My sissy fantasy is getting fucked while crossdressing
My sissy fantasy is getting fucked while crossdressing
 Amateur(Gay),Crossdresser(Gay),Masturbation(Gay),HDVideos,CrossdressingNewbies(Gay),Fetish(Gay) 
 14 min                  31
xhamster        
 2022-12-17 12:01:54 
I just love the feeling of getting all dolled up
I just love the feeling of getting all dolled up
 Twink(Gay),Amateur(Gay),Crossdresser(Gay),Masturbation(Gay),HDVideos,CrossdressingNewbies(Gay),Skinny(Gay),Twinks(Gay) 
 14 min                  39
xhamster        
 2022-12-05 00:04:23 
Getting fucked while crossdressing in the ultimate taboo
Getting fucked while crossdressing in the ultimate taboo
 Black(Gay),Amateur(Gay),Crossdresser(Gay),Masturbation(Gay),HDVideos,CrossdressingNewbies(Gay),While(Gay),Myself(Gay),GetFucked(Gay),What(Gay),LikeIt(Gay),Fetish(Gay) 
 13 min                  28
xhamster        
 2022-11-12 12:01:14 
I only fuck sissy boys in their asses
I only fuck sissy boys in their asses
 Twink(Gay),Amateur(Gay),Crossdresser(Gay),Masturbation(Gay),HDVideos,CrossdressingNewbies(Gay),Skinny(Gay),Twinks(Gay),SissyBoys(Gay),Down(Gay),Want(Gay),GetFucked(Gay),DowntoBusiness(Gay),Fetish(Gay) 
 14 min                  20
xhamster        
 2022-11-07 00:00:06 
My crossdresser ass is here waiting for you hard cock
My crossdresser ass is here waiting for you hard cock
 Amateur(Gay),Crossdresser(Gay),Masturbation(Gay),HDVideos,CrossdressingNewbies(Gay),HotGay(Gay),GayMen(Gay),GayAss(Gay),GayCrossdresser(Gay),GayCock(Gay),GayGuys(Gay),GayJOI(Gay),Fetish(Gay) 
 14 min                  22
xhamster        
 2022-10-24 12:00:05 
I want to take my crossdressing to the next level
I want to take my crossdressing to the next level
 Twink(Gay),Amateur(Gay),Crossdresser(Gay),Masturbation(Gay),HDVideos,CrossdressingNewbies(Gay),Skinny(Gay),Down(Gay),Want(Gay),What(Gay) 
 14 min                  32
xhamster        
 2022-10-07 12:00:04 
I want you to get dressed before I fuck you
I want you to get dressed before I fuck you
 Twink(Gay),Crossdresser(Gay),Latino(Gay),HDVideos,CrossdressingNewbies(Gay),Skinny(Gay),Twinks(Gay),Down(Gay),Want(Gay),Treat(Gay) 
 13 min                  38
xhamster        
 2022-09-19 12:00:04 
Girl clothes are so much sexier
Girl clothes are so much sexier
 Twink(Gay),Crossdresser(Gay),Latino(Gay),Masturbation(Gay),HDVideos,CrossdressingNewbies(Gay),Skinny(Gay),Twinks(Gay),Want(Gay) 
 14 min                  36
xhamster        
 2022-08-27 00:03:35 
I was a little nervous at first this is super hot
I was a little nervous at first this is super hot
 Twink(Gay),Amateur(Gay),Crossdresser(Gay),Masturbation(Gay),HDVideos,CrossdressingNewbies(Gay),Skinny(Gay),Twinks(Gay),InFrontof(Gay),InFront(Gay),Sucks(Gay),Want(Gay),Bitched(Gay) 
 13 min                  37
xhamster        
 2022-08-21 12:00:03 
I know crossdressing like this is totally taboo
I know crossdressing like this is totally taboo
 Black(Gay),Twink(Gay),BigCock(Gay),Crossdresser(Gay),Masturbation(Gay),HDVideos,CrossdressingNewbies(Gay),GayLove(Gay),Skinny(Gay) 
 14 min                  38
xhamster        
 2022-08-15 12:00:12 
Maybe I can be beautiful too
Maybe I can be beautiful too
 Twink(Gay),Amateur(Gay),BigCock(Gay),Crossdresser(Gay),Masturbation(Gay),HDVideos,CrossdressingNewbies(Gay),Skinny(Gay) 
 14 min                  36
xhamster        
 2022-07-25 00:00:21 
I just want to become beautiful
I just want to become beautiful
 Twink(Gay),Amateur(Gay),Crossdresser(Gay),Masturbation(Gay),HDVideos,CrossdressingNewbies(Gay),GayJOI(Gay),Skinny(Gay) 
 17 min                  41
xhamster        
 2022-06-22 12:04:12 
I want to feel his hard cock in my crossdresser ass
I want to feel his hard cock in my crossdresser ass
 Black(Gay),Twink(Gay),Amateur(Gay),Crossdresser(Gay),Masturbation(Gay),HDVideos,CrossdressingNewbies(Gay),BlackGay(Gay),HotGay(Gay),GayAss(Gay),GaySissy(Gay),GayCrossdresser(Gay),GayCock(Gay),Skinny(Gay) 
 17 min                  42
xhamster        
