Sissy Milking Videos (1,009)

Filter by
Date added
reset
Duration
reset
Quality
reset
VR
reset
Source
reset
Tied Up Crossdresser Slave Gets Wanked Off By The Pantyhose Encasement Queen (MP4 FULL HD)62% HD 0:12 / 21:21
Report this video
Tied Up Crossdresser Slave Gets Wanked Off By The Pantyhose Encasement Queen (MP4 FULL HD)
Clips4sale 1 year ago
Strict Sissy CBT Bondage Procedure (1080p)69% HD 0:25 / 15:56
Report this video
Strict Sissy CBT Bondage Procedure (1080p)
Clips4sale 1 year ago
4K - FULL CREAM COMPILATION NEO 566% 4K 0:14 / 38:40
Report this video
4K - FULL CREAM COMPILATION NEO 5
Clips4sale 1 year ago
Gloryhole Slut *MobileHD*50% 0:03 / 3:59
Report this video
Gloryhole Slut *MobileHD*
Clips4sale 3 years ago
Femdom Anal Annihilation: Big Boob Mistress Drains Prostate and Balls with Extreme Anal Fisting Part 5 of 5 (1080p)66% HD 0:30 / 9:03
Report this video
Femdom Anal Annihilation: Big Boob Mistress Drains Prostate and Balls with Extreme Anal Fisting Part 5 of 5 (1080p)
Clips4sale 1 year ago
Amazing Big Balls, and Cummm61% HD 0:39 / 15:33
Report this video
Amazing Big Balls, and Cummm
FapHouse 6 months ago
Sissy Milked and Cumming on FuckMachine65% HD 0:10 / 7:01
Report this video
Sissy Milked and Cumming on FuckMachine
LoyalFans 2 years ago
Hot Milk Inside the Ass to Ward off the Cold HD 0:39 / 15:24
Report this video
Hot Milk Inside the Ass to Ward off the Cold
FapHouse 1 year ago
Sissy Hard Anal Double **** HD 0:10 / 12:27
Report this video
Sissy Hard Anal Double ****
LoyalFans 2 years ago
(4K) Femdom Anal Annihilation: Full-Length 60-MIN Huge Strap-on Cock, CBT, Extreme Fisting (4K)67% 4K 0:30 / 1:04:09
Report this video
(4K) Femdom Anal Annihilation: Full-Length 60-MIN Huge Strap-on Cock, CBT, Extreme Fisting (4K)
Clips4sale 1 year ago
it s this sissy milkboy s first time HD 0:30 / 17:30
Report this video
it s this sissy milkboy s first time
PornBox 7 months ago
Anal Piggy Punishment: Big Boob Mistress, Pegging with Chastity, Extreme Humiliation, and Deep Fisting FULL-LENGTH (1080p)66% HD 0:30 / 58:54
Report this video
Anal Piggy Punishment: Big Boob Mistress, Pegging with Chastity, Extreme Humiliation, and Deep Fisting FULL-LENGTH (1080p)
Clips4sale 1 year ago
Cuffed and Fucked 72063% HD 0:55 / 11:59
Report this video
Cuffed and Fucked 720
Clips4sale 2 months ago
Latex Closeup Doggystyle with a View From Below66% HD 0:39 / 17:05
Report this video
Latex Closeup Doggystyle with a View From Below
FapHouse 6 months ago
Milking My Rubber Slut (1080p) HD 0:01 / 10:02
Report this video
Milking My Rubber Slut (1080p)
Clips4sale 3 years ago
Sissy Baby Step Son Part 3 Diaper Pansy Torment65% 0:11 / 13:50
Report this video
Sissy Baby Step Son Part 3 Diaper Pansy Torment
Clips4sale 2 years ago
Milked Cum Eating Sissy Bitch *MobileHD*65% 0:15 / 11:07
Report this video
