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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.
This makes you wonder a lot of things. :)Â
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http://transeroticart.tumblr.com  said:J. B. Hopkins is an amazing artist who specializes in depictions of sissy boys.  Often the scenarios involve forced feminization, femdom, mild BDSM, pegging and other fetishes.  Beyond that we do not know anythin
badlab13: Ok sissy open wide while Mommy Dearest plugs your sissy hole with your butt Paci. Behave or I will not use lubricant and make you suck it first before pegging you!
youcanwearmypanties: Sissy gurl hubby has got pink lingerie to match his wife’s!! Meanwhile she is pegging his sissy gurl ass!!. Meet guys who like to dress up as chicks, get dressed up and play with their dicks. this is all possible at Cross Dressing
thekestrelkid: Sissy wedding night. What every gurl dreams about. Reblog if you do. #sissy #anal #shemale #pegging #strapon #wedding
sissydonna: sissy-maker: Sissy-Maker Where Boys become Girls Where Boys Will Be Girls I want to be pegged so bad
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
continuousstateofdesire: ezadaslave: ezada: Pegging My sissy slut Pushing a big strapon deeply into the ass of Her sissy slut is a pleasure of Lady Ezada Sinn who, by nature, has the right to do whatever She likes to do!
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. She is in Sissy Heaven!#sissy #anal #shemale #pegging #strapon #strap-on #forcedfem #feminized #fisting
thekestrelkid: Either in an evening dress or their wedding attire, these sissies love to be taken on all fours.#sissy #anal #shemale #pegging #strapon #strap-on #fisting
thekestrelkid: This is the way a bitch boy should be taken as you break him in. Turning him slowly into the sissy he really is.#sissy #anal #shemale #pegging #strapon #doggy
straponpegging: domyoursissycock: Pegging my sissy is the best! @sexysissy713 Another big fantasy me being dressed like a sissy while my wife fuckes me 😈
Take Mommy’s cock.
