Category: Jack Off With Mommy

Sissy Maid Training Mommy

Sissy Maid Training

I’m a slutty, slutty mommy who believes in sissy maid training for my sons to be disciplined for me. It makes me so happy when I have the opportunity to transform my sweet sons into little  sissies who cater to their mother’s every whim. My baby boy’s clitty is absolutely darling, and dressing him up in adorable frilly dresses with matching stockings, panties, and training bras is just too much fun! To make me happy, he said he wanted to do anything, so today he is my little maid and I can play with him however I please.

It’s the most adorable little French maid ensemble I’ve ever seen. He looked exquisite in his short skirt and thigh-high white stockings. I had ordered him to draw me a nice warm bubble bath, and since he was such a good boy, I let him wash my huge milky tits as well. Next, he proceeded to take care of Mommy’s hair. It felt really nice to be pampered by my son in his sissy outfit. Now that he did such a good job of taking care of me, I allowed him to enjoy himself after I had finished drying off. Until he came right in his panties, I rubbed his little peter through his sissy slut panties. Now for step two of Sissy boy phone sex with mommy Regina, Finding a cock to train him on, Mommy does have a nice big strap on to help open up that ass.

Trixie Is Your Mommy Slut

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I’ve finally managed to catch you jerking yourself off little one! I knew you’ve been doing it for months and that it’s so new to you but don’t you worry honey. Mommy’s here to teach you every thing you need to know and then some. After mommy’s taught you how to jerk yourself off nice and hard and all about hoe to tease that huge teen ball sack of yours, I’m gonna crawl right on top of you and place that sweet cock of my sons right at the hole of your mommy’s tight slutty pussy hole! Watch your mommy’s milf tits bounce up and down and smother your horny face while I fuck my horny young son! Tell mommy how much you love her tight holes while you cum inside me over and over again! Mommy wants your teen cum dripping out of all my holes so i can clean it up with my fingers and swallow it all up! Be careful to not ‘accidentally’ breed your milf mommy after finishing inside me!

wet mommy pussy ready for young cock

wet mommy pussy

It’s a blessing and a curse to be a young milf. I have boys coming in and out of my house all the time. My stepdaughter is a cute girl, and she attracts the football players and all the popular guys from her school. Everyone from the star athlete to the theatre heartthrob to the brainy hot geek comes over to fawn over her. Then they see me, and it is over for her. They are hypnotized and mesmerized. They want this wet mommy pussy.

I think quickly and fast and figure out ways to sink my teeth in the right under my stepdaughter’s nose. One of the best incidents happened when the linebacker from her school was coming over for dinner. I was quick to think on the top of my head and asked him to help with a jammed window. My husband was still at work, and that little bitch stepdaughter was lost in the store. I made her grab some extra spices and kept sending her a list of things so she could take her time at the store.
I had her little friend help out with dinner and a “jammed window” the only jamming that would be happening would be his young cock in my hot pussy. My tot was fast asleep thanks to a few yummy melatonin gummies, and my stepdaughter was at whole foods two cities over. I was getting my pussy pleased while my husband was about an hour away, and I wasn’t going to stop till this fucker creamed in me and got me pregnant. The more tots, the better the money I will be snatching from a divorce settlement in the future. My husband hasn’t called me pregnant since our last tot was born. So I do what I won’t have all the fun while concocting and plotting. I love being a mommy whore!

