Taking Charity to the Pool

I turned to Twitter to help find a hottie I could beat my meat to. I was hoping for some sexy amateur MILF. I’d been following an “Uber Driving Slut” lately. She looked a lot like Karen McGifford the woman we saw at Minerva’s market only younger. She would make it appear her tits fell out of her shirt to boost her tips or even suck cocks and fuck guys if she thought they were cute enough and then film it and put it on Twitter. Her husband knew all about it but he wasn’t submissive. He just liked watching the videos of his wife fucking dudes as much as the rest of her fans. She had this typical suburban housewife look but she was very daring. She once drove a guy to the airport with jizz all over her face and talked to him the entire time while pretending she didn’t realize her face was frosted with the last passenger. The guy asked her about it and she casually said “Oh that? I just sucked the dick of my last customer. Do you want a blowjob too?”

Instead of looking to see what new sexy shenanigans that woman was getting up to on Twitter, I found myself reminiscing about touching Stacy’s pussy in the darkened alley the night before instead. Once I finished thoroughly jerking off I washed my hands and took my clothes off. I grabbed a towel and wrapped it around me, put on some sandals and ran downstairs.

Lucy and Simon were completely naked and holding their towels. They were laughing and joking and pointing at each other’s genitals when I came downstairs. It seemed innocent enough, though.

Lucy was indeed flat-chested, but she had broad round areolas that suggested one day she’d have a lot bigger boobs. She had just a wisp of golden hair above her pussy.

Simon was a smaller version of me. Brown curly pubes to match the hair on his head and just as bony and awkward. The only difference was he didn’t seem to care that he was naked in front of my father.

Lindsay stopped me before I made it to the living room and grabbed my arm. “Do you have a boner? is that why you have your towel on?” she whispered in my ear. Even in whispers Lindsay’s voice grated my nerves like fingernails on a chalkboard. It was more so now that she had so much dirt on me.

“No!” I squealed like a stuck pig. I didn’t intend to sound like that, but my sister had surprised me when she latched on to my arm.

“You know why your dick is always hard?” Lindsay said as she reached down to my waist and ripped away my towel to expose my naked body, “Because it thinks you are a pussy too!”

“I told you he would be shy!” Lindsay smiled over to the living room and waved my towel like a flag of victory. Lucy and Simon chuckled and so did Eddie and my father.

She whispered again in my ear, “Don’t act surprised with how I talk to you in a few minutes. I am going to very nice and supportive. I don’t want you to give me any smart-aleck comments,” my big sister took me by the hand over to where the others were like she was leading a reluctant child...

I was really embarrassed, even though I was in a room with three other naked people, if you counted Charity. I had already grown so used to her ever-present melon shaped bosoms that if Charity wore clothes it might have seemed strange to me.

“Don’t be shy when you are at the pool. I need you to assert yourself,” Lindsay told me as if she was talking to a small child. I got the impression she was reminding me to be assertive with Charity without raising suspicion so I nodded. “You are in charge. That means go straight to the pool area and do not leave until we come there to take you to lunch. I want to talk to dad and just have a little alone time with him or else I’d be out there enjoying the sun with you!” she smiled.

I couldn’t believe everyone else was buying that Lindsay ever intended to go naked at the pool or that she was kind to me for no reason, but they bought it.

“Keep an eye on your brother and sister and watch out for Charity. She isn’t allowed to tell you what to do, but if something happens and you aren’t sure what you should do, then you can always ask her!” Lindsay’s tone suggested she thought I was learning to cross the street by myself for the first time.

I nodded.

“Master Davidson was kind enough to loan Angelica’s knee pads to Charity until we buy our own,” she said. There was no trace of sarcasm in my sister’s voice and that scared me because it was so out of the ordinary.

“This is her leash,” Lindsay held up a long strand of leather that was attached to Charity’s eyelet. “It has already been attached to her collar for you, so you don’t have to figure out how to do it. Just leave it on when you get there. Dad wants her to crawl to the community center. Don’t drag her or walk too fast. She isn’t permitted to swim without permission. I think they frown on slaves in the pool anyway. Pick a spot with some shade and then tie the leash to the beach chair where you leave your stuff,” Lindsay handed me Charity’s leash.

Charity’s eyes were wide and hopeful like she couldn’t wait to get started on this journey. She blinked at me twice and then hugged my father while he was seated on the couch.

She kissed him on the lips and told him, “Bye, I love you. Thank you for letting me go to the pool, Master!”

Dad told her he loved her too. They sounded almost like any vanilla couple who were saying a quick goodbye.

“What are you supposed to do with her before you leave the house?” Lindsay asked me.

