Jizz

I'm gonna need a wingman

LegalTeens

Wingman needed, must love boobs

LegalTeens

Quick, I need a wingman!

nsfw_wtf

ULTIMATE WINGMAN (sensation white editions) (NSFW)

funny

You can be my wingman anytime

TomCruise

I need a wingman, stat!

RealGirls

Wingman falls to the Ham Planet

fatties

Every guy is wondering 'who can I get to be my wingman?'

RealGirls

Anon is god tier wingman

4chan

Best wingman ever.

BlowJob, Blowjobs

Chun Li - Ultimate Wingman

gaming

"You can be my wingman anytime"

gonewildcurvy

When your wingman has boundry issues

cringepics

[Picture][UPDATE] Some random chick texted me. Me and my buddies decided to be world's best wingman. Things got a bit out of hand.

teenagers

I relate Ghazan. Most Friday nights I end up playing wingman too

TheLastAirbender

Best grampa wingman [sora no otoshimono]

manga

Having a wingman is truly one of the greatest... wait.

Warthunder

Wingman

lolgrindr

18 M Wingmanned like a boss, to end up being the third wheel in a orge.. Went home.. Cheer me up ladies? ;D

ladybonersgw

Wingman of the Century

gifs

My best wingman

GayWincest

Her wingman went rogue

StraightGirlsPlaying

No better wingman than a wing-daughter.

wincest

Wingman

glitches_gone_sexual

My wingman gets me into trouble at the bars

ladybonersgw, GentlemenGW

Top wingmaning (NSFW)

trashy

Nice help-out there from her wingman

amateurcumsluts, UncutCumslut

My mate wingman'd me by telling a chick my dick was 'thick as Glade can'. It's actually a little thicker.

MassiveCock

[B/S] The perfect wingman

taboocaptions

The best wingman

ImGoingToHellForThis

Rest in piece wingman blade

EDC

WingMan

AwkwardScroll

My wingman's a pussy

NSFWFunny

[wingman] I think part of Bill was disappointed she wasn’t

taboocaptions

Yune best wingman (Micaiah upskirt pantyshot)

Fire_Emblem_R34

[B/S] The best wingman is a woman

taboocaptions

Bodyswap Wingman, or: Helping a Harem Protagonist Finally Get the Girl

wholesomehentai

I have a chubby female slutty wingman who sends me pics like this when she gets laid. She met this guy maybe an hour before this pic was taken.

CheatingSluts

[M/S] The perfect wingman

taboocaptions

[A/N] A reluctant wingman

taboocaptions

Peach, the best Wingman

bowsette

Wingman

u_tfwnowork

Your sister is so nice. She's gonna make sure your crush falls for you. [crush] [wingmanning you]

xxxcaptions

Your wife is your best wingman [Cuckquean, Neighbor, Pool]

xxxcaptions, CuckqueanCaptions, u_TheRopeIsForMyBoat

Wingman Daughter ftw

wholesomehentai

M/S It's easy picking up girls with a stunning milf as a wingman

wincest, u_DiversePleasure45

Wingman on a date. [FF7] (@mindcreator)

yuri

The Best Wingman [Artist: Markydaysaid]

BNHARule34, rule34, hentaicaptions, cuckoldcaptions, HentaiCity

My sister is lesbian, so we always wingman for each other. I wasn’t that into a girl I matched with on tinder, but my sister was, so I let her use my body to hook up with her. While she’s away, I’m preparing to get laid in her body. How’s my outfit?

bodyswap

Starlis is looking for a wingman...

CosplayDeviants

His wife is his best wingman

NSFW_Caption, xxxcaptions, CompersionNSFW

Mfw I see Project Wingman gameplay but I have a computer that can barely run minecraft

acecombat

When your wife is also your wingman...

snapcaps, VanillaCaptions, u_dinothedragon

41 year old single mother of two looking to settle down with her "wingman for life" barks out orders how you should act and demands you acknowledge her existence within 24hrs or less. Bonus Aubrey Hepburn quote

WhereAreAllTheGoodMen

There can be no greater wingman than your teenage daughter.

Incest_Captions, FatherDaughter, Familygame