 2022-06-22 00:00:21 
Lets get this hot crossdressing session started
Lets get this hot crossdressing session started
 Twink(Gay),Crossdresser(Gay),Hunk(Gay),Masturbation(Gay),Muscular(Gay),HDVideos,CrossdressingNewbies(Gay),HotGay(Gay),GoGay(Gay),Skinny(Gay) 
 16 min                  42
xhamster        
 2022-06-21 00:02:37 
I just get so hard when I get all dolled up
I just get so hard when I get all dolled up
 Twink(Gay),Amateur(Gay),BigCock(Gay),Crossdresser(Gay),Masturbation(Gay),HDVideos,CrossdressingNewbies(Gay),Skinny(Gay) 
 17 min                  36
xhamster        
 2022-06-19 00:00:28 
I can see he really like it when I crossdress
I can see he really like it when I crossdress
 Black(Gay),Twink(Gay),Amateur(Gay),Crossdresser(Gay),Interracial(Gay),Masturbation(Gay),HDVideos,CrossdressingNewbies(Gay),GayMen(Gay),GayLove(Gay),GayGuys(Gay),Skinny(Gay) 
 16 min                  32
xhamster        
 2022-06-04 00:01:01 
I just love getting all dolled up like a total slut
I just love getting all dolled up like a total slut
 Twink(Gay),Amateur(Gay),Crossdresser(Gay),Masturbation(Gay),HDVideos,CrossdressingNewbies(Gay),GayLove(Gay),Skinny(Gay) 
 14 min                  42
xhamster        
 2022-05-23 00:00:09 
I love it when he wears lingerie for me
I love it when he wears lingerie for me
 Black(Gay),Twink(Gay),Amateur(Gay),Crossdresser(Gay),Interracial(Gay),Masturbation(Gay),HDVideos,CrossdressingNewbies(Gay),BlackGay(Gay),HotGay(Gay),GayAss(Gay),GaySissy(Gay),GayLove(Gay),Skinny(Gay) 
 15 min                  33
xhamster        
 2022-05-17 00:02:25 
I know its crazy but wearing lingerie gets me so hard
I know its crazy but wearing lingerie gets me so hard
 Twink(Gay),Amateur(Gay),Crossdresser(Gay),Masturbation(Gay),HDVideos,CrossdressingNewbies(Gay),GayMen(Gay),GayLove(Gay),GayGuys(Gay),Skinny(Gay) 
 13 min                  48
xhamster        
 2022-05-09 00:02:13 
I have a big alpha make cock for your crossdresser ass
I have a big alpha make cock for your crossdresser ass
 Twink(Gay),Amateur(Gay),BigCock(Gay),Crossdresser(Gay),Masturbation(Gay),HDVideos,CrossdressingNewbies(Gay),BigDickGay(Gay),FirstTimeGay(Gay),BigCockGay(Gay),GayCum(Gay),GayAss(Gay),GaySissy(Gay),GayCrossdresser(Gay),FirstGay( 
 15 min                  37
xhamster        
 2022-05-05 00:00:44 
I think he wants to pound my tight crossdresser ass
I think he wants to pound my tight crossdresser ass
 Twink(Gay),Amateur(Gay),Blowjob(Gay),Crossdresser(Gay),Interracial(Gay),HDVideos,CrossdressingNewbies(Gay),GayMen(Gay),GayAss(Gay),GayCrossdresser(Gay),GayGuys(Gay),Anal(Gay),Skinny(Gay),Young(Gay) 
 14 min                  33
xhamster        
 2022-05-01 00:02:20 
I look so hot I need to take a picture
I look so hot I need to take a picture
 Twink(Gay),Amateur(Gay),Crossdresser(Gay),Latino(Gay),Masturbation(Gay),HDVideos,CrossdressingNewbies(Gay),HotGay(Gay),GayJOI(Gay),Skinny(Gay) 
 15 min                  35
xhamster        
 2022-04-18 00:01:00 
I can see how he looks at me that he wants to fuck
I can see how he looks at me that he wants to fuck
 Amateur(Gay),Blowjob(Gay),Crossdresser(Gay),HDVideos,CrossdressingNewbies(Gay),GayMen(Gay),GaySex(Gay),GayFuck(Gay),GayGuys(Gay),GayFuckGay(Gay),Anal(Gay),Fetish(Gay) 
 14 min                  43
xhamster        
 2022-04-15 00:04:54 
I can tell he wants to fuck me so bad
I can tell he wants to fuck me so bad
 Twink(Gay),Amateur(Gay),Crossdresser(Gay),Masturbation(Gay),HDVideos,CrossdressingNewbies(Gay),HotGay(Gay),GayMen(Gay),GaySex(Gay),GayFuck(Gay),GayGuys(Gay),GayFuckGay(Gay),Skinny(Gay) 
 15 min                  30
xhamster        
 2022-03-21 00:00:04 
My first sissy adventure was hotter than I ever imagined
My first sissy adventure was hotter than I ever imagined
 Twink(Gay),Amateur(Gay),Crossdresser(Gay),Masturbation(Gay),HDVideos,CrossdressingNewbies(Gay),HotGay(Gay),GaySissy(Gay),FirstGay(Gay),GayCock(Gay),GayJOI(Gay),Skinny(Gay) 
 14 min                  42
xhamster        
