Pearl's Phone Sex Blog

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.

Jack off with Mommy at the Yard sale

Jack off with mommy

It was a jack off with mommy annual event in our neighborhood. My annual garage sale. I’m not a hoarder so every Spring I clean out my closet and lingerie drawer and sell it all. It’s so much fun to watch my neighbors show up, trying to be all discreet. They creep over a few at a time. And no one ever tries to haggle. They know I have the good stuff. I even have a few used toys if you’ll just ask.

You were my first customer. I was watching you out of the corner of my eye as you held a pair of panties up to yourself. I stifle a giggle as you try to tell me that they were for your wife. Your wife is a 250 lb oinker so I know that these are for you. I always suspected that you were a panty boy and now I know the truth. “I think they will look great on you.” I whisper, watching you turn red. “Shhhh, it’s our secret. Just let me know when you are ready to model them for me. I love a man who wears panties. Would you like the matching bra, too?” You look like a fish outta water as you gasp for air. I know I’ll be seeing you soon.

By the end of the sale, I have a fistful of cash and a list of names signed up for sissy lessons. Wouldn’t you like some of my sexy things, too? You can model it for me and send me pics. Mommy loves little faggot boys who beat their meat into their panties. Your secret is safe so come share with me.

 

Mommy Son Phone Sex with Pearl

mommy son phone sexWhat can I say? Mommy son phone sex just feels damn good. I love young cock. And these boys need a mom like me to train them. Don’t you remember the first time that your mommy put your cock on your cock. Maybe she was washing your balls or helping you put on your underoos. her soft fingers touched you and suddenly, that was all you could think about. You were so turned on.
You lie awake that night with your hand on that cock, jerking it raw. Mommy’s soft tits pressed against you when she said goodnight and you almost creamed your sheets. You moaned out loud. You didn’t see me in the doorway in my short gown. I was smiling and you knew you were busted. “It’s alright, sweetie.” you whispered as you slipped into bed beside me. I felt your hand touch my cock as you drew my head to your breast. Tonight would be the first of many…..

Happy Mother’s Day from your sissy boy mama

mommy phone sex

Happy Mother’s Day.   It’s time for your annual sissy parade. Let mom help you get all slutted up so we can expose your sissy ass to the public. Mother’s Day is the perfect day to do it. All of the moms will be wearing their Sunday finest. It’s time to roll on those silk thigh highs, put on your fancy panties and join the other women as we celebrate. I’ll be honored to fix your make-up, sissy boy.

Raising cock pleasing sissy “daughters” is my favorite job as a mother. If your own mom doesn’t accept you, run to me with open arms. I’ll embrace you and train you to be the best. We’ll tuck that little willie away in a thong and I’ll teach you to flounce that ass. Then I’ll break that boy-pussy in myself with a strap-on before I start you on real meat. Don’t worry. I’ll be easy and sweet unless you are an annoying whiny little bitch who needs some hardcore mommy ass kicking first.

You don’t even have to be a sissy to come play with me. I’m an older woman but don’t think for a moment that I will pass up some rock hard young cock. Mommy fantasies need to be thoroughly explored and role-played. If you ever had a crush on your stepmom or wondered what Mommy’s pussy felt like…….It’s time we had a talk, young man. This fine vintage cunt is aching for some boy batter . Make this a day for Mom to remember forever. I’m here with open arms and open legs. Forget candy. Mama wants cock!!!

Sissy Boy Phone Sex Mommy for you

sissy boy phone sex

Ready for some sissy boy phone sex play time, little boy? Your big, obedient mommy is here to make sure you get the proper training. I’m a no-nonsense mom who expects my boys to be able to serve any cock in town after they are trained. A rigorous schedule of feminization is followed by cocksucking lessons. Are you ready to flounce it for me, little sissy? Purse those pretty pink lips and wiggle that panty ass. That’s a good girl. Now let’s work on that pussy power.
A good sissy needs to be sweet, obedient, submissive, and able to accomodate any size size of cock. Today’s lesson is simple. Mommy is bringing out the big fuck toys and the strap-on. You are getting that first lesson in taking a cock in that new boy-pussy. Don’t worry. Mommy will be kind. It will only hurt a little. I’m not really a mean mommy. I will kiss your booboos and give you a titty. Like a real mom, I just want the best for my sissies. Don’t be afraid. Come to me and I will teach you all that you need to know. Your secrets are safe with me.

After school detention for you.

Jack off with MommyYou caught my eye the minute you walked into my classroom. Way bigger and taller than the other students, I knew you were special. I checked out your tight jeans and round little ass, then grabbed a quick peek at your package. I just knew that you were packing the meat. You seemed to know exactly what I was thinking. You grinned at me, looking at my big firm tits and short skirt.

