Category: Sissy training phone sex

Milf Pool Party

Milf Fantasy Stories clara

I’ll ride his cock anytime! I was thinking before he knocked on the door. “Come right up, I’m just trying some new bathing suits for the pool party sweetie.” I yelled to my nephew.  He’s back from College! “Help me pick out which one of these you think looks best for the party tonight.” He picked the blue and green striped bikini-“help me put it on?” As I took my top off, he began to blush. “Oh honey, you’ve seen my big tits so many times growing up, help tie me up please?” as I felt his hands brush my skin I guided them toward my breasts. “Aunt Clara…” I could feel his dick harden against my thigh, “are you sure…” he stuttered, I guided his hands toward my pussy. “Yes sweetie.” As I started to take his pants off and get onto my knees, he tasted his fingers. I pushed him onto the bed to sit on his face while I sucks his cock. The tongue he has on him felt so hungry! Getting so wet I decided to slide and drop this pussy on his thick cock.  He came so quick- I couldn’t blame him, but I’ll  sure can’t wait to have another round tonight!!

Sissy Training GiGi

My grandson is such a little sissy! He is always begging to wear my heels and slutty outfits. It has gotten to the point that when I suck his little cock he always begs me to lick and suck on his ass! This anal sex granny can take the hint so now I am going to make him submit to his sexy GiGi. Today I just up in a crop top halter top and a slutty little Jean skirt with a g string and some fishnets. He was smiling from ear to ear when I finished him off with some makeup! I like my sissys to wear bright pink lipstick when they’re sucking my twat. As soon as those lips were pink and shiny, I shoved his face in my dripping snatch and made his sticky lips kiss all over my clit. He moaned and fingered his clit until it shot all over my feet. His hot pussy juice all over my feet made me cum all over his pretty made-up face! He my pussy wet her now that I have made him do Sissy sex. We just need to work on training him to only come when GG says so!

My Son is a Sissy

Sissy Boy Phone SexLately I’ve been noticing my panties in my son’s room. I’ve come to realize that my son is becoming a little sissy boy and I want to make sure he knows what that means. I walked into his room tonight and there he was with my fucking panties on touching his thick cock through my panties. He was so scared when I walked in, and he should be because I’m going to show him what I do to little sissy bitches in my fucking house. I grabbed him by his little arm and bent him over my knee and asked him how long he has been a little sissy. He told me for about a year, and I said that’s okay but since he lied about it that means he needs to be punished. I started to rub his little soft round ass with my hand and gave him 20 smacks. I could tell that it turned him on, and I told him to get on his knees in front of me and be a good little sissy slut and make mommy cum on that pretty little face. He did such a good job so I thought I would reward him by letting him cum. I brought in mommy’s favorite anal beads and put them right into his tight hole while I was sucking on my little sissy boy’s cock. He was so close to cuming and I let him cum all over my lactating mommy titties and made him lick up all of his cum and drink my tittie milk.

Sissy Boy Mommy Slut For Roxanne

My youngest step brat is a good sissy boy mommy slut. I use him as my sissy maid and fluffer slut. Whenever I have a john, I do not feel like even putting my mouth on.

Sissy boy phone sex

I use my sissy boy to suck his cock and get it hard for me. After I get fucked since I’m a mommy whore I get full creampies in my cunt hole. Even if I’m being a breeding whore, I want my cunt cleaned. My sissy boy will lick me until I don’t have any more semen in me. He will scoop any nut out of me with his tongue and make sure my lips are all clean. We have done enough sissy maid training that my sissy boy knows if I need to empty my bladder, I will squat over him and let my mommy piss stream spray drench him. Mommy loves how he is such a good sissy boy that I treat him my jerking off his dick and let him cum all over my hands. He doesn’t mind cleaning up his cummy mess like he has been trained to do.  

Pregnant phone sex pissing

Pregnant phone sex

There are times that being a pregnant phone sex whore isn’t all it’s cracked up to be. Nights when this brat is laying right on my bladder make me run potty every hour and I have to cover up the sound of me peeing like a racehorse! I have peed for men on the phone before, but you never know if they are into piss games and I never want to say hey baby, I have to run pee. Can you give me a couple of minutes? Last night I was going to piss myself and ran to the bathroom, forgot to mute and let out the loudest stream into the potty. I was so embarrassed until my caller asked are you pissing? That’s so hot! He told me he would be the toilet paper to my pregnant pussy! ANd I learned a new fact, I’m not sure if its correct but he swears that a pregnant woman’s pee is sweeter than normal and he would drink me up like I was a hot toddy! I would gladly let any man be my toilet! 

Sissy Maid Son

Sissy maid training

 

I’m really proud of my son’s sissy maid training, she’s really stepped up her sissification almost all on her own.  Sure, I gave him a bit of guidance to point him in the right direction, but I never broke him down mentally like I did with all of my other femboys.  She’s either advanced this far all on her own or she has another sissy mistress helping her along.  It doesn’t matter to me either way because she’s really happy with herself and her sexy little clitty, plus my house has never been cleaner!

