Tag: Sissy phone chat

Sissy Maid: Follow My Instructions

Sissy maid training


A sissy maid that is employed by me has to do a lot more than wash dishes and do my laundry. Obviously, you will be doing any chores I assign to you, but I have a few extra activities that a regular maid will not do. You will require extensive training before you can really be called my maid. You have to take corporal punishment well, even if you haven’t done anything wrong. Sometimes I just like to spank your ass. You also have to be in a chastity cage every minute you work for me. You are more of a sissy slave than a maid, and no slave needs to be getting off without my permission. In addition, a maid must be willing to vet all of my sexual partners thoroughly. That means you’ll have to be good at taking a hard fucking. None of the men that I have ever fucked (and they are few and far between) got to fuck me before showing how good of a lay they are. You don’t have to do anything but let them use you and rip your pussy apart. Once you have been sufficiently degraded, you need to report back to me how good he was. If he’s shit, he might need to practice on you until he gets it right. You’re okay with that, aren’t you, maid sex slave? 

Gotcha Professor; A Sissy Phone Chat Roleplay That Will Make You Hard

Sissy Phone ChatSissy phone chat will suck you in when you are a cross-dressing faggot craving the penetration of a superior women’s strap-on. I know that when you admire a beautiful woman it is not the sexual desire of ravaging her body that plagues your mind. Instead, it is envy that pierces deep within your soul knowing that you, a man, just wish you could be in that pretty lady’s clothes. That is why whenever you show up at that college party, I can tell by the way you are looking at me, Professor, that you want to be naughty but not like all the other professors with their horny teacher’s assistants. 

It doesn’t take much convincing for you to take me back to your place. A single-person basement efficiency. You make good money working for the school, so why live in a dump like this place with thrift store furniture? I know it isn’t because of fancy clothes, because you would rather dress like a whore. However, the air smells of sweet perfume. Hookers. You do like to get your rocks off. You have no wife so it must be an embarrassing fetish that keeps you blowing your bullseye with women of the night. 

You lead the way to the bedroom showing me to the bed before excusing your way to the bathroom. Lingerie hangs ever so slightly from the top drawer of your dresser. Now I can’t help but snooze, stepping up to my red healed platform wearing feet and slowly and quietly pulling out that drawer. It brings a subtle giggle to my sexy lips. Panties, and lots of them. Some bras too. Inside the drawer was a variety of pretty panties all tangled up as if they were having an orgy of their own. You enter the room mid-conversation pausing, words stuck on your lips. Slowly I hold up a lacy pair of purple panties lined with a lilac silk pouch that would be against a pretty puss. 

It’s honestly adorable the way you stumble over your words slowly sulking closer to the ground. Your panties are still in my hand as I slowly walk your way. I reach down and lift your chin, ordering you to your knees. Gently I kiss your forehead and order you to dress up nice and pretty for me and you may get a reward. I order you to show me the rest of your toys, and of course, you do holding up a big 10-inch black strap-on dildo. I can hardly hold my excitement as you dress in your best lingerie. All the naughty nothings that I will be doing to you with this deep dick penetration of mine. I’ve got you now professor, you are mine all mine.

some mean domination phone sex

domination phone sex

Some mean domination phone sex after a long day. It would be best if you told me what to do. It’s time you learn from a bossy babe how to be the best sissy. A little rough attitude and strict rules will keep you in line.

Yes, you know you’ll enjoy my big dildo because seeing you deepthroat on such a massive plastic cock gets my wet cunt going and getting it off.

There’s a reason why I like to make men sissies. Emasculating a man is one of the most powerful things a woman can do. Making you choose between your manhood and a world of submission is easy. Yes, you may have reservations, but you will never be a man again after signing up for my sissy lessons.

Let Me Show You Sissies How It’s Done

Femboy training

I am disappointed in all of you. Man after man have come here to run through all of my students and you still don’t know how to please a cock correctly. Come watch me and I will show you what a real sissy whore will do. Before I do so, however, I’m going to put you all in chastity. I don’t want you all to get distracted rubbing your clits while I am teaching you valuable skills. When you get down on all fours, look back at him while he’s fucking you. Even though you are a disposable cum rag, some guys like to see the cum rag’s fuck faces. Squeeze his cock when he is completely inside of you, so that he never wants to slide it out. Do your exercises so that you can hold onto that cock for as long as you can. Unless they ask for your gaping hole, no one wants a loose pussy. I see you’re all hard in chastity right now. You had better not touch your clits until I’m done getting fucked!  

Sissy slut needs sissy phone sex

sissy phone sex

I like when little sissies pretend they don’t want huge cocks. You can fake it all you want. You know you’re craving cock. Ever since I’ve begun sissy phone sex with specific clients, I have noticed that I am so into making a sissy like that come to their knees and begin to worship, wanting to be a sissy.

