I always knew I had a small cock but I never realised how much I enjoyed being told about it until late in my final year of high school.
As teenage boys are, I was keen to be de-virginised. I also believed all my friends when they told me stories of their own sexual escapades, although they were probably 90% bullshit I felt like I was missing out.
I was a little shy with girls, I was quite insecure about my cock size. I didn’t measure up very well judging from my furtive glances at my peers’ endowment in the showers following football games and PE classes at school.
I felt like I had to lose my virginity ASAP and saw a golden opportunity when my parents went away for a long weekend early in the year. Normally my little sister and I were forced to go away with them but I pleaded study commitments and managed to wrangle the house to myself for three days. I now had a place to do the deed all I needed was the right girl.
The two candidates that immediately sprung to mind were Tina and Ada. They were a couple of years below me at school (Year 10, I was in Year 12) and were renowned among our group for giving it up after a few drinks. They really liked to let all the boys in their year level know they were going out with guys in the more senior grades.
My parents and sister left on the Friday morning leaving me with the run of the house. It didn’t take much convincing to get Tina interested in coming to my place that night under the pretence that there was to be a party “strictly by invitation only” I told her. I also told her that drinks were on the house – now that got her interest. What she didn’t know was that she was in fact the only invite.
I told her to roll up around 7:30 and when I got home at 4 o’clock I’d wished I’d said earlier. Time dragged like never before as I kept going over scenario after scenario of me fucking Tina like a porn star. B 5 o’clock I couldn’t take it any more and had to jerk off, it took me about ten pumps of my little dick and I was shooting a load. This calmed me down for a little bit but it didn’t make time go any quicker.
All I could think about was Tina and her petite little 5 foot frame. In her school dress that very cheekily exposed much of her slender, pale thighs she must have fuelled the masturbation fantasies of half the school. Her perky little boobs were as obvious as her push up bra could make them and she took every opportunity she could to be noticed by the males in the school - which with her long blonde hair and the collective hormones of teenage boys was not very difficult for her.
I was beside myself as first 8 o’clock and then 9 o’clock rolled around. I figured Tina had got a better offer and pictured her getting gang banged by the local football team. For some reason this got me hard as a rock as I pictured a burly well hung older man pounding into her as she begged for more. I was just about to have another tug when the door bell rang.
Butterflies sprang up into my stomach and my erection vanished as I ran to the door. I stood at the door for a few seconds collecting myself and heard two girls giggling. Ada had come with her! The clock said 9:50. I opened the door, there stood Tina in a short, short black skirt that exposed all of her slender legs down to her knee high black leather boots. Her perky little tits were once again being down favours by a push up bra and were encased by a silver sequin encrusted spaghetti string singlet that left her flat midriff exposed. With her stood Ada who sported a fuller figure, her smouldering Italian looks and olive complexion were adorned with the biggest tits in all of my high school. The white shirt she wore had a number of the top buttons open showing off her cleavage to full effect with her curvy hips and round, plump arse complement by a tartan mini-skirt. The heels she stood in gave her calf muscles the perfect definition.
I soaked all this in during the first few seconds after opening the door and it was very difficult for me to pick my jaw up off the floor and try to act cool. “You’re late” I managed to force out “I said seven thirty”
“You also said there’d be a party” replied Tina
“It’s a private party” I responded trying to be cool. The two girls burst out laughing.
“Is it just” said Tina cheekily “so you bullshitted me huh? It seems it was all a plot to get me here alone.”
“Well I…” stammering, I hadn’t really thought this far ahead.
“Don’t sweat it” Ada interjected “just tell me where the open bar is” as she pushed through to get into the house. I stood aside keeping eye contact with Tina who stood on the doorstep smirking with arms folded in mock defiance.
“I ah… guess you caught me” I said with a nervous grin all the while trying not to come in my pants.
“Naughty boy” said Tina stepping inside and talking as I showed Ada and her into the living room “we were at a stupid Year 10 party, nothing but drunk little boys there.”
“We were gonna hit the town but then we thought we might come around and see you” continued Ada who had very forwardly fetched three glasses from the kitchen “and have a few drinks”
“So you weren’t lying about the drinks too were you?” asked Tina with a playful pout and her hands on her hips that had my cock stirring in my pants.
“No. I’ll get us a bottle” I said. I had earlier that week made a copy of my father’s liquor cabinet key. I had anticipated him taking it with him and as I took out bottle of vodka I looked upward and thanked God for what I was about to receive.
After a few drinks we were all fairly drunk but I really had no idea what to do and was to nervous to try and make a move. “I’m bored Roy” announced Tina
“Maybe we could play cards” was all I could think of and I nearly kicked myself before adding with a throat dry from my nerves but a boldness supplied by the liquor “we could play strip poker”
“Ooooooooo how naughty” giggled Tina “do you want to see us in the nuddie?” she tittered with Ada.
“Or maybe we’d get to see him in all his glory” said Ada “I wonder what he’s packing down there”
“Only one way to find out” her friend answered “go get the cards Roy” said Tina as she finished her drink in one gulp.
It was agreed that each hand the winner would be able to choose which person would remove a garment of clothing. Although I had a better understanding of the game I was outnumbered two-to-one. It also didn’t help that the girls insisted that straights and flushes be removed because they didn’t understand them. That was how I ended up down to my boxers with the two girls down to bra and panties. I’ll never forget how sexy they looked with their tight 15 year old bodies on display, nor will I forget how hard my 17 year old cock was looking at them.
Tina won the next hand and there was little doubt who was going to lose the next garment; or so I thought. To my surprise and delight she chose Ada. With no hesitation Ada unhooked her bra and let her firm d-cup breasts spill out. Her huge tits were complemented by a relatively small aureole and some thick nipples that stood out portraying the arousal that the alcohol and a voyeuristic temperament had given Ada.