“Please turn in your homework before you leave.” I told the class. You were the last one to leave and you hadn’t even brought a book to my class. “After school detention for you, buddy. Starts in 10  minutes.” You licked your lips as you left, leaving me with a wet pussy and breathing a bit heavy.

You walked into the classroom and shut the door behind you. “Detention is cancelled today. Everyone is gone.” You walked over and kissed me, unzipping your fly.  “Suck my cock, teacher, and you’ll get your missing assignments.” I dropped to my knees and took your young, rock hard monster into my mouth. Your hand went into my hair as you face fucked me.

I stood up and took you by the hand. “Fuck me. Right here on my desk.” I ordered, spreading my legs. I almost screamed with pleasure as your 10 inch cock pushed into my juicy cunt. You jackhammered me hard. “Do I get an A, teacher?” you moaned. “Oh, yes. Fuck my Asshole. That’s your A.”

We spent the whole afternoon fucking and sucking. You came so many times. That’s why I love the young dick. “Detention again tomorrow, young man” I tried to be stern as you left. “Absolutely, but find a cute student to play with us.”  I nodded with anticipation, thinking about which student I wanted to lick my pussy.

Sissy learns the sexual ballet

jack off with mommy

Every good sissy needs to know how to dance. Dancing and fucking are arts that a girly boy must be exceptional at. The first form of dancing is my sexual ballet. Learning the flexible poses and spins while dressed in a lacy pink tutu is a great way to become a sissy. The ability to do those contortionist bends will make for some unique fucking positions. Can you imagine doing a Balançoire while being fucked from behind? Or how about a sexy Cambré, bent over at the waist, ready to receive what your pussy craves the most? As a sissy Danseur, you wouldn’t be wearing just the leotard but also the frilly tutu that makes you the star of the show. Standing Demi-pointe, you will stick that sweet ass up and out, balancing on the balls of your feet, waiting for that first hard thrust. Bent completely over in a Fish dive position, you will beg for that cum.  To finish your lover off, you will perform a Grand plié as he fills up your boy-pussy with cum. Never before has the ballet been so sexy. The cum runs down your leotard where your lover has torn a hole so he can stuff his cock into your tight starfish as you perform your pas de deux.

sissy training phone sex

Next lesson: Salsa dancing with a sexy Latino who loves that sissy pussy.

Pearl’s Midnight Wet Dream

Jack off with mommy

I’d had a few drinks when I headed off to bed. I was too tired to even pull out my vibrator and give myself a quickie. I had barely dozed off when I felt him touch me. He was tall and young and had a cock of steel. “Taste my cock.” he whispered revealing a thick flesh sword. I felt him reach down to touch me and my pussy began to throb. His fingers delved deeply into my soaking gash. My clit was on fire with desire. I needed to feel him inside of me, feel his lips on my clit. I ached to suck the cum from his balls. I thrashed helplessly as he seemed to touch me all over. I awoke gasping for air, my cunt twitching and gooey, and a lingering scent of male sweat and cologne in my bedroom. Had I really had a midnight visitor or was he a figment of my imagination? I can barely wait to fall back to sleep so I can find out.  

Mommys Dirty Secret

mommy phone sexMommy has a dirty secret. She has been watching you grow up and knows that you jerk your cock at least 5 times a day. Mommy is waiting for that day when you tell her that you want to play. I’ve been leaving panties all over the house that smell like my pussy. I know you grab them and use them for your naughty pleasure. And those accidental touches are not really accidents, son. I’ve been rubbing my big tits on you trying to get a response. You’re such a shy boy though. I’m going to have to make the next move. Maybe let you see me naked in the shower and ask you to wash my back. Surely then I will get a good look at that growing meatstick of yours and an opportunity to take advantage of my own son. Mommy is just so damn horny and she knows you have the cum and the stamina that she’s craving.

Mommy breaks in a Sissy.

jack off with mommy

My poor little sissy. He still hasn’t learned how to properly suck cock. I think it’s time to go out and get some practice. He says no because he doesn’t want to be recognized in public wearing his mini skirt and thigh high stockings. But he’s such a pretty girl and that sweet mouth is begging to be used along with a tight little man-pussy. Oh, yes. it’s time. I saw him last night on his knees trying to suck a big black cock. He gagged and sputtered. My nigga loved dominating him and just face fucked him harder. He nutted so hard that cum came out of sissy’s nose.

So put on your pretties, your lacy thong. Get those balls shaved smooth. Cause your training starts tonight as I guide you on being the perfect little cum guzzling tranny slut. Our first stop is a local glory hole where you can learn to suck a cock correctly. Maybe after a few dozen loads pumped down your throat, you will be able to give head with some finesse. If not, I am gonna just back you up against that padded hole and let the savages rip that asshole wide open. Oh, they are gonna love that tight little boy-cunt so much!!! And I will be laughing at you while they do it!!!

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