Sissy In The Middle

Mistress Pamela Was very happy with Sissy Erica and her performance but was getting bored.  She needed a new challenge.  One day when she was out for drinks with her girlfriends a man named Dan introduced himself and Mistress allowed herself to join him at another table for a drink.  They hit it off and quickly became an item.  Dan loved the sex.  It was the hottest he had experienced ever and he could never wait until the next time they were together.  

One day Mistress decided to test him and see if she could break his manhood and slowly turn Dan into Dana, her new sissy.  She had found her new challenge.  The next time they were together she wore some of her sexiest lingerie.  She did a little striptease for Dan and as she lost her clothes, so did he.  She told him to remove his panties.  He heard her call his underwear panties but let it slide.  He took them off.  She stood and caressed her body through her silken lingerie (what was left on her body) and began to moan in true lust.  Dan, please remove my panties for me, but use your lips only.  Dan's cock got even harder as she said this.  He got on his knees and did as she said, getting more excited as he removed the panties.

Mistress Pamela stared longingly into his eyes and said "Please Dan, please slide my hot silky panties up your sexy long legs and up over your huge, hard,  cock.  Do it!"  Without saying a word he slid the panties on and all the way up and into place.  He loved the feel of the material as it slid over his hard cock.  The sex they had that night was great!   Every time they got together after that, Dan would wear her panties.  Soon after that she started having Dan wear her panties home.  She would tell him to be sure he wore them next time they were together.  She would make him show her his panties as soon as he entered her house.  Sometimes he would have to show her as he stood on the front stoop before he could enter the house.

It wasn't long until she had  him slipping into a pair of silk stockings on a regular basis.  She started with thigh highs.  With each new item of lingerie Dan started wearing, the sex got hotter and he got easier to work with.  Eventually they would move from fucking to him eating her pussy, with promises that they would fuck again soon and it would be mind blowing.  Eventually she had Dan completely transformed and started his formal sissy training.  She had slowly be starting to call him Dana and sissy finally accepted it.

Eventually the day came when they were to get married.  They went to  Vegas and married in a chapel.  Dan wore the bridal lingerie she gave him, under his suit along with open toed shoes.  Mistress Pamela looked beautiful in her wedding gown.  Mistress Pamela had special plans for sealing the deal on their marriage and couldn't wait to get Dana back to the hotel room.

At the hotel they entered the room and there was Sissy Slut Slave Erica waiting patiently.  Erica was dressed in a pink version of the bridal lingerie that they were wearing.    Dana was told to stand still and wait patiently.  There was a sissy in the middle now and Dana didn't know what do to.  While she stood there Erica gave Mistress a long deep kiss and had her hands all over Mistress body.  This was according to plan.  Erica then did the same thing to Dana.  Next Erica helped Mistress out of her dress and removed her panties (with her lips).  Mistress moved to the bed and watched as Erica very slowly and sensually undressed Dana down to her lingerie.  Erica then started playing with Dana's clitty thru her sexy lingerie and watched as it grew hard.

Next Sissy Dana walk Sissy Erica to a chair across from the foot of the bed and sat her down.  Erica was stripped to her panties and bound to the chair.  Sissy Dana produced a chain with nipple clamps on each end and attached them to Erica's nipples.  Dana gave the chain a couple solid tugs for good measure.  What Dana didn't know was that Mistress had abused Erica's nipples all through the night last night.  Her nipples were already super sensitive and more nipple torture just drove sissy Erica over the top.  In order to keep Erica quiet, Dana produced an O-ring gag and inserted it in Erica's mouth and strapped it tight.  

All night long all sissy Erica could do was watch and listen as the couple had hot exciting sex all night.  There was everything from eating pussy to Dana being fucked by Mistress.   Eventually Mistress did to Dana what Dana had done to Erica.  By morning Dana who had been edged all night long was ready to burst.  Sissy Erica didn't have the ability to cum creamy.  Sissy could only produce pussy juices and would sometimes just leak juices with no control.  Erica sat in a pair of sexy panties just soaked in her juices.

