Taking That Cherry

"Alright Sissy, now that you understand that you'll be in panties from now on it's time for you to understand where you fit in in our household! I. of course, am in charge! You will obey me without question! My maid Fiona comes next, you should know that Fiona was once my husband too but she makes a much better maid than a man! So Fiona is your superior and who knows, if you please us maybe some day you will be a personal maid for me too!!!!
"Me....a maid...I don't understand..."
"Of course you don't Sissy! We haven't even begun to train you yet...why neither Fiona or i have penetrated you yet! I'll be taking that cherry tonight and after that Fiona can have you when she wishes, Won't you like that Fiona?"
"Oh yes Ma'am, I can hardly wait!"

Which One

"Hello Sissies! Your wives have been generous enough to lend you to me for the evening to serve at my party! Put your things in the guest bedroom at the top of the stairs . I've laid out two outfits! One of you will be doing general Sissy Maid duties while the other will be used as a toy for my guests to amuse themselves! Which one is which I leave completely up to you!"
The two sissies stood quietly! Not sure what to say or do!
""Get going right now! Kaaren! Leeanne! I expect you back down here in 15 minutes for my inspection!"
Both sissies bolted for the stairs! Each one certain of the role they wished to play! It was going to be an interesting evening!!!

Saturday Matinee - The Unexpected

The crew of Deep Explorer 9 had been carefully screened and prepped for the years long mission! There had been concerns about the possibility of conflicts with a mixed sex crew and so a crew of three men had been chosen!
No one suspected the ingenuity of the crew! Captain John Atlas and Lieutenant Tony Machovero had planned this almost from the start! Their crew mate Corporal Leslie Passivito had been perfect! Not too big, not too assertive, eager to please!
They had planned the genetic transformation and had made certain the equipment was on board when they lifted off!!!
What they hadn't expected was the effect the genetic manipulation had on the Corporals mind! They felt his mind control seize them as soon as they woke him!
He really didn't mind being a woman he had two boy toys to play with and he enjoyed himself making them do all the unspeakable things of his fantasies!!!!

Fluffing

Sometimes his cock is so nice and tasty looking that she wants it all to herself, and really, just look at it....who can blame her! But just because I'm not going to get him hard and wet for her, there's no reason I shouldn't get her nice and wet for him! I enjoy it, she enjoys it and he seems to be enjoying himself too!!!

I'm Sorry Sweetie

"I'm sorry Sweetie, but I just have to make sure! A lot of wives are bringing their sissies to the party and maybe Leeanne will be there and I don't want you to be tempted!!!

Something For You

"I don't think he liked me very much!"
"Oh no Sissy he liked you very much!"
"Really? I mean he called me a little sissy bitch!"
"But Sweetheart...you are a little sissy bitch..."
"Well...I guess so..."
"Honestly Sissy! He even left a gift for me to give you, he really wanted you to have it!"
"Oh I love gifts! I can't wait!"
"That's good Sissy cause here it comes!!!! Make sure you don't miss a drop!!!"

This Is How

This is how she found me when she got home and she was delighted! What followed was several hours of wonderful pleasure for her and....pleasurable frustration for me! I was grateful that she never thought to ask how I managed to lock both cuffs! I'm entitled to some secrets after all!!!!

But Why?

"But Gary, I don't understand! You look adorable but I never thought you'd wear dresses!"
"Are you kidding! Have you seen the death rate for Red Shirt males! At least as a red dress I stand a chance of getting through this trip alive!!! As Mr. Spock says, it's the logical thing to do!!! And it feels really really nice too!"
"The Captain and Spock won't be back for a while...."
"I'd love to get under your dress baby!"
"I'd love to get under yours too!"
"Let's boldly go!"

Learning Fast - Sissy Training

This summary is not available. Please click here to view the post.

