Ms. Carter and Miss Candy Ch. 04

"I'm sorry," Mitch said, "but this is part of the rules."

Then he walked out of my bedroom, leaving the door open. Russell's friends—Thomas, Keith, and Mark—strode into the room with smug looks upon their faces. Mark was perfectly healthy. Russell had lied to me about Mark's injuries. Mitch had lied to me about Mark breaking into his home. They were all in it together, and now they had me exactly where they wanted me.

"I'm sorry, Mom," my son was standing in the corner of the room wearing one of Miss Candy's wigs and a sundress. "I'm so sorry," Russell said, while he grinned at me.

Hands reached out to grab me and spun me around. There were cocks everywhere.

Then my alarm went off.

I wasn't certain if I had been more terrified or aroused during that dream.

-----

It was 5:00am Wednesday morning. This was a school day, but I didn't need to go to work. My tongue stud was still healing and would be extremely difficult to explain as a teacher. At least I was getting better at speaking. My voice wasn't clear, but I could be understood.

I shut off my alarm and tried to plan out my day. Mitch hadn't ordered, or even suggested, anything for us to do yet. I hadn't seen or heard from him since the night before when he ate my pussy and fucked the life out of me. It occurred to me that Mitch had probably given me more orgasms the previous day than anyone else had in my entire life - except myself, of course. I remembered and fucked my fingers for an intense hour or two. I started laughing at how amazing that moment had been, but it quickly turned to crying that I had been so deprived before that.

Russell came into my room. At some point recently we stopped closing our bedroom doors. Probably shortly after I sucked his cock when Mitch wasn't around. Maybe it was after I sucked my son's cock in front of a room full of strangers. Either way, he entered my bedroom to find out why I was crying. It didn't bother either of us that we were naked. I dried my tears and looked down at my boy. There was something very wrong that I had never noticed before.

"Is that?" I stammered out. "Are you wearing a penis cage?" My son's face flushed red, then he tried to hide it with his hands.

"It's not what you think," Russell told me, "Mitch let me keep the key."

My 18-year-old son and I were being blackmailed by another 18-year-old boy. Apparently, one of Mitch's latest demands was for Russell to wear a penis cage, but my son thought it was okay because Mitch let him keep the key. Well, I guess that was better than the alternative.

"That's just vulgar, young man," I said with mock seriousness, "If you are going to wear that, you should at least trim back your bush." We laughed like only family could. Russell said he had been thinking about that, and asked if I could help him. Thanks to laser hair removal, I hadn't shaved since I was about his age, but I said maybe we could pick up some razors and such at the store later today.

"Thanks, Mom," he said, then turned around and went back to his room. Somehow, I wasn't surprised to see the little blue jewel back there.

"My son is wearing a butt plug and a penis cage," I thought to myself as I rolled onto my side and went back to sleep.

-----

Master - Bitch needs to do something re hair. Everything from the neck down.

The message arrived while we were eating breakfast. In a break from tradition, neither of us had bothered to shower or get dressed yet. Russell looked a little uncomfortable sitting on the hard wooden chair without a cushion. No surprise given his latest accessories.

I started typing a response, that we were planning on shopping for razors this morning, when a new text message appeared.

Master - Tara will be there at 10am. See you at noon

"Who's Tara?" Russell asked, after I showed him the message.

"Tara is the stylist who helped me on Saturday." I decided not to mention that she was also Mitch's sister. It wasn't exactly private knowledge, but after visiting their parents' home yesterday, I wanted to say as little as possible about Mitch's family.

"We should both get showers," Russell said, between spoonfuls of oatmeal, "and at least one of us should get dressed."

Somehow, we decided it would be more efficient to shower together. Given how comfortable we were naked together and my son's cock being locked up, it just seemed practical. Russell may have spent a little too long soaping my breasts and I might have spent a little too long on his lower back, but it really was faster than both of us showering separately.

I took my time getting ready. I wanted to show Tara that I really appreciated her efforts the other day. By the time I finished with the outfit, the cosmetics, and the wig (the long 'natural' redhead, trimmed to just above the shoulders at the sides, but long and straight down to mid-back) and dolled myself up, I think I could pass as Russell's older sister—and not much older, at that.

Russell had a more difficult time deciding what to wear. He wasn't sure whether he should wear briefs or panties; a sundress or shorts and a shirt; etc. He kept pacing back and forth in the nude trying to make up his mind.