I won the next hand and had a hard choice. Did I want to see Ada’s pussy or Tina’s breasts. In the end the breasts won out and my dream and I had to pinch myself as the two girls stood before me in nothing but their knickers.
Tina again won a hand and this time she chose me. “You’ve seen us Roy, it’s only fair that we see you”
“Yeah come on Roy show us your manhood” put in Ada
“We’re sick of the Year 10 weenies Roy, we want a Year 12 whopper” put in Tina as the two girls began to outdo each other in teasing.
“So let’s see how much of man you are”
“Or maybe he’s just a little boy”
“Which is it Roy? A big man or a little boy?”
“There’s only one thing that decides Roy. Let’s see how you measure up as a man”
“Well come on, what are you waiting for?” said Ada “let’s see that dick” she demanded draining her glass and slamming it down on the coffee table setting her magnificent tits jiggling.
I was reluctant but had no choice to lower my boxer shorts and reveal my four and half inch erection to them.
“Ohhhhh” groaned Tina “he is just a little boy.” I covered my shame with my hands “don’t cover up Roy! You’ve seen us, we get to see you”
I had no hesitation in obeying and found myself utterly turned on to have my cock the focus of attention. They both stood in front of me in the panties, their hands on their knees as they stooped to get a good look at my rock hard little prick
“What can we do with that little thing?” moaned Ada
“That is definitely the smallest I’ve ever seen” added Tina
“Me too, and I seen a lot!”
“Dam Roy, that is a tiny little cock” Tina said and then flicked my knob with her finger. That was all I needed: I came on the spot dribbling leaving a small glob on the carpet as it dribbled out my pathetic little dick.
“Holy shit he hardly came at all. Even his loads are tiny” said Tina pointing at the small droplet I had deposited and bursting out laughing with Ada.
“Let’s go out and find ourselves a man” said Ada as the two girls started to dress despite my protests. “Please” I said following them down the hall still naked
“Fuck off pin dick. You can’t do anything for us with that tiny weenie” was the only response I elicited as they exited.
“Wait a minute” Tina said after they were outside “Roy, I’m sorry come out here for a minute” she added with some remorse in her voice. Our front door was set some way back from the street so I stepped out surreptitiously with one hand over my meagre genitals. “I really am sorry” said Tina leaning forward and pecking me on the cheek “sorry you’ve got such a small cock!” she added and slammed the front door behind me. The two girls laughed their heads off as they set off down the driveway with me locked out of my house; naked.
If I thought that was embarrassing that was nothing when I got back to school on the Tuesday and everyone had been told of my “short comings”. From that day on my nickname for the rest of my school days was Pee Wee Shot Gun.
Saturday, March 8, 2008
Punishment of the Penitent Pind Dick Part I
Looking back it was a relief to finally be cuckholded by my girlfriend, Jacinta; or as I now am obligated to referto her: Mistress Jazz. The truth had come out when I witnessed Mistress Karen’s big cocked sub (Dave) fill Jazz to bursting point with his man meat, so much bigger than what I brought to the bedroom. I had been informed that I would never bother a woman with my miniature five incher again.
When we arrived home from Mistress Karen’s, Mistress Jazz began her new role as the dominant partner in our relationship.“As I have told you before you have fucked, or what you call fucking with that little lump of flesh, for the last time”she continued “Having now seen what I have missed out on fucking you Skinny, as you will now be referred to, I will have sex with as many MEN as I wish. I’m sick of trying to make excuses for your small cock, like I’m too wet and that I prefer oral. The fact is you barely touch the sides and I need a real man with a man size cock to make me come properly.” Mistress was right, I had rarely been able to come in a woman as my skinnylittle cock would fail to gain sufficient friction and would often slip out during heavy thrusting. I would normally have to finish by jerking off or receiving a hand job. Mistress informed me that was because wanking is all small cocks are good for. “If you are a good little bitch I might evenl et you watch. You are still to be punished for two years of daring to poke your small member into me, but first you will have to pay penance to the previous four women you have failed to satisfy in your inadequate sex life. The first step is to prepare you for your new life”
I was taken to the bedroom where I was shown my underwear drawer. My boxer shorts were all gone and it was now full of pink g-strings, some frilly and lacey. “Strip” Mistress ordered. I was naked in seconds, loving the dominance of my Mistress, my cock began to become erect. “I think you know your role deep down” said Mistress observing my excitement.“From now on you will wear only these” she said as I put on the humiliating pink g-string. “Of course body hair isa luxury for men, not little boys. You have a date at the waxing salon Skinny”
I was allowed to clothe myself and drove Mistress and I to the beauty salon. I was taken to the private waxing area out the back and Mistress had me strip embarrassingly infront of the young beautician she giggled as she saw my pinkunderwear. “If you think that’s funny” said Jazz “wait til you see what’s underneath. Show her your shame” Mistress ordered. I was compelled to obey and stood in front of the attractive young stranger with my small cock (even smaller with the nerves I was feeling) jutting out above my grapesized testicles.
“That IS a small package” remarked the beautician in a way that made me think my lack of size had been discussed in the salon before “I’ll have to give you a discount on wax, we won’t need much to do that little thing” she added as the two women burst out laughing.
“I suppose you see a few cocks in this line of work” said MistressJazz
“Oh yeah, it’s great. I can work out who the hung guys are without having to do all the dinner and dancing crap. That way I can’t be disappointed by little things like this”she said yanking my cock none to gently “There’s nothing worse than getting a guy home only to discover they don’t measure up”
“So have you seen any smaller than this Sarah?” inquired mistress
“No, this is the smallest I’ve ever seen. I feel for you” tittered Sarah
“Don’t be, this little boy’s just been cuckolded”
With that I was put through the excruciating ritual of af ull body wax, something I would have to do on a weekly basis.