My book club meeting was at my place last week and the girls couldn’t stop commenting on how spotless my house was.  I told them all about my new maid and called her in so I could introduce her to the gang.  They all marveled at my sissy son’s marvelous pink hair and sexy maid outfit.  Even Miss know-it-all Janice asked where we found hot heels his size because she has problems finding shoes big enough to fit her giant hobbit feet!  

The gals had a great time bossing my girly boy around and making him wait on them hand and foot.  Their drinks were always fresh and the dishes were always cleared with a quickness.  The club organizer, Yolanda, liked bossing my maid around so much that her fat pussy got really wet and soaked the cushion of her chair.  Of course that had to be cleaned too, but she stayed seated and made my horny helper polish her puss with his mouth as he scrubbed her spot.

I love my girly son, even if he didn’t clean my entire house.  The fact that he does, though, makes me appreciate her even more.  It’s great for me because someone has to clean up all the cum.

 

My Son, The Sissy

Sissy mom

 

I’m proud as fuck to be a sissy mom and of my ever blossoming soft little son.  She’s full of surprises, constantly kink hopping to help himself figure out exactly who she is sexually.  I think it’s a smart move for any pan sexual.  How do you know what you do and don’t like until you try it?  I think she’s really found his thing, though.  He’s fully embodied her silly little sissy side.

She absolutely has to get my opinion on all of his prissy outfits.  From frilly pink dresses and maid uniforms to leather corsets and fishnets, she loves to try on his wussy wear for me to see what I think.  She’s great at it, too.  My mama’s boy should get paid to model his effeminate ensembles, she makes them fucking work with legs that don’t quit and an ass I would kill for!  

Of course, being a true sissy boy mommy, I have to show her the ropes and teach her what being a girly guy is truly about.  It isn’t all fun and games for my pretty little pantywaist, she gets the same training as everyone else.  There’s no cutting corners, she has to follow all of the rules and listen to everything I say.  But, just like the others, when she’s been a good girl I’m sure to please her little clitty and let it dribble anywhere she wants.

 

These Tits Were Made For Sucking

Jack off With Mommy

Come here baby boy, these tits were made for sucking. Mommy loves her little adult baby. But he knows I’m not like the other mommies. I’m so sweet and nurturing I take care of his every need. I make sure my baby boy always has a clean pamper on his little bottom, and a paci, bottle, or Mommy’s own swollen and milky nipple in his mouth. I make sure he gets dressed up like my little sweet boy, and I take my time using him to take photos and make money off of. So many of Mommy’s other clients love humiliating adult babies, and I sort of get off on it, too!

Anal Sex Mommy

While I dress him up int he cutest little baby boy bonnest and a sexy adult diaper, I make sure my baby has a rattle and his paci too! Let’s not forget that I have to get him ready to make this special movie with me. Mommy has her perverted PDaddy Adult Baby Rape Fantasy having degenerates to come over and film something special where Mommy dresses up and pegs her baby boy. I have to get his little poop chute all ready to take Mommy’s massive strap on! I can only wish I had my own cock to penetrate that innocent little hole with!

He’s going to thank me while I hurt him because I told him to, and his little pee pee is going to be rock hard inside that soft, cozy adult diaper! I’m going to make him so desperate to go pee pee in his diaper so I can make him have a humiliating bathroom pee emergency accident! Mommy is quite the fan of omorashi and wetting, and being able to degrate and humiliate my little adult baby boy Roger Thomas Martin is my favorite thing!

Breeding Phone Sex

 

Sissy Maid Training with Mommy

sissy maid training

It really makes me happy when I get calls for sissy maid training. It’s so much fun to help a sweet sissy like you who loves to be of service to others. I think that’s pretty common for sissies, but usually, it comes in the form of cock sucking or something sexual. But I’m told fairly often that transforming into a feminized maid is a huge dream of sissies everywhere. Their tiny little clitty cocks get so excited when they’re all dressed up in a proper maid outfit with hair, makeup, nails, and of course, a pair of sexy stilettos.

Can you imagine yourself prancing around in your heels with your feather duster? Imagine how cute you’re going to look and how sexy you’ll feel. You will probably even get more than money at the end of your cleaning session if you do a great enough job. Aren’t you excited about that? I wonder what your “bonus” will be? He might let you give him a blow job, but you could get really lucky, and he’ll fuck your pussy really deep and hard. Either way, I know you will be happy with the payment you receive for your cleaning services.

Milky Milf

milf phone sexYou love this milf phone sex whores big milky tits don’t you baby! I get so turned on when you want a drink, my sweet little boy. That relentless greedy sucking and moans make mommy so horny. Even grown men sucking on my milk laden tits gets me aroused. My panties are soaked now and I know that this is wrong, its incest with my little son. That milk spurting out over the sides of your sweet cupid shaped lips as you fondle the other milky tits, I laugh and decide to squirt a little milk down your face! Its time to sit on mommies stomach and put that boy fuck rod right between my milky mammary as mommy pushes them together and let you tits fuck in the milky cream I have lubed up my tits for you. Look at your boy cock fucking mommies titties! Mommys lovers love to titty fuck! Your being a big boy just like the men you watch fuck me! Its time for a mommy phone sex titty fuck full of milk and cock cream!