Sissy PhoneSex Archives - Page 4 of 8

September 29, 2014

Published by Madison at September 29, 2014

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This hurts me more than it hurts you

I caught you looking up my skirt again when I was babysitting. I told you last time that you would be punished. I am a woman of my word. I am gonna put you in diapers and dress you up as my little girl. That’s right…put you back in diapers. I force you out of your clothes and into a diaper and plastic pants. I put a pink dress on you and pink panty-hose. You look absolutely ridiculous. I tease you and make you use your diaper. Then, I make you sit in it. You keep sniffling and crying. I give you a big pacifier to shut you up.You have never seen my backroom…today is the day. I have an entire nursery just for you to spend the day in. It doesn’t matter what you say, you will stay in this dress until your mommy comes to pick you up. As a matter of fact, If you keep talking, I’m going to put your pictures on facebook and call some of my friends over to tease you too. Oh, now you will be quiet. I thought so. I am the babysitter from hell and I don’t take any excuses. This should teach you a lesson on looking up skirts. Rachel 888.430.2010

June 12, 2014

Published by Madison at June 12, 2014

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Today I think I’m in the mood for some sissifacation phone sex. I love getting sissy calls. They’re just so submissive and cute! Plus the fact that they let me dress them up in any cute little outfit I desire doesn’t hurt either! Sometimes I can’t even decide what I want to put them in! So so many choices. Everything from garters, stockings, panties, lace panties, latex, rumba panties, dresses, skirts, short shirts, boots, heels, the list is endless! Sometimes the fun comes from just picking something out! What does my sissy want to wear today? Tell Mommy Ava so she can get your outfit ready for you. Maybe after we dress you up we can take a trip to the mall to show off your new outfit? I’m sure everyone would love that! It’s just one of the things that gets me excited about sissy phone sex. Ava 888*430*2010

January 24, 2014

Published by Madison at January 24, 2014

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“So you want a taste of Mommy’s milk?”

“So you want a taste of Mommy’s milk?” Well then my darling Aby, you say you been good and been following mommy’s direction. But is that so? Now, now you can’t keep lying to mommy. You know what will happen if you keep lying? Mommy will deprive you of this luscious tasting milk. I know you have been wanting to feed now, haven’t you? Well too bad.. You been such a naughty Aby! You are simply restricted from tasting mommy’s milk. Too bad for you, you already know that when your sucking on mommy’s huge nipples it gets mommy nice and wet. That’s right…. Maybe then you’ll learn to behave and be a good baby Aby. Mommy Lauren 1*888*430*2010

November 5, 2013

Published by Madison at November 5, 2013

Ass Training Sissies

I love ass training sissies. Although I have many in my care, I especially enjoy the ones I have from the very beginning. Being able to train them through from taking a finger, all the way to a 10 inch strap on is just so much fun. When a sissy comes to me they are usually very nervous. They know what they want but are sometimes embarrassed or ashamed to admit it. I take them in my care and treat them gently, knowing that I’ll have them begging for more soon enough. After I get them into matching panties and bra and a pretty dress, I get their training started. I always start them with a finger, usually holding them over my lap and slowly sliding down their panties so I can caress my sissy’s ass with one hand as I rub their hole with a lubed finger. I push my finger in slowly, massaging inside sissy to ease them open more. After a while I push in a second finger, then a third. By this point, my sissy is always moaning and rubbing against my lap. They rock their hips matching my thrusting fingers. From fingers we move on to various sized plugs. I love watching my sissies squirm as I maneuver the toys inside them, starting with the smallest. They of course learn to love each one and in fact crave more. Often my sissy will make a big creamy mess on my lap while I pump a toy inside them. And then in no time at all my sissy is ready to take my strap on like a good sissy should. When it’s sissy’s special first time I dress them in the prettiest dress I can find with a new panty and bra set. I let them suck my strap on first, taking it deep in their throat like a good sissy. She rubs her big sissy cock while she sucks me. Then I bend her over and pull her panties to the side, squeeze a glob of lube down her crack and rub it against her hole with my strap on. I have my sissy spread herself open for me so I can push the tip into her tight little hole. I can tell it’s hard for her to hold her cum as my strap on pushes further in. Slow steady pumps at first, turning into deeper harder thrusts, making my […]

September 3, 2013

Published by Madison at September 3, 2013

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Teaching Sissy

When the doorbell rang my sissy shot out of her seat and scurried to the door, standing to the side, her eyes darting between me and the door. She folded her hands over the front of her dress and took a deep breath as I opened the door. Standing behind the door was Mr. Grant. Mr. Grant is a very dear friend of mine and has always been a regular guest as my house. You see, he has a great appreciation for my sissies, ABies, and pets. When I invited him over to break in one of my newest and sweetest sissies he accepted enthusiastically. My sissy had gone through all of my basic training. When we’d begun she was actually quite resistant. She’d insisted that she was a man, a true red blooded man, however it wasn’t long before she was begging for the next plug size up to be inserted into her tight pussy. Today would be her first experience with a real man, and I couldn’t be more proud hehe. Like a good sissy, she led Mr. Grant into the sitting room where she served him a drink and sat politely next to him. “Now sweetie,” I said, “Mommy’s gonna show you just what to do and then you’ll do the same thing, mmkay.” With that said I unzipped Mr. Grants pants and reached in to pull out his growing cock… Mommy Liz 888-430-2010

August 22, 2013

Published by Madison at August 22, 2013

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Kidnapped into Sissy Hood

You stand on the corner waiting for the cab to take you back home you are just so tired from all the shopping you had to get done before the party tonight thinking to yourself what made you plan this party tonight of all nights.So rushed and you don;t like being rushed.The cab pulls up and you start to get in but dam already someone was in there they looked at you and smiled said that you could share the cab with them so in you get. She opens her purse and pulls out a bottle and offers you a drink thinking to yourself i am thirsty big time so you reach and take a drink it burns as it hits the back of your throat,but no matter still felt good and wet.You look over and the lady smiles and you think to yourself she is kinda of pretty in her own unique way and she did have a beautiful smile.He started to relax and enjoy the ride home oh yes home he was so looking forward to being home.Getting things ready for the huge party your throwing tonight.Then you start to drift off your head nods back and forth try as you might your eyes would not stay open finally giving in the cab driver has the address so no matter he will wake me just so very tired.Not a sissy not a sissy that is what wakes you when you finally become fully awake you look down and there you have on this outfit its a girl’s outfit you touch your head what the fuck i have on a bonnet too.I am no dam sissy i am a man then the voice speak out of the shadows and says just keep telling yourself that your not a sissy. Minnie 1.888.430.2010