Poor Sheen pt 6

Poor Sheen pt 6

Spencer chose Gina to take his load and started fucking her tight cunt furiously from behind.  Sheen continued to edge himself, growing more and more excited at the frantic fucking noises beside him.

Oh, fuck yeah, give me that cock baby.  Fuck my dirty hole.  Use me like a filthy whore, fuck that cunt, fuck it.

Sheenie, I want you to watch Spencer fucking Gina's cunt.  That's it look at him while you stroke yourself.

Sheen looked up and saw Spencer's cock plunging in and out of Gina's pussy.  He stroked his cock faster at that sight.

Put your face right up there Sheen and stroke your gurl cock while you watch.  See what a real man can do?  He's fucking her good and hard.  Your cock is bigger, but it would never be able to satisfy a woman, not when it's attached to a sissy wimp like you.  Stroke your pathetic sissy cock bitch, stroke it while you watch.  That's it get up right in there.

Sheen moved between Spencer's legs, his face was inches from Gina's cunt.  He could smell the mingled juices as Spencer's glistening cock slid in and out.  Sheen kept stroking his cock furiously while Dagmar continued to fuck him up the ass.

"I'm gonna cum baby!" Spencer's body tensed up and his cock pumped a huge load of cum inside Gina's cunt.  "Oh fuck yeah!" He quivered as the orgasm ended and he pulled his cock out.

Oh would you look at all that cum ladies?!  What a mess!  Real men certainly know how to leave their mark, don't they?!  The ladies all giggled and laughed in agreement.

What do you think we should do about all that cum dribbling out of Gina's used hole?  What's that?  Oh I almost forgot, we have our very own sissy maid here to do all our housework, don't we?  Now clean up Gina's cunt Sheenie,  Mistress ordered.  Clean it with your tongue!

Sheen paused momentarily, but knew better than to object.  He began to tongue Gina's well used cunt, licking up slick gobs of Spencer's cum as it oozed out of her.  Sheen secretly relished the taste of Spencer's cum, and it wasn't the first time he'd tasted it either.

That's it, stroke that cock while you swallow it all, don't you miss a drop sissy.

Sheen did a good job, eating Gina's cunt clean for five minutes straight while he edged his hard prick.  It was enough for Gina to cum on his face, a nice added bonus.

Ha Ha,  look girls, Sheen is still hard!  He must have liked eating all that real man cum from my cunt.  Did that turn you on sissy?

Mistress snapped her fingers and had Sheen lay down on the floor belly up.  Dagmar got on top of him and put his legs over her shoulders and began to plow him with her strap on.  For some reason this really stimulated his prostate and he let out a small spurt of cum that shot onto his belly.

Thwack!  Did I say you could cum bitch?!

I'm s,s,sorry Mistress.  I didn't mean to.

Clean that up, eat your own sissy cum.

Sheen used his fingers to scoop up the small gob and brought it to his mouth while his other hand continued its stroking.

That's it sissy eat that cum while you stroke your pathetic sissy cock.  Can you taste the difference?  You just ate a whole cream pie full of real man cum, and now your tasting your own sissy wimp cum.

Dagmar was still pounding his ass as all the ladies watched with delight at what a sissy wimp he was masturbating his pathetic cock in front of all of them.

"I can hardly wait to tell everyone at work" Lola said to Sue as they snapped pictures with their phones.

"I know" Gina agreed as she got a nice clear pic of Sheen in his maid outfit masturbating his own cock.

Just as Sheen's balls started to tighten for an orgasm, Dagmar pulled the dildo from his ass and ordered him to stop stroking himself.  Sheen's cock jerked in the air hoping to get stroked once more so it could cum, but that last stroke would never arrive.  When the twitching stopped, Mistress inserted a butt plug up Sheen's ass and clamped and locked a cock ring on him.

Well, that's enough for now.  Let's put hur in hur cage for tonight.  Now put on your night time clothes Sheenie.

Sheen crawled to his cubby and changed into a frilly see through nightie and matching panties that hugged him tight down there ensuring the butt plug would not get out.

Poor Sheen was led to his dog cage and put inside with his hard prick in the cock ring.  The ring was so tight his cock wouldn't be able to get soft.

"Stroke that cock while you're in there Sheen."  Mistress ordered as she shut the cage door for the night.  "But don't you cum!"



Next Week...Bobbi cums back!

Spencer chose Gina to take his load and started fucking her tight cunt furiously from behind.  Sheen continued to edge himself, growing more and more excited at the frantic fucking noises beside him.

Oh, fuck yeah, give me that cock baby.  Fuck my dirty hole.  Use me like a filthy whore, fuck that cunt, fuck it.

Sheenie, I want you to watch Spencer fucking Gina's cunt.  That's it look at him while you stroke yourself.

Sheen looked up and saw Spencer's cock plunging in and out of Gina's pussy.  He stroked his cock faster at that sight.

Put your face right up there Sheen and stroke your gurl cock while you watch.  See what a real man can do?  He's fucking her good and hard.  Your cock is bigger, but it would never be able to satisfy a woman, not when it's attached to a sissy wimp like you.  Stroke your pathetic sissy cock bitch, stroke it while you watch.  That's it get up right in there.

Sheen moved between Spencer's legs, his face was inches from Gina's cunt.  He could smell the mingled juices as Spencer's glistening cock slid in and out.  Sheen kept stroking his cock furiously while Dagmar continued to fuck him up the ass.

