https://www.fapbox.com/tags/sissy-training/ Thu 04 Jun 2026 13:53:02 +0200 https://www.fapbox.com/videos/34146952/mrs-sophie666-strapon-sissyfication-training/
]]> Thu 26 Jun 2025 11:42:25 +0200 https://www.fapbox.com/videos/34146952/mrs-sophie666-strapon-sissyfication-training/ https://www.fapbox.com/videos/33817335/hospital-1-sounding-and-electro-scene/
Sissy Sarah was my patient for 24 hours, secured in Segufix over the entire time. I did several exams and tests on her. This is the sounding and electro session scene. After I have milked her using with the Magig Wand. This is a session film with no staged scenes. The very close and intimate camera moves through the action like a spectator observing voyeuristicly everything in detail. ]]> Tue 15 Apr 2025 05:43:17 +0200 https://www.fapbox.com/videos/33817335/hospital-1-sounding-and-electro-scene/ https://www.fapbox.com/videos/33761661/elvira-monster-mash-sissy-training/
Elvira has you in her dungeons. She decided you going to entertain her guest at her annual monster bash. That means monster of all types going to fill your little hole. You will blow them all. To test your skills she uses various monster dildos on you, to see how much you can take. ]]> Thu 20 Mar 2025 21:36:40 +0200 https://www.fapbox.com/videos/33761661/elvira-monster-mash-sissy-training/ https://www.fapbox.com/videos/33732916/newbie-sissy-training-meeting-2-stretching-sissy-cunt-with-fingers-facesitting-pussy-worship-arya-grander/
NewBie Sissy Training: meeting #2. Stretching Sissy Cunt with Fingers. FaceSitting. Pussy Worship. Arya Grander ]]> Fri 14 Mar 2025 22:07:38 +0200 https://www.fapbox.com/videos/33732916/newbie-sissy-training-meeting-2-stretching-sissy-cunt-with-fingers-facesitting-pussy-worship-arya-grander/ https://www.fapbox.com/videos/33777441/it-gets-bigger-and-bigger/
After the Sissy has cleaned the Mistress's house well, there is now a reward, a brand new strapon. And it gets bigger and bigger, as the Sissy realizes to her shock. Out of sheer fear she whines and begs the Mistress that it is much too big for her tight asshole, but all she manages to do is get the whip on her rubber ass and then the asshole is made to fit the extra large dick. ]]> Wed 12 Mar 2025 17:21:10 +0200 https://www.fapbox.com/videos/33777441/it-gets-bigger-and-bigger/ https://www.fapbox.com/videos/33716378/bi-humiliation-cum-clean-up/
Sadistic as ever, Miss Louisa and I make these boys french kiss and pathetically suck and wank each others cocks until one of them cums! We instruct these horny boys to slurp up every single drop of spilled cum. How does it taste? ]]> Thu 06 Mar 2025 23:48:21 +0200 https://www.fapbox.com/videos/33716378/bi-humiliation-cum-clean-up/ https://www.fapbox.com/videos/33738256/chastity-training-and-test-of-the-headscarf-sluts-lady-victoria-valente-part-3/
Another week in the cock cage has passed, today I'm testing you again! Look at that, you're wearing a new outfit, satin blouse and pretty stockings with new heels. And your face is also more beautifully made up than usual! I'm testing you again on the points of wearing a headscarf, catwalk headscarf performance and dancing. I notice that you've been practicing diligently and I see a certain improvement, but the whole thing still doesn't convince me! I take the cock cage off you and you can masturbate in front of me. Look at how horny you are! Hands behind your back! Now you're not going to cum! You can play some edging games, that's all! The whole thing is supposed to really frustrate you! Then I'll lock you back in your cock cage, headscarf slut! Keep practicing! And I hope you have fun with another week in the cock cage! ]]> Sat 15 Feb 2025 14:16:55 +0200 https://www.fapbox.com/videos/33738256/chastity-training-and-test-of-the-headscarf-sluts-lady-victoria-valente-part-3/ https://www.fapbox.com/videos/33816398/cum-dumpster/
What could be more degrading than being starved to the point where you'll consume just about anything...? Even the contents of the massage parlour waste basket that Myself and Miss Louisa kindly intercepted on the way here. We're going to make sure you consume every single last condom we fill your slutty, greedy mouth with. The visible disgust on our faces but pure enjoyment running through our minds. A meal you won't forget! ]]> Mon 10 Feb 2025 21:39:34 +0200 https://www.fapbox.com/videos/33816398/cum-dumpster/ https://www.fapbox.com/videos/33731721/sissy-dress-up-spitroast-clara-dee-pov-virtual-sex-with-elle-eros/
It's date night, and your wife Clara has a surprise. Her friend Elle is joining you again! They've prepared some pretty pink lingerie for you, and a cute little dress. Clara does your makeup, and then they have you pose and show off how pretty you look! You're such a pretty little sissy, they can't wait to fuck your holes with their strap-ons. KEYWORDS: Virtual sex, sissy, pegging, strap on, airtight, spitroast, sissy dress up, pussy, Clara Dee POV, pegged, POV pegging, sissification, feminization, roleplay, dildo, strap-on, spreading, pussy spreading, spread pussy, GFE, wife, reality, praise, encouragement, soft femdom, gentle femdom, clit rubbing, boobs, real boobs, real tits, shaved pussy, hairy pussy, girl next door, small tits, small boobs, MILF, Length: 13 minutes ]]> Sat 08 Feb 2025 07:33:19 +0200 https://www.fapbox.com/videos/33731721/sissy-dress-up-spitroast-clara-dee-pov-virtual-sex-with-elle-eros/ https://www.fapbox.com/videos/33811806/cbt-i-fuck-his-dick-in-close-up/
I know he loves getting his cock fucked like a tight little pussy. I love penetrating him with my metal long tools. Inserting big things into her and jerking her urethra makes me want to cum. Keywords : Wartenberg wheel, cbt, dick peehole fucking, Steel Sounding Plug Multi Beads Plug Rods ]]> Sat 08 Feb 2025 06:54:52 +0200 https://www.fapbox.com/videos/33811806/cbt-i-fuck-his-dick-in-close-up/ https://www.fapbox.com/videos/33787450/dominafire-femdom-pegging-compilation/
Asian Mistress DominaFire Anal Pegging femboy sissy slut rough ]]> Thu 16 Jan 2025 15:13:26 +0200 https://www.fapbox.com/videos/33787450/dominafire-femdom-pegging-compilation/ https://www.fapbox.com/videos/33753914/top-10-sissy-ideas-2023-pegging-butt-plugs-piss-chastity-diapers-enema/
Well, 2023 is finishing and we've realized that we didn't make the compilation for our sissy fans!! ]]> Tue 31 Dec 2024 11:26:42 +0200 https://www.fapbox.com/videos/33753914/top-10-sissy-ideas-2023-pegging-butt-plugs-piss-chastity-diapers-enema/