26 Results Found:


18.12.2024
Description: The hot blonde chick and her sissy lover have had many good times together and today is just another one of them. It all centers around the strapon cock that she wields with such confidence and skill. She warms his ass up with a little bit of thrusting and then she makes him bend over and take it from her thrusting. This is a beautiful, badass chick with a dominant streak and she’s more than happy to turn a man into a quivering little bitch for her pleasures.

Model(s): Emilia C, Gilbert | Duration: 11min 35sec | Type: SD | Size: 168mb

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


04.12.2024
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


27.11.2024
Description: Gilbert deserved to be fucked that ass so he pleaded with Judy to whip out her rigid strapon dildo rock his butt. Soon the scent of tight crossdresser bunghole filled the air as she pounded his tight hot sissy butt like crazy as she used that rock hard dildo to horribly pound that steamy sissy butt of his. The horny cruel dominatrix just loves to get hormones boiled up and nothing pleases her more than fucking a tight hot sissy butt.

Model(s): Stephana, Gilbert | Duration: 14min 36sec | Type: SD | Size: 213mb

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


23.11.2024
Description: Sultry Emilia is looking for her steel hard strapon so she can beat down on crossdresser Gilbert and start slamming that sissy's bunghole of his. She loves busting open a gooey funky butthole and as the two get their passions red hot the girl gets busy on that tight hot sissy butt of his. Her rock hard strap on dildo 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): Nora, Sebastian | Duration: 20min 32sec | Type: HD | Size: 447mb

Model(s): Nora, Sebastian | Site: StraponSissies.com | Category: Videos


26.10.2024
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


07.08.2024
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


27.07.2024
Description: Turn about is fair play as Emilia the horny cruel dominatrix took Gilbert's cock big time and then decided she wanted some of his tight hot sissy butt. After making him put on his sissy boy skirt and wig He fell to her by sucking her strap on cock so it would be lubricated enough to fuck his tight hot sissy butt. She put that hard sturdy strap on to work big time in his sweet raw bum and just continued pounding that sissyboy's butthole to the extreme.

Model(s): Emilia C, Gilbert | Duration: 16min 46sec | Type: SD | Size: 244mb

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


03.07.2024
Description: The frilly boy looks so good in his black stockings and his colorful outfit that you can’t really blame this girl for wanting to give the sexy sissy a hard banging. She has a nice red strapon cock between her legs and she intends on using it for a good butt humping just like the slutty sissy wants. His asshole has been craving penetration for weeks and he’s about to get the greatest gift from her. She’s going to show him what a real woman feels like when she gets fucked.

Model(s): Meggy C, Gilbert | Duration: 8min 20sec | Type: SD | Size: 120mb

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


21.02.2024
Description: Watch as horny Emilia takes her rock hard strap on dildo and helps sissy Ernest get dressed up 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 sucking her strap on cock 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 horny cruel dominatrix then stuffs that gripping hot sissy ass of his and destroys him.

Model(s): Emilia C, Gilbert | Number of pics: 85 | Resolution: 1505x1000

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


07.06.2023
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


19.04.2023
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


01.10.2022
Description: The sexy sissy can’t wait for his mistress to arrive. He needs to fuck his own asshole and he looks so pretty in his little dress and his sexy black stockings so it’s extra fun watching that plastic cock move into his asshole. He has great passion for a hard pounding and he takes this one pretty well. It gets a little rougher when his lady shows up and guides her schlong into his butthole and fucks him hard and deep. His takes every inch of cock up his bum.

Model(s): Stephana, Gilbert | Duration: 15min 12sec | Type: SD | Size: 222mb

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


11.05.2022
Description: The pretty boy is wearing a maid’s outfit and his mistress is approving of the job he has done around her house. He keeps things nice and clean and he’s going to get a reward for being such a good little maid. That reward is her big strapon cock sliding into his asshole and she is so ready to bang him. She’s going to stuff that butt of his with her big dick and she’s going to make him scream in pleasure. He loves being fucked and she loves doling it out.

Model(s): Helena, Gilbert | Number of pics: 68 | Resolution: 1504x1000

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


13.04.2022
Description: You can tell that’s a man wearing the colorful, loose fitting top but he sure does look like a sexy sissy. His asshole will probably be the ultimate pleasure zone for this strapon cock and the blonde chick intends on fucking him hard. She doesn’t care if she’s going to be sore in the morning because her pleasure is all that really matters. It’s going to be a big dick sliding inside him and it’s going to be so hot to watch.

Model(s): Emilia C, Gilbert | Number of pics: 76 | Resolution: 1505x1000

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


26.03.2022
Description: To prove his submissiveness, sissy Gilbert begs Stephana and starts giving her a strapon blowjob hoping she'll bust open his tight hot sissy butt and make him her slave. The rigid strapon dildo that she is weilding is just right for digging into a nasty hot ass and as soon as she's ready she starts pounding that sissyboy's butthole with glee. His tight sissy boy butt is soon destroyed leaving him nothing more than a cowering butt sissy slave.

Model(s): Stephana, Gilbert | Duration: 13min 1sec | Type: SD | Size: 189mb

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


15.01.2022
Description: That girl looks kind of tall and her nose doesn’t quite look feminine. Wait a minute, that’s not a girl that’s a sissy! The little sissy boy looks sexy in his outfit and he knows that’s what it takes to turn his lady on and once she’s turned on she always puts on her strapon cock to do some naughty fucking. She makes him suck on it to get it wet and then she introduces it deep into his asshole, taking him from behind for one hell of a lusty scene.

Model(s): Subrina, Gilbert | Number of pics: 79 | Resolution: 1505x1000

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


27.10.2021
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


06.10.2021
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. He’s also going to have to bend over and take it up the ass, another thing he has become very good at. She’s going to fuck him like a little bitch and it’s 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


24.07.2021
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


10.04.2021
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

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

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