Sissy Cosmo

My wife just mixed me one of her special Cum Cosmos.  Yummy!

It's Happening

There was no doubt about it. The changes to my body, and to my complexion and facial features were becoming permanent.

The Good, The Bad, And The Ugly (Of Tucking)

 

My wife insists that I tuck my clitty, to maintain a smooth, feminine front.  And that's good.

Sometimes, however, when I bend over while wearing the short skirts she insists that I wear, I reveal more than is ladylike.  And that's bad.

  The ugly?  The ugly truth is that my wife gets off on seeing me like this.

The Blind Date

So, my wife is going on a blind date tonight with a friend of her best friend’s boyfriend.  Actually, they’re going on a double date.  My wife has been teasing me about it all day as I helped her get ready.  Now, she is nearly hysterical imagining his reaction when he removes her corset - actually - when I remove her corset for him.  You see.  That’s her plan.  She wants to bring him to our house after they drop off Jill and Bob, and I am to greet them at the front door wearing my pink French maid outfit.  Then, she is going to introduce me to him as her sissy husband.  I am to serve them drinks and then, when she gives the signal, I am to undress her and, then with a bit of flourish, remove her corset and present her to him.  When he sees her huge breasts for the first time, he is going to think he died and went to heaven.  When he gets her in the bedroom and fucks her, he’s going to know it.

Sissy Titty Torture

“I promise!  No more wanking my clitty without permission.”

It's Self Evident

Why this sissy was born to be one

As if....

Serving Her Boss

I was returning from taking the dogs for a walk.  I noticed a strange car parked in front of my house.  It wasn’t there when I left an hour ago.  As I got closer I noticed movement.  Inside of the vehicle.  Plus, the car was shaking too.  Then, as I got closer it hit me!  The car belonged to my wife’s boss.  He’d been over for dinner last Saturday.  I walked slowly as I approached and couldn’t believe what I saw.  That was my wife inside!  Fuck!  And her boss had brought a friend.  I slipped past and into our house without being seen.   Then, I watered the dogs and went to bed.  To wait.  I knew what my wife would want when she was done with her boss and whoever he'd brought along for the ride.

The Sissy's Dilemna

What should the sissy choose?  A champagne pussy?

Or a creampie pussy?

Such decisions are too difficult for a sissy to make.  Perhaps Mistress can decide? 

Crossed Up

 

Jesus Christ!  That bitch’s zipper is down!

The Crossword

 

Hmmmm.  A five letter word for a guy who likes to wear women’s panties.  Crossdresser?  No.  Too long.  Tgirl?  No.  Ends in Y.  Oh!  That’s right!  It’s me!  Sissy!  Yaaaayyyy!

Red (And White) Wine

My wife’s latest idea for me.  Her reasoning is that I love red wine - soooo, how much better if…..

Sissy Surprised

My wife was out of town for the weekend, visiting her sister. Even though I was alone, I knew that her rule was, ‘If I’m at home, I’m dressed in girl’s clothing.”

And so I was when there was a knock on the door. Stupidly, I opened it without looking to see who was there. Finding her boss and another of her co-workers at the front door was confusing. Her boss had been over before. Fucking my wife. He knew about me. The other guy, I’d heard of, but as far as I knew, he’d never been over. 

Assuming they stopped by to see my wife, I explained to them that she was out of town. 

Her boss answered, “Yeah. We know. We’re not here to see her,” he explained as they walked right in without being invited.  "We're here to see you sissy!"

He shoved me backwards, making me stumble, falling to my knees.  Before I fully realized what he was doing, he’d stuck his hand down the front of my pants and squeezed my clitty. Hard!

“Bill,” he addressed my wife’s co-worker. “It ain’t much, but she has a little dickie. Here! Check it out,” he said as he pulled it out.  "But she won't be using it tonight."

I knew then that I was in for a long night. I wondered if my wife knew they were here.

Once You Go Black...

This is a sissy who has finally been permitted by his wife to fully experience the pleasure of her black lover.  Until now, she's only been allowed to fluff him for her wife.  Now, because she's been a very good sissy, her wife let her taste her black lover's sperm directly from the source.  Can she ever go back?

The Hotel Pickup

“Oh baby!” my wife said to me as the guy we picked up in the hotel bar fucked her.  “Thank you so much for this sweet anniversary gift.  I haven’t felt a cock like this in me since, well, before I married you.”