Mistress was extremely pleased now that she had two sissies to play with whenever she wanted.  The possibilities of what they could do together were endless.

                                                               The End

Mark and the Birthday Sissy

Mark and Scarlet had been dating for a couple years.  Mark would soon be celebrating his 30th birthday and Scarlet wanted to make it special for him.  She will treat him to a hot surprise.  She has it all planned out.  Recently Scarlet hired a new sissy houseboy to take care her things for her.  This sissy's name is Erica.  Scarlet really liked Erica and saw lots of potential in her.  She hoped to keep this sissy on for a long time and decided to introduce Mark to Sissy Erica on his birthday night.   Scarlet would take Mark out for dinner at a ver nice hotel restaurant.  At just the right time she would excuse herself for a minute and hurry up to the hotel room to get ready.  Amber would text Mark a message that would tell him the room number and to heat to the room now.

That special night finally arrived and eventually Mark made it to the hotel room to be greeted by Sissy Erica dressed like the slut she is  Once in the room he looked around and spotted Scarlet.  Now his loins were really starting to heat up.  Scarlet was wearing a pink long gown that hid her lingerie underneath.  She also wore white elbow length gloves and an evil smile on her beautiful face.  Underneath the gown she was dressed in the sexiest lavender colored lingerie and sheer black stockings, and was looking extremely hot.  He could tell just by the look in her eyes that she was the one in control tonight, and he was okay with that.  Sissy Erica was wearing pink shimmering stockings and a matching garter, Sexy sheer lacy bikini panties and a matching pink bra that hooked in the front and had holes in the cups for her nipples to stick out.  To the great pleasure of Mistress Scarlet, Erica's nipples had been played with so much that they were so read pointy and puffy and they protruded greatly from her bra.  This excited Mistress Scarlet.  Sissy also had on leather wrist and ankle cuffs as well as thigh cuffs.  There was a short spreader bar attached between her ankles to keep her from going anywhere.  Her left hand was hooked to the left thigh cuff keeping it at her side.  Her right hand was free for now.

Scarlet walked over to Mark and kissed him long hard and deep.  As she did, she ripped his shirt off his body, button popping everywhere.  Her hands slowly caressed his huge chest eventually making their way to his wonderfully firm ass.  She moaned as she fondled his prize ass.  Next she moved to his belt and begin removing his pants.  She told him she wanted that huge tool he was hiding from her.  Marks started to remove the long gown from Scarlet and was truly surprised when he saw what she wore underneath.  His cock grew 5 times its normal size when her saw the lingerie she was wearing. 

Sissy was on her knees crawling to the couple when she was told to remove his pants and suck his cock so it would be ready to fuck Mistress long and hard.  Sissy licked and sucked and when it was time she lay on the bed next to Mistress while Mark slid his huge ten inch cock in Scarlet's pussy.  When he was about to cum Mark pulled out of Scarlet and shot an amazing load of thick creamy cum all over Erica's face and chest.  Erica was completely covered in cream.  Scarlet told Mark she wanted to squirt for him tonight, which he loved.  Sissy was told to get on her knees at the foot of the bed.  Mark worked Scarlet in that special spot and soon she started squirting her juices all over sissy's face and in her mouth..  Sissy started moaning during the squirting because it excited her that much.   Mark looked at sissy and decided to see what her pussy could do with his manhood.  Sissy got on her hands and knees and stuck her ass up in the air.  After a little lube Mark started slowly sliding his long hard thick hot rood  in the sissy's  pussy.  The evening continued on like this and by the time all were asleep Erica had been used more than she could have dream in one night.

