Search results: Training Sissy
Showing 1 - 28 of 12,931 videos (0.041 seconds)

anal,cumshot,dildo,blonde,hot,sexy,tranny,shemale,beautiful,cumming,orgasm,cum-swallow,dirty-talk,caged,sissy,deep-anal,huge-load,anal-orgasm,cock-cage,jessica-bloom

HD

Ramming The Sissy's Tight Hole With Massive Monster Dildo: Jessica Bloom Goes Wild!

07:17 0 Views 89%

blonde,milf,rough,amateur,curvy,solo,latex,humiliation,domination,bdsm,close-up,strap-on,beauty,femdom,cougar,dirty-talk,cfnm,glamour,newbie,alternative,humiliatrix,punishing,pawg,sissification,ass-worship,edging,bratty,girl-next-door,solo-girl,sexy-clothes,onion-booty,pretty-face,sissy-humiliation,female-pov,young-woman,slut-humiliation,slave-degradation,whore-humiliation

HD

Sissy Seduction: MILF Domination & Humiliation With Arya Grander

14:58 193 Views 87%

POV,femdom,hypno,sissified,mesmerize,sissyfication,female-domination,femdom-pov,slut-training,sissy-training

Worship My Divine Ass: Hard-Core Sissy Humiliation With Goddess Kyaa!

01:45 7.5k Views 67%

slut,blondes,training,femdom,big-tits,big-boobs,female-domination,slut-training,sissy-training

LANCE HART TAKES A POUNDING FROM ASHLEY FIRES

01:57 6.8k Views 75%

shemale,training,sissy,hypnosis

HD

The Filthy Sissy Slam

05:16 693 Views 65%

ass,blondes,humiliation,legs,pantyhose,fantasy,femdom,laundry,feminization,up-skirt,cock-tease,role-play,female-domination,slut-training,sissy-training

Submissive Sissy Begs To Be Suffocated By 3 Goddess Asses In Intense Training Session

01:39 1.5k Views 89%

anal,spanish,hentai,training,femdom,joi,succubus,sissy,demon,audio,espanola,esclavo,demonio,sex-slave,slave-training,sissy-training,sucubo,anal-joi,joi-espanol,hentai-sucubo

HD

Sissy Gets Dominated By Succubus In JOI Anal Encounter With Spanish Dirty Talk!

09:46 1.7k Views 75%

handjob,wife,cum-swallow,cim,femdom,dominatrix,goddess,cfnm,sissy,domme,cei,cum-eating-instruction,cum-eating-training,sissy-training,cum-in-nouth,cum-fedding,humiluation,cum-of-cum

HD

FEEDING A NAUGHTY SISSY WITH CUM

07:15 58 Views 0%

handjob,strap-on,femdom,pegging,sissy,crossdressing,female-domination,slut-training,sissy-training

Pathetic Perv Gets Dominated By Hot Mistress In Strap-on Pegging Session

02:08 19k Views 50%

tattoos,shaving,sissification,slave-training,femdom-pov,sissy-humiliation,femdom-humiliation,sissy-training,hair-removal,sissy-slave,sissy-sluts,sub-training,submissive-slave-training,sissy-pov,petra-hunter,dallas-dominatrix,encouraged-feminization,encouraged-hair-removal,encouraged-sissy,encouraged-crossdress

HD

Bare-Assed Bottom Boy

07:54 172 Views 77%

sissy-trainer,sissy-hypno,sissy-training,sissy-hypnosis,sissy-faggot,sissy-affirmations,sissy-affirmation,sissy-training-hypno,sissy-training-hypnosis,sissy-faggot-training,how-to-be-a-sissy

HD

Slutty Sissy's Dirty Desires

58:31 1.5k Views 100%

sissy-trainer,sissy-hypno,sissy-training,sissy-hypnosis,sissy-hypnosis-training,sissy-hypno-training,sissy-overnight-loop-file,sissy-hypno-long,long-sissy-hypnosis-file

Bimbo Transformation: From Sissy To Slut!

58:00 2.1k Views 0%

blondes,femdom,slave-training,female-domination,femdom-pov,slut-training,sissy-training,paypig

Whipped And Submissive Secretary Learns To Serve In Mind-Blowing Femdom POV Experience!