You Just Don't Understand

"But Daddy..."
"Don't you "But Daddy" me young lady I don't want you spending time with him...he's a hoodlum!"
"You just don't understand girls Daddy!"
"You just go to your room and think over the choices you've made!!!"
"Alright but you'll see..."
She went to her room and pulled the Book of Dark Magic from it's hiding place! Finding the spell she wanted she waited for the opportune time...

One moment he was having a beer in the den and suddenly he was here!!! Oh my god!!!! What the hell is happening!!!!
Before he could say or do anything her boyfriend grabbed her head and began roughly fucking her mouth!!! And somewhere in this strange body, his daughters body, he felt the desire, he felt the heat begin to grow!!!

For Her

For her it's a whim. a momentary desire!
For Sissy it's a duty, it's fulfilling his Mistress's wish, it's the most important thing in the world at that moment!!!!

So Many

I hear it all the time....so many wives won't do anal...

But I'm so glad she loves it! I've never had her ass like this but I do love to watch...

 

...and it does leave her sweet, sweey pussy available for my tongue....

...and it leaves me in the best spot possible to clean them both up! A cum covered cock and a cum filled ass!!!! Sissy Heaven!!!!!

Sweetest

As she laid there in her pretty panties it was obvious! She had the sweetest little pussy you ever saw!!!

Monday ManCandy

Some are born loving ManCandy and some learn to love ManCandy! ManCandy plays a vital  part of Sissy Training and although most claimed they didn't like it at first they learned to appreciate it very quickly! Their partners were more than happy to make sure they got it as often as possible!
ManCandy! If you don't love it at first don't worry you'll learn!!!!

Watch Me Kaaren

"Watch me suck his cock Kaaren! Watch me wrap my lips around his big throbbing cock! This is what you wanted, this is what we wanted...."
As if she had to tell me! His cock in her mouth had all my attention!!!! I couldn't wait to taste him on her lips!!!!

I Love This Dress

Back in high school, the girls in my dance class used to leave tutu's in my locker to embarrass me and I had to pretend that I didn't want to slip them on right then and there!!! This dress reminds me of those tutu's! How I'd love to wear this and dance for all to see, while my partner slips a hand up my thigh to lift me for the finale!!! Oh my....it would be wonderful!!!!

Saturday Matinee - The Gate

Troy Carter and his assistant. Tommy Dillon stood staring at the device! It was obviously built for a person to step through judging by the footpads and the dimensions!
After tossing a few rocks through and watching them disappear only to reappear three minutes later they stepped forward to examine it more closely!
"I'm going to go through it Tommy!"
"No Troy, we don't know anything about it!"
"I have to try it! Who knows....it might lead to anywhere!"
"No Troy!" screamed Tommy as the scientist stepped into it and with a crackle of electricity and a whiff of ozone he vanished!!!
Tommy started the stopwatch and waited the three minutes and despaired when Troy did not re-appear!
He waited for roughly an hour before he started to pack up to leave the site where they had found the device! As he turned to go he heard it come to life and a strangely familiar woman came out of the electrical glare!
"I'm back!!! Oh thank god I'm back!!! Oh my god Tommy...is that you? How can you still be here after all these months?"
Suddenly Tommy realized why the woman was so familiar!
"Troy? Is that you?!?!?!? How...Why....."
"How long has it been Tommy? How long since I passed through?"
"Just a few minutes, what happened how did this..."
"I've been gone for 10 months Tommy! Time is different there! They have no women of their own Tommy! None of their own!!! They've set these traps all around the world! If they catch a woman they breed them, but if they catch a man they change them like they changed me and use them for their sick pleasures! Warn the world Tommy Warn the.....Oh No!!!! Oh please god NO!!!!!"
Tommy stood dumbfounded as large green hands reached through and pulled Troy back!!!! His screams mixed with the electrical sparks and in a whiff of ozone he was gone!!!!

