
CARISSA'S HUMILIATION PLAYGROUND
Chastity Slave's Cuckold Reward (mp4)
10/2/26 5:47 PM•11 min•1568 MB•mp4•1080p
10/2/26 5:47 PM•11 min•1568 MB•mp4•1080pPrice$14.99 USDCategorysissy trainingRelated CategoriesChastity,Cuckolding,Femdom,Mind Fuck,Tease & DenialKeywordsCarissa Montgomery,Cuckold,Cuckolding,Femdom,Femdom Pov,Tease And Denial,Mind Fuck,Chastity,Chastity Device,Pussy Peek,Cock ControlPerformersCarissa MontgomeryDescriptionCarissa acknowledges that you are hot and yes, she is interested in you, but she wants you to know the way to get the key to heart starts by her getting the key to your cock! She has the cutest little pink panties for you to wear and your cock can be caged up nice and tight while you wear them! Do you think you can handle her? Do you really want to be with her? She's going to make you watch her get fucked by the gym rats while you stand there in your panties, in pain from your caged cock. Is that worth it to you? She is more woman than most men can handle but this is your chance to prove how much you appreciate her! (Video is 10 minute long and features POV Carissa at her seductive best!)
Cock Sucking 101 For Sissies (mp4)
9/18/26 6:23 PM•13 min•1828 MB•mp4•1080p
9/18/26 6:23 PM•13 min•1828 MB•mp4•1080pPrice$16.99 USDCategorysissy trainingRelated CategoriesDildo Sucking,Dildos,Femdom,Sissy Sluts,Slut TrainingKeywordsCarissa Montgomery,Dildo Sucking,Sissy,Sissies,Sissy Training,Cocksucking,Cock Sucking,Blowjob Training,Gag Reflex,GaggingPerformersCarissa MontgomeryDescriptionClass is in session sissies and it's time to work on our cocksucking skills! All good sissies need to know how to rub, lick and suck cock perfectly. It doesn't matter if you have a small mouth like mine! We need to start a bit smaller and work our way up to the big, fat cocks so you can properly please when you are called on! Let's practice together, so watch me closely and pay attention to all the little tricks that I will teach you! Soon you will be a dirty, little cocksucking sissy that all the manly men will want to facefuck! Let's get to work!
Bound Stroked and Left For Girlfriend To Find (mp4)
8/21/26 6:59 PM•15 min•2269 MB•mp4•1080p
8/21/26 6:59 PM•15 min•2269 MB•mp4•1080pPrice$15.99 USDCategorybondageRelated CategoriesFemdom Pov,Hand Over Mouth,Handjobs,Mind Fuck,Ruined OrgasmsKeywordsCarissa Montgomery,POV Handjob,POV Bondage,Mind Fuck,Hand Over Mouth,Tapegag,Tapegagged,Masturbation,Femdom,Lingerie,Ruined Orgasm,Cheating,Bound HandjobPerformersCarissa Montgomery, BrunoDescriptionCarissa gets contacted from her ex and he wants to hook up. Carissa is no dummy but she has a soft spot for her ex but she's definitely not going to make things easy for him! He's quite brazen actually. He has Carissa come over while his girlfriend is busy doing her Zoom calls for the day! That's a chancy thing to do! Carissa shows up in an outfit that will make your mouth hit the floor. She seductively talks and flirts with him before deciding to pull some rope out to tie him to him chair. She then tapegags him and then decides to use this opportunity to vibe herself in front of him. What a show! After getting herself off, she says it's now his turn! She strokes his throbbing cock and covers his mouth at the same time. What man can hold out with Carissa stroking him?? Not many! As she seductively encourages him to cum you can tell she has a further plan! As soon as he finishes cumming she smacks his cock a bunch of times and tells him he should have never broken up with her! She leaves him bound and stroked for his girlfriend to find! (Video is 14 minutes long with a fully verbally engaged POV)
Prostate Exam Misadventure (mp4)
8/7/26 10:04 PM•13 min•1840 MB•mp4•1080p
8/7/26 10:04 PM•13 min•1840 MB•mp4•1080pPrice$17.99 USDCategorymed examRelated CategoriesHumiliation,Latex,POV Strap-On,Strap-OnPerformersCarissa MontgomeryDescriptionDoctor Carissa is here for you consultation and things do not look good. A small penis and lack of a good amount of cum are not a good combination. After slapping on her latex gloves and inserting her fingers, she comes up with the perfect solution. It appears that cock is all you need and will improve your health considerably! Doctor Carissa provides the strop-on to help fuck you into a healthy prostate! (Video is 11 minutes long)
- 8/4/26 9:49 PM•15 min•1634 MB•mp4•1080p
8/4/26 9:49 PM•15 min•1634 MB•mp4•1080pPrice$15.99 USDCategorymade to cumRelated CategoriesBound Orgasms,Cbt,Chastity,Edging Games,Leather GlovesKeywordsCarissa Montgomery,Edging,Made To Cum,Chastity,Caged,Leather Gloves,Cbt,Flogging,Bound Orgasm,Rope On CockPerformersCarissa Montgomery, BrunoDescriptionWhen a slave does what he is asked and completes all tasks correctly with no issues or complaints, then that slave moves to the top of my slave list! This one has pleased me very greatly by making my life much easier and his reward will be well-remembered! Watch as I edge his poor caged cock! I have all kinds of tricks and implements at my disposal to make this as fun for him as it is for me! He even gets the ultimate reward of some gentle licks up and down his restricted cock!! He ultimately is blindfolded before his edging treatment is greeted with some great relief! This is one VERY HAPPY SLAVE! (Video is 13 minutes of slave edging ending with a caged cumshot dripping down my latex glove!)
