A Brother's Secret

This story was the start of a Role Play right here in the Lit forums. I played the Dominant female cheerleader and the crossdressing sub brother was played by jacklangston. Unfortunately this is all there is to this role play, but maybe one day I'll add another chapter or two.

This story contains humiliation, domination, femdom, minor incest, crossdressing, cbt, and public nudity. If you don't like this go read something you do like.

*****

Our parents are out of town for the week, so it's just you and me. Whenever I'm home alone I like to dress up in your clothes and pretend I'm a girl. One day while our parents are gone, and you're at cheer leading practice, I decide to go to your room and dress up. You come back early because you forgot your pom poms. I don't hear you come in, and you catch me dressed up in one of your homecoming dresses. You think it's really hot, and decide to make me your little bitch.

I am Jack, 21/m, brown hair, blue eyes, 6'0, 130lbs, love wearing all of your clothes, bras, panties, dresses, shirts, costumes. I even make fake breasts from balloons filled with water.

*****

"What the Fuck are you doing in my room, WEARING MY CLOTHES?" Are you some kind of pervert, or do you just want to be some cross dressing sissy." I scream at my brother, when I came home to get my cheer bag, which I forgot when I left for school this morning.

I pulled out my cell phone and started taking pictures of my brother dressed in a hot pink mini skirt, knee high stockings and heels. and a tube top he stuffed with something that barely looked like a set of tits. I laughed at him trying to get up and stop me.

"You're gonna be my bitch now bro, or these pics go on Facebook, and get emailed to everyone you know including mom and dad. This is going to be fun." I smiled waiting for his reaction.

*****

I hear my sister scream, and quickly turn to see what's going on. My mind is racing, wondering how this could possibly have happened. I'm usually very careful. I just sat there stunned that she had caught me. Before I knew it, she had her phone out taking pictures of me. If they got out, I'd be ruined. I lunged at her to try to take the phone away, but she moved to the side and I fell on the floor. I had no choice but to start begging. "Please, sis, please for the love of god don't do this. Please just delete those pictures. I'll do anything! Please, please, I'm so sorry" I look up at her, tears in my eyes.

*****

I laugh at the sissy laying at my feet. Relishing the power I now have over my brother. I look down at him and smile. Not a kind loving smile, but a 'your ass in mine smile.' "Anything huh? Well then brother dear, things are going to change around here. First off when I come home from practice, I want dinner on the table and you to be completely shaved. I don't want to even see a hint of hair anywhere except your head." I walk over to my closet and start looking for something, "and you will be wearing this as you serve me tonight," as I pull out my Halloween costume from last year. A black French maid outfit. Complete with fishnet stockings and 8" heels.

"If you do this, I will consider keeping your perversions a secret. Don't do it, and everyone you have ever talked too will see you dressed like a sissy boi slut." Before he can respond I toss the outfit on my bed grab my bag and walk out of the room

*****

My sister asks "Anything huh?" and I shake my head yes quickly.

She tells me to make dinner when she gets home and to shave myself, then throws her French maid costume at me, the tight one from her Halloween pictures that I couldn't stop jerking to. She grabs her stuff and leaves me in her room, still in her clothes, surprisingly turned on. I had always been interested in dominant women, and she was hot, but I didn't like the fact that she had blackmail on me. She could post them to Facebook anytime she wanted! "Oh well," I say to myself "there's nothing I can do."

I go to the bathroom and grab my razor, shaving every inch of hair from my armpits, chest, legs, and finally my balls and above my dick. It felt so weird being completely smooth everywhere, although it did make my legs look more feminine, which was hot. After a quick shower, I put on her French maid costume, it was incredibly tight, not to mention short. It felt like my ass was hanging out. I put on the fishnets, which felt great against my newly bare legs, then squeezed into the heels. My sister and I were almost the same size except when it came to shoes, they were very uncomfortable.

I carefully walked down to the kitchen, which was a challenge in the heels, and started making one of the few things I actually knew how to, spaghetti, and waited for my sister to come home.

