Category Archive: Sissy boy phone sex

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.

You Need to be Punished

Sissy Boy Phone Sex

You’ve made Mommy very upset, Son. I had one of my fuck buddies coming over to screw my brains out, but then I get a call from school that my bastard brat got into a fight at school and I had to come pick you up. My fuck buddy backed out because of you, so now you have to be punished. The pregnancy hormones are really sending my libido into overdrive today and I needed that cock I had coming over. So you just had to do for now.

I threw you to the bed after stripping you. You got on all fours as soon as I commanded it because you heard the anger in my voice. Grabbing a belt from my drawer, I bent you over and slapped that little, bare bottom until it was tomato red and you were crying. Then I took one of my dildos and jammed it into your ass. How does that feel, you little cock sucker? You squealed as I fucked your boy hole, begging me to forgive you.

Now that my pussy was wet, it was time for you to make up for what you cost me. I laid back and told you to eat Mommy’s cunt. I was already so horny from the runt kicking inside me that having you lick my honeyhole made me cum pretty fast. But I still wanted you to fuck me, so you kneeled as you stuck that little pecker in my slit. Humping me until you were panting and shaking, you busted a nut inside Mommy. I got the cum I wanted, and you hopefully learned not to ruin Mommy’s plans anymore.

You say Sissy like it’s something bad.

sissy momI’m not your regular old run-of-the-mill mommy. My specialty is tranny girls, sissy boys, and playing dress up. Plus good old fashioned spankings for naughty boys. When you need a real mommy with experience, you need to come get some tutoring from me. I will make you into a real life sexy slut. I love getting your pics and showing you exactly what you can become. Bring a toy for our calls and we’ll stretch that new boy pussy to handle the biggest cock. Mmmmmm, I know you love cum.

So, go raid your wife’s or daughters panty drawer. Or order some from me to play in. This mommy is going to teach you the ropes. Don’t be shy, little sissy. I can tell from the way you walk that you’d make a natural slut. With that round little ass and cock sucking lips, you’ll get more cum than you can handle. All you need is a little training and you’ll be on your way. I’m your new non-judgmental mommy and I will bring out the best in you. Don’t be shy. Share your fantasies and come get off with me. I know that little clitty needs some attention.

Show me those panties!!!

jack off with mommySometimes you just need to Jack off with Mommy. I’m a sissy boy mom. I love taking you wanna-be sluts and making you into cum slurping little faggots. I know you steal my panties or maybe your own mama’s, or your wife’s. They have no idea on how to deal with a sissy like you, but I do.

One call with me and I will own your little faggot hole. I’m sweet to my newbies but I won’t be so easy when it comes to breaking in that pussy. It’s your secret desire to be a girl and I plan to Ass-ist you. Here’s my orders. Shave those legs and those nasty fuzzy balls. Steal some panties or I can sell you a pair or two. Grab your butt plug, dildo, and lube. And you will also need a glass.

We’re going to have a roleplay and it’s gonna feel so real. I will tease and demean you, gently at first. Once we get that boy-pussy all nice and wet, you’re gonna fuck that pretty booty for me. Or maybe I’ll pull out my training strap-on. Then I will get rougher and call you names. You know that makes your clitty swell in those panties. When you can’t take any more, you’ll cum in that glass for mommy. Then I will give you two choices. Drink it like a good little cum slut. Or freeze it and make it into a cum-sicle for our next call. Yummy frozen cummy for my panty boy.

Come meet your new sissy mommy for that special training that I know you need.

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.

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 left a note on your desk

Dear Baby Boy,
I visited you at work today to check your diaper and change you if necessary and I watched you walk around. It didn’t look like you had your diaper on. Now you know that you have accidents all the time and you have to wear that or explain why you have peed your pants to your co-workers. When you get home tonight we are going to have to have a talk about rules and discipline.
Mommy does the things she does with you so you grow to be a good, well-mannered boy. Mommy is going to have to discipline you tonight, so you need to get over Mommy’s lap. You get 10 spankings, and your little cock doesn’t get to cum tonight. I hope this will teach you a good lesson.
Love,
Mommy Meredith

Sissy boy phone sex

Good Little Boy

sissy mom

Mommy needs a good little boy to pamper and care for. I will change your diaper if I have to, make sure that little wewe stays clean for mommy.  Mommy doesn’t like dirty boys. Now while your other little friend fucks me, Im going to sit you in front of him so you can rub your little soft dickie on mommy’s clit. Then you will fuck me with your cute little dick, and watch me how good i start sucking your little friends dickie. Yummy mommy likes little soft dicks. Both of you little boys fighting asking me who is better at sucking my clit and nipples. Also asking me witch one of your dicks is bigger and gets harder. Baby no need to fight mommy is all yours, my sweet sweet boy. Of course you are my one and only, but you know mommy likes to have fun with your little friends too. Do you want to have fun with mommy baby?

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