Tag: sissy boy mommy

Little cock and big cock

Family fucking Roxanne I took my little bambinos out to eat last night for dinner because I had made a little extra money from shaking my ass on that pole and my baes were starving since the weak before was skimpy, but I guess I still did not have enough to cover all of dinner. I did not know what I was going to do. Thank god that the manager enjoyed trip over to the Philippines for paticular reasons if you catch my drift. He had a taste for much smaller cock. I had my son with me and he had to do some “extra” work to help me cover the bill for dinner. I thought it was going to bother me seeing such a small dick and a larger dick playing together but it actually turned me on quite a bit. MY son took it like a champ and only cried only a little bit. I may see if we can get free food elsewhere too and have my boys pay more often.

Sissy maid training with Peggy and Nicolette

sissy maid trainingNicolette and I both know that some boys just need sissy maid training… even when they say they don’t. My daughter’s husband is that kind of boy, he is very effeminate in the way he moves and the way he speaks and he acts certainly doesn’t ever act like a grown man. Honestly, I think the only reason my daughter married him in the first place is because she walks all over him, she has no respect for him at all. It was so easy to convince her to let us play with him, all she asked is that we record it all so that she could watch it later and laugh at him.

Nicolette and I ambushed him at home, we told him that he was going to learn how to be our little sissy bitch and he didn’t even protest! He just followed us into my daughter’s closet and let us dress him up like he was our little dolly. Poor boy cried when he saw us taking pictures of his shame but his little clitty was rock hard so his pitiful whining wasn’t very effective in making us want to stop… if anything it made us want to humiliate him more!

sissy training phone sex

We made him get down on his hands and knees and pulled his panties down so Nicolette could whip his pathetic ass while I put on my biggest strap on cock, he was no longer pretending that he didn’t like it… in fact he was begging for more! His ass was red and raw from his spanking and his tiny dickie was hard and oozing precum everywhere and when I shoved that strap on dick balls deep inside him he instantly came! Pathetic little bitch can’t pretend to be a man anymore, we own his little sissy ass now!

Halloween Humiliation

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I had a blast this Halloween! My son has been awful this last month. His attitude is shit and he keeps back talking me. He is acting like he is the man in the house when really he is mommies little bitch. I was tired of his smart mouth by the time we were getting ready for trick-r-treating. I got him the ninja costume he wanted and picked out. Now he hates it. I was done with my little bratty baby, that’s when my brilliant idea hit me. I stripped him down and put a cloth diaper on his ass and lets not forget the rubber panties! I put him in a onesie and slapped a bottle lased with laxative in his mouth. If he was going to be a big baby then that is what he was going to dress up as and be dragged around the neighborhood like the giant man baby he is! As soon as we got to the first house the laxative kicked in! He shit himself just as the door opened. A big waft of shit smell and they slammed the door in his face. My brat was humiliated by the end of the night. Watching him walk around all night in a shitty diaper and see doors slammed in his face made my pussy so fucking wet. I made him lick my creamy pussy through my dirty sinky panties! That’s the best treat he got all night long.

Mommy phone sex with super hot and horny Trisha

mommy phone sex

Call me Mommy and let me teach you everything you need to know about how to touch a woman and where. Mommy and son will play fun games and mommy will guide you through the whole, exciting experience. I know what I am doing and love to teach you how to touch yourself, how to touch me and we will have the best time!

Mommy will put you over her knee after pulling your pants down, and reprimand you for being such a bad boy and looking at all that porn. When mommy sees how excited you are, she may allow you to get on your knees and please her. Mommy will show you her pussy, and teach you where to lick it and how. Don’t you want to fuck mommy? Mommy loves when her little one is patient and attentive, willing to learn and be told exactly what to do. Mommy can make you cum harder than you have ever cum in your life.

My Diaper Baby

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I love my son as much as my girls; I know he is going to be a diaper baby forever! Even when he becomes a big adult, he’ll always be my little diaper baby! Even when I change his diapers now it makes me think about all the men I talk to that are still obsessed with diapers. They have as many mommy issues as you would think! They need a naughty mommy that is going to touch that tiny little cock when they’re getting changed. Just like every diaper change now I am sure to inspect that cock until I get that little boner throbbing. I want to feel it twitching a growing in my hands. I will stroke it, kiss it, and suck it till it’s slimy with precum. That’s just what I want… and he clearly wants too because he never cries. It will be like this forever, a bonding time that only a mother and son can share together. I made that cock, and I am going to wipe it clean, with a wipe and then my mouth… and then it will time to powder it all even that little bottom and on goes that diaper! Perfecto, my darling. This is how a date is supposed to go! A Mother/Son date that is…

Mommy breaks in a Sissy.

jack off with mommy

My poor little sissy. He still hasn’t learned how to properly suck cock. I think it’s time to go out and get some practice. He says no because he doesn’t want to be recognized in public wearing his mini skirt and thigh high stockings. But he’s such a pretty girl and that sweet mouth is begging to be used along with a tight little man-pussy. Oh, yes. it’s time. I saw him last night on his knees trying to suck a big black cock. He gagged and sputtered. My nigga loved dominating him and just face fucked him harder. He nutted so hard that cum came out of sissy’s nose.

