Tag: sissy boy mommy

Sissy Mom

sissy mom

I enjoy being a sissy mom. My oldest daughter had a little friend who was  not like other boys. I discovered him once playing with my sexy lingerie. He was not playing in the way most boys do. He was not rubbing his little dickie on my silky panties or my nylons. He was trying my things on. He was very embarrassed when I busted him, but he needed nurturing not punishment. I wanted to cultivate his sissy side, not shame it. I came into the room, kissed his forehead and tussled his hair. I told him to let me help him dress. I put a garter belt on him and some classic black stockings with the seam up the back. I had to pin the garter belt in the back so it would stay on him because of his small frame. I let him slip into some heels. I even put some pink lipstick on him. He gave me some runway moves. He came to life dressed up in my sexy things. I told him it could be our secret. I knew his parents. Very pious. They would never encourage his natural inclinations. Religion kills sexual exploration. He came over every day after school for years to play dress up. At my house, he could be who he wanted to be. He could explore his sexuality.  He is a full-grown sissy now. He no longer lurks in the closet. He has a sissy trainer who is his wife, a family, a good job and he still comes to visit the sexy mommy who encouraged him to be himself all those years ago. If you have no one who understands your love for the feminine and pretty things in life, call a sexy mommy. Mature women love sissy training phone sex.

My Sissy Mikayla Is the Prettiest Slut

sissy training phone sex

It was a sissy training phone sex day this mommy would remember forever! My sissy slut Mikayla loves to be dressed up and used. I know how sweet she is and how much she loves her pale pinks and yellows and cream-colored baby doll dresses. Oh, lest I forget her sundress and flutter panties. See I adore dressing her up and showing her off to my other mommies here! Eaddie Has told us that this sissy whore looks so beautiful in a pearl necklace. I didn’t know she meant a cum pearl necklace. Eaddie Is a hot sissy boy mommy who loves making Men into little girls. She showed Mikayla her panties and told her how pretty she was!

sissy boy mommy

And Polly had the great Idea after we got this yellow sundress and tights on Mikayla to bring her to the bridal store!  such a hot sissy mom with skills in making my pretty girl into a living doll! So after Eaddie and Polly were done dressing Mikayla the sissy girl up we made her look in the mirror. I pulled out big milk filled titty and loving gave my sweet pretty girl a nice drink. I wanted this to be the most sensual experience “she” had ever had!  Polly was an expert on hair and makeup and Eaddie was calling a few big dicked men for a surprise once we were at the bridal store. We had our princess ready to go. We took turns dotting and primping her!

sissy mom

Eaddie was excited about our surprise and as polly and I handled the gowns and made Mikayla a pretty bride, Eaddie opened the door to our dressing room and had one of her big dicked sons come in and pull down “her” Panties and tights so that dick could cum all over our pretty girls panties. Eaddie laughed as polly said pull those back up! Let Mikayla stew in that cum for a while. But I wasn’t done. And with a twinkle in our eyes, we let in three more big dicked men for Mikayla to suck and passed her around in her wedding dress! Fun Times! Cum and play with a trio of sissy loving Milfs!

Mommy’s Sissy Boy

sissy training phone sex

Mommy loves being a dirty whore! I am always bring round a new young well hung hunk around to fuck me nice and good. My teen boy loves to creep around mommy’s bedroom and spy on mommy when I am being a dirty fucking mommy. I love getting fucked by multiple man and being loud enough for my son to hear how many orgasms I get from getting pounded by strange men. I knew my pervert sissy fag was always around the corner watching me get pounded by his teachers, all his friend’s dads, his t ball coach, even his own little teen friends. I know his little peepee gets so tingly and hard watching mommy’s holes getting stretched out by every man he knows. Just when my sexual partner is about cum, I call that pervy little sissy into the bedroom. I love embarrassing him and calling a faggot and a little pervert for watching his mommy get fucked. It must mean that he wants to get fucked just like mommy. I have his T-ball coach pull his cock out of my warm wet mommy pussy and I made my sissy son suck the juices off his thick cock. I make sure to train that sissy faggot’s mouth to fit the entire cock and push his head all the way down on it. I love watching that faggy choke on that mommy juice covered dick while I shove a finger up his boy pussy. I make that little cock sucker suck and slurp on his coach’s cock until it’s nice and slimy. I made my sissy faggot slut get down on all fours with his bussy propped up. Then his coach slid that thick spit covered cock right into that boy pussy and fucked him so hard while mommy watched, I love watching the cummies leak out his bussy.

