Chasing Diamonds

Lisa curled an eyebrow then repositioned his hand.

"This isn't a mirror universe Poindexter, ...THAT'S my heart."

Marty blushed then started reciting as if taking an oath.

"I, Martin, solemnly swear to be a good friend, a decent roommate and a passable sissy bitch boy so help me God."

Lisa snickered before holding up one hand while grabbing his crotch with the other.

"I, Lisa, do solemnly swear to be a good friend, a tolerable roommate and to mercilessly whore your sissy bitch ass out whenever I'm not balls-deep inside it, so help me God."

"What Onlyfans and a suspiciously lax VIP policy hath brought together, let no man tear asunder." Marty answered, "I now pronounce us Roommates slash Power Top and Occasionally Bratty Bottom."

Marty shook her hand.

"A Bratty Bottom huh?" Lisa with a decidedly sinister chuckle, "I've got something that'll fix that."

"I hope it's a big something," Marty replied with an insolent grin.

They started to giggle uproariously.

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*Martin*

And thus began the by far strangest point in my already odd life.

Previously I would have said getting paid to play and debug video games for a living was as odd as it gets.

Having my, at the time, best friend and business partner ask me to crossdress and go out with him publicly to make the girlfriend he was simping for jealous was more odd

Having Josh sell our part time business to a triple A gaming company at the behest of the girlfriend who was stringing him along was more annoying than odd.

Meeting a cosplayer who cosplayed the character that many do not know you originally created and designed to be futanari before the previously mentioned triple A gaming company changed your designs to make them more family-friendly was even more odd-- but fun.

Then I found her Onlyfans page and was dancing at a local club which was odd but convenient.

Lisa was actually storing a lot of her stuff at the club so we simply had to pack it in an Uber and drive to my apartment.

I wasn't bullshitting Lisa about getting her top quality gear for her Onlyfans. I had most of it already thanks to the crossdressing incident.

The digital camera and lights were hanging around the apartment as was the audio and video editing and production stuff.

In fact Lisa's first new pictures co-starring her "gimp sissy slave" went up a few hours after she was moved in.

She took a few fetish shots posing with thigh high heeled boots on her new bed.

Then she begged me to model the Catherine costume and once I had dolled up, her gimp-boy sissy brought her favorite sextoy to masturbate with on camera.

Which is how her online subs met Martina.

Her subscribers loved it and as the quality and quantity of her output increased her subscriber count skyrocketed.

And yes she and I had sex, a lot of fun and kinky sex. At first it was solely for fun, the whole Friends with Benefits concept let me enjoy our sexual relationship without the odd feelings when someone in Dubai paid her a thousand dollars to eat her dinner nude on camera.

We obviously started to do it on camera. With me wearing a latex gimp mask-blindfold, it was weird at first, but as she pointed out, the mask helped me play the part of Martina. A role mostly separate from my day-to-day life.

One day a few subs wanted to know why Martina didn't shave. That was my introduction to shaving on the regular. The nanosecond I started that, Lisa had me put on a latex maid's outfit and hang around for the stroking.

Her subs skyrocketed. Martina started wearing a cock cage on cam and eventually Diamond talked me into walking around with a butt plug occasionally just so I could further train my ass and know how comfortable or not I was with stuff up there on the regular.

That's when I noticed that some men and quite a few women are much more relaxed and flirty around an obviously submissive bottom.

I'd be lying if I didn't admit to going through Martina's fan mail occasionally touching myself as I imagined some of the fans cranking out a few tasty ones to my femboy persona.

I encouraged her to do reaction videos to popular trailers and video games.

I wrote her review scripts for her so she sounded knowledgeable. Then she had the novel idea of livestreaming her gaming. She'd play a game while I sucked her to completion or I'd play a relatively low stakes game and she'd stroke and tease me until I exploded.

That got us hundreds of new subscribers. Apparently there's a lot of people who enjoy watching a femboy lose to an easy to beat boss because he had a sissy-gasm.

One of the most popular reactions was to episodes of a vampire-themed anime, specifically a BDSM flavored character arc that featured pet play.

Apparently the only thing more fun than watching a vampire princess femdom someone into her rutting sex pet was an actual futaDomme making her sissy-slave orally pleasure her while she enjoyed it.

