Chapter 16

I decided to go for it! I had played with her titties, and she hadn’t stopped me. The ass was different because as you know I am ass-fiend and I was afraid I might do something I definitely shouldn’t do.

The ass was a very intimate part of the body to me. Almost as much as the pussy and I felt that my Dad would have a hard time accepting that I touched her boobs but that he’d probably want to kick my ass for touching her butt.

I couldn’t resist the temptation, though. Charity’s ass was hard as a rock when she clenched her butt muscles. It was a perfect contrast to her silky, fat melon-shaped titties. “Clenched or unclenched, Sir?” she asked me playfully.

I didn’t understand until Charity unclenched and I could see the tip of the black plug peeking out between her cheeks when she relaxed her ass muscles.

“Unclenched,” I said as I stared longingly at the flat rubberized surface that was forcing her asshole apart.

“You sure? You won’t go all ass-crazy and get super horny, will you Sir?” she teased me playfully.

The man that had told us what a nice mom and son we were overheard that. He smiled at us and led his slave away on all fours. I don’t think he was offended at all.

“You are very sweet, Sir. My ass is quite hard, Sir. You don’t have to be afraid of touching it,” She told me that I could rub the lotion into her butt exactly the way I had her applied it to her tits.

“Your tits are jiggly, but your butt is like Mount Rushmore,” I observed playfully.

She giggled and joked that maybe one day my father would carve a president’s face in her ass.

I tried to picture that and told her I liked it pristine and natural like it was.

“You are such a charmer. You are making this a lot less awkward than I thought it would be. Thank you, for that sir,” she was THANKING me for joking about her ass and touching it? I wondered if this was some really realistic wet dream. It seemed too good to be true. I didn’t want to jinx things by talking more and putting my foot in my mouth. Instead, I focused on massaging her ass with my hands. She told me I could be rougher with her ass, but truth be told I just have very weak hands because I was squeezing her buttocks as hard as I could at the time.

We were communicating so openly that I wanted to tell Charity that Lindsay had instructed me to make her life miserable and see what she thought about it. I hated keeping secrets, and I felt super guilty that my mission today was supposed to be making her life miserable. Charity had opened up to me and was joking in a way that made me think we were getting closer than ever. I didn’t want to disrupt the fun we were having, but I wondered how she’d react if she knew I was supposed to be slapping her ass and treating her like shit for some reason.

“Thank you for bringing me with you today, Sir,” she thanked me while I experimented with her reaction to me pulling her ass cheeks slightly apart only to watch them elastically bounce back together around the butt plug.

“We made you walk like a dog, and you can’t even swim in the pool,” I chuckled and said I didn’t see how that was worth a thank you. It hadn’t even been my suggestion that she come. I felt like that I didn’t deserve any praise for that.

“I get to see my family in the pool, having fun. You could have faced me away like Dancer, and I would miss being able to watch Simon and Lucy frolicking,” she smiled broadly and thanked me even though she had to come along in the most sexually humiliating way I could imagine.

I hadn’t been looking out for my brother and sister. I assumed they were okay, or I would have heard people screaming. The lazy river was shallow enough; all you had to do was stand up. The lagoons weren’t that deep, and no one was in danger, even without lifeguards. There were plenty of people who would have done something if someone was in trouble. Charity was so sweet and considerate that she was grateful just to be facing the pool and permitted to watch other people have fun.

There was nothing sarcastic about how she expressed her gratitude. She wasn’t being facetious or trying to get sympathy for how unfair it was other people had fun while she watched. Charity reminded me of a loyal dog that was just thankful to go on a walk with her owners.

“I don’t see why you are thanking me,” I shrugged and pointed out that most of the slaves were facing towards the pool.

“I lack the words to accurately express how grateful I am that you are treating me like every other slave here today, sir. Just know that is all I could have wanted. I thought the three of you would find it disturbing or offensive,” She said.

I was having difficulty processing an adult other than my dad that cared what I thought about anything. It did seem strange to me that she was so happy about being treated less than equal but I would never have called it disturbing or offensive.