No Excuses, Shrink Or Else (mp4)
7/17/26 5:49 PM•12 min•1709 MB•mp4•1080p
7/17/26 5:49 PM•12 min•1709 MB•mp4•1080pPrice$13.99 USDCategoryfemdomRelated CategoriesBikini,Mind Fuck,Pantyhose/Stockings,Shrinking FetishKeywordsCarissa Montgomery,Shrinking,Mind Fuck,Stockings,Micro Bikini,Mind Control,Femdom,Femdom PovPerformersCarissa MontgomeryDescriptionA slave wants to submit to the brutal task of losing weight and shrinking and he has left me angry and disappointed with his lack of progress. From here on out he will repeat the mantra that I give him. Over and over. Hopefully, he follows this mantra because I am losing my mind dealing with him! (Video is 10 minutes long)
- 7/10/26 5:39 PM•13 min•1853 MB•mp4•1080p
7/10/26 5:39 PM•13 min•1853 MB•mp4•1080pPrice$16.99 USDCategorycuckoldingRelated CategoriesButt Plug,Chastity,Dirty Talk,Femdom Pov,HumiliationKeywordsCarissa Montgomery,Femdom,POV,Keyholding,Chastity,Butt Plug,Humiliation,Dirty Talk,Cuckold,Cuckolding,CagedPerformersCarissa MontgomeryDescriptionWell look at you! What a good slave! All prepared for me! Let's get this shiny cage on that cock of yours because it's going to swell once I start telling you some things! Oh yes, we also need to put this butt plug right up your ass too! Are you getting hard already? I haven't done a thing yet!! Is it what I'm wearing? I think that thing is going to need a swat or two! On to bigger things now, and when I say bigger, I mean BIGGER! That's right, I'm talking about COCK! A nice spit roast is the way I like it! Yep, that's a fat one in mouth and an even fatter one pounding away at my pussy! Is all this talk too much for you? Are you throbbing and dripping?? Too bad! I may take these keys and NEVER let you free! (Video is 11 minutes long)
Dr Carissas Erectile Dysfunction Advice (mp4_
6/20/26 5:20 PM•13 min•1887 MB•mp4•1080p
6/20/26 5:20 PM•13 min•1887 MB•mp4•1080pDescriptionThank you for coming to see me today! According to the notes here, it says you are having some problems getting an erection? I think I should be able to find the source of this issue and get to the bottom of this issue. We have to go over a few things but I'm already noticing that you are staring at my legs and heels? Hmmm. Is that a slight bulge in your pants? I think we are getting somewhere already!! Maybe you are nothing but a panty sniffer too!! (Video is 12 minutes long)
- 6/12/26 5:43 PM•10 min•1466 MB•mp4•1080p
6/12/26 5:43 PM•10 min•1466 MB•mp4•1080pPrice$13.99 USDCategorygooningRelated CategoriesJerk Off Instruction,JOI,Lingerie,Mind Fuck,Orgasm DenialKeywordsCarissa Montgomery,Gooning,Gooner,Orgasm Control,Femdom,Mond Control,Cum Denial,JOI,Jerk Off Instruction,LingeriePerformersCarissa MontgomeryDescriptionYou know you can't help it. In fact, you actually want it. You want me to own your brain. You want me to control and mold you and your jerking ways. You want to jerk off all the time. Morning. Afternoon. Evenings. Bedtime. You just can't help it. Yes, I have control, and I will let you know when you can and when you can't come. I don't hear any complaints. You know why? Because that's just the way we want it. (Video is 9 minutes long)
- 5/1/26 7:15 PM•12 min•1784 MB•mp4•1080p
5/1/26 7:15 PM•12 min•1784 MB•mp4•1080pDescriptionHow long have I had you in chastity? It's been a long time hasn't it? Today is the day you can celebrate your release! You've been so well behaved, that I feel that you deserve some kind of reward! I'll bet I can just guess what's on your mind. How about I let you stroke your cock while you watch me make myself cum with my Hitachi! Yes, you would LOVE that! I've barely started and you look like you are already about to cum. I will have NONE of that! Now smack your cock hard over and over until I say stop! Hopefully that keeps you in check because your Mistress needs to make herself cum! Reaching around and touching my pussy while I vibe my clit will absolutely give me the orgasm I so badly need and deserve! But you?? BACK UP! Stop gawking so closely! Just stroke to my commands and quit staring at my pussy! Now slap yourself 20 times!! I'm done with you. Back in chastity you go! No orgasm for you!! Have better control of yourself next time! (Video is 11 minutes of making myself cum and tease and denial FOR YOU!)
