November 12, 2015
A girl in red panties is sitting in a chair while sporting them.
Published by Diaper Sissy at November 12, 2015
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Silk Panties

My new sissy is not doing well with his training. Of course, I have to insist that my sissy wears panties all the time, who knows when I will want to see my pretty little girl! However, he didn’t like the lacy ones that I got him, he insisted that they were itchy. I offered to buy him a different brand and different cuts so that he could find some lace panties that he really liked. Finally I gave up on the lace and decided that silk was the way to go. There was no way my new little sissy could resist some soft smooth silk against his little bum. It turns out, in fact, that he couldn’t. He wears his new silk panties all the time now and talks about how much he loves them all the time. So for any mommies out there that have trouble with sissy training, try silk panties! –Barbie <3 888-430-2010
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November 8, 2015
A pink skirt with frills that was maintained on the floor was quite attractive to both see and wear.
Published by Diaper Sissy at November 8, 2015
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All Pretty in Pink

Part of being a good little sissy is making sure to always listen carefully and perfectly obey everything that mommy tells you to do. You are not to ask questions or talk back. You must always remember that I am in charge here, and the better you behave for me, the sweeter I can be to you! I know that the ruffled pink dress I picked out for you might seem scary at first, but there is a first time for everything! You’ve never had to be submissive in this way to someone else before, especially a hot MILF who has been doing this for quite some time. Don’t worry baby, I will help you through it. I wouldn’t have picked you if I didn’t think you would make the best little sissy girl for me. I think once I get you all dressed up and ready to go out, that you will really come to enjoy the dresses and skirts! Don’t be shy! XOXO, Barb 888-430-2010
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November 5, 2015
A Mmmys Boy Adult Caption this is caption is relevant to adult users. And this is mature words.
Published by Diaper Sissy at November 5, 2015
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Obedient Sissy

My sissy and I went shopping earlier, and we got a lot of cute skirts for him to wear. I let him sit down on the bus ride home, with our bags at his feet, and I stood in front of him. The bus was very crowded, and there was a man behind me staring at my ass the whole time. I glanced back for a moment and saw him rubbing himself through his jeans. I got a very wicked idea and told him my sissy would gladly take care of that for him. He looked surprised, but my sissy looks like such a pretty girl that he didn’t even think about it. He unzipped his pants and pulled out a cock bigger than any my sissy has sucked before, and he stepped forward and thrust his meat deep into my sissy’s pretty mouth. My sissy started gagging, but the stranger didn’t pay any attention, and kept pumping down my sissy’s throat until his eyes were watering and his mascara started running. Finally the stranger came, zipped up his pants, and got off at the next stop. My sissy got a big bowl of ice cream when we got home for servicing that man so well. I’m very proud of him for being so obedient and sucking cock on public transportation. Barbie 888 430-2010 –Barbie <3 88-430-2010
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November 2, 2015
A Hot and Sexy Lady is standing on the floor, exposing her sexy boobs in a nude pose, looking hot and sexy.
Published by Diaper Sissy at November 2, 2015
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Public Diaper Humiliation

I got to talk to one of my callers tonight. He’s one of my favorite callers cause he’s a big diaper lover so you can bet that he really loves diaper lover phone sex. He called me earlier and was so excited to tell me about his day. You see he loves public diaper humiliation so he just got home from the store. He loves to go to this little ma and pa store since there’s this sweet little ol lady there who helps him every time. The first time he came in there and wore sweat pants over his diapers and always made sure the top of his diapers are sticking out. Not only did she see his diaper he drew even more attention to himself when he told her he needed to know where the adult baby wipes were because he made a mess in his diaper! She even had to give him the bathroom key so he could change his stinky diaper. He always has new and exciting stories for me when he calls. Public humiliation phone sex is just so hot sometimes. Crissy 888 430-2010
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November 1, 2015
A Domination of Role Playing The thoughts on the wall are all black in colour.
Published by Diaper Sissy at November 1, 2015
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Bend Over for Mommy

