this. All you have to do is just do what I tell you to on cam. You'll be wearing a mask so nobody will even know it's you. It should be cake." She paused and then said desperately, "I know you wouldn't touch a manly girl like me with a ten foot pole but please I need you to do this for me." She said all of it really fast and pleading. I was stunned. It seemed like she felt like this was the biggest favor I could do for her in her whole life. I made a show of pondering for a minute (I wont lie, I actually WAS on the fence.) I had no idea what might happen if I was to actually be sexual anywhere near her for real. I might come right away and then she would know about my perversion. Objectively, her request actually seemed pretty reasonable. It was just a favor between siblings and nobody had to know it was me. I played unsure, "What all will you be doing to me? As long as you don't touch my... penis" I said cautiously, "then everything should be fine. I see no real reason not to help you out." She looked worried again. Well, I kind of made another mistake. You see, the way it works is that when I put on a show, there are donation checkpoints. At every checkpoint, I have to do something specific. Some of the checkpoints require me to touch you." she threw her hands up, "I know! I know! I know! But please! Please, you can just imagine it's somebody else, just enough to keep yourself hard and that will be enough." I accidentally responded a little to honestly. My Used-To-Be-Tomboy Sister, Tommi "Yeah... Right!" I scoffed. She looked hurt. Oops, not how I meant it. "Hey, you don't have to be mean about it, I know I'm not that great looking." she said with a slightly down look. "No no! That's not how I mean it! Whatever... just... ok! I'll do it." I think it worked as she immediately cheered up grinned from ear to ear as my cock instantly became rock, pulsing, hard from ear to ear as I saw her smile. She jumped up and down and gave me a huge kiss accidentally right on the lips as she hugged me and said, "Thank, thank, thank you! I'll find some way to repay you I promise! Ok, I'll be right back." She ran out of my room. What... the... fuck... did I just agree to? I was fucked. The fear set in like a ton of bricks as I collapsed into the chair in my room with my hand on my head. I tried to calm my nerves, telling myself I was going to be ok and that I just needed to calm down. It wasn't working. I decided to just try to breathe. After a few minutes, I had just about caught my breathe when my door opened up again. I stifled a groan as my sister walked into my room wearing a tiny, tight black leather dress with stockings that nearly reached up to the bottom of the dress. The bottom of the dress barely concealed her amazing ass and her tits were nearly spilling out of the top. Her pale skin looked amazing contrasting against the black of the dress. I found myself salivating as I glanced back and forth from her face to her cleavage. In her hand, she had a leather mask with an attached ball gag. I reflexively pulled away, instantly feeling regrets. She noticed. "Oh my god! I know what that look means. Listen, you can't back out now, you already agreed." Her tone was very stern and I felt kind of powerless to do anything at this point. Little did I know that in just a short while, I actually would be powerless. "Hurry up and put this on and then come into my room quietly. Stay off camera until I call you over." She dropped it in my lap and pulled my gaze up to her face by my chin. She looked at me affectionately before slapping me hard in the face. SLAP! Her face turned serious, her green eyes ablaze. "Listen. I'm going to dominate you in there but I still love you, brother. Don't take it personally." She sashayed out of the room in her black heels. I looked back dumbfounded and shook my head to try to clear the reality of it all for a second. I put on the mask after a few seconds, trying to gain my composure. It was difficult to figure out how to get it on and even once I figured the zipper out it was still uncomfortable. I realized it was probably just supposed to be that way. My mouth couldn't close with the gag in it and my saliva was kind of pooling around my lips. I could barely see through the eye holes of the mask. I finally regained my composure I walked toward her room. Creeping in quietly, I shut the door behind me. Our rooms were set up in such a way that her's was all the way in the back of the house and there was a bathroom that we shared between my room and her room. That meant that we were basically not going to be overheard, which was good. As I walked in, I heard her speaking sternly toward her laptop. She was bent over, straight legged, typing on her computer while demanding for some faceless person to stop stroking their cock. I stood there admiring her ass as she bent over sticking it out magnificently. He must have spoken back to her. She