"I'm gonna cum baby!" Spencer's body tensed up and his cock pumped a huge load of cum inside Gina's cunt.  "Oh fuck yeah!" He quivered as the orgasm ended and he pulled his cock out.

Oh would you look at all that cum ladies?!  What a mess!  Real men certainly know how to leave their mark, don't they?!  The ladies all giggled and laughed in agreement.

What do you think we should do about all that cum dribbling out of Gina's used hole?  What's that?  Oh I almost forgot, we have our very own sissy maid here to do all our housework, don't we?  Now clean up Gina's cunt Sheenie,  Mistress ordered.  Clean it with your tongue!

Sheen paused momentarily, but knew better than to object.  He began to tongue Gina's well used cunt, licking up slick gobs of Spencer's cum as it oozed out of her.  Sheen secretly relished the taste of Spencer's cum, and it wasn't the first time he'd tasted it either.

That's it, stroke that cock while you swallow it all, don't you miss a drop sissy.

Sheen did a good job, eating Gina's cunt clean for five minutes straight while he edged his hard prick.  It was enough for Gina to cum on his face, a nice added bonus.

Ha Ha,  look girls, Sheen is still hard!  He must have liked eating all that real man cum from my cunt.  Did that turn you on sissy?

Mistress snapped her fingers and had Sheen lay down on the floor belly up.  Dagmar got on top of him and put his legs over her shoulders and began to plow him with her strap on.  For some reason this really stimulated his prostate and he let out a small spurt of cum that shot onto his belly.

Thwack!  Did I say you could cum bitch?!

I'm s,s,sorry Mistress.  I didn't mean to.

Clean that up, eat your own sissy cum.

Sheen used his fingers to scoop up the small gob and brought it to his mouth while his other hand continued its stroking.

That's it sissy eat that cum while you stroke your pathetic sissy cock.  Can you taste the difference?  You just ate a whole cream pie full of real man cum, and now your tasting your own sissy wimp cum.

Dagmar was still pounding his ass as all the ladies watched with delight at what a sissy wimp he was masturbating his pathetic cock in front of all of them.

"I can hardly wait to tell everyone at work" Lola said to Sue as they snapped pictures with their phones.

"I know" Gina agreed as she got a nice clear pic of Sheen in his maid outfit masturbating his own cock.

Just as Sheen's balls started to tighten for an orgasm, Dagmar pulled the dildo from his ass and ordered him to stop stroking himself.  Sheen's cock jerked in the air hoping to get stroked once more so it could cum, but that last stroke would never arrive.  When the twitching stopped, Mistress inserted a butt plug up Sheen's ass and clamped and locked a cock ring on him.

Well, that's enough for now.  Let's put hur in hur cage for tonight.  Now put on your night time clothes Sheenie.

Sheen crawled to his cubby and changed into a frilly see through nightie and matching panties that hugged him tight down there ensuring the butt plug would not get out.

Poor Sheen was led to his dog cage and put inside with his hard prick in the cock ring.  The ring was so tight his cock wouldn't be able to get soft.

"Stroke that cock while you're in there Sheen."  Mistress ordered as she shut the cage door for the night.  "But don't you cum!"



Next Week...Bobbi cums back!

Poor Sheen pt 5

Poor Sheen pt 5

Oh you look so ashamed of yourself Sheenie.

Yyyes Mistress, so ashamed, so very ashamed.

You don't know real shame do you?  Well, perhaps I can teach you a lesson sissy.

As if right on cue, Sheen heard the doorbell.  From down the hall he heard a female voices and chatter, then footsteps as Spencer showed the new guests in.

Look Sheen, we thought you might be lonely so we invited some friends of yours, Mistress said.

Sheen looked up in horror as several of his female coworkers stood in the doorway with their mouths wide open.  There was pretty Gina and Lola from HR and Sue from accounting all looking on as Sheen continued to masturbate and give head to the big rubber strap on cock while still being pounded up the ass by Dagmar.

Ha Ha!  I always knew he was a sissy wimp, but this is even worse than I could have ever thought!

The ladies sat down to watch Sheen be humiliated for their pleasure.

Mistress snapped her fingers and ordered Sheen to eat her pussy.

The ladies from work were delighted to see how obedient Sheen was.

S/he's so subservient, I love that in a gurl.  Hmm, I think I've found some new things for Sheen to do at work.

Spencer came back in the room and immediately began flirting and kissing with the new girls.  How the hell was he doing that?  Sheen felt so jealous.

Aw, Sheen looks like he wishes he was Spencer.  Spencer's a real man darling, he's gonna get his cock sucked and fucked like a real man deserves.  Now grovel for mommy Sheen.

Oh please, may I suck on the big rubber cock for Mistress?  May I further offer my ass for Mistress Dagmar's pleasure.  I'm a sissy and deserve punishment for being a sissy.

The ladies lined up to let Spencer get a piece of them.  One girl straddled his cock and then lowered herself onto him while the other two stood next to him while he fingered their cunts.  He worked his fingers in and out of their tight holes like a musician playing an instrument.

Oh, fuck yeah baby, finger that cunt, feels so good.  Is he making your cunt feel good too Gina?

Hey sissy!  Come over here.  Spencer motioned for Sheen to crawl over and he meekly obeyed.
Here, lick the pussy juice from my hands.

