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!

Caption of the Month - XVII

Here we are, again!  There's just something so quintessentially sissy about this caption!  I love it!  Great Job, again, Cool Sissy Porn!

Re-Blog Wednesday - 76

Sissy Vid - 8

Here's a great vid that I just can't ever seem to get over.  I just wish hypnosis was as effective on me as it is the victim in the video.  Stick around until about the 5-6 minute mark for the hypno portion!

Cap of the Week - LXXIII

I really love this cap because it encapsulates what so many of us crave

...chastity...humiliation...wanton depravity...

Plus, it has the added bonus of having sissy-censors on it!

This piece of work given to us by Cool Sissy Porn!

Sissy Review - XI

 

 

Gonna go really old school today and talk about a site that’s near and dear to my little panty-wearing heart, Locked in Lace.  For those of you who don’t know, LiL is an old (ca. 2009) forum that expanded to house quite an extensive catalogue of content both original and borrowed.  Seriously, it’s got everything from captions to stories to games.  Plus, they have an extensive built-in role-playing community for those of you who just can’t get enough play (choices generally include: forced sissification through indentured servitude to the Lacy Place Casino, and forced sissification through general slavery at the MR Corporation).  While their games are old school flash games, they’re still worth a look.  The waitress simulation is far more entertaining and stimulating than a game about getting your ass grabbed should be.  Plus, the interactive story The Office Pool almost makes me cum in my panties just thinking about it!  Seriously, it’s a quality forum that has a little bit of something for everybody.  If you can’t find something that you like here, then you should be able to find a link to what you do like.  With a community this extensive, someone is going to know where to go in order fill the hole in your little sissy heart!

 

As far as my gripes…well…when you have a community that extensive you can’t always ensure quality.  The stories’ quality range from great to…passable, and the captions have some great original stuff…and some not-so-great stuff (poor photo shops, the grainiest of the grainy pictures, etc.).  A lot of their projects remain unfinished, but, again, it’s a huge community, so I can’t begrudge them when things start going by the wayside.  I will say this, though, there does seem to be a lot of long-term projects that do get finished.  Just like any other good forum, where the admin start wavering, the true-believing members will pick up the slack!

 

Update Schedule: Constantly.

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

Extra Points: Longstanding, loyal community.

Paid content: None

Would like to see more...finishing of projects.

Final Rating 5 out of 5 Indentured Casino Bunnies

 

 

Re-Blog Wednesday - 75

My Life as a Sissy Maid XXVIII

Cap of the Week - LXXII

There's something I absolutely love about this picture.  The blackmailed element...the look in the sissy's face...how her mouth fits so perfectly around the cock...

I 💓 Hypno Gifs - 24

Re-Blog Wednesday - 74

Retro Caption - 27

I always loved this one. I love how dominant the girlfriend is, and how the sissy has backed herself into a corner, forcing her to suck cock!  Unfortunately, I can't seem to find it's origin.  Let me know if you know, do I can give credit where it's due.

Cap of the Week - LXXI

Goddamn, I love this caption!  This is the perfect mistress with the perfect attitude!  She is beautiful and strong!  Great work, Sissy Dru!

Sissy Biography - XI

It wasn’t long after my time with Paige that I met the girl I would eventually marry.  Even though we haven’t really delved into the sissy-side of things, it doesn’t matter to me, really.  Even if we never get around to it, I can’t imagine having married anyone else.  I still love her like no other woman I’ve ever met and we’ve been together for over five years.

While Paige would have been fun to be with in terms of continuing our foraying into sexual deviance, my wife is my wife.  There’s no comparison.

All this being said, there have been a couple of instances where I tested the waters.  These were, of course, early-on in the relationship.  With the right finessing it might have led into something…interesting, but so far it hasn’t.  Again, not for lack of delving certain waters.

My first experiment happened about six months in.  We lived a couple of towns away from each other at the time and it was a bit of a commute to see each other, but we made it work.  Our sex-life was pretty damned amazing, and she had made a few comments that she might be a bit liberal minded when it came to branching out.  I decided I was going to see if I could push her in the right direction with a bit of a white lie.

So, my brilliant master-plan was brilliant in its mastery:  I knew she had to work the morning after I arrived, so, while packing for the weekend, I “forgot” to pack any boxers.  After discovering my error (while she was at work, naturally) I would, in my “off-beat but still somehow loveably brain-addled way that makes everybody who comes into contact with me think I’m the goddamn bee’s knees (right?!),” come to the conclusion that, since I’m not will to wear the same pair of boxers two days in a row (what am I, a heathen?), and since I’m not going to go commando (heathen!), I was going to borrow a pair of her panties to wear for the day.

Goddamn genius.

The morning came and I waited for her to go to work, took a shower, and made my way to her panty-drawer.

Another thing that’s great about my wife:  We have similar tastes in panties.  I don’t know if you’ve noticed throughout all of these little write-ups, but I tend to favor bikini-cut panties, specifically string-bikini, if I can get them.  I know some sissies prefer thongs, but I guess I’m just not as slutty as they are; I have always preferred the bikini, the silkier the better, the sissier color the better.  Of course, if they can give me solid panty-line all the better; there’s something about that possible casual exposure that just gets me off!

…

Maybe I’m a little sluttier than I thought. 

