Innocent guys stand around the bar arms crossed and fidgety as they look on in utter awe at the tight asses and pert breasts of bootie shaking, whored-up, wannabe socialites.

The creeping impaired look on as vultures swarm these vixens, showering them in a sea of attention that they eat up like a bulimic stripper at a Chinese buffet with a puke bucket.

Knowing there’s no way they’ll ever exchange words with the club-light enhanced enchantresses, the wallflowers instead clamor to a glimmer of hope that they might graze a breast or an ass cheek when one swaggers by.

As the night comes to an end, the awkward and unconfident observers go home alone to pleasure themselves with thoughts of the unattainable sensually grinding to Flo Rida. Sometimes they’re so apprehensive that their sexual fantasies turn into porn films where they themselves aren’t even starring, but instead they conjure the image of the Affliction-clad toolboxes they saw cling to the ladies at the club.

This all could have been averted if they just made a fucking move. Girls love a guy with balls. That’s kind of hard to find these days so if you could at the very least fake like you have some, a girl who’s drunk and impressionable could buy it and you might be lucky enough to get her on her knees. The girls have done it before, why wouldn’t they do it again?

Introduce yourself, but then play it cool. Don’t cling to her like she’s your favorite jerkoff pillow. Make her wonder about you. Don’t fix your eyes on her tits, ass, or belly ring… Look her in the eye. The reason being that it’ll make her nervous, and therefore set you apart from the rest of the lecherous scavengers that have been questing after her.

Suddenly she’ll be wondering:

         “Why isn’t he looking at my boobs, why isn’t he looking at my ass, I’m dressed like a whore can’t he see that? Oh god, I look like shit. Excuse me while I go throw up.”

If you make a move and a broad thinks you’re an asshole and finds you annoying, she’ll still have more respect for you – the guy who takes a shot – than the pussy who stands in the corner all night with the dudes like he’s at a junior high dance. Remember, just because you are a pussy, doesn’t mean you’re getting pussy. It doesn’t matter that the broads have bisexual tendencies.

Groups of guys constantly spend their boy’s night out cockblocking themselves with worry.

      What do I say to her?

      What if she doesn’t like me?

      How do I ask her out?

      When do I kiss her?

      How do I make a move to go further?

      When do I stick my dick in her?

      Is it okay to come on her face?

      When’s the right time to stick it in her ass?

      How do I know if it’s okay to ask for a threesome?

      When is the right time to pee on her?

      Would she think it was weird if I asked her to fuck me in the ass with a strap-on?


There’s an endless stream of questions guys are constantly contemplating which simply get in the way of buying a girl a drink, ripping her clothes off, and fucking the shit out of her. It’s simply that easy. Just try to be safe, girls could be dirty.


      My humorous, erotic, autobiographical novel “The Wingman Chronicles” is now available on Amazon. Check out description, customer reviews and a free sample right here.

My filthy novel The Wingman Chronicles


By James Holeva

I try to turn every haircut I get into a one-night stand. It’s my way of tipping the girl. Often times, if you go to a girl who has her own one-woman shop, on a day that isn’t too busy, you could get a post haircut present.

If you’re in need of a sure thing – you’re having trouble getting a girl to go out with you, just getting back out there after a breakup, the very sight of you repulses women, whatever – get a haircut.

It’s the perfect creeping opportunity – a built in date. No matter how much of a loser you are they have no choice but to talk to you. They can’t blow you off, ignore you, or ask a cockblock of a friend to get rid of you.

You might be one ugly, scary, gargoyle looking motherfucker, which means in the bar, in the street, at the mall… you approach a girl and they’ll run the other way into the arms of a bouncer, police officer, or rent-a-cop, but that’s only because leaving is an option.

Why do you think most guys who kidnap women are creepy looking?

A haircut is your way to abduct a woman the legal and safe way. Which reminds me, always have condoms concealed on your person when you’re getting your beauty treatments.

If you’re a good looking cat with game, this should be easy. If you’re recently out of relationship prison with a woman — whether a minimum, medium, or maximum security facility — it’ll give you a chance to talk to a girl again, where she doesn’t have the opportunity to get away. Imagine like she’s tied up, but you aren’t committing a felony. Pretty cool, huh…

Look for “The Wingman Chronicles” hitting book stores in next year to read the rest of the story!


Wednesday, July 13th 2011


The Quarterback Whore

Is it weird that my boyfriend wants to bang my mother?

No… The reason he probably entered into a relationship with you is because you have a hot mom. Let’s face it… If the Mom is gross, it won’t be long before you are. Consider yourself blessed. I think a Mother-Daughter orgy is in order. Think of what it would do for Momma’s self esteem. Let’s face it, how many good years does she have left? I think you owe it to your Mom to throw her a bang from your beau.



A friend’s fiancé texted him after three years together saying she “couldn’t do it.” And kept the ring. Any suggestions or advice?

She’s a golddigging whore who got what she wanted. I’d say kick the bitches ass, but she’s probably a pussy and would call the po-po. So if you want to help your friend sneak into the bitches’ house when she’s sleeping, and get it back. And take a few other souvenirs along, too.


