Tag: sissy training phone sex

Sissy Training Milf

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When you are training to be my sissy there is one main rule you must remember. I am your Alpha. Yes, I am a female, so? You call yourself a man to your colleagues but when you step into my room you’re my slave. When I get my hot black slit fucked my sissy boy better be there ready to beg to suck the cum out of my twat and clean it all up. Before you can you must also thank the man who filled me up for allowing you to taste his yummy load. You’re lucky I let you get this close to my beautiful pussy because your little dick can’t even begin to satisfy me. Even during the nastiest times you will be around to be my sissy will be in training! I refuse to rough up my delicate ass after taking a shit when I can just have my bitch clean my shit and piss with his face. Being a sissy in training has its perks though! You get to spend all the time I want you to with me!

Mommy breaks in a Sissy.

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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?

Make me cum for Mother’s Day

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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.

Phone Sex Mommy Nicolette is a Sissy Mom Too

phone sex mommyI want to be your phone sex mommy! You can be any age you want too! As a P mommy, I have played with sons of all ages.  And I have sons of all kinds. Currently, I have a school boy who thinks he is a school girl! Naughty little boy who likes to wear mommy’s panties.  He had an accident at school yesterday that tore his jeans during recess. The whole school saw that he was in women’s panties and laughed at him. They called him a sissy. He ended up in the principal’s office. I had to go bail him out of jail. I have told him time and time again, he can wear my panties at home, but never at school. School age boys and girls can be very cruel. The principal suggested I get him counseling. Like the principal never stole a pair of his mother’s underwear before. Every guy goes it. Doesn’t mean they are gay or even a sissy. Some boys  just like to feel close to mommy’s pussy. Some like the feel of the silk on their little dicks. Some realize they have little dicks that get lost in boxers so prefer the tight fit of mommy’s panties on their junk. I asked my son when we got home, why he disobeys me by wearing my panties to school? He told me he thought he might be a sissy. I asked him how he even knew about such things at his age, and his response was from you on the phone! He has been listening to me be a sissy mom for all my phone sissies. Luckily, my boy toy husband is very open minded. When I told him that his son thinks he is a sissy, he didn’t shame him or even punish him. He just pulled out his cock and ordered his sissy son to suck daddy’s big dick. Sissy school is in session at my house!

Sissy needs some Mommy Love

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Oh, Michael, you poor sissy. Someone really needs to teach you how to dress properly. That frock you’re wearing looks like you stole it from your granny’s closet. It’s so frumpy and pathetic, kinda like you. I train sissy boys and it looks like you need some lessons. If you’re gonna be a sissy, be frilly or be sexy. Flaunt that shit. But those awful dresses have to go. I see that I need to take you by the hand and give you some guidance.

Taking you shopping was fun but your sense of fashion sucks. I was helping you out of a tight dress when I saw your penis. OMG. I had to laugh. It was the tiniest little thing I’ve ever seen. How can you pee out of a button? I really get it now. You’re not a sissy because you want to be. You’re a sissy because you have no other choice. There’s no way you can ever please a woman with that nub. It would be like jerking off my clit. Please keep it tucked in your panties where no one has to look at it, much less touch it. At least in your fluffy penis pouch, it looks like you have more cock.

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I was feeling so mean after we finished shopping that I made Michael be my pay piggy and buy me steak and lobster for lunch, while she received a cold tuna sandwich and lukewarm tea.  Such a pathetic loser should have to pay for everything. Finally, I ordered him to put on his new princess outfit and handed him a sign to carry.

PLEASE TEASE ME ! GIGGLE AT ME ! LAUGH AT ME ! OUT ME, HUMILIATE ME & PUNISH ME AS I DESERVE !

And I laughed and laughed as people stared and pointed at the pansy fairy faggot…..

