Makeovers - Getting my Hair Permed

I still blush when I think about it.  My makeovers and dressing session with Florence eventually evolved to my getting my first "perm" and having my hair in old fashioned rollers.  

Florence had a friend called Elaine that she would bring in specifically for requests by clients who wanted a fuller feminization that included having their hair done.  Elaine would charge a significant fee for this service, the amount I would never know because Florence was ever-so-generous with me, no likely charmed by my youthful charm!

Whatever she did charge the men who visited Florence to have their hair done, Elaine did admit to me that she truly enjoyed "being able to feminize men, though not in a kinky sense."  It was evident that very first time she did my hair, even though I was blushing with embarrassment the whole time!

I didn't even want Florence to see my face.  But the next time was a little easier and by the third time Elaine had me in "the chair" it almost felt natural.

Almost, but not quite.  But with my hair a little longer each time and with Elaine becoming more familiar with me and what I might look best in, things became not just easier but far more enjoyable.

I always felt very girly in curlers and the fascination with them has continued to this day.  Yet it has been ages since I've had my hair done that way.

But the most memorable moments of those makeover sessions when I had my hair done was when all was said and done and my hair had been cut, washed, set and dried, Elaine would comb my hair out and let me look into the mirror to see the results...

Those memories will last a lifetime!

Love,

sissy terrie 💓💓💓💓

Makeover Memories

The following is the second in a series of a young sissy's experiences with makeovers at the hands of an older woman....you can read the first installment here.

 

"You look absolutely beautiful.  You've come a long way since that first time we did this" Florence told me.   I could tell she was pleased with me as well as with herself.  After all, the girl I saw in the mirror was the product of her work.

I had to admit I looked stunning and 100% passable and I felt like a million bucks.  I stood in front of the full length mirror in her shop and struck my most feminine and sexy poses.  Florence hadn't completely finished my makeover just yet but wanted me to try on some heels and look in the mirror.   Standing behind me she moved closer, moved the hair from my blonde wig aside and planted a kiss on my cheek.  I blushed.

It wasn't the first time we'd kissed.   It took some time but after the first couple of appointments with Her, our intimacy seemed to increase each time we saw each other.  Her soft touches, a kiss here and there and before I knew it I'd developed a deep crush on her and she knew it.  Soon we were embracing passionately and eventually, I began to pleasure her orally.  

"Here" she said breaking me from my reverie as she handed my the tube of lipstick.  "I think you're ready to put on the finishing touches yourself.  And I'd like to watch you."

I took the tube of Cover Girl lipstick from her, smiled and with a little anxiety, began the application.  Though I was nervous because I wanted to please Florence, it felt so very natural.  

"Use this instead of the full mirror" she said handing me a small compact.  "When you're out and about and need to freshen up, you're not always going to have a nice big mirror to look into."

Florence watched me slowly apply the lipstick.  I was careful not to smudge any and when I was done I puckered them and blew myself a kiss into the tiny mirror.  She smiled, pleased with what I'd accomplished.  

"You know honey" she said.  "Women like me are very, very hard to find.  I just happen to have a thing for pretty boys and men like you.  Unfortunately, I'm old enough to be your mother."

Florence's comment surprised and confused me.  Was she saying she didn't want any more intimacy?   I wasn't sure quite what to say.

"I've taken you about as far as I can with your femininity.  Have you thought about expressing it in other ways?" she asked me.  

"I'm not sure what you mean" I told her.  "I mean, no...I don't want to have an operation if that's what you're asking me.  I mean, sometimes I wish I was a girl but....I wouldn't want it all the time."

"I'm not necessarily talking about having surgery honey.  There are other ways to experience femininity without a sex change" she said with a slight chuckle.  "Let's be honest, you look absolutely stunning this way.  You know darn well any man would find you very attractive."

I blushed a little more.  Did Florence think I was gay? Or even bisexual?  Why would she get that idea?  Especially after our intimate times together.  She was always satisfied with my oral attention and even though we never had intercourse, she always aroused me and would pleasure me with her "touch."

"Have you ever thought about being with a man?" she asked me point blank.

She saw right through my hesitancy to answer.  

"Of course you have" she said.  "Most all men who dress think about it.  After all, it's almost impossible not to when you've embraced the level of femininity you've achieved.  You should probably give it some thought.  I only want you to be happy in life."

I smiled at her and didn't say anything.  She could tell it had been on my mind.  Before I could say anything she had taken the lipstick and compact out of my hands, set them aside and took my by the hand  to her office in the back of the shop.  

"It might mess up those pretty lips, but right now they belong to me" she said.  "And between my thighs."

Love,

sissy terrie

Makeovers - Joyful Memories

Over the years I've had a number of professional makeovers.  Some were just so special and more memorable than others and only a couple not worth the money I spent.  But I'll remember my first dressing session that included a makeover as the most special of all.   

"Florence" owned a dress shop that along with catering to women of all ages, offered discreet dressing and makeover sessions for crossdressers.  I was only 22 at the the time and in my first year of graduate school in large city.  Florence's shop was about an hour's drive out of the city.  I'd seen her ad in a free weekly newspaper and decided to call her.  

My anxiety was obviously apparent but Florence immediately told me to relax.  I visited her three times for dressing sessions before I went for a full makeover.   It was the first of several with Florence and each time she always made me feel special and understood.  We had a very special intimacy.

 

At Florence's dress shop I got to wear many pretty things, but what brought me the most joy was the process of getting ready. 

Florence taught me plenty about lots of girly things (fashion, makeup, etc) but more than anything, she taught me how important it is to be kind and understanding to other people. 

Love,

sissy terrie 💗