Tag: sissy training phone sex

Mommy Wants to Teach You Well

Sissy training phone sex

Do you want to jack off with Mommy and have some fun well you can do it don’t worry I’m ready for you? My little boy, you’re just so sexy you need your mommy to feed you good milk I have some I’ll feed you well I won’t let you starve you can eat my yummy cum. Mommy’s little boy is the favorite in the world he just dresses up like I want him to. I want to dress you up like a pretty little sissy oh my goodness we’re going to have fun. Don’t you know sweet boy that mommy just can’t help herself that moment that I caught you smelling my panties from my hamper it gave me permission to do whatever I wanted? Now Mommy has to train you to teach you just how to be a sissy, in fact, the best in the world. Don’t worry Mommy’s going to dress you up like a little girl and make you sell your nice tight booty two boys big boys with big dicks and big toys. Mommy’s going to tape you I want to videotape you well Mommy’s going to do it mommy loves the Way You Are. Now, why don’t you take your cute little nose and buried in mommy’s wet tasty pussy right now? Believe me, sweet son Mommy needs you to practice so that you could be the best cunt eater and dick sucker ever. I’m going to make so much money from selling my little boy’s mouth and asshole all day long. I want you to know son I won’t have any rules whatever the guys and girls want to do to you is allowed there are no problems with me what so ever. I love my sweet cum-filled cock boy I love all the little tricks that I’m going to teach you, and I love all the little skills that you already know. I want to watch you getting fucked by three guys at one time that’s called running a train, and they are going to run a massive big cock train on you. Are you ready little boy for the action to come, I know we’re going to have a good time. I’ll take pictures of your facial expressions while you’re taking big 10 inch cocks up your asshole. Now do as Mommy says and lick my wet pussy until I squirt all over that pretty little face.

Tranny Fuck

 

Sissy boy phone sex

A tranny fucked me last night, she gave me the best dick I’ve had all week, and I’ve had a lot of dicks, so that’s something to say. I love to be in this extreme way because she was crazy for me and I was mad about her 11-inch cock. That gorgeous black tranny drove me wild she was really something of an eager bitch, I loved her she was so fascinating. She slapped my puckered ass as she pushed her cum-filled cock deep inside of me. I was simply full of joy feeling all of her enormous tranny dick. From now on I know what I will do I have got to fuck a tranny or two. I really want to be wicked, and I don’t care what anyone speculates. I am a cock loving whore man or woman tranny or big dick boy it will all fly with no questions. Big dicks are my favorite, I love them so don’t even try to stop me. I love black trannies because they’ve got the biggest cocks you could ever see or could ever feel they’re amazing. Like I said this black tranny was a motherfucking killer she was not only stunning, but that fucking big ass dick was terrific and railed me. I mean she fucked me over the sofa had me fucking screaming and hollering her big fucking cock deep inside of my fleshy dripping pussy, oh goodness it was better than anything. One thing that I’ve learned about tranny fucking is that trannies get out of control they go everywhere all at the same time they suck your pussy fuck your pussy lick your ass hole and everything else in between. That is a complete treat, and I can’t get enough of it, from now on there are no cocks that I won’t fuck because I’m not ever going to miss out again.

Sissy boy mommy

 

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.