Sheen lapped at his hands like a dog, relishing the taste of Gina's cunt juices on one hand and Lola's on the other.  This was a real man unlike sissy Sheen.  Sheen dare didn't look up, but out of the corner of his eye he could see Sue riding up and down on Spencer's hard cock.  He timed his stroking to Spencer's fucking and imagined how good it would feel if his cock was where Spencer's was.

Yeah, fuck yourself on my cock baby.  Now grind it, grind that cunt on me while my cock is all the way inside you.

Oh, fuck, that feels so damn good.  My cunt is on fire, yes!  I'm gonna fuck my own cunt with your cock.

Suck Sue's titties while she fucks herself on my cock ladies.

Gina and Lola leaned forward to suck Sue's tits while still getting finger fucked by Spencer.

See what I'm doing Sheen?  You're not gonna get to do this.  Your cock and hands will never get to be inside a woman again.  That is unless you consider yourself to be a gurl, cause you WILL be fingering your own ass.

The thought of that excited Sheen as he stroked his cock faster and faster.

Dagmar was really giving it to Sheen now and he was trying to hold on and not cum.

The girls kept rotating so each got to fuck Spencer while the other two would get fingered.  Each time Sheen would lick Spencer's fingers clean, tasting and relishing the flavors of the different women.

Dagmar complimented Mistress on her training.  I'm surprised your sissy hasn't cum yet, you've done an excellent job training hur.  So obedient, just like a good gurl should be, isn't that right sissy Sheen?

Oh you look so ashamed of yourself Sheenie.

Yyyes Mistress, so ashamed, so very ashamed.

You don't know real shame do you?  Well, perhaps I can teach you a lesson sissy.

As if right on cue, Sheen heard the doorbell.  From down the hall he heard a female voices and chatter, then footsteps as Spencer showed the new guests in.

Look Sheen, we thought you might be lonely so we invited some friends of yours, Mistress said.

Sheen looked up in horror as several of his female coworkers stood in the doorway with their mouths wide open.  There was pretty Gina and Lola from HR and Sue from accounting all looking on as Sheen continued to masturbate and give head to the big rubber strap on cock while still being pounded up the ass by Dagmar.

Ha Ha!  I always knew he was a sissy wimp, but this is even worse than I could have ever thought!

The ladies sat down to watch Sheen be humiliated for their pleasure.

Mistress snapped her fingers and ordered Sheen to eat her pussy.

The ladies from work were delighted to see how obedient Sheen was.

S/he's so subservient, I love that in a gurl.  Hmm, I think I've found some new things for Sheen to do at work.

Spencer came back in the room and immediately began flirting and kissing with the new girls.  How the hell was he doing that?  Sheen felt so jealous.

Aw, Sheen looks like he wishes he was Spencer.  Spencer's a real man darling, he's gonna get his cock sucked and fucked like a real man deserves.  Now grovel for mommy Sheen.

Oh please, may I suck on the big rubber cock for Mistress?  May I further offer my ass for Mistress Dagmar's pleasure.  I'm a sissy and deserve punishment for being a sissy.

The ladies lined up to let Spencer get a piece of them.  One girl straddled his cock and then lowered herself onto him while the other two stood next to him while he fingered their cunts.  He worked his fingers in and out of their tight holes like a musician playing an instrument.

Oh, fuck yeah baby, finger that cunt, feels so good.  Is he making your cunt feel good too Gina?

Hey sissy!  Come over here.  Spencer motioned for Sheen to crawl over and he meekly obeyed.
Here, lick the pussy juice from my hands.

Sheen lapped at his hands like a dog, relishing the taste of Gina's cunt juices on one hand and Lola's on the other.  This was a real man unlike sissy Sheen.  Sheen dare didn't look up, but out of the corner of his eye he could see Sue riding up and down on Spencer's hard cock.  He timed his stroking to Spencer's fucking and imagined how good it would feel if his cock was where Spencer's was.

Yeah, fuck yourself on my cock baby.  Now grind it, grind that cunt on me while my cock is all the way inside you.

Oh, fuck, that feels so damn good.  My cunt is on fire, yes!  I'm gonna fuck my own cunt with your cock.

Suck Sue's titties while she fucks herself on my cock ladies.

Gina and Lola leaned forward to suck Sue's tits while still getting finger fucked by Spencer.

See what I'm doing Sheen?  You're not gonna get to do this.  Your cock and hands will never get to be inside a woman again.  That is unless you consider yourself to be a gurl, cause you WILL be fingering your own ass.

The thought of that excited Sheen as he stroked his cock faster and faster.

Dagmar was really giving it to Sheen now and he was trying to hold on and not cum.

The girls kept rotating so each got to fuck Spencer while the other two would get fingered.  Each time Sheen would lick Spencer's fingers clean, tasting and relishing the flavors of the different women.

Dagmar complimented Mistress on her training.  I'm surprised your sissy hasn't cum yet, you've done an excellent job training hur.  So obedient, just like a good gurl should be, isn't that right sissy Sheen?

Poor Sheen pt 4

Poor Sheen pt 4

The ladies pushed Sheen to his limits.  He was on his knees for nearly four hours eating cunt.  Spencer the butler was the only other male present, but unlike Sheen he was allowed to fuck.  The ladies sucked Spencer's smallish cock right in front of poor Sheen's face.  Sheen wondered why they wanted him when his own cock was bigger.