I cleaned up the fetish stuff from some of Lisa's Onlyfans material and reposted them to YouTube. Top2Bottom Gaming started a whole new revenue stream for Lisa. Plus by linking to the Onlyfans the subscriber count exploded.

I even started building a Souls-a-like game during my downtime. Kind of a Hollow Knight meets Memoirs of Geisha. The player COULD slog through the game beating their heads against a series of increasingly thick brick walls while wearing standard armor or clothes to win but the players who chose to don certain girly outfits and cosmetic flourishes that possessed a combination of gameplay buffs could take advantage of the combination of status effects and enemy debuffs that would essentially turn even the hardest difficulty into story mode. In other words, if you wanted to Get Good - you had to Go Girly.

We celebrated 1 million YouTube subs with dinner at the restaurant I was dumped in. I thought it would be humiliating but in fact it kinda felt triumphant.

Turns out Steve the manager was a lifestyle sub for the head chef. Once he knew I wasn't just a wannabe day player who didn't appreciate proper boundaries, aka a creepy creep getting what all creepy creeps deserve, he asked Ida, his Dominant, if he could give us the VIP treatment.

It felt pretty good being validated for my fetishes instead of getting kink-shamed.

Ida stopped at our table and we actually had a good little chat about food and the lifestyle. I was doing most of the cooking around the apartment so when the joke was made I should put that online I laughed, ...I figured who in their right mind wants to watch a femboy gimp slave cooking recipes for a big dick domina?

Turns out a few hundred subs on YouTube and Onlyfans both, several of whom had very specific recipes they wanted to see me prepare while Mistress Diamond messed with me.

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*Martina*

"Welcome to Mistress Diamond's Kitchen where we are preparing Diamond Cheeseburgers." Mistress Diamond announced.

"As always manning, and I mean that in its loosest connotation, the kitchen is my sissy bitch Martina, ... say hello to the audience Martina."

The dolled up sissy who waved at the camera wore an apron over his clearly naked form that barely concealed his caged dicklet.

"Oh yes Martina had some strongly worded opinions on a hamburger recipe submitted by a subscriber," Mistress Diamond said cheerfully, "unfortunately he forgot he only gets to have MY opinions not his own so now he gets to stay ball-gagged and caged."

Diamond held up a plastic vibrating cock cage and displayed the toy like a game show hostess or model.

"Incidentally Martina got this lovely little gift from an admirer," Diamond chuckled, "apparently when you little monsters chat with us, a wireless signal activates the toy so feel free to tell Martina what a horny sissy slut he is."

The chat notification pinged which caused the toy wrapped around Martina's dicklet to start buzzing causing him to moan hotly around the ball-gag.

"Now, what do obedient cumsluts say when Mistress gives them a present?"

Martina moaned as Diamond used another toy with a bulbous tip to tease his ass.

"If you even think about cumming before you finish cooking my meal you'll deeply regret it." Diamond growled, "now get to it."

Diamond and Martina started the cooking demonstration, with Martina delivering standard patter and commentary around his ball-gag so folks at home saw instructions coming up onscreen that matched what he was grunting as he prepared the meal.

The main difference between this and any other cooking demonstration was Diamond indulgently praising Martina as he displayed each ingredient.

When he prepared the meat Diamond made him show the folks at home while she mimicked his actions while stroking his balls and shaft.

He finally put the burgers on the grill alongside the buns which he toasted before seasoning both.

"Good boy," Diamond cooed in Martina's ear while relentlessly edging and teasing Martina.

The notification bell signaled the continuous vibrating torture and Martina started twitching around, wiggling his hips as stimulus from both ends had him quickly on the brink of climax.

Soon enough he started to prepare the butter sauce for basting both his burgers and the buns.

Diamond slid behind Martina and began rubbing him as her hand reached around and cupped and massaged his balls.

"Now Martina is going to brush on our butter sauce including the extra special secret ingredient." Diamond hissed.

Martina nodded, moaning as Diamond started to rub his balls, already swelling and aching with his pleasure at his submission to the vibrating toy around his sex and the toy teasing his ass.

"Now remember that good little cocksluts cum on time but if your bitch is as disobedient as little Martina here, you might want to reduce temperature on your grill at this point until his orgasm reflex is properly trained to cum when YOU WANT him to, -- isn't that right Martina?"

Martina moaned and whined as he approached his climax and Diamond placed a dish of sauce underneath his twitching hardness.

