A Treat

Kaaren loved my breasts.

And I would be lying if I told you I didn’t enjoy this.

But Kaaren would never stop if I didn’t make him.

After this I would want a man who could make me squirm on his big cock and Kaaren just didn’t measure up.

So it required planning to make sure that both of us had what we craved.

Mrs K

Quiet Sissy

One of Kaaren’s favorite fantasies.

How he longed to have the pretty school girls humiliate him like this.

How lucky for me that I got to be the one to make it happen.

Mrs K

Last Test

Not so shocking nowadays but Kaaren would have loved it.

He would have been humiliated by showing up dressed as a girl and even more so by having to suck off one of his teachers!

And he would have loved it!!!

Mrs K

Watching

Not every man was comfortable with my sissy husband around.

Almost like they thought that being a sissy was contagious.

But once they got past the initial discomfort it wasn’t such a problem.

Mrs K

So Busy

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The Woman of my Dreams

Kaaren was a voracious reader.

His interests were wide ranging and quirky.

He loved history, particularly early American history, the colonial era.

He loved to read about science and to try to understand concepts that he found difficult.

He loved science fiction too, that was his favorite I think.

A bookstore owner he’d met when he was young had recommended books to him and had been a huge influence on a lonely boy looking for escape.

He told me that it broke his heart when the store closed down.

We both enjoyed books and when his face wasn’t buried between my legs he would be nose deep in a good book.

It amazes me that he found the time for everything but somehow he did.

Mrs K

Forward

I’m sure this was the way Kaaren wanted some of his college dates to go.

Maybe, maybe not.

I’m pretty sure my dildo wasn’t the first one inside him but, just judging by the way he carried on it might have been.

Either way this would have been a pretty typical night in our house.

He made such cute noises when I fucked him.

Mrs K

Rules

Yes Kaaren did have playtime with another sissy on more than one occasion.

We both enjoyed it very much.

But the other couple moved away and I couldn’t find a replacement like them.

Two men together. Dressed in lovely frills. It was my fantasy come to life!

With the two women in charge.

Bliss.

Kathy and Stephanie/Steve flew back for Kaaren’s funeral and it was wonderful to see them again.

If only it had been under better circumstances.

But I have my memories.

The look on Kaaren’s face when we made them make out and caress each other was priceless.

Judging by what Kaaren wrote here it was pretty memorable to him too!

Mrs K

Remember Me Coach?

I honestly can’t fault Kaaren for having a fantasy like this after hearing all about the abuse that he endured in high school gym class.

My poor little sissy spent so many years being so unhappy .

I like to think that he was so happy living with me that he had put all this behind him but just the fact that he wrote this tells me otherwise.

Mrs K

Recovery

 I was asked about my recovery from the auto accident I was involved in and I thought some of you might want an update.

All in all I had fifteen surgeries on my leg including a cosmetic procedure that dealt with a lot of the scarring.

I’m full of titanium rods and plates along with plenty of screws holding it all together. If you were to kick me in the leg it would probably hurt you more than me.

I’m still walking with a limp but it’s not as pronounced as it was and I’m still continuing with physical therapy.

I have mostly retired from my job but my boss has retained me as a consultant. 

Spending more time at home is a mixed blessing. I don’t miss the commute to work but it can get lonely sometimes.

I still have almost all of Kaaren’s things. I’ve tried several times to box them up and move them into the garage but in a day or so I put it all back while having a good cry.

I’ve been seeing a man that I met at physical therapy. He was injured in a motorcycle accident and lost three toes. He laughed about it when he told me about the accident. He pointed out that he went off the road at high speed and is still amazed that he’s alive., 

It’s the laughter that got to me. And he made me laugh with him. I haven’t done much laughing since Kaaren’s been gone.

He said he wished he could take me out dancing but he lost his twinkle toes in the accident.

It’s not too serious between us but I have to admit he is very good in bed. If anything, it’s me that’s been holding back. Not because I don’t want him, I do, very much so. Truth be told I think it’s because he’s not Kaaren.

I know it’s not fair to him but I can’t help it. Luckily he’s been pretty understanding and patient with me.

