The Blue Diamond Club Ch. 01

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Crossdresser's role playing has unexpected results.
3.1k words
4.33
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16

Part 1 of the 3 part series

Updated 10/19/2022
Created 09/17/2014
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A Crossdresser's Misadventures

Had I gone too far? My rectum was half full of warm soapy water and about to be topped off with hot jizz - from someone pretending to be my father. My skirt had ridden up to my waist, and my garter belt was barely still clinging to my now shredding nylon stockings as my hairless cock and balls flapped with each thrust of my new Papa's cock regularly sliding inside my asshole. I looked at my bright-red toenails peeking out of the black peep-toe pumps with my legs wrapped around his torso as I cried, "Please sir, cum inside me. I want it so fuckin' bad." He was breathing hard, but without letting go of my arms pinned over my head, Papa continued the rhythmic pumping and placed his lips on mine, inserting his tongue.

It started only a few hours before on a dull Saturday afternoon. I was freshly dressed in fem attire. With my legs freshly shaved, I looked cute in the mirror with a formfitting hot pink silky blouse tucked into black leather mini skirt, seamed stockings and four-inch spike heel pumps. I'd done my makeup; blue eye shadow with that smoky look and bright-red lipstick. You look too hot to stay in again tonight; I thought. Maybe I should have thought twice, but I was ready for some nasty action.

Turning to Craigslist, I spotted an ad that stood out:

Older trim Bi Male...very clean

age: 48 height: 5'8"

Enjoy all forms of sensuality...anal stimulation...role play and fantasy...

erotic enemas...safe fucking...groups

CD's, TV's, M/F couples, gay & bi guys - all welcomed

Send stats... pics... details of specific interests

He was twenty years older. In my heels, I'd tower over him by five inches. I moved the cursor to close the tab. However, one thing was holding me back. My cock was rock hard inside my satiny panties. I felt a rush of excitement as my CD clitty strained against the fabric. My erect clit didn't always make the safest decisions, but it knew what it liked.

I pulled up a couple picts from the hard drive. I've always liked the ones of me in a blue satin pencil skirt and matching platforms. They showed lots of my slender legs and curvy ass. I decided to add something to make him especially responsive; I dropped my panties and took a selfie of my throbbing clit and labeled it "Right now - thinking about you."

In the email, I expressed my desire for a take charge type and inventiveness in role playing. Attaching the photos, I clicked send without remorse and waited for a reply.

The wait wasn't long; ten minutes tops. The guy was into everything and up-front about it; a total prev. I liked that he could express his desires. It's such a turn off to deal with someone who can only reply to a sexual offer with a brief sentence that translates to nothing more than "Yeah, let's fuck." This guy had ideas and told about himself. The pictures included some nice nude face shots. He looked well build, his manhood stiff, and that he knew how to use it.

We exchanged phone calls and an hour later I was on my way. My cock quivered with excitement, and precum wetted my panties on the drive. He'd told me to bring some extra outfits to model, which thrilled me. I carried the bag with me to his front door and rang.

He'd mentioned on the phone that we'd start with an unspecified role-play game. I was to go with it, enjoy and there'd be a big surprise later.

"Hi, I'm Paul, come on in," he said as the door opened. He wore only tee-shirt and shorts, and I could see was in great shape for his age, standing with an air of authority.

I smiled with approval. "I'm Cassi." I walked in, my high heels clicking on the tile entry flooring, yet he remained in place rather than stepping back.

He took my right hand. "Please to meet you Princess." He ran his eyes up and down my body, taking me all in while lingering the longest on my shapely legs. Paul had a devilish glint in his eyes; his smile told me he liked what he saw. "You are a hot little tramp, aren't you?" With that, he kissed me full on the lips. As the kiss lingered, I could feel his tongue dart in and out of my mouth. I felt his hand run up and down my ass.

While still holding my hand, he led me into his living room. The furnishings said 'divorced'; a cloth couch and a leatherette easy chair dominated the room. Across the kitchen counter, he mixed us drinks as we made small talk. He insisted I sip a girly Cosmopolitan Cocktail through a thin straw that I let caress my cherry red lips. I noticed the protruding budge in his shorts. Since he wasn't wearing underwear, it was easy to glimpse his erection.

"Impressed? To tell you the truth, Princess, I'm a member of the Blue Diamond Club," he said with a sly laugh.

"I don't know what that is, baby."

Again he laughed. "If you're a good girl, I may let you join. You'll see what it's all about shortly. In the meantime, you'll address me as 'Papa'. I'm going to be your daddy tonight. Ever fucked your daddy?"

So this was going to be an incest fantasy. This was different from anything I'd done before. "No, sir, I've never let him fuck me. I've been a princess too long." I stooped to my knees. With a slight tug, I released his erect member through the leg of his shorts. The head was nicely cut, and I guessed it to be about seven inches long. I opened my mouth and slowly inserted it. I moved his cock back and forth across my lips lapping at the tip.

