Jon Van de Moore, Lead Actor, Big Ego

Oscar Wilde famously messed with the people around him as often as he could. As an open homosexual in a nation that had declared it illegal, which I think is not okay, he was jailed and ridiculed regularly. Yet his success as a playwright and story author afforded him social popularity. He also gave us a quote that has been the subject of discussions so many times that I think it would please him to know that it caused so much consternation.

“Life imitates art far more than art imitates life.”

I argued the point once with a girl who I was trying to explain my acting process to. She obviously couldn't get it because she kept saying, "That's great, pretty boy. I just want to fuck."

Currently, I am 28. Performing in my second professional production, an off-Broadway reimagining of The Importance of Being Earnest by Oscar Wilde. I was playing the title role, Jack, whose real name, SPOILER, is Ernest, the befuddled man who is trying to get him and his friend Algernon access to the young women, Cecilie and Gwendolyn. Who are hot and eat finger sandwiches. In this version, Cecilie is black, which is really hot when you think about it because it's over a hundred thirty years ago.

I was doing great. I usually do. I mean, I was getting roses and shit from admirers; mostly well-off benefactor women over the age of fifty. I call them BILFs. I even "thanked" a few of them personally, gifting one of them with my impressive sexual prowess during previews, in my own dressing room, right before the show.

“Wow, that was not what I expected,” she said as I zipped up my costume and checked my makeup. I saw in the reflection that she looked disappointed; probably because I had to cut it short. The show must go on.

“Sorry about that, Maril,” I told her.

“It’s Cheryl,” she said as she came out of my private bathroom I share with the guy playing Lady Bracknell.

“I’ll make sure you get yours the next time.”

“Lovely…,” she said and headed out to take her seat.

It was like that for me. I'm six one, in excellent shape, and I have wavy brown hair and brooding green eyes. Women and men threw themselves at me regularly, but I had to pick and choose. I had to be discerning. Some people are too aggressive and would wear me out, and I had my craft I had to think of. I figured my limit was two fucks during the day and one after the show. So far, that had been working.

Maril wasn't that great anyway.

It was Friday night in the second week of the run that things took a turn.

Claudia, Costume Mistress, Head Seamstress

That boy Jon is an idiot. He does have charm, and he certainly has the good looks. He's sexy enough, I mean, for a mostly white, surprisingly intelligent, egotistical man-baby.

I’ve been a costumer for twenty-three years. I know my stuff, and I can repair faster than a sewing machine when I have to. At forty-seven, I’d say I’m pretty nice-looking. My hair is natural curls. My shape is full, and my best feature is my skin. As we like to say, black don’t crack.

Imagine my total lack of surprise when Jon started flirting with me and eventually moved onto out-and-out hitting on me when the flirtation wasn’t landing.

"I like to take my time with mature women's bodies. They've earned it."

Child, please.

Don’t get me wrong, I love a nice young dick in me every once in a while. I never did marry because I could never settle on just one. I like to pick and choose; quality control.

And this boy? He had everything I would want for a dress-rehearsal-to-closing-night romance. Except for one thing: patience.

I first got a feel for a problem when, during his third fitting, I was fixing the inseam on his second act trousers. He looked down with an arrogant fake modesty. "Sorry if you have to move some stuff around. I have a lot getting in the way."

I raised an eyebrow, grabbed his balls a little too tightly, finished the measure, and started pinning. He winced and held his voice, probably to not let anyone know I had control of the ball(s).

I smiled. "There wasn't enough to be a problem. All done." I usually remind them there are pins so they need to go slowly with removal. Usually.

"Sonofabitch!" he called from the changing room. Oops.

OK, maybe he didn’t deserve that; he’s relatively harmless. He gives us backstage crew a lot of smiles and a few laughs. And a few of them get a regular looking after.

However, you should’ve seen the woman coming out of his dressing room opening night. She was definitely unfulfilled and was not happy about it. He strutted out like a peacock.

He saw me waiting in the wings, as is my custom until curtain. He did not need to discuss something like a quick change. His dresser would handle it, but he made a point of coming over to me anyway, right before “places” was called.

“Hey, C lady.” I don’t know if he was referring to costumer or Claudia. Neither was cute.

I smiled. I like to wear something nice to opening night despite having to work. I had a low-cut corset-style dress. It wasn’t pulled tight by any means, but my size D cup brown titties gave a nice landscape and valley.