 2022-03-17 00:02:13 
I want to look as feminine as possible
I want to look as feminine as possible
 Twink(Gay),Amateur(Gay),Crossdresser(Gay),Masturbation(Gay),HDVideos,CrossdressingNewbies(Gay),GayAss(Gay),GayJOI(Gay),Skinny(Gay) 
 17 min                  35
xhamster        
 2022-03-11 00:00:11 
I want to get my dick sucked by a sissy
I want to get my dick sucked by a sissy
 Twink(Gay),Blowjob(Gay),Crossdresser(Gay),Hunk(Gay),HDVideos,CrossdressingNewbies(Gay),GaySissy(Gay),GayCock(Gay),GayCockSucking(Gay),GaySuck(Gay),Skinny(Gay) 
 13 min                  22
xhamster        
 2022-02-25 00:02:03 
I was so nervous the first time I put on lingerie
I was so nervous the first time I put on lingerie
 Twink(Gay),Amateur(Gay),Crossdresser(Gay),Hunk(Gay),Masturbation(Gay),HDVideos,CrossdressingNewbies(Gay),FirstTimeGay(Gay),GaySissy(Gay),FirstGay(Gay),GayCock(Gay),GayCockSucking(Gay),GaySuck(Gay),Skinny(Gay) 
 16 min                  42
xhamster        
 2022-02-07 00:00:02 
Look how fucking sexy I am
Look how fucking sexy I am
 Twink(Gay),Amateur(Gay),Crossdresser(Gay),Hunk(Gay),Masturbation(Gay),HDVideos,CrossdressingNewbies(Gay),HotGay(Gay),GaySex(Gay),GayFuck(Gay),GoGay(Gay),GayFuckGay(Gay),Skinny(Gay) 
 14 min                  27
xhamster        
 2022-02-03 00:00:41 
Crossdressing is a whole new level of hot
Crossdressing is a whole new level of hot
 Twink(Gay),Amateur(Gay),BigCock(Gay),Crossdresser(Gay),Hunk(Gay),Latino(Gay),Masturbation(Gay),HDVideos,CrossdressingNewbies(Gay),HotGay(Gay),GaySissy(Gay),Skinny(Gay) 
 14 min                  42
xhamster        
 2022-01-30 00:00:04 
I have a secret fetish for wearing lingerie
I have a secret fetish for wearing lingerie
 Amateur(Gay),BigCock(Gay),Crossdresser(Gay),Masturbation(Gay),HDVideos,CrossdressingNewbies(Gay),GayLove(Gay),GoGay(Gay) 
 15 min                  25
xhamster        
 2022-01-24 00:00:03 
I love dressing up like a women when I jerk off
I love dressing up like a women when I jerk off
 Twink(Gay),Amateur(Gay),Crossdresser(Gay),Masturbation(Gay),HDVideos,CrossdressingNewbies(Gay),GayMen(Gay),GayLove(Gay),GayGuys(Gay),GayJerking(Gay),Skinny(Gay) 
 14 min                  33
xhamster        
 2022-01-16 00:00:32 
My sissy ass needs to get fucked hard
My sissy ass needs to get fucked hard
 Black(Gay),Twink(Gay),Amateur(Gay),BigCock(Gay),Hunk(Gay),Masturbation(Gay),HDVideos,CrossdressingNewbies(Gay),BlackGay(Gay),HotGay(Gay),GaySex(Gay),GayFuck(Gay),GayAss(Gay),GaySissy(Gay),GayCock(Gay),GayFuckGay(Gay),Skinny(Ga 
 15 min                  28
xhamster        
 2022-01-08 00:00:29 
Get in here and put on your lingerie
Get in here and put on your lingerie
 Amateur(Gay),BigCock(Gay),Crossdresser(Gay),Hunk(Gay),Masturbation(Gay),HDVideos,CrossdressingNewbies(Gay),GayAss(Gay),GayJOI(Gay),Skinny(Gay) 
 15 min                  36
xhamster        
 2021-12-23 00:00:04 
Tonight I finally get to be a sissy slut
Tonight I finally get to be a sissy slut
 Twink(Gay),Crossdresser(Gay),Hunk(Gay),Masturbation(Gay),HDVideos,CrossdressingNewbies(Gay),HotGay(Gay),GaySissy(Gay),GoGay(Gay),Skinny(Gay) 
 14 min                  38
xhamster        
 2021-12-22 00:00:04 
My tight crossdresser ass is ready for a big cock
My tight crossdresser ass is ready for a big cock
 Twink(Gay),Amateur(Gay),Crossdresser(Gay),Hunk(Gay),Masturbation(Gay),HDVideos,CrossdressingNewbies(Gay),HotGay(Gay),GayMen(Gay),BigDickGay(Gay),BigCockGay(Gay),GayAss(Gay),GayCrossdresser(Gay),GayCock(Gay),GayGuys(Gay),Skinny( 
 15 min                  26
xhamster        
 2021-12-19 00:00:05 
First I have to put on my makeup
First I have to put on my makeup
 Twink(Gay),Amateur(Gay),Crossdresser(Gay),Hunk(Gay),Masturbation(Gay),HDVideos,CrossdressingNewbies(Gay),GaySissy(Gay),FirstGay(Gay),Skinny(Gay) 
 13 min                  38
xhamster        
 2021-12-15 00:00:05 
First I have to put on my makeup
First I have to put on my makeup
 Twink(Gay),Amateur(Gay),Crossdresser(Gay),Hunk(Gay),Masturbation(Gay),HDVideos,CrossdressingNewbies(Gay),GaySissy(Gay),FirstGay(Gay),Skinny(Gay) 
