Jack And Jill 11

I should have been on holiday with my boyfriend, but I had dumped his cheating ass at the last minute. At the airport. A long train ride ahead of me to a home full of reminders of the bastard who, no doubt, would soon find willing pussy in Costa del Sol. Or a short taxi ride to my parents' place. My parents had also just flown away on holiday, but I knew where the emergency key was hidden.

Except the key wasn't there, and the front door was locked, but thankfully the door from the kitchen to the back garden opened. Inside, I dropped my bags, kicked off my heels, and went to look around. I could definitely hear something. Voices. Strange voices from upstairs.

I crept up quietly, even as it dawned on me that it was just the television - or the internet, probably, since it sounded an awful lot like porn, and it was coming from my brother's room. We both still had rooms here, though we had both flown the nest years ago.

He hadn't even closed the door. There was no reason to if everyone else was out of the country. I peeked carefully round the door frame - and pulled back in shock. I'm no innocent when it comes to sexual kinks, but I wasn't prepared for this. He was watching internet porn, all right, two women with cocks fucking a man - which was weird enough, but what shocked me was that my brother was wearing a dress and fishnet hold-ups. I recognised the dress. I had worn it the Christmas before. And those were probably my hold-ups too.

Jack is two years younger than me, and only a little taller, and has always been weedy and a bit effeminate. It wasn't that surprising the dress fit him so well. He was even wearing a bra underneath, padded with God-knows-what, giving him a voluptuous - if rather misshapen - figure. His lips were bright red, and his eyes dark with mascara, and long, blonde hair fell about his shoulders. It looked like a cheap wig from a fancy dress shop.

Most startling of all was the cock thrusting up from under the hem. It was quite possibly the biggest I had ever seen in real life. Certainly the longest. I had always known Jack was well endowed, but I had never seen it erect before.

The nice thing to do would be to go downstairs and make a lot of noise. Give him a chance to hide all the evidence of what he was doing. The really nice thing to do would be to let him finish before doing that. But I was already in a bad mood, with my ex-fucking-boyfriend, and from missing two weeks in the sun, and now because my little brother had turned a nice dress into a sex aid and would likely get cum all over it. I would never wear it again.

Taking my phone, I switched to camera (with the flash off) and starting recording. Only the tip of the phone protruded past the door frame, and I was able to watch Jack on the phone itself.

Watching someone masturbate gets boring quickly, especially if they're taking their time getting to the fun bit at the end. I nearly stopped recording - but then he did the most erotic thing I have ever seen.

Bending his head down and sticking his tongue out, he was able to lick the end of his cock as he continued to stroke it. He was stroking it faster now - and how I wished he was able to bend a little further! I watched the phone screen fascinated - my own private porn channel - and squirmed in delight as a fountain of cum erupted from my brother's cock, splashing against his lips and cheeks while he continued licking the convulsing member in his hands.

"Bravo!" I cried, and he screamed like a little girl. Sort-of. Laughing, I fled across the hallway into the bathroom and locked the door, giving myself time to copy the video into the cloud for back-up.

Jack banged on the door. "Ali!" he cried. "Don't!"

"I am going to put this on the internet," I shouted back, "and send links to all my friends."

"Please! No! I'll do anything you want!"

I smiled. "Anything?"

He barely hesitated. "Yes."

The upload completed. I opened the door. "I am on holiday for two weeks. Here. If you do everything I say during these two weeks - and I mean everything - then I will delete the video."

He nodded unhappily. "Okay."

The poor boy was a mess. In his haste to wipe his cum from his face, he had smeared lipstick across his cheeks, and his tears were leaving trails of mascara. "You can start by fixing your make-up," I said.

He blinked with surprise. "Yes, Ali," he said after a moment, curiosity sparking suddenly within the depths of his misery.

"Call me 'Mistress'," I said sharply. I was still angry enough with him to make it convincing.

"Yes, Mistress," he said. "Sorry, Mistress." He wasn't fighting it at all. Was this another of his fantasies? To be dominated by his own sister?

It took all my self-control to maintain my dwindling fury. He looked suddenly so sweet, and he was my brother, after all. And was this technically incest? We weren't touching each other, but we were both obviously a little turned on by my dominatrix attitude.

"And for God's sake go shave. I've never seen a girl with so much hair. I don't want to see a single hair anywhere on you. Except your head."

"Yes, Mistress," he said, and I dismissed him with a wave.

