Caption of the Month - XV

What can I say?  I love this caption!  I feel like every sissy can relate to this caption.

Cap of the Week - LXV

1) Lizzy Fucking Caplan!
2) Fucking great humiliation and control of her sissy!
3) Panties, chastity, every goddamn thing! 

This is a great fucking caption!

Sissy Review - IX

Today we’re covering a favorite of mine, Sissy of Spades.  Being in operation since 2014, this tumblr has done a fine job of proliferating some A-class captions, gifs, and videos for the entirety of its existence.  If you’re a lover of BBC, you are in for a treat as the bulk of the tumblr’s entries revolve around white submission and black supremacy with a fairly large cross-section of prostitution (“forced” and otherwise).  While the videos don’t always involve sissies and/or TG individuals, they’re almost always incredibly erotic and accessible to a large base.  The tumblr updates multiple times per week (sometimes multiple times per day), and you would think that, with the amount of content these people put out, the quality would decline at some point or they would get repetitive, but they somehow manage to dodge this pitfall, and then cum on your face for good measure.

There’s only a few issues that I have with Sissy of Spades, and they’re really not too big of issues, anyways.  First, it has a significant section of its content dedicated to bimbo-ization, specifically plastic bimbo-ization.  Like I said when reviewing Panty Bimbo, I recognize that this is explicitly a taste thing, but plastic bimbo-ization is definitely not my thing.  Second, as far as the prostitution aspect goes, you’re mileage may vary. When done right, the prostitution angle can be incredibly humiliating and erotic, when done wrong, it can be an overwrought, unattractive mess.  The prostitution on SoS is a mixed bag, but not enough to really detract from the tumblr.  But, again, with the amount of content they put out, you can’t really blame them if some things fall a little flat.  All in all, this is a damn solid tumblr among solid tumblrs. 

Update Schedule: Frequently.

Typical Posts: Captions, gifs, and videos.

Typical subject: BBC, White Submission, Bimbo-ization (plastic and non), and Prostitution (“forced” and non).

Extra Points: Lotta, lotta non-repetitive, high quality content. 

Paid content: None

Would like to see more...well-done prostitution caps/gifs, and less plastic bimbo-ization in order to cater to my specific tastes.

Final Rating 4.5 out of 5 submissive, white sissy-boys working a BBC.

Re-Blog Wednesday - 67

My Life as a Sissy Maid XXVI

Cap of the Week - LXIV

There's not really a thing I don't like about this caption.  The chastity, the unsatisfying orgasm, the confusion...god, how could you not love it?!

Sissy Vid - 7

Here's a great vid.  Goes pretty heavy on the hypno side of things.

Via: X-videos

Re-Blog Wednesday - 66

Old School Milovana - 7

 

Here's the beginning of a 10 part series that I've always loved.  Of course, I've always had a thing for Melanie Walsh.

Via: Milovana

Cap of the Week - LXIII

I just love he look on her face, and can't help but fantasize about the panties she's holding...also, I love the superimposed sissy in the background.  This one's from Shattered Heterosexuality.  A tumblr I've never seen before, but am interested in getting to know.

Retro Caption - 25

Here's an old great one from an old great (defunct) site.

Re-Blog Wednesday - 65

I 💓 Hypno Gifs - 22

Here's an old classic from way back when.

Cap of the Week - LXII

There's something about his caption that drives me a bit wild.  The girlfriend, the "ex," and their conspiring to leave the sissy alone to face whatever's to come...Whew!

Sissy Biography - IX

Of course, not all of my sissy outings were as smooth sailing as my trip to Victoria’s Secret.  My adulthood had more than a few weird scares wherein I may or may not have accidentally outed myself as a sissy to a third party.  This became a concern the longer I lived by myself as, I mentioned in a previous post, it creates an environment more conducive to expanding the boundaries of a person’s behavior, rather than reining them in.  As such, I had begun to push my own boundaries farther and farther out as time went on.  Panties became complete cross-dressing.  Cross-dressing led to humiliation.  Humiliation led to bondage.  Bondage led to chastity.  Chastity led to anal play, etc., etc., etc.

