Category Archive: Sissy training phone sex

Discovering your feminine side

Mommy son phone sexI come from a long history of incest.  It’s sort of a family tradition. Fucking my boys was never a big deal to me. Teaching them to be men and how to touch a pussy only helps them. It wasn’t until my middle son, Steve, taught me a lesson and changed my life.

Steve was always a gentle soul. He hated sports and doing stuff with his brothers. He preferred to hide in his room and watch TV. I was getting ready to go out. That’s when I noticed something funny with my make-up. It was all messed up and some of the lids weren’t tightened. I was baffled. But when I went to put on my favorite slutty dress, it was gone. A light went on inside my head. I ran to my panty drawer and opened it. All of the tiny bikinis were gone and a few bras.

I kicked Stevie’s door open and there he was. All dressed up in my clothes, wearing make-up. “I want to be a girl, Mommy.” he sobbed. I rushed to hug him, whispering. “It’s ok, sweetheart. Mommy will help you. Pull down your panties and show me your pussy.”

And that is how I became a sissy boy mommy. So, if you are like my Stevie and hiding your secret, you can come to me for gentle support and lessons on being a girl. Let’s start with stretching that new pussy. be sure to bring your toys when you call.

 

Sissy Boy Therapy

Milf fantasy storiesYou’re up late tonight. You’ve already jacked off three times but you need some Milf fantasy stories to really empty those balls. It’s time you talk to a real life mommy who gets what you really need. No amount of phone sex moaning is going to satisfy you when what you really want to be is a sexy slut.

Think of me as your phone sex therapy mommy. Having a sissy boy of my own, I totally get your needs. The way you want to dress up. I can even send you the perfect pair of panties. Nice and fragrant, to make you think of mommy. You want to please mommy, right? So put on those panties, grab that trainer ass toy, and let’s start this session.

Tell me about that cock you crave. Is is big? Do you want to be submissive and forced to gag on it or just allowed to nibble and tease? Does mommy need to stretch that pussy first with a dildo or strap on? Or are you an eager slut who wants that boy pussy pounded hard? One call with Mommy and we can explore your special needs. Your clitty will explode in those panties. Quit denying the faggot truth and come talk to me soon.

Sweet Sissy Princess

Sissy boy phone sex

The little man was tucked away in bed  in his room giggling under the blanket.  I had to take a peek at what was going on.  Just to see what was so funny.  I pulled back the blanket and to my surprise he had on a complete pink bra and pantie set on.  I had to ask what are you doing.  he looked up and smiled and said being pretty for bed.  He had a complete hard on bulging through those cute little pink panties.  In his cuties voice he asked could I touch his pee pee.  I started rubbing my little guys pee pee as he requested.  My  little man princess loved it.  We would play dress up every night at bed time and more.  He would always ask could he rub his pee pee on me.  Love keeping the little one happy.  His strokes was ever so soothing as he would be sucking on my breast as if he was nursing.  His quick pumps in my wet juicy cunt had him really excited.  That wasn’t what got him off.  He had cum so hard when I put him across my lap and I would just finger and fist him.  He even enjoyed a little spanking too.  His load was so heavy after a full fist fucking he would go straight to bed afterwards.  Night Night my sweet sissy princess.

Sissy Lessons with Mama Pearl

Sissy maid trainingSissy maid training classes are now in session, boys. Sign up now to learn to be that cum slurping little faggot that deep down you really want to be. In my special tutored classes you will meet our sissies who want to be just like you. Together we will dress up and do our make-up. You will transform from masculine guy to a sexy, flouncing girly-girl.

Lesson two will be playing with a variety of ass toys. Bring your favorites and show the class how much cock you can take. We got to get that boy-pussy stretched wide open. No man wants to fuck a cry-bebe faggot. You need to take that fuck stick to the hilt and love it.

Lesson three. We will practice on each other. Learn how to approach and flirt to get your needs met. Lots of roleplaying to get you feeling good and confident. Bring that sexy lingerie and those lace panties and learn how to rock them. High heel or stilettos required.