The Sissy Touch

“Like this sissy,” my wife directed my hand.  “From now on, whenever I allow you to masturbate, you may only do it like this.  No more jacking off like you used to.  You’re a sissy now.  Always remember that.”

Sissy Sex - Equestrian Style - Yee Haw!

Giddy Up!

My Fall To Grace - Chapter Four

My Fall To Grace, Chapter Four has been posted.

Grace Andrews is a beautiful, confident, successful woman.  She could have any man she wanted.  She chose Dan Thompson, a successful Washington, D.C. attorney.  This second story of mine, that will be released in installments on Fictionmania, chronicles their relationship as it grows and flourishes, developing into something perhaps neither one could have envisioned the first night they met in a D.C. bar.  I hope readers enjoy my effort.

Much love,

Leeanne

Oh My!

Street Sissy

My wife just called me from her office.  She’s on her way home with her boss for dinner.  She insisted that I change into this outfit and wait for her in front of our building to greet them.

How To Train A Sissy

“Fuck Joan! You really did turn your husband into a sissy! I can’t believe how he’s prancing around in that maid’s dress and high heels.”

“Yep! And it didn’t take long either. She’s a natural.”

“And you say I can do the same with my Bob?”

“No sweat. The secret is a CB-6000.”

“CB-6000? What’s that?”

“A chastity cage. Works like a charm. They fall right in line.”

“Wow! But what about, you know, sex?”

“She wasn’t much use there anyway. That’s where Tyrone comes in. And he has a friend - Jermaine - who I understand is hung like a horse.”

“Okay. I’m convinced. When can we start?”

“No time like the present. Call Bob and tell him to come over.”

The Lunch Date

My wife called me to see if I wanted to meet her for lunch.  It sounded like a good idea, so I met her at her office.  Before we left to eat though, she seduced me in her office.  The next thing I knew, I was eating her out.  I was noticing something different about her when she told me she’d just been fucked by her boss, and I was eating his sperm.  That was the moment I knew I was her sissy.  The moment I didn’t stop sucking her pussy when she told me that.

Cuffed

At first, I didn’t understand why my wife insisted I wear cuffs while she entertained lovers tonight.

 

Then later, I understood.

And then, after this, this

Watching

“That’s right sissy,” my wife called back to me.  “Stay right there when John arrives.  You can watch.  But you may not touch yourself.”

Even Birds Know

Even sissy white birds understand that “once you go black, you’ll never go back.”

The Happy Couple

“What do you think sissy?  Don’t we make a pretty couple?” my wife asked me.

Mother-In-Law

I had this clever idea today. I was going to wait, in this position, for my wife to arrive home from work, and surprise her. I was going to be the main course for dinner. 

Imagine my shock when she surprised me by bringing her mother home for dinner.

All Work, And No Play, Makes Sissy An Unhappy Girl

I know I’m just a sissy and all. But fuck! I’m getting a little tired of always having to do the dishes while my wife gets fucked by my no good brother.

Sissy Shame

On the bed beside me, my wife was being fucked. I didn’t know by whom. But she continuously was calling out the name, “Sam,” which happened to be my boss’ name. Would she? Would he? The answer to at least one of those questions was decidedly, “Yes!”  The unanswered question was the second one.  Would I be able to tell when I saw Sam at work tomorrow?

Sissy Body Awareness

I’ve grown much more comfortable with my body - the one my wife has slowly transformed through diet, exercise and a carefully administered regimen of female hormones.

 

How To Fluff

My wife had taught me well.  How important it was, when fluffing a cock for her, not to simply suck her man’s cock, but to love her man’s cock.  To prepare it with the proper reverence.  After all, I loved her.  And if I loved her, I should want only a cock - a big, man’s cock to be precise - prepared with tenderness and love entering her pussy.

Necktie

Even after my wife feminized me, I still found use for at least some items of my old wardrobe.

Surprised?

Is that what that look in the sissy's eyes is?  Or, is it anticipation?  Of what she is about to receive?

Willing?

It may not look like it.  Based upon the photo.  But I assure you.  This sissy is right where she belongs.  And where she wants to be.

And where her wife wants her as well...

My Fall To Grace - Chapter Three - Posted

My Fall To Grace - Chapter 3

I just posted my third chapter of my story, "My Fall To Grace."