 13 min                  27
xhamster        
 2021-12-15 00:00:05 
This lacey outfit makes me feel so sexy
This lacey outfit makes me feel so sexy
 Twink(Gay),Amateur(Gay),Crossdresser(Gay),Hunk(Gay),Latino(Gay),Masturbation(Gay),HDVideos,CrossdressingNewbies(Gay),HotGay(Gay),Skinny(Gay) 
 13 min                  44
xhamster        
 2021-12-07 12:00:14 
I get so hard when I see myself in the mirror
I get so hard when I see myself in the mirror
 Twink(Gay),Amateur(Gay),Crossdresser(Gay),Hunk(Gay),Latino(Gay),Masturbation(Gay),HDVideos,CrossdressingNewbies(Gay),HotGay(Gay),GoGay(Gay),Skinny(Gay) 
 13 min                  28
xhamster        
 2021-11-25 12:00:12 
I get so hard when I see myself in the mirror
I get so hard when I see myself in the mirror
 Twink(Gay),Amateur(Gay),Crossdresser(Gay),Hunk(Gay),Latino(Gay),Masturbation(Gay),HDVideos,CrossdressingNewbies(Gay),HotGay(Gay),GoGay(Gay),Skinny(Gay) 
 13 min                  38
xhamster        
 2021-11-25 12:00:12 
Get your cock hard while I get dressed
Get your cock hard while I get dressed
 Black(Gay),BigCock(Gay),Crossdresser(Gay),Hunk(Gay),Interracial(Gay),Latino(Gay),Masturbation(Gay),CrossdressingNewbies(Gay),GayMen(Gay),GayCock(Gay),GayGuys(Gay),GayJOI(Gay),Skinny(Gay),HDVideos 
 14 min                  42
xhamster        
 2021-11-05 00:00:40 
I saw this lingerie and I knew I had to wear it
I saw this lingerie and I knew I had to wear it
 Twink(Gay),Amateur(Gay),Crossdresser(Gay),Hunk(Gay),Muscle(Gay),CrossdressingNewbies(Gay),Skinny(Gay),HDVideos 
 15 min                  39
xhamster        
 2021-11-01 00:01:20 
Crossdressing makes my heart beat so fast
Crossdressing makes my heart beat so fast
 Twink(Gay),Amateur(Gay),Crossdresser(Gay),Hunk(Gay),Latino(Gay),Masturbation(Gay),CrossdressingNewbies(Gay),GaySissy(Gay),GayCock(Gay),GayCockSucking(Gay),GaySuck(Gay),Skinny(Gay),HDVideos 
 13 min                  29
xhamster        
 2021-10-26 00:02:03 
It all starts with a little bit of makeup
It all starts with a little bit of makeup
 Twink(Gay),Amateur(Gay),Crossdresser(Gay),Hunk(Gay),Latino(Gay),CrossdressingNewbies(Gay),GoGay(Gay),Skinny(Gay),HDVideos 
 14 min                  46
xhamster        
 2021-10-16 00:00:18 
Let me take you on your first sissy adventure
Let me take you on your first sissy adventure
 Twink(Gay),Amateur(Gay),Crossdresser(Gay),Hunk(Gay),Latino(Gay),CrossdressingNewbies(Gay),GaySissy(Gay),FirstGay(Gay),GayCock(Gay),GayJOI(Gay),Skinny(Gay),HDVideos 
 14 min                  46
xhamster        
 2021-10-12 00:00:12 
You get to witness my first time crossdressing
You get to witness my first time crossdressing
 Twink(Gay),Crossdresser(Gay),Hunk(Gay),Interracial(Gay),CrossdressingNewbies(Gay),GayMen(Gay),FirstTimeGay(Gay),FirstGay(Gay),GayGuys(Gay),GayJOI(Gay),Anal(Gay),Skinny(Gay),HDVideos 
 10 min                  53
xhamster        
 2021-10-08 00:01:13 
Crossdressing always gets my cock so much harder
Crossdressing always gets my cock so much harder
 Amateur(Gay),Crossdresser(Gay),Latino(Gay),Masturbation(Gay),CrossdressingNewbies(Gay),GayCock(Gay),GayJOI(Gay),Skinny(Gay),HDVideos 
 11 min                  27
xhamster        
 2021-09-28 00:01:21 
I finally feel like a real sissy slut
I finally feel like a real sissy slut
 Amateur(Gay),Crossdresser(Gay),Hunk(Gay),Latino(Gay),Masturbation(Gay),CrossdressingNewbies(Gay),HotGay(Gay),HomemadeGay(Gay),AmateurGay(Gay),GaySissy(Gay),GayLove(Gay),GoGay(Gay),Skinny(Gay),HDVideos 
 11 min                  36
xhamster        
 2021-09-22 00:00:45 
I want to take this to the next level
I want to take this to the next level
 Twink(Gay),Crossdresser(Gay),Hunk(Gay),Masturbation(Gay),CrossdressingNewbies(Gay),GaySex(Gay),Skinny(Gay),HDVideos 
 12 min                  22
xhamster        
 2021-09-18 00:03:06 
Seeing him in lingerie gets me so hard
Seeing him in lingerie gets me so hard
