A Sissy Girlie-Boy - part 2

It's been six weeks since Mommy first dragged me to Frank's Hideaway.  Since then, I've been coming to the bar every Saturday night.

Tonight is just like every other Saturday night.  Following Frank's instructions, Mommy delivered me to the bar at 8:30, half an hour before the bar opened.  I take my position on the stool that Frank assigned me at the far end of the bar.  There are three other girls parked at the bar tonight -- real girls, not girlie-boys like me.  They never talk to me.  Tonight I'm wearing one of the new dresses that Mommy bought for me.  It is a tight black dress with sheer mesh sleeves.  The dress is so short that it doesn't even properly cover me when I sit on my stool.  I'm also wearing some strappy black platform shoes with very high heels.  Frank tells me that I look perfect and that, dressed like this, that he's sure that I will be very busy tonight.

And just like every Saturday, I look like a total Sissy faggot.  With just a hint of make-up, no wig, no fake boobs, I am obviously not a real girl.  I am a Sissy boy in a dress. 

At 9:00, the bar opens and the men start to pour in.  By 9:15, I have a crowd of about 5 or 6 men hovering around me, trying to buy me drinks, brushing up against me trying to get a feel.  I do my best to smile and seem interested in all the attention.   By 9:30, one of the men has paid Frank to take me into "the back room".   I get up from my stool and let me first "date" of the evening lead me into the back.

And so begins another horrifying Saturday night for me at Frank's Hideaway.

Six weeks ago, when Mommy first brought me here, Frank explained to me how things work in his bar.  Men -- dozens and dozens of men -- come to Frank's Hideaway for the chance to spend some "private time" with one of the bar girls.  Frank's customers pay him $100 to take a girl into "the back room" for 25 minutes.  The back room used to be a dining room.  Now it's set up with four small cubicles, each with a couch, a small table and curtain for a door.

Frank explained that I would be his newest bar girl.

I shouted, "You're both crazy!  You can't make me do that!"  And I ran for the door.  But in my high heels, I couldn't run fast and Frank caught me before I was even half way to the exit.  Mommy slapped me hard and started screaming in my face that I had better cooperate or I would be sorry.  Mommy told Frank to beat me if I ever misbehaved.  Mommy ordered me sit sit on a bar stool and to listen carefully to Frank's instruction. 

For the next ten minutes, Frank told me everything I needed to know.  I was crying the  whole time.  Mommy slapped me twice more telling me to stop balling like a little Sissy.  Frank explained that after a man pays the bartender $100, I have to take him back to one of the cubicles and "entertain" him.  Frank pointed out that 25 minutes isn't very long, so that I need to work fast because the customers get very angry if they don't get to cum before the 25 minute bell goes off.

"Please no," I whimpered.  "please don't make me do this." 

"Shut up and behave, Sissy!"  Mommy shouted, slapping me again, this time harder than before.

Frank continued by explaining that once the 25 minute bell goes off, I only have 5 minutes to get myself cleaned up before it's the next man's turn.  And any time I'm not with a customer in the back room, I need to be at the bar on my stool.  Most men want blow jobs, Frank explained, but some would want to fuck my ass.  Therefore, Frank advised, I better arrive well lubricated.  That's when I fainted and fell off my stool.

That was six weeks ago.  But right now it is 9:30 and I am being led by my first "date" of the evening back to one of curtained rooms.  He looks a little familiar, maybe he's been a customer before.  He has a hand squeezes my ass hard as we walk together.

Once in the cubicle, I draw the curtain closed.  He is already seated on the couch and he tells me to come sit on his lap.  I do and he starts feeling me up and kissing me.  I start moaning and panting because I know that makes the men excited.  He sticks his tongue deep into my mouth and I suck on it.  I start rubbing the bulge in his pants.  I can tell that he enjoys that.

"Do you want to suck my cock?"  he asks.  "Oh, yes please," I reply breathily, doing my best to get him excited.  He smiles.