Lesson four is the best. I will have some sexy tranny-loving men with large cocks come in and show you how it’s done. I will fuck and suck and demonstrate on these meat sticks before I allow you to join in for your first taste of another man’s cum.

Are you ready to begin your new life as a tranny? Come join Mama Pearl for some therapy and education.

Johnny and his giantess girlfriend

Jack off with Mommy

One of my favorite Jack Off With Mommy clients is a little Asian man named Johnny. Johnny loves his giantess girlfriend and I adore my little sissy. It’s like having my own little doll. I dress him up and take him out on the town as my personal pet. It’s so much fun to introduce him as my tiny boyfriend and make him sit on my lap or in a high chair. People think he must be packing a huge cock or a fat wallet, when in fact, he has neither. I just like the superior feeling it gives me making him into a little submissive slut.

Sometimes, we go out with my besties, Selina and Addison. We all pick up some big black studs. We know poor little Johnny is so jealous of their huge cocks since he is so tiny. Teasing him  makes us laugh so hard. We all get fucked up together and go to the Land of Giants.  There Johnny is a perfect sized human dildo for us. We cram him into each others pussies, drowning him in juices. He begs to be smaller. I tie a string around his feet and cram him inside of me, like a tampon. To humiliate him I ask my black stud to fuck me, pushing Johnny Tampon deep up against my cervix. We laugh and tell him that’s what a real cock looks like in a pussy. Johnny gets so excited that his tiny cock spurts all over my insides.

Maybe you have an equally wild fantasy. Don’t be shy. We love to roleplay the unique and unusual. Nothing is too crazy for us. Tell us your thoughts and we’ll make it feel like the real deal.

Late night Tranny fantasies

Sissy training phone sex

Just admit it. Sissy training phone sex is what you are on here looking for. You’re not just another hard dick looking to get jerked off.  You have some special needs and you want the perfect mommy to help you. Sweet boy, quit hiding from your desires and come tell Mommy. You see, I’ve known your kind before. My older brother and my own son are both sissies. I trained both of them to be cock sucking little sluts. I can train you too.

I mean, you’ve known from a young age what you really are. You are a closet faggot who hides the fact that you want to be a girl. You want to be dressed up. You want to be properly and gently trained. I want to hear those fantasies. I’m an older sissy mommy with experience so no shame, no judgment.

Your need to wear panties and lingerie doesn’t shock me. In fact, i will sell you some that are perfect for you. You also need an ass toy to start your training. Oh, it will feel so good and so right inside of you. My strap-on is also available to help you stretch that new pussy.

Quit trying to sleep when all you think about is cock. Bring it to Mommy and I will explore all of your faggot or tranny fantasies. You will be so pretty and fuckable.

Training my new sissy

jack off with mommy

Jack off with Mommy while I teach you how to be a sissy success. Mommy knows what ti takes to be more than just a dress up game. You have to become a real girl. A slut. One that can please men with your cock sucking skills and a love for cum.

“Mommy, how can I be a real girl.” you ask. “Can I wear your clothes?” Sweetie, it’s more than just wearing my clothes. Any boy can put on women’s clothes. You just look like a drag queen. You have to learn how to wear those clothes. I mean wear them like a woman. With class and a flounce.

And your cock sucking skills need work too. You look like a pig slurping at the trough. Any whore can do that. You need “the look” as well as the skills. Look at him with those big eyes, nibble a bit, leave him waiting for more. Now take that meat rod down your throat. Deeper. Oh yeah. Now gag just a little. Make him feel like a man. You’ll get that cum that you crave so much.

I can teach you this and more. Come on, little sissy. No one has to know your secret except us. Be the best sissy that you can be. Just reach out to Mommy…

 

Mommy Pearl’s Sissy Slumber Party

sissy training phone sexThe younger the better, the sweeter the meat. Training sissy boys is what this mommy loves the best. Sissy boy training phone sex weeds out the girls from the men. I love discovering that you are a sissy. Why wouldn’t you want to be a cum slurping little faggot? Cum tastes soooo good. And that man-pussy is just dying to be violated for the first time.

