A Reversal of Fortune

"Yes Mistress"

"And when you don't you submit to my punishment. Right? In fact if I just feel like it, you will submit to my punishment, Right?"

"Yes Mistress".

"Good boy. Now I need to get going. But I want you to grind yourself to orgasm in front of me demonstrating your submission to me."

I didn't need to be asked twice. I began grinding away moaning and whimpering with pleasure. Then suddenly I came, a beautiful warm squirt all over my pillow. I just lay there.

"OK, now clean that up with your tongue. Every drop. We don't want that staining the pillow."

I got back up on my knees, my belly sticky with cum and began licking the pillow.

Donna got up. Stuck her hand down inside her pants. I could see her inserting her finger in her hole through the outline of the fabric. She pulled the hand out, bent down and put it in front of my nose and then touch my lip with the tip of her finger. I knew what to do. I sucked them clean, like an animal I sucked, so beautifully delicious.

"Now here is my number. Text me saying you want me to be your mistress. I will send you the rules. And then I will own you. Does that sound good Geogine?"

"Yes mistress."

She dropped a business card and quickly walked out of the room, down the stairs and out the front door.

I looked at the card. Her title was "Director Business Development, Bechtel Corp".

Wow. This was going to be quite a ride.

PART 6 - The Routine

I have just arrived at the front door of Donna's apartment at my appointed time, 7:30 am sharp on a chilly spring morning. This is how I start every day, except on those nights she graciously texts me before 8 pm in the evening, letting me know my services won't be required. Sometime when she is getting fucked by some stud who stays the night, she tells me to show up a little later after whoever has gone so I can clean her up while still fresh. Not my favorite part, but I would never turn down a chance to lick her pussy. Never.

So here I am again at her front door. I unlock the door with a key on a big pink fluffy keychain, something difficult to discreetly get in your pants pocket. She loves doing stuff like that. Not blowing my vanilla cover, but having me do things that make people do a double take and wonder, or maybe they don't and I am just paranoid. Anyway, the embarrassment of knowing people are looking at me while I follow her kinky directions is all part of her brilliant method.

I enter the foyer, shut the outside door behind me and start to undress. I shiver a little as I fold my clothes and place them on the little wooden bench. Neatly folded of course. I have learned the hard way messiness has consequences. Then I take the soft leather dog collar off the hook and put it around my neck. She has explained how collaring is a sign of respect and submission. Of course while she educated me on this point as I laid across her lap with a hair brush punctuating all the rules and responsibilities being conferred.

I have now been under Donna's control and guidance for a month. At first it took some getting used to, truly mind bending. Constantly thinking about her beautiful tight ass and moist vagina. A sort of mental worship, an obsession.

Now it feels as if I have always lived this way and couldn't imagine life without her discipline. She ensures sex and her sexiness is alway on my mind; her smell, her beauty, and her strength.

Of course there are certain boundaries she has set, for example I will never be allowed to cum inside. That she made that crystal clear. Both my penis size (my clitty, as she often says) and my semi-feminization in her presence makes me not worthy, essentially useless in that department.

But she allows me to bow down at her feet and make her cum with my mouth almost every day. She can be generous, giving me the relief I need when I am really desperate. It generally involves a lot of begging and sometimes cuming in very embarrassing or humiliating ways, but it still feels magical.

After my collar is in place I opened the backpack she always leaves in the foyer to see if I will be wearing anything else during today's session. I reach in and feel something frilly. Pulling it out I see they are pink panties all lacey and fluffy. If you can imagine the most unmanly underwear ever made, this is it. As I slide them up my legs, my cock began to harden in spite of me trying to suppress it. It's a testament to what panty slut I had become under Donna's control. Of course, I really can't blame her. She only brought it to the surface from the dark depths, something I had always concealed, even from myself.

OK, time to enter. I softly rap on the inner door and wait. I hear a giggle, and then her distinctive deep sexy voice saying "enter please". I turn the knob to open the door and then get on all fours, push the door with my nose, and crawl in. As the door swings fully open, I look around the room. Donna is sitting with her legs crossed on her wooden kitchen table chair with a steaming cup of coffee on the table next to her. She is in a soft draping T-shirt with the outline of her erect nipples visible. Good to know I have some effect on her. She has no pants on, just those beautiful tanned legs facing me. Though I can't completely see, I am pretty sure she is not wearing panties. Her sitting in that chair means one thing; a spanking is coming.

Then I hear footsteps and that giggle again. I look over and there is a woman coming out of the bathroom, probably in her fifties, but perfectly fit and nearly as beautiful as Donna. She has a loose swoop shirt with a sports bra visible. She is wearing shapely maroon workout tights. I look up at her face as she smiles looking at me crawling along in my bright pink panites and collar.