I slide off his lap and position myself on my knees between his legs.  I help him take off his pants.  His big cock is already starting to get erect.  I stuff his cock into my mouth and get to work.  I frantically attack his rod with my lips, my tongue, my teeth.  With my hands, I play with his balls.  I moan while I suck on him.  In just a few minutes, I feel his muscles tense.  He is going to cum any minute.   I relax slightly knowing that he will finish before my 25 minute deadline.  He grabs my head hard and pushes my face into his crotch.  His cock is down my throat and I want to gag, but I fight it.  He explodes in my mouth and it feels like a gallon of hot cum is pouring into my mouth.

"Swallow it, Sissy," he says.  "Swallow it all!" 

I work hard to swallow and lick up every drop.  And just as I finish giving his cock a thorough tongue bath, the 25 minute bell goes off.  The man stands up and roughly pushes me away, knocking me to the floor.  He pulls up his pants and pushes through the curtains to return to the bar.  I hear him mutter, "Disgusting Sissy whore," as he leaves.

I race to the ladies' bathroom to brush my teeth and to put on some fresh lip gloss.  I have only a couple of minutes before my next "date."  Two of the other bar girls are also in the restroom, cleaning themselves up.  One of them snarls, "Get out of here.  This room is for 'ladies', not Sissy faggots!"  The other girl laughs and says, "I hear the Sissy doesn't get paid for blow jobs -- he pays to give blow jobs!"  They both howl with laughter.  I try to ignore their abuse as I frantically scrub the taste of cum out of my mouth. 

I race back to  my stool just as the 10:00 bell sounds.  My next "date" is waiting to walk me to my cubicle in the back room. 

And so my nightmare continued until the bar closed at 3:00 in the morning, I was pretty much in the back room all evening -- I think I had 9 or 10 dates tonight!  I had men cumming in my mouth and in my bottom all night long. 

Mommy picked me up at around 3:15 and got an envelope of cash from Frank for my share.  I handed her my tips for the night and she was very angry that I hadn't collected more.

"Well, Jackie," Mommy said on the drive home, "I have great news for you!  Starting next week, Frank wants you to work at the bar on Friday nights too!  Isn't that wonderful!"

I cried all the way home. 

A Sissy Girlie-Boy -- part 1

Ever since Daddy left, I knew that things have been difficult for Mommy financially.  She was working two jobs, but still there never seemed to be enough money in the house.  Mommy was becoming desparate and depressed.

But that was before Halloween.  You see, for Halloween, I girl I knew from school and I dressed up as Bonnie and Clyde -- only I was dressed as Bonnie and she was Clyde!  I wore a white flapper dress, complete with a long blonde wig, lots of make-up and big fake boobs.  Well, our costumes were a big hit.  We even won first prize in the "couples costume" category at the High School Halloween party.

When Mommy saw me in my Bonnie costume, she seemed really shocked.  "Oh my!" she gasped when she saw me.  "You really look like a girl!  Your legs are gorgeous."  And then after a minute, she said, "Hmmmm, this isn't the first time you've dressed up like a girl, is it?"

Well, she was right, but I denied it.  For years I had been dressing up in Mommy's clothes whenever I was alone in the house.

The next weekend, Mommy asked me again about dressing up as a girl, but this time she wasn't so gentle about it.  "I know you've been getting into my things and playing dress up everytime I leave the house.  It's true isn't it?  You are really a little cross dressing Sissy, aren't you?  Well since you like wearing dresses so much, I've come up with an idea for you to prance around in dresses AND make a little extra money for the family."

I tried to protest, but Mommy wouldn't have any of it.  She had me dress up as a girl again, wearing the same white flapper dress and high heels I had worn on Halloween.  Only this time, she didn't let me wear a wig or falsies and she put only a little make-up on me.  "Mmmmm, yes, that's the look we want," Mommy said.  I looked sort of girlish -- but it was pretty obvious that I was really a boy.  "Why am I dressed up like this Mommy?" I asked. 

"You'll find out soon, sweetie,"  Mommy replied.  "Just practice your girlie walk again for me."

