Category: Sissy boy mommy

Sissy Boy mommy Dominatrix

Sissy boy mommy

Sissy Boy’s mommy Dominatrix Regina knows how to handle unruly men and boys alike. 

This particular story comes from a man who pays for my mommy’s services. Besides the fact that my offspring enjoys my milk, I have men who pay for play for a mommy experience much like you do over the phone. And I would love to have you recreate the mommy dominatrix scene that happened just the other day. 

Now this client has a wonderful backstory about his aunt who made him a baby for her. Humiliated and regressed from when he was just a little boy all the way until he was in his teenage years. And Mr. Sissy’s baby really enjoyed it. He longed for a mean woman to put him in his little boy place. He had put it out of his mind, until some years later when he was able to afford an escort with lactating tits. That would be this Mommy! But by now his obsession with a dominating woman had evolved into him becoming a completely utter slave boy. After some months of just using my mommy titties and being put in diapers and bondage.

I decided that this man needed something just a little more. The fact that he had a nice decent dick did not elude me. I knew I would have to put all my sissy training phone sex skills to use on this one. I decided that my sissy slave would need to completely pleasure me and humiliate himself before he ever got another taste of breast milk or milf cunt. Cumming on my boots and licking my pussy was just part of our naughty playtime. But in the end, my big sissy baby little boy did what he was told so he can get some mommy milk. And I sure hope you do what you are told, so you can be my good baby boy.


Sissy training phone sex

Sissy boy mommy seeking a new cocksucking faggot, any takers

Sissy boy mommy Looking for a Sissy mom? Well, panty boy don’t be so shy, search no longer… I know plenty of men who would love to stretch that sissy hole of yours. It’s not your fault honey, it’s daddies he’s the one who couldn’t help but stretch that tight asshole when you were younger. I know you loved the feeling..  Now that you are older you cage your weenie and massage your prostate while thinking of the first time ever that daddy slid his way into your pucker and your hands clenched into your twin mattress.  You can admit after all these years that have gone by you chose not to play victim and instead realized you actually get turned on by the memory.. You come to me hoping I’ve got a daddy with a big meaty dick for you so you relive your hottest reality.

A Sissy boy mommy always has a line of dicks and many that would love to have a femboy like you dressed up in momma’s lingerie ready to surrender and swallow up a load in that cum guzzling hole of yours. Actually I have 3 here with me now, hoping I am able to find a hot loving sissy slut who can give a mean blowjob. Just keep in mind you don’t have as much experience as I do so you need to keep your hormones in check and allow mommy to lead the way.. No worries You are going to become a perfect slut as long as you properly follow instructions.. For starters you are going to be down on your knees sucking the balls of his big black cock while I ride his dick reverse cowgirl.. I want to make sure his cock is stiff and ready to give your neck a beating.. The saliva you hack up as he throat fucks you will be smeared on your asshole to get you lubed up.. Then we will have the guys take turns gangbanging you and draining their balls deep inside of your gaping gloryhole.. That’s what Sissy training phone sex is all about, honey! xD 

Sissy Son Becomes Mindless Slut for Father and Brother

Sissy training phone sex

The best part of being a sissy is being used like a mindless slut. Men with big cocks love brainless fuck dolls they can fuck the shit out of. You can fuck a man in all sorts of positions, but the feminine mindset is always that you are a toy to be used. For this, you need training turning off your brain and letting men with big cocks use you. That’s why I brought your older brother and your father here to be your guides. Get on your knees and keep your mouth open so they can face fuck you and use your throat like a pussy pocket. When they tell you to bend over, you bend over without a thought. The best kinds of sluts are the obedient kind. When they both fill your tight hole with both of their cocks, all you need to do is be a good little bitch and take it. You know you love being a mindless slut, having your holes used and abused until you’re dripping cum out of every hole. Don’t think, just get fucked. You are here to make your brother and your father feel good.

Naughty Mommy whore gets bread by desperate son

Mommy whore I rode my desperate son until he loaded my cum guzzler with his Biggest cum shot… His eyes rolled back and his legs spasmed; based off his reaction I knew for certain he had never fucked an experienced Mommy whore before or for the most part, not one nearly as good as me. I needed to wake him up for school, he had snoozed his alarm and it was already a quarter past 8, with just 30 mins to spare for him to get fully dressed.. I knew a nice wake me upper was all my sweet innocent boy needed! His morning wood was bulging through his Hanes trousers..

I figured, what better way to wake him, than to drain his swelling scrotum. I slipped my way beneath his covers and worked my way up the mattress, gliding my warm Wet mommy pussy lips up his leg to wrap my mature cunt around his throbbing cock. I wanted that creamy load more than ever.. The look of his veiny thick dick was such a tease, momma wanted to feel him pulsing inside of my coochie..