Brad F.

Why are penis’s gross?

Well Brad you have a guy’s name so it’s nice to hear you find penises gross. Stay with that mentality. But, speak for yourself. I’ve been told my cock is a work of art. Spread the word.



Should I offer money up front since dinner/movie and whatever else is gonna be close to $200.00 anyway, and that bitch could get a card payment out of it?

I think so… Then all parties understand the agreement. But I would get something in writing.

If you asked me a few years ago I would say that a lot of girls would take offense, but in this economy I think a guy offering to pay for their services would be a welcome advance compared to the douchebags and bullshit they hear on a regular basis.



Can I touch your butt again?

Hmm… As long as you’re not a dude… Sure. Keep coming out to shows and I’ll let you graze, slap, and squeeze the ass anytime. Stay away from pinching though because it hurts.



I know girls use tampons for there women problems… Is it alright for a man to use a man-pon, if you have swamp ass and are a heavy sweater? Is it something you have to explain to your girlfriend?

If you require some sort of, “man-pon,” I would keep that from a girlfriend… Completely. However if you’re looking to get rid of a clinger, then by all means bring your Man-Pon for a bedroom show and tell. You’ll never see the bitch again.


Christina A.

Why do guys get whiskey dick?

So they won’t be able to make a drunken mistake without a condom, and end up with a drunken mistake for the rest of their life. I’d rather drink Jack and Jameson than take them to soccer practice!


Amy A.

Are bumps on a penis normal or something to worry about?

Amy, I would have this penis you speak of, see a doctor. I am not qualified to provide a medical diagnosis of cock. And please don’t send anymore pictures.


Dirty Harry

How come some girls have smelly snatches and some girls don’t?

Some crotches are working more than others… Chances are the girls more likely to fuck, have had more cock traffic, and therefore have a worse stench. It’s like a public bathroom is usually smellier than a bathroom at someone’s home because they’re getting more use.


Last night I facebooked a chick? Good or bad?

Good… Facebook has replaced Myspace as the world wide creep engine. It’s where power moves are made… Dates, relationships, and random bangs… I think people are  more comfortable if they know someone via facebook. Something about that list of activities, photos and statuses to read makes the girls comfortable. Just make sure you’re not talking about smelly snatches in your statuses. That might not work in your favor.


Joe L.

    1. If a girl says no to sex but she’s smiling, does she really mean no?

No she doesn’t… She just doesn’t want to come off like a whore. Enjoy the challenge. She wants you to work for it. Let’s get creepin’ (Disclaimer: A smile doesn’t give you a greenlight to rape her.)

    2.   Is it rude to tell a girl she always drags her teeth?

Although she might take it that way it’s your duty to tell her. The reason she rakes the teeth is because no guy ever told her the truth before. Do it… And you’ll be experiencing less pain, and helping all the guys she’ll blow after you. After you deliver the message, have her get in touch with me. I’ll evaluate her progress.

   3.   How do you proberly handle “overgrown bush” situations?

Grit your teeth, close your eyes, and imagine you’re eating a tasty peach.

   4.   Is it wrong to high-five after sex?

On the contrary, it’s only proper if you want to keep it a non-exclusive friends with benefits situation. It’s like high-fiving after a good run, weight training session, or bike ride with a workout partner.


How many girls like to get anal and then finish off with a blow job?

More than you think… A lot of girls are nasty. So enjoy  them. Don’t come out and ask for the anal/bj in that order… Just let the nastiness occur. If it’s in her, it will.


Kat D.

What’s a flexsexual?

I’m guessing some sort of gymnast. Sounds hot. If you know any send them my way.


How do you get cum out of hair-extensions?

Just lick it off… Wait that might not work, but would be fun to watch. You know just leave it there… You’ll pick up more guys than ever before. You’ll help guys to live out their Cameron Diaz fantasy.


Bobby D.

How many girls have given head in a Porta-Potty?

Almost all… Ever had lawn seats at a rock concert?



If you’re butt-fucking your girlfriend for the first time, and she says it hurts or she starts to cry do you tell her to suck it up and keep on pounding or stop? Practice makes perfect you know…

Keep going… No pain, no gain. She’ll thank you later.


Alex M.

When receiving a blowjob what is the proper way to “notify” her when you are about to cum, when asked to do so?

Don’t. Women like to be surprised. And if you must just use the classic “I’m almost… I’m almost… I’m just about… I’m gonna… I’m right there… Fuck you’re so fucking good… Oh yeah… Just about… On my way… Ready, ready… Yeah… I’m CUMMING!”



What is the best position you recommend for man and woman?

When a girl gets on top it makes us cum the quickest, but feels really good… We have the most control in the missionary or doggy style. It depends on the girl… If she’s got a nasty face you’re gonna wanna go doggy style or reverse cowgirl so you don’t have to look at her. Same goes if she’s got a great ass. Where as if she’s got tremendous tits you’re gonna want her to ride you cowgirl style so they bounce up and down… And if she’s got beautiful eyes and full lips missionary so you could make the most of kissing during sex.


Pat L.

What do I need to do to make a baby with all of the Coors Light girls?

