Ten Orgasms

"That's it Sissy....make me cum on that tongue....make me cum ten times and I'll take that cage of and suck your tiny cock....I'll swallow all your sissy cream...."

She said this all the time but after two or three orgasms she always made me stop....I asked her about it once....and after she spanked me for impertinence....she told me that she would certainly pass out before I got her off ten times!!!!

Now I just think of it as encouragement instead of potential reward!!!!

 

 

Sunday Brunch

"I don't know Sissy....I just felt that you could have done better...."

"I tried my best Ma'am!!!!"

"What do you think ladies?"

They all shouted out for a spanking....I'm not sure it was really a fair trial!!!!

Saturday Afternoon

 It's Saturday.....no chores....no cooking....we order in....nothing for me to do.....just me time!!!!

A nice hot bath with all my favorite scents added....and taking my time to shave the very sparse hair on my legs.....

A little music.....and I could stay there for hours!!!

Unplanned

She hadn't planned on it tonight....

She wasn't wearing any of her sexy stuff....

Just her regular panties and bra....

But when she came into the bedroom and found him there naked on the bed...

Looking so docile and vulnerable.....

She knew....

She knew she had to fuck him.....

She knew he needed it....

She knew she needed it....

Sissy School - Hard

It's hard to keep up with all your lessons in Sissy School....there are so many distractions!!!!

The Correct Angle

Sometimes it's just a matter of getting the correct angle...

Just imagine....I thought learning geometry was a waste of time....live and learn I guess!!!

No Please

 "I'm going to make you cum Sissy!!!!"

"No please....I'm not allowed to cum...."

"It'll be our little secret...."

"No it won't....she'll know!!!"

"I won't tell her so how could she know?"

"I don't know how she'll know but she will and I'll be punished....please stop!!!"

"Too late Sissy.....can you feel it?"

"Oh god.....Nooooooo!!!"

 

 

Hump Day

The important thing to remember on Hump Day is to be as receptive to new things!!!

Relax

"Relax Sweetie....your wife asked for the complete sissy makeover but she didn't want us to remove this...."

Which

"Which one do you want to watch me use in place of your little clit Sissy?"

"I guess you'd like the smaller one...."

"Okay Sissy.....I'm going to cum on the smaller cock.....so I want to watch you cum on the big one!!!!"

All Day

All day she told me how she wanted me in her mouth....how she needed something hard to run her tongue over....how she looked forward to my balls against her chin as she swallowed me....

The fact that I knew what was coming still didn't change the disappointment I felt when she finally did take me in her mouth....

It's been a long time since she fooled me like that....

SheLikes To Read

Much like me, she loves books!!!

And sometimes she can't tear herself away in the middle....

So I wait....the lube is a little cold....but I stay where I was told....face down, ass up...because I don't know if she's going to put the book down after the chapter or after she finishes the book....

And honestly....her cock is worth waiting for!!!!!

 

 

Monday ManCandy

You're running a little late today and even worse....you're running on empty!!!!

You're never going to make it unless you stop and fill up as soon as you can!!!

Thank goodness you know just where to go!!!!

ManCandy!!! Free lip gloss with every fill-up....available 24/7!!!

Sissy School - A Weekend Visit Home

No matter how long you've been away, it's nice to be back home and enjoy the things that you're most used to!!!

Maid Duties

Since I became her sissy maid I have taken over many of the chores around the house....I do all the cooking and cleaning.....I take care of the laundry.....I take care of her social calendar...I take care of the yard in the spring, summer and fall and I shovel the driveway in the winter!!!

But the best part of my duties is when she has a friend over and I get to make sure he's ready for her....it makes it all worthwhile!!!!

 

 

Cuckold

He may be in her mouth but I can tell from her eyes that I'm on her mind!!!

Suspect

He always insisted that I be naked....no frills or satins or lace....

He always insisted that she release me from the cage....

And every time he fucked me he gave me the reach around....

As he buried his cock inside me I was beginning to suspect that he might be gay!!!

I wonder if my wife knows....

 

 

Key

The key to a sissy passing in public is to dress in a way that doesn't call attention to yourself...

Of course my wife has other ideas....

