Category Archive: Sissy humiliation phone sex

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July 21, 2016

by Phone chat numbers slut

There’s nothing I love better than training a sissy. Making a man into a tranny slut is better than playing dress up when I was young. I do his make-up and put him into something frilly, sexy, or lacy. Every sissy wants to feel silk on his cock. Then the fun begins. I start with some teasing when I see that tiny cock of his. You know a big girl like me could hold you down and violate your new pussy. I do enjoy some fisting. But what really makes me wet is when you play the role and your voice changes. You become the little faggot slut of your dreams. I will teach you to walk and flirt like a girl. You’ll learn the proper techniques for cocksucking and how much fun swallowing sperm is. I’ll be your big BBW girlfriend and you’ll be my little sissy trainee. I’ll put you on your knees, slowly lick your shithole until you’re moaning. Then it’s time for my strap-on right in your new pussy. Make sure you bring that ass toy when you call me!!! I’m gonna stroke, bang, molest, and totally fuck that new cunt until you believe that you’re a girl. You’ll be calling back for more.

BBW Sissy Trainer Delphine

855-213-2229

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Sniff my nasty panties.

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July 8, 2016

by Phone chat numbers slut

I know how much daddy loves the smell of my used panties. So I wore mine all weekend. The little cotton crotch was almost stiff with pussy juice and dried cum. I put them to my nose so I could smell myself. There was a faint hint of urine and I could see just a smudge of shit where I didn’t clean my asshole very good. Or maybe daddy had just fucked my booty hole too hard and it leaked a little cum and poop. Anyway, I was sitting on the toilet taking a pee and kicked my undies off unto the floor. I knew this would get daddys attention. I giggled as I imagined him with my panties on his head, sniffing my secret smell. His hand would be on his cock as he licked them. And being the good little daughter I am, I’d be waiting in my bedroom with no panties on under my nighty. I knew my daddy would be coming in for a little goodnight kiss. I’m such a naughty girl. Wouldn’t you love a pair of my dirty panties for your very own? Just ask. I’ll send you a nice crusty, gooey pair. Mmmm. They smell so good. Please fill them with your cum, daddy.

Tiny Teen Jenny

888-229-1702

Tags: Girlfriend phone sex, panty boy phone sex, phone chat lines, phone chat numbers, teasing phone sex, Teen sex blog

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Put those panties on.

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July 1, 2016

by Phone chat numbers slut

I found the evidence today. A pair of panties tangled up in your jeans in the hamper. MY panties. Oh, I warned you already about the punishment I’d inflict if I caught you again. And here it is. Complete with cum stains. This one is gonna hurt. I’m taking pics for FB and posting them. “My sons loves to wear my panties.” followed by tagging your name so that all of your friends see your dirty little secret, your shame. They in turn will share that post and soon it will go viral. You will be known everywhere as the panty wearing little sissy. No girl will date a sissy. You do get one last chance though. Call Mommy and apologize for being such a sissy slut and I might just forgive you. No one will have to know what you wear underneath your football jersey.

Sissy Mommy Pearl

855-267-8781

Tags: grandma sex blog, mature phone chat, Mommy Phone chat, panty boy phone sex, phone chat lines, phone chat numbers

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Phone chat numbers for discipline.

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June 17, 2016

by Phone chat numbers slut

Busted. That’s what you are, young man. I see you in my panty drawer again. I warned you the last time what would happen. I promised that your punishment would be strict and severe. Now drop those panties and bend over that bed. Since you want to wear panties, you don’t need those balls. How about if I spank them hard with a fly swatter? That’ll sting a bit but it won’t teach you a lesson. I have a better idea. I think I’ll rubber band them and let them fall off. Oh, imagine the pain as they swell and turn purple and then black. You’ll be a girl for sure after that. Your little penis will shrivel up and you can wear panties all you want. We’ll call your asshole your pussy cause that’s where men are going to stick that big fat cock. Then you can wear all the panties you like.

This time, I’m just gonna bust that ass and leave some welts but next time you can count on becoming a girl. This mama doesn’t play games. She gives punishment out to bad little boys.

Disciplinarian Queen Pearl

855-267-8781

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Let me take your money and your cum.

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June 8, 2016

by Phone chat numbers slut

I can be a sweet mommy or I can be a wicked slut. When it comes to my boys, I’m nurturing but tough. But when I go out on the town, I’m looking. I turn into a cougar looking to add men to my collection. I weed out the sissies and take control of them. A little blackmail and they give me what I want. I see nothing wrong with a little financial domination to make a little extra. I give sissies exactly what they want. A taste of my fat black strap-on. They arch those asses right up in the air for me and I ream them out good. I love laughing at the little throbbing cocks as they whimper and beg for more. I believe they love being used this way. They seem to love it more when I threaten to expose their dirty secrets. Oh, imagine the shame if friends and family knew what they did behind closed doors. Better pay Mommy well to keep our little secret.

