Tuesday, July 31, 2012


I could tell this guy that my wife went out with tonight was really getting off on the situation.  My wife was nearly naked, sucking his cock while he remained fully dressed.  Meanwhile, I’m kneeling on the floor, across the room, wearing a pink baby doll, stockings and high heels, my caged clitty visible just beneath the hem, watching her suck him.


“Sissy!  Would you please answer the front door?  I believe John is here,” my wife asked me, referring to her boss who was taking her to dinner.

“Dressed like this?” I asked, referring to the light blue babydoll and heels she had me wearing as I'd helped her dress for her evening out.

‘Of course!  You’re a sissy!  Besides, John knows all about you.  Now run along.  Fix him a drink and tell him I’ll be right out.  Do I look okay?” she asked before I left.

“You, lo, look beautiful,” I assured her.

She smiled knowingly at my acknowledgement.

Size Matters

When she let her girlfriend set her up on a blind date, she had no idea the guy she was setting her up with was so, so .......

My Fall To Grace - Chapter Ten - Posted

I've just posted on Fictionmania a new chapter to my story being shown there - My Fall To Grace - Chapter10
   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, 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. Readers Note: This is a long story.  I'll keep installments coming.  I love getting reader feedback.

Monday, July 30, 2012

My Fall To Grace - Chapter Nine - Posted

I've just posted on Fictionmania a new chapter to my story being shown there - My Fall To Grace - Chapter 9
  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, 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. Readers Note: This is a long story.  I'll keep installments coming.  I love getting reader feedback.

Sunday, July 29, 2012

Cheerleader Discovers Sissy

[NOTE - Anyone who is just beginning to read my blog, might want to read the following entries about my sissy journey before reading this entry: A Little More Background, Am I Sure I Should Do This?, I'm Afraid, These - Where It All Started, Then, These, Miss Flo, Caught For The First Time, About My Last Post, Bikini Panties!!!, A Virgin Bride (And Groom), Exhausted Sissy Needs Stress Relief!, Sissy Marries Cheerleader, and Sissy Makes Life With Cheerleader.  These are the previous posts that tell the story about my sissy journey.]

After our last child went away to college, my cheerleader and I settled into a new life together.  Of course, we still had contact with our children, and they came home for holidays, but things were different when it was just the two of us at home.  It was almost as if, now that there were no children in the house, my cheerleader relaxed a little bit when it came to some of the more “kinky” things I tried to introduce into our sex life.  She began seeking them out more.
For example, she’d suggest I use the dildo cock on her, rather than wait for me to ask her if she wanted it.  I’d ask her, while fucking her with the big dildo cock, if she liked big cocks.  Where before she’d let me do it, but didn’t seem comfortable talking about it, now she was more vocal.  She would say that she loved big cocks.  That she loved being fucked by big cocks.  She’d thank me for fucking her with big cocks.
She was more comfortable with me wearing lingerie to bed every now and then when we made love.  I was so happy with the increase in her comfortableness.  Any opportunity that I had to dress up was a boon for me.  She must have noticed how much more gentle and feminine I was in my lovemaking when I wore panties and a nightgown.  Not that I wasn’t generally gentle, but I think she could sense my role shift when I dressed femininely.
And then, one day, a significant moment in our marriage and sex life occurred.  My cheerleader always made me lunch.  On this particular day, she wrote me a note and put it inside of my lunch bag.  When I opened my bag for lunch that day, I found the note.  I could not believe what she’d written.  It meant so much to me that I still have the note.  This is what she wrote:

            “Dear *****,

            The first thing I want to say to you is that I love you.  And I will love you forever.  I guess you know that your crossdressing has not always been easy for me.  I have gone along with it because I can tell you enjoy it.  Mostly, I worry about people finding out.  I realize none of our friends could possibly know about it, as you never show any signs to the world of being anything other than a man.  But, I’ve come to know differently.  And while I wonder if I would have have accepted it if you told me right off the bat, I can’t change it now.  I see that.  And I love you.  You are a kind and sweet man and I can’t see my life without you.  And, I have to admit, there have been parts of our sex life that I’ve enjoyed because of it.