In case anyone is interested my friend and former assistant Stacy has moved into an executive position and she’s getting married! I couldn’t be happier for her.. I wonder if she’s still using her strap-on? I haven’t asked and she hasn’t told me. Her fiancé is a soft spoken and sweet man. I can picture him bent over for her but my mind is always in the gutter!

I thought about selling the house. I was showing the realtor around and she asked me about Kaaren’s room.

It was so pretty and girly that when I told her that it had been Kaaren’s bedroom she just assumed that she was my daughter.

She mentioned that a lot of parents downsized after the kids moved out and I started to cry.

I haven’t followed through with listing the house.

Don’t know if I can.

Anyway, physically I’m getting better. Mentally the pain of loss is still there and probably always will be. But it’s becoming easier to bear as time goes by.

I have a date tonight and he’s going to come home with me. I’m going to rock his world.

That’s all for now. I still have hundreds of posts to go through. Kaaren was quite prolific. Hopefully I’ll get to post them all.

Be well.

Mrs K

A Few Hours

I had a hard time getting used to wearing heels.

Kaaren however was a natural at it.

Where I nearly broke my ankle Kaaren was practically dancing around the house.

He would surprise me with his talents all the time.

He could dance, play the piano, and he had a wonderful and twisted sense of humor.

And I won’t even mention how well he sucked a cock!

Or how many times he could make me come.

He was amazing.

Mrs K

Oktoberfest

Kaaren loved the Oktoberfest and he particularly loved the dirndl dresses.

How sad that he didn’t have the cleavage to wear one.

I should have taken him to Germany to celebrate it. But I always thought that there was going to be more time and I was always so busy working.

Let that be a lesson. Never put off till tomorrow because tomorrow may never come.

Mrs K

Oh No!!!!!

Time passes and the things you thought you couldn’t bear change.

Kaaren was wearing pretty yellow panties the day I met him.

And he wore a pretty yellow bra too.

And he was crying because it was so humiliating.

But I loved it.

The things that embarrassed him then compared to later just seem just so tame.

Yes there were times when I wanted him looking his prettiest when I came home, sometimes because i was bringing company and sometimes just because I enjoyed it.

I really understand what Kaaren was writing about here and it’s so funny and at the same time it’s so real.

Mrs K

TV Guide - Star trek - The Lost Episode

Oh my!

Kaaren never had one that big.

He had a great sense of humor.

Pretty, submissive and funny!

He was the whole package.

Mrs K

Always Working

This was the truth.

I remember when Kaaren would be sitting at her little desk working away on her blogs for hours.

I once had him in a little pink dress with white knee socks and Mary janes with his hair in pigtails while he worked.

He was just so cute!

I remember making him blush by whispering all types of things in his ear.

Making sure he knew that I would need all his attention when he was done.

His desk sits now just as he left it, I can’t seem to be able to get rid of it even though it makes me so sad.

But sometimes I can almost see him there. That mischievous little smile. My special girl.

“Just a few minutes more sweetheart and I’m all yours” he’d say.

I would give anything to have just a few minutes more.

Mrs K

My Feet Are Killing Me

Kaaren was complicated.

Most of the things we enjoyed started out innocently enough but then Kaaren was very rarely innocent.

The foot thing was something that just seemed to happen.

He would occasionally offer me a foot rub and he was very good at it.

I grew to love it as well.

Slowly it became more intimate. Almost without realizing it, it had changed from a simple foot rub into a full foot worship session.

I never asked or demanded that he drop to his knees and rub and kiss my feet. I never asked him to lick my soles and heels.

I never asked him to suck my toes like they were little cocks.

It was a little ticklish but I found out that I really liked it.

And so…I never asked him to stop.

Mrs K

Covid Pounds

 I don’t think this was very nice of Kaaren.

I knew that I had gained a little weight from being locked down during the pandemic.

But I did lose it again when I realized that some of my clothes were getting too tight on me.

I guess it says something that Kaaren never said anything like this to my face and didn’t post this one.

But you could never really tell if he was just trying to provoke a spanking.

He loved getting his bottom warmed up over my knees.

And I always loved to see Kaaren do the swallowing. 