 Twink(Gay),Blowjob(Gay),Crossdresser(Gay),Hunk(Gay),Masturbation(Gay),CrossdressingNewbies(Gay),HotGay(Gay),GayMen(Gay),GayGuys(Gay),Anal(Gay),Skinny(Gay),HDVideos 
 12 min                  50
xhamster        
 2021-09-14 00:01:10 
Ive always wondered what lingerie feels like
Ive always wondered what lingerie feels like
 Twink(Gay),BigCock(Gay),Crossdresser(Gay),Hunk(Gay),Latino(Gay),CrossdressingNewbies(Gay),GayMen(Gay),GayLove(Gay),GayGuys(Gay),HDVideos 
 16 min                  38
xhamster        
 2021-03-21 00:00:17 
White lingerie looks so good on my ebony body
White lingerie looks so good on my ebony body
 Black(Gay),Amateur(Gay),BigCock(Gay),Crossdresser(Gay),CrossdressingNewbies(Gay),EbonyGay(Gay),Skinny(Gay),HDVideos 
 11 min                  54
xhamster        
 2021-02-22 00:00:22 
This is my first time crossdressing like this
This is my first time crossdressing like this
 Amateur(Gay),Crossdresser(Gay),Hunk(Gay),Masturbation(Gay),CrossdressingNewbies(Gay),FirstTimeGay(Gay),GayLove(Gay),FirstGay(Gay),GayJOI(Gay),HDVideos 
 15 min                  45
xhamster        
 2021-02-02 00:02:29 
I am all dressed up and ready to take some cock
I am all dressed up and ready to take some cock
 BigCock(Gay),Crossdresser(Gay),Hunk(Gay),Masturbation(Gay),CrossdressingNewbies(Gay),GaySissy(Gay),GayCock(Gay),GayCockSucking(Gay),GaySuck(Gay),HDVideos 
 13 min                  29
xhamster        
 2021-01-25 00:01:58 
Lets start with a little makeup
Lets start with a little makeup
 Crossdresser(Gay),Latino(Gay),Masturbation(Gay),CrossdressingNewbies(Gay),HDVideos 
 15 min                  40
xhamster        
 2020-12-25 12:01:14 
My first sissy adventure was better than I ever imagined
My first sissy adventure was better than I ever imagined
 Crossdresser(Gay),Latin(Gay),Masturbation(Gay),HDVideos,CrossdressingNewbies(Gay),GaySissy(Gay),FirstGay(Gay),BetterGay(Gay),FirstGayEver(Gay),FreeFirstGay(Gay),FirstEverGay(Gay),GayAdventure(Gay),SissyGayTube(Gay) 
 13 min                  83
xhamster        
 2018-06-11 12:01:19 
I am such a sexy crossdresser slut
I am such a sexy crossdresser slut
 Crossdresser(Gay),Hunk(Gay),Masturbation(Gay),HDVideos,CrossdressingNewbies(Gay),SexyGay(Gay),GaySexy(Gay),GayCrossdresser(Gay),GaySlut(Gay),SlutGay(Gay),FreeSexyGay(Gay),FreeGaySlut(Gay),FreeGayCrossdresser(Gay),FreeGaySexy(G 
 13 min                  100
xhamster        
 2018-06-03 12:01:55 
Dressing up like a woman gets my cock rock hard
Dressing up like a woman gets my cock rock hard
 BigCock(Gay),Crossdresser(Gay),Hunk(Gay),Latin(Gay),Masturbation(Gay),HDVideos,CrossdressingNewbies(Gay),HardGay(Gay),GayHard(Gay),GayCock(Gay),RockGay(Gay),HardGayTube(Gay),GayHardCock(Gay),CockGay(Gay),FreeGayCock(Gay),Hard 
 12 min                  81
xhamster        
 2018-05-30 00:00:46 
I need my sissy ass fucked hard
I need my sissy ass fucked hard
 Amateur(Gay),Bareback(Gay),Crossdresser(Gay),Hunk(Gay),HDVideos,CrossdressingNewbies(Gay),GayAss(Gay),GaySissy(Gay),HardGay(Gay),GayHard(Gay),SissyGay(Gay),AssGay(Gay),GayNeed(Gay),FuckedHardGay(Gay),HardGayTube(Gay),FreeGayS 
 14 min                  36
xhamster        
 2018-05-22 00:00:27 
Tonight I finally get to be a really sissy crossdresser
Tonight I finally get to be a really sissy crossdresser
 Amateur(Gay),Crossdresser(Gay),Hunk(Gay),Latin(Gay),Masturbation(Gay),HDVideos,CrossdressingNewbies(Gay),GaySissy(Gay),GayCrossdresser(Gay),SissyGay(Gay),GaySissyCrossdresser(Gay),GayCrossdresserTube(Gay),GaySissyTube(Gay),FreeSis 
 13 min                  73
xhamster        
 2018-05-18 12:02:27 
My tight crossdresser ass is ready for a big cock
My tight crossdresser ass is ready for a big cock
 Amateur(Gay),Bareback(Gay),BigCock(Gay),Crossdresser(Gay),Hunk(Gay),HDVideos,CrossdressingNewbies(Gay),BigCockGay(Gay),BigAssGay(Gay),GayAss(Gay),GayBigCock(Gay),GayBigAss(Gay),GayCrossdresser(Gay),BigGayCock(Gay),BigGay(Gay 
 15 min                  63
xhamster        
 2018-04-24 00:00:07 
I like getting my sissy ass pounded while crossdressing