When we arrived home from Mistress Karen’s, Mistress Jazz began her new role as the dominant partner in our relationship.“As I have told you before you have fucked, or what you call fucking with that little lump of flesh, for the last time”she continued “Having now seen what I have missed out on fucking you Skinny, as you will now be referred to, I will have sex with as many MEN as I wish. I’m sick of trying to make excuses for your small cock, like I’m too wet and that I prefer oral. The fact is you barely touch the sides and I need a real man with a man size cock to make me come properly.” Mistress was right, I had rarely been able to come in a woman as my skinnylittle cock would fail to gain sufficient friction and would often slip out during heavy thrusting. I would normally have to finish by jerking off or receiving a hand job. Mistress informed me that was because wanking is all small cocks are good for. “If you are a good little bitch I might evenl et you watch. You are still to be punished for two years of daring to poke your small member into me, but first you will have to pay penance to the previous four women you have failed to satisfy in your inadequate sex life. The first step is to prepare you for your new life”
I was taken to the bedroom where I was shown my underwear drawer. My boxer shorts were all gone and it was now full of pink g-strings, some frilly and lacey. “Strip” Mistress ordered. I was naked in seconds, loving the dominance of my Mistress, my cock began to become erect. “I think you know your role deep down” said Mistress observing my excitement.“From now on you will wear only these” she said as I put on the humiliating pink g-string. “Of course body hair isa luxury for men, not little boys. You have a date at the waxing salon Skinny”
I was allowed to clothe myself and drove Mistress and I to the beauty salon. I was taken to the private waxing area out the back and Mistress had me strip embarrassingly infront of the young beautician she giggled as she saw my pinkunderwear. “If you think that’s funny” said Jazz “wait til you see what’s underneath. Show her your shame” Mistress ordered. I was compelled to obey and stood in front of the attractive young stranger with my small cock (even smaller with the nerves I was feeling) jutting out above my grapesized testicles.
“That IS a small package” remarked the beautician in a way that made me think my lack of size had been discussed in the salon before “I’ll have to give you a discount on wax, we won’t need much to do that little thing” she added as the two women burst out laughing.
“I suppose you see a few cocks in this line of work” said MistressJazz
“Oh yeah, it’s great. I can work out who the hung guys are without having to do all the dinner and dancing crap. That way I can’t be disappointed by little things like this”she said yanking my cock none to gently “There’s nothing worse than getting a guy home only to discover they don’t measure up”
“So have you seen any smaller than this Sarah?” inquired mistress
“No, this is the smallest I’ve ever seen. I feel for you” tittered Sarah
“Don’t be, this little boy’s just been cuckolded”
With that I was put through the excruciating ritual of af ull body wax, something I would have to do on a weekly basis.
Punishment of the Penitent Pin Dick Part Ia
After my first waxing Mistress deemed I was ready for my penance to the women I had disappointed sexually throughoutmy life. There was Joy, a female friend when growing up whoI had lost my virginity to in a one-off sexual encounter.There was Rhianna, who I had enjoyed a casual relationshipwith for a few months in my early twenties. Mary was anotherwho I had been with on a few occasions, the relationshipended when I found her in bed with my friend Carl (who I noticedupon discovery of the two boning that he had a not inconsiderablysized penis). Lastly there was Paula who I had had a longterm relationship with for a year before I met Jacinta.
Mistress told me I had to catch up with them in order to apologisefor having sex with them with such a small dick and offerto pay them penance. “Deep down you know you can’t satisfya woman with that needle dick” said Mistress “and you mustbe punished by each one to make up for it”
It was highly humiliating contacting Joy who I had not seenfor some time. . Humiliating, but highly exciting as thesame time, knowing I was going to get my just deserts. Joylaughed at me thinking it was a joke. Mistress then tookthe phone and explained everything. I was put back on theline to Joy who said “It was disappointing to lose my virginityto that little thing. I got such a shock when I saw what a realcock looked like, god it was good. You put me off sex for ayear. Quite the minute man, as well as a miniature man. Ithink I can put you to use” She was a stunning creature whenI knew her in our teens with long blonde hair, a trim figureand a perfect bust. She had lost none of her looks and nowearned a very good living as a stripper.
She had me clean her house from top to bottom, butt naked.This was made more humiliating by the fact she had a few friendsover (friends from the strip club with bodies to die for)at the time who would all pass comments at my inadequacy.“He’s got a cute little arse” one said “and a cute littledick. It’s like a toy dick.” The humiliation was fantasticand I went about the place fully erect much to the amusementof the female trio. “The little boy likes us talking abouthis little dick” said Joy.
“Doesn’t it get any bigger?” asked one of her friends
“Nope that’s it” said Joy, setting them off laughing
“He popped your cherry with that?” the friend said incredulously.
“Sort of, four thrusts and he was done, I barely felt it.That’s why I never did it with him again. It was up to a realman to burst my hymen about a year later. ”
This humiliation had me so turned on I couldn’t help butstart to masturbate. “The little fella’s getting readyto burst” said Joy “but we can’t have him messing up the househe’s just cleaned. Lie down on your back if you wish to wank”she ordered. I did as instructed and lay on my back furiouslytugging my tiny tocko. Joy then picked up my legs standingme on my shoulders “open your mouth” she barked. As I didso I discovered I was staring my dick in the eye (so to speak)I reached the vinegar stroke and ejaculated into my ownmouth “Now swallow every drop” I did as ordered and was droppedback to the ground as the three women laughed hysterically.
“You can put your panties back on and go home.” Joy told me.My first penance was paid but more was to come.
Mistress told me I had to catch up with them in order to apologisefor having sex with them with such a small dick and offerto pay them penance. “Deep down you know you can’t satisfya woman with that needle dick” said Mistress “and you mustbe punished by each one to make up for it”
It was highly humiliating contacting Joy who I had not seenfor some time. . Humiliating, but highly exciting as thesame time, knowing I was going to get my just deserts. Joylaughed at me thinking it was a joke. Mistress then tookthe phone and explained everything. I was put back on theline to Joy who said “It was disappointing to lose my virginityto that little thing. I got such a shock when I saw what a realcock looked like, god it was good. You put me off sex for ayear. Quite the minute man, as well as a miniature man. Ithink I can put you to use” She was a stunning creature whenI knew her in our teens with long blonde hair, a trim figureand a perfect bust. She had lost none of her looks and nowearned a very good living as a stripper.
