Category: Sissy maid training

Gwens Forced crossdressing

forced crossdressing One of my specialties is forced crossdressing. And this time of year is amazing for men who need to be dolled up and slutted out. Now look at this picture, one of these isn’t like the other. One of these sexy vixens is a shemale sissy, with a tiny dick. Can you pick me out here posing with a few friends after we took turns making our sissy slave whore into a beautiful slutty fuck doll! I have so many ideas on how to make you the perfect princess with a penis! Stockings, short little sexy Christmas dresses, silver cock cages with bells hanging from your balls. As you learn how to walk with a swish to that ass and balance in heels over six inches. Shaved, lotioned, and prim all sexy and feminine. But as you look at the part there is more sissy maid training that must happen. Just like our little sissy ladyboy, we had to teach her to clean out pussy, to take a dildo up her sissy pussy and submit to not only women, but a nice big fat juicy cock one day soon. It’s up to sexy sluts like me to make the perfect princess despite having a cute little penis! Perhaps you in your little slutty Christmas outfit can cum see me and submit the was a sissy la-la should! There is much sissy fun to be had with this Mature Domme Momma!

Sissy Maid stories to live by

sissy maid stories The bubbles lapped my skin as the water swooshed back and forth. I had been reading some new sissy maid stories and was lost in the thought of my newest sissy. My body was alive at the thought of my sissy Sucking the UPS driver’s cock as a tip. We had been making good progress, and the outfits He bought to dress up in had become more sissified every weekend. He had taken my strap once and had taken three weeks to come back and see me. I was sure that would be the last session we had. But this morning I received a sissy novel on my doorstep and A bottle of wine and a Bath set. We had a “date” soon, and I was crafting a plan to keep him in my care for a long time.
I had fired my part time housekeeper and the house looked like a single busy business woman, lived alone. I stepped over discarded hose and panties, over towels and lotion bottles; giggling to myself. I had added to the mess with Hiding sissies butt plug under a pile of jackets and leaving a note beside it. Sissy was going to clean my house and sissy was going to either Present herself fully, or find another Mistress, My boots and black leather outfit With the crotch cut out would set the scene. It was Sissie’s favorite outfit. A leather loving sissy who would orgasm if he was allowed to click my boots too long.
The note read: Things you need, Your butt plug. (lube or no lube) The shopping bag in the closet behind My favorite Boots and Paddles.
If you wish to submit fully to me, and give me control to lead you into true sissydom, You know what to do. If you wish to end your contract you may gather your things and walk out the back door to hide your shame, No refunds on my Mistress tributes.

It took him 15 minutes. I waited dressed with my legs propped up on the couch. Sissy came crawling with her ass in the air, one pair of panties on and a pink leather paddle in his mouth. Sissy whined at my feet like a good puppy sissy.

We would begin his sissy maid training fresh. I had new ideas from his book.

Gwens a phone sex mommy

phone sex mommy Oh my sweet snookems do you need a phone sex mommy? I know baby, you’re such a bad boy. You’ve been doing things like sneaking into my wardrobe and dresser. I notice a couple of nighties are gone,and more than a few pairs of panties have been worn and returned all crusty with cum. Naughty! But I think the worst thing you did was put my dildo back with your ass juices all over it! You wanted to be caught !I think you deserve a spanking, my lovely! A nice firm spanking!
Look at me, why are you so bad, you could have asked me to play dress up. Now come here and let me dress you proper! First a pair of silky sheer panty hose, and let’s not forget some special panties with a little extra material to hide that erection! I even have tucking panties for a sissy slut who is a little bigger than most of my slaves. Give Mistress Gwen a good show. Dance around and twerk real nice and slow! Oh, baby you make my milf cunt so wet as I insert a bejeweled butt plug in your sweet sissy hole! Oh now watch as I lay back and play with my pussy and direct you to properly use every toy I have in my arsenal!
You know you love sexy women masturbating while you show me what a good slave you will be for me!sexy women masturbating

Sissy Humiliation Of BBC Fag Richard

Richard is the topic of conversation today. I love to expose him to all my friends. My girlfriends and I love to laugh at Richard because he just can’t get it up for women! Yes, It’s True! Richard is a Sissy Cock Slut that wears pantyhose and crave for that big black cock. Big black cock is also known as BBC and Richard is also known as the pantyhose wearing BBC sissy slut.

