Archive for the ‘Sissies First Time Dressing’ Category

Friday, January 18th, 2013 by admin

Well, My Dear Sissies,

Mrs Loving has had a very exciting holiday season. Besides being with family and friends I met and began the training of Sissy Pinky. Sissies come in all ages and sizes. I am aware that most of the sissies on my site are young so I thought it was the time show a training of a mature sissy. Sissy Pinky and I emailed several times. He told me he loved getting all pretty and dressed up but that he had never shown this side of himself to any other person. It was touching to hear his story of being excited and lonely at the same time.  After joining my site and watching my movies he felt that I would be gentle and sweet compared to the other Mistresses her had read about. He was so very nervous that he needed to be comforted and to know that he would be safe and cared for if we did a session together.

He came to San Francisco last week and Rikki filmed a nice long video of Sissy Pinky’s first ever time to dressed up in ribbons and bows and be seen by another person. It was quite a session. It took time for her to relax but with attention and care she began to open up, relax and let her inner sissy out to play. Once I had her dressed and in make up and hair she blossomed into a little slutty tease that need some direction. We both had a lovely time for our first meeting and looking forward to the next one.

Frilly bra Sissy brought with her

Putting her into her pink satin and frilly garter belt

Hear she is with Make up and hair worshiping my panty gusset

Sissy Monika’s First Feminization Session With Mrs Loving

Saturday, October 16th, 2010 by admin

Mrs Loving Greet A New Sissy Trainee Sent By His Mother

Mrs Loving Greet A New Sissy Trainee Sent By His Mother

Telling Her Sissy Her Training Rules

Telling Her Sissy Her Training Rules

Mrs Loving Helping Her Sissy To Relax

Mrs Loving Helping Her Sissy To Relax

Lets Get Those Ugly Boys Clothes Off You

Lets Get Those Ugly Boys Clothes Off You

Does Your Mother Know You're Wearing Girls Panties

Does Your Mother Know You're Wearing Girls Panties

What A Cute Sissy Ass You Have

What A Cute Sissy Ass You Have

Mrs Loving's First Look At His Sissy Clitty

Mrs Loving's First Look At His Sissy Clitty

She Puts Him In His Very First Girls Brassiere

She Puts Him In His Very First Girls Brassiere