8 XXX : Sissies

27 5'11" 175lbs former chubby guy finally fit and confident in my body

imgur.com category @AlphaGW

putting in my biggest silicone plug :o

gfycat.com category @keriberry_420

Wondering if I'd fit in here, first attempt at an ass pic

imgur.com category @Joey_pouch

my biggest belly ever, finally did an all-day stuffing followed by inflating until I felt fit to burst~

imgur.com category @reiinapop

Biggest plug ever (f)

gfycat.com category @keriberry_420

First time to fit the whole butt plug in for my master to enjoy :)

imgur.com category @showstopper1122

My ass swallowing the biggest plug I own ;)

imgur.com category @VivaciousVixen212

I was told my first plug would fit in here..

imgur.com category @[deleted]

Does this fit here?

imgur.com category @nimdaboon

I've been working towards being able to be penetrated. Here's my first time successfully taking a small plug.

imgur.com category @BromosexualOvertones

You finally got up the nerve to ask out your crush, and to your surprise she said yes and to come pick her up that same afternoon! You were too excited to notice the cars of the two biggest jerks in school parked out front. She says if you stay and watch

gfycat.com category @Whitesissycuckman

While home alone with my mom i was finally able to release all the tension between us... all over her face.

gfycat.com category @suckmydiddle