Archive for the ‘Sissy Lessons Phone Sex’ Category

Pretty Sissy

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You’re going be a pretty sissy when I’m done with you. I’m willing to do all the hard work for you. I’ll take care of the clothes and makeup. You just relax. I’ll have you feeling just as sexy and slutty as I am. It’s not gonna happen by it’s self. That’s why I’m going help you.

I have the perfect outfit to get started in. I love when your clitty gets hard when you try on the new pink silky panties I bought you. How do you like the fabric rubbing against your ass cheeks? I also bought you your own personal pink dildo. I want you to show me how slutty you want to be. I watch you bring the dildo to your mouth making it slippery and wet. I watch you try to take it deeper while the tears stream down your face and you start gagging and squealing like a girl.

You still have a ton of work to do before you become the perfect sissy. The first lesson is to learn to deep throat your dildo for me. Once you’ve accomplished that, we can move on to a nice fat cock and we can continue our lessons.

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JulieWritten By: Julie
Call Julie @ 1-866-949-4110
Email-  jerkit4jules@aol.com

 

 

Gang Bang Daddy

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   Well aren’t you just the cutest little thing! 

I rush home from school hoping to have the house to myself, but there you are. I hear strange sounds from my bedroom, so I quietly open the door to see. There you are in my sexy lingerie. I try not to laugh, but everything is just all wrong for you. You try and make excuses, something about a Halloween costume. I know the truth.

                I tell you that I can make you into such a sexy bitch, but you will need a makeover. Those hairy legs need to go! 

I shave your legs and then lots of sweet smelling  lotion for those sexy legs. You sit at my vanity as I put on your makeup. Lots of mascara and shiny lip gloss. The men love to see smeared makeup rolling down your face after you give a blowjob.

Now stockings to show off those sexy long legs and of course, heels to show off your fuckable round ass.

You look amazing! So naughty and sexy.

Oh no! Now you are all dressed up with no place to go.  Don’t worry, your baby girl has a plan. I start texting all my guy friends from school. Now it’s a party!

You drool as you see all the football players from school arrive. Time to turn you out.

 

  

WritteDelaneyn By: Delaney
Call Delaney@ 1-888-566-2337

 

 

 

Hey Panty Boys, I Want the Details!

| Isabelle's Blog, Lingerie Phone Sex, No Limits Phone Sex, No Taboo Phone Sex, Panty Boys Phone Sex, Panty Worship Phone Sex, Sissification Phone Sex, Sissy Lessons Phone Sex, Sissy Phone Sex | 0 Comments

My dearest little panty boys, I know you picked up some new panties at Victoria Secrets. It’s so easy this time of year to buy new panties. I’m dying for you to tell me all about them. Maybe even send me pics of you in your new little panties.

I want to know all the details! What color are they? Where did you get them? Was it exciting to hand them to the sales lady when you were buying them? Did she give you a little wink or little smile? Of course she knew they were for you!

Don’t they feel so good?  I bet they look so cute on you. What style did you buy, bikini or thong?

I can’t wait for you to call me and tell me all the details. Then, I am going to make you cum so super hard in your brand new sexy panties!

 .

 

IsabelleWritten By: Isabelle
Call Isabelle @ 1-866-704-9517
Email- isabelleisgoing2rockurworld@aol.com

 

 

Sissy Lessons with Phone Sex Lexi

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Are you a sissy like one of my good callers? It’s funny Michelle is the “femmie name” I gave to a regular client of mine. She’s a true sissy through and through.

Her and I have spent a lot of nights on the phone talking and sharing our inner most taboo secrets, doing our nails, or trying on new clothes for each other. I have taught her well in the ways of being a prim and proper sissy. Not to mention, a mind blowing cock sucker! I must admit, my sissy training has definitely paid off very well.

We ordered her the perfect dress and lingerie. Oh yes! Michelle is going on her first date with a hot stud. How lucky is she? I want her in white lace crotchless panties when her date pops that tight, virgin ass cherry.

I just know that she’s rubbing her little clity right now thinking about her very special date night to come. All her cock sucking lessons will surely pay off nicely. 

You have a lot to learn from Phone Sex Lexi! I love making you into my little girly sluts.

