Sissy Training Archives - Page 2 of 5

April 20, 2016

A girl is sitting on the edge of the bed and wearing black lingerie underwear.

Published by Diaper Sissy at April 20, 2016

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Sissy Phone Sex

Are you a sissy boy phone sex lover? Don’t try and deny it now! I saw you wearing my stockings around the house when I wasn’t home. I noticed all of my lingere was a little stretched out and even had some hair on it. That hair certainly wasn’t from me, so it had to be you. Still denying it? Well that’s alright because I have proof. I set up a little nanny cam in my bedroom before heading off to work this morning and sure enough when I came home I checked it and you were on video going through my panty drawer! If that wasn’t bad enough I kept watching how you held up all my panties and bras to your body to see how you looked in them. And when that wasn’t enough you even went and put them on you! No wonder they’re all stretched out you’re a man putting on womens panties! You’re such a little slut for sissification phone sex aren’t you? #abdlmommy #sissyphonesex #sissytraining Ava 1-888-430-2010 Click HERE to chat with the phone sex mommies

January 18, 2016

In this image, a lovely girl stands in the room, wearing a lizabeth print dress and looking cute.

Published by Diaper Sissy at January 18, 2016

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Sissy Baby Fun

I love spending time with my favorite little sissy baby. Do you want to spend the day with Mommy? Lets get you dressed first. I pull out a pretty pink babydoll dress and you raise your arms so I can put it on you. I pull out a blonde wig and place it on you and a pink headband to match. You tell me you want to look pretty like mommy so I place some pink blush on your cheeks. I put on your shoes and socks and we’re ready to hit the mall for some shopping. Everybody is staring at us but you don’t care. You show off and twirl in your pretty pink dress. We go to the women’s department to pick out some new panties for you to wear over your diapers. We find a silky lace pink thong and you beg me to get it for you. You’re my favorite abdl-baby, so of course I do. We leave the mall and you can’t wait to try on your new panties. Liz 888-938-7382

November 1, 2015

A Sweet and Seductive Lady The woman was just partially clothed. And she has the appearance of a candy doll.

Published by Diaper Sissy at November 1, 2015

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Sissy Whorehouse Halloween

Oh man did I have the best halloween ever. There’s never a bad time to add humiliation phone sex to your holidays! This year I got to dress up my little sissy sluts and boy did we have some fun. Instead of a little haunted house we decided to turn our garage into a little Halloween sissy whore house. Instead of passing out candy we passed out blowjobs! My little sissy sluts all stood in a line on their knees as one guy after the other started coming up and pulling their cocks out to get sucked by my sissies. There was this really hung guy in a Zorro mask who was so hot he kept looking at me while my little sissy cock whore made sure his knob was well polished, bobbing it all the way down her throat. So many guys of all shapes and sizes started lining up. There were black guys with their big cocks, a couple of white guys and one Asian guy. My sissies were really put to work tonight at our Halloween sissy whorehouse. And that’s why I love sissy whore phone sex. Ava 888 430-2010

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

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 cock if you ever want to be able to take a real cock up that ass. Just imagine a real man grabbing onto those hips of yours and stuffing his big thick rod inside that hot little hole. Are you ready for a real cock? I’m going to keep pounding that ass of yours until you can take it like a good bitch. Stick that ass out for me so I can slap it . Are you ready to cum? You better be rubbing that little pecker between those legs of yours. Be a good little bitch and have some strap on training phone sex. Candy 888 430-2010

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 you every night to pound that little hole of yours. You’re going to become my pegging bitch while I teach you how to take cock. And when I think you’ve earned it, i’ll start bringing in real cocks for you to please. With some pegging phone sex you will soon be the biggest cock whore around. All of those holes of yours will be filled. As they should be. So do you think you have what it takes to be my sissy student? Can you get through my training? Well there’s only one way to find out isn’t there. Candy 888 430-2010

October 1, 2015

A Magnificent Dress by a Renowned Designer It was a very pleasant sight to behold, and the dress was looking so lovely.

Published by Diaper Sissy at October 1, 2015

Training My Sissy

I’ve got something special planned for you tonight, so why don’t you start by coming over here and sitting on the bed? I’m going to make you feel like such a pretty girl tonight, and you’re going to love me being your Mistress. It’s time to start the feminization process of your Sissy training; and I want to begin with getting you into these cute little panties and matching bra! So pull off your clothes.. and hurry up, or you’re going to get a hard spanking. Once you’re completely naked, I’m going to push you back and slide these panties onto you, and then the bra, both frilly and pink. I’ll slide some cute stocking up onto your legs, slowly pulling them all of the way up, then I’ll put you into a pair of hot pink high heels. After you’ve gotten used to walking in those tall stilettos, it will be time to put you in a short pink dress that ties behind your neck… Looking beautiful already, now it’s time for the fun stuff… xoxo Brittney 888-430-2010

September 10, 2015

The woman was wading while in black stockings and had a naked sex. She is currently seated on the sofa.

Published by Diaper Sissy at September 10, 2015

Categories

Small Penis Humiliation

Mommy is finally home from work and you know what that means! It’s time for mommy to have some fun with her abdl! We play lots of games together don’t we? Well today mommy is going to play her favorite! It’s called find the pee pee! That’s right you have a tiny little peeny weenie don’t you? Aww it looks so cute nestled between your legs. I bet mommy could find it if she started rubbing it like a little clitty huh? That’s exactly what it is! A little clitty for mommy to play with. Even pee pee is too big of a word because at least you can somewhat see it. Now yours can’t even do that can it? It disappears inside your tummy like an outtie belly button does it? Mommy can’t do anything with a little wee wee as small as that! Good thing you still have your tongue or you would be completely useless to mommy! With something as useless as that you deserve some small penis humiliation! Crissy 888 430-2010

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 those panties in my dirty hamper last night before taking a shower. Why would you have mommy’s panties in your drawer? Dirty ones at that! Do you like to sniff your mothers dirty panties? Or maybe you even like to wear them. What a poor excuse for a teenage son you are. Well you’re going to be in for a shock next time you open up that drawer young man. If you like wearing panties so much then I shouldn’t have to keep wasting money on those expensive boxers of yours. Adult baby Mommy is going to get rid of them all and fill that drawer with all sorts of frilly silky and even lacey panties that you love so much. That’s what you get for stealing my panties.

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

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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 strap. You can’t even hold a cup! Your dick is soooo small; I can’t even use it as a toothpick!!! I have to go and find a REAL man to satisfy my appetite. You know, someone whose dick is bigger than a hummingbird? A real man who knows what to do with his cock. Someone who won’t be a waste of my time. Someone who WON’T dribble out his cum. Someone who can keep it HARD for more than 2 minutes. Someone I don’t have to PITY fuck or FAKE my orgasms for. You need lessons to even think about fucking ME! The only thing your good for is fluffing my lovers, and being a good little sissy fag!