*****

I had no idea what had come over me when I saw my dumb ass brother dressed in my clothes. But the thought of controlling his life for the indefinite future was a real turn on. When I got to school, I went onto the locker room to change. As I stripped off my clothes I realized I was dripping. Since our cheerleader uniforms were white my arousal would be VERY noticeable. I went into a stall and began to rub my clit trying to get myself off so I wouldn't be so fucking horny. As I rubbed I pushed one finger into my pussy and started moaning. I must've gotten too loud because I heard a voice call out to me, "Anysa is that you?"

Shit I thought to myself so fucking close. "Yeah it's me," recognizing Paulette's voice. She was my BFF since we were in diapers.

"Coach Heidi is pissed you're late for practice. She sent me to find you. Do you need a hand or are you almost done." Paulette asked me.

I giggled at what she said, thinking about asking for a hand to finish up. We had kissed at a few parties playing truth or dare but neither of us had ever been with a girl. Paulette was more experienced with boys then me. She had been with 4 guys so far, screwing a total of 19 times. I only had 2, and been with them a combined total of 7 times. "I'll be out in a minute," I told her and when I heard her leave, I finished dressing.

I went out to practice and we did our routines for the upcoming game this weekend. After practice, Coach Heidi had me run 20 laps for being late. I finished the laps, rinsed off in the shower, and throw on my clothes and drove home.

I walked in the door, and smelled spaghetti cooking. I made a mental note to make sure my new toy learned to cook other dishes. I walked in the kitchen and sat down at the table.

"Sissy I've been home for 2 minutes and you have not greeted me properly, or offered me a beverage. I will have to punish you later. Now I want to eat."

*****

I set the plate of spaghetti in front of her as she complained about what a poor job I was doing. "I'm sorry, sister, I don't really know what I'm doing. What would you like to drink?" I was still a little wobbly in heels as I walked around the kitchen.

*****

"Bring me a glass of wine, and get yourself a plate," I tell the families new sissi boi, "I have plans for tonight and you will need your strength."

Once I have my dinner in front of me, I look at my plate. I stand up walk over to sissi, and slap her face. Before she can recover, I pull up the skirt exposing her boi clit and dump his plate of spaghetti right on his engorged cock.

I smile sweetly at sissi and tell her, "I know how much you like meatballs, and since you forgot to make some, I found these," I reached down and squeezed with all my strength, "some for you to eat. Now hurry up and eat we have shopping to do. But first lick my hand clean."

I held my sauce covered hand out for sissi to lick clean.

*****

I walk over to the cabinet to get a bottle of wine. Nervous when she says she has plans for me tonight. When I turn around, I'm met with a hard slap n the face. My skit if pulled up and I feel hot pasta and sauce all over my dick and balls. I'm met with more pain when she squeezes my balls hard. She tells me to lick her hand clean, so I take it in my hands and lick every inch until all the sauce is gone. Since she told me to hurry up and eat, I get another plate from the cabinet and dump some spaghetti on it.

*****

Once we finish dinner I tell my sissi to put on some of his own clothes, and to wait for me by the front door on his knees. I go and take a shower, dry my hair and brush it out. I throw on a tank top without a bra, and a pair of booty shorts and knee high boots with thigh highs, all in black. I add some black eye shadow, and lipstick giving me a very Goth look, but also very domineering.

I go downstairs and see my sissi is waiting for me. "Do you have your credit card darling brother," I say standing behind him, "If you want to be a real sissi we need to go buy you some clothes and shoes, and at least one wig until your hair grows out."

I walk in front of him, and stand there looking at him on his knees. "Don't forget, I have the pictures, and not only on my phone and my laptop, but on a thumbdrive safely hidden so don't even think about trying to disobey me, or deleting the pictures. From now on when we are alone, you will call me Sistress, and your name is sissi. One mistake, one disobedient act, one time making me unhappy and the whloe world will see you in my clothes. Understand sissi?" I stand there and waiting for my brother to accept the inevitable, which we both knew he would.

*****

I go to my room and change into some normal clothes, which felt a little strange after spending all day in a dress. I went down by the door and got down on my knees, waiting the whole time it took her to get a shower and dress.