Cougar Mom Pearl

855-267-8781

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Sissy Humiliation Phone Sex Fun

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June 2, 2016

by Phone chat numbers slut

Sissy humiliation phone sex is so much fun for me. I love shaming pathetic cross dressing cock sucking pansies with little dicks. When a sissy calls me, I can hear it in her voice. The girly shrill, the whining, the lisp, the pathetic stories. I run a sissy school. I take pathetic losers and turn them into sissy maids. Something a woman can actually find useful. Sissies need training; they need a strong mistress to own them. For me, a sissy has a lot of value to a dominant woman. For one, they are so much fun to humiliate. I know. I look too mature to be a mean girl, but sissies deserve ridicule and public humiliation. In fact they crave it. Never feel bad for a sissy. The entertainment value alone is worth having one in your life. You can dress them up in frilly dresses and make them prance around in public singing shameful little ditties. Sissies also make fun shopping companions. They can model all the clothes for you and carry your bags. Plus if you find one who can pretend to be a man 9-5, she can support your shopping sprees if she has a good day job. Sissies serve drinks and cater to a mistress’s needs when properly trained to do so. Sissies give great pedicures and back massages to a mistress who has had a long day. They need direction, however, a strong hand; but once trained, they make the perfect doting maid. Don’t even get me started on how good they are for date nights. They can fluff cock, clean cream pies and even procure you real men. So if you are an unattached sissy in need of some guidance to become the best sissy you can be, put on some panties and call me. Sissy school is always in session.

Sissy Trainer Farah

1-888-495-7259

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Perverted Phone Sex Needs Fulfilled

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May 29, 2016

by Phone chat numbers slut

Well are you a real dirty man and desire some perverted phone sex outlet? You are in luck when you get with me and trigger my super naughty hot phone chat. Seriously, your little Sissy pecker will twitch in those pretty panties you are keen on wearing.

Your such a naughty sissy aren’t you, and you NEED me to tease you with my kinky phone sex. My sensual voice directing you to dress up pretty for me and to suck cock will make you weak. We will get into some super naughty fun as your age play fantasy comes out. It is no surprise just how quickly you cream those pretty panties once we start to really get filthy. Are you able to let loose sissy?

Felecity

877-458-8632

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Sissy Boy In My Panties Again

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May 27, 2016

by Phone chat numbers slut

As I walk into my office, I find you prancing around in my panties and high heels. This is the third time I have caught you in my clothing. This time its one of my favorite pair. It is pathetic how you like to dress like a little panty fairy boy. You work in a strip club for fuck sake! Maybe you would like to prance around the stage for all those hard, horny men? Maybe that is your fantasy. After all, then you might get to see a real cock instead of the tiny package you have fit into my bikini panties. I warned you that would happen if I caught you in my clothing again and here you are. You might as well finish dressing in one of my full stripper costumes. I think my Little Bo Peep costume with all the ruffles would be perfect for such a girly man. You will be tonight’s entertainment. You will have all those cocks standing erect for you as you dance and strip. Are you ready my little sissy? You never know what is going to happen when you step onstage. Maybe you will get lucky and get to take one of those big hard cocks down your throat or up your sweet little ass tonight. I see that tiny prick has gotten a stiffy thinking about the possibilities. You will be an excellent main attraction. I know you are ready so go shake that sweet little ass for those real cocks!

Deanna

855-581-7667

Tags: panty boy phone sex, perverted phone sex, sissy humiliation phone sex, sissy phone chat, teasing phone sex

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The Double Trouble Mommies Daphne and Darla

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April 26, 2016

by Phone chat numbers slut

The first time I met Darla, I did not like her. The way she fussed over her precious son. But then I started noticing things. It’s not that he was crying when he fell but she would almost overreact on purpose to make him cry like a sissy. That is when it clicked. She is training her son to be her sissy! I wish I would have thought about that! My son is sometimes affectionate but not like Darla’s son. He would be crying and saying sorry, telling his mommy how pretty she was and he kept trying to kiss her on the mouth. I knew she was a dirty P-Mommy just like me. Every time he fell down she would rush him into the women bathroom.

I fallowed her and brought my son with me. We waited a few minutes and walked in. We could see Darla’s son on his knees in front of the toilet but we didn’t see her feet. I stood on top of the toilet and looked over. I was instantly wet and my knees became weak at what I saw. Darla had her leg in the air as her son was eating her pussy like he was never going to have it again! She sat up real quick and started to panic. She opened the door with her panties down and her legs were shaking. I interrupted her as she was about to cum. She ran to the door and locked it. She started to say something and I kissed her. I kissed her so deep she became weak in my arms and I started fingering her pussy. I wanted this nasty p-mommy and her pussy eating sissy son!