Oh I can see the questions running through your little pathetic brain sissy Sheen.  You're wondering why you are down there and Spencer is up here with us.  Well, you see it's not the size of the man, or even his cock that makes him a real man.  That's what Spencer is, a real man, unlike you sissy.  Now let that thought brew in your simple mind.  Keep stroking yourself sissy because no one else will be touching your cock.

Sheen didn't dare look up, but he could see Spencer's lower body thrusting and hear the sounds of fucking.

Now keep eating pussy Sheen, like a good gurl should.

Dagmar, a tall blonde walked over and removed Theodore from Sheen's ass.  Everyone laughed when Sheen's asshole made a sucking sound as the giant dildo was removed.

Oh look he's gaping, Dagmar exclaimed.  All the ladies ran over to see the spectacle.  Sheen was so deeply ashamed as he held his butt cheeks open so all the ladies could get a good look at his stretched out anus.

Dagmar wasn't through though.  Oh no, Sheen's nightmare punishment wasn't over yet.  He knew this when he felt the head of the strap on dildo pushing at his sore stretched out asshole.

Oh, does that hurt Sheenie?  Dagmar said in a gentle voice.  There, there, Mommy's going to make it hurt just a little more.  You don't mind do you sweetheart?

She started fucking Sheen.  First slowly, then faster and faster and with harder and harder thrusts.  The sensations combined with his stroking was driving Sheen insane with lust.

The ladies were really enjoying Spencer's stiff cock.  He was laughing along with the girls as they watched Sheen masturbate while getting butt fucked for all to see.  Precum kept dribbling out of his stiff prick onto the floor.

Don't you cum bitch, not til I say!

Y,y,yes Mistress.

Sheen was using all his concentration not to cum. He did not want to disappoint Mistress.

The ladies pushed Sheen to his limits.  He was on his knees for nearly four hours eating cunt.  Spencer the butler was the only other male present, but unlike Sheen he was allowed to fuck.  The ladies sucked Spencer's smallish cock right in front of poor Sheen's face.  Sheen wondered why they wanted him when his own cock was bigger.

Oh I can see the questions running through your little pathetic brain sissy Sheen.  You're wondering why you are down there and Spencer is up here with us.  Well, you see it's not the size of the man, or even his cock that makes him a real man.  That's what Spencer is, a real man, unlike you sissy.  Now let that thought brew in your simple mind.  Keep stroking yourself sissy because no one else will be touching your cock.

Sheen didn't dare look up, but he could see Spencer's lower body thrusting and hear the sounds of fucking.

Now keep eating pussy Sheen, like a good gurl should.

Dagmar, a tall blonde walked over and removed Theodore from Sheen's ass.  Everyone laughed when Sheen's asshole made a sucking sound as the giant dildo was removed.

Oh look he's gaping, Dagmar exclaimed.  All the ladies ran over to see the spectacle.  Sheen was so deeply ashamed as he held his butt cheeks open so all the ladies could get a good look at his stretched out anus.

Dagmar wasn't through though.  Oh no, Sheen's nightmare punishment wasn't over yet.  He knew this when he felt the head of the strap on dildo pushing at his sore stretched out asshole.

Oh, does that hurt Sheenie?  Dagmar said in a gentle voice.  There, there, Mommy's going to make it hurt just a little more.  You don't mind do you sweetheart?

She started fucking Sheen.  First slowly, then faster and faster and with harder and harder thrusts.  The sensations combined with his stroking was driving Sheen insane with lust.

The ladies were really enjoying Spencer's stiff cock.  He was laughing along with the girls as they watched Sheen masturbate while getting butt fucked for all to see.  Precum kept dribbling out of his stiff prick onto the floor.

Don't you cum bitch, not til I say!

Y,y,yes Mistress.

Sheen was using all his concentration not to cum. He did not want to disappoint Mistress.

Poor Sheen pt 3

Poor Sheen pt 3

Take that cock bitch!  Suck it down your slut throat!

With those words Mistress shoved the 12 inch dildo all the way up Sheen's ass in one rough push, ripping his ass open.

Sheen let out a scream of pain.

All the ladies laughed.

Tears were running down his face as the dildo fucked it's way in and out of his ass.

Oh look, the sissy wimp is crying ladies.  Your mascara is running Sheenie.

More precum dribbled from the head of his engorged cock forming a small puddle on the floor below him.

Lick that up while I'm fucking your ass, lick it up so all the ladies can see what a sissy you are.

Sheen did as he was told, pulling Theodore from his mouth and using his tongue to clean the hardwood floor.  His ass was on fire as the dildo continued its never ending pounding in and out of his swollen ass.

Maybe that's enough for now, what do you think ladies?  No?  Oh, you're so naughty and so very right.  Did you think you'd be getting off the hook so easily Sheen?

Mistress placed the used dildo at Sheen's lips and ordered him to clean it with his mouth.

But, but Mistress, it's unsanitary.

Thwack!  You dare question my orders?  Thwack!

Ahh, no Mistress.

Sheen lowered his mouth over the dildo.  It was still warm from his own ass and it slid into his mouth easily with all the lube covering it.

And now that you're not pleasuring Theodore with your mouth, perhaps we can find something else for him to do.  Here's something.

Mistress began to shove Theodore up Sheen's ass ripping him wide open.  He was able to take only an inch or two as it stretched his ass to the limits.

Ahh, it hurts Mistress, it's too big!

Thwack!  I decide what is too big, I decide what your limits are.  Do you understand that bitch?!

Y,yyy, yes Mistress.