responded with mirth. "Oh really? You'll meet my slave soon enough and if you don't stop mentioning it, I'll never... let... you... cum... again. Do you understand, slave? Now, take your hand off of your dirty, filthy, tiny, useless prick." She said forcefully, her mouth hanging open. She kept that face until a few seconds later when... Brrring! There was a sort of bell noise. My sister immediately started laughing and then said, "Haha, I'll take that as a, Yes Mistress. Oh and thanks, slave." she said dryly. Thanks for what? She stood up and began shaking her ass back at the camera. She made eye contact with me and turned away from the camera, putting on a "help me" expression. She didn't have this fully under control. I was torn. Part of me felt encouraged to help and then other part of me (which was mostly comprised of my eyes, cock, and brain, ok it was most of me) couldn't think about anything but fucking that sexy ass that was shaking only 10 feet away from me. It was surreal that this was happening. She walked over to me and put a collar with a chain around my neck. She leaned up and whispered in my ear, "I know this is difficult for you but please try to get turned on a little bit so that you can stay hard. It will be over soon, I promise." She kissed me on the cheek as she turned around and tugged on the chain pulling me into view of the camera. Bitch mode engaged... She began speaking for the camera in a disinterested tone. "So, here's my slave as all of you can see. Good slaves, like this one, don't question their mistresses but I understand that none of you are good slaves so I can't blame you. Maybe you can make it up to me. I'm sure you'll try... pathetically." It was difficult to see through the mask but it didn't take long for her to completely grab my attention anyways. I didn't know she could talk like this. It was a shocker. Somehow I was still flaccid. I guess it was nerves, it definitely couldn't be the heat this time, I chuckled inwardly. She turned toward the camera sharply and stated firmly, "Does anybody know what this slave has done wrong?" There were some tiny pings of messages scrolling across her chat room. "Good job! A good slave doesn't wear clothes unless his mistress has given permission." But, she never told me to take my clothes off. I began to try to speak but the ball gag was in the way. I only got a few muffled syllables out before she slapped me hard in the face. SLAP! "QUIET, slave! You'll speak when asked to speak, understood?" She turned toward the camera with an arrogant laugh, "Jeez, one compliment and he loses his pathetic little mind." Back to me, "Say, Yes Mistress." I responded through the gag, barely able to see, Mffffmffffff. "I can't hear you!" SLAP! MFFFFMFFFFF! "Good! Now stand up straight and don't move." She reached over and grabbed a pair of scissors before turning to me and snipping them in my direction. I was a little scared. "Don't move!" She began cutting my clothes off. I winced. She made a show of getting very close to my ear and loudly hissed for the camera, "I said don't move, slave," using this opportunity to whisper in my ear, "I'm sorry. I'll pay you back for the clothes, I promise." As she pulled away she sucked my earlobe into her mouth and bit down. It was pleasurably painful. In just a few minutes, I was in nothing but my boxer briefs and the mask. "There, much better. Now you get a tiny reward. On your knees." She put on a show for the camera as she sauntered around beside me affectionately grabbing my head in both hands. Just then, she forcefully crushed my face between her breasts. I was completely caught off guard as I was dipped in this heaven. I was getting really, really hard at this point. She smelled amazing and my head was swimming in soft, pillowy pleasure. She kept shaking her tits in my face for a good minute or so. I was throbbing and soon all I wanted was to move my lips to her nipple and suck. I couldn't reach them though through the dress and the gag. "That's enough, I can see you're enjoying yourself way too much, slave. This isn't about you." She pulled head up toward the ceiling by my hair and slapped me hard on the face as she said, "Wait here on your knees!" She walked off camera giving me a thankful look like she was sorry for putting me through this. I realized she must not be THAT sorry right as she came back with a pair of handcuffs. "Hands behind your back!" I complied. Click. Click. "Good, now stand up and walk toward the camera." She walked to her closet and rolled out what looked to be a large cross on wheels. I quickly noticed that it had straps all over it. Oh God. "Put your arms straight out slave." I did so. Brrring! After she said, "Thank You" again arrogantly, I realized that it must have been the sound that signaled a donation. She had me tied up in just a matter of seconds. There were two straps down each arm and leg and 2 straps across