Double dildo sissy
Double dildo sissy
 Twink(Gay),Crossdresser(Gay),Gaping(Gay),SmallCock(Gay),HDVideos,GaySissy(Gay),Anal(Gay),Sissy(Gay),Dildo(Gay),SissyCrossdresser(Gay),SissyTwink(Gay),TwinkAnal(Gay),SissyAnalTraining(Gay),SissyPussy(Gay),Tattoo(Gay),AnalToy(Gay), 
 0 min                  2
xhamster        
 2024-04-08 00:03:47 
Stretching Open My Ass With a Butt Plug
Stretching Open My Ass With a Butt Plug
 Amateur(Gay),Gaping(Gay),SmallCock(Gay),HDVideos,Anal(Gay),Sissy(Gay),SissyAnalTraining(Gay),OpenMyAss(Gay),ButtPlugs(Gay),AnalStretch(Gay),GayButtPlug(Gay),AnalStreching(Gay),AnalStretchingTraining(Gay),White(Gay),Uncut(Gay),A 
 6 min                  3
xhamster        
 2024-02-17 12:03:16 
This Dildo Is Too Girthy For Me!
This Dildo Is Too Girthy For Me!
 Amateur(Gay),Crossdresser(Gay),SmallCock(Gay),HDVideos,GayAnal(Gay),GayDildo(Gay),Anal(Gay),Sissy(Gay),Dildo(Gay),ExtremeDildo(Gay),CrossdresserAnal(Gay),SissyAnalTraining(Gay),AnalStretch(Gay),AnalStretchingTraining(Gay),White(G 
 2 min                  1
xhamster        
 2024-02-17 12:02:42 
Playing in chastity while wearing the locking buttplug with a timelock
Playing in chastity while wearing the locking buttplug with a timelock
 BDSM(Gay),Masturbation(Gay),HDVideos,GayBondage(Gay),GayCBT(Gay),Solo(Gay),German(Gay),Caged(Gay),ChastityCum(Gay),AmateurSissy(Gay),GayChastity(Gay),AnalToys(Gay),While(Gay),SissyAnalTraining(Gay),Lock(Gay),BondageEdging(Gay),Ca 
 18 min                  1
xhamster        
 2024-01-23 12:00:47 
Training further to be Francis Malice
Training further to be Francis Malice
 HDVideos,Anal(Gay),Solo(Gay),Dildo(Gay),AmateurSissy(Gay),AnalToys(Gay),SissyAnalTraining(Gay),Using(Gay),Want(Gay),GoodSissy(Gay),Fetish(Gay),AnalToy(Gay),Leather(Gay),Homemade(Gay),AnalMasturbation(Gay) 
 1 min                  4
xhamster        
 2024-01-16 12:01:28 
Cucumbers Make Great Toys
Cucumbers Make Great Toys
 Gaping(Gay),HDVideos,Anal(Gay),Chubby(Gay),Solo(Gay),GayAnalTraining(Gay),AnalToy(Gay),Deepthroat(Gay),Homemade(Gay),AnalMasturbation(Gay) 
 1 min                  17
xhamster        
 2023-12-10 00:05:01 
Femdom fucktoy prostate milking sissygasm cum
femdom fucktoy prostate milking sissygasm cum
 Amateur(Gay),Webcam(Gay),GayDildo(Gay),Anal(Gay),Cumshot(Gay),Dildo(Gay),British(Gay),HandsFreeProstateOrgasm(Gay),AmateurStraight(Gay),AmateurSissy(Gay),VibratorCum(Gay),ProstateToy(Gay),AnalToys(Gay),SissyAnalTraining(Gay),Pros 
 2 min                  17
xhamster        
 2023-12-09 00:04:43 
Big Dildo Doggystyle
Big Dildo Doggystyle
 Amateur(Gay),HDVideos,GaySex(Gay),GayAnal(Gay),Solo(Gay),Dildo(Gay),FapHouse(Gay),Toyed(Gay),GaySexToys(Gay),BigDildos(Gay),GayAnalTraining(Gay),GaysSex(Gay),CloseUp(Gay),AnalMasturbation(Gay) 
 1 min                  20
xhamster        
 2023-10-09 00:02:25 
Trying out new XXL plug and further hole training
Trying out new XXL plug and further hole training
 Amateur(Gay),Fisting(Gay),Gaping(Gay),SexToy(Gay),HDVideos,GayTraining(Gay),Anal(Gay),Solo(Gay),Dildo(Gay),Polish(Gay),SloppyHole(Gay),DildoTraining(Gay),AnalToys(Gay),GayGape(Gay),HoleTraining(Gay),ButtPlugs(Gay),GayAnalTrainin 