“Ask her to turn around and spread her ass cheeks so that I can check her butt plug?” I said.

“All you have to say is Present your plug, son. You don’t have to be that explicit,” my Dad frowned at me. I didn’t know that I was supposed to say that.

“Present your plug?” I said it like a question and not an order.

Charity slowly spun in place so that her ass faced towards me. She bent over, spread her legs wide, and grabbed her ankles. I could see the black latex-rubber turnip was seated between her asscheeks.

“What do I do?” I asked.

“You don’t have to do anything. When you have had your look, just tell her, ‘as you were’, my Dad suggested. When I gave the order, Charity stood back up and faced me. Her tits jiggled a little. She didn’t look embarrassed at all that we had all just looked up her ass and saw her bald pussy flaps.

“You should give a core command with a little more gusto like you mean it and aren’t making a request,” Eddie demonstrated by telling Charity to bend over again with a drill sergeant style “PRE-ZENT ASS!”

“Is the core command present ass or present plug?” I said.

“The plug is in the ass so the slave will figure it out. You can say it either way. Present is fine for now since you are only checking her ass and not cunt, tits or mouth,” Eddie said. He wiggled the plug to check to see that it was firmly in her asshole and then flicked it before giving her the order to stand up.

“I suggest you give her the order at the pool when you find a beach chair. There will be some old-timers who will see an unescorted slave with a bunch of kids and get offended if one of you doesn’t look like they are supposed to be there with her,” he suggested. “You don’t need to keep checking while you are there and don’t be offended if a Principal Dominant comes over and double checks. They don’t know you yet.”

“Yeah,” I agreed. Eddie looked at me like he wasn’t sure if I understood but shrugged. “When you want her on all fours to follow you just tell her to ‘Heel’. If you want her to stand up for any reason then you can just tell her, ‘at ease’, or ‘as you were’, like you did earlier. It really isn’t rocket science,” Eddie acted like it was no big deal but I was already nervous I would blow this and forget something.

“Heel Charity,” I said more forcefully, and Eddie told me that I was a natural although I think he was just being charitable.

Charity got down on her hands and knees, ready to crawl with her palms flat on the carpet.

“Have fun,” Lindsay smiled and placed a small canvas satchel around Charity’s neck. “This bag is too heavy for her to carry in her mouth. I took the liberty of putting together your suntan lotion, floaties in case you forget how to swim, stuff like that. I knew you might forget to bring them down.”

Lindsay was such a cunt! She was family and I was supposed to love and accept her but she made it so damned hard. This blackmail thing had permanently created a rift between us that I’d never forgive. I let her be petty towards me and hoped my Dad would put a stop to it.

I couldn’t say much anyway because I had forgotten the suntan lotion and extra towels in my haste so Lindsay wasn’t wrong. I just wished she wasn’t such a brat about it.

Lindsay also warned me to play along with her acting helpful and considerate, but it sounded more to me that she was treating me like a child.

Dad was talking to Charity and giving her instructions. He noticed what was going on but our sibling rivalry had been going on for so long that it hardly seemed out of place to him.

“Buh-bye, now! Don’t forget to put on your sunscreen,” Lindsay waved us out the door.

I held the leash in my hand, and I felt powerful as a full-grown, naked woman padded along behind me. She couldn’t move fast because the satchel around her neck was swinging almost as much as her tits were as she tried to keep pace. Simon and Lucy ran ahead a little bit but we where close enough that we could talk. They were excited to get there.

“Neither of you seem all that nervous about being naked?” I observed as we left the house.

“I am just pretending I have the world’s tiniest bikini on,” Lucy smirked playfully.

“If we are all naked it is much easier to do it,” Simon shrugged. He did look like he was a little apprehensive now that I mentioned it.

“That is what I do too, Sir” Charity said from the ground behind us. We turned around and looked at her. I didn’t expect she was going to talk to us.

“Oh? should I not have spoken? Was this a private conversation?” Charity appeared very sensitive to the possibility she may have offended us and was ready to apologize without any hesitation.

“No, I just didn’t expect you were going to say anything. You can talk,” I wasn’t sure if I could tell her she had to be quiet and I didn’t want her to be anyway.

“One of the reasons that I decided to submit to your father was that I knew people who lived in loving BDSM relationships and they were quite happy,” she explained.

“Oh?” I asked her to elaborate, and Charity seemed flattered I cared.

“I used to know a girl who was a submissive to her husband. They were a big influence on me, and she was a mentor when I found my life falling apart and needed a change. They introduced me to a website called bondagelife.com. It featured the life of Rachel Greyhound. She is a slave like Fawn. Completely shaved from head to toe and she is on webcam 24 hours a day to be observed. She thrives on her submission, and I strive to be like her,” she said.

