Inadequate Ch. 05

Inadequate

by yfnsp

Chapter 5, Much to Learn

The next morning, Saturday, after I had served breakfast - I was naked except for my cock cage - Rex put a collar around my neck and attached a leash.

I had only been allowed a slice of dry toast. "You'll thank me later," Rex said, although I remained pretty hungry.

"We're going out to earn the money to replace your lingerie," Rex told Cathy. "I know you'll be a good girl while I'm gone, but I'm having a friend come over to supervise you anyway. Marci is very strict, so be sure to do everything she says."

With that said, he led me out to his truck, a large 4-door pickup. He made me wait while he put a towel on the front passenger seat before allowing me to climb in. We headed toward downtown and I thought about the events of the previous night.

Alone in my room, the maid's room (formerly my office), and horny, I had tried anal masturbation using my dildo and, when that failed to bring me off, with two fingers up my butt and my thumb on my perineum, as recommended by the prostate orgasm page I found by googling. That didn't work either.

Later, I was awakened by noises coming from the master bedroom: a lot of thumping, the squeaking of bedsprings, and occasional vocal outbursts. Awakened, and aroused, I listened to what could only be the sounds of vigorous fucking.

So, while Rex and Cathy were racking up orgasms, my count remained zero, and I had lain there, sucking on my fingers until I finally fell back asleep.

I marveled at their accomplishment; Rex's capacity, his resilience, and the sheer quantities of his cum, were astonishing! And I was so proud of Cathy, she had come so far in such a short time. Rex had brought out a side of her that I hadn't even dared to dream could exist. My admiration, like my gratitude to him was unbounded.

A sudden jolt to the truck's suspension brought me out of my horny reverie. We had made a turn and were crossing the railroad tracks, onto the Southside.

Now we were driving past some of the more upscale minority owned businesses in the city. We turned into an alley and parked in back of one of the buildings that faced the main street.

There was no one in sight as Rex took my leash and led me to the back door and I realized that I wouldn't have cared if I were seen like this, naked, collared, and in chastity. It was actually arousing to be helpless in this state.

Rex had a key. I stood by, my nipples hardened by the early morning chill, as he unlocked the heavy door. We entered a dark hallway that led to a brightly lighted area at the front of the building. The atmosphere was redolent of old woodwork and after-shave.

"Hey, Rex!" An exuberant voice spoke. "How you been doin'?"

We had entered the large space at the front. It was clearly a barbershop, decorated in a mixture of modern - three state-of-the-art barber's chairs and bright recessed ceiling lights - and antique - dark woodwork and brass-framed mirrors.

We were greeted by two well groomed black men who seemed to be on very friendly terms with Rex.

"Who's this?" the taller one asked.

"Have you brought us a present?" asked the older, heavier man, grinning.

Rex shook their hands and replied, "This is my new cocksucker. I'd like to install him at the gloryhole for tips, if that's okay with you guys."

They seemed to like the idea. Rex led me part way back down the hallway and put me in a broom closet. There was a cushion on the floor under a circular hole in the side wall through which the white tile of a bathroom could be glimpsed.

I knelt and Rex pulled the chain above my head that illuminated a bare lightbulb suspended over me.

"Bon appetit!" he said jovially as he closed the closet door and left me.

I didn't have too long to wait, although I was impatient in my eagerness. My first gloryhole! I had fantasized about this, as I had also dreamt of servicing "Big Black Cock."

Within a few minutes I could hear the opening of the store and the growing din of multiple voices. Soon, my first customer appeared, obscuring my view of bright tiles and filling the hole with flesh.

It was a beautiful and colorful sight. A rich brown shaft hung through the portal, with a dark, purplish-red section that began about an inch below the big plumlike head, which I leaned in toward and scooped up with my tongue and engulfed in my mouth.

I heard a satisfied grunt as I began to suck. The smooth flesh swelled and stiffened as my tongue and jaws worked it, milking it of delicious precum. Soon I was bobbing my head vigorously, driving the thick shaft down my throat and eliciting sighs and moans from my partner on the other side of the wall. He sounded almost as ecstatic as I felt.

When he came, it felt like an earthquake. Not only was there a palpable tsunami of cum pumping through the pulsing pipe, but the wall between us shook repeatedly from my feeder's quaking legs bashing his hips violently against it.

My sense of joyous fulfillment was multiplied by his jubilant cry of "Fuuuuuuuck yeah!" as he emptied his balls into my hungry belly.

