Jobe, Cross Dresser Extraordinaire

I used to be pretty bored. Not last week, or a mouth ago, but the last twenty five years. Life has just always seemed to be… dull. But lately, things have been looking up. I grew my hair out recently, I've got black hair, I'm tall and skinny, perfect body to pretend you're a girl in.

I'm the public relations man for a large company. Most of my work is done outside the office but I'm still there a few days out of every week. I can put on emotions pretty good. Here comes Tom for example, he has no idea that I think he's the dumbest guy that works here.

"Hey Joe, can I talk to you for a second?" I thought, No you idiot leave me alone.

"Sure Tom, what ya need?"

"Well, this report you handed in is due on Friday." He handed me a folder.

"Well Tom…its Wednesday." He looked at me as though I were an idiot.

"I know," he lowered his voice. "Right now I don't have any assignments. If you turn this in now I'll have to tell my boss I'm ready for my next project, Joe, I'm on level ten in Flash Whack A Mole."

Internet games, God what an idiot. "Okay, so I'll hold on to this till Friday and you and I both won't have to work."

"Thanks Joe!" Off Tom went to play Whack A Mole. I can't stand it when people call me Joe. It's Jobe. There's a B.

Except the Boss, she can call me Joe. Hearing her say my name, in whatever way she wants to, is lovely. I think she's so beautiful, I suppose most people wouldn't think so. She's short, small breast, pale skin… and she's and most obvious dyke you've ever seen. The minute she opens her month you know she's a lesbian. And she has an air about her… I can only describe it as a masculine kind of presence.

I can't stand girly girls. I hate it when people act… well, overly happy. I rarely smile; people think I'm bored with them when I don't pretend to be cheerful, and… their right of course.

I'm headed to see the Boss, the high point of my day. But first I had to get past her damn secretary.

"Hey Joe what's up?" There she goes. Well I was thinking about how much you annoy me.

"Nothing Jill just came to see the boss." So don't say anything else, huh?

"Well I hope you have a good time." Damn you!

"Are you trying to say something?" I didn't mean to say that out loud, it's a good thing I didn't swear at her.

"Just that you seem to drop in a lot."

"Yeah, Jobe and the dyke boss are in a secret love affair." She giggled. I hate it when girls giggle. It grates on my nerves. When men make a low laugh like that they chuckle, the boss chuckles, she's a man inside I think.

I made my escape into the boss's lair.

"Oh, I'm glad its you Joe, I thought it was somebody that worked for me." She's always giving me crap. We both love sarcasm, I like the way she mocks everyone around her. I wish I could do that, but then I'd probably get fired. But wait… something isn't right… is it Wednesday? It is… she should be grumpy as hell. It could only be one thing.

"Did you have sex before you came in today?" She was shocked. "JOE! Not so loud… I mean… NONE OF YOUR NONESENSE TODAY JOE! GET THE HELL OUT OF MY OFFICE!"

I started to leave. "Hey!" I stopped and turned around.

"Yeah?"

"How'd you know?"

"Well its Wednesday and your happy, it could only be one thing."

"SHUT UP AND GET OUT!" She's really cool.

I wondered; Was that the high point of my day? After I escaped another drilling by Jill I made for the safety of my cubicle. If only it had a door I could lock.

Tom may have been on to something. For the next few hours I played some intense games of Whack A Mole. I didn't see how you could get to level ten; I couldn't make it past six.

My mind started to wander… the boss had only been the boss for a few weeks but we'd gotten to know each other fast. It occurred to me then that perhaps I could see her again at lunch. I don't know why it hadn't occurred to me but now that the idea was in my head I vowed to stop at nothing to eat lunch with the boss.

I spent the next hour fantasizing about eating lunch with the boss. I know, I'm a perv. Then came the fateful hour.

I was about to head over to her office when I felt the distinct impact of a fist on the back of my head.

"Ahh!" I turned around and there she was, as radiant with anger as ever and twice as sexy for it.

"You! You're coming to lunch with me!" She stood behind me giving me her fiercest glare, hands on hips.

I rubbed the back of my head, "Your request fills my heart with a joy the likes of which have not shined in this mortal coil since the days of my youth."

"Wha… well… Where going to Wendy's!"

Wendy's was just down the street. My boss ate with the same anger that she did everything else.

"You know boss, I think that the foods already dead."

"Shut up ass munch." She attacked her fries. "You know though, Wendy is my first name."

"I didn't know."

"Just don't call me it."

"Sure boss."

