Punishment of the Penitent Pin Dick Part III

Making contact with Mary to pay my pin dick penance to her wasn’t easy. I had discovered her being unfaithful to me more than three years ago. I had walked in to her bedroom (to surprise her for our six month anniversary with a buncho f flowers) to discover her having sex with my friend Carl.
Mary had not tried to apologise or even contact me. She had moved and it took me some weeks to track her down. In this time my girlfriend, Mistress Jazz had taken a big cocked lover who she would fuck daily, letting me only listen at the door. I would be permitted to watch once I had paid my penance to the four women I had previously frustrated with my snack sized erection. I had already made penance to two of them and was desperately seeking Mary. I eventually ended up calling her mother (who had never been fond of me) and had a hell of a time convincing her to give me Mary’s contact details.
In the end Mistress Jazz spoke to Mary’s mother (Kay) and point blank explained the reasons for me contacting her daughter: I had to make up for my penile shortcomings by being punished by Mary as she saw fit. Kay was greatly amused by this and certainly enjoyed gloating down the phone to me. “Yes Mary told me about your little thingee” she told me “grossly inadequate. Jacinta is right to have you punished, too many little boys go around pretending to be men and failing to measure up where it counts.”
Kay had Mary call me who was completely unapologetic for her infidelity. “Of course I fucked around on you, what did you expect with that little prong?” she stated matter of factly “I fucked half your friends before I let you catch me with Carl. They were all bigger than you, with that skinny little thing between your legs. Carl was the biggest and I knew he was a keeper so the best way to get rid of you and that annoying little pee pee was to let you see me with a real man. I just wish I had of cucked you like your girlfriend has, you might have come in useful for something. You certainly weren’t any use in the bedroom. As for your punishment, I’ll give it some thought and get back to you.”
She left me hanging for three days before calling and saying I would be required at her house that night. Mary was a statuesque woman, slightly taller than me and very fit having studied ju-jitzu for years. When I arrived I knew I was in for a torrid time. She was dressed in black lingerie with a short leatherskirt and knee high boots looking every inch a femme domme.“You will not be required to wear clothes tonight, strip so that I may observe your manhood”. I did as I was instructedand was soon naked before Mary. “You know what separates the men from the boys don’t you? Their cocks, and I’m afraid you are a very little boy.” Having said that she ordered me into the bedroom where I beheld what I was in for that night.A riding crop, a paddle, a cat o’ nine tails and Carl completely naked with his massive tool standing at full attention. It was bigger than any I’d seen, about ten inches long and as thick as a beer can.
“Now that’s what a man’s cock looks like” said Mary. Carl looked at me with a mocking expression “Must be cold in here” he said gesturing to my little penis, dwarfed by his thick erection.
“He’s here to be punished for his fucking me with that thing”said Mary “firstly he must be spanked” Mary sat on the bedand ordered me over her knee. “If you’re going to fuck like a naughty little boy you must be punished like one” She began to spank me “each time I spank you, you will say ‘Thank you mistress may I have another’ is that clear?” she said raining a stinging slap on my reddening buttocks.
“Thank you Mistress, may I have another?” I uttered dutifully
“Why are you being punished?” she asked between blows
“Because I have been a naughty little boy” I replied getting turned on as she continued to spank me like an insolent child. My penis was fully erect and I began to hump Mary’s leg
“Are you fucking my leg?” Mary asked sternly
“Yes. I can’t help it” I replied. Her tanned leg was silkys mooth and the humiliation and spanking had me turned on so much I could not help myself.
“How dare you” she yelled grabbing my balls in her hand “if you do that again I will crush these little peanuts, do you understand?” she demanded gripping my balls tightly forcing me to groan in pain “well, do you?”