 14 min                  19
xhamster        
 2023-07-14 12:01:41 
Sex machine
Sex machine
 Amateur(Gay),Bear(Gay),Crossdresser(Gay),Daddy(Gay),Gaping(Gay),HDVideos,Anal(Gay),Mature(Gay),Chubby(Gay),Canadian(Gay),SissyLingerie(Gay),SissyAnalTraining(Gay),GaySexMachine(Gay),Fetish(Gay),AverageBody(Gay) 
 5 min                  16
xhamster        
 2023-06-18 12:00:52 
Getting into place to be fucked
getting into place to be fucked
 Amateur(Gay),Crossdresser(Gay),HDVideos,Anal(Gay),Chubby(Gay),Sissy(Gay),SissyCrossdresser(Gay),SissyAnalTraining(Gay),SissyFuckMachine(Gay),AmateurSissyCrossdresser(Gay),Middle-Aged(Gay),AnalToy(Gay) 
 0 min                  17
xhamster        
 2023-06-11 00:03:27 
Wanking and cumming with vibrating anal plug inside of me
Wanking and cumming with vibrating anal plug inside of me
 Amateur(Gay),Masturbation(Gay),HDVideos,GayCum(Gay),Chubby(Gay),Solo(Gay),BoyWank(Gay),AnalToys(Gay),MasturbationCum(Gay),GayBedroom(Gay),GayAnalTraining(Gay),Middle-Aged(Gay),European(Gay),Vibrator(Gay),AnalToy(Gay),Reality(Gay), 
 1 min                  15
xhamster        
 2023-06-10 12:01:18 
Sissy Sexy Lexi rides large dildo
Sissy Sexy Lexi rides large dildo
 Asian(Gay),Crossdresser(Gay),Gaping(Gay),Anal(Gay),Skinny(Gay),Young(Gay),SissyCrossdresser(Gay),CrossdresserDildo(Gay),Younger(Gay),AmateurSissy(Gay),Youngest(Gay),SissyAnalTraining(Gay),Rides(Gay),Fetish(Gay) 
 0 min                  21
xhamster        
 2023-05-14 00:01:00 
SISSY in NYLONS - Masturbation with ANAL Toy - Prostate Milking and NO Hands CUMSHOT
SISSY in NYLONS - Masturbation with ANAL Toy - Prostate Milking and NO Hands CUMSHOT
 Twink(Gay),Masturbation(Gay),HDVideos,GaySissy(Gay),Anal(Gay),Cumshot(Gay),Solo(Gay),German(Gay),HandsFreeCumshot(Gay),Handsfree(Gay),HandsfreeCum(Gay),AmateurSissy(Gay),ProstateToy(Gay),SissyBoys(Gay),SissyAnalTraining(Gay),Siss 
 8 min                  22
xhamster        
 2023-02-18 12:04:20 
My new huge dildo
My new huge dildo
 Amateur(Gay),BigCock(Gay),Hunk(Gay),HDVideos,GayDildo(Gay),Anal(Gay),Solo(Gay),Dildo(Gay),XxlDick(Gay),AnalTrainingJoi(Gay),AmateurBwc(Gay),European(Gay),White(Gay) 
 5 min                  28
xhamster        
 2022-06-30 00:01:02 
Anal workout sex machine 6
Anal workout sex machine 6
 Amateur(Gay),Massage(Gay),SexToy(Gay),HDVideos,GaySex(Gay),GayAnal(Gay),GayAss(Gay),GaySissy(Gay),Anal(Gay),Young(Gay),Chubby(Gay),Solo(Gay),Dildo(Gay),Swedish(Gay),AnalToys(Gay),SissyAnalTraining(Gay),FuckingMachines(Gay),GayA 
 1 min                  32
xhamster        
 2022-04-20 00:00:48 
Beginner sissy anal training, trying to reach sissygasm
Beginner sissy anal training, trying to reach sissygasm
 Amateur(Gay),Masturbation(Gay),SexToy(Gay),HDVideos,GayPublic(Gay),GayAnal(Gay),GaySissy(Gay),GayTrain(Gay),GayOutdoor(Gay),GayTraining(Gay),Anal(Gay),Russian(Gay),SissyAnalTraining(Gay),SissygasmTraining(Gay) 
 5 min                  30
xhamster        
 2022-02-21 12:03:16 
Watch My Cock Get Hard As I Stick A Butt Plug In My Ass - YouSoughtCumshot
Watch My Cock Get Hard As I Stick A Butt Plug In My Ass - YouSoughtCumshot