After a couple of hours of practicing how to sit and walk and talk girlishly, Mommy ordered me to get in the car.

We drove all the way downtown and went into the area with all the warehouses.  I had never been in this part of town before.  We parked in front of a bar called "Frank's Hideaway."  It looked like a sort of dangerous place.  It was still early and the bar didn't look open yet.  Mommy told me to get out of the car and go into the bar.  

"What?!?" I screamed.  "I can't go into a bar dressed like this!!!  I want to go home!"  That's when Mommy slapped me.  "Get out of the car right now, you little Sissy," she snarled.

Mommy literally dragged me into the bar.  "Hello Frank," Mommy said to the man behind the bar.  "This is my son Jack...or should I say Jackie, the one I told you about on the phone yesterday."

"Of course," replied Frank as he looked me over.  "Yes, he looks great; just the way I hoped he would.  I always wanted to have a girly-boy like him for the bar.  He'll do well here.   But he'll need some new clothes."

"I know," Mommy replied.  "Don't worry, I'll take care of that."

"Now Jackie," Frank said.  "Let me tell you how things work around here..."


To be continued...

Sissy's Anniversary Surprise

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A Sissy's New Bra

Sissy Monica looked down sadly at his expanding breasts.

Mother had started her Sissy son on a rigorous feminization program ever since finding a collection of graphic forced feminization magazines under his bed.  "Is this what you want, you pathetic faggot!" she screamed when she found his secret stash.  "I can make this happen to you, you know.  You're not much of a man anyway are you?  You're a pathetic excuse of a male, just like your father was!"

And from that day day forward, Sissy Monica was forced to live his life as a girl.  Sissy Monica was so ashamed of Mother's discovery and so scared of her temper, that he didn't fight back. 

At first, he continued to go to high school as a boy, transforming back into a Sissy girl as soon as he got home.  Mother filled Sissy Monica's closet and drawers with pretty girl clothes and taught him how to put on make-up and fix his hair.  At first, to make Sissy Monica look really girlish, Mother filled the cups of his bra with realistic silicone breast forms.

But that was months ago.  But since then, after Mother's strict regiman of dieting, figure training and hormones, Sissy Monica's body had started to change. 

Recognizing these obvious changes in her son's body, Mother gave Sissy Monica a very exciting gift.  It was a padded bra.  Mother ordered him to put it on.

Sissy Monica slipped the straps on over his skinny shoulders while Mother watched.  He expertly fastened the clasp behind his back.  To his horror, Sissy Monica realized that his own boobs neatly filled the cups of his new bra.  You see, Sissy Monica no longer needed to wear the breast forms -- his own breasts had swollen quite dramatically in the last few weeks.  Sissy Monica now had a curvy, womanly bust with just his own boobs in his own padded bra.

"Ohhhhh!" Mother cooed, "Look at you!  My little Sissy Monica has blossomed into a real lady!  Tomorrow let's go shopping for a cute swimsuit for you!"  Sissy Monica started to cry, realizing that he would be stuck forever as a Sissy girl and never again be able to live his life as a boy.

Sissy Monica never returned to high school after that day.  But later that spring Mother and her "daughter" Sissy Monica went on a 10-day Carribean cruise during which Mother delighted parading her reluctant Sissy Monica in the prettiest and most revealing cocktail dresses and swimsuits, putting her Sissy's new cleavage on display for all to see and admire. 

Sissy's Sexy New Lingerie

 "Oh Sissy Belinda!  Come here!" my Wife shouted from her bedroom, ringing a bell that could be heard throughout the house.  I had been dreading this moment all night. 

Four hours ago, before going out on a date with her new boyfriend, my Wife handed me a box from a fancy lingerie shop downtown.  "There is a very pretty new bra and panty set in the box.  I want you to be wearing this and looking your sexiest when I get home.  And I want you wearing this pink bow in your hair.  And this lacey glove.  Do you understand?"

