Archive for the 'Sissy Lessons' Category

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Let’s Play Dress-Up!

Published on in Lingerie Phone Sex, Mommy Phone Sex, Panty Boys, Phone Sex, Sissification Phone Sex, Sissy Lessons, Sissy Phone Sex and Stockings and Garter Belts. 0 Comments

I am cleaning your room.  I find my sexy Victoria Secrets catalog hidden under your mattress.  You have circled certain items.  I assume you were just looking at the pretty ladies for a little “inspiration” for personal playtime before bed, but the circles have me puzzled.

I hear you come home and scold you a little for taking my catalog without permission.  I ask you repeatedly why you have circled certain bra and panty sets, a little pink nightie, and a very sexy black teddie with attached garters and stockings.  My frustration starts to show when I don’t get a straight answer from you.

Finally you admit that you really like lingerie.  You think that it is really pretty and girly. You like how it feels against your own skin.  You tear up and softly whisper that you wish you could wear some really pretty girly things.  I lean down and wipe a tear from you face and take you to my closet and lingerie drawer.

I pick out a super cute little red cami and red panties.  They are extremely soft and lacy.  You try them on and model them for me.  I have you slip into my sexy red shoes and black satin robe to complete the look.

Oh, I love the smile on your face! I take you in front of the mirror so we both can admire how lovely you look in my lingerie.  Well, let’s see what else we can find for you to try next!

Kisses,

Mommy Morgan

My Submissive Sissy

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Finding you standing in my bedroom all dressed up in my panties and my nightie, and some of my jewelry. I could even smell some of my expensive perfume on you. You’re dressed just like me. I watched you from the door way as you admired yourself in the mirror. Prancing around, practicing to walk like a woman. Your erection was a little hard to hide. I do have to say, I was a little surprised but I knew exactly what I was going to do with you from this point on. I walked into my bedroom wrapping my hands around your waist, whispering in  your ear “what a naughty boy you’ve been.” I’m thinking you need to be punished now. Making you crawl up onto my bed laying face down spreading your legs. Making you wait with anticipation as I pulled out my strap-on. Making you feel so helpless as I pushed up your silk nightie and ripped off your panties. Rubbing my strap-on along your tight aching hole. Watching you squirm all over my bed with pleasure as I started to have my way with you. Stretching that little fuck hole wide open. Teaching you a lesson not to go through my girlie stuff with out asking me first. I’ll be the one dressing you up and fucking you like my whore.

Charlie

You like the feeling!

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I know that it is hard to ignore the feeling you get when you put on pretty, silky, lacy outfits. The feeling of high grade silky pantyhose and real silk panties against your skin. The thought of it makes your little bitch cock get hard. Don’t worry my bitch, I understand and here to help you. I would love to degrade your sissy bitch ass. Take you out and make you put on some beautiful clothing. I think you should model the slutty outfits in the store, I’m pretty sure everyone will be laughing at you! Oh, then what is my plan for my sissy boy? Guess you will have to call and find out.

Nobody Knows You Like I do!

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Nobody knows your deep dark secrets but me. You might be in a business suit during the day but when you come home and that suit comes off you’re my whimpering, submissive pet. When you’re at the office, you think about me dominating and humiliating you. You just never know what I’ll have you do, I may just have a huge hot, load of jizz that I demand you to clean out of my pussy. Or, I may have several well hung men waiting for you when you walk through that door. I might dress you up first so you look like a true cock sucking slut when you take their enormous dicks into your slutty lil mouth.

I only know what you truly want and sometimes you might not like it at first, but then you cave. Start to realize that your life finally has somewhat of purpose being my subbie pet.

My Pink Panties for My Favorite Pantyboy

Published on in Domination Phone Sex, FemDom Phone Sex, Humiliation Phone Sex, Lingerie Phone Sex, Panty Boys, Panty Worship, Phone Sex, Sissification Phone Sex, Sissy Lessons, Sissy Phone Sex, Submissive Phone Sex, Tease & Denial Phone Sex and Tease Phone Sex. 0 Comments

Let’s play!  You are the cutest little pantyboy with the smallest little cock! Oh my. I giggle every time I think of it.

But to be really hottest,  I really don’t want to look at it.  Let’s cover that little thing up.  It won’t take much because you are so small.

