Birth of an Office Sissy Phonesex

Jake had been working for me for about a year now. He was unlike most office assistants. For one, he was male. Most office assistants are women, but somehow Jake was perfect for this position. I didn’t hire him because of his looks. I prefer strapping young studs, and Jake was far from that. He was very short for a man, I towered over him with about 4 inches between the top of my head and his. The thing that made him perfect for the position though, was that there was no sign of defiance or hesitation when I asked him how he felt about taking orders from a woman.

“I would do anything you told me to Miss.” The way he said it woke something up inside of me. It was like a carnal instinct being jolted from a dormant state. He’s spent the last year bringing my coffee to me in the mornings, running out to get me lunch, picking up my dry cleaning. He did anything and everything I asked of him, and each time he fulfilled a request of mine, his life became a little bit better.

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BBC Sissy Phone Sex

His sissy name was Becky.  God they always picked such cheesy girl names.  Becky, Courtney, Freja (what ever the hell that is).  I had him on all fours on the coffee table.  His clean pink hole was shave smooth just like I had instructed.

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Sissy Panty Hose PhoneSex

I could hear the delight in his voice as he/she pulled the panty hose up their leg for the first time.  It was a week ago I gave him/her a shopping challenge.  I helped him/her find the right sizes and I made him do it all on his own.

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Sissy Baby and His Special Phone Sex Paci

Sissy Baby Phone Sex

I had a special surprise for Sissy Baby J…he crawled over to me as I held up a pretty little pink paci and waved it in front of his face. “Look what Mommy’s got for you baby. Go ahead and suck on this.” His eyes got wide, and then he smiled. “Thank you Mommy.” What Baby J didn’t know was that his paci was very special, enchanted, even…

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On the First Day of Xmas, my Phonesex Mistress Gave to Me

Merry Xmas Sissy!

On the first day of Christmas, my mistress gave to me a pair of her dirty panties…

“Gather round my pets! It’s my favorite time of year here at Miss Silver’s School for Sissies.” Mistress Silver looked stunning in her black pencil skirt, black button-up silk blouse, black pantyhose, and black strappy heels. Her blond hair was softly curled and cascaded around her face. She wore black framed glasses and red lipstick. She carried a red velvet sack, and the sissies couldn’t wait to see what surprise their sensually devious mistress had for them. Like a flock of lambs, they gathered among their Mistress, and when she was sure she had all pupils in her presence, Miss Silver ordered them to their knees.

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My Son’s Feminizing Phonesex Awakening Ch 2

Come now darling, you were always meant to be my girl

Click here for Ch. 1 of my son’s feminizing awakening

“But Mommy, I’m not a girl! What are you talking about.”

I don’t know if Chucky was still in denial, or if he really thought that I was crazy. A part of him had to know that he was born into the wrong body. I just had to help him see that mommy always knows best. He needed to say the words. They needed to come from him.

“Remember last Thursday when you came home and said the boys were making fun of you in the locker room?”

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My Niece Alice Phonesex Part 1

844-332-2639 x 224

My little niece was so adorable today. In her Sunday best, she wore a modest white dress. The no sleeves over the arms and a semi circle over her chest, a cute ribbon belt around her waist, and stockings over her legs into modest mary jane shoes. She sat so patiently, her makeup already done. A light foundation, lip gloss, and eye shadow. All that was left was her hair, I made sure the long sandy blonde wig was pinned securely into place before I brushed the shiny soft locks and curled them.

“We’re going out to lunch today my sweet.” I smiled, meeting her eyes in the mirror. “Your first time in public all dressed up. Exciting isn’t it.”

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Hot Wife Is A Waste For Phonesex Sissy Boys

sissy cuckold domination phone sex

Tom                     1-844-332-2639 ext. 342

I don’t know how it happens but the sissiest bitches get the hottest pussy. When she opened the door I about broke my zipper my cock got hard so fast. This chick was everything and then some. I’m talking tits and ass and the looks she was just gorgeous. She invited me in and offered me a drink. Her husband fixed it for me and I thought the faggot was going to spill it all over me trying to get a good look at my dick. She starts to ask him ain’t I good looking, and ain’t my body better than the sissy boy will ever have. He gets a soft voice and lowers his head looking at his feet admitting he will never measure up to me.

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