my chest. I was very immobile, I realized. "There." She said with a foxy smile, walking her hand up my chest one finger at a time. "Now you can't misbehave." SLAP! Somehow, I still hadn't learned to expect the slap. It took me by surprise. "I see you're getting nice and hard for me!" She said with a nigh imperceptible shakiness in her voice as her eyes jumped down to my cock. "Let's see just how hard you can get." She walked deliberately around me in a full sexy circle, grazing my skin here and there with her fingernails. When she got all the way around me. I realized that we were too close to the camera for anybody to see our faces. We were faced sideways. The camera had me in view from upper chest down to my calves. She was standing in front of me on one foot with the other knee bent tickling my chest with her fingernails. She leaned her face in close and then I felt her grab my cock. The sensation was immediately intense. My sister had her hand wrapped around my cock. It felt amazing. Her face was an inch from mine and her green eyes were a bit glazed over as she started to lazily stroke me. She was breathing heavily on my face as she picked up the pace and whispered so only I could hear, "Why does your dick have to be so big? It will be hard to belittle such a nicely sized dick." She said with a playful smile and a wink. Brrring! The "Thank you" was lazy and automatic. This is right about when the show really started. My sister turned around quickly after thanking the last guest and bent her knees, squatting almost all the way to the floor. Then, she stood up slowly, ass first as she slammed her perfect behind directly into my crotch. I couldn't help but groan through the gag as she started rubbing her ass furiously around my crotch while she was bent over in front of me. I couldn't move a muscle but even if I could I wouldn't have chosen to be anywhere else on earth at that point in time. I noticed there was some soft dance music playing as she ground herself against me. I could tell the viewers were loving it too as ringing was basically nonstop at this point. Brrring! There was no thank you. She looked back at me and had the sexiest, most arrogant look on her face as she ground her ass against me. Her point was made, "I don't have time to say thank you while I'm dancing." She threw her head up and arched her back as she really started grinding against my cock. Brrring!Brrring!BrrBrring! It was going off almost constantly for the next two minutes or so while I enjoyed the most sensual standing lap dance I had ever seen or even imagined in my life. Brring! Brring! It wasn't stopping. Just then, I remembered what she had said about the checkpoints. It sure sounded like it had to be approaching some sort of checkpoint if the ringing was any indication. I was worried that if she got too carried away, then she'd end up having to touch me. I prayed she would stop this amazing dance show for that reason. My dick on the other hand just wanted her to keep going. She did. I had to warn her. MFFFF! She looked back at me while grinding her ass against my crotch. "What was that, slave? What's wrong? Is my ass too good for you? Is it too much? Are you going to cum in your boxers?" Oh god, I realized. This is only going to make matters worse. Just as I was thinking it, there was a definite increase in donations. I sighed inwardly. "Too much for you huh?" She leaned forward, put her hands against the wall and started pushing back into my crotch, slamming her ass into me harder than ever. This went on for a minute or so as I groaned and groaned. The donations were incessant. After a bit, she pulled all the way forward and stood up and I lost that sweet contact between my dick and her ass. She turned her head back toward me with one finger in her mouth as she said seductively, "Oh I guess it is too much isn't it?" I was relieved. Just as she was about to turn around, she slammed back against me again, punctuating each word with another hard slam against my cock as my eyes flew wide open. "Well... that's... just... too... bad... now... isn't... it..." Each word made me groan loudly. I was losing it. She danced for another couple minutes to the music. I was getting harder and harder and I was really starting to lose my ability to think straight. My cock was crying for release. Brrring! Brrring! Brrring! After a little bit, they slowed down. She seemed to calm down a little bit. I think she realized that she was losing herself a little bit too much. She stopped dancing on me, which was a little bit of a relief. I felt like I might have come if she kept that up for too much longer. Luckily for me, I've always been the opposite of most guys I know of. If I'm extremely turned on, I seem to last for as long as I want instead of coming too early. This quality was definitely helping me to keep my dignity intact in this situation. She stood up and went over to her laptop