Tears were again streaming down Sheen's face as Mistress was able to work in more and more of the fake cock.  3, 4, 6, 8 inches glided in and out, pulling the soft inside tissues of his anal cavity as it went.

That's it Sheen.  Take that cock and suck that dirty one down your throat.  Sheen's cock was really dribbling precum now.  He was worried he might not be able to keep from cumming as Theodore was stimulating his prostate, squeezing it.

Oh Mistress, please, may I cum?

No!  You may not.  Your punishment has just begun dear.  Did you think that was all you'd get for punishment?

Thwack!

Thwack, thwack, thwack, thwack!!

Ahhh, what was that for Mistress?!!

Oh, no reason, a girl sometimes feels like it.

Thwack!

And that one's for questioning me.

Thwack, thwack, thwack and those are because it's Friday.

B, b, but  today is Wednesday Mistress.

Thwack!  Don't you correct me.  If I say it's Friday, then it's Friday!

Mistress shoved the 24 inch dildo all the way up Sheen's ass except for maybe two inches that were still out.

Sheen let out a horrifying scream.  Sweat cascaded down his body and added to the puddle that had formed under him.  His body shuddered at the full intrusion of the rubber cock's soda can girth tearing him open.

Before he could recover from the pain, Mistress ordered Sheen to stand and serve the ladies refreshments.

And don't you let that dildo cum out of your ass.  That's it, squeeze those boy cunt muscles and keep it in, no cheating, no hands.

All the ladies laughed at Sheen waddling around the room in 6 inch heels and a maid outfit all the while trying to balance the tray of snacks and drinks and attempting to keep the dildo lodged up his well used ass.

The ladies were dressed so beautifully in their lovely summer dresses.

Claudia, a 40 something MILF was seated on one of the couches.  Sheen asked her if he could serve her a drink.  She smiled and without a word pushed Sheen down to his knees.  She spread her legs and pointed at her panty covered cunt.

Sheen knew what to do.  He reached up her skirt and removed her soaking wet panties.  Then began eating her pussy.  She was musky and hot.

The other ladies gathered around to watch.

That's it sissy eat her pussy.  Lick it nice and good.  Make sure she cums on your face bitch.

Sheen took his time, just as he was trained. He was to pleasure her as long as she desired it.

One of the other ladies began working the dildo in and out of Sheen's ass again.  Sheen moaned in pleasure.

Oh look, the sissy likes being fucked up the ass.  What a sissy wimp.

Soon the other ladies had made a circle around Sheen and were demanding to have their pussies licked as well.

Sheen's mouth was so tired, but he kept licking and sucking all the while getting fucked up the ass with that giant dildo.  Since he was a sissy he was not allowed to manipulate or penetrate their pussies with his hands and of course never his cock.

Take that cock bitch!  Suck it down your slut throat!

With those words Mistress shoved the 12 inch dildo all the way up Sheen's ass in one rough push, ripping his ass open.

Sheen let out a scream of pain.

All the ladies laughed.

Tears were running down his face as the dildo fucked it's way in and out of his ass.

Oh look, the sissy wimp is crying ladies.  Your mascara is running Sheenie.

More precum dribbled from the head of his engorged cock forming a small puddle on the floor below him.

Lick that up while I'm fucking your ass, lick it up so all the ladies can see what a sissy you are.

Sheen did as he was told, pulling Theodore from his mouth and using his tongue to clean the hardwood floor.  His ass was on fire as the dildo continued its never ending pounding in and out of his swollen ass.

Maybe that's enough for now, what do you think ladies?  No?  Oh, you're so naughty and so very right.  Did you think you'd be getting off the hook so easily Sheen?

Mistress placed the used dildo at Sheen's lips and ordered him to clean it with his mouth.

But, but Mistress, it's unsanitary.

Thwack!  You dare question my orders?  Thwack!

Ahh, no Mistress.

Sheen lowered his mouth over the dildo.  It was still warm from his own ass and it slid into his mouth easily with all the lube covering it.

And now that you're not pleasuring Theodore with your mouth, perhaps we can find something else for him to do.  Here's something.

Mistress began to shove Theodore up Sheen's ass ripping him wide open.  He was able to take only an inch or two as it stretched his ass to the limits.

Ahh, it hurts Mistress, it's too big!

Thwack!  I decide what is too big, I decide what your limits are.  Do you understand that bitch?!

Y,yyy, yes Mistress.

Tears were again streaming down Sheen's face as Mistress was able to work in more and more of the fake cock.  3, 4, 6, 8 inches glided in and out, pulling the soft inside tissues of his anal cavity as it went.

That's it Sheen.  Take that cock and suck that dirty one down your throat.  Sheen's cock was really dribbling precum now.  He was worried he might not be able to keep from cumming as Theodore was stimulating his prostate, squeezing it.

Oh Mistress, please, may I cum?

No!  You may not.  Your punishment has just begun dear.  Did you think that was all you'd get for punishment?

Thwack!

Thwack, thwack, thwack, thwack!!

Ahhh, what was that for Mistress?!!

Oh, no reason, a girl sometimes feels like it.

Thwack!

And that one's for questioning me.

Thwack, thwack, thwack and those are because it's Friday.

B, b, but  today is Wednesday Mistress.

Thwack!  Don't you correct me.  If I say it's Friday, then it's Friday!

Mistress shoved the 24 inch dildo all the way up Sheen's ass except for maybe two inches that were still out.