Edged For Mistress Carissa's Amusement (mp4)
4/10/26 9:47 AM•16 min•2414 MB•mp4•1080p
4/10/26 9:47 AM•16 min•2414 MB•mp4•1080pPrice$18.99 USDCategorycbtRelated CategoriesCock Tease,Dick Slapping,Edging Games,Flogging,Made To CumKeywordsCarissa Montgomery,Edging,Rope On Balls,Tease And Denial,Cbt,Cock Slapping,Dick Slapping,Made To Cum,Flogging,Edging Games,Ball Stretching,Straps,Bound SlavePerformersCarissa Montgomery, BrunoDescriptionWhat do we have here?? Look like someone is here for my total amusement! He's all strapped in and ready for some edging and denial! And I'm just the Mistress for this! Just watch how tight the rope gets and how purple that undeserving cock gets! You know just how much I enjoy making him have to hold back! Every now and then, a couple swats are warranted to keep him in line! After the Hitachi is attached, he can't hold back anymore! Ooops! Looks like someone has made a mess on my fingers! Of course, he has to lick them clean!! What a lucky slave! I'll bet you wish it was you! (Video is 15 minutes of slave edging!)
You Know You Want To Worship Them (mp4)
3/27/26 8:26 PM•13 min•1924 MB•mp4•1080p
3/27/26 8:26 PM•13 min•1924 MB•mp4•1080pPrice$13.99 USDCategoryfeet joiRelated CategoriesCum Countdown,Dangling,Foot Worship,Garter & Stockings,POV Foot WorshipKeywordsCarissa Montgomery,JOI,Cum Countdown,Stockings,Garter And Stockings,Arched Feet,Spread Toes,Jerk Off Instruction,Femdom,POV Foot Worship,Heel Dangle,Femdom PovPerformersCarissa MontgomeryDescriptionYes you know how much you want to drop and worship them! My perfect soles, My perfect arches! The way I spread my toes through the sexy stockings I have on! It's just all too much for you! I know how much you like it when I dangle my heels, don't you? And the way I bend over and arch my back and kick up a heel?? It's way too much for you! I also know how much you want to whip that thing out and decorate my stocking covered feet - Yes, I will give you a countdown and you get to cum at that exact moment! The only catch is you have to lick up your messiness! I think that's a deal! (Video is 12 minutes long)
- 3/20/26 6:57 PM•13 min•1882 MB•mp4•1080p
3/20/26 6:57 PM•13 min•1882 MB•mp4•1080pPrice$14.99 USDCategoryjerk off instructionRelated CategoriesCum Countdown,Femdom Pov,Garter & Stockings,JOI,Pvc-VinylKeywordsCarissa Montgomery,Jerk Off Instruction,JOI,Pvc Panties,Pvc Stocking,Boots,Cum Countdown,Cum Eating Instruction,Dirty Talk,Mind Fuck,Panty Sniffing,Ass SniffingPerformersCarissa MontgomeryDescriptionYou bought us matching outfits so that you can look "just like me"? Haha!! Well, I think we all know that you won't ever look anything like me but let's get on with it! I know what you want? You want to worship these sexy legs of mine and sniff my panties don't you? Of course you do! I know you! Get your nose in there and sniff! You LOVE it! Looks like you're starting to get quite a bit of "swelling" in your matching panties aren't you?? You just keep those panties on and put your little hand in there and stroke yourself! I'm going to give you a countdown and you are going to cum right in your panties got it??? And then when you finish cumming in them, take them off and stuff them in your mouth!! Don't act like you won't like it! You know that's your ultimate prize! Now make sure you thank me!! (Video is minutes long)