and started chatting away. After just a moment she gasped loudly and then stood up and looked at me. There was dread in her eyes. Her voice was calm and collected, chastising even, while her face was apologetic as only I could see it. "Oh Good! I see we've hit a checkpoint tonight, you perverts! You useless pricks must think this show is somehow for your enjoyment. Well, I'm sure you've been stroking your cocks for me how you know I like so I guess you deserve a bit of a reward." "Oh, and thanks." She looked like she was worried I might kill her. I was confused. She came up close to me so she could whisper in my ear and said quietly, "I don't know what happened. I... they... It's never gone that high before. I didn't think it would get that high during a show ever. I can't stop now though. It went all the way past the checkpoint where I would have to touch you straight to... I'll definitely lose these guests forever if I stop now. Listen, this is going to require some help from you. You just have to pretend like you're going to cum every once in a while. I'll act like I'm not letting you cum until I'm good and ready for you to. Just stay hard please?" She said all this hurriedly with her hands on my cheeks. I was in a daze until I noticed she was grabbing the scissors again. She crouched down in front of me and started to cut my underwear off and I started to squirm a little bit. My cock was about to be free and then I would surely cum if she was really about to start touching it. What would my sister think of me then? I decided that I should stop this now to save myself. Mmmmffff. Mmmmmfff! I said with wide eyes as I looked down at her Cheshire grin. "Oh, no worries, slave. You'll get to come soon. Just let me get these awful boxers out of the way," she said with a pouty face. In no time, my boxers fell away and my 7 inch cock fell out toward her and bounced off her face. She gasped slightly. Just then, I felt her delicate fingers wrap around my cock and begin to stroke. This time there was no cloth between her soft hands and my hard cock. I wanted to shoot my load right there. I looked up toward the ceiling and exhaled the biggest breath of my life as she stroked me up and down. My sister was stroking my cock and looking up at me seductively with those beautiful green eyes of hers. "There you go, slave. How does my hand feel? Is it nice? Good!" She picked up the pace. "Are you going to cum for me?" I whimpered into the gag and my body started to shake. It was building and I felt like I might cum. "Yeah? Are you getting close? Are you going to shoot that load all over my pretty face?" I was screaming into the gag at this point trying to make it stop. Utterly terrified of what might happen if I actually came like this. It would probably hit her right in the face. But she didn't stop. She kept stroking and stroking, her electric green eyes never leaving my face. She had her mouth open between the filthy words that were coming out of her mouth. I wanted so badly to replace those dirty words coming out of her mouth with my cum. That couldn't happen though. She was my sister. I had to stop this. MFFMFFFFFFFFMFFFFF! I tried desperately to get her to stop as my cock inflated to the max, engorged with my impending orgasm. Luckily, she let go, but before I even realized what was happening, she was standing face to face with me. SLAP! It hurt this time. "You pathetic excuse for a slave! You aren't allowed to cum until I tell you to." She spit on my masked face and pulled my hair, "Do you understand?" I could only muffle thanks into the gag, though she didn't know what I was saying. At this point the donations were erupting. She leaned in and whispered hotly into my ear, "Holy shit, I actually thought you were going to cum for a second there. I think I got a little wet." She had a mischievous smile on her face when she pulled away. I had never seen her with that look on her face before. She turned away and to the camera. "There, that was your tease and denial! I hope you pathetic losers out there enjoyed it. That's all the reward you'll be getting... unless you hit ANOTHER checkpoint that is." As she said it, my heart sank. She was encouraging them. Did she completely forget that this had already gone way too far or did she just not care anymore? The smell of pussy on the air made me think that maybe it was the latter. She adjusted her dress before leaning over to her laptop again. This time she turned around with a huge smile on her face for me. I had a hunch as to what that meant. She shrugged at me as she happily confirmed, "Another checkpoint" as if to say, "Don't blame me big brother. I'm not the one that tied you to that cross and nearly made you shoot your cum in your own sister's mouth." My god! She was driving me insane. She ever so slowly walked back away from the camera and past me where I was standing tied to the cross contraption, feeling