Milked Cum Eating Sissy Bitch *MobileHD*
Clips4sale 3 years ago
Milked Cum Eating Sissy Bitch *4K* 4K 0:15 / 11:07
Report this video
Milked Cum Eating Sissy Bitch *4K*
Clips4sale 3 years ago
Step-mommy Fucks Daddy's Ass Before Leaving HD 0:39 / 15:53
Report this video
Step-mommy Fucks Daddy's Ass Before Leaving
FapHouse 6 months ago
(4K) Anal Piggy Punishment: Pegging with Chastity, Humiliation, and Deep Fisting (4K)66% 4K 0:30 / 58:54
Report this video
(4K) Anal Piggy Punishment: Pegging with Chastity, Humiliation, and Deep Fisting (4K)
Clips4sale 11 months ago
Jessica Simpsin Party on Dec 29, 201963% HD 2:00 / 1:15:26
Report this video
Jessica Simpsin Party on Dec 29, 2019
Flirt4Free 5 years ago
The Feminization Room - Remy D gets caught and transformed by Princess Dandy and Megan Daw (shaving, makeup, feminization, sissy, chastity, crossdressing, double domination, pegging)54% 0:30 / 58:28
Report this video
The Feminization Room - Remy D gets caught and transformed by Princess Dandy and Megan Daw (shaving, makeup, feminization, sissy, chastity, crossdressing, double domination, pegging)
Clips4sale 8 months ago
New Cumshot Compilation54% HD 0:39 / 23:07
Report this video
New Cumshot Compilation
FapHouse 6 months ago
COCK IN A FROCK 761% 4K 0:30 / 15:22
Report this video
COCK IN A FROCK 7
Clips4sale 7 months ago
4K - Lusty Shower Vol 1757% 4K 0:14 / 28:26
Report this video
4K - Lusty Shower Vol 17
Clips4sale 6 months ago
A Bound Prostate Milking for the Sissy Slave58% 0:20 / 17:51
Report this video
A Bound Prostate Milking for the Sissy Slave
Clips4sale 1 year ago
Slut Milking (1080p)49% HD 0:12 / 15:15
Report this video
Slut Milking (1080p)
Clips4sale 9 months ago
FULL CREAM COMPILATION NEO 267% 4K 0:59 / 32:01
Report this video
FULL CREAM COMPILATION NEO 2
Clips4sale 2 years ago
Horny Cheating Housewife Ria Bentley Does Anal With the Milkman66% HD 0:30 / 25:34
Report this video
Horny Cheating Housewife Ria Bentley Does Anal With the Milkman
Clips4sale 5 months ago
Glam Slut Milking Session (4k)74% 4K 0:10 / 10:17
Report this video
Glam Slut Milking Session (4k)
LoyalFans 4 months ago
Transvestite with Big Dick Enjoys a Lot, a Lot of Milk Dripping Into His Mouth HD 0:39 / 11:07
Report this video
Transvestite with Big Dick Enjoys a Lot, a Lot of Milk Dripping Into His Mouth
FapHouse 3 weeks ago
Cum Eating Panties Slut (MP4)64% 0:13 / 13:30
Report this video
Cum Eating Panties Slut (MP4)
Clips4sale 11 months ago
EXTREME PROSTATE ORGASM - EROTIC PROSTATE MILKING, Hands Free Orgasm, HFO Mind Fuck33% 0:30 / 28:26
Report this video
EXTREME PROSTATE ORGASM - EROTIC PROSTATE MILKING, Hands Free Orgasm, HFO Mind Fuck
C4S 10 months ago
Perverse Pink Domina! Kinky Pink Couple's Fetish Heaven!63% 0:30 / 32:27
Report this video
Perverse Pink Domina! Kinky Pink Couple's Fetish Heaven!