“I also got to hear you call me your stepmom. You could have come alone, and yet here you are applying sun lotion to me instead of swimming,” she said so affectionately that I felt guilty about playing with her butt.

“Then again you ARE trying to see how many times you can pull my ass cheeks apart like a spring and watching them snap back in place without me saying anything, aren’t you sir?” she teased me playfully. I stopped immediately because that was exactly what I had been doing.

“If you want to play a little with my butt, I am not going to say anything, Sir,” she told me with a shrug. “It’s kind of funny,” Charity even shook her butt after I stopped and clapped her ass cheeks together for my benefit.

“I thought you had to tell my father everything,” I said.

“I will, and I’ll probably be punished for saying this, but I get it. You are fascinated by my big, dirty, nasty butt, Sir. There is no shame in that if you like asses like mine - some guys do. I am no porker, but I am not perfect, either. I’ve got plenty of cellulite back there. If you want to look at me, then be my guest. Only a silly girl would get naked and then insist you not look at her butt,” she explained.

I instantly imagined Stacy showing me her ass and shaking it for me then scrunching her nose at me in disgust when I looked. Stacy was a show-off but always on her own terms.

“I am naked at all times precisely so nothing can be hidden – even my backside. All my foibles, imperfections, freckles, moles, and wrinkles too! You won’t see anything on my butt that isn’t on any other butt. I don’t have an extra hole and there is nothing special about what comes out of mine,” she chuckled. I pictured warm nacho cheese flowing out of her ass instead of poop.

She may have thought her ass was far from perfect but to me it was fascinating. Her liberal attitude about looking and even touching it not being a big deal made it even more inviting.

“If you want to get it out of your system and see how it jiggles and what it can do I think you’ll see that as a toy, there isn’t a lot you can do with it until you start sticking things inside my hole,” I was shocked when she made the offer.

“I should warn you that I always tried to shove the square peg in the round hole when I was little!” I was joking about playing with shapes when I was little.

“That COULD be interesting,” Charity raised her eyebrows a few times suggestively and she looked intrigued by the possibility of a square peg getting shoved into her round hole. She didn’t explicitly say she would let me do it but she shook her ass again playfully for my benefit. Then she sang a cute little jingle to the tune of the old Slinky commercial.

What walks downstairs, alone or in pairs, And makes a stinkety sound? A butt, a butt, a marvelous ass! Everyone knows its Stinky. It’s fun for a girl and a boy!

I laughed and said that song was twisted – especially the part about boys and girls playing with their own asses and exploring them like they were toys.

“My brothers used to sing that to me when I was little. They were making fun of my big butt!” she said.

“Hah, you had a big butt even then?” I laughed.

“It wasn’t the same size as it is now but for a girl my age with a flat chest it looked like I was carrying two bags of marbles in my back pockets at all times!” she laughed.

“You had a flat chest?” I was even more surprised when I heard that. Charity had such a nice set of knockers I couldn’t imagine her any other way. Her boobs were nice and round like fluffy pillows. I could attest they were not fake after I felt how squishy and jiggly they were.

“Yeah, it is amazing, huh? Sir?” Charity jiggled her tits in a clockwise fashion for me and moved one and then the other independently while raising an eyebrow at me.

“Wow, I didn’t know you could do that!” I was shocked as she moved the other one the same way.

“There are a lot of stupid human tricks I have learned how to do over the years, Sir!” Charity chuckled and told me I’d have to give her a cherry stem some time and let her show me how she can tie it in a knot with just her mouth.

I wondered if she learned that from my father or before they ever met. I tried to imagine a scenario in which she would have needed that skill and couldn’t. Then it dawned on me it sure would be helpful to be know how to tie a cherry stem in a knot when eating pussy. I had never gone down on a girl but it was something I was looking forward to doing almost as much as fucking one! I fantasized about Charity teaching me how to do that and tried not to feel guilty about it. She had a delicious looking wet pussy that reminded me of a pink grapefruit I just wanted to dig out.

I rarely looked right into Charity’s pussy because I didn’t want to get caught staring and have to explain myself. I made myself steal glances at it and then memorize the image in my spank bank for later. I was taking a lot of those mental pictures today!