I made a mental note to check that out.

“You would be okay with them shaving your head like the pony girls?” Lucy asked her.

“If Master felt that would teach me to be more submissive or he simply liked how it looked, then I would shave my head as bald as any other part of me,” she assured Lucy.

“I’d hate to lose my hair,” Lucy flipped her pretty, long, golden hair.

“It is just cosmetic and if losing my hair pleased your father then I would shave it myself, Miss Lucy. There are a lot of changes in store for me. I don’t know, they may even make me shave my head to be in the orientation. I hope it doesn’t freak you guys out,” Charity’s conversation was a little less stilted and laced with the high protocol speech she had used at home. She was talking more like how she used to talk. I wasn’t sure if that was because she was further away from Dad and didn’t feel it was necessary or because she was growing more comfortable with us.

“I am more worried about you!” Lucy said with compassion. “You are going to be locked into a cage every night. Isn’t that a little scary?” she asked.

“No Ma’am, not at all. The fear of the unknown is only scary if you don’t have faith and trust in your Master. I know that my Master has reasons for his decisions, and I accept that my place is to be in a cage at times just as it is to crawl while you walk,” she said.

“You should be afraid though,” Simon was half-joking when he said that once she was locked in a cage and couldn’t go anywhere, Lucy might come and talk her ear off.

“Oh, I would not mind that at all. “I was worried you would be so disgusted with me that you wouldn’t want anything to do with with me. We did not talk much when I had my old life but I’d be glad if that changed. I wish it had been different then, and that is my fault. If any of you have questions, concerns or just want to talk your father has instructed me to be as honest and open with you as possible.” Charity beamed with pleasure that Lucy might want to talk to her even as a slave.

“Hah, Honest as you can? Dad says honesty is like pregnancy. Just like being pregnant, you either are, or you are not,” Simon said. That was true. My dad was a fan of using that expression. There was no ‘as honest as possible’ in his world. You either told the truth, or you didn’t.

“That was a poor choice of words, sir and I am sorry for the misunderstanding,” Charity apologized. “Your father feels there are some things you will understand in your own time and in your own way. I was instructed to refer you to him should you ask about those things,” she said.

“What things?” Lucy demanded immediately in the most precociously adorable way possible.

“You would have to ask your father, Miss Lucy,” Charity smiled sweetly.

“Solid logic,” Simon approved of the witty response that Charity can’t’ tell you what she can’t talk about or else she’d be talking about what she is forbidden to discuss.

We joked about that a little as we walked through the neighborhood. We weren’t even close to the pool.

“Too bad we couldn’t take the golf cart,” Simon lamented that he’d rather ride than walk.

“Charity would have had to run if we did that,” Lucy reminded him that would be difficult in Sunday morning Florida Sun.

“I don’t mind, Ma’am. I will run until I drop. Please never feel guilty about what I have to do. I know you have a lot of compassion, and I applaud you for that, but if you truly want to show me a kindness, then do not feel bad because I am being trained. It is what I asked for and what I love, Ma’am,” she said.

I really liked what she said. I felt terrible jerking her leash as she stumbled behind us on the sidewalk.

We walked past nearly identical houses on our street. A pretty slave was outside in high heels washing her Master’s golf cart. She waved at us as if it were perfectly normal that three naked teenagers would be walking an adult woman on a leash down the street.

“You don’t think some of this is cruel though?” Lucy seemed to be chewing on what Charity had just told her about not being concerned about her. “You have to eat food off the floor while the rest of us eat fresh food. You are in a cage. You can’t walk while we do. Why does it all have to be so mean?” she asked.

“Imagine you were walking a dog on this street and there were lots of cars, Miss Lucy. Would it be kind to let the dog run loose?” she said.

“No! the puppy could get hit by a car!”

“Yes Ma’am, the dog doesn’t see it as cruel to be kept on a leash. They are happy because they know their owner loves them enough to take them for a walk and will stop them from running off and getting into trouble. Is it cruel to feed the dog a bowl of dog food while the humans sit at the table?” she asked.

“You aren’t a dog, though!” Lucy conceded Charity’s point but had her own.

“I am not a free person, though. My role is to serve, and you are doing me a bigger favor than you know treating me like one. I thought you might freak out and call me a bad stepmom,” Charity admitted.

“Why would we do that?” Simon asked.

“I know a lot of what you see me do seems very naughty on the surface. I don’t expect you to pretend you don’t see it that way. I told myself when we moved here that I was being selfish for wanting a life like this with your father, around you.

