Halloweenie Ch. 01

Halloweenie Ch. 01

by BJ Michaels

"Why do I have to be the girl?" I whined to Margaret. "Why can't you have your boyfriend wear the costume?"

She gave me the oddest look and said, "Are you nuts? Who's going to believe HE'S a girl?"

Huh? What does THAT mean? I wondered.

She scolded me. "Johnny, lighten up -- it's Halloween -- there 'll be a lotta guys dressed like girls...now sit still and stop squirming -- I'm almost done with your makeup."

I share a two-bedroom apartment with my best friend, Mike, and his girlfriend, Margaret. The 'Innocent Schoolgirl' costume was her idea, and I didn't like it at all.

I complained to Mike but he wouldn't hear it.

"Would you please just go along with what she wants," he said to me, "she can be a real bitch if she doesn't get her way!"

"I know -- I know," I replied, "...but don't you think it's ridiculous and totally unnecessary to have all my body hair removed?"

"It's called 'realism' John...she said your pubes were sticking out of those girly undies and who'd believe a schoolgirl with hairy armpits? It's only a costume, John, don't get your panties in a twist, hahahahahaha...."

"Very funny," I scowled at him, "...this is Margaret's revenge, isn't it? She's still mad about me catching you two in a make-out session, am I right?"

"John, it's not so much that you caught us," he said, "...it's that instead of going to your room and leaving us alone, you stood there and watched her blow me..."

"You guys were on the living room sofa -- what else was I supposed to do?" I asked him.

"You were supposed to give us privacy and go to your bedroom!" he snapped at me.

"So what? What's the big deal?" I asked him, "it's only sex...."

"Dammit John, you know how shy she is," he angrily said to me, "...she was finally getting comfortable going down on me and now she says she's never doing that again -- thanks a lot, friend!"

"Okay-okay, I'm sorry," I said to him staring at the schoolgirl outfit on my bed., "...but explain THIS to me, will you? A white blouse -- a white skirt -- white anklet socks and white patent leather shoes - what's with the pink, nylon undies? Wouldn't an innocent schoolgirl wear white, cotton underpants?"

"Yeah, I told her the pink panties were overkill," said Mike reaching into his pants pocket, "here -- put these on instead" and tossed me a pair of girls, white, cotton underpants.

I breathed a sigh of relief. Sure, they were still girly undies, but at least they weren't nylon or pink.

"She's going to be here any second -- hurry-up and put on your costume or she'll dress you herself!" he warned me and left me alone.

I saw lettering on the front and back of the underpants and stopped and held them up.

On the front were the words "Itty Bitty Clitty" with an arrow pointing downwards and the seat of the undies read: "Insert Here" also with a downward pointing arrow.

Insert WHAT in WHERE? I wondered as I slipped the underpants up my legs into place.

The white shirt was so tight my hard nipples poked-out the soft fabric. I had trouble with the buttons -- they were on the wrong side...it really is a woman's blouse!

When I held up the white, pleated skirt I winced at how small it was in my hands.

Damn, this piece of cloth will barely cover my crotch, I thought. What kind of 'innocent schoolgirl' would wear clothes like these?

***

Margaret suddenly announced, "Voila, I'm done with your makeup," and backed away to admire her work.

The strange expression on her face caused me to panic.

"What's wrong? Why are you looking at me that way? I'm hideous, aren't I? I told you I wouldn't make a very realistic girl...."

"Ohhhh, on the contrary, Johnny, or should I call you 'Joanie'? WOW -- you're one of the cutest girls I've ever seen!" she grinned at me. "What do you think Mike? Isn't 'Joanie' adorable?"

I expected my best friend to back me up and make a sarcastic remark but his eyes narrowed as he said, "Oh yeah, I'd definitely do her!"

"Thanks a lot, friend," I sarcastically replied and turned to Margaret and asked, "...why did you call me 'Joanie'?"

"It doesn't make sense to call such a pretty girl, 'Johnny,' does it?" she smirked.

She directed me to the the full-length bathroom mirror. I took a quick look, turned away then swiveled my head and looked again. Holy crap, I didn't recognize myself -- Margaret had really transformed me into a pretty girl!

The bitch laughed out loud and said, "You better be careful at the party, girlfriend, you're gonna have a lot of horny guys trying to get into your pants!"

I did not see the humor in her comment so I did not join in their laughter.

***

Three-days later Margaret was angry with me. "I hope you realize, Johnny, if you don't end this little farce you're playing with my boss, you're probably going to have to put-out for him tonight!"

"What are you talking about? It's only dinner and a movie," I protested.

