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Training you to be the perfect sissy isn't just about the girly clothes and the bimbo hair and makeup. It's also about changing the way you feel. Sissies are less than serving girls, less than objects of amusement, less than simply submissive. They are victims! Sissies need to understand that they have no say in what happens to them, how they are used, who is using them and where they are being used. So besides being emasculated as part of their training they need to be made to feel like a victim - a vulnerable, helpless damsel in distress. The best way to so this is to put you through more and more extreme bondage predicaments while feminized. You'll be dressed in your tightest corset, your girliest frills, your highest heels, your longest wig, and your prettiest makeup and then you'll be gagged and bound. Training you to begin with by hogtying you on the floor and watching you struggle and moan into your gag while I verbally humiliate you - but things will quickly escalate. Knowing I'm nearby to untie you if you start to panic isn't really going to make you feel too vulnerable so next I'm going to leave you in prolonged, uncomfortable bondage while I head out with the girls for the night. But it's not until I've left you bound somewhere public that you'll really start to feel vulnerable. Chained to a hotel bed in all your sissy frills waiting for the maid to find you - that's more like it... or maybe leaving you tethered to a tree where the gays meet - that might work huh? Can you imagine being discovered in all your sissy clothes? At the mercy of whoever finds you?... ]]> Sun 20 Sep 2026 23:23:12 +0200 https://www.camwhoresbay.com/videos/1211906/cruel-girlfriend-my-bondage-sissy-victim/ https://www.camwhoresbay.com/videos/1210396/cruel-girlfriend-your-turn-on-the-mattress/
We have a special place at the CruelGirlfriend Dreamhouse just for newly acquired sissies that are struggling to accept their new position in life. We just refer to it as 'The Mattress' but it strikes fear into all our sissies hearts. The Mattress is a filthy, cum-stained, ruined mattress - thrown on the floor of our storage room. It has restraints at each corner which we use to secure our sissies before they are left there for the duration of their punishment. Punishments can be anything from a day up to a whole week - it depends on how cruel we're feeling and whether or not another sissy deserves the mattress even more. It doesn't matter how good a sissy you think you are - it's inevitable you will end up on 'The Mattress' sooner or later so when that time comes - you'd better be prepared! Sissies are brought to the mattress fully clothed in their uniforms. Usually a flimsy, satin French maid's dress but sometimes a schoolgirl or a whore. You will be 'O' gagged and sometimes blindfolded and then tightly secured with the restraints - pulling you helplessly into a spread-eagle position. This is how you will be left until your first client arrives - the first of many. You'll be fucked on the mattress until your client cums - he'll throw his used condom on the floor, wipe his cock in your dress and leave some money in the jar. Then you'll wait for the next client to arrive to do something even more degrading to you. Your helpless, cum-soaked body will stay chained to the mattress until we decide you've learned your lesson - or the jar is full - whichever takes the longest. ]]> Sat 19 Sep 2026 08:13:09 +0200 https://www.camwhoresbay.com/videos/1210396/cruel-girlfriend-your-turn-on-the-mattress/ https://www.camwhoresbay.com/videos/1206069/big-ass-blonde-brickbabe-squirts-in-longest-solo-masturbation-video/
Watch this hot blonde babe Brickbabe in a solo masturbation session! She's a sexy milf with a big ass and natural tits, and she loves to play with her sex toys, squirt, and ride her dildo. See her up-close pussy action and fast fingering skills as she cums hard with her Hitachi magic wand. ]]> Wed 09 Sep 2026 16:48:22 +0200 https://www.camwhoresbay.com/videos/1206069/big-ass-blonde-brickbabe-squirts-in-longest-solo-masturbation-video/ https://www.camwhoresbay.com/videos/1137226/morgpie-step-sister-always-takes-the-longest-showers/
Morgpie - Step Sister always Takes the Longest Showers... Finally Figured out Why¡ ]]> Sun 15 Feb 2026 16:45:20 +0200 https://www.camwhoresbay.com/videos/1137226/morgpie-step-sister-always-takes-the-longest-showers/ https://www.camwhoresbay.com/videos/1108784/enmarchenoire-the-longest-double-blowjob-world-reco/
EnMarcheNoire - The Longest Double Blowjob - World Record ]]> Tue 23 Dec 2025 11:11:15 +0200 https://www.camwhoresbay.com/videos/1108784/enmarchenoire-the-longest-double-blowjob-world-reco/ https://www.camwhoresbay.com/videos/1108787/enmarchenoire-the-ultimate-blowjob-experience-3-the/
EnMarcheNoire - The Ultimate Blowjob Experience 3; the Longest Run ]]> Tue 23 Dec 2025 09:24:19 +0200 https://www.camwhoresbay.com/videos/1108787/enmarchenoire-the-ultimate-blowjob-experience-3-the/ https://www.camwhoresbay.com/videos/1059830/nylon-taty-the-longest-dangling/
Nylon Taty the longest dangling ]]> Sat 17 May 2025 09:24:07 +0200 https://www.camwhoresbay.com/videos/1059830/nylon-taty-the-longest-dangling/ https://www.camwhoresbay.com/videos/708250/moon-christine-longest-doubledong-hidden-in-pussy/
Moon Christine - Longest doubledong hidden in pussy ]]> Thu 25 May 2023 17:28:22 +0200 https://www.camwhoresbay.com/videos/708250/moon-christine-longest-doubledong-hidden-in-pussy/ https://www.camwhoresbay.com/videos/646926/sencual-pussy-licking-oral-sex-the-longest-ho-party-p/
Sencual Pussy Licking, Oral Sex (the Longest HO Party PART 1) ]]> Sat 14 Jan 2023 14:17:18 +0200 https://www.camwhoresbay.com/videos/646926/sencual-pussy-licking-oral-sex-the-longest-ho-party-p/ https://www.camwhoresbay.com/videos/469941/pk-longest-stream/
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Absolutely the Greatest and Longest Squirt Ever. Unbelievable ]]> Sun 21 Mar 2021 20:54:38 +0200 https://www.camwhoresbay.com/videos/359120/absolutely-the-greatest-and-longest-squirt-ever-unbeli/ https://www.camwhoresbay.com/videos/221044/the-longest-double-blowjob-world-record/
The Longest Double Blowjob - World Record ]]> Fri 27 Mar 2020 08:05:02 +0200 https://www.camwhoresbay.com/videos/221044/the-longest-double-blowjob-world-record/