Rubber Sissy
08:53
Total rubber enclosure for training of the new sissy - Sasha de Sade - secretsissy2
CD Trap Sissy Training
03:07
EeeekKK!! my 1st video on X Hams.... Im a CD trying to transition into Trans or TS or IDK! Im just having fun .... enjoy - tsnylonmichelle
Me sissy faggot femboy anal dildo fisting
01:17
I really like the training,the goal is to finish without hands ... - Twokisses
Training my pussy
00:58
Trying to be a good sissy and train my boy pussy - Hiddendesires90210
Intense Anal Shocker Ramming 9inches In All At One No Lub
00:41
Training my sissy shemale on how to take a dick up the ass take 9inches and ramming it all in at once making her scream in pain fighting trying to get away but I keep pushing till the balls touch her - Sadee Rain - TGirlSadee
Anal Training My Sissy In Public To Take A Huge Dick
09:03
Training my hot sissy on how to take a huge dick deep in her ass as she try to get away and take it but it seem to be to much dick to push onto her at once during her 1st anal training outdoors - TGirlSadee
Hello Sissy
08:33
Train your sissy sluts to be submissive cock addicts. - M4sterJ
Prostate milking a sissy cow 4K (short clip)
01:24
You can't get a more perfect sissy training then a prostate milking session! You will not regret seeing this when a sissy is constantly leaking cum in your face as a cow! - KimsaTrans - Kimsatrans
Sissy Dildo Trainer (advanced)
17:02
1st vid on my daily anal-training playlist. 17min 02sec. Builds up speed slowly, good place to start. - AnalSissySlut222
Thicc sissy solider slut training to serve the military
06:25
Gagged cum-dumpster sissy trap training my wrecked hole for soldier cock. Huge dildos, double anal, triple anal, fisting and more. Comment what you'd to do to me if you were my commanding officer - AngelSissyWhore
The Bitch Training & Forced Feminization of Clarrise Thorne
00:21
A well bred & trained submissive Sissy French Maid can fetch a lot of money as a Sissy Cuckold Slave Husband. PLEASE HELP US ME EARN TUITION FOR THE Tia Tizzianni SISSY INSTITUTE. Message Me for fun! - ClarriseThorne
A Guide To Sissification - Beginner - First Steps
31:53
I have finally finished the second video of my guide to sissification. This part turned out to be very different, I think. I hope all of you will still enjoy it. - useme42
Sissy soldier slut anal training (preview version)
05:58
Sissy soldier slut training my ruined hole to better serve the Australian military. - AngelSissyWhore
TS Alexis Grounding my BBC
03:17
Riding n’ grounding my Daddy’s BBC like the good slutty Gurl I am ! - TSalexisNC
Stretching my tight sissy slut slave bum for London Master
01:20
Master ordered me to continue training my bum, in order to take cock, cum and piss whenever he orders. X - Rizlam1
9 inch black dildo
03:23
Sissy Laura Lou lubes up her huge 9 inch black dildo with her mouth, then bounces up and down until she moans. Hops off and gives it a taste. After seconds she hops back on to finish off her training. - ssquirtss
Ghetto Faggot
03:49
Just being a black cock loving feminized white punk - Kimber Haven - Kimberhaven
Sissy slut rides 12 inch BBC dildo.
00:21
Short video of me training for a sissygasm on a huge BBC dildo. - Sluttycdkelsi
Sissy schoolgirl buttplug and deepthroat training
01:48
Masked shemale whore wearing a big glass buttplug trains her throat with a dildo - AngelSissyWhore
Forced Sissy Crossdresser Handjob By Femdom Step Mommy Mistress
02:17
Sissy crossdresser handjob and shoejob with anal dildo training and stretching by mrskeswick who always wears shiny pantyhose, silk blouses and high heels. Double D breasts - adbcfnmboytoy
Poppers and Cum PMV
07:37
Sissy training and encouragement. lots of facials, cum in mouths, . anal. women & trans being fucked. - puchu3k
London sissy pussy butt plug stretch, wank, cum in own bum
06:31
Slowly stretching my very tight pussy while wanking. Then scooping up my own cum on the butt plug before easing it back into my tight bum. Owner is very happy with my training. Enjoy. :) x - Rizlam1
Sissy monster dildo training 2
03:13
A snippet from a sissy session this week. My ass just swallows that monster right up. Turns me into a brainless slut. - Brownsubslut
taniax travesti makes sissy training
02:12
chastify cage and bbc dildo, is all you need for make yourself more submissive and fem yourself - taniaxtorres
Nely sissy big ass bitch twerk latina culona tranny ladyboy
16:34
Nely sissy big ass bitch twerk latina culona tranny ladyboy modo avião vai decolaaaa!!!! - nelycd
DEEP training AB15 HUGE BBC DILDO
02:07
Deep training session with AB15 (12inches) HUGE BBC DILDO , i try to ride balls deep and fast ! - Subbysucker
Who's Your Daddy
04:27
Keep these sissy training videos playing at all times to reinforce your conditioning. - M4sterJ
sissyeric crossdresser dildo training
04:51
sissyeric rides dildo facing camera, reverse cowboy, sissy crossdresser, bottom submissive, feminization, humiliation, small cock, bra panties, thigh highs, public exposure, gay panty bottom, cuckold - sissyerica34a
Sissy dildo training - Camelia fucked by machine
07:48
Sissy Camelia in her routine training pounding her sissy pussy with a fuck machine - LopetravBxl
30 mins anal training for sissies
30:00
3rd on playlist. Gives stats like section length and number of thrusts, + a total number of thrusts (if you can keep up the pace of course). I could not get through this without cumming for ages. - AnalSissySlut222
Dildo slut training
01:03
Stretching my tight sissy hole ready for some real Cock. - Sissy69Slutx
My New 12 Inch Toy
08:57
Shoving a foot of dick up my ass like butter - Kimber Haven - Kimberhaven
Mindless monster dildo fucking
05:33
Different day different outfit. Love destroying my hole. love shoving these toys straight in there with no warm up. Listen to my brainless moaning when riding these toys - Brownsubslut