Let's Be Clear

"Let's be clear Dear! If my daughter wants her husband to wear panties and suck her boyfriends cocks then that is exactly what you'll do! Do you understand me Sissy?"
"Ow....Ow.....Yes Ma'am....Ow"
"Very good then, just another twenty five or so and we'll head to the bedroom and find you something pretty to wear!"

Coming

"Leeanne! Kaaren! We're ready to go shopping!"
"What could be keeping them? Your Kaaren is back in her cage isn't she?"
"Yes! What about your Leeanne?"
"Locked up tight!! I laid out their pretty outfits, honestly how long does it take to get dressed?"
"Let's go Sissy Girls! What's taking so long??!?!?"

Eventually - Sissy Training

As Sissy's training progresses the only reason you'll have to bind his hands is to keep him away from the cocks that are there just for you! But for now Sissy needs to be in bondage so he will recognize that he no longer has any power, that you are in complete control!!!

Signs

Despite the signs forbidding fucking the company Sissy the executives had come to consider it one of the bonuses that came with the job!!! The female employees were used to waiting to use the limited bathroom facilities and frequently had to queue up, but they were surprised to see the long line of men waiting for the washroom!

Small Town Girls - Kiss Like A Girl

It's hard to keep secrets in a small town and Johnny and Tommy, or Joanie and Tammy as they preferred to be called had always been so careful but they had been caught by Tommy's Cousin Jen.
Jen loved teaching the boys to be girls! The afternoon she spent teaching them to kiss like girls was the most fun she'd had in a long time! They were adorable and so eager to learn!!!

Sometimes

Sometimes their ideas about fluffing are a little different from mine! But I like the variety!!!! And really, all I had to do was keep my tongue wet and that wasn't so hard...my mouth was watering from the moment he took his pants off!!!!

So Far

So far no one had really noticed, but Sissy was getting worried. How much longer would she be? Why had she taken my jacket when she already had her own? Why did I have to come to the Mall at all when all she wants me to do is wait here???
Finally Sissy felt the need to text her wife!
"How much longer?"
After a moment Sissy's phone rang!
"What are you asking me about Sissy?"
"Please Ma'am, how much longer will you be....people are starting to notice me here!"
"Oh my goodness Sissy I forgot all about you! I'm just about to pull into our driveway!"
"Oh no!!!! How will I get home???"
"Well Sissy I think if you'll look in the little pocket on your apron you'll find bus fare! I'll be waiting for you at the bus stop!"
"Oh my god I can't do that!!! How can you ne so cruel?"
"Cruel!!!! I said I'd meet you at the bus stop didn't I???? But if you think I'm cruel then you can just walk home from the bus stop!!!! It's only a few blocks!!!"
"Wait I didn't mean to....hello....hello....hello..."

I Warned You

"I warned you if I caught you in your sisters things again I'd punish you! So you just stay here in her room and don't even think of taking those clothes off! Imagine! A boy wearing his sisters bra and panties!!!"
"You want to dress like a girl then you stay in here and you can play with her dolls like a little girl!"
"When your sister get's home we'll let her decide whether or not you get a spanking too!!!"
When his mother shut the door  he was so relieved! If he hadn't had that doll she might have seen how excited he was getting; more so with every word!!! He hoped his sister decided on a spanking! His bottom was tingling in anticipation!!!

Just Don't Understand

When a man comes home and finds his wife with another man...or woman...at least it's something he can understand! But when a man catches his sweet little wife with a Panda....well that's something different!!!!
Those goddamned Pandas! Problems breeding? I don't care if they never breed again but stay the hell away from my wife!!!!

Sissy School - A Weekend Visit

After a weekend visit home Sissy's wife made sure she was properly dressed to return to Sissy School! Although Sissy had performed well and had satisfied his wife and her lover in many ways, his wife said a lot  more training was in order!!!

Monday ManCandy

There really is no argument! Oreos are delicious and  Double-Stuffed Oreos are even better! After all how can you go wrong when you promise a mouthful of delicious tasty cream!
But in taste tests we've found that, when the two are compared side by side, ManCandy wins every time!!!
ManCandy! You don't have to twist it open to get to the cream! In fact we'd prefer it if you didn't!!!

