CREEPIN’ W/ THE WINGMAN — OLE TYME CHARLEY’S — PLAINS, PA

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.

 

Anonymous

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.

 

Anonymous

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.

 

Anonymous

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.

 

Anonymous

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.

Dave

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?

 

Anonymous

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!”

 

Anonymous

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.

https://wingmanchronicles.wordpress.com/2011/04/11/fun-in-ac-the-train-story/

 

RV

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.

 

Anonymous

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!

 

Gorgeous

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?

 

Hope

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:

https://wingmanchronicles.wordpress.com/2011/03/08/the-mental-orgasm/

 

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.

Anonymous

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’ W/ THE WINGMAN — SARCASM COMEDY CLUB — CHERRY HILL, NJ

Saturday, June 25th 2011

 

Matt L.

1.   What is the minimum amount of money a guy should receive to suck another guy’s dick?

It depends on the guy’s skills. Just joking. I’m really not the guy to ask about such homoerotic questions. If that’s your thing, Matt, that’s cool… But you’re better off finding pricing information from a man who you know, enjoys or at least, is willing to suck cock.

2.   When is it inappropriate to laugh during sex?

When you’re complimenting a girl. It’s kind of a give away that you’re lying from the heart.

3.   Is that the right hole?

If it feels good it’s always the right hole.

 

Anonymous

How do you feel about frontal male nudity?

I don’t like to see it, but I like to show it.

 

Anonymous

What are your feelings on a rusty trombone?

I’m not a fan of anything to do with my ass… And I don’t eat ass.

 

Blowme aka your Mom

Is it okay to give your Mom and Dad pointers after you walk in on them?

Of course. I think that would be a nice thing to do. Let’s face it Mom and Dad probably aren’t with the young trends. If you could provide a tip or two I’m sure your parents would be very grateful. My parents ask me into the bedroom with them, and I’m always glad to help. I appreciate family.

 

Tara

1.   What is the best cleaning product to get semen out of fur?

Tara… I think that fur is gone. Next time you’re meeting a stuff. Where a cheap imitation or at least cover yourself with a cum poncho. I always keep a bag nearby with rain gear for these situations.

2.   If a vagina isn’t used, will it seal up and close?

I’ve convinced girls that it would, and used that to get them into bed. It was creative marketing. But honestly, I’m going to have to go with no. Although it will turn into a dried out cactus crotch which is basically the same thing.

 

B. At what point in a relationship do you share a copy of a house key?

Haven’t you been listening? Never.  That’s like inviting a vampire into your house… But worse. Vampires are less crazy than some girls. Read my crazy bitches piece.

https://wingmanchronicles.wordpress.com/2011/04/11/combating-crazy/

Anonymous

Do women have a fourth hole?

Yes… As well as fifth, sixth, seventh, and possibly eighth… Ears, nostrils, belly button if it’s an innie. Heroin whores have way more.

 

Reggie

Is it appropriate to grab somebody by the ass in the grocery store?

Of course… It’s a great way to say hello. More people should do it. And if it leads to sex, stay out of the frozen food section because you might not be able to get it up. And if it leads to jailtime, there’s bound to be casualties of war.

 

Ess

How do you get your man to shave his balls without hurting his poor little feelings?

Get him drunk, and when he’s passed out shave his balls in his sleep. If you want to be more up front, just stop blowing him until he manscapes.

 

Anonymous

As a guy would you rather date a woman with a 7 face and 10 body, or a 10 face and 7 body?

Either way 7 to 10 are solid scores in face or body. Personally, I’d rather date a girl with a 10 face and 7 body, because the face would be shown off. I’d rather bang a girl with a 10 face and 7 body because fucking has very little to do with the face.

 

Anonymous

What’s the proper way to perform the Cleveland Steamer?

Not to… Unless you’re looking for a good way to breakup, get revenge, or keep a crazy ex away. Unless they’re really fucked up, shitting on them in any way, shape or form should do the trick.

 

Anonymous

What is a dirty sanchez?

A sex act that has become cliché… But it’s not my style. Read Urban Dictionary you dirty motherfucker.

CREEPIN’ W/ THE WINGMAN — FIG CAFE & HOOKAH LOUNGE — JENKINTOWN, PA

Friday, June 17th 2011

 

Anonymous

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.

https://wingmanchronicles.wordpress.com/2011/04/11/fun-in-ac-the-train-story/

 

B.

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.

 

Waxdoll

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.

https://wingmanchronicles.wordpress.com/2011/04/11/rules-of-the-train/

 

Anonymous

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.


Emilia

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.

 

Jen

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.

 

Ward

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…

 

Tabby

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’ W/ THE WINGMAN — SHAKERS BAR & GRILL — HAZLETON, PA

 (formerly Shenanigan’s)

Friday, June 10th 2011

 

Scott K.

How do you get laid in Hazleton?

Same way you get laid anywhere else… Lies, mind games, and money… And don’t forget alcohol – it’s a weapon of mass creepin’.

 

Matthew K.

How do you let a girl know she smells respectfully?

You’d think you’d be doing her a favor by telling her “your cunt smells like a porta john,” but sadly, she might not see it that way. If she’s hot or the best you could get (be honest) just stay away from oral, and if she’s nasty anyway… Then tell her the truth and see what happens. If she’s cool and cleans up, yippee, if not, you’ll be doing yourself a favor and dropping the nasty bitch.

Really some women need better hygiene. Don’t they have any respect for themselves?

 

Ava

Is it okay for a guy to have a wingwoman?