01:46 900 Views 70%

shemale,strapon,bdsm,orgasm,cuckold,sissy,chastity,cummy,sissification,feminization,permanent-chastity,sissy-training,sissy-blowjob,sissy-cum-slut,sissy-feminization,sissy-clitty,sissy-chastity,limp-sissy,sissy-course,cummie

HD

Thirsty Twinks Transformed - Sissy Training Vol. 3

10:40 305 Views 71%

joi,cei,self-facial,sissy-slut,jerk-off-instructions,joi-cei,sissy-training,sissy-husband,cum-countdown,blowjob-training,sissy-joi,surprise-ending,bi-joi,imposed-bi,clara-dee-joi,sissy-wife,sissy-dress-up,sissy-deepthroat,pussy-reveal-joi,suggested-bi

HD

Slutty Hubby Gets Lessons From Clara Dee In Hot Blowjob Training Session!

00:24 443 Views 94%

POV,femdom,cei,female-domination,femdom-pov,slut-training,sissy-training

Satisfy TerraMizu's Femdom Desires With Sissy Slut Training

01:54 489 Views 98%

Shameless Sissy Slut Training!

26:32 0 Views 74%

slave,training,sissy

Obey And Submit: Sissy Slave Training Extravaganza!

15:45 86 Views 84%

cuckold,joi,sissy,praise,cei,self-facial,ruined-orgasm,sissy-training,sissy-anal,sissygasm,cum-countdown,anal-joi,sissy-joi,sissy-cuck,clara-dee-joi,gentle-femdom,sissy-wife,sissy-dress-up,positive-femdom,cuck-training

HD

Naughty Hubby Turns Sissy Wife Into Anal Addict - Clara Dee's Jerk Off Instruction

17:38 0 Views 63%

training,sissy,preparation

HD

Naughty Sissy Gets Schooled In Pleasure

00:58 0 Views 81%

dildo,pussy,domination,tranny,tv,trans,femdom,crossdresser,rubber,silicone,cd,sissy,trap,sissy-trainer,female-domination,sissy-slut,sissy-training,sissy-fag,sissy-crossdresser

HD

Seduce And Submit: The Sissy Trainer POV #BratPerversions

00:38 0 Views 62%

domination,training,sissy,sissification,feminization,sissy-humiliation

HD

Ms. Lacy's Transformation: From Macho Man To Sissy Bimbo Boy Toy!

06:54 0 Views 76%

training,sissy,hypnosis,hypno

Femboy Gets Wet And Wild In Erotic Shower Trance

29:48 1.7k Views 100%

dildo,ass,booty,gay,training,sissy,sissification,feminization,solo-masturbation,big-dildo,fit-body

HD

Naughty Sissy Fun Time In The Living Room

13:10 1k Views 62%

femdom,dominatrix,joi,humiliatrix,sph,cock-worship,cei,female-domination,findom,sissy-training,sissy-hyno

Dominant Woman Controls Submissive Boy With Erotic Mind Control

11:35 0 Views 64%

rus-sissy,russian-salve,sissy-salve-rus,rus-slave-hypno,sissy-russian-slave,mistress-slave-rus,sissy-russian-hypno,russian-sissy-training,sissy-training-rus,mistress-rus,femdom-russian,rus-femdom,femdom-sissy-ru,ru-femdom,sissy-ru

HD

Russian Submissive Gets Dominated And Trained To Serve Master

08:11 56 Views 100%

bitch,humiliation,slave,training,sissy,puppy,degrading

Sultry Submissive Abbi Stone Learns Obedience In Kinky Humiliation Play 3

13:40 901 Views 0%

POV,humiliation,bdsm,fetish,mistress,femdom,dominatrix,domina,cuckold,joi,sissy,humiliatrix,domme,sph,cei,female-domination,findom,sissy-training

Massive Cock Adoration Sissy Conditioning

08:56 5.9k Views 67%

It never hurts to see what other fans of LetMeJerk are looking for

About Training Sissy Videos

Looking to jerk to some of the best Training Sissy porn out there on the Internet today? Well you're in luck, because here at LetMeJerk, we provide our valued users with free access to some of the best Training Sissy porn videos on the planet!

Our Training Sissy collection also features related categories like: Sissy-training, Sissy, Femdom, Training, Female-domination.

With 12,931 Training Sissy videos to choose from, you'll find exactly what you're looking for. Watch in HD quality and enjoy our user-friendly interface designed for the best browsing experience.

Approximately 54% of our Training Sissy videos are available in HD quality, ensuring you get the best viewing experience possible.

Our Training Sissy collection is updated regularly with new content, so be sure to bookmark this page and check back often for the latest uploads.