just a side note, cause i know how much hate not knowing: the age of the boy in this story is 14, and his sister is 16.
It all started when I started watching porn on the internet, I was horny all the time and seemed list I could masturbate forever. I especially loved anal scenes, with the girl having a massive cock shoved up her ass and moaning like no tomorrow. Watching all this porn, I started becoming aware of my own sexuality. I’m straight, but I always fantasise about being the girl in these porn movies, getting fucked, having a huge cock in my ass, or giving a blowjob. To fulfill these fantasies of mine, when I was alone in the house, I would go into my sister’s room and try on her clothes, trying to look as girly as possible. I loved wearing her short skirts the most, the girly look, my legs showing, and the way they barely covered my ass. I would dress up, and sit in front of my computer watching porn and jerking off wearing my sister’s clothes. Eventually, even wearing girl’s clothes could not satisfy my need to be those girls, so I got a little more adventurous. I grabbed a wide handle hair brush from our bathroom, lubed it up with some soapy water, and shoved it up my ass. The moment it went in I knew there was going to be pain, as moments later the worst pain of my 14 year life hit me like a train. I collapsed onto the ground and sobbed for over ten minutes until the pain went away. When the pain was gone, I got back up and tried to push it in more, there was no more pain, just a filling feeling inside my ass as I finally got it all the way in. Being 14 at the time and not very creative with this stuff, I couldn’t figure out how to move it in and out while at the same time be comfy while jerking off, so I just pushed it in as far as it would go, lay down, and did my thing. It took a long time to cum the first time, but when I did; it was the most intense orgasm of my life. After that, there was no going back.
A year after my experiments, I had tried anal with many objects of the house, trying to find the perfect thing, but never found a good one, the best I had was a different hair brush with a really long and wide handle. I would use it every day, dressing up in my sister’s clothes, putting on a porno, getting down on my hand and knees with it up and ass and jerking off while watching the movie. One day however, while I was doing this, my mind was gone and oblivious to the world around me, and I failed to hear my sister come home. She could hear the porno playing, and she could hear my moaning, so she came upstairs in hopes of catching me and ratting me out to our parents. When she opened the door she got the shock of her life. There on his hand and knees was her little brother, dressed in some of her sluttiest clothes, with a hair brush shoved up his ass, and the look of pure ecstasy on his face. She just stood and stared for a few seconds before grunting loudly for me to hear. Hearing her there, I wiped around, and saw my sister in the doorway, with a look of pure disbelief on her face. She didn’t say a word, she just walked out and closed the door, leaving me to finish.
When I was done, I took my sisters clothes off and folded them, and went to take them back to her. When I opened my door, there was a note on the floor that said to come to my sister’s room. When I got there, she was sitting on her bed, arms crossed, and a serious look on her face. I told her I had her clothes and tried to hand them to her, but she pushed them away and said she didn’t want them anymore, that I could keep them. Then I sat down on her bed next to her, and she started explaining about how much shit I was going to be in when she told our mother what she just saw. Hearing this I knew how much trouble id is in if our mother found out. So like any sibling would, I started to beg, plead, and try to make a deal with her. When the words, “I’ll do anything” came out my mouth, I knew I was fucked, because she just smirked, and said id better do anything she wants, anytime, or it’ll get out.
A few days later, if finally happened, my sister came into my room and told me to get dressed in her clothes and get in her room. I did as I was told, and went to her room. She had me sit down in front of her mirror and she started to apply makeup on me, I tried to ask what we were doing but she just said to shut up. When we were finished, she had me lay on her bed while she rummaged through her dresser. My eyes went wide as she pulled out a dildo from the drawer, a big one, at least ten inches long, and pink. She through it at me and told me to put it in and masturbate, because she wanted to watch me do it. I knew I had no choice in the matter, so I shoved it in and started to jerk off. It was really hard to get hard with my sister watching me, but I kept trying, eventually I got hard and started at it again. As I masturbated, I could see my sister in the corner of my eye; she had her hand down her pants and was playing with herself. I realized she was getting off on this. Noticing I was slowing down she yelled at me to keep going, and soon after I came, really hard. She stopped playing with herself and told me to get out, calling me a sissy, and a slut. So I walked out of her room, my head hanging, and her dildo still buried in my ass.
The next few times were pretty much the same, she would make me dress up and masturbate with the dildo in my ass, and she would play with herself, but eventually she got bored of it. So one day, she told me to stop, and she went over to a box in the corner, and pulled out a strap of some kind. To my horror, she put in on, and on the crotch portion of it, was a giant dildo, same length as the one in my ass, but at least double the thickness. She started laughing and saying stuff like “this is what you want, isn’t it you sissy? You want to dress like a girl, well, then I’m going to treat you like one and give you what you want.” Seeing this, I got up and ran for the door, but my sister was on my fast. She jumped on me and held me down while she pulled out some rope from her pocket and tied my hands behind my back, then tied my feet together. She dragged me onto her bed and positioned me properly and placed the head of the strap on to my ass. I started to cry and scream, so she grabbed a pair of her underwear and shoved them in my mouth. I still tried to scream through it, but then she slapped me hard on the ass, telling me to stop or id get the spanking of a lifetime, slapping my ass hard a few more times for good measure. I stopped screaming, but I kept crying. She repositioned herself behind me and shoved the head of the strap on into my ass, which made me squeal lightly and then she stopped. She then revealed to me, that this is how she gets off, she loves to dominate boys, and fuck them in the ass with this strap on. Then unceremoniously she shoved the entire length of the strap on into my ass making me yell out into her panties. She wasted no time starting slow; she ripped in out of my ass and shoved it back in, over and over. She fucked my ass for over 30 minutes, and by the end my ass was raw and numb. She then flipped me over onto my back and started fucking me again, this time jerking me off while she did it. while doing this she started talking dirty to me, calling me a little anal slut, a sissy, bitch, then at the end when I was about to come, she yelled out “You’re going to be my sissy slave forever!” and slammed the strap on in as hard as she could, which sent me over and I came so hard, I thought it hit the ceiling. Then she collapsed onto me, and we just lay there for a few minutes before she got up, slammed the strap on into me a few more time, and pulled it out. She took her panties out of my mouth and untied me, and I got up to leave. She stopped me and asked where I was going, and she pulled me over top of her knee, lifted up my skirt, and gave me a painful spanking. When it was over, she told me I could leave, but to remember what she said. As I walked out of her room, I said softly.... “I will be your sissy slave forever”