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Sissy Mom Nicolette: Springtime is for Sissies

sissy mom springI’m a Springtime sissy mom. What does that mean? It means that as the temperature gets warmer and the flowers begin to bloom, I start to clean house. But in my house, that means something different than just putting winter clothes away. It means getting sissy boys ready for the new season. My friend Gloria has a son who we think was born in the wrong body. He is no man. When he was knee high, he was wearing mommy’s panties and playing dress up in her clothes. I would come over and he would be prancing about in high heels wanting us to join his tea party. Gloria just laughed it off as his experimental stage, but I knew he was a sissy boy even then. My best friend has resisted my pleas to just make him a full fledged sissy. We had lunch the other day, and I begged her to bring him over for my springtime cleaning ritual. She finally agreed. Springtime is for sissies!

sissy boy phone sex springWhen they arrived, I slapped a collar on Derek and informed him his new name was Denise. He appeared scared and aroused simultaneously. Every woman can use a sissy in her life. They make excellent maids, bitches and fluffers. It is when they are in that girl not ever going to be a man stage that they are annoying little whiny ass fuckers. They need a dominant mommy to convert them to full fledged sissy and become their master. They need my springtime ritual. Denise was held down while I fisted her back door pussy. I wanted to pop her sissy cherry while Gloria rubbed her little clit stick with the vibrator. A sissy’s first cum is special. Just as special as a sissy’s first fuck. I let her mommy take her tight virgin ass with a strapon while I fucked her pretty little mouth with mine. Tag teaming a sissy is so much fun. After a sissy’s first fuck, comes dressing the sissy. I had a pretty pink frilly springtime dress laid out with a white bonnet and some white sandals. Gloria couldn’t believe the transformation. Thanks to my sissy springtime ritual, she now has a full time sissy who will cook and clean for her, plus pamper and amuse her; even procure cock for her and clean up her cream pies. A sissy is a dominant mommy’s best accessory. Are you ready for your conversion? Sissy boy phone sex awaits you.

Dreams of a Sissy Training Mommy

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I had a kinky dream last night. I was training this sissy boy to be a good little cocksucker. She was so pretty and her tits were perfect. I was wearing a monster black cock strap-on and I had her bent over. Her tight little shithole was gaping from the fucking I gave it. I was loving the feel of those balls as I banged hard against them. It was like my fake cock suddenly become real and I was getting those amazing sensations in my nutsac. I reached around to grab her by the throat. I heard her whimper as I pushed 10 inches into that anal cunt. I didn’t even care, which is strange, because I am a sissy trainer who is usually patient and gentle. Dammit, I’m a mommy, not an animal.
But this whore was mine. I pulled out of her boy box to turn her around to suck em off. She whimpered as I shoved my shitty cock into her throat. I found that making her gag felt so good. That throat squeezed down hard on my fuckstick as I pushed deeper. I felt my balls tighten. She ceased to become a person to me as my cock become to pulsate in that hot mouth. I never wanted to be a man before but this was fucking fantastic. I screamed out loud as my big dick exploded all over her face.
When I awoke, I found that my belly was dripping with something sticky and white. I dipped a finger into it and smiled. I was covered in cum and it was delicious. Come share your wicked dreams with me!!!

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Mommy’s Frat Boy

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I pushed the vibrator deeper into my pussy. It felt so damn good. You’d think I’d be satiated after all of the cock I got last night but when I woke up this morning and felt his cum still oozing from my battered cunt, I got all turned on again. He is my best friend’s son. We went to college together and she made me his godmother when he was born. I never expected to be his FAIRY godmother.
I hadn’t seen him in several years while he was away at med school. He was an awkward geeky boy with crooked teeth and glasses. I never even thought about his cock even though I love it young. But when I visited Linda yesterday, I almost fell over when he came through the door. The geek was gone along with the braces and bad skin. He flashed a sexy white smile at me and hugged me. “Nice tits.” he whispered, making me laugh.
Linda had an appt and invited me to stay until she got back. He and I got busy getting to know each other again. We talked and laughed until he looked at me all serious. “I’ve always wanted to fuck you, Pearl.” He reached for me and I didn’t say no. His cock was thick. When he pushed it deep into my deprived pussy, I was a goner, a shameless begging whore. He made me cum twice before he stopped. “Let’s go back to your place.” he moaned. He ate my pussy like a starving man. I sucked his cock and licked him clear to his asshole. Then he was back inside of me, driving me wild. His pistoning hips churned my insides into butter and I was more than ready for his cream. When he finally allowed himself to cum, it was like a scream of pain and bliss.
I awoke to find him gone with a note that said, “I’ll be back tonight, Pearl. I took your panties with me. Tonight, I will show you yet another side of me that I think you’ll love.”
So, it looks like a have a brand new sissy boy on my hands. A mommy can never have too many. I can barely wait to hear his secret. Just in case, I have a big black strap-on lubed and ready for him. It’ll be my pleasure to take that ass cherry.