Chapter 28

Lessons I gave my son on dildos and vibrators had been easy for Freddy to understand. You stuff them in a hole and wiggle them around. I showed him how to use them on the outside of my clit or the nub of my asshole, even fucking me between the tits with them. It doesn’t do a lot for me – but guys seem to like it.

The biggest dildos I used on myself were intended to stretch me out and were sometimes spiked to cause pain. I demonstrated with a huge black dildo that I called “Mandingo”. It was a guest favorite to see me take this python as far up one of my holes as it could go.

“Almost anything can be made to fit in my ass, or cunt if you have the time, patience and lube,” I joked. I told him that was not true for things down my throat. I demonstrated by gagging myself until I choked and explained how it cut off the flow of air after a while.

He was shocked when I told him that breath play is a real thing and that some of my gold customers like to choke me but know better than to make me pass out completely. I also showed him how some customers like to constrict my tits or pussy with rubber tubes until they turn blue. He thought that was hilarious. I had a long conversation with him about blood flow and how it had to be monitored. He seemed fascinated by the science involved. I think he was looking at these lessons almost as a science experiment - with me as the subject.

There was a difference now though. I think having actual SEX had really changed things between us permanently. He was much more comfortable with what I was teaching him. It made it easier for me to show him everything and it made him feel less guilty about watching my tits turn purple while I rubbed my cunt furiously into a froth.

Once we crossed those lessons off our checklist, I began to show him implements that only induce pain. “The act of sharing pain – giving and receiving sometimes makes me closer to someone than if they share intimacy and sex, Sir,” I explained.

Freddy nodded although I knew he was most uncomfortable with the items that really hurt me. I started with a Spanish horse that Master Randy had made when he lived here. He left it behind. It consisted primarily of two wooden planks that formed an edge in the middle. I straddled it and pushed my cunt-meat flat down on it. Then I put my feet in stirrups and placed my hands behind my back.

“Usually, I am cuffed and gagged as well,” I demonstrated by asking him to push a lever. The wooden lever was simple. It dropped heavy sandbags that pulled my feet down in the stirrups and forced my weight down on the wooden edge. I screamed in pain and anguish. “Some guests keep me up here for the entire session and play with me,” I said.

Freddy wasn’t shocked and didn’t run away – but he wasn’t interested either. I decided to stick with the more basic punishment implements first. I asked him to help me off the Spanish horse.

“So you couldn’t get off if someone left you like this?”

“No sir, I couldn’t,” I admitted. I pointed out that if my feet were locked in the stirrups and I was bound and gagged it would be even more difficult.

“So you are like a fly who is waiting for the spider to make a meal of you and you can’t move at all in their web?”

“That’s a good metaphor, Sir.”

“Aren’t you afraid one day the spider is going to do something you REALLY don’t like?”

“That’s part of the bondage – it’s a predicament, and I am at someone else’s mercy to get out.”

“Did you ever worry that I’d stick something up your ass when one of your previous Masters tied you up in the living room?” he asked.

It was a good question. “Yes, you seemed obsessed with assholes, and I couldn’t have stopped you.”

“Would you have been mad if I had?” he asked. I could tell he must have thought about it.

“At the time, yes – you weren’t permitted to play with me like that,” I admitted. I probably would have hung him by his short-hairs. I had made Myra wear a butt plug when she put a quarter in my ass.

“Yet, you’d let a total stranger do anything they wanted to you back then?”

“Yes Sir, I know it sounds strange but I didn’t think you were mature enough to handle playing with me.”

“No, you just didn’t want ME doing it, because it made you uncomfortable.”

He didn’t want any rebuttal. He told me to continue talking. He was right of course. I wasn’t comfortable with him or his sisters playing with me back then but I’d literally fuck a hobo if I was bored and horny. I had simply told myself the reason was that I didn’t think they were mature enough. They were mature enough to see it, know I did it, and talk to the people who did it to me.

I felt guilty again, but I had done what I had done and there was no taking any of it back. “Well, now you can play with me any way you like, Sir. Okay?”

“Yeah,” Freddy told me to continue with his lessons.

I didn’t show Freddy every tool he could use to hurt me. I did try to give him a wide selection of them though. “I can absorb a lot of pain – so don’t be afraid to experiment. Just please don’t make me stick my finger in a light socket,” I wasn’t going to do that again! A customer paid a lot of money to shock the shit out of me over and over.

I suppose I would do that again if he came back and the girls let him use me. It felt like my arms, legs, and entire cunt was numb when he got done with me. I’d rather be shocked by a stun gun than continuously put my naughty bits into an electrical outlet.

I started with simple paddles, floggers, and wooden dowels. I showed him how to hit with force and to apply torque with his hands. His sisters had studied what Randy did and seemed to pick it up naturally.