She had me clean her house from top to bottom, butt naked.This was made more humiliating by the fact she had a few friendsover (friends from the strip club with bodies to die for)at the time who would all pass comments at my inadequacy.“He’s got a cute little arse” one said “and a cute littledick. It’s like a toy dick.” The humiliation was fantasticand I went about the place fully erect much to the amusementof the female trio. “The little boy likes us talking abouthis little dick” said Joy.
“Doesn’t it get any bigger?” asked one of her friends
“Nope that’s it” said Joy, setting them off laughing
“He popped your cherry with that?” the friend said incredulously.
“Sort of, four thrusts and he was done, I barely felt it.That’s why I never did it with him again. It was up to a realman to burst my hymen about a year later. ”
This humiliation had me so turned on I couldn’t help butstart to masturbate. “The little fella’s getting readyto burst” said Joy “but we can’t have him messing up the househe’s just cleaned. Lie down on your back if you wish to wank”she ordered. I did as instructed and lay on my back furiouslytugging my tiny tocko. Joy then picked up my legs standingme on my shoulders “open your mouth” she barked. As I didso I discovered I was staring my dick in the eye (so to speak)I reached the vinegar stroke and ejaculated into my ownmouth “Now swallow every drop” I did as ordered and was droppedback to the ground as the three women laughed hysterically.
“You can put your panties back on and go home.” Joy told me.My first penance was paid but more was to come.
Punishment of the Penitent Pin Dick Part II
Rhianna was the next woman I had to pay penance to. My mistress(Jazz) had cuckholded me and ordered me to pay penance tothe women I had insulted by fucking with my smaller thanadequate sized penis. She was a full figured woman witha coke bottle figure and breasts you could get lost in.
She hung up on me calling me a sick pervert when I told herwhat I had in mind. Mistress called her back and talked herround, explaining the joys of fucking a real man and punishinga naughty little boy.
“You’ve never had a big one?” I heard mistress say “wellyou’ve never lived, I know just what to do”. Mistress tookme to our local adult store where we went to the dildo section.She spoke loudly to me so that all in the store could hearher comments such as “Oh this one’s much bigger than yourlittle thing. Then again that wouldn’t be hard”. In theend I had to purchase an eight inch dildo with considerablegirth. What also happened was that Mistress’ conspicuouscomments about my lack of size attracted the attentionof one of the men in the shop who had been perusing the videosection. He approached us in the car park saying “hey honeyif you want a real dick, you should see what I bring to thetable”.
“I would like that” Jazz said “Skinny” she said turningto me “pull out his cock, let’s see what he’s packing” I wasforced to undo the fly of the hung stranger and pull out hislarge flaccid member. “Wow, look at that skinny” cooedmistress “that’s bigger than yours gets hard. Come on dear,get him hard, I’m getting wet just looking at that big thing”
“Come on pee wee” encouraged the stranger “get me hard foryour woman” I was forced to masturbate his large cock toerection, it ended up nearly the same size as the big dildowe had just purchased. “Let me see yours” he said. The situationhad me highly excited, I looked at Mistress who nodded herapproval and I lowered my trousers and letting my five incherection show. The stranger laughed and said “I can seewhy you gotta look elsewhere honey”. Mistress hitchedup her skirt, opening the back door of the car she bent overthe seat and presented her beautiful, dripping wet shavedpussy for penetration. Pulling her lips apart and imploringthe stud to “put it in, please”.
To see Mistress begging for cock was a huge turn on, I knewshe would never beg a small cocked boy like me but a real manhad her overpowered like a schoolgirl. The Man startedteasing her with just the tip slowly moving an inch of hiscock in and out of her pussy. This had Mistress even moreturned on “Please put it all the way in, please” she pleaded“this is like fucking that pindick”. The Real Man then plungedhis fat eight inches into her to the hilt having her groaningin pleasure. She came then and there crying her pleasureinto the car seat. The Man fucked her hard for five minutessoon reaching the vinegar stroke.
“I’m gonna come” he gasped
“Do it on my pindick” said Mistress coming as she spoke.The stud did as requested and pulled out shooting a hugeload of come coating my own small cock in his juices. “Pullyour pants up, you may not come” Mistress ordered me preventingme from taking myself to orgasm or even cleaning the otherman’s semen from my cock. I was ordered to drive to Rhianna’sin my sticky knickers sporting the hardest erection I hadever had while the Real Man took Mistress Jazz home to ourplace where she was to get further attention from his largetool. “Rhianna will know what to do” said Mistress “everythinghas been arranged. Now if you’ll excuse me I’m going to ourbed to fuck this Big Man’s brains out. Off to Rhianna’s nowlittle boy. You must do whatever she orders, if not furtherpunishment will ensue.”
I drove to Rhianna’s with the eight inch dildo sitting onthe passenger sheet in its paper bag. I thought with halfterror and half excitement that it would be used on me. WhenI arrived at Rhianna’s she was alone and wearing some sexyblack lace lingerie with candles lit. Upon answering thedoor she immediately said “You are not to say a word, youwill do exactly as ordered and satisfy my every whim. Youfucked me a number of times and never once fulfilled my needs,now you will get the same treatment. Do you have a presentfor me?”
“Yes I do” I responded presenting the big fleshy dildo.Rhianna grabbed it and slapped me across the face with it.