"You've become quite a little cock sucker, haven't you? You've sucked lots of cocks, since I sent you to college. You're a dirty little skank now." With that, he pulled me up and in one, swift motion dragged me across his knee. He swatted my ass firmly and resoundingly. My leather mini was unceremoniously hiked over my hips, and my panties pulled down to my thighs. Papa then landed a sharp slap against my exposed buttocks. I breathed deeply, knowing another blow would be coming. He smacked my other cheek with even more force. The way I wriggled on his lap told him I approved. More slaps rained across my butt turning it warm and red.

He led me to his sofa, and I sat across his legs. He ran his hands up and own my nylon encased thighs as we kissed passionately. My ass still shuddered from its spanking. His hand worked its way to my crotch and I felt a jolt of electricity as he caressed my shaft.

"You have a nice little clitty, my dear." My penis is at best five inches when fully erect, which may be why I've always identified with being a 'gurl'.

My head was spinning from the attention of my swollen clit and the strong booze. Papa pulled his hand up toward my face. His palm covered with my precum; he made me lick it clean.

Soon afterward, we moved to his upstairs bedroom. Beside the bed hung an enema bag that bulged with fullness, and a tube set freshly lubed. "All for you, Princess. Get into position."

He positioned me on the bed on my knees and ass in the air. Papa wiped my sphincter clean and inserted the tip and ran the tube what felt like a foot past my anal opening. He released the hose clip, and I felt warm water flowing into me. He had me lay flat and rimmed my asshole with his tongue for a fabulous five minutes.

"Go to the bathroom and release most, but leave about a third. It'll increase the entire sensation for you."

By the time I returned to the bedroom, he was still rock hard.

Papa examined my swollen clit and began to gently stroke my erection. Slowly at first and gradually picking up the cadence. Mentally, I fought hard not to cum. I wanted to keep my horny buzz going while getting fucked. My precum was self-lubricating for Papa as he rubbed his hand over my cock and balls. For several minutes, I heard someone moaning. It took some time before I realized the moans were coming from me.

With a few more skillful strokes, I released my pent-up load. I gushed in a warm white stream that left a thin soggy trail up my shirt and blouse and reaching as far as my throat. Without thinking, I screamed a torrent of verbal obscenities, like I was a teenaged virgin experiencing her first orgasm in the back seat of an SUV.

"Oh shit, I didn't want to cum yet," said as I recovered my senses. Usually I preferred to ejaculate after I'd been fucked.

"Don't worry about shooting your load, I can help you out, Princess. I want you to enjoy this nearly as much as I'm going to." With that, he reached onto his nightstand, grabbed something and placed it into my opened mouth. The pill was tiny, and I swallowed accidentally. I felt a sense of panic. I didn't do recreational drugs.

Papa saw the look in my eyes and sought to reassure me. "No, it's not a drug. Well, not the kind that will get you high. I've just given you some Viagra. In about twenty minutes, you'll be harder than iron and eager to fuck like a jack rabbit. Welcome to the club."

I didn't believe him, but relieved to hear wasn't something else. I wanted to be sober enough to drive home. I managed a decent come-hither look and said, "While we're waiting, why don't you take me?"

After going down on his hard cock, I split open a condom wrapper and unfurled it over his saliva drenched erection. I wiggled my hips as Papa grabbed my hands and pulled them above my head, pinning my hands securely to the pillow. In one spry motion, he maneuvered his hard-on into my rectum. I was pleasantly surprised by a wave of pleasure as he pumped away at me. The pills were kicking in. He planted his lips onto mine, and his tongue violated the recesses of my mouth as he thrust his cock into my asshole.

He talked dirty to me the entire time; most of it telling me what a filthy slut I was. "I've heard you're selling your hot little ass after school, Princess. You're a filthy whore, aren't you?"

My head swirled with excitement as I confessed, "Yes, Papa, I've been hooking on the side. I've been very bad." Oh my lord, was I enjoying myself. My penis was becoming hard yet again.

Matching the rhythm of his thrusts into me by moving my hips in-sync with his gyrations, I yelled, "Please sir, cum inside me. I want it so fuckin' bad." I felt myself begin to release in concert with Papa's eruption. As I felt his pulsations, I deposited more sticky cream onto my smooth belly. A pool of sperm ran into and filled my navel.

We panted heavily. I felt the sweat leaking from under my wig. I cradled myself in Papa's arms as we caught our breath.

"The little blue pills are Viagra? They do wonders," I observed. Since the pills were diamond shaped, thus the nickname.

"The secret to my success. I'd had less and less interest in sex for the last twenty years until a doctor offered me a free sample. I was barely able to get semi-hard until I joined the club. Now I can go a couple times a night. I've never fucked anything but women, but now I get so horny that it opened my horizons," he said as he offered me a drink and slid another diamond into my mouth. This time I swallowed willingly.

Papa's face took on a diabolical expression. "Your surprise happens in about fifteen minutes. Grab your bag, get cleaned up and put on that other outfit to model for me?"

I tried my best to wheedle a hint; even using a little girl pleading for candy voice, but to no avail. He slapped my ass a few times until I scurried off to the bathroom.

