roleplay Archives - Page 4 of 23

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

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

October 12, 2015

A girl is punishing her boyfriend, and a man apologises to her, and the girl is using sexy products.

Published by Diaper Sissy at October 12, 2015

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Naughty Diaper Sissy

My sissy baby likes to pee while I change him. As soon as I take off his soiled diapers, he pisses from his little sissy clitty, and I am tired of it. Today, I showed him what it felt like. I took off his diaper earlier, and when he started to pee, I grabbed his pee-pee and angled it up, so his piss sprayed all over his chest and face. He was very surprised, but not as surprised as he was when I took him off the changing table and set him on the ground. I took off my jeans, spread my legs, and lowered my clean, shaved pussy onto his lips. “Lick,” I told him, and he did. My little sissy fag is very good at licking my pussy, but his punishment wasn’t over. I shifted down just slightly and said, “Drink.” He was very surprised, but then he felt my piss start to drip into his throat. He sputtered, but I pinched his nose shut so he had no choice but to drink. He swallowed all of his mommy’s piss, and then kept licking my dirty pussy until I squirted all over his face, and then he drank that up too. He may be rude sometimes, but my little diaper sissy is very obedient. — Barbie <3 888-430-2010

October 9, 2015

A girl is lying in bed, exposing her sexy boobs and looking lovely.

Published by Diaper Sissy at October 9, 2015

Categories

Mother May I

Are you stroking your cock right now? You are? I didn’t tell you you could touch yourself now did I? Let me make something real clear right now. You’re about to experience the most intense orgasm denial phone sex you’ve ever had. And when you’re with me, I am in control. Your cock is my play thing. A simple object for my amusement and I will use it any way I see fit. You will crave release like a person would crave water in hell. Your balls will be blue while I tease and deny you of the pleasure of cumming. I will get you so close to the edge. So much pleasure that you can’t even think straight your head will be so dizzy with desire. And then, right when you’re about to reach that edge, I’ll stop. I told you I like to tease. And cumming is something you’re going to have to earn if you’re with me. So are you up for some extreme tease phone sex? Crissy 888 430-2010

September 27, 2015

A Nude Breast Nipple lady is sitting on the bed, showing off her nude boobs while wearing a sexy porn toy. The man is also nudely lying on the bed.

Published by Diaper Sissy at September 27, 2015

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Seductress Mommy Candy

I am 36 and what I love best is seducing a man much younger than me. You will grow to love everything there is about fantasy milf phone sex. It’s one of the hottest experiences you’ll ever have! I love stealing the virginity of a young boy because virgins are so cute and very eager to please! My neighbor has a gardener who just turned 18 so I told her I needed some yard work done. I just wanted to have him all to myself. When he came over I explained that I had always been watching him through my hedges with his shirt off mowing my neighbor’s lawn. He said between his classes and doing yard work to pay for his college, he just hasn’t had time for a girlfriend. So cute. I took him to my bed and told him that he never has to worry anymore about getting laid because I’m going to pay him to do a little plowing for me if you catch my drift. Let’s hope he loves fetish phone sex as much as I do! Candy 888 430-2010

September 13, 2015

Boy Sissy Sex The boy was dressed in a sissy outfit with high-heeled slippers and tights.

Published by Diaper Sissy at September 13, 2015

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Pretty Little Diaper Sissy

I am a loving, nurturing MILF. I do not like to have to repeat myself or raise my voice. Unless in a sexy role play, my typical demeanor is one that commands obedience and a submissive attitude. The perfect little sissy would know their place and acknowledge my full dominance over every aspect of their life without me ever having to utter a word. That is a tell-tale sign of a perfectly trained sissy slut. When mommy comes home from a long day and is tired, do you think she wants to have to worry about wiping down the kitchen before bed? No! She most certainly does not. Now, a good little sissy knows right away how mommy looks when she is tired and should be a good pet and get right to cleaning up without having to be told! You make it spotless while mommy sinks into a nice, hot bubble bath and relaxes for the night. After all, doing my bidding is why you are here! XOXO, Barb 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.

September 6, 2015

Wearing a pink dress, a fetishistic back girl flashes her bare butt.

Published by Diaper Sissy at September 6, 2015

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Be Mommy’s Perfect Sissy

It is so nice when I have a good little submissive to play with however I see fit. When they do not talk back or fight the things I say, I am one happy MILF. I have a big, lonely house. One thing I have been wanting to get into the house lately is a pretty little sissy girl to do everything I say without giving me any lip! I have all sorts of plans for her, mainly letting her know that no matter what, mommy is in charge! When I hide that cock inside of an adult baby diaper, you had better not be surprised! You knew this was coming when you signed up wanting to be my perfect little sissy. I will be so good to you as long as you are good to me as well! I promise we will have such fun changing your diaper when it is messy, getting you all dressed up and looking pretty each and every day, and taking you out to hang with all of my friends! XOXO, Barb 888 ** 430 ** 2010

August 29, 2015

A Boob Sex with a Nude Lady, who is dressed in bikini drees.

Published by Diaper Sissy at August 29, 2015

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Cuckold Sissy Phone Sex With Mommy Candy

Are you looking for a sexy MILF mommy to take care of you? Are you an adult baby in search of adult baby phone sex? Do you fantasize about fucking your hot mom? I’m Mommy Candy and I love all things taboo. I love being a mommy to my sons and all their friends. I also love taking care of adult babies and being a cuckold mommy. I have a soft spot for all my sissy baby and sissy sluts! I love dressing you up and parading you in front of all my boyfriends. Sissy training is one of my specialties and turning you in to a cuckold sissy is my ultimate goal. No matter what your mommy fantasy is, I’m here to fulfill all your dreams. I love talking to all of you and taking care of your needs. So what do you need from mommy? Call me in the month of September and I’ll give you five free minutes to get to know me. We can share our dirty fantasies and play out all of our desires. This special may not be combined with upsells or any other specials.