She squinted hard at me, and said, "Listen carefully, John: a man who thinks you're a girl and has a crush on you is taking you out on a third date, in your experience, Johnny, what do YOU expect from a girl on the third date?"

Just thinking about it made me blush. Margaret had to say it out loud though.

"He's going to want at least a handjob, he might even insist you take it in your mouth - IN YOUR MOUTH, JOHNNY!! Do you really want to go that far with a guy simply because he's spending money on you?"

"I have fun with him," I softly protested.

"You're both guys, Johnny - GUYS!!" she barked at me. "You are 'Johnny' NOT 'Joanie' - and the last I knew YOU-ARE-NOT-A-HOMO!!!"

"Well, no, no I'm not," I agreed.

She turned to her boyfriend and said, "Mike, tell your friend he's being ridiculous -- he's NOT A FREAKING GIRL!!!"

He sounded like a robot. He simply parroted his girlfriend. "John, you are not a freaking girl...."

His voice sounded strange so I glanced towards Mike, and oh-my-hell, he not only had a weird, sheepish grin on his face, but a growing bulge in his slacks, as well. Holy crap!

***

Ending the relationship on the phone would have been rude. I needed to 'man-up' and do it in-person but after he spent a small fortune on our filet and lobster dinners I figured it would be cruel to dump him so soon so I decided to wait until the movie was over.

Well, in hindsight, I guess I made a tactical error during the movie. After he slid his hand under my skirt a second time and began rubbing my nylon-clad upper thigh, I grew nervous and took hold of his hand and held it tightly. He seemed content holding my hand and I breathed a sigh of relief and we continued watching the movie.

I should have known better though, what kind of guy is happy with just holding hands?

A few minutes later he caught me off-guard when he took my hand and pressed it to the crotch of his thin and expensive Italian slacks. A rather rude and crude gesture, if you ask me, and then I felt it - oh-my-gawd, he had a boner!

I tried to pull away my hand but he wouldn't let me. In fact, he began to slowly move my hand back-and-forth the full length of his hard-on. I became dizzy and my breath caught in my throat.

Out of sheer desperation and self-defense, I leaned over and whispered in his ear, "Not here, sweetie, I'll take care of it for you in the car after the movie, okay?"

He seemed satisfied with my promise. This time he allowed me to take my hand off his dick but the damage had already been done. I spent the rest of the movie with his arm draped over my shoulders wondering what the hell I was going to do when we got into his car after the movie.

***

Margaret was sitting on the sofa when I got home. I grunted "Hello" and headed straight for my room.

She called out, "Hold on there, young lady, come over here and tell me all about your date, hahahahaha...."

"Very funny," I snarled at her and continued towards my bedroom.

"JOANIE -- GET OVER HERE - NOW!" she barked at me.

Gawd, I hate myself for being so weak and easily intimidated.

"Where's Mike?" I asked when I was sitting beside her.

"He's working the graveyard shift tonight," she said. "So how did it go, girlfriend? Did he make a move on you? Did you have to put-out for him, hahahahaha...."

My face turned beet-red and I averted my eyes from hers.

"Oh-my-hell, you DID put out for him, didn't you? Hahahahaha..." she howled with laughter, "what did he make you do? Did you play with his dick, or did you go down on him? hahahahaha"

I was so embarrassed I didn't even try to speak.

"Oh-my-hell -- you went down on him, didn't you?" she exclaimed with bulging eyes. "YOU SUCKED MY BOSSES COCK! HA-HA-HA-HA-HA-HA-HA-HA...."

I fought back: "I"M NOT A FAGGOT - I did NOT suck his cock -- I, uh, you know, I used my hands...."

More laughter. I'd never known such embarrassment in my life.

"Oh my God, Johnny, I was just joking...did you really give him a handjob?" she asked incredulously.

She knew the answer just by looking at me.

She stopped laughing long enough to remark, "That's the funniest thing I've ever heard...what the hell were you thinking?"

She didn't wait for an answer. She suddenly lifted the hem of my skirt high enough to see the huge wet spot on the crotch of my girly undies.

She exclaimed, "OH-MY-HELL -- YOU CAME INSIDE YOUR PANTIES -- HAHAHAHAHAHAHA -- YOU HAD AN ORGASM STROKING MY BOSSES COCK - HAHAHAHAHAHA...."

I vehemently denied it. "I DID NOT HAVE AN ORGASM...it's leakage -- that's all it is...."

She dropped the hem of my skirt and dismissed me by saying, "Yeah, sure, whatever you say, girlfriend...."

I stared at the floor a long time in awkward silence. When I had the nerve to look at her she had a strange gleam in her eyes.

