https://www.fapbox.com/tags/sissy-crossdresser/ Fri 05 Jun 2026 03:53:58 +0200 https://www.fapbox.com/videos/33815648/dungeon-of-love-mistress-fucks-her-sissy-step-daughter-with-a-strapon/
It was just super! Recently we visited one castle in Europe. When we went down to the basement, the magical atmosphere of the Middle Ages quickly awakened in us the desire to have sex. Of course, I dressed my sissy boyfriend as a girl and fucked his sweet hole well with a strap-on. ]]> Mon 14 Apr 2025 17:16:08 +0200 https://www.fapbox.com/videos/33815648/dungeon-of-love-mistress-fucks-her-sissy-step-daughter-with-a-strapon/ https://www.fapbox.com/videos/33720282/the-hottest-cumshot/
The mistress gives the guy a prostate massage and milks his dick so that he gets a very powerful orgasm! The girl does such a sensitive handjob, just look at this cumshot! The cum just flows like a high mountain waterfall! She likes this spectacle so much, and the guy has no choice but to lie there and cum whenever she wants! Spend this evening with us! Hot couple of blondes Justin Sweetsun and Emily Candys! Enjoy! ]]> Tue 18 Mar 2025 20:14:16 +0200 https://www.fapbox.com/videos/33720282/the-hottest-cumshot/ 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/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/33803684/awakening-of-sissy-slut-michelle-after-christmas-night-club-celebration/
Becky woke me up after we got home late after midnight from celebrating Christmas at the club. There is only one way to fully awaken me up on weekend. I need a gentle and skillful hand or mouth nearby, no matter female or male. So I couldn't resist her hand and mouth, and especially after she undressed me and dressed me in a festive pink bra and panty set. It was her Christmas present to me. I ejaculated on her pantyhose, and then she sent me to the bathroom and went to the kitchen. But I was incredibly horny wearing this new pink set. I returned to the bedroom and quickly ejaculated for the second time in her pantyhose. Becky had sent me to the bathroom alone on purpose. She knows I like to cum alone sometimes, especially if once or twice wasn't enough and she had other things to do. So, I did it, and the third ejaculation woke me up completely. But it turned out that Becky had been watching me ejaculate again through the half-closed door, and she liked it. ]]> Sun 02 Feb 2025 04:31:27 +0200 https://www.fapbox.com/videos/33803684/awakening-of-sissy-slut-michelle-after-christmas-night-club-celebration/ 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/ https://www.fapbox.com/videos/33788791/sph-and-sissification-for-slut-arya-grander-and-mistress-priest/
SPH and Sissification for slut! Arya Grander and Mistress Priest. ]]> Fri 27 Dec 2024 14:08:00 +0200 https://www.fapbox.com/videos/33788791/sph-and-sissification-for-slut-arya-grander-and-mistress-priest/ https://www.fapbox.com/videos/33784396/sahu-bhauj-ku-odia-re-fucking-ta-bia-ku/
]]> Mon 23 Dec 2024 13:40:02 +0200 https://www.fapbox.com/videos/33784396/sahu-bhauj-ku-odia-re-fucking-ta-bia-ku/ 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/33769223/asian-mistress-pegging-german-sissy-slut/
Dominafire strapon fucks german anal sissy ]]> Sat 28 Sep 2024 21:06:04 +0200 https://www.fapbox.com/videos/33769223/asian-mistress-pegging-german-sissy-slut/ https://www.fapbox.com/videos/33731627/so-hot-cumming-after-7-days-in-chastity-and-anal-training/
Emily and Justin explore the world of femdom submission again! Mistress Emily puts the flattest cock cage on Justin! Only the balls are left for this sissy boy! She starts touching his ass and fucking it! She trains this anal sissy so that this guy becomes obedient and wants to cum so badly! Then she takes off his chastity belt and starts fucking his ass with her fingers, while she milks his cock hard, controlling his orgasm! And of course, a hot ruined anal cumshot at the end! Just look at this cumshot! And enjoy with us! ]]> Thu 05 Sep 2024 23:34:43 +0200 https://www.fapbox.com/videos/33731627/so-hot-cumming-after-7-days-in-chastity-and-anal-training/ https://www.fapbox.com/videos/33783052/the-first-education-of-the-sissy-p2-a-classic/
At the request of our fans, the first education of the sissy slut - A classic from 2001 ]]> Sun 04 Aug 2024 14:26:20 +0200 https://www.fapbox.com/videos/33783052/the-first-education-of-the-sissy-p2-a-classic/