Caption of the Year - 2018

WHOOO!  It's been a big year with a lot of great captions.  Let's go by them month by month, and see which one came out ahead!

I fucking loved the implicit story of this one...

Goddamn!  This one's soooo sensual...so sexy...I want a wife like this!!

The look on both of these girls' faces...

God...what I would do to live the life of this sissy-slut...

She's so beautiful, and the conflicted look on her face...

Again...such a lifestyle...what I would do to have such a taste...

Holy fuck!  The look of contempt!  The fucking truth to what she speaks!  This one almost took it!

Another message that every sissy heeds at some point!

God!  How do you not love this caption!  The sissy...the trepidation...the inevitability!

Oh, to have such an alpha-male to teach me my place!

And, of course, the latest.  Still a great message for all the sissies!

All of these have been great captions!  But, if I had my pick, it would have to be this one, for the caption of the year!

She's beautiful!  She's pantied!  She's emasculated by her wife in front of all the other men!  What more could you ask of a caption! 

Congratulations for being Sissy-in-Black's Caption of 2018!!

Caption of the Month - XVIII

Here's the December's caption of the month!  A great little caption, with a great little message, about great little bumps!  This cap is coming in early due to the impending Cap of the Year for 2018!

Can't wait, can you?

Cap of the Week - LXXVIII

I have to say, I love the concept, here.  Unable to cum, but allowed the chance, if one is willing to play the ultimate sissy game...that is, if these gurls are playing fair...

Re-Blog Wednesday - 80

Sissy Christmas - II

Here's a blast from the past!  Good god, this video has always gotten me off luck goddamn nothin'!

Cap of the Week - LXXVII

This is kind of an odd-duck for me, but I can't help myself.  Lexi Belle has been a sissy-idol of my for quite some time.  I feel like I owe it to her to give her some sort of recognition!

Sissy Review - XII

Whilest in the throes of my typical online sissy-meanderings, I happened upon a tumblr that I’ve seen making the rounds recently, Pleasant Princess Candy.  A relatively new tumblr, (est. April 2018), I feel this site is going to continue to strongly establish itself as a damn staple.  Its central theme centers on the basic premise of sissy-blackmail, and, from there, branches out as far as it possibly can.  This can mean anything from forced prostitution to indentured sexual favors.  Wherever it goes, the captions themselves are well-put together, well-written, and generally knock my goddamn socks off.  Hell, sometimes the captions stop at the premise, giving us a snapshot of the image that leads the sissy into blackmail, and yet they do in a manner that gives a brief, tantalizing glimpse of what is in store for the poor sissy.  If your fetish menagerie includes submission on any level, then this tumblr has the ability to satisfy, and the potential to drag you down exponentially further into the depths of submission.  So long as the tumblr can keep up this level of quality, it has the potential to become a damn juggernaut in the sissy-circles.  If it can keep on keeping on, then its tipping point will come!

I don’t really have a lot of criticism to render about it.  Of course, it’s relatively new, so it hasn’t had a lot of time to accumulate issues, like becoming formulaic (Cum Loving Hubbies?) or to fall victim to other stagnation.  When centering on such a specific niche, the danger is always there, and the temptation to become lazy hangs over one’s head like a blackmailer’s cellphone picture.  Maybe its time will come, maybe not, but, for now, this is a tumblr I’m actually excited to watch unfold.  I hope it can keep walking that tightrope!  

Update Schedule: Frequently.

Typical subject: Blackmail, Submission, Bullying, Indentured Work, Forced Prostitution, Slavery, and on and on and on...

Extra Points: Knows its subject, and executes it well.

Paid content: None

Would like to see more...time to develop.  Hopefully, it can keep this level of energy!

Final (Tentative) Rating 4.5 out of 5 Grainy Blackmailed Sissies

Re-Blog Wednesday - 79

My Life as a Sissy Maid XXIX

Cap of the Week - LXXVI

What can I say?  I'm always partial to panty-lines...also, I think this pic is from Emma Stone, which is one of my favorite actresses ever!

Retro Caption - 28

I've always loved everything about this caption, the picture, feminization, the taboo.  This was the kind of caption only Alexis Michelle could deliver.  Unfortunately, her blog is defunct, now.

Re-Blog Wednesday - 78

I 💓 Hypno Gifs - 25

Cap of the Week - LXXV

I fucking love this caption! 

Sissy Biography - XII

Unfortunately, there's not much more to tell on that particular story.  We had a nice rest of the weekend and went back to our lives.  Eventually, we moved in together and had a conversation about weird stuff to get into, but it never materialized beyond that.  It's been a bit of a drought ever since.  Not that I'm complaining as I eventually proposed and married the girl.  I'd say things are going pretty damned swimmingly.

Really, there’s only one more story regarding my sissy journey, and it’s a short one.  On the weekends, I usually do some late-night online-gaming with some old friends from high school.  During this time, I’m usually shut-up in my office so I don’t disturb my wife, who’s in another room doing her own thing.  It’s not uncommon for me to slip on a pair of panties that I wear underneath my clothes as I game.  We usually wrap-up around midnight or so, and by then my wife is usually fast asleep.  During this time, it’s not uncommon for me to get online and have some low-key sissy-time in my panties.

This one particular night, I had apparently went longer than usual.  I had finished up and was in the middle of changing out of my panties, when my wife opens the door without knocking, seeing me with a pair of turquois high-cut briefs around my ankles and my cock still rock-hard. 

“Oh, my god!” She laughed and slammed the door.

I nearly passed out, but was cognizant enough to hear her make her way (quite quickly) to our bedroom.  I quickly changed into my normal male boxers, pulled my pants back on and hurried into our bedroom.  Apparently, my addled brain thought that if I was quick enough, I could get ahead of the story and control the headline.  Relationships work like congressional scandals, right?

Truth be told, I don’t even remember what BS excuse I gave, but I do remember getting a sarcastic “uh-huh” when I said it.  We both went to bed and haven’t spoken of that moment since.

Really, that brings us up to speed on the whole “sissy biography.”  There hasn’t been any forward movement.  There’s a part of me that keeps coming up with scenarios that would end up with me getting caught en femme, and there’s a part of me that’s too terrified about that idea to do much of anything.  I’ve thought about locking myself in chastity and putting my keys on her keyring, but, like all sissies, I’m still terrified of the reaction I’d get.  When I’m hot and bothered, it seems like the easiest thing in the world, but any time after I come down, reality comes crashing in.  Well, who’s to say what will happen?  Who’s to say I won’t get caught, again?  Hell, there’s no small part of me that hopes she finds this blog and puts two and two together.  Wouldn’t that be a dream?

Anyway, thanks for hearing me out.  It was weird seeing all of my experiences in print for all the internet to see.  Hopefully, it was of some entertainment to someone out there.  But, until I think of something else worth sharing I guess I’ll always remain your closeted...

-Sissy-in-Black

Re-Blog Wednesday - 77

Showing my age on this one!

In all honesty, it's this girl:

Princess Glimmer of She-Ra fame.  There was something about those colors and that hair and that bodice that I absolutely loved.  I could not get it out of my head.  Obviously, I was not very old when this all started.

I also always like it when the characters were taken captive and had to submit to the villains, but that's for another caption, I'm sure.

Cap of the Week - LXXIV

I can't really explain it, but there's just something about this caption.  The look of the mistress.  The position of the sissy.  The high heels.  The stockings.  The sweaters.  The whole thing just screams "Sex" to me!