Grace Andrews is a beautiful, confident, successful woman.  She could have any man she wanted.  She chose Dan Thompson, a successful Washington, D.C. attorney.  This second story of mine, that will be released in installments on Fictionmania, chronicles their relationship as it grows and flourishes, developing into something perhaps neither one could have envisioned the first night they met in a D.C. bar.  I hope readers enjoy my effort. 

Much love,

Leeanne

My Fall To Grace - Chapter 2 - Posted

My Fall To Grace - Chapter 2 

I just posted chapter two to my story, "My Fall To Grace."  I hope everyone enjoys the story.

Grace Andrews is a beautiful, confident, successful woman.  She could have any man she wanted.  She chose Dan Thompson, a successful Washington, D.C. attorney.  This second story of mine, that will be released in installments on Fictionmania, chronicles their relationship as it grows and flourishes, developing into something perhaps neither one could have envisioned the first night they met in a D.C. bar.  I hope readers enjoy my effort. 

Much love,

Leeanne

Sissy Makes Life With Cheerleader

My Beautiful Cheerleader

I left off my account of my personal sissy journey of self-realization with my marriage to my high school cheerleader crush.  I think it is important to clarify that, while the events and activities of my life that have led me to where I am today were occurring, the concept of "being a sissy," that I now understand, wasn't even a thought process for me.  I saw myself as a man.  Even though I loved all of my girly dress-up opportunities, I never thought, "Gee!  I should have been born a girl!", or, "I wish I could have a sex change and become a girl!". Nope!  I was simply a guy who liked wearing women's lingerie. 

But there was more, and I did struggle with it.  That I was never able to have sexual intercourse until I met my cheerleader, was a problem that I was completely aware was a problem.  And part of the problem was I could never admit the problem.  And, moreover, I had to lie about it to make sure no one ever knew the truth.  Even my cheerleader didn't know, when we married, what she'd done for me that first time we made love.  As far as she knew, I was a typical man who enjoyed sex.  But, what she did do for me, was to make it possible for me to stop obsessing about it.  Because, with her, it was no problem.  And given my track record, I was so thankful for her being that woman who helped me "solve my problem," even if she was unaware that she'd done so, that I was like a puppy dog who would follow her anywhere after that.  And, she did love my "special talent" quite a bit.  Even now, we each realize that my "special talent" lies in what I do with my mouth, as opposed to what a woman needs a man for.

So, after I married my cheerleader, we settled into our life.  She was my savior, and in many ways, I was hers as well.  Remember, her crap ex-husband ran out on her, leaving her with two children to raise.  I stepped in, and if I say so myself, did a good job.  We built a very happy and good life together.  Our sex life was amazing.  And, it stayed hot for a long time.  Because I was so hyped from finally being able to fuck, I initiated a lot of that.  And she was up for it also.  Only in time did my draw to lingerie return to me.  My cheerleader was throwing away some old clothes one time, and I was carrying it to Goodwill.  I noticed a few bras, bodybriefers, and nylon nightgowns in the bag. I don't really remember what caused me to do it, but I pulled them out and kept them. I took them home and hid them in my closet, and so began a part of my marriage when I hid something from my cheerleader.  I would never have thought she'd accept that.  While she was really a hot lover, and loved sex, her thoughts and view of the world made me think anything out of the mainstream would be considered "sick.". And I didn't want to risk anything, even with her.  Maybe, especially with her.

For a good while after finding her lingerie in the Goodwill bag, when I could, I began dressing in her things.  It was about then that the Internet was really taking off, and my curiosity led me to discover crossdressers. I was amazed to find how many beautiful "girls" there were.  I began to wonder if I could pull it off.  I had to know.  I researched and researched.  Soon, I had a plan for how I'd give it a shot.  I couldn't risk delivery of women's clothing or a wig to my house, so I knew I'd have to buy what I needed from a store.  I couldn't do that in my hometown.  Too many people knew me.  So, I planned it for a conference I had to attend alone out of town.  I researched stores in the city of the conference and planned out every detail.  I was, as you might imagine, scared to death when I went shopping for my clothes, makeup and wig, but I was determined.  Confident that no one knew me, I was prepared for whatever store clerks might think of me.  I didn't care.  They'd never see me again the moment I walked out of their store.  All I knew was that I had to try.  And I did.  And it was amazing.  I'm pretty sure I looked like crap.  But I didn't care.  I was dressed up like a woman.  Fully.  Completely.

When I returned home from my conference, I hid all of my woman stuff in the garage where no one would find it.  The lesson I learned from my mother many years before - that men who dressed like women were perverted sex freaks - had stuck.  I could not let my cheerleader know.

