Kris's Challenge

Background

While messaging online (That was on Friday 10th March btw), a friend and I were discussing how I’d tried a lot of things and that I was always thinking of something new to try. I asked Kris to give me a challenge and this is what he came up with.

The Challenge

Go out, dressed as a guy, and chat up girls…and try to pull one. (Oh yeah, to you people who might not know. In England, to pull someone is to successfully ask them out, or home).

Sounds easy enough right? I did it but it was complicated to organize and really, really hard to get the guy thing right. See what happened.

What Happened

Setting up
Something like this needs some planning. Can you imagine if I just threw on some guy’s clothes and went out on the street? “Hey, that chick’s dressed like a guy.”

First thing, I called an old mate Patrick. He’s a make-up artist for TV and movies and stuff. It took about two hours (you reading this Mr Challenge Man?) of make-up and some artificial stubble, strapping my tits down, and all kinds of other bollocks to make me passable as a fella. Then Patrick had to teach me how to move like a guy. Now, as you’ve probably guessed, Patrick is gay. That’s a gimme. Well, he may be gay but he’s not a girly gay. If you didn’t know or had your gaydar switched off you’d think he was straight, not macho straight but a regular guy.

So, he watched me walk, laughed and slapped his forehead. Over the next hour or so he coached me. By the end he seemed happy enough that I could get away with it for a night, maybe a few hours. The voice was next. My voice is soft but not that breathless, brain-dead model soft. I can drop it a bit and growl, specially when I’m horny. Patrick pretty much told me that if horny worked to lower my pitch, then think horny. I’m laughing as I write this part coz, come on, how hard do you think it is for me to think horny? It’s my natural state. Come on, Patrick, what kind of dick are you? Duh!

Last bit was what to wear. That part was easier. Just standard guy going out to dance gear. Yeah yeah, I hear you but really, how much trouble does your average guy go to? Just chuck on whatever’s nearby. A cap to hide my rolled up hair and ready. Sorted.

On the town

I had to travel pretty far from home coz people know me around here and I didn’t want to get tumbled right at the start. How the fuck am I going to get away with this? Anyway, I found a club that was pretty packed and figured I’d better get into the whole thing or else I was going to freak and bail. First off I grabbed a lemon stolly then thought “Oh fuck!”, ditched the chick drink and got a lager. How do you know how to do this shit when you’ve never done it before? How does a guy pull? Then it came to me. Fuck it, I’ve been pulled that many times, I just gotta like reverse it.

The first coupla chicks give me the “oh please!” look and turn away. Yeah, it’s funny how good you get at ignoring guys when you’re in a club with your mates. When it’s late it’s worse coz they’re all pissed (drunk) and it’s harder to get em to take no for an answer. So I’m there and scoring a big zero, but I keep trying. Sorry guys. You must think we’re the biggest bitches but look at it from our point of view. A hundred dicks with fellas attached wandering about trying to get a fuck before the music stops and there’s us, looking to them like we’ve got a huge sign over our heads saying ‘FUCK ME’.

Anyway, I found one chick who was a little pissed herself and started chatting. She was slurring her words a bit and she kept saying how I was soooo sensitive and not like other guys. We wound up snogging a bit but after a while she got up to go for a piss and just didn’t come back.

Now it was getting late. I was standing around thinking I didn’t care if I pulled or not. It’s a challenge, not a contract so sorry Kris, I’m outta here. Up went the bottom of my glass of lager, the fifth or sixth of the night, I lost count, downed like water. OK, home time. I’m almost out the door, feeling the cold air blasting in from the windy street outside and I see this sad looking chick sitting by herself at a table in a darkened corner by the door. She looks up, gives me one of those downhearted “oh hi” kind of smiles and drops her eyes back to the glass in front of her. She’s picking at her fingers and really looking empty. Just another depressed chick I think. Probably dumped by her boyfriend or stood up. Who knows? When you go to as many clubs as me you see it all the time and these chicks wind up being as familiar as the long bar or the thumping music.

I think ‘why not’ and gesture to sit down. She gives me that ‘whatever’ kind of sideways flick glance and goes back to examining her glass.

“I’m Chris” I say

“Julie…Jules” she replies.

“Drink?”

“Yeah, alright…” Her eyes brighten a tiny bit “…Baileys and milk” Her voice carries no enthusiasm but at least she’s talking.

“Be right back” I say and wade through the dicks and chicks back to the bar.

When I get back she seems to have gotten her shit together a bit and actually smiles at me. She thanks me when I hand her the drink and we make conversation. Turns out she was supposed to meet her boyfriend Rick here but he phoned her about twenty minutes before I saw her to say he wasn’t coming. Something to do with a car and some weed. He pulls this shit all the time according to Jules. She wants to dump him but “…you know?” Yeah, I know. She’s got a dipshit for a boyfriend but at least she’s got one. This kind of sad bullshit goes on every day. Chicks hanging around coz they’re too fucking down on themselves to imagine they’re worth more than the crap they’re handed. So there she is, sitting at a table in the corner of a trance-thumping club feeling sorry for herself and trying to find the strength to get up and go home.

It takes a while but after the usual “…so what do you do?...” chat, she puts her hand on mine and says “I really like you. Thanks for talking to me.” Thanks! Like I’m doing her a favour. This chick really needs to get some bottle. No wonder her boyfriend treats her like shit.

Long story a bit shorter, I ask her if she’d like to come home with me. She makes a show of hesitating and “How can I, I’ve got a boyfriend…” and then says yes, of course.

Once in the door of my flat, she lunges at me like a hungry wolf and we wind up on the bed. We’re kissing and grinding at each other and I’m running my hands all over her body. I can feel she’s wet, right through her knickers. She’s panting and groaning and the temperature in the room is getting to critical.

Then she puts her hand between my legs and everything stops.

Her eyes go through about a thousand emotions in the blink of an eye. First, confusion, then fear, anger, more confusion, then outrage.

She says something about not being like that and wriggles around a bit, making her way off the bed and then I touch her wet pussy again. She raises her hand to slap my hand away but instead she pushes it harder against her. I pull her back towards me again and the look in her eyes again cycles, but this time it goes from confusion, to resignation, then to lust.

Jules fucks my hands until she cums, and cums within seconds strangely enough. She overcomes her prejudice quickly and we spend the next few hours bringing each other to climax after climax. The first time her tongue rubbed against my pussy was the first time she’d ever done anything at all like that with a woman. Even when she was a kid, she told me, she’d never felt any kind of desire to even try it. By the end of the night I think she was converted.

She asked if I’d be her girlfriend if she fucked Gary, her boyfriend, off but Christ, the last thing I need is some chick who attaches herself to the next thing that comes along. She rings me every day and just about an hour ago, while I was in the middle of writing this, she called to say she’d dropped Gary coz she’s met this “…really nice girl who thinks I’m lovely…” Shit, she sure loves riding that roundabout. I hope this chick she met isn’t just a female copy of Gary but she probably is. Some chicks never learn.

So Kris, I did it. Anyone got another challenge? Once I get over this flu, I’m ready to take the next challenge.

©.2006, Lisa
http://lisa-scribbles.blogspot.com/