Spying on Sister

This story contains incest and a trans character, if that is something that is not of interest to you, please do not continue. All characters are fictional and are over the age of 18.

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Growing up I always knew my sister, Mallory, was a trans girl. When she transitioned it wasn't a big ordeal in our family. Our parents understood, accepted and supported her. I was 8 and she was 14 at the time my parents sat me down and tried their best to explain to me what was happening. I didn't really comprehend it at that age, it just sort of slowly went to having a sister rather than a brother for my young mind. It wasn't really discussed much or brought up after that. We were just a normal family, well for the most part. We ate dinner together and all, but it also seemed as if everyone wasn't big on sharing what was going in their lives. It all seemed normal to me though. We didn't fight and argue, so it seemed like a healthy household to me.

Having a 6 year age gap, my sister and I weren't really close. She was in college by the time I started high school, so other than breaks and holidays, I didn't really see her too often for a few years. After she graduated college, when I was a senior in high school, she moved back with our parents and we would talk more but still seldom hung out. I was 18 at the time and she was 24. Although we were talking more, I still wouldn't say we were close, but we definitely had more of a sibling relationship than ever before. I never really thought of her sexually, that is until around the time this story takes place. If asked, and I really thought about it, I guess I would say I always thought she was pretty, but I never had any inappropriate thoughts about her.

In high school I didn't really go out much, and didn't have many friends, so it left a lot of free time, especially on the weekends. I would spend the majority of my late night free time surfing the web and looking at porn. I would watch the generic lesbian, amateur, or MILF porn mostly. After a couple of years of that, it seemed that it wasn't turning me on as much, so I subconsciously dove deeper into more taboo porn my junior and senior years. This deep dive lead me to begin watching incest porn videos primarily. Of course these were all staged, but it was the taboo fantasy of it all that made it hot. I came to realize the more taboo and naughty it was, the more it turned me on. I guess the fact that is was supposed to be wrong, and isn't publicly accepted, is what made it so hot for me.

When I started watching those genres with more frequency, I realized how horny it made me, and eventually I got to thinking about my sister. Was this just fantasy, or would I do something with her if given the chance? Then that took me down a whole new path. One night while thinking about my sister and slowly stroking myself, I decided I would watch trans porn. I watched a few videos and they turned me on like never before. Soon trans porn was all I watched. It wasn't a fetish for me, I had come to realize I wanted my sister sexually, and this was as close as I could get to having her.

One Saturday night, about 1 o'clock in the morning, I was sitting at my computer in my room, trans porn playing on the computer. My shorts were around my ankles and I was working my hard dick in my hand. On the screen was a trans girl in her mid 20s riding a very large cock. As she rode, her cock bounced up and down with each thrust. The way her semi hard cock was bouncing was one of the more erotic scenes I have ever viewed. I was wishing it was me that she was riding. More so, I wished it were my sister riding me. I also had thoughts of wanting to crawl through the screen and take her into my mouth as she rode this large one. I had absolutely never thought about sucking someone before, until now.

I was into this scene and was working close to an orgasm after previously edging a few times to other videos. Stroking up and down and picking up the pace, knowing I was going to blow a large load very soon. Just then , out of the corner of my eye, my attention was suddenly drawn to my bedroom door. I quickly shot my head in that direction where I saw my sister standing in the doorway, wide eyed.

"Oh shit, damn sorry! I just saw your light was on and thought you fell asleep so I was going to turn it off" she said standing there almost acting like everything was normal.

She was standing there for what seemed like an eternity, but looking back was only a 5-10 seconds. I was so shocked I didn't even think to cover myself, or even pause the video. I was certain she saw my hardness and also saw what I was watching. She simply turned and left my room, but not before I saw a slight smirk appear across her lips. I quickly closed the internet browser and pulled my shorts up and sat there, embarrassed. "What happened to knocking," I thought to myself. But she never knocked, she would just barge in. Not in a rude manner, that's just what she did. Which is why I always waited until I was certain everyone had gone to sleep before having a jerk session.