This went on for a while.  I began wanting my cheerleader to be involved, but could never get up the nerve to tell her.  Instead, I began leading our sex life into more variety.  A little, especially from her standpoint, more kinky. For example, I got her to agree to try out a dildo.  She liked it.  She was uncomfortable at first, but she liked it.  When I saw how she liked it, I pushed the envelope.  I got a big one - shaped like a cock.  She really liked it.  I began inserting fantasy into our sex.  I'd lick her while I used the dildo on her.  I'd talk about her getting fucked with a big cock while I licked her.  She would never talk like that, but she liked it.  A lot.  I could tell.  She was hooked.

 

  Then, one night while we were making love, I got up the nerve, and told her I thought it would be fun if I wore a pair of panties.  She froze up immediately.  I'd gone too far.  She did not react as I'd hoped.  The subject was dropped.  I apologized profusely for suggesting it.  But then about a week later, when I got home from work, without a word spoken, she handed me a present.  When I opened it, she was watching my reaction closely.  My cheerleader had bought me a pair of panties.  She told me she'd decided if it was something I wanted to try, she was willing to let me.  But, the lie was still there.  She was "letting me try it out.". The truth was, I was simply drawing her in to something I had already tried out.  I was beyond "trying it out.". But, with her, it was a step forward.  She may not have known the entire story then, but she knew her husband wanted to wear panties.  

The Actual Panties My Wife Bought For Me

We made the first time we made love with me wearing my new panties an event.  Our children stayed at their grandparents' house.  We built a fire, and we put a sleeping bag on the floor.  I got inside wearing the panties, and brought the big, fat, dildo cock.  My cheerleader was great.  I think she really suspected even then that my desire to wear panties had not just "materialized" out of the blue.  She made it easy for me.  We had an amazing night of sex.  I licked and sucked her for hours, finishing with a great fucking with the dildo, and then me.  She always wanted to end with me inside of her because she said she loved feeling my hot sperm fill her pussy.  She still loves that.

We went on like that for a while.  She was tolerant of me wearing the panties.  A few months after that, I asked her if she would mind if I wore a nightgown.  I could tell this was going a bit too far for her.  I must have caused her suspicions to rise.  She saw my desire as a problem, as I realize many women who find out their husbands like wearing women's lingerie must feel.

She began checking behind me on the Internet, and hit jackpot.  Not only did she find the many cross dressing sites I visited, but she found a chat room where I went to play out my feminine fantasy.  I even had posted a few photos of me, and that really freaked her out.  She eventually confronted me.  I thought she was gone.  But instead, she arranged a long weekend away - just the two of us - to talk it out.  I was scared to death, but I was afraid she was going to leave me too.  And I loved her.  I love her.  I decided I had to, as we say in the law, tell the truth, the whole truth, and nothing but the truth.  And I did.  We went for a long walk one of the days we were away, and I told her everything, from the beginning to the end, including that she was the first and only woman I'd ever made love with.

She was definitely stunned by all that I revealed.  I think what confused her the most was that there was no way - no way- for anyone to have ever guessed that I might be a man who'd wear women's underwear.  That I was a sissy.  But, even then, the "sissy" word did not come up.  I didn't realize it, intellectually anyway, even then.  On the other hand, she was deeply touched by my honesty (finally), and concerned that I'd lived with this truth about myself for so long without ever being able to share it.

Well, I wish I could tell you that my cheerleader reached a moment of acceptance and that everything was hunky dory after that.  But that isn't what happened.  Instead, we lived with the knowledge of the "truth" for a while, with no reactions taking place.  We simply went on with our lives.  I continued to sneak wearing lingerie, with her permission - just not in her face.  And I had to promise no more photos on the Internet.

We moved on.  We continued having great sex, including the use of my cheerleader's new best friends, the big dildos.  Every now and then, she'd invite me to dress up for bed. And I'd joyfully accept.  I think even she realized that, on those nights, I enjoyed it more.  And she even did too.  There was a slow erosion of resistance going on.

And we went on like that for a while.  Until our last child went away to college.  And then, something happened.  And the next time I write about my journey to being a sissy,  I'll tell about it.