Here, sweet baby, you can wear my favorite little pair of pink panties.  These soft little pink panties will do the trick to camouflage your tiny little dickie.

Wow, my soft pink panties make your sweet little butt look so cute!  You have the cutest little bump right there in the front of your panties! Haha!

Let’s have some fun!

Let’s Play! Maybe I have something super cute to go with those special pink panties.

Hugs and Kisses,

Skylar

My Naughty, Slutty Panty Boys!

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Happy Halloween to all my naughty little panty boys!

I am in a very nasty mood and want to dress you up, super extra slutty and whorish tonight! It is time for some more sissy lessons!  Time to humiliate you!

Turn you out all dressed in sheer black lace lingerie, stockings, heels.  Turn you into that whore that you can only be for me!  Take you to a Party and let you service my friends and let that little bottom of your ass be used and abused. Pass you around like a toy!  Force you to suck big cocks and force you to  worship my pretty lady ass!  I give all the ladies a lipstick and watch them write a naughty word on your body!  I love to degrade you and humiliate you, my whore panty boy! Look at all the pretty ladies laughing at how much of a whore you are!

Halloween is the perfect opportunity to go the lingerie store for the first time. You can tell a little lie.  You can tell the sales lady that your little slut outfit is for your Halloween costume.    ha ha!  Only you and I know the truth, don’t we? We know you are a slutty little panty boy!

Skylar

How bad do you want it?

Published on in Anything Goes Phone Sex, Ass Worship Phone Sex, Blackmail Phone Sex, Body Worship Phone Sex, Cock Control Phone Sex, Cock Tease Phone Sex, Coed Phone Sex, Control Phone Sex, Domination Phone Sex, Erotic Stories Phone Sex, Fantasy Phone Sex, FemDom Phone Sex, Hardcore Phone Sex, Humiliation Phone Sex, Naughty Confessions, Orgasm Denial Phone Sex, Panty Worship, Princess Phone Sex, Pussy Worship Phone Sex, Sensual Domination Phone Sex, Sissy Lessons, Spoil Me Phone Sex, Tease & Denial Phone Sex and Young Phone Sex Voice. 0 Comments Tags: , , , , , , , , .

Yes, you naughty man!! I know you drool over my sexy body all the time and why wouldn’t you? Your hot cock tease loves making you throb. I know you pretend to be working when truly you are watching every move I make. My fine booty shaking back and forth teasing you all the time. My sexy giggles that you can never get out of your head. You find yourself craving Miss Sidney at all hours of the night, unable to sleep, needing to be used so desperately. Aching to serve your Princess 24/7 if that’s what it takes. Hmmm what shall I do this time to make you earn it? I have totally put your limits to the test time and time again. This is a challenge I simply can’t refuse you pervy man child! Come prove to me how bad you want it and maybe just maybe I will give you a taste.

sinful_lil_sidney@yahoo.com

Email me to set up your naughty phone sex session!

Sex Therapist Sid

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Most of you know me for the ball busting, cock teasing hottie I am but I have many talents yet to be explored. Just ask my naughty man, you know the one who worships his Princess above all others. The one who would do anything at all just for one tiny kiss on my fine booty or a warm trickle of my golden on his tongue. Oh how he loves to be edged in his place, put on his knees before me, forced to hold his seed until I feel he has earned it. And believe me, when I say he very seldom earns any kind of release at all.

Well, I thought it was time we had a nice long heart to heart. After all, he has been calling his Princess Sid for a few years now and it’s always a good thing to clear the air. We talked about his fetish fantasies and pervy thoughts of young, underage pussy. We also discussed his deep infatuation for my panties, especially my dirty ones and how he has willingly bought more than a few pair worship and adore. I can’t begin to tell you how this therapy session really brought light to his fetish needs and how much better we both felt afterwards. Especially me, his sexy yet compassionate therapist, willing to take any measure necessary to ensure his well being. Of course, this includes wallet fucking, edge play, some blackmail and a list of other resourceful tools needed. I used them all to encourage his taboo confessions and got exactly what I wanted out of him.