I thought about my sister walking in on me a lot over the next week. It had become a large part of my thoughts and I thought it must be tied to the amount of porn I have been watching. I started getting ideas that a brother shouldn't get about his sister. The more I thought about it, the more it aroused me that I had been caught by her. Those thoughts turned into me thinking about catching her. I thought about different ways I could "accidentally" catch her in compromised state, like she did to me. Surely I couldn't catch her now without it being obvious that my actions were intentional.

I came up with my genius plan during one of my late night jerk sessions the following weekend. I was going to install a spy camera in her room to try to catch her undressing, or hopefully something better. I found one online that was fairly cheap, about the size of a quarter in diameter, and I could also set it up to automatically sync to my computer wirelessly. It was motion activated so I wouldn't have to sort through tons of video. Also, with our rooms sharing a wall, I felt confident the wireless feature would work as intended.

Once the camera arrived I put my plan into motion during the next free window I had when my sister was at work. I set up the camera facing the door to her bathroom, and her bed was in complete view as well. I placed it behind a plant on her dresser, which seemed to hide it pretty good. I set it up the software on my computer and walked in her room to test the functionality. I walked into her bathroom and back out, then went over and laid on her bed. I went back to my room to make sure the file made it to my computer and to also make sure I could see everything clearly though the plant. Everything came out perfectly. The video was really good quality and I could see all the spots in her room where I thought it would be best to catch her in a state of undress.

I was so excited when she came home that I sat and watched the camera feed live as she went into her room. She walked to her dresser and put her purse on it and stood there for a few seconds. I was so nervous that she was going to block the camera with her purse. As she stood there sweat started beading on my forehead as I began thinking that she was going to find the camera. That would be just my luck, getting caught before I got to see anything. Turns out she was just getting some clothes from her dresser and headed towards the bathroom. That eased my nervousness a bit, but my excitement remained as I thought I might get what I was looking for on the very first night.

Luck was not with me as Mallory came out fully dressed with a towel in her hair. I was still able to admire her a little bit though as she had on a pair of tight pink booty shorts that showed off her trim legs and shapely ass. She also had a small white tank top that stopped just above her belly button on her flat stomach. Her breasts were small and I could clearly see her hard nipples poking into her tank top. Although this wasn't what I was after, it got the blood pumping to my lower region. To complete the anticlimactic evening, she simply crawled under her covers, played on her phone for a bit, then shut off her light and went to sleep. I on the other hand pulled up some trans porn and took care of myself, thinking of my sister of course.

The next few days were similar. No good action at all. I thought about moving the camera into her bathroom which would all but guarantee my seeing her naked, but I didn't know if it would be too far from my computer to sync the videos. It got to the point where I wasn't even excited to review the videos because I had been let down 3 days in a row.

The 4th day was a Friday. I came home from school, watched TV for a little bit, then we had dinner as a family like normal. Everything seemed normal until after dinner my sister came into my room. It wasn't out of the ordinary for her to pop in but she was asking me about my plans for the night and how late I would be up. She on the other hand was obviously dressed for a night on the town. She had on a tight fitting black dress that hugged her small breasts, and small curvy hips. It stopped a couple inches above her knees which left plenty of room to still show off her sexy legs. I tried not to look her up and down but I did steal a few glances. Her long brunette hair was also straightened and fell just below her shoulders. She had her makeup all done, complete with red lipstick. This may be one of the very first times I looked at my sister as a total package. She was really drop dead gorgeous. I couldn't believe it took me this long to realize it.

"I don't have any plans. James is going out of town with his parents for the weekend so there's really not much for me to do. I'll probably just play some computer games until I bore myself to sleep," I told her.

"Awe my poor Chrissy," she said in an almost fake pouting voice using a nickname I despised. "Well I'm going out with some friends but maybe if you're up when I get back you can show me how to play those silly computer games or we can watch a movie or something."

