Owning My big loser

Stranger than Fiction - Sandy's Story Part 2

My Sweet Little Submissives,

Gather round boys and girls, it's story time!!

I spoke with Cassandra today for the first time in a little bit. Between the holidays and life in general getting in the way, it's been difficult for us to keep in touch lately, but I was finally able to get an update about the goings-on in what may be the most off-the-wall submissive life story that I'm ever likely to encounter first-hand. But before I update everyone as to her current situation, I should probably begin by picking up where I left off... (do forgive me, Sandy, if I get a few details mixed up. It's been a while.)

And for those of you unfamiliar with this little saga, I suggest you scroll down to read  Part 1 because it's a little difficult to follow otherwise.

Hold on to your seats, boys and girls, lest you fall flat out of them. 

Our story continues with the weekend following the babysitting incident. Cassandra was quickly informed by his wife Susan that he was to become Dan's property - his plaything for a time. Cassandra was beside himself? Herself? For the sake of keeping confusion to a minimum, we'll go with her / she for the time being. Anyway.

The week leading up to that weekend was quite the mindfuck. She loved how feminine Dan made her feel, but the methods that he used were degrading and painful. He loved to spank her and spoke down to her often, regardless of how submissive Cassandra was for him. Nothing was ever quite enough for Dan. When they met in the courtroom (on opposing sides, no less) his gaze was smoldering. If Cassandra so much as lifted a finger to defend her case, Dan would request to speak with her one-on-one for a "private consultation." After relentless badgering and a quick session involving her pants around her ankles, Cassandra would leave the room with a reddened ass and the irrefutable knowledge that it was not only in their private life that she would be required to submit to Dan.

Her home life had changed drastically as well. Susan no longer regarded her as a husband (not that she ever really did to begin with) but as a girlfriend. She and Dan's wife, Karen, would sit around the kitchen table with Cassandra, discussing the men in their lives (Steve for Susan, and Dan for both Karen and Cassandra.) They would trade beauty tips for Cassandra's benefit and fuss over one another's hair. In a nutshell, it was sissy cross-dresser's dream come true. Of course, it really didn't come as much of a surprise to Cassandra when Susan mentioned looking into getting a divorce. It was somewhat expected at this point. But what did Cassandra care? She had a man to take care of her... a married man, perhaps, but a man nonetheless.

The weekend involved much of what Cassandra would have expected - a lot of time on her knees and a series of spankings that hurt her in the most wonderful way. There were a few added bonuses too, though. As it turned out, Dan wasn't the only one capable of "babysitting." In fact, the whole group of them (Susan, Dan, Karen, and Steve) had planned quite the interesting turn of tables for our dearest Cassandra. During her weekend visit, Dan decided to step out for a bit. While Dan was out taking care of business, a familiar face from the past was sent to take care of Sandy.

And this is where we meet Jack. When Sandy first met Jack, Jack was a brat kid in bad need of discipline. As his babysitter, Sandy was quick to give it to him.... but apparently not enough to break him of his attitude. Jack grew up to be a decent enough guy eventually, but still held on to his cockiness, along with (can you guess??) a rather sadistic grudge against our Miss Cassandra. Word has it, when Susan and Dan concocted the plan to ask Jack to "watch" our girl, he jumped at the opportunity. The babysitting job was relatively short, but ruthless. To quote Sandy (it's been a while, so I'll have to paraphrase), "There was a certain glimmer in Jack's eye almost the entire time. I got the feeling that he was enjoying himself a little too much."

Sure, Cassandra, anything you say. ;) You loved it. Who the fuck do you think you're fooling? LMAO!!

By the time Dan got back, Sandy's ass was sore and red (for various reasons) and Jack could not have looked more pleased with himself. Apparently, Dan was pretty pleased as well. Over the next few days, Cassandra heard excited murmurs under the breaths of all involved - Susan, Steve, Dan, even Dan's wife, Karen. The only person that wasn't in on the secret was Cassandra. Just before the weekend came around, they finally filled her in.

Now as I mentioned before, Dan is married. So while he could have taken Sandy as his permanent property, it was decided across the board that he wouldn't. You see, Sandy lives in South Carolina, a state which has recently legalized same-sex marriage (November 2014). With this newly acquired privilege before them, it was decided that in order to humiliate Sandy further, he would be forced into marriage with another man. Two candidates were brought to the table - Jack and Pete.

