Niles IL
Age 18-100

Sponsored

Log in to enable the Gallery view Login

Log in to use the Filtering feature Login

Straight Men for Gay Encounters in Niles IL – Real Ads — Page 4

Hey! Please review DL:

May 03, 2026

Find Transsexuals Near You Interested In Casual Encounters! Sponsored

Fat top little wiener (Niles/Des plaines) 40

May 01, 2026

Any real ts girls hosting tonight. hung and handsome here (Mobile in Chicago) 36 Verified

Hung seeks hosting ts/cd tonight (Ohare area) 36 Verified

Apr 30, 2026

Hung and handsome seeks sissy cd or bj pro near elk grove or melrose park (Elk Grove Melrose park) 35 Verified

Nl host - far north by evanston off sheridan rd (Far Northside) 49

Apr 28, 2026

F*ck my mouth - discreet (Lincoln square) 46 Verified

Apr 19, 2026

Seeking horny bi perv to service (Logan square Avondale Irving Park) 35 Verified Premium

Let’s have some fun (Logan Square) 32 Verified

Apr 17, 2026

Mature cd or trans (Ohare) 54 Verified

Apr 14, 2026

Anyone in evanston just looking to chat maybe more (Evanston) 42

Apr 11, 2026

Curious looking for cd/car play (Nw burbs/mobile) 41

Apr 10, 2026

Transguy visiting northside 4/26-5/3 (Edgewater) 38

Apr 07, 2026

Catch you wearing panties. (NW burbs) 35

Apr 06, 2026

Mature oral top for hosting oral bottom (Chicagoland you host) 63

Latino for passable with great dsls must host available now (Anywhere) 37 Verified Premium

Apr 04, 2026

Pretty sure my ass is bigger than your gf's (Oak Park) 32 Verified

Apr 02, 2026

Who got the blues (Des Plaines Niles Chicago) 40

Fat guy in need of release (Near niles) 39

Apr 01, 2026

Playing with panties (Northside) 40

Mar 30, 2026

Sissy/cd/trans c0ck in my mouth (Elk grove) 31 Verified Premium

Looking for a long session (Albany park) 27 Verified

Discreet m4trans seeking connection (Logan Square) 33

Mar 28, 2026

Im hosting someone on their knees (Northwest side) 58

Looking to be served (Northwest side) 62

Mar 18, 2026

Hello there looking needing a gay ts or cd for fun now (Loop / Jefferson park ns) 29

Looking for cd girl (Norridge) 40 Verified

Mar 10, 2026

Male-presenting woman seeks nice guy (Rogers Park) 42

Mar 06, 2026

Masc guy looking for after gym. (Chicago) 39 Verified

Mar 01, 2026

Cd, trans, or femme? let’s connect (Logan Square) 47

Feb 26, 2026

Looking for real cd/trans (Rogers Park) 51

Need a real man (Cicero ave and Pratt st) 57

Feb 18, 2026

Cd looking for other cds for fun (Ask me) 25

Feb 13, 2026

Looking to give you some vitamin d (Portage park) 40

St8 guy looking to get ri mmed deep and hard. can't host (North side chicago) 44

Feb 12, 2026

Late night sex??? (Meadow Park area) 48

Construction guy looking for a throat goat for after work fun in lakeview. (Lakeview) 39 Verified

Feb 09, 2026

Ihosting all night and morning (Edgewater) 36

Feb 08, 2026

Cmnm fun, looking for a guy that likes playing doctor (Near North or West Burbs) 51

Just a str8 muscle masc guy who loves 0ral. . (Lakeview or near) 35 Verified

Feb 07, 2026

Need a gurl now!!! mixed blk & wht bull looking for cd, ts or fem whose 100% bttm (Evanston/Northside) 45 Verified

Feb 05, 2026

Need to get throated (Logan Square) 50

Feb 03, 2026

Classy ts woman ready for fun (Chicago) 31

Feb 02, 2026

Any chubs out there in the harwood heights area any age ? (Harwood Heights/Norridge) 24

