December 25, 2018
He wears pink clothing and the Swedish Diaper.
Published by Diaper Sissy at December 25, 2018
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Diaper Check for a Cuckold Husband

Do I smell something stinky? You went poopy in your diaper already, little diaper sissy? Well, shuffle yourself over here to I can give you a diaper check, see if that horrible smell really is you. I don’t care that my new boyfriend is here, I already told him about how you were my husband before, but you were horrible at it, so I had no choice but to turn you into my diapered sissy baby! So you are going to walk on over here, get your diaper checked, and […]
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December 6, 2015
Published by Diaper Sissy at December 6, 2015
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MILF sex

  “Oh you fuck me so good.” Jamming that large dick; into my hot pussy. Oh these young men, who could ask for more? “Fuck yeah give it to me.” They can go forever and with a few words you can command them to do whatever your desire may be that day. Mommy is feeling very nasty and naughty and wants all her favorite men. With some discipline and instruction they will be fantastic lovers for the rest of their lives. But I get to have them all first. I […]
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December 6, 2015
A Sexy Girl is bathing in the bathroom, holding the scrib and looking hot.
Published by Diaper Sissy at December 6, 2015
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Extreme Fetish Phone Sex

Hi there extreme fetish phone sex lovers! My name is Crissy and they don’t call me the queen of extreme fantasies for nothing. I don’t care how dirty, raunchy, or twisted you think your fantasy is because nothing surprises me anymore. I’ve seen it all and done it aIl and I’m always up for something new, wild and crazy. Maybe you’re one of the ones who need a mommy? Or maybe you’re just a cuckold looking to talk about why your wife brings home other men to fuck her in […]
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November 12, 2015
He is a handsome man wearing a black clothing and wearing makeup.
Published by Diaper Sissy at November 12, 2015
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Forced To Be Pretty

You’re in big trouble now! Mommy Lauren caught you in the bathroom, playing with a lipstick she had left on the counter. She had always thought you were a big sissy and now she knows for certain. She’s not going to let you off the hook so easily. Mommy Lauren tells you to sit down on the toilet and stay still, she’s going to make you so pretty. She takes the lipstick out of your hand and tells you to pucker your lips. She applies a thick layer of hot […]
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October 29, 2015
The lady had a pair of sexy bosoms and was dressed in a western attire.
Published by Diaper Sissy at October 29, 2015
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Strap On Training

I think it’s about time for some good ol fashioned pegging phone sex. You lubing up that ass for me you little pegging slut? Mmm I’m going to stand behind that little ass of yours and put on my nice thick strap on. It’s the big black one just like you like it. I’m going to rub my big mushroom head all over that little puckered hole of yours. Are you ready for my cock? This is your training you little slut. You need to learn how to take my […]
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October 27, 2015
a pair of sissy pants in pink and white The lady was dressed in a frilly sissy panty that was pink and white in color and did not have any designs on it.
Published by Diaper Sissy at October 27, 2015
Categories

Dressing Up My Little Baby

My little boy is so much better as a sissy in a dress. Brian turns into Briana like magic when I slip him into a lacy skirt and top. Briana squeals with delight at anything pink and loves to play with mommy’s makeup. I see how Briana looks enviously at my painted nails, but I can’t let her use my nail polish on her own fingers like she wants- she would make such a mess! My makeup is fine though. She’s darling with a bit of barbie pink lipstick on […]
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October 7, 2015
A Sissy Pegging woman can be seen standing in front of a man while she is pegging him while wearing the sex porn toy.
Published by Diaper Sissy at October 7, 2015
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Sissy Pegging Phone Sex

If you have any lube I suggest you use it now! I want you to bend over for me and spread em. It’s about time for some strap-on phone sex! Being a closet fag such as yourself, you don’t have many options as far as sissification training, so I’ve decided to take a step and be your guide. My strap on is going to open up that little ass of yours so that it’ll be taking all sizes of cock in no time! I’ll use my big black strap on […]
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September 6, 2015
A Hot Girl is in a nude pose and she appears to be hot and sexy.
Published by Diaper Sissy at September 6, 2015
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Mommy’s Dirty Panties

Well what do we have here? I was just about to finish putting your laundry away like the caring mother I am. But then I got to your underwear drawer and I was in for a surprise. I moved some of your briefs to the side to make more room when the back of my hand brushed up against something silky. I closed my fingers around the fabric and low and behold there are my pink panties I wore last night. I’m certain this isn’t a mistake because I put […]
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August 22, 2015
A Nude Ava Lady is posing for the photographs while sporting a stunning black attire.
Published by Diaper Sissy at August 22, 2015
Categories

Cuckold Sissy Hubby

I bet you think your dick is great… well its NOT! It’s a tiny, little pee pee, and you are a pathetic little cuckold bitch! I’ve eaten fries BIGGER than your puny little pecker. And I KNOW you touch it a lot. There you are diddling your dick in the corner, how PATHETIC!!! But what I can’t understand is how you find the fucking thing! What do you use for a jock strap? A thimble and some thread? Oh wait… you have to be a jock to use a jock […]
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