Friday, July 31, 2020

What Would You Like

"So Sissy.....what would you like for your birthday this year?"
"I'd like to suck a really big cock and get a huge load shot into my mouth while you watched me.... "
"Well with the way things are I can only promise that I'll get you that sometime later.....what would you like right now?"
"What would I like.....I'd like for you to decide what I need....just like always....."
"I can do that for you Sissy....."















Birthday

"Do you like my new dress Sissy?"
"Oh yes....very much!!!"
"I'm going to spank you and paddle you and maybe use the cane for a few strokes.....then I'm going to sit on your face until I come .....then I'm going to get my biggest strap-on and I'm going to fuck you....hard...until you spurt your sissy cream....then I'm going to get down and watch you lick it all up....every drop....and do you know why I'm going to do this Sissy?"
"I'm not sure.....maybe because it's my birthday?"
"That's right Baby.....Happy Birthday Sissy....."











Thursday, July 30, 2020

Cuckold

"C'mon....quick....get them off....he'll be here soon and I want you in a pretty dress when your brother gets here......I can't understand how he got such a nice cock and you.....well you didn't....."












Caged

It's not just to keep me from touching it.....it's also to avoid my clitty touching the pretty panties.....
The cage has stopped all of that.....thank goodness....it was so embarrassing to have to tell her that I'd made a mess in my panties again!!!!











Wednesday, July 29, 2020

Her Work

Most of the time she sends me away while she's working....I'm to much of a distraction she says.....but every now and then she spreads her legs and welcome me....
Those are the best times!!!!











Hump Day

Sometimes you're just so busy that you don't even notice that it's already Hump Day!!!
It's so delightful when it's a surprise!!!!













Tuesday, July 28, 2020

Sissy Traiming - Slowing Down

"Why are you slowing down Sissy....when I told you to worship my ass I meant it...you will worship my ass until I tell you to stop.....I really don't care how long it's been.....just keep those lips and tongue busy....."














Pool Maintenance

The hardest thing about having a pool is keeping up with the maintenance!!!!
But I always do my best to motivate the pool guys to do a good job.....













Monday, July 27, 2020

Pause

I pause as I clean the mirror and I remember when a young boy would look in a mirror just like this and see the girl he so wanted to be....
Now I pause and worry about a smudge in my makeup or a stain on my dress....
Times have changed....















Monday ManCandy

At first glance it seems you're unsure if you want to swallow the creamy treat that's filled your mouth!!!!
But nothing could be further from the truth.....just because you didn't swallow it quickly is easily explained.....
You want to keep it in your mouth for as long as possible....the flavor washing over you....it's so good.....but as hard as you try some will slip into your tummy and soon you'll swallow the rest.....
ManCandy!!!! The mouthful that satisfies in more ways than one!!!!














Sunday, July 26, 2020

Not Much Protection

She decided that it was time for a spanking....
I usually have no problems with that....in fact I'm usually pretty eager....
But then she offered her boyfriend the option of spanking me......I wasn't at all happy about being put over a man's knees....but if it was what she wanted then what could I do....
She told him that he could spank me as hard as he wanted but he couldn't take my panties down.....there would be no bare ass spanking!!!!
It's an interesting thing that some people make a distinction with a panties on/panties off spanking....
As someone who has received both, I can honestly tell you that there's very little difference between the two....
As far as being spanked by him.....maybe he was nervous....but she has spanked me far harder and far longer.....but I did enjoy feeling his big cock poking at my tummy!!!!













Sissy School - A Weekend Vist Home - CANCELLED

No....the school didn't shut down again....this time I cancelled my weekend at home!!!
One of my best friends at school had just come bag and she had gotten the treatment and we both wanted to take some time getting to know how it all felt!!!!











Saturday, July 25, 2020

Normally

Normally I would have never kissed my neighbor Steve like this.....but I didn't know his secret and he didn't know mine.....until our wives decided to introduce Stephanie to Kaaren....
And I closed my eyes and our lips met and it was pure sissy bliss!!!!