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LexiWritten By: Lexi
Call Lexi @ 1-866-924-5732
Email: phonesexlexi@gmail.com

 

I Love Panty Boys!

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Lately, I’ve been thinking of my love for panty boys. I love taking off my pretty pink panties and putting them on a willing panty boy and showing him off.

I like helping them learn to suck cock just the right way, and then watching him take a nice big cock for me as I cheer him on. It turns me on!

 I’d like to extend an open invitation to all panty boys, closet bi’s, girly sluts, and outright fags. Call me. Share my panties, and share some cock. Discover what it’s like to be a Pretty Princess with me.

Don’t worry straight guys, I haven’t forgotten about you. If wearing panties isn’t your thing, maybe I could put on a fashion show and model my sexiest lingerie for you. I just bought about $200 dollars worth of new stuff at Victoria Secrets. I’d love to show you what I have, then have you take it off before you fuck me!

Shopping with Bailey

| Bailey's Blog, Lingerie Phone Sex, No Limits Phone Sex, No Taboo Phone Sex, Sissification Phone Sex, Sissy Lessons Phone Sex, Sissy Phone Sex | 0 Comments

Awww, look how precious you look! You’re such a pretty girl.

Come over here, let me help you a little. Your makeup needs a little fixing. There, that’s better. Now you’re absolutely gorgeous! I have a soft spot for pretty panty boys like you. I know how badly you want to embrace your feminine side. There’s nothing wrong with it. I’m more than happy to help you make that happen. I don’t judge. In fact, it turns me on a lot. I’ll tell you what, if you’re going to my beautiful girlfriend, then you should have all the benefits that come with it. After all, there’s nothing more fun than an afternoon of shopping with my little sissy. If I’m going to spend the time getting you to look perfect, we have to go out and show you off, don’t we?

Just think, we can go to the mall and you can model different outfits for me. Of course, we’ll have to stop off at a lingerie store. You didn’t think I’d leave out the best part, did you?

When we’re done and we can’t carry anymore, we can go grab some lunch. Lunch is almost as fun as the shopping. Just think, we can have a few glasses of wine and share secrets we know about the people we know.

Once we’re done with lunch and feeling a little buzzed, then we can go home and try on the lingerie again. Did I tell you how I love the feel of silk pressed up against my body. Just thinking about it makes me want to go shopping right now.

What are you waiting for? Let’s go do some damage.

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BaileyWritten By: Bailey
Call Bailey @ 1-877-504-7189
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Email: sexybailey101@aol.com

 

 

Feminization Training Phone Sex

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Are you looking for feminization training? Well, then you need to prove just how good of a sissy you can be for me. I am going to pull you by your long wig and wrap your wimpy hands firmly around my strap-on. Do you feel how realistic my rubber cock is? Feel how hard, firm, thick, and long it is? I am going to make sure to teach you a lesson, a cock sucking lesson, as you’ve been a naughty cross dresser sissy lately.

When it comes to feminization, I have no limits. Our sessions can be a simple GFE (girlfriend experience) where we share secrets, or tips about clothes, make-up, boyfriends, etc. Or, as hardcore as me dressing you up and making you suck off my well hung black friend. You decide but you will be a good sissy slut for me, oe there will be consequences.

 

 

KimberleyWritten By: Kimberley
Call Kimberley @ 1-866-835-6067
Email: naughtygirlkimberley@aol.com

 

 

 

 

Now it’s Your Turn

| Angie's Blog, Anything Goes Phone Sex, Cock Curious Phone Sex, Cock Worship Phone Sex, Fetish Phone Sex, Mature Phone Sex, No Limits Phone Sex, No Taboo Phone Sex, Sissification Phone Sex, Sissy Lessons Phone Sex, Sissy Phone Sex, Small Penis Humiliation Phone Sex, Strap-On Play Phone Sex | 0 Comments

 I know you like being dressed up all pretty in my panties. You like having your face made up with Miss Angie’s bright red lipstick all over your sexy mouth.

You  pretend to be such a strong man in public but you know how twisted your fetish really is. Watching you dress up just for me makes me keep all your dirty little secrets. But, we both know the only way for you to get that little cock hard is to be a sissy panty boy, doing everything Miss Angie asks of you!