Closing myself in my room, I collapsed onto my bed, laughing until tears rolled from my eyes. Maybe breaking up with my ex-asshole and losing out on a beach holiday would be worth it in the end. I wondered how far I could push things with Jack before the whole incest factor creeped us both out.

Turning my brother into a slutty little girl would be so much fun. My initial thought had just been to torment him with it, but seeing him so receptive... Maybe this wasn't just a fetish. Maybe he was trans. Maybe instead of simply dressing him in my clothes, which was fine for playing in the house but not really for taking him out, I could turn him into a real girl.

I searched the web on my phone, looking for shops that catered to cross-dressing men and trans women, but mostly they were online shops. I couldn't find anything local. And what I wanted wasn't cheap - but I had potentially saved a tonne of money by not going on holiday, so after a long hesitation I pressed the 'Buy' button.

But it would be days before they arrived, and I had itchy fingers. I wanted some stuff immediately. I wanted to play with my new slave. During my searches, I had found a large sex shop that wasn't far away. I grabbed my purse, and the keys of my dad's car, and headed out.

*

Jack was still in his room when I got back. I opened the door to find him naked on his bed, carefully shaving a last bit of hair from his balls. "I've decided on a name for you," I said. "For the next two weeks, you will be my little sister Jill."

"Yes, Mistress," he said.

I tossed him the uniform from my last year at school. Black skirt, black cardigan, white socks and a white button-up shirt. "Wear this after you've showered."

Half an hour later he stood in front of me downstairs, a very embarrassed school girl with silly blonde hair and bright red lipstick, and an unconcealed erection.

"You took my clothes without permission this morning, Jill," I said. "And I'm guessing that's Mum's lipstick and mascara."

"Yes, Mistress. Sorry, Mistress."

"Perhaps, but words are not enough. You got cum on my dress. Naughty girls must be punished, or they will learn nothing." I pointed at the dining room table. "Bend over there and raise your skirt."

"Yes, Mistress," he whispered fearfully, and did as instructed. I wished it were my ex there, presenting his bare ass for punishment. I would have spanked him so hard...

With his hairless legs pressed together, so that his cock and balls were hidden from me, Jack was the very picture of a schoolgirl awaiting punishment from her teacher. I showed him my new leather paddle. "You deserve to be punished," I said, "and I expect you to thank me properly for each spank. Do you understand?"

"Yes, Mistress." He whimpered as I caressed his thighs with the leather.

I was in no hurry, and teased him for a while, before smacking him properly, though not very hard. He cried out, more with surprise than pain. "Thank you, Mistress," he said quickly.

I alternated between teasing and spanking, enjoying the increasingly rosy glow of his cheeks and thighs. I soon lost count - but I wasn't counting. I had never decided on a number. "Spread your legs," I said, and he did. I bent and peered between his legs at his cock. It was as hard as ever, with a thin strand of glistening precum trailing down. "You little slut," I said. "Stay in this position."

I left him there. From the sofa I had the perfect view through to the dining room and his bare, rosy ass, and through his legs to the cock that twitched mournfully. Phoning my best friend Fiona, I caught her up on all the gossip with my ex. "Hey," I said eventually. "Why don't you come spend the weekend with me? You can meet my new friend Jill." Jack tensed visibly, but didn't dare move. "You'll like her," I added. "She's a bigger slut than me."

Fiona laughed. "Not possible," she said. "I'll see you tomorrow."

I relaxed and watched TV for a while, catching up on my soaps while keeping half an eye on Jack. After a long while, his erection faded until his cock dangled limply. From my shopping bag, I took another new toy. "Put this on," I said, placing it on the table in front of him. "And give me the key."

Jack's eyes widened in fear at the sight of the steel cock ring and chastity cage. "No," he whimpered. "Please no." A moment later, he hurriedly added, "Mistress."

"'No'?" I said, as if surprised. "'No'?" I repeated angrily. "Have you learned nothing? Must I punish you again? Was I too soft with the leather?"

"Forgive me, Mistress!" he cried. "I'll put it on."

"Do so," I said sternly. "Then go and make dinner. I'm hungry."

"Yes, Mistress," he said.

I left him to figure out how to assemble and fit it. (If he hadn't been my brother, I would have done it myself.) Either the thought of wearing it aroused him, or my anger had excited him, but either way he had difficulty getting the ring and cage fixed. I switched over to Netflix and watched something scary with zombies, being not in the mood at all for romance.