She finished quickly. She saw that I was only half done. "Shit Joe you eat like a bitch."

We both chuckled. I nearly chocked on my Jr. Beacon, which made it really funny to her.

"It's always funnier when someone gets hurt." She was really in a good mood. She started to chat with me, telling me all about her self. At first I prompted her to tell me about herself but before long she was volunteering more and more personal information.

I listened to every word she said, I had to know more about her… she was the most interesting person I had every met. In many ways she was an angrier version of me.

"This morning I had sex with a whore that lives next door." It's a good thing I was done eating. "Yeah, she in the oldest profession ya know?"

"I can't believe you just told me that." She was a hurricane, there was no stopping her.

"I like her cause she acts great. I like to dominate my lovers and she really makes me feel like she's my little bitch."

"Your so cool." She didn't seem to hear.

"You know Joe I used to think I was a lesbo but now I think the reason I like women is that I just need to be on top ya know? I need to fuck not get fucked ya see?"

"I can't relate…" Holy shit! Is she coming on to me?

"With which part?"

"I wouldn't know about being a lesbo."

"HAHAHAHA! Oh look, it's time to go back to work, chop chop Joe."

The rest of the day was a blur. What the fuck had just happened to me?

I decided that Wendy had come on to me. Even if she hadn't I wanted her, and when guys like chicks they let them know, right? I suddenly started to feel very excited. I didn't just want to come on to her I wanted to wow her, do something that would say; "Hey I may be guy but I can still be your bitch."

And so I invented Jubilee. She wears a long skirt, a baggy sweater, braids her long black hair into pony tails and wears red lipstick and fake nails. My own nails aren't long enough you see. Of course she'd shaved her body real good. The baggy clothes disguised my male (if girly) frame.

I looked good as a girl. I wasn't my type mind you, but I was dressed for a certain dyke.

Wendy was shy with me Thursday and Friday, she seemed down. I think she thought I had sent her some negative signal. But it would soon be remedied.

I knew the first bar she always went to start her hunt. Jubilee was waiting for her there.

I wasn't nervous at all; I could see that more then half the people that saw me couldn't tell I was a man. I would let Wendy get a little drunk, and then I'd be sure to go undetected. She always started off with two beers.

I could see her go into hunting mode. After her second beer she sat up and looked around, scanning the room for possible playmates. I ordered a beer and didn't look at her.

Then some punk sat down next to me. Oh shit.

"So how much?" The comedy.

"Dude, I'm a guy."

"I know, you look good though, at first I thought you were a girl, so how much."

"I'm not a Harlot." I love the word harlot. It's an old word for prostitute, if you didn't know.

"Everybody's got a price. What's your name?" He seemed like a smart guy. So why was he trying to pick up a cross dressing whore?

"My price is too high for you."

"Really? Here's the deal, I have some friends that love sissy boys and I owe them big, so if you could help me out…"

I realized that I had been using my girl voice. Shit.

"Listen here punk; I'm no damn sissy boy. I'm dressed up like this cause…" I looked back and saw that Wendy had already left. "Shit! Damn! Fuck! Ass! Bitch!" I looked back at him. "I'm should brake your neck you fucker."

"Wow now, I'm sorry I caused you trouble, how about I make it up to you? Do my job and I'll give you five thousand dollars cash."

Well, I had no idea where Wendy would go next so…I smiled, "Well, everyone has their price don't they? I'm afraid I'd have to ask for the money up front though."

He led me out to his car and gave me a purse full of money. I had forgotten to bring a purse. "You mean I get five gees and a purse, I'm feeling like a slut now baby!"

He drove me downtown to an old apartment building and led me up to the third floor. I was a bit nervous by now, but also kind of excited.

He led me into an apartment, then into the master bedroom. Sitting on the bed were two girls, dressed in cheerleader outfits.

Ridiculous. The one on the right smiled, "Wow, and I didn't think you could do it Roger. Thanks for the treat, you can go now." My escort made his exit. The girls introduced themselves as Sarah and Mary.

They both had nice breast. We guys always notice a women's breast before anything else. Sometimes it's hard not to stare. It's like there's a magnet in your eyes that draws them there. With practice, I've learned to turn the magnet off, but in this obviously sexual situation it had come back on.

Something occurred to me, "You know, I was sure I was brought here to be a bitch for some guys." They looked at each other and smiled.

"Nope, were all bitches here… but you in particular. We'll just call you Cunt, okay?"

"Sure." Whatever.

