Jizz

(f) going on a date tonight, do you think he will like me?

GoneWildPlus

What would you do if you knew I was wearing this under my clothes on our date

gonewildcurvy

I wore this on a date with a friend last week

gonewildcurvy

Found on a dating site...at least her finger is off the trigger?

ghettoglamourshots

Got a little dressed up tonight. Let's go on a date?

ladybonersgw

Wanted to bang a guy who asked me out. Got stood up on the date. Oh well, his loss, right?

gonewildcolor

Awesome hat, but would not wear out on a date

CandidFashionPolice

wife is out on a date --more in comments

Hotwife

18 and has a baby? Check. Showing off tits on a dating/hookup app by breastfeeding said baby? Check. Yep this is certified trashy.

trashy

Let's play a game! We are going on a date, what should I wear?[f]

GoneMild

Out on a date (Anasheya)

futanari, cutefutanari

Found this gem on a dating site.

awfuleverything

I'm only 5'8" but I usually can't wear heels on a date :/ [f]36

TallGoneWild, PetiteGoneWild

Wanna go on a date? Maybe we even could cuddle and have sex afterwards?

traps

[f] got stood up on a date. think you can cheer me up?

gonewild

Princess Boo on a Date with Luigi

bowsette

I can put it on our date

RealGirls

Take me on a date?

traps

We went on a date and I sent him this from the bathroom ??

TheMomNextDoor, LingerieGW

I'm going on a date today, but the plug will be our little secret ? [f]

asstastic, rearpussy, Sexsells, Skryker

Mom tried Molly for the first time on our date night. Turns out she loves it!

hentai

You had only been on one date [Horny, Slut]

xxxcaptions

Frankie on a date (renatoforfun) [Foster's Home for Imaginary Friends]

rule34, FrankieFoster34

What would you do i[f] you saw me on a date like this?

gonewild, PetiteGoneWild, A_Cups, Fornhub

She took me on a date last Saturday and drove around all day like this. I enjoyed my topless chauffeur!

HugeHangers, u_Lilpsychcdxx

When you tell your gf to be safe on her date with a new bull

CheatingCaptions, CheatingSluts, Hotwifecaption, ilovesluts, u_tilly_50

Where would you take me on a date???

AnaChuu, Thighs, Booty_Lovers, undies, UnderwearGW, GirlsinLaceFishnets, SexyOutfits, voluptuous, CurvesAreAwesome, u_SinxLp

Would you go on a date with me?

traps, Asiantraps

I think this outfit can be complemented with a skirt, and I can go on a date!??

AsiansGoneWild, JavJux

Taking Tsunade On A Date. ?

AnimeMILFS, OppaiLove, thick_hentai

POV: you on a date with me | 23yo CD in WA

sissypersonals

Straightening my hair and Stretching my holes before going on a date ?

PetiteGoneWild, xsmallgirls, collegesluts, AsiansGoneWild, LegalTeens, TokixPoki

this is what i would wear on our date vs what i'd wear when i invite you inside after ;)

gothsluts, adorableporn, OnOff, PetiteGoneWild, u_dovidd

[ohkami ryosuke] Two mangakas go out on a date

wholesomehentai

Ive done anal on first dates :)

AnalGW, EdibleButtholes

No idea on the date, I'm thinking early to mid twentieth century.

OldSchoolCoolNSFW

Take me on a date and we'll see where it leads ?

RealGirls

Friend Wanted To Last Longer With His New Girl. So I’ve Been Helping Before He Goes On Their Dates

QualityBlowjob, DeepthroatTube, SwordSwallowers, u_nimblybimbly436

[32F] Single mother expects to be wined and dined "old school" now that she is going on "real dates" and no longer hooking up. Just more proof that relationship-minded men are burdened to cover the financial and emotional discounts that CC Riders reckless

WhereAreAllTheGoodMen

Take me on a date ?

amateur_shemales, Sissies, trapsarentgay, trannyslut, FemBoys, GoneWildCD, sissyplace, u_ts_milk

How I look on the date, and what I look like after you come over

RealGirls

Imagine we’re on a date and I give you a sneaky flash??

RealGirls, nsfw_gifs, altgonewild, VerticalGifs, GoneErotic, Babes, GirlswithGlasses, NotMyP0rnAlt

Now you can see what's under my dress on a date

GodPussy, pussy, Innie, u_noimporta1, u_Ecstasy_dream, u_beardedblackdragon, u_meliodaszafrado

Would yo go on a date with me ?

BigBoobsGW, ThickChixxx, BestTits, PetiteGirls, SlimandStacked, SlimThick, TheThiccness, needysluts, Babes, camwhores, BreedingMaterial, naturaltitties, barelylegalteens, petite, ThotClub, funsized, knockmeup, Mexicana, Stacked, Nudes, latinas, Slut, Gonewild18

What would you do if I wore this little, black dress with no panties on our date?

Nudes, SunDressesGoneWild, u_MK2000TDI, collegesluts, VerticalGifs, u__Fokusnik_, Nude_Selfie, InnocentlyNaughty

Newly single and low N-count but already heading down the path. Does she sleep with the guy she's been on 7 dates with and spends all day with or the rando she just met and will never see again?

WhereAreAllTheGoodMen

Can you take me on a date? This is my outfit

barelylegalteens

are you going on a date with my pussy?

pussy

Imagine we are on the date you know that i am not wearing panties....;)

nopanties, Upskirt

how would you like me to be dressed on our date??

xsmallgirls

POV: On a date with your Elven GF

ElfHentai

"I'd never go on a date with you, Senpai."

NagatoroHentai, Hentai4Everyone

If you take me out on a date, this outfit is definitely coming off at the end ;)

RealGirls, adorableporn