Tag: sissy training phone sex

Cuck A Slut

Sissy boy phone sex

Donald Love’s our arrangement we have an open relationship, and I think that’s okay with me, after all, I get to enjoy myself to the fullest. One weekend we went out to a Swingers Bar I was dressed in a skimpy low cut top that showed off my huge Double D’s, and I had a short tight pink skirt on that hugged my ass like a lot lizard prostitute at a truck stop. Donna was looking Debonair, as usual, he’s a money man, and he smells like money as well as looks like money, it turns all of the whores on. As soon as we walked into the bar, a couple eyed us and walked our way with haste. The young lady was about 24 years old she was tall 5 ft 9 with blazing blue eyes and long blond hair that touch the tip of her nice scrumptious tight bubble ass. I smiled and asked her what was her name she told me it was Daphne as she smiled back at me in a coy, flirtatious manner. Daphne, I said you look hot, she responded you look fucking hot too, and I love huge tits like yours. I thanked Daphne and ask her did she want to drink of course she said we hardly even noticed her boyfriend but we asked him to tag along too. I could tell something about Daphne’s boyfriend though. I could say that he was a cuckold who wanted to see his girl get fucked hard by my boyfriend. You can guess that I was going to make sure he got exactly what he wanted, my pussy started to thump thinking about Daphne’s hot tight cunt in my mouth. I whispered in my boyfriend’s ear we’ve got to take her back with us he smiled and winked at me letting me know that was the plan. We had a few drinks before leaving the bar I got into Donald’s F350 before we were in the truck comfortably I started sucking Daphne’s beautiful 36 double d tits while her boyfriend looked and smiled. I could tell Daphne’s boyfriends cock was getting hard he was biting his bottom lip like he couldn’t control himself and I loved every minute of it. We were all so fucking aroused that none of us could wait to get back to our house instead we fucked and sucked each other right there in the truck. I want you to join in and have a cum dripping good time. I am a horny slut who needs more ass dipping sex than other whores. I need you even if you like cuckold fucking. I love it all, and I want your load to bust all over me.

Mommy has a Sissy Boy

Sissy boy phone sexI want you to bend over and get on your knees for Mommy because Mommy wants you to suck her boyfriend’s cock and balls. Do you hear me, my sweet boy, I want you to be nasty with guys, and you better be the nastiest one for Mommy. Mommy likes when you take a big fat 11in cock into your mouth. I get so wet seeing you gagging on a big thick cock. Mommy’s boyfriend has a big fat horse cock, and it feels so good. Mommy is going to push you down on his big fat thick solid cock and make you ride him, jumping up and down on his cock with your asshole. Mommy likes it so much to watch her son getting fucked by her boyfriend. I want you to get fucked by him every single night. I need you to take that cock, mommy is going to whisper in your ear, relish in that cock, catch every inch of that big fat 11-inch dick. I love the way you do it you like my big fat tits too. Mommy wants to smoke a cigarette while you ride that big solid cock. I want to videotape you too, I will watch my friends as they go wild on you. My slutty friends will play with their pussies while you’re getting fucked, they will piss all over you, they will piss all over your body as you’re being fucked by a big fat hard cock. Are you ready

A new nursery

Sissy boy mommy

You are my sweet baby boy, you know that. So Mommy is going to try to do everything your little heart desires. As you know, last week your bedroom was under top secret remodeling while you slept next to Mommy. Well, today is the day my little sweet sissy boy gets to see his new room and all that is in it. First, we have to get you all dressed up for the occasion so you fit right in your new room. Head to toe you are going to be my little pretty sissy boy with your new robin’s egg blue bonnet and baby doll dress, little white knee socks and little white mary janes on your feet.
Walking you over to the door you are cooing and giggling waiting to see what is behind the door. I open it up for your uncoordinated little hands and show you your nursery. Complete with a height chair, crib, changing table, and rocking chair… everything Mommy’s baby sissy boy would need to grow up big and strong. What do you say Mommy’s baby sissy boy, want to go into your new room and explore?

 

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.

 

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.

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.