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Sexy MILF Phone Sex

milf phone sexI am a sexy milf phone sex slut. Younger guys love me. Young guys naturally gravitate towards older women. They want to cash in on our knowledge and experience. I was at the grocery store yesterday and picked up a stalker. He was a barely legal boy. He followed me up and down the aisles. Once I realized he was following me, I swayed my ass more. I bent over a few times so he could linger at my ass. I have a fine one too. He followed me out to the parking lot. He was not speaking, so I had to make the first move. Thankfully, I am a bold woman and that is never a problem. I asked him if he liked what he saw. As I said that, I was standing in front of him with my hand on my right hip and my head cocked to the left. My eyes sized him up and I liked what I saw. He could barely put syllables together. I guess I took his breath away. I took the cum from his cock too. I pushed him into the back of my SUV and gave him the best head he will ever have. He did not last long with these sexy mature lips on his shaft, but we did not have much time before we got caught being naughty in the parking lot of Whole Foods. Maybe if we were at Walmart people would have watched, but Whole Foods it was probably a misdemeanor, LOL. I gave him my business card in case he wanted to hook up again. I mean I can appreciate a big cock if it belongs to an 18-year-old boy or an 80 year old man.

Horny Sexy Mommy Whore Lorena

mommy whoreThis sexy mommy whore is always horny for young cock. My brats went back to school recently. I got used to having them around for the virtual learning. I had to go out and find some young dick to suck. If things were the same from when I was a schoolgirl, I figured there would be some boys at the mall arcade. That is where the boys who skipped school would hang out on cold days. I put on a sexy skin-tight outfit and went trolling at the arcade. I lucked out. I had my pick of the litter. The arcade was slamming with teen boys who wanted to bang a hot milf. I acted nonchalant as I checked out the boys I could select from. I went with a high school boy who was tall and black. I assumed his cock would be bigger than my sons’ dicks combined. I took him into the family bathroom and fucked him on a toilet seat. Can you tell how horny I was? I was so desperate for his young black cock, I had to fuck him in a public bathroom. His cock felt like a sword going inside me. Damn, he impaled my mature pussy. I gushed on his cock as he let off a volcanic load of cum in my pussy. Maybe my youngsters going back to school is not such a bad thing after all?

National 529 Sounds Just Fine To Me

Wet Mommy Pussy
Just the thought of National 529 Day excites me so much and makes my wet mommy pussy slip and slide like a hot evening in July. It’s the reason I fuck so well and so often! I love knowing I’ve been saving up for my sweet ones to go straight into the Domination Academy once they’re of that proper age. No matter which path my sexy sluts choose, dirty Dom, sexy Sub, or sassy Switch, I know I’m prepared for their future education here in fornication nation. As these delicious teen balls drop, while these wonderful tits blossom on sultry little chests, my earnings grow tax free. I know my hard earned slutty money is safe in savings to support the future tuitions and expenses of my slutkin menagerie.

My little whores will, of course, have to work very hard to pay Mommy Polly back every single cent she spends on their education as Future Sluts of America. I didn’t immigrate from France for my darlings not to grow up with grace, class, and fat, juicy asses. While they study at the Domination Academy, my lovelies need to pull side jobs depending on their skill levels, or sign up and get paid to be used as a demonstration subject down in the torture chamber.

I can use these savings for my own retraining, if that’s what I desire. And maybe I will, go back to classes with my hot teen asses. To be the MILF on campus again would be something to behold, and i’m sure just the thought makes my brat’s cocks like rocks and pussies run like rivers. Want to contribute to their 529’s? We accept Amazon gift cards and sexy cyber sessions. Why make us wait?
Mommy Phone Sex

Mommy Gabby’s Panty Wearing Sissy


Milf chat I adore my filthy, panty wearing little sissy boy. Pump! He comes over just to worship my body, and to beg me to let him pump pump pump that perfect penis right into me! His cock makes me drip even though he’s a sissy. He wears those pretty panties with such pride! I can’t help but get nasty turned on from it. How fucking sexy is it to have a knickers loving sissy slave right there at your disposal whenever you might possibly want him!? Pump! Though I should say, my sweet panty sissy sure does fuck Mommy Gabby just right. Every nerve in my hot little body gets lit up like a mother fucking Christmas tree every single time I see him ring my line. I always know Mommy is going to cum, and get a sticky, nasty load from my pump pump pump panty sissy slut right inside my tight wet cunt! He makes me cum so hard my nipples drip! How about that shit? Pump! I absolutely can not wait for him to come by and give me another incredible fucking. I know this pussy needs it.  Cum!

