Tag: sissy boy mommy

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.

 

my boy wants the best of both worlds

milf chat

I showed my son how to use a pocket pussy. It was great to get into some milf chat. Boys have an epic imagination, and their mind runs wild. When he told me he was having both sexual fantasies of men and women, I let him know it was okay. My boy can be a sissy who learns to fuck pussies and get fucked in his ass pussy, too. There’s no shame in being fluid, especially in 2022! My boy can be my girl whenever he wants.

I am ready to go out with him and show him how fun being open and ready to try new experiences can be.

Im going to show him how to fuck cunts and ass and get fucked. My strap-on comes in handy for times like this for me.

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.

Suck It Up, Sissy Boy

Sissy boy mommy

 

I am the most hard-core and intense sissy boy mommy by which your wussy ass will ever have the pleasure of being owned.  My sorry little sissy slaves do exactly what I say because they know that if they don’t their asses will regret it in every way imagineable.  I have torture methods for disobedient sissies that would make your fucking head spin.  I might clamp down those puffy nips, hook them up to a few fuck machines and stuff them full of fake black cocks, coming at them from every direction, until they scream out in agony and dribble cum out of their laughable little clitty’s.  To get more out of them, I’ll strap them up to a milker and force load after load of runny sissy splooge out of them that they know I’ll make them drink.  My pathetic little piss ants better do exactly what I say or there will be hell to pay. I’m gonna dress you up like a pretty little whore and make some money off your wussy pussy and that tight little ass of yours, you pathetic sissy bitch.

 

Flock of Sissies

Sissy boy mommy

 

I fucking love being a sissy boy mommy!  I have a whole flock of sissies at my beck and call just waiting for me to give them some depraved attention.  They love being my wimpy little whores and dressing up sheerly for my enjoyment.  I make them dress themselves in front of me in some mismatched slutty panties and old lingerie while I describe to them how every piece of clothing they put on will be torn off of them.  I slap some shiny pink lipstick on their thin lips to make their milquetoast mouths look like a target for all the thick cocks I’m going to make them take.  Their mushy maw’s and wussy pussies get stretched and abused by anyone and everyone that I choose.  They gladly do whatever fucked up things I ask and I can tell they like it because, when I laugh in their pathetic little faces, their little clitty’s get so hard!  They don’t get to touch them, though, not unless I say they can.  They’re my sissies, they belong to me.

 

Phone sex Mommy Advice

phone sex mommyWhen he called this phone sex mommy it was for advice. He was in his 20’s, successful and living with his first girlfriend. She was much older than him and had taken his virginity. My caller was anxious that he couldn’t keep up with a woman much more experienced and older. When pressed he confessed that he had asked her about her fantasies. And that had led them to a MMF threesome. You guessed it she wanted to use her young boyfriend to service cock while they both got fucked. Turns out they had already attempted this once and my poor young guy was under the impression she just wanted to be fucked by two men, and have him possibly watch as she got hers! But he was sucking and fluffing that cock for him, in an almost forced way. And now after this affair of two men and a Milf he was curious what she really wanted from him. That prompted his call to this sissy boy mommy. She wanted him to be fucked by a BBC and used as a cum catcher for a bull cock. I giggled as I knew where this was going. This young man who had only been with this Older woman, was about to be turned into a sissy for his Ladies pleasure! Of course I encouraged him to go through with it, because a bisexual man is so fucking hot! Don’t you think so, too?

Sissy Boy Mommy Play

sissy boy mommyThis sissy boy mommy is on the Rag for Christmas and My son already knows what’s up! Mommy needs her pussy cleaned up and her cramps relieved by his mouth. And you know every time I change my Tampon, he needs his boy pussy plugged up too. But it’s more than that. I always have to pee and he drinks it with such gusto! Drinking mommys pussy juice is more than my cum and mommy Honey for him. I push his little face deep in my cunt and grind so he gets every last drop! I had my best milf friends over today. And I explained that my son was a little different than most and he needed to have his period right along with me. My friends were delighted that I took the time to properly train him. But they wanted to show off their way of taking care of their needs. One was was more interested in the new strap-on I had bought for our Christmas day activities, And wanted to fuck him like the little whore in heat he was. I was so wet at the thought of another woman fucking my son with her mommy whore dick that I just had to let her be the first to strap fuck my little sissy slave son! I had one request, to suck my son off as she had him on his back and he ate my pussy! So as I brought him in the big bathroom for his changing, one of the mommies showed him how she changed her extra super tampon with a hairy milf pussy and the other strapped up to fuck his boy pussy. Mommy and her friends would love to do some sissy training phone sex with you, two mommies are better than one!

Who’s your mommy whore?!

mommy whoreWho’s your mommy whore?! I yell at my sweet little sissy son. My thick mom dick buried in his ass cheeks as he squeaks out, “You are Mommy!” That boy pussy belongs to me all year long. In and out I push faster and deeper as that boy dick spouts a thin stream of precum all over my panties, my son is wearing. Stolen panties in exchange for a mommy strap fuck!

I flip my little sissy over so I can fuck that cunt the right way. My tits leaking milk as I bounce that pink bald dick all around. I know soon, my big mom tits will be covered with my sons jizz. It just takes the right amount of long stroking and rhythmic thrust that only a woman can give to make him shoot his sissy boy load tit high! Nothing to fear as my cum eater fag son will clean me right up after!
It feels so good to be a sissy boy mommy!
So who’s your mommy? Can I fuck your boy pussy?

Sissy Mom Candice

sissy mom

A sissy mom Knows how to take care of that wee penis. Or shall I say clit? My own son is not extremely small for a man, rather just an average Joe. He has always dressed up in mommies pretty playthings and asked to be used as a girl during our incest play times! It has never failed that my sweet dumpling wanted to be ass fucked by his sister with mommies super duper strap-on! I have to say he is my Pretty boy whom I can’t get enough of. I sucked his panty clad “Clit” and his freaky sister pushed deep in that boy’s pussy. My son makes such sweet moans of pleasure that I have to reach down and finger my own milf pussy! This is what I love about double teaming him with my daughter! We use up that sissy hole and get clitty juice and then invite our Bulls over. Soon, my son will be sucking cock and taking a real dick up his ass. Until then he must be satisfied with eating mommy and sisters cream pies out! Wouldn’t you like to dress up and be my fluffer? Mommy is waiting for her sissy boy!

Sissy Boy Mommmy

sissy boy mommy“Mommy why isn’t my pecker as big as the other boys in school?” This was the reason I became a sissy boy mom. At first I was stunned. What do you say to your son who is supposed to be already through with growing and his little pecker, is… well, little still? I told him his dickie poo was perfect for mommy and left out the part where I knew he would be a little dicked man for a while now. I asked if he thought he might do well as a little lady, and at that my sensitive boy crumpled to the ground and cried his little heart out. I went and got his favorite pair of panties of mine. The silk red ones with the cute rosettes and rubbed them on his face. His tears dried up as he smiled meekly. “They still smell like your pussy mommy,” I told him to put them on and nothing else while I turned on some Barry Manilow and we slow danced across the living room. Having a little dick isn’t the end of the world. Sometimes you just need a skilled Phone sex mommy to help work through your small dick inadequacies!