Category: Sissy training phone sex

Phone Sex Mommy for Sissies and Adult Babies

phone sex mommyBeing a phone sex mommy is a rewarding job. This morning, before I signed on to work, I was blowing my sons before they left for school. I got their cum in my mouth then spit it into my coffee so I can enjoy that boy crème a throughout the day. After the boys left, I started checking my work email. I had some nice surprises.  I have several adult babies and sissies who call me regularly. Not every mommy’s boy gets to fuck mommy. Some are too shameful for that honor. They lack a quality dick for mommy or they lack any masculinity to please mommy. Instead, those little losers, get to soil their diapers and dress up in girly clothes for me. I love being a sissy mom. I was running a sissy contest last week to see which of my sissy boys was the biggest sissy of them all. I got several of the pictures this morning. Oh my, I have some pathetic little losers who call me. One sissy was in a bonnet sucking on a bottle filled with cum with a butt plug that looked like a teething ring up his ass. Another sissy looked like Shirley Temple from the Good Ship Lollipop. She was all in frills with patent leather shoes, sucking on a lollipop in the shape of a penis. Another sissy was in Pull Up diapers, a baby bonnet sucking on a real cock that said, “Baby’s Milk” on it.  I was beyond delighted with the sissy pictures they sent me. More entries are still coming in. Sissies and adult babies do not receive the gift of my warm wet mom pussy. They do, however, get my laughter and public shaming. If you are a sissy or adult diaper lover, that is what you want most from mommy anyway, right?

mom fantasies with Daphne

Mom fantasies I’m sure you have had them. My boys are always thinking about mommy, and mommy is thinking about them, Today I sucked them all of  That’s what mommy did today. As a mommy, you try your hardest to make your guys happy. I sure do try to make my boy really happy in many ways. I have been told I spoil my boys a little too much. I can’t help it. I mean who wouldn’t want to spoil boys like mine. I got very lucky my boys are so handsome and very well hung. I sure did pick the right guy to mate with. If it weren’t for my hubby’s big dick and good looks I don’t think I would be this hyped up on good cock. When I met him I had no idea I would be this cock craved mommy. I love sucking my handsome guys off at all times of the day. I randomly go in their room and begin to jerk them and blow them. I mean I love waking them up with a nice start to their day. It’s always fun.

Breeding whore Momma

breeding whoreBreeding whore momma is what I have been for quite some time now. I love the games the boys and I run. We always have the ongoing challenge who can dominate mommas pussy and get her knocked up. So far my husband has been winning taking the lead each time I have been knocked up every year by him but this year is the second year my boys are competing to get mommy knocked up daddy might have to retire because the boys are back and they have made it their mission to get momma bred. I love seeing how determined the boys are and how bad they want to stuff mom up and jizz inside me. I have my bets on them but there may just be a repeat of last year if they don’t deliver. Mommy is very fertile and always wanting a hot load inside her cunt. Imagine mommy begging to cum deep inside and as she begs you bust right then and there. Waiting desperately to see who ends up being the champ.

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…