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.

A Sissy Girlie-Boy -- part 3

Ten weeks ago, Mommy made me start working at "Frank's Hideaway" as one of the bar girls.  Only, I'm not a girl.  I'm really a boy.  But I dress like a girl and the men who come to the bar like to have sex with me.  You see, there are a lot of men who get really turned on abusing and fucking Sissy Girlie-boys like me.

But I hate going to the bar and I hate being used as a Sissy whore by lots of strange men.  But Mommy makes me do it.  At first it was only on Saturday nights.  But now I have to work on Friday nights too.

Giving blow jobs is really disgusting.  And getting fucked in the ass really hurts.  But Mommy gets so angry whenever I complain.  I try to be brave when I'm at the bar.  But I usually cry in the car -- both on the way to the bar thinking about what I'm going to have to do when I get there -- and on the way home as I try to forget the awful things I had to do all night.

Even though it's really horrible, I've gotten very good at making men cum.  You see, I only have 25 minutes with each "date."  That's not much time and if the man doesn't cum, they get really angry and complain to Frank.  And when customers complain, Frank doesn't pay me -- I mean doesn't pay Mommy -- my share.   

But at first I wasn't good at pleasuring men.  I still remember my first night at the bar.  Mommy started getting me ready at about 3:00 in the afternoon.  Mommy bathed me and powdered me.  She fluffed up my hair and covered it with hairspray.  Then she did my make-up:  just some light foundation, eye liner and mascara, and pale lip gloss.  Then she handed me my new underwear:  a black strapless bra -- 34AA -- and an incredibly tight and uncomfortable pair of black panties.  Mommy hooked the bra behind my back and helped me squiggle into my confining panties.  "We can't have any unsightly bulges!"  Mommy chirped.  

And then she showed me the dress.  It was a tight strapless mini dress with black and grey and white stripes.  My bra made it look like I had tiny little breasts.  Mommy helped me into the dress and fussed until she was satisfied.  I felt practically naked and was very aware of the cool air on my exposed arms and shoulders.  She had me slip on a pair of shiny black high heels.  And then she let me look in the mirror.  "Mommy, oh no!" I shrieked when I saw my reflection.  "I can go out looking like this.  I look so, so, so..."

"Slutty?" Mommy unhelpfully finished my sentence.  "Yes, you're right.  You do look like a little slut!  OK, you win.  You don't have to wear this dress tonight.  You can wear it next week.  Here, put this one on."  Mommy said as she handed me another dress.

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...