So put on your pretties, your lacy thong. Get those balls shaved smooth. Cause your training starts tonight as I guide you on being the perfect little cum guzzling tranny slut. Our first stop is a local glory hole where you can learn to suck a cock correctly. Maybe after a few dozen loads pumped down your throat, you will be able to give head with some finesse. If not, I am gonna just back you up against that padded hole and let the savages rip that asshole wide open. Oh, they are gonna love that tight little boy-cunt so much!!! And I will be laughing at you while they do it!!!

Mommy Phone Sex or Sissy Mom Sex?

mommy phone sexSundays are mommy phone sex days.  Mommy gets dressed up in her Sunday best. Maybe you get to see her putting on her sexy pantyhose. Or catch a glimpse of her in her sexy undergarments. Are you turned on or jealous that she gets to wear such pretty things and you can’t? A sissy mom would never punish you for wanting to play dress up in her clothes. She would actually encourage it. I have 6 sons and not all of them share the same fetishes. I have two boys that love mommy’s panties, but for vastly different reasons. One of my older sons was a panty stealer. He would take them out of my dirty hamper to jack off in them. He loved the smell of my ripe pussy, the flavor of the cotton lining. Like most teen boys, he was just curious about mommy’s pussy. Once he got to eat and fuck the real thing, he lost interest in my panties. My youngest son from my first marriage however, liked more than my panties. He liked all my sexy clothes, my shoes, even my makeup. He is a sissy boy, but I love him. I encourage dress up. Even gave him a girl’s name since clearly he is more of a daughter to me than a son. We shop together for clothes, he even fluffs some cock for me and does little sissy maid tasks. Sometimes I am a very nurturing mommy, other times I am getting off on publicly shaming my sissy boy. So if you like mommy’s panties for reasons other than mommy’s pussy, don’t feel ashamed. You just need a sissy training mommy to help you be the best sissy you can be. Who is ready for dress up time? Sissy school is now in session.

Mommy’s Boy Becomes A Real Sissy

Sissy training phone sexI told you the next time I caught you in Mommy’s panties there were going to be consequences. Knowing you could not resist doing it, no matter how many times mommy told you, I planned for such an occasion. I o into my room and get the new outfit I have bought for you. When I present you with your pretty pink dress, blonde curly wig, white stockings, and ruffly panties, you complain. You say you don’t want to dress as a sissy, you only want mommy’s panties. I tell you there will be no more half assed crossdressing. Since you want to wear panties so much. you will wear the complete outfit. Hearing the sternness in Mommy;s voice, you begin to comply. You put on the ruffly panties quickly, loving the way the satin and lace feels as it glides over your cock. More hesitantly, you put on the dress and wig. Not knowing how, Mommy helps you get into the stockings. The feeling of the silky stockings is overwhelming as it slides up your skin and I see your erection begin to grow. Mommy knew you would love this. A cute pair of Mary Jane shoes complete your outfit. You say you feel ridiculous, but your rock hard cock tells another story. Now its time for Mommy’s little sissy boy to service Mommy. My pussy is dripping wet and ready for your tongue. Oh, you thought you would fuck me? No, sissy’s don’t get to fuck Mommy. Sissy’s serve Mommy and Mommy’s friends with their tongues. You will get me prepared and watch Mommy fuck a really big cock. After I am finished I will need you to clean my pussy for me. That’s right, you will suck all the cum from Mommy’s pussy. I know you love the taste of male cum just as much as you love putting on these sissy clothes. If you are a really good boy, I may even let you suck my pussy juice off my friend’s cock. You always did want to suck a great big cock, didn’t you?

Momma’s Big Adult Baby!

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My sweet son get’s what ever he wants. He knows how badly mommy wants a new sweet angel to gush over, and care for just like she did him when he was new to the world. God just thinking about how sweet the fresh new ones are to in this world makes my pussy wet! That is why my sweet adult son loves to dress up as a wittle adult baby! He goes potty in diapie and mommy gets to clean him up! His poopies are stinky! But I get to clean his ass, I love wiping all of his shit off his cock and balls. I am so genital with his big boy cock that he get’s hard for him mommy. Some times I get so fucking turned on as I wipe my sweet adult baby boy’s ass I have to suck his cock before I finish cleaning him.. I have to stick his big cock deep into my pussy and fuck him while he sits in his dirty diaper!!

Make me cum for Mother’s Day

jack off with mommy

It’s Mother’s Day and I can’t believe the party my boys threw for me. All of my little sissies did the hottest lingerie show for me. I have way too many pairs of panties myself so I let them raid the panty drawer.  Let me know if you want to buy some for yourself. Then you can really jack off with mommy as you wear your special sissy panties that I hand pick for you. Feel how your cock swells when  you put them on. That’s because you really are a girl at heart. A girl with a penis is a great thing. Let me show you what I mean. I want to see you bent over with your panties down as mom guides a hard dick into that boy pussy. I’ll teach you how to fuck and suck so you can be the hottest sissy around. Mommy will break you in right for Mother’s Day. Bring that ass toy with you. You’re gonna need it.