8 XXX : date caption

Lunch Date [Public Masturbation]

imgur.com category @HourGlassAss

Dating a libertine [Female-led open relationship] [Mild intellectual humiliation]

imgur.com category @N2vm

online dating works! [sissy] [gif]

imgur.com category @jdog638

Worst third date ever! [BDSM]

imgur.com category @PM_YourPics_2Caption

Futa World: Dating [Futa][Self-Suck]

imgur.com category @LightFantastically

Sissy first date!

imgur.com category @Thedude8997

Date night

tumblr.com category @Mypostsmakeyouwet

Dirty date night dare.

imgur.com category @Mypostsmakeyouwet

Hotwife home from a date.

imgur.com category @Mypostsmakeyouwet

Hotwife dressed for date

imgur.com category @qm2x1798

Hotwife getting home from a first date

imgur.com category @Mypostsmakeyouwet

Hurri218's girlfriend has a hot date

imgur.com category @Mypostsmakeyouwet

She's dating my mom [Bully, Lesbian, Alpha Female]

imgur.com category @SilversAndGold

Can't Believe She's Single [Blind Date]

imgur.com category @[deleted]

[busty] dream date {/r/taboocaptions}

imgur.com category @clowns4mom

First Date [Cum Licking]

imgur.com category @[deleted]

Her unexpected date

imgur.com category @trezobel

Your gf asked for an update about your date

imgur.com category @iForgotiSwear

Your girlfriend is late for your date and this is why.

gfycat.com category @4TE4

What your sidechick says after the second date

imgur.com category @iForgotiSwear

You dated for how long?

gfycat.com category @[deleted]

It's rude to not call her after your first date.

gfycat.com category @random_sissy_sub

Date Night

gfycat.com category @random_sissy_sub

Tinder date with D.Va [Anal] [Exhibitionism] [Cumslut] [Mentions of cum-eating] [kyoudasha]

imgur.com category @rw_caption

Office Synergy Part 2 [Wholesome][Co-worker][Older Woman][Date Night]

imgur.com category @MooMaster69

Valentine's Date w/ teh Waifu [Persona 5] [Spoilers] [Romance]

imgur.com category @maskthedowncast

Futa First Date [Futa on male] [blowjob] [meek top] [attempted dirty talk]

imgur.com category @NadiaBlack

Shy trap tinder bio [Trap, Femboy, Dating, Wholesome]

imgur.com category @StaggeredBadger

[M/S] Josh and the daughter are actual dating now.

imgur.com category @clowns4mom

[sisters] Double date cross over

imgur.com category @clowns4mom

Why doesn't she ever date?

imgur.com category @clowns4mom

When I get home from a date ... (crosspost r/cuckoldcaptions)

gfycat.com category @heyjoewhatsthat

Date night with mom [m/s][gif]

imgur.com category @TheGreenScar

[F/d] Dating Rule

imgur.com category @darklightsun

She Only Dates Chinese But Fucks White

imgur.com category @CompileEros

At least cleaning her before her dates is less humiliating than cleaning her afterwards.

imgur.com category @gr0undstone

You hated going on a double date with the black couple next door...

imgur.com category @slutlover03

Her Latest Tinder Date

imgur.com category @CompileEros

Second Date

imgur.com category @PervyWanker1

Blind date goes well.

imgur.com category @1recnamorcen

First Date

imgur.com category @PervyWanker1

Bathing for her date

imgur.com category @ayj984l3

First Date Jitters

tumblr.com category @DoesAsHeIsTold

What inevitably happens on all dates as a sissy

imgur.com category @[deleted]

Date Night [Snapchat]

imgur.com category @Captions4U

Sissy First Date

imgur.com category @PHXCurious

Date night for confident female.

gfycat.com category @onehardguy

[M/S] My Valentine's Day Date With Mom

gfycat.com category @badsluttymomma

Shy mom thinks she's too old to go on a date

gfycat.com category @[deleted]

[B/S]No need for dates

imgur.com category @L0lz_popz