The Blue Diamond Club Ch. 02

Subtitle: A Crossdresser's Misadventures

A couple of weeks had gone by since my introduction into the Blue Diamond Club. I'd been too busy with work to pursue anything more; at least, that was my excuse. If I'd been honest, I feared how much further I'd be willing to go. I hadn't dressed in anything fem since that night. Instead, I masturbated in the dark of night thinking about what I could do if nudged. That slight push arrived on Friday night when I received an e-mail from Papa. It said that Joe was hoping to hear back from me – "at least e-mail him a response," he admonished.

I decided to prep myself even for the e-mail. I dressed in a short leopard-print skirt, sheer dark stockings, and a pair of strappy boot style sandals. I went so far as to put on makeup and lipstick. It seemed a bit much for e-mailing, but I wanted to feel sexy.

I explained that I enjoyed our encounter, and I'd love another, but how about a different set of roles, this time out?

Joe replied a short time later:

Hey Princess,

I'm hoping you'll play along with my

little fantasy. I want a gurl like you

that can meet my needs, and I have lots

of unique needs. It gets me off to know

I have to pay for those wants. It's not

like I can't afford it. I like paying for

my pleasures. I ain't no cop, just a kinky

dude with BBC and an unending load. Think

it over.

Joe

My hands shook as I typed the reply. Was I actually considering his offer? I wrote back:

Joe,

Couldn't we just pretend I'm your whore for

the night? I can get pretty raunchy and am

open to all kinds of nasty. Can go with the

hooker role, but I don't need to get paid.

What kind of kink are you looking for?

Cassi ;-)

Joe replied almost immediately:

Princess,

Believe me, baby, I'll make you earn every

cent. Evening starts out on the town – I

know a great hotspot. But you're gonna drop

those panties whenever you're told. I'm also

into light B&D ---> we can finish that off

back at my place. You can bail anytime, but

I think you'll want to stick it out. I want

you, and I want to pay. Also, no condoms.

I've got no bugs and test results as proof,

if you can too.

Buy some sexy-ass outfits for a night at the

club and a dominating night in. I'll pay for

those too.

Joe

My entire body trembled. I decided to play along, figuring I'd leave the money when I left. At least, I'd have a wild night fucking. I sent my agreement, and we made the date for Saturday. I quivered in nervous anticipation the next day, most of which I spent shopping for the right outfits.

For the club, I picked out a pink fuchsia pleated skater skirt with a wet-look fabric that would flounce if I danced and a bright cap sleeve crop top that exposed my midriff. A set of chunky black platform heels completed the ensemble. For the rest of the evening, I chose an ass hugging black leather micro-mini and a rear lacing corset style top in spandex. The shoes I got were faux leather peep toe gladiator strappy high heels with a 5-inch heel. Joe was tall; we'd be at eye level.

That evening Joe arrived in a metallic white Mercedes S550 sedan. I sank into buttery leather seats and crossed my legs in a feminine manner as cool jazz played on the radio. As we roared off, he told me we were headed to a gay-straight mixed club near the downtown area. We make small talk as he drove along the freeway before he pulled off after fifteen minutes. He pulled into a dark, empty side street and parked near the curb. "OK, bitch, time to start earnin' your money," he said as he unzipped his linen trousers.

"Here?"

"Yeah, right here. It's dark. No one's around, and the windows are tinted. Get to sucking."

I pulled his stiff cock out and put my head between his legs. It looked like his rod had grown even bigger since the last time I'd seen it. Fortunately, I'd been practicing on a jumbo sized dildo since I first tried his. I handled it more skillfully this time, working the head back and forth between my lips and licking the tip as I drew in the top. Gradually, I worked five inches into my mouth and with each stoke got more of his cock into me. I'd gone up and down about twenty times; the tip seemed to tickle my tonsils, when Joe exploded into my throat without warning. Half the load shot directly down my gullet, and the rest pooled in my mouth.

"Drink it down, Princess. I don't want a drop of jizz on my leather seats." He handed me a tissue, and I swallowed several times to get down the residual. It had a sweet yet salty taste. He zipped up, as I fixed my lipstick.

"That's why I'm willing to pay, baby. I like to treat the crosser gurls like they're disposable. It's not you; it's just what gets me off. I'm a gay man in a sham marriage; to a woman I see a couple times a year. It works for both of us. I'm not looking for a relationship, just to do anything I want with a hired sissy. Keep a tab going and it's all good."

I sat still trying to digest the last of the slimy glop I'd taken in. "OK, I know the rules now. We're all good."

As we reentered the freeway, Joe told me to pull my panties off and show him my clit. I rubbed it gently as he exceeded the speed limit. I could tell he was already hard again.

"Oh, you didn't think you'd get to rest tonight, did ya? When I need to bust a nut, I'm good for a gallon. I barely dropped a pint in you so far," he laughed when he saw my eyes widen.

My panties stayed on the car floor when we went to the club door. The place looked like an abandon electronics factory; there were no markings on the exterior of crumbling cinderblock and brickwork. If it wasn't for the cars parked in the vacant lot next door and a line of people waiting to get in, the building would have looked deserted. Once inside, patrons were greeting by a gigantic neon club logo that said Club Serpentine Rouge, surrounding what looked like a red phallic shaped sea serpent, rising rigidly from the ocean. The back of my hand was stamped with the same emblem that could only be viewed under UV light for reentry.