The girls motioned for me to sit between them and I did. Sarah got off the bed and sat in a chair, watching us. Mary put her hand on my chest and pushed me back on the bed and hopped on top of me. She pushed her lips against mine and kissed, soft at first, then harder. She didn't let up.

She pushed her tongue into my mouth, she ground her face into mine, and it was as if she was trying to fuck my face with hers. Her tongue darted in and out, fucking my mouth like a pussy. I sucked on her tongue like it was a cock and she went wild. Her hands flew over my body, pinching and squeezing everything.

Finally she pulled back; spit covered her chin and dripped on my chest. Slowly, she lowered her face to my ear and began to lick it; she pushed her tongue inside it, wiggling it around. I giggled. Then she started sucking on my earlobe, pulling it with her teeth, biting it softly.

Then she bit me hard. "Ahhh! Hey…" I tried to sit up but she pushed me back down, I could have pushed her off if I wanted to, but I wanted to see where this was going. She started to chew on my ear, biting it hard; gnawing on it is the word. I was in pain. I whimpered just like a girl and I could feel in her bites that she loved it.

When she finally stopped she sat on my chest panting. She looked at Sarah. Sarah said, "Not yet, don't get two eager we got all night."

She bent her face down to my neck and licked it slowly. Of course, she soon started biting me and doing her best to suck the life out of me. No surprise from my end.

Ounce she'd had enough she told me to get on the floor next to the bed, which I did. She presented me with her foot and the command, "Suck my toes Cunt."

First I licked under her toes, this didn't satisfy her. "I said suck them Cunt." She pushed her foot into my month; her hands moved to the back of my head and started pushing her foot into my month. She forced her toes in, and her foot hit the back of my throat.

Sarah spoke up, "Wow, I can't believe that little pussy month can take that much."

She wiggled her toes inside my mouth and pulled her foot half out, and then shoved it back in. She got a rhythm going, fucking my mouth with her foot. "You love sucking my nasty feet don't you Cunt?" She pulled her foot from my mouth then and pulled my face up to her breast. "Kiss me some now Cunt."

I tried to reach under her clothes but she slapped my hands, "Do it though the clothes, come on now, I'm almost ready for a fuck."

So I fondled and kissed her breast though her shirt. I felt around for each nipple and pinched it though the cloth. She smiled and looked at Sarah, "I'm really ready now Sarah."

"Go ahead."

Mary pushed me off her, and shoved me on the bed. "On your stomach Cunt!" I did as told. Her hand reached down under my long skirt and stroked its way up my leg. She moved her hand over my panties; around to the front she cupped my hard balls in her hand, squeezing gently.

I had almost had myself convinced she was really just a kinky girl that liked it rough, oh well.

She pulled my panties down to my knees and her hands left me for a moment. I heard Sarah chime in, "Not going to get her pussy ready?" Mary laughed, "You know that's not the way I like it."

I felt the head of 'her' penis touch my asshole. She pushed it lightly and against my hole and said, "This is gonna be the best fuck you'll ever have Cunt." Her hands reached up under my sweater and she dug her nails into my skin. Then she pushed her cock into my ass.

The pain was horrible, of course. With no lube whatsoever my ass burned as her huge rod slid into my asshole. She began to fuck my ass with total abandon. "Shit Cunt, your ass is so tight! Don't tell me you've never been fucked before."

I screamed in pain. She laughed, "Shit Mary this bitch is a virgin." Her strokes continued, "That bitch boy did a great job of finding us his replacement. I'm gonna fuck this ass all night. Come on Cunt, you don't like to talk? Tell me you like it. Or maybe you still need to be broken it, Sarah, you've watched long enough come let this slut taste your meat."

Sarah sat on the bed in front of me; in her left hand was a short whip. Smiling, she lifted her skirt up and pressed her crouch against my face. I could feel her hard cock pressing against her panties as she let her skirt fall over my head, making my whole world the burning pain in my ass and this tent for two, me and her cock.

I felt her hands pull my sweater up and the whip came down on my back. "So blow me already, and it better be good, or I'll just use your month as a pussy." I began to lick her balls and cock though her panties. Her hand came into view and pulled her panties down. Her cock sprang out, touching my lips. "It knows what it wants Cunt now give."

She pushed her cock forward slowly. I could feel the head pass between my lips, slid over my tongue, hit the back of my throat and push down into me. I closed my mouth around it and she slowly slid it out, till the head was between my lips.

