Pegging my gay panty wearing little brother

I caught my sissy little brother wearing my panties and other clothes and shoes many times and told I was going to peg him if I caught him doing it again. I showed him some websites on line and what it is all about. I'm a lesbian. A few weeks later I caught him wearing my panties again so I quietly entered his room and gently laid down next to him and told him to pull my panties down or will make sure everyone in school knows he wears girls clothes and is a f*****. He cried like a little b**** and begged me not to so I slapped his face and he did as he was told. I got in bed with him and lubed up a finger to lube him up and he was so tight. He said he has never put more than a finger in himself ever. I got so turned on knowing I was not only putting the little b**** in his place but popping his cherry to. He whimpered as I penetrated him. I was and still am such a top/dom woman and loved being mean and sadistic to f***** little brother. I f***** him for a long time that night I had lots of o******. The next day was Saturday and he couldn't sit and was walking gingerly. One night next week I came into his room after school wearing my strapon, he showed me he wasn't wearing panties and begged me not to peg him again it hurt so much. I told him to take off his underpants and tossed him a pair of my panties to put on. I walked over and slapped him around a little and he did as he was told. I pegged him again just as hard and nasty as I did the first time and orgasmed a lot. I told its ok to wear my panties and clothes but if I will do you whenever I want to or I will tell everyone you dress up and still f*** you. So i left and went back in to my room grabbed some panties, a bra, cute nightie and a skirt and pretty pink blouse and came back to his room. I gave him the clothes and told him to have a good time being girly I also gave him a small d****. I came back an hour or so later and found him dressed in panties, bra, skirt and blouse and when I reached up his skirt I could tell he was masturbating a lot. I asked if he was using the d**** and he said no so I told him to lift up his skirt and pull HIS panties down and lay on the bed and spread his legs. I took his hand and helped him guide it in to his butt and showed him how to f*** himself. I twisted on the vibrator part and he squealed. I watched him do himself for a few minutes and he got himself off really quickly. I said Mom and Dad will be home for dinner in an hour or so and walked out. He looked exhausted at dinner and he blushed a little when I asked if he had a lot of homework. I'm now 24, he is now 21 and out of the closet gay but still a closet crossdresser. I still invite him over to my place that I share with my girlfriend and he dresses up for us. We both peg him.

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  • Caught and pegged by lady I was housesitting for. Was a short teenage male with longer hair, but I secretly loved dressing up in girly clothes and kept my armpits and legs shaved. Now I had her house and clothes to myself.

    Enjoying myself getting dressed up daily and had even gotten her dog to mount me and f*** me up the ass a few times. Had styled my hair like a girl and put on some of her makeup and perfume. Had just taken the knot, when she walked in the door back early. Tried to quickly cover up but was caught on all fours with a skirt hiked up and panties showing and her dog by me. She seemed surprised finding me wearing her clothes, but her male cousin had and me, Aaron, was a sissy too. She then realized we were tied. Angered, she asked if I liked dressing up and letting her dog s**** me, and I nodded yes and let out a little moan. She told me to look at her and slapped me across the face hard several times. She took several pictures of me dressed and some closeups showing her dog was inside me and my face. She said Sissy E-r-i-n is a sick little pervert. I cried.

    Her dog finished, she told me to get on her bed on all fours. She came in later and lifted the skirt over my back and pulled down my panties. She took a belt and begin beating my bare ass with it laughing as I cried. She lifted her skirt revealing a large strapon. She said if Miss Erin was a sissy pervert that liked having a d*** up her ass, she would give me what I liked. She grabbed me and pushed the d**** in quickly as far as she could and f***** me hard. My ass was hurting from the beating and the f******, but she soon stopped and moaned and shook like she was getting actually getting off on f****** and dominating me. Then she started again.

  • The money for housesitting would go towards replacing her clothes I had worn while letting her dog f*** me.

    She threatened me with the photos of me with the dog and used me for her pleasure when she wanted to.

    She moved away a couple years later.

    A lesbian friend of mine found out my secret when she caught me dressed up getting screwed by a male dog. She began having me dress up and pegging me regularly saying it was practice for when she and her girfriend were in bed.

    I didn't mind. I enjoyed being dominated and she seemed to enjoy pegging me. She even liked watching me get screwed by dogs.

  • He wanted to get f***** up the ass and dominated, but was too scared to have a guy do it. It was fantasy of his that you made happen. Hate to break it to you sister, but he used you. He must have been so excited when a d*** threatened him with pegging, so he let you catch him wearing your panties and only put up token resistance. He surely wore your panties every day, hoping you'd catch him and follow through with your threat. As you were f****** him, he was dreaming that your strapon was the real thing, so you could come inside him.

  • I love pegging myself while dressed in pantiles

  • I was caught by my older sister while trying on my younger sisters knickers and school dress, I was thirteen at the time and had just started to get my pubic hair Angela my sister told me to pull my knickers down as she said I was a naughty girl and she was going to spank my bottom, I said No please Angie I'm going to get changed l won't do it again She said sternly Get your knickers down now unless you want mom to know about you. I reluctantly pulled them down to my knees but she told me to push them down to my ankles then to lift my dress I slowly lifted my dress I felt embarrassed as she started laughing then saying she could see why I was trying on knickers. She said my little girly clitty was really at home in knickers. My peepee was starting to get stiff so she got some sticking plaster and taped it back between my legs she said That's better now let's have you in the bathroom so we can finish yuor girly look. She took a pink lady razor and shaved my pubes into a small v shape now two years on and I'm still kept the same, once a week she tapes and shaves my petal , I have to be in my knickers so she can pull them down and walk me to the bathroom with my clitty tightly taped. Angie just loves to humiliate me as she shaves what she calls my girly mound and my sissy p**** which she says is in for a little Christmas present to make me into a proper little princess. I hate my little girl knickers but I do get used to wearing them every Friday so maybe I am a sissy afterall.

  • Just wish I had a sis like yours .I would buy her a vibrator to use in me

  • I too would love you to be my sister but I am still a virgin. That is I've never had any thing up my botty, my sister dresses me like a little girl in pretty dresses and panties and puts my hair in bunches with matching ribbons. I am not allowed to wear tights because she says little girls need to be able to sit on their potty and tights are just another thing to pull down. She keeps my peepee taped back and keeps me smooth and pink as she tells me this is how a little girl should be. She keeps me in nappies at night with tied on plastic panties so I can't touch my peepee.

  • Man i wish i could be your brother, i'd love to wear your clothes and let you f*** me whenever you want

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