Super Sissy Sunday Thoughts

There's loads of indifference here about today's Super Bowl, with no real rooting interest for either team it's going to be just another game with hopefully a few interesting commercials and just maybe, someone will flash their pretty panties during the halftime show.  Who knows?

On a totally unrelated subject, I just happen to be thinking about...

...when I was young and I just knew I was different.  I thought there was really something wrong with me.  Whey did I love wearing panties (and other girly things) so much?

As scary as it was, I had all these weird fantasies that played through my mind.  My aunt would never do such a thing...or would she?

I never thought it would actually happen but thanks to my loving, understanding and beautiful Wife, many of those fantasies did come true!

Have a happy Super Bowl Sunday!

💋💋💋

sissy terrie 💓

Honesty Is the Best Policy

OMG!

 I never would have thought!

My advice:  Be honest. Tell your prospective partners about your proclivities.  

It worked out for me.

Love,

sissy terrie 👄

Boys With a Bra

If you're a crossdresser whose interest in girly things was sparked at an early age, I'm sure you remember the struggles you had putting on a bra by yourself.  The first time I successfully got my sister's bra on I had to do it backwards - fastening the hooks in the front, twisting it around and sliding my arms through the bra straps after I had it facing the right way!

But once you get the hang of it it's like riding a bicycle!

This morning I was running a little late for a meeting on Zoom and I got my bra on in nothing flat.  I was so rushed for time I didn't even take the time to put some panties on.

No worries.  I wasn't totally naked and free under my jeans.  The omnipresent Holy Trainer had things well covered.

Love,

sissy terrie 💓
 

Frilly Fantasies

My mom taught some classes during the summer when I was younger.  When my two older sisters were too busy with other things like work or some type of summer camp, my aunt would "babysit" me.  I hated the term and mom would usually say something like "She's keeping an eye on you" but occasionally she'd slip, sometimes embarrassing me in front of my sisters or worse, friends, neighbors or cousins of mine.

In the complex mind of a young boy with a penchant for panties and other girly things, the emotions such embarrassment would evoke were incredibly difficult to understand.  As much as I didn't want her to embarrass me, the fantasies it produced in my mind were both pleasant and prominent.

I never got any such gifts from my aunt in real life.  But in my fantasy world, such gifts were plentiful, pretty and always pink!

Love,

sissy terrie 💗

 

Sissy Dreaming

I knew I would never have her curves.  But that didn't stop me from trying on her things.  

I'd fantasize about having breasts and a girlish round ass.  Sometimes, I'd stuff her bra with some of her panties or stockings, shaping them as best I could to make myself presentable. I'd dream about what it felt like to have real breasts.

I was careful, peeking out the window of her room to make sure she wouldn't be home earlier than usual. 

My big sister, suspicious that I might had been rummaging around in her things, once threatened me that if she ever found out I was doing that, would tell everyone she could.

At first I didn't dare come close to her room.

Eventually I couldn't resist the urge any longer.

Love,

sissy terrie 💙

Home Alone

Let's be honest with each other.  We did some silly and naughty things during our early crossdressing years when we were home alone.

Some were silly....

While others were naughty...

Both were fun.

Love,

sissy terrie 💖

Sissy Boarding School

Today's post is courtesy of Kevin (aka Karen) whose wife just recently officially made him/her a sissy cuckold.  Karen wrote the very first post for this blog at my request.  We had corresponded a few times and when I told her I was thinking of starting a blog and described what themes I wanted to feature, she volunteered to write a short story for me.  I hadn't heard much from her after that until two days ago when she sent me this little vignette, complete with pictures!   I hope you enjoy and I hope Karen continues to contribute when she can.

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    "First year students get the most basic of our rooms.  They're comfortable but simple.  If you get through your freshman year, next year's room will have more amenities" the dean of students said to Karen.  Her name was Ms. Smith.  She had a very pleasant smile but with an authoritative way about her.  "As you would expect gurls in their junior and senior years have the nicest rooms."

    Kevin's mother had decided upon this particular boarding school when she grew tired of catching Kevin rummaging through her things as well as his older sisters too many times.  As a single parent with a full time job, Kevin was becoming a little too much to handle. 

    "Get yourself settled.  Ms. Johnson will be stopping by later to issue you your uniform for class tomorrow and something for you to wear for dinner tonight" Ms. Smith said.  "Any questions?"

    "No ma'am" Karen said.  Ms. Smith just smiled, turned away and walked out of the room.

    The room was certainly not what Karen was used to.  Very tidy, feminine and totally void of any "maleness" like his room back home.  Though Karen had an affinity for girly things his room had all the markings of fourteen year old boy, with pictures of his favorite sports heroes on the wall and other boy things scattered about.  

    Everything in this room seemed so feminine with shades of pink everywhere and all types of little dainty things.  The twin bed in the middle of the room looked comfortable but Karen had a hard time imagining living here for four years.