 Amateur(Gay),BigCock(Gay),HDVideos,BigCockGay(Gay),Anal(Gay),AnalPlug(Gay),HornyGay(Gay),AssPlaying(Gay),GayAnalTraining(Gay) 
 0 min                  37
xhamster        
 2022-02-17 12:00:46 
Watch My Cock Get Hard As I Stick A Butt Plug In My Ass - YouSoughtCumshot
Watch My Cock Get Hard As I Stick A Butt Plug In My Ass - YouSoughtCumshot
 Amateur(Gay),BigCock(Gay),HDVideos,BigCockGay(Gay),Anal(Gay),AnalPlug(Gay),HornyGay(Gay),AssPlaying(Gay),GayAnalTraining(Gay) 
 0 min                  44
xhamster        
 2022-02-17 12:00:46 
Sissy playing with a knotted dildo
Sissy playing with a knotted dildo
 Amateur(Gay),Crossdresser(Gay),SexToy(Gay),HDVideos,Anal(Gay),American(Gay),AmateurSissy(Gay),SissyAnalTraining(Gay),SissyDildoTraining(Gay),SissyChastityTraining(Gay) 
 5 min                  28
xhamster        
 2021-12-01 12:04:52 
Sissy playing with a knotted dildo
Sissy playing with a knotted dildo
 Amateur(Gay),Crossdresser(Gay),SexToy(Gay),HDVideos,Anal(Gay),American(Gay),AmateurSissy(Gay),SissyAnalTraining(Gay),SissyDildoTraining(Gay),SissyChastityTraining(Gay) 
 5 min                  25
xhamster        
 2021-12-01 12:04:52 
Bri teasing and fucks dildo
Bri teasing and fucks dildo
 Amateur(Gay),Latino(Gay),Masturbation(Gay),SexToy(Gay),Striptease(Gay),GayDildo(Gay),GayCrossdresser(Gay),Anal(Gay),American(Gay),SissyCrossdresser(Gay),SissyDildo(Gay),AmateurSissy(Gay),CrossdresserAnal(Gay),SissyAnalTraining(Gay) 
 4 min                  53
xhamster        
 2021-11-21 12:03:33 
Bri teasing and fucks dildo
Bri teasing and fucks dildo
 Amateur(Gay),Latino(Gay),Masturbation(Gay),SexToy(Gay),Striptease(Gay),GayDildo(Gay),GayCrossdresser(Gay),Anal(Gay),American(Gay),SissyCrossdresser(Gay),SissyDildo(Gay),AmateurSissy(Gay),CrossdresserAnal(Gay),SissyAnalTraining(Gay) 
 4 min                  52
xhamster        
 2021-11-21 12:03:32 
Cd anal solo huge plug n play pt 2
cd anal solo huge plug n play pt 2
 Amateur(Gay),Crossdresser(Gay),Gaping(Gay),Masturbation(Gay),SexToy(Gay),HDVideos,GayAnal(Gay),GayCrossdresser(Gay),GaySolo(Gay),Anal(Gay),GayAnalDildo(Gay),GayAnalTraining(Gay) 
 1 min                  49
xhamster        
 2021-10-27 12:01:23 
Broccolibutts - Teen boy anal training
Broccolibutts - Teen boy anal training
 GayPorn(Gay),Twinks(Gay),Amateur(Gay),EmoBoys(Gay),Masturbation(Gay),HDGays,AnalTraining,Training 
 7 min                  142
xhamster        
 2017-10-19 11:01:45 
More anal training and show
more anal training and show
 Amateur(Gay),Gaping(Gay),Latin(Gay),SexToys(Gay),Webcams(Gay),AnalTraining,Training 
 2 min                  51
xhamster        
 2017-10-10 06:00:25 
Chrissie Anal Training for Sir M
Chrissie Anal Training for Sir M
 Amateur(Gay),Crossdressers(Gay),SexToys(Gay),SmallCocks(Gay),HDGays,AnalTraining,Training 
 1 min                  83
xhamster        
 2017-10-05 13:00:06 
Anal training
Anal training
 Men(Gay),Amateur(Gay),SexToys(Gay),AnalTraining,Training 
 0 min                  62
xhamster        
 2017-09-23 20:00:37 
Sissy anal training
Sissy anal training
 Twinks(Gay),Amateur(Gay),Crossdressers(Gay),Masturbation(Gay),SexToys(Gay),SissyTraining,AnalTraining,Sissy,Training 
