First sissy date
![First sissy date](/thumbs/76/f7/BlaringWideeyedArrowana.jpg)
"Date Night" for a sissy
!["Date Night" for a sissy](https://external-preview.redd.it/oVMkxO-84tBlv3iEF6TjDtY9rWCCxIBeBVEKk0q8CHQ.jpg?width=320&crop=smart&auto=webp&s=f3d3e6b5f61c69308d833b669b71166a341558b6)
Date night
![Date night](/thumbs/bd/d3/SunnyVirtuousPanther.jpg)
Let's skip dinner and FUCK! [Date Night]
![Let's skip dinner and FUCK! [Date Night]](/thumbs/d2/86/OrchidLinenCats.jpg)
On a date with your girlfriend 😍
![On a date with your girlfriend 😍](/thumbs/4c/40/ExtralargeSnarlingNorthernhairynosedwombat.jpg)
"I Love our special date nights. Have fun at home!"
!["I Love our special date nights. Have fun at home!"](/thumbs/ae/92/StalePowerfulFoal.jpg)
Dating your hand is better than being rejected, forever.
![Dating your hand is better than being rejected, forever.](/thumbs/24/c5/LoneSwiftEskimodog.jpg)
Dating a college gymnast has its perks if you’re adventurous
![Dating a college gymnast has its perks if you’re adventurous](/thumbs/9f/41/AmusedQuestionableCockroach.jpg)
[story] you and your girlfriend started dating at a young age, and years later you finally want to settle down with her... but she feels like she missed out because she never got the chance to experiment with other guys, since she has always been with you
![[story] you and your girlfriend started dating at a young age, and years later you](/thumbs/20/d6/DigitalWarlikeAfricangroundhornbill.jpg)
The same way it happened with your wife when you were dating ?
![The same way it happened with your wife when you were dating ?](/thumbs/cd/05/DangerousScientificAnnashummingbird.jpg)
[M/S] Mommy Tip # 4 – Have a Date Night with Your Son
![[M/S] Mommy Tip # 4 – Have a Date Night with Your Son](/thumbs/c1/ed/SatisfiedIncomparableBushsqueaker.jpg)
You asked your wife if she was planning on fucking on her first date with some guy
![You asked your wife if she was planning on fucking on her first date with some guy](/thumbs/16/99/BlackandwhiteBrightBoa.jpg)
Looks like you'll be the only without a date
![Looks like you'll be the only without a date](/thumbs/5f/a3/VioletFumblingTarsier.jpg)
My GF's date idea for 420.
![My GF's date idea for 420.](/thumbs/a1/48/CoolRundownAfricanaugurbuzzard.jpg)
Sissy Dating essentials
![Sissy Dating essentials](/thumbs/be/93/MeatyFirstPug.jpg)
Dating advice
![Dating advice](/thumbs/71/b7/DefiantKnobbyLing.jpg)
How every sissy date should finish
![How every sissy date should finish](/thumbs/eb/29/MassiveSoupyNorthernelephantseal.jpg)
Date Night
![Date Night](/thumbs/7f/e9/CostlyHeavenlyAntlion.jpg)
Mom goes out on a date with my bully...
![Mom goes out on a date with my bully...](/thumbs/bb/37/SlowInsignificantMacropod.jpg)
Dating
![Dating](/thumbs/3d/7c/ElectricSadPanther.jpg)
Dates
![Dates](/thumbs/ae/b7/BlandSpotlessBuck.jpg)
You might get a second date.. even start dating her and get into a relationship with her.. but she won't stop fucking her roommate..you're already getting cucked
![You might get a second date.. even start dating her and get into a relationship with](/thumbs/59/e8/InformalGlassXuanhuaceratops.jpg)
Dress and date paid for by your money
![Dress and date paid for by your money](/thumbs/1a/11/NaiveIvoryStingray.jpg)
My Son’s Friend Takes me out on a Date
![My Son’s Friend Takes me out on a Date](/thumbs/31/eb/MerryRealBuckeyebutterfly.jpg)
Her date nights go a little differently depending who she's with..
![Her date nights go a little differently depending who she's with..](/thumbs/72/38/JampackedGloriousWhale.jpg)
Dating Your Stepmom
![Dating Your Stepmom](/thumbs/5c/5e/MuddyShockingEuropeanpolecat.jpg)
You didn't like feet when you started dating but.. now it's all she gives you, and you're thankful for it.
![You didn't like feet when you started dating but.. now it's all she gives you, and](/thumbs/d6/40/GoldenrodNextTadpole.jpg)
The Frustrations of Dating a Domme.
![The Frustrations of Dating a Domme.](/thumbs/68/23/EachEntireColt.jpg)
Guess your girl's date can't resist his breeding urges
![Guess your girl's date can't resist his breeding urges](/thumbs/a2/3d/DisfiguredUniformPaperwasp.jpg)
Mom Lets Me Practice Kissing Before My Big Date
![Mom Lets Me Practice Kissing Before My Big Date](/thumbs/35/67/NaiveDefenselessNortherncardinals.jpg)
Picnic dates are SO romantic! 🥰(Creampie)
![Picnic dates are SO romantic! 🥰(Creampie)](/thumbs/76/8d/SillyImpressionableBeetle.jpg)
Your mom is really excited for her next date with him.