    Despite its simplicity the room had a lovely view of the school's beautiful grounds.  Karen's room overlooked a lovely flower garden with brick pathways, grassy areas, bird baths and nice looking garden furniture.  It all seemed very peaceful and serene.  In the distance were lots of trees, fields and rolling hills.  "Kevin" was going to miss baseball and other sports.  There didn't seem to be any athletic fields in sight at all.

    Karen walked around the room.  At least there was a private bathroom even though it was pretty small.  She noticed it didn't have a shower and sitting on top of the toilet was a little tent card with the reminder: "Remember to take your seat!"   "There will be no standing to pee.  Ever." she remembered Ms. Smith saying downstairs in the large common living room of the dorm just after Karen kissed her mom goodbye earlier that afternoon.  It was all starting to be a bit overwhelming.

    Karen would make the best of it she thought as she put her small bag of personal belongings on the bed.  New students had received specific instructions of what to bring with them.  Other than the clothes on they wore when they arrived, the only other clothing items they were to bring were three pairs of simple white cotton panties.  Everything else was to be provided by the school.

    As she sat on the bed Karen looked around and decided to take a look inside the closet in the corner of the room.  It was wider that the one she had at home, with two doors that opened away from each other.  She opened the doors to discover the most beautiful collection of feminine finery in pretty pastels that she had ever seen.

    She couldn't believe what she saw.  How in the world was a school like this going to help her break what her mom called "this nasty habit of yours"????  As she ran her hands across the collection of pretty dresses, gowns and petticoats she couldn't help but feel the stirring in her loins...

To be continued.

Karen

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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

Sissy "Hand-me-downs"

When you're the youngest child in a family, particularly a large one, there's a good chance you're going to have to wear hand-me-downs.   And you usually do it with at least some mild resistance.

I was the youngest in a family of three kids with two older sisters.  Unfortunately I was never "made" to wear hand-me-downs, instead sneaking into their lingerie drawers and other places to secretly wear their things.

However, I still fantasize about being made to wear their hand-me-downs.

Anyone else have similar fantasies or other real life stories to share?

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 💗

Behind Closed Doors

I like to refer to the 50's and 60's as the golden age of femininity.  I really wish I could have experienced it first hand.  Fortunately with sites like Pinterest, Tumblr and others, those of us who are fond of femininity can do so vicariously through the many girls and gurls of that time.

I came upon this picture of the beautiful Elizabeth Taylor.  I remember watching her in the movie "Cleopatra" and becoming mesmerized by her eyes.  I wasn't nearly as thrilled by what she wore as Cleopatra as I was by her in this gorgeous pink when she played Ruth Wiley in "Elephant Walk.

The scene depicts Mrs. Wiley lonely and neglected by her husband John who remains dominated by his late father's influence even after the man's death.  

When I see the photo, I cast myself as the lonely but temporarily content sissy, dominated by the lust for his big sister's pretty things, enjoying himself behind closed doors.

Love,

sissy terrie 👄

"I need to know..."

She wasn't supposed to be home until well after 4.  It was only 2:15.  I never heard her car pull into the driveway.  Nor did I hear her enter the house or walk upstairs.  Her summer internship at the newspaper had begun the week before.  She was working in the newsroom for the evening edition, shadowing one reporter or another, some copy editors and doing different things.  She was in her junior year in college and wanted to be a journalist.  Frustrated with her switching majors and having a bit too much fun in her first two years, my parents had laid down the law and told my big sister to get serious.  It seemed to have worked.  She was really into this newspaper gig.

That was fine with me.  Still too young to work but old enough to be home alone at times, these summer afternoons provided me an opportunity to engage in my favorite pastime - dressing as a girl.  With two older sisters, there were of plenty of things to wear around the house.  It was always a question of timing.  This particular two weeks found my other sister away at some honors program at a high falutin' prep school, studying Greek Mythology or something similar.  My own days were spent with some baseball in the morning and pretty bras in the afternoon.

I was like a kid in a candy store.  After showering I would go through their things, decide on some bra and panties to wear and start all over again.  The bras, panties, slips, stockings and thing put me into my own little world of femininity.  But this particular afternoon that world seemed to crumble when I heard my oldest sister gasp...

"What the.......?" she shrieked.  "What are you doing?"

There I stood in front of lingerie drawer in bra and panties.  She was hysterical, shouting, screaming and even crying.  What was I supposed to do.  I tried to explain I was just goofing around and immediately apologized and took the things off and ran into my room.  I was screwed.  When I finally came out I saw that she had done the same.  The door to her room was closed.

"Please" I said standing outside the door.  "I am so sorry.  I'll do anything.  Please don't say anything to anyone."  I stood there for what seemed like an eternity.  Finally, she opened the door.  She could tell I'd been crying and must have sensed how bad I felt and how scared I was.  

"We need to talk" She said.  "But first there's something I need to know.  How long have you been doing this?"

And so we talked.  For a very long time. 

Love,

sissy terrie 👄