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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!
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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?


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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.




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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.


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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...

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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...
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Date pt. 5

Bobbi moaned in pleasure as Rick's fingers worked their way in and out of hur tight little asshole.

Oh Ricky, please finger me, it feels so good.

You gonna be a good gurl and do as I say?

Yes, oh yes.

You gonna be my little sissy slut?  Gonna suck me and put out whenever I want, aren't you?

Yes, Ricky, yes.

His middle finger was all the way up Bobbi's ass now.

You know why?  Because you're a horny slut.

Yes, I'm a horny slut, Yes, oh Ricky that feels so good, please don't stop.

Rick's fingers kept fucking hur in the ass, then sensation was wonderful.  Bobbi's tiny gurl clit was pressed up against hur silky thong.

You want me to fuck you?

Oh Yes!

Rick turned Bobbi around on hur knees and lifted hur dress up over hur ass.  He paused to look at that nice firm ass and puckered asshole waiting to be fucked.

I'm gonna make you a real gurl now Bobbi.  Are you ready to made into a real gurl?

Oh yes, I need it, I need your hard cock up my tight little hole.  Please.

Rick rubbed the head of his hard prick against hur hole, making little circles.

Bobbi tried to push back against it, but Rick pulled away.

Not til I say you horny little slut.

He slapped hur ass with his hard cock.

Please, I need it your hard cock Ricky, I need it.

Alright, I guess you deserve to be fucked a little.

With that, Rick slowly shoved the head of his cock into Bobbi's tight gurl hole.

Bobbi let out a scream.

Oh, fuck!  Yes, I've been waiting for this.  Please make me a real gurl, please.

Rick slowly worked his cock in and out of Bobbi.

When she loosened up enough Rick began to really give hur a pounding.  His balls were slapping up against Bobbi and Bobbi loved the sensation.

Oh yes, fuck me, fuck hard Ricky.

All the excitement finally got to Rick and he couldn't hold back any longer. He let out a scream as his cock let go a big load of cum into Bobbi's ass.

OH, fuck!

Bobbi came at the sensation of Rick's cock pulsing in hur hole.  She filled hur little thong with hur own sissy gurl juice.

When he had calmed enough, Rick pulled out of Bobbi and snapped hur thong back over hur dripping stretched out and sore hole.

Now, I'm gonna drop you back at home.  Wouldn't want your Dad to be upset now, would we?

But Ricky, I want to stay out with you longer.

No, this is how it's gonna be.  I fuck you and you go home with an ass full of my cum after.

Oh Ricky you're so mean.  I hate you.

In front of Bobbi's house, as soon as Bobbi's car door closed, Rick sped off in his car.  Bobbi stood there feeling so used and sore, Rick's cum was dribbling out of hur ass.  She loved it and couldn't wait to be used again next time!

I love you Ricky.




Bobbi moaned in pleasure as Rick's fingers worked their way in and out of hur tight little asshole.

Oh Ricky, please finger me, it feels so good.

You gonna be a good gurl and do as I say?

Yes, oh yes.

You gonna be my little sissy slut?  Gonna suck me and put out whenever I want, aren't you?

Yes, Ricky, yes.

His middle finger was all the way up Bobbi's ass now.

You know why?  Because you're a horny slut.

Yes, I'm a horny slut, Yes, oh Ricky that feels so good, please don't stop.

Rick's fingers kept fucking hur in the ass, then sensation was wonderful.  Bobbi's tiny gurl clit was pressed up against hur silky thong.

You want me to fuck you?

Oh Yes!

Rick turned Bobbi around on hur knees and lifted hur dress up over hur ass.  He paused to look at that nice firm ass and puckered asshole waiting to be fucked.

I'm gonna make you a real gurl now Bobbi.  Are you ready to made into a real gurl?

Oh yes, I need it, I need your hard cock up my tight little hole.  Please.

Rick rubbed the head of his hard prick against hur hole, making little circles.