Clips4sale 1 week ago
Morning Cumshot63% HD 0:39 / 2:10
Report this video
Morning Cumshot
FapHouse 2 months ago
Sit on My Giant Cock and Swallow My Cum and My Piss51% HD 0:39 / 3:15
Report this video
Sit on My Giant Cock and Swallow My Cum and My Piss
FapHouse 2 years ago
Sissy Slut Clit Milked HD 0:39 / 8:48
Report this video
Sissy Slut Clit Milked
FapHouse 11 months ago
Sissy Club Slut: Femdom Fisting, Pegging, Dick Sticking Part 2 of 2 (1080p)61% HD 0:22 / 29:58
Report this video
Sissy Club Slut: Femdom Fisting, Pegging, Dick Sticking Part 2 of 2 (1080p)
Clips4sale 1 year ago
Reward for my leather sissy Katja (handjob and cumshot)72% 0:11 / 7:04
Report this video
Reward for my leather sissy Katja (handjob and cumshot)
Clips4sale 2 years ago
Sissy Milk Maid Cleans mp457% 0:06 / 9:30
Report this video
Sissy Milk Maid Cleans mp4
Clips4sale 8 months ago
4K - FULL CREAM COMPILATION NEO 364% 4K 0:08 / 44:51
Report this video
4K - FULL CREAM COMPILATION NEO 3
Clips4sale 1 year ago
Chastity Sissy F Machine Milking - Jessica Bloom Cums Hands Free and Swallows Cum66% HD 0:39 / 21:03
Report this video
Chastity Sissy F Machine Milking - Jessica Bloom Cums Hands Free and Swallows Cum
FapHouse 1 year ago
Two Monstruous Load of Cum HD 0:39 / 10:24
Report this video
Two Monstruous Load of Cum
FapHouse 2 years ago
Milking machine HD 0:39 / 3:42
Report this video
Milking machine
FapHouse 2 years ago
Satin Crossdresser Milked By Zara (WMV) 0:14 / 12:31
Report this video
Satin Crossdresser Milked By Zara (WMV)
Clips4sale 5 months ago
Eat Cum Because You Are Gay CEI JOI Cumshot45% 0:28 / 11:17
Report this video
Eat Cum Because You Are Gay CEI JOI Cumshot
Clips4sale 2 years ago
Sensitive Milking for Tied up Crossdresser66% HD 0:39 / 8:17
Report this video
Sensitive Milking for Tied up Crossdresser
FapHouse 1 year ago
Scotland the Brave Takes It in the Ass66% 4K 0:30 / 22:18
Report this video
Scotland the Brave Takes It in the Ass
Clips4sale 5 months ago
The Feminization Room - with Remy D and Megan Daw49% HD 0:10 / 58:28
Report this video
The Feminization Room - with Remy D and Megan Daw
LoyalFans 8 months ago
Alexxa Von Hell converts her boytoy into a cum eating slut HD 0:34 / 12:34
Report this video
Alexxa Von Hell converts her boytoy into a cum eating slut
Clips4sale 1 year ago
Dont be a pissy sissy!54% 0:11 / 5:03
Report this video
Dont be a pissy sissy!
Clips4sale 3 years ago
Femboy plays with their foreskin HD 0:42 / 14:41
Report this video
Femboy plays with their foreskin
Clips4sale 2 years ago
Somnophiliac Sleepover63% HD 0:10 / 18:20
Report this video
Somnophiliac Sleepover
Clips4sale 3 years ago
Cuffed and Fucked WMV 0:44 / 11:59
Report this video
Cuffed and Fucked WMV
Clips4sale 4 months ago
INTENSE PROSTATE ORGASM - PROSTATE MILKING, Hands Free Orgasm, HFO Mind Melt41% 0:30 / 28:26
Report this video
INTENSE PROSTATE ORGASM - PROSTATE MILKING, Hands Free Orgasm, HFO Mind Melt
C4S 10 months ago
Sissy Girl Moaning and Milked Like a Cow HD 0:39 / 1:06
Report this video
Sissy Girl Moaning and Milked Like a Cow
FapHouse 1 year ago
Futa Ladyboy Milking TS Dick Dry HD 0:39 / 11:50
