https://www.porn-portal.com/tags/chastity-humiliation/ Sat, 02 May 2026 04:37:39 UTC https://www.porn-portal.com/video/129325/last-week-4-chastity-encouragement-stay-locked-locktober/
This video is part of the Locktober series and focuses on motivation and self control during the final week of the challenge. Locktober encourages participants to stay locked for the entire month as a test of discipline, patience, and commitment. In this talk I discuss how to stay focused, why the last week is often the hardest, and how to keep your mindset strong when temptation gets stronger. The video offers encouragement, guidance, and reminders about long term goals, self control, and the mental aspect of chastity challenges. If you have made it this far, the finish line is close, so stay disciplined and keep going. Educational and motivational content for adults interested in chastity challenges and Locktober events. Adults only. ]]> Tue, 17 Mar 2026 02:17:14 UTC https://www.porn-portal.com/video/129325/last-week-4-chastity-encouragement-stay-locked-locktober/ https://www.porn-portal.com/video/98152/cruel-milf-and-her-chastity-pig/
The nervous 49 year old virgin is naked and in chastity, Mistress looks fuckoff in her black teddy, nylons and high heels. They’re in her hotel room. She restrains his legs and hops onto his caged cock to dry hump it. She scratches his chest with her long, sharp manicured nails. His cock strains in the cage. She uses a permanent marker to label his body with the words CHASTITY PIG, VIRGIN, PATHETIC. He will be paddled, whipped and caned next. She puts him in a leg lock over her lap and starts beating his ass with her hand. Next he is beaten with her new ferocious palmattoria paddles and he squirms so hard that he tears her expensive stockings. He is pelted with the heavy leather Canadian prison strap, very very hurtful. But he is a dim, pathetic virgin fool and deserves it. Next he gets the cane and squirms like a worm. She lies down next to his body in bondage and he has to listen to her using the vibrator on herself until she cums. ]]> Fri, 06 Mar 2026 02:34:31 UTC https://www.porn-portal.com/video/98152/cruel-milf-and-her-chastity-pig/ https://www.porn-portal.com/video/96625/shaking-chastity-orgasm-intense-anal-prostate-machine-cumshot/
Shaking Chastity Orgasm - Intense Anal Prostate Machine Cumshot ]]> Mon, 16 Feb 2026 09:19:36 UTC https://www.porn-portal.com/video/96625/shaking-chastity-orgasm-intense-anal-prostate-machine-cumshot/ https://www.porn-portal.com/video/60576/basic-training-to-become-a-sissy-maid-locked-up-and-punished/
Today, the slut receives her final basic training as a sissy maid. She has been locked in a chastity cage for four weeks and is now willing to do everything her mistress demands of her. At the end of the lesson, she whines that she wants to be freed from the tight chastity cage, but instead she is mercilessly fucked in her sissy hole. ]]> Sun, 08 Feb 2026 03:58:16 UTC https://www.porn-portal.com/video/60576/basic-training-to-become-a-sissy-maid-locked-up-and-punished/ https://www.porn-portal.com/video/97323/sissy-gasm-time/
Making my little slut sissy gasm with the wand then making her taste her cum like the slut she is ]]> Fri, 06 Feb 2026 10:28:57 UTC https://www.porn-portal.com/video/97323/sissy-gasm-time/ https://www.porn-portal.com/video/91707/i-made-him-cum-into-his-mouth-self-facial-ruined-orgasm-chastity-cumeating-humiliation/
When I felt he was ready, I told him to curl a bit and get his head under his dick. It was so sexy to hold his dick and aim it at him. I loved that I was controlling where it was going to shoot. I could feel him getting hard in my hand as he was approaching orgasm. Knowing what was about to happen, I felt a shimmer in my stomach. And then as I felt the first spasm, I stopped jerking him, I just kept aiming it. It was so hot to watch him get a cumshot right into his mouth. ]]> Fri, 30 Jan 2026 18:35:55 UTC https://www.porn-portal.com/video/91707/i-made-him-cum-into-his-mouth-self-facial-ruined-orgasm-chastity-cumeating-humiliation/ https://www.porn-portal.com/video/98287/bg-chastity-sph-with-huge-dildo-pegging-and-cock-comparison/
