SIssy Training Phone Sex - Phone Sex Kisses

December 29, 2014

Published by Madison at December 29, 2014

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Caught You!

So you had no idea I was coming home early. You had no idea that I was going to catch you today. You really didn’t think I would notice you wearing my panties? Of course I noticed. Now, you are in trouble! No, you keep those panties on. You can wear them all night over that pamper. Oh, You didn’t think I knew about that either. Oh, I did. You know you are no good at keeping secrets from me. It’s alright…. I have the perfect plan. I’m going to put this little dress on you and make you drink out of this ba-ba. I have a bib for you and tight little panty-hose to put on you so your pamper is nice and tight on your bottom. This way, when you fill up your diaper, you will definitely feel all the warmth and how soggy you made them. You get to sit in those pampers until I decide its time to change you. It may be a long, wet night for you. Then, I’m gonna dress you up in this cute little outfit. When I get done dressing you up, I am inviting all of my friends over to see you all soggy and sissified. They will all laugh at you and tell you that you look like a big baby. Maybe this will teach you to leave my panties alone. You are such a panty thief! Rachel 888.430.2010

November 2, 2014

Published by Madison at November 2, 2014

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Dress up Time

It’s time to dress you up. I make you strip down to your birthday suit. You will not need these clothes anymore tonight. I wash you in the bath and shave you. I have the perfect outfit to put on you. I put on red thongs, a sexy red bra, and tight pantyhose. Next, a tight black mini skirt and red shirt. Red lipstick and high heels. You look perfect my little sissy. Tonight you get to entertain the men at my party. I want you to do everything I taught you. Everything I taught you about making them cum. I want you to make me proud. I better see lots of happy men coming out of the bathroom with red lipstick all over their collars and groin areas. If you do a good job, there will be a treat for you at the end of the night. Rachel 888.430.2010

October 25, 2014

Published by Madison at October 25, 2014

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Ms Ava’s Sissy Training

I have always loved feminizing sissy boi’s from the time I was a little girl. I forced my younger brother and his friends in to dressing like little babies and diapered them before putting them in cute little dresses and panties. I would make them sit in my lap and scold them by spanking their bottoms…..It was not long before I started dating and started to dress my boyfriends like little sissy fags and teasing them with my strap on…teaching them to pleasure men like a pro and preparing them for the big day when they can take a real cock. Ava 888*430*2010

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

September 8, 2014

Published by Madison at September 8, 2014

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Sissy Princess

“My pretty little sissy baby. Where are you?” I turn the corner into your nursery. There you are sitting on the carpet in your pink sun dress.. The one with the tiny little yellow flowers on it. You know it’s my favorite because you look so adorable in it. The way the end ruffles up and I can see your diaper. I bet you would look even cuter if I put some rumba panties on you wouldn’t you? I walk inside of your room and pick you up. “Well lookie at the baby!” I cover your face with smooches holding you close to me. Uh oh do i smell something? I raise you up and sniff your bottom. Oh you bet I do. Somebody needs to be changed. I set you down and tell you i’ll be right back. It’s time for a sissy diaper change.

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

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

July 21, 2013

Published by Madison at July 21, 2013

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Sweet Treats

I come in from my date and see you waiting on the couch. Did you stay up just to wait for me? Did you not hear me tell you that I had a date tonight? No sense in looking up at me with those sad puppy eyes! I need a real man to take care of my needs, and lucky for me I found one! The owner of that new bakery, just at the end of our street, is a big virile treat indeed! His big hands felt so good running over my silky skin. His firm muscles rippled under my hands as I ran them hungrily over his chest and ass. Oh what a handful that man is! He’s quite a mouthful too! Under those tight jeans of his, I found a very large, very able package, and I worked him like no woman has ever worked him before. Worshipping his hardness with my hands and mouth, until I couldn’t wait any longer to feel his pulsing hardness deep inside me. Now, quit your pouting! Come here to me and see what I’ve brought home for you. The sexy man is so nice, that he made sure to send home a hot, fresh treat just for you. See how creamy and yummy it looks? Are you ready to eat up your dessert darling? Sara

June 11, 2013

Published by Madison at June 11, 2013

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Sticky Day Out

Know what today is? It’s sissy cuck’s big day out! I planned a little trip to the friendly neighborhood adult bookstore. You see, while they sell many adult books and movies, they also have a little operation in the back of the store, which can be very profitable. Just a simple little business… gentlemen pay a fee, which is dependent on what will be offered, and then they partake in the goods. What we’re offering is VERY profitable. The chance to gangbang sissy slut AND a sexy MILF. We’ll start by having you just sit off to the side so you can get a good look at all the men standing around me, sizing me up, and rubbing the front of their pants. Then they’ll start to take my clothes off, pulling me this way and that way, unbuttoning their pants and moving closer to me. They’ll feed me their cocks and stuff my pussy while you watch pathetically. Don’t worry dear, you’ll get a similar treatment. I’ll get mouthfuls of cum while others will creampie my pussy and ass… that’s just for you sweetie, they wanna watch you slurp their jism from my holes. Now once you’ve started cleaning my pussy they’ll be tearing your panties off and pushing up your dress. These gentleman have a taste for sweet sissy pussy and they’ll be eager to tear you open. Now make sure you behave yourself like a good sissy slut. These gentleman are paying good money to use you! Lizabeth 888-430-2010

June 2, 2013

Published by Madison at June 2, 2013

Naughty Nanny for Naughty ABies

Your Mommy and Daddy have left you all alone with Nanny Ella tonight. Seems they have big plans and won’t be home until very late, so Nanny will have plenty of time to spend with her little one. Do you remember the games we played last time? You had never played Doctor before, but you caught on very quickly and were a good little patient for Nanny. Maybe this time, you can be the Doctor and Nanny will be the patient! Would you like that? Would you like to explore Nanny’s body? You looked so cute in your sissy outfit last time, that Nanny brought a special toy for us to play with this time. Just think how hard your little peepee will get when Nanny slides this new strap on inside you! Yes, I see thinking about that makes the happy bump in your diaper. Nanny can’t wait to see you make big boy cummies after she teaches you the fun of this new toy. Mmmmm….make cummies for Nanny! Yes, that’s a good ABy! Nanny Ella 1-888-430-2010

April 22, 2013

Published by Madison at April 22, 2013

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Popping Fag’s Cherry

When little bitch bois call me I know exactly what they need. Hearing how nervous and shy they are always makes me giggle. Silly little losers! You can’t hide what you want from me! Princess Jenna always knows heehee! I can hear your breathing getting ragged while I tell you exactly what I’m going to do with you. Your whimpering when I describe my nine inch strap on just makes my pussy even wetter. Are you ready for me to take your ass cherry?? Lemme hear you beg for it! I don’t care how much you whimper and cry while I push you over the wooden horse, I can see your pathetic cock getting stiff and the precum smearing. Heeheehee loser fag, I know you can’t wait to take my cock in your rosebud cunt. Let me hear you scream like a bitch for my cock. Are you gonna cum? Huh wittle faggy boi? Heehee, you’re gonna make that nasty little worm squirt aren’t ya? I wanna see you cling to that horse while I tear your rosebud cunt up! You’re mine now little bitch boi! Once I take a faggots cherry they belong to me. That means from now on, you’re my little fuck toy! Jenna 1.888.430.2010