I pull your pretty panties to the side and you take my big strap-on deep inside your man pussy. As much as I love fucking your sissy holes, it’s time for you to take the real thing. I know how much you secretly desire my lovers cocks, and now it’s your turn.

 

 

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Written By: Miss Angie
Call Angie @ 1-866-662-5209
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Email- missangieknowsbest@aol.com

 

 

 

Transforming Into a Fabulous Sissy

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So you have a desire to be girly! It’s much fun to be a girl!

There is so much more to being a pretty girly girl or a cute sissy than simply putting on a silky pair of panties. It’s hard work to look good. There’s many details and so much to learn. So many tricks and secrets to luscious long hair, lovely lips, and heavenly hips.

Let me teach you how to look classy and feel fabulous.

Have you been experimenting with cross-dressing but are you having trouble pulling it off? Something not quite right? When you look in the mirror do feel silly instead of feeling sexy? Do you feel like one hot mess instead of a beautiful girl? No worries, sweet cheeks!

Give me an opportunity to help to you be a beautiful girl. I can give you some make-up tips, and share some beauty secrets. After all, that’s what girls do. I can suggest some exercises that will shape your body into one bodacious babe if you want to make your transformation complete. Or you can cheat and get some body shapers that can create that effect.

We can shop online together. I can help you pick out really beautiful lingerie that makes you feel and look so sexy. Understanding the difference between sexy and trashy is crucial. You can be a hot slutty girl, but never under any circumstances, look trashy. We can select the right colors that compliment your hair, eyes and skin tone. My only goal is to make you to feel confident and beautiful.

 

IsabelleWritten By: Isabelle
Call Isabelle @ 1-866-704-9517
Email- isabelleisgoing2rockurworld@aol.com

 

 

 

You Are A Fag

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Let’s face it, you are a fag.  That’s cool though, as I love fags. Most girls watch guy with girl porn, but I watch guy on guy.  You’re still trying to decide if you are gay.

You dislike pussy, even mine? You are a queer. Fucking face it, you love cock. You are gay. Maybe it’s time for me to show you just how much of a queer boy you are.

I love how you blamed your boring girlfriend and told me that if she were more experimental. Guess what? You would still be a cock sucking fag.

Guess what else? Maybe I should just contact her and blackmail you. Maybe, I would be doing you a fucking favor, so you can get all the cock your fag mouth and ass desire? I am just here to help in the end. Now, if you believe that!

I’m in the room looking hot as fuck, your boring girlfriend is there, and then we have a tall muscled guy with a 10 inch cock. You’re down on your knees before he can even unzip his pants. Guess what, you are a fag!

 

 

 

 

MalayaWritten By: Malaya Maxxx
Call Malaya @ 1-866-659-8370
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Email: malayamax@aol.com

Valentine’s Day Panties

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 You have been snooping in my bedroom again, haven’t you?  You see the sexy red satin panties on my bed. For a brief moment you think about me in them, but then your thoughts go in a very different fucking direction. You check the time, and know I won’t be home for several hours. You giggle, as you rub them against your face, feeling how soft they are. Checking the clock again, you  slowly strip as you watch yourself in my full length mirror. You put on Bump and Grind, and begin to dance as you slip on my red panties. You run your hands down your body, feeling so sexy.

You hear laughter at the door, and turn around to see me and 2 friends watching you. Don’t you look so adorable?  My girls dance with you for a few, as I pick out sexy lingerie for you. A red clincher, red 6 inch stilettos, red satin bra, cherry red lipstick, and a red wig. You look like a slut! You’re so excited, and begin to dance some more. 

You beg us to take you out for the night with us. We pick the perfect dance club. There is always hot professional men looking for a walk on the wild side. You flirt with the bartender, and you get all our Painkiller cocktails for free. That gives us all an idea. We’re all giggling but you have no idea why. I talk to the bartender and soon men are waiting in line at our table. I take their money and follow you into the restroom. You pull up your dress and take off your panties. A line is forming, and I watch you take 4 cocks at once. Quite impressive, I must say.

Happy Valentine’s Day to all my Sissy Sluts!

