Category: Sissy boy mommy

My Diaper Baby

mom fantasies

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.

Jack off with Mommy for the first time.

jack off with mommyEvery boy has a need to Jack off with Mommy. It’s important to have a strong mommy figure in your life. Maybe your mommy worked too much or maybe she was a total whore who neglected her young son. Either way, you have this craving for a mom. I know every boy needs one. Whether it’s to call for advice or to fantasize about. Mommy was your first love and you lived for a peek at her tits or a flash of skin in the bathroom. Your first pair of panties belonged to mommy. The ones you picked up and looked at. Maybe you even sniffed them, and it got your boy dick hard enough to jack off with mommy.  If you were a lucky boy, your mommy sat you down and told you all about women and sex. Perhaps she gave you a look at her tits or pussy. If you were my son, I’d have done more than that. I would’ve taken that dickie into my mouth and given you a blow job.  Or if I was feeling horny, spread my legs for a better look and perhaps even let you poke your throbber into this slit. We wouldn’t have stopped there but I’m not giving you any more details until you give me a call. Come Jack off with Mommy soon.

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?

Forced into sissy maid training

sissy maid training

I caught you again, you little asshole. Stealing my panties so you can jerk off in them. You wanna be a girl so bad. I’ll make you one. I toss a pair of panties at you as you whimper, your hard dick softening. “You’re not going to need that hard-on. Mommy has big plans for you.” I grin. “Now put this on.” I hand you a frilly dress with pink ruffles. “No, Mom, please.” you beg. “No sir, mister. I told you that my bedroom was off limits and you disobeyed me for the last time. It’s time for your punishment.” I giggle as you don the sissy dress, your long skinny legs all hairy. I march you to the bathroom and shave them, along with your balls. You are crying now. “Better quit that bawling. It’ll smear your mascara.” I sit you down at my vanity and apply some garish make-up. Foundation, bright pink blusher, and blue eye shadow. I fluff your hair and spray it stiff with hairspray. You look like a drag queen.

“Follow me.” I order. I take you out to the front porch and point at a chair. “Sit.” I hand you a large sign written in bright colors. “I steal Mommy’s panties so she made me into a girl.” Just then several teens walk by, including your crush. They point at you and laugh as they take pics. “I just made you famous, sweetie. Bet you won’t be stealing anymore of my things.” I’m still laughing as I walk inside, leaving you on the porch to face your shame.

sissy boy phone sex

Momma’s Big Adult Baby!

Milf fantasy stories

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.

Mommy Specials for you.

jack off with mommy

Are you ready for something special? How about a hot phone sex special? You never called me and now is your chance to see if I can rock your cock. A good mama always give her boys the “special.” I’m a very naughty mommy and I love incest phone sex and all of those things that young boys fantasize about. Remember trying to get a peek of mom’s tits? Or those times you snuck that pair of dirty panties back in the hamper all gooey with your cum.

Don’t be a shy guy. I’m a sweet mom who dotes on her boys needs. I know how to handle a young man who is afraid to tell mom how much he wants her. Let’s do a horny roleplay and I’ll be the mommy you wish you had. Let me take your virginity or introduce you to my strap-on. You’ll always have fun when your mommy is like me. Newbies always welcome. I cater to cowards.

mom fantasies

Mama Pearl on Being a Cock Sucking Mommy.

cock sucking mommy

Every young woman needs a cock sucking mommy like me to teach her the ropes. There’s an art to cock sucking and once a girl learns it, she will never want for anything. Men love a girl who is good with her mouth. He’s more than just a meat popsicle you know. This is aimed at my cock loving sissy boys, too. Listen to this experienced cock sucking mommy and I will teach you to give the best head ever. If you are shy, go to your local glory hole and practice on some anonymous cocks until you learn to swallow and feel confident with your technique.

Take some advice from Mama. I will train you right. Cock sucking can be great. Once you get a big meatstick in your mouth, pumping away, you’ve gotta know how to handle it. Slurp it, make some noise. Moan. Whimper. Don’t be quiet. Sound is like gasoline. It adds heat and fire to that blow job. Keep that tongue moving. Swirl that head, suck those nuts, use that hand to make things feel tight and juicy. Don’t just be a bobbing head doll. Fondle and tickle those sacs while he fucks your tonsils. Slide a fingertip into his shithole and see how he reacts. If you don’t get your make-up smeared all over your face, you’re not doing it right. Next, work on that gag reflex. Men love to make you choke on that dick but no one wants to get puked on….Well, most don’t…but that’s another blog!!! Learn to swallow that beast. Let those balls slap your chin. When you feel them draw up tight, you’re almost there.

You’ll hear him begin to moan. Some men beg. Stop several times and make him wait. It’ll make him cum so much harder. His fingers will clutch your hair and he may grab your head and push himself into into your mouth, faster and deeper. Now wait for your prize. Yes, that cum is your reward. Slurp up every drop, roll it around in your mouth, show it to him. Wear it or share it!!! Let it dribble down your tits. Now swallow and smile. He’ll be in love, sweetheart. Take it from an experienced cock sucking mommy who wants her little girls and boys to give and get the best blow job ever!!! Take it from mama. It works!!!

jack off with mommy