Have I told you about Pete yet? Pete is another lawyer at Dan's firm; Cassandra's stiff competition. Pete is younger than Dan, but just as cocky and aggressive. He's also single, and thoroughly loves putting Sandy in his place in the courtroom.... and more recently, outside of the courtroom as well. Considering the ongoing theme of this particular story, I'm sure we can all figure out pretty quickly what that entails. ;)

Since both candidates showed an interest in owning Cassandra's ass til death do they part, a challenge was put forth - whoever could turn our girl into the bigger bitch would be declared the winner. Each got a weekend alone with Cassandra, during which the rest of the group would check in periodically to see what progress was being made. The experiment had its purpose, I suppose, but frankly? They should have just asked me. I knew who would win before either of the guys had taken their turn.

It's funny the things you can pick up in a person's voice when you're not actually looking right at them. Whenever Sandy talked about Jack, his voice took on this wishy-washy tone that pretty much reeked of mediocrity. In his head, he probably knew he would have an easier time with Jack, so he quietly claimed to hope that he would win out. But Submissive Slut Sandy wanted more than that. The pure intimidation and excitement in his voice whenever Pete's name came up was a total giveaway. His voice would quiver and his breath would shudder..... he sounded like a girl on the verge of orgasm, for fuck's sake. Pete was a man, and in Cassandra's mind, Jack was (and would always be) a boy by comparison. Pete would win, hands down.

The results are in, by the way. Pete won by a landslide. I love being right.

So now for the update:

Sandy has been put on suspension by his law firm. Why, you may ask? Or maybe you're asking why that's relevant. Either way.

As previously mentioned, part of Pete and Dan's domination over Cassandra has been tearing her apart in the courtroom. These guys are a pair of lawyers that go up against Sandy on quite a regular basis, and needless to say, within the past few months, he hasn't won a single case against them. His track record is basically in the toilet.

Their most recent victory over Sandy was due to circumstance.... circumstances that they created, no less. Just before he was due to appear in court, the group brought him the clothes that he was to wear to his litigation. Specifically, lingerie, a rather tight-fitting women's suit, a scarf, and heels. As you can imagine, Sandy's nerves were shot to hell. It wasn't until the very last minute that they decided to undress him down to his lingerie, throw the men's suit over his panties, and shoo him off to court. It was the ultimate mindfuck, and it worked wonders. He was an absolutely train wreck and performed so poorly that the judge asked him after the hearing was over if he was okay. It was an absolute nightmare come true.

But that's not the only reason that Sandy's been put on suspension. It certainly enough of a reason, but it's not the straw that broke the camel's back. It was his divorce that provoked his firm to take action.

Susan filed for divorce. As part of the continuation of Cassandra's humiliation, she stated that the cause of the divorce was Sandy's adultery with another man. He was forced to state the names of all the men that he had been with... Pete and Dan included. You might think that this would be confidential information, but seriously? Of course lawyers talk, especially concerning other lawyers. Sandy's firm got wind of the situation and put two and two together. He was losing his cases on purpose (or so it would seem to them.) Of course, we know that Cassandra's submissive nature would allow nothing less, but what's done is done. Unless Sandy ends his relationship with Pete by the time his suspension is over, he will be sans a job. And since we all know that's not going to happen....

What can I say, Cassandra? Hope you're ready to be a housewife!

That's all for now.... which is okay, because that was PLENTY. Whew!

Kisses,
Drea.

More Pictures Added to the Collection :D

 

My Sweet Little Submissives,

My boys have been so good lately!  Just look at the pictures I've been gifted with in the past few days.  :D

First allow me to introduce you to Brian.  As you can see, Brian likes to swipe his wife's panties (without her knowledge, of course) and take pictures of himself in them.  Wonder what wifey would think??? I'm half tempted to find out...

Then we have Michael.

 

Oh, Michael. Showing your face and everything!  LOL (By the way, he actually gave Me verbal permission to put his face on My blog.   Shameless little dirty boy!)  Love the teeny tiny maid outfit.  So adorable :D

 

And if that wasn't enough....

 

 

Whoa, MAMA!! Flexible much?  LOL  Someone's been practicing his yoga!

 

 

That's all for now boys and girls, but just to keep you all updated, keep an eye out for the next addition of Sandy's Story.  I just heard from him yesterday and he was able to fill me in on a few more details that allow me to flesh out the rest of the story a bit more.  Coming soon!

 

Kisses,
Drea.