- 3/13/26 6:17 PM•14 min•2016 MB•mp4•1080p
3/13/26 6:17 PM•14 min•2016 MB•mp4•1080pPrice$14.99 USDCategorysissy trainingRelated CategoriesButt Plug,Crossdresser,Dildo Sucking,Maid Fetish,Sissy SlutsKeywordsCarissa Montgomery,Sissy Training,Sissy Maid,Crossdressing,POV,Butt Plug,Dildo Sucking,Heels,Stockings,Dirty TalkPerformersCarissa MontgomeryDescriptionOh My!! Aren't you going to look so adorable today! I'm going to dress you up to look just like me! Look at this pretty maid dress! I'll bet you can't wait to get yourself in it and prance around and show off your slutty skills! But Wait! The best part is getting you all dressed up first! The anticipation will build that way! I have some crotchless panties for you and some silly smooth stockings! Of course, we need to have some nice fuck-me heels right? Put them on!! Now let's get that dress on because I have a nice fat dildo cock for you to suck on! Watch me first! Push that in your mouth and show off the cockhead bulge in your cheek! What a good slut! Remember, plenty of lipstick rings on this thing!! Now before we get you ready for the real thing, you need to bend over and put your plug in! That hole of yours needs to be plugged nice and tightly while you show off your maid outfit!! Are you ready for some real cock now? I'll bet you are!! (Video is 12 minutes long)
Gag Yourself and Jerk Off For Me (mp4)
3/10/26 9:50 PM•12 min•1716 MB•mp4•1080p
3/10/26 9:50 PM•12 min•1716 MB•mp4•1080pPrice$14.99 USDCategoryjerk off instructionRelated CategoriesCum Countdown,Duct Tape Fetish,Femdom Pov,Gag Talk,JOIKeywordsCarissa Montgomery,Jerk Off Instruction,JOI,Cum Countodwn,Cleave Gag,Panties In Mouth,Tape Gag,Tape Gagged,No Panties,Pussy Peak,StrokingPerformersCarissa MontgomeryDescriptionSome mumbling gag talk jerk off instruction is the order of the day today! Yes, that's right! Pull out that cock of yours and start stroking yourself while I take you through the motions! First, I'm going to tease you with some pussy peaks. Of course, I "forget" to wear panties as I seductively pose myself to give you just enough glimpses to keep you on edge. Then we pull out the hardware so make sure you have your panties, a cleave gag and some duct tape while you play along with me! You are going to pay close attention while I pack my mouth and double gag myself and instruct you on your cock stroking. Maybe if you play along properly, I will reward you by letting you shoot your suppressed cum all over my tape-gagged mouth! Now that will be a dream come true wouldn't it? (Video is 11 minutes long)
Oops! Another Handjob Relapse (mp4)
2/7/26 12:07 AM•9 min•1161 MB•mp4•1080p
2/7/26 12:07 AM•9 min•1161 MB•mp4•1080pPrice$12.99 USDCategoryhandjobsRelated CategoriesCuckolding,Cum Play,LickingPerformersCarissa Montgomery, BrunoDescriptionI've had this ongoing issue where I just see a random guy and decide without much thought of the consequences, that I want to give him a handjob! This has been going on for years and my hubby has been aware of this problem and I keep promising that I won't do it anymore. The problem is that I just can't stop! I find myself in this same situation yet again! This good-looking guy I found gave me extra pleasure because it turns out that he has a nice-looking cock with silky, smooth balls! I just can't resist! Here we go again! My hubby calls while I'm stroking away and although I try my best to keep this secret, I make the mistake of licking my fingers a few times and have to explain that I'm baking a cake! Will he buy it?? I don't know but I'll tell you what, I think half the fun I get from this is the thrill of jerking off a stranger while my hubby has no idea! What a turn-on! (Video is 7 minutes long and is an actual full handjob video!)