 6 min                  45
xhamster        
 2017-09-15 11:00:09 
Anal dildo training
anal dildo training
 GayPorn(Gay),Amateur(Gay),Gaping(Gay),Latin(Gay),SexToys(Gay),AnalTraining,AnalDildo,Training 
 1 min                  96
xhamster        
 2017-09-13 15:01:49 
Anal vibrator training in red black
Anal vibrator training in red black
 Men(Gay),GayPorn(Gay),Amateur(Gay),Crossdressers(Gay),SexToys(Gay),HDGays,AnalVibrator,InTraining,BlackVibrator,AnalTraining,RedAnal,RedBlack,Training,BlackAnal,Black 
 3 min                  85
xhamster        
 2017-09-07 13:00:11 
Asshole stretched and gaped after anal dildo training
Asshole stretched and gaped after anal dildo training
 Twinks(Gay),Amateur(Gay),Gaping(Gay),Latin(Gay),SexToys(Gay),StretchedAsshole,AfterAnal,AnalTraining,Stretched,AnalDildo,Asshole,Training 
 2 min                  103
xhamster        
 2017-08-10 04:00:29 
Slow anal training - 02
Slow anal training - 02
 Amateur(Gay),BigCocks(Gay),Fisting(Gay),Gaping(Gay),SexToys(Gay),HDGays,AnalTraining,Training 
 7 min                  96
xhamster        
 2017-08-05 03:00:29 
Anal Training
Anal Training
 Men(Gay),AnalTraining,Training 
 2 min                  74
xhamster        
 2017-07-22 13:00:23 
Latex gimp anal training
latex gimp anal training
 Amateur(Gay),BDSM(Gay),BigCocks(Gay),Daddies(Gay),SexToys(Gay),HDGays,AnalTraining,LatexAnal,Training 
 7 min                  69
xhamster        
 2017-07-22 03:00:11 
Ass anal training
Ass anal training
 Masturbation(Gay),SexToys(Gay),HDGays,AnalTraining,AssTraining,Training,AnalAss 
 1 min                  72
xhamster        
 2017-07-19 19:00:38 
Ass Clapping And Spread After Anal Training
Ass Clapping And Spread After Anal Training
 Men(Gay),GayPorn(Gay),FatGays(Gay),HDGays,AssClapping,AfterAnal,AnalTraining,AssTraining,AssSpread,Clapping,Training,AnalAss 
 0 min                  91
xhamster        
 2017-05-20 10:01:22 
Beginning Anal Training #2
Beginning Anal Training #2
 GayPorn(Gay),Amateur(Gay),Daddies(Gay),Masturbation(Gay),SexToys(Gay),HDGays,Beginning,AnalTraining,Training 
 5 min                  70
xhamster        
 2017-04-30 10:15:15 
Anal training in chastity in public staircase
Anal training in chastity in public staircase
 Amateur(Gay),Masturbation(Gay),Webcams(Gay),HDGays,AnalinPublic,InTraining,InPublic,Staircase,AnalTraining,PublicAnal,Training 
 2 min                  73
xhamster        
 2017-04-14 12:15:28 
Horny Dutch Bi Student 24yo Anal Stretch Training (clean)
Horny Dutch Bi Student 24yo Anal Stretch Training (clean)
 Men(Gay),Amateur(Gay),Gaping(Gay),SmallCocks(Gay),Webcams(Gay),HDGays,DutchAnal,HornyStudent,BiAnal,StudentAnal,AnalTraining,Stretch,Student,Training 
 3 min                  107
xhamster        
 2017-04-10 09:30:18 
Anal training and teasing on couch p2
anal training and teasing on couch p2
 Men(Gay),Amateur(Gay),Gaping(Gay),Latin(Gay),SexToys(Gay),AnalTraining,Training,Teasing 
 2 min                  75
xhamster        
 2017-03-24 13:00:35 
Anal training and teasing on couch p1
anal training and teasing on couch p1