“I said not a word pee wee, just nod or shake your head. I don’twant to hear from you. Understood?” I nodded yes “Good.Now let’s remind us why you’re here. Get naked.” I silentlystripped down with Rhianna bursting out laughing whenshe saw the frilly red panties Mistress had dressed me in“You’ve come already?” she asked mistaking the Real Man’scome for my own. “How dare you” she slapped me with the dildoagain “I’m the only one to come today, now lie on your back”
“It’s not my…” I began as I started to lie down
“What did I say?” yelled Rhianna pushing me to the ground.With her full figure and my slender build she weighed aboutthe same as me and was able to pin me to the ground, straddlingmy chest with my arms imprisoned at my side by her legs “Isaid silence you pathetic little boy. The only way I’m goingto get you to shut up is to sit on your face” With that she movedup and did just that sitting with her pussy over my mouthand her anus on my nose “Now lick my pussy and get me nice andwet pee wee.” I gave her head for what seemed an eternitynibbling her lips and tonguing her clit with the skill requiredof a pindick. She ground into my face making it hard for meto breath and making sure that my nose was well and trulyup her arse. “Oh yeah, you always were good at this” she said“then again you have to be when you’re cock can’t hit thespot.” I continued to tongue her clit as she orgasmed. “Ohthat’s good” Rhianna purred “but not as good as the deeppenetration you can’t provide. I never had a big cock, althoughI’ve always wanted one, apparently it’s bliss. Seeingas though you aren’t a full size man we have to go take advantageof your present.” She got off my face and ordered me to openmy mouth. “Hold that there” she commanded placing the baseof the dildo in my mouth. It was so thick I could barely getmy mouth around it “I’m so wet after that toungue lashing,you’re a good pussy licker bitch.” Rhianna slowly loweredherself on to the eight inches of plastic I held in placein my mouth groaning with delight. “Oh god that’s so good”she exclaimed “you could never hope to provide this sortof pleasure” she teased as she started to move backwardsand forwards with the dildo buried up to the hilt spreadingher pussy wider than I ever had. Once again she made sureher anus was around my nose and began to fuck the fake cockharder and harder.
“Oh my goooood” she screamed as she started to experienceher first ever deep vaginal muscle contraction “ohhhhhhI’m seeing stars, this IS so much better. Yesssssss”. Shefucked away for forty minutes “God I’ve missed out fuckingsmall guys like you” my jaw started going numb so that I couldno longer hold the dildo in place. “Fuck off” she yelledat me as I finally gave way and let the dildo spill out of mymouth “This hunk of plastic is a better lover than you’llever be, I’m going to carry on myself, get dressed and getout”
I clothed and left Rhianna furiously fucking herself withthe dildo taking herself to places of deep penetrationaldelight that I would never take her. I drove home and wouldbe able to observe a real man pleasuring my mistress in asimilar way. I couldn’t wait to wank my little pee wee cockin tribute. I also knew I had two more women to be punishedby for my past pathetic pumpings with my puny penis. I lookedforward to the sweet humiliation.
She hung up on me calling me a sick pervert when I told herwhat I had in mind. Mistress called her back and talked herround, explaining the joys of fucking a real man and punishinga naughty little boy.
“You’ve never had a big one?” I heard mistress say “wellyou’ve never lived, I know just what to do”. Mistress tookme to our local adult store where we went to the dildo section.She spoke loudly to me so that all in the store could hearher comments such as “Oh this one’s much bigger than yourlittle thing. Then again that wouldn’t be hard”. In theend I had to purchase an eight inch dildo with considerablegirth. What also happened was that Mistress’ conspicuouscomments about my lack of size attracted the attentionof one of the men in the shop who had been perusing the videosection. He approached us in the car park saying “hey honeyif you want a real dick, you should see what I bring to thetable”.
“I would like that” Jazz said “Skinny” she said turningto me “pull out his cock, let’s see what he’s packing” I wasforced to undo the fly of the hung stranger and pull out hislarge flaccid member. “Wow, look at that skinny” cooedmistress “that’s bigger than yours gets hard. Come on dear,get him hard, I’m getting wet just looking at that big thing”
“Come on pee wee” encouraged the stranger “get me hard foryour woman” I was forced to masturbate his large cock toerection, it ended up nearly the same size as the big dildowe had just purchased. “Let me see yours” he said. The situationhad me highly excited, I looked at Mistress who nodded herapproval and I lowered my trousers and letting my five incherection show. The stranger laughed and said “I can seewhy you gotta look elsewhere honey”. Mistress hitchedup her skirt, opening the back door of the car she bent overthe seat and presented her beautiful, dripping wet shavedpussy for penetration. Pulling her lips apart and imploringthe stud to “put it in, please”.
To see Mistress begging for cock was a huge turn on, I knewshe would never beg a small cocked boy like me but a real manhad her overpowered like a schoolgirl. The Man startedteasing her with just the tip slowly moving an inch of hiscock in and out of her pussy. This had Mistress even moreturned on “Please put it all the way in, please” she pleaded“this is like fucking that pindick”. The Real Man then plungedhis fat eight inches into her to the hilt having her groaningin pleasure. She came then and there crying her pleasureinto the car seat. The Man fucked her hard for five minutessoon reaching the vinegar stroke.
“I’m gonna come” he gasped
“Do it on my pindick” said Mistress coming as she spoke.The stud did as requested and pulled out shooting a hugeload of come coating my own small cock in his juices. “Pullyour pants up, you may not come” Mistress ordered me preventingme from taking myself to orgasm or even cleaning the otherman’s semen from my cock. I was ordered to drive to Rhianna’sin my sticky knickers sporting the hardest erection I hadever had while the Real Man took Mistress Jazz home to ourplace where she was to get further attention from his largetool. “Rhianna will know what to do” said Mistress “everythinghas been arranged. Now if you’ll excuse me I’m going to ourbed to fuck this Big Man’s brains out. Off to Rhianna’s nowlittle boy. You must do whatever she orders, if not furtherpunishment will ensue.”