Not Much

Sure....you'll get no argument from me....I'm not much of a man.....men don't go out into the alley to blow a guy under any circumstances!!!!

But even though I'm the one bent over with his cock in my mouth....I'm also pretending that I didn't notice the lacy panties he was wearing.....and it wasn't my little red umbrella....

 

 

Sex All The Time

No one can have sex all the time....it's just not possible.....you have to have something else that's important to you in your life....for me it's always been books.....I love books....I tried to use a Kindle but I hated it.....I love the feel and smell of a good book...

If I had a chance to just roam about a library or bookshop I'd probably forget all about time and lose myself in the worlds they show me....

The world of the past...I love the Colonial/Revolutionary Era of the early USofA....

The world of the present....I mourn for the state of the world as it is now...

The world of the future....all the possibilities!!!! The great sci-fi authors got so many things wrong but they got some things so right that it's scary!!!!

And I could easily get lost in any of those worlds....until I hear my wife's sweet voice call me....and then all my thoughts turn to sex again....

Not A Big Deal

I mean....it's just us....just the two of us....and Stacy....I just didn't think it was a big deal that I had worn to mismatched socks....

Apparently it was a bigger deal than I thought....and I will definitely remember to never do it again!!!!

Peeking

I peeked in on her in her home office the other day....risking a spanking, but it was worth it....and she was enjoying herself watching lesbian porn and taking care of her own business....how I wished I could step in and offer her my tongue....but I realized that if she wanted me all she had to do was call....this was what she needed right now...and I reluctantly closed the door and never mentioned it....but I've been replaying it in my mind ever since...

 

 

 

 

 

 

 

 

Hump Day

There's really no better way to get through Hump Day than with the help of your dear friends...

Not Often

 It doesn't happen all that often but sometimes you get a pinch and need to rearrange things in your cage....oh well....no one said being a sissy maid was going to be easy...

Be Quiet Sissy

"Shhh....be quiet Sissy....you don't want your family coming in here and seeing you getting fucked like the little bitch you are....or maybe you do.....wouldn't they be surprised!!!"

Heels

 She found a delightful way to teach me to walk in heels.....

"Just put one foot in front of the other....like walking on a tightrope....and move your whole body....shake that ass!!!!

And it worked!!!!!

 

 

Monday ManCandy

 In the midst of the global pandemic...and the associated lockdowns....tempers can run a little short.....

"You greedy Sissy bitch.....you didn't leave any for me!!!"

But there's always more.....the white creamy treat is available although it might take a few minutes more....

And after all you trained Sissy to enjoy it .....and she's so damned cute....

ManCandy!!!! First come first served!!! But seconds are okay too!!!

Maid Service

The proper Sissy Maid is always ready, willing and able to serve....

Sunday Brunch

 I really wasn't sure what to prepare for the ladies Brunch today so I asked the Butcher what he recommended....and he delivered!!!!

Something New

Every time she tells me that she wants to try something new....I'm excited....and terrified!!!

But I'm always willing!!!!

Okay Honey

"Okay Honey.....breathe out and relax....you're going to love this!!!"

She was so right!!!!

Cuckold

I soon got used to sucking her lovers cocks....in fact I came to enjoy it very much....

Taking him in hand and putting him inside her....that took a little longer....and I still....at times...wish it was me inside her instead of him!!!!

That Extra Effort

Her boyfriend got her most of the way there....now it was up to you to take her all the way!!!

Do your best like any sissy cuckold should!!!

Workout

With the gyms all closed she, and her sister, had to find another way to workout....

After some thought they realized that this worked out their thighs, glutes and abs....

She worked her way up to doing three sets of 500 and was very proud of herself....but her sister blew that mark away....her third set had been going for almost an hour and showed no sign of slowing down!!!

Lets See

"Alright Sissy....now lets see how the vibrating plug responds to remote control...."

There was a lot said after this....but none of it was very coherent!!!!

Hump Day

Usually by Hump Day you have most of your weekly chores done.....but not this week....it's amazing how one house guest can disrupt a schedule!!!!

Remember

"You've become a very good cocksucker Sissy....but you have to remember the balls....I'll help you this time....but next time you have to remember the balls all by yourself!!!"

