Archive for the 'Sissy Lessons' Category

Page 14 of 33

Lipstick and Panties

Published on in No Taboo Phone Sex, Phone Sex, Sissification Phone Sex, Sissy Lessons and Sissy Phone Sex. 0 Comments

I know you’re a devoted sissy at heart but it’s time we bring you out into the real world and make some use out of you, just like you’ve always dreamed of. You’ve been keeping your secret for a very long time now. You’ve told me that your wife suspects something. She’s been noticing that some of her panties and bras have been missing even her favorite shade of lipstick. You better hide them better, it won’t be long before she finds her missing items. It’s time to get you ready. On your knees, sissy slut and show these nice big cocks that you’re ready to be the hottest cock sucking sissy slut.

It won’t be long before you have a nice hot load dripping down your face.

Faith

Xoxo

Phone Sex Special

Published on in Age Play Phone Sex, Anal Phone Sex, Anything Goes Phone Sex, Barely Legal Phone Sex, BBC Phone Sex, Bratty Teen Phone Sex, Bukkake Fetish Phone Sex, Crossdressing Phone Sex, Cuckold Phone Sex, Cuckolding Phone Sex, Cum Eating Phone Sex, Extreme Age Play, Feminization Phone Sex, Freaky Phone Sex, Jailbait Phone Sex, Lingerie Phone Sex, Loser Phone Sex, Panty Slut Phone Sex, Panty Worship, Pantyhose Fantasy, Pantyhose Fetish Phone Sex, Pathetic Loser Phone Sex, Peeing Phone Sex, Phone Sex Specials, Raunchy Phone Sex, Sissification Phone Sex, Sissy Lessons, Sissy Phone Sex and Underage Roleplay. 0 Comments

Hey pervs Halloween is almost here and I know some of you will be in your sluttiest lingerie. No worries about dressed up and no place to go because your Princess is going to take you and pimp you out.  I know you love the feel of panties against your clitty. Look, you already have a wet spot. What a slut you are.  Slip into the little dress I bought for you and the pretty silky stockings. I love watching your transformations.

What is next? Stiletto heels to accent your ass that needs a good pounding, a wig and lots of cock sucking red lipstick. Looks to me like you are all ready to go out with me. Just one rule sissy bitch and that is you do just what you are told.

From now till November 1 I have a special for my cum slurpers.   15 minutes is $25.00 and if I demand longer 20 minutes is $35.00. Don’t keep your Princess Torrie waiting!

Lingerie Shopping

Published on in Anything Goes Phone Sex, Big Tits Phone Sex, Crossdressing Phone Sex, Feminization Phone Sex, Flirting Phone Sex, Lingerie Phone Sex, Panty Boys, Panty Slut Phone Sex, Sissification Phone Sex, Sissy Lessons and Sissy Phone Sex. 0 Comments

I love to treat myself with each new season to some new lingerie. I went shopping myself yesterday as I love to take my time and friends sometimes get impatient. I was also in a very flirty mood so I wore a tight little mini dress, a red thong, no bra and a pair of wedge heels.

The mall was very packed for a Wednesday night and I was enjoying the lustful stares from both men and boys. Most stared at my big boobs barely staying in my dress. I took my time, flirting and teasing my way to shops I love to get my sexy and slutty items from.  I noticed a young man was following me. He stayed far enough behind but I knew he was there.

While I was looking at the panties he shyly approached me and asked if I could help him out with a gift for his mom. I could tell by the look in his face and the way he gingerly touched the soft fabrics that those panties weren’t for his mother. We picked out several in “her” size. I could see a little boner and wet spot in his pants.

“You know sweetie, I could help you with a whole girly transformation”, I whispered in his delicate ear. He was so shy and tried to convince me it was really for his mom. I knew better and suggested we go to my house for a complete make over. Over white wine we talked and he admitted he always wanted to look beautiful like a woman. Mommy Debi to the rescue!

My husband, my wimp

Published on in Anything Goes Phone Sex, Cheap Phone Sex, Cheating Girlfriend Phone Sex, Cream Pie Phone Sex, Cuckold Phone Sex, Cuckolding Phone Sex, Cum Eating Phone Sex, Sissy Lessons, Sissy Phone Sex and Size Queen Phone Sex. 0 Comments

My husband could never figure me out really. The pathetic little worm really tried. He tried to touch me, and I revolted. Why would I want to be touched by someone so weak and pathetic? I knew what I was to him. The trophy wife everyone wants. Well, little did he know his trophy wife wanted more. That’s right. I didn’t sign up for a life long bullshit commitment to that tiny cocklette of his. No way! Married? Yes. Although I consider myself single and really looking for some fun ;).