 

 

Barbie Fashion Show

It was early morning and all Mistress’s women were gathered for breakfast.  Sissy was late for the meal and would have to be punished.  Once everyone was finished with breakfast, Mistress told Sissy to return to her room and prepare for the day.  Be back here in ten minutes slut!, said Mistress.  Sissy found a note on her bed and her clothes laid out for her.  Sissy dressed in a pair of pink nylon bikini panties, a matching bra and pink sheer tights and her black & white french maid dress.  Sissy did her makeup and put on her wig just as the note said to do.  Her makeup was made to look more slutty than usual at Mistress Scarlet’s command.

Sissy returned a minute late to her Mistress with the excuse that her makeup took longer than usual.  Mistress does not like excuses and you know that slut, Mistress said. You will clean the breakfast dishes from the table to the kitchen one item at a time before you do anything with them in the kitchen.   You will wear these headphones and listen a recording I have selected while you work.  Understand Sissy?, Yes Mistress, Thank You Mistress, sissy said.  The recording was a very descriptive session with a Mistress and her slave.  It told a story that included all the things that turned on Sissy Erica: Bondage, spanking, cock sucking, licking up cum, licking Mistresses shoes clean while everyone watched and having creamy man cum and womens pussy juices shot all over Sissy’s body.

After  about fifteen minutes Mistress reminded Sissy to keep her panties and stockings dry today or else.  It was too late and Mistress knew it.  It was all part of her plan. After Sissy was done with her assignment Mistress told her to sit as Mistress queued up a hot lesbian video that would get Sissy all excited.  The video lasted 30 minutes.  Sissy was informed there was a fashion show today and that Sissy would either be the model or the entertainment.  Mistress had Ashley wheel the Sissy in her chair to the room where the fashion show would be held.  Sissy wasn’t allowed to get up until Mistress said she could.

Sissy in her chair arrived in a room filled with couples (Mistresses and their male slaves).  Her chair was wheeled up onto a solid glass platform so everyone could look up and see up her dress.

Mistress Scarlet announced that Erica her Sissy had misbehaved this morning so she had to be punished.  Scarlet told how Erica was missing the part that made her cum creamy like a man.  Instead when Sissy cums she cums like a woman all nice and juicy.  It embarrasses Sissy Fuckslut Erica when I tell people about this, Said Mistress.  A camera was set up so that everyone could see her clitty close up on a big screen when Sissy stood up out of the chair.  Mistress had been priming Sissy all morning so when she stood she was sure to soak herself and leave a huge puddle on the glass floor.

Stand up Sissy and remain standing.  Pull up your dress as you stand and keep it up.Sissy fuckslut cumdumpster Erica did as she was told even though she didn’t want to  She knew what would happen when she stood.  Sissy heard everyone react to all the juices that were coming from her clitty.  She soaked her pink panties and quickly started soaking her tights.  Mistress announced that Sissy liked to move her clitty around to soak the entire front of her panties.  Move it around Sissy.  Really soak those pretty panties.  As Sissy did this Mistress placed a collar on Erica and pronounced her as not only Mistress’s Sissy but her Sissy Slave.  After a few minutes of spilling her juices, the floor was covered with her wetness.  Clitty juices were running all the way down to Sissy’s ankles and the wetness shown easily on the pink color of the tights.  Sissy was commanded to drop to her knees and start licking up those juices.  After Sissy finished licking her juices , a woman from the crowd came up to her, placed her foot in front of Sissy and told her to lick her shoes clean and not to miss a single spot.

As Sissy slave finished licking the shoes more women came to her with similar requests.  Mistress Scarlet handed the leash connected to Sissy’s collar, to another Mistress from the room.  She told her to take Sissy for a walk if she would like.  Sissy was walked all around the room.  Some of the women needed Sissy to rub her face all over their pussies to wipe up the juices that had started to flow from watching her on stage.  The male slaves were either told to cum on sissy’s face or have Sissy suck them off and swallow every drop.

Later on Sissy was used as the model and made to beg to be dressed in certain costumes.  Sometimes she was forced to tell the room how much she loved to be forced to suck cock until it would shoot all over her little face.