Bobbi tried to push back against it, but Rick pulled away.

Not til I say you horny little slut.

He slapped hur ass with his hard cock.

Please, I need it your hard cock Ricky, I need it.

Alright, I guess you deserve to be fucked a little.

With that, Rick slowly shoved the head of his cock into Bobbi's tight gurl hole.

Bobbi let out a scream.

Oh, fuck!  Yes, I've been waiting for this.  Please make me a real gurl, please.

Rick slowly worked his cock in and out of Bobbi.

When she loosened up enough Rick began to really give hur a pounding.  His balls were slapping up against Bobbi and Bobbi loved the sensation.

Oh yes, fuck me, fuck hard Ricky.

All the excitement finally got to Rick and he couldn't hold back any longer. He let out a scream as his cock let go a big load of cum into Bobbi's ass.

OH, fuck!

Bobbi came at the sensation of Rick's cock pulsing in hur hole.  She filled hur little thong with hur own sissy gurl juice.

When he had calmed enough, Rick pulled out of Bobbi and snapped hur thong back over hur dripping stretched out and sore hole.

Now, I'm gonna drop you back at home.  Wouldn't want your Dad to be upset now, would we?

But Ricky, I want to stay out with you longer.

No, this is how it's gonna be.  I fuck you and you go home with an ass full of my cum after.

Oh Ricky you're so mean.  I hate you.

In front of Bobbi's house, as soon as Bobbi's car door closed, Rick sped off in his car.  Bobbi stood there feeling so used and sore, Rick's cum was dribbling out of hur ass.  She loved it and couldn't wait to be used again next time!

I love you Ricky.




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Date pt 4

Rick tweaked Bobbi's nipples through hur bra, twisting them gently.  Bobbi arched hur back in response, pushing hur tiny A cups out for Rick.

Oh Ricky, please stop, I promised Daddy I'd be a good gurl.  Please, I want to, I  mean I don't, I....Oh, please don't stop.

Oh, you know you want it slut.  Here, feel my cock baby.

Rick grabbed Bobbi's little feminine hand and put it on his crotch.  Bobbi was excited to feel his stiff cock through Rick's jeans and began squeezing and rubbing it.

That's it baby, show me how much you want that cock.  You're not a cock tease are you?

No, I'm a good gurl.

Bobbi tried to remove hur hand from his crotch but he grabbed hur wrist and held it there.  Rick had moved on to sucking and licking Bobbi's tits now.  Bobbi was moaning from the sensations she was having.

Oh Ricky, that feels so good, so so good.  Please don't stop.

Rick's hands slid down and squeezed Bobbi's ass.  He felt hur thong through the dress.

Oh Ricky, please stop, don't, please.

Hur words said no, but Bobbi's body kept saying yes.

Rick slid his hand up hur dress and started massaging hur ass.  Then he slipped his fingers under hur thong.

Bobbi tried to protest, but she was cupping hur breast and feeding it to Rick at the same time.

Ricks fingers found their way into Bobbi's ass, first rubbing hur little rose bud, then probing hur, a little deeper each time.

Oh Ricky, oh that feels so good.
Rick tweaked Bobbi's nipples through hur bra, twisting them gently.  Bobbi arched hur back in response, pushing hur tiny A cups out for Rick.

Oh Ricky, please stop, I promised Daddy I'd be a good gurl.  Please, I want to, I  mean I don't, I....Oh, please don't stop.

Oh, you know you want it slut.  Here, feel my cock baby.

Rick grabbed Bobbi's little feminine hand and put it on his crotch.  Bobbi was excited to feel his stiff cock through Rick's jeans and began squeezing and rubbing it.

That's it baby, show me how much you want that cock.  You're not a cock tease are you?

No, I'm a good gurl.

Bobbi tried to remove hur hand from his crotch but he grabbed hur wrist and held it there.  Rick had moved on to sucking and licking Bobbi's tits now.  Bobbi was moaning from the sensations she was having.