My story is quite simple. I am here to humiliate the men just like my husband. The ones that are weak, pathetic, and couldn’t fuck their way out of a wet paper bag!! You know that you are nodding along with this aren’t you? haha You know what you need to do now!


 Yahoo&AIM: Cum4LaceyJames
1-866-949-4109

Philip the Cum Dump Loser

Published on in Anal Phone Sex, Anal Training Phone Sex, Anything Goes Phone Sex, BDSM Phone Sex, Big Cock Fetish Phone Sex, Cream Pie Phone Sex, Crossdressing Phone Sex, Cum Eating Phone Sex, Deep Throat Phone Sex, Deviant Phone Sex, Goddess Worshipping Phone Sex, Golden Showers Phone Sex, Panty Slut Phone Sex, Pathetic Loser Phone Sex, Scat Phone Sex and Sissy Lessons. 0 Comments

Some men just like to tempt fate it seems. Imagine having a 2 inch little willy and not warning a woman before she sees the fucking joke for herself?  I do love to fuck and I do love big dicks, that is a given. I am going to take a wild fucking guess that if you don’t warn me in advance that means you want to be abused.

I do believe that Philip is somehow proud of his clit and also craves the abuse.  He waits in his little pink panties while I make some calls. I do crave big cock and I also want to humiliate his pathetic ass for not telling me in advance about his joke of a willy. I get the pounding I ache for while Cum Dump watches drooling. He wants his turn so bad but he does need to be severely punished. Once I am done getting cock, I send the men to the kitchen to load up again while having a beer.

“It is toilet time, so get over here”, I command. He tilts his head back as I piss into his mouth. I feel him shaking with anticipation of what will be happening next. Philip sticks his tongue deep in my ass waiting for the cum covered treat.  Stupid little snot rag has already squirted in his panties. The men return loaded and ready to go. Philip gets on all fours and takes the men in both his fuck holes. After a good fuck I do enjoy some entertainment.

Last Days Of Summer

Published on in Anal Phone Sex, Anal Training Phone Sex, Anything Goes Phone Sex, Crossdressing Phone Sex, Deviant Phone Sex, Feminization Phone Sex, Lingerie Phone Sex, Mommy Phone Sex, Panty Slut Phone Sex, Sex Toys, Sissification Phone Sex and Sissy Lessons. 0 Comments

We are having a bit of a heatwave and I am sure it is last one of the Summer. My stepson will be going off to private school next week and this is last few days with him. He is such a hot little thing that I never could keep my hands off him from the first time we met. Even after I divorced his dad we stayed very close.

I have noticed subtle little changes in him from year to year and taking a trip together brought it all out in the open. He loves older women and he is sort of all boy. I mean he has no desire for men but he loves to dress slutty and for me to fuck his adorable little ass with a strap-on. Kind of a fucking shame I found this out on our trip or we could have even had more fun this Summer.

When he arrived the first day I noticed he had two huge suitcases and a train case.  He did have amazing style for a boy his age and I assumed the train case had colognes, shampoos and such. He only took one of the suitcases on our little road trip and when we checked in to our hotel he seemed nervous. Apparently he had brought the wrong one and he had with him his slut clothes.

Seeing him so upset I knew it was time to have the talk. It went very well and he was so excited for his desire to dress like a woman to be out in the open. We planned out first night with him dressed in a tight little red dress with red silky panties under.  I helped him dress and put on his makeup. Fuck, he sure did make a sexy little slut dressed up. We had a wonderful dinner and he got so excited at the way men looked at us. He made me promise to fuck him and not some of the flirting gentlemen. It was the hottest few days fucking my new little lesbian lover.

So Sexy…

Published on in Anything Goes Phone Sex, Lingerie Phone Sex, No Taboo Phone Sex, Panty Boys, Panty Slut Phone Sex, Phone Sex, Pussy Eating Phone Sex, Pussy Worship Phone Sex, Sissification Phone Sex and Sissy Lessons. 0 Comments Tags: .

All the laundry is done and we have fresh clean panties and bras. I even have a few pieces of your favorite lingerie. I am sure you feel like slipping into a pair of those sexy panties for me. I watch you as you slide them up your thighs. Your fingertips running along the waistband. I can tell you’re getting excited just by the way you explain to me how good they feel against your skin. Let’s take a look and check out how pretty you look. What’s that? A little wet spot on your panties?!? I think somebody is really excited now. I stand in front of you and I pull my panties down so you can get on your hands and knees and serve my pussy before I dress you up in my favorite lingerie. You look so sexy, I can’t wait until our bodies are rubbing up against each other.