“I should show pictures of me to Lucy of when I was her age. She probably won’t feel so inadequate then,” she laughed then reminded herself that she brought nothing for the move to Sunny Manor because she wasn’t entitled to any possessions even her baby pictures.

“Dad made you throw away your baby pictures?” I was appalled at my father. That seemed unnecessarily cruel.

“I burned all my old life. It was important for me to start fresh. Your father would have insisted I save all that old crap that belonged to Mary. That was a different lifetime ago. I asked for this treatment and so did that girl on the tennis court,” she explained. “I had to beg him to let me get rid of my old baggage and memories. Some were good, some were bad, some were meh but they belonged to Mary. I want to make new memories!”

“That is a big commitment. You sure you won’t regret it? There is no undelete to get them back,” I reminded her.

“You have such a kind heart to worry about things outside of your control, Sir. I have no regrets and no desire to look back at Mary’s life,” she told me. “I saw the look on your face when you saw that woman being punished on the tennis court,” she smiled warmly.

“Was it that obvious I was turned on?” I laughed but I was blushing at the same time. I didn’t think Charity would notice me staring at the girl.

“Ha-ha, that isn’t what I meant. I could tell a part of you wished to stop and comfort that girl. You wanted to ask her what was wrong and see if you could help her, didn’t you, Sir?” she said.

“Yes,” I admitted that was absolutely true. I liked seeing her naked in that predicament too though! I was conflicted. I had never seen anything like a naked woman left out on a tennis court with a racket up her ass. It was shocking and a part of me wanted to rescue her while a part of me wanted to see how much further the handle could go.

“She didn’t look like she liked it, though. She was shivering,” I said that I doubted she asked for a tennis racket up the poop chute.

“No, she asked to be judged and taught obedience. She asked to be punished when she fails so she can learn from her mistakes and be motivated to serve her betters, Sir. Things aren’t always going to be pleasant for me. I am enjoying what you are doing and our conversation. I won’t enjoy everything that happens and I am okay with that. I accepted that is going to be my reality before we ever moved here. I know that I will probably be tempted and even sometimes cry, beg to stop and whine or complain. I hope it doesn’t make you feel bad to know that it isn’t a kindness to let me out of what I asked for,” she said.

“Wait, rewind to that part about how it is pleasant for you right now? You mean like when I am rubbing lotion on you? That is pleasant?” I wanted to hear her tell me she was getting horny by my touch. I know it was wrong, but I like to give pleasure to other people.

“You are doing just fine, Sir,” she told me and let the matter rest in silence with a wry grin that suggested she totally meant she was enjoying the extended rub-down with the lotion I was applying to her body even if she didn’t say it.

In retrospect, I didn’t want her to say she was horny from my touch. It would have been too weird considering who I was doing this with. The idea that it MIGHT be a turn-on to her was enough of a turn on to me.

I was pretty shocked I was able to get away with doing this in the open at the pool and that she had not complained. I was enjoying the smoothness of her legs. Her pussy smelled very musky but not in a bad way. There was a tiny sliver of pussy dew dripping from her pussy onto her leg. I also observed her nipples had become increasingly hard. I didn’t touch her pussy though or anything around her crotch.

“It’s my turn to be embarrassed, Sir,” she admitted when she realized I noticed the signs of her arousal. “It looks like I have a wonderful problem of my own and no way to take care of it,” she applied the euphemism from earlier that she used to describe my dripping erection but used it to describe her own state of arousal.

“It is perfectly natural for women to get wonderful problems too, Sir. if you rub the genie’s bottle enough then wishes get granted,” she told me.

I licked my lips and wondered what wishes she’d grant me. I liked that metaphor a lot! It was super-hot.

“Naturally, I should keep my mind on serving you and Mister Simon and Princess Lucy and not on dirty thoughts. I am sure you will have to inform your father of my disgraceful behavior so that it can be addressed,” Charity seemed conflicted with her own emotions as she said that.

“Do you need to go into the bathroom and finish yourself off?” I asked her without addressing her conflicts or promising to turn her in. I felt Charity would have been happy if I shamed her about being turned on, but I liked seeing her dripping wet.