Sissy Mom Loves Summer Solstice

sissy mom

This sissy mom loves the summer Solstice because it means that I get to see my first sissy boy ever! see There is a huge sissy boy festival happening and on the night of the Solstice my sissy Ryan will be able to see me and Please me as a thank you for bringing out his true colors. Ryan is what I refer to as a P-sissy fag. He loves little boy cocks and being about to fuck little girls with his cock. This solstice Ryan was going to have a chance to fuck his very own brat. Having a little dick was very good for him. He could indulge in slutkin sex without worrying if he would ruin those little pussies and asses.  I mean I understand. I have had men shrink their cock back to the size it was when they were in diapers.  It was nothing to give Ryan the best sissy training and the best tiny asses and pussy of my offspring just a couple of years ago. And to be honored to give away his sweet angels virginity to her own daddy.

But.. here is the thing. I know that this big event has me so fucking horny. I have been giving my sissy boys extra special sissy boy phone sex. I have been fucking my sons and daughters like crazy. And then every night I am using my biggest and best sex toys with my sissy boys. and every one of my P-men has been getting really dirty p-mommy sex. I am so excited to be using my first sissy boy again. I am and will always be a p=mommy and when I can give sissy boys that same experience I just wet my mommy panties. Speaking of I need to find P-sissy Ryan some new pretty panties as a gift. I think I will just give him my dirty panties, wink wink.

Sissy Training Phone Sex W/ Mommy Eva

Sissy training phone sex is something I have taken a part of for many years, and it is at an all time peak as more sissy faggots start feeling comfortable in being the little clitty, panty wearing cock suckers they crave to be. I’m the kind of mommy every good sissy desires. I’m sexy, a little nerdy, and a very fiery red head that can set the spark off inside you and make you thrive for being a super sexy sissy. You will want to do all the things I tell you to do to make you the pretty little cock sucker you crave to be. Be the woman you are and I will assist and guide you into making you such a little subby slave sissy to that big bad cock full of the cream filling your bum bum or throat needs. It’s alright if you feel a little shy at first and just wish to talk to an open and understanding mommy. I have been very understanding with my son that loves to watch mommy fuck while wearing mommy’s soiled panties after I’ve worn them all day in the hot son showing houses and flirting… getting these panties creamy… with the hard bodied sexy maintenance guys. He’ll even wear them when I dripped a fresh fucked load of cum in them and returned home hours after without cleaning up. Yes, my son will dress up in my lingerie if it’s what the guys fucking me want, but most of the time they just want to humiliate him with me and make him a dirty ass licking cock sucker faggot. We get into many kinds of things together and I love taking him shopping and buy panties that I will expose to the clerks and other shoppers around that they are ones he will wear when he starts his school year.

Sissy Training Phone Sex

Cum Swaping w/ MIlf Phone Sex MOMMY

milf phone sex

My sweet milf pussy is a reservoir of cum.  MY sexy sweet boys love cleaning mommy out. Now I expect them too take that cum out of my pussy and feed it back to me. I love snowballing cum and hot cum swapping with my Sons. I even get my daughters in on the fun and will get those cunnies pumped full of cum for my boys to suck out. My sweet clean up boys enjoying young pussy that has been pumped full of sperm. A big drink of my tit milk to wash it all down. I love sucking these young cocks as well though, Then it is mommy cum swapping with my little girls. I think it is fucking hot to give them a mouthful of those brothers cum while finger fucking those bald clamshell pussies as I give them that brother cum!