            I want to try something, if you are willing.  If you don’t want to, I understand.  But I am willing to take this thing another step if you want.  So, here is my proposition.  This weekend, Saturday night, I’m going to fix us a special dinner.  I want us to have a very private and romantic dinner together.  And then, when we go to bed, I want you to dress up for me.  All of the way.  Or, almost all of the way.  I don’t want you to wear your wig.  I don’t think I can handle that.  But, otherwise, all of the way.  I want to see what it will be like to make love like that.  And bring the biggest dildo to bed too.  And I only ask one thing of you.  When we’re making love, I want you to tell me every single thought you are having.  Every single one.  I want to know exactly what you think when you are dressed as a woman.  We’ll do this, this time, and see how it goes.  Then, if we both agree, maybe we’ll do it some more.  If you are willing, don’t say a word.  I don't want to discuss it.  I just want to try it.  So, if you come home from work tonight and kiss me like you always do, but say nothing, then that means you agree.  Otherwise, say so.

            If you decide not to, then that will be that.  I’m not saying how I’ll react.  I don’t know.  But I’m willing to try.  For you.  And no matter what you decide, or what happens, I will always love you.



That is the letter.  Exactly what she wrote to me on that day.  Needless to say, I was stunned to read her letter.  I was, up to that point, so happy that she hadn’t left me when she found out about my inclinations, and even more so, that she permitted me some opportunities to express myself from time to time, albeit limited.  I never expected any more from her.  To tell the truth, her letter actually scared me a little.  It was one thing, even for me, to slip into bed wearing panties and a nightgown.  She was basically telling me to dress up all of the way.  I assumed she meant a bra, breast forms, garter belt and stockings.  Completely femmed up.  Would I be embarrassed to do that in front of her?  Could I really do it?  And was she calling my bluff?  Did she really want to see?  Or was she secretly hoping I would chicken out and not do it?  For the rest of the day my stomach was churning with butterflies.

When I walked in the front door that evening, my cheerleader came to the door to greet me.  I could read the expectant look in her eyes.  What was I going to do?  I approached her and kissed her softly on the mouth.  I said, “I love you.”  She smiled back at me with a knowing twinkle in her eye, and with an unspoken understanding passing between us, she smiled and said, “I love you too.”
We then went on with our evening, and even the rest of our week.  I can still recall the sexual tension that was in the air that week.  I was nervous about the weekend.  She, on the other hand, seemed anxious for it to arrive.

When we awoke on the fateful Saturday morning, we each went about our day.  She told me we’d eat dinner around seven on the patio.  As the day wore on, I became more and more nervous.  Should I back out?  If I did, would my cheerleader use my decision as a way to end my dressing up altogether?  No.  I was going to do it.  I was going to do it.

We ate dinner, and the unspoken tension was incredible.  She never said a word.  All week she’d never said a word.  But every time I looked at her it was as if she was sizing me up.  Was I really going to do it?  And her eyes were literally sparkling with her own anticipation.
When dinner was over, she stood up and told me she would do the dishes.  She told me to go get ready and get in bed.  She would join me when she was finished.  She wanted me to get dressed in my feminine attire, and then wait for her in bed.  I was so nervous.  I cannot even begin to describe how nervous I was.  I was afraid.  I was excited.  I wanted it.  I feared it.  My emotions about what we were about to do were all over the roadmap.  But it looked like we were going to go through with it.  Unless I backed out.  And I wasn’t going to back out.  Not at that point.  And looking back on it, I am so glad that I didn’t.

I went to our bedroom, into my closet, and undressed.  Then, I put on the lingerie I had decided I was going to wear.  I’d dressed up in it many times before, and I have worn it many times since.  It remains one of my favorite ensembles.  I even have photos of me wearing it.  The only thing I didn’t wear that night, was the wig, and the heels.  And since a picture is worth a thousand words, here are three photos of what I wore, one showing the bra and waist cincher with garter, one showing just the babydoll, and another showing how I was dressed when I got into bed to wait for my cheerleader.
I got dressed, set the large, cock-shaped dildo beside our bed, and crawled under the covers to wait for my cheerleader.  When I heard her walking up the steps, I still remember the worried sense of anxiety I felt.  As she entered our bedroom, she smiled as she looked at me.  I had the covers pulled up, so all she saw was my face and shoulders.  But the breast forms caused a hump where my chest was, and I noticed her glance at them.

