Category: Sissy maid training

Sissy Boy Mommy Has Some Explaining to Do

Sissy Boy Mommy life is pretty much just like having a girl.  We love going to Victoria’s Secret and trying on sissy boy mommypanties together. I use to be upset that all my panties were always missing.  That is until I walked in my room on day and discovered that my little man had gone through all mommy’s dirty undies and was inhaling them. Like a drug going up his nose only it was just the aroma of my dirty, smelly, sex ridden, cum filled panties that my son was inhaling for the smell alone.  My heart was so filled after that day.  I knew what I had to do.

What is that you ask? I had to put him through sissy training.  I wasn’t really sure how to not go all in with it since I do so much different things through my work here on the phones.  So we went on a shopping spree, bought some pretty little dresses to dress him all in.  Pink and purple with some white pretty lace.  Knee high stockings for his little boy legs.  Mary Jane shiny black shoes with a small heel to prance around and twirl around in.   I make him do his makeup to look his absolute best.

Then he has his practice time where he takes orders from mommy.  Being the pathetic cocksucking bitch that he is, he isn’t treated like a girl here because here is where things get dirty, he’s a sissy bitch with a little boy pussy cunt that will get used and abused from this point on.  He’s learned on my dildo’s about sucking cock and I have some of my biggest black cocked friends on the schedule to come by to get their cocks sucked in a few days.  They think it’s by me but I can’t wait until they

From Sissy Slut To Breeding Phone Sex Slut In Minutes!

Breeding phone sex

Why don’t you sit right there and be a good breeding whore for Mommy. All dressed up in your pretty pink ruffles, just waiting to be praised and played with like the good little slut you try so hard to be. Such a good little slut, your make up done just like I’ve instructed, sitting there on your knees. Just wondering what the day has in store for you.

Such a good little sissy ready to do as I wish. Your little clit making you whimper like a dirty little slut with each spoken word. My favorite little slut to tease and torment, to turn into the cutest sweetest little hole for all the big massive cocks to fill.

Turned into a little breeding whore by yours truly.

Your hole continuously filled with that white creamy goodness. Making you whimper and beg for more like the dirty little bitch you can’t help but being.

Come be bred with me, show me what a good little slut you are.

Sissy Maid Training is a prerogative of mine.

Sissy Maid Training is a prerogative of mine.  You need to learn how to be a good sissy for your Mommy and man. Sissy maids are awesome! You are a sissy boy and I have been training you to become a good sissy boy. You have progressed as you know how to dress and how to get a man to fuck you in your sissy boy pussy.

You now get to train on how to be a good sissy maid. That is right. You need to see to your man and Mommy’s needs around the house too. You need the right little maid costume, short. Want to see that little sissy pussy of yours when you bend over to do the dusting, scrubbing the floors, that pussy should be readily assessable.

Your man comes home and seeing you cleaning. Little maid outfit looking so cute. Lifting the skirt up just a little, you feel cock rubbing along your pussy. Don’t stop cleaning as he presses deeper into you. That’s it. Take all of him into you. He buries himself in you. Pounding you, tighten that pussy around that cock. Beg him to fill your pussy up. You want and need him to fill you up. Just like that. Cum with him.

Sissy maid training

Phone sex blogs make me want to squirt

phone sex blogs

I love providing content on phone sex blogs because I have many stories to tell. Many times, people tell me they’ve never been with a girl that can squirt. In one of my blogs, I talked about how much of a squirter I am.  There’s no denying that I love to play with myself, but I do enjoy some good dildos and vibrators. Fingering my twats is always ideal, but when I want to spurt out some squirting juices, I have to use a very good dildo to hit my G-spot so I can squirt. There’s no denying my love for a good orgasm. One afternoon I felt encouraged to play and cum well so I decided to record myself and send it to my stepson. I know he’s going to love seeing his hot stepmom squirt!

Lenora Catches Her Son In Drag

Sissy boy phone sex

Lenora Catches Her Son In Drag 

I had spent the weekend away from the house and decided to surprise the kids to see what they were up to. When I showed up however I was the surprised one. My house was completely silent and for a while I figured no one was home. Heading to my bedroom I opened the door to find myself right in the middle of a Sissy by phone sex fantasy. 

There was my son dressed up in my pink lace teddy, matching lace thong and a pair of my thigh high stockings. He even had the boobs stuffed. What the fuck!!!!! I started to yell what are you doing right now are you fucking kidding me. He turned around, but that just made it so much worse. He had my fucking 9 inch pink dildo shoved deep into his little boy pussy. How dare he violate my shit. Boy do I have a plan for him. 

Sissy boy mommy Christina transformed another sissy

Sissy boy mommyI love being a Sissy boy mommy; being able to train young men and teach them how to be perfect dolls! A Drag Queen that struts like Beyonce with lips like Angelina Jolie. I love watching sexy feminine boys perform live at drag shows in custom fits that they made at home. Its such an adventure to see these things; such creative minds like theirs can create. Especially, because momma manages to make a few friends.. A sexy milf and a young tranny whore tag team is everything an older man dreams of..