I like getting my sissy ass pounded while crossdressing
 Amateur(Gay),BigCock(Gay),Crossdresser(Gay),Hunk(Gay),Masturbation(Gay),HDVideos,CrossdressingNewbies(Gay),GayAss(Gay),GaySissy(Gay),AssGay(Gay),CrossdressingGay(Gay),FreeGayAss(Gay),LikeGay(Gay),FreeSissyGay(Gay),AssGayTumblr 
 17 min                  66
xhamster        
 2018-04-04 12:01:38 
White lingerie looks so good against my dark brown skin
White lingerie looks so good against my dark brown skin
 BlackandEbony(Gay),Amateur(Gay),BigCock(Gay),Crossdresser(Gay),Hunk(Gay),CrossdressingNewbies(Gay),HDVideos 
 16 min                  101
xhamster        
 2018-03-09 07:00:13 
My sissy fantasies are all coming true
My sissy fantasies are all coming true
 BlackandEbony(Gay),BigCock(Gay),Crossdresser(Gay),Hunk(Gay),Masturbation(Gay),CrossdressingNewbies(Gay),HDVideos 
 14 min                  64
xhamster        
 2018-03-04 07:00:26 
Your very first sissy adventure starts now
Your very first sissy adventure starts now
 Amateur(Gay),Bareback(Gay),Crossdresser(Gay),Hunk(Gay),HDVideos,CrossdressingNewbies(Gay) 
 17 min                  75
xhamster        
 2018-02-25 08:00:34 
I love crossdressing while have phone sex
I love crossdressing while have phone sex
 Amateur(Gay),BigCock(Gay),Crossdresser(Gay),Hunk(Gay),Masturbation(Gay),HDVideos,CrossdressingNewbies(Gay) 
 15 min                  90
xhamster        
 2018-02-21 12:00:44 
Tonight I get to be a really crossdressing slut
Tonight I get to be a really crossdressing slut
 Amateur(Gay),Crossdresser(Gay),Hunk(Gay),Masturbation(Gay),CrossdressingNewbies(Gay) 
 14 min                  66
xhamster        
 2018-02-17 04:00:10 
I love getting all dolled up in sexy womens clothes
I love getting all dolled up in sexy womens clothes
 Amateur(Gay),BigCock(Gay),Crossdresser(Gay),Latin(Gay),Masturbation(Gay),CrossdressingNewbies(Gay) 
 13 min                  60
xhamster        
 2018-02-11 07:00:32 
I crave big cock when I crossdress
I crave big cock when I crossdress
 Amateur(Gay),BigCock(Gay),Crossdresser(Gay),Hunk(Gay),Masturbation(Gay),HDVideos,CrossdressingNewbies(Gay),BigCockGay(Gay),GayBigCock(Gay),BigGay(Gay),GayCock(Gay),GayBig(Gay),FreeGayBigCock(Gay),BigCockGayFree(Gay),GayTube 
 15 min                  72
xhamster        
 2018-02-06 23:00:20 
I am all dressed up and ready to get fucked
I am all dressed up and ready to get fucked
 Amateur(Gay),Crossdresser(Gay),Hunk(Gay),Masturbation(Gay),HDVideos,CrossdressingNewbies(Gay),FuckedupGay(Gay),AllFreeGay(Gay),UpGay(Gay),Gayup(Gay),AllGayTube(Gay),GetGay(Gay),FuckedupGayTumblr(Gay) 
 13 min                  101
xhamster        
 2018-01-29 23:00:12 
I am such a gorgeous crossdressing slut
I am such a gorgeous crossdressing slut
 Amateur(Gay),BigCock(Gay),Crossdresser(Gay),Hunk(Gay),Masturbation(Gay),HDVideos,CrossdressingNewbies(Gay),GaySlut(Gay),CrossdressingGay(Gay),SlutGay(Gay),GorgeousGay(Gay),FreeGaySlut(Gay) 
 14 min                  220
xhamster        
 2018-01-25 07:15:53 
I want to take some hard cock while crossdressing so bad
I want to take some hard cock while crossdressing so bad
 Amateur(Gay),BigCock(Gay),Crossdresser(Gay),Hunk(Gay),Latin(Gay),HDVideos,CrossdressingNewbies(Gay),HardGay(Gay),GayHard(Gay),GayCock(Gay),GayCrossdressing(Gay),CrossdressingGay(Gay),BadGay(Gay),GayHardCock(Gay),HardGayTumblr(G 
 14 min                  60
xhamster        
 2018-01-21 07:00:43 
Watch me transform into a sissy girl
Watch me transform into a sissy girl
 Crossdresser(Gay),Hunk(Gay),Latin(Gay),Masturbation(Gay),HDVideos,CrossdressingNewbies(Gay),GaySissy(Gay),SissyGay(Gay),FreeGaySissy(Gay),FreeGayGirl(Gay),FreeSissyGay(Gay) 
 14 min                  86
xhamster        
 2018-01-17 07:00:37 
My cock gets hard as steel when I crossdress
My cock gets hard as steel when I crossdress
 Amateur(Gay),BigCock(Gay),Crossdresser(Gay),Hunk(Gay),Masturbation(Gay),HDVideos,CrossdressingNewbies(Gay),HardGay(Gay),GayCock(Gay),HardGayTube(Gay),GayHardCock(Gay),HardGayTumblr(Gay),CockGay(Gay),FreeGayCock(Gay),HardCockG 