sinful_lil_sidney@yahoo.com

Walk-ins Always Welcum~

Forcing My Sissy Slut

Published on in Anything Goes Phone Sex, Ass Worship Phone Sex, BDSM Phone Sex, Black Cock Worship Phone Sex, Chastity Training Phone Sex, Cheap Phone Sex, Cock Control Phone Sex, Cock Tease Phone Sex, Control Phone Sex, Crossdressing Phone Sex, Cum Eating Phone Sex, Cum Shots, Cum Swapping Phone Sex, Domination Phone Sex, Edge Play Phone Sex, Erotic Stories Phone Sex, Fantasy Phone Sex, FemDom Phone Sex, Feminization Phone Sex, Fetish Phone Sex, Forced Bisexuality Phone Sex, Forced Sex, Golden Showers Phone Sex, Guys Sucking Cock, Hardcore Phone Sex, Humiliation Phone Sex, Mistress Worship, Nipple Clamps, No Taboo Phone Sex, Princess Diary, Princess Phone Sex, Role Play Phone Sex, Sensual Domination Phone Sex, Sex Toys, Sissification Phone Sex, Sissy Lessons, Sissy Phone Sex and Spoil Me Phone Sex. 0 Comments Tags: , , , , , , , , , .

You say that you would do anything for your Princess Sidney so I put it to the test. I showed up unexpectedly with a bag full of delicious sex goodies. I never leave home without my nipple clamps, butt plug, dildos, strappy, and a few other favorite fetish toys. As always, I instantly took complete control of your pathetic man pussy and made you strip down and get naked for me. Dressing you in a lovely pink baby-doll nightie, ruffled panties, ribbons in your hair and whore red lipstick on your lips. You whimpered and moaned, begging for some mercy but I gave none. We practiced cock sucking with my black strappy, and I made you get down on your knees to worship Princess. Edging and teasing you with my sexy bubble butt, the one you absolutely adore, worship and grovel for.

Finally, I gave you a sexy golden shower and forced my warm liquid down your sissy throat. You wanted more and begged for me to use you but I had other plans.

Oh sissy, the look on your face when my big black stud came in to join us. Huge chocolate cock in hand already stroking at the sight of his bitch. I shoved you back down to your knees and rubbed his thick,black cock up and down your face, teasing your mouth. Forcing you to worship his beautiful black pole with your whore red lips, pushing your head down so you could take every inch. Did you like the way his thick, creamy fuck batter taste sissy?  I know you did because you swallowed every last gooey drop.

Princess Sidney

To be Trained

Published on in Anal Training Phone Sex, Anything Goes Phone Sex, BDSM Phone Sex, Big Nipples Phone Sex, Big Tits Phone Sex, Body Worship Phone Sex, Boy Toy Phone Sex, Cheap Phone Sex, Cock Control Phone Sex, Control Phone Sex, Domination Phone Sex, Erotic Stories Phone Sex, Fantasy Phone Sex, FemDom Phone Sex, Feminization Phone Sex, Fetish Phone Sex, Forced Masturbation Phone Sex, Guided Masturbation Phone Sex, Hardcore Phone Sex, Humiliation Phone Sex, Latex/Leather Fetish, Mistress Worship, No Taboo Phone Sex, Orgasm Phone Sex, Panty Boys, Panty Sniffing Phone Sex, Panty Worship, Phone Sex, Pussy Worship Phone Sex, Role Play Phone Sex, Sensual Domination Phone Sex, Sex Slave Phone Sex, Sissy Lessons, Sissy Phone Sex, Strap-On Play Phone Sex, Uninhibited Phone Sex and Your Naughty Ashlee. 0 Comments Tags: , , , , , , , , , .

It’s not always an easy feat, training eager little submissive panty sluts. Just because the desire to serve a sensual Goddess is present doesn’t always ensure it’s fruition. In fact, I am very meticulous in my training and require you to be so as well, if I give an assignment I expect completion. I do not tolerate disobedience or anything even mildly resembling it. Your Mistress has ultimate power and now owns your slutty panty loving ass. Essentially, you belong to me, you are my bitch boy and satisfy my every desire you will. This may all seem a bit harsh but I know you wish to please me, so be a good boy and perhaps you will be rewarded.

I consider myself to be a very sensual phone Mistress, erotic, sexy and wide open to exploration of all kinds. I love the concept of mixing pleasure with pain so If you are a naughty panty boy punishment will be the inevitable. I do love hearing you whimper and watching you squirm under my control.

Sensual Kisses,

Mistress Ashlee