Cleanup

No one is rushing in to help me clean up after he showed me why he's the man and I'm not.....
The rule of the house is that any cum spilled here must be swallowed by me....and so my wife and her bull were greatly amused by my using a hand mirror to allow me to see where it was so I could scoop it up and swallow it down.....
I was halfway through when I heard them start to fuck behind me.....I had to hurry....there would be another load soon!!!!














Friday, July 24, 2020

My Analyst Expands Her Practice

"Just try to relax.....I do this with all my new patients....."
"But Dr. Mentia I've never.....I mean really never...."
"Listen ....I've been doing this for years and I have had extensive experience with sissy men....."
"What do you mean by....extensive experience?"
"Alright....I shouldn't tell you this but Sissy Kaaren is one of my patients!!!!"
"Really?"
"Absolutely....so just lie back and we'll see if we can stimulate some of those repressed memories....."














The Darker Years - My Sissy Story Continues Part 3 New School

 This part of my story contains the darkest moments of my life.....it has taken me years to be willing to tell it.....I'll understand if you don't want to read it....but it feels like I'm unloading a lot of personal baggage and it finally feels good to tell it all to someone....

You really must read   How It BeganNot Always Fun Nothing To See HereMy First PantiesA Couple of FirstsCaught My First Bra,   My First High School DanceKerri's House, Endings and Beginnings, The Darker Years - My Sissy Story Continues, The Darker Years Part 2 - My Sissy Story Continues  for this post to make sense. Obviously the dialogue is not verbatim but it's as close as I can remember it. The experiences were real as were the people involved. I began this blog intending to tell how I came to be the Sissy girl I am today and this is the the beginning of the next part of my story, I intend to continue to tell more of my experiences, both good and bad and I hope you, my sweet readers, will come along on the ride.


Summer ended all too soon and it was time to begin a new life in a new school where I knew no one....
I had spent the summer in a druggy haze for the most part while I dodged between my alcoholic father and my mother who had withdrawn so profoundly into her grief that she seemed almost like a ghost of the woman she once was.....
It's hard to be the new kid in school, particularly in a rural area where most of these kids have known each other since pre-school. That first day when I walked in I immediately knew that I was in trouble.....these kids had grown up together and had sorted themselves into their cliques years ago and new members need not apply!!!
It didn't help that I was small....I was way behind on the growth curve and in some ways I never caught up!!!
Several of the guys immediately zeroed in on me.....I was smaller than them and I had long hair and that was enough for them!!!!!
I was pushed and bumped and I knew I was in for worse as I heard their laughter!!!!
The first day......in gym class.....I was knocked to the floor.....almost unconscious.....an elbow under the board......I was sent to the nurse....who put a cold pack on my swollen eye......
I remember her so well.....she was one of the best people I have ever known...
"Sweetheart, you got to watch out for yourself here!"
She really cared about me......
It was almost as if she knew I was already a target!!!
There were a couple of them that had immediately zoomed in on me as the vulnerable newcomer....and they were right!!!! Most of them were a head taller than me and they had at least 50 to 75 pounds more than me!!!!
The only thing that kept me from the ultimate high school humiliation that first day in gym was getting carried to the nurse instead of the showers!!!
Look....even then I knew I was small.....really small and as each year passed I started to get used to the idea that I was small and I was probably always going to be.....in my old school this hadn't been an issue.....but they knew me there....I wasn't a target there!!!!
When I got home I popped a couple of pills and for the first time in my life I considered suicide....it would be so easy.....a couple more pills....a touch of the razor at my wrists.....a short drop with a rope around my neck!!!! There were so many options and all of them were more attractive than my life as it was!!!!
But I let the haze come and I relaxed and felt nothing....
Within the first two weeks of school I had been to the nurse six times....the last time she had suspected broken bones and had called an ambulance!!!!
My parents picked me up at the hospital where it had turned out to only be a deep tissue bruise.....I was supposed to rest and stay away from physical activities for a couple of weeks.
My father sneered at me as we drove home....
"Just like a goddamned sissy faggot.....can't even compete in gym for Christ sakes....your brother would have knocked that kid on his ass...."
He went on but I didn't listen.....I didn't need to hear what a disappointment I was...I knew that already and besides I had already decided that that was going to be my last night on earth.....I had about 13 or 14 Quaalude's at home in my stash and I figured if I took them all tonight and washed them down with a couple of beers that I wouldn't wake up in this shitty world where there was no love and no hope and only nasty brutal people who would only hurt me.....I couldn't think of any reason to keep going....