 15 min                  64
xhamster        
 2018-01-16 07:00:37 
Come fuck my crossdresser ass in the kitchen
Come fuck my crossdresser ass in the kitchen
 Crossdresser(Gay),Hunk(Gay),Latin(Gay),Masturbation(Gay),HDVideos,CrossdressingNewbies(Gay),GayFuck(Gay),GayCrossdresser(Gay),AssGay(Gay),GayAssFuck(Gay),GayCome(Gay),GayCrossdresserTube(Gay),GayTubeFuck(Gay),FreeCrossdresserGa 
 14 min                  97
xhamster        
 2018-01-12 07:01:46 
Strip me down and give me that hard cock
Strip me down and give me that hard cock
 Amateur(Gay),Bareback(Gay),Crossdresser(Gay),Hunk(Gay),Latin(Gay),HDVideos,CrossdressingNewbies(Gay),HardGay(Gay),GayHard(Gay),GayCock(Gay),StripGay(Gay),GayHardCock(Gay),FreeHardGay(Gay),HardGayFree(Gay),GayDown(Gay) 
 14 min                  81
xhamster        
 2018-01-09 07:00:44 
My sissy fantasy is getting fucked while crossdressing
My sissy fantasy is getting fucked while crossdressing
 BlackandEbony(Gay),Amateur(Gay),Crossdresser(Gay),Hunk(Gay),Masturbation(Gay),HDVideos,CrossdressingNewbies(Gay),GaySissy(Gay),SissyGay(Gay),GayFantasy(Gay),FantasyGay(Gay),CrossdressingGay(Gay),FantasyGayTumblr(Gay),FreeSissyGa 
 15 min                  55
xhamster        
 2018-01-05 07:00:52 
This is my first time being photographed while crossdressing
This is my first time being photographed while crossdressing
 Amateur(Gay),Crossdresser(Gay),Hunk(Gay),Latin(Gay),Masturbation(Gay),HDVideos,CrossdressingNewbies(Gay),FirstTimeGay(Gay),FirstGay(Gay),GayCrossdressing(Gay),CrossdressingGay(Gay),FirstTimeBeingGay(Gay),GayTime(Gay),FreeFirstGa 
 14 min                  85
xhamster        
 2018-01-04 07:00:20 
I love getting all dolled up in womens clothes
I love getting all dolled up in womens clothes
 Crossdresser(Gay),Hunk(Gay),Masturbation(Gay),HDVideos,CrossdressingNewbies(Gay),LoveGay(Gay),AllFreeGay(Gay),FreeallGay(Gay),FreeGayLove(Gay),GayinLove(Gay),UpGay(Gay),InLoveGay(Gay),GayinYoutube(Gay),GayinClothes(Gay) 
 13 min                  82
xhamster        
 2017-12-31 07:00:31 
I love getting all dolled up in womens clothes
I love getting all dolled up in womens clothes
 Man(Gay),Crossdresser(Gay),Hunk(Gay),Masturbation(Gay),HDVideos,CrossdressingNewbies(Gay),LoveGay(Gay),FreeGayLove(Gay),GayinLove(Gay),UpGay(Gay),Gayup(Gay),InLoveGay(Gay),ClothesGay(Gay),GayinClothes(Gay),LoveGayTumblr(Gay) 
 11 min                  95
xhamster        
 2017-12-22 07:00:13 
I am crossdressing for the first time and its amazing
I am crossdressing for the first time and its amazing
 Man(Gay),BigCock(Gay),Crossdresser(Gay),Hunk(Gay),Interracial(Gay),HDVideos,CrossdressingNewbies(Gay),FirstTimeGay(Gay),GayFirstTime(Gay),FirstGay(Gay),AmazingGay(Gay),GayCrossdressing(Gay),CrossdressingGay(Gay),FirstTimeGayTub 
 14 min                  96
xhamster        
 2017-12-20 09:00:53 
I feel so much sexier when crossdressing
I feel so much sexier when crossdressing
 Men(Gay),Blowjobs(Gay),Crossdressers(Gay),Hunks(Gay),Masturbation(Gay),HDGays,CrossdressingNewbies(Gay),CrossdressingGay(Gay),FreeGayCrossdressing(Gay) 
 17 min                  110
xhamster        
 2017-12-18 04:00:07 
Dressing in white lingerie is so taboo and sexy
Dressing in white lingerie is so taboo and sexy
 Men(Gay),Crossdressers(Gay),Hunks(Gay),Masturbation(Gay),HDGays,CrossdressingNewbies(Gay),SexyGay(Gay),WhiteGay(Gay),GayWhite(Gay),GayTaboo(Gay),SexyGayTumblr(Gay),GayLingerie(Gay),SexyFreeGay(Gay),SexyGayWhite(Gay),FreeGayWhi 
 13 min                  94
xhamster        
 2017-12-15 08:01:17 
I need some alpha male cock in my crossdresser ass
I need some alpha male cock in my crossdresser ass
 Men(Gay),Crossdressers(Gay),Hunks(Gay),Masturbation(Gay),HDGays,CrossdressingNewbies(Gay),GayMale(Gay),GayCrossdresser(Gay),FreeMaleGay(Gay),GayCock(Gay),CrossdresserGay(Gay),AssGay(Gay),AlphaMaleGay(Gay),GayAlpha(Gay),GayMaleF 
 15 min                  67
xhamster        
