Tag Archive: sissy boy mommy

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!

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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.

Sissy Mom Regina Loves You!

sissy mom

Being a sissy mom means that I have my boys who I must tend too!  I really do fall in lust and love with every sissy boy. Every sissy boy needs a young sweet princess to play with. And yes One of my own sons is very much a sissy. See the boys on the street have been making fun of him every since they pissed in the snow and figured out my teenage son was less than average in his dick growth. Now I could lie and tell him it will grow, but I don’t He came to me crying his little sissy tears. ANd I dried them and asked him if it was really a bad thing his dick was small? I gave him a good feeding out of my tits and let him jack his cock off all over his mommy to make him feel better.  See That little dick means he can dress in mommies silky panties and I then whispered, his baby sis seemed to think it was perfect for her cunny! My sissy knows the love of a big cock and soon his little ass aka pussy will be opening up for grown men cocks now that he knows the truth about himself. That mouth has seen so much cock. I mean did it really take other teenagers to tell him his cock was too small for him to figure it out. His brother is a year younger with much more meat between his legs.  So many sexual doors have just opened for My sissy son with the ivory smooth skin and perfect asshole to have gaped. Now, who is first in line for some little boy ass? Or who would like some sissy training phone sex? I have the milkiest tits and the cutest panty collection for you! 

Phone sex Mommy Tales of Little Man

phone sex mommy

I am the perfect phone sex mommy to men that are short of Stature. I have my 50-year-old man who is Jockey sized who loves a dominate taller woman.  He makes my pussy wet with his Micheal Jay Fox Good Looks and Tom Cruize Skin Color! A man who loves the 6 ft  Amazon Dykes of the Hamptons! He wants to be broke in half by this Mommy. Bent over my knee and spanked like the little boy sized body he has! And my small handsome man has this little waitress that would dwarf among the fabulously long legged tall Price is Right Models. My oldest is taller than him and so is most of her 6th-grade class!  Why I just want to take my sexy brat sized man and little waitress female and be there slut dom mommy for the night. Dress them up as I do my little sluts and have some perverted P-mommy fun with them! I won’t forget my paddle either! I will force them to suck my milky tits as I take turns sucking each of their little sexes. Come here to mommy let me pinch those small cute little cheeks and have my way with you between my pussy glazed like a donut in my pussy juices.

Discovering I Was A Sissy Boy Mommy

Sissy boy mommy

I realized I was a sissy boy mommy when I was vacuuming my little boys room. I didn’t think to check under his bed. As soon as I ran the vacuum underneath, I knew that was a mistake. I quickly turned it off and pulled it out to see what it had just tried to suck up. To my surprise it was a dirty magazine and not just any dirty magazine either. It was a sissy magazine.

It seems my little boy wants to be a sissy. You want Mommy to dress you up in lacey panties and a matching bra. You want to wear fishnet stockings. But most of all it seems you want to suck on a big thick cock. When you came home, I was sitting on the sofa with a couple of my girlfriends. Your dirty magazines were laying on the coffee table and you were turning bright red.

I told you that the girls and I have decided to make you our little sissy for the night. I made you strip naked in front of all of us. We put you in a pair of hot pink panties and fishnet stockings. We made you tuck your cock and balls in between your ass cheeks. Then we gave you a banana and told you to pretend it was a dick. We decided who better to teach you how to suck cock than three dirty whores.

Watching you prance around in your hot pink panties and deep throat that banana made our mommy pussies so hot and wet. We made you eat all three of our hot wet cunts. If I had of know that you were that skilled with your tongue, I would have turned you into my sissy slut sooner. You got so turned on that you ended up blowing your load in your pretty pink panties.

Mom fantasies

Full time mommy slut

wet mommy pussyI have a way of making all my boys feel good. I am a full-time mommy slut, and my wet mommy pussy sure does put in work. I like to make my boys feel extra special and even though I am at work making other boys feel good when I get home my undivided attention belongs to them. I make their perfect cocks cum with my mommy’s mouth and my hand too, Lately I have been getting more daring and letting them fuck my tight ass. I can’t wait one of them can fuck my cunt and ends up breeding mommy. I think that will be the day I submit. My boys keep me so busy in every which way.

Phone sex whore Peggy is training a sissy

phone sex whore“Phone sex whore Peggy is training her son to be a sissy!” That is what I overheard my neighbor telling her friend and I know I should be pissed that she is gossiping about me but I’m really not. It’s the truth, why should I be mad? My son is a little sissy boy, he always has been and now that he is getting older it’s time to take his training to a whole new level. I set up a date for him so of course I had to get him all ready and turn he into a she. First up was a nice warm bath to get him smelling sweet and then I dressed him in some sexy lil panties with a matching bra and a sexy black mini dress over them. Then came stockings and heels and then I did my sweet sissy boy’s makeup. By the time I was thru with him he was looking so cute and sexy and I knew that he would be very ready to get that cherry popped. I had a sissy lover coming over, he loves a boy like my son with a tight little boy cunt and I knew that by the time the night was over he would be the whore he had been dreaming of being for so long. Just getting him ready like that had my pussy dripping wet and I had to stop to make my lil sissy boy eat mommy’s pussy before our company arrived but of course my friend showed up while I was grinding on his lil sissy face. He was fine with it tho, it got him rock hard so he just lifted up my son’s dress and slid his rock hard cock right into that tight boy cunt right then and there! It was the best night ever!

Mommy Wants to Teach You Well

Sissy training phone sex

Do you want to jack off with Mommy and have some fun well you can do it don’t worry I’m ready for you? My little boy, you’re just so sexy you need your mommy to feed you good milk I have some I’ll feed you well I won’t let you starve you can eat my yummy cum. Mommy’s little boy is the favorite in the world he just dresses up like I want him to. I want to dress you up like a pretty little sissy oh my goodness we’re going to have fun. Don’t you know sweet boy that mommy just can’t help herself that moment that I caught you smelling my panties from my hamper it gave me permission to do whatever I wanted? Now Mommy has to train you to teach you just how to be a sissy, in fact, the best in the world. Don’t worry Mommy’s going to dress you up like a little girl and make you sell your nice tight booty two boys big boys with big dicks and big toys. Mommy’s going to tape you I want to videotape you well Mommy’s going to do it mommy loves the Way You Are. Now, why don’t you take your cute little nose and buried in mommy’s wet tasty pussy right now? Believe me, sweet son Mommy needs you to practice so that you could be the best cunt eater and dick sucker ever. I’m going to make so much money from selling my little boy’s mouth and asshole all day long. I want you to know son I won’t have any rules whatever the guys and girls want to do to you is allowed there are no problems with me what so ever. I love my sweet cum-filled cock boy I love all the little tricks that I’m going to teach you, and I love all the little skills that you already know. I want to watch you getting fucked by three guys at one time that’s called running a train, and they are going to run a massive big cock train on you. Are you ready little boy for the action to come, I know we’re going to have a good time. I’ll take pictures of your facial expressions while you’re taking big 10 inch cocks up your asshole. Now do as Mommy says and lick my wet pussy until I squirt all over that pretty little face.

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