After all the dress up was over, Sissy was tied to a frame on the glass platform and made to beg for a bowl of hot cum from all the males slaves that were present.  Beg for it Sissy.    Tell everyone here how much you want to swallow this bowl of creamy man cum.  Eventually Sissy begged enough to please everyone and was given a bowl of cum to drink.  Swallow every drop Sissy, every drop.

Sissitricity

Sissy Sensory Overload

It was a beautiful day filled with sunshine and warm tmperatures.  Mistress had called early this morning at 5 am, with specific instructions for me.  I was to get the MP3 player and headphones out and listen to "Feminization Brainwashing" and then listen to "Silky Panties 2".  While listening to Silky Panties 2, I was to be wearing my new fat blue butt plug and nipple enhancers.  Mistress had plans for the day and wanted me ready.

As soon as the MP3's were finished I was to bath, do my makeup and slip into the sexiest bra and panty set I owned and a full nylon black body stocking.  Next I was to dress in a short skirt and sheer top.  Mistress would be there to pick me up at 7:30 (just when all the neighbors are walking out to their cars to leave for work.  It seems like everyone on the block always parked on the street.  At 7:30 sharp Mistress pulled up out front and honked so that everyone turned to see who was there.  While she had their attention I walked to the car dressed like a slut.  Everyone knew it was me and I kept looking around to see who was watching.  Mistress had commanded me to stop at the sidewalk where people could see everything, Lick my lips seductively and blow them kisses.  following the kisses I was to call out as loud as I could "Please, I Beg you all, please com over tonight at 6 pm and use me how ever you like.  I am a sissy slut".  

By the time I reached the car and tried to get in I was so so humiliated.  Mistress had locked the door and made me stand there even longer before letting me in her car. We drove to a local restaurant for breakfast and when we went in Mistress had us seated at a table in the very front of the room.  After breakfast we got in the car and as we drove, Mistress told me I would be starting my day as a sissy maid at a friend's home.  As soon as we were in the front door I noticed a maids uniform laid out in the living room.  I was told to stand right there in the living room and change out of my skirt and top and into the maids dress.  I did as I was told without a word.  "Sissy, you are to respond to anyone you see in this place as your mistress or master.  You will do just as you are told.  The same rules apply as if it was me telling you what to do.  Do you understand?" said Mistress Carolyn.  "Yes Mistress, I understand and will obey Mistress", I said.

 

My first chore was to cleanup the breakfast mess.  While I was in the kitchen two beautiful blonde women entered.  One wore only a pair of pink bikini panties and the other black sheer stockings and garter.  As I looked at the panty lines of the first woman  I remembered the conditioning I had received when I listened to my daily audio file.  My mouth started watering and I knew she was wearing panties because I was also wearing panties.  All of a sudden she told me to get on my knees and lick her pussy through her panties.  The next thing I knew i was soaking her panties with my tongue because my mouth just kept watering.  As I licked, the other woman moved to my direct line of sight and all I could see was her nylon covered legs.  She then asked "well Sissy, do you like what you see?".  I answered "Yes, I just can't take my eyes off your beautiful legs Mistress".  She said "Excellent, just keep licking my sister until I tell you to stop".  "Yes Mistress".

Soon the house began to fill with nothing but beautiful women, all wearing sheer nylons of black, red or pink.  The most beautiful of the crowd entered the kitchen and commanded me to get on my knees.  ID did and then had my hands tied to a spreader bar.  Next the same thing was done with my feet and another spreader bar.  I wasn't going anywhere.  I was told to open wide and catch whatever came from the woman's pussy.  The next thing I knew she was squirting juices at my face and anything I messed went to the floor.  I would be cleaning the floor later, this I knew from my previous training.

