Hello, Horny Readers! I’m thrilled to have become reacquainted with an old friend recently. He’s probably the most voracious ass slut I’ve met through My Femdom phone sex endeavors. I’ve frequently mentioned him when talking about why I’m such a fan of the Cyberskin Dream Dick. He’s fucked a variety of dildos, including a huge purple monster. That makes him a challenge to impress as far as fuck sticks are concerned. Yet, he discovered a whole new dimension with the Dream Dick. Anyway, since W/e last played, he seems to have developed a kink for small penis sissy humiliation (at least when he’s horny). Recently, Miss Constance has challenged him to surrender to it in a most creative way!

You see, despite his fondness for railing his fuck hole with an ardor that has not yet been equaled in all the instances of exhibitionist Skype debauchery of which I have been privy, and despite his penchant for becoming triggered by coerced feminization roleplay, he has been resistant to the idea that he is, in fact, a sissy!

His defense?

  • He has a “very respectable-sized” cock.  *eyeroll*
  • He likes to stroke said “cock”.
  • Aside from the occasional pair of panties, he has never had the urge to girl-it-up.

A new way to prove you’re a small penis sissy!

Mistress Constance decided that She would lay a wager on this sissy fuck slut in denial. He was to measure his supposedly adequate member against his favorite dong for fucking, a Cyberskin. The control? A transparent Fleshlight model called “the Ice”.

Want a Cyberskin of your own? Just click the pic! There are other colors (or at least one) available on Amazon.

Now, the Ice allows for 8.5″ of insert-able length, and a girth that would make any boy (and certainly any woman who had it inside her) feel chuffed. That’s just about right for the Cyberskin. Miss Constance instructed him to:

  1. Lube up and insert the Cyberskin as deeply into the Ice as possible
  2. Mark where the tip lay, on the outside of it, and
  3. Get his own “manly member” as hard as he possibly could, slide it into the stoker, and make a mark where his tip landed.

Oh, don’t worry–he wasn’t expected to measure up to the Cyberskin. Precious few men can do that. He only had to come within two inches of it. *smirk*

You might wonder why T/hey didn’t just use a tape measure to compare lengths. Well, because boys can’t seem to resist the temptation to embed the metal tab at the end of a tape measure into the flesh of their pelvis in the hope of eking out the extra-odd inch.

T/hey decided that this method would keep O/ur subject honest.

Well is he, or is he not a small penis sissy?

If he came within two inches, he’d get to stroke with the Ice until he had himself a nice manly orgasm. He could content himself with the knowledge that although he may not be packing enough to satisfy a size queen like Me, he could still consider himself worthy to fuck the average, non-discriminating pussy.

If he didn’t, he’d have to:

  1. Immediately withdraw from the stroker,
  2. Get that now-clitty soft,
  3. Plug his sissy pussy with one of his many ass toys,
  4. Clap himself into chastity,
  5. Put on some pretty sissy lingerie, and
  6. Call Miss Constance to be regaled with the knowledge that as far as sex is concerned, he is a designated sissy bottom!

Here’s where I’d say, “I won’t keep you in suspense”, but there is none, is there?  *giggle*

You probably knew how this would turn out the moment you started reading this post.

*insert game show “you lost” sound effect here*

Not only did he fail the length test, but while he had to strain a bit to squeeze the lubed dong into the Fleshlight, his little member floated around inside of it like a swizzle stick in a cocktail glass!

Time to prance, small penis sissy!

I envy Mistress Constance. She’s going to have a lot of fun the fun witnessing this newly-minted small penis sissy’s humiliation, and upbraiding him for his false macho! The newly-minted small penis sissy sent Me pictures verifying the results. I enjoyed a hearty laugh while viewing them! I wasn’t any more surprised than you likely are, but I’m still tickled by incontrovertible proof of a sissy’s status, even when it isn’t needed!

At least Miss Constance has promised Me more photos to giggle over, and I’m sure this rediscovered playmate and I will relive his humiliation for a long time to come! Perhaps, even build upon it!

So, do you have a Fleshlight Ice by chance? The Fleshlight brand has other clear designs, but the Ice is the only clear one I could find that’s made to accommodate a big cock or dildo. Do you have a big, girth-y, realistic dildo, suitable for measuring yourself against?

I’d be happy to make like Price Waterhouse and ensure the integrity of your results!


Miss Rachel, Certifier of small penis sissies everywhere!


P.S.:  I got to thinking about how some men describe themselves as “average” in the pants.  Average is fine for the average woman, I decided, but . . . I’m not the average woman.  So, if you would describe yourself as average, and you’re not interested in small penis humiliation, it’s better that you keep your measurements to yourself in session.

Listen in below for more on that.