like I was about to be crucified, cock hard as a rock. As she walked, she reached behind her back and started untying the strings that held the dress together in the back. It dawned on me what was about to happen and my cock got harder than I thought was possible. It took forever but eventually, all the strings were loose. She stood on one hip as she looked back over her shoulder and then removed her dress over her head. As her panty-clad ass and back came into view, I was transfixed. She kept lifting the dress off her head as her middle back came to view and then her bra... wait where was her bra? The dress was off. There was no bra. She turned around holding her amazing breasts, one in each hand, wearing nothing but her heels, panties, and stockings. She looked to be having a great time as she slinked back toward the camera. She was just about to pass by me as she walked toward the camera when she turned suddenly, grabbed me by the back of the head and just as I saw her tits come into view, she smashed my face into her breasts. It was indescribably soft. Nothing mattered at that point as she fuck my head with her tits. Just as suddenly though, she was gone. She kneeled down and wrapped her breasts around my cock. She started to move up and down as I realized in a haze I was tit fucking my sister and it felt amazing. She moved up and down, looking up at me with that sexy smirk on her face. Her freckles made her look so innocent but no girl can be innocent with a throbbing, purple cock sliding in and out between her tits and this one was definitely not innocent. I begin groaning into the gag right away. I couldn't get enough and at this point, I just wanted her to make me blow my load all over her. After a while, she stopped. I looked down as she moved even lower. Her face was just below my cock head. My Used-To-Be-Tomboy Sister, Tommi "So, slave. Do you think you deserve my mouth?" I was speechless. She wasn't actually going to put my cock in her mouth was she? My lack of a response seemed to anger her. She stood, her face out of the view of the camera. SMACK! She whispered. "Listen, just bear with me. It's almost over. There's only one more checkpoint and it will probably be nothing. You're doing great. You're staying hard so... nicely." She said the last part between labored breaths and after flashing an embarrassed smile, kneeled back down. "You respond when I ask you a question, slave! I said, do you think you deserve my mouth? Are you going to be able to keep yourself from coming in my wet hot mouth? I know it will be difficult." She said with a pout, looking up with those big green eyes. If only she knew. MMMFFFF! I responded like a good slave but I wasn't saying what she thought I was saying. She smiled. "Good. I'm going to have fun with your cock now. You had better not cum!" She ever so slowly licked from my balls all the way to the tip of my cock. I was leaking precum pretty steadily at this point and some of it dribbled onto her tongue. She swirled her tongue around my cock head before smacking her lips and making an mmmm sound. Then, she took my cock into her mouth. My body went limp as she slid her hot wet mouth down the shaft of my cock. She was barely touching my shaft with her lips but it felt like she was blowing me at full speed. She hadn't even closed her lips around me yet. The tip of my dick hit the back of her throat and she just sat there for a second, not closing her lips, not moving at all. I could feel her breathe passing down my cock. My body was radiating heat like it was on fire. She began to draw my cock out of her mouth ever so slowly. Her lips were grazing me occasionally on the way up. I was disappointed just as I was about to leave the warmth of her mouth but just as this thought occurred to me, she took all of me back into her mouth in one go. She closed her lips and began sucking and bobbing like a pro. I couldn't breathe and my body felt like it was on fire as she sucked and sucked and bobbed and bobbed up and down, up and down. I had never felt anything this amazing in my entire life. I might have passed out, or come, I'm not sure which, but then I was saved by the bell. Brring! Brrrring! Brrring! Her fans seemed to be loving this. Not as much as me though, I thought. I was nearing orgasm and she kept sucking and sucking. I vaguely remember making uncontrollable noises through the gag as she gave me the most amazing blowjob I have ever and probably will ever have in my life. Just as I was about to come, she took her mouth off of me and let out a loud scream. I whimpered into the gag as I looked down and saw her coming on her own fingers as she gripped my thigh strongly. "AHHHHHH! I'M COOOOOMIIIIIINNNGGG!" Her body convulsed and she nearly lost her balance as she breathed heavily and shook out her orgasm. She had my cock in her hand in a death grip as she came. It was a truly beautiful experience. Her eyes came