He was smirking as if he had an “I told you so” prepared

“Break a leg, Jon.”

If it’s a fellow actor wishing that, the customary response is “you too”. If it’s a crew member saying it, you usually just say “thank you,” or “have a good show”. Not Jon.

He took my hand and kissed the back of it. “You are most kind,” he said with his character’s posh British dialect. Then he took a glance at my cleavage, raised an eyebrow, and winked at me. He leaned in, his breath warm and minty. “Perhaps after curtain tonight you should like the opportunity of joining me for imbibement festivities at the local public house?”

He was asking me out for a drink while still making it sound like it would be a privilege for me to be in his presence.

I smiled but just barely. “Go get some young tail, Jon.”

I headed back downstairs, prepared to put out any costume fires.

Jon Van

Friday night. Week two of the run.

Claudia is a challenge. I mean, I know she wants to fuck. I can see that in most women's eyes. But with her there's a fence or wall, or fence? Yeah, fence — 'cause I can see through it, but it keeps me out, you know? I was trying not to think about it, but nearly dropped a line in the second garden scene.

I had recently taken Simone, the woman who plays Cecilie, to bed, and we had a great time. She was a great kisser and an even better cocksucker. I mean this girl had technique. I held off so that I could give it to her from behind. I always called that the dominant style. Doggy seems so puerile. After my first cum, she had asked me to slow down. Wanted to really vibe on the Jon Van experience. Can’t say as I blame her.

But I admit that she was my warmup-of-color for Claudia. So far, she’s the only woman to say no to me. At least during this show. It happened before, but I was coughing, and it was during Covid, and she was— whatever.

Getting Claudia to go to bed with me, or at least just fuck me in the dressing room, was becoming an obsession. She had said “no” three times and said if I asked again, she was going to report me. I saw a little spark in her eye. I think she meant that as a challenge.

Claudia

Quick background: in the play, Lady Bracknell is Gwendolyn’s mother, and Cecilie is Gwendolyn's bestie. In other words, it’s Lady Bracknell's job to keep these women pure and to pick good men for them to marry. She is a very cold and strict taskmaster. Often played by a man in drag, let’s think of Darth Vader in a corset and gloves.

Now, I don’t wanna shock anybody, or come off as reversed racist or some bullshit like that, but when black women get together and talk about sex, it’s deep and real.

Sweet little Simone (who was playing Cecilie) asked if I would talk to her privately. She came early for the Wednesday matineé with a coffee for me.

“This white boy is really fine, Auntie, but he has no idea how to get a woman off. I told him he needed to rub my button while he was on top, and he literally said, ‘Can’t you do that? I’m busy?’ Like, what the fuck!”

She laughed, but I could tell she was frustrated.

I laughed as well. “You interested in this boy? Because from what I can tell, he’s just a player and not a good one.”

“He hit you up?”

Perceptive child. “Girl, he’s getting nothing but ‘no thank yous’ from Claudia Driscoll. He’s pretty, but I don’t have time for that wham-bam-missed-the-jam.”

“What he needs is somebody to slap him upside the head and tell it like it is. The sad part is that he is hung and it is really fine.”

“Mmmm, girl! I know that. Don’t forget, I’ve done his fittings.”

She howled and slapped my shoulder. Then she sipped her Starbucks. Her face got a little serious.

“I don’t know, I just wanted it to feel better than it did. And it kind of fucks with my head on stage. Why the hell do I want something so good-looking when I know it is so bad for me? It’s like being tempted by a gallon of ice cream.”

“Well, if I was his teacher, I can tell you he wouldn’t leave that classroom until he knew exactly where a clitty was and what to do with it. It’d be ‘Clitoris 101’ taught by Lady Claudia Bracknell—and he better fucking pass!”

“You’re crazy! Hell, I’d hire you out to do that.”

In that moment, we both laughed, and then there was suddenly silence. She looked at me and raised an eyebrow. “He is so into his method. You'd have to do it like it’s an acting class!”

Now this could be very entertaining, I thought. “Give me the weekend.”

"You serious?"

I leaned in and whispered. “Simone, if he don’t make you cum the first time, the next time then I’ll buy your fuckin’ Starbucks for the rest of the run.” I held out my hand, and she shook it.

“You’re on!”

