Tag: sissy training phone sex

Naughty Sissy Faggot

You’ve been a very naughty sissy faggot. Mistress Levi let me play with you and I told you to be a good girl and put on that sissy maid uniform but what did I find you doing? I found you sniffing my panties when you were supposed to be cleaning. What a pervy little girl you are.

Dominatrix Phone SexI thought I could leave you alone as I got ready for my date. But naughty girls need to get punished. So come here, lay yourself over my knee. That’s right, I’m going to take this hair brush and spank you for being a naughty girl.  Smack! Right across that diapered booty. You squirmed and whimpered but I did another Smack! Right across that padding. Giving you three, four more before I notice a warmth press against my thigh. “Did you wet on me prissy sissy?” You squirm and whimper, your cheeks going red before admitting. “Yes, Ma’am.”

Sissy Phone SexI pat your ass a few times with my hand. “Very naughty sissy.” I chide. “Let’s get you changed.” letting you get up and change your diaper for a clean one. “My date is almost here.” I let you know. “I’m going to put a cage around that naughty little bitch clit so that you can’t get to excited with your itty bitty clitty. Then I want you to stand in the corner until he gets here. If you’re a good girl maybe I’ll let you service him for me to show just how good you are.”

Sissy Training Phone Sex

Sissy Training Phone Sex is HOT!

Sissy Training Phone SexI love my sissy sessions. The prettier they’re willing to get, the happier I am. She came to my door in the sweetest pale-pink dress, complete with a parasol and some strappy heels. I invited her inside, offered her a drink, and told her that my friends would be by in a few minutes. She told me that her goddess knew where she was, what she was doing, and that she hoped to have an amazing time to tell her goddess all about later. I told her that would all depend on how good a girl she was. When my friends got there, I invited them in, settling them on either side of her on my couch. Tranny porn picturesI told that little prissy sissy that she was to take their cocks out and start stroking them. She was a good girl, doing exactly what I asked of her. Between the fellas and me, we started stripping her pretty dress off, only to find some matching, pale-pink lingerie underneath. I called her a fruity little fag, and made her get down on her hands and knees in that pretty matching set. One of the fellas squatted in front of her, shoving his dick down her throat, face-fucking her. The other pulled those pretty panties aside, pushed a finger up inside of her. He spit on her sphincter and then replaced his finger with his dick, pushing up into her. He stretched her so much, that she was groaning on that dick in her mouth. She was the best little tinkerbell transvestite I’ve seen in a while. Watching her get plowed got me all hot and bothered, too.Hot ass sex

You want my advice, do what I say

Sissy phone sex Janelle

I have a distant relative that the family calls the little fairy fag of the family. Her name is Sissy. She called me today and wanted some advice on being a good submissive. I am hot, take care of my body and know how to get exactly what I want with my pussy and perfect titties. Sissy is the opposite of me. She is a little fairy queen with a little cock, insecure and never goes after what she wants. I am a dirty fucking whore, but the men that touch me have to be loaded and know how to use their cock and their tongue.

Guided masturbation JanelleSissy is somewhat naïve and doe not know how to present her goods and she gets taken advantage of a lot. I kind of feel bad for Sissy. So I told her she could come over and that I would give her some pointers on how to please a dominatrix by being a good and obedient sissy bitch. I told her I do not want to waste my time so I told her she will have to do exactly what I said no matter how gross or mean. Sissy agreed and decided to come over. I was amused and I kind of took advantage because I wanted to see just how far Sissy was willing to go.  Guided masturbation SissyI made her do things like drink her own piss, put a pacifier in her ass hole and then suck on it and a few other things. Sissy did really good. I noticed that Sissy had a really small tinkerbell weiner though. I wanted to see how hard it got and how long when hard. I made Sissy play with herself and lick my cunt since I was spending my time helping her out. I could not help but laugh, it was pitiful. Sissy really is a little tinker bell faggy waggy princess. That cock can not even count as one. Sissy should have a vagina.

