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.



Friday, June 17th 2011



Is it at all appropriate for a wingman to be present during sex, cheering and criticizing?

Yes definitely… I commit to my clients. It’s like Mick and Rocky. Read my train story for a true depiction of team work.



What do you do when she farts mid anal sex?

Keep going but hold your breath… A true player commits.


Kel (was nice enough to leave her phone number)

How big is your penis? And girth?

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.



What do you do when he asks you to fuck your elbow?

Let him do it. He’s a guy who likes to use all of the performance space. He’s not a coffee house singer/songwriter who stands in one spot, he’s a fucking rockstar. Enjoy the show.


AJ aka Melon Man

When you are Eiffel towering a girl, do you look the other guy straight in the eye the whole time?

Well Melon Man, if you’re good friends with him. There’s no better moment two long time compadres could experience than enjoying a girl like she’s an amusement park.

Just joking… Enjoy the uncouth adventure but stay away from anything remotely guy-on-guy. See my “Rules of The Train” blog.



Why does my boyfriend always want to put it in my ass when I have such a brilliant vagina?

We all like to go where we’ve never been. It’s like a lot of people from America want to go to Italy or Paris… But to the people who live there, it’s not a thrill. Once he’s gotten the ass, he’ll be going for the ear.


If you’re trying to send a dirty picture to your boyfriend and accidentally sent it to his dad, and he sends one back, do you keep going???

Judging by the three question marks you enjoyed the picture. If you’re into him, enjoy the picture and keep going. It could be meant to be. And there’s no better way for a father and son to bond than to share a broad. If you could help enable that, do it.



Will you take my friend Audrey’s virginity?

Have her come out to a show and introduce herself. I’ll give a yay or nay when I see her. If I give a nay, get me around last call or accost me in the bathroom. Resilience is a quality I admire in a creeper.



Is it natural for girl’s to squirt? And is it dangerous to your dick?

Some girls are squirters… Especially if you provide a solid mental orgasm. No it isn’t dangerous to your dick. Her pussy will tense up like a vice grip as she’s clawing your back but the cock is strong… I can’t speak for the scratches or bite marks that will end up on other parts of your body. It depends if the girl’s a cat…



That was the most horrible lap dance I ever had. Mine are so much better!!

Bullshit… I remember that lap dance and I was good. It was like poetic gyration. And thanks for the Lap Dance that encored the show. You tore it up to “Pornstar Dancing.” You have a real future ahead of you. Let me know what club you’re working at, and I’ll stop by. I will expect a free VIP complete with complimentary extras.

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

Pussy Power!

   Sometimes I’m a wingman for women, too. It’s easy because they hold weapons of mass destruction between their legs.


The only reason women get fucked over by guys is because they don’t realize the power they have over guys. They’re stupid.

Females are in a natural position of male control and dominance because they have a weapon of mass destruction concealed conveniently between their legs. Anybody of remedial intelligence should realize by now that the pussy has the power.

The problem is so many girls meet guys who string them along for an eternity, and the ladies somehow forget that they themselves are armed and dangerous.

Don’t give me that, “who is a player like you to comment on such a situation? You’re the problem.”

No, no, no. If you’ll remember from the piece I wrote last week, I’m a high class player. What I do is not breaking a bitch, an adventure with me means everybody wins. We all get fucked… But in a good way. Remember, I’m an old school gentleman.

Sadly, though, even the most confident, self-empowered women are often allowing hack, wannabe players to control them and break them down. It’s awful when that happens because once they finally break free from their jail sentence, they’re extra careful. Even around a high class player like me who would provide her a mental orgasm to a level she could only have with another woman. It’s bad for the guys who deserve to get laid.

The biggest problem is women allow themselves to get so wrapped up in the wrong guy, and they get this idea that their man has the desirability of Johnny Depp, or me. That usually isn’t the case. These broads go into a constant negative mode saying:

“He’s with another girl. I know he’s with another girl. He’s done with me. I’m never gonna hear from him again.”

It’s been twenty minutes.

“I just know he’s fucking somebody. I know he fucks other girls all the time.”

ME: “Is he good looking?”

GIRL: “No. “

ME: “Is he rich?”

GIRL: “No.”

ME: “Is he smart?”

GIRL: “No.”

ME: “Is he smooth?”

GIRL: “No.”

ME: “Is he confident?”