Incest Gives Me a Wet Mommy Pussy

wet mommy pussyI always have a wet mommy pussy. Between talking dirty to men and playing with my own brood, my cunt is never dry. In fact, I think I have a wetter pussy in my 50s than I did in my 20s. Part of that is because as I have matured, I have learned more about what pleases me sexually. I had a boring upbringing. No incest. No one touched me inappropriately. I lost my virginity in college. I married and divorced my college sweetheart. Everything happens for a reason, right? My nasty divorce happened at the right time so that I would be receptive to my horny teen boys. If I had not been emotionally vulnerable and sexually frustrated, I might never have fucked my first-born son when he was a teen boy. He jacked off all the time, and I now know he wanted me to catch him. I am always telling my phone sex mommy callers that it is never too late to fuck mommy. Often, a boy just needs the right circumstances to fuck his mommy. Timing is everything. It was for me and my boys, and I have not looked back since. I am happy to be a P mommy. And since I got a second chance to get it right thanks to my sons, when I remarried, I started younger with my son and daughter from my second marriage. I love grooming my little girl for daddy daughter love. And of course, I enjoy grooming my youngest son to be mommy’s sex slave. If only I had known the joys of incest and young cock and pussy when I was first married. But luckily, it is never too late to become a mommy whore. If it happened to me, it could happen with your mommy too. You just need the right mommy with the right experience to guide you. Perhaps, that is me.

Hot Phone Sex MILF

phone sex milf

Hi there, boys. Are you looking for the hottest, kinkiest phone sex MILF around? I have to admit that I really love taking care of and teaching all the neighborhood boys how to fuck. They always come to me very inexperienced, yet eager, and I love teaching them everything I know about how to please a woman. When my son was younger, all of his friends used to come over a lot during the summer. They loved seeing me in my tiny bikinis and they always fall over who got to help me with my sunscreen.

I think they used to fight over that because they knew the winner would get to fuck me. But if I’m being honest, anyone who wanted a piece of me could very easily get one. Just being around all of that teenage dick energy made me ready to take on every boy there. Do you wanna hear about any of the orgies we had? I would love to tell you everything. And all you gotta do is get on the phone and give me a call. I can’t wait to make you cum while I tell you what a nasty MILF slut I am.

BBC sissy boy mommy Strikes again!

sissy boy mom He is the reason I am a sissy boy mom. A BBC loving pipe whore who cant get enough of stealing mommies big black fuck rods! This sissy boy even has a queen of spades tattoo like this piggy slut cougar!  I make him roll that bowl every few minutes because I know his deepest secrets are mine. In a few minutes. My BBC pipe whore has done so much nasty shit while he is high!  He calls me asking if mommy can please share her black Adonis cock with him. He still gets his mommy fuck, but only after he has seen her bounce on a few cock s and get filled to the brim with huge hanging hard black dick cum. He says he is the best cock sucker this side of the Mississippi. I beg his pardon, nobody out sucks this milf, well not a sissy fag , although I am beginning to wonder!  I challenge him and he tells me he is sucking on a 13 inch black dildo because he is too high to go to the glory hole. In reality he is just scared because of what happened the last time I sent him there. See, men know a pipe whore who loves that glass dick. And black men know they can toss him around and double stuff him like an Oreo cookie, with lots of black cock cum in between his ass cheeks and down his whore throat. Some men need a filthy mom, some men need a nurturing mom. See, last night I went straight from this hour long Black cock freak right into a long slow sensual session of feminine dress up play. I held back for this second sissy, and just let him explore clothing like panties and dresses in beautiful soft colors. My second sissy called me back begging for more. I know what sissy men need, and I know that the majority of you love that I am a piggy slut mommy whore for BBC just like you!