Mrs K

Too Late

Kaaren was complicated.

His deepest fear was that he would be exposed as the sweet sissy that he was.

At the same time, his biggest turn-on was being exposed as the sweet sissy that he was.

I was always careful about exposing my “special girl” to people. 

There were rules. Laughter was okay but real ridicule was not.

Most of the women were amused and curious and could be a little playful.

Most of the men were a little uncomfortable and embarrassed, as if just being close to a sissy would somehow rub off on them. No pun intended.

He always said that he was far more humiliated in front of a man than he was with a woman.

Perhaps there was a tiny bit of masculinity somewhere in him that rebelled against being exposed to a man.

But embarrassed or not he was pretty enthusiastic when it came time to get down on his knees.

When he would pull the cock out of a man’s pants any embarrassment would just fall away.

He enjoyed men but he adored women.

He loved to serve women and he got pleasure from doing as he was told. It made him feel loved.

Like I said, Kaaren was complicated.

Mrs K

So Much To Love

My Kaaren really loved to suck a nice cock.

It was one thing that he and I shared.

I was just a teenager when I first gave a boy a blow job and I thoroughly enjoyed it. So did the boy as I recall.

Kaaren had been writing his life story on his blog but sadly he never finished.

Maybe I can fill in at least some blanks.

Kaaren and I had broken up a couple of years before we went to college. We ended up at the same school.

I had won several scholarships and my parents college fund paid for a small off campus apartment while Kaaren lived in the dorm.

His mother had a bank account that she had hidden from her husband and used it to pay for Kaaren’s education.

Kaaren’s father was a mean drunk who had disowned him. He had actually wished Kaaren dead on multiple occasions.

The way Kaaren explained it to me was as horrible as you can imagine.

His mother died suddenly and his father didn’t tell him.

The way he found out was when his checks started bouncing.

His father had discovered the account and emptied it leaving Kaaren with nothing.

No tuition, no place to live and no home to return to.

When I found him he was living on the street begging for spare change and obviously doing drugs of some kind.

I convinced him to come home with me and together we got him straightened out.

But I’m getting ahead of myself here.

That first night I got him out of his filthy clothes and washed up.

In my opinion his clothing was in such a condition that they were for the trash.

I figured i could get him something to wear at the local Goodwill store the next day and so with no alternatives I gave him a set of my pajamas to wear.

Seeing him in my pink bunny pjs reminded me of how cute he always looked in my things before we split up.

Anyway, time passed. He was living on my couch for a while and we were getting along well after he stopped with the drugs. I helped him through that and we got closer to being the good friends we had been once.

I had bought him some clothes and he was grateful. However I didn’t buy him anything to sleep in.

I told him that i had plenty of things he could borrow and no one would see him but me so there was no need to be embarrassed.

I knew he was enjoying wearing my clothes and I was enjoying seeing him in them.

At the time I was dating a guy from the school football team. Not one of the star players mind you, but I got a little social status just from dating a player even if he mostly sat on the bench.

We used to come to my place to have some private time together because he lived in a fraternity house with a bunch of jocks, not my cup of tea.

Now I had to explain who this person staying with me was without upsetting things.

I told Vince, my boyfriend’s name was Vince, that Kaaren was my younger cousin and that he was a girl.

I figured that if I did a little work on Kaaren that he could pass without a problem as long as I kept them as far apart as I could.

Vince had the IQ of a fence post and was only interested in my skills in bed so he readily accepted whatever I told him.

I knew that Kaaren was listening to us having sex so i wondered if he would peek if I left the door open just a little bit and sure enough after the first night i spotted him.

Vince wasn’t a good lover but he was okay. He was bigger than most of the other guys I had screwed over the years. Many times after he’d cum I’d have to finish myself off while he snored next to me.

After letting Kaaren watch a few times I snuck out of bed and sat with him.

He wouldn’t admit to peeking at first but I told him I didn’t mind, and I really didn’t. It surprised me that I enjoyed knowing that he was watching.

Then I cuddled with him and we talked about our past. I told him that I missed the way he made me come.

I told him how much I loved the way he used his tongue. It was dark in the room but I could tell he was blushing.