You Were Late For The Gangbang Cuck (mp4)
1/30/26 7:35 PM•12 min•1750 MB•mp4•1080p
1/30/26 7:35 PM•12 min•1750 MB•mp4•1080pPrice$14.99 USDCategorycuckoldingRelated CategoriesDirty Talk,JOI,Lingerie,Mind Fuck,Tease & DenialKeywordsCarissa Montgomery,Cuckold,Gangbang Talk,Lingerie,Tease And Denial,JOI,Jerk Off Instruction,Mind Fuck,Dirty Talk,Cum DenialPerformersCarissa MontgomeryDescriptionWhat the hell is wrong with you?? You're late! I just had the HOTTEST gangbang with FOUR studs who fucked me silly! What's you excuse? It doesn't matter really. You were supposed to be here and watch the party! These guys took turns fucking my mouth, my big titties, my pussy and even my ass! They even fucked me in all holes at once! They fucked me every conceivable way and you weren't here to watch and be my cleanup cuckold!! I'm just getting wet telling you all about it! There was cum flying everywhere! You missed a golden opportunity to be cleanup and I was even thinking of letting you clean off my cum-covered pussy! But Nooooo, you had to be late! No excuses! Are you getting hard hearing about this? It sure looks like it!! Maybe I'll let you pull your cock out and stroke yourself a bit! Woo, all of this talk about me being fucked and cum covered looks it's making you ready to explode! Not today! Put your cock away and lick the dribble of off your fingers because that's all the cleanup you get to do! Put it away and get downstairs and organize my dungeon. (Video is 11 minutes of POV super dirty gangbang talk that will leave you feeling humiliated!)
- 1/16/26 5:26 PM•12 min•1806 MB•mp4•1080p
1/16/26 5:26 PM•12 min•1806 MB•mp4•1080pDescriptionOh slave! You are really something! Look at how hard you are already? Well, get a good look because that's all you are gonna get! Just admire me and my beautiful pussy because all you are going to do is stroke yourself and watch me while I make myself cum! MAYBE, I'll let you cum. Or on the other hand, I probably won't! Too bad!! (Video is 11 minutes and features solo masturbation content)
JOI: Reward Or Punishment? (mp4)
1/2/26 8:37 PM•13 min•1838 MB•mp4•1080p
1/2/26 8:37 PM•13 min•1838 MB•mp4•1080pPrice$11.99 USDCategoryjoiRelated CategoriesBondage Device,Cbt,Chastity,Cock Tease,Cum CountdownKeywordsCarissa Montgomery,Cbt,Ball Press,Electric Play,Spiked Cock Cuff,Cock Tease,Dirty Talk,JOI,Jerk Off Instruction,Cum Countdown,Slave TrainingPerformersCarissa MontgomeryDescriptionWe are gonna try a different approach for that cock of yours my slave! I have some clever devices for you to try on today! These are the kinds of things that are going to make getting a hard cock, quite difficult! Just take a look at these things! Some mild discomfort to say the least! All of this joy that I get watching you in such misery will be rewarded today! I just may let you free and allow you stroke that cock for me!! Show me what you got!! (Video is almost 12 minutes long)
Christmas Miracle For My Chastity Slave (mp4)
12/12/25 9:54 PM•12 min•1786 MB•mp4•1080p
12/12/25 9:54 PM•12 min•1786 MB•mp4•1080pPrice$12.99 USDCategoryfemdom povRelated CategoriesChastity,Cock Tease,Cum Countdown,Jerk Off Instruction,JOIKeywordsCarissa Montgomery,JOI,Jerk Off Encouragement,Jerk Off Instruction,Cum Countdown,Chastity,Chastity Cage,Cock Tease,Slave Reward,Slave Training,Reward,Femdom,Femdom PovPerformersCarissa MontgomeryDescriptionSanta Carissa has decided to give you a gift since you have been a fairly good slave and have been buying me such nice gifts lately! Today I have just what you needed! A brand-new chastity cage for you! It's just your size! Small, for your teeny, little cock! Here, take a look. I'll show you how to put it on! Nice and snug! No growth allowed here! Obsessed with my legs and feet? No problems here! The restriction will keep you on task! However, it won't stop me from fucking with you and showing off all of my sexy features! It's what I do! Being the giving person I am, I'm going to reward you a Christmas gift - the gift of the freedom to jerk off one last time before you get locked up for good! Go ahead and listen to your Mistress as I guide you through a good cock-jerking. Go ahead and stroke it! Think about all of the cuckold scenarios I tease you with. Stroke it while I give you the countdown to cum! Have your gratitude for Santa Carissa! (Video is ten minutes long)