GIRL: “No.”

ME: “Does he have a cool job with mystique and/or financial potential?”

GIRL: “No.”

ME: “Does he have game?”

GIRL: “No.”

So where is this Warren Beatty appeal that’s wrangling all the pussy?

It all comes from the challenge to please a guy that seems at times like he can’t live without you, and moments later like he never wants to see you again. Girls utilize a hot and cold strategy just as much as guys, except guys don’t have an almighty vagina to hold over the girls.

First off, why the fuck do you care about this guy? And second, what makes you believe that any other girl could actually be interested in him?

Girls always have a feeling that the guy, who won’t make it official, is out trying to hook up with other girls. And he is. He wants to prove to himself that he could get other ass. Some guys can, but in a lot of cases, these guys could try all they want but just can’t close.

A female friend of mine was having some problems with a dude who didn’t want to commit. Although I’m not about commitment right now, I did my best to be my friend’s wingman, so I said “why don’t you just step up and cut him off for a while?”

She said, “My greatest fear is that if I cancel on him now, he’ll just end up fucking somebody else.”

I’m like “You know it’s really not that easy.” He’s way more likely to be jealous that you’ll hookup with somebody else. It’s so much easier for a girl to get laid. Pretty much any girl could call up a random guy and get laid anytime she wants.

GIRL: “Hey Billy, this is Tina. You don’t know me, but I was thinking maybe I could come over and suck your dick… Would that work for you?”

GUY: “Ugh, yeah… My Momma still up but she go to bed by midnight. Actually come over now and I’ll slip some drugs in her cup a’ tea so she pass out. Momma got the bed in the house, so I’ll put her on the stoop.”

Unless you’re a celebrity or a sultan, it’s not so easy for guys. I know how to creep, I’ve been with a lot of chicks. But it’s still rare to be able to call a girl… No date, no woo, and just fast forward to fucking.

I can’t call a girl and be like: “Yo Nikki, it’s James. I was thinking I’d come over and blow my load in your face tonight. No, no dinner. I already ate. I just wanna pin your knees behind your ears.”

Yeah, that’s not happening. The pussy has the power. When you ladies start realizing your pussy has the power you’ll eliminate a vast abundance of relationship drama, and be free to enjoy the limitless control you have over guys.

If you want to regain the power, it’s time for a time out.

I do it with drunken strippers who cause an embarrassing scene and yack in my car, and you could do it with your indecisive man. How will he ever learn without discipline?

All you have to do is nothing. The next time he contacts you – text, Facebook, email, phone, Skype, smoke signals, singing telegram – you ignore him for twenty-four hours from that moment. But if that twenty-four hours takes you into the wee hours of the night, you round to the next day, in the afternoon.

You don’t want to make contact in the middle of the night because that’s a sign of weakness. It shows you’re lonely, alone, and thinking about him. Early morning doesn’t work either because that shows him you wake up and he’s the first thing on your mind.

I know you’re going to look for ways to skate around this. You’ll rationalize: “I didn’t text him, I emailed him… He saw I was in the Facebook chat… I answered the phone but that’s because I answered real quick and couldn’t see who it was.”

Those are weak excuses, and if you continue to act weak on your own, how could you ever take the power in this relationship tug o’ war?

Why Time Out?

It will shift the struggle for power. He’ll be blowing up your phone, and his stomach will be in knots because he’ll be scared to death that you’re in the throes of passion with another gentleman caller. Remember, it’s so much easier for a girl to get laid. And even if they won’t admit it every guy knows the pussy has the power.

Text Decoy

When trying to play it cool or conduct a time out, girls and guys; we all have a roller coaster ride of emotions  going through our bodies that keeps us on the edge of a breakdown making it nearly impossible to not make contact. You’ll find yourself wanting to say everything from “I love you,” to “I hope your dick falls off and burns from all the dirty whores you’re fucking.”

You know some things nice, others, a little hurtful. Relationships are tough.

Since your feelings will be erratic and those messages might not better your situation, you need to find yourself a text decoy.

Whatever you want to say, say to a good friend instead. You could even have them respond in character. I did the same with my friend Brian. All was going great until Brian’s wife read some of the messages. She was pissed.

Last time I went over there she tried to videotape me. I said “No! Absolutely not! I am not like that… No way I’m doing it on film.”

What… She made a good dinner. And Brian is very good looking. And big. I’m still sore.