to as she stood after about 30 seconds of panting. All the while, donation after donation was rolling in. How was she not a millionaire by now? She caught her breath and went back to her computer. "Take notes, slaves. That is how you make your mistress cum hard! I think he deserves a reward, don't you?" She said but then made an audible pause. "Oh, well it DOES seem like we've hit another checkpoint. This one is guests's choice." She walked over to me and whispered, "Don't worry. I set this up with the guy to donate and then choose something simple. It should be a breeze. You're doing amazing by the way." She slapped me hard on the face for seemingly no reason as she smiled a somewhat crazy smile and turned back toward the camera. "So, what does the lucky winner want to see? A footjob? Maybe some toe sucking? What will it be?" There was a pause... "Oh! I see! Well, let me go prepare, then!" She walked off camera. Her body language showed dismay as she grabbed her hair in one hand. She stood like that for a bit before throwing a silent mini tantrum causing her tiny red nipples to bounce up and down. After a while, she turned to me with another apologetic look in her eyes. She walked back into the view of the camera and once she got close enough, she whispered, "Fucking asshole promised! He wants a tip tease! He told me he would ask for something tame. I'm so sorry, I know this is gross. I don't really have a choice though!" At this point I really started to freak out. She didn't know that I was this close to cumming and if a tip tease was anything like I thought it would be, we were in big trouble. Mmmffff!mmmmffff!mmmmfff! I tried and tried to get her to respond, to cut me loose, anything. I was a little sick with fear. All that I felt was a slight motion as I heard the sound of a crank. I was being leaned back. I was almost flat when the table turned around again and my top half was raised up slightly. Just enough to see the top of the camera. My cock was raging hard and sticking straight up. She gave me one last look of sorrow before she straddled my chest and sat down full on my chest. It was at this point that I noticed the smell. She smelled intoxicating. I could feel her wetness on my chest as she sat and I realized her panties were gone. "Alright then, slave. You get a special treat today." The donations were rolling in at this point. She began gyrating her hips as she rubbed her pussy on my chest leaving a small wet spot right in the middle of my chest. I was fucked. She leaned down and put her tits in my face again. This time, I was just trying to ignore it. Her soft breasts had my head surrounded in flesh. It was difficult but I managed to keep my mind about me. After a bit of that she sat up and slapped me hard on the face. SLAP! "So, slave. I'm going to ride the tip of your dick until I orgasm. You don't get to feel any pleasure out of this. All you get is the torment of being so close yet so far away from what you want the most." She began to slide backwards on me down toward my waiting cock. "How does that sound to you?" I knew exactly how it sounded. Amazingly erotic but incredibly dangerous. I was in trouble. She kept sliding back until my cock head reached her opening. It was so wet that I felt it immediately. "OOOHHH!" She gasped as she started to move her hips in circles. She was rubbing her clit on my cock and judging by the expressions on her face, she was loving it. "Oh, that pathetic cock is nice, slave. I like putting just the tip of it against my clit. It feels... so nice!" She said with a sharp intake of breath. I could tell she was losing control as her tits began to rise and fall with each moaning breath. She scooted back about an inch further and my cock went about an inch inside her pussy. Oh god, it felt amazing. I wanted it all but I knew that was the worst possible thing that could have happened right then. She wasn't stopping, though. "Oh, your cock feels sooooo nice. I'm going to ride it with just the tip inside until I come. How would you like that, huh?" MMMMMFFFF! I responded. "Oh, don't worry, slave. I'm sure you can hold out, she said with a wink." The look on her face alone was almost enough to make me come. It was the most incredible mix of arrogance, excitement, fear, and anxiety. She wasn't stopping and I got worried. She just kept sliding backward. Another inch of my cock slid into her wet, tight hole ever so slowly. I groaned louder than ever. I was almost fucking my sister at this point. This couldn't happen. I tried to lash out and break my bonds but it just caused me to shake as violently as the bindings would allow. This seemed to bring her to her senses as she started coming back up off my cock. She started fucking just the tip of my cock. It felt amazing but at the same time, It wasn't enough. I definitely didn't feel like I was getting closer to coming. Maybe this wouldn't be so bad. After