Draw The Line

This is where I draw the line.....how much humiliation does she think I can take.....my little clit strains in the cage under my pink ruffles panties....yes it's hot, but sometimes things are just too much....she knows what I like and what I don't....and I don't mind him burying that big cock inside her....she enjoys it....I don't mind if she sucks that big cock....I don't even mind if he flips her over and enjoys her ass....but I draw the line at kissing....she says she can't help it....and she always apologizes for upsetting me....but she still does it all the time!!! 

Later....when we're cuddling together....and she's telling me how it felt....she'd kiss me and I'd swear I could taste him on her lips....and I would tell her how much it upset me....and she would apologize....and we would cuddle and kiss some more....and it would be forgotten until the next time....

 

 

Cute

"I don't care how cute you look in your sisters clothes....I warned you what would happen if I caught you again!!!"

"I know Grandma!!!"

"In fact I'm going to call some of my friends to show them how adorable you look....what \do you think of that.....they'll all see you for the Sissy you are...."

"Ohhhhh Grandma!!!!"

"Oh my goodness....did you just....on my clean sheets!!!!"

"I'm sorry Grandma!!!!!"

"Are you really sorry?"

"No....not really...."

Prettiest

"By the time I'm done with you you'll be the prettiest girl there!!!"

"But I'm not really a girl...."

"And what difference does that make?"

Monday ManCandy

She knows what you need to get out there into the cold February air.... it wasn't available on hand this morning so she ran next door....through the cold....to get some so you could have a warm tasty breakfast....

ManCandy!!! She knows how to keep your breakfast warm until it's ready to be served!!!!

 

 

Sissy School - A Weekend Visit Home - CANCELLED

Sissy wanted to go home this weekend but there was an interesting seminar being offered and she didn't want to miss it....

"So you see sissies....you can't suck it and he can't stroke it....he can't bend any of you over and fuck you....but he can still cum....and this weekend we're going to explore just how many ways you can make him squirt..."

 

 

 

 

 

 

 

 

 

 

 

 

Test

After they discovered his sissy secret the girls spent the whole afternoon getting him ready...

Now they would see if he would pass the test!!! 

Talked It Over

 "We talked it over Mr. Tomlin....we all saw you peeking up our skirts....and we all noticed there really wasn't much of a bulge in your pants even when you were hard...."

"So we got together and decided that since you liked peeking at our panties so much that we would let you wear them...."

That's right Mr. Tomlin.....every day one of us will give you a pair of our dirty panties  to wear.....you will wear them all day....we will be checking....and then you will hand wash them and try to guess which one of us they belong to....if you guess wrong you'll be punished..."

"So do you have anything to say?" 

"I don't know....how many ways can I say yes!!!!"

See How Easy

"See how easy it is Baby....all you have to do is put on some pretty clothes and open your mouth....and all the boys will come....."

She really was the best step-mother a sissy boy could have!!!!

 

 

Concentration

Sure....it's easy for you Sissy....all you have to do is bend over....she has to figure out the angle that will please her the most....while considering whether or not she wants you to squirt your sissy cream....

So while you're moaning like a little bitch....she's busy considering the entire situation....

Just like always!!!!

Laughed

I could still hear them as I was catching my breath....

"So....did you enjoy fucking my sissy?"

"Yeah it was fun....he was tight...."

"Better than me?"

"Oh no Honey....no one's better than you...."

"I hope you saved some for me...."

"You just wait and see!!!!"

And they laughed as I felt his cream trickle out of me.....and I felt good!!!

A Moment

 "You look just beautiful Sweetheart!!!!"

"So do you Sissy...."

We love each other and all the rest just makes it so much better!!!

 

 

Hot

She was so hot ....the hottest girl at the club.....and when she invited him to her home for a night of crazy sex....he jumped at the chance!!!!

But this was the craziest thing ever!!!!

When she pulled out the strap-on....he just wasn't sure if he could do this...

But here he was.....watching her using her big cock on her husband while he stood there transfixed....

And when she looked at him and said....

"It's your turn next...."

He wasn't at all sure what she meant.....and somehow....he couldn't wait to find out!!!!

A Glimpse

 Nothing can change a sissy husbands mind faster than a glimpse of the key....after a few months there's almost nothing you won't do.....