The music pounded out a pulsating techno beat that felt like an extended orgasm set to rhythm. It bounced off our bodies and felt like a prelude to sex. On the floor dozens gay men danced and jumped in time to the beats as multicolored beams of light shot randomly overhead. A few straight couples moved away on each other near the sides; the men rubbing their hands over their barely clothed female partners nubile bodies. Here I was outfitted like a hooker, but I was conservatively dressed compared to most of the women gyrating on the dance floor. Joe moved his mouth closely to my ear and through the pounding beats, I barely hear him say, "Welcome to the Red Serpent."

I spotted a few other trannies, but recognized none of them. We had a couple of drinks as we took in the scene, and I waited to see what he wanted next. Joe moved me to the dance floor about twenty minutes later. Several gay men nodded in approval when they realized I was a male in drag. My skirt flared as I swayed in time with the seductive music. My skirt was long enough that if covered my naked crouch and ass, but I'm sure some men knew I was free of underwear.

Joe grabbed me by the hand and pulled me to a staircase, leading me upstairs. A brawny bouncer in a crew cut at the top stood between us and a dimly lit battered black door. Joe slipped him a wad of small bills, and the bouncer stepped aside without uttering a word. We entered a private restroom. It consisted of a single stall and a urinal, but was otherwise deserted. Joe removed his pants and motioned us toward the stall.

"Com' on, Princess. I got us ten minutes."

I knew what he wanted; I'd seen 'American Hustle'. I was about to get fucked in a toilet stall. I moved to walk inside.

"No, baby, me first." Joe bent over, leaned on the john and pointed his ass toward me. "Go on, put your prick in me, bitch."

He looked over his shoulder impatiently. "Yeah, that's right, I need my ass fucked. Get to pumping. That's what I'm paying you for."

I grabbed his shoulder and worked my way into him. His asshole had been well stretched; becoming an easy entry. He bent over as I pumped against his buttocks. He cursed loudly with pleasure, but with the abundant musical reverberation, it would never be noticed. "Ah, fuck yeah, drill it."

I moved one hand down to stroke his cock and balls. I squeezed hard as Joe whimpered with agony and delight. He shot a stream of spunk over my hand shortly before I came inside his puckering asshole. We stood to see two men peeking over the door of the stall, grinning like morons.

"Sorry, but we slipped past the bouncer. That was marvelous. You two are a delight," one said as he pulled out his cock, and the other man dropped to his knees and began a blowjob. Joe grumbled about nobody respecting privacy anymore, as we returned downstairs. He handed me a twenty and said, "Buy yourself a drink. I need about fifteen minutes alone." He started to walk away, but stopped and said, "Take one of those blue diamonds. I want you hard."

So he knows about the Viagra. I guess it wasn't any great mystery. I hadn't seen him take any, but I was just his whore for the night. It was none of my business.

I sipped an energy drink and fended off a few guys hitting on me. Too bad, some were cute, but I was on the job, so to speak. I could always come back another time.

It took twenty minutes for Joe to return. He was accompanied by a massively large black male that I assumed had to be a young pro-football player. I had no idea who he was, but other men glanced his way.

Joe addressed him while barely looking toward me. "This is Cassi, the Princess I was telling you about. Want to take her for a spin? Wear a cover."

The footballer nodded, and Joe dropped his keys into the man's gigantic hands. I started to stammer that I hadn't planned on this part of the deal, but something told me I'd better play along. The footballer put one of his enormous paws on my ass and rubbed it as we headed toward a side door.

"Joe seems in a mood," I observed.

"He's calling himself Joe tonight. Good one," the footballer laughed, "Yeah, Princess; he doesn't like to speak to someone that's just fucked him for a while. Don't take it personal. He likes his space. By the time I'm done with you, he'll be a gentleman again."

The back door of the Mercedes was opened, and I was placed on my knees onto the rear seat with my skirt pulled up. He spit on my crack for lubrication and shoved his hard cock into my waiting hole. Despite his size, his cock wasn't as thick as Joe's, but roughly the same length. His hair had been done up in small braids and pulled back into a ponytail that fell into my face as he began to move his cock inside me. The entire car seemed to rock as he banged away. My own cock was getting stiff from the attention and the effects of the blue pill. I lost track of time and sensed the slithering sensation of this unnamed stranger's cock gliding through my rectum.

He finished with a couple of sharp pushes that nearly knocked the wind out of me. He pulled off the condom and dropped it onto the cracked pavement. The lot was likely full on used condoms. I watched my step as we headed back to the club. I managed to grab my panties from the front of the car and pulled them back on after we returned to the club. At least, the footballer expressed his appreciation of our activity.

Joe smiled as I walked toward him. "Did you show my man a good time?"

"He enjoyed himself," I said in a clipped icy tone.

"Oh, come on now baby, don't be that way. I wouldn't offer you up to him if you weren't something special. There's things I have to do to get along in life. Providing the finest tranny ass is a part of it. Believe me, you are worth the investment."

"This isn't a game, is it?"

"Not the one you were thinking. I told you, you'd earn the money. It's all good, right?"

I calmed myself. Tonight I was the prostitute, for real. I vowed I'd never do this again, but there was no other way home. I'd go along, as long as I had too.

I smiled sweetly back at Joe. "It's all good, sir. I forgot my place; that's all."

"That's fine. You get double for my man. Keep that tab running."

Chapter 2 to follow...