Oh Ricky, that feels so good, so so good.  Please don't stop.

Rick's hands slid down and squeezed Bobbi's ass.  He felt hur thong through the dress.

Oh Ricky, please stop, don't, please.

Hur words said no, but Bobbi's body kept saying yes.

Rick slid his hand up hur dress and started massaging hur ass.  Then he slipped his fingers under hur thong.

Bobbi tried to protest, but she was cupping hur breast and feeding it to Rick at the same time.

Ricks fingers found their way into Bobbi's ass, first rubbing hur little rose bud, then probing hur, a little deeper each time.

Oh Ricky, oh that feels so good.
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Bobbi's Date w Rick cont...

Rick slid Bobbi's sweater off hur shoulders and she made a fake protest.

No, Rick, You promised you'd be a good boy.  I'm an old fashioned gurl, No, be good Rick.

You weren't so old fashioned at Mr J's poker party the other night, were you?  I just want a little more of that ass baby.

Don't talk to me like that Ricky, you make me sound like a dirty slut.

But that's what you really are isn't it?  You crave that hard cock, don't you?  You don't care if they're big or small, you just crave hard cocks.  You seemed to like sucking all those dirty cocks at MR J's house.  I saw you in the window the other night too, trying to tease me.

I wasn't trying to tease you Ricky, I wouldn't do that.  You have a filthy mind and a filthy mouth.

And this filthy mouth is gonna taste you.

Rick put his mouth over Bobbi's and kissed hur deeply.  Their tongues danced.  Bobbi felt tingly all over as Rick's hands fondled hur small flat chested breasts through her clothes.

Oh Ricky, you're making me so hot.

Rick kissed his way down hur neck.  He paused enjoying the view of hur dainty shoulders framed by the thin straps of hur dress.  He could see the white of hur bra straps, they had a lacy edge on them.  He remembered seeing hur in the window in hur bra and panties and it turned him on so much to have hur right here.

Rick slowly slid one dress strap, then the other off hur shoulders.

No Ricky, No, you're being bad, you....you promised to be a good boy.

Rick knew she wanted it.  He peeled the top of hur dress down exposing hur bra covered tits.  He paused again, enjoying the sight of hur small tits in their virginal white lacy bralette.

Rick slid Bobbi's sweater off hur shoulders and she made a fake protest.

No, Rick, You promised you'd be a good boy.  I'm an old fashioned gurl, No, be good Rick.

You weren't so old fashioned at Mr J's poker party the other night, were you?  I just want a little more of that ass baby.

Don't talk to me like that Ricky, you make me sound like a dirty slut.

But that's what you really are isn't it?  You crave that hard cock, don't you?  You don't care if they're big or small, you just crave hard cocks.  You seemed to like sucking all those dirty cocks at MR J's house.  I saw you in the window the other night too, trying to tease me.

I wasn't trying to tease you Ricky, I wouldn't do that.  You have a filthy mind and a filthy mouth.

And this filthy mouth is gonna taste you.

Rick put his mouth over Bobbi's and kissed hur deeply.  Their tongues danced.  Bobbi felt tingly all over as Rick's hands fondled hur small flat chested breasts through her clothes.

Oh Ricky, you're making me so hot.

Rick kissed his way down hur neck.  He paused enjoying the view of hur dainty shoulders framed by the thin straps of hur dress.  He could see the white of hur bra straps, they had a lacy edge on them.  He remembered seeing hur in the window in hur bra and panties and it turned him on so much to have hur right here.

Rick slowly slid one dress strap, then the other off hur shoulders.

No Ricky, No, you're being bad, you....you promised to be a good boy.

Rick knew she wanted it.  He peeled the top of hur dress down exposing hur bra covered tits.  He paused again, enjoying the sight of hur small tits in their virginal white lacy bralette.