She thanked me and headed out. Now, how would Lady Bracknell teach Jack how to make a woman cum?

Jon Van

I was surprised Claudia sent me a note that she wanted to talk to me after the matineé. I knew she was wearing down. Hard to resist John Van when he’s in predator mode.

I was about to knock on the door of her workroom in the basement, but I decided I should just walk in. A good entrance makes for a better scene.

She was sitting on her small blue couch. She had on a nice African-colors dress with a full skirt that showed off those hot, sexy chocolate titties. There really was something about black women’s nipples that I just can’t explain. I was excited to have them in my mouth finally.

“Close the door. Sit.”

Okay… I did. She crossed her legs and drank some coffee from a mug.

“We have a problem, young man. Do you know what it is?”

No. “Uh, no,” I answered with a chuckle. I wanted to lean back and spread my arms in my classic relaxed position. That always got them. But something about her eyes made me sit up straight. I felt like Jack was in the ‘headmistress’s office.’

“You are a very selfish man, Jon.”

I was gonna respond, but she held up her hand. “No, no. Not for discussion. You have disappointed many women in your life, Jon, and I imagine a few men. But recently, you disappointed someone close to me, and that, my dear, is unacceptable.”

What the fuck? Who?

I must’ve shown the question on my face. My face says a lot. The critics say that all the time. Like, all the time. Gets rather annoying.

She went on. “You think sex is fun, yes? No need to answer. You literally have that tattooed on your hip.”

“Saw that, did you? I like the little squirt drops on the X, like it —“

“Yet it’s not for your partners. Fun. It is commonly a frustration for them.”

“Wait, what are you…?”

She set down her mug and stared at me. Like really stared. Like she was burning into my soul. Like I was having open heart surgery or some shit. It was creepy and really fucking sexy.

And I had a hard-on.

Claudia

Oooo, look at this boy sweat. It’s working. I glanced down with an analytical eye and smirked slightly at the growing bulge in his jeans. Yes, definitely working.

“I see that my criticism is arousing you. Do you get turned on by thinking about how much you disappoint the women you are with?”

Let’s see him untie that knot. I don’t think he’s clever enough.

“I, uh, I don’t…”

“No, you probably do not.” All right. He is mine. This is so fun. I am actually a little wet myself. That will help.

“I do not think you’re evil, Jon. I just think you are misguided. You have exceptional sexual prowess, and you are an extremely attractive young man. Dare I say it, almost irresistible.”

He needed that compliment to proceed. I lightly ran a finger along by cleavage. His eyes were glued to it.

“I am here to educate you. To train you up as it were. Women need to be satisfied, or they will stop coming back. Just how many second dates have you had in, let’s say, the last year?”

He floundered. The highly intelligent mind that he used for his craft could not comprehend a sense of failure.

“I can’t say. Not many.”

“Not any, I would imagine. The quickies with the bored society ladies don’t count. Do you know what a female orgasm even looks like?”

He scoffed and made to answer. Then wisely hung his head. I noted his cock twitched.

“I have a task for you. A challenge if you will. Stand up. Remove your jeans and whatever underwear you have on. Don’t make me ask twice.”

His eyes went wide, but he stood. Getting naked was usually easy for him. It was kind of cute to watch him struggle in this moment. Dayam! There it was; Simone was right, this boy was hung. It was hard and had to be over 8 inches; certainly hefty enough to fill any cavity it penetrated. But it was selfish and needed a lesson.

“You have impressive equipment. Let’s see if you use it well." He arrogantly stroked like he was trying to win a blue ribbon. "Uh-uh. No touching." He quit and blushed. "I want you to please me with your mouth. I want you to make me orgasm.” I spread my legs and hiked up my full skirt. My naked, brown, pink, and purple pussy pulsed in front of him. I took a finger and ran it up and down the wet in an attempt at enticing him even more.

He fell to his knees and dove in like a dog who had been waiting for the bowl.

“Fuck no!” I grabbed his head and pulled it back. He was shocked and certainly embarrassed. “You’re not some pig at a trough! This is a delicacy, and it needs to be treated as such until you can respect it enough. Stick out your tongue!”

He waited. Still in shock, I suppose. I grabbed his face and squeezed it, and he stuck out his tongue. I smiled. I lowered his head back to my now fully aroused love pit. Gripping his hair, I ran his flat tongue up and down my labia, allowing him to not just taste me but spread my thickening arousal over all the right places.