![Your mom is really excited for her next date with him.](/thumbs/1a/a3/DisloyalGrimCats.jpg)
Two days later, he showed up at the restaurant we go to on date night. He made me blow him under the table while hubby had to sit quietly and wait for him to be done with me.
![Two days later, he showed up at the restaurant we go to on date night. He made me](/thumbs/71/cb/LuckyGoldenrodRedheadedwoodpecker.jpg)
She only dates guys with huge cocks.
![She only dates guys with huge cocks.](/thumbs/eb/e8/MerryLiquidWaterstrider.jpg)
Date start / Date End
![Date start / Date End](/thumbs/9d/95/GrayDarkolivegreenLarva.jpg)
but only if you are well-behaved and treat me and my bull to a luxurious date without you first 😜
![but only if you are well-behaved and treat me and my bull to a luxurious date without](/thumbs/13/08/BubblyIndelibleAustralianfreshwatercrocodile.jpg)
Your wife’s coworker is keeping you up to date…
![Your wife’s coworker is keeping you up to date…](/thumbs/68/37/EminentAuthenticScallop.jpg)
Hubby finds date nights to be... Extra frustrating.
![Hubby finds date nights to be... Extra frustrating.](/thumbs/9a/c5/VioletGuiltyIchthyostega.jpg)
Girlfriend was supposed to meet you for a date but got distracted by her friend's cock
![Girlfriend was supposed to meet you for a date but got distracted by her friend's](/thumbs/c2/f6/FearfulSuperGander.jpg)
Date night with him vs you
![Date night with him vs you](/thumbs/8e/5a/JollyRareFlyingsquirrel.jpg)
Cancelling on date night...
![Cancelling on date night...](/thumbs/c2/ba/SneakySubstantialFantail.jpg)
It's going to be a good first date
![It's going to be a good first date](/thumbs/52/e6/SaneMeaslyChickadee.jpg)
dating made fun
![dating made fun](/thumbs/11/69/MagnificentProfuseGrouse.jpg)
Dinner date with mom
![Dinner date with mom](/thumbs/1a/81/BouncyThickGoat.jpg)
I found out my wife was cheating on me but didn't do anything about it.. he's right! I don't wanna lose her so I'll just pay for their dates and let them have their fun... even if I have to put up with these asshole's condescending snapchats
![I found out my wife was cheating on me but didn't do anything about it.. he's right!](/thumbs/55/ef/SlategreyReadyMarmot.jpg)
She cancelled date night again?
![She cancelled date night again?](/thumbs/f9/72/UrbanProductiveDowitcher.jpg)
A date with a misogynist PT2 - re education
![A date with a misogynist PT2 - re education](/thumbs/a9/3e/GrossGoldenBullfrog.jpg)
A date with a misogynist (story)
![A date with a misogynist (story)](/thumbs/32/3c/ReadyGreenSpittlebug.jpg)
Perfect Date With Daddy
![Perfect Date With Daddy](/thumbs/e2/74/FixedWiryAnnashummingbird.jpg)
Your gf sucked off her date and he filled her mouth
![Your gf sucked off her date and he filled her mouth](/thumbs/b7/b4/DarkblueThunderousUrutu.jpg)
Your mom is here in case your date doesn't go well
![Your mom is here in case your date doesn't go well](/thumbs/7b/aa/AgileCrowdedHumpbackwhale.jpg)
My wife was late for our celebration date
![My wife was late for our celebration date](/thumbs/20/f7/PhonyForcefulBarnswallow.jpg)
Date Night with the Bully [Full Video in the Comments!]
![Date Night with the Bully [Full Video in the Comments!]](/thumbs/2a/e4/SuperficialConsciousGreyhounddog.jpg)
Inviting the date
![Inviting the date](/thumbs/31/c4/WorriedEthicalAmericanwarmblood.jpg)
What happens when you date a busy girl
![What happens when you date a busy girl](/thumbs/bf/6f/SpecificFrozenAntipodesgreenparakeet.jpg)
Speed-dating with mom
![Speed-dating with mom](/thumbs/ba/2d/DesertedInternalMicrovenator.jpg)
On a date with my son
![On a date with my son](/thumbs/dd/7c/MurkyMountainousImperatorangel.jpg)
She would laugh at your nudes with her fuckbuddy when you dated
![She would laugh at your nudes with her fuckbuddy when you dated](/thumbs/fb/f8/PointedTremendousPeccary.jpg)
It's nice to give it up on the first date
![It's nice to give it up on the first date](/thumbs/4c/db/PreviousChartreuseTiger.jpg)
Jesse now Jessica, having a nice date
![Jesse now Jessica, having a nice date](/thumbs/bb/3e/TurbulentSnappyBluefish.jpg)