Jan 30, 2026

In search of someone over 40 top for bottom (Andersonville/lakeview) 39 Verified

Jan 28, 2026

Your hands, my needy body (Evanston) 56

Special hands for me? (Evanston) 57

Jan 27, 2026

Latino top looking for bottom cd/ts (Oak park) 30

Jan 20, 2026

Hung and freaky latino looking 4 phat booty and deepthr (Irving Parm) 29

Looking for netflix and chill date with thotty femme (Portage Park) 28

Jan 19, 2026

Top looking for cd tonight (Norridge) 39 Verified

Jan 17, 2026

Early party fun saturday afternoon (Logan square) 33 Verified

Jan 11, 2026

Uhost itravel (Oak Park) 27

Jan 10, 2026

Come to me please don’t flag (Chicago/niles) 40

Jan 08, 2026

Looking for manscape (Belcraigan) 45

Sissy 4 older (Nw side) 46 Verified

I'm looking for a asian cd (Franklin Park) 33

Looking for a ts/cd (Mount prospect) 23

Dec 30, 2025

Try Something New...Hook Up With a Trans Girl Sponsored

Blue collar good looking muscular top (Northside) 38 Verified

Dec 27, 2025

Looking for ts (Rogers Park) 30

Dec 26, 2025

Casual fun (Logan Square) 31

Looking for nice, bbl level peach for anon fdau (Portage Park) 30

Dec 21, 2025

Sub for dom cd (North burbs) 57

Dec 13, 2025

Fart sub looking (Edgewater) 35

Dec 10, 2025

Looking for smooth, jiggly booty (nasty talk me til i nuuuut) for dark room pump n’ dump/fwb (Northwest Chicago) 30

Throatpie (str8 dom looking) (Irving Park) 28

Need a regular fem with a wet, deep thr (Old Irving Park) 28

Dec 09, 2025

Wheeling dam play? (Wheeling) 30

Dec 07, 2025

Mature man looking for mature gay man (Chicagoland (You Host)) 63

Dec 06, 2025

Fat straight top (Des Plaines/Niles) 40

Very horny straight guy (Northside) 40

Smooth submissive total bottom c d gurl hosting now (Arlington Heights) 52

Smooth submissive total bottom girl looking for tops. i’m hosting looking for now. (Arlington Heights) 56

I am hosting this evening all night and sunday morning (Arlington Heights) 53

Dec 01, 2025

I am seeking a dominate master (OHare) 54

In need of relief (Deerfield) 36

Nov 28, 2025

Straight clean ddf guy looking for a bottom 0ral fwb (Northside) 35 Verified

Nov 27, 2025

Hot curvy lady looking for gentlemen (Chicago) 26

TXT ME ON SIGNAL; Lisajuice.22

Nov 25, 2025

Newbie looking to give head (Mount prospect) 23

Nov 24, 2025

First time (Jefferson park) 34

Serious post please. wear panties and a tiny skirt for me…. (Logan square) 41 Verified

Nov 23, 2025

Throat goat (Skokie) 28

Nov 22, 2025

Straight latino male for some fun tonight (Lakeview) 38 Verified Premium

Nov 19, 2025

Straight egyptian guy looking for fun (NW Suburbs) 32

Nov 18, 2025

Straight looking for head (Northside) 30

Nov 17, 2025

Thicc boi next door wants a sneaky session (Chicago) 27

Nov 13, 2025

Hot and hung for passable ts (Logan/Avondale) 39 Verified

Curvy female looking for male (Chicago) 26

Nov 11, 2025

Looking for head (need fwb) (West Ridge) 30

Nov 10, 2025

Hmu looking for some fun fun to thrôat it or slide in me i do car play or can host (Chicago Area) 25 Verified

Nov 09, 2025

Looking for a fwb.. to experience domination (Logan Square) 31 Verified

Nov 05, 2025

Are you young and curious? discreet? (Elk Grove/Schaumburg) 65

Oct 31, 2025

Vers/hung ts nut lover (Elk Grove Village) 25

Oct 30, 2025

Service in uptown… love them construction workers…delivery guys (Uptown Buena Park Wrigleyville) 29 Verified Premium

Classy ts woman ready for di** (Chicago) 30

Oct 29, 2025

Straight masc seeks sub sissy (Oak Park) 52 Verified

Oct 27, 2025

Looking for a younger cute twink who can host on the northside (Uptown) 45

Mwm off today and looking to play (Wicker park) 43

Oct 22, 2025

Looking for ongoing fun! (Chicago) 30

Oct 20, 2025

Your personal c*cks*cker……vers (Nearby) 29

Oct 18, 2025

Ts looking for fun (Neighborhood trans) 28

Don't see what you're looking for?
Post here