To Be A Gangsta

Ahem, OK... I'm ready, are you? Of course you are, you followed the link here... But you may not realize that this story is the sequel to Jobe, Cross-Dresser Extraordinaire. So now you know. If you've never read that go check it out. Or get ready... set...

Being sidetracked is a bitch. I'm such a failure, I swear. Always thinking with ya pecker Jo? Little bastard causes me no end of trouble. A night wasted, anyway... eh... where was I... Oh yeah failure, time to be depressed.

I'm such a loser blah blah blah blah blah blah. I can't believe blah blah blah blah blah blah blah blah blah blah balh. Why did I blah blah blah blah blah blah blah blah blah blah.

Okay, I'm over it. Time for a pep talk. I can do it! I believe blah blah blah blah blah blah blah. Next time I'll blah blah blah blah blah blah blah blah. With a little blah blah blah blah blah blah.

Blah.

Damn I feel ready to procrastinate until my chance has past me by and all that's left is regret that I never tried. Yeah time to play some Flash Whack A Mole. Damn them little mole bastards are fast.

The Buddhist should use flash games as a form of meditation. After ten hours of trying desperately to reach that perfect score, that unattainable goal, the figures dancing in 2D on the screen... your mind grows numb, you no longer think about what your doing, and yet the points come faster, urging you on, and then you feel it. You suddenly know, no, not know...

COMPREHEND. You reach an understanding of the game, you see how Tom got to level ten, it flows through you... filling you up, and then it breaks like a tidal wave, leaving a clam wind blowing inside you, and surely this is nirvana.

Or not... ya know whatever. Maybe your not so amazed by free arcade games, but their really something.

What was I doing before I got off on this? If you're going to insist on listening to my private thoughts I might as well fill you in. I've been trying to score with my boss lately. Yeah I know, will you shut up and let me tell the story? Damn.

Anyway she's gay, well, hopefully bi, but but she sure loves them hoes. Bad news is I'm a guy. But hey, I've got long black hair, that's a start right? Don't bring me down I do that to myself. But look, win or lose, as long as you can say you gave it your best shot its cool. Last night I attempted to pick her up at a bar by dressing a girl, but I got... ah... a little off track. But I ain't no quitter. That's right I say ain't, lay off me.

Yes I know I'm sitting around playing flash games when I should be "giving it my all." I swear I'm gonna get right on this when I beat Fox895's high score. I almost got it... just a little...

The phone rings, like a monster interrupting a few teens sexual exploits it could not have come at a worse time. Abandoning my quest for glory I head for the phone.

"Hello?" I answered. I think to myself, this better be as important as Whack A Mole.

"Hey Jobe, what's up?" Tom's voice... on my phone, it took a moment to sink in. Son of a bitch!

"How did you get my number?" Perhaps a better question would have been, how could my life be this bad?

"The PHONE BOOK DUMB-DUMB!" I'm not even gonna make another negative comment, I can deal with this.

"So what ya want Tom?"

"I was just thinking we should go get some beer's, Sunday night, work is tomorrow let's have a good time, what do you say?" Negative thoughts... can't stop... Great idea, get hammered so you'll be as miserable as possible for work.

I was about to blow him off, but perhaps my time spent in battle with the moles had brought me to a higher plane. The time has come to deal with this Tom fellow, to make sure that he never says another word to me. I had a wonderful idea. I would don my disguise, meet him at the bar and make a pass at him. Tom should be sufficiently disgusted to leave me the hell alone.

I'm a ruthless bastard; Mao Zedong has nothing on me. What? Don't know who Mao was? Well look him up! Damn, I ain't ya dictionary.

I got dressed with a certain amount of joy, not to much, don't want to get to cheery, have to have a straight face when I go in for the kill, ya know? Its times like these when I notice myself having some of that self respect those teachers are always going on about. Let's all give ourselves a pat on the back, go ahead. Pat pat, I did. Oh, and might I say I am a sexy beast, I hooked myself up with some phat blue lipstick it matched my blue skirt. I could fuck myself if I met me.

Tom was at the bar nursing a beer when I walked in, some friends were with him, oh... this would be so sweet. I set my face in a smile, and rolled on into battle.

"Hey, Tom!" I used my most girly voice, Tom and his friends looked at me. Tom didn't show any recognition. But he dug himself a nice hole for me to toss him in.

"Hey there pretty lady, why don't you sit down and have a beer?" My thoughts exactly cock knocker.

