https://www.fapbox.com/tags/chastity-orgasm/ Thu 04 Jun 2026 07:39:28 +0200 https://www.fapbox.com/videos/33738745/intense-prostate-milking-in-chastity/
Intense Prostate Milking in Chastity (Hands Free Cum) The grand finale of sub c's anal adventures - Back in a familiar place, flat on his back with his legs suspended before him so Mistress has full view of his tight little arsehole and chastity cage. I begin by slowly tickling and teasing the lube all around his sensitive hole, ensuring every nerve ending is ignited by My touch, then I begin to work My fingers in his hole, one then two, then back to one.. finding that sweet spot and once I've found it there's no stopping Me, milked and ruined in his chastity cage just from Mistress fingering his asshole, with the wink of approval from Me he blew his load all over his leg, I didn't touch his cock once. A testament to My skill and his weakness. ]]> Tue 04 Mar 2025 01:49:00 +0200 https://www.fapbox.com/videos/33738745/intense-prostate-milking-in-chastity/ https://www.fapbox.com/videos/33778778/hot-wax-ball-squashing-torment/
My boy in training has been permitted one release out of chastity today under the guidance and instruction of Myself and Miss Lady Louisa. Strapped to the bench and hooded so he has no idea what is about to commence, we set upon the task of making him cum but not without certain challenges. First, his tiny little balls pressed in perspex, tightened with nuts and screws so we can see all the pressure building up beneath. Secondly, hot candle wax dripped directly onto his disgustingly erect cock and straight down his tiny pisshole. If he is to cum, he's to break the wax. With all of these things happening to his poor body, he has no choice but to take it all if he wants that much ached for release! ]]> Mon 03 Mar 2025 20:20:52 +0200 https://www.fapbox.com/videos/33778778/hot-wax-ball-squashing-torment/ https://www.fapbox.com/videos/33725810/ball-slapping-cum-extraction/
A deft silence as the beauty off Mistress Diana makes her way over to her subject, waiting patiently, exposed with his knees held aloft, awaiting her control. At least once per month, Mistress delivers the most cruel chastity torment to her locked boys, now it is this ones turn to see what she has too offer! This one has been locked up for some time & Mistress Diana is finding new ways every time to deliver the most cruel punishments. Silence from Mistress as all you hear is the sound of he Slubb ignite, teasing the cage from top to bottom, it doesn't take this one long to get to the edge of orgasm. She finishes her boy in one of the most cruel ways possible. His tender, red, full balls receive a good slapping! Tapping away, bringing this one right to the edge before he can't take any more. A delicious ruined orgasm & not even a single touch on that pathetic cock, how embarrassing... ]]> Mon 03 Mar 2025 10:54:33 +0200 https://www.fapbox.com/videos/33725810/ball-slapping-cum-extraction/ https://www.fapbox.com/videos/33776465/anal-training-and-cumming-in-chastity/
This young inexperienced sub has somehow found his way into My hands and needs to be prepared in everyway possible for the future that lies ahead of him. Starting with his anal training. He's only felt the wrath of My strap-on a few times before now and locked away in chastity, this is a sensation overload for his poor inexperienced body, prostate swollen he cannot help but unleash a stream of disgusting slavecum all over himself as Miss Diana works her slender fingers inside of him. Then again after she has thrusted her cock deep inside his ass. Much more training needed for this boy.... ]]> Thu 27 Feb 2025 02:08:17 +0200 https://www.fapbox.com/videos/33776465/anal-training-and-cumming-in-chastity/ https://www.fapbox.com/videos/33750775/non-stop-pegging-gives-me-7x-anal-orgasm-i-rewarded-with-1-for-her-sissy-dick/
After warming up her bussy with my hand dildo, it was time to fuck her sissy ass with my medium cock. OMG!! She started to cum like a bitch just from the ass!! I changed to a bigger dildo to see if the effect continued, and he was also cumming in chastity, so finally I removed the cage and touch her clit to reward such a nice behaviour. ]]> Sat 21 Dec 2024 06:25:40 +0200 https://www.fapbox.com/videos/33750775/non-stop-pegging-gives-me-7x-anal-orgasm-i-rewarded-with-1-for-her-sissy-dick/ https://www.fapbox.com/videos/33743954/chastity-slave-training-increasing-frustration/
Chastity slave today I want to make it clear that we are just at the beginning of your frustration! I'm going to improve it even more! Now I want you to promise me that you will carry every weight for me, no matter how small. Of course the chastity cages are now getting smaller and smaller! And you will constantly think of me. But now let's play an awesome game. No, you shouldn't take the cage out now! Get your vibrator, try to excite your cock in the chastity! To do this, put on a silk scarf from me, tie it tightly around your neck and sniff it. I change the silk scarf because I'm just trying on silk scarves again. You get a certain amount of time from me to fiddle around with the vibrator on the cock cage. Then I'll count you down to 0. Oh, it didn't work even though you begged for an orgasm. Now you confess to me that you have fallen for me. Say it loud and clear... ]]> Wed 10 Apr 2024 18:09:03 +0200 https://www.fapbox.com/videos/33743954/chastity-slave-training-increasing-frustration/ https://www.fapbox.com/videos/33809713/lover-gets-orgasm-fucking-wife-cuckold-chastity-belt-strap-on/
From wife lover gets orgasm, cuckold - chastity belt, strapon and humiliation ]]> Thu 29 Jul 2021 18:03:41 +0200 https://www.fapbox.com/videos/33809713/lover-gets-orgasm-fucking-wife-cuckold-chastity-belt-strap-on/ https://www.fapbox.com/videos/33757913/chastity-slave-whines-like-a-bitch-orgasm-denial-with-pussy/
My pet won’t stop whining like a little bitch! I know he’s dying to fuck me, so this drives him crazy! I rub my pussy over his cock edging him over and over, but I never let him cum ]]> Sat 15 May 2021 07:56:39 +0200 https://www.fapbox.com/videos/33757913/chastity-slave-whines-like-a-bitch-orgasm-denial-with-pussy/