I drove to Rhianna’s with the eight inch dildo sitting onthe passenger sheet in its paper bag. I thought with halfterror and half excitement that it would be used on me. WhenI arrived at Rhianna’s she was alone and wearing some sexyblack lace lingerie with candles lit. Upon answering thedoor she immediately said “You are not to say a word, youwill do exactly as ordered and satisfy my every whim. Youfucked me a number of times and never once fulfilled my needs,now you will get the same treatment. Do you have a presentfor me?”
“Yes I do” I responded presenting the big fleshy dildo.Rhianna grabbed it and slapped me across the face with it.
“I said not a word pee wee, just nod or shake your head. I don’twant to hear from you. Understood?” I nodded yes “Good.Now let’s remind us why you’re here. Get naked.” I silentlystripped down with Rhianna bursting out laughing whenshe saw the frilly red panties Mistress had dressed me in“You’ve come already?” she asked mistaking the Real Man’scome for my own. “How dare you” she slapped me with the dildoagain “I’m the only one to come today, now lie on your back”
“It’s not my…” I began as I started to lie down
“What did I say?” yelled Rhianna pushing me to the ground.With her full figure and my slender build she weighed aboutthe same as me and was able to pin me to the ground, straddlingmy chest with my arms imprisoned at my side by her legs “Isaid silence you pathetic little boy. The only way I’m goingto get you to shut up is to sit on your face” With that she movedup and did just that sitting with her pussy over my mouthand her anus on my nose “Now lick my pussy and get me nice andwet pee wee.” I gave her head for what seemed an eternitynibbling her lips and tonguing her clit with the skill requiredof a pindick. She ground into my face making it hard for meto breath and making sure that my nose was well and trulyup her arse. “Oh yeah, you always were good at this” she said“then again you have to be when you’re cock can’t hit thespot.” I continued to tongue her clit as she orgasmed. “Ohthat’s good” Rhianna purred “but not as good as the deeppenetration you can’t provide. I never had a big cock, althoughI’ve always wanted one, apparently it’s bliss. Seeingas though you aren’t a full size man we have to go take advantageof your present.” She got off my face and ordered me to openmy mouth. “Hold that there” she commanded placing the baseof the dildo in my mouth. It was so thick I could barely getmy mouth around it “I’m so wet after that toungue lashing,you’re a good pussy licker bitch.” Rhianna slowly loweredherself on to the eight inches of plastic I held in placein my mouth groaning with delight. “Oh god that’s so good”she exclaimed “you could never hope to provide this sortof pleasure” she teased as she started to move backwardsand forwards with the dildo buried up to the hilt spreadingher pussy wider than I ever had. Once again she made sureher anus was around my nose and began to fuck the fake cockharder and harder.
“Oh my goooood” she screamed as she started to experienceher first ever deep vaginal muscle contraction “ohhhhhhI’m seeing stars, this IS so much better. Yesssssss”. Shefucked away for forty minutes “God I’ve missed out fuckingsmall guys like you” my jaw started going numb so that I couldno longer hold the dildo in place. “Fuck off” she yelledat me as I finally gave way and let the dildo spill out of mymouth “This hunk of plastic is a better lover than you’llever be, I’m going to carry on myself, get dressed and getout”
I clothed and left Rhianna furiously fucking herself withthe dildo taking herself to places of deep penetrationaldelight that I would never take her. I drove home and wouldbe able to observe a real man pleasuring my mistress in asimilar way. I couldn’t wait to wank my little pee wee cockin tribute. I also knew I had two more women to be punishedby for my past pathetic pumpings with my puny penis. I lookedforward to the sweet humiliation.
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.
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.
Punishment of the Pentitent Pin Dick Part IV
My final penance to a woman I had disappointed with my inadequate cock was to Paula who I had had a year long relationship with. Like the vanilla relationship I had with Jacinta who had now cuckholded me, we managed to tip toe around the issue of my under endowment. Paula would say that size didn’t matter and we would have anal sex which she said she enjoyed more with a smaller than average cock. Although the relationship seemed a happy one it had ended after about a year. Paula had found someone else and moved on saying that we had grown apart.
When I contacted her with the news that my Mistress was making me pay penance to all the women I had insolently screwed without adequate equipment she reacted differently to all the others. She actually thanked me saying “It was your little knob that made me realize how important a real cockis to me. Without you I would have gone on thinking six inches was enough, of course your skinny little five inch worm is nowhere enough so it got me to thinking if there’s too small then is there too big? My conclusion is: there isn’t. I certainly haven’t come across it.”
Upon discussion with my Mistress (Jazz) who explained to Paula that I had to pay my penance, Paula decided that I would come along to a swingers party that she threw once a month. “At this party” she informed me “I have four real men come along, and all my female friends who have to put up with their husbands' and boyfriends' small and average cocks. We tell them it’s a make up night” she laughed. “Seeing as though you must pay penance, I have a job you can fulfill at this event.”
The next party was in two weeks and I ticked off the days. In this time my girlfriend Jacinta (or Mistress Jazz since I had been cuckholded) would take me out to a night club. I would be required to scan the gents toilets for a big cock. It was very difficult and highly humiliating having to furtively scan my fellow urinal user’s endowment. I got caught a number of times but luckily managed to avoid any physical harm. Each night Mistress Jazz would take home a well endowed stud identified by me and get her brains fucked out. Until I fulfilled my last penance with Paula I was only permitted to listen at the door. I longed to be able to watch my girlfriend be pleased by these real men.
When the night finally rolled around I received quite a shock. A dozen women were at Paula’s and all were quite tipsy. I arrived first of the males but as each man entered he was required to be measured by Paula (which turned her on greatly).“There is a minimum to enter” she would state “Twenty centimeters in length and fifteen centimeters in girth”. All men who entered met these requirements. There were Paula’s four regulars but also three of the men who I had discovered for my Mistress.
“I was scouting for talent” Mistress Jazz informed me laughing.