I sat beside him and wrapped my arm around his shoulder, speaking in my normal (drop dead sexy) voice "When you said we'd have some fun I thought it would be just the two of us like normal." Tom was speechless, and his friends stunned, he looked like a fish out of the water with his jaw gaping.

Lipstick: eight dollars. Ear-rings: eighty dollars. The look on some assholes face when you go straight gangsta and fuck his ass up: priceless.

Tom's friends made their assumptions, and looked at Tom with an expression of horror. I watched as my mere presence and a few words led Tom into a heated debate concerning his affection for men. My work done I quietly snuck off, cause when your this gangsta you gots to worry your gonna get your ass handed to you by some punks you got freaky on.

I moved over to the other side of the bar and ordered a beer, because I deserve it, pat pat. One beer became two, and two three, he invited four who hammered my ass good. I am under the influence ladies and gentleman.

Some women sat beside me. Don't ya know my victory party couldn't just go straight from sitting down, getting smashed, and then puking? No, somebody always has to get up in my jelly.

"Hey, what's your name?" This girl seemed familiar. She ordered me a beer.

I liked her already. "The name's Nancy... err, no it's Stacy, no wait. There's way too many names like that in these stories, I am Daisy Hornblower of Waymoot!"

The stranger rose an eyebrow, "Oh yeah, you sure Daisy?"

"Err, yeah, pretty sure. That's the closest hobbit equivalent to Catherine Long. I'll go with it anyway." My speech fell naturally into my role, years of D&D role playing at my disposal. Yes good sir, I will slay this dragon for you.

The interloper tipped a beer to her mouth, a serious look on her face, and then I recognized her, Wendy. The Boss, she was sitting next to me, getting drunk. Why hadn't I recognized her right off the bat? Damn. I'm more smashed then I realized, why didn't I eat something? Yes I know I was planning on getting wasted but I still feel I've shown a lack of foreseeing hindsight. I should have expected some bullshit like this would happen to me.

Have you ever been drunk while doing something important? If you're lucky you'll have the focus to repeat to yourself, "Don't fuck up, don't fuck up, and don't fuck up."

I felt Wendy's hand on my thigh, like the litany against fear I begged myself not to fuck up. She leaned over, her lips next to my ear. She whispered, "How about coming over to my place?" Her hand caressed my thigh, sending a shiver up my spine.

"Oh boy, yeah." Could I sound any dumber? Wendy paid the bill and escorted me to the street corner, my heart was pounding as we rode the taxi to her apartment. Her hands were all over me. I squeezed my legs together to keep her from discovering my cylinder companion. She kissed my ear and sucked on my neck.

I'm gonna have to go to work with a hicky tomorrow. I could see the cab driving in the rear view mirror; I don't think the show caused him any pain.

I kept my stumbling to a minimum as Wendy escorted me up to her room. Of course I knew she'd find out, I mean, it might take five minutes, it might take ten minutes but it was gonna happen. But in the words of Canderous; "Win or lose, as long as a battle is worthy then honor is gained. If there's nothing at stake, your life, your possessions, your world, then the battle is meaningless."

Alright maybe that doesn't exactly apply here but give me a break, it ain't easy bein greasy. But at least being able to focus like this is a clear sign that my buzz is wearing off, that's definitely good.

Wendy practically dragged me to her bedroom and pushed me down on the bed. She sat on my chest and looked down at me smiling. I reached up and slipped my hand up her shirt, her skin felt so soft, I was in heaven... drunk.

Wendy bent down and pressed her lips against mine. Her tongue probed my mouth, I sucked on it and swirled mine around it. Wendy's hands held my head, keeping me at an angle where her tongue could reach every corner of my mouth. I had never been kissed like that. Her passion was so raw; so aggressively, it felt like she wanted to eat me up.

She pulled away for a moment; tossing her shirt and bra she pressed her lips against mine with the same hunger. My hands pinched her nipples, twisting and squeezing them. They roamed over her stomach, down her back, tracing her spine.

My lungs burned for air, her lips stole my will to breathe, soft and so demanding they pressed against me. All I could do was close my eyes and feel her hot lips and tongue. Her hands gripped my hair and pulled my head back, our mouths parting. A few strands of spit hanging from our lips. I gasped for breath as she licked my neck. Saliva dripped from her mouth and ran down to my shirt.

She pulled herself away for a moment and discarded her jeans; I stared at her white cotton panties. Girls always look so hot with just panties on. It's like you can see anything you want, but ah... not that. It taunts you, it begs you to come closer and see what it's like under there.