You know what always makes mommy soooo happy? I think you might have an idea of what inside that naughty little mind of yours.. When mommy has had such a long and stressful day, nothing would be enjoyed more than coming home to see an obedient and willing little sissy on their hands and knees on the bed, bent over and waiting for mommy to come stuff a big strap-on deep into your ass. I can see you look back at me from where you kneel. You look so submissive and sweet, waiting for me to come up behind you, put my hands on your hips and slide into you. Spankings are a given, of course! I love spanking that ass over and over again as I push in and out of your tight little hole. Leaving nice red hot hand prints on your butt-cheeks always brings a smile to my face. XOXO, Barb 888-430-2010
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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  
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October 27, 2015
A Sissy Barbie Girl the lady was dressed in an extremely deluxe version of a traditional white southern belle attire.
Published by Diaper Sissy at October 27, 2015
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Halloween for Sissies

It’s that time of the year! That enchanting smell that comes with fall weather, pumpkin spice lattes, and Halloween. What better opportunity is there for a sissy to go out on the town in the frilliest of gowns?  Imagine how much fun you can have just preparing for the event. Going to the store and finding a Barbie pink dress with a full skirt so that you can wear a diaper underneath with no one the wiser. A trip to the makeup counter for a bright lipstick to match. After that, returning home and trying it all on in front of your mirror, looking at what a beautiful sissy you are. That’s so exciting! I love hearing about sissies dressing up in girly clothes and hiding a diaper underneath. Maybe with lacy underwear over it! Are you planning on going out in your sissy wears? Call Mommy Laura and tell me all about it. Lauren 888*430*2010
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October 26, 2015
Back to school time is a special occasion for everyone. Back to school is still written on the blackboard in the image.
Published by Diaper Sissy at October 26, 2015
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A Fun Weekend with Mommy

Just this weekend, I finally followed through and taught my son how to suck his daddy’s thick cock so that he can be a good little sissy slut. First, I told him his daddy likes his girls to be very pretty, and that if he wanted to be like mommy, he would have to be very pretty too. I had him strip down and put on a pair of lacy, black panties and a pretty bralette. My baby boy’s pretty clitty is so little it fits nicely into the panties, even though I can see how hard he is. Then, I put him down on his knees and showed him how to unzip his daddy’s pants and tug down his boxers. Hubby was very hard at this point, and I knew he would not last long. Finally, my baby boy opened his mouth as wide as he could and popped his daddy’s head into his mouth. I put my hand on the back of his head and pushed him down on Hubby’s cock until he was gagging. He could only take four or five inches of it, but it didn’t matter because Hubby came as soon as he hit the back of my son’s throat. He spilled his seed right into his throat, but baby boy wasn’t ready and ended up spitting most of the sticky white cum onto the ground. I told him we couldn’t let any of it go to waste, so I pushed his head down and made sure he licked it all up from the floor. Then, to reward him, I gave him a long, deep kiss and squeezed his baby clitty until he came all in his panties. I loved tasting his daddy on him. Maybe we can start his sissy training soon. I hope one day my son grows up to be a good cock sucking sissy bitch just like his older brothers. — Barbie <3 888-430-2010
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October 25, 2015
The lady was dressed in a white western costume dress with panty, and she was showing off her ample assets.
Published by Diaper Sissy at October 25, 2015
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Sissy, Sissy

Well what have we here? A big whinny sissy boy! Do you really think that I will let you get away with this naughtiness? Bad behavior does not get rewarded! You will come over here right this minute. Stop that whining now. Where ever did you get that dildo from? Don’t try and pretend that I didn’t see you in the corner with your hand in your diaper, and playing with that big dildo. I saw it and now you will pay for it. Come here! Where did you get this dildo from? Oh my! Not the babysitter when she stayed last weekend with you. Now let me check that diaper first. Of course as I suspected you made a big mess in your diaper from playing with that pecker. You came all in it and now you need to be cleaned up.  But first things first, bend over my lap. Yes that is my leather paddle you see. I am going to use this leather paddle on your bare butt. Stop whining, sissy boy! I am going to show you where this dildo goes for you, sissy boy. Call Tawny (888) 430-2010
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