27 Results Found:


07.10.2017
Description: The sissy maid is cleaning the house but his mistress is interested in him servicing other needs. She wants to have her strapon cock sucked and his mouth has been very well practiced so he will do a good job. Hes also going to have to bend over and take it up the ass, another thing he has become very good at. Shes going to fuck him like a little bitch and its probably going to hurt but this naughty babe loves making a man hurt.

Model(s): Helena, Gilbert | Duration: 18min 46sec | Type: SD | Size: 274mb

Model(s): Helena, Gilbert | Site: StraponSissies.com | Category: Videos


22.07.2017
Description: Emilia turned on to the max when she realized she'd get the chance to use her rock hard dildo on sissy boy Gilbert and started things off by watching him giving her a strapon blowjob so that it would stuff into his tight sissy anus. The nasty dom bitch goes right to work with her rigid strapon dildo in tow and as their passions red hot she attacks his moist bitch boy ass with that steel hard strapon and destroys his sissy boy big meaty asshole.

Model(s): Emilia C, Gilbert B | Duration: 13min 55sec | Type: SD | Size: 202mb

Model(s): Emilia C, Gilbert B | Site: StraponSissies.com | Category: Videos


25.01.2011
Description: Gilbert was getting ready for his big meaty sissy asshole to get fucked crazy by Emilia and soon as they got that libido up She zeroed in on his gripping hot sissy ass. The poor fool took that thick meaty strapon so deep into his sweet raw bum that his howling scared the neighbors. She then banged that butt like a madwoman and soon she left him with nothing much left except a plundered brown eye.

Model(s): Emilia C, Gilbert B | Number of pics: 66 | Resolution: 1505x1000

Model(s): Emilia C, Gilbert B | Site: StraponSissies.com | Category: Pictures


18.11.2010
Description: Poor Gilbert must suffer the humiliation of nasty dom bitch Jaclyn as she whips out her rigid strapon dildo and with her horny passions up she intends on destroying some sissy boy moist tight ass. He loves a rock hard strap on dildo to bust open his tight helpless butt but he doesn't realize that she is bent on destroying his gripping hot sissy ass. As she dominates him she got real horny and unmercifully took that rock hard dildo and rammed it up his sweet raw bum totally humiliating him.

Model(s): Jaclyn, Gilbert | Duration: 15min 49sec | Type: SD | Size: 231mb

Model(s): Jaclyn, Gilbert | Site: StraponSissies.com | Category: Videos


02.11.2010
Description: Emilia is going to bust open a ripping sissy asshole if it's the last thing she does and getting hold of Gilbert and slamming that sissy's bunghole is just what she's going to do. She wants nothing short of a destroyed whiney boy ass for all her troubles and poor dude is going to get the worst of it. She got real horny and whipped out her steel hard strapon and went to work on his tight sissy anus. She banged that butt until that rigid strapon dildo almost melts from the fury.

Model(s): Emilia C, Gilbert | Duration: 14min 51sec | Type: SD | Size: 216mb

Model(s): Emilia C, Gilbert | Site: StraponSissies.com | Category: Videos


17.10.2010
Description: There was no escape for Gilbert ripping sissy asshole as the lusty submissive sissy tried to evade the wrath of Jaclyn steel hard strapon. She used that weapon to stuff it into his gripping hot sissy ass and soon she stood over his destroyed whiney boy ass and forced the sissy to engage in some filthy ass to mouth action. Never cross swords with her and her rigid strapon dildo or you might end up like him!

Model(s): Jaclyn, Gilbert | Duration: 13min 22sec | Type: SD | Size: 194mb

Model(s): Jaclyn, Gilbert | Site: StraponSissies.com | Category: Videos


03.09.2010
Description: Here comes redhead Jaclyn the nasty dom bitch who intends on slamming some tight hot sissy butt and none other than Gilbert is her target. She starts the sissy boy off by his giving her a strapon blowjob getting it all wet and slimey so it can squeeze on into that tight hot sissy butt of his. That rigid strapon dildo plows into that nasty hot ass or His and then she starts pounding that sissyboy's butthole until she totally owns it.