”Yes Mistress” I gasped as she released her grip “Carl, get the cuffs” she said. Carl produced some handcuffs from the bedside table and snapped them tightly to my wrists. They were then placed on a hook on the ceiling and the height was adjusted so that I was just on my tip toes, hanging helplessly.“Now spank him Carl” Carl began to spank me, not with his hands, or the paddle but with his meaty cock that was rock hard and as long as both my butt cheeks. “Feel that?” asked Mary “that’s a real cock pounding your arse”
“This cock’s been in every girl you ever fucked” said Carl “except that hot little Jazz, but she’s next. Man that tiny little thing of yours made it easy for me to get into their pants. They were all gagging for a real man after being with you. I suppose I should thank you”
This was a revelation, Carl had been a friend of myne untilI discovered him screwing Mary. To realize he had been slamming his cock that was twice as long as myne and over twice the circumference into every woman I ever had reltionship with turned me on so much. To know he gave them what I could not was for some reason unbelievably arousing. “It’s so much better with a big cock” added Mary “to be filled up properly is indescribable” I could not hold out any longer and I ejaculated there and then without any contact to my cock. “What is it about pindicks that has them shooting all over the place when in the presence of a real cock?” said Mary “it’s like a little puppy wetting itself next to a Mastiff” she cackled “isn’t that right poodle dick? Now look at the mess you’ve made. You will be punished properly for this”. Carl picked up thecat o’ nine tails and Mary took up the riding crop and theywent to work giving me a thorough thrashing. Mary soon stopped leaving Carl to continue to flog my back. Once again she went into the bedside table this time producing a bag ofpegs. While Carl made my back red raw with the whip Mary beganto peg my flaccid little weiner. My tiny cock was hiddenamongst a forest of pegs as was my scrotum. My nipples were next. “That’s enough” she said to Carl who put down the whip.“And now the final humiliation” said Mary. She opened up the bedroom door and there was Mistress Jazz and to make matters worse, Mary’s mother Kay. “I just had to see this”she told me gloatingly looking at my pegged up genitals she stated “I’m not sure what’s bigger, a peg or his pathetic little cock”
“Now I’m gonna fuck your girlfriend” said Carl “that makes every girl you’ve ever been with” Mistress Jazz stripped and mounted the bed on all fours
“Oh it’s just so big. I can’t wait” she said staring at the massive shaft of Carl. Carl began to eat her pussy out, rimming her arsehole and tonguing her clit. Jazz was soon squealing in delight “Wow you’re so good at this, better than that little pee wee” she said looking me in the eye “especially because I know a real cock’s coming my way”. Carl had madeher wet enough and slowly began to feed his cock into Jazz’sslippery hole. It took him some time to stretch her out but eventually she had all of him inside her.
“Every girl you’ve ever screwed with that tiny little thing has had that monster cock splitting them in two” Mary whispered in my ear as Jazz moaned in ecstasy. Carl began to thrust slowly with his whole length going in and out of my girlfriend’s gaping orifice as she came again and again from the furious friction of the giant cock. I became erect forcing the pegs on my cock to cause me great pain. “Seeing as though you have failed to provide Jazz with any vaginal pleasure, we think we should prevent you from receiving penile pleasure” explained Mary sternly in my ear as she began to insert two fingers up my arse, finger banging me as Carl pounded Jazz harder than ever she had been fucked before.
“Sodomise me” yelled Jazz in ecstasy “fuck my vigin arse. I want a real man to break my arse in.”
I couldn’t believe it, Jazz had always been opposed to anal sex, even when we were having vanilla sex. She would become too wet for my little love muscle to stimulate her she would not consent to me penetrating her in the back passage citing discomfort and giving me only a hand job. Now she was going to let this monolith of a cock up her rear.
Carl produced some KY jelly from the bedside table and lubed up Jazz’s arse. Once again he slowly fed my girlfriend his cock but this time he was penetrating her virgin backside. Jazz was silent but clearly enjoying the extreme submission as Carl gently thrusted back and forth. Mary began furiously finger banging my own virgin arsehole “see what real men get to do. They give us real pleasure and we are only too pleased to acquiesce to their desires. Now Carl has been places you will never go, just like he takes us places that you could never take us too”.
“That arse is so tight” said Carl “I’m ready to blow”
“Do it up my arse please, please come in my arse” said Jazz. To see my dominant girlfriend who would order me around and humiliate me due to my inconsiderable endowment completely submit to a real man was the biggest turn on I could imagine. Carl came in my girlfriend’s arse and pulled out leaving come dribbling from her crack like a dirty whore. She gladly turned around and licked the shit and remaning semen from Carl’s cock. “My submission is a luxury only for real men with proper cocks” Jazz informed me. She approached me and kissed me passionately letting me taste her shit and Carl’s come on her lips and tongue.
“Your penance is complete” said Mary “I’m so glad to see you’ve been cuckholded and that your little cock will never bother another woman again”
I was let down from my restraints and slumped to the ground with my arms so sore from having been taking my body weight during Carl’s hour and a half fucking of my love. As he walked past he slapped me with his semi erect cock leaving a semenpearl on my cheek. I had one more woman to apologise to for jabbing with my undersized little prick, and then I would receive the long awaited punishment from Mistress Jazz.

MIstress Jazz - The Beginning Part III

The three audience members to my shame all burst out laughing. The humiliation was the biggest turn on I have ever experienced and I ejaculated on the spot.