Sheen let out a horrifying scream.  Sweat cascaded down his body and added to the puddle that had formed under him.  His body shuddered at the full intrusion of the rubber cock's soda can girth tearing him open.

Before he could recover from the pain, Mistress ordered Sheen to stand and serve the ladies refreshments.

And don't you let that dildo cum out of your ass.  That's it, squeeze those boy cunt muscles and keep it in, no cheating, no hands.

All the ladies laughed at Sheen waddling around the room in 6 inch heels and a maid outfit all the while trying to balance the tray of snacks and drinks and attempting to keep the dildo lodged up his well used ass.

The ladies were dressed so beautifully in their lovely summer dresses.

Claudia, a 40 something MILF was seated on one of the couches.  Sheen asked her if he could serve her a drink.  She smiled and without a word pushed Sheen down to his knees.  She spread her legs and pointed at her panty covered cunt.

Sheen knew what to do.  He reached up her skirt and removed her soaking wet panties.  Then began eating her pussy.  She was musky and hot.

The other ladies gathered around to watch.

That's it sissy eat her pussy.  Lick it nice and good.  Make sure she cums on your face bitch.

Sheen took his time, just as he was trained. He was to pleasure her as long as she desired it.

One of the other ladies began working the dildo in and out of Sheen's ass again.  Sheen moaned in pleasure.

Oh look, the sissy likes being fucked up the ass.  What a sissy wimp.

Soon the other ladies had made a circle around Sheen and were demanding to have their pussies licked as well.

Sheen's mouth was so tired, but he kept licking and sucking all the while getting fucked up the ass with that giant dildo.  Since he was a sissy he was not allowed to manipulate or penetrate their pussies with his hands and of course never his cock.

Poor Sheen pt 2

Poor Sheen pt 2

Sheen grabbed the lube and started fingering his own ass in front of the whole room of polite society ladies.  They were all laughing at him and talking about what a pathetic excuse he was for a man.

Mistress came up behind Sheen and pulled his hair, lifting his head up and backward.

There now you can see all the pretty ladies you'll never get to fuck.  See how they're all laughing at you.  They think you're a pathetic sissy wimp.

Now Sheen, go to the drawer and I want you to pick out an appropriate device to punish yourself with.  DON'T disappoint me!

Sheen crawled on his hands and knees, head down, to the cabinet where Mistress kept her instruments of torture.  He opened the doors and began opening the third drawer from the top.

I said DON'T disappoint me.

Y,y,yes Mistress

Sheen's trembling hands moved to the next lower drawer.

That's it bitch, you know what to do, don't you?

The drawer slid open, gliding on it's ball bearing tracks smoothly.

Sheen looked in the drawer.  There were many dildos in there, all of which Sheen had seen many times since part of his duties as a sub sissy was cleaning, maintaining and proper storage of all Mistress' toys.  Occasionally, as a treat, Sheen was allowed to watch Mistress pleasure herself with one of her many dildos. If he'd really been good, he was allowed to lick her juices from the dildo as well.  Mistress so enjoyed watching her sissy deep throat the dildos.

Sheen used to be a man, but here, he'd been transformed by Mistress into the pathetic sissy he now was.  Sheen meekly selected a large blue dildo and began to bring it out.  He presented it to Mistress.

Once again, you have disappointed me, and in front of company no less!

Thwack, the riding crop slapped Sheen's beet red ass, THWACK, THWACK, THWACK!!

I'm sorry Mistress, so sorry, I didn't mean to...

Nonsense, you did this on purpose, I think you wanted me to punish you.  Well, it's punishment you shall get then bitch.  Go get Theodore.

Just hearing that name caused a panic in Sheen.

No Mistress, I promise I'll be good, please, not, not Theod, d, d, not Theodore.

Oh, stop your stammering cunt.  You're going to take him because that is what you deserve, isn't it?  THWACK, now go hurry up, go, NOW!

Sheen scurried over to the drawer like the good little subservient bitch he is.

He gently placed the blue dildo back in the drawer making sure to do it as per Mistress's approved method.

Very good, now Theodore.

Sheen closed the drawer and opened the very bottom one.  There was only one thing in there, held in place by a purple velvet wrapped soft foam cut out that matched it's exact shape.  Sheen picked up a massive dildo and brought it to Mistress.

Mistress, I bring you Theodore, he said as he handed the giant rubber penis to her as if it were Excalibur itself.

Very good Sheen.  I do hope you lubed yourself up well, because today will be the day that you finally will take the full length of Theodore.

No, please Mistress, please don't make me.

Thwack!

You will do as you are told.  Now come and kiss Theodore.

Sheen lifted his bowed head and kissed the head of the giant prick.

That's it, worship that cock, just like a gurl.  Make Theodore feel good.

Sheen began to gently kiss it and lick it as if it were a real cock.  He felt so humiliated.

Very good Sheen, you look just like a real gurl, doesn't he ladies?

All the women laughed at the sight of poor pathetic sissy Sheen kissing and licking the giant dildo cock.  His face was bright red.

Now take Theodore in your mouth Sheen.  Last time you disappointed me, I want you to get at least an extra two inches down your slut throat today.

Sheen's head began to bob up and down.  His mouth was stretched all the way open trying to engulf the head of the giant cock.

He worked it in and out slowly as he'd been instructed, but as it neared the back of his throat he began to gag.

Now now Sheen, don't you disappoint Mistress.  You're embarrassing me in front of company.

Sheen pushed on, working more and more in and out.  He so wanted to please Mistress.