"Russell," I said, "it doesn't matter. Just put something on."

"First impressions matter, Mom," my son responded.

My heart skipped a beat. I hadn't told Tara who I was or that I was being blackmailed; but I did mention that my son was almost the same age as Mitch. Tara would know that we were mother and son, and even if she didn't see 'Mitch's SLUT' tattooed on my back there was no way she wouldn't notice 'Mitch's BITCH' tattooed on my son. Especially, since she was here to remove all his hair.

I frantically grabbed my phone and sent out a message to Master: Tara knows I have a son. She'll see his tattoo.

It was just before 10:00am. There was a knock at the door. I looked up in horror while my son wrapped himself in a towel and went to answer it.

-----

"Hi, I'm Tara!" I heard the bubbly explosion greet Russell at the front door, "You must be Jessie! So glad to meet you!"

"Oh, um, hi Tara," my son stammered, "I'm Rusty, er, Russell. You can call me Russ if you like." I turned the corner and saw Tara standing there with a large suitcase in each hand. Was she moving in, or was all that just for what she was doing to Russell today?

"Does Miss Candy live here?" Tara answered, a little confused.

"Yes, I do," I announced myself. "Hi Tara! Russ, help her with her luggage, won't you?" Tara shoved her way through the door and put down the suitcases by herself. Russell closed the door behind her. Tara hugged me closely and then held me at arm's length.

"Candy!!" she exclaimed, "you look younger every time I see you!! I'm hella impressed!"

"It's all thanks to you," I complimented her. Tara let go of me and spun around to Russell.

"Let's try this again," Tara said as if speaking to a very slow person, "I am Tara. This is Candy. And You. Must. Be. Jessie." Russell wasn't slow, and this time he picked up on it easily.

"Oh! Hi Tara," my son tried to match her enthusiasm, "I'm Jessie, apparently. How was your trip?"

"Much Better," Tara remarked, "now next time, don't go flashing your tits to the whole neighborhood when you answer the door!" I couldn't tell if she was scolding him or joking, but 'Jessie's' nipple rings were on display.

-----

For ninety minutes, Tara and Russell disappeared into the hall bathroom. I paced around the house for a while, then decided to start preparing lunch for four. I paced around the house for a while, then decided to peek through Tara's luggage. It seemed like she had a mobile hair salon and maybe two weeks of clothing and wigs for each day. No shoes or underwear, so I guessed she wasn't planning on staying here—unless she had more bags in her car. I peeked out the window and looked for a car I didn't recognize, but nothing was parked out front and beyond that, they were all cars I didn't recognize. Maybe Wendy was right, we'd lived here for years yet I never paid any attention to our neighbors.

I sat down in the recliner and flipped on the TV. I didn't find anything good, but there was always something. Finally, Tara emerged from the bathroom. I heard the shower kick on. She found me immediately and plopped down on the couch to join in the finest late-morning crap TV.

"So," I said without thinking, "I guess you know some things you shouldn't." I couldn't help it. Even though she had been nothing but courteous and went out of her way to play pretend; the fact that she knew about my "family situation" weighed heavily on me.

Master still hadn't responded to my earlier message.

"Have you ever licked kitty," Tara said, turning to me. I sighed. So, this would be the price of her silence. Mitch had told me she was a 'dyke.' I would provide her with sexual services just like her 'little brother.'

"Not in a long time," I said, "but I think I still remember how." Tara stood up and walked over to where I was seated. She got right up to the edge of the recliner and pulled down her skirt. I looked straight ahead and couldn't believe what I was seeing.

"You might have a little difficulty with this one," Tara said while flashing me her caged penis. She pulled her skirt up and sat back down on the couch.

"Honey," she said, "We all have our secrets."

"Does Mitch know?", I blurted out, stupidly.

"My little brother wouldn't like it if I showed you that," Tara commented, "but yes, of course he knows. If we're sharing secrets, can I ask you something?"

"Of course," it seemed like neither of us had anything left to hide from one another.

"Is that little shit blackmailing you two?" Tara asked rather bluntly. Well, it turned out there still was something that needed to be hidden after all.

"If he were," I posited hypothetically, "Could I even tell you?"

"Of course," Tara responded. "You can trust me, honey."

"Let me rephrase," I spoke to her like she spoke to Russell, "If He Were Blackmailing My Son And I, Would I Even Be Able To Tell You." Tara was the smartest person in her family, but not the sharpest knife in the drawer. It took her a little while to process this, but eventually she got it.