SO the truth is to be known. I will even share the conversation that made that sissy squirt, well maybe a snippet only;

Rebecca: I think everyone needs to know Richard is a pantyhose wearing sissy nigger cock sucking faggot.

Richard: O god  (*Smirk can’t you just tell how much Richard is shaking in her pantyhose!?!)

Rebecca: And that he can only cum from having that sweet white boy ass owned by the BBC…

So, as you can see my sissy cock slut Richard the pantyhose wearing BBC lover is real and in need of being outed. Everyone say hi to Richard and he will be happy to service that BBC.

Sissy humiliation

cock tease

tease and denial

 

I love being a little cock tease! There is nothing that I find sexier than a worthless pig begging to just shoot his load all over my huge ass tittys or hell anywhere on me for that matter. My pussy gets soaking wet and I love it especially giving my little sissys blue balls. It is not my fault their cocks are too small to fit into my tight fuck holes but they can sit like the worthless pigs they are and watch me get worshipped like the Queen that I am but a huge thick cock, and then they can clean up the sticky mess by using their tongues. I know my sissys are just dying to lick my cum off of a thick hard cock. If they are good I might not beat them and force a big black cock down their throats until they choke and post a picture to all of their social media so everyone will know they love dressing up and cocks.

Forced Feminization Continuation

Our first session has introduced you to the Forced feminization side of cuckold sex. You are made into a slave to my superior pussy and to all of my bigger superior alpha male lovers. They are amused by you, slave. It’s the most amusing thing for me to see Mr. manly with a small penis complex get put into his place. It’s a fact that you men with your guns and big trucks are all harboring desire to suck dick. You have no dick. You can’t please a woman. Fuck, you are complete assholes to women. But, then one takes you by the balls in the bedroom after realizing you have no fucking purpose in using that dick with her.

Little man syndrome is wide spread. This is especially true with the backwoods boys that love their hemi’s and guns. Well let me tell ya something, I love my control and strength. I am the perfect Mistress to make you cower beneath me and be denied the chance to cum for me. You will not get that little dick near my pussy or my mouth. I laugh at you and kick you in the family jewels. I tell you that the breeding stops now. You are now worthy of making more of your DNA. I will cage you and humiliate you. That is what you will get used to!

Forced feminization

Our first session went so well with how much you obeyed me. I am what you crave. I am your Mistress and you will continue to train with me. I am an educated control freak with a perfect body. You know if you get my time it will cost you. I will make you weak for me and crave more of my humiliation.

Sissy Maid Training With Goddess Gwen

 

Sissy Maid Training

Sweet man did you not realize you needed my sissy maid training. You came to me for a little sissy play. You have been a cuck for your wife for a couple of years now. But the more you look at those big dicks going in and out of her sweet whore holes, the more you begin to want that cock in your mouth! It is now your realize that you need something more. One day you looked in the mirror and saw that clit sticking up to the sky. You were thinking about her, taking that dick in her pussy and you daydreamed that you were her in pretty lace and ruffles. You had your skirt flipped up and was taking the dick in your “womb” and ass hole. It was just a dream, you had been reading too many erotic sissy maid stories lately and you had envisioned being a slut in frills and pearls. 

This is where your Goddess Gwen Comes in. Offering to make you into the extract thing you want to be. I French Maid sissy slut!

sissy maid stories

You arrive at my place and I am in the sexiest maid outfit with my feather duster in my hand. I promptly hand it to you in exchange for the tribute you have for your mistress. A big fat wad of cash! If you need to be a full on sissy whore, you need to pay up piggy! We start with full exfoliation and hair removal. Your sissy maid outfit is read for you. Dressing you up in soft feminine colors and tights and even heels. The sexiest thing is your panties and bra under your ruffled skirts. I have a few girlfriends who know how to treat a sweet dumb whore like you. My pussy gets licked in front of you as We dangle a cock cage. You are ordered into a series of timed events. Dusting with a huge butt plug in your ass. I enjoy ordering you back to the fireplace leg as I check it. Uh oh! Someone gets the little dick cage!

sissy humiliation

 

Now for you sissy humiliation training. You kneel at my feet and kiss my heels begging for release, but I had other plans for you as my best friends and I invited our big dicked boyfriends over! You are going to learn to serve a big fat cock and suffer at the hands of hot Goddess!