"Oooook," I said in a confused drawn out manner.

Like I said, my sister and I aren't really close so her wanting to hang out with me was rather odd. On top of that her wanting me to teach her how to play computer games after she had given me so much grief the past year about how much I played them.

With a chipper tone she said, "Hey I just want to see what is so cool about them. Is that OK?"

"Yea I guess. I can show you if I'm up when you get back I guess," I said. Trying to sound slightly annoyed.

"Alright, well don't play on your computer all night or you won't want to teach me when I get back," she said this as she turned to leave but not before she added a wink to her statement.

As she closed my door I thought how weird that whole scenario was. I shook it off and went to my computer a fired up my game. I figured I'd play a couple rounds then I'd watch some porn before going to bed. I wasn't overly concerned about being awake when she got home.

When I finally decided it was porn time, I thought I would first check the spy cam footage to see if there was anything good. I wasn't expecting anything, it was more of a formality so I could delete the useless clips to free up the memory on my computer. The first couple files were of her dancing to music and coming in and out of her room with laundry and folding it. Nothing spectacular at all. The next file I opened she was laying out the black dress that she had on when she came into my room. I thought if there was any good footage today it would be now when shes getting ready to go out. She walked into the bathroom and shut the door. I was crossing my fingers that she was showering because her dress was still laying on the bed which meant she would be coming out in a towel at the minimum and would have to drop it at some point.

The anticipation was killing my as my eyes were locked on her bathroom door. Eventually I saw the bathroom door start to crack open. She opened it very slowly and must have been standing behind it because I couldn't see her at all. Finally I saw her start entering the picture. To my amazement she had the towel on her head and she was completely naked otherwise. My eyes skipped past her breasts and immediately went to her crotch. My eyes were met with her dangling penis that was swaying back and forth as she walked. My jaw nearly hit the floor. I felt flush as I immediately grew to attention in my shorts.

She walked to the end of the bed and was looking almost dead at the camera. I figured she must be looking at herself in the mirror of her dresser. She had a bottle of lotion in her hand and she worked the cap off and dabbed some in her palm. She set the bottle on her bed and began working it into her arms, then moved to her chest and rubbed lotion all around her small breasts and took her time on her hard nipples. She got more lotion and started applying it to her flat tummy, then to my amazement, went to her beautiful package. She was working the lotion into her member so slowly to the point that I didn't know if she was really trying to moisturize it or if she was going to start stroking for an orgasm. She continued until it was semi hard. When she stopped and pulled her hands away it was hard enough to be protruding from her body with a slight downward curve which made it clear she wasn't fully hard, but it was so erotic nonetheless. Her cock looked so amazing to me and turned me on so much. I paused the video and lowered my shorts. I was at full attention and began stroking myself. Her penis appeared to be about 5 inches in its current state so I figured it had to be close to 7 inches if it were fully hard. She was completely shaved around it and the sack below appeared small and also bare of any hair. The sight in front of me was hotter than any porn I had ever seen.

I pressed play on the video and she continued moisturizing. Mallory turned her back to the camera and put her right leg up on her bed to apply lotion. This gave me a great view of her plump ass. I began to wonder if this were a live feed if I would have the courage to barge in there and take her from behind. It was a bold thought since I knew this video was from earlier and I wouldn't have to even weigh the option too seriously. She moved to her left leg in similar fashion, still giving me a great view. She then walked over and grabbed her dress and slipped it on. I was disappointed it was over even though I had been given the absolute best show since installing the camera.

I decided to continue watching then I would go back to the part with her stroking and jack myself to completion. She went into the bathroom and I could see in the mirror that she was doing her hair. Knowing that was going to take awhile, I fast forwarded until she came out again. She paced around the room a bit seemingly in deep thought. She finally walked over to her nightstand and grabbed something from the top drawer. I couldn't tell what it was but it was small enough to conceal in her closed hand as she walked to the dresser and retrieved something else, out of site of the camera. She then backed towards the foot of the bed and sat down on the edge. What unfolded next took me by complete surprise.

