Putting your Sissy to Work

When you grow tire of having your Sissy around all the time -- or just want some extra money -- don't be afraid to put your Sissy to work!

I've had good success finding jobs for many of my Sissies as secretaries and receptionists.  But not all Sissies have the skills for this type of work.  

But the recent explosion of legalized gambling all across the country has created lots of new casinos -- and lots of new cocktail waitress jobs!

Sissy Sandi had been a stay-at-home Sissy, serving his Master and Mistress for almost five years.  Sissy Sandi had been kept very busy preparing meals, cleaning the house, washing and ironing clothes, bathing and massaging his Master and Mistress -- and performing nearly continuous oral sex on both of them.

But when Master decided that he wanted to go into semi-retirement, he agreed with Mistress that it was time for Sissy Sandi to contribute more than his talented lips and tongue to the well-being of their "family". Sissy Sandi would have to earn a paycheck.

With my help they arranged for Sissy Sandi to get a cocktail waitress job at the new casino that opened 20 minutes from their home. But first, following my advice, they had Sissy Sandi's boobs plumped up. Don't those huge tits look so sexy spilling out of his cute little outfit?

Sissy Sandi's new job has been a huge success! He now works a ten hour shift -- from 5:00 PM until 3:00 AM -- seven nights a week, 365 days a year. And the tips he earns are amazing!

Master and Mistress are so happy with the new arrangement,  But of course, it isn't so much fun for poor Sissy Sandi.  He doesn't look too happy in this picture, does he?   He is so embarrassed parading around in such a revealing and sexy costume.  He wears a tightly laced and uncomfortable corset to give him that delightful wasp-waisted look.  His pathetic little cockette is cruelly constrained to ensure not even a hint of an unsightly bulge.  His feet ache after spending so many hours fetching drink orders wearing his four inch high heels.  And worst of all is the constant pawwing and groping by drunk men that he has to endure with a smile every night.

And of course, Sissy Sandi still has to take care of his Master and Mistress at home.  So after he returns home from an exhausting night at the casino, there is always a list of chores awaiting him when he returns.  And Master and Mistress still expect breakfast in bed at 7:30 sharp every morning!

A Sissy Honeymoon

For the last two years, I have been under the strict and controlling hand of Master Roman.  He has trained and transformed me into an exquisitiely feminine, obedient and docile Sissy.

At first I resisted my captivity and transformation.  But Master Roman skillfully -- and often cruelly -- destroyed my will to resist as he forced my inner femininity to blossom.  Eventually I learned to embrace my new existance as Master Roman's obedient Sissy servant.  My life now revolves around pleasing and serving my Master -- and nothing else.

I must have succeeded in pleasing Master Roman because he asked me to marry him!  We had a lovely, private ceremony where I took my vow of obedience and servitude, and then Master Roman whisked me down to Jamaica for our Honeymoon. 

As we stood under the waterfall, I could feel Master Roman's cock getting hard as he pressed against me.  He held me tightly in his big strong arms, kissing me.  His hands moved up to my soft little breasts that had developed from the hormones Master Roman had been giving me.  He untied the little bikini top that I was wearing.  I moaned softly as his fingers played with my swollen, sensitive nipples.

"Who are you?" Master Roman whispered into my ear.

"I am your obedient and loving Sissy Wife," I replied as he had trained me.  He smiled.

"And who am I?" Master asked.

"You are my Husband and my Master who I will serve and obey and for the rest of my life.  My only purpose is to please you," I said, reciting the acceptable answer. 

Master nodded and replied, "That's right.  And now to please me I want you to suck my cock."

I instantly fell to my knees and quickly pulled Master's cock into my mouth.  The water where we were standing was fairly deep so I struggled to breathe as I pulled his enormous hard rod into my mouth. 

As he started to cum, Master Roman said, "Sissy Wives don't need to breathe.  They just need to suck cock."  He then pushed my head underwater and held it there.  Even though I was practically drowning, I felt so fulfilled knowing that I was performing a service that pleased my Husband/Master so greatly.  It felt wonderful to being a good Sissy Wife, on my knees, feeling my Master/Husband's hot cum blasting into my mouth and down my throat.  Even as I started to lose consciousness, I ensured that I had thoroughly drained my Master/Husband and had swallowed every drop.

When I regained consciousness, I was on the floor of our hotel room.  These was a note jammed in my bikini bottoms that said, "Get cleaned up and put on new bikini.  Meet me in hot tub next to the big pool.  Hurry.  I need another underwater blowjob right now."