My Fall To Grace

My Fall To Grace

Grace Andrews is a beautiful, confident, successful woman.  She could have any man she wanted.  She chose Dan Thompson, a successful Washington, D.C. attorney.  This second story of mine, that will be released in installments on Fictionmania, chronicles their relationship as it grows and flourishes, developing into something perhaps neither one could have envisioned the first night they met in a D.C. bar.  I hope readers enjoy my effort. 

Much love,

Leeanne

The Versatile Sissy

Traditionally, I believe most think of the sissy in a certain manner.  The good sissy, after all, first and foremost, serves her Mistress, or her wife, or, in some instances, her Master.  For example, it is completely natural to find a sissy serving her Mistress or wife preparing for a date.

Likewise, foot worship, or any form of worship, is completely within the realm of expectations for a good sissy.

And, of course, any good sissy should be expected to serve his Mistress or wife and their lovers.  At all times.

Then, there is housecleaning.  Of course.  What good would a sissy be if she could not be expected to do the heavy lifting for her Mistress or wife?

Laundry and ironing?  Duh!

Dishes?  Of course!

 And then, there are some of the more personal services that a sissy naturally performs.  Such as, fluffing.

An absolutely essential task for a good sissy, and really should go without mention (however, I will) is assisting her Mistress or wife with feminine hygiene.

But these are some of the services one would expect a sissy to perform.  But, as we know, sissies are so much more.  We see sissies branching out to excel in many different areas.  For example, musicians.

Or Gambler,

How about an ornamental display?

 Or, Hell's Angel?

 How about transportation?  Giddy up!

 A sissy is naturally suited to being a bathroom attendant.

 A sissy photographer.  Uh huh!

 Sissies are perfect for home decor, such as wallpapering.

 How about a sissy carpenter?  I'd like to see that!

 

Or Lawn Girl

  Ventriliquist?

 Sissy Firefighter?  Hot!

Sissy Search and Rescue?  With Sissy's best friend.

Sissy Pastry Chef?

Sissy Voyeur?  Nice job!

Lamp?

How perfect would a sissy ballerina be?

Yee haw!  Sissy cowgirl!

Heep big squaw

How amazing would a sissy spy or assassin be?

She would be a devilish little sissy

This would be interesting - a sissy gatekeeper

I'd like to have this sissy stop by for roadside assistance

We'll have a cabaret old time sissy!

I pray for a sissy nun. Amen.

Any sissy would be an excellent shoe salesgirl

Such a sweet sissy witch!

Sissy Santa's Helper.  Santa would love to have her sit on his lap!

Would this not be entertaining?  A sissy juggler?

She could crawl under my house any time.  A sissy pest control specialist.

She'd make me laugh.  A sissy cartoon character.

Any building would be better off, and cleaner too, with a sissy janitor.

This could be useful.  A sissy notepad.

Sissy Snake Charmer?  Hisssss!

Sissy Trapper!  Isn't her beaver lovely?

Sissy Pugilist!  Bam!  Boof!  Pow!

Sissy Grillmaster  Mmmm good!  She could hold my wiener!

Aarrgh!  Sissy Pirate!  She could walk my plank!

Sissy Refrigerator Repair Girl.  Sleeping on the job.  Bad sissy!

Sissy Pet Sitter.  Doggie likes!

Ssshhh!  Sissy Librarian.

Sissy Cook?  Hot!  Oh no!  Not this sissy!

Of course, we'd expect to find a sissy secretary.

Lovely!  A sissy runway model.

How perfect would she be as a sissy stewardess?

This would be different.  And useful.  A sissy wine taster.

First Mate?  She could rock the boat!

Sissy Mail Girl!  First Class Delivery!

This would be one of my favorites.  Sissy Stick Shift.  I'd want to drive all the time!

A Sissy Vase?  Uh huh.  A rose is butt a rose.  Butt a sissy...

The perfect place to rest your brandy - a sissy end table.

She could entertain your friends, and make a little cash.  Sissy Pole Dancer!

Sissy Car Wash!  Oh yeah!

Sissy Nurse.  I'd love for her to take my temperature.  Use the anal thermometer please!

Now, we reach the end.  Admit it ladies.  Why carry the baby Tyrone impregnated you with for nine months?  Let your sissy carry the baby.  Sissy Mommy!!

Or, and I admit I'm partial to this sissy.  Sissy Eye Candy.  After all, don't or Mistresses and wives love looking at us pretty sissies?

However, you choose to use your sissy, you can be certain that she will be the right girl for the job.  There is literally nothing that a good sissy cannot be properly trained to perform.