“I wished it worked that way for me, but I don’t think a finger or two will sate my unfulfilled arousal once I am wound up and dripping wet, Sir.”

I loved hearing her say she had unfulfilled arousal. I wanted her to repeat it.

“I am not allowed in the women’s bathroom anyway, Sir,” she reminded me that there was an open area for slaves that was behind a wall. I told her she could probably play with herself in there.

“I’d be punished for sure if someone caught me unsupervised masturbating anywhere, Sir!” Charity admitted. I loved that she seemed like she was considering my suggestion but couldn’t act upon it.

I also liked the mental visual that Charity could masturbate as long as she was supervised. I was too shy to make that suggestion though but I fantasized about telling her I’d watch. I could picture her thanking me and telling me what a huge favor it was to keep my eyes glued on her fingers while she tickled her pussy in the most intimate ways until she coaxed herself into a full unabashed orgasm right in front of me!

“They do love to punish slaves here. I don’t see why they would punish you for pleasure though,” I admitted I still didn’t get the reasons behind a lot of the things they did at Sunny Manor.

“Trust me when I say that they have a number of ways to punish women and men differently here. The number one way for both genders is constant arousal and edging without actual orgasm,” she admitted.

I loved hearing that. I joked that I thought the number one type of punishment would be pain.

“Pain can be part of how they manage that constant arousal without release, Sir,” she said. I didn’t understand what she meant, but I liked the concept. “Pleasure, on the other hand, can be used to punish a slave with constant, unrelenting orgasms,” she told me.

“I am a Libra,” I told her my horoscope sign and said that I prefer somewhere in the middle.

Charity had a lovely giggle, and she wasn’t just laughing as a polite response. “You are helping me more than you know to make what might have been awkward feel like a chance to get to know you better and thank you for that, Sir,” she said. Her nipples looked like they ached, they were so hard now! Charity’s pussy was dripping down her thigh even more than before.

I wanted desperately to reach up to just where her pussy lips end and her leg meets and wipe it off and then taste it. She had rubbed my semen into her skin earlier as if she didn’t even realize she was doing it. In my fantasy, Charity tasted like clear American Honey and I slurped it all up but I was not bold enough to do it.

“Should I stop putting the lotion on you?” I asked. “It puts the lotion on the skin, or it gets the hose again,” I joked with a quote from the classic movie Silence of the Lambs while continuing to rub her sexy body.

Charity laughed even harder and begged me to stop joking because she almost unclenched and dropped the butt plug where she stood. “As far as applying lotion though and seriously, that is completely up to you, Sir. I don’t want you to feel you have to touch me. I know what you must be thinking,” she consoled me in a knowing and understanding manner. “It is probably weird to you that I have goosebumps all over, and my cunt is wet. You probably think I am the dirtiest slut you have ever met,” she said and apologized for putting me through this.

“I’ve met some pretty dirty sluts, over the last few days,” I joked that she technically wasn’t the dirtiest of all of them by comparison. I liked that she called her pussy a cunt and openly admitted it was wet. That word was as taboo to women as the N word was to most black people. I knew she HAD to use it, according to her protocol, but it was still sexy-hot hearing an actual woman describe her wet cunt and apologize to me for it. It seemed so surreal that I found it hard to believe I had actually heard her say it.

“I never knew how funny you were until today. I always thought you were a quiet loner,” Charity changed the subject while I continued to work the cum-infused lotion into her skin. I felt a little guilty that it contained my spunk and I didn’t tell her. I would have but she’d tell Dad and I had zero explanation for why I had done that.

“You really made me laugh so hard today. You asked that girl at her birthday party if they were going to hang her sister from the ceiling and beat her until Candy fell out of her ass!” she laughed again as she retold my joke. It really boosted my self-esteem to be complimented like that for my humor.

“Yeah, that is more of a self-defense mechanism for me when I am in an awkward situation, and I have to talk to someone. I tell a joke to defuse the situation,” I said.

“If it is any consolation, I do the same thing sometimes. I just don’t tell jokes as funny as you do. I could genuinely picture Dancer being hung above their buffet table and beaten with rods by all the little kids until wrapped candy dropped from her cunt and showered everybody!”