Wendy hopped back on me and crawled up to straddle my face. My tongue licked over that barrier, that thing in my way stopping me from tasting what I wanted. I pressed my mouth into her mound, sucking and licking it through the cloth. She moaned and reached down, pulling her panties aside to give me access to the prize. I dived right in.

My tongue had a mission, this was it's chance to get inside Wendy and the little bastard was overjoyed. I ran it up her cunt, flicking her clit; I pushed aside her lips and pressed my voyager inside her. Her sighs and moans spurred me on. I sucked on her mound while forcing my tongue in as deep as I could get it.

The walls of her pussy squeezing it, my lips pressed against her pussy lips. I kissed her cunt like she had kissed my mouth, wanting to devour it. A sweet flower that poured honey into my mouth. My tongue felt at home in her moist pink tunnel, it wiggled around and circled the entrance, her juices flowed over it into my mouth.

Wendy panted and moaned, she ran one hand through my hair while twisting her nipples with the other. She ground her cunt into my mouth as she came, her body shuddering, sweat ran down between her breast. She dismounted me and lay on the bed next to me, sighing.

"You're a strange one Jobe." Damn, ah well; better that she knows I guess. She continued, "I never would have figured you for such a fairy."

I countered, "Hey, I'll have you know I'm straight gangsta. Dress like a girl, dress like a guy, it's all the same to me, so long as I get what I want. I'm ruthless, a thug in sheep's clothing..." I rambled on about how great I am.

Wendy (who was clearly denying how enthralled she was by my mojo... err) knelt in front of a dresser and rummaged around. Pulling out a strap on and "equipping" herself I suppose you could say. I was not surprised, but knowing what a dominating bitch Wendy is (I say that with no ill will, it's part of what attracted me to her) I figured I'd put up a bit of resistance so she could have the pleasure of breaking me in or whatever.

"Hey now, your not gonna like... you know... with that..." Damn I'm a good lair, thanks D&D.

Wendy looked over at me, I imagined myself through her eyes, me in a skirt, sprawled on the bed with her juices running down my chin.

"Oh I would not have picked you up normally, since, you know, you're a guy. But seeing what a fairy you are I just got all these fun images. You'll do what I say or some of your buddies might find out, I'm sure Tom would be a little surprised."

I barely contained my laughter, he wouldn't be quite as shocked as she thought, and here my plan to get with her had worked in an entirely different way then I'd imagined.

"What are you smiling about?" She glared at me. I replied, "Just admiring how ruthless you are. I guess you got me, I'll do whatever your want sugar lips."

"You can start by NEVER CALLING ME SUGAR LIPS AGAIN, and then you can get over here, on your knees."

"Don't you mean 'on your knees bitch'?"

"SHUT THE FUCK UP AND DO IT CUNT!" Roar tiger, roar.

I crawled over to her and looked up into her eyes. There wasn't really any need for me to be told, hell I wanted to anyway.

"Mmm, that's a beautiful cock you have mistress. Please let me touch it, God, I need your cock." Wendy stared down at me her eyes staring as I begged her to fuck her little toy. I reached out and wrapped my hand around her tool, "Oh Wendy, I can't wait for you to fuck me."

I jerked her rubber manhood, "Little Daisy is such a slut, she needs you to be her owner." I put the head in my mouth, my eyes looking up and telling her how wet this was making her bitch.

"Wow, ah, you're pretty good at begging Daisy." Wendy watched me suck her dick with growing lust.

I pulled it out of my mouth and ran it across my lips, "It's easy when you mean it mistress." I'd like to give a shout out to my old dungeon master, yo Parryman, YOU DA BOMB!

Wendy smiled and ran her hands through my long dark hair. "Well get on your stomach on the bed, and lose the underwear." Those fucking panties got GONE.

Wendy knelt down behind me and lifted up my skirt, running her hands over my ass she kissed each cheek and started to lick them all over. I would never have expected her to tongue my asshole, it would seem Wendy was a dirtier girl then I had thought, not that I mind, who does when their in this position?

She licked up my crack, then pelled her tongue down over it, she kissed the entrance, then put her finger against it and pushed it in. "Well that went in easy."

I smiled, "Well, I'm not a virgin back there Wendy."

"Wh-What?"

"I've been fucked in the ass before, sure. I love it." I looked back to watch her reaction.

