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First Date Caption
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First sissy date
First Date With Mom
Betty, a busy weekend
First Date
Let's skip dinner and FUCK! [Date Night]
![Let's skip dinner and FUCK! [Date Night]](/thumbs/d2/86/OrchidLinenCats.jpg)
Maybe try dinner and a movie next time instead
Your first date went great! She even invited you back to her place!
Your first date with him was a little rough at first... but then you started to like it.
Would our first date be ruined if it ended like this? 😷💧
It’s not cheating, she just lost a bet - she said she was sorry :(
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How the date starts vs How the date ends
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You asked your wife if she was planning on fucking on her first date with some guy
First Date
You’re a sissy
First date: Get coffee, and he'll give you his cream!
First date with Daddy
Alt GIF by filmmagick
A Sissies first date
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Dating
First date
Memories
Dates
Casual
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
Spare no expense when dressing your gf for her date
Dress and date paid for by your money
Fav
Effective
A successful first date
Best first date ever 😍
How did your first date go...?
Is squirting on the first date a good thing?
A Sissy's first Date
First date
First dates
but only if you are well-behaved and treat me and my bull to a luxurious date without you first 😜
Hot mom is bringing her loser son along on as a chauffeur on your first date so you can bully him
I’d say our first date went well ;)
It's going to be a good first date
What are you like on a first date?
Your crush goes on a date with your buddy at the gym. She likes guys who work out
She has to look good for your first date, doesn't she?
Look for some new dates GIF by sissyanalslutt
It's nice to give it up on the first date
Girl gets knocked up on the first date
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Such a great first date!
Mommy Helped Me With My First Date Jitters...
The first date
You love getting dolled up in public...
I downloaded Grindr because I was a little curious...
She's the one
You finally downloaded grindr...
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Your wife gave him anal on the first date yet she never gave you (Captionsforever on imagefap)
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