Have A Seat

"Oh hi Tom come on in and have a seat, I'm so glad you could stop by!"
"Um....maybe I should wait outside...."
"Oh nonsense, I'll be done here in a couple of minutes and I'm sure Sissy wants you to stay! Don't you Sissy?"
"Yes Ma'am! If you say so!"
"That's just the right answer Sissy!"

He Laughed At First

He laughed at first when he saw me enter the bedroom! He called me a sissy faggot and who could argue....pink maids uniform and makeup didn't really hide the fact that I was a male....not much of one but still....biologically a male!
She shushed him and urged me on and soon after I took him into my mouth he stopped laughing! Instead of faggot, he called me "Baby", instead of abuse he stroked my hair! My wife and I had opened his eyes to new possibilities!
Oh, and he was delicious!!!!

Saturday Matinee - Love Slaves

Come see the true story of Doctor Arthur Perry! Captured and abused by the Amazons!
The Amazons, a tribe of wild women who live deep in the jungle! Each one is as beautiful a she is deadly!
See the despair of Doctor Perry....the only man left alive after the Amazons took his party prisoner!!"
Imagine his horror when he realized that he was the only male in their village!
Imagine the unspeakable acts he was forced to perform!
Imagine his relief when rescue finally came!!!
See his re-capture the following year and his harrowing escape after serving his Amazon mistresses for months!
See him re-captured again when he went back for unknown reasons!!!!
Imagine where he is now after the last rescue party called off their search!!!
They say that at night in the jungle you can still hear him screaming!!!!

Morning

I cleared my throat as I brought her coffee, it was time for her to get up!
"Mmmm good morning Sissy! Isn't it a beautiful day?"
"Yes Ma'am", I said as I handed her the cup, "I'll have your breakfast ready in 10 minutes, if that's alright with you?"
"That would be fine Sissy! I'm in such a good mood! I think this will be a wonderful day!"
I would be in a pretty good mood too if I had cum as many times as she did last night!

A Little Romance

They first met at the bus stop. He was on his way to work and she was on her way to school.
After some time they exchanged smiles and then they were saying good morning!
Introductions soon followed and then conversations! They had so many things in common that they shared a laugh, they might have been brother and sister!!!
Finally, inevitably he asked her to dinner and she accepted! They seemed like they were made for each other!
After several dates she invited him in! They kissed passionately as he pulled at her clothes! When he opened her belt and began to open her shorts she stopped him!
"There's something I should tell you before we go any further!!!"
His face was flushed and he was breathing heavy with desire!
"Can you tell me while I'm sucking your cock!!! Please, I've waited so long!!!"
It turns out they really were made for each other!!!!

Trouble

He liked her leather pants, even with the frilly panties on they held him so tightly that you couldn't see even the slightest bulge! The pink bra also fit him so well that it was as if she'd bought it for him!
He danced to the music and it was so loud that he didn't hear her when she quietly entered the room and began video recording!
It all explained so much...the clothes in the laundry that she knew she hadn't worn....the bra's that were stretched....the panties with little stains....
His life was about to change as she reached to tap him on the shoulder.....

I Know

I know I'm small but this really seems unnecessary! She knows I thrive on humiliation but this just seems like too much! Well maybe not.....especially if she invited all her friends to.....well....you know.....it could be  a lot of fun!!!

The Perfect Arrangement

it is really the perfect arrangement...don't you think so Sissy?

Fifty strokes for me....

Fifty strokes for you....next week we move up to Seventy-five!!!

Where Are You

"Sometimes Sissy, I look at you and you seem like you're not here at all, it's like you're a million miles away! What are you thinking about Sweet Girl?"
"Oh nothing in particular...just daydreaming...."
"I'll bet it's about sucking cocks! Isn't it?"
We both laughed as I blushed bright red! She knows me so well!