about a minute of her fucking the tip of my dick, I looked up to her breasts. Her nipples were amazing. Nice, round little buds, pointed ever so slightly outward on a pair of white, slightly freckled tits that seemed to defy gravity as they barely swung while she gyrated. I could feel myself getting harder at the sight. I continued my gaze upward until I saw it. Her face... The mixed expression from before was gone. It had been completely replace with a carnal, frenzied passion. It looked like she had lost her mind completely. She was fucking the tip of my dick faster and faster. Every ten thrusts or so, she would sneak another eighth of an inch of my cock into her pussy. Pretty soon, she was fucking almost a quarter of my dick and it felt amazing. I wanted so bad to be actually fucking her at this point but it was still mostly the tip as I involuntarily tried to thrust deeper into her warm, wet cunt. This was when I realized that I was approaching orgasm. She was fucking enough of my cock that I was on a downhill ride to coming inside my sister and she didn't even know it. I started to protest. MMMMFFF! MFFFFF! MMMMFFFF! At every thrust I protested but eventually it just turned into groans of absolute pleasure. I was doomed. She just wouldn't stop slipping more and more of my twitching, hard cock into her wet, hot pussy. My hips were pathetically trying to fuck deeper. I was surely doomed. My cum was boiling up my shaft, about to blast off inside her and ruin everything. Luckily at about this time, the pace of the donations increased and she was broken out of her stupor for a second by the sound. Brrrring! Brrrring! Brrrring! She looked... was that annoyed? She turned around and faced the camera at this point. She started talking to her fans as she slipped just the tip of her brother's dick back into her opening. "You see this dick just barely inside my pussy? This is what a good cock slave looks like. Make sure you get a good look." The donations were coming in almost nonstop. "This dick only comes when its mistress wants it to unlike the lot of you. I told you I had a slave and you didn't believe me. The fact that you needed your mistress to prove it to you is punishable and trust me, you WILL be punished." She was still riding the tip my cock as she spoke. I was getting closer and closer to orgasm. I was losing my mind at this point. I just wanted to fuck. That was all I could think about. Please just fuck me. I wanted to come balls deep inside my sister's pussy. Just then, she stood up, turned around and slapped my pulsing cock hard. It swung about as she looked back and the camera. She turned the table so that the camera was ninety degrees from us, pointing at us from my right side as I was lying on my back. She straddled me and put the tip of my dick back into her pussy. It felt wonderful as I moaned uncontrollably, muffled by the gag. "See, slaves? I bet you wish you were inside this pussy right now. I bet you would do anything to be inside me right now wouldn't you? Too bad you can't handle it. In fact, this slave here is the only slave that could handle this tight pussy. In fact, I think I might just give this slave a little taste of this pussy here and now." Oh god, what was she saying? My orgasm receded a bit when she slapped me but there was no way I would be able to hold off for long all the way inside her. "You'd love to see that wouldn't you, you perverts?" Jeez the donations were rapid fire. I call bullshit that she only had a small number of "fans." It sounded like the whole damn internet was tuned in to watch her brother fucking escapade. "Well, I would say I'm sorry for you but I'm not. You deserve your punishment." She punctuated the words as she gyrated the tip of my dick just inside her. "You have been bad, slaves, and you... deserve... THIS!" Just as she said it, she slammed her ass down onto my thighs and threw her head to the sky as she screamed out. My cock went fully into her in one amazing thrust. I'm not sure how long this lasted but she sat on me, her hair hanging down behind her as her head was thrown back. Her back was arched insanely, causing her tits to look amazing as they sat even higher on her chest right above her flat rippling stomach. She was twitching slightly for about 15 seconds until finally she turned to the camera. I was deep in the wettest pussy I had ever felt and it was amazing. With a sly wink and a wave goodbye she ignored the donations and chat explosion as she slammed her laptop shut... Nothing happened for a few moments. It was dead silent except for her panting. Even the music stopped when she shut her laptop. You could practically hear my dick as it twitched inside her. She looked at me with that same crazed look as before and then started to lift up slowly as I shut my eyes tight, wincing in pleasure. It was finally over. I rejoiced. My cock screamed. She was coming off my dick excruciatingly