....Crying....I heard a woman crying.....then nothing......then lights so bright.....and people calling my name.....wake up they kept saying.....wake up....but I wanted to sleep....I wanted to sleep forever....I didn't want to wake up.....

It was two days....they pumped my stomach but the drugs had almost done their job by the time my Mom had found me in my room....I had locked the door but I guess that it wasn't as strong as I thought it was....my father kicked it open with one shot!!!

I remember waking up in an empty room....no one there....just me.....
When I sat up my head exploded in pain and down I went again....I curled up in a fetal ball and clutched at my head....
That's where the nurse found me eventually....she called the doctor as she checked my IV to make sure I hadn't dislodged it......
Two doctors came to see me.....they introduced themselves but through the fog and the pain I couldn't remember their names.....
They asked me a million questions and I gave maybe two answers.....
I needed to sleep....I needed this world to go away......I needed to die......I didn't understand why they were bothering me when all I wanted was to take my leave....

I was there for a couple of weeks and I had a couple of Shrinks talk to me and have "sessions" with me......they told me that killing myself wasn't the answer to my problems and I told them to fuck off because they didn't know my problems...
 After I left the hospital and returned home things hadn't really changed....I repaired my door and replaced the lock with something a lot stronger...neither one of them cared....as soon as I was home everything was the same again....they were both lost in grief for their son and I was just a distraction....

When I returned to school things were very different....apparently my suicide attempt had been the school gossip all the while I was absent. I tried to buckle down and just blend in but that just wasn't going to be an option for me...