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Date Part 2

Rick picked hur up at 8 PM sharp.  He had the coolest car and he must have washed it before he came to get hur because it was all pretty and shiny.  He took Bobbi to a sushi place, very classy and nice.  Bobbi got a little tipsy drinking sake and started to get more and more flirty with Rick.  She'd pick up the sushi with her fingers and feed him, then make him lick her french tip manicured nails.  She giggled when he did it.  She knew poor Rick was under hur spell completely.

As promised Rick was a perfect gentleman at dinner.  He opened the car door for Bobbi and treated hur like a princess.  He kept telling Bobbi how beautiful she looked.  Bobbi was really getting hot from all the compliments and manly attention.  Rick drove them up to look out point, he knew a spot away from all the other cars where they could have some privacy.

They talked for a while and Rick made some silly jokes.  Bobbi liked his big strong arms.  He asked Bobbi if it would be ungentlemanly to ask for a little kiss.  Bobbi said she thought he'd earned a kiss, but just a little one.  Rick leaned in and kissed hur, soft and gentle at first.  Then the passion started to build and the kissing became more and more intense.  Ricks hands began to wander all over Bobbi's body, feeling hur through the tight dress she was wearing.
Rick picked hur up at 8 PM sharp.  He had the coolest car and he must have washed it before he came to get hur because it was all pretty and shiny.  He took Bobbi to a sushi place, very classy and nice.  Bobbi got a little tipsy drinking sake and started to get more and more flirty with Rick.  She'd pick up the sushi with her fingers and feed him, then make him lick her french tip manicured nails.  She giggled when he did it.  She knew poor Rick was under hur spell completely.

As promised Rick was a perfect gentleman at dinner.  He opened the car door for Bobbi and treated hur like a princess.  He kept telling Bobbi how beautiful she looked.  Bobbi was really getting hot from all the compliments and manly attention.  Rick drove them up to look out point, he knew a spot away from all the other cars where they could have some privacy.

They talked for a while and Rick made some silly jokes.  Bobbi liked his big strong arms.  He asked Bobbi if it would be ungentlemanly to ask for a little kiss.  Bobbi said she thought he'd earned a kiss, but just a little one.  Rick leaned in and kissed hur, soft and gentle at first.  Then the passion started to build and the kissing became more and more intense.  Ricks hands began to wander all over Bobbi's body, feeling hur through the tight dress she was wearing.
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A Date for Rick?

Rick started hanging around at Mr J's place a lot more.  In fact he was over almost every night after work, hoping to see pretty Bobbi.  Bobbi was playing hard to get though, so she'd purposely not come home or pretend not to see Rick when she walked by.  She'd wear cute little outfits to tease him; short skirts or short shorts.  One time when no one was home she walked around the living room in hur bra and panties right where she knew they could see hur from Mr J's window.  She could hardly contain her smile, knowing how excited poor Rick must have been to see hur like that.

Rick finally got up the courage and asked hur out one Friday and Bobbi told him maybe, even though she really wanted to go.  Rick was upset, so Bobbi teased him more.

Well, I guess I'll go out with you Rick, but only if you promise to be a gentleman.  My dad will kill you if you try and feel my body through my clothes you know.

Oh, I promise Bobbi, I'll be a perfect gentleman.

OK then, you can take me out tomorrow night.  It'd better be romantic though.
Rick started hanging around at Mr J's place a lot more.  In fact he was over almost every night after work, hoping to see pretty Bobbi.  Bobbi was playing hard to get though, so she'd purposely not come home or pretend not to see Rick when she walked by.  She'd wear cute little outfits to tease him; short skirts or short shorts.  One time when no one was home she walked around the living room in hur bra and panties right where she knew they could see hur from Mr J's window.  She could hardly contain her smile, knowing how excited poor Rick must have been to see hur like that.

Rick finally got up the courage and asked hur out one Friday and Bobbi told him maybe, even though she really wanted to go.  Rick was upset, so Bobbi teased him more.