A Sissy Wife's job is never done.

Sissy Behavior Modification

As a professional Sissy Trainer, I have learned how to be very strict.  And I'm not afraid to dish out severe punishment when required to get my Sissies to comply with my requirements.  I'm not shy about using my cattle prod or landing out a few dozen lashes with my riding crop when I'm dealing with a reluctant Sissy.  But as a woman who stands 5' 7" and weighs 130 pounds, sometimes I just don't have what it takes to give a Sissy the punishment he deserves.

Sissy Daisy was a real problem for me.  Even though his physical transformation had proceeded beautifully, he refused to embrace his future as a submissive Sissy pleasure toy.  He insisted that he was a man!  HA!!!  And he refused to entertain male guests that I frequently invite to my home.  For his disobedience, I tried everything:  beatings, starvation, locking him in a dark closet for days at a time.  But nothing worked.  It was time to bring in an expert.

I brought Sissy Daisy over to visit my friend, Master Steed.  Master Steed, you see, is a sadistic, brutal man who enjoys inflicting pain on bad little Sissies.  He is insanely strong and muscular.  And best of all, he is hung like a horse!  When your Sissy needs some extra encouragement, Master Steed is the one to call.

I dragged Sissy Daisy into Master Steed's home and we waited in the living room.  Sissy stood silently in the corner wearing a pretty sundress while I made myself comfortable on the sofa.  Sissy Daisy was so nervous, not having any idea where he was or what was about to happen to him.  I set up my camcorder on a little tripod because I love having a souvenir of these visits to Master Steed's home.   I was getting very excited just thinking about the show I was about to witness. 

Then Master Steed entered the room, shirtless, his huge muscles bulging.  Sissy Daisy was instantly terrified.  He tried to run from the room but Master Steed was on him immediately.  Master Steed hit the Sissy hard, once in the face and once in the stomach.  Sissy Daisy screamed in pain and his tears began to flow.  In one swift motion, Master Steed ripped the sundress off of my Sissy, leaving him completely naked and exposed.  For the next 20 minutes, Master Steed slapped, spanked, pinched, twisted and otherwise tortured my misbehaving little Sissy. 

And then the best part.  Gripping my Sissy's throat, he spun the Sissy around and rammed his massive dick into his tight little bottom.  Sissy Daisy was sobbing like a little bitch and begging for me to make his punishment stop.  I nearly came myself watching my little Sissy getting raped.

That's when I noticed Sissy Daisy's nipples were getting hard!  That little Sissy bitch was getting excited by being fucked by a real man!

I couldn't stop myself.  I jumped up from the sofa and grabbed Sissy Daisy's hard nipples.  I pinched and twisted them hard while  I shouted into the little boy bitch's face, "I can see that you are really enjoying this, aren't you Sissy?  Your nipples don't lie!  You like having a huge cock up your tight little boy pussy, don't you?"

Well, needless to say, Sissy Daisy has been a delightfully obedient Sissy ever since that day.  No more protests, no more denial.  He'll service my male guests and do whatever else I tell him to do.

And just for fun, once in a while I make Sissy Daisy watch his special video with me.  I certainly wouldn't want him to ever forget that special day. 

A Sissy Girlie-Boy -- Part 6

It's been six months since Mommy made me start working at Frank's Hideaway. 

I don't cry in the car on the way to the bar anymore.  I don't care.  I don't care about anything anymore.

I take a lot a Ecstasy and I let the men at that bar buy me Cosmos and shots.  I'm too young to drink, but nobody cares.  Tonight I'm wearing a sparkly red dress.  It's very short and very clingy.  The men really like me when I dress like this.  Mommy has bought me a lot of sexy new dresses recently.   Mommy is really happy.  She has a new BMW and lots of new jewelry and even a mink coat.  But she wasn't so happy when I first started at Frank's Hideaway.  I still remember my first night at the bar.

After being fucked by Manny at my "audition", Mommy was really mad at me for screaming so much while Manny raped me.  She told me that I better learn to "shut the fuck up!"  After Manny was done with me, she told me to get myself cleaned up and that she would be back before the bar opened.  I did as she told me.  I went to the ladies room and brushed my teeth and tried to clean myself up as best I could.  I fixed my make-up and returned to the bar.  A few minutes later, Mommy returned to the bar and handed a package to Frank who was already behind the bar getting ready for the first customers to arrive.

Mommy handed me a couple of Valiums and told me to take them.  She said to me, in a very threatening way, that I better not mess up tonight.  She said that we were very lucky that Frank was letting me work there.

