
CARISSA'S HUMILIATION PLAYGROUND
5/28/20 5:45 PM•11 min•244 MB•mp4•720pPrice$10.99 USDCategorysissy trainingRelated CategoriesChastity Male,Dirty Talk,Femdom Pov,Garter & Stockings,Strap-OnKeywordsCarissa Montgomery,Heels,Sissy Training,Strap-on,Femdom,Humiliation,Stockings,Cuckold,Chastity,POV,Femdom Pov,Dirty Talk,Legs,Blonde Goddess,Close UpsPerformersCarissa MontgomeryDescriptionIt's been a long day at work and I need entertained now! All day I was prepared for this. I had my strap-on tucked in my dress all day and I am absolutely ready to go! You like how I have a big cock under my dress?? Well show me how much you like by sucking on it for me. I know you'll do it but I want you to choke yourself on it. I want to sissy your sissy eyes water as I choke you on it! I think I may have trained you so well that you are able to take the whole thing down! Good little sissy! Tonight I think I will let you watch me get fucked by my husband if you entertain me! I'm going to fuck your ass first and you're going to be put in chastity! I don't want to see you getting a hard cock while I fuck you sissy hole. I'm going to bend you right over my counter and that ass will be all mine. Just remember, you allow me stretch that hole, I may let you watch me get fucked! Who knows, maybe I'll allow my ass to get fucked too and maybe fill me with a creampie..... Oh what do you know?? He's here! Honey, I need your cock!
3/26/20 9:52 PM•11 min•314 MB•mp4•1080pPrice$10.99 USDCategorysissy trainingRelated CategoriesButt Plug,Dildos,Femdom,Feminization,Make Me BiKeywordsCarissa Montgomery,Body Stocking,Sissy Training,Feminization,Femdom,Latex Gloves,Dlido,Humiliation,Boot Fetish,Knee High Boots,Ass Fucking,Shaved Pussy,Inflatable Buttplug,Asshole Fingering,Big TitsPerformersCarissa MontgomeryDescriptionToday, I'm here to aid my little Wannabe sissies in their desires to get their sissy-hole loosened up and ready for some hard fucking! As you can see, your Mistress is dressed Fabulously with knee high boots and a sexy body stocking with the crotch fully open. This is for you to see how I will have you spread yourself open so you can get that sissy asshole ready.
On my medical table, I have various items to help with the stretching of that hole. So let's start by me slipping on my latex gloves and get some lube on my fingers to start the penetrating of your sissy-hole. Let's start with my inflatable buttplug! We can stick that in your sissyass and slowly inflate it as it spreads your hole wider and wider. This will allow me to spread it with my fingers wider and spit in that hole to keep it lubed up.
This is where we move up to my large dildo cock! OOO! This will make you hole begin to gape for me! I will hold this dildo and handfuck your sissy fuck-hole! Maybe I should spit in that asshole again so it can get ready for the bigtime??
Well here it is! My big black one with ridges! You're not going to lay on your back for this one! You're going to squat over it and lower yourself down and take each ring until it's fully in your asshole! Are you ready for the challenge?? Sure, you are you little sissy!! Now practice and get ready to see me!!!
9/21/19 10:58 PM•14 min•303 MB•mp4•1080pPrice$13.99 USDCategorysissy trainingRelated CategoriesAss Humiliation,Dildo Sucking,Femdom Sex,Pegging,Strap-OnKeywordsCarissa Montgomery,Boobs,Domination,Femdom Sex,Strap-on,Latex Gloves,Ass Humilaition,Female Domination,Sissy Training,Femdom,Big Tits,Pegging,Asshole FingeringPerformersCarissa Montgomery, slave GuiseppieDescriptionI'm so sick of these little slaves needing to be masked. It's time to make them have to pay and this one is going to start by getting his mouth fucked a bit. I'm going to fuck his mouth like a little porn star and ALL my Mistress friends will use him too. After thoroughly using his mouth I show my appreciation by spitting on him, in his mouth and on his cock. It's time for him to get strapped down to my spanking bench so I can smack him and ready his asshole for my strap-on cock! At least he is trained well to Thank me over and over! I put my latex gloves and prepare his asshole for my fingering of his wide, slutty fuckhole! He takes the probing VERY well and again Thanks His Mistress. After some deep finger penetration, he is clearly ready for his Mistress to give his hole a good fucking. He takes it with total ease and again, Thanks me repeatedly. Well Trained! I fuck him good and hard like a good little slut and as I finish off, I remind him that his hole is mine and I plan on sharing it with ALL my Mistress friends!
Carissa Handfeeds a Sissy His Cum (HD WMV)
8/5/19 12:44 PM•13 min•496 MB•wmv•1080p
8/5/19 12:44 PM•13 min•496 MB•wmv•1080pDescriptionHere is an all new hot clip! Mistress Carissa found herself a little sissy faggot who likes to wear women's panties! She brought him to her Dungeon so she could have her own Amusement with him. This little sissy had to be masked because he didn't want his friends to know how much he likes to wear panties. Mistress makes him bend over her spanking table and smacks his little panty-wearing ass with her bare hand until its' bright red. She then informs him one of his purposes is to suck on her BIG Strap-on cock. She primes him by making him suck on her fingers. She notices that this is giving him a wet spot in his panties which she wipes up and makes him eat. She then makes him straddle the table and straps him down for some dildo sucking. He's obviously had some prior practice as he turns his head sideways to allow Mistress Carissa's dildo deep in his mouth as she face fucks him. She notices he is getting very slobbery as he sucks her schlong. She then decides to tease him that she's going to peg him but instead only dry humps him. Mistress Carissa's decision for this sissy is to have him get down on his knees and suck her strap on while he jerks his cock for her. She pulls his panties down to reveal his stiff sissy-dick. She slaps it around as she goes to put on some latex gloves. She then demands that he now stroke his little cock while he aggressively sucks her strap-on cock. She then stands right next to him and strokes her cock in unison with him and urges him to continue to stroke his cock so he can cum for her. However, the plan is for him to jerk his cum directly into her latex-gloved hand. She demands that he cum for her and as he does Mistress Carissa grabs as much of the sissy slaves' cum load and feeds it to him. He VERY willingly obliges and she then tells him that he needs to go a clean his sissy faggot self up!