Smiling warmly, she motions to me with her bright red polished fingernails, "Don't be shy. I won't bite, at least not just yet."

She turns to Donna and says "Oh, my dear, you have done very well for yourself. He looks like great fun, and apparently so well trained" the woman says.

"Thanks Mom" Donna says. "You taught me well."

"Well, with your Dad it took a very long time to progress this far, but of course it was a different time. Young women today are much more in touch with what they want and know how to just go get it."

Donna looks down at me as she says, "Let's hold off on the compliments until you see how he performs"

Regaining my composure after the surprise, I say "Good morning ma'am" as I look up at Donna's mother.

Donna says, "Georgy, my mother hates being called 'ma'am'. Really hates it. Why don't you just call her Mommy?"

"Mistress, that seems a little weird calling her Mommy. I would prefer something else."

Donna sighs, "Georgy, time to get up on my lap." She pats her bare thighs. Then says firmly, "Now."

I crawl over to her, my pink panty clad ass swaying in the breeze. I get up and lay across her beautiful lap.

"Now present yourself"

I raise my thighs off her lap by pushing my toes and my hands against the floor pushing my ass in the air. Donna slowly slides my panties over my erect penis, off my butt and lowers them down to my knees.

"OK, relax" she says.

I settle back down onto her supple lap.

"Now keep those panties at your knees, don't let them fall to the floor. You know what happens if they do?"

"Yes, Mistress."

"We both want to avoid that unpleasantness I needed to administer last time you let them slip down"

"Definitely Mistress"

"Good boy"

Hearing her say ' good boy' makes me feel warm all over even in this compromised state and knowing the pain that will come from a maintenance spanking.

"All right now. I was going to just give you your maintenance spanking, but given your talking back to me when I made a request for you to properly address my mother this will need to be a punishment spanking. Not a serious punishment spanking, but a punishment spanking nonetheless. Do you agree?"

"Yes Mistress". I grit my teeth knowing what is coming.

"Mom, I think you will enjoy this. Georgy becomes very entertaining during his punishment spankings. He becomes a whiny pleading little girl."

"Oh Donna, you have such a delicious nasty streak"

"I learned from the best, Mom."

."Now Georgy, let's get your clit between my thighs like a good slut." I wiggle a little as she guides my cock between her thighs. It feels so absolutely wonderful to be there.

"Now - no cuming! You know the rules."

"Yes Mistress. I know the rules."

"Good boy". Again the warmth washes over me.

"A clit? Calling his prick a clit. Very nice touch dear."

"Thanks Mom." Donna says as she lands her first bare handed smack on my ass.

Whap, whap, whap... She gets her rhythm going as a warm sting starts to rise in my ass.

After about a minute I begin to whimper softly starting to enjoy the friction on my penis between her thighs. Donna notices me starting to rock back and forth a little and stops.

"Mom, would you do me a favor and help me out with Georgy? I think he could use a little more humility and neediness."

"Of course dear. It would be my pleasure. What would you like me to do?"

"Can you take off your tights, grab a chair and swing it around so it is facing his face?"

"Sure thing" her Mom says as she pulls off her sneakers and peels down her yoga pants. She, like her daughter, has beautifully perfectly toned legs. Unlike her daughter, I see she has a carefully trimmed landing strip of hair leading to her pussy. I see a few drops of moisture clinging to the hairs at the bottom. I feel my already gorged member get harder between Donna's thighs.

"I can feel somebody is enjoying the show". Donna says as she swivels her torso to grab something off the table while I remain splayed across her lap.

I try to stay focused on keeping my knees sufficiently apart to keep the panties from falling to the floor. She likes me in this position because with my legs spread she has easy access to my balls whenever she feels like working her mischief.

Her Mom places the chair facing near my head.

Donna says, "Mom, can you please pull it back a few feet. I want Georgy to be able to grab your knees, but not be able to rest his head on them. We want him to get a bit of exercise."

"Absolutely dear."

"Georgy, now reach out and put one hand on each of her knees and keep your back straight as you stare at her vagina. Can you do that for me?"

"Yes Mistress".

Then she chirps, "Georgy, and why don't you say hello to Bertha? I think she wants to join the party also."

I audibly groan accidentally. I know well, Bertha is not a person, it's a hair brush. A heavy old fashion wooden hair brush my Mistress brings out when I am going to receive a serious punishment spanking. Bertha's imprint will remind me of this session for days afterwards.

Donna rests the cold head of the brush that she must have retrieved from the table on my tender ass, and just lets it sit there. She then lifts the brush and slides between my legs and taps my balls, reminding me of her power and my vulnerability without saying a word.

"Oh, Donna, you kept the brush I gave you on your 18th birthday. How sweet." her mother says, "You used to squirm and squeal so adorably when I used that on you as a child. Your father on the other hand hated that brush. I guess I put a little more gusto on the swings when I used it on him."

