Tag: sissy phone sex

Best Sissy Trainer Addilyn Here to Steal Your Manhood

Best sissy trainer Addilyn is the woman that will steal any manliness left within you. You are not made to be manly. Look at yourself in the mirror. Take notice of your pathetically small little boy like. dare I even call it a penis… I mean just look at it!

Now take a look at a real man in his naked glory. Look at a real man with a flacid penis, see, even limp he is still bigger than you are hard. Now look at these big bulls plowing a woman in her pussy and ass. See that loser? Look at those hard throbbing fuck sticks!

Let’s make sure that we are becoming clear on your inability to man up… You will be taking part in my domination phone sex focused on feminization of you. You will be easy since you are already not manly enough to please a woman with that thing between your legs. I bet when I mentioned those big bulls fucking that woman you started to salivate and feel something tingly in that clitty.

Best Sissy Trainer

Let’s see if you are capable of cleaning a cunt that has been creampied. First you will put on some panties and watch that big bull dick fuck me. Look closely now and put your tongue out. Lick that dick as it slides out of my cunt. And don’t worry, once you manage to clean the sperm from Mistress’s cunt we will move on to the cock sucking.

Domination Phone Sex

Sissy Training is My Specialty, and So is Being a Loving Mommy

sissy trainingSissy training is my specialty, but I get a lot of mommy calls too. I guess you could call me a sissy mom. I have two trans sons. When I first started this job, my boys were schoolboys. Just young boys who liked to play dress up in mommy’s clothes and play with make-up. I knew then that they were special. I mean boys their age played with cars, Legos and trucks. They wanted to wear jeans and t-shirts. I let them be who they were. I think it is harmful to stifle a young one’s natural exploration to find out who he or she is. Most women are not as enlightened as me, though. I get all sorts of sissy phone sex callers who talk to me about how they were shamed and ridiculed, even punished by their parents when they got caught wearing mommy’s pretty things. Some of these men are pretty fucked up because their parents just did not understand.

I like to recreate the mothering experience with callers. Be that nurturing, loving, encouraging mother that they should have had. The kind of mother my boys have. My twins are living their lives in that in-between world that scares so many people these days. They go to an arts school where their creativity  can blossom. They go to a school where they can wear dresses and makeup to school daily. They have friends. They have boyfriends. They thrive socially. Regular school was not so welcoming, but I recognized that immediately and switched their schools. What mother does not want her offspring to thrive? When they are 18, they can decide if they want to have sex reassignment surgery, or become trans girls. Whatever they choose, I will support because that it what a good parent does. They support their offspring. And the best sissy trainer supports you. Nurtures you, encourages you and only punishes you in order to train you properly.  Mommy is waiting for you boys.

His first Sissy training session went well

Sissy trainingThere is a new sissy in town and he’s going to be squeezing his little link into his first pair of Sissy panties! He was at work when his asshole started feeling all slimy, he couldn’t help the tingly sensation that ran through his body.. He needed a fix, even if that meant in the parking lot of his place of employment.. Risky business! He took his 15 and called me up from the back seat of his compact car..

He didn’t have any toys so we settled with his fingers! He slicked his tips up by slurping and sucking them, like they were a fat cock.. Then smacked the excess saliva that he scooped up from his chin onto his manhole.. The windows of his car were not tinted but they did naturally fog after a while of his huffing from the sensational fuck he was giving himself; while I whispered humiliating things into his ear.. He or should I say she?

Anyway, the faggot is aware of his position.. Not every call will he get off; sometimes he may even just have to sit back and listen to me breathe.. I mean whatever it takes to talk to a hottie, you couldn’t stand a chance with in reality! uhh, the good in fantasy, huh? haha, Sissy training has only just begun, we went shopping for some fun stuff..

So far we’ve gotten a clear 7.3in soft realistic dildo to gag his bussy with and a plus size contrast lace mesh slip with a matching thong… It’s even got a satin bow that sits right between his knockers. I can’t wait until it arrives so I can show the world that a Sexy BBW does exist.. His juicy phat ass is going to look amazing sucking up a g string.. He has never had his man hole stretched with anything besides his finger.. Lucky him, I am the sexy bitch who’s going to break him in. Welcome bitch, You’ve got yourself the Best sissy trainer on the net, Good taste!

Domination phone sex Open Psyche

Domination phone sex

Sissy cunts need Domination phone sex in order to know their places. So many sissies running around here needing a proper mistress to fill their promiscuous cup.  Some men run around thinking they are capable of handling what they lack inside by pretending to be something they aren’t. Capable. They have no sense of direction and they will die lonely old men never knowing the satisfaction of submitting to a highly anointed mistress. The sub that can close his eyes and travel within to the darkest corners of his perverted sissy cunt. Realize he still have more within him that he could give over. Here in the beginning with Genesis the male sissy can carve out his space to blast open his psyche and realize what all can make his cock hard. What all can stimulate his pathetic mind into controlling or loosing control? What does a Femboy cunt feel to fill whole?