I gave him a soft appreciative moan, and he began to move his tongue on his own accord. I loosened the grip in his hair but did not let him take full control. He wasn’t ready.

“The labia swell with arousal. See? Not as sensitive as the clitoris, but they do need some tenderness before you take them hard. Stiffen your tongue. That’s it, now slide it between the folds. Do you feel the different textures? Do you sense the swelling and need there?”

He nodded and moaned slightly. His eyes were closed. It was as if he was tasting pussy for the first time. And maybe he actually was.

I reached down with my manicured fingers and spread the top part of my lips, exposing my clit from the hood.

“A woman’s clitoris can be sensitive, sometimes even overly. But it will always need attention. See how it is swollen slightly? Almost like a miniature erection? What do you do with erections when you’re with your men?”

He tilted back slightly, his cock pulsing between his legs. His eyes wide, mouth open.

“Boy, it ain't no secret. Do you really think that I haven’t seen some of them flying in and out of your dressing room?” I hadn’t actually. I just heard the rumors and now had confirmation. “Answer me, young man. What do you do with a stiff cock?”

“I, um, I l-lick it.”

“Do it.” He did, with slow strokes on my nubbin, and then a nicely inventive circle. Huh, he had some skill. “What else do you do with it?”

Without answering, he took his lips and tightened them around my eraser-size nub. He sucked it gently at first. I gave him a legitimate grind up into his face. My hand in his hair gripped him more tightly, and I felt an orgasm beginning to boil, albeit on the back burner. The focus was training right now, not satisfaction.

Jon Van

I am still unsure what was happening, but this was the best tasting pussy I had ever had. Most of the time, I don't even taste anything before they tell me to quit. I put a finger at her hole and slid it in. She liked it.

"Smart boy. Slow circles. Wiggle back and forth as you slide in and out. Now, not every woman will want the same thing. I, for example, like two fingers in to make a scissoring motion."

I did it.

“Yesss, just like that."

Heh…Scissors, costumes.

I went a little faster and harder, hoping she would cum so we could -

Claudia

"Stop!" I yanked his hand out and held it to his face. "'Just like that’ does not mean faster and harder, does it?"

He was panting. Just the right amount of fear in his eyes. "Answer me!"

"No, no it doesn't. Sorry, I don't know - "

"What you are doing?"

"What you want..."

He sat back on his feet, and I felt a twinge of sadness for him. He really was lost.

"I'm not very good, apparently. I mean, I try to execute, but I always hear from women that bigger is better, so I assumed..."

I rolled my eyes and tutted in disgust. "Yes, you did. Well, big is great. But attentive is better." I pulled him to me and we kissed. He wanted to go full tongue wrestle, and I growled and pulled back. "What the fuck, piggy? You're at the trough again!"

"Sorry, Miss Claudia."

Huh, I hadn't asked for that, but it felt nice. Maybe it was time to appeal to his artistic bent.

"It's Lady Claudia." I pulled down my bodice and my decolletage bounced into full frontal. "Now," I dropped my voice lower and colder, "let's see if you know what to do with these, Mr. Van de Moore." He was halfway between gob-smacked and fearful of failure.

"Slow, sensible, firm, and attentive." I offered my left breast like I was nursing a child. And in a way, I was. He placed a hand softly but firmly on the side and breathed deeply. His tongue was first, and since I was right steamed inside, it felt glorious. He was soon swirling and nibbling before full-on sucking. By the time he had his mouth full, I was swaying to his beat. I pulled him off, and he shook in surprise.

"Good lad. Now, let’s see what happens when a lady gives you the gifts of her oral charms. Stand up." He almost leapt up and it bounced and splashed some pre-drips onto my boobs.

"Sorry..."

I slid forward on the couch and gripped it firmly with both hands. It was hot and pulsing. A nice thick vein on top and a fat purple-pink head. He was achin' for some quakin'. I took the head into my mouth and swirled my tongue around, being sure to tickle the frenulum. He moaned and put his hands on my head. I slapped them away, and he put them behind his back.

"This is fellatio. Not oral intercourse. She will let you know which she wants. Be...what?"

"Uh, uh, attentive." I nodded and took him back in.