Sissy Mom Hot Roleplay

sissy mom

I took a part-time job working as a rent a pig at the local mall when my brats were in school. Being the sluttiest security officer allowed me to find a nice sissy dick, that shops during the day to avoid the eyes of the mainstream.  Businessmen drop in to view the panties at Victoria’s not so Secret, pretending to be looking for wives and girlfriends when the crowds are gone. I met him here and with my big tits hanging out and watching him shop, he became aware of his body and became demure. I took the chance to ask him if he would like me to model something, knowing full well it was he who wanted to model the sexy panties, bras, and nighties. But I was still taken up on the offer and he put an armload of silk and lace for me to try on for him, This slutty mommy tried on so much and we even put extras on his card as I promised him a private show back at my place. I love closest sissy boys with an AMEX.

Back at my house, it was him modeling for me, and my strap on came out to play as I had my pretty sissy sucking and then riding me. And after I got his cummies I feed him from my heaving milky tits and let him get dressed and go back to his minions at his office building, with promises of me dominating and my brats to play with after school.

 

Do you need even more sissy training phone sex, I have it on good Information these babes are the hottest and you will find mommies, Doms and pretty girls for your wildest sissy play times!

sissy training phone sex

Seducing the boys

mom chat

Mom chat have you feeling frisky. I like making my boys closest friends drool over me. I am not the poster mommy. I am far from the Stepford housewife approach of things. I want to let my outfits speak for themselves. I enjoy making men weak. I also enjoy making boys nervous aswell. I love being a fantasy and a long lingering memory. Knowing you will compare every girl you take to bed to me after our passionate affair makes me one happy milf. I know girls half my age will never compare to my skills and the way I fuck. I often get in trouble trying to collect those boys. My latest secret rendezvous was during the boy’s sleepover. They had friends flocking all over the house. Mommy wanted her cunny to cum, so I went to my private room and started to play. I noticed I had a fan not too far away. I spotted one of the boys watching me rub on myself. I was so into it that I told him to come close. I began grabbing his cock and putting it in my hands. I was jerking the boy and wanted to blow the boy too, I did just that. I started to suck and fuck him. I had no shame. I was going to get off good. I’m such a breeding whore I might even be pregnant from the encounter.

 

 

breeding whore

Dirty Mommy Whore

mommy whore

Spring is in the air and that means this dirty mommy whore is measuring every boy cock she can find. See I know those cocks grow the most as the seasons’ change and little Chase and Leroy were all too happy to whip out those peepees and let mommy Regina measure them. Chase had grown a quarter of an Inch but Leroy had gained 2 whole inches since I last measured him. Now you know that I had to use my mommy mouth to get a good idea of just how fat that had grown. MMM, slurping boy cock is my favorite. Those hips just pounding into my mouth and guiding young hands to the back of my head to give them adequate lessons on fucking mommies face. That’s right Pump pump pump for Mommy! Now, my girls, had the same spring examination done right in front of chase and Leroy. I measured blooming tits and how much those cunnies were changing for mommy. I also asked My girls why these neighbor boys had grown so different and they were the same age. They both knew it was because Leroy was a black boy and chase was White. And they both knew that Little Chase would be forever Little in his cock. My little whores do seem to be right about that as Chase Daddy never grew beyond his boyhood. A fact I can account for as he was my sissy slut in training! But shhh, that’s Mommy Reginas secret obsession wink wink. I am so wet thinking about him as we speak!  Maybe that would change as I fed both boys Magic mommy milk. Perhaps I shall be having another Milf Chat to see if mommy’s tits could make these boys bigger, the better to fuck mommy and her daughters!

Mommy’s Special Boy

You’re a good little sissy boy for Mommy, aren’t you? It makes me so happy to dress you up in your sister’s bras and panties like the little fag you are. That’s right, put on a sissy fashion show for Mommy and the neighbor. Bend over and show us your boy pussy. Do your faggy little dance that I taught you; that’s right, shake your cute little ass for the neighbor. I promised the neighbor that I had the perfect sissy slut for him, so don’t let Mommy down!

sissy boy phone sex

I get so wet seeing my little boy in his pretty outfits, and even wetter when I can watch him be used up by huge cocks. Bend over for the neighbor, sweetie, and beg him for his dick. Look at you squirm as he shoves himself in your tight little boy cunt! Come here and lick Mommy while you take that huge cock in your sissy ass. Be a good boy and let the neighbor blow his load inside you, that’s right my baby cumslut. Doesn’t that feel so good? Be a good sissy boy and cum in those pretty silk panties for Mommy.