Calling All Sissy Girl Training Applicants!

Online Sissy Training

I don’t just train any curious faggot that comes into my chat, I train only the best sissy girl training applicants! I’m an exclusive online sissy trainer and I demand your utmost devotion to our training sessions. When you are mine, I will make you the best little sissy panties slut that you can be! I’ll have you strutting your stuff in high heels and kinky lingerie in no time! I’ll own all those perfect bimbo fuck holes so only the best cock will do when it comes to fucking my pretty sissies. You’ll have a great time shopping for clothes and cock with me and when we are out and about, you’ll be on display like my perfect little sissy cock tease! Mistress phone sex is just the beginning! We will find some hard BBC to please and make a game out of who can take that big dick the deepest! You will love having Mistress Raine as your best sissy trainer BFF!

Humiliation Phone Sex: ON your knees like a little bitch!

Humiliation Phone SexLet’s play a game little dick, one of humiliation phone sex roleplay fun. We will pretend I am the prison warden and you are the little punk prison bitch meant to be sodomized at my will. That means you will have to be a good little snot and obey each and every command I give you or your back pussy is going to be beaten to fuck by lots of thick studly man meat. I’m sure the thought of you being gangbanged by that many studs makes your widdle dicky twitch a little in excitement anyway. 

You can start by worshipping the ground and the sexy heels I walk on. On your hands and knees put that pretty little ass in the air for all the prison guys to look at and cat all. Kiss my heels. Suck on my heel like it was a cock that you were trying to bring pleasure to. Kiss up my legs wrapping your thighs around my heel so I can step on your pathetic bean bags while you thank me. You are lucky to serve my perfect hot young body. 

Service my perfect ass hole. Perhaps if you are lucky I might place a toot on your tongue. Men would line up to lick my anus and you are doing it for a chore. Let me use your tongue like a dick fucking you deep inside my ass. Lord knows it does more for me than your worthless little dick does. If you are a good little worthless worm you can lick my ass hole while one of my prison studs services my dripping wet cunt. We may even laugh as I drown you in my squirting pussy juices from fucking his perfect cock. No cumming for you of course otherwise you take my stud next time.

 

Online sissy training with Tiffany got kinky

Online sissy trainingHer first week crossdressing was a success! We’ve already found her a BBC Master to keep her tamed.. She is a slave to his Big black cock, left with no choice but to surrender when he destroys her bussy and leaves her with a creampie!

She has adjusted quite well to her new duty as a Sissy slut being dominated by an alpha male.. She called me up for intense Online sissy training and sent me some personalized photos so we could work on getting her up on as many sites as possible. This made our hunt for the biggest cock we could come across, easier…

She’s already been anal stretching for a while so she is no newbie to ass play. She has just finally accepted her fate, being better at servicing a man than a woman.. Plus, she’s already done so much damage that she has managed to destroy her nervous system.. her dick has shriveled up and shrunk about 3 inches.

These are the consequences sissies accept when they find out how good an anal orgasm feels. To her I am already the Best sissy trainer in existence.. Yet, training has only just begun! She seems to take orders quite well and isn’t a mouthy little bitch. Sometimes sissies forget their purpose is to serve and tend to be far too needy. She’s quite different. She knows I am who she idolizes and in order to be the best she can be she is going to have to follow my lead. In due time she will have what it takes!

Bareback breeding is my gift to her whenever I see overall improvement. An entirely new wardrobe is what we are currently working on, all she needs is guidance. Forced feminization isn’t necessary!

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? 

Best Sissy Trainer Coraline is Part Phone Sex Therapist Too

best sissy trainingI am not so egotistical to say I am the best sissy trainer here, but I am one of the best. I think what makes me good is that I am equal parts sissy trainer, mom and phone sex therapist. There is no cookie cutter sissy caller. You must know how to listen to a sissy when she is talking. Some do not want cock, some are all about the cock. Some want sissy humiliation, others want encouragement and nurturing. Some like to dress up in frilly dresses and be exposed as sissy faggots. Yet others just want to wear panties and stay in the closet. A good sissy trainer does not treat all her sissies the same way. I am part sissy phone sex therapist. I listen to my sissies. I help devise a sissy plan that best fits them. Jake for example, lives in a rural city. He wants cock, but it is hard to get cock in a small town. It is also hard to dress up and go to glory holes when your town has no glory holes and everyone in town knows everybody else. I have been encouraging Jake to travel. He finally did and he called me from San Francisco the other night. He wanted some encouragement on where to begin. In a large city full of gay men, sissy faggots and all kinds of alternative folks, Jake could blend in. I sent him to a glory hole first. I found an adult bookstore near his hotel and instructed him to go there. I was with Jake the entire time. He wanted me to hear him suck his first real cock and I did. I was like a proud mama bear. My months of sissy training finally being put into practice. It was hot hearing Jake swallow cock after cock. I helped Jake get what he wanted out of the sissy life. His journey is just beginning, however. Maybe I can help you with your sissy journey too.

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.