Tag: sissy maid training

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

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 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.

Mommy Fucks Sissy Maid Son in Ass

Sissy maid training

 

The most important parts of sissy training is learning to take orders and being able to take cock well. My son has been my sexy sissy maid for a week. I put her in the cutest French maid uniform and tied a bell to her tiny balls so I could always hear him coming.  I see my little one folding the laundry on the couch. I come up behind her and grab her hips. She asks me what I’m doing and I tell her she needs to shut up and take my cock. I push her panties to the side and ram my pre-lubed 9-inch dildo into her tiny ass. She could barely take being fucked like this, which means she needs more training. Her tiny little screams made my pussy wet, and I took some of my pussy juice on my fingers and used it to lube up the cock even more. I wanted to go deeper and shoved it harder until I was balls deep inside my little one’s ass. She squirts in her panties and I put them in her mouth, letting her taste her cum. 

Cock sucking mommy Colleen needs your Jizz

Cock sucking mommy

 

Hello, I’m the local cock sucking mommy Colleen. I started sucking cock when I was young laying on my bed and family members would come get me excited. My mom said it started with her tits and that’s why I have this cock sucking addiction. Next thing I remember I would walk down the street and down along the avenue I would guide grown men. They would always follow and I would always end up down on my knees, worshipping cock. Oh they all say they follow in hopes of helping but the only way they could help me was by giving me their golden nectar.  They say I look so classy but I act so slutty. Some girls grow up to be nurses. I choose to be a street nurse; giving and receiving love and cum. Imagine how awesome it feels to bring a man back from the brink of over indulgent not worth your precious time to the most amazing blow jobs

Sissy training phone sex with Mommy Penelope

Sissy training phone sex

Sissy training phone sex with sweet Mommy Penelope. Have you been wanting a sissy boy mommy to make you the best slut you can be with Sissy boy phone sex? There’s nothing I want more than a sweet little baby to call my own and treat like the cutest littles sissy slut imaginable!

Come right over here and crawl in Mommy’s lap sweetheart, let me show you just how much fun we can have together. Cuddling and treating you so sweetly, and so nicely while I give you all the love and kisses. That’s how you deserve to be treated, having you so close, rubbing your little sissy clitty.

The only thing I want you to do my little love is to come to make sweet sweet cummies for me while I play with you. Mommy Penelope has laid your pretty little sissy outfit out for you, and I’m ready to show you how good little sissy babies are supposed to be treated.

Sissy boy mommy

Sissy Maid Training From Anal Sex Mommy

Since i am knocked up now I need much more help, i make my sissy boy do so many things for me. Prefect for Sissy maid training, he made sure to pick up after me and clean my messes even shave my Wet mommy pussy. 

Sissy maid training

One night I was so horny that two of my favorite bulls to come over and fuck me. They took turns fucking my mouth and cunt hole. I squirted a few times and they still had not busted yet. I decided to use my sissy boy, he will be perfect for a good bull nut milking. I called him and he was still wearing the sissy panties I gave him. I told him to help mommy out and milk her friends. Like a good sissy whore, he got on all fours and started sucking cock as I guided the other big black cock in his boy pussy. I’m an Anal sex mommy so I love watching a dick go deep in an asshole. He got fucked as mommy watched making sure he did a good job. One after the other my bull friends started cumming. My sissy boy tried to swallow every drop. All I could see was the cum dripping out of his sissy gapping asshole. Mommy made sure her sissy boy cleaned their cocks with his mouth before they went home. After that she went to sleep with her sissy son cleaning her cunt.