Relax, I’m just joking. Somebody has to break the tension of  the relationship wars. There’s nothing homoerotic in this player’s life.

Online marketing  

   It’s amazing how the most meaningless Facebook status or tweet could turn even the toughest guy into a little bitch. It’s even more amazing how despite what many women go through with a guy, they’re still afraid to post even the most innocent status. Do it.

Mention you’re out doing something with a guy friend, say you’re spending the night clubbin’, out for sushi… Have male friends comment on your page.

I’ve known some girls who were so nervous that guy friends would leave an innocent Facebook comment about meeting up, or whatever, and they’d immediately delete it. That doesn’t sound like the behavior of someone who deserves to win the war.

If you want power, punish him. If you’re afraid to hurt him, then you’re weak and obviously don’t deserve power. You’re always thinking a move like that will drive him away, but in actuality, it’ll pull him much closer.  People are as powerful as they feel inside.

Play like you just don’t care

    The problem is things are going to start going well and it’s going to feel so wonderful, and you’re going to want more than anything to make a spontaneous grand gesture for him. Do not! It will only put you right back where you started, and you’ll again be fighting to regain power.

Sometimes you gotta whack a guy.

   Sometimes you could strike, take over the power, and the guy will actually step up and be who you want him to be. More often, however, the situation is not going to change. The guy will fear losing you and it will shift briefly, and then it’ll flip right back. History will continue to repeat itself, and the cycle of hell will continue. You could usually tell fairly quickly if that’s what’s going on, and if that’s the situation it’s time to make the problem go away.

I’m not saying kill him, that could be hard to get out of and hitmen can’t always be trusted. But it’s time to say goodbye.

You’ll leave with power… But you must move on with no contact whatsoever. You’re like a drug addict, who just got released from rehab, and must totally abstain to stay clean. Addicts tend to think they could still snort a line of coke socially and keep it in moderation. They can’t. Must we reference Charlie Sheen. Well if you want to be winning, and the situation isn’t right, you’ll whack the guy for good.

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.”

In the UK get “The Wingman Chronicles” right here.

Creepin’ at the Hospital Teaser

How do you get laid, while you’re laid up?


Sadly, no matter how good your coverage, under the current administration insurance companies refuse to offer sex workers as part of your health care package.

I don’t believe it myself, but despite my charming bravado I lack the political clout to make a difference. So it’s up to you.

If you’re laid up in a hospital, and you want the best treatment, it’s your responsibility to fight for it.

There’s nothing that will cure a man’s illness, or injury, and the mental anguish that accompanies, more than an ejaculation induced by someone other than himself. Personally, I think that should be in a nurse’s job description. They’re emptying your bed pan, why can’t they blow you, or at least administer a hand job?

She could wear a rubber glove if it’ll make her feel better.

I mean these nurses say they want to make a difference, here’s their chance. Even a good old fashioned wet dry hump will aid in your recovery.

Anyway, until nurse/whore becomes a combination occupation, the creeping is up to you and me.

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

Dumpster Diving Teaser


I sat in my friend’s living room with him and the evening’s bargain-basement prey, sipping Lion’s Head and talking nonsense as I counted the minutes till I could take her to the bedroom.

She was good looking in that slightly beat up, small town, simple minded, non-reading, a few teeth out of place kinda way. Eh, she was definitely adequate in my drunken state; as well as the chain-smoking, jack-swilling, staggering prom queen of the dive bar we were at.

I was surprised the grimy establishment didn’t have heroin needles strewn across the floor.

My friend would not stop with the incessant yammering, attempting to bond with my lady of the night. I was staying there because his house was in walking distance from the shithole he dragged me to.

“What do you do?” he asked her. “Have another drink. Would you like a Xanax to go with your beer?”

Shut the fuck up already! I wanna get laid. And for god sakes no Xanys… she’ll go right to sleep.

If she’s passed out before I could get laid that would be catastrophic. I might have spent three to four bucks on her at the bar. I was ready to get what I paid for.

I’m sorry he couldn’t wrangle a girl to bring back. I initiated opportunities, but I guess his ace pickup line — “I’m the greatest football player to ever come out of Lackawanna County” — wasn’t working on the dirt bar socialites.

Finally, I whispered to my girl to go to the bedroom, and as I was walking away my buddy grabbed me.


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