 

HarleyWritten By: Harley
Call Harley @ 1-866-415-6699
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Email: Aol/Yahoo- cumrideharleyphonesex

 

Jade’s Closet

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http://www.smittenkittens.net/Journal/wp-content/uploads/2019/12/jade1.jpgAre you jealous of my naughty schoolgirl outfit? You wish you could wear something like this, don’t you? I bet my hot, little outfit would look so good on you. In fact, I have many outfits in my closet for you to wear. After I pick out the perfect, slutiest outfit, I’ll do your makeup. All my girlfriends want me to do their makeup, so you’re in good hands.

My strap-on will defiantly be coming out and shoved in your slut holes, along with other toys from my collection. Don’t get to use to the rubber though, because soon enough you’ll be experiencing the real thing.

I will make you look and feel really girly. I know you’ve been fantasizing about this for awhile now, and this is the time to make you the perfect sissy you’ve been wanting to become. Once you step into my closet, there’s no going back to your plain ole boring self again.

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Written By: Jade
Call Jade @ 1-866-949-4312
Email- juicyjade4fun@gmail.com

 

Sissy Ends Up In Military School

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A Mom came home from her job. Her co-workers made plans to celebrate the completion of a big project that night at the bar. There had been so many late nights, and Mom felt guilty about leaving her teenage son alone so much. Instead of going out to celebrate, she left an hour early because she wanted to cook him a special dinner and hang out with him. 

She drove home and entered the quiet house. She checked his bedroom and found it empty. Mom goes to her computer and looks up his location through an app on his phone. Shocked to learn that he must be home, but she must be doing something naughty because he is so quiet. Without making a sound, she searches the house, and the last door she opens is her bedroom. She finds her son! 

Mom discovers him wearing her expensive lingerie, sucking on the dildo from her nightstand. WTF? Her son is a Sissy! The Mom falls to her knees and breaks down and bursts into tears. The son stands there ashamed and begs for forgiveness. Mom spends the night researching solutions on how to turn him from a sissy to a real man. She wakes her son at dawn and gives him the news. 

The furious mother informs her son that he needs discipline and needs to be surrounded by alpha men, real men. He needs a mentor, someone who will break him of his sissy ways. Mom has already arranged to send him to military school, a boarding school. Being a single mom, maybe she cannot teach him how to be a real man. She hugs him and says this is the best thing for him. He will leave today. 

On his first night in the dorm, all the boys identify him as a sissy, and they treat him as such. They force the new boy to dress like a sissy, frilly panties, bra, thigh-high stockings, and lipstick. They hold him down and fuck his little sissy boy mouth. The boy loves his new home. His fantasy becomes his reality. Now he can be a cock sucking sissy whore every night! 

 

Sarah JesseWritten By: Sarah Jesse
Call Sarah Jesse @ 1-866-500-3859
Email: Aol/Yahoo- badsarahjesse

 

Mirror, Mirror

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Mirror, Mirror on the wall, who’s the slutest of them all?

YOU ARE!

It used to be that I was the mega slut but now that you’ve been trained by the best, you now take the title. Let’s get you all dressed up from head to toe so you can take a bow.

I came up with a wonderful way of how you can thank me. I know you graduated from the dildo in your mouth then to your ass. Before long, you finally got up enough courage to answer a Craigs list ad and sucked your first cock. It was a proud moment for both of us.

So how can we take this to the next level? You and I know you’re  ready and I have no doubt you can handle this task.

The best way of thanking me is to have your first gang-bang. Now, before you panic; I’m not suggesting 100+ guys! I was thinking maybe 15-20. I know this is something we’ll both enjoy. Nothing would make me happier and prouder than to see my little slut dripped in cum. Don’t worry, I’ll be there cheering you on while your holes are being stretched and violated by huge cocks. I hope you’re excited as I am.

The One and Only, ~M.M.~

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MemphisWritten By: Memphis
Call Memphis @ 1-866-629-7037
Email: memphismonroe80@aol.com

 

Princess For a Day

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The bitch is on a rampage today! I walk past your desk in my loud stiletto heels and tell you I want to see you in my office right now!

When you walk in, I have you close the door behind you. I tell you to sit down and I ask how my little Princess was today? You seemed shocked that I would call you Princess. I tell you that I noticed you were wearing women’s panties when you bent over to pick something up, and this isn’t the first time I’ve seen you wearing something feminine. Your sad, pathetic face turns immediately red and you are very embarrassed, telling me it will never happen again.

