Category: Sissy phone chat

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!  

Mistress Makes Sissy Fuck Her Own Brother

Phone dominatrix

 

Who better to pimp you out to than your own brother? He dominated you even when you both were younger, him being the more manly of you two. I bet you two have had a few wrestling matches that gave you a hard clit. You won’t be wrestling this time, you’ll be taking your brother’s long hard cock in your cunt. Suck your brother’s superior cock first. Take his cock into the back of your throat so your brother can know how good of a cock sucker you are. Then, get on the bed and spread your legs. You’ll want to watch your brother’s wet cock slowly slide inside your cunt and then start pounding you. Keep telling him how amazing it is to be fucked by him, how you’ve always wanted to be fucked like this by him. Tell him how you used to watch him jerk off in his room and play with your clit, wishing you could get on top and ride him. You’ve always wanted to be your brother’s bitch. 

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.

Big Cock Fucks Sissy in G-String

Sissy panties

Don’t you love it when a man just pushes your panties to the side and fucks you like a little fuck doll and uses you like the cum rag you are? Of course you do, you cock addict sissy slut. That is why you like to wear those tiny thongs that barely cover your ass. You want to make sure that each man that fucks you has ease of access to your pussy. Your feminine cunt gapes so much that a big cock could fuck you with your panties on, your G-string wrapped around his cock as it slides in and out of you, covered in his juices and your shit. You would love it, too, enjoying the pull of the string on your ass and the feeling of the fat cock pounding you hard.  You can lick all of the cum off of the panties and suck his cock so your belly is filled with his cum. You love being his cum dumpster, don’t you? Then don’t miss one drop. 

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.