Report this video
Futa Ladyboy Milking TS Dick Dry
FapHouse 2 weeks ago
SISSY MILKING (EN-720) HD 0:30 / 6:30
Report this video
SISSY MILKING (EN-720)
Clips4sale 10 months ago
Prostate milking blowjob making sissy fill my mouth with her milk then swallowing68% HD 0:39 / 10:30
Report this video
Prostate milking blowjob making sissy fill my mouth with her milk then swallowing
FapHouse 3 years ago
Pretty Sissy Anal Milking60% HD 0:11 / 14:10
Report this video
Pretty Sissy Anal Milking
Clips4sale 3 years ago
A Naughty Trans Maid Making Fresh Milk for Her Lucky Boss HD 0:39 / 1:43
Report this video
A Naughty Trans Maid Making Fresh Milk for Her Lucky Boss
FapHouse 1 week ago
You Better Workout Slut - Workout and Selffacial Proteinshake 0:39 / 3:05
Report this video
You Better Workout Slut - Workout and Selffacial Proteinshake
FapHouse 2 years ago
Unloading These Big Balls of Hot Milk55% HD 0:39 / 15:27
Report this video
Unloading These Big Balls of Hot Milk
FapHouse 10 months ago
Sissy Club Slut Part 2/2: Sissy Femboy Fucked with Femdom Pegging, Anal ****, and Huge Dildo Fucking with Mistress Stellina Obscura55% HD 0:10 / 29:59
Report this video
Sissy Club Slut Part 2/2: Sissy Femboy Fucked with Femdom Pegging, Anal ****, and Huge Dildo Fucking with Mistress Stellina Obscura
LoyalFans 2 months ago
CUM injection and BIG TOYS for the perfect PEGGING SISSYGASM!75% HD 0:30 / 17:28
Report this video
CUM injection and BIG TOYS for the perfect PEGGING SISSYGASM!
Clips4sale 9 months ago
For Milk Fans HD 0:39 / 1:30
Report this video
For Milk Fans
FapHouse 1 week ago
Ava Venom and Nova Escobar Double Trans Femdom Spitroast Muscle Bottom44% HD 0:10 / 23:56
Report this video
Ava Venom and Nova Escobar Double Trans Femdom Spitroast Muscle Bottom
LoyalFans 5 months ago
Sissy Gamer Gurl Part 3/3: Slave Fucked with Deep Anal 🤜 , Cock Milking, & Cum Eating HD 0:10 / 7:09
Report this video
Sissy Gamer Gurl Part 3/3: Slave Fucked with Deep Anal 🤜 , Cock Milking, & Cum Eating
LoyalFans 4 months ago
Valentine's handjob 202460% 0:11 / 10:32
Report this video
Valentine's handjob 2024
Clips4sale 1 year ago
Post Orgasm Cum Milking Jessica Bloom Big Trans Dick Milking Machine HD 0:39 / 24:34
Report this video
Post Orgasm Cum Milking Jessica Bloom Big Trans Dick Milking Machine
FapHouse 1 year ago
I Believe You Already Know What This Is Going to Do Dubai Style Well Arab Weather I Give My Big Load of Milk for You to Fulfill HD 0:39 / 11:32
Report this video
I Believe You Already Know What This Is Going to Do Dubai Style Well Arab Weather I Give My Big Load of Milk for You to Fulfill
FapHouse 1 year ago
camshots sissy compilation61% 0:15 / 5:01
Report this video
camshots sissy compilation
AnalVids 1 month ago
Indian Trans Woman Gaurisissy Pressing and Milking Her Boobs in Pink Saree HD 0:07 / 0:39
Report this video
Indian Trans Woman Gaurisissy Pressing and Milking Her Boobs in Pink Saree
FapHouse 6 months ago
Milking The Maid70% HD 0:10 / 39:52
Report this video
Milking The Maid
LoyalFans 7 months ago
CV POV Making cum in your throat! 1:00 / 14:42
Report this video
CV POV Making cum in your throat!
