Sissy Slutty Cuck Maid Phonesex, Part 3

Your boss pulls his still hard cock out of my tight pussy, his swollen length still twitching from his orgasm. You gawk at it, still reeling from the situation you’ve found yourself in–you’re in a maid outfit, complete with heels and a barbed butt plug, fondling yourself as you marvel at your boss’ big cock and my cream-filled cunt–when I roll onto my back and snap, “Get over here and clean up this mess! Don’t you dare let this cum go to waste!”

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Sissy Slutty Cuck Maid Phonesex, Part 2

You see me, your barely legal wife, bent over your side of the bed. Behind me is your boss, the man who made you wealthy and allowed you the comfort of the home you clean and the wife you never get to fuck. One of his legs is propped up on the bed, so you can see his full monstrous length penetrating me. One of your hands lifts the skirt of your maid outfit, while the other rubs your clitty through your silk panties.

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Sissy Slutty Cuck Maid Phonesex

You strut through the flat, dusting every surface of hard furniture and decor in sight. Well, you’re doing your damnedest to strut–you feel more as if you’re waddling, what with the large barbed butt plug I had you insert before your shift. Your platform heels give you a six inch boost, and it exhilarates you knowing that your shoe height is more than the length of that tiny thing in your silk panties. And to think, you were instructed to have all the curtains open and the blinds drawn, so that passersby can see you, a grown man, wearing a slutty maid outfit with white stockings. Due to the shortness of your frilly skirt, they’ll also see your panties and plug. This adds a healthy blush to your face as handsome men and gorgeous women stroll by and laugh at you.

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The Sissy Clit – Sissy Phonesex with Ilene

Sissy Phonesex with Ilene

The sissy clit is very important. Just a man should find the clit on a woman, a sissy should find her sissy clit. Not only should she find it, but, most importantly, she should learn to play with it correctly.

To be clear, where the sissy clit is at, is where a cock would be on a man. However, since you’re a sissy, and well, it’s usually much smaller than it would be if on a man, this is your sissy clit. Now, you’ve noticed that your sissy clit does drip, and it should. In fact, as your sissy desires grow, it will drip more often. That’s good. You will feel that wetness in your panties and you will be reminded how much of a sissy you are.

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Sissies Do Love Showing How Pretty They Are – Sissy Phonesex with Ilene

A sissy is nothing more than a Drag Queen without the beauty and couture. Sissy’s are more of a “boy in a dress” They will never reach the high standards of a Drag Queen, and will never be a beautiful and perfect as an Alpha woman, but, they are very fun to play with.

I love to dress mine up and show them off at garden parties, brunch, different gatherings like that. Gatherings where my girlfriends are perfect in dress and beauty head to toe and my sissies are envious and do anything to try and live up to our level.

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Your New Teen Mistress Phonesex

Do not be deceived by my age and innocent face. Do not doubt my ability to dominate your effeminate ass. My body might be cute and petite, but you’ll still find yourself hypnotized by my slender legs and round teen ass. You see my short, tight clothes with their girly colors and patterns, and you see the you that you never explored when you were younger.

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Imitation is the Sincerest form of Flattery – Sissy Phonesex with Ilene

Sissy Phonesex with Ilene

You want to be me, look like me, act like me, fuck like me. Your whole world revolves around me. You study me, try and walk like me. You beg me to dress you in the same clothes I wear, to do your hair like I do mine.

You want to be me.

You sneak into my dirty clothes and pull out my panties. You put them on, hoping my smell becomes yours. You slide on my stockings, hoping your legs look half as good in them as mine do. You try to fix your makeup as I do mine.

You want to be me.

You watch how I fuck, you watch how I suck, you study the rock of my hips, the moans of my enjoyment, the movement of my tongue. You practice, you bend over, you beg my Alpha males to fuck you like they fuck me.

You want to be me.


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When “She” Begs To Be Pegged – Sissy Phonesex with Ilene

Sissy Phonesex with Ilene

When it comes to my sissies, I’m a pushover, what can I say. They are so damn cute with their little dresses on, their makeup, and when they have pigtails, I’m done.

The other night, one of my sissies begged me for something in the cutest way possible. See, she loves when I use my strap-on and she recently got into trouble for not keep my shoes organized, so, I told her 1 week with no strap-on.

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She’s Just Adorable In Her Panties – Sissy Phone Sex with Ilene

Sissy Phone Sex with Ilene

The number one item that sissies love is panties. Not just any panties, cute, frilly panties. A Sissy would never be caught wear plain ole granny panties, and never enjoy wearing men’s underwear, nope, cute panties are the choice for sissies.

I had a sissy I was playing and training and she loved her panties. She had over 100 pairs and always bought new ones each week. Every time she bought a new pair she would call me up and model them on Skype for me. Of course, I would take screenshots, and we would even test them. By testing them I mean how durable they are.

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A Good Sissy Knows Her Place – Sissy Phonesex with Ilene

Sissy Phonesex with Ilene

I truly love a good sissy. They are fun to play with, willing to please, and I never get a true sissy trying to top from the bottom. Which is exactly why I can always tell a true sissy from a wannabe panty sniffer.

A good sissy knows her place. Basically, her place is wherever I decide, and she never complains. I’m rarely mean to my sissies either, mainly because my sissies know their place. For example

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