Daphne

855-769-5871

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Your new Mistress is here.

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April 26, 2016

by Phone chat numbers slut

Hey, little sissy. You looking for a Mistress to take control of your life? A mature woman like me who knows exactly what you need. A firm hand and no excuses. You obviously cannot control it yourself. You and that tiny thing you call a dick. No wonder you wear the panties in that house. I bet your wife has no idea that you wear her frilly things. Or that you love to suck cock. Being a mom with a sissy son of my own, I will treat you discreetly but kindly. However, if you deceive me or fail to tell me all the details of your latest tryst, I will dole out a punishment. Maybe it’ll be a revealing blog telling people all about you or maybe it will be financial blackmail as I make you buy your Mistress anything her heart desires. Are you ready to be my property?

Sissy Mommy Pearl

855-267-8781

Tags: Grandma Phone Sex, grandma sex blog, mature phone chat, Mommy Phone chat, phone chat lines, phone chat numbers

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Hot Phone Sex Happens When Calling Reesa’s Phone Chat Number

February 23, 2025Who doesn’t love calling a phone chat number 24/6 to help you get ofI couldn’t help myself, the sight of my boyfriend’s young daughter was too much for me to resist. She had just come out of the shower, her body still glistening with water and innocence. As she walked past me in nothing but a towel, I grabbed hold of it roughly and pulled her close against my chest. Her small breasts pressed against mine as she let out a soft gasp. “What are you doing?” my boyfriend asked from downstairs, unaware of what was happening up here between us now that we were alone together like this…or so we thought! “I can’t control myself,” I whispered into her ear before lowering one hand down towards where no one should go – especially not someone so young. ! With gentle yet forceful movements on my end (hers being more reluctant), we began to play. Her pussy felt hot and wet against my fingers, even through the thin fabric of her towel. I could feel how ready she was for me or her dad as I teased her cunt hole with gentle circles around it. She squirmed in my grasp but didn’t try to pull away – instead, she seemed curious about what was happening between us despite knowing deep down that this wasn’t right or proper behavior for someone so young! “Does it feel good?” I whispered into her ear again while continuing our forbidden play time fun “Yes,” came out softly from those lips formed by innocence itself before parting them slightly wider invitingly when another finger slipped inside hinting at just how eager (or desperate)she might be feeling deep down inside where no one else has ever gone before [...]

Phone Chat Numbers for sissy whore training

February 21, 2025Phone Chat Numbers are a perfect spot to find a dominatrix hottie to train you. Something inside you has been stirring since you ran into sissy whore porn. You saw a big black bull fucking a tight white sissy man pussy and it had your cock hard. “Don’t worry it’s ok to faggy thoughts” I said to you as you walked in. “Tonight I’ll show you what your made to be” I wink and hand you a pair of panties. “Put them on and wait on all fours, like a bitch in heat” I instruct as I walk away. When I come back you were waiting with your ass in the air wiggling in excitement. Your body starts to tremble and your eyes get big when you see who walks in with me. Its a big naked black bull. His monster cock swing in between his legs like an extra leg. I knew you were needing to be trained when I saw tour mouth start to water. “Open your slut mouth and eat bitch” I say as i grab his cock and point it at your face. The moment your lips touch his black dick, something clicks in you. You starts sucking his cock in ways a hooker whore would. When I looked down and saw that your clitty was stiffening inside your panties, I start to laugh. “What a filthy whore you were made to be” you hear me say, as I move your panties to the side and expose your sissy cunt. Buy I wanted to tease you, I wanted you to beg. Therefore I spank you a bit more while teasing your sissy hole with my fingers. “Please mistress, let me get broken in like a sissy whore gets” you start to beg over and over. Seeing and hearing you submit is the reason why I love to be a sissy trainer. “Break this sissy bitch in and fill that ass up” I say loudly. Once my guest hears that he knows what to do. I use his big black cock to break many of my bitches in. That’s why he quickly hot behind you and rammed his massive cock meat in you. As you grunt and moan I laugh and cheer. “Now you’re the hoe you were made to be” I say laughing. Soon your ass was filled and your panties were drenched from your sissy clit. [...]

Phone chat lines have submissive pain sluts to dominate!