Mallory scooted back and sat on the bed but not before she pulled her dress up to her hips. She rolled back and lifted her legs in the air and exposed her ass and crotch, which weren't covered by any under garment. Her hands came into view holding a small bottle. She dabbed some onto her fingertips and began rubbing it on her asshole. I was stroking myself watching the scene unfold. Next she reached to her side and appeared with something shiny, silver in color. She began rubbing circles around her ass with it while using her free hand to spread her cheeks wider. She then began inserting the object, which I now realize was a butt plug, into her ass. Almost in sync with her inserting it, I shot my load all over my shirt. It caught me so off guard, holding off my orgasm wasn't an option.

Apparently satisfied with the positioning, Mallory stood up and walked to the dresser and when she came back into view she was pulling a pair of white panties up her legs. After she situated herself in her dress while looking in the mirror, she grabbed her purse off the dresser and took a couple steps towards the door. She then turned around quickly and bent down with her face right in front of the camera. She brought her hand to her mouth, then folded it down with puckered lips and blew a kiss. I was shocked. Completely shocked. I could feel my face heat up and I bet I was as red as an apple at that point. She knew. I was busted. I was dead meat.

I sat in awe, not moving. Then I got up and paced the room frantically trying to think of any explanation I could give to her. Should I go get the camera? Should I act like I don't know anything about it if questioned? My life was over. I was so embarrassed and full of guilt from my actions.

Then it dawned on me. Her conversation in my room, and her winking at me about being on the computer too much. Hell, she put on a show knowing full well I would see it. She couldn't possibly be mad if she did all that knowing the camera was there. But what did all this mean. She wanted me to see her? Could she have the same incestuous thoughts that I have? Is this some sort of genetic trait? I was admittedly confused. One thing was for sure though, she wanted me to catch her.

I laid in bed thinking of the events that had unfolded. I had so many questions. Also, I just wanted to crawl in a ball and not face any of them, or this situation altogether. I played out hundreds of scenarios in my head. I didn't know what I was going to do, or better yet, what she was going to do. My plan was to avoid her at all costs. Hell, I may just run away at this point to avoid any and all awkward conversations and having to admit what I had done.

At some point I finally dozed off. I didn't realize it of course until I was being gently awaken by someone moving my arm back and forth and whispering, "Chris, are you awake?"

I was groggy as I rolled over and saw my sister. "Fuck," I thought to myself. Here it goes.

Instant panic set it and my heart felt like it was beating out of my chest. Luckily it was dark and she couldn't see the fear in my eyes. I lay motionless but she obviously new I was awake by this point.

"I thought you were going to stay awake until I got home," she said in a quiet voice as to not awake our parents.

"What time is it?" I asked.

"About 1:30. I thought you'd be up playing on your computer still," she said softly.

My eyes widened when she mentioned the computer as I had a vivid flashback of her stroking her cock, "What? No, I fell asleep at like 10:30 I think"

"Oh, well since you're up now, can you show me how to play the game?" she asked.

"Mallory, I was asleep and I'm not getting up to play," I said in a hushed, slightly annoyed tone.

"Did you play a lot while I was gone or something?" she asked.

I paused before I responded, "No, I didn't play at all tonight."

She cocked her head to the side, "You didn't get on your computer at all?"

"Nope," I responded quickly but with an unintentional quiver in my voice.

"I don't believe you," she said as she looked towards my computer.

I didn't say anything. I just laid there.

"Well fine. I guess I'll just go to bed too," she said with a mock sad voice.

With that she turned and walked out. I laid there staring up at the ceiling feeling a mix of relief and anticipation because I knew this whole ordeal wasn't over. It might be over for the night, but at some point I was going to have to face the inevitable. I sat there for a few more minutes before glancing over and realizing she left my door open. "Dammit, Mallory," I thought to myself.