I’m the kind of mommy that you can feel safe sharing your secret with. I love your pics and watching you transform into a slutty girl. I would never break that confidence or threaten to share your pics, unless you asked me to tease you just a bit. We’ll be like like a couple of young girls sharing make up and sex secrets. There is so much that I want to teach you on how to please a man.

Be sure to bring an ass toy for our first session. You’ll be learning to suck that cock for me. I want to hear you slurp and gag. After it’s all good and wet, drool dripping onto your now worthless penis, I’ll get to the good stuff. You’re gonna bend over for mama, show me that perfect little starfish, that pucker-pussy. And I’m gonna to teach you to fuck yourself like a girl. After all, that thing needs stretched if you’re gonna handle the kind of cock you crave. And we girls all want that perfect kind of cock. The one that stretches us wide open and makes a creampie of of our girly fuckholes.

I’m here all night for your private lesson. It’s like a slumber party, but with COCK!!!

 

 

Sissy training phone sex with Mommy Pearl

sissy training phone sexI’m ready to start your sissy training phone sex lessons. I’ve known since you were a boy that you were special. The way your sweet ass wiggled when you walked. The way you lisped your words. That little flounce when you were pissed. But it wasn’t until my panties started disappearing that I figured out the truth. At first I thought you were just like your older brother, stealing them to jerk off into. But I snooped while you were at school and it blew my mind. In a small set of plastic drawers in the back of your closet, I found your secret stash.

It was filled with beautiful lingerie and panties. I recognized some as mine and some as your younger sister’s. I had wondered what you spent your allowance on and now I knew. There was a box of makeup and Ebay receipts. My son was a sissy. OMG!!!  I snooped a little more and found one of my old vibrators. I put it to my nose and got a faint whiff of ass. I giggled to myself, thinking of you fucking yourself, wearing your panties. I quickly put everything away.

Tonight is ours, my sissy boy. Your sister is sleeping over at her friend’s place. Your brother has another week of college. It will be just me and you tonight as I reveal what I know. Tonight we will start your transformation into the cock sucking sissy that you desperately want to be. Mommy has a big black strap-on and a wicked smile on her face. Your secret is safe with me.

Sissy boy punishment

Sissy boy mommy

Someone has been a very naughty little boy, catching you jerking off without Mommy’s permission is very very naughty. First things first…we have to go to the store because you are out of diapers. I put you in the back seat and strap you into your car seat making sure you can’t get out. I have a cup of water in my hand and you ask for a drink. As I am handing it to you I “accidentally” spill the whole cup onto your pants crotch area and down your pant legs. “Oh my, too late to change your pants baby, we have to get going.”
We arrive at the store a moment or two later and the water on your pants hasn’t dried. I come to the back seat and undo your car seat and say let’s go into the store. You pull on my hand a yell no at me. My eyebrows go up in an “oh really” look at you. “Get out of that car right now young man, before I take you over my knee right here in this parking lot.” You start to step out and your pants…you definitely look like you’ve peed your pants. I grab your hand, walk into the store, grab a cart and make a B-line for the diapers. I grab about four of the biggest boxes they have and load them all into the cart. I grab your hand again and pull you along to the check outs. People are staring and even laughing. Think it’s at Mr. pee pants? Or that I have a cart full of diapers that you clearly need.
I put you into the back of the SUV and start to take your pants off. “What are you doing Mommy??” I give you a stern look and tell you that I am going to put your diaper on. The look on your face and the begging that came with it was quite a lesson for you. I get the diaper under you and use the baby wipes from the car and clean you off. A passerby saw your big cock being wiped down like a baby and she looked shocked. I fasten the diaper on you and tell you to get your pants on. In the car ride on the way home I ask you “Do little boys jerk off without Mommy’s permission?” A valuable lesson for my little baby boy.

Sissy training phone sex

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