It didn't take long for the bullying to begin again.....I spent a lot of time with the nurse....
Finally she'd had enough and I was called to a meeting in the principals office with the nurse and the gym teacher, to discuss my well being....
She was mad....."They're going to kill this boy if we keep him in there with those animals!"
Gym teacher Vivino just laughed...."They're growing boys....they get a little rough sometimes but that's just how they are...."
She wasn't letting go...."And how many of your other students wound up in the hospital....how many of your other students tried to...."
She trailed off but I knew the rest of the sentence....
They all looked at me....pity in her eyes, indifference in the principals eyes and daggers in the coaches eyes...
Finally the principal sighed....
"Well Mrs. Dugan, what do you suggest we do....he needs Phys. Ed. to graduate?"
"Isn't there some other way to satisfy the requirement....look at this boy....he needs our help!!!
The coach laughed....
"What he needs is to get in there with the guys...he needs to toughen up...he needs to be a man!!!!
I cringed inside....if being a man meant being like the guys who made my life hell....like being my father.....I wanted no part of it....but even though they were talking about me....about my life....I didn't speak up on my own.....I was afraid....confused....
Mrs. Dugan was not to be deterred and she slammed her fist down on the principals desk...
"This boy is in danger.....these hooligans have targeted him and he needs to be protected and obviously Coach Vivino isn't able to do it in his class.....I've checked the curriculum and he can satisfy the PE requirement by taking the dance class....I think that would be the best place for him!"
The coach snorted.....
"Dance class.....why don't you just put him in a dress for Christ's sake....why don't you sign him up to be a cheerleader!!!"
Mrs. Dugan, god bless her, got right in his face....
"Maybe you'd rather have those boys kill him!!!! is that what you want, you macho, shithead, son of a bitch!"
I had never heard teachers talk to each other like this but she was angry and she was fighting for my life....it was more than I was doing!
All three of them started yelling at each other then and it took a while for them to hear me when I asked to be transferred to Dance class....
The principal and the coach sat and stared at me like I was some kind of alien while Mrs. Dugan put the transfer papers on the desk....
"Are you sure this is what you want son?" the principal asked looking me in the eyes...
"Yes Sir!"
"Alright." he said as he signed the transfer form, "I hope this works out for you....Mrs. Dugan I expect you to keep an eye on this situation!"
"I certainly will!!!!"
"Coach Vivino I don't want to hear about any of your boys causing this young man any harm...."
""Harm....what more harm can you do to a boy than putting him in goddamned dance class....they'll turn him into a faggot for sure...."
That was then....you could say things like that then....
It wasn't long before I felt the hostility of the girls.....there was one other boy in the dance class and he was certainly gay......and we kind of clung together in a mutual defense against the nastiness we faced in class....
Madame wasn't happy to have two boys in her class as she was trying ti train beautiful ballerinas....
She tried humiliating me by making me act the female role in various dances....but that wasn't enough to make me want to go back to the physical abuse I had experienced....
One day after class the other boy tried to kiss me....it was awkward....I wasn't a homo as we used to say....I like to think that I let him down easy....
Some of the more motivated assholes in school made a point of looking for me....maybe it made them feel like real men when they beat up a guy who was so much smaller than them that I couldn't possibly resist....
This was when I made my second try at checking out.....not pills this time....this time it was the knife at the wrists.....thankfully the scars have faded  after all these years but they're still there....
Again through some type of serendipity I was saved.....
Again I spent a week or two in the psych ward.....
And when I came home it all started again....
The third time was in the garage with the car running and that one landed me in a mental hospital for some time.....I was a danger to myself they said....
I actually finished High School while I was in the hospital....and I was surprised by my acceptance into a good college with a partial scholarship!!!!
My mother told me that she had a bank account that would cover the rest of my tuition....she said it was all she could give me.....
Her heart had been broken by my brother's death and nothing was ever going to fix her....
My release date loomed and I was looking forward to getting away from all the shit my life had become....
Finally the Shrinks set me free.....and I came home for a few weeks of abuse until I could move out to live in the dorm at my university....
Tuition and room and board were all taken care of.....I had a roommate but we were OK with each other.....apparently most of the assholes I went to High School with didn't come here......don't get me wrong....there were plenty of assholes here but I wasn't on their radar....




























Thursday, July 23, 2020

Chores

"Are your chores all done Sissy?"
"Yes Ma'am...."
"And you know my rules?"
"Yes Ma'am...."
"Alright then....you can play video games as long as you play them the way I like..."
"I will Ma'am...."
"Alright then Sissy.....I'll be along later to check...."















Ceremony

It was the biggest Sissy event of the year!!!!
The Caging was eagerly anticipated by the women....and the sissies too!!!!
"Step up Alison....."
And a cage was fitted onto her and with the click of the lock she was secured for her Mistress....
"Step up Beatrice...."













Wednesday, July 22, 2020

Back To Work

"Well Thomas....a couple of months spent working from home and you show up now in a pretty dress.....let's see what else is new shall we?"












Hump Day

It seems like you've been carrying double the workload since the virus hit.....Hump Day reminds you that twice the work equals twice the rewards!!!!


















Tuesday, July 21, 2020

More Elegant

Most of the time she used a condom to catch my sissy cream when I was milked....but sometimes she decided to add a little elegance....she liked it and so did I.....and when I drank it I felt like a very proper sissy!!!!









I'm Ready

I'm ready for this.....I'm ready for the humiliation.....I'm ready to get down on my knees and suck his cock....I would do anything for her!!!!
He's never seen me like this....but then I've never seen him naked in my our her bedroom either....
Yes....I'm ready!!!!














