Category: Sissy boy phone sex

Forced into sissy maid training

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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.

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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.

Mommy Whore Shares Son For Doctor’s Day

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It was time for a check up for the boy. You discover he has on satin panties and ask him about them. Embarrassed he replies that he just loves the way they feel. You admit that he does look rather sexy in them and that they showcase his young cock nicely. You tell him he needs to remove them for the exam. He does and you inspect his parts. You comment that his ass looks a bit stretched and you need to check to make sure everything is ok inside. That is when I notice the bulge in your pants and realize this will not be a routine doctor’s visit.

You use your finger to inspect his ass and decide you need something that can reach deeper to check it out really well. You give me a wink and I know what you have in mind. Since it is Doctor’s Day and you are being so nice, how could I refuse yo this pleasure? Actually, I wouldn’t refuse you anyway. A dirty mommy whore like me gets off on watching her little sissy boy get abused. I watch as you take your cock out of your pants. You use the KY to prepare his ass and your cock. I finger my pussy as I watch you begin to push that bulbous head into his tight little ass. He whimpers, partly in pain, part pleasure. You begin to stroke your cock in and out of his ass. You and he both look like you are in heaven and I finger my sloppy wet pussy even harder. You say that his ass seems to be fine and you need to check his tonsils. You pull out and move to his mouth, proceeding to fuck that sissy mouth with your dirty cock. I watch you and I stroke my clit even harder. I am on the verge of coming when I see you start filling his mouth with your cum. I wait for him to finish swallowing and then sit on his face and ride it to my own orgasm.

What a fun way to celebrate Doctor’s Day! Best of all, the visit was free!

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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 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.

This Mommy Loves Sissy

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All the other girls here are so mean to our company sissy. They love to publicly humiliate him just because he likes to wear cute little frilly dresses and diapees. He has such a tiny cock, he is already humiliated. It’s really more of a large clit than a cock. He spends his time with Mistress Levi. She owns him. Occasionally however, she loans him out to us other girls. When its my turn to have our little sissy, I show him plenty of Mommy’s loving attention.

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At my house, Sweet Baby Sissy has his own little crib set up. I have special onesies for him to wear and I give him his juice in a bottle or a sippy cup. I make sure his bottom is clean and use baby powder on his bum, so he always smells nice and fresh. I even lotion down his skin, so that it stays nice and soft. He even has his own special teddy here that he loves to cuddle. He is such a good boy when this Mommy is sissy-sitting. He never gives me a lick of trouble, unlike my own rebellious ones.

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Sissy loves his Mistress. He loves being dominated and humiliated. But sometimes, he has to come visit Mommy Meredith and get my own special type of Sissy treatment.

He Looks Hot In My Pretty Panties

mommy son phone sex I walk into the bathroom and stop dead in my tracks. Standing in front of the mirror is my oldest son with his hands wrapped around a rather large erection. What makes me pause for a moment is realizing he is stroking his cock while wearing a pair of my panties. It is not just any panties either. They are a pair of my favorites. They are a cute little pair of thongs that are purple with pink designs on them.  He looks rather embarrassed to have gotten caught. I don’t want to embarrass him further, but I have to ask what he is doing in my panties. He confesses he loves the way the soft fabric feels on his skin. I guess I can understand that as that is one reason this is one of my favorite pair.
 What confuses me further is that seeing him in my panties is actually making me excited. He looks so hot with his manly cock coming out the top of these girly panties. He is already dripping pre-cum from the tip. Not being able to hold back any longer, I drop to my knees and begin bathing his dick with my tongue and licking up all that sweet juice that is trickling out the top. I tell him how hot he is and how much I adore his cock. Before we leave the bathroom, he gives  me one of the best fucks I had gotten in a while. He fucked my hot pussy with all the vigor and stamina that only youth have, filling my cunt with his baby making seed.  I tell ya, if wearing my panties gets him that worked up, he can wear them every day!

Sissies love MLK Day fun.

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Martin Luther King Day has already come and gone. Sadly, it seems to have become part of the race war rather than the peaceful world that MLK wanted. I didn’t add to the confusion however. I am 100% pro-black. Black cock, that is!!!
Ok, it’s my dirty secret but I love black cock. Black men know how to rock a woman’s world. Not only do they have superior cocks that make a white boy’s look like a cocktail weiner. They also have that smooth groove. Oiled and sensuous. What white girl can resist a blacksnake worked by a snake charmer? I think all sissy white wimps should have to witness a black cock doing his thang. That big purple plum head. The smell of musky balls topped with tight curls. I want that white sissy to feel it. Taste it. And understand why us girls crave it.
Tell me the truth, little faggot. Are you wanting some, too?  Can I force you to say the words? Whimper for me and I’ll help you discover what’s missing from your pathetic life. Got those panties on? Better bring that oversize ass toy when you call. It’s time to practice. Your big sissy mama is gonna train you right.

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Dreaming of Sissy

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In my wildest dream, I have my very own Sissy. It’s something that I’ve wanted forever. A cute panty boy to share my lacy things with and dress up all frilly. So much better than having a brat. My sissy would be my friend and my confidente. She’d listen to my goals and dreams and I’d also help her become the sissy of her dreams.
If you are a sissy or wanting to be one, maybe I could become your mistress. I’m a real life teacher who provides the finest of sissy training and sissy lessons online. I am not cruel but I will provide the humiliation you crave. Whether it’s humiliation, degradation, public display, blackmail threats, or fear of being exposed, we’ll have such a good time. Can you imagine the horror of being sent to a certain location and having to ask a stranger to take your picture for proof? I will push you to the edge, as close as you will allow me too.
Oh, and the clothes. I will personally sew you some of the frilliest things you have ever worn, totally fabulous sissy clothes so you can flounce in public for me. What sissy wouldn’t enjoy that? Maybe along the way, you can even get some cock.
Anyway, that’s my dream right now. Are you my new sissy? Stop searching now and help me achieve my goal as I help you reach for the stars.

 

Your New Year’s punishment starts with sissy training phone sex!

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OK come on over here and sit right next to mommy. It’s a new year and that means it’s time for your sissy training phone sex. I told you at the end of 2015 that I was going to teach you how to be a good sissy for the year 2016 and that is mommy’s goal. So with that being said it’s time for you to get all dressed up and ready to play with mommy and learn the right way to please a nice big cock just like mommy can. So first let mommy get your little pink dress out and get it on you. Along with mommy’s sexy satin tough evening thigh highs and my 5in knee high boots. Wow look at mommy sweet little sissy boy. Very sexy now that your all dressed up let the real fun begin. I have invited a very special friend of mine over tonight and you get to help your mommy out. So the first thing we are going to do when he gets here is walk out and let him get a good look at Mommy’s sissy boy. Then we are both going to get down on our knees unzip his paints and pull out his big 8in throbbing cock. That right you got it now that his cock is out you need to rap your hand around the base of his dick just like this. That good you got it now open your mouth and let mommy guide your mouth on to his big dick. Just like that see you got it, what good cock sucker you are, See I told you that sissy training phone sex would be a lot of fun. Now that you can handle sucking a big cock Its time to move on to bigger and better thing. We both know that you really enjoy your New Year’s permanent punishment pansy no need to try to hide it. Mommy Eaddie is here to give you any and all punishments that you need.