 GayPorn(Gay),Amateur(Gay),Latin(Gay),SexToys(Gay),Webcams(Gay),AnalTraining,Training,Teasing 
 1 min                  78
xhamster        
 2017-03-24 12:00:09 
Femboy Tommy first anal submission training to be a shemale
Femboy Tommy first anal submission training to be a shemale
 Bareback(Gay),BDSM(Gay),BigCocks(Gay),Crossdressers(Gay),Gaping(Gay),AnalSubmission,AnalTraining,FirstAnal,Submission,Training,First 
 5 min                  121
xhamster        
 2017-03-22 06:15:22 
Anal training and gaping asshole preview 01
Anal training and gaping asshole preview 01
 GayPorn(Gay),Amateur(Gay),Gaping(Gay),Latin(Gay),SexToys(Gay),AnalGaping,AnalTraining,Asshole,Training 
 0 min                  71
xhamster        
 2017-03-15 22:00:07 
Anal training and gaping asshole preview 02
Anal training and gaping asshole preview 02
 GayPorn(Gay),Amateur(Gay),Gaping(Gay),Latin(Gay),SexToys(Gay),AnalGaping,AnalTraining,Asshole,Training 
 0 min                  73
xhamster        
 2017-03-15 22:00:07 
Dildo anal training
dildo anal training
 GayPorn(Gay),Amateur(Gay),Gaping(Gay),Latin(Gay),SexToys(Gay),AnalTraining,AnalDildo,Training 
 0 min                  68
xhamster        
 2017-03-05 19:30:09 
Sissy Anal Training
Sissy Anal Training
 Crossdressers(Gay),SexToys(Gay),SissyTraining,AnalTraining,Sissy,Training 
 7 min                  60
xhamster        
 2017-02-28 22:00:41 
Huge anal dildo training gay
Huge anal dildo training gay
 GayPorn(Gay),Amateur(Gay),BigCocks(Gay),SexToys(Gay),HDGays,AnalTraining,HugeDildo,AnalDildo,HugeAnal,Training 
 5 min                  99
xhamster        
 2017-02-27 00:00:22 
Gaped wide hole - anal training and teasing
gaped wide hole - anal training and teasing
 GayPorn(Gay),Amateur(Gay),Gaping(Gay),Latin(Gay),SexToys(Gay),AnalHole,AnalTraining,Hole,Training,Teasing 
 0 min                  96
xhamster        
 2017-01-26 23:45:52 
Anal training fail part 2 January 2
Anal training fail part 2 January 2
 Amateur(Gay),SexToys(Gay),HDGays,Part2,January,AnalTraining,Training 
 2 min                  70
xhamster        
 2017-01-06 00:00:30 
January 2 anal training part 2
January 2 anal training part 2
 Amateur(Gay),SexToys(Gay),HDGays,Part2,January,AnalTraining,Training 
 2 min                  74
xhamster        
 2017-01-06 00:00:19 
Failed anal training January 2 p1
Failed anal training January 2 p1
 Amateur(Gay),SexToys(Gay),HDGays,Failed,January,AnalTraining,Training 
 2 min                  70
xhamster        
 2017-01-05 18:15:12 
Deep dildo anal training
Deep dildo anal training
 GayPorn(Gay),Amateur(Gay),Gaping(Gay),Latin(Gay),SexToys(Gay),DeepDildo,AnalTraining,DeepAnal,AnalDildo,Training 
 1 min                  65
xhamster        
 2017-01-04 23:00:29 
Training anal with small toy.
Training anal with small toy.
 GayPorn(Gay),Amateur(Gay),Gaping(Gay),Latin(Gay),SexToys(Gay),HDGays,AnalTraining,SmallAnal,Training,Small 
 0 min                  96
xhamster        
 2016-12-25 13:00:14 
Anal training dilation
Anal training dilation
 Amateur(Gay),Fisting(Gay),Gaping(Gay),SexToys(Gay),Webcams(Gay),AnalTraining,Training 
 3 min                  80
xhamster        
 2016-12-22 09:15:17