She didn’t say a word though.  She walked into her closet, and returned a few minutes later.  Nude.  She wasn’t going to wear anything.  Here I was, a man, dressed in a woman’s nightgown, with a peignoir, and stockings held up with garter clips, and a bra filled with DDD breast forms.  And yet my cheerleader, the real woman, was going to join me in our bed, totally nude.
I will never forget the look in her eyes as she pulled the covers back to join me that night in bed.  She stood next to the bed for a moment that felt like forever, as she examined me, to see what I looked like.  She said nothing though.  Instead, she crawled into bed beside me and snuggled right up, cuddling her naked breasts right up against my mine.  She looked me in the eyes, kissed me gently, and said, “You look pretty.”  I didn’t know what to say.  No one had ever called me pretty before.  I said, “Thank you.”

We stayed just like that for a while.  We kissed.  I touched her breasts, tweaking her nipples, because I knew she liked that.  As I expected, she began reacting to my touch.  She pulled my mouth toward her breasts and I began kissing and sucking them.  Soon, I was being directed toward her pussy.  She was so wet.  I’ll never forget.  Whatever her own concerns about me dressing in lingerie were, she was turned on.  I began pleasuring her with all that I had, and she lay back and enjoyed it.  I licked, kissed, and sucked her pussy for a long time.  She seemed in no hurry.  
Then, she spoke.  And the words she spoke should have been a clue, or a warning, but I didn’t understand at first.  She asked, “Are you ready?” 

Was I ready?  I thought I’d been showing her that.  I asked her, “Ready?” 

She responded, “To fuck me?”

I told her I was.  I was ready.  I was so ready.  And so I turned to position myself.  I reached to pull down my panties so I could enter her.  This was the moment that turned everything that night.  She had a plan.  This was not something she was going to let just take its course.  She was controlling things.  Her hand reached up to stop me. 

“No.  Not you.  The big cock.  The really big cock.  Are you ready to fuck me with the big cock?”

Oh!  Yeah.  I’d forgotten.  She had made a point of me bringing it to bed with me.  So, yeah, it made sense.

“Okay,” I answered. 

I reached for it next to the bed and brought it into position.  Just as I did, my cheerleader spoke.

“Don’t you think you ought to get it ready for me sweetie?”

I looked at her, questioning her request.

“Do you want to suck it?” she asked, gazing deeply into my eyes, as if trying to read my thoughts. 

I didn’t respond right away.  That’s when she said what made me realize she’d undergone a shift in thinking.  “Remember, you have to say what you are thinking.  The truth.  I want you to be honest.  Do you want to suck the cock for me?”

So.  The moment of truth.  I nodded.  I did.  I did want to suck the cock for her.

“Say it,” she told me.

“I want to suck the cock.”

“You do?  You want to suck my lover’s big cock?  To make it hard for me?”

Her lover?  She was going to fuck with me.

“Yes,” I admitted.

“Go ahead then,” she said.  “I want to watch you.”
I brought the cock to my mouth.  I remembered thinking I didn’t want to seem like I’d done it before, even though I had.  I opened my mouth and slid it in a little.  My eyes closed. 

“Open your eyes,” she said.  “I want to see you.”

She was intent on toying with me.  I opened my eyes.  I sucked the tip.  I slid it in more.

“You’ve sucked cock before, haven’t you?” she accused me.
I hesitated.  “Truth baby,” she reminded me.

With the cock still in my mouth, I nodded. 

“You like sucking cock?”

I nodded.

“Do you wish it was real?  A real cock that you were sucking to get it ready to fuck your wife?”

Fuck!  How did she know?  And who was this woman?  My cheerleader had never said things like this before.