Sex Therapy Porn for Cuckolds and Sissies

sex therapy pornSex therapy porn is necessary for sissies and cuckolds. I make all sissies and cuckolds watch porn. Porn like women cheating with big black cocks. Porn like losers sucking big black cocks. Porn like sissies getting feminized and pegged. Not all men are created equally. Some are born with small dicks. I love phone therapy and real time therapy. I do not try to cure sissies or cuckolds. I want to make them the best cuckolds and sissies they can be. I want them to reach their full potential. I have subliminal porn films I show them. I have interracial cuckolding films. I have pegging videos. That is just phase one of phone sex therapy with me. The second phase, I bring in men. Black men, white men, men who have big cocks and do not mind a sissy bitch or a cuckold swallowing their load. Maybe I am less a therapist and more a trainer, LOL. Honestly, I think men need to live their true lives. A man with a 3-inch dick should not be a player. He should not be acting macho and take charge. He should not be trying to conquer women. No woman I know wants conquered or courted by a man with a 3-inch dick.  Men with little dicks are easy to discard from our lives, but cuckolds and sissies are useful to have around. So, when a couple comes to me for therapy, I help save marriages, by shifting the power dynamics. I put the wife in charge of her man. I make the man in charge of making sure his wife is taken care of sexually and pampered properly. Sissy maids keep a house clean. They run the errands. Cuckolds bring their women big cock, fluff that cock and clean up the aftermath. If you have a little dick and are not getting pussy, let this phone sex therapist train you for a meaningful career as a sissy or cuckold.

Best Phone Sex Is Sissifying Humiliation

I know how the best phone sex works for pathetic little men, they’re not even men, really. Sadly my husband is as little a man as the best of them and I do mean little. It’s laughable and I love to exploit it to the highest and bring in ladybois with much bigger dicks than him. I love tits and a cock, it’s the perfect package. I love most to humiliate my hubby over it all. Making his little pecker swell and leak, it’s amusing. I get to taunt him how even a chick with a dick is hung better than he is. I make him suck that cock while he wears the silkiest full bottom covered pink shimmery panties. A pink panty wearing sissy slut cock sucking little pecker cuckolded hubby. It’s fucking kinky. I have taken strap-ons to his manhole and helped him take a nice big black cock in that puckered cum dumpster. Best to pull them panties down and pump into that little sissy hole and fill it with cum. We pull his pretty pink panties with cum drippings in them right back up over that fucked hole and make him sit in those panties until it all leaks out and he does his best to push that creampie from his ass and soiling his pretty panties.

Best phone sex

 

You Will Do As I Say

forced crossdressing

You need a strong woman in your life, but you are terrified of a strong woman , aren’t you? You like your women to yield, submit, obey and stand down, don’t you? Well Mr. Stepford you can take that dream elsewhere. What you’re getting from me is forced crossdressing. Yeah, I’m going to make sure that you wear each and every uncomfortable piece of women’s clothing, panties, shapewear and feminine hygiene products that I can find. We will start with my placing a tampon up inside of you and then trap it inside with restrictive Spanx panties right over the top.

Did you think it would be a sexy game of me punishing you with making you wear a lacy thong? It’s so not about your panty fetish, you perverted little troll. It’s about discomfort, domination and the force of a powerful Goddess dishing out forced cross dressing on your helpless ass. There isn’t any way around it, you will submit, obey and yield to me. I will make your pathetic ass stand down. Your inferior male body will be held in the confines of women’s clothing of my choosing. You wear for my entertainment, not yours. Am I making myself clear?