"Yes, Ma'am," I meekly replied.  And while my Wife was out on her date, I dressed in the outfit as ordered.  I carefully tucked my pathetic little cockette away to ensure there would be no unsightly bulges.  I worked very hard to make my hair and make-up look sexy too.

My wife had returned home about an hour ago and was entertaining her new lover in the Master bedroom.  I had been waiting in silence in the laundry room, which was now also my bedroom.   And now I had been summoned.

I raced up the stairs to my Wife's master bedroom because my Wife hates to be kept waiting.  There I found my Wife and her lover sitting in bed naked, breathless from having just made love.

"You see, Charles, you didn't believe me.  This is my Sissy husband.  I call him Belinda now," my Wife explained to her muscular and handsome lover.

"No way!" he exclaimed in disbelief.  "That hot chick was your husband?"

"Well, unfortunately, technically he still is my husband, but you neededn't worry about that."  Then to me she said, "Well don't just stand there, Sissy Belinda.  Show us what you got.   Give us some sexy poses and show us what a pretty and pathetic little Sissy you've become.  I want to take some more photos of you."

As instructed, I struck several provocative poses, while my wife snapped away with her camera.  I could see the sheets cover Charles' lap begin to stir as I did my thing.  Obviously he was enjoying my performance and getting excited.

"And Charles, Sissy Belinda doesn't just look and act like a girl.   Oh no, he also sucks cock like a girl.  Isn't that true Sissy?"

"Yes Ma'am," I replied shamefully.  This was not the first time that my Wife had brought a lover home and forced me to "entertain" him.

"Well then, don't just stand there. Get over here and wrap your lips around this," she commanded as she threw back the sheets.  I gasped with when I saw her lover's monstrous cock.  My wife roared wife laughter seeing the shock on my face.  "Get busy Sissy!"

My Curvy Sissy

There is nothing I enjoy more than a slender, waif-like Sissy.  Their skinny little arms so pretty and weak.  Their slender little bodies so defenseless...

But not every Sissy can be carved into lithe little ballerina.

When Sissy Pamela came into my clutches, he was a bit older and a bit larger than the Sissies I usually work with.  But I thought he had potential and so I went to work on him.  Sissy Pamela was brought to me by his wife.  He thought that after he was transformed, that he would return to his wife for a lifetime of lesbian bliss.  Of course that was never going to happen.  His wife was tired of her Sissy husband and had already taken a new lover -- a real man -- and so Sissy Pamela was all mine, no strings attached.

And I was delighted with the results!  Sissy Pamela is a deliciously curvy Sissy.  It cost a fortune in plastic surgery bills to get the look exactly right.  His soft white flesh contrasting so prettily with the lingerie I dress him him.  His big soft boobs practically spilling from his bras.  His pretty round ass jiggling ever so slightly when he walks around in his high heels.  Delicious!

After nine months of training and surgery, his transformation was complete.  I told him that his wife had come to pick him up and take him home.  He was so excited!  I squeezed Sissy Pamela into the very sexy outfit you see at the right.  I had it custom made for him.  It's not comfortable but he does look gorgeous in it!  His hair and make-up were done just perfectly.  And then I paraded him into the lobby area where his wife was waiting -- sitting on her handsome lover's lap!  At first, poor Sissy Pamela was too confused to be completely humiliated.  It took a lot of explaining to convince him that he wasn't ever going home, that his wife had left him, that she now had a real man for a lover, and that everyone was now laughing at him.  Tears were flooding down Sissy Pamela's face when he finally realized that all of his dreams -- and his freedom -- were gone forever.

But here's the best part.  Who do you think would be most interested in a soft, curvy, fleshy, jiggly Sissy?  Big black men, of course!  Sissy Pamela has been an excellent investment for me because I can whore him out morning, noon and night to a long list big black bulls who can't get enough of my voluptuous creation.  My best clients are a group of five Offensive Linemen for the local NFL team.  They "visit" Sissy Pamela -- together -- at least twice a week. 

As a captive sex toy for powerful and demanding black men, poor Sissy Pamela's life is a horrifying nightmare of nearly continuous forced sex and abuse.