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...