Model(s): Jaclyn, Gilbert | Number of pics: 43 | Resolution: 1505x1000

Model(s): Jaclyn, Gilbert | Site: StraponSissies.com | Category: Pictures


22.08.2010
Description: Gilbert is such a sissy boy on the stairs that he must have a tight sissy boy butt stuffed deep into his tight hot sissy butt and horny Emilia would like nothing better to do. The two of them got real horny and soon Irene was breaking out her rock hard dildo and heading straight for his sissy sweet raw bum. The horny cruel dominatrix whipped out that hard sturdy strap on and went to work. He was famous for doing some nasty sucking ass entombed strapon cock and after sexing things up he proved himself.

Model(s): Emilia C, Gilbert B | Duration: 15min 38sec | Type: SD | Size: 228mb

Model(s): Emilia C, Gilbert B | Site: StraponSissies.com | Category: Videos


21.07.2010
Description: Gilbert must suffer the humiliation of nasty dom bitch Emilia as she whips out her hard sturdy strap on and with her hormones boiled up she intends on destroying some sissy boy steamy sissy butt. He loves a steel hard strapon to bust open his big meaty asshole but he doesn't realize that she is bent on destroying his tight hot sissy butt. As she dominates him she turned on to the max and unmercifully took that massive strap on and rammed it up his nasty hot ass totally degrading him.

Model(s): Emilia C, Connor C | Duration: 14min 53sec | Type: SD | Size: 217mb

Model(s): Emilia C, Connor C | Site: StraponSissies.com | Category: Videos


13.07.2010
Description: Gilbert wanted to get his tight sissy anus banged by a hard sturdy strap on but when he made the mistake of getting Stephana's hormones boiled up he bit off more than he could chew. The slut tore into his moist bitch boy ass with that steel hard strapon and the sissy boy could barely breathe as Irene tore into his big meaty asshole and owned him. The action got even more furious as her rock hard strap on dildo almost broke in half pounding that ripping sissy asshole of his.

Model(s): Stephana, Gilbert | Duration: 14min 51sec | Type: SD | Size: 216mb

Model(s): Stephana, Gilbert | Site: StraponSissies.com | Category: Videos


18.05.2010
Description: Here's horny cruel dominatrix Jaclyn who is on the prowl for some gripping hot sissy ass and she's going to make sissy Gilbert a candidate by having him sucking her strap on cock to get ready for the destruction of his gripping hot sissy ass. Her hard sturdy strap on and rides that boy's nasty hot ass like a bucking bronco and after slamming that sissy's bunghole she reduces him to a cowering butt sissy slave who falls down and worships his mistress and her steel hard strapon.

Model(s): Jaclyn, Gilbert | Number of pics: 90 | Resolution: 1505x1000

Model(s): Jaclyn, Gilbert | Site: StraponSissies.com | Category: Pictures


11.03.2010
Description: Gilbert had the urge for a rigid strapon dildo to teach him a lesson and horny cruel dominatrix Jaclyn was just the teacher he wanted. She broke out her trusty rigid strapon dildo and decided to go to work on him as he started giving her a strapon blowjob to get it slicked up. Soon that steel hard strapon was stuffed deep into his tight sissy anus. The horny cruel dominatrix busted right through his tight hot sissy butt and soon the sissy boy was happy.

Model(s): Jaclyn, Gilbert | Duration: 25min 21sec | Type: SD | Size: 372mb

Model(s): Jaclyn, Gilbert | Site: StraponSissies.com | Category: Videos


23.02.2010
Description: Gilbert is waiting for a rock hard strap on dildo to slam into his big meaty asshole, he begs Emilia to own him. She obliges him by busting open his tight sissy boy butt and soon she was in total command of his gripping hot sissy ass. She got real horny and made super good use of her massive strap on and poor dude tried his best to take all that strapon in his nasty hot ass and not cry. Soon the nasty dom bitch was laughing with glee at the destruction her hard sturdy strap on had wrought.

Model(s): Emilia C, Gilbert | Duration: 14min 23sec | Type: SD | Size: 209mb

Model(s): Emilia C, Gilbert | Site: StraponSissies.com | Category: Videos


17.12.2009
Description: Jaclyn is hunting for some ripping sissy asshole and when she gets hold of Gilbert she gets that sexual passion up. She knows he needs to have his gripping hot sissy ass boned to the brim with a steel hard strapon and she humiliates the fool by stuffing one deep into his sweet raw bum and fucking him silly. She doesn't let up and the wild girl just fucked that transvestite butt ferociously and then made him blow her rigid strapon dildo.

