24 Results Found:


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


18.03.2023
Description: The sissy bitch looks good in his little blonde wig and his sexy red dress and he’s looking forward to being dominated and taken by this gorgeous girl. She’s going to use his asshole like a playground. She’s going to fuck him deep and she’s going to fuck him hard and if he doesn’t like that big plastic cock ramming up into his asshole then he can go cry to someone else about it because she doesn’t give a damn.

Model(s): Stephana, Gilbert | Number of pics: 59 | Resolution: 1505x1000

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


25.02.2023
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


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


21.05.2022
Description: He would really like this sexy short haired chick to fuck his sissy ass with a strapon but she needs a little convincing. When she sees that he looks good in his little sissy clothes she gets kind of turned on and all of a sudden she wants to give his butt the banging it deserves. She pushes the toy inside him and then straps it around her waist so he can be given a proper fucking. It’s the kind of butt nailing that makes his dick hard and makes him want to cum.

Model(s): Meggy C, Gilbert | Number of pics: 71 | Resolution: 1505x1000

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


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


04.11.2020
Description: The sexy maid is working hard to keep his lady’s house clean and she wants to reward him for being such a sexy boy. In his little maid outfit he looks so feminine and she can’t help but be attracted to that. She loves how tight his ass is and how long and sultry his legs look in those beautiful stockings. She loves how he’s a total bitch for her strapon cock and she’s going to jam that thing up his asshole and make him scream.

Model(s): Sheila A, Gilbert | Number of pics: 71 | Resolution: 1504x1000

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


26.06.2019
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


30.03.2019
Description: Stephana is shmoozing around for some nasty sweet asshole to fuck and the horny cruel dominatrix is zeroing in on crossdresser Gilbert. She breaks out her rigid strapon dildo and soon she gets her hormones boiled up and starts him ready by sucking her strap on cock that gets her wet and ready. Soon the woman is banging his steamy sissy butt and the crossdresser takes all of that steel hard strapon deep into his tight helpless butt that totally destroys him.

Model(s): Nora, Sebastian | Duration: 15min 37sec | Type: HD | Size: 339mb

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


17.11.2018
Description: Meggy was on a bend to use her rigid strapon dildo and bust open a tight hot sissy butt and Gilbert is going to be her next victim. She breaks out that rock hard dildo and heads straight for his steamy sissy butt like it was a bullseye. The nasty dom bitch got her hormones boiled up by treating the sissy ass jerk and then stuffed his gripping hot sissy ass like it was a sausage casing. She loves to fuck that sissy ass and further degraded him by making him do some giving her a strapon blowjob tasting his own ass.

Model(s): Meggy C, Gilbert | Duration: 14min 38sec | Type: SD | Size: 213mb

Model(s): Meggy C, Gilbert | 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

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

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