Then I kissed him.

Not a friend kiss. I was so turned on and Vince had left me unsatisfied again and I was filled with lust and need.

And I slowly pushed him down till he was between my legs and he didn’t hesitate at all.

Vince didn’t use a condom and I was full of his cum, Kaaren had watched and knew what I was asking him to do.

Without any hesitation at all he began to lick me. Just knowing that he was tasting my boyfriend’s juices excited me so much that I had a fantastic orgasm in no time at all. But Kaaren didn’t stop until I’d had another and i had to push him away.

And as I caught my breath he gave me his cute mischievous smile and thanked me for letting him please me!

That was the night that I knew that I wanted him back. I wanted him to be mine forever!

I know what you’re probably thinking and you’re correct. It wasn’t long before I convinced him to go to the source and suck Vince’s cock.

So one night, after a few drinks, I let my little virginal cousin Kaaren get down on her knees and suck my boyfriend’s hard cock.

I knelt next to him and held his hand while he bobbed his head and took a surprising amount of cock into his mouth.

I had dressed him in a pretty little nightie and the sight of him like that almost made me come.

When Vince filled his mouth with his cum I nearly fainted and Kaaren nearly broke my hand,squeezing it so hard as he worked to swallow the huge load.

As we had arranged Kaaren headed for the bathroom while I hustled Vince out the door.

Later I discovered that Kaaren had cum in his panties while Vince had cum in his mouth.

Then he used his mouth to make me feel so good, over and over and over!

And he never asked me to do anything for him in return. But I just had to do it and I gave him a blowjob and it was sweet and he came so quickly and he was so grateful!

And this beautiful sissy and I fell asleep. And we fell in love.

Even Though

Yes my Kaaren loved pretty lingerie.

I tried to get it, but sometimes it was just underwear, not meant to be sexy. Didn’t make a difference to my Sweetheart.

I went out with a nice man last night. My first date since Kaaren passed away.

I dithered over what to wear, even underneath. Normally if I wore something special I intended for it to be seen. But I didn’t think that was going to happen.

It felt really strange to be with a man in a potentially romantic way.

I had lovers before and during my marriage, with Kaaren’s permission, but this time it felt oddly like I was cheating.

He was a very nice guy and we had a very pleasant evening and I may see him again.

He said he liked my smile, if he only knew that I was picturing him in pink frills.

I can’t help it. 

Mrs K

Standing By

I’ve got a date on Saturday night.

My first date since my Sweethearts passing.

I’m excited and nervous and I’m not sure I’m ready for it but he’s a very nice guy that I’ve known for quite a while.

I’ll miss having my sissy waiting for me when I get home.

Aside from his cleanup duties it was so nice to have a “girlfriend” to tell all about it while we cuddled in our bed after I came home.

Wish me luck!

Mrs K

Sunday Is Game Day

Kaaren and I both loved to watch football on Sundays.

Sometimes we’d have company and we’d miss considerable portions while our attentions were elsewhere.

Poor Kaaren missed so many games while he was on his knees in front of us.

But having orgasms while your team is winning is a lot of fun.

Kaaren was happy to provide me and any guests with an enthusiastic game day effort.

Mrs K

Do Sissies Ever Sleep?

Kaaren slept very little. Not because I made him rise early but because it was just natural for him.

He was up before me every day and many times was still up when I retired.

I miss having my coffee served to me first thing in the morning.

I also miss having him make me come while I having my breakfast.

But I guess our friend Dee must have inquired about his schedule and he wrote this answer.

I have no idea why he didn’t post it himself.

Mrs K

OK

Over the years there were several instances where I had Kaaren remove posts that I felt could lead to his being identified.

That was a hard and fast rule.

I am successful in the corporate world and I tried my hardest to avoid scandal.

My husband as a sissy cuckold would have been a scandal.

When i saw this post I was going to delete it because I actually thought that this was a pic of Kaaren.

The resemblance is uncanny. This could be him. It took me a couple of looks to make sure. 

Maybe some day, after I retire, I’ll post an actual pic of Kaaren but for now this is as close as it gets.

Mrs K