“Yeah, that isn’t a Hershey’s kiss, Hector! Put that back!” I imitated a concerned parent at the party telling his son that what just fell out of her ass wasn’t candy.

“Oh my god, you are twisted! That is so nasty and at the same time, funny! I had no idea you were like this, and now I wish I had talked to you when I was Mary!” she said.

I had returned to rubbing lotion into her butt again. I was making a Mr. Miayagi Wax-On/Wax-Off gesture in a pattern of circular motions so that Charity’s big butt would jiggle. Charity was making me nervous by complimenting me like she was. The more she complimented me, the more I focused on her ass jiggling. I wasn’t used to people saying nice things or recognizing my humor other than when I was online with my friends on Xbox.

“Are you doing Karate Kid on my butt, Sir?” Charity asked me with a wry grin on her face while she looked straight ahead and let me continue jiggling her buttocks. I rubbed lotion in a semi-clockwise fashion three times then reversed directions. When she guessed what I was doing, I had a new level of respect for Charity and her sense of humor.

“No such thing as a bad student, only bad teacher, Charity-San!” I imitated the wise old Asian teacher from the classic movie.

“That movie came out when I was your age. How do you even know what that is?” She looked straight ahead and laughed as I moved on to another part of her body.

“Netflix, baby!” I loosened up with Charity some and my quashed my nervousness.

“You remind me of me because you look like you want to jump in a hole when someone gives you a sincere compliment,” Charity observed “But I am going to do it anyway, Sir. You are a really good teacher,” she said.

“Hah, I have not even taught you the 2 Rules of Miyagi-Ryu Karate! Charity-San!” I tried to deflect her attempt to compliment me with a little humor. I didn’t feel like I had taught her anything, and she was just polite.

“I don’t mean me. When we first arrived here, and your sister started to have her little freak-out. You reminded me so much of your father. The first time he took me to 1763. It was this freaky public dungeon on the outskirts of Atlanta. There were all these naked people with leather and whips and chains. It looked like something right out of a wicked fantasy. Let me tell you. I was freaked out. I expected you guys to flip out like I did when you toured Sunny Manor, but you kept your composure the entire time. I wanted to leave and go home, but your Father said things to me that night that made me feel safe with him. I knew he had a plan for me and that he wanted me above all else,” she said.

“I said that to my sister?” I joked.

“No, but you knew just what to say, and now she is out there playing and splashing around!” She nodded in the direction of the pool.

I turned my head and saw Simon floating casually down the lazy river by himself in an intertube as calm as a cucumber. Lucy had bonded with several girls her own age, and they were tossing a colorful beach ball around without a care in the world. She was talking and giggling, and I have to admit I felt for even a brief moment, like I was less of a complete fuck up for being able to make that happen today. The more she made me feel that way the more I came out of my shell and opened up.

“I am her big brother. What was I supposed to say? I had to make her feel safe. I mean, look at this place? It is safe here,” I looked around and saw no dangers. There were dozens of naked people all around with tattoos, piercings and fetish gear, and yet everyone seemed completely harmless and were minding their own business.

“There are some in the family who might have done it differently. Sir” Charity looked down. I knew she was talking about Lindsay. I didn’t say anything, but I didn’t have to. I knew what she meant.

“I am not the perfect brother you make me out to be. I had to go beat off just to touch you, and I don’t want to make this weird, but I like putting this lotion on you more than I would, to swim,” I said.

“You saw a LOT of things that got you horny, Sir. That wasn’t all me,” Charity looked flattered despite denying it had been all her doing. “I already feel bad enough that I tempted you into playing with my butt until you got it out of your system,” she admitted.

I didn’t see it as tempting me at all. I saw it as being lucky enough to be in the right place at the right time and being ALLOWED to play with her ass. All I needed was the confidence to go through with it and her permission and supportive comments gave me that.