Well, I guess I'll go out with you Rick, but only if you promise to be a gentleman.  My dad will kill you if you try and feel my body through my clothes you know.

Oh, I promise Bobbi, I'll be a perfect gentleman.

OK then, you can take me out tomorrow night.  It'd better be romantic though.
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Old Man Johnson Part 2

Bobbi showed up a little late to the poker party, but for the men it was well worth the wait.  She had decided to wear an ultra short maid outfit with stockings and a garter belt and five inch heels.  The men all went silent when she walked in and removed her coat to reveal hur outfit.  Mr J introduced hur to the boys and told her what she'd be doing.  Basically, she could hang out and watch TV on the couch in the living room and they'd be right there at the dining room table.  When they wanted food or drinks they'd call her over and she would bring it to them.

The food was easy, as they had premade sandwiches and other things all ready to go in the kitchen.  They also had the beer in a large cooler full of ice.  Some of them liked cocktails, so Bobbi was to make those as well.  It seemed easy enough and all the men were so nice, they all tipped Bobbi when she'd bring them their refreshments.  As the night wore on, they got louder and the alcohol started taking effect, the men started getting more touchy, putting their arms around Bobbi's skinny little waist or giving hur a pat on the bottom.

Bobbi was enjoying all the attention, some of the guys were pretty cute.  She noticed that some of them were getting hard in their pants watching hur.  Bobbi teased them, bending over to pick things up or leaning over so they could peek down hur top at hur tiny A cup tits.  She'd put hur hand on their shoulder and whisper in their ears "Can I get you anything?", running her hand through their hair.

Some of the guys weren't doing so good at the table, but Bobbi's presence helped keep them calm, which was part of the reason Mr J had wanted hur there.  They'd take a break and sit with hur on the couch and watch TV.  One guy flipped the channel to an adult one and Bobbi pretended to be embarrassed.  The guy, Rick, teased hur about it.  Then he started putting his arms around hur.  Bobbi didn't resist.  His hands were running all over hur little body and Bobbi was getting so excited when his fingers rubbed hur nipples through hur top.  They started kissing and Bobbi's hands were all over him too.

Bobbi took out Rick's cock and started sucking him.  The guys facing the couch saw it and soon everyone was watching.  They all got up and walked over to see.  Soon they all had their cocks out and Bobbi was down on hur knees pleasuring all those hard cocks with hur mouth and hands.

It wasn't long before Bobbi was completely covered in cum.  Hur face, tits and dress were completely drenched.  She decided to go upstairs and wash hur face as she couldn't go home like that.  When she came back down, most of the guys had gone home and they'd left a giant stack of money for her.  Bobbi had made more money that night than in a year of working hur minimum wage job at the store.  Mr J gave Bobbi a kiss and said thank you, handing hur the money he was going to pay hur plus an extra hundred.  He was to become one of Bobbi's sugar daddies, but that is another story!
Bobbi showed up a little late to the poker party, but for the men it was well worth the wait.  She had decided to wear an ultra short maid outfit with stockings and a garter belt and five inch heels.  The men all went silent when she walked in and removed her coat to reveal hur outfit.  Mr J introduced hur to the boys and told her what she'd be doing.  Basically, she could hang out and watch TV on the couch in the living room and they'd be right there at the dining room table.  When they wanted food or drinks they'd call her over and she would bring it to them.

The food was easy, as they had premade sandwiches and other things all ready to go in the kitchen.  They also had the beer in a large cooler full of ice.  Some of them liked cocktails, so Bobbi was to make those as well.  It seemed easy enough and all the men were so nice, they all tipped Bobbi when she'd bring them their refreshments.  As the night wore on, they got louder and the alcohol started taking effect, the men started getting more touchy, putting their arms around Bobbi's skinny little waist or giving hur a pat on the bottom.