“I’ve read about men who like that.  On your Internet sites.  They call them sissies.”

She said the word!  She knew the word!  She knew!  And she was making me face it!  This was a set up!  My cheerleader knew precisely what she was doing.  So, I had to decide.  Was I going to let go and reveal it all?

I sucked the cock further into my mouth, moaning as I did.  I began sucking it like I had so many times before when no one watched me.  My cheerleader watched me intently.

“Yeah baby,” she encouraged me.  “Get him big and hard for me.  Do you wish he could cum in your mouth?” 

I nodded vigorously.  I let the cock slip out of my mouth long enough to say, “Yes!”

She smiled at me.  “So you want to taste cum?”

I nodded as I rammed the cock down my throat.


Now?  What did she mean?

“Come on,” she said.  “Let’s do it now.”

I didn’t know what she meant, but she moved from under me and maneuvered me onto my back.

“Keep sucking the cock,” she told me.  

I sucked it vigorously for her.  She was smiling as she watched me.

My cheerleader then got between my legs and pulled my panties down enough to slip my penis out.  I was hard as a rock.  Then, she lifted my legs up and began lifting me higher.  Suddenly, I realized what she was doing.  I continued sucking the cock.  My cheerleader lifted me up until my own penis was positioned directly above my face.  She began jerking me off as I sucked the cock, encouraging me to suck it.

I had never seen my cheerleader so aggressive in our lovemaking.  I understood what she was going to do and I didn’t want to stop her.  I sucked the cock as she masturbated me.  She was looking right in my eyes and grinning like crazy.  I could feel it coming and so could she.

“Get ready,” she said.  “Stop sucking the cock.  Open your mouth.”
I did, and as I did, I began spewing my own sperm into my mouth, aimed there by my cheerleader.  A lot of it hit my face, but she aimed most of it into my mouth.  I still remember the look in her eyes.  She was loving watching me swallow my own cum.  As soon as I was done, she took the cock from my hand and stuck it back into my mouth and made me keep sucking it.  I was stunned at what had just happened.  Stunned and embarrassed. 

I remember still my cheerleader’s reaction.  She said, “Wow!”  Right.  Wow!  I could barely look her in the eye at that point.  I’d just sucked a cock in front of my cheerleader and then let her shoot my own cum into my mouth.  As usually happens, my “desire” waned at that point, but she wasn’t through.

“I need the cock baby,” she told me.  “Now.  Use it on me.”
And so, even though I’d had my release, I had to use the cock I’d just been sucking to fuck my wife.  I did it until she had a screaming orgasm.  Then, and only then, did she relax and cuddle back up to me.

I was still embarrassed at what we’d done.  And I didn’t know what to say.  But my cheerleader wasn’t without words.  “I think I liked that baby.  We might have to do that again.”

I’ll never forget thinking to myself, ‘Can I do that again?'  It was like this was my wildest desire, and now that it happened, I wasn’t sure I could handle it.  But we did do it again.  Not that night.  But on other nights.  And more.  And soon, I’ll tell more.  But this night goes down as a major turning point in my life with my cheerleader.

Friday, July 27, 2012

The Monthly Pajama Party

This was now a monthly event.  Right after my wife feminized me, she convinced her sister that she needed to do the same to her husband.  Then, just for laughs, they would make the two of us have sissy sex together, and sometimes, even, make us do each of their boyfriends.  Slowly, the word of our sissy exploits spread among their friends.  Now, once a month, my wife and her sister host a pajama party for their girlfriends, sometimes inviting men to provide sexual services.  But mostly, it’s so they can watch and tease their sissy hubbies as they make us do each other, and any man they invite.

Finish What You Start

“Are you sure you’re ready for this sissy?” my wife asked me.  “Jermaine fucked me three times tonight.  There’s going to be a lot of cum.  And I expect you to finish what you start.  Every!  Last!  Drop!”


A sissy and her Mistress, enjoying some "we" time.

