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.

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