 

 

  

 

 

 

 

 



 

  



It's Good to be Pleased :)

My Sweet Little Submissives,

I am overwhelmingly happy to announce that thanks to all My good boys that continue to call and do such a wonderful job keeping Me entertained, I have been given my FOURTH Performer Gold Award on Niteflirt!! Keep up the good work, boys :D 

Now for the updates:

Poor Michael.  His Mistress / Wife has seen fit to put him in chastity and tease him by allowing him to call Me... without access to his pretty little peewee.  LOL  All locked up in his panties and hard as a rock.  Guess you should have kept the panty cumming to a minimum, huh, sweetie?  What do you think it was that sent her over the edge, exactly?  Was it the time She came home with Her best friend to find you sitting in your cum-soaked panties in the chair by the door for Her?  Or maybe it was that time you dripped cum all over Her house after one of your episodes because you couldn't find the rubber panties you were supposed to be wearing in case of an accident.  :/  Now really, Michael, you should have known better.  You could have dripped all over the furniture!  Serves you right, really.  ;)

G. - I suppose you've waited long enough.  I've finally decided to take you off of My blocked list.  Lesson learned, I hope? LMAO I told you not to test me.  :)  I would have taken you off sooner, but I've been so busy lately.  You understand.  You know how hectic things get for me.  You have no one to blame but yourself, after all.  If you'd never put yourself on My naughty list in the first place, you would never have had to wait to get unblocked!  Let's hope you're ready to be a good boy for me now.  Be sure to have the sounding device and nipple clamps when you call.... you know how I hate to wait.  It takes away from My momentum, and we certainly can't have that.

As for the rest of you, continue being Good Boys for Me. ;)  I love you all, My sweet little subs!

Kisses,
Drea.

Just a quick hello :)

My Sweet Little Submissives,

Just a quick little note to say-

Hey Joseph ;)

Such a sweet little thing.... those testicles are just a couple of barely there lumps!!  Adorable.  LOL  

Kisses,
Drea.

Tis the Season! :D

My Sweet Little Submissives,

You've all managed to work your way onto Santa's naughty list by now, I assume?  You know your Mistress expects no less of you ;) LOL  Hope you're all doing well.  It's a busy time of year for me, but then again, "tis the season", I suppose.  

My Bobby decided to give Me an early present this year.

So cute!  It was even more interesting watching it on cam.  He even manages to stroke it like a cocksucking queerboy, doesn't he?  Pinkies up, Bobby!! :D  LMAO  And what's more, this isn't the last of his gifts to Me.  You SAY you're willing to suck cock live on cam for Me, babe.  Now you just have to prove it.

I also got a nice little treat from my cumslut Denise!

All dressed up like a bitch and sucking it like a pro....  but I would expect nothing less from a such a sweet little submissive cockwhore.  Keep up the good work, Denise. ;)

I am less than happy with a small number of you, however.  Most notably you, G.  First you fuck up by your own admission, then you claim that you'll take the punishment.  And what was that punishment?  No cumming for another two calls, period.  Did you actually think that calling me again five minutes after we hung up would count towards your punishment??  You're officially blocked for three days.  Don't try me, bitch, I will make your ass regret it.  I hope your cute little tight-ass secretary bends over in her short little skirts all day in front of your loser ass.  Is the cockcage getting tighter yet?  Awww. Poor you.  L. M. A. O.

As for the rest of you, be on your best behavior....  or else.  ;)

Kisses,
Drea.

 

It's good to be in control ;)

My Sweet Little Submissives,

Hope you've all been behaving yourselves.  ;) For anyone who may be curious, I do intend to fill you all in on the rest of Sandy's story, but it's a lot to write out and quite frankly, you boys have been keeping me very busy.  Just thought I'd get in a little update.

Big D. - SOOOO much fun.   The insane amount of kink toys he brings to the table is both mind-boggling and incredibly exciting.  I only wish you weren't so SHY! Mistress wanna see, too.  :p  I mean, I get it, I really do. I don't blame you one little bit. But.... but.... (okay, full-on pout mode here) those little whimpers you give Me are so fucking ADORABLE. Sure, I can imagine how your body quivers and your cock trembles and whatnot, but it's just not the same as actually getting to see it for myself. 
/pout session

K. - My oh my the things you will do to yourself for Me.  LOL  I hope your balls are feeling better, btw.  ;)  He's such a good little sub boy.  Very obedient, just the way I like them.  And you held yourself together so well, too!  Impressive, I must say.

Drew - Swallow any cum tonight?  Hope those two guys got back up with you, sweetie.  You're in bad need of some action, and cock is pretty much the only thing your puny-dick self can swing. LOL

That's all for now :)  Be good!

Kisses,
Drea.