“You’ll have to train him better than that” said Carol
“Oh he’s always coming at the drop of a hat” said Jacinta“I can’t get more than twenty minutes out of him if I’m lucky. I had to teach him to lick pussy real good”.
“Is that so” said Carol “am I allowed to sample the delights?”

“If you give me a go of Dave’s… thing” answered my dripping wet girlfriend
“But Jazz…” I began
“Shut up” screamed Jacinta “I’ve put up with that little tiddler of yours for two years, you won’t deprive of my first opportunity to fuck a real man!”
“Bloody hell look at it” said Carol pointing at my now flaccid cock “It’s like a cocktail frank over a couple of grapes” This set the trio laughing again.
“And Dave’s looks like a rolling pin over a couple of poolballs” said my wife with no exaggeration. “Now lick her” ordered Jacinta.
I approached Carol “Crawl!” ordered Carol. The loss of control and humiliation I was experiencing had my little cocktail frank engorging with blood again as I crawled on hands and knees toward Carol. I reached to pull down her bikini bottoms but my hand was slapped away. “Pindicks don’t get to touch me, use your teeth”. As punishment formy insolence Jacinta spanked my arse hard.
“Don’t try that again” she ordered.
I managed with some effort to remover Carol’s bottoms and began to lap at her clit. “You’re no good at this” she said sternly and she grabbed me by the hair impelling me forward. My hands were roughly pulled behind my back by Jacinta and Dave handcuffed my wrists to my ankles. I lay helplesslyhogtied with my miniscule erection pressed into the floor.“Now watch what a real cock can do for a woman” barked Carol spanking my arse again.
I could only watch as Dave slowly slid his mammoth cock into my girlfriend’s sopping vagina, stretching her three times as wide as I ever had; it was sinfully sweet to watch. Soon Dave was hammering into Jacinta as she screamed in ecstasy, reaching platforms of orgasmic delight to which I could only dream of taking her.
Dave showed no sign of slowing as Jacinta continued to scream in pleasure like a Banshee “Oh yes it’s so big. Oh finally areal man” she yelled making eye contact with me “Oh yeah bigger is SO much better” she said through gritted teeth. While all this was going on Carol had left the room and now re-entered with a riding crop in hand.
She held the riding crop in the air above me and said “and now for your punishment for being such a naughty littleboy” and she brought the crop down whistling upon my waiting buttocks. She began to rain blows upon my back and butt all the time reaffirming my pindicked inadequacy “littleboys don’t fuck with their little dicks” she yelled “little dicks are only good to wank with. Only real men may fuck, do you understand?” She finished
“Yes I do” I murmered
“Yes I do what?”
“Yes Carol, I do”
“Carol? How dare you!” boomed Carol “Only a real man may refer to me by name, I am Mistress Carol to you!”
SLAP down came the riding crop again on my red flesh the pain combining in a crescendo with the humiliation of watching my wife being pleasured by a big cocked stallion. “Do” SLAP“You” SLAP “Understand?” SLAP.
“Yes” I responded knowing the mistake I was making and rubbing my little dick on the ground in anticipation of the
SLAP “yes” SLAP “who?”
“Yes mistress Carol” I cried in ecstasy as the final strike of the crop had me coming where I lay.
“It’s nearly time” said Dave who was now slowly stroking in and out of my exhausted girlfriend.
“Then do it” said Mistress Carol
Dave then pulled out of my wife as I was removed from my hogtied position and brought to my knees where my wrists were hastily re-cuffed to my ankles.
“You’ll have to clean up that pathetic little spot of come”said Mistress Carol observing where I had orgasmed as I lay “but first here’s a real load for you.” Dave then forced his oversized member into my mouth and began to fuck my face, forcing me to gag as he continually hit the back of my throat.“Take this pee wee” said Dave as he unleashed a manful load of semen into the back of my throat. He did not remove his cock until I had swallowed the last of what he had.
Mistress Carol pushed me back to the ground with her foot and made me lick up the pathetic puddle of my own juices I had left on her floor. I lay there looking at Jacinta who lay for the first time in her life fully sated, caressing her own nipple and smiling at me.
“You’ve fucked for the last time” she informed me through her flushed grin “from now on you only get to watch me fuck real men”
My shameful penis began to swell again at this thought as my tiny testes ached.
“Your punishment for trying to touch me without permission is complete” added Mistress Carol “however your punishment for fucking a woman with that puny little thing you call a cock is still coming”
But that’s another story…