"Like any decent cooking demonstration we did some prep work beforehand to make things easier," Diamond hissed, "Tell the folks at home how many loads I fucked out of you, Martina."

Martina held up five fingers before he exploded over and over into the cup which Diamond set on the counter.

"And there we have it, the perfect creamy addition for all you sissy sluts looking for a perfect little meal to serve your Goddesses."

With Diamond's futa-cock hotdogged between his thighs sawing back and forth, Martina took a brush and, mixing the concoction together, brushed it over both of the burgers and the buns.

The scene cut to the taste table Diamond sat with her cut open juicy burger with Martina still on her lap.

"I think this sissy bitch needs a little more cream on his burger don't you folks?"

Diamond withdrew the vibrating toy and bent Martina over the table and with quite a loud groan, shafted herself deeply inside his hungry boy-pussy. Bucking her hips rhythmically, she sang the praises of his warm tight hole and the vibrations from the cock cage she could feel even deep inside him as she was.

Martina moaned and whined around his ball-gag as his prostate was repeatedly overstimulated until with a groan he exploded his load on the table. Diamond dipped Martina's burger in the mess and then waved the treat before her. Martina took a big bite. Which Diamond rewarded with praise and kisses.

"And this is why we solicit you little monsters for recipes, according to Martina we have a few other meals that we can use Martina's special sauce for, tune in next time and you'll see."

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*Martin*

As you'd probably expect, I installed a second cam focused on the food so I could switch to it for the YouTube cut. According to our analytics several people actually watched both versions so they'd beat off to the sex then go check out the actual recipe on YouTube.

I'd be lying if I tried to say that the next lifestyle change was entirely unexpected.

Diamond's fanbase was growing but unbeknownst to me was so was Martina's. OK obviously I knew Martina was popular with Lisa's subscribers.

The comments, emails and suspiciously detailed fetish scenarios -- a disturbing amount of which I found strangely exciting to read and occasionally pleasure myself to -- were confirmation of that.

She was doing stuff in the scene that had attracted curious eyes.

Apparently I was a popular submissive. How popular, you ask?

Popular enough to be recognized out in public, especially as once we got big, Lisa wanted me to girly-up more frequently, and not just simple cross-play.

Martina needed a wardrobe expansion. Not just underwear either. As Lisa's tools got better, so did her standards for what she produced with them. Martina was as much a part of her online persona as her boots or her makeup all of which she decided to upgrade dramatically. And the cosplay enthusiast in me was just as eager to see how far I could take this Martina thing.

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It was a strange new day when Marty stepped into a clothing store looking for something not for himself but for Martina

Marty obviously had shopped for himself before but shopping for his femboy online persona was different but one of the subscribers sent a digital coupon code so he figured he'd take advantage.

Marty walked into a midtown store and drifted through the aisles looking for a swimsuit. Mistress Diamond was doing a beach themed episode of the cooking segment. Martina needed a swimsuit and this wasn't like cosplay where he could hide any insecurities about crossdressing behind a geeky commitment with getting details correct.

He found a few potential items and carried them to the checkout area. The attendant was staring into the middle distance when Marty inconvenienced her by existing.

"Are you shopping for your wife or girlfriend?" She asked in a bored customer service drone, wearing a smile as fake as her jewelry.

"Yes ma'am," Marty deadpanned.

There was something about her condescending smile that reminded Marty of the girl that dumped and cuckolded him for his fetishes

"I'm shopping for my wife and -- or significant other."

Her smile faltered and Marty suspected she was going to say something savage but a soft but commanding voice got both their attention.

"Celeste, take your meal break -- I've got this one."

Celeste glared at Marty a moment, "Thanks Jordan," she grumbled.

"In fact, why don't you take a full hour -- I think this one's gonna be a good little while-- I'll just leave your cashier's ID plugged into the terminal when I ring up his sale."

Marty caught Jordan's wink and immediately backed him up.

"Actually it's sales -- plural." He replied.

"There you go, the easiest commission you'll make this month and all you have to do is take a long lunch."

"OK I get it this is me leaving," Celeste grumbled but walked away leaving Marty alone with presumably her supervisor.

Once Celeste wandered away, Jordan turned to look at him. Martin looked closer and realized Jordan was actually a very pretty femboy.