She came down and stood in front of me, looking incredibly sexy with all her black on, while I listened to her threaten me. I was getting turned on again. She asked if I had my credit card, and I said "yes." Then she told me to call her Sistress, which was even more of a turn on. She asked if I understood and I replied "Yes, Sistress." With that we went out to my car, me in the drivers sat and her in the passenger's seat.

*****

I told sissi to drive to a local clothing store known for it's skimpy outfits. Most of the customers were hookers and strippers. We parked in the lot and I saw it was fairly empty. I walked up to the door and waited for sissi to catch up. sissi opened the door for me and I walked in stepping hard on his foot whispering, "Don't ever make me wait," and continued into the store.

I went up to the first clerk I saw and told her in a loud voice, "My brother and I are going to a pimp's and ho's party this weekend. we decided that I would dress as the Pimp and he would dress as the ho. So we need a whole outfit for him, shoes to wig, maybe more than one so he can change if he gets covered in cum."

The saleslady laughed saying, "That sounds like a lot of fun. I wish I was going," She looked my brother over and lead us to a rack of material that hardly qualified as clothing.

"Perfect," I said looking at the frilly material and girly colors. I began to go through the outfits looking for some to have sissi try on. Meanwhile, sissi was getting sized for shoes. "Something strappy, and toeless, which means a manicure and pedicure too."

The sales girl looked at me strangely and gave me a quick smile. She went to find shoes while I pulled out 3 outfits for sissi to try one.

First was a purple and black bathing suit that exposed more skin than it covered. Lots of straps and shiny buckles. Next was a little blue schoolgirl skirt with a white button down short sleeve blouse and white thigh high stockings. Finally there was a nice red cocktail dress, not for parties but allowing easy access for a cock to go in the wearers tail.

I handed the outfits to sissi and told him to go try them on. I started walking around looking for underwear and the proper decorations for a sissi.

*****

She took me to a local outfit store, and my heart was pounding I was so nervous. She made it to the door before I did, and I was punished by a hard foot stomping. She practically told the whole store that we were here to buy me girls clothes, and there was something about me being covered in cum, I was too embarrassed to notice.

While I was fitted for shoes, my Sistress was picking out skimpy outfits for me. I couldn't believe all this was happening. She dismissed the shoe lady and gave me the outfits to go try on.

In the dressing room I started with the purple and black bathing suit thing. I undressed and put it on. It was tight, and you could very clearly see my rock hard bulge showing through. I looked good though, it'd be even better with breasts, I thought to myself.

Out of habit, I started touching myself and stroking. I didn't want to cum yet, but this was all so erotic. I was about to explode. Hopefully my Sistress wouldn't walk in on me...

*****

I found the perfect pair of shoes to go with the school girl outfit. I walked to the dressing room and threw open the curtain. sissi had her boi clit sticking out the leg hole and was rubbing it.

"YOU REALLY ARE A FUCKING PERVERT, AREN'T YOU," screaming so loudly everyone in the store looks over and sees sissi in his clothes and his boi clit sticking out. I grab the empty hanger from the floor and start to beat the boi clit into submission, "You will not ever get hard or cum without my permission. Your body belongs to me now! l and only I can grant you release. Do you understand you freak?"

Without waiting for sissi to reply, I drive my knee into his groin, and step back, "Now hurry up and try on the other two outfits, we still have more stops to make, and leave the curtain open, I don't want you to play with yourself."

Jack tried on all three outfits as the clerk and everyone else watched him. I made him buy all three outfits, with matching shoes, and purses. I made him wear the schoolgirl outfit out of the store.

I took Jack by the hand and lead him into the tattoo shop next door. I told Jack I wanted him to get his navel pierced, and maybe a tramp stamp too. Jack's face blanched, but I gave him a threatening look and he hung his head.

After his belly was pierced, I decided to have him pierce his ears too. I got him big gold hoops for his ears, and a big red ruby for his navel. Jack looked deliciously girly, and he paid and we left.

As Jack drove home, I reached under his skirt and started to stroke his erect boi clit. I Took a firm grip on it and told him, "One traffic violation, and you don't cum for a month. If you cum before we get home, I send these pics to mom and dad."

I smiled as he tried to drive while I was bringing his perverted fantasies to life. I began to plot more ways to torture him, and I hoped he would play along.