At long last, Jack succeeded and brought me the key. I lifted his skirt to see his cock in its confining cage, struggling futilely to erect itself. I checked to see that it was securely locked in place. "Good girl," I said approvingly. "Now go make dinner."

"Yes, Mistress."

Half an hour later I was munching through pizza, a bottle of red wine at the ready. I made Jack sit cross-legged on the floor to eat his, and afterwards sent him to clean the dishes and tidy the kitchen. It was good to have a slave for this, if nothing else.

That done, I had him strip, and gave him a crotchless bodysuit to wear. He looked both kinky and sexy at the same time, the black lace covering him almost everywhere, and the shiny steel cock cage curving out and down. From my bag, I took a large realistic dildo with a suction cap.

"Hold this," I said, giving it to him. "Tomorrow, Fiona and I are going to watch you fuck yourself with this." Again his eyes were wide with fear, but he kept his mouth shut. "Tonight, however," I continued, "I just want to watch you suck it. Have you ever sucked a cock before, slut?"

"No, Mistress."

"I know you want to. I watched you lick your own cock, and I know you wanted a cock deep in your throat, filling your belly with cum. You'd like that, wouldn't you?"

His cheeks flushed bright red during my nasty speech. He nodded. "Yes, Mistress."

I took the cock from his hands, and walked over to stick it to the wall next to the television. "Well, here's your chance to practise."

"Yes, Mistress. Thank you, Mistress."

He knelt in front of it and took it eagerly between his lips to suck gently, then slowly used his tongue to wet the head and shaft with his saliva until he was able to wrap his lips tightly about it to suck properly.

I was impressed. He might never have sucked a cock before, but I had to wonder what else he had sucked. "I want to hear you, slut," I said, and he moaned in response.

I returned to the sofa and continued watching the zombies, who moaned with hunger for flesh as my brother moaned with hunger for a different flesh. I played with myself as I watched this double feature, incredibly turned on by the sight of my brother doing his best to deep-throat the huge dildo.

I had been calling him a slut, but I wondered how much he would enjoy being used as one. What would he do if surrounded by a gang of men determined to use his mouth and ass and fill him with their cum? Did I dare to find out?

I added my own moans of pleasure as I surrendered at last to a shattering climax.

*

"Wake up, little sister," I said, smiling cheerfully. I wondered how well Jack had slept and whether the chastity cage had tormented him. "Go shave and shower, and do what you need to do. When you're clean and dry, use your fingers to work some of this into your ass." I put a tube of lube on the pillow in front of his eyes.

He groaned. "Yes, Mistress."

"Don't take too long," I warned as I exited.

Naked apart from his cock cage and blonde wig, and looking very uncertain, he joined me downstairs. "Bend over and spread your legs," I said, pointing to the table.

"Yes, Mistress," he said, but hesitated when he saw what was waiting for him. On the table was a butt plug. Not a big one, but still daunting. This one was steel, and had a good weight to it, and had a large flat crystal under the base.

"Do as you're told, girl," I said impatiently.

"Yes, Mistress."

Once he was in position, I smeared more lube all over the plug, and pressed the tip against the tight ring of muscle. I pushed, but only the tip nudged inside. Jack whimpered nervously. "Oh stop that," I said. "We need to get your ass good and ready for the dildo. Now relax."

"Yes, Mistress," he whispered.

I pushed harder, and slowly, slowly, the egg-shaped head of the plug stretched him wider and wider. As the very widest part of the plug finally pushed in, I let it rest for a few seconds before pushing the plug in properly. All that remained visible was the large crystal. "Very pretty," I said.

I had him wear the school uniform again. "You'll have to wear your own shoes, unfortunately." The cut of the skirt was loose enough that the bulge of his caged cock could only be seen at certain angles. I spent a while helping him with make-up, keeping it understated. It would be strange enough seeing a school uniform on a Saturday. I didn't need to amp up the slut factor to get him noticed. It was more fun than I expected - just like two sisters applying their make-up together.

"Perfect," I said at last. "Let's go."

We went, but we went slowly. I could tell from his twitching that the butt plug was teasing and distracting him, and his anxiety at being dressed like that outside of the house made him constantly look round.

The bus was nearly empty. We sat together at the back, and he clenched his teeth at the sudden vibrations as the bus pulled into traffic. Lifting his skirt, I could see that he was engorged within his prison, the tip glistening with precum. "See," I said. "I knew you'd love this."