All of this attention was electric to me.  My senses tingled with excitement at being used in this way by such beautiful women. Eventually I was led to the living room where there were women and men.  One person in particular caught my attention.  She saw me looking her way and began to come towards me.  She had freckles, long curly red hair, beautiful blue eyes accented by perfectly shaped eye brows. As I later learned, her name was Scarlet.  She had long lean legs that seemed to go on forever.  They were legs I couldn't take my eyes off of.  She started talking about my mouth and how she thought I could probably suck some serious cock with a little of her training.  As she talked she just kept an eye on my clitty and commented on how the conversation seemed to be making it grow awfully hard (and long =, As long as any sissy clitty can get).

Mistress Scarlet commanded me to start begging to be able to suck some long, hard, hot, manly cock.  She must have loved hearing me beg because she made me keep it until She knew I was totally turned on by my own begging.  All of a sudden I felt someone sliding a huge butt plug in my sissy pussy and it was there to stay for a while.

As I begged women would come up and rub my body with their nylon covered legs which turned me on even more.  The electricity in the room was growing every minute.

Dedicated to My Mistress

Let your inner sissy out

Erin and Sloane had been friends all throughout college.  They have been sharing a house for a few years now.    He was 25 and she was 27.   Sloane knew Erin would do anything she would ask of him.  Whenever Sloane had a night when she couldn't sleep she would slide across the hall and slip into bed with Erin.  One Friday night it was late and she couldn't sleep.  When she entered Erin's room she saw him slip a magazine under the covers. She smiled because she loved catching him in the middle of his business.  Sloane was wearing a pink teddy and black stockings held up by garters.

She slipped in under the covers with him and asked what he was up to and smiled.  He replied he was just doing a little reading.  As he spoke he felt her small soft feminine hand on his long hard hot member.  She began to slowly stroke him.  You know better than to lie to me, Erin.   How was the porn you were looking at?  His cheeks went pink embarrassed hat he had been caught.  In her other hand she had an Ipad.  She brought up the internet and found some interesting sissy porn.  She noticed that when they found images of men being forced to suck a tranny's cock he got excited.  Eventually Sloane positioned herself so she could suck off  the hard cock in front of her.  It wasn't very long but it was hot and hard and ready to blow.  She looked up at him and made Erin agree that if she satisfied him tonight he would have to do whatever she wanted for the next week.  In return Erin  you must do exactly as I say from now on.  You must be completely obedient.  That means when I tell you to do something, do it, no questions asked.  Undersatnad?  Erin said yes that he would do just as she says with no questions or she could punish him.  Sloane liked the punishment clause. It had been a long time since Erin had been with a woman so he agreed.  Minutes later he felt the most explosive orgasm rising from his loins as Sloane worked her magic on his cock although it was the size of a large clitty.

All of a sudden he shot his load, a load Sloane wasn't truly ready for.   She had been expecting a load of hot thick cream but when he came it was hot and juicy like her girlfriend's pussy juices when she squirts into Sloane's hot little mouth.  As he came she held it all in her hot mouth.  Afterwards Sloane went to kiss Erin.  She kissed him deep and long letting his juices run into his mouth from hers.  As the juices entered his mouth he let out a long low moan of pleasure.  This got Sloane's attention.     I want you to start by putting on the teddy, stockings and garter I have on.  She undressed and helped him into the lingerie.  She stood in front of him completely naked caressing her own body.  She could see this was having an effect on Erin.  He looked hot and she could see his  inner sissy starting to come out and his cock starting to rise again.

Sloane knew that Erin occasionally got in her panty drawer and borrowed some of her things.  She had plans to bring out the true sissy in him.  She would become his Mistress and have complete control of him 24 /7.  She had just completed step one.  Saturday morning she awoke first and crept back to her room to slip into a pastel pink baby doll and white stockings and garter.  She then wrote a note telling Erin NOT to go to the bathroom but to join her in the kitchen and to stay dressed in your lingerie and left it on the bed next to him. 