“Before we start” announced Paula to the assembled group “we have a newcomer. Step forward skinny” she said to me. I approached Paula who had centre stage in the living room.“You haven’t been measured yet. Lower your pants and get yourself hard” I did as bidded and lowered my strides to the giggles of the group.
“I don’t think he’ll quite make the cut with that little thing” guffawed a member of the audience to the general laughs of the throng. The humiliation had me erect in seconds.Paula applied the tape measure to me: “thirteen centimeters by eleven centimeters. Dear me.” She tutted “this boy will have to perform another duty. Seeing as though he can’t service us, he will have to clean us. You will be our slops bitch” she told me “every time one of these men come up one of these lovely ladies it will be your duty to clean them…with your tongue”
This brought whoops of approval from the assembled group. Then my Mistress added “if he is going to be a cleaner he should dress like one.” At this point I was obliged to don a french maid outfit. The skirt jutted out like a tutu at the waistso that my humbly sized package was always on display as were my buttocks (which were repeatedly slapped throughoutthe night by passers by).
The fuck fest that followed was an eye opening experiencefor me. All these women loved getting a real cock so much more than the ones they had at home. They were taken to places a small cocked man would never take them.
Throughout the night if one of the real men yelled “SLOPS!” I had to attend the scene of his latest conquest and clean his come out of the pussy of the satisfied women he had just serviced. Over the four hour duration of the party I wasrequired as slops bitch to each man at least twice for a total of twenty one cream pies.
All this time Mistress Jazz simply observed drinking aglass of wine that I was ordered to keep topped up. At the conclusion of the party my Mistress selected the three biggest of the men to take home. Humiliatingly I was forced to drive them home remaining in the maid’s outfit. I hadto dash up the driveway and open the front door to avoid the neighbours seeing my small cock jutting out from below my female attire. Once inside Mistress placed a collararound my neck with a leash on it. “You have fulfilled your penance to all the past women you penetrated with that pathetic pin dick, now your penance to me is just beginning…”
When I contacted her with the news that my Mistress was making me pay penance to all the women I had insolently screwed without adequate equipment she reacted differently to all the others. She actually thanked me saying “It was your little knob that made me realize how important a real cockis to me. Without you I would have gone on thinking six inches was enough, of course your skinny little five inch worm is nowhere enough so it got me to thinking if there’s too small then is there too big? My conclusion is: there isn’t. I certainly haven’t come across it.”
Upon discussion with my Mistress (Jazz) who explained to Paula that I had to pay my penance, Paula decided that I would come along to a swingers party that she threw once a month. “At this party” she informed me “I have four real men come along, and all my female friends who have to put up with their husbands' and boyfriends' small and average cocks. We tell them it’s a make up night” she laughed. “Seeing as though you must pay penance, I have a job you can fulfill at this event.”
The next party was in two weeks and I ticked off the days. In this time my girlfriend Jacinta (or Mistress Jazz since I had been cuckholded) would take me out to a night club. I would be required to scan the gents toilets for a big cock. It was very difficult and highly humiliating having to furtively scan my fellow urinal user’s endowment. I got caught a number of times but luckily managed to avoid any physical harm. Each night Mistress Jazz would take home a well endowed stud identified by me and get her brains fucked out. Until I fulfilled my last penance with Paula I was only permitted to listen at the door. I longed to be able to watch my girlfriend be pleased by these real men.
When the night finally rolled around I received quite a shock. A dozen women were at Paula’s and all were quite tipsy. I arrived first of the males but as each man entered he was required to be measured by Paula (which turned her on greatly).“There is a minimum to enter” she would state “Twenty centimeters in length and fifteen centimeters in girth”. All men who entered met these requirements. There were Paula’s four regulars but also three of the men who I had discovered for my Mistress.
“I was scouting for talent” Mistress Jazz informed me laughing.
“Before we start” announced Paula to the assembled group “we have a newcomer. Step forward skinny” she said to me. I approached Paula who had centre stage in the living room.“You haven’t been measured yet. Lower your pants and get yourself hard” I did as bidded and lowered my strides to the giggles of the group.
“I don’t think he’ll quite make the cut with that little thing” guffawed a member of the audience to the general laughs of the throng. The humiliation had me erect in seconds.Paula applied the tape measure to me: “thirteen centimeters by eleven centimeters. Dear me.” She tutted “this boy will have to perform another duty. Seeing as though he can’t service us, he will have to clean us. You will be our slops bitch” she told me “every time one of these men come up one of these lovely ladies it will be your duty to clean them…with your tongue”
This brought whoops of approval from the assembled group. Then my Mistress added “if he is going to be a cleaner he should dress like one.” At this point I was obliged to don a french maid outfit. The skirt jutted out like a tutu at the waistso that my humbly sized package was always on display as were my buttocks (which were repeatedly slapped throughoutthe night by passers by).
The fuck fest that followed was an eye opening experiencefor me. All these women loved getting a real cock so much more than the ones they had at home. They were taken to places a small cocked man would never take them.
Throughout the night if one of the real men yelled “SLOPS!” I had to attend the scene of his latest conquest and clean his come out of the pussy of the satisfied women he had just serviced. Over the four hour duration of the party I wasrequired as slops bitch to each man at least twice for a total of twenty one cream pies.
All this time Mistress Jazz simply observed drinking aglass of wine that I was ordered to keep topped up. At the conclusion of the party my Mistress selected the three biggest of the men to take home. Humiliatingly I was forced to drive them home remaining in the maid’s outfit. I hadto dash up the driveway and open the front door to avoid the neighbours seeing my small cock jutting out from below my female attire. Once inside Mistress placed a collararound my neck with a leash on it. “You have fulfilled your penance to all the past women you penetrated with that pathetic pin dick, now your penance to me is just beginning…”
Punishment of the Penitent Pin Dick
After paying penance to all the women whom I had botheredwith my pesky little pee wee penis, my girlfriend/mistresssaw fit to inflict her own punishment for the two years Ihad dared to do the same to her.
