Slow and playful

"You know, I knew you had a little dick long before today." She says, her hand lingering over your crotch with more purpose now, making it a little difficult for you to speak coherently.

"W... what do you mean?" you say, anticipating the answer with great arousal, allowing yourself to indulge in the feeling of being humiliated.

"There was a day early last year where you wore a pair of rather tight jeans. It was pretty obvious. ALL the ladies on staff were giggling about it... Mr. Little Johnson." The name had always brought you great humiliation, and it still does, but hearing it from her lips, while she plays with your erection through your slacks brings another feeling, one you enjoy immensely. That, combined with the thought of the women you work with laughing about your small penis causes you to groan quietly.

"Oh, you like that, huh? Well what would you say if I told you Mrs. Adams , Ms. Welsch and I played a game where we guessed how big your cock was. I said four inches, and my guess was the nicest." You groan again, this time a little louder. With a devilish smile, she slowly pulls the zipper on your pants down, and begins to play with the head of your stiff cock through your boxer briefs.

"So, big guy... how big is it when you're all excited?" She asks, and continues stroking you, now unbuckling your belt and unbuttoning your pants, giving her much better access. You don't answer at first.

"Oh come on, you can tell me. I know you've measured it. All the little guys do... know what? Don't tell me. I like finding out on my own." She suddenly stops stroking you, and removes her hand from your pants, causing you to whimper slightly.

"Calm down naughty boy." she says with a chuckle. "I will take good care of that little thing, don't you worry. You're going to have to earn it though. Now... stand up."

You obey immediately. Being unbuckled and unbuttoned, your pants drop to your ankles. Your cock presses against the front of your boxer briefs. Shes grabs the entire thing over the fabric, giving it a light yank, just to establish some dominance. "ooooh. I think my estimate might have been a little generous. This is just a little guy. I'll tell you what, let's play a game. I'm going to measure little Eli, and if it's more than four inches, I will spend tonight rocking your world like you have never imagined."

"And if it's not?" You ask, wanting nothing more than to hear the answer.

"No no no naughty boy. That's not how the game works. You're not risking anything if you know the forfeit beforehand. So, do you wanna play?"

"Yes!" you say, a little over enthusiastically, causing her to giggle.

"Well alright then... I'll be right back." She walks out of the room, leaving you standing there with your pants on the ground, and your cock almost aching.