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Guys first encounter with a Sissy!

Daddy made me CUM SO MUCH from my sissy clitty by FUCKING my brains out! (Original Content!)

Fucking my Sissy subby on cam for the first time! ✨

When your Hotel receptionist recognized by big white butt from Grindr, he made me his little sissy white boi and fucked my butt deep. Sharing more in comments!

*IT'S ACTUALLY HAPPENING!* The frightened trepidation and magic of a sissies first time

Marine fucks sissy cd for the first time ! Link to my onlyfans below!

Daddy: 250 lbs of Muscle BANGIN' Sissy Mikah: 150 lbs of petite hottie (ORIGINAL CONTENT)

Where did you get your first one, sissy?

🌈Virgins, Sissies & Gooners are my fave subs, 😈 but u may come serve as u are slave👸🏻 (Strap-on not mandatory) First 5 to hmu get a $5 discount tonight![selling] 👻SC: lady.ells 💙Telegrm: elliebeanss

My hard latin cock is ready to train you and destroy your sissy useless clitty right now.. Who dare first? [domme]

Hy bois, this is my sissy-slut, Kate The prime example of what forced feminization can do to a weak boi (Watch it with audio and also check the first comment) :) ;)

A guide to sissy's first time sucking cock (Part 1)

A Sissies first date

You show me first 🍆

When it first slides in😍😩 (20)

my slutty hole needs filling, who wants to go first?💦

It will fit no worries, I will go slowly first.

Last night my girlfriend gave me a hard time with her strapon. The first insert vs the last pullout🥺

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Competing for who receives your cum 💦 Who would you fill first, me or my trans sis?

can't wait till i can order my first chastity cage.. sucking my dildo gets me so hard.. cant resist to play with my clitty

You were terrified at first... But everything worked out in the end.

Where do you want to put your tongue first babe~?😇🍑🍆

What’re you playing with first~?😇🍑🍆

A sissy never forgets her first taste...

After dressing me in a maid outfit I was told this was my first task!

I love when I give someone their first anal orgasm ❤️

My first post here 👅.

My very first video caption.. hope it’s not too bland 🖤

I gave My sissy her first creampie 💦

For our first date Mommy played dress up with a sissy slut then fucked him in the ass!

Your first time

Longer version of my first and with sound.

Which are you tasting first?

My first dildo and cage... I'm addicted. 😳

this is REALLY the first step

Here's my first video size test. I wonder how many of you can make it to the end without cheating

What are you like on a first date?

When my GF first bought me a maid outfit I thought it was for fun. Now when I forget to do the chores this is how she punishes me...

I had too much fun in a cage for the first time...

Very very first pounding....

Well since I'm locked up... you can go first. 🥺

You may be nervous at first, but after? You’ll be addicted 💖

your first bj(s)

What would you suck first? 😈

Who’s getting head first?👅

I was forced to drink my own piss, at first I was hesitant but now I feel like an absolute slut

I had my very first creampie am I a good girl now💦🥺?

My first session with my XL Chance on cam.... I don't think my butt will ever be the same

If you came over, what would you play with first?

My GF said I could sleep, but ONLY if I let her tie me up and attach this shock collar first... Let's just say I wasn't feeling very tired after that... - Full vid on my 0nlyfans and Fanzly

My First Sissygasm Video

My first ever caged felt so good

biggest dick gets to fuck first (hint: it’s always you)

What are you going for first? Gock or ass? 🫣🍆🍑

My first Dua Lipa sissy hypno video

My first ever sissy hypno / caption & I made it all by myself ❤️ with my content

getting knotted for the first time til i cum handsfree 🪢💖 >///<

22. I may not be your first college sissy, but I’ll be your favorite 🔥

My first time def gonna do more