All I could think of was the baby-making seed he was going to plant inside of me!  Yes honey, of course I prepped before I fucked him; I lubed him up with saliva right before I rode him like a Harley.. I wrapped my mouth around his shaft and drooled, rubbing my cunt while soaking his dick up! My sweet lover boy was relieved, he was the jolliest boy after mommy got through being his Breeding whore.. I grabbed a warm washcloth and cleaned his dick off from my pussy resin.

I knew he was going to need some help after the morning fuck I just gave him. He got dressed quickly and wandered off to school.. He loves his whore of a mom and I know in this lifetime I will be irreplaceable, Not to be cocky or anything but I’ve got my way of leaving a handprint not only on your cock from jerking you off but on your heart and tender mind.. Come fuck me and see for yourself, this hot momma has earned her bragging rights. 

The Breeding whore got fucked so hard it made me wet

Breeding whoreI got so turned on spying on my son fucking his girlfriend; that I wound up fucking myself with a foreign object.. I was hiding in his closet hoping to get a good peek at how well he fucks her tight hole.. I got more than just a peek! He had her bent over the foot of his bed finger fucking her pussy on his knees… Her pussy was so plump and wet.. uhh, it was so fresh!

I grabbed a Gatorade bottle and began pumping my pussy.. It hurt a bit but once it got into my super soaked Wet mommy pussy, I realized how deprived I was.. The bigger the meat, the better the fuck! I watched as he pushed her down to her knees and dick whipped her with his cock across her face.. He teased her with his throbbing dick by having her drop her jaw and repeatedly hitting the back of her throat with his monstrous rod.

I was thrilled, in suspense as I heard her plead with him to fuck her sopping wet pussy.. He resisted and continued to walk her like a bitch on all fours around the room.. He then had her bend over in front of him face down ass up on the floor and reach back and spread her cheeks.. She grinded and whined all over her fingers then began smacking her bald shaved pussy.. He had no idea his Cock sucking mommy was masturbating to him fucking a Hot teen slut as if I were watching a live porn…

Finally, he gave in to her naughty moves and rammed his dick without word into her cunt.. I heard her cry out in agony but the good cry, I could tell by her whimpers she was getting the fuck I’ve always wanted.. I fucked myself faster and harder, I accidentally let out a loud moan and squirted all over the closet door and floor… They could hear my pussy streaming.. I couldn’t hold back.. The more I tried the harder and more intense it was! He blew his load in her Breeding whore cunt, opened the closet door, dragged me out by my hair and forced his creamy cock down my throat..

Phone sex whore gave son JOI

Mommy phone sex My horny son jacked his cock off while I instructed! When I walked in and saw him helplessly stroking while staring at Horny milf pictures, I knew he needed mommy to guide him through masturbation.. His cock was throbbing and his balls were swollen.. I assured him Mommy was here to help him with his hard dick..

I pulled my dildo out and advised him to do exactly as he saw mommy do. I grabbed some baby oil and lathered my 9 inch silicone dildo.. I wanted him to imagine momma was stroking his big dick as I drizzled his cock in lube.. While he was stroking I told him how bad momma would love to jack his cock off for him.. but I just wanted him to learn to be an independent boy!

Whenever momma isn’t around I want to be able to send him a  nude of my  pussy and patiently wait for a video of him milking his penis.. I stripped myself of my spaghetti strap tank top.. Giggled, while telling him that, eventually I would let him slide his cock between my perfect knockers..

I slowly slid my hands up and down the dildo as he followed my lead.. I could tell by the look in his eyes he wanted to stroke faster as I teased him with my hard nipples. I drooled on my rubber cock and began to pick up the pace.. His cock was leaking precum, he was beet red and whimpering.. I knew my boy was ready to explode but he knows if he cums without mommies approval that would upset me.. He hate’s to make mommy upset! Jack Off With Mommy

I told him to listen closely to my voice, close his eyes and grip his cock tightly.. I wanted him to imagine his cock was deep inside of my wet mommy pussy.. As he jacked and squirmed, I had him begging me to cum.. I leaned over him and gently caressed my breasts, breathing intensely over his abdomen, he couldn’t take it anymore; he exploded all over my tits.. When he opened his eyes he couldn’t believe I let him do such a thing!

Mommy Son phone sex for ABDL Play

mommy son phone sex

Mommy Son phone sex: becoming a little stinker in diapers!  