Thursday, July 26, 2012

Tonight's The Night

My wife, presenting me to Keyshawn, her black lover.  Tonight, she has told me, I am going to lose my sissy cherry.  Until tonight, I assumed she was exaggerating how big his cock was.  But she wasn’t.  He is hung like a horse!

The Moment of Truth

I was feeling very nervous.  Nervous.  And shy.  And exposed.  And humiliated.  I hadn’t seen my two best friends since my wedding.  And the reason should be fairly obvious.  There was no way that I could face them after what my wife had done to me since our wedding.  But they had been calling non-stop, and I knew they were suspicious that something was wrong. 

Finally, the other day, my wife told me it was time.

“Time for what?” I asked her.

“Time for you to face your friends.  And to tell them the truth.”

“The truth?  What truth?” I asked her, nearly in tears.

“That you are a sissy silly,” she explained, as if it was obvious, and that I was a dunce not to get it.

At first, they didn’t believe it.  Until my wife made me strip for them and show them two things.  One was my clitty, proving I was not really a genetic girl, despite how hot I looked.  The other was a tattoo the three of us had gotten on a Spring Break trip in college.  That was the cincher.

It disturbed me to see the erections forming in their jeans as I stood before them.  And it worried me too, because I feared my wife might get an evil idea and then, well, you know….


This cock.  Me.  My wife.  We have something in common. Tonight.  I’ll suck it.  She’ll fuck it.

The Ready Wife

“What are you standing there looking at sissy?” my wife asked me impatiently.  “Go get Tom and tell him we’re ready for him.”

The Introduction

“John,” my wife said. “Meet my husband. Sissy. John. John. Sissy. We’ll see you in the morning sissy. Come along John. Let’s go fuck.”

Wednesday, July 25, 2012

Lost & Found

No.  This sissy hasn’t lost something under here.  She's found something.  And it is creamy and thick and salty and delicious.

Mystery Date

My wife assured me that I had nothing to fear.  All that she required of me was complete submission.  Still, I wondered who her date was going to be tonight.
Still, I thought it strange that he never spoke a word.  Not when I sucked his cock.  Not even when he fucked me in my sissy pussy.  What was the big secret?

Tuesday, July 24, 2012

Exquisite Joy!

I’ve seen that look on my wife’s face many times.  The look a woman has when she is being touched in places, and in ways, every woman deserves. I’ve just never been the cause of it.

Consumating The Marriage

“Honey,” the bride said to her sissy husband.  “Sit in the corner over there while I tip the bellman.  That’s a good sissy.  Remember our agreement?  I marry you.  But I don’t have to let you put that little pee pee in me.”

Monday, July 23, 2012

The Business Dinner

I could tell that my wife was pleased.  She had a very important business dinner to attend tonight.  She’d asked me to pick out special lingerie for her to wear, as she always feels more confident, she says, when she knows that underneath of whatever business attire she wears she is all woman, and all sexy.  Unlike some of her business dinners, spouses were not invited to this particular one.  Looking at her now, I was now having doubts about my selection.   My doubts and concerns escalated after she casually mentioned that the guy from accounting, who I knew she had a crush on, was going to be at the dinner also.

Sissy's Just Dessert

In the beginning, when my wife told me she expected me to fluff her lovers, I was repulsed by the idea of sucking another guy’s cock. Now, as a reward for me behaving and doing a good job as her sissy, she let's her lovers do this to me every now and then.

My Fall To Grace - Chapter 8 - Posted

I've just posted on Fictionmania a new chapter to my story being shown there - My Fall To Grace - Chapter 8
 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, 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. Readers Note: This is a long story.  I'll keep installments coming.  I love getting reader feedback.

Sunday, July 22, 2012

The Sissy Chauffeur

I knew that look from my wife.  We were at one of her office functions.  And I could tell that someone - some man - had caught her eye.  She was going to bring him home with us.  I told her I’d be out front waiting for them with the car.  You see, I was going to drive them home and help her get ready for bed with whoever it was.

Saturday, July 21, 2012

The good sissy

I just had to re-blog this wonderful post by Sissy Sarah Jayne

sissy sarah jayne: The good sissy:  A good sissy must be able to keep a cleaner house than any ordinary housewife....... ....and must know how to keep their Master b...