Hire me as your Wingman… And woo them with hype and lies. They’ll believe the bullshit when it comes from me. Also, don’t tell them this was your question.

One Eyed Wonder Weasel aka Two Walnuts

Is it more embarrassing for a man to not be able to “get it up” or to cum prematurely before a three-way with two girls?

To not be able to get it up… Cumming quick is expected under such circumstances… And you could always cum again. The first round is a warmup so you don’t pull a hammy.


Michael H.

If you were in the super market and you spotted a girl sportin’ a camel-toe, would you warn her or just laugh your ass off?

I’d use it as a pickup line… “Hey… Your toe’s showing.” She’d be happy I gave her the heads up and was nice enough to notice, and it would lead to some a conversation, and ultimately an uncouth adventure. Obviously, I’d be holding in my laughter the whole time until I told my friends the story.

Here’s an instance where I couldn’t hold in a laugh during sex.



At the age of 85 they are still having “fun” so how would they keep things fresh in the bedroom after being with the same person for that many years.

They’re so senile at that age they don’t remember each other anymore so every time they bang it’s like a one-night stand. Plus those old guys are pumped with so much Viagra they’d stick their dick in a toaster oven… Just so they could get soft enough to go out in public without getting arrested.



What is your favorite asset of a woman besides eyes? And would you like to come on mine?

After eyes… It’s a tie between tits and ass. I appreciate both equally. And, assuming you’re a sexy girl (I’m a club is half full of available ass kinda creeper) then yes… But if you’re nasty… I’ll say maybe (depends on the amount of alcohol)… And if you’re a dude, no offense but NO!



What is the size of your penis? Diameter and length… (Inquiring friends want to know.)

8.5 inches… Like I said in the show, “Huge but manageably huge… As big as you want that you could work with.”

While I never measured girth… I’ve gotten compliments on it as much, if not more than the length. Send a pic and if you keep coming to shows, I might let you see for yourself.


Dirty Harry

I always get rug burn on my face when I go down on my girlfriend. Is that normal?

It depends… Is your girlfriend a seventies porn star?



Where is the strangest place you have had sex?

In a high school girl’s vagina… With her father in the room.

Let me explain… I was in high school, banging my first girlfriend in her parent’s basement, and we heard her father walking in. I quickly reached for the blanket, and covered up. I was scared out of my mind.

She was on top of me cowgirl style as I sat up straight, and I quickly slid her to my right but my penis  remained inside her. Her Dad walked in, and proceeded to have a conversation with us — sports, movies, general chit chat. He was in the room well over five minutes, and the whole time we just remained still, but my penis never left her.

How many orgasms can you give a woman and make her beg for more?

Over, and over, and over again… I once came nine times in nine hours, fifteen times in thirty-six hours. But, each of those ejaculations led to multiple orgasms for the broad. Plus there was cunnilingus, finger-banging, and breast induced orgasms involved. I have the mental edge… Read this piece:


Michael H.

Is there any type of sexual act you’re embarrassed to ask for? If so, what?

No… I’m not a sick fuck. Dominatrix deals and role-playing are in the main stream. For you to ask a question like this, you obviously have some issues. I imagine you pay for a lot of sex. I’ll have to give you the numbers of some sex workers I know. I get a referral fee.


How do you properly play with a man’s ballsack? What do they want? What’s weird? Too much?

Ball work is a solid component to any good blowjob. It’s rude to leave them hanging there. They get lonely. Start by lightly grabbing… Then rubbing, licking and sucking. Stay away from biting or grinding nails (fake or real) into them, or squeezing them violently. Obviously there are exceptions.

I once knew a stripper who had a regular customer that would pay her to step on his balls with her eight-inch stripper heels. There are some sick tickets out there. As always, feel out the situation. The more balls you play with, the better you’ll get. You’re welcome to practice on me, and I’ll provide constructive criticism. But I’m telling you now the stripper heel deal is gonna be a no-go.

Creepin’ With The Wingman — Answers To Your Filthy Questions

   In my life doing comedy a lot of people have said I’m too dirty, but the crowd who comes out is far filthier than I could ever be. Quite frankly, I’m offended. I feel degraded, disgusted, and sexually harassed. And I wouldn’t have it any other way.

   If you’ve seen me lately on The Dirty Kid Comedy Tour, seen my one man show The Wingman: “Let’s Get Creepin’ Comedy Tour,” or watched me headline other shows you know a portion of my act is called “Creepin’ With The Wingman.” In it, members of the audience write down their questions on getting laid, sex, dating, and relationships on index cards, and I answer them on-stage.

   Well, the questions I get are dirtier than anything in my X-rated show. Where do you sick motherfuckers come up with this shit? Being that there isn’t enough time for me to answer all the questions on-stage, and the questions are so fucking disgusting, I thought I’d start answering your queries here on my blog. I’ll be posting questions and answers from some recent shows. Check them out, and maybe you’ll find yours. Hope you’ll come out to a show, and let me be your Wingman soon. Come out for comedy that gets you laid.

   Let’s get creepin’.


   “The Wingman” James Holeva