My makeup was a mess that I hurriedly cleaned up adding even more eye shadow and lipstick. I changed to a pair of fishnet stockings, red spike heel sandals that had a single wide band with small silver studs at the toes and zip up heels. I pulled on a matching red shape hugging spandex skirt and black spaghetti strap top. I changed to a blonde wig that flowed past my shoulders. A quick glance in the mirror told me I looked like a total street hooker as my penis began to revive.

Downstairs, it sounded as if Papa had turned on the television. Perhaps he was playing some porn? I sashayed down the staircase and strutted into the living room, eager to show off. Papa had remained naked, and I hoped to see him stiffen when he saw me.

That is when I saw my surprise. In the chair sat a middle-aged black man. I guessed him to be in his late forties. He worn only a pair of boxer shorts that the tip of his penis poked through the slit.

Papa gave me the once over. "Joe, this is my daughter, Cassi. I call her Princess. She's just home from college and become quite the little slut. She's been spreading her legs for just about anything with a cock. Hell, I just fucked her brains out before you got here."

Joe's penis continued to rise out of his shorts. He was huge; at least 9 inches and thick. "She looks like a real hoe. Hey, Princess, why don't you turn around and let me check out that ass of yours?"

I did as asked and my knees began to quiver.

"That is a mighty fine piece of ass you have there, child." He shook his head and rubbed his cock.

Papa said, "Here I am sending the girl to get an education, but she spends most of her time fucking and sucking. But you know what, Joe? They still haven't taught her to accept other races. Can you believe my little Princess has never fucked a black man before?"

Joe shook his head in a mock gesture. "Shameful. It's time I schooled that ass. Come 'er, you little bigot."

Using my best southern accent, I said, "Why I do declare, I'd be afraid to fuck a black man. Y'all are so big. What if my lilywhite ass-pussy can't fit that monster?"

Papa commanded me, "Get down on your knees put it in your mouth."

I pulled Joe's shorts off and took as much as I could into my oral cavity. His cock was dark mahogany in color and smooth, with a flaring mushroom head. I worked to get as much as possible, still I struggled with it.

Papa pulled up my tiny skirt and exposed my crotchless panties. He grabbed a container of Vaseline and greased my puckering hole with two fingers, then worked in three and finally four. He glided his fingers up past the knuckles.

"Your little princess is a real tart. She must be whoring herself out."

"I told her she had to help with the tuition. She sells her ass on weekends."

"Hey, Princess, how most do you charge for that fine piece?"

I pulled Joe out of my mouth. My jaw was starting to ache from trying to engulf that nine incher. "I get $150 from all the white boys, but my ass is yours for free."

On my knees, Joe gradually slid his full manhood into me doggy style. With his well build physique, he was easily able to control my pretended gestures of resistance. I was grateful that he entered me gently, but I pretended to complain in my southern girl accent "Oh Papa, his shaft is just too big for me. I can only handle those little white pricks. Have mercy, sir." Joe reached around to my thighs as he pumped away. I heard a squishing sound as he slid in and out.

Papa put his cock into my mouth, and I sucked it down easily. By comparison, taking him in whole was easy.

I tasted a few trickles of precum but didn't get a blast of the full ejaculation. Instead, Papa pulled out and left the room. He returned minutes later with a camera and proceed to take pictures of Joe pumping away at my ass. I felt a twinge of remorse and shame with each flash. "You can use these to advertise. I'll bet black men would pay $200 to screw your hooker cunt."

Joe began to cum heavily into me. I could feel every pulse. He pulled out and removed the condom. It felt as if there was a full quart of semen in the reservoir, which he poured onto my ass. He squatted and spread his legs as Papa inserted his cock into Joe. I stood and began to stroke my protruding clitty as they watched.

"Princess, put that into my mouth, I want a taste," Joe said as Papa moved back and forth.

A short time later, both of us came into Joe. He slobbered the goo down the length of my shaft and onto my scrotum, where it dripped onto the rug.

The three of us lay in a heap cooling off. My ass throbbed from all the attention.

Papa explained that he'd tried to get together with Joe for some time, but the pictures of his whorish little daughter sealed the deal. I managed to make Papa promise he'd keep the pictures he'd taken of Joe and me to himself and send me copies.

A half-hour later I cleaned up once more, still dressed in my blonde hooker getup and was about to leave. I grabbed my bag and was almost out the door, when Joe pulled me aside. He slipped me a piece of paper with his phone and e-mail. "You're gonna charge two hundred to the brothers? Couldn't I get the white-boy rate?"

I winked and said, "For you, baby, I'd go a hundred, and I'm totally worth it." I kissed him once more inserting my tongue between his lips.

A week later I had a doctor's appointment and scored myself some blue diamonds. I was in the club.

Chapter 2 to follow...

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2 Comments
DeborahAnneDeborahAnneover 9 years ago
My First

My first time getting a cock pushed into my cute little butt was from my step dad, I also sucked his cock and swallowed his cum, later on I got a nice black man to suck and fuck me, I think of the two cocks I liked the black mans better, his cum was sweet. da.cd@frontier.com

AnonymousAnonymousover 9 years ago
Laudable and wholsome!

Most of the time it's poop and gas!

But it's way more fun gettin' cum in my ass!

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