Monday, July 20, 2020

So You See

"So you see Sissy.....a little makeup....a nice wig....and some lingerie and here you are....the girl of your dreams....the girl of my dreams too!!!!"
"Thank you Ma'am....."
"Come to bed with me and be my girl....."
"Yes Ma'am....I can't wait!!!!"













Monday ManCandy

You know she's behind you....waiting patiently until you get yours.....that's what love is all about!
She knew you were a voracious sissy when she married you and she was happy to see that even now, you were taking care of all your nutritional needs!!!!
ManCandy!!!! It's the glue that keeps you together!!!!












Sunday, July 19, 2020

Sunday Brunch

I pulled open the doors to announce that Brunch was ready.....but she had a mouthful already.....and it looked delicious.....so I went to keep everything as warm as I could....
In fact I was feeling a little warm myself....













Pretending

She watched as her sissy husband pretended he'd never done this before....he was such a good actor.....her lover enjoyed the idea that his cock was the first one in that greedy sissy mouth.....if he only knew....
She never got tired of watching this.....not ever!!!!











Agreed

"It's alright Daddy.....my new stepmom and I agreed that this is what's best for you.....now go put on your dress and resume your duties!!!!"














Saturday, July 18, 2020

Pool Party

When her little brother showed up at her pool party the girls all grabbed him....
"If you want to come to this party you have to wear a bikini!!!!!"
They were all laughing until they got his shorts off and saw that he was wearing panties....
"Well it looks like wearing a bikini won't be a problem for you will it?"
He blushed but didn't say anything as the girls stripped him.....his hard little cock told them all they needed to know!!!!












No Choice

He had no choice in it but her lover helped make sure that he did his job!!!!
He was going to do it anyway but this actually made it better!!!!













Friday, July 17, 2020

A Show

Yes I love it when my wife and her friends want me to put on a show with another sissy...
But the rule is that neither of us is allowed to cum!!!!!
And it's so hard....no pun intended.....
But really....I can't complain.....how often do I get to suck such a sweet smelling, pretty cock.....













Different

Her strap-on felt so different this time....maybe it was the blindfold driving his imagination....but it felt bigger and warm too.....he liked it very much and he let her know how much....
Then he realized how strong her thighs had gotten....he'd have to start working out with her.....but damn this time felt so different....and so much better....













Thursday, July 16, 2020

Tan Lines

Well.....these tan lines were going to be pretty hard to explain....



















One

"You know I'm not really a girl Baby?"
"I've only got one cock Honey.....as long as you've got one hole for me to put it in we're going to be OK...."















Wednesday, July 15, 2020

Hump Day

Sure....there are times when you think you've taken all you can handle....then Hump Day comes around and you realize that you can handle whatever life throws at you!!!!












Your Diary

"I read your diary Bro.....I read how much you wished you could wear my slutty clothes...I read how much I turned you on.....I read all about you trying to see me naked....you're such a little pervert aren't you?"
"Yes....please.....stop....I didn't mean...."
"Quiet bitch.....you wrote so many pages about having sex with me.....with me!!!! Your own sister!!!! So I decided to make your sick little perverted dream come true....so now I'm having sex with you.....is it all you dreamed of?"
It was....he knew it was wrong on so many levels but it was just sooooo good!!!!












Tuesday, July 14, 2020

Exam

"There now....that wasn't so hard was it....now just relax and I'll be finished with your exam soon...."
"How soon Ma'am?"
"Well Sissy....that differs from sissy to sissy.....but basically it boils down to at least an hour.....unless you cum....then it might be much longer!!!!"