That's it Sheenie, open that slut throat all the way and let it slide in.

Sheen was concentrating so hard on swallowing the dildo that it shocked him when Mistress shoved a finger up his ass.  His body tensed and he instinctively pulled away.

Are you refusing me bitch?  Don't you ever do that.

Sheen tried to apologize, but he couldn't speak with the dildo down his throat.  He almost choked on it when the riding crop came down on his ass.  THWACK

The next thing he felt was Mistress shoving a large dildo up his ass.

That's it, keep sucking that cock while you're getting fucked...SLUT.

All the ladies giggled and whispered to each other.  Sheen's face was beet red with embarrassment and shame as the rubber cock slipped between his lips and Mistress continued her relentless ass ramming.

The sight of Sheen being degraded in public pleased Mistress and caused her vagina to moisten.  Dirty thoughts entered her mind.  She knew just what to do to poor Sheen next to further humiliate him.

To Be Continued...

Sheen grabbed the lube and started fingering his own ass in front of the whole room of polite society ladies.  They were all laughing at him and talking about what a pathetic excuse he was for a man.

Mistress came up behind Sheen and pulled his hair, lifting his head up and backward.

There now you can see all the pretty ladies you'll never get to fuck.  See how they're all laughing at you.  They think you're a pathetic sissy wimp.

Now Sheen, go to the drawer and I want you to pick out an appropriate device to punish yourself with.  DON'T disappoint me!

Sheen crawled on his hands and knees, head down, to the cabinet where Mistress kept her instruments of torture.  He opened the doors and began opening the third drawer from the top.

I said DON'T disappoint me.

Y,y,yes Mistress

Sheen's trembling hands moved to the next lower drawer.

That's it bitch, you know what to do, don't you?

The drawer slid open, gliding on it's ball bearing tracks smoothly.

Sheen looked in the drawer.  There were many dildos in there, all of which Sheen had seen many times since part of his duties as a sub sissy was cleaning, maintaining and proper storage of all Mistress' toys.  Occasionally, as a treat, Sheen was allowed to watch Mistress pleasure herself with one of her many dildos. If he'd really been good, he was allowed to lick her juices from the dildo as well.  Mistress so enjoyed watching her sissy deep throat the dildos.

Sheen used to be a man, but here, he'd been transformed by Mistress into the pathetic sissy he now was.  Sheen meekly selected a large blue dildo and began to bring it out.  He presented it to Mistress.

Once again, you have disappointed me, and in front of company no less!

Thwack, the riding crop slapped Sheen's beet red ass, THWACK, THWACK, THWACK!!

I'm sorry Mistress, so sorry, I didn't mean to...

Nonsense, you did this on purpose, I think you wanted me to punish you.  Well, it's punishment you shall get then bitch.  Go get Theodore.

Just hearing that name caused a panic in Sheen.

No Mistress, I promise I'll be good, please, not, not Theod, d, d, not Theodore.

Oh, stop your stammering cunt.  You're going to take him because that is what you deserve, isn't it?  THWACK, now go hurry up, go, NOW!

Sheen scurried over to the drawer like the good little subservient bitch he is.

He gently placed the blue dildo back in the drawer making sure to do it as per Mistress's approved method.

Very good, now Theodore.

Sheen closed the drawer and opened the very bottom one.  There was only one thing in there, held in place by a purple velvet wrapped soft foam cut out that matched it's exact shape.  Sheen picked up a massive dildo and brought it to Mistress.

Mistress, I bring you Theodore, he said as he handed the giant rubber penis to her as if it were Excalibur itself.

Very good Sheen.  I do hope you lubed yourself up well, because today will be the day that you finally will take the full length of Theodore.

No, please Mistress, please don't make me.

Thwack!

You will do as you are told.  Now come and kiss Theodore.

Sheen lifted his bowed head and kissed the head of the giant prick.

That's it, worship that cock, just like a gurl.  Make Theodore feel good.

Sheen began to gently kiss it and lick it as if it were a real cock.  He felt so humiliated.

Very good Sheen, you look just like a real gurl, doesn't he ladies?

All the women laughed at the sight of poor pathetic sissy Sheen kissing and licking the giant dildo cock.  His face was bright red.

Now take Theodore in your mouth Sheen.  Last time you disappointed me, I want you to get at least an extra two inches down your slut throat today.

Sheen's head began to bob up and down.  His mouth was stretched all the way open trying to engulf the head of the giant cock.

He worked it in and out slowly as he'd been instructed, but as it neared the back of his throat he began to gag.

Now now Sheen, don't you disappoint Mistress.  You're embarrassing me in front of company.

Sheen pushed on, working more and more in and out.  He so wanted to please Mistress.

That's it Sheenie, open that slut throat all the way and let it slide in.

Sheen was concentrating so hard on swallowing the dildo that it shocked him when Mistress shoved a finger up his ass.  His body tensed and he instinctively pulled away.

Are you refusing me bitch?  Don't you ever do that.

Sheen tried to apologize, but he couldn't speak with the dildo down his throat.  He almost choked on it when the riding crop came down on his ass.  THWACK

The next thing he felt was Mistress shoving a large dildo up his ass.

That's it, keep sucking that cock while you're getting fucked...SLUT.

All the ladies giggled and whispered to each other.  Sheen's face was beet red with embarrassment and shame as the rubber cock slipped between his lips and Mistress continued her relentless ass ramming.