Anyways, I started delving wrist-deep into her drawers, finding a few different hip-huggers, and a few different bikinis that would fit the bill.  Of course, the next question was what color to choose.  I mean, choosing a hard-core pink or purple might tip my hand too much, but picking a tan or a white would be too plain for the task at hand.

I tried on a few pairs (all right, maybe more than a few), making sure to model them appropriately in the mirror (tucked, of course, as girls seem to be disappointed when I don’t tuck), so I could tease myself mercilessly make sure I had the appropriate look and fit.

I decided on a pair of light blue bikini panties, with lace leg bands.  I figured the blue was colorful enough without being completely effeminate.

I was, of course, rock hard, my erection working itself underneath me in its tucked prison.

Around noon or so, I got a call from my, then, girlfriend, telling me that she was through with her shift and was ready for me to pick her up for lunch.

The reality of the situation hit me, as the blood drained from my head.  Was I really going to meet her for lunch and tell her that I was wearing her panties?  The whole concept seemed overwhelming.  Reading about this stuff was one thing, but actually going through with it was quite another.  Would I actually be able to go through with the sordid affair?  

The more I thought about it, the more I realized that the reality was too big to wrap my head around.  I came to the conclusion that, if I really wanted to go through with the plan, I needed to focus on a small part I could achieve that would make sure I was stuck in a position where I couldn’t chicken out.

I stepped outside of her apartment, and locked myself out.  I didn’t have a key, so there was no going back short of breaking in.  As nervous as I may have been about my girlfriend, I sure as hell didn’t want to explain myself to the cops while wearing panties.  The only way to go was forward...forward to my girlfriend.

I pulled into the parking lot, and walked to her office, my entire body feeling flush, as I could tell that everyone was watching—everybody knew.  When I finally made it to her office, she was finishing up some paperwork and counting down the seconds until we could be free for the rest of the weekend.  I shifted my weight, and felt myself shift in her panties, beginning to engorge.  We chatted for a bit with me standing in her doorway as she sat at her desk.  I tried to keep from being distracted by my panties, but could feel myself failing, every movement rubbing my pantied cock in electric ecstasy.  Eventually, there was a lull in the conversation, and I realized that it was time for me to make a decision: to either act the coward and figure a way out of my predicament, or to man-up and tell my girlfriend I was wearing her panties.

I started off strong.

“So, uh…[throat clearing], yeah…”

She looked confused, oddly enough.

“So, I may have forgotten to pack any boxers.”

“Oh, no.  That’s hilarious.  So, are you just going to wear the same pair all weekend?”

“Well, it’s been so humid, that that seems gross to me.  So-“

“Why honey, are you going commando?”

“Well…no,” I broke eye-contact and cleared my throat again, “I figured that that would be worse on my pants than wearing the same pair of boxers.”

She looked confused.

“So, I might have borrowed a pair from you.”

She flinched with a confused look of amusement.

“So, wait,” she said, shaking her head, “are you saying you’re wearing my panties?”

I lifted the waistband over my belt.

“That is so, cute!” She said.

I inwardly breathed a sigh of relief.

“So, why the blue?” She asked.

I explained in a joking tone that I wanted a color that wasn’t overtly feminine, but that beige was too bland.  I mean, after all, what was the point of wearing panties if I was just going to wear a neutral color.

“Well, next time,” she said, “check with me first.  That way we can make sure they fit you all right.  I don’t want you stretching out my panties.”

I explained to her that I tried on a few pairs, just to make sure I wouldn’t stretch them out.

“Uh-huh.  I’m sure you did,” she taunted.

The rest of our day together went as normal.  We had lunch, and generally enjoyed each other’s company.  Of course, for me the day had taken on an entirely new erotic tone, as I spent the entire time in my girlfriend’s panties.  She didn’t seem to mind at all.  I knew that, with the proper prodding, this relationship could lead to proper sissy-lifestyle.

I had to tell myself several times, not to get too excited, and that such good things take time, but that didn’t keep me from fantasizing about a future of forced femme and chastity and sissy-servitude and everything else I’ve ever wanted.  I managed to keep a lid on myself, though.

Throughout the entire day there was only one moment where she acted like she even thought about me wearing her panties.  We had met up with some friends and were playing a board game.  I lost a particularly easy point and cursed aloud.  She turned to me, a knowing, impish smirk on her faced, and said, “Don’t get your panties in a twist.”

I felt myself fully engorge in record time.

That night, we made love so furiously that we slept half of the next day away.

To be continued…

Re-Blog Wednesday - 73

I effin' 💓 these gifs!

Cap of the Week - LXX

I love the lingerie in this caption.  She looks so sexy and ready to play!

Caption of the Month - XVI

I have to say, this was a hard choice, but I managed to muddle through!  When push comes to shove, I will almost always stray to the slow corruption of masculinity into sissy-hood.  This is really a great caption!

Re-Blog Wednesday - 72

A Halloween Post...

Being as it's Halloween (every sissy's favorite holiday), I've decided to give a treat to every sissy out there who's been gracious enough to frequent my humble corner of the internet.  So, here's a series of your blog-sissy in a maid's costume, dressed appropriately for any and all services that will be asked of her...

I assure you, that's not a spare tire around my gut...it's the waist cincher...

Anyways, Happy Halloween all you sissies out there!