An old man driving a golf cart tooted his horn. He had a golf ball mounted on the front as a hood ornament. The wheels of the cart had golf-ball shaped hubcaps. There were two collared slave women harnessed naked jogging slowly behind the cart. The older of the two had silver hair, an eternity collar and comfortable looking shoes. Her pubes were grey and her nipples were elongated. She had a tattoo on her ass that said “Sexy Granny!”

The second woman might have been her daughter. They looked about twenty years apart but had very similar features. She had an eternity collar and silver hoops in her pussy, nipples and one through her nose. They waved at us as they trotted by. I could see what appeared to be a white golf-ball between each of their butt cheeks.

“Should we ask them to give us a ride?” Simon asked.

“Dad said we should not talk to strangers and we were to walk there,” Lucy reminded me before I could answer.

“I thought I was in charge?” I said before telling Simon we’d continue to walk.

Simon shrugged and didn’t argue with me. I hoped that he didn’t feel intimidated the way Lindsay made me feel sometimes and understood my reasons for making the decision. It was the safest option and the one my dad would have expected us to choose.

We talked most of the way to the community center. I have to say that I enjoyed this time because without Dad and Lindsay standing over our shoulders, we could talk a little more freely. Charity forgot to call us Sir or Ma’am at times and spoke in a very casual manner. I thought about correcting her.

My sister had told me to be strict and ruthless with Charity. It isn’t my nature to be strict or ruthless with anyone. I’ve never had the option but now that I had it I didn’t want it. Charity was willing to be held to strict standards and I would do that much but I didn’t want to make her miserable at all. I liked seeing Charity’s bright face as she looked up with love in her eyes and followed us like an obedient pet.

Charity was also trying hard and being an excellent sport by not complaining about being led on a leash for what felt like half a mile. She had trouble at times keeping up but she was stubbornly enthusiastic about following behind us and never once looked embarrassed even when other people walked right past and looked down at her ass crack. Charity acted like she was out for the walk of her life, and this was a big adventure despite it clearly being physically demanding to crawl all the way there.

As we approached the Community Center I heard Lucy shout “Playground!”

We hadn’t seen it on the tour originally. An ornate fence surrounded a small outdoor playground with the typical looking swings, jungle gym and merry go-ride.

“You are way too old to play in there,” I told her that it was for babies.

“How come they are in there?” Lucy pouted at me and pointed out there were two older women on the see-saw, laughing and bouncing up and down. The two naked women weren’t particularly attractive or unique. They were both collared and seemed to be having a good time on the see-saw bouncing all the way up and then waiting for the person on the other side to bend down slightly and spring into the air to force them back down.

At first, I thought they had lost their marbles until I saw one woman shift herself up slightly when she was raised in the air. The two women were fucking themselves out in the open on cock-shaped dildos that were embedded in the see-saw.

I noticed there were slots in a lot of the playground equipment that a person could use to attach a dildo.

“I think you may be too YOUNG for this playground,” I quipped and quickly guided my siblings through the gate of the tennis court. I did not want to be the one my dad blamed for letting them watch these two horny bitches go at it and fuck themselves on the see-saw.

I thought the tennis court would be a vanilla respite from the kink.

The first thing I saw when we started walking through the clay courts was a nude collared woman half-squatting on the ground so that her hands were flat on the hot clay and her ass was sticking up, but her knees were bent. The words “I came without permission,” was written on her back and it appeared she had been left there to quiver and mutter to herself. The end of a tennis racket had been shoved far up her ass.

“Wow,” I said in amazement. I had been looking at porn since I hit puberty, I’d been through the tour on-premises and even walked down Groper’s Alley, and yet I still wasn’t ready for seeing this hot woman’s ass stuffed with a tennis racket. Her pussy flaps were dripping wet. I noticed her wrists had been zip-tied to her ankles so that she couldn’t change that position.

“Oh my,” even Charity looked impressed when she looked over at the helpless slave on the court.

“What does it mean? That she came without permission?” Lucy asked a real hot potato.

“It means she had pleasure in her pussy when she should have been focusing on someone else’s pleasure, Miss Lucy” Charity said.

“Oh like she was playing with herself?” Lucy asked and I nearly did a spit-take in shock that my little sister knew what that was. She was nearly in high school so of course she would know. I just tended to think of her as this naïve little girl.

“Yes Ma’am, or her mind was in the gutter and she was thinking dirty thoughts,” Charity explained.

“How can you tell when a woman cums?” I felt dumb for asking but I wanted to know for future reference.

“You may not be able to tell. It depends on how they are wired, Mister Matthew. The female body is a very mysterious thing. Some women squirt a liquid but most of them time you’ll have to take our word for it,” she smiled as she crawled behind me.

“So why would they punish that woman if they weren’t sure if she came?” I asked.