"You know what, girlfriend?" she finally said, "There's one thing Mike absolutely refuses to do for me in bed...."

Uh-oh, what is she getting at? I wondered.

"...so maybe I'll have YOU do it for me...would you like that, girlfriend -- would you like to kiss and lick my pussy for me?"

My heart sank like a rock in a still pond. It was my turn to think, 'OH-MY-GAWD'....

***

She said to me afterwards: "How does it feel to be my bosses little slut and MY lesbian lover? Hahahahahahahaha...."

I was fuming. "You had your fun, Margaret, I'm not doing either of those things ever again!"

The smile vanished from her face. "Oh, but you are, girlfriend, my boss is smitten with you and wants to see you again...."

"No way -- no where -- no how," I protested.

Margaret sneered at me. "What do you think Mike will do when I tell him you're queer? You know how much he hates faggots -- what's he gonna do to you when I tell him you're a panties-wearing sissy who LOVES going down on men?"

"I've NEVER gone down on a guy -- Mike's my best friend," I argued, "...he knows me -- he knows I'm straight -- he knows I'd never do anything like that...."

"Johnny, don't be a simpleton, he already suspects you might be light in the loafers, what's he going to do when I confirm it to him?"

A cold shiver raced up-and-down my spine. "He'll kill me...." I softly admitted.

"WRONG - he'll beat the living shit out of you BEFORE he kills you!" she snarled at me.

I panicked. "What am I supposed to do? I can't keep dressing like a girl and dating your boss!"

"You're going to do BOTH of those until I say you can stop...my boss is crazy about 'Joanie' -- you'll go on a couple more dates with him and then I'll figure out a way to end the relationship...."

I protested, "But he's gonna want more than just, uh, you know...."

"Handjobs?" she sneered at me. "Yes, I'm sure you're right...hey, we still have some banana's in the kitchen, bring me one of them and I'll teach you how to go down on a man...."

Her evil laughter followed me to the kitchen. I had never felt so helpless and impotent in my entire life.

***

Margaret insisted on helping me dress for my 'date' with her boss. She LOVES humiliating me!

"Ooooooo..." she cooed entering my bedroom, "...look how cute you are in your pretty bra and panties!"

When my face flushed a deep red, she added, "Don't be embarrassed, Joanie, we girls dress and undress in front of each other all the time, hahahahaha...."

I stared at the floor as she slowly looked me up and down.

"Uh-oh, we have a small problem," she suddenly said, "...he might notice that tiny lump in your panties, Joanie...."

She abruptly left the room and returned seconds later with an Ace bandage.

"Lower your panties, girl, so we can hide your teeny-weeny between your legs," she said as though it were a normal request. "We don't want my bosses wandering hands to accidentally discover your tiny man-bump down there, do we?"

I hated her for constantly insulting my perfectly adequate penis.

She added: "Remember, girl, you'll need to play offense with him...when he begins to feel up your titties put your hand on his thigh to distract him...start French kissing him and massaging him down there until he has a nice boner...."

I couldn't believe she was talking to me this way -- I couldn't believe I meekly LET her talk to me this way....

"...don't wait for him to open his pants and take out his dick -- no, you do it for him and make sure you go down on him right away so he doesn't get too frisky and discover your secret...."

"GO DOWN ON HIM? I'm not going down on ANY guy!" I angrily said to her.

"I'm afraid you're going to have to, sweetie, I told him your Halloween, 'innocent girl' costume wasn't quite who you really are...that in reality, you're kind of a tramp and slut...."

I was appalled. "WHY WOULD YOU SAY THAT TO HIM?"

"Hey, it's what I knew he wanted to hear...and you better treat him right, girlfriend, I'm up for a big promotion and raise -- you'll be very-very sorry if you ruin it for me, Joanie!"

Oh-my-gawwd...

"But what about afterwards? What if he wants to reciprocate -- he'll find out I'm not a girl - what do I do THEN?" I asked her.

She furrowed her eyebrows and chuckled, "I've heard stories about him...he's a flirtsy-squirtsy-arrivederci kind of guy...after a girl swallows his load he leaves her high-and-dry -- he doesn't even TRY to satisfy her -- you shouldn't have a problem...."

Huh? After I swallow his load? WTF???

Margaret held out the skirt she wanted me to wear. It looked shorter than the one I wore to the Halloween party. She suddenly pulled it back and threw it on the bed.

Uh-oh, she had that crazy look in her eyes again.

She unfastened her jeans and pushed them and her panties down her legs. My heart sank -- I knew what I'd hear from her next....