All Week

"Annie....we've worked on your boyfriend all week while you've been on vacation....and he's ready to be presented back to you.....he's fully trained and restrained....he'll be obedient and faithful....and he'll behave while you enjoy a real man....he's all yours to use as you please....what do you think?"
"How about his tongue girls?"
"Maybe not the best I ever had but pretty damned close...."
I liked it......he had staying power...."
"Really nice....I wouldn't mind borrowing him on some lonely night...."
"Okay....which of you has the key?"
"Key? Oh we threw those away....I hope you don't mind...."















Monday, July 13, 2020

Please

She had put his little cock in a cage....
She had dressed him in slutty lingerie....
She had buzzed most of his hair off....
She had dyed what was left a sissy pink....
Now she told him to wait....
Get on all fours and wait....
Now she was going to fuck him....
She told him she was going to make him her bitch.....
She told him how big her big black strap-on was....
She told him that he was going to take it all....
She told him she was going balls deep inside him....
She told him that she was going to fuck him hard....
She asked him if he had anything to say before she went for her big dildo....
He only had one thing he wanted to say after all of this....
"Hurry please!"











Monday ManCandy

Lately you've begun to wonder.....after all this time....how can you go back to the office and not have access to your favorite treat at any time of the day?
Can you succeed in just having your fill in the morning and making it last all day?
You're not sure.....but it's true that when he came to deliver yours last week....he never left and he's been delivering all week!!!!!
ManCandy!!!! Ready whenever you need it!!!!











Sunday, July 12, 2020

Custom

She saw the opening and started her business with just her sissy husband to help her....several months have gone by and they have been very successful......pairing sissies with dominant men or women  has been working out so well....
Now whenever a customer came to them they could show the selection they offered....
"Do you want something special or maybe you see something you like on the rack?"
















Sissy School - A Weekend Visit Home

Wow!!!! Home again after all this time....
She welcomed me home and explained that she was going to leave me restrained until she got home from her errands......
I gave her a big smile and told her that I loved restraints......
She shook her head at me as she left....
Her boyfriend worked out how best to use the restraints in no time at all and with him in my mouth all I could think was how nice it was to be home!!!!














Saturday, July 11, 2020

Never

I don't know why she tells me to put on this dress.....I can never get the bow in the back right by myself....I think she just enjoys bending me over and spanking me like a naughty little girl.....truth be told.....I kind of like it too.....but everybody shhhhh....don't let her know that......it'll just be our little secret!!!!














Perfect

They were the perfect couple....they did everything together....
Down at the local gloryhole she invited them in and he did all the rest!!!!















Friday, July 10, 2020

Never Before

She told me to go into the bedroom and lie down.....
She said she had something special for me.....
She said she was going to make my cock feel like its never felt before!!!!
So many fantasies ran through my head....
But none of them was even close to the reality of the chastity cage she locked me in that night....













Unexpected

When they invited him to come to their place for a threesome this wasn't what he had in mind....but he found that he was enjoying this very much....so were they!!!!











Thursday, July 9, 2020

Coffee Break

It was nice when she stepped out of her home office to have a coffee break....we'd talk for a minute or two and then we'd make the most of it!!!!













Mom

He didn't know why his best friends Stepmom had one and he didn't care.....he had lusted after her since puberty and he wasn't going to let a little thing like this stop him!!!!













Wednesday, July 8, 2020

Still

"Still caged huh?"
"Yep....she says I haven't earned release yet...."
"That's probably true....you are a naughty girl....."
"True....."
"So...."
"So?"
"So I guess you're the one doing the sucking again...."
"On no....not that.....poor me...."
"Funny.....now get down on your knees....."
"Yes Sissy!!!!"














Hump Day

With only essential workers available on Hump Day you'll find that sometimes you'll have to do most of the work yourself!!!!









Tuesday, July 7, 2020

Quarantine

All the guys had finally had enough....and after the first one confessed his desires they were all very surprised to find they had more in common than they could have imagined!!!!














Me Too

"But I thought that having sex meant that I would get to cum too!!!"
"Silly boy....I don't know where you get these crazy ideas...."