shopping with the sissy fairy fag

sissy phone sex

I have my prissy sissy with me today. He is so fun to hang out with. We go to the mall to look at makeup. Of course, being the panty pooping crossdresser that she is she complains about the store I choose. She begins to act like a fruity fag. I take her to the bathroom and bend her over my knee. I pull down her white cotton panties and begin to spank her.

sissy training phone sex

She screams about how mean I am. I tell her I am doing this for her own good. I pull out my cock holder. I adjust it to her teenie weenie clit size. I place it on her. She complains it hurts. I tell her to stop being such a poopie pansy as I tighten it up. We head back out to the mall. She complains all the way home about not getting any makeup. I tell her it’s her own fault. She folds her arms and pouts. What I prissy sissy she is.

spanking phone sex

Sissy phone sex with our site mascot is so fun!

sissy phone sexSissy phone sex with our site mascot is so funny! See, sissy is a fake man lawyer, a real big shot where she comes from and to me it is hysterical that she really thinks no one knows her secret there! I mean seriously, she walks around her town in her little sissy dresses and wears funny signs and takes pictures… she even poops her panties and walks around like that! Who wouldn’t notice that shit going on around them??? Come on, everyone sees her, everyone knows her and honestly, even if they had never seen her dressed like a sissy they would still know she was a total faggot!

small cock humiliation phone sexShe swishes when she walks, every mannerism is very feminine, she even gets her nails done and wears her little hoopy earrings! But we are supposed to believe that she is a man? Hahahaha she is no man, she is a tinkerbell transvestite, a poopy panty wearing wannabe princess, a fruity fag, all that but definitely NOT a man! That little teeny clitty she has between her legs is no cock either, its definitely just a clit, something to rub on not something for her to stroke.

humiliation phone sexNo our little site mascot is definitely not any kind of real man, she is just the little sissy fairy faggot that we love to tease and laugh at! In fact, she is even paying for this humiliation right here too! I bet half of her town sees these blogs about her and whispers behind her back about what a little sissy she is, there’s no fuckin way that they can’t see thru her act! Lets face it sissykins, all those judges you go before are laughing at you. They all know your secrets, they know you are nothing but a poopy panty wearing little sissy fairy faggot! Think about that next time you go to court…

Deep Throat Princess’ Strap On

Sissy Training Phone Sex

As you know, a sissy’s training is never done. One of the first things a sissy needs to learn is how to deep throat my princess strap-on. A princess can never get enough of a sweet sissy mouth on her cock. I want you to strip completely naked. Don’t worry, I have seen plenty of tiny clitties before. Yours is no different. Get on those soft knees of yours and suck it down slowly. Gagging up a little spit is par for the course, just use it as lube honey! I know that makes your clittie throb and your sissy clitty pucker and ooze. Pretty soon you will be begging me to fill you up, but I won’t! You have to sit up and beg like a little poodle. Aww..come on, whimper for me!

Snuff Phone Sex with The Sitter!

Snuff Phone Sex

He wanted to play a game with me and I was tired of dealing with this little fucking brat. So I decided to take things into my own hands. I figured if this little shit wanted to play a game we were gonna have my kind of fun! I tied him down on the Kitchen island. He thought it was fun at first. He giggled as I took the very sharp kitchen scissors and started cutting his clothes off. He smiled as I started cutting his panties off. When I pulled them off I could not help but laugh at his tiny at his tiny cock. I went into the kitchen and turned the gas burner on. I placed each of their knives they had on the gas stove to let them get red hot. I went back to my patient who at this point was screaming to let him go. I grabbed his tiny hard cock and started rubbing it. His body started to relax and he tried to fight the pleasure that was being forced onto him. I made him cum and separated his balls with clamps as he seized in pleasure. I started to rub his cock again. Harder this time. Forcing him to get hard for me. He was begging me not to touch his cock. Begging and pleading. I smiled and put a clamp on the tip of his cock when he was rock solid. I went back to my knifes and started slicing through his tiny balls. He started to scream when he saw the smoke coming up from his legs. When he smelled his burning flesh, he started to feel it. The knife wasn’t as hot anymore and I was basically sawing through his ball sac. Every time he would pass out from the pain I would stop, put my knife back on the stove and begin to stroke his cock until he was rock hard. He was going to be awake during every last part of this. I didn’t want him to miss me playing with him.