When Erin awoke he saw the note and regretfully did as it said, even though he did have to pee big time.   Sloane was going to teach him his first lesson on obedience and she was going to enjoy it!  She handed Erin a pair of pair of panties that matched the teddy and told him to slip them on.  He did and then watched as she took his cock and positioned it sideways.  From now on you will be known as Sissy Erica.  Do you understand?  Erica responded "Yes Ma'am" .  Sloane stood and turned on the water letting it fill the sink.  Just the sound of the water alone gave Erica the urge to go.  Sloane warned Erica not to go and if you make a mess in the kitchen you will clean it up.  She turned off the water and turned to face the sissy.  She place her palm on sissy's cock and slowly rubbed back & forth causing more urgency.  Pushed Erica against the counter , grabbed his wrists and cuffed him to some u-bolts she had installed.  Sissy stood there helpless. and all of a sudden felt the urge to go.  Ask permission and you can go take care of business but you are not allowed to play with yourself.  

Erica was very suggestible and knew Sloane would be mad at him for not obeying her.  He asked permission and she undid the cuffs and let sissy go.  Be sure to come right back.  Both Sloane & Erica stayed in their sexy lingerie until noon. During the morning Sloane was able to place Erica in a hypnotic trance.  She implanted many suggestions that would make Erica want to behave like the sissy she was.  She would also know that Sloane was her Mistress and that sissy should respond to any woman as a mistress and do what they say.  Sloane decided to change her name and go by the name Mistress Sloane.

The first test was about to take place.  Sloane had gone to her room and come out dressed in a sexy short dress and black tights.  When sissy saw this she thought she should dress ass well.  Mistress Sloane stopped her.  Sissy Erica  was to remain in her lingerie.  Company was coming and Erica was expected to serve drinks and take care of their guests needs.   The doorbell rang and Erica was told to answer it and greet our guests.  When Erica opened the door he saw the VP of the company he worked for.  She stood there with a woman wearing a schoolgirl outfit. Rachel introduced her friend as Stephanie and they entered the house.  Rachel recognized Erica and greeted her with a smile and blew her a kiss.  Erica was feeling completely humiliated by now.  Sloane called out "sissy, in your place" and Erica dropped to her knees in front of Sloane and waited for her orders.  This impressed Rachel very much.  Sloane told Sissy Erica to kneel in front of Stephanie and bury her head in Stephanie's sweet spot.  Erica did as she was told and was quickly introduced to a big fat long hard cock that was begging to be released from the confines if the panties Stephanie wore.

Sissy Erica was told to beg to suck that huge cock and let it cum all over her face.  Sissy begged and begged and begged.  Finally Mistress Sloane gave her permission.  Sissy Erica dove in and licked and sucked like this was the last cock she would ever see.  Stephanie (Steven) came all over the sissy's face.  Misss Rachel wanted to see Stephanie suck Erica's little clitty.  She told Stephanie what to do.  "Just remember Steffy, the help is NOT allowed to cum.  If she does you will be severely punished.  Stephanie shook her head in understanding and said "Yes Mistress, as you order".  Stephanie stood Erica in front of the fireplace and tied her in place with extra stockings.  Sissy Erica was securely bound in a spread eagle stance.  Stephanie pulled Erica's panties down to her knees and began working on the little sissy clitty.  The women watched with delight and the clitty got excited and grew hard and as long as a sissy clitty can get.  When the time was right, Stephanie backed away and returned to her chair quietly and began rubbing her own hard cock.

The two women started kissing each other and caressing each other.  The wanted each other and this excited Erica even more.  The women looked over as they heard Erica moan.  Sissy Erica's clitty juices were starting to flow.  As they stared they saw a stain of wetness growing in the panties.  Erica was so excited she could't control it.  This was a first and Erica had no control over what was happening.  As the panties filled with wetness the rest began to spill to the marble floor in front of the fireplace.  Sissy was worried now.  She had no idea what Mistress Sloane would do.

Mistress Sloane walked over, adjusted Erica's bindings and told her to get to the floor and startt licking and sucking the juices from the floor.  There were to be no wet spots left when she was done.


This was just the beginning of the week for Sissy Erica and her playmate Steffy.

The End