"Well," she said, "let me put it this way. My little brother and I shared a room when we were growing up. I couldn't exactly hide who I was from him. Somehow his friends found out too. Given your experience, I guess you can figure out how that went."

"How old were you when he—" I started. I couldn't imagine. I didn't want to imagine. It wasn't just him. He brought his friends along. I really really didn't want to imagine.

"Honestly, I don't remember," Tara told me. "I'm pretty sure Mitch was the first one to use my mouth. I'm also pretty sure he wasn't the first one to use my boypussy. My teenage years were just kinda a blur of cocks and suicide attempts."

"I can't even—" I started to say, "is there anything I could do?"

"Not then, not now," Tara said, "but that's not the question you should be asking."

"Jesus Christ," I exclaimed, "were you a student of mine?"

"Not that I know of, Miss Candy," Tara answered, "but again, not the right question."

My mind swirled with thousands of unanswerable questions. This beautiful woman in front of me was raped and used by her younger brother and his friends for years. She attempted suicide more times than she could remember. And despite all this...

"Why are you," I stammered. "How is it that you seem to be friends with that son of a bitch?"

"That's the right question," Tara complimented me, "and the answer is, it's complicated."

"Yeah," I thought about my own feelings toward my blackmailer. "It would have to be."

"It would be easy to say that he's family," Tara started, not realizing I had met her parents, "but that would be bullshit. The truth is, despite everything, I never did anything for my little brother that I didn't want. His friends were another matter."

"When he found out," Tara looked at me with a seriousness that didn't sit right on her face, "about my suicide attempts, and what his friends were doing, well..." She trailed off for a bit before answering flippantly, "I've never seen those friends of his again. I doubt anyone has."

"That," I said with equal parts seriousness and dark comedy, "sounds like the Mitch I've come to know."

Clearly, we both had questions for each other, but it was close enough to noon. We were interrupted by Mitch's knock at the door.

-----

"What are you ladies up to?", Russell/Jessie asked when he came out of the bathroom and met us in the living room. My son was completely smooth and clean shaven, except for his eyebrows and the new haircut on his head. It was shorter than before, but longer than a buzzcut. It was too manly to be a pixie cut. In fact, it accentuated his manly features. Which was just bizarre because everything below his face looked elegantly feminine. Even the pink cock cage looked exceptionally feminine now that he was completely clean-shaven.

"Two hours wasn't enough time?" Mitch asked. Russell/Jessie hadn't noticed the man standing there talking to us.

"I told you it wouldn't be," Tara responded. "We've gotten her this far. Remember how long Candy and I spent shopping before she was ready for you!"

"Whatever," Mitch said, then he gestured to my son and twirling his finger, "Turn around." Russell/Jessie spun around on his heel to show us his backside. Any thought of 'him' became 'her' as my mind suddenly screamed, 'OMG! She's HOT!'

"I guess she'll pass," Mitch agreed, then asked, "what's for lunch?"

-----

The four of us sat around the kitchen table eating lunch. For basic decency, "Jessie" had a towel wrapped around "her" waist. Mitch had said she should stay naked, but Tara overruled him.

Eating a meal with Tara there was the polar opposite of Mitch. She never stopped talking, except after she coaxed someone else into talking. Mitch was his usual taciturn self, but she even managed to get him involved in the conversation. Unlike my experience with her on Saturday, I didn't find myself or Jessie replicating her accent or inflections, but that was probably because we were still struggling a bit with our tongue piercings. However, we did try to match her energy and enthusiasm. With all the conversation, it took us almost an hour to eat.

After lunch, Mitch sat in the living room watching TV while 'us girls' brought Tara's suitcases back to my room and swarmed on Jessie/Russell trying on clothes and wigs. Then we stripped her out of everything again and spent time teaching her to do her own makeup. She was a little slow on this part.

"Haven't you ever watched a YouTube video?" Tara demanded, while scrubbing another failed attempt off my now-daughter's face. Jessie hadn't. Russell had never even considered make-up. Even after we went shopping for sundresses, that part of the process had never even occurred to him. Honestly, I wondered if Russell had ever considered cross-dressing or anything like it. He sat at the mirror. I could see frustration on his face.

