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                  102
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                  222
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                  82
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                  111
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                  65
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 
Dressing up like a women is so super hot
Dressing up like a women is so super hot
 Men(Gay),Crossdressers(Gay),Hunks(Gay),Masturbation(Gay),CrossdressingNewbies(Gay),HDGays,Likea,SoHot,Dressingup,SuperHot,HotWomen,Super,Dressing 
 16 min                  71
xhamster        
 2017-10-12 23:00:10 
I am looking forward to taking some cock while crossdressing
I am looking forward to taking some cock while crossdressing
 Men(Gay),Crossdressers(Gay),Hunks(Gay),Latin(Gay),Masturbation(Gay),CrossdressingNewbies(Gay),HDGays,Looking,Taking 
 17 min                  61
xhamster        
 2017-10-02 07:00:08 
I want you to watch my first sissy crossdresser adventure
I want you to watch my first sissy crossdresser adventure
 Men(Gay),Crossdressers(Gay),Hunks(Gay),Latin(Gay),Masturbation(Gay),CrossdressingNewbies(Gay),HDGays,IWant,IWatch,Sissy,First 
 14 min                  78
xhamster        
 2017-10-01 01:00:20 
I like getting fucked rough while crossdressing
I like getting fucked rough while crossdressing
 Men(Gay),Crossdressers(Gay),Hunks(Gay),Masturbation(Gay),CrossdressingNewbies(Gay),HDGays,GettingFucked,Rough,Getting,Fucked 
 15 min                  78
xhamster        
 2017-09-29 09:00:24 
Nothing gets my cock harder than crossdressing
Nothing gets my cock harder than crossdressing
 Men(Gay),Crossdressers(Gay),Hunks(Gay),Masturbation(Gay),CrossdressingNewbies(Gay),HDGays,Harder 
 15 min                  79
xhamster        
 2017-09-26 03:00:18 
This sexy white lingerie really suits me
This sexy white lingerie really suits me
 Men(Gay),Crossdressers(Gay),Hunks(Gay),Masturbation(Gay),CrossdressingNewbies(Gay),HDGays,ReallySexy,WhiteLingerie,SexyLingerie,SexyWhite,White,Sexy 
 15 min                  88
xhamster        
 2017-09-21 14:00:11 
Watch me turn myself into a sissy girl
Watch me turn myself into a sissy girl
 Men(Gay),Crossdressers(Gay),Hunks(Gay),Masturbation(Gay),CrossdressingNewbies(Gay),HDGays,SissyGirl,WatchMe,Sissy 
 13 min                  72
xhamster        
 2017-09-21 02:00:12 
Crossdressing in white lingerie makes my black cock so hard
Crossdressing in white lingerie makes my black cock so hard
 Men(Gay),BlackGays(Gay),Crossdressers(Gay),Hunks(Gay),Masturbation(Gay),CrossdressingNewbies(Gay),HDGays,MyBlackCock,WhiteLingerie,BlackLingerie,HardCock,WhiteCock,WhiteBlack,BlackCock,Hard,White,Black 
 13 min                  66
xhamster        
 2017-09-19 07:00:39 
I want to be bent over and fucked while crossdressing
I want to be bent over and fucked while crossdressing
 Men(Gay),Crossdressers(Gay),Hunks(Gay),Masturbation(Gay),CrossdressingNewbies(Gay),BentOverandFucked,BentOverFucked,IWant,Fucked 
 14 min                  65
xhamster        
 2017-09-14 08:00:31 
I cant wait to put on this hot little lingerie set
I cant wait to put on this hot little lingerie set
