Jizz

This will happen if there is a snowday [NSFW]

chicago, pics

My best shots from Pride today

chicago, lgbt

(When you see it) found this in r/funny yet again...belongs here...wonder who it was?...(funny nsfw, I think)

chicago, funny

"CTA can be one hell of a train ride, you never know what you'll see, i.e; this... (Possibly /NSFW)" (via /wtf)

chicago, WTF

Boystown [NSFW]

chicago, WTF

No shame.. And no fucks given for these two at Lolla...

chicago, pics

Giving you that look

TheHangingBoobs, shewantstofuck, JudgmentalWomen, Getanerection, u_Jewish_Gurl_Chicago, SluttyUSGirls

Someone in Chicago is putting these on bike posts

pics, picsonly, chicago

Vertigo's Cross Building Entertainment (NSFW-ish)

chicago

Edward “Easy Eddie” O'Hare lawyer in Chicago worked with Al Capone and later helped prosecutors convict Capone of tax evasion. A week before Capone was released from Alcatraz, he was shot to death while driving on November 8, 1939, see comments. [749x900]

HistoryPorn, chicago

Took a picture of the drive to work this morning

chicago

Auto-Show Camel-Toe

chicago

TRIGGER WARNING. (xpost)

chicago

Saw these pieces of human garbage standing all around the Willis Tower today

chicago

Stay classy, Red Line (this morning)

chicago

Someone put a dildo on the bean.

chicago, NSFWFunny, pics

Controlling Her with a Single Thumb

Manhandled, assfingering, facedownassup, LipsThatGrip, NSFW_GIF, asshole, buttfinger, Dominated, from_behind, gifsbabes, popass, reddtube, ThumbinPooper, u_agacharse, u_Jewish_Gurl_Chicago, Siksung

Laundry Quickie

Manhandled, u_DrugsAndFrenchFries, u_Jewish_Gurl_Chicago

Kitchen Counter-Top

Manhandled, jobuds, u_agacharse, u_Pnonni, u_memellop, u_Jewish_Gurl_Chicago

On Their Tip-Toes

Manhandled, u_Jewish_Gurl_Chicago, u_bear_chief_

Bent Over the Kitchen Sink

Manhandled, Sirspreciouso, u_Jewish_Gurl_Chicago

Watching Myself Grow

XChangePill, expandolicious, u_Jewish_Gurl_Chicago

NSFW - Walking around Wicker Park looking at houses when.....

chicago

Keys for size.

chicago

Slightly bigger?

BreastEnvy, Ifyouhadtopickone, 2busty2hide, jobuds, tightdresses, burstingout, JizzedToThis, iwanttobeher, u_Jewish_Gurl_Chicago

First city specific carts ever? Props Chicago

chicagotrees, oilpen, chicago

Want a beer?

WomenBendingOver, rearpussy, u_zishwon, buttplug, iwanttobeher, u_Jewish_Gurl_Chicago, nakedinthekitchen, ToplessServant, iwanttobeagirl, u_cdarwin57, uMrMister

Detroit's New Victory Dance (nsfw)

chicago

Who's your daddy? NSFW

trashy, oversharing, youseeingthisshit, WTF, chicago, Cringetopia

Can't imagine how this happened.

chicago

Sissy identity - the "Man" in the mirror

Sissyperfection, u_Jewish_Gurl_Chicago

HE wears the pants

Sissyperfection, u_flsissyfucker, u_Jewish_Gurl_Chicago

Marry the man of your dreams, sissy

Sissyperfection, u_Koklick, u_Jewish_Gurl_Chicago, u_Balls_D33p69, u_adfxh1234

Weak and effeminate? No problem honey, a real man will take care of you ?

Sissyperfection, u_Koklick, u_Jewish_Gurl_Chicago

Sissy realizes cock gives pleasure

Sissyperfection, u_hotwife4hubby95, u_Jewish_Gurl_Chicago, sissycaptions, FeminineMenFanclub, u_tranylvr, u_legoluigi431

Pink/Brown line humor

chicago, MildlyVandalised, NSFWFunny

Belleniko

NSFW_Plowcam, u_Jewish_Gurl_Chicago, u_Gaia_prime

Thank the chef

IWantToBeHerHentai, u_Jewish_Gurl_Chicago, u_hmslave16, u_Roguexcxc, u_NotHornyOnMain3, u_plznop

Marina Visconti's POV as she fingers herself

NSFW_GIF, femalepov, u_PuppyPenjulum, porn_gifs, popass, u_Jewish_Gurl_Chicago, RealJilling, u_45df78, gettingherselfoff, u_forwhomthebeltols

[Homemade] Don't take the Nanny on Vacation...

HerPOV, POV, u_Jewish_Gurl_Chicago

Layla London

nsfw_gifs, x_porn, popass, u_Jewish_Gurl_Chicago, u_charliefox4278, u_nikirash0848

Mike, currently Jenna, happy to be the rebound

XChangePill, u_Jewish_Gurl_Chicago, sissyhypno

Shower With Hottie

Showersex, GirlsShowering, GreatView, allpornnsfw, u_Jewish_Gurl_Chicago, u_evilmorty39

breed me and make me your housewife?

BreedingMaterial, u_Jewish_Gurl_Chicago

Love teasing my girlfriend like this before she begs me to ruin her insides (18M / 23F)

amateurgirlsbigcocks, u_Jewish_Gurl_Chicago

Pound me against the wall

IWantToBeHerHentai, u_Jewish_Gurl_Chicago

Who knew my boss could make me shake like this?

quiver, holdthemoan, u_Easy_Shame, u_Jewish_Gurl_Chicago

Going to have trouble walking after last night

doggy, u_Jewish_Gurl_Chicago, thatBounce

Milked The Biggest Cumshot All Over Me. Cows Were Watching.

reversepov, u_Jewish_Gurl_Chicago

Sizing up

amateurgirlsbigcocks, u_Jewish_Gurl_Chicago, u_MrWolF_Dom

After you put your load in me, I’ll put a load in the wash.

BreedingMaterial, u_Jewish_Gurl_Chicago, u_bppmb

Ava Addams Standing Fuck

standingout, u_Jewish_Gurl_Chicago, BetwixtOpinions, ALLtheNFSW, MakeNsfwGreatAgain

(oc) when he teases you and thrusts right in

FirstInsertion, u_TikcuS99, u_thespatialcowboy, femalepov, u_Jewish_Gurl_Chicago, VerticalGifs, u_boniclydexxx

Her mouth says no but her body says yes

hentai, HentaiGoliath, HentaiCity, IWantToBeHerHentai, u_9640b, ChiquisLewd, u_Jewish_Gurl_Chicago

Does this count

quiver, disgraceddaughters, u_Jewish_Gurl_Chicago, Fuckherlimit, u_jrjohn59, LOVELISTONOSZ_2