Indeed Marty was mildly jealous that Jordan was clearly more experienced than him or at least relaxed enough to not project the nervous energy Marty usually felt whenever he dolled up away from the camera which made Jordan's next words surprising.

"You look pretty different in real-space," Jordan observed, "you're actually a pretty hot looking civilian."

"I'm sorry,...have we met?" Marty mused.

"I'm a fan," Jordan laughed, "I comment on all your posts -- that digital coupon was from me."

"You watch Diamond's Onlyfans?"

"Me and a couple hundred other subscribers," Jordan snorted, "so why are you getting dolled up?"

"A beach themed episode," Marty replied, "someone who's a big fan of Pulp Fiction wants me to make an actual real life version of a Big Kahuna Burger."

"The Hawaiian place Brad gets his last meal from," Jordan laughed, "that'll be awesome."

"Diamond wanted me to wear proper beach attire."

"Oh with a cute sunwrap please let me put you in a sun wrap and some makeup -- the pricey stuff, not whatever you've been shoplifting out of the drugstore clearance bin and using so far."

"Wow, don't hold back -- tell me how you REALLY FEEL," Marty replied dryly, "Now I'm starting to remember your comments."

"Honey you're representing every loud and proud femboy and sissy out there. We are living vicariously through you, since we want to look hot; of course we'd want YOU to look hot."

"Okay let's do this," Marty replied with a resolve he didn't fully understand but didn't want to fight.

Jordan and Martin headed for the change rooms with Jordan grabbing a few cosmetics on the way.

Jordan sat Marty down and started working on his make-up. Getting a full make-up tutorial from an experienced femboy was definitely an education-and-a-half. Martin learned a lifetime of tips that afternoon.

Then Martin started trying on the outfits he'd picked out then Jordan tossed those because they made Marty look cheap.

"Aren't I supposed to look like a cheap slut?" Marty snorted.

"No you're supposed to look slutty, not cheap," Jordan whispered, "-- there's a difference."

Jordan picked out a two-piece bikini which was handed to Marty. It was strangely exciting. Martin quickly realized the material, tight and stretched across his curves, was stimulating his throbbing arousal.

"This is the best part of being a sissy-sister," Jordan whispered in Marty's ear, "the right kind of clothes and you barely have to touch yourself to get off."

Jordan didn't try to hide his own swollen member as he reached inside the bikini bottom to fist Marty's arousal.

Jordan stood behind Marty rubbing his aching hard shaft, humping against Marty's ass while stroking him.

Finally Jordan practically ripped the bottom half of the slutty two piece off, pressing himself against Marty's backside as he started to rub and tease Marty's chest and hard nipples through the tight bikini top. Jordan's hands traveled down Marty's belly to his needy dicklet, hard and already perilously close to spewing a hot load.

"You know you're my hall pass,"

"Hall Pass?" Marty moaned.

"Me and my partner have an agreement about real life people we'd fuck if we had the chance," Jordan explained, "You're on my list."

Jordan pulled out a cell phone and took a selfie of himself standing behind Marty obviously rubbing himself against his butt while giving the aroused young femboy a kiss.

Jordan bent Marty forward who whispered to him that Jordan's cock felt good on his ass.

"Who broke your ass-cherry, sweetness," Jordan whispered. His fingers teasing and edging Martin's sex.

"I joined the swim team in school," Marty replied, "the swim coach asked one of the guys to help me practice my form, -- we worked on way more than that."

"Tell me what happened,"

"He drove us home and took the scenic route. It was the first time I parked with anyone and I got fucked."

"He fucked you with his big cock did it feel good?"

"Not as good as yours," Marty whispered between grunts as he felt several inches of Jordan's cock-meat work its way deep inside his boy-pussy. Martin started grinding against Jordan's body trying to claim as much femboy dick as possible. Jordan fucked him hard and Marty moaned in pleasure. Jordan pounded his brown hole until with a gasp he released a strong flood of creamy goodness inside Marty. The young man dropped to his knees and inhaled Jordan's dick cleaning it off and getting it ready for the next of was ultimately three rounds.

At the end after Jordan sucked him off a final time he told Marty he loved meeting him and to cum again anytime.

Celeste was happy to win the monthly sales award, getting a transfer to a different store with higher turnover. Jordan was so happy with her transfer Jordan invited Marty back to meet his significant other who definitely appreciated getting a live reenactment of Jordan's hall pass.