 Men(Gay),BigCocks(Gay),Crossdressers(Gay),Hunks(Gay),Masturbation(Gay),CrossdressingNewbies(Gay),HDGays,ICant,OnSet,HotLingerie 
 16 min                  58
xhamster        
 2017-09-11 07:00:26 
Crossdressing is a whole new sexual experience for me
Crossdressing is a whole new sexual experience for me
 Men(Gay),Amateur(Gay),Crossdressers(Gay),Hunks(Gay),Masturbation(Gay),CrossdressingNewbies(Gay),HDGays,ForMe,Sexual,Experience 
 15 min                  49
xhamster        
 2017-09-06 07:00:11 
My tight crossdresser ass is ready for some cock
My tight crossdresser ass is ready for some cock
 Men(Gay),BigCocks(Gay),Crossdressers(Gay),Hunks(Gay),Masturbation(Gay),CrossdressingNewbies(Gay),HDGays,TightAss,MyAss,CockAss 
 12 min                  40
xhamster        
 2017-09-02 08:00:24 
Crossdressing just gets my cock so rock hard
Crossdressing just gets my cock so rock hard
 Men(Gay),Crossdressers(Gay),Hunks(Gay),Masturbation(Gay),CrossdressingNewbies(Gay),HDGays,RockHardCock,RockHard,HardCock,Hard 
 17 min                  79
xhamster        
 2017-08-26 10:00:52 
I am such a pretty little crossdressing slut
I am such a pretty little crossdressing slut
 Men(Gay),Crossdressers(Gay),Hunks(Gay),Masturbation(Gay),CrossdressingNewbies(Gay),HDGays,PrettyLittle,Pretty,Slut 
 13 min                  80
xhamster        
 2017-08-24 01:01:29 
I love dressing up like a beautiful woman
I love dressing up like a beautiful woman
 Men(Gay),BigCocks(Gay),Crossdressers(Gay),Hunks(Gay),Masturbation(Gay),CrossdressingNewbies(Gay),HDGays,LikeaWoman,Likea,Dressingup,ILove,BeautifulWoman,BeautifulLove,Dressing,Beautiful,Love 
 13 min                  55
xhamster        
 2017-08-20 07:00:34 
I want to get fucked in my tight ebony sissy ass
I want to get fucked in my tight ebony sissy ass
 Men(Gay),BlackGays(Gay),Crossdressers(Gay),Hunks(Gay),Masturbation(Gay),CrossdressingNewbies(Gay),HDGays,TightEbonyAss,IWant,TightAssFucked,InMyAss,EbonyAssFucked,FuckedinAss,TightAss,Sissy,EbonyAss,MyAss,EbonyFucked,InAss,AssFu 
 15 min                  76
xhamster        
 2017-08-17 07:00:58 
I want to take some hard dick dressed as a sissy
I want to take some hard dick dressed as a sissy
 Men(Gay),BigCocks(Gay),Crossdressers(Gay),Hunks(Gay),Masturbation(Gay),CrossdressingNewbies(Gay),HDGays,IWant,HardDick,Sissy,Dressed,Hard 
 14 min                  95
xhamster        
 2017-08-12 20:00:50 
Womens clothes are so much sexier
Womens clothes are so much sexier
 Men(Gay),BigCocks(Gay),Crossdressers(Gay),Hunks(Gay),Masturbation(Gay),CrossdressingNewbies(Gay),HDGays,Clothes 
 14 min                  86
xhamster        
 2017-08-11 07:00:32 
I love getting my sissy ass pounded while crossdressing
I love getting my sissy ass pounded while crossdressing
 Men(Gay),Bareback(Gay),BigCocks(Gay),Crossdressers(Gay),Hunks(Gay),CrossdressingNewbies(Gay),HDGays,ILove,Sissy,AssLove,Pounded,MyAss,Getting,Love 
 17 min                  68
xhamster        
 2017-08-07 07:00:28 
I am dressed like a sissy and ready to take some cock
I am dressed like a sissy and ready to take some cock
 Men(Gay),BigCocks(Gay),Crossdressers(Gay),Hunks(Gay),Masturbation(Gay),CrossdressingNewbies(Gay),HDGays,Likea,Sissy,Dressed 
 12 min                  63
xhamster        
 2017-08-03 07:00:15