What a little bitch

sissy phone sexOMG what a little bitch you are! Look at you pathetically sobbing because I won’t let you ruin my dress, you have your own slutty clothes go wear those! Since you want to act like a little bitch sissy, I think I will treat you like one today, go get dressed we’re going out. I’m going to take you over to my friend’s house where there are lots of horny men waiting to pay me to abuse you. I’m going to make sure that they all take a turn on you! Your little man pussy is going to be stretch wide open and dripping with cum… you will have a belly full of it too. They are all going to take a turn on you, they’re all going to make you the whore you’ve always been meant to be!

He wishes I’d give him this pussy

Sissy Phone SexOne of my pathetic sissy boys called tonight. He wanted to do an over the phone sex fantasy. I was totally down of course. I can get off to making fun of him on the phone just as well as in person. I lay down in my bed and get relaxed. I make sure and clarify that he is not fucking me on the phone either. He sighs but I know he loves everything I do to him. Otherwise, he wouldn’t keep coming back! He loves to be called a dirty little bitch. He is a nasty slut kitten who loves to take big cock in his mouth and ass. I give him a story. We are at his house. He wanted to have a house party. ( I know how cute and desperate) He leaves it up to me to put it all together. I invited over two of my girlfriends. I will call them slut and whore. Really the names fit them perfect! They are some sluts for sure. ==giggles== I command my phone bitch to strip down naked. He tries to ask where everyone is at but I cut him off. I tell him not to speak if he is going to argue or that will be two lashings added for the next time he is in my presence.  He obeys. It is silent on his end. He likes the whippings of course. He definitely doesn’t want to acquire more than his weekly total. I tell him we brought some toys. The slut pulls out a big black novelty dildo. The kind you are supposed to give as a gag gift. This dirty fucking skank loves those big cocks up his ass. the slut lubes the huge cock up nicely. we don’t want to hurt our little bitch boy toy too much. Just enough to make him cry and cum.  she slips it into his loose slut hole. He instantly begins to moan. Take that cock you little slut kitten. He moans louder. The whore then takes her pussy and spreads her legs right in front of his face. I command him to eat that pussy like it’s Chinese food. ( His favorite I might add.) He buries his face deep into her cunt. She squirts almost instantly. There you go, my little slave, eat that nasty cunt. She cums again and again. He makes her pussy get everything soaking wet. All the while he has that big elephant cock inside his ass. He asks me if he can cum. He is so eager to please. He listens to all my rules and follows them. I reward him with permission to cum. I hear him moan and sigh on the phone. I’m glad he called me. I needed someone to boss around. These pathetic cock suckers brighten my day.

Sissy Training Phone Sex – Luncheon

Sissy Training Phone SexOne of my favorite pansy boys contacted me today for a date. My lovely, evil mind concocted the perfect date, so I told him to put on his favorite intimates, a sexy red dress, and to make sure his bra was properly filled out, and his hair and makeup was done. He met me at the restaurant I requested, meeting each and every one of my requirements with style.

We walked in together, and heads turned immediately. It was a classy establishment, and our dresses were just this side of tasteful. We ate our meal, discussing what his goals were for the rest of the day. Little did he know what was coming.

After the waiter brought the check and he paid for it, I stood from my seat and waited for him to stand from his. Then, right there in the middle of the restaurant, I grabbed his arm and whipped him around to face me. I pushed him to his knees, being the tall fellow that he was, and I pressed his face into my breast. He quickly sprung it free and took it into his mouth like a good little bitch. I whispered for him to free his cock from under that lovely dress and start stroking it for everyone to see. He followed my orders very nicely. What he didn’t expect was for the waiter who had just served us to walk up behind him, get down on his knees, and ram his big dick into my bitch boy’s ass. He squealed into my tit before succumbing to the fucking. It was, indeed, a delicious luncheon date.