My Used-To-Be-Tomboy Sister, Tommi

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.