"You enjoy getting it this way?" Perhaps my acting is top notch, but the truth can be hard to swallow. "Yes Wendy, I can't wait for you to take me, I'm all yours."

"Holy shit!" Wendy reached inside her harness and I saw her hand going wild. She pressed her lips back on my ass, her tongue eating out my ass like I'd done for her cunt.

"Oh shit Wendy, ahh, that's so good. Give it to me... come on... I need it. Fuck your little bitch, she's ready for you." Wendy stood up and took hold of my hips. She lay her cock over the crack of my ass, then ran the head down to my entrance.

"Yes, right there, push it Wendy, fuck me. I can't wait any longer." The soft rubber head of the cock pressed itself against my ass. I quiver in anticipation and then Wendy forced the head into me. Grunting I pulled a pillow to my face biting it and wrapping my hands up in her sheets. She drove down into me, the rest of her member diving into my ass.

Her hand came around and found my penis hiding under the skirt. She hadn't even touched me yet and I hadn't thought about it. This was too good to expect to feel her soft warm hands on my shaft, but there it was. I moaned into the pillow, arching my back against her. She squeezed and jerked my cock for a moment, then placed both hands back on my sides; she ground her hips into me.

The burning in my ass was so hot; she pounded me with a ferocity I'd never experienced. My whole body trembled as she took me. But suddenly she stopped.

I was desperate, "No don't stop Wendy please." I am Jobe's inner bitch.

She chuckled "Turn over bitch." I pulled off her rod and lay on my back. She bent over me and took my face in her hands, pressing her lips against mine. I wrapped my legs around her, pulling her to me, I felt like such a slut, with anyone one but Wendy I might have been uncomfortable, but with her naked body against me how could I give a fuck? Well I would give her a fuck, but not like, I mean, whatever.

One of her hands held the back of my head and the other wrapped around my back. I felt the head of her cock and my hole again and her arm pulled me towards her. I moaned into her mouth as she entered me. Her cock parted my cheeks and entered my depths with much less pain. She started to fuck me as fast as she could, ours lips still pressed together. Our teeth banged, we bit each others tongues; it didn't matter.

I thought this couldn't get any better, but I was wrong. Her hand left the back of my head; I leaned into her to keep our tongues together. My eyes closed as I felt her hand on my cock, she jerked me as fervently as she fucked me. It was too much, my ass being pounded, my tongue exploring her pretty mouth, and her fingers pumping my cock.

My body quaked as I spurted onto her breast, strands of cum covered her hand and ran down her chest. She pulled her face away and stared at her hand. I lay back, watching her happy and serene after my orgasm. "It's been a long time since I've had any of this stuff on me." Wendy stared at her cum coated hand; I reached out and took it, pulling it to my mouth. She watched as I gave my best performance of the night, licking my cum off her hand slowly, with an obvious relish. When I had it all in my mouth I went after her breast.

There's something about a women with cum on her tits that's just so hot. I'll be damned if I know what it is, but it's there. The only sounds were of her heavy breathing and the smacking of my lips as I slurped up the cum from her soft skin. I looked up at her proudly, opening my mouth to show her all my white jizz filling my mouth. She did exactly what I'd hoped, gave me a wet, cum soaked kiss.

We lay on the bed and just kissed, on and on. Stopping only to breathe and stare into each other's eyes. My cock rose from its break, ready for whatever Wendy needed. She felt it pressing against her stomach and unbuckled her equipment. Tossing it aside she mounted me. It was too good to be true; I would get to fuck Wendy. She took my rod in her hands and pointed it up; slowly she lowered herself onto me, impaling her delicious body on my manhood.

Her cunt was so wet; her lips parted with ease and allowed me access. This was slow and sensual, a complete turn around from the hard fucking of a moment ago. I was reminded of the words of Tenacious D; ya don't always have to fuck her hard.

I reached down and rubbed her clit as she bobbed up and down on me. Wendy was lost in her on little world, and I did love the show. She moaned and ran her hands over her breast. Panting she started to fuck me faster. She must have cum then, she squealed (she sounded like chipmunk or something, I'll have to taunt her about it later) and shuddered, but didn't slow down.

I swear she leaked like a faucet, sweat and cunt juices dripped onto my stomach, wetting my balls and flowing over my sore asshole. I felt myself close to cuming. Wendy read my mind.

"Just a bit longer, hold on..." She gasped for breath, the exhaustion of all this fucking catching up to her. I needed to hold off... Martha Stewart naked on a cold day! Sound advice Powers.