The sight of Sheen being degraded in public pleased Mistress and caused her vagina to moisten.  Dirty thoughts entered her mind.  She knew just what to do to poor Sheen next to further humiliate him.

To Be Continued...

Poor Sheen

Poor Sheen

What the fuck did I say bitch?

Sheen was almost in tears.  He was down on his knees, head bowed to Mistress.

I'm sorry Mistress.  I know I need to show my obedience.

That's right bitch!  That cock should be hard whenever a lady is present.  Now get it up now!

Thwack!  The leather tipped riding crop came down swatting Sheen's tender flesh.

Stick that ass out cunt.
 
His ass was already red from the previous whacks he'd already received in training.  Sheen arched his back and stuck his ass out for Mistress.

Thwack, thwack, thwack, the crop came down again in 3 quick bursts.  The pain stung, then lingered.  Oddly Sheen's cock began to swell despite the pain, or maybe it was because of it.

That's it, make it hard you little sissy bitch!

Yes, Mistress.

Faster!  Stroke it so everyone can see how pathetic you are.

Sheen was stroking his cock faster and faster now.  It got rock hard at the thought of all the ladies in the room watching him jerk off in front of them.

Don't you cum bitch, you don't cum unless I tell you, understand?!!

Yes, Mistress, a sissy cunt like me doesn't deserve the privilege of cumming without a woman's consent.

That's right bitch, and don't you forget it, ever.

A drop of precum ooozed out of the head of Sheen's cock and dribbled on the floor.

You stupid bitch, look what a mess you've made.

I'm sorry, I didn't mean to, it was an accid....

Thwack, the riding crop whipped Sheen's ass.  Thwack, thwack, thwack, three times again.

Sheen let out a shriek of agony as the pain ripped through his body.

Aw, was that too much for you sissy?  Can't take the pain?

A tear ran down Sheen's cheek.

I'm s s s sorry Mistress, didn't m m m mean t t t to..

Thwack

I'm not interested in your lame excuses bitch.  Now clean up that mess you've made.

Sheen began to stand, but just as he started to rise Mistress' stiletto heel pushed him back down.

Did I say you could stand sissy?

No Mistress, but how, how, I'm mean I was...

Thwack

You stupid slut, obviously you are to clean it with your mouth.  Now get down there and clean up that mess.

Sheen leaned forward and began licking his own precum from the floor.

Oh, look at that ass ladies.  It looks like it needs a good fucking.  See how swollen it is from the 12 inch dildo I used on it earlier?  I think it needs more punishment.  I think we need to teach this bitch a lesson.

Oh please Mistress, my ass is so sore, please.

Thwack!

You don't make demands on me or any other woman bitch.  Now arch that back and shove that ass out.

Mistress threw a tube of lube on the floor next to Sheen.

Now lube up that ass and get ready for a pounding bitch.

To Be Continued...

What the fuck did I say bitch?

Sheen was almost in tears.  He was down on his knees, head bowed to Mistress.

I'm sorry Mistress.  I know I need to show my obedience.

That's right bitch!  That cock should be hard whenever a lady is present.  Now get it up now!

Thwack!  The leather tipped riding crop came down swatting Sheen's tender flesh.

Stick that ass out cunt.
 
His ass was already red from the previous whacks he'd already received in training.  Sheen arched his back and stuck his ass out for Mistress.

Thwack, thwack, thwack, the crop came down again in 3 quick bursts.  The pain stung, then lingered.  Oddly Sheen's cock began to swell despite the pain, or maybe it was because of it.

That's it, make it hard you little sissy bitch!

Yes, Mistress.

Faster!  Stroke it so everyone can see how pathetic you are.

Sheen was stroking his cock faster and faster now.  It got rock hard at the thought of all the ladies in the room watching him jerk off in front of them.

Don't you cum bitch, you don't cum unless I tell you, understand?!!

Yes, Mistress, a sissy cunt like me doesn't deserve the privilege of cumming without a woman's consent.

That's right bitch, and don't you forget it, ever.

A drop of precum ooozed out of the head of Sheen's cock and dribbled on the floor.

You stupid bitch, look what a mess you've made.

I'm sorry, I didn't mean to, it was an accid....

Thwack, the riding crop whipped Sheen's ass.  Thwack, thwack, thwack, three times again.

Sheen let out a shriek of agony as the pain ripped through his body.

Aw, was that too much for you sissy?  Can't take the pain?

A tear ran down Sheen's cheek.

I'm s s s sorry Mistress, didn't m m m mean t t t to..

Thwack

I'm not interested in your lame excuses bitch.  Now clean up that mess you've made.

Sheen began to stand, but just as he started to rise Mistress' stiletto heel pushed him back down.

Did I say you could stand sissy?

No Mistress, but how, how, I'm mean I was...

Thwack

You stupid slut, obviously you are to clean it with your mouth.  Now get down there and clean up that mess.

Sheen leaned forward and began licking his own precum from the floor.

Oh, look at that ass ladies.  It looks like it needs a good fucking.  See how swollen it is from the 12 inch dildo I used on it earlier?  I think it needs more punishment.  I think we need to teach this bitch a lesson.

Oh please Mistress, my ass is so sore, please.

Thwack!

You don't make demands on me or any other woman bitch.  Now arch that back and shove that ass out.

Mistress threw a tube of lube on the floor next to Sheen.

Now lube up that ass and get ready for a pounding bitch.

To Be Continued...