Freddy had trouble separating me as his mom that he didn’t want to hurt - and me as the pain-slut who was volunteering to be a training dummy.

My son is thoughtful and wouldn’t ordinarily hurt a fly. Yet, he seemed interested in understanding what made me tick. He wanted to understand if the pain gave me pleasure or if it was truly intended to keep me from misbehaving.

“Sometimes a bit of both, Sir.” I admitted truthfully. I explained how the endorphins induced a tingling sensation and the adrenalin rush kicked in to block the pain and send a different signal to my brain.

“So, if you do something really wicked, I could actually be turning you on if I paddle you?”

I admitted that I was a confusing mess and that usually the pain, coupled with being asked humiliating questions about my shortcomings usually did the trick. “If someone just silently dishes out punishment, I can usually absorb pain like a sponge. When they actually make me look at myself for what I am – that is when it starts to actually feel like discipline.”

Freddy had no idea what I was talking about. I had given him so much information already that I was afraid he would be on overload. I may have underestimated my son though. He wanted to understand by doing and that was fine with me.

I guided him through giving me a spanking while I bent over. I recommended he used a paddle so that it would absorb the shock instead of his hand. I taught him the finer points of where to hit, how to hit, and how to put a nice spin on the pain. I get spanked all the time though and the hardest slice on my ass didn’t bother me. He could see that.

That’s when I gave him examples of questions, he could ask me. “You can ask me about what I did wrong, what I am learning, how I feel about serving you. Insist I give clear responses that completely answer the question and do not babble.”

“Do you like serving me?” he asked as he applied the paddle to my bubble butt.

“Yes Sir, I was nervous about teaching you all of this at first, but now I am glad I did,” I admitted. It was cathartic to hear myself admit it without shame and humiliation.

“Would you care if Barbara knew that you are my pet now?” Freddy remembered my old nemesis from work. The one who saw me walking around Wal-Mart with my ass hanging out.

“Yes Sir, that would be incredibly humiliating. She would never understand why I obey my son,” I told the truth.

Freddy observed that my pussy got wetter, and my asshole puckered when he asked me questions about people finding out about our relationship.

“Only a wicked twat gets turned on by serving her son,” he said. The words didn’t sound natural coming from my sweet son’s voice – but it definitely mortified me when I heard him say it because he was right – I had crossed a line most mothers would never dream of crossing.

“Yes Sir, I am a wicked twat! And a dumb whore, I’ve run off every competent Master that wanted to keep me in line. Now I serve my teenage daughters and son because I am a horny bitch that put my needs above theirs – and through your kind graces you have seen fit to put me in place and keep me there!”

I think my words were harsh but truthful. I got the impression Freddy needed to hear me tell him that it was okay to put me in my place. We went on like this for ten minutes or so – each spank was followed by another question.

He seemed to grow in confidence with every swing and focused more on revealing the true me and my motivations for agreeing to be a slave. He didn’t let me give half-answers either. He asked me a few funny questions too like “Have you had enough or should I drive a bull dozer up your ass?”

Most of them the questions he asked affirmed that he was in charge and that wasn’t going to change anytime soon. It was an important step that I had never intended in teaching him about women. He was learning how to stroke my mind – as well as my body.

Once I got him over the hurdle of actually using a paddle on my ass, I showed him how to smash my nipples with a wooden dowel and how to spank my pussy.

I taught him how to pinch my nose and cover my mouth and when to let go (If I turn blue and pass out). I taught him how to grab me by my throat and squeeze without crushing my windpipe. “It sometimes excites me to gasp until I am out of breath, Sir.”

We laughed a lot, so it wasn’t all pain and sadism. I showed him how to put me in a position with my back against the wall and my hands behind my back as if I were sitting on an invisible chair – until my legs gave out. He liked that a lot because my tummy started quivering and my legs began to shake.

I showed him how to hit me with everything from the netting of a tennis racket, to an actual leather whip. He didn’t break the skin, and I warned him about body parts he should never aim for (like the face) – but I gave him plenty of room to practice.

I showed him how to tie me up with rope – including binding my tits until they turned purple. I told him that was probably too painful to do to the girls but that It happened to me a lot. “Some days I will wear rubber binders around my boobs all day - it’s to remind me to behave myself and that I am just a pain-pig, Sir.”

Freddy enjoyed my lesson in Shibari bondage. I didn’t teach him to hang me from the hardpoint – I was worried he might drop me. I did show him how to apply the rope to my mid-section, tits, around my cunt, and ass so that I was balanced. Too many amateur bondage enthusiasts will tie only one portion of the body, and then I’d fall flat on my face when they lifted me off the ground.

“Bondage is a big part of what I do – immobilizing me and limiting my movement – caging me.” I showed him how I slept. He laughed when he realized I slept gagged most nights.