Dirty Debi

Published on in Age Play Phone Sex, Anal Training Phone Sex, Anything Goes Phone Sex, BBC Phone Sex, Big Cock Fetish Phone Sex, Cougar Phone Sex, Cream Pie Phone Sex, Crossdressing Phone Sex, Lingerie Phone Sex, Panty Boys, Panty Slut Phone Sex, Sissy Lessons and Sissy Phone Sex. 0 Comments

I got the nickname Dirty Debi when I was about 12. I would do all the things my friends wouldn’t. It didn’t matter much if it was boys, male teachers, female teachers or my friend’s daddies. I just love sucking and fucking and didn’t care with whom. As I got older things started to change. I noticed that I loved a certain type of man and I craved being the one in charge.

I still love sex the dirtier the better and it really just depends on my moods. While I love my men cute, fragile and girly I would never turn down a huge, thick hard black cock. When I can combine the two I am in dirty girl heaven.

You are dressed up so pretty for me in your lace panties and bra. I adore watching you prance around in your stockings and heels. Seeing your pretty soft hand wrapped around my strap-on makes my mommy’s cunt so wet. I do have a surprise for you today. When mommy is done fucking her baby company will be joining us. After I get a good pounding from my hot as fuck black lover we will just see where it takes us. I know you will be watching while you play with your little clit. Is my baby in the mood for some BBC today?

xoxo Dirty Debi

Good Subbie!

Published on in Anal Training Phone Sex, Bisexual Phone Sex, Boy Toy Phone Sex, Cock Sucking Phone Sex, Control Phone Sex, Crossdressing Phone Sex, Domination Phone Sex, FemDom Phone Sex, Feminization Phone Sex, Forced Bisexuality Phone Sex, Humiliation Phone Sex, Phone Sex, Pussy Eating Phone Sex, Sex Slave Phone Sex, Sissification Phone Sex, Sissy Lessons and Sissy Phone Sex. 0 Comments


I love molding a nice little subbie. I took control of a cute, innocent, fresh subbie last night. I dressed him so pretty and sexy. I took this opportunity to introduce him to my big, well hung stud, Lee. I told Lee to use my slutty sub.

I could tell he was nervous, but I told him “be a good whore and do as you are told.” Nothing makes my pussy wetter than watching my sweet, fragile sub being fucked with a massive, thick cock until he can barely stand it.

Lee has my subbie on all fours fucking, and stretching his tight ass. I love seeing Lee’s big cock disappear into that narrow ass. Lee stops and wants lips wrapped around his dick. I am so proud of my subbie being such a good little cock sucker. I get creamer, and creamer as I hear him gag and choke. I see Lee is pumping faster, letting me know he is ready to cum. I tell Lee to shoot his cum all over subbie’s sweet face. I grab subbie’s face and forcefully push him between my thighs. “Get to work bitch,” I say. He buries his tongue into my dripping, tight, pink pussy. Bringing me to a screaming orgasm.

I demand the best from my subbie’s


Marilee

Bedtime Story

Published on in Anything Goes Phone Sex, Auntie Phone Sex, Boy Toy Phone Sex, Crossdressing Phone Sex, Deviant Phone Sex, Dirty Panties Phone Sex, Domination Phone Sex, Erotic Stories Phone Sex, FemDom Phone Sex, Feminization Phone Sex, Humiliation Phone Sex, Panty Boys, Panty Slut Phone Sex, Sex Toys, Sissy Lessons and Sissy Phone Sex. 0 Comments

There once was a boy who couldn’t get enough of looking, touching and smelling his auntie’s lingerie. Every day after school he went to her room and first emptied her dirty pantie hamper. He loved to rub them against his skin, smell them and lick off auntie’s pussy juice and anything else on them. That made him happy for awhile. Sometimes he would take a pair and wrap them around his cock jerking off to the wonderful smells in her room.

Soon that wasn’t enough for him. He opened her walk in closet and squealed excitedly at all the pretty lingerie on the softly padded hangers. His little wee cock was immediately hard again. He was a prissy little thing and went for all pink. When auntie got home she found him in her room wearing a pink baby doll nightie, pink crotch-less panties, pink stockings and even some pink pumps. Auntie stood at the door watching him rub his hands over his soft pink clad lingerie body. His little dick looked more like a clit as it left wet spots on the panties.

Auntie found it very exciting and all she could think about was bending her sissy slut over the bed and giving him a hard pounding.  “What do we have here”, she asked.  The boy was startled and tried to explain but he could not hide the truth from her. What the boy didn’t see in his snooping was her large collection of toys. Auntie put on the big black strap-on and bent him over the bed. “Now don’t just lay there”, she said. Press that little wet pussy against my cock and show me how much you want it”, she whispered in his little ear.

Let’s make our own bedtime story.  Mistress Brianna