Model(s): Jaclyn, Gilbert | Number of pics: 46 | Resolution: 1505x1000

Model(s): Jaclyn, Gilbert | Site: StraponSissies.com | Category: Pictures


13.12.2009
Description: Gilbert deserved to be banged that butt so he begged blonde Judy to whip out her hard sturdy strap on and do him right. Soon the scent of musky whiney boy ass filled the air as she pounded his gripping hot sissy ass like crazy as she used that massive strap on to mercilessly pound that moist transvestte ass of his. The nasty dom bitch just loves to get hormones boiled up and nothing satisfies her more than fucking a gripping hot sissy ass.

Model(s): Emilia C, Gilbert | Duration: 13min 3sec | Type: SD | Size: 190mb

Model(s): Emilia C, Gilbert | Site: StraponSissies.com | Category: Videos


19.11.2009
Description: Stephana is shmoozing around for some tight sissy anus to fuck and the horny cruel dominatrix is zeroing in on crossdresser Gilbert. She breaks out her hard sturdy strap on and soon she gets her passions red hot and starts him ready by sucking her strap on cock that gets her wet and ready. Soon the woman is banging his moist transvestte ass and the crossdresser takes all of that rock hard strap on dildo deep into his big meaty asshole that totally destroys him.

Model(s): Stephana, Gilbert | Duration: 13min 58sec | Type: SD | Size: 203mb

Model(s): Stephana, Gilbert | Site: StraponSissies.com | Category: Videos


15.11.2009
Description: Sultry Emilia is looking for her steel hard strapon so she can team up with crossdresser Gilbert and start pounding that sissyboy's butthole of his. She loves busting open a nasty hot ass and as the two get their hormones boiled up the girl gets busy on that tight hot sissy butt of his. Her steel hard strapon just destroys the sweet raw bum of the crossdresser and soon she's so thoroughly banged that butt that both of them collapse.

Model(s): Emilia C, Gilbert | Number of pics: 68 | Resolution: 1505x1000

Model(s): Emilia C, Gilbert | Site: StraponSissies.com | Category: Pictures


26.10.2009
Description: Watch as horny Meggy takes her rock hard strap on dildo and helps sissy Gilbert put on his makeup and then heads for his tight sissy anus. The nasty dom bitch has a fetish to bang some tight hot sissy butt on a regular basis and forces him to start giving her a strapon blowjob so that she can get that steel hard strapon all wet and slimey so she can start pounding that sissyboy's butthole of his. The nasty dom bitch then stuffs that tight hot sissy butt of his and destroys him.

Model(s): Meggy C, Gilbert | Duration: 14min 33sec | Type: SD | Size: 212mb

Model(s): Meggy C, Gilbert | Site: StraponSissies.com | Category: Videos


12.09.2009
Description: There was no escape for Gilbert tight crossdresser butt as the lusty submissive sissy tried to evade the wrath of Emilia rock hard strap on dildo. She used that weapon to stuff it into his gripping hot sissy ass and soon she stood over his anihilated sissy butt and forced the sissy to engage in some filthy sucking ass entombed strapon cock action. Never cross swords with her and her hard sturdy strap on or you might end up like him!

Model(s): Emilia C, Gilbert B | Number of pics: 79 | Resolution: 1505x1000

Model(s): Emilia C, Gilbert B | Site: StraponSissies.com | Category: Pictures


19.08.2009
Description: Jaclyn is prowling for some tight crossdresser butt and when she gets hold of Gilbert she gets that sexual passion up. She knows he needs to have his gripping hot sissy ass boned to the brim with a rock hard strap on dildo and she humiliates the fool by stuffing one deep into his nasty hot ass and fucking him silly. She doesn't let up and the wild girl just fucked that transvestite butt ferociously and then made him blow her hard sturdy strap on.

Model(s): Stephana, Gilbert | Duration: 14min 1sec | Type: SD | Size: 204mb

Model(s): Stephana, Gilbert | Site: StraponSissies.com | Category: Videos

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All models were at least 18 years old when they were photographed or videotaped

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