"Yes, Mom. Well, Georgy appreciates this brush. He knows it makes him a better sub. Don't you Georgy. Why don't you thank my Mother for giving it to me?"

"Mommy, thank you for giving my mistress Bertha. It is an important part of my discipline." I say, not able to tip my head up enough to look her in the eyes. I just stare at her pussy while I speak.

"You are most welcome Georgy".

Then, POW! The sting shoots through my body as Bertha makes its first contact. "Ouch" I squeak.

"Now Georgy, you know the rules. No sounds. We don't want to have my nosey neighbors stopping over again."

"I am sorry mistress, I couldn't help it. I was just surprised. I will be quiet from now on. Promise"

Bertha then lands three more times in quick succession. I hold in any sound. I am concentrating on not letting my panties drop and holding onto Mommy's knees keeping my back stiff. I so want to be a good boy and get through this making my mistress proud in front of her mother.

The next slap hurt so much I couldn't help it. A loud "Owwww" comes out of my mouth.

"Oh, poor dear. I know you can't help it. I know you are trying, but you just can't do it. Let's get you some help. Why don't you get up, crawl over to my panty drawer and pick out a pair that will help you stay quiet."

I gently push myself up using Mommy's knees as support. I slide my dick from between Donna's legs, all the while careful not to let my pink panties fall to the floor. My penis is already missing the warmth of her legs. I then lower my knees to the floor encased in the panties and on all fours shuffle to the dresser in the corner and pull open my panty drawer. I pick a high waisted black nylon pair, stuff it in my mouth and crawl back.

"Good boy. Now let's get you back up here and get your spanking over. We don't have all morning."

I slide back up onto her lap, everything back in position; panties on knees, prick between her knees and staring back into her mother's pussy. Donna now begins again. Strong hard strokes about 3 seconds apart. Just enough time for the pain to cascade though my body before the next wave comes. I really try to stay still but with every strike I jerk a little. My penis between legs rubs back and forth as I let muffled grunts out through the panties. I start to sniffle a bit, holding back the tears.

This is so embarrassing. Donna and her mother chat as the blows continue to rain down, as if nothing out of the ordinary is going on.

Suddenly Donna stops. My ass is throbbing and my dick is very sensitive at this point. I slowly move my hips, ever so slightly drinking in the sensation in my crotch. I am trying to appear still, hoping this is over.

"Mom, can you tell from Georgy's face how much he wants to cum? He is being a little naughty, stimulating his clit pretending not to do anything and definitely not asking permission."

"I definitely see that. What a naughty little boy."

Donna reaches around and pulls the soaked panties from my mouth. "Now what do you have to say for yourself Georgy?"

"I am sorry, mistress, but I so need to cum. You know what a helpless slut I am. And staring at Mommy's pussy. I can't help myself." I plead for mercy.

"Well... here is what we are going to do", as she twists around to the table again, I hear Bertha being placed back on the wood surface and I hear Donna pulling rubber gloves on. "Georgy, you are going to tell my mother how much you want to give her pleasure with your mouth while I milk you. Understand?"

"Yes mistress." I am deeply relieved.

I feel the first KY Jelly covered digit penetrate my ass, then a second alongside it. Involuntarily, I raise my hungry asshole up for more. She finds my prostate and gently starts to rub.

As the fog of humiliation and pleasure rolls over me, I begin begging.

"Mommy you have the most beautiful vagina, I so want to lick your pussy. I want to lick it for hours and hours, I want to give you pleasure. You feel so good...." I go on and I.

Her mom reaches down and starts gently massaging her own clit as I beg and plead.

Soon I feel like I am peeing. A slightly pleasurable feeling, but mostly embarrassment and relief. I know this is as good as I am going to feel when being milked. It never gives no real orgasm.

Donna says, "It feels like someone has made a mess they are going to need to clean up".

I know the drill. I slide off her lap. I kneel down in front of her and start licking her feet, massaging them with my tongue, working my way up her legs to the cum frosted inner thighs. I lick voraciously, consuming and cleaning every drop.

"Now that's my good little cum slut. Why don't you head to the foyer and head off to work? Mom and I have things to do. I will see you this evening at 6pm sharp."

"Yes mistress. Thank you for the discipline and being allowed to relieve myself. It was very nice to meet you Mommy. Your daughter is very beautiful and smart."

"I know she is. Yes indeed. Now run along little pet. Til we meet again... uhmmm" As she spoke she plunged her fingers deep into her vagina.

She was quickly headed for an orgasm and it was clear that I was not supposed to be there when it crested. Once she came I knew they might change their mind and not let me go. I quickly scurried out to the foyer and off to work.