She spread her legs wide, placed her hands on her hips and in a husky growl said to me: "Get on your knees, my pretty little bitch, it's time for you to lick my pussy again!"

"Dammit, Margaret, you're my best friends girlfriend, I can't keep doing that for you!" I complained.

Would you rather I make you suck your best friend's dick?" she snarled at me.

I was on my knees in a New-York-Minute choking and gagging while slurping away on her oily and smelly snatch.

***

I had to whizz like a race horse but couldn't go into the men's room wearing a pink blouse and matching short skirt, am I right? I stood before the ladies room door pondering my options.

A woman's voice suddenly said to me, "It's alright, dear, they keep the bathroom very clean here -- just follow me inside...."

In my girly whisper I said, "Thank you, maam" and did just that -- I took a deep breath, followed her into the ladies room and made a mad dash for the first open stall I saw and latched the door shut.

I stood before the toilet, lifted the hem of my skirt to whip out my dick when a voice in my head cautioned, 'Whoa, boy, what are you doing? You gotta sit down in here to take a leak!'

I reached under the skirt, pushed the feminine undies down to my knees and sat down on the toilet seat to pee like a girl.

I couldn't wait for Margaret to get me out of this so-called 'relationship' with her boss. She promised tonight would be my last 'date' with him, and the last time I would ever dress like a girl.

Yeah, sure, she warned me I might have to go down on him later in the car, but it would be a small price to pay for freedom, wouldn't it be?

I heard the bathroom door open and the sound of high heels on the tile floor. Through a crack in the toilet door I watched two older women primping and preening in front of the mirror.

"Did you see that little girl with Mister Van Fleet?" asked one woman.

My ears pricked-up at the mention of his name.

"You mean his slut-of-the-week?" said the other woman.

"Who's she trying to fool with all that padding in her bra?" asked the first woman. "I'll bet she's a 32-double A...."

"It won't matter to Mister Van Fleet," said the other one, "he's more into asses than boobs...but the girl looks like she's only eighteen or nineteen...."

"Why is he always interested in girls that age?" one of them asked.

"Four words," answered the other woman, "oral and anal sodomy...."

"MILLIE -- you're terrible! Hahahahahahahahaha...."

"No, I mean it," said the woman. "...word around the office is he's frightened of va-jay-jays and doesn't want anything to do with them!"

"Nah, I don't believe that at all -- I think he knows if he knocks-up his 'slut-du-jour' his wife would divorce him and take everything he's got!!"

"Yeah, that's probably very true...."

I was stunned. His wife? HIS WIFE????

I was alone in the ladies room when the women left. I finished peeing and readjusted my dick inside the panties. My heart ached. I was devastated. The rat-bastard is married? How could he lead me on like this?

Whoa-whoa-whoa, John, you're a GUY -- he's a GUY -- you're playing a ROLE - what the hell is wrong with you?

I lifted my skirt and was satisfied I saw no manly bulge in the pale pink panties and that my garter belt and nylon stockings were also in place.

***

"You've been awfully quiet since dinner, sweetheart, is something wrong?" he asked me on the ride home.

I didn't say a word but my mind screamed, 'Yes, you asshole, you're married and cheating on your wife!'

"Come over here and sit next me, cutie," he said in the darkness.

I wanted to punch the cheating bastard in the face but reminded myself this is all an act, and after tonight it would be over. I scooched over next to him until our legs were touching.

"That's a good girl," he said patting my nylon-clad thigh..

What a condescending prick, I thought.

We continued on in silent darkness. The route he was taking puzzled me. There wasn't anything on this side of town except for 'The Overlook,' a scenic area above the water where horny teenagers go to make out. Uh-oh, we're not going there, are we?

A cold shiver raced up and down my spine when he turned left onto the gravel road leading to The Overlook.

Nooooooooooooooo, screamed my brain. He's going to make me do homo-sex things for him, of course, he thinks I'm a girl so it wouldn't be homo-sex to him at all....

What everyone likes best about The Overlook is the privacy. The cars are only twenty-feet apart but the parking spots are separated by bushes, shrubs and fir trees. There could be ten cars nearby, but you feel like you're all alone.

"Have you ever been out here, sweetheart?" he softly asked me.

"Oh no, never...." I said to him.

Is it a lie if I've been there as a guy but not as a girl?

***

"Sweetheart, move over for me," he said when he found a secluded spot and turned off the ignition, "the steering wheel is in the way."

I wanted to ask him 'In the way of what?' but simply replied, "Okay" and did what he wanted.

He put his arm around me and pulled me close to him. I was grateful it was too dark to see his face.