“How do you sleep with drool running down your chin?” he seemed amused by the notion that I slept like a dog in a cage. He had seen the cage in his sister’s room but I do not think he ever put two and two together about how I was locked in the cage. He was usually in bed before they put me in the cage.

“It took a lot of practice, Sir” I showed him how the girls slid broom handles through the sides under my tummy, tits, and over my back so that I’d have to sleep in a crawling position. “I usually get fucked so hard all night that I sort of pass out this way now,” I said.

“Don’t you miss sleeping in a bed?”

“Sometimes, Sir. The only use I have for a bed is for fucking someone,” I admitted with a churlish grin. I was shocked when he bent me over the bed and began to spank my ass.

“I can spank you on the bed too,” he was joking but he was quite right. I was glad he was growing comfortable with me and a little terrified that we had long since crossed the threshold that he would ever see me as anything more than a human pet.

In a way, it was a liberating feeling. I could show him everything and not worry that I would need to tell him to forget what he saw or heard me say. He would never again see me as an authority figure – I knew that much was true.

I showed him the different kinds of gags that could be used on me. Ball gags, rubber ball gags, dildo gags that have one end going down my throat and one end sticking out so I can face-fuck a man’s asshole and peg him. Freddy knew about my gags but I wanted to make sure he understood I had some that could hold my mouth open wide, and some that could shut me up really well.

He loved how the drool fell out of my mouth and down on my chest.

I encouraged him to taste it, and also taste the salty sweat on my tummy. I wanted him to get a good idea of the scents of a woman’s pussy when she was aroused and the taste too. He didn’t eat me out. I wasn’t going to make him do that. I wouldn’t have stopped him either.

He did find out how elastic my cunt flaps are. I showed him how the clitoris worked and where my pee-hole was. He was fascinated. “It’s like a dick but inside you,” he mused.

“If only I could fuck myself with it,” I chuckled.

He put his head up to my pussy lips and pulled them down around his face. He didn’t eat me out – I didn’t think to teach him that. Instead, he pulled them like I showed him and sang “Do your ears hang down? Do they wobble to and fro, do your ears ... hang ... down?”

It was a nursery rhyme I used to sing to him at night. I tried not to think about the fact that a mother shouldn’t be teaching her son these things. The girls had ordered me to educate him in all things women – and he was now my owner as well. I had a difficult time processing that my son was my owner – much more difficult than seeing Myra and Athena in the same light.

Freddy had a hard time believing that I let men melt candle wax on my pussy or zap me with stun guns. I showed him but he had no interest in trying it out on me. He laughed while I jerked and spasmed on the floor after I zapped myself. I probably get shocked at least once a night -and always on my cunt, tits or asshole – men can be merciless. That is why they pay 150 dollars or more to play with me though. I do things their wives would never dream of allowing them to do.

I explained that to my son as well. “I am a whore – but the things I do are free with a donation.”

I thought it best to literally show him everything -tell him everything. There was no point in hiding things now.

“Fart for me,” he said at one point.

“What, Sir?”

“Bend over, spread them and fart for me.”

“I am not sure you want to smell a stinky-mom fart, but as you wish,” the girls had challenged me to show him the good, the bad, and the ugly – this was definitely in the ugly category.

I bent over, spread my cheeks and tried to muster up a fart without accidentally shitting myself.

“I saw Athena fart once, at least I think I did. She was standing in the spread cheeks position. She didn’t think I was watching, but I was. I didn’t think girls fart - at least not the same way boys do

He put his sisters on a pedestal – especially Athena. She was like an angel to him. Even though when they were younger, she could be ruthless to him and often blamed him for shenanigans she and her sister got into like a broken lamp or a stolen snack. He never held things like that against her.

“It was like her butthole opened up and yawned – and then a nearly silent, delicate, sort of fart-whisper came out that sounded like fripppp,” I watched Freddy relive that moment, with his eyes closed.

Unceremoniously, I let out a trumpet-like blast to prove to him that girls can indeed rip nasty cheese if they have too. “I try to fart between clients because most men would be disgusted by this.”

Freddy laughed hysterically. “I saw your asshole open and belch!!”

I shivered again – quite humiliating, but his good-natured laughter softened the gut-punch of embarrassment.

“Don’t you hear us rip farts in the morning when we all shit together?”

“Yeah, but I don’t count that because I can’t see what’s going on when we are standing in line.”

“I want you to ask permission to fart anytime I am around and then show me. I want to hear it and see it. I don’t want you to do any silent ones.”

I wasn’t sure if the girls were okay with him giving me new rules. I told him that I would as long as Athena and Myra approved.

“I am going to tell them they need to do it for me too,” Freddy folded his arms stubbornly.