I had already been cuckholded but until I served my penanceto the four women I had irritated with my prick I had beenunable to watch Mistress Jazz with the well hung studs sheregularly had service her in our bedroom. I had been obligatedto simply listen at the door masturbating to my own inadequacy.
Finally I had served my penance and was allowed to enterthe bedroom while Jazz was being serviced. However, myrole was not unconditional she told me “Your punishmentfor my two years of sexual frustration received from yourinadequate endowment will be ongoing.”
The first step had been to make a plaster cast of my erectpenis and make a wax model for display in our bedroom. Fromthen on I was required to do the same for any lover Jazz broughthome that so consented. Most of the well endowed men werehappy to have me do it and took great pleasure in my humiliation.As I was an accountant Jazz decided to put my mathematicalacumen to use. I was required to calculate a score each penisthat Jazz entertained and report to her and the owner ofit as to exactly how much more they filled her up.
The equation presented was the circumference of the cockmultiplied by the length. In this way my embarrassing 13cm(5 inch) length x 10cm (4 inch) circumference penis wasrated at 130 points. When Jazz brought home a 20cm (8 inch)x 15cm (6 inch) man his score was 300 points. I was forcedto humiliatingly thank this stud for filling my wife withexactly 231% more cock.
One of the two more humiliating sessions involved a manwith a shorter yet thicker endowment than me his 12cm (under5 inch) x 17cm (6.5 inch) cock rated at 157% per cent biggerthan made. Jazz rode him reverse cow girl and had me on allfours facing away from her as she finger banged my arseholeall the time yelling “157 per cent, 157 per cent!”.
The even more humiliating equation involved the man whopleasured my wife with her biggest yet: 29cm (nearly 12inches) x 21cm (over eight inches) for monolithic scoreof 609 - providing a humiliating 468% more pleasure.
The plaster cast of this porn star sized cock took prideof place amongst the collection.
The plaster casting was only part of my penitent servitudeas a pindick cuck. The rules that were written by Jazz (alawyer) that allowed me to watch real men please my girlfried/mistresswere as follows:1. You will prepare Mistress Jazz for her session by committingoral pleasure upon her, so lubing her pussy for the RealMan.2. If the Real Man should so wish, you will also preparehim by committing oral pleasure upon him3. You will collar and leash yourself at the foot of thebed, naked like the dog that you are4. You will calculate and report the penile score as setdown by Mistress and thank the Real Man for pleasing Mistressas you never could5. It is your duty to clean up all come and other fluids,with your tongue – like the dog that you are6. If the Real Man should stay the night you will uncollaryourself before Mistress and He awake and prepare breakfastin order to thank him further7. Should Mistress wish to fuck him again in the morningyou will be required to again prepare Mistress’ pussy andthe Real Man’s cock should he so wish8. If Mistress does not wish for more sex in the morningbut the Real Man does it will be your duty to provide manualrelief for him once again cleaning any fluid leavings withyour tongue9. Any other duties as directed by Mistress
I had already been cuckholded but until I served my penanceto the four women I had irritated with my prick I had beenunable to watch Mistress Jazz with the well hung studs sheregularly had service her in our bedroom. I had been obligatedto simply listen at the door masturbating to my own inadequacy.
Finally I had served my penance and was allowed to enterthe bedroom while Jazz was being serviced. However, myrole was not unconditional she told me “Your punishmentfor my two years of sexual frustration received from yourinadequate endowment will be ongoing.”
The first step had been to make a plaster cast of my erectpenis and make a wax model for display in our bedroom. Fromthen on I was required to do the same for any lover Jazz broughthome that so consented. Most of the well endowed men werehappy to have me do it and took great pleasure in my humiliation.As I was an accountant Jazz decided to put my mathematicalacumen to use. I was required to calculate a score each penisthat Jazz entertained and report to her and the owner ofit as to exactly how much more they filled her up.
The equation presented was the circumference of the cockmultiplied by the length. In this way my embarrassing 13cm(5 inch) length x 10cm (4 inch) circumference penis wasrated at 130 points. When Jazz brought home a 20cm (8 inch)x 15cm (6 inch) man his score was 300 points. I was forcedto humiliatingly thank this stud for filling my wife withexactly 231% more cock.
One of the two more humiliating sessions involved a manwith a shorter yet thicker endowment than me his 12cm (under5 inch) x 17cm (6.5 inch) cock rated at 157% per cent biggerthan made. Jazz rode him reverse cow girl and had me on allfours facing away from her as she finger banged my arseholeall the time yelling “157 per cent, 157 per cent!”.
The even more humiliating equation involved the man whopleasured my wife with her biggest yet: 29cm (nearly 12inches) x 21cm (over eight inches) for monolithic scoreof 609 - providing a humiliating 468% more pleasure.
The plaster cast of this porn star sized cock took prideof place amongst the collection.
The plaster casting was only part of my penitent servitudeas a pindick cuck. The rules that were written by Jazz (alawyer) that allowed me to watch real men please my girlfried/mistresswere as follows:1. You will prepare Mistress Jazz for her session by committingoral pleasure upon her, so lubing her pussy for the RealMan.2. If the Real Man should so wish, you will also preparehim by committing oral pleasure upon him3. You will collar and leash yourself at the foot of thebed, naked like the dog that you are4. You will calculate and report the penile score as setdown by Mistress and thank the Real Man for pleasing Mistressas you never could5. It is your duty to clean up all come and other fluids,with your tongue – like the dog that you are6. If the Real Man should stay the night you will uncollaryourself before Mistress and He awake and prepare breakfastin order to thank him further7. Should Mistress wish to fuck him again in the morningyou will be required to again prepare Mistress’ pussy andthe Real Man’s cock should he so wish8. If Mistress does not wish for more sex in the morningbut the Real Man does it will be your duty to provide manualrelief for him once again cleaning any fluid leavings withyour tongue9. Any other duties as directed by Mistress
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