SIssy Training Phone Sex Archives - Page 3 of 6

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 […]