I ask you to stand up and take off your clothes. You don’t seem willing but I remind you that I sign your paychecks. You take off your pants and you have on silk pink panties with white bows on each side. Once you unbutton your shirt, I notice you have on a matching bra as well. I tell you to keep both your bra and panties on.

I didn’t realize you wanted to be a Princess? Why didn’t you say so? I grab my makeup bag from my purse. After I make your face pretty, I have you stand in front of me and rub your clit through your panties. I pull out my strap-on from my desk drawer and put it on while you’re still playing with yourself. You seem scared by the size of my cock, but I tell you if you want to be a good little Princess and keep your position here with the company, you must follow orders. I demand you to bend over my desk. I slide your panties to the side, and you feel the head of my strap-on going inside your pussy. I hear you whining like a little bitch and that forces my hips to thrust faster and harder. The bitch boss loves turning little Princesses into cock whores.

 

 

Written By: Christine
Call Christine @ 1-866-949-4310
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Email: bitchbosschristine@aol.com

 

The Prettiest Sissy

| Jenny's Blog, No Limits Phone Sex, No Taboo Phone Sex, Shaving Phone Sex, Sissification Phone Sex, Sissy Lessons Phone Sex, Sissy Phone Sex | 0 Comments

When you slide on your favorite pair of nylons something doesn’t feel right. Don’t get me wrong, it feels good but not silky smooth like you hoped it would be. I want to be your personal guide to make you feel like the prettiest sissy in the whole entire world.

First, let’s draw you a hot bubble bath. Every sissy needs a little pampering. After your done relaxing in the tub, sit on the side of the bath tub and lets shave those hairy legs and transform them into silky, girly legs. Next, I want you to look in the mirror at your cock and balls. I want you shave them completely and turn that into a beautiful, hairless pussy. Once you are all done shaving everything, I want you to put on some good smelling lotion all over your body.

Now comes the fun part. I want you to slide on a sexy pair of bra and panties. Slip on your stockings on your new pair of legs. Feels so good, doesn’t it? You can’t keep your hands off your legs because it feels so amazing. Your skin is so soft and with the pair of nylons on your freshly shaven legs gets your clitty hard. All you have to do now is call me and I’ll take it from here.

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Written By: Jenny
Call Jenny @ 1-877-292-5338
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Email: sexyliljenny4u@aol.com

 

 

Sissy Talk 101

| Jenny's Blog, No Limits Phone Sex, No Taboo Phone Sex, Sissification Phone Sex, Sissy Lessons Phone Sex, Sissy Phone Sex | 0 Comments

I had a caller the other day that asked me a frequently common question: What are you wearing?

I just got home from a date and hadn’t changed yet but I told him I was wearing a little black dress, black thigh highs and heels. He seemed overly turned on. After a few minutes of talking to him, I figured out he was getting hot with what I was wearing because he wanted to dress like me. I knew right away I had the perfect outfit for him in my closet. I could hear the excitement in his voice when I was describing what he would look like with my pretty pink corset, and all the accessories to match.

He was pretty new to this so I went into detail of how he should look from head to toe and explained the process. I’m experienced in sissification and transforming you into what you’ve always desired and trust me, no one can keep a secret like me.

There’s nothing I love more than bringing out your inner sissy.

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Written By: Jenny
Call Jenny @ 1-877-292-5338
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Email: sexyliljenny4u@aol.com

 

Looking For My Barbie Doll!

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That’s right, I’m looking for my Barbie Doll to play with. I want to give you special beauty assignments, such as first by shaving all the hair off your body. Then giving you ballet workout to really tighten your core.

Next, would be placing you on birth control and hormone supplements so I can watch your hair, nails and most of all having your breasts grow for me.

I can’t wait to paint your toes, nails and do your makeup to perfection. I want to put you in that extra tight pink push up bra and matching pink thong panties. I will also make you walk in those extra tall “cum fuck me” heels. Let’s not forget doing your long hair and painting those lips to match your nails. You can even carry a purse for me while you prance around.

Just remember though, once you look like a sissy slut, you’ll be fucked like a slut. I can’t wait to use all your fuck holes and make that sweet tight Barbie pussy mine!

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Written By: Parker
Call Parker @ 1-888-307-4889
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Email- playfulparker4phone@aol.com