Friday, July 20, 2012


“That’s a good girl,” my wife’s boyfriend said as he forcibly held me against the wall.  “Your wife won’t be home for another few hours.  Until then, just be a nice, sweet, agreeable little sissy, like you always are, and I promise not to hurt you.  Now, first thing, I want you to give me one of those good blowjobs you give every time I fuck your wifey.  Then, well, then we’ll see if I want to give you a little something extra.  Sound good?  Now go on.  On your knees.”

Patience Is A Virtue

My wife called from work.  She’s horny.  That’s all she has to say to me now.  And I know.  Know what she expects.  I’ve been in this position for over two hours.  Waiting.  Waiting to hear the garage door open.  Waiting to hear her car pull in.  Waiting to hear the kitchen door open, and then close.  Waiting for her heels to march up the stairs to our room.  Waiting to hear her remove her clothes.  Waiting to hear her strap on her nine inch cock.  Waiting to hear her say, “Hello pet.  I see you’re ready for me.”  And then, waiting to feel the cold, fat, bulbous head of her cock touch my sissy pussy.  And I’ll keep waiting for as long as she makes me.

Uniform Check

My wife had invited her girlfriends over for drinks tonight.  My job?  I'm her sissy, so, of course, I'll be serving them.  Just checking to make sure everything is just so before I begin greeting and serving them.


Yep!  My wife knew what she was doing.  My body no longer remotely resembled a man’s, other than my tiny, yet useless, appendage tucked firmly out of view.


My wife's boyfriend didn't believe it when she told him the pretty girl serving them drinks was her husband.  Now, she's making me prove to her date that I really am her sissy hubby.  He believes her now.  He just can't believe it!


The perfect frame for a perfect little sissy clit.

Thursday, July 19, 2012

And Now For Something Completely Different

It’s a little squirrelly, I know, but I think the little fella is nuts over this chick.  Soon, she'll have him wearing a French maid's dress and cleaning out her nest.

Key To A Successful Marriage?

Different Fathers?

“Oh God sissy!” my wife cried out to me in the corner of the room as she fucked my brother.  “How could your mother have two sons, one such a pathetic sissy, and the other such a man?  Your brother’s cock is fucking huge!   Maybe your mother cheated on your father,” she added the final stinger.

Sex From A Sissy's Perspective

The sissy’s vantage point to sex.  Watching.  Watching his wife fuck a man.  Waiting.   Waiting for the man to fill his wife’s pussy with sperm.  A man’s sperm.   Ready.  Ready to clean every drop of that sperm.  From the man.  From the sissy’s wife.  Fucking.  Cosmic orgasm.  Or orgasm denied.  It's all a matter of perspective.

The Internal Conflict

The internal sissy conflict never changes when I see my wife with a man.  It hurts.  And it turns me on.

Real Breasts

“See what I’ve been talking about sissy?” my wife said as she cupped my new breasts. “Don’t they feel good?”

Wednesday, July 18, 2012

Silly Sissy

“Of course I plan to bring a man home tonight sissy!” my wife explained to me, her voice laced with exasperation.  “Why else would I have had you dress me like this?”
I know.  It was stupid for me to think it may have been for my benefit.

The Pleasure Is Mine

It’s weird.  But more and more, as much as it pleases me to know that my wife is being well attended to by the men she brings home to fuck her, it please me even more that I get first crack at them, so to speak.  I’m the one who gets the initial taste of these splendid cocks.  Lucky sissy!

The Proof

My wife wanted proof, she'd said.  It wasn't enough that I did her laundry.  Or that I fixed her meals.  Or that I willingly helped her dress sexually and sensuously for her many dates with men.  She needed proof that I would do anything for her.  Any! Thing!  And that is how I ended up here.
With her brother.  And my brother.

The Tease

“Yes dear,” I whispered to my wife on the phone. “Dinner is ready. And so am I. So hurry home, and you can decide if you want me for dessert.  Or the main course.”