At the train station we waited for Fiona, who gave me a huge grin when she saw me, and we greeted each other like long-parted lovers. "This is Jill," I said, after.

"Hi!" she said. "I'm Fiona." Jack looked terrified, and clearly didn't know what to say.

Fiona frowned suddenly. "Jack?" She turned to me in confusion. "Is that Jack?"

"Not for the next two weeks," I said, grinning. "Jill is my little slut-sister and personal slave."

Fiona looked back at Jack, and after a moment burst out laughing. Juck meanwhile blushed a furious shade of red. "I'm sorry," Fiona said, catching her breath. "It's very nice to meet you, Jill."

In no hurry to get back to the house, we wandered about the shops, stopped for lunch, Jack almost silent the whole time while Fiona and I chattered away. We spent a while deciding on appropriate make-up for Jack, and bought him a cute handbag to keep it in. In Ann Summers, we looked at all the lingerie and sexy costumes, but nothing excited us. There were a few interesting toys, and Fiona surprised me by buying a vibrating plug for Jack. "That looks beautiful," I said, admiring the sleek black design. "I want one."

"I'll buy you one for your birthday," she said, laughing.

We jumped in a taxi and headed to the house, and the first thing we did was plug in the new toy to charge it. I ordered Jack out of his skirt, and sent him to make coffee and prepare dinner, and I watched Fiona watch him, her eyes lingering with curiosity on the steel cage in front and the glittering gem behind. "He's a prettier girl than I am," she complained.

"Don't be absurd," I said, and kissed her.

"I have a boyfriend," she said, after a while.

"I won't tell if you don't."

"I already told."

"What did he say?"

"To record it for him to watch later."

I laughed. "Give Jack your phone. We'll put on a show for him."

We did it in the kitchen against a backdrop of chopped peppers and carrots and pots of bubbling, steaming water and stewing mince. We soon had each other naked, clothes strewn across the kitchen as we exaggerated our passion for the benefit of our audience, present and future. If, somehow, the video ended up on the internet, there would be nothing to be embarrassed about - a sudden image came to me of my mum criticising me for not switching the cooker off and putting away the knives.

Fiona and I have never been romantic. We have been friends since childhood, and our comfort as lovers is based on an understanding that, for both of us, it is just sex. It started when we shared a boyfriend for a few months, and since then we have been meeting up a few times a year.

I sucked hungrily at her nipples and kissed my way down to a pussy that was completely bare. ("I lost a bet with my boyfriend," she explained later.) Even more surprising was the plug in her ass. "What the fuck, Fi?" I said. She had never been into anal play before.

Fiona laughed. "That was my birthday present," she said. "I agreed to wear it for two weeks in exchange for two weeks in the Seychelles. We're going in October."

"How do you like it?"

"Well enough. I've worn it for a month now."

"I hope he gives your ass a good fucking on those golden sands."

"I wonder if there's a cocktail for that. 'Anal Sex on the Beach', perhaps. Vodka, Schnapps, and..."

My tongue against her clit distracted her from her bizarre cocktail recipe.

*

By the time we had eaten and my slut-sister-slave had finished tidying the kitchen, the new toy was fully charged. Not only was it a beautifully designed vibrator, as a plug it would keep Jack's sphincter stretched nice and wide. The steel one he had worn all day had a much thinner stem.

I ordered him to bend over as before. If getting it in had been difficult, getting it out proved to be equally so. "See? This is why you need a bigger plug," I said. "Your ass is just far too tight."

But out it came at last. Fiona was ready with more lube for Jack's ass, and the new plug was lubed and ready. She pushed firmly, twisting as she did, and the plug eased its way in. Jack's breathing was heavy as he lay there.

"Are you going to thank Mistress Fiona for her gift?" I asked.

He turned to her. "Thank you, Mistress Fiona."

"That hardly seems adequate," I said. "If Mistress Fiona bought me a vibrating plug, I would get down on my knees and beg her to let me eat her pussy out."

Fiona smirked. "I'm going to remember you said that."

I echoed her smile. "I can't wait for my birthday."

"Well, you'll just have to." Since our steamy session in the kitchen, Fiona had been walking about wearing only her black vest and red lace knickers. Now she wandered over to the sofa and sat with her legs spread wide. "Although," she added, "my pussy is itching for a licking."