Frozen

As the cum hardened into ice, "Princess" Elsa shrugged her shoulders!
"What do you expect? I kept asking you to let it go!!!"

About as I expected

When her friends dropped by to see how she had sissified and chastised her husband their reaction was pretty much what I expected!!! But, although I can't prove it, I'll bet their panties were wet when they left!!!!!

Remember

Remember that first time you put on a skirt? Remember how it made you feel??? After that I wanted to wear skirts all the time....I still do!!!

The Clinic

The Doctors at the clinic were very thorough! They took their time and they waited until their colleagues had all had time to run their own tests! Then they would repeat the tests again to verify their initial results! Only after they were satisfied would they all sign off on the medical form that my wife kept on file!
I made my usual appointment for my re-check in two weeks and went home! I had no idea that prostate exams were so involved but my wife assured me it was for my own good!!!

Monday ManCandy

I'm sorry but a proper lady just doesn't let strangers put their penis in her mouth! My dear it just isn't done! Please leave it in my hand! I thank you, but we must mind our manners!!
ManCandy! It's what the elite love to eat!!!

Refused

He refused to go out without that damned fedora on his head! He clung to this last reminder of the man he used to be and for now his wife allowed it! Soon, she thought to herself, soon it would be gone and his transformation would be complete!!!

Mom Had Been Right

Her Mom had been right! Using the paddle on him was exhilarating! She laughed each time he promised to be good! He promised to do anything she asked! A few more swats with the paddle and then it was into the pink panties and chastity! He'd get used to it after a while!!!! In the meantime she swatted him again and his cries made her laugh again!!!!
Life was going to be full of laughter, at least for her!

Saturday Matinee - On The Street

"Shut up!!! I don't want to hear it!!! I can't believe you!!! I went to prison for you! I took the rap...I never gave you up!!!!"
"Rocko, wait...please...I can explain..."
"Just shut up! Five years and you never even visited me...not once! No calls. no letters! What was I supposed to think!!!"
"Rocko, please...."
"Shut up damn you! After all that I get out and come home and I find you out on the street....with him!!! With his hands all over you!!!! Dressed like that!!!! I bet you put that dress on for him didn't you???"
"Rocko it's not...."
"Shut up! I couldn't take it...I saw him holding you....I saw him caressing you...I saw him kissing you...I just had to shoot him..."
"Rocko...please...the police....you'll never get away!!! Please...."
"Shut up! I did it and I think any man would do the same as I did! After all you're my brother and no matter what it's my job to protect you!!!!"

I Think It's Time Sissy

"I know you're been confused by your feelings since I released you Sissy! I've watched you experience meaningless orgasms that only left you more unsatisfied! Sweetie I'm going to let you cum and then I'm going to get the cage again! I think you understand now that you truly get pleasure from giving pleasure! I think you need the cage and I think you love it too, even if you won't admit it to yourself!"
I felt tears streaming down my cheeks! I didn't want her to be right...I wanted to be free,,,didn't I?
"But I don't want to wait another year!!!! It was so long and so hard....um...difficult I mean...."
"No sweet Sissy, you have my word that it will not be a year! You've proved that to me already! I would never ask that of you again!"

Sissy School - Late

"What is the meaning of this Sissy Kaaren? Do you realize it's hours past curfew?"
"Yes Headmaster...."
"And just look at you! Coming in through the service door barely dressed! This is disgraceful behavior!"
"Yes Headmaster...."
"I'll wager you were over at St Dunstans School for Boys again, weren't you? Don't you lie to me it will only make it worse for you!"
"Yes Headmaster...."
"Kaaren I've spanked you until my arms ached and still you behave like such a sissy slut! What am I going to do with you?"
"Hmmm...I don't know what you had in mind but I've got a few ideas that I'll bet you never thought of..."
"Go close and lock the door Sissy! We have to have a long,,,,talk!"