Red Paddle Part 3

It's time for Sissy to learn to worship his Mistreses asshole.  She gets on her knees and spreads her ass cheeks and tell sissy to get busy and sniff and lick her asshole

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Petticoat Punishement 4

Ms Simone has lovely large mommy breasts that she takes out for Sissy Monika's nursing and milking.  She cuddles her sissy in her arms and place her soft full breast into her sissy mouth and tells her to nurse from her tits while being milked.  Ms Simone oils up Monika's clitty for a very long and satisfying milking.  She rubs her softly and gently making sissy harder and harder.  The need to come and spurt sissy cream is over  urgent.  Cliity swells to it hardest and soon erupts into to stream of sissy come spurting high into the air

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Pantyhose Bondage Session 4

With his pantyhose cut open and his cock exposed Mrs Loving bends him over and lubes up for her anal work.  She slides a finger deep in his sissy asshole pussy and begins finger fucking his ass hole while with the other hands she begins the teasingly slow milking.  Watch as she milks him and he comes all over her black shiny thigh high boots

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Learning To Suck First Cock Session 3

Mrs Loving holds and comforts Sissy Monika as she receives her first cock in her sissy pussy. Monika receives it rather well with the help of Mrs Loving. With this part of the training complete she then feminizes Dade by dressing him in a little pink cami and matching panties. Mrs Loves playing with two sissies at the same time and it really shows. She's smiling all the time she's stroking and rubbing both their sissy clitties. The clip ends with Dade sitting one side of Mrs Loving and Monika on the other. Both of these sissies masturbate while being encouraged. Monika gets excited when Dade spurts and leans over to drink his come.

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Feminization Session 2

Mrs Loving began removing his ugly boy clothing when she discovered he was wearing white satin girls panties with sissy ruffles on the butt.  He was embarrassed at her discovery and he explained that he had to wear them.  It took some coaxing but she got Monika to admit that he really like wearing them.  It was obvious because the more they talked about his panties the harder he got.  That made him even more embarrassed but Mrs loving seemed to enjoy seeing him like that and even giving his erect penis a little pat before taking the rest of his clothes off.

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Mrs Loving finishes with Sissy Christine's make up and then put on the very pretty and feminine blond wig.   Sissy is so pretty that Mrs Loving gets hot and can't keep her hands off him.  After the make up and wig she puts sissy in the pretties pink LG dress and pink feminine panties and then the real training begins with Mrs Loving putting on her strap on for sissy to suck

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Feminization Session 1

He was a little scared and nervous at being with Mrs Loving but his mother told him he must go and be very good and do everything he was told.  The first thing Mrs Loving did was to tell him his new name was going to be Monika.Mrs loving told Monika that she had been asked to feminize him into a pretty sissy girl.  He wasn't sure about it but it sounded exciting at the same time.  He had often dreamed of wearing a pretty, lacy party dress, but he never told anyone.

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Make Up Feminization Session 4

After a long session of training Monika she's ready for her reward.  What she didn't know was that I was going to get her used to receiving a man's cock in her ass or sissy pussy.  When I told her that I was going to be opening her up with a dildo at the same time I milked her sissy clitty she got very nervous. I promised her that it wouldn't hurt and she would really enjoy it.  She did enjoy it and so did I!

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