Oh, darling, I know these thoughts of having your dick squshed into a diaper make you feel naughty!  You need to be Mommy’s little boy or sexy baby boy even. Mommy Regina thinks might be one of those boys that still tinkles with his bed needing to be put in diapers every night. I wish you had a mother like me when you were growing up, Nurturing, Sweet, and sexual! I know now that it’s been way too long since you were in diapers 24/7! Adult baby boys have no self-control over what so ever and that’s why you cum crawling to me. Or could be my big mommy milkers that draw your ABDL ass in, wink wink! Let me just get out the baby wipes, the baby powder, and a few thick soft diapers. I am prepared to transform you into my sweet baby. Do not forget those plastic pants either, a naughty boy like you is sure to wet through! As an experienced ABDL Mommy, I know even the strongest and thickest diaper can not always hold your potty. Now, come and sit on my lap! Mommy needs to feed her breast milk and stroke your head. Be a good boy for this hot Mommy and drink up! 

Soon the feeling of a warm wet and full diaper will have you wiggling around. I will change you and pat your ass dry. If you are a super good boy, Mommy will give that wee little peter a kiss and make you explodies all in your diaper for me! I have the big tits full of mommy juice for your to suckle and all the ABDL accessories a naughty boy in diapers loves. You’re my adult baby in diapers and I’m your loving Mommy and Lactating phone sex whore for all ABDL’s even little girlie sissy ones.

Sissy boy phone sex is how you get inside mommy!

Sissy boy phone sexI had him dressed up in the prettiest dress I could find for sissy boy phone sex. It was a fresh and clean white that’d fail to hide cum because it was just that white. It had pink and black frills on the bottom which drew the eye to his hips and ass like nothing else. Its top had a lacey flower like bow that was made out of the perfect shimmery red material. The whole thing made my legs a little slippery and that was before I had him in it. Staring at him in a dress I’d have wanted to wear some years ago when I was less a dom mommy and more an innocent girl just trying to get a cock in my ass, it gave me lots of beautiful memories. Like the time a man pulled me into his car and reassured me he just wanted to get me home safe. I remember he said his cock came out accidentally and I totally believed him, even when it accidentally ended up in my mouth and filled my cheeks with slippery goodness. At the time I was just so happy someone was looking out for me that it didn’t click to me that maybe this wasn’t a good guy doing a good guy thing until my ass was leaking cum and he was trying to slip into my pussy for a fun round two and seeding of my soon to be wet mommy pussy.

Oh right, the boy I had dressed up. Yeah he was cute, he wanted to play mommy and sissy son. I like having sissy cum in my sissy mom mouth so I was all for it. There’s nothing like making someone’s dreams and desires come true while taking a little something amazing for the roud yourself. I’m a whore and I enjoy being a whore, so holy fuck was I ready to get him inside me. I didn’t let him leave without a creampie, I’ll tell you that. A rich and thick and creamy one that leaked down my legs just in time for me to go see my husband.

Mommy Fucks Sissy Maid Son in Ass

Sissy maid training

 

The most important parts of sissy training is learning to take orders and being able to take cock well. My son has been my sexy sissy maid for a week. I put her in the cutest French maid uniform and tied a bell to her tiny balls so I could always hear him coming.  I see my little one folding the laundry on the couch. I come up behind her and grab her hips. She asks me what I’m doing and I tell her she needs to shut up and take my cock. I push her panties to the side and ram my pre-lubed 9-inch dildo into her tiny ass. She could barely take being fucked like this, which means she needs more training. Her tiny little screams made my pussy wet, and I took some of my pussy juice on my fingers and used it to lube up the cock even more. I wanted to go deeper and shoved it harder until I was balls deep inside my little one’s ass. She squirts in her panties and I put them in her mouth, letting her taste her cum. 

Horny milf Pictures of Wet Cunt

Horny milf pictures

My son loves it when I take Horny milf pictures for him to share at school with his friends. Those little perverts run around barely old enough to wipe there asses with my pictures all day. Most of these guys aren’t old enough to make their own lunches but they find themselves every lunch with pictures of me in the bathroom stalls and their little dicks in tow jerking and cumming all over the place. It got so bad the principal called me with some. Fortunately it was from his son and they are very open. All it took was me sucking off that little one’s cock in front of his daddy and everything was fine. Some Daddies are so awesome about sex with brats and including any & all willing mommies. My brat says he has made close to 1000 this year of 2023 so far and he says he squirts everyday with his little buddies; sometimes on each other. I laugh so hard thinking about all their little hands touching each other and my dirty pictures getting covered in young sticky baby batter. How many young cocks have cum to Jack Off With Mommy this year so far? I’m hoping everyone in his class has pumped their loads and imagined my cum dump hole.