Clips4sale 2 years ago
COMPILATION Blowjob 0:27 / 1:01:30
Report this video
COMPILATION Blowjob
Clips4sale 2 years ago
Naughty patient Katja (diaper pee, milking and cumshot)68% HD 0:11 / 25:59
Report this video
Naughty patient Katja (diaper pee, milking and cumshot)
Clips4sale 3 years ago
Ava Venom Bound Gagged and Edged to Cum Eruption Ft Mistress Celene46% 0:30 / 29:26
Report this video
Ava Venom Bound Gagged and Edged to Cum Eruption Ft Mistress Celene
C4S 5 months ago
Gloryhole Slut *FULL-HD*66% HD 0:03 / 3:59
Report this video
Gloryhole Slut *FULL-HD*
Clips4sale 3 years ago
Hogtied And Gagged My Nylon Slut (1080p) HD 0:09 / 9:24
Report this video
Hogtied And Gagged My Nylon Slut (1080p)
Clips4sale 4 years ago
Daddy Ken Fucks N Fists Me Til I Shoot Femboi Clit Cum up Like a Fountain! Candy Ass Sissy HD 0:39 / 15:46
Report this video
Daddy Ken Fucks N Fists Me Til I Shoot Femboi Clit Cum up Like a Fountain! Candy Ass Sissy
FapHouse 1 year ago
Captured and Milked By A Prostate Obsessed Alien 4K 0:29 / 21:11
Report this video
Captured and Milked By A Prostate Obsessed Alien
Clips4sale 2 months ago
Slutty Cum Extraction (1080p) HD 0:05 / 12:19
Report this video
Slutty Cum Extraction (1080p)
Clips4sale 3 years ago
CD Teases and Milks Part 1 HD 0:07 / 0:39
Report this video
CD Teases and Milks Part 1
FapHouse 6 months ago
Bitch Sandwich! mp4 0:11 / 5:00
Report this video
Bitch Sandwich! mp4
Clips4sale 4 years ago
Cutie Trans Hucow Melody Teaches Us How to Milk a Cock with Your Butt66% HD 0:39 / 26:52
Report this video
Cutie Trans Hucow Melody Teaches Us How to Milk a Cock with Your Butt
FapHouse 1 year ago
BBW Step Mommy Teases Sissified Cross Dressing Slut 0:09 / 8:29
Report this video
BBW Step Mommy Teases Sissified Cross Dressing Slut
Clips4sale 8 months ago
Gloryhole Bitch *MobileHD*65% HD 0:03 / 3:59
Report this video
Gloryhole Bitch *MobileHD*
Clips4sale 3 years ago
Squeeze Me Where?52% HD 2:00 / 4:08
Report this video
Squeeze Me Where?
Flirt4Free 5 years ago
Get Milked At My Party (1080 HD) HD 0:11 / 11:43
Report this video
Get Milked At My Party (1080 HD)
Clips4sale 3 years ago
Fire Elf Giving a Oily Footjob HD 0:39 / 17:18
Report this video
Fire Elf Giving a Oily Footjob
FapHouse 1 year ago
Trans girl milks herself with a pocket pussy until she cums all over her girlcock 💦 HD 0:10 / 2:48
Report this video
Trans girl milks herself with a pocket pussy until she cums all over her girlcock 💦
LoyalFans 6 months ago
Perverted Nurse 0:39 / 2:32
Report this video
Perverted Nurse
FapHouse 2 weeks ago
Cock milking HD 0:10 / 5:06
Report this video
Cock milking
LoyalFans 9 months ago
Sissy Baby Nurse Sucks 0:30 / 24:53
Report this video
Sissy Baby Nurse Sucks
Clips4sale 10 months ago
Sexy and Milky Bombshell HD 0:39 / 1:35
Report this video
Sexy and Milky Bombshell
FapHouse 1 month ago
Gloryhole Bitch *FULL-HD*45% HD 0:03 / 3:59
Report this video
Gloryhole Bitch *FULL-HD*
Clips4sale 3 years ago
Good Sissy Milking - WMV - 1920 0:25 / 13:44
Report this video
Good Sissy Milking - WMV - 1920
Clips4sale 1 year ago

Related searches

femdom trans chastity penny barber trans cumshot compilation amateur crossdressing creampie compilation amateur creampie penny barber sissy heather vandeven masturbation training sissy used cum denial shemale cumshot compilation sissy milking sissy compilation chastity orgasm chastity fuck chastity creampie sissy facial
Categories Pornstars
Categories Pornstars

© 2025 Pornmd.com. All rights reserved.

Search for
Random