Stranger Than Fiction - Sandy's Story Part 1

My Sweet Little Submissives,

Throughout the coarse of talking to all you beautiful boytoys, I have heard some serious whoppers.  It's often difficult to tell which ones are true to life and which ones are just well thought-out fantasy, but every now and then you come across an individual with such a rare gem of an eye-popper that you can't help but believe it.  The details are there, the answers are consistantly the same... this is the retelling of someone's actual life experience.  

READER BEWARE - this is a long fucking story.

Such is the case with Sandy a.k.a., "Cassandra".  Cassandra has been a sissy almost his entire life - Mommy Dearest took extra special care to see to that, as did his sisters.  They'd dress him up and primp and pamper him until he knew deep down that all he wanted out of life was to be a pretty girl.  He trudged through life pretending to be the boy that his body insisted he must be, went to college, got his degree, became an attorney, yadayadayada...

Enter Susan.  Susan is (currently) Cassandra's wife... though not for much longer.  ;)  Susan was kind enough to embrace and dominate his feminine quirks, dressing him to her taste and fine-tuning the raw beginnings that his mother set in place.  She, of course, continued to date and get fucked by real men while her sissy stayed home and played... housewife? Maid? Either way, as happy as everyone involved was with the situation, there always seemed to be something missing.  

Now if it seems like I'm glazing over the facts a little bit, keep in mind... this is just the back story.  The real story begins with Steve.

When Steve and Susan first started dating, Cassandra had no way of knowing that this particular match-up was about to change his entire life for good.  How could he?  His wife had been through tons of guys in the past - no big deal.  None of them were really longterm material, just a bigger dick for her to fuck than the little clitty he had to work with... not that he ever did  more than cum in his panties anyway.  But after a few months of dating, Susan brought Steve home...

And insisted on Cassandra being the one to answer the door for him.

This was the first night I ever spoke to Cassandra.  He was literally shaking with that intoxicating combination of fear and excitement; asking Me how he should greet Steve, and whether he should ask his gorgeous wife if he was to answer the door dressed as a man or a woman.  What would Steve say?  What would Steve DO?  LOL!  Finally I calmed him down enough for him to gather up his courage and approach Susan about dressing himself up as a woman (which was so obviously what he wanted to do anyway.)  Susan was pleased, to say the least.

Later that night, Cassandra contacted me again to give me an update.  Steve had shown up, apparently very pleased to see good ole Cassie dressed up like a proper lady, and proceeded to take full advantage of the situation.  Translation: Cassie got fucked GOOD.  It was kind of a big deal, actually.  Up to this point, Cassandra had only ever played with toys.  The thought of experiencing the real thing had been nothing more than a pipedream and he was filled to the brim with ideas of what might happen next.  Funny thing is, he had every reason to be.

Again, I got a call.  Same night, not too long after the first update - Susan and Steve were staying out late, and they were sending out a BABYSITTER for Cassandra.  Um.. okay!  LOL   We tossed around a few options for potential "babysitters" that Susan might send to watch over him.  A couple names were mentioned, but there was one name in particular that put dread in Sandy's voice - Dan.

Dan was the husband of Susan's friend, Karen.  Dan was also a fellow attorney, working for a competitive law firm.  Already, Dan and Sandy had faced their share of run-ins in the courtroom... almost always with Sandy on the losing end.  He was an arrogant SOB that Sandy was incredibly intimidated by, and Susan knew it.  It only makes sense that if a babysitter had to be brought in, it would be him.

And wouldn't you know, that's exactly who showed up at Sandy's door!  Keep in mind, Dan already had some idea of what went on between Susan and Sandy.  His wife was her best friend, after all, and well... girls talk.  A lot.  It would be fair to assume that what Dan didn't already know (if anything) Susan had filled him in on by the time he pulled up into the driveway.  From there, Dan had the distinct pleasure of humiliating Sandy to the Nth degree.  He stripped him down, fucked him, spanked him, and proceeded to give him a bath.  Babysitting, huh?  Well... I guess.  Sandy certainly did get taken care of, at any rate! LOL  Sandy was shaved clean, put in his nightgown, and put to bed, using Dan's cock as a pacifier.  He awoke the next morning to witness his wife and her date standing over him laughing their asses off.

There is so much more story to tell, and trust me, it only gets weirder from this point on.  Let me assure you, this is NOT a product of my imagination.  If anything, I would say it was too much too quickly and a little overboard in terms of what is realistic and what's not.  But then again, as the title says, sometimes fact really is stranger than fiction.

To Be Continued.....