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
Slutty Sissy CD recorded play with dildo and gets horny
03:30
Sissy Crossdresser gets horny while play and tease with dildo in her mouth and ass - Etherea
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
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
Who's Your Daddy
04:27
Keep these sissy training videos playing at all times to reinforce your conditioning. - M4sterJ
Me sissy faggot femboy anal dildo fisting
01:17
I really like the training,the goal is to finish without hands ... - Twokisses
Sissy hypno teil3
00:32
I'm a stupid Sissy whore and brainwash for my beautyful Goddess Anya!!! Sissyslut Marleen - GoettinAnyasNutte
Sissy schoolgirl CD shows off and trains smooth butt w dildo
03:48
Just some clips of me dressed up and toying my asspussy with a 9inch dildo. Lots more coming soon! Thanks for watching ;) - butt_slut_
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
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
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
Poppers and Cum PMV
07:37
Sissy training and encouragement. lots of facials, cum in mouths, . anal. women & trans being fucked. - puchu3k
Rubber Sissy
08:53
Total rubber enclosure for training of the new sissy - Sasha de Sade - secretsissy2
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
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
Training my sissy ass for The real thing
00:21
Using Dildo to gape my boy hole and wait for a real cock to come song Nd abuse me - Gingerpotato
Sissy dildo training - Camelia fucked by machine
07:48
Sissy Camelia in her routine training pounding her sissy pussy with a fuck machine - LopetravBxl
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
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
Leyendecker Work Bitch Tribute
04:50
My HorseCock training on Leyendecker Work Bitch Sissy training video - Deborah95
Sissy huge anal gape and hands free cumshot!
04:43
Sissy training her sissy pussy to please her daddy with some anal gaping, so it will be easier to enter for daddy whenever he pleases. This gaping practise ends up in a hands free anal cumshot, just l - KimsaTrans - Kimsatrans
Sissy soldier slut anal training (preview version)
05:58
Sissy soldier slut training my ruined hole to better serve the Australian military. - AngelSissyWhore
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
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
BBC fucking shemale Doggie style
02:23
Daddy fucks me every way he wants to and I am proud to service his cock and worship his big black cock all the time! - TSalexisNC
Painful Anal Training On My Sissy Bitch Outdoors with 8inch Dildo
09:57
using my 8 inch dildo on Sadee tight ass giving her an amazing anal shocker as I push it all in and make her jump and fight but I keep pushing it in deep and dont comes back out - TGirlSadee
Sissy schoolgirl buttplug and deepthroat training
01:48
Masked shemale whore wearing a big glass buttplug trains her throat with a dildo - AngelSissyWhore
Dildo slut training
01:03
Stretching my tight sissy hole ready for some real Cock. - Sissy69Slutx
Sissy in tiny chastity on BBC dildo
05:09
A short video of me in a cute dress and tiny chastity training for bbc - nwtammi
Sissy slut rides 12 inch BBC dildo.
00:21
Short video of me training for a sissygasm on a huge BBC dildo. - Sluttycdkelsi
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
TS Alexis Grounding my BBC
03:17
Riding n’ grounding my Daddy’s BBC like the good slutty Gurl I am ! - TSalexisNC
My New 12 Inch Toy
08:57
Shoving a foot of dick up my ass like butter - Kimber Haven - Kimberhaven