slowly, millimeter by millimeter when she must have slipped because she slammed back down hard. It felt like I almost came as I reentered her warm pussy and my breath was knocked out of me. She then started to rise again only slam back down when my cock was almost out. I finally opened my eyes to look at her. I'll never forget what I saw. Her face was scrunched up as she looked deeply into my eyes. She was crazy with lust as she impaled herself on my shaft over and over while biting her bottom lip. It hit me that we were fucking and my dick twitched, almost firing off into my sister's young womb. She was riding the full length of my cock with each thrust. I was in and out of heaven over and over. My mind was lost as I groaned into the gag. My cock and my body felt like they would explode. She kept riding me, crying out with each thrust. "OH FUCK! OH FUCK! IT'S SO GOOD! I'M SORRY BROTHER! I wont be much longer! JUST... A BIT... MOOOOORE!" Just a bit more was right. It was when I realized that I was about release the biggest load of my life deep inside my goddess sister's pussy that I realized I should do something about this. This couldn't happen. I started thrashing as much as I could and screaming into the ball gag. MMMMFFFF! MFFFFFF!!! MFFFFFFF!!!! MFFFF!!!!! She slowed down a little. Oh my god, yes. She heard me. She understands. "Bro, you don't have to act anymore. Didn't you see me close the laptop? I just need to come on your cock. It's too much. It won't take long!" She said this between labored breaths as she maintained eye contact, still fucking me at about 95% speed. I kept screaming and thrashing as she slammed down onto my cock once, twice, three times. I was losing it. MMMMMMFFF!MMMMMFFFFF!!MMMMMMFFFF!!! Just then, a flash of panic crossed her face as she realized what was happening. It was soon replaced with those crazy green eyes from before as she said, "Oh my god bro! You're going to come aren't you? I'm not on the pill! Fuck! Don't cum, I just need... TWO MORE... SECONDS! Hold on just a sec broOOOOOOOHHH God! I'M COOOOOMMMIIING!!!" She went dead silent as her pussy gripped my cock and began contracting and sucking like it was hungry for my sperm. I couldn't take it any more. My sister was about to unknowingly milk every last drop of cum from my balls, straight into her womb, and there was not a damn thing I could do about it. I relaxed into my bonds and resigned to my fate. It was the most serene feeling in the world, deciding to let my cum go inside my sister. My cock got harder than it's ever gotten in my life as it started throbbing with the beginning of my own orgasm. "OOOHHHHH FUUCKKKK!!" My sister said as she was coming and twitching all over. Each squeeze of her cunt felt amazing on my cock as I felt my dick begin to pump sperm to the rhythm of her pulsing pussy. I felt the first spurt fly all the way into her womb. She screamed out, "YOU'RE THROBBING!!! I CAN FEEL IT!!! COME INSIDE ME BIG BROTHER!! OOOHH GOD FILL MY DIRTY PUSSY UP WITH YOUR CUM!!" She must not have cared that she was about to be impregnated by her brother. It didn't matter that she told me to, though. I was going to come inside her anyways, as deep as I possibly could. And I did. I blasted rope after rope of my cum into my sister as she came on my cock over and over. It felt like it lasted for days. Her pussy was squeezing my cock and my cock was blasting cum deep inside her pussy. Her womb couldn't hold all of my cum as it started to leak out of her while we were coming. I kept coming for a few more spurts as we both started to come down from our mutual orgasm. My sister collapsed on top of me with my still hard cock dribbling the last of my cum into her. It was surreal. I had never had an orgasm like that in my life. I will likely never have another one like it ever again. I just laid there, chest heaving. We stayed like that for a few minutes just trying to catch our breath. Eventually, I tried to speak. mmmffff! "Oh my god! I'm sorry. Let me get that off you." She took it off and untied my bonds with my cock still buried inside her. My jaw was sore from the gag. I looked at her affectionately and said, "I can't believe you did that to me!" She looked back in mock surprise and said, "I can't believe you came inside my pussy big brother!" Then, she slapped me really hard on the cheek. SLAP! This time I was free though. I rolled us over onto the floor with my still hard dick buried inside her. Her vibrant green eyes found mine as I lay on top of her. She looked afraid, excited, shy, sad, and happy all at once as she looked back and forth between my eyes, unsure. I was furious and horny and frustrated and she was obviously startled by my sudden attack. I looked deep into her eyes as I started to piston my cock in and out of her pussy. She opened her mouth wide and her eyes wider along with a strained, almost painful gasp. I was in control this time...