It’s no secret I have an open relationship with my offspring and other family members. In my family, sex is a good thing; something that is talked about and celebrated and practiced often. Therefore, I have very few rules in my household. But, the main rule is respect. Not just respect for our bodies, but respect for each others things. We just don’t walk into someone’s room and borrow their stuff without permission. My brother, who has been visiting for a week, knows the family rules; they were the same rules in our household growing up. Imagine my shock, when I took my beautiful daughter out to dinner to this really fancy restaurant and saw a woman in a dress just like one hanging in my closet; this pretty pink floral cocktail dress from Betsy Johnson. Her dresses are not cheap. I tapped her on the shoulder to compliment her and low and behold it was my brother in drag. And in MY dress. He acted very nervous and almost spilled wine on my dress. I could read the situation. He was on a date with a man and I doubt that man knew his date had balls. My brother had shaved, donned a wig, did his makeup flawlessly and apparently helped himself to my wardrobe. Pretty sure the shoes were mine too. I didn’t want to make a scene, so I just said, “Sorry, I thought you might be my sister, clearly I was mistaken. Enjoy your dinner.”
My daughter and I had a lovely meal and we plotted revenge on my brother. How long as he been wearing my clothes? I honestly had no idea he was a sissy boy. He has a huge cock too. He must have taped it to his thigh to pull off that outfit. I wonder if he dressed up when we were still living at home. Like ever borrowed our mom’s clothes? I was irate that he borrowed my clothes without permission, but also upset that he never confided in me he was a sissy boy. I could have had so much fun with him growing up playing dress up. He could have been my life size dolly. Well, my daughter and I beat him home and we had our revenge plan all in place. He wanted to play dress up, well we were going to play dress up.
He is obviously fond of pink, so we decided when he came home we would dress him up as a baby doll. He tried to apologize. Claimed he didn’t know how I would feel about his “feminine” side. Well, he knows darn well I am very open minded. He just wanted to wear that dress and knew if he asked I would say no. I told him when rules are broken, there are consequences. He had to take his just punishment. I told him to get my dress off immediately and return to the living room naked. He did as he was told. My daughter and I then sprinkled baby powder all over him, even his ass; making sure we got some in his ass crack. We then put him in a diaper with plastic panties to secure the diaper. He looked so embarrassed. We even painted his toes and nails a pretty pink. Then we dressed him in a pink satin dress with a matching bonnet, some little white stockings and did his hair in pig tails. I made him clean my house in that outfit. He had to get down on his hands and knees and polish the floor with little pink hand clothes. Took him hours. I gave him a pacifier to shut him up. And a bottle of warm milk to make him pee his diaper. His whining was pathetic. Don’t like the humiliating consequences, don’t do the crime. We named him Josephine.
After hours of snapping humiliating pictures and posting them on his Facebook page, and sending them to all his contacts in his phone, my daughter and I decided we were horny. We broke out the strap on we often use with each other and decided to tag team my brother’s sissy ass. I mean sissy boys do love it up the ass, right? His ass felt really tight too for a sissy. But we didn’t let that stop us. He was hard as rock too, so he didn’t mind the ass pounding he was getting. While I was fucking his ass, his niece milked his cock for him. She is the best little cocksucker I know. Then she made him snowball with her. It was so hot seeing them swap that load of cum back and forth, although not sure my brother enjoyed the taste of his own cum. I never understood that in guys. My cum tastes yummy. Anyway, by the time we were done violating our baby doll, we could see his regret; feel his shame. He looked sore, dejected and humiliated. I told him that I love him; that would never change, but from now on if he wanted to borrow some clothing, tell us first so we could help him play dress up. We are one big happy family after all, and there never should be secrets.