I knew Myra used to be rather shy about showing her bottom. However, since they took over, they’ve stopped being shy in so many ways. I assumed they would go for what he said.

“I am allowed to play with your flaps or just stick my finger inside you?” Freddy began rubbing his fingers around my pussy while I remained bent over.

“I think at home you can touch me anywhere, Sir”

The rules that the girls had decided upon were mostly for themselves – and I had only just heard about them that morning. I had trouble remembering all the rules for myself – there were a lot of new ones.

Freddy on the other hand seemed to know them by heart already. “I can touch Athena and Myra anywhere – even outside of the house. I can pull their pussy lips, right?”

“Well, that’s not up to me any longer, Sir. I would imagine that if you yank them as hard as you did me, it may hurt them. I am used to having my flaps tugged and pulled. Let me show you how to lead me around.”

I wet my nipples with my finger and frigged them until they stood up straight. I put his hands on my tits, and even though I am a good bit taller than my son, I bent down and demonstrated how he could pull me around by my nipples.

“You can lead me by my cunt as well,” I tied a cord around my clithood and showed him how to use it like a leash and also how he could just hook two fingers and guide me around.

“Master Randy used to pull you by your nose and ears,” Freddy reminded me.

I had thought about Randy every day since my daughters took over. I wondered what he would think, knowing I surrendered my existence to my daughters (and now my son). He probably would think I was batshit crazy. Why did he have to tell me he loved me? That was the kiss of death for our relationship.

I could have worked out anything else – but that was just not going to last. He’d eventually fall back OUT of love with me and then where would we be?

What was done was done now though, and there was no looking back. I told Freddy that Randy was a different kind of Master and he had a lot of upper body strength. I let Freddy try to pull me by my ear and my nose. He would have yanked it off my face before he budged me.

He laughed and asked what else he could do. I showed him how to attach a leash and make me crawl. I told him that in general practice, I am to crawl out front and to the right so that my asshole and cunt are seen. I demonstrated a wide-stance crawl that exposed me fully.

“Sometimes the girls want me to follow quickly, and they will tell me to heel,” I showed him how I could follow on his heels rapidly. I also taught him to hit the back of my feet and thighs with a ruler when he wants to chase me around while I am on all fours.

Once Freddy started to get a little overwhelmed, I gave him some lotion and asked him to rub me down all over. “This is called after-care. I used to have a Master that would cuddle with me after he beat the snot out of me. He’d often give me a bath or massage me after a particularly grueling session. At the time, I didn’t appreciate it. I thought he was being too soft. However, I do miss it sometimes.”

I had shown him every part of me – bottoms of my feet, pussy, tummy, belly-button, nose, hair – you name it. Now, I asked him to take his time and rub lotion everywhere. “sniff, pinch, touch, poke, grab,” I grabbed the side of my ass cheek and gave it a nice jiggle and then a slap.

Freddy REALLY enjoyed massaging me – like a lot. I liked it too. He was methodical and started at my shoulders and then rubbed my back all over. I felt a little guilty letting him do that to me while I did nothing in return. He enjoyed exploring my body though – every crinkle, wrinkle, fold, and flap.

He spent a long time just circling his finger around the folds of my asshole. “I can see which way your turds come out,” he said brightly.

I shivered because I had almost forgotten it was my son, and I was snapped back to the reality that this was the boy I had in diapers only a few years earlier.

“That dark patch is just natural. My asshole is clean back there,” I’ve seen plenty of pictures of my asshole. It could probably stand a little bleaching. It has a very natural flow of dark skin around the anus.

“You can play with my asshole all you like, but I have an entire front half to explore too,” I giggled. I think Freddy would have lost himself memorizing the crinkles in the rim of my butthole if he could have.

When I rolled over, and he started massaging my tits, he asked me, “When I am touching you or you are jerking me off – will you touch yourself? The way you liked to be touched?”

“I am not supposed to focus on my pleasure, Sir. I am supposed to be pleasuring you,” I explained.

“I think it makes me horny to see you get turned on and I don’t know how all of this works,” he indicated my body with a wave of his hand. I was so much bigger than Freddy physically. I could understand why he was intimidated.

“Yes, but could you order me to do it? If your sisters see me playing with myself without permission, they will think I am tricking you into letting me get my wicked jollies and taking advantage of your generous nature.”

“I don’t see why your jollies should be any more wicked than mine,” Freddy was getting aroused again. I could feel his hard dick on my tummy.

“I am a wicked cunt, Sir. I get turned on being fucked hard and slapped.”

“You also seem like you are getting turned on just being touched like I am doing now,” Freddy observed. He was correct.

“That is true, you are doing a good job, Sir. If I wasn’t in discipline though, I’d be out hunting for peckers to suck – ignoring you.”

“No you wouldn’t. You can get all the dicks you want here, Mom.” Freddy reminded me.