Bobbi was enjoying all the attention, some of the guys were pretty cute.  She noticed that some of them were getting hard in their pants watching hur.  Bobbi teased them, bending over to pick things up or leaning over so they could peek down hur top at hur tiny A cup tits.  She'd put hur hand on their shoulder and whisper in their ears "Can I get you anything?", running her hand through their hair.

Some of the guys weren't doing so good at the table, but Bobbi's presence helped keep them calm, which was part of the reason Mr J had wanted hur there.  They'd take a break and sit with hur on the couch and watch TV.  One guy flipped the channel to an adult one and Bobbi pretended to be embarrassed.  The guy, Rick, teased hur about it.  Then he started putting his arms around hur.  Bobbi didn't resist.  His hands were running all over hur little body and Bobbi was getting so excited when his fingers rubbed hur nipples through hur top.  They started kissing and Bobbi's hands were all over him too.

Bobbi took out Rick's cock and started sucking him.  The guys facing the couch saw it and soon everyone was watching.  They all got up and walked over to see.  Soon they all had their cocks out and Bobbi was down on hur knees pleasuring all those hard cocks with hur mouth and hands.

It wasn't long before Bobbi was completely covered in cum.  Hur face, tits and dress were completely drenched.  She decided to go upstairs and wash hur face as she couldn't go home like that.  When she came back down, most of the guys had gone home and they'd left a giant stack of money for her.  Bobbi had made more money that night than in a year of working hur minimum wage job at the store.  Mr J gave Bobbi a kiss and said thank you, handing hur the money he was going to pay hur plus an extra hundred.  He was to become one of Bobbi's sugar daddies, but that is another story!
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Old Man Johnson

Old man Johnson was especially appreciative of Bobbi's transformation, he was always so friendly and nice, complimenting Bobbi and telling hur how pretty she looked.  Bobbi had used to help him with raking leaves and doing yard work, but now that she was a gurl, old man Johnson wouldn't hear of hur doing any hard work.

Come sit with me on the porch Bobbi.  You look so pretty in your new outfit, did your mom get you that?  Why don't we have some lemonade?  Bobbi would tease him too, letting him see a little lace under her shirt or a little too much thigh.

One time Bobbi almost fell in her 5 inch slut shoes.  Luckily Mr J caught her in his strong arms before she fell.  Oh, you're light as a feather dear, he said.  Bobbi just blushed.  S/he told Mr J she'd make him dinner sometime for "being her big strong hero".

Oh that's OK sweetie, but I do have an offer for you.  I'm hosting a poker night at my place this Friday and I need a beer girl, if you want to make a little money and you're not busy.

Hmm, I'll have to check.  Bobbi pulled out hur phone to check quickly and saw she was free after 8.  OK Mr J your on.

OK, good.  I'm sure the boys will be happy to see you there

To be continued...
Old man Johnson was especially appreciative of Bobbi's transformation, he was always so friendly and nice, complimenting Bobbi and telling hur how pretty she looked.  Bobbi had used to help him with raking leaves and doing yard work, but now that she was a gurl, old man Johnson wouldn't hear of hur doing any hard work.

Come sit with me on the porch Bobbi.  You look so pretty in your new outfit, did your mom get you that?  Why don't we have some lemonade?  Bobbi would tease him too, letting him see a little lace under her shirt or a little too much thigh.

One time Bobbi almost fell in her 5 inch slut shoes.  Luckily Mr J caught her in his strong arms before she fell.  Oh, you're light as a feather dear, he said.  Bobbi just blushed.  S/he told Mr J she'd make him dinner sometime for "being her big strong hero".

Oh that's OK sweetie, but I do have an offer for you.  I'm hosting a poker night at my place this Friday and I need a beer girl, if you want to make a little money and you're not busy.

Hmm, I'll have to check.  Bobbi pulled out hur phone to check quickly and saw she was free after 8.  OK Mr J your on.

OK, good.  I'm sure the boys will be happy to see you there

To be continued...
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