Domme School

Mistress Dee feeding her slave dog treats as a reward for giving her strap-on a quality BJ.

I’ve been toying with the idea of becoming a pro dominatrix for a while now. I’ve had a few slaves in the past: a British cash pig who paid my rent in exchange for degrading emails—some sissy lawyer who had to ask my permission in order to cum. I even briefly had a lifestyle slave who would come over and do my housework. He’d scrub the toilet while my girlfriends and I shouted abuse at him or spat in his mouth or made him wear our underwear—whatever. However, those relationships all quickly fizzled, mainly because I’d freak whenever a situation pushed past my comfort zone, aka training-bra-level domina stuff.

A couple months ago, a fetishist friend of mine gave me the number of Mistress Dee, a prominent New York dominatrix. He said if I really wanted to become a successful domme I should spend some quality time with her, adding that Mistress Dee is “New York’s reigning queen of forced-bi.” Forced-bi is when you make straight guys suck cock as a form of degradation, and since not all dommes do this, it’s sort of a big deal. I decided to call up the Mistress and ask if I could tag along with her for a few days, hoping the experience would help me decide if the pro-domme life was truly what God or Satan or whoever had always intended for me. To my surprise, she said yeah, she would love to have me. Quite a few of her clients are into having “civilians” observe their sessions—I guess it adds to the humiliation factor—so this arrangement could work out for her too.

My first visit to Dee’s home is at three on a Tuesday afternoon to watch what her email described as a “1-hour in-person w/ male submissive.” She answers the door wearing a sheer red thong and nothing else. She has wavy chestnut hair, porcelain skin, huge tits for someone so petite. “Cool, you’re not ugly,” she says and motions for me to come in.

Dee’s place is a spacious studio apartment in the West Village with wooden floors and an antique fireplace, Björk playing from her laptop. “Just to warn you,” she says between swishes of Listerine, “the guy sort of looks like a troll. Like he’s old and short and has this weird hunchback thing. I think it might be scoliosis? Whatever, he’s harmless. Oh, and he’s super into latex,” she says as she pulls a black latex military dress and matching knee-high boots from her closet. The dress is so impossibly tight it takes her nearly ten minutes to squeeze into it. I’m finding it difficult to speak, mesmerized by her giant breasts. “All ready!” she shouts when she’s finally dressed, then, “Oh shit, I forgot I have to piss on him,” as she runs to the kitchen to chug three glasses of water.

When the doorbell rings Mistress Dee instructs me to hide in the bathroom and not to come out until she says so. She says the slave doesn’t know I’m here and she wants him to be surprised. So I wait in the bathroom with my ear pressed against the door, feeling excited or nauseous or both, I can’t tell. Soon I hear what sounds like a belt being undone and shoes coming off. I hear Dee’s muffled voice saying, “I did a three-hour dungeon session last night, and these boots got pretty filthy. Now be a good boy and make them sparkle for me.” A few minutes later she calls my name and I emerge from the bathroom feeling like a stripper popping out of a birthday cake. I find the slave naked on all fours, aggressively lapping up the myriad day-old bodily fluids from Dee’s boots. “Oh, I forgot to say, I have a friend over,” she giggles. “You may greet her.” He crawls over to me—panting, shaking, sweating, drooling—and gently kisses my bare feet. I try not to laugh but fail.