November 6, 2015
In Mommy's Slutty Outfit, a woman is shown walking along the street while sporting a miniskirt.
Published by Diaper Sissy at November 6, 2015
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Mommy’s Sexy Clothes

Your fetish for slutty clothing started at a young age and you know exactly what started it all. Your mother was always strutting around in tight skirts, low-cut tops, and high heels. Your friend’s parents would comment that the way she dressed made her look like a whore but you always thought she was the prettiest woman you’ve ever seen. Imitation is the sincerest form of flattery, isn’t it? So you think she would be happy to see how hot you look when you wear the same type of clothing she likes. Her legs seemed like they were a mile long in those miniskirts, and yours do too! The tight fabric shows off the lines of your tiny thong. That silky top feels so nice on your nipples. A streak of ruby red lipstick and fake eyelashes complete the look. You’ll never look as good as your mommy, but it’s your fetish to try! Mommy Lauren at 888-938-7382  
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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 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 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 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
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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 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
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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 her chubby baby lips. I brush her hair, sometimes curling it, and always put in a little ribbon bow. She says that her friends tease her but I tell her they’re just jealous of how pretty she is. That makes her blush bright red. She’s the best sissy a mommy could ever wish for! Want to talk to a mommy about your pretty clothes? I’m Mommy Lauren at 888*938*7382   
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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
A girl's gown is shown in the image, and it is very pretty in light pink.
Published by Diaper Sissy at October 25, 2015
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Perfect Sissy Boy

I got the chance to play with the most well behaved little sissy boy the other day! He told me that he just loved to be put in adult baby diapers. They got him so excited! Well knowing that, I made it my personal mission to have him make a big mess of a certain sort in his diaper for me. He listened to everything I said, and when I had him lay across my lap and give him a few hard spankings just because I can, he could hardly contain himself! It was so sweet how submissive he became as soon as I had the tape of his diaper fastened around his waist. After I took my time spanking his bottom, I had him slip his hand inside of his diaper and start playing with his little pecker. I love seeing it poke out from behind the diaper whether it is big or small. XOXO, Barb 888-430-2010
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