 

Whatever fetish I was indulging would eventually normalize, leading me to search for the next great frontier.  Whenever I had a girlfriend, the fear of getting caught became the thrill of possibly getting caught, which eventually led to the hope of getting caught.  Thoughts would often become actions which would occasionally put me in high stakes situations which left me at legitimate risk of becoming exposed.  One such occasion occurred relatively early-on in my post-college life.  I was just starting to step out of my sissy-safe-circle and really began to push limits of what I had grown used to in my private space.

 

I’d been dressing under my clothes for quite a while.  By this point, I had progressed from merely panties to black stockings and a garter-belt.  It was fall at the time so my shoes and pants covered my legs and feet; no one would know that I was walking around as a sissy-in-hiding feeling the tug of her garters as she strolled around like a secret girly slut.  Sometimes, when I was feeling really daring, I would forego a belt, so my pants would sit on my hips leaving the possibility of the waist sliding down just enough to expose the top of my garter-belt or maybe the waistband of my panties. 

 

 

 

One particular day, I decided to go the full nine-yards: hot-pink hi-cut panties with a thick lacy waistband underneath my black stockings and garter-belt.  Not only had I decided to forego the belt, but I also decided to wear a shirt that was a size too small. The idea was that, if I raised my arms too high, my midriff would expose itself just enough to leave the possibility of exposing what I was wearing underneath.  I was off of work this particular day (it was the first day of my vacation), but I had a few errands to run before my vacation officially started.  These errands included going to the post office to halt delivery of my mail.

 

I arrived around 11:00 am or so, trying to beat the lunch rush, and was relieved to see that there were only two or three people ahead of me in line.  I would be in and out, and off to my vacation spot!  I stood quietly and thoughtfully, imagining how I was going to spend my well-earned time off when…

 

“I thought you would have left by now,” said a very familiar lady.

 

I turned around to see my boss, a tall blonde woman in her late 40’s.  She had the look of a woman who had been a studious book-nerd in college, and aged pretty well.  Her sharp demeanor was off-putting to a lot of people, because she was brilliant and refused to dumb herself down, expecting others to rise to her expectations.  This often led to a high turnover in her department, but those who made it through were forged by goddamn fire! 

 

We got along well because I was competent at my job and never wasted her time with excuses.

 

We chatted, but I’m sure I was obviously uncomfortable the whole time.  After all, if making eye contact with a cashier was difficult, how uncomfortable was it to actually speak to someone I knew…someone I respected…someone I saw everyday.  My panties and garters seemed to irritate my skin as we spoke, a new hypersensitivity borne of the crushing reality of just how real this damned situation was.  I was fucking sissied-out wearing the outfit with the highest exposure quotient!  My every word seemed like a surreal exercise in public speaking, as I had to concentrate on every last thing I said in order to keep from stuttering like a panty-clad moron.

 

I think I covered well, or at least well enough to where she didn’t seem to notice my discomfort.  Eventually, the line moved forward, and I realized that I still needed to fill out my Halt-Mail Form.  I pulled out my pen and immediately dropped it on the floor. 

 

I don’t know how long I stared at my pen, lying on the floor, taunting me with what should have been a simple task.  All I knew was that my boss was standing directly behind me in line, and I was wearing a goddamn Victoria’s Secret catalogue underneath my pants…my idiot “shirt too small” that would ride-up over my beltless pants the moment I reached for anything.  How in the hell was I going to bend over and pick the pen up without being outed to my fucking boss?!  I had to do something.  It wouldn’t exactly scream “normal” if I left the pen on the ground, would it?  I couldn’t walk over it, turn around to face my boss, and then bend over to pick it up.  Even if that did conceal my sissy-shame, it would make me look like a crazy person—a crazy person in front of a person who I needed to impress if I wanted to move up in the department. 

 

Right about the time I thought about how much I needed to have this woman on my side, I got blindsided by another:  Did I have panty-lines?!

