Continue the Tour

Continue the Tour

 
Mature Sissies First Feminization Training

Other Movies You Might Like


Mature Crossdressing Sissy Is Dressed Up and Milked


Sissy Husband And Wife Both Trained


Forced On Their Knees For Feminization


















 
Mistress Rain DeGrey's NEW Sissy

Mistress Rain DeGrey's NEW Sissy

Full Length Feature Movie

Mistress Rain DeGrey has just joined Mrs Loving's staff. Mistress Rain is known for her strict and effective "Rules For Feminization" If you want to be feminized and sissified by Mistress then you'll have to agree. Mistress Rain is much more demanding than Mrs Loving but then some sissies need a firmer hand and actually desire it. In her first movie she firmly sets the rules for Allison and what she expects of her sissy trainees.

Some sissies just need a spanking










 
Ms Simone Makes Her Sissies Squirt

Ms Simone Makes Her Sissies Squirt

Full Length Feature Movie

Ms Simone has Sissy Monika and Sissy Lauren to entertain her.  Dressed in her finest vintage full slip and pantyhose over white panties, Ms Simone has the sissies panty each other.  With tents in their girly panties she makes them rub their panty covered cliffy together while she plays with their cocks. She makes them do sissy things to each other before taking their cocks out of their panties and jerk them.  Watch and see how much fun Ms Simone has with her personal sissies

See and Hear Ms Simone make them jerk off and come on her pantyhose



video of two frilly sissies Two clitty cocks
video of Mistress making sissies masturbate for her
Mistress expose her panyhose gusset to inspire sissies to come
Look at all that sissy come on her pantyhose













 
Mrs Loving's First Session with Allyson

Sissy Allyson's First Time Being Feminized and Milked

Full Length Feature Movie

Mrs Loving is in rare form for Sissy Allyson's very first feminization session. Allyson had always dreamed of female domination but not like this! Mrs Loving has fun with her new panty slave sissy.  She first puts Allyson in three pairs of panties and makes him walk with his cock between his legs to look like a girl.  Allyson's clitty cock grows with attention it gets from Mrs Loving's soft capable hands. The first thing a new sissy must endure is anal pussy fingering with Mrs Loving's lubed up black latex gloves.  Then and only then can her sissy pay tribute to her panties.

You've been sush a sweet sissy.  Take my panties home with you and sleep with under your pillowLet's get your ass pussy nice and slippery and open you upNow, get on your knees and kiss my feet and work your way up to my panties and then stopAwww, There you go my sissy.  What a nice big sissy spurt you have for Mrs Loving







 
Mother's Little Crossdressing Sissy

Mother's Little Crossdressing Sissy

Full Length Feature Movie
Sissy Monika comes home from school and finds mommy waiting in her bedroom.  "I'm so glad your home from school my sweet little sissy.  Let's get you out of your boy clothes.  Mommy bought you a new pink satin sissy dress and panties to play it.  Time to get you dressed.  Mommy has some fun new surprises for you".  Mother as a full lush body and she's training her Sissy Daughter to service her sexually.  Mother's body craves SISSY SEX


First, let's get those boys clothes off you             What a sweet sissy daughter I have all in pink satin              Yes, dear, you know how Mother likes your tongue in her ass            Mother's fucking you with her strap on and milking you at the same time









 
Transformed From Pete To Sharon

Transformed From Pete To Sharon

Our Latest Full Length Feature Movie

Mrs Loving completely transforms Pete into Sharon. Pete has worn panties and lingerie before, on his own, but he has never been full dressed as a woman with wig and make up.
With the help of Sissy Rikki, Mrs Loving gives Pete the first look at himself as Sharon.
You know by now how much pleasure Mrs Loving gets from playing with sissies clitties and balls and in this session she has more fun than ever. Watch as she makes Sissy Rikki and Sharon lick and suck each other. Watch as she plays with their clitties as the same time making them spurt their sissy cream come all over each other

Mrs Loving loves seeing her sissies lick and suck each others clitties and balls





Inspected in panties before dressing begins
 Checking fit of panties

First time ever in a woman's slip

Sucking Sharon's balls as instructed



Sharon getting her first taste of Rikki
Ritual panting by Mrs Loving
Sharon sucking and Mrs Loving stroking
A very, very hard sissy soon to squirt





 
Ms Simone Smothers Monika In Her Pantyhose Gusset

Ms Simone Smothers Monika In Her Pantyhose Gusset

Full Length Feature Movie

Sissy Monika is all ready in trouble when this video begins.  Ms Simone begins Monika's punishment by making her prance about in her sissy outfit.  Humiliating Sissy even more, she commands Monika to expose her cock and ass pussy. Not moving fast enough Ms Simone pulls Monika closer, pulls her pink frilly panties down and harshly slaps her big cock.

Ms Simone takes of her dress and full slip and sits on monika's face grinding the gusset of her panties and pantyhose into her mouth and nose smothering with her pussy fragrant crotch

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Teased And Humiliated Sissy Husband

Teased And Humiliated Sissy Husband

Full Length Feature Movie

This movie features an actual real life sissy husband and his wife.  his wife just wants to understand what's going on with her husband so she meets with Mrs loving to tell her story. They were seeking guidance from Mrs Loving in helping them understand what sissyhood means and how it can be incorporated into a marriage in a way the makes everyone happy.

The wife and Mrs loving dress the sissy husband in frilly panties and a little girls party dress. They ask him to model and show off and that makes him hard and excited in his nylon panties.  The meeting ends with Mrs Loving show the wife many ways to milk a sissy husband's penis until he squirts


Here, Im showing his wife how a sissy must take care of his body..trimming hair, nails etcThis is the little girls party dress he had hidden.  I think he's going to look very sweet in itI'm showing his wife how sissies like to be stroked by an extra pair of nylon or satin pantiesI told his wife that If you milk a sissy often enough they will provide you with hours and hours of entertainment








 
Mrs Loving Milks Two Sissies at Once Sissy Maid Training Part 4






Click The Picture To SEE More Sample Pictures

Sissy Maid Training Part 4

In Part four Mrs Loving has the sissies on their knees with their asses in the air.  First she opens their ass pussies with her fingers, lube and black latex gloves  then moves to their cock and balls and begins the slow pull back milking that sissies crave and need.

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