"Here," I said, taking over after Tara finished drying his face. "You don't have to learn all this in one day. Let me make you beautiful for Mitch." Russell blinked and Jessie looked up at me. Tara stepped back to watch as I applied the cosmetics to my darling, little girl. A few minutes later, she looked into the mirror and discovered herself as a beautiful woman.

-----

The wigs Tara had brought weren't up to the quality of the wigs I had bought, but they were passable. Tara approved of the selection of sundresses we had chosen. She had something special tucked away for Jessie to wear today. Something that hadn't been part of the clothes Jessie had tried on for us earlier. With the right cosmetics, the right outfit, the right wig, and clean shaven all over... Jessie looked like pure, unadulterated, liquid sex. Tara positioned us in front of the mirror. I wish we had taken a picture. Candy and Jessie looking as damn fine as reality would allow. Looking in that mirror, it was difficult to tell which one of us was more attractive. Looking in that mirror, it was even difficult to tell which one of us was older.

Mitch turned off the TV and waited for us to emerge. Tara strutted her stuff out first and took her pose. I followed along second, taking my pose. Jessie came out third, taking her pose. Mitch looked at the three of us in stunned silence. We looked exceptionally fuckable. I'm sure Mitch probably dreamed that the three of us would drop to our knees and crawl to him right then and there. I certainly wanted to, but it didn't happen.

"My work here," Tara exclaimed proudly, "is done!"

With that, she set to collecting her things and putting them all back in her luggage. Almost like she was running late to catch a train, she lugged her suitcases back down the hall towards the front door.

"Won't you at least stay for dinner," Jessie asked.

"Yes, please stay for dinner," I followed, "I insist."

Tara wouldn't hear of it. She made polite excuses and was ready to go. At least she let Jessie carry one of her suitcases out to her car. I ran to my bedroom and fished a crisp bill out of my purse. Tucking it away discreetly, I hurried out of the house after them. I caught up to them while Tara was hugging Jessie goodbye, having already loaded her luggage into her car.

"You didn't think I was going to leave," Tara said while she embraced me warmly, "without a big hug for my favorite Candy?" I hugged her back tightly. I didn't want her to go.

"Don't mention it," I said, pressing my hand into hers, with the money between them.

"Thank you," she said, turning our hands so hers was on top, then letting go so the bill remained in my palm.

"This can't have been—" I started, but she cut me off with a finger to my lips.

"Honey, I've got a Sugar Daddy to take care of me," Tara told me. "Did you notice his latest investment?" I looked at her car, which was quite expensive and far better than mine.

"Not that, silly," she told me, "These!" She grasped her tits with both hands. They were larger than I remembered, but I had assumed it was just a supportive bra.

"The next time you see me I might be all woman," Tara confided in me, "Unless daddy decides he prefers me the way I am. Either way, I'm happy, and you could use that," she nodded at the money in my hand, "much more than me."

I hugged Tara closely once again, then we parted our ways.

"How much did you try to give her?" Mitch asked when I came back inside.

"It doesn't matter," I told him, "She wouldn't take it."

Mitch just nodded slightly. After I closed the door, I noticed Jessie standing next to the TV looking at Mitch uncomfortably.

"Well," Mitch had noticed, as well, "Spit it out."

"I know it's just a matter of time before it happens," Jessie said. Her voice was still very masculine, "I just need to know when so I can prepare."

"What are you talking about?", Mitch asked her.

"When..." Jessie took a deep breath and continued, "when are you planning to fuck my ass?"

"You're not ready yet," Mitch answered.

"I know that", Jessie responded, "but I need to know how much time I have to prepare."

"I can use your mouths again on Friday." Mitch was getting irritated. "Your ass will only be ready for stage 2 by then. Then comes stage 3 and stage 4. My cock is stage 5. Understood?"

Jessie and I exchanged a look but didn't want to ask what any of that meant. We didn't want to upset Mitch further, yet our silence wasn't helping things.

"Come over here and show me your boypussy," Mitch demanded. Jessie complied, presenting her bare ass to the boy her own age sitting in the recliner. I didn't know why, but I felt myself summoned to come closer as well. I stood next to Mitch's chair.

"Hold this," Mitch removed Jessie's butt plug, and handed it to me. Old habits die hard, I bent down and took the foul thing in my mouth. Mitch and Jessie both turned to stare at me. I shrugged—it was a stupid thing to do, but the damage was already done. Spitting it out into my hand wouldn't change what I had just done.