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This isn’t me in the picture, but I have done this with two of my ex-boyfriends (who I won’t name) and also one other guy who was dating my roommate at the time.
blackcuckoldress: razornick: That flailing cock is hypnotizing! Reminds me a lot of Wendy.  She likes my cock to stay hard whenever she straps on her dildo and uses my sissy hole like this.
Strapon training is cuckolding 101
It’s just not safe to travel with panties in your suitcase. He Was Detained and Sissified!
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Chelsea Poe, Mz Berlin
Unsuspectable Crossdresser - Submit your hot pics
Unsuspectable Crossdresser - Submit your hot pics I need some help running the blog, if you are interesting let me know :)
Yes, I know this isn’t a gif, but this was such a jawdropping “wtf?” for me that I had to share it. I’d hate to be in that man’s heels…
xrayeyesblue: Within every woman there is a domme waiting to be discovered, nurtured, worshiped and served.
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Gianna
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julieluvcock: ilovesuckintrannycock: what-is-chastity: Like seeing Sissy’s in What is Chastity? Try: Amateur Bondage What is a Strap On? Fetish Latex Cock and Ball Torture (CBT Would love to try this on! Would love to be forced to wear this
The best Strapon Pegging action on Tumblr Like seeing Sissy’s in What is Chastity? Try: Amateur Bondage What is a Strap On? Fetish Latex Cock and Ball Torture (CBT)
what-is-chastity: I told you it would not be easy. You beg for release but you really crave denial. Isn’t that so? The best Strapon Pegging action on Tumblr Like seeing Sissy’s in What is Chastity? Try: Amateur Bondage What is a Strap On?
littlemisschastity: Had a request for a shot of Little Miss Chastity going reverse cowgirl on Lady Sapphire’s strap-on. Also had a request for a pic of the sissy’s hole, fresh from a fucking. I thought the two looked good in GIF form, hope you like!
poly-qos-bdsm-cpl: Could not agree more but there is one difference. I only mount my sissies strap on on his face. I bought years ago a great leather face harness that holds a beautiful 10 inch black cock dildo that I fuck his face with. I have had him
shadwickc: womenwhopunish: Asian Femdom Boot Fetish Dominant Feet Femdom, Sissy and Cuckold Captions Strap-on Women You need staying power with this powerful domme. Whatever she decides on.
annabrighteyes: Found this on Pinterest on a sissy captions board with more repins than any of my stuff, haha. I love it but I think mistress would be horrified that she’s “the man” strap on or no haha
sweet-sissy-natalie: sugarkittysina: Reblog if you would like to fuck that (my) ass SugarKittySina you look so hot, Sina. But as I’m a sis like you I would have to strip on a strap on over my caged clitty *giggle* but you definitely look gorgeous
sissydonna: littlemisschastity: Had a request for a shot of Little Miss Chastity going reverse cowgirl on Lady Sapphire’s strap-on. Also had a request for a pic of the sissy’s hole, fresh from a fucking. I thought the two looked good in GIF form,
straponfuckers: Sissy strap-on male slave pegging team work That’s it, fuck him harder, fuck him like the sissy slut boy he is. All dressed pretty and sucking my cock like a good whore, taking it in the ass. Yes you are, you are our slut now
straponfuckers: Strap-on girls superior pegging teamwork on sissy`s hub I want to be that guy!
sissyemilystoner: your-sissy-cumslut: Come on pet, just pretend its my cock, its just how you’ve always imagined. A lot more real than the strap-on you were used too, I think you’ve love the taste of this more! i would suck that cock right between
thekestrelkid: The look on her face says it all. #sissy #anal #shemale #pegging #strapon #strap-on #ForcedFem #feminized #FemDom #fisting #FromBehind
thekestrelkid: Two sissies, one dildo. don’t worry, momma will take care of you!#sissy #anal #shemale #pegging #strapon #strap-on #forcedfem #feminized #fisting
thekestrelkid: Sissy’s need to be caged and fisted.#sissy #anal #shemale #pegging #strapon #strap-on #forcedfem #feminized #fisting
thekestrelkid: The look on her face says it all. Bitches like some cock.#sissy #anal #shemale #pegging #strapon #strap-on #forcedfem #feminized #fisting
sissylorraine: tusspuss: Sissyboy impaling herself on my big strapon The Alpha, including Her strap-on, in Domme all black… The sissy in all pink. As it should be!!!