Now, I have had many a dick in my mouth over the years. And my last boyfriend was as sizable, if not more. But I will admit that Simone was right. He was hung, and it was pretty. I had to caution myself to not let him take me as hard as I wanted. He had to learn restraint.

I had him deep a few times but never the throat. That he had to earn. To his credit, he followed my stage directions and held still. "Mmm, good lad. Lovely cock."

I stood, and as we kissed again, this time with more passion and movement, I dropped my dress. When he opened his eyes, I took his hands and led him to the couch.

"Last lesson for today. You have a show in two hours."

I pushed him back, so he lay down. I straddled that delightful pole. I swiped it a few times over my snatch, and we both moaned. Oh, that head...

I lined it up and pushed it into me. The leaky knob popped in with an audible squish, and I lost my breath. I closed my eyes and took a long, slow descent. He was silent, and I realized he was holding his breath.

"Fuuuu...Ohh, Jonny boy. That is - fuck - something." I was all the way down, and he was all the way up in it. As I rose and fell, he was frozen, despite his cock throbbing inside. I finally opened my eyes.

"How...nghh...how does it feel?'

"Amazing. I've never felt this way before." He was genuine, reverent.

I started to grind as I came down. "When they start this move, they are ready to have you start your own. Now go easy, boy."

He ground up with precision and perfectly choreographed firmness. It was fucking glorious. I was soaking him, and my orgasm was driving up the hill ready to launch off the cliff.

"Now, use your hands. Find my clit and rub it in a circle. How I talked about, be - YES! Just like that."

And he stayed just like that. Not faster. not harder. Fuck. I was not long for this world.

"Now, move down when I go up and meet me in the middle." He followed directions perfectly. We were soon making that old blue couch recall its youth when it lived in an old director's apartment.

I grabbed his other hand and slammed it onto my right tit. "I gave you aggressive force. Now match it so I can cum!" He gripped and pulled, and I screamed. "Fuck! Yes, Jonny Boy!"

He was grunting and moaning and soon joined me in dirty talk. "Fuck, Lady C! I'm so close. You are so hot and wet and— OH FUCK!"

He stiffened and his grip nearly popped my tit. But I didn't care. As his cock head swelled and fired off his first firehouse blast, my climax exploded like fireworks on Juneteenth.

"OH FUCK. YESssss!" I shook as the electrical shockwaves rattled every nerve. I would probably have collapsed on his chest had he not been gripping my right breast and my left ass cheek. We both stiffened, held, and collapsed in unison. A perfect mutual orgasm.

It was several minutes of sweaty panting and tremoring before I lifted up. I held his pretty face, and we kissed with no movement, just pressure.

"Well done, lad.” I smiled. "How are you feeling?" I ground a little, feeling his load of cream ooze out.

"I feel like I just lost my virginity all over again."

"Good answer." I returned to the stern voice of the teacher. "And what did we learn?"

He sighed. "Do I have to explain it all, Lady C?"

I chuckled and sat up, my abused breast aching. "I guess not. I suppose you have proven yourself with this audition. But can you repeat the performance?'

He smiled that million-dollar smile that will open every door he wanted. "You know it. I am glad I am getting a Callback"

I laughed at his theatre joke and playfully slapped his chest. He was never going to fully lose the cockiness.

I slowly let him wetly slip out, and I sat back. That truly was a nice cock. He extricated his legs and sat upright. We naturally snuggled. Nice touch, Jon.

"So, was it Simone?"

I smiled. "What do you think?" He softly smiled. "If you really want to show me you are not just a one-night-only performer, you will take that girl to bed and make her scream louder than I did."

He put on his posh voice and kissed my forehead. "Yes, M'lady. I shall."

Jon Van

My second date with Simone that following Sunday evening lasted until Monday. Luckily, we are dark on Mondays (no performances), and we were able to stay in bed most of the day. With the help of DoorDash.

I did everything Lady Claudia had instructed and even learned a few things from my costar. She likes her nipples "popped."

She thanked me for a great time and complimented my tempo and patience. I was equally complimentary. A new thing for me.

I guess I was finally understanding the importance of being earnest.

CURTAIN

Thanks for reading. If you liked it, please hit the heart. If you really liked it, go tidy up, then hit the star.

And as ever, please leave a commentary. I shall endeavor to reply post haste.

Yours,

Lord Matthew Cumsquick