 2017-12-12 07:00:47 
My first time crossdressing was so hot
My first time crossdressing was so hot
 Men(Gay),Crossdressers(Gay),Hunks(Gay),Masturbation(Gay),CrossdressingNewbies(Gay),HDGays 
 14 min                  59
xhamster        
 2017-12-07 00:00:34 
This red lingerie looks so good on my ebony body
This red lingerie looks so good on my ebony body
 Men(Gay),BlackGays(Gay),Crossdressers(Gay),Hunks(Gay),Masturbation(Gay),CrossdressingNewbies(Gay),HDGays 
 14 min                  106
xhamster        
 2017-12-02 23:00:13 
My first time as a crossdressing sissy was liberating
My first time as a crossdressing sissy was liberating
 Men(Gay),Crossdressers(Gay),Hunks(Gay),Masturbation(Gay),CrossdressingNewbies(Gay),HDGays 
 14 min                  66
xhamster        
 2017-11-30 07:01:17 
I just discovered crossdressing and it is so hot
I just discovered crossdressing and it is so hot
 Men(Gay),Crossdressers(Gay),Hunks(Gay),Masturbation(Gay),CrossdressingNewbies(Gay),HDGays 
 14 min                  57
xhamster        
 2017-11-29 06:00:15 
I want to bend over and get my crossdresser ass pounded
I want to bend over and get my crossdresser ass pounded
 Men(Gay),Crossdressers(Gay),Hunks(Gay),Latin(Gay),Masturbation(Gay),CrossdressingNewbies(Gay),HDGays 
 13 min                  82
xhamster        
 2017-11-19 12:00:13 
I picked my crossdressing outfit carefully
I picked my crossdressing outfit carefully
 Men(Gay),Crossdressers(Gay),Hunks(Gay),Masturbation(Gay),CrossdressingNewbies(Gay),HDGays 
 15 min                  64
xhamster        
 2017-11-16 14:00:48 
I want an alpha male the fuck my crossdressing ass
I want an alpha male the fuck my crossdressing ass
 Men(Gay),Crossdressers(Gay),Hunks(Gay),Masturbation(Gay),CrossdressingNewbies(Gay),HDGays 
 12 min                  63
xhamster        
 2017-11-14 20:01:16 
I want to bend over and take it in my crossdresser ass
I want to bend over and take it in my crossdresser ass
 Men(Gay),Crossdressers(Gay),Hunks(Gay),Masturbation(Gay),CrossdressingNewbies(Gay),HDGays 
 14 min                  64
xhamster        
 2017-11-10 08:00:33 
There is nothing wrong with crossdressing in lingerie
There is nothing wrong with crossdressing in lingerie
 Men(Gay),Crossdressers(Gay),Hunks(Gay),Masturbation(Gay),CrossdressingNewbies(Gay),HDGays 
 14 min                  65
xhamster        
 2017-11-06 07:00:13 
Watch me get all dolled up in white lingerie
Watch me get all dolled up in white lingerie
 Men(Gay),BlackGays(Gay),Crossdressers(Gay),Hunks(Gay),Masturbation(Gay),CrossdressingNewbies(Gay),HDGays 
 10 min                  68
xhamster        
 2017-11-02 05:01:14 
I am going to get my ass pounded while crossdressing
I am going to get my ass pounded while crossdressing
 Men(Gay),BigCocks(Gay),Crossdressers(Gay),Hunks(Gay),Interracial(Gay),CrossdressingNewbies(Gay),HDGays 
 14 min                  89
xhamster        
 2017-10-29 07:00:30 
Crossdressing in this red lingerie is making me so hard
Crossdressing in this red lingerie is making me so hard
 Men(Gay),BlackGays(Gay),Crossdressers(Gay),Hunks(Gay),Masturbation(Gay),CrossdressingNewbies(Gay),HDGays 
 17 min                  78
xhamster        
 2017-10-25 01:00:10 
I have never been so hard before
I have never been so hard before
 Men(Gay),Crossdressers(Gay),Hunks(Gay),Latin(Gay),Masturbation(Gay),CrossdressingNewbies(Gay),HDGays,Hard 
 10 min                  76
xhamster        
 2017-10-21 08:00:30 
I have some sexy new lingerie I want to try out
I have some sexy new lingerie I want to try out
 Men(Gay),Crossdressers(Gay),Hunks(Gay),Masturbation(Gay),CrossdressingNewbies(Gay),HDGays,IWant,NewLingerie,Newto,SexyLingerie,Sexy 
 11 min                  72
xhamster        
 2017-10-17 00:00:35 
I cant wait to try crossdressing out
I cant wait to try crossdressing out
 Men(Gay),Crossdressers(Gay),Hunks(Gay),Masturbation(Gay),CrossdressingNewbies(Gay),HDGays,ICant 
 17 min                  52
xhamster        
 2017-10-13 23:00:12