This is a custom video! Contact me or Layne Love if you’d like your own! Aw, what a tiny little cock you’ve got there. I’ll humor you and play with it for a while. What’s that? You want to cum? Not a chance. Only big cocks deserve to cum, and I definitely don’t let little dicklets fuck me. You’re just too small, and I’ll take measurements to prove it! Now get the strapon harness on, because I want to ride a real cock until it makes me cum SO hard. First I’ll fuck this huge strapon cock until I’m satisfied, then we can lock up that useless little nub of yours in a chastity cage. Oh, what’s that? It’s just a piece of silicone? I’ll show you what a piece of silicone can do! Turn around and give me that hole of yours, and we’ll make you appreciate a real cock. Then I’ll put those legs of yours on my shoulders and make your little caged dick bounce as I pound that ass til I think you’ve had enough! ]]> Wed, 28 Jan 2026 06:57:55 UTC https://www.porn-portal.com/video/98287/bg-chastity-sph-with-huge-dildo-pegging-and-cock-comparison/ https://www.porn-portal.com/video/98132/sissy-boy-locked-in-chastity/
A blonde girl licks a guy's balls while he's wearing a chastity belt! Wow! All he can do is watch as they lick his balls, and he can't do anything. He's a sissy slave who can't cum today! And a hot and cute amateur blonde licks his balls until they shine! It's so arousing, but he can't do anything but watch! The guy is a eunuch who can only watch! The girl continues to lick again and again, sometimes smiling, sometimes laughing at this wonderful sight! Enjoy with us! ]]> Tue, 02 Dec 2025 01:53:05 UTC https://www.porn-portal.com/video/98132/sissy-boy-locked-in-chastity/ https://www.porn-portal.com/video/40903/my-husband-ejaculates-in-his-chastity-cage/
My husband has a small cock, it's locked in a chastity cage but sometimes I have to empty his prostate so I use dildos in his ass and in the end he ejaculates his cock still in a cage ]]> Thu, 13 Nov 2025 00:33:40 UTC https://www.porn-portal.com/video/40903/my-husband-ejaculates-in-his-chastity-cage/ https://www.porn-portal.com/video/60765/mistress-izar-tests-a-queening-still-with-a-surprise-for-her-sub/
Mistress Izar has been sent a Queening still that she's testing out and giving her sub a treat as were at the end of Locktober ]]> Thu, 06 Nov 2025 00:54:39 UTC https://www.porn-portal.com/video/60765/mistress-izar-tests-a-queening-still-with-a-surprise-for-her-sub/ https://www.porn-portal.com/video/60824/bar-flirt-fantasy-chastity-and-sissy-transformation/
We met as strangers. You remember my smile, the way my fingers traced the rim of my glass, the heat in my eyes when our conversation drifted into dangerous territory. You remember saying yes when I suggested we go somewhere more private. After that, the details blur. Now you’re here — in my lair — and I’m seated before you in my black leather corset and teal bra, every curve and line chosen to keep you on edge. Your little cock has become my clitty to play with, a symbol of the sissy pet you’re becoming. I draw the moment out, edging you until you’re trembling with need. I tell you exactly what you are now, how you’ll serve me as my perfect lesbian plaything. And just when you think you might be allowed release… I close the lock, leaving you aching, wet, and beautifully broken in your submission. A delicious fantasy of seduction, transformation, and prolonged denial. ]]> Wed, 13 Aug 2025 11:29:31 UTC https://www.porn-portal.com/video/60824/bar-flirt-fantasy-chastity-and-sissy-transformation/ https://www.porn-portal.com/video/98156/trained-to-obey-the-start-of-his-new-life/
He wakes up face-up, naked, confused... and I’m already sitting beside his cage, calm and in control. Dressed to destroy in black lipstick and a corset, I begin describing what life looks like under my rule. There will be pain. There will be edging. He’ll eat pussy, suck cock, and even be trained to take it deep. And he’ll thank me for it. I release his cage to begin his “orientation,” playing with him as I outline the rules. He can be a good boy and submit to my every desire... or face the consequences. Sensual, psychological FemDom. Obedience training. Reality bending. And you? You’re next. ]]> Tue, 12 Aug 2025 21:14:46 UTC https://www.porn-portal.com/video/98156/trained-to-obey-the-start-of-his-new-life/