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Phone Chat Numbers for Violent Fantasies Serve as Therapy

February 15, 2025Phone chat numbers for sadistic bitches are what you need. With the economy, politics and life stress in general, it feels cathartic to get those violent impulses out in a safe space with no judgement. I am a sick bitch. And not for the faint at heart. Never for the faint of heart. I do not indulge in vanilla fantasies. I only entertain dark fantasies. Yesterday, I helped a man get out his impulses for his bitch boss. She cock teases him, then threatens harassment. Plus, she passes him over for promotions and raises all the time. So, he needed an accomplice for his revenge fantasy. And he picked the right bitch for the job. I love violent sexy role plays. We kidnapped his bitch boss and tortured her for hours. I took her to my dungeon torture chamber. We tied her up to this medieval rack I have. Stretched her almost too tightly. Any tighter we would have ripped her in half. And that would be a fast death. She did not deserve that. Plus, he had to mutilate her tits and her pussy first. The goal with me is to inflict optimal pain before death. A quick death is never satisfying. You need to make the moment last. My Phone Lines Serve as Therapy for Men I egged him on like the devil on his shoulder. He lit her nipples on fire. And boy do I love the smell of burning flesh. I find it rather intoxicating. He cut off her clit. But her screams of pain only made him and I more aroused. With her bloodied tortured body, I watched as he fucked her. And as he plowed her bloody cunt, I shocked her tits. She convulsed and twitched as he continued to fuck her. But that made us torture the bitch more. Eventually, we ripped her in half. Sometimes, a violent role play is therapeutic. And that’s why my phone chat lines exist. [...]

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February 12, 2025Phone chat lines is a great place to find bbw sluts like your niece. Just like my uncle you used me to make you and your friends cum. It starts with you using my juicy jugs to stiffen your dick. You squeeze my jugs around your uncle cock and use them to jerk off. After a bit your friend walks in and right away I open my mouth. His big dick is pushed down my throat while he pinches my nipples. “Don’t stop I’m almost balls deep” he said as he kept pushing his cock down my throat. At the same time you jerked off and played with my fat pussy. It made my chubby cunty wet but I just wanted to get his friend off and be done. But I didn’t do it fats enough. Because soon my uncle was spanking me, telling me to bend over. “Bend over its time to really milk dick the right way” my uncle said sternly. Feeling his big hard dick push deep inside my cunt, made my fat cunty drip. At the same you pushed your big uncle cock in my mouth. You both used me and fucked me hard, not caring if I liked it or not. “Fat nieces are made to milk big dick” you grunt as you fuck my mouth. “Keep going fat little slut” your friend moans as he pumped my cunty. Soon you both were filling me up. My mouth was getting a big uncle load and my fat cunty was getting your friends thick gooey nut. Now I’ll milk my uncle and any friend and I love it. I cum just as hard as they do. They’ll give me a big load in any hole, because that’s what nieces were made for. [...]

Phone sex blackmail you better watch out I got audio.

February 8, 2025 Phone sex blackmail you better watch out I got audio. Now, I know you liked the talk and your confession. You know about the candy, the sweet little demon that you just had to have the bald bare younger pussy. Not even old enough to grow hair yet. So young, so spoiled now. I have the audio; I have the zoom. Recorded it all. Blackmail…hmm such a bad word. To point out that yes, I am blackmailing you. To begin with I want you to get me some more candy, next, I want you to be a lot nastier with the toys. No more will you ask them to say I want you to take me. Spoil my fun. Tell me what p-daddy you are. They aren’t goblins or demons, even brats. No, they are now just fucking toys. Made to be used. You have the candy, I want it. I have toys you like. In other words, I will continue to blackmail you, as long as I have the leverage you will do as I say. Phone Chat Numbers brought you to me. Now, you are under my thumb and I demand you be dirty to the toys. Until I finally get off numerous times. Then you can cum but only then. Until next time, it must be remembered that I still have the audio. [...]

Phone chat numbers have Giantess Blondes

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My Phone Chat Numbers are For BBC Faggots and Cuckolds

January 26, 2025My phone chat numbers are for cuckolds and black cock faggots. And there are a lot of black cock faggots out there. Men tell me they just want their wives to enjoy some real dick. But I know the real reason they want to be cuckolds. They want those big black dicks too. However, they do not want to admit that because they think if they do, it means they are gay. You can be straight but gay for big black cock. It is easy to get mesmerized by a huge BBC. They are leaps and bounds better than the average white dick. Bigger, thicker with better stamina than white dick. That is just the facts. So, if you call my phone chat lines, I will take you down the rabbit hole of big black cocks. I cuckold my husband. And I have for 30 some years. He went from a cuckold husband who knew I fucked black men, but never wanted the details, to a black cock sucking faggot. And trust me it is so easy to do. Smart men know they cannot compete or compare to BBC. Those men recognize their short comings. You Can Be Straight But Gay for Big Black Cock But there are still men out there who refuse to recognize black cock superiority. But I bet they would crumble if they saw their hot wife getting some black cock. I still remember the first time my husband watched a black man fill my fuck holes with a gallon of jizz. He had this look of awe on his face like he could not believe what he was seeing. I tell men all the time seeing is believing. And that goes both ways. Women need to see a big black cock to realize how much bigger they are compared to their husbands. And men need to see a BBC fucking his wife to understand he cannot compare. Let me help you be a good cuckold and BBC faggot. Cuckold therapy is the best kinky phone sex. [...]

Phone chat lines with a sissy trainer

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