At a few minutes before 9:00, Mommy positioned me on a stool and again told me to do everything Frank told me and to, "...for God's sake, stop your God damn screaming!"  Mommy said she would return at the end of the night and with that Mommy was gone.

The bar was very quiet.  There were two other bar girls -- real girls -- positioned on other stools at the bar.  They were talking to each other and laughing and pointing at me.  I would learn that the other bar girls would never be nice to me.

The bar opened at 9:00 and the men started pouring in.  After a few minutes,  men started to gather around me.  It wasn't long before I started to feel some hands grabbing my ass while some other hands started to brush against my shoulders, my legs....

At 10:00, I was told to escort my first "date" of the night into the back.  I was terrified but I knew I had better do my best to cooperate.  My "date" was an older man, mostly bald, sort of fat.  He smelled like cigarettes.  He threw an arm around my shoulders while we walked to the back.

Once in my cubicle, he pulled down his pants and he said, "Come on baby, let's go!"  I hesitated, not sure what he wanted me to do.  "Come on!" he shouted.  "I only get 25 minutes!  Get going!"

His face was getting red and I could tell he was sort of drunk and getting pretty angry.  I figured he wanted a blow job, so I quickly got on my knees.   He fished his cock out of his underpants and jammed it into my face.  I closed my eyes and opened my mouth...

And that scene repeated itself all night long.  Man after man, cock after cock...I worked hard to make each man cum as fast as I could.  I knew I would be in trouble if I failed to make any customers cum in the 25 minutes they paid for.  I would rush to the ladies room in between each date and try my best to clean up in the five minutes allowed.

And then my 12:30 "date" wanted something different.  He wanted to fuck my ass.

"Get over here, bitch," he said.  "Frank said you have a problem with making too much noise, so he gave me this."  He was holding the package that Mommy had handed Frank just before the bar opened.  My "date" reached into the package and pulled out a ball gag.  "Get over here and open your mouth."

I did as he ordered and he fastened the ball gag tightly around my head.  "There," he said, "now you're ready."  He grabbed my panties and yanked them down and pushed me over the arm of the couch.  With my bottom stuck up in the air, my "date" rammed his hard dick in to me hard.  I tried to scream in pain, but with the gag in my mouth all that came out was a muffled moan.  "Oh yeah," he said, "you like that, don't you baby!"  He continued to bang away at me until he came, all the while I screamed in near silence through my gag.

And the night -- and every Friday and Saturday night since -- continued like that until 3:30 in the morning. 

A Sissy Girlie-Boy - Part 5

"Get on your knees," Manny instructed.  I did as he said.  He stood and said, "Take off my pants."  I struggled to unbuckle his belt because my hands were shaking so much.  "Hurry up," he said.


I managed to unzip his pants and pulled his pants down.  And that's when I saw it -- the most enormous cock I had ever seen.  It must have been 10 inches long and really thick.  It sprang to life, right in front of my face, as I freed it from his pants.  I fell backwards from the shock of seeing this monster.  "Get up, you stupid Sissy!" Mommy screamed, as she kicked me.


I hurried back to my knees.  I wasn't really sure what I was supposed to do next.  But Manny made it perfectly clear.  "Suck it, bitch," he said, grabbing the back of my head and pulling me hard into his crotch.  At first I didn't open my mouth, but then Manny roared, "I SAID SUCK IT, YOU SISSY BITCH!"


Terrified I opened my mouth and put Manny's massive tool inside.  It tasted terrible.  I couldn't believe this nightmare was really happening to me.  But anyway, I must have been doing something right, because Manny started moaning as he pumped his big dick in and out of my mouth, his hands firmly holding my head in place.  "Mmmm, yeah," Manny said.  "That bitch has one sweet Sissy mouth."


"Jackie's really enjoying that, isn't he!" Mommy said with evil delight.


"Come on, Manny," Frank said impatiently.  "Let's go, I need to get back to work."


"Get up on the couch," Manny instructed, pulling his cock from my mouth.  "Get on all fours, like a Sissy doggie and stick your ass in the air."


I did as he commanded.  Manny roughly yanked my tight panties down.  I could feel him rubbing the tip of his cock inside the crack of my ass.  I knew what was coming next.  I squeezed my eyes tightly shut and prayed for this to be over.  And then I felt Manny start to push his big rod into my lubricated bottom.  As the tip of his cock started to enter me, it was painful and horrible but I thought I could tolerate it.  But then he started to push the rest of his massive dick into me.  I screamed in pain as inch after inch of his massive cock drilled deeper and deeper into me.  I was sure that his cock was going to rip me apart from the inside.