I felt like I turned a corner in my own maturity. I had shown restraint and not started shoving things up her ass or seeing just how wide I could pull her ass cheeks apart. I also felt a growing confidence in myself that made me lighten up and not be so shy. I still felt like a goofy kid on some level but Charity treating me like I wasn’t had really given me a nice boost to my self-esteem.

“The funny thing is that I don’t feel I’ll ever stop being fascinated with butts. However, even though you told me I could jiggle your ass open and closed as much as I liked. I don’t feel like I need to right now. I could be doing it and yet here I am rubbing lotion on your feet,” I told her as I knelt and looked right up at her pretty pussy lips as she stood with her legs apart over my head.

“I admit I said some things that may have been inappropriate to my future stepson, or any boy your age, in any case. I’ll leave it to your discretion if you wish to inform your father so that he can address it. I think this is a bit of an impossible situation neither of us anticipated when we left the house this morning. I don’t think we’ve done anything torrid and if you got a little jolly out of touching me, just know that I got a little jolly out of being touched. It was only natural you’d see how my body worked when you touched me. You still have my shins and feet to do and a few spots you missed, but I am not going to hold you up from the pool. You’ve been very thorough on some body parts,” she said.

“What spots did I miss?” I said.

“The one where I have my dripping wonderful problem, Sir. I think your father wouldn’t mind if you played with my butt until you got your curiosity satisfied, but he may think I am incorrigible if I let you see the different ways you can open and close my cunt flaps, Sir.”

“Did you ALLOW me or did I just do it?” I asked her. I was trying to seem dominant.

“I allowed you to do it. If at any time I wanted to leave, I could have. I didn’t have the heart to stop you. You seemed so curious, and it was flattering to have someone so interested in every nook and cranny of my body. You made me feel like I was a teenager,” she said. “I know it was a temptation for you to open and close my butt cheeks. You can order to me pull my butt cheeks apart as wide as I can anytime you want. I don’t see much difference in you pulling them apart, instead of instructing me do it myself, Sir. You had to touch my butt to apply lotion to it,” she said. It sounded like she was justifying what just happened between us.

“Yeah, I’d have to touch your cunt to apply lotion to it as well,” I said with a churlish expression on my face. I wasn’t disagreeing with her logic or arguing. I just wanted her to understand that technically that meant I could touch her there too. Touching her cunt was a line I was still afraid to cross for many reasons.

“My cunt is hairless and vulnerable to the sun, Sir” Charity’s hands were behind her head, and she didn’t look like she was going to stop me. She didn’t tell me to touch it but she definitely implied I should. I felt my dick twitch with pleasure at the mere thought of it.

I won’t lie. I was severely tempted to lotion up her pussy as thoroughly as I had her ass, but at the same time, I could picture my Dad finding out and going nuts.

I settled on putting a lot in my hands and then slapping it on to her cunt as quickly as I could.

“Oh my! That was unexpected,” she said after the satisfying slap. Charity looked impressed with me that I had slapped her cunt and told me with an approving wink, “that works.”

I said that I had half-a-jar of lotion left and I felt like I had covered most of her body twice over.

“I am surprised you have any leftover at all,” she smiled at me and implored me not to worry about her and go have fun. “Just tell me what position to take and tie my leash to the chair please,” she insisted.

“What position would you prefer?” I asked. I felt charitable and wanted her to hold a position comfortably. I knew Charity was a bit of a perfectionist and would be rigid, so I wanted to pick a good one she could maintain.

“Please don’t make me choose, Sir! It removes my sense of submission and puts me back into Mary’s headspace. I know you don’t know all of the core positions and neither do I, but I see a lot of women squatting,” she said.

“Yeah, I see two kinds of squatting,” I had noticed two distinctly different positions at the pool. I was indecisive and nervous. Both positions fully exposed the slaves in very obscene ways and looked difficult to maintain for long periods of time.

“It is painful to watch you interact with your slave,” Master Thorne spoke up from a few tables over. Master Thorne spoke in a deep commanding voice. He spoke very bluntly and made no apology for interrupting with his observation. He introduced his own slave Ruthie. She was a woman that could quite easily have been fifty to sixty years old, but she was in great shape. She had huge hanging knockers and a nice big butt. She was older but she had kept up her body very well.