He gets the best of all worlds. A Sissy mom trains their sluts to be prim and proper! Nylons, garters and any sorts of pantyhose is a must.. its how you create a mysterious look that gets men wondering.. The more attention you have of theirs, the more fun we will have.. Draining those deprived cocks of the unforgettable sex they have never experienced; until today. A nice facial contour and 24hr outlast lipstick, we don’t want your lips to smudge when you are deepthroating.. Lets make sure you look like a Total: Hot slut. At all times! I am a sexy Mom with big tits and curvaceous well kept body; the definition of a MILF. I will teach you all my tricks, Sissy boy.

Lenora Scores a New Slutty Sissy Maid!

Sissy maid training

Lenora Needs Her House Cleaned

Who says that cleaning and household chores are a woman’s job. This is the main reason that I love having a great little slave. My house needs to be cleaned and I know just what to do! A Sissy maid training session.

Come right in and strip down from those man clothes you are not a man. Throw on this little french maids outfit for me. Obviously, this is not your full uniform what would be the fun in that little sissy. I grab a butt plug tail with a feather duster for the tail. Bend over bitch while I slide this inside of you. 

Perfect now, we are going to start with some dusting, Clench that fucking duster tight so it does not fall out. Bend those fucking knees and dust the tables. Feel that toy as it rocks back and forth in that tight little fuck hole of yours.

Sissy Son Eats Mommy’s Wet Pussy

Sissy boy phone sexI know my sissy son is a cock-addicted slut and he doesn’t deserve to come anywhere near my pussy, but I need my pussy eaten so bad and I knew he was too weak to fight me. Sissies like him can be used by anybody, even me. I rubbed my wet pussy on his face, squeezing my thighs on his head. I told him I would fuck him with my strap-on if he ate Mommy’s sweet pussy. That cock whore became my pussy slut, slurping up my cum and eating me out like a good cunt eater should. I want his dick sucking lips kissing my pussy and making me squirt.

When he made me cum ten times, I decided to reward my slut with a big, black strap-on. He hasn’t had a cock this big before, and I didn’t give him any warning when I slid the entire cock inside of him. He kept begging me to give him a break, but I knew that he loved feeling that cock inside him destroying his insides. Besides, I don’t take orders from sissy whores.

Sissy maid training worked well on my now cock craving son

Sissy maid trainingI am a Sissy mom and I might even be the reason why.. I couldn’t help it!! I’ve always wanted a daughter but didn’t manage to have any. So, I let his hair grow out and started buying him barbies and makeup.. I sort of groomed him into being the cock craving faggot he is. When he came to me about his woody, instead of telling him his peenie was for mommy’s pussy hole I led him to my ass. He shot his first load inside of my asshole!

I wanted him to know what it was like to have his prostate massaged so I would have him watch porn with me while we self trained sucking on rubber dicks! As we would train I would tell him that he was never going to have sex with a woman, he was going to be a whore for cock.. Mommy’s personal cum eating slut! I wanted him to follow in my footsteps… I taught him his man pussy could make him tons of money.. I wanted him to enjoy being used by men and accept that he was and still is nothing but a fuck toy, nothing but holes to be used. I started inviting men over to use and abuse all of his sissy holes.

I obviously had to prepare him for that day through Sissy maid training… I started using a strap on and having him use his hands to stroke while he sucked on my bulging rubber dick! He was finally ready for the world.. I started off by having one of my reg clients come over and jacked his big veiny dick into my sissy sluts mouth.. He dropped his jaw and took it deep! I wanted his first time anal stretching on a nice piece of meat. I was rooting for him, as he slid his virgin ass down a 10 inch stiff dick! I promised him if he took it like a champ he would have a nice box of treats left on his bed for him to enjoy.. My sissy fag has become an addict to pleasuring cocks.. he even brings men home from gay bars and we take turns slurping, fucking and draining their cocks! He did well as a first timer and he’s only improved since. His faggetry makes my Mommy whore cunt soaking wet!

Sissy Son Becomes Mindless Slut for Father and Brother

Sissy training phone sex

The best part of being a sissy is being used like a mindless slut. Men with big cocks love brainless fuck dolls they can fuck the shit out of. You can fuck a man in all sorts of positions, but the feminine mindset is always that you are a toy to be used. For this, you need training turning off your brain and letting men with big cocks use you. That’s why I brought your older brother and your father here to be your guides. Get on your knees and keep your mouth open so they can face fuck you and use your throat like a pussy pocket. When they tell you to bend over, you bend over without a thought. The best kinds of sluts are the obedient kind. When they both fill your tight hole with both of their cocks, all you need to do is be a good little bitch and take it. You know you love being a mindless slut, having your holes used and abused until you’re dripping cum out of every hole. Don’t think, just get fucked. You are here to make your brother and your father feel good.