 

By the time I had decided on how to proceed, I’m pretty sure I had overthought to the point of forgetting how I would normally bend over to pick up a pen.  Hopefully I didn’t stare for too long before deciding on my course of action: bending at the knees all the way to the ground.  As I reached over, I felt my shirt hike-up, but I couldn’t feel where it stopped.  It could have stopped at the waistline, or it could have lifted to my lower back—I honestly couldn’t tell.  I retrieved my pen, slowly extending my knees as I stood, and looked directly into my boss’s eyes.  You know, like normal people do, right?

 

By this point, my mind had gone into overdrive.  When I looked in her eyes, I couldn’t tell if she was giving me a look, or if I was imagining it.  Was she smirking?  Did she almost say something, or did she clear her throat?  Was she waiting for me to say something?  If you were to ask me, I would guess I held this stare for roughly 15 minutes.  I felt frozen, like a cornered animal too scared to think (did she just raise an eyebrow?). 

 

The person in front of me in line broke my reverie as he was called up to the counter.  I snapped to, and spun on my heel to finish filling out my card, feeling hot under the collar (again!).

 

I imagine I handled that particular moment about as well as a person who had never spoken to a fellow human being before would have.

 

I finished filling out my card, and decided to do whatever it took to keep from turning back to speak with my boss.  There was one person in line, and obviously they would be finished in just a minute or two, so I could move on and spare myself the embarrassment of looking her in the eye.

 

Obviously, there was a stirring in my loins at the anxiety I was feeling.  This made me doubly determined to stay facing away.  The last thing I needed in this situation was an uncomfortable erection in front of my boss.  The more flush I became, the more my situation came into focus: I was in public, wearing hot-pink sissy-panties, dressed like I wanted to get caught.  What the hell did I expect to happen?! 

 

The more I try to steer my thoughts away from these thoughts, the more I failed at doing so.  The more I failed at doing so, the more aroused I became.

 

She cleared her throat—her powerful, womanly voice cutting through me…did she know?  Was there a part of me that wanted her to know?  What would happen if she saw my panties?  Who would she tell?  If she only saw my panty-lines, could I explain them away?  Would I make it worse, if I did so?

 

I breathed deep, trying to keep my erection to a minimum.

 

What the hell was taking this guy so long?!

 

I tried to keep my frustration in check as I absolutely did not want to accidentally instigate conversation, again.  So long as I faced forward, I could go back to the office and play the whole thing off as an awkward encounter in public.  If I was drawn back into conversation, I could very slip from “casually awkward” to “guy that probably has several doll heads in his basement, plus he wears panties” in just a few minutes.

 

Painfully, thankfully, the man in front of me finished his business and I strode to the counter, Halt-Mail order card in-hand, awkward erection hopefully unnoticeable.  I handed the card over, the cashier filled out some paperwork and I was out the door.  Easy peasy.

 

On the way out, I managed to catch my boss’s eye, to which she gave a smirking nod.  That face stayed with me through my entire drive home.  I had no idea what it meant.  Did she see?  Did she know?  Was it all in my head?  These three thoughts spun in my head for the entire drive home; these thoughts and one other:

 

I was so rock-solid hard that my cock-head was rubbing against the front of my panties with every tiny inconsistency in the road, causing the drive back to be frustratingly sensual.  No small part of me wanted to cum in the car.  I fought the urge, as I realized I had other tenants to potentially walk by on my way in, and the last thing I needed to was to explain why I had a big wet-spot on the front of my pants.

 

Some 15 minutes later and I was parked and running up the stairs to my front door.  I practically slammed the door open, I was planning on tearing off my shirt and pants (an probably quickly donning a pair of black pumps) to shamelessly masturbating in front of my mirror with my hot-pink panties and my black stockings and garter-belt, but I needed to perform an experiment.  I strode over to the mirror and squatted down.

 

Panty-lines.

To this day, I still don’t know if she noticed the panty-lines or if my shirt rode up enough to out me completely.  She never mentioned it, we spoke about meeting at the post office.  The only other thing I know about that day is that I came fast, I came hard, and a small part of me came hoping that I had accidentally outed myself to my boss as the panty-wearing sissy that I am.

Re-Blog Wednesday - 64

Labor Day...

  

If there were such a thing as a sissy union, I'd totally wear these until I got my stripes!