Of course… I’ve used them many times. I’ve used a bisexual wingwoman, and even conned my sister into being my wingwoman. Check out these blog entries.

 

Anonymous

How do I get you in bed?

Well I hope this question is from a girl… If you indeed are a girl and you’re hot, just come to a show, introduce yourself, drop to your knees, and get to work. If you’re on the less attractive side… Just wait for last call and corner me in the bathroom.

 

Eric

What do you do when you go down on a girl and she smells?

Put a close pin on your nose… Or wait till you have a cold and can’t taste anything. While it sucks to have a cold and be at the Chinese buffet, it’s great when a dirty whore invites you to dinner in her personal porta-john.

 

Lana

How do I use my pussy to control a man?

With-hold.

See my Pussy Power blog entry: https://wingmanchronicles.wordpress.com/2011/03/30/pussy-power/

 

HDB

How do I get laid?

Hire me… And walk up to a girl, use confidence, swagger, and hype to get her into bed. The key is, don’t give a fuck about what happens. Just enjoy yourself, and take as many swings as possible. You need to swing the bat if you’re gonna hit a home run.

 

Anonymous

What’s the difference between a fuck buddy and a friend with benefit?

A fuck buddy is only used for fucking… Although sucking, touching, and rubbing are allowed… But talking is strictly forbidden… Unless it’s dirty.

A friend with benefits is a genuine friend that you care about, enjoy spending time with, and have fun fucking… A fuck buddy situation works best when you detest the person but they get you off, and get the fuck out.

 

Lou Skunt

Do midget strippers charge half price?

Not as often as you’d think. In really low-end shitholes, in this economy, sometimes they’ll do a two-for one… I know, it sucks. But it’s not like we have to pay double for amazonian strippers.

 

Dawn

Why is it that when a couple is in a relationship the guy is allowed to “flirt,” and the girl is not?

There’s a double standard and guy’s love to flirt but are even more jealous and clingy than girls are. Don’t allow the double standard. If your boy is gonna chat up every broad he sees, you do the same with every guy… If you’d like, I’ll even help you make him jealous.

And if you send a picture I approve of, and need a change of pace, I’d have no problem providing you an uncouth adventure.

 

Tinawina

If you rape a prostitute, is it considered shop lifting?

It is… The price of the pussy dictates the penalty. It’s a misdemeanor if it’s under $300… High class hos fall under felony grand larceny.

 

Justin H.

If you give the hooker an extra $5, will she really put her finger in your butt?

It depends on the girl. I had a friend who couldn’t convince a hooker to slip him a finger. He said one finger, what’s the difference? She had standards. She was a whore with standards.

CREEPIN’ WITH THE WINGMAN — RODANO’S IN WILKES BARRE, PA

Wednesday, May 25th 2011

 

Nicole E.

Why do guys need to force their dick down your throat while the girl is giving head?? We can do it! (without help)


Why do you like to hold our heads down when we’re munching your twat, and nibbling your clit? It’s all about control. It comes back to pushing the girl or guy you like when you’re on the playground in first grade.

Even when we’ve relinquished control (like when our dick’s between someone’s teeth), we still want to act like we have a little.

Honestly, it’s because a blowjob feels so fucking good and guys (people in general) are impatient and so they respond. Personally, I think when people learn to be patient they could have a hell of a lot more fun sexually. I am proud to say I know how to sit back, relax, and fully enjoy getting my cock sucked.

I guess laziness is good for something. It’s all in how you look at things.

However, while I know you girls could blow us without help, I think a lot of broads enoy having a dick forced down their throat… Just like they enjoy having their hair pulled or being thrown against the wall and having their clothes ripped off. As I say in my act (although I didn’t have time for this bit Wednesday night) “women want you to degrade them, but they want you to degrade them with class.”

 

Jenn Y.

What is the dirtiest place you ever had sex?

My ex girlfriend’s twat.

 

Ron

Have you ever had a threesome?

   Many… I enjoy a good threesome because of the team effort. A lot of guys will actually say… “You know a threesome isn’t really that good.” 

   That’s bullshit. Two broads are messing around with each other, and pleasuring you… That’s like saying an all you can eat buffet isn’t that good.

   Obviously there’s higher levels of all-you-can eat buffets, just like there’s higher levels of pussy… But as long as you don’t see the effects of disease set in until the next day, I see no reason why either all you can eat buffet wouldn’t be one of the greatest nights of your life.

   What’s hard, besides your cock, is the pressure. For many guys pleasing one woman is a high pressure task, you add a second broad to the mix and you have the responsibility of a Don in the middle of a mafia war. It’s this fantasy for so long that so much anticipation is involved that guys expect too much. Don’t stress, don’t worry, don’t freak out… You’re banging two chicks. What could be better?

   Have your fun, realize how awesome the adventure is, but know that who really has the most pleasure are the girls. You’re just the opening act. After you cum get the fuck out of the way, have a Gatorade and enjoy the headliner’s performance. If you’re lucky you’ll get invited back for an encore.

   For obvious reasons I prefer two broads, but I’ve also enjoyed myself in a strictly hetero two-guy, one girl train… You could read more about that right here. Let’s get creepin’.

FUN IN AC AKA THE TRAIN STORY:

https://wingmanchronicles.wordpress.com/2011/04/11/fun-in-ac-the-train-story/

RULES OF THE TRAIN:

https://wingmanchronicles.wordpress.com/2011/04/11/rules-of-the-train/

 

 

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’.

   Thanks,

   “The Wingman” James Holeva