Category: Sissy Training Phone Sex

Sissy Phone Sex Gets Dominated

Sissy Phone SexMy little sissy bitch came over again the other night. I had him get completely naked, and settle himself down on my floor on his knees. He had to grab his sack in one hand and use the other to stick a finger up in his ass. While he sat there obediently, I finally started to undress myself. I took my time about it, shrugging slowly out of my dress. I worked that down below my tits, along my waist, over my hips, until it hit the floor. I kicked the dress aside, now standing there in nothing but my panties and heels. His cock was standing hard at attention, flexing with the muscles that spasmed with how horny he was. I could see he was struggling not to work his finger in and out of his ass, and I leaned down to grab hold of his cock. I stroked it for a minute, my tits right in his face, and his arm trembled with his effort not to fuck himself. When he managed to control himself, I patted his cheek and stepped back. I turned slowly around, my thumbs just inside the waist band of my panties on either side. Once I was facing away from him, I started to tease those things down my ass, slowly revealing inch after inch of my perfect ass cheeks, my crack, then my ass hole and my cunt. I dropped the to the floor, staying bent over so he could get a good look at my cunt and ass hole in front of his face, backing up so that he could smell it as well as see the dripping wetness of my pussy. I heard him moan, and looked back to see him still behaving himself. At that point, I went ahead and dropped to my knees, backed my ass up, and worked his cock head into that tight, wet hole. When I gave him the command, he grabbed both my hips and started pounding away at me like a dog in heat. He fucked me so hard and fast, and he was such a good boy. He didn’t even cum until I told him he could.

you can look but cant touch

sissy phone sex

You are such a sissy boy! Yes, I am speaking to you. I’m going to strip down naked in front of you. My pussy is so fucking wet!! I bet you want to fuck me don’t you. ===giggles=== No way!! That small thing you call your cock. Oh my god as if. Awwww. I’m sorry baby don’t be sad. Why don’t you sit down in my chair while, I lay down on the bed with my toys. I will let you watch me fuck my tight cunt you little pansy boy. You want to watch don’t you. ===giggles=== I am going to take my dildo and shove it up into my fuck hole. God this cock is so big! Don’t you wish it was you enjoying this amazing cunt. Keep watching, don’t close your eyes sissy boy. Jack off your cock in the corner like the good little dog you are. Get it nice and hard and watch me fuck myself until I squirt out my juices all over the bed. Listen to me as I moan loudly for that dildo. I love making you watch me pleasure myself. I will keep teasing by rubbing my hard clit until I see that small little cock squirt what you would call a load. It’s so sad you can’t fuck me.

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…

Sissy in training

Sissy phone sex MayI have interviews all next week for a new assistant and I am not sure that any of the potential applicants are going to measure up to my old assistant. I am going to have to interview them one at a time. I need to make sure they are articulate and that they can sock a mean cock. I simply can not think some times and my assistant needs to know how to clear my mind and my pipes. I need a good pair of dick sucking lips to climb under the conference table, spread my legs apart and start sucking my juicy tip. I need to be able to release all of my pent up energy and frustration from work into the back of a willing throat that will swallow every last drop. I want a good little assistant that will follow my every direction without hesitation and do exactly what I say. It is going to be very hard to find a replacement for my last assistant indeed.

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.