I flicked the head with my tongue, circled it slowly, and felt it start to go in again. This time she didn't stop until her balls touched my chin, and my face was buried in her public hair. I heard slurping noises over my head. I imagined them kissing each other while their cocks were buried deep inside my moist mouth and ass.

Mary's fucking had slowed down but it started to pick up again, "I hope you're ready to have your first load of cum Cunt." Sarah started to fuck my mouth like it was a pussy. Didn't she say she wouldn't? My body rocked between them, they grunted and talked dirty.

"Oh shit yes bitch, get ready to drink my cum, oh god."

"Fuck, you're the best whore I've ever fucked; I'm looking forward to you being my Cunt for life."

Then I felt Mary blow her load into my ass, her cocked twitched and she screamed, filling my ass with her juice. A moment later Sarah pulled herself out of my month and her cum sprayed all over my face.

Mary's dick softened inside my ass, and Sarah sat back on the bed. "I don't think she knew Mary."

"I thought not, that just made fucking her ass all the better." Sarah bent over my face and slowly licked every bit of her cum off, Mary crawled over to her and they kissed.

"That was fascinating." My first words since beginning.

Mary smiled, "Don't go thinking we're done Cunt." She presented me with her limp dick. "Get me ready for some more." I hesitated, looking at the dick that had just fucked my ass. "Don't make me get myself ready, I think you've gotten the idea of what I like."

I opened my mouth and took her limp dick between my lips, flicking and rolling my tongue around it. "That's a good little whore."

Sarah smiled down at me. "Mary loves it rough and I like to watch her getting what she wants. So we make a great couple. Was this really your first time?" I nodded. Mary pulled her now hard dick out of my mouth and asked, "Are you enjoying this?"

"I find myself rather entertained."

"You're a weird one."

"Oh yeah."

We talked, and while we did Mary ran her penis around my face, over my lips and pushed it against my cheeks. Mary and Sarah were she-males (Obviously) they both loved to have sex fully clothed and liked men who'd let them fuck them.

I didn't know how much I enjoyed this, but I thought they were cool.

Sarah sat on the floor and motioned for me to stand in front of her. She pulled up my skirt and took my dick in her hands. She started to jerk me off while Mary sat on the bed, stoking her amazingly long ramrod.

It wasn't long before Sarah started licking up and down my shaft. She did it with a slow relish that couldn't have been show. She loved sucking cock, no doubt. Before I came she stopped. Mary took my hand and led my back to the bed, where I resumed my former position. She paused, and then flipped me onto my back. When she inserted herself into me this time she did it slow.

Her hands roamed up to my nipples and gave me light pinches; she wanted me to enjoy it this time. She slowly fucked in and out of my ass, and it did start to feel good. I moaned and told her, "Okay, faster, fuck me harder." Her pace increased and Sarah came over. She bent over and took my cock in her mouth.

Mary began to go full speed, with Sarah's hot lips on my meat it didn't take me long to scream, "I'm gonna cum!" Sarah pulled her lips away and started jerking me off. When I felt Mary's seed fill my ass for the second time that night I came all over my chest and stomach. Sarah greedily licked up every drop.

Mary pulled her limp dick out of my ass and Sarah took her place. Sarah's cock filled the void and it felt wonderful. Mary sat on my chest and pushed her limp dick into my mouth yet again. How much could this girl take?

It took her a while to get hard, and I enjoy the way her cock felt as it slowly grew, filling my mouth like a balloon. Sarah started to fuck my face as hard as she could. She pounded my head against the bed and slammed her cock as deep as it would go with every stroke. I loved it. When I felt Sarah's hands start to jerk me off as she fucked me I thought there was no way I could cum again so soon.

But I was wrong, Sarah shot her cum into my already cum filled ass, Mary's cock twitched and pulsed in my mouth, trying to shoot a load it didn't have, and I came all over my stomach. Mary sat for a long time in my mouth, "Your pussy mouth is so warm and juicy, I could stay here all night." Sarah, who is the biggest cum junkie in the world, licked my cum off my stomach and pulled out of my ass.

I couldn't see Sarah with Mary still mounted on my face, but I wasn't too surprised when I felt Sarah's mouth on my ass. Her tongue delved inside my rectum, I knew what she wanted, the hot loads of cum she and Mary had planted in my ass. I felt her sucking, and the cum flowed into her mouth. Sarah laughed, "See what a whore my friend is, drinking cum out of your dirty ass, hopefully you'll learn to love cum like that, since you'll be begging us for more sooner then you know."