I like making sissies do poppers and talk to me all about their dirty fantasies. You know you have one too many of those naughty cock fantasies that make you want to succumb to a big dick. Open your mouth and take that jizz. It’s going to be a wild ride with a slut who can indeed teach you to swallow every load.

Now you will begin to admit that you are a sissy.

Sissy phone fun with lingerie

sissy phone

My lingerie is one of the ways I trap my sissies. Whenever I find a new outfit, I get rid of one. The collection I have is insane. I have a whole floor dedicated to my sensual cosmic playwear.

If a sissy gets gifted a hot lingerie outfit by me, they know they have to find someone willing to fuck them in that outfit.

The mission needs only a few hours to be completed. Once the sissy gets the guy who will use them for the night, they progress to the next level. A sissy phone session with me will bring up all the ways to make you the right cock sucker and to be able to enjoy the jizz factor of it all.

When a sissy becomes obsessed with wanting to be feminized, they will be able to be the perfect cum slut only if they listen to my every command.

Sissy Phone Chat Mistress Addilyn

This is your New Sissy Phone Chat Mistress, Addilyn. It’s in your best interest to be a good little sissy girl and obey your Mistress and respect me for who I am. That’s right sissy this is Boot Camp for your training to be a good little cock sucking sissy slut.

First off we will discuss the fact that your small peeny is not a cock. You have a clitoris and it belongs in panties. I want your first task before calling me to be completed. That task is to obtain a pair or pretty panties that you will start wearing. Wear your panties when you call me. And the next task is to have a butt plug that you will also be wearing regularly to train that ass pussy. These two things are a must for our sessions to really get intense and real. If you find yourself to be even more advanced I think it would be good to also have a nice big black cock dildo for you to train on as well. Talk soo sissy slave.

Sissy phone chat

Missy gets Sissy maid training

Sissy maid trainingSissy maid Training was due for a bottom-feeder bitch like Missy. She came to be with a holier than thou attitude, and that just wouldn’t do! First I had Missy strip off all of her masculine clothes. No fucking pants, boxers needed ever again! Naked now, I needed to see the body type I was dealing with. Missy came in at about 5ft11 with a slim frame. Not much ass but we could work with this. Next on the agenda was to have Missy shave off all of that nasty course body hair. Nothing above the dick nothing on the balls and of course I have to get right between those ass cheeks and shave that ass hair off. Although I did enjoy sitting on her lap with her little kitty between me and my pussy while I straight-blade shaved her face. That sissy clit would need to be tucked away in a cage as I put some sexy makeup on my new little whore. But this is what Missy loves, being forced to be the feminine creature that she truly is. Sometimes when men come to me and denial of who they are they have a bit of a cranky attitude. That’s nothing I can’t deal with. Next when a sexy little maid outfit complete with the Lacey bra soft panties and thigh highs. Next would be cleaning assignments. Perfectly dusted shelves in my library would be a great task to start out with. Everything must be done while wearing 6-inch stilettos as well. But did my sissy whore understand her assignment? No, she half assed it so I had to whole-ass her on the end of my strap-on.

Using these Sissies to Pay my Way

Domination phone sex


My sissies are such big sluts that I never have to pay for anything. Any time I need a service done or need to buy something, I just get one of my sissies to suck their cocks. For example, there was one time I was getting my car fixed and the mechanic asked me to pay a lot more money than was quoted. I got one of my sissy whores and told her to take care of the bill for me. She sashayed over to him, pushed her breasts against him, and then got on her knees so she could suck his cock. Before he had a chance to react, he was getting sucked off by my sissy fag whore. She put his entire cock into her mouth and bobbed her head while playing with his balls. When he finally came inside her throat, he told me I didn’t have to worry about the bill. Pimping out these sissy sluts is one of the best decisions I’ve ever made. 

Sissies Gape Their Holes for You

Phone dominationI love teaching sissy fags how to be better sluts. This time I am teaching them how to gape their assholes. Who doesn’t love a sissy that can take their big cock and not have to struggle fitting it in each time? You get to see how much of a big slut they are and how thirsty they are for cock, bending over and gaping their formerly tight pussies for you. I’m going to pimp my bitches out to hundreds of men and see if they can stretch their pussies out. Those tight holes will become gaping holes for cocks to stick in. No cock can resist putting itself in a gaping hole and a sissy’s job is to be a fuck toy to anyone that walks by. Sissies won’t be able to sit down once they start gaping, showing off their wide open pussies for everyone to use and abuse. Once the cock is inside, they’ll start milking it with their pussies like good little sluts do.