Jizz

Tell (m)e how the night would end if I were on my way out the door to pick you up for a date.

ladybonersgw

This would make dating, um, interesting....

lolgrindr

Who would you date?

crazyamy

[F] Would you date me if you thought my face was cute? (new pics)

gonewild

My fiancee would dressed up as prostitute when she is scheduled to date another guy. She is begging for him to fuck her horny pussy like this pose.

Cuckold, wifesharing

I wonder what the second date would be... [Semi-NSFW]

Tinder

Had a first date tonight, I thought the rock gym would be a good idea.... she landed bad!!

climbing

[NSFW] I'm aware you guys may hate this, but oh well. I missed the date for the GGCC Art Book. This would have been my submission.

gamegrumps

Wife asked her date to fuck her without a condom. Would you?

wifesharing, bestofwives

I think a date cut me o(f)f because I posted here... What do you guys think? :/ Would you do the same?

gonewild

Getting ready for dinner, would you be [m]y date?

ladybonersgw

Side by side comparison of my GFs 20 year old ass in a thong vs my GFs 26 year old ass in a thong.. she's gained 30 pounds since dating me (& eating like I do) but I think it plumps her ass up just right:) which one would you fuck?

WouldYouFuckMyWife

Quick [f]lash getting ready for dinner... Do you think my date would mind me showing off before he gets to see? :)

gonewild, GoneMild, UnderwearGW

10/10 would ask the captain the permission to date her

nsfw

Where would you take her after a date?

AsianHotties

Why would a model ever date you? [wholesome] [it cos the 3.4" u packin] [jk Im sure you have a huge dick] [unless ur one of the, like, 3 sissies who read these captions, in which, u got a tiny dick, slut.] [catering to the masses] [#contentcreator]

xxxcaptions

I would if she ever dated someone that she tried and succeeded to keep this part of her life hidden from..

ericacampbell

Tonight is date night ... thinking about starting a kik group. Send me a DM on here if you would he interested :)

hugenaturals

Let's see how this is received here. With my due date approaching, I thought I would share my moment of conception. Of course discovered later that I just happened to record that day haha.

PreggoPorn, VerticalGifs

If you get a chance to go on a date with her, would you resist looking at her cleavage?

AlettaOcean

Wife sent me this from a tinder date. What would you do if she swiped on you?

Hotwife

I wish Reddit had a Story feature, much like other social media platforms so I can keep you all up to date on what I'm wearing, or more, what I'm not wearing... Would you be interested in updates like this?

u_NotUrBigTiddyGothGrl

M/27/6’1” [271lbs - 208lbs = 63lbs] 6months. wife of 1 year(dated for 6 years) left me due to late-onset mental illness, insisted she would never be able to be intimate with me again. Messed my self esteem up, so here I am! Excuse the nudity, I had to sho

progresspics

If I wore this on our first date would you be pleased? ?❤

bbwselfies

(19F) Sometimes I let her out to play :P Would you be my play date?

gonewild

[24F, 5'2'', 95 lbs] Dating during the pandemic has been really hard. I really wish my boobs were bigger. Just an A cup would be nice.

normalnudes

You Would Fuck Me Raw? You Must Know I Do Anal On First Dates ?

DegradingHoles, DirtySocialMedia, EdibleButtholes, FeetToesAndSocks

Which outfit would you like me to ware on a first date?

OnOff

[F] I may not be perfect, but at least i would do anal on the first date

assholegonewild

Anyone wanna do a roleplay Im so horny and this would help I could be 2B and you can be whoever. date serious girl on momentgirl.com - SNAPCHAT : eliselouvat69

nierNSFW

(f) 48 - I rarely do this Make-Up, but if, would you date me?

40plusGoneWild, milf, HotMoms, amateur_milfs, AgedBeauty, milfsdoporn, cougars_and_milfs_sfw, wifepictrading, onlyfansgirls101, BestOfOnlyfans, OnlyFansBabyGirls, OnlyFansNewGirlz, onlyfansprom, onlyfanspromo, Onlyfanspromoss, OnlyfansPromosx, OnlyFansPromotions

Be honest, Would you fuck me on first date?

fitgirls

What would you do If I got naked in front of you at a First Date? ?

xsmallgirls

Deleted Tinder, Okcupid, and Bumble, I don't want to get laid, I don't want to date, why would I when I could watch these beautiful black men all day? 2021 Year of Porn!

WhiteBoySex

We go on a date together and I´m wearing this, what would you do?

BustyPetite, Slut, collegesluts, BigBoobsGW, OnlyFansPromotions, SlimandStacked, boobs, onlyfansgirls101, PacksLatinas, u_hateinsta

What would you do if I just did a random titty drop on the way to our first date?

TittyDrop, 18_19, gwpublic, pititey, TrafficTits, CommutingGoneWild

Your Muslim Mom wanted to update you regarding her outfit choice for our date. She told you not to worry because she would have never removed her burqa. That doesn't mean I can't have fun with her holes.

IFYM, bangmybully, raceplay, jerkofftomymom, Cuckik, cuckoldparadise, cuckhumiliation

Nylons for a date. Would you appreciate them ?

nylon

Point the arrow in the air if you would ejaculate inside me on the first date!

TikTokNudes

Our date would start with an innocent cuddle, and quickly turn into something a little more fun.. ?

RealGirls, Nude_Selfie