"For God's sake, Jackie, SHUT UP!" Mommy shouted over my own screams. 


"Yeah, shut up, Jackie," Manny repeated, laughingly.


The next thing that I remember, Manny wrapped his big arms around me, one around my waist and one across my chest.  With his steel rod pumping inside of me, Manny lifted me off the couch.  I was literally suspended beneath him as he banged away at me.  I continued to scream in pain and begged him to stop.  Still carrying me beneath him, Manny turned away from the couch and towards Frank and Mommy.  It was horrible being fucked by this giant -- but it was made even more horrible that I was now face-to-face with Mommy while it was happening.  And that's when Mommy slapped me -- hard -- across the face.  "Stop that awful screaming!" she shouted into my face.

And then Manny started breathing really hard.  His arms wrapped more tightly around me -- so tightly I could barely breathe.  I knew what was about to happen.  His pumping became harder, almost violent.  His big hard cock became bigger and harder.  And then he came.  I could feel his hot cum blasting into me.  I started to cry.

After a minute, he pulled out of me and literally dropped me on the couch.

"Not too bad," Manny reported to Frank as he left the cubicle, without even looking at me after dumping me on the couch.  "But he gonna have to shut the fuck up.  No one wanna listen to all that."

"Get cleaned up," instructed Frank.  "Customers will be showing up soon."  To Mommy he added, "That Sissy better not make so much noise with my customers."

Mommy just glared at me as I continued to cry.

A Sissy Girlie-Boy -- part 4

Mommy helped me into the other dress.  "Yes, I think this dress will be good for your first night at the bar," Mommy said.  It was awful.  It was strapless like the other one, but this one was leather and had a shiny zipper right between my teeny little "boobs."  I thought I looked really trashy.  "Please, Mommy, PLEASE don't make me go to the bar dressed like this!"  I begged.  Mommy whacked me hard with the hairbrush she had just used to do my hair. 

I hated the idea that I was being primped and prettied to spend the evening in some bar where strange men would be staring at me and...well doing other things to me. 

"Oh, I almost forgot!"  Mommy said.  "Quick, lift up your dress and bend over."  I did what Mommy asked.  She yanked down my tight panty and jammed the tip of a tube of lubricant up my bottom and squeezed the tube.  I shrieked as the icy cold gel was blasted into me.  "You'll thank me for that later,"  Mommy said. 

Mommy handed me a small purse that had my make-up and the rest of the lubricating gel.  "We're late,"  Momy said.  "Get in the car."

I continued to plead with Mommy to change her mind.  I said I would do anything -- anything -- if she would change her mind.  But she just ignored me and pushed me into the car.

When we arrived at Frank's Hideaway, it was about 7:00 -- two hours before opening time.  Frank was there and he told Mommy that I looked perfect.  He seemed really happy.  "OK," Frank said, "Let's try her -- I mean him -- out."  Then Frank shouted into the back, "Hey Manny, come out here."  Manny was a giant of a man -- huge like a football player.  He had a thick neck, huge hands and a dark complexion.  "Manny's our bouncer here.  He also helps me audition all the new girls.  Manny meet Jackie."

I just stood there until Mommy poked me.  "Nice to meet you, sir," I whispered nervously.

"Manny, take Jackie into the back and let's see what's he got," Frank said.

"Never done it with no Sissy before," Manny rumbled in his deep bass voice.  "Come on, Jackie, let's go."  Manny grabbed my hand and pulled me into the back.  I was very scared but I was completely out of control of the situation, so I tried to just endure what was happening to me.  To my horror, Frank and Mommy followed Manny and me into the first of the little rooms in the back.

Manny sat down on the couch and said, "OK Jackie, let's go."  I had no idea what that meant or what I was supposed to do. 

"Don't just stand there!  Go over to him," Mommy snarled as she shoved me hard, nearly making me topple off my high heels.  As I stumbled over to where Manny sat, he grabbed my arm and pulled me onto his lap.  He wrapped his huge arms around me and started kissing me.  Hard.   I tried to pull away as he jammed his huge tongue into my mouth, but his arms were wrapped tightly around me like a steel cage and I was completely immobilized.  "OK, Jackie, enough kissy-kissy fun.  Let's see what else you can do," Mommy commanded.

"Get on your knees," Manny instructed.  I did as he said.  He stood and said, "Take off my pants."  I struggled to unbuckled his belt because my hands were shaking so much.  "Hurry up," he said.