It was my first load of the day, and only the second cock I had ever experienced.

That number would be dwarfed over the next few hours. I lost count somewhere in the twenties. By lunchtime I was feeling quite full, the occasional belch filling my head with the flavor of cum. I had swallowed loads from a vast variety of cocks. They differed in shape and size, but each was delightful in its own uniqueness.

When Rex returned to pick me up at closing time, my jaws were aching. My stomach felt a little queasy. He had to help me walk at first; my legs were too stiff from kneeling to support me.

After sitting on the toilet for a much-needed pee, I was placed in one of the barber's chairs, where the younger of the two barbers gave my hair a close buzz-cut while Rex emptied the tip jar and counted up.

"Almost 200 dollars," he said. "Not bad! That'll almost cover the first purchase I made."

"The first?" I asked, wondering.

"Cathy deserves the only best lingerie, so you've got to earn a lot more than this!" he replied.

I have to admit that, even as tired as I was, the prospect of doing this again was appealing.

"Say, would you either of you guys like to fuck her?" Rex asked our hosts. "Just twenty bucks."

I was thrilled when the older guy said, "Sure, I'll give her a spin."

He reached out a hand to mine and led me down the hall to the office. "I'm Darryl," he said, gently laying me down on the couch there, "but you can call me 'Daddy'." He winked at me and began to strip. He had a nice body, a little thick, but very solid looking; his skin was a nice dark tan, like toffee, I thought.

When he was completely naked and had stacked his clothes neatly on the desk, he took my ankles in his hands and pushed them up, rolling my pelvis up to expose my ass. I admired his long, tapered cock. Circumcised, it was thicker in the middle than behind the head, which was neat and compact, giving it a torpedo-like shape.

"Nice booty," he said. "Here, grab your ankles."

I moved my hands to behind my knees and pulled them up to my shoulders, relaxing my sphincter while thinking what a perfect shape his tool was for penetrating a tight man-cunt.

Darryl squatted and, placing his hands proprietorially on my buttocks, he leaned forward and began to lick my tiny rosebud. A tingle shot up my spine, making my caged cock flutter.

"Oh, Daddy!" I cried out.

"Yeah, baby, give me that pussy!" he growled lustily before planting his lips firmly and forcing his tongue into my tight hole.

I could feel my pucker relax, opening up to his skilled ministrations, his mouth sucking as his tongue alternately fluttered and probed. By the time he rose to align his cock to its target, I was beyond ready.

"Put it in me! Please! Fuck me, Daddy!" I urged, desperate with need.

His bullet-shaped head slipped right in, thrilling me from head to toe. And then he put his weight behind it and steadily plowed a good half his length into me, widening my hole to his broadest girth.

He held it there for a minute, neither advancing nor retreating, as my rectum adjusted, spasming erotically as it opened up receptively.

Then he laid himself down between my raised knees and pressed his chest against mine. I felt his warm weight sink me into the cushions as I wrapped my legs around his waist. His lips found mine and, as his hips rocked, pulling his cock back and then forward, deeper into me, he kissed me, deep and passionately.

I kissed him back, letting his tongue explore my mouth and tangle with mine. I felt like a woman; he was kissing me, fucking me, treating me just as if I were a girl.

Now he was really fucking me, thrusting his long cock in and out of my pseudo-lady-part in long, firm, impassioned strokes. I loved it!

When he came, he held me in a tight embrace, immobile and still. The only motion was the sharp pulses his cock made and the velocity of his steaming spunk as he pumped his entire load into the depths of my bowels.

Hearing our moans of orgasm, Rex came in and inserted a large butt-plug into my well-fucked hole.

"Don't want any messy leaks," he commented, although, as I found out later, he had another reason.

I confessed to Rex, when he prompted me on the drive home, that I had never felt so feminine as I had in Darryl's arms. I believed I now knew how a woman feels when she's being made love to by a man.

"Yeah? Did you like that?" Rex asked. "Would you like to become more feminine?"

I blushed. "I don't know. Maybe." I answered, not admitting that I had fantasized about being a woman.

"Well maybe we should do that!" he suggested.

He handed me my phone as he drove. He must have taken it from my desk at home. My instinctive anger at this violation of my privacy vanished as soon as it began. What rights did I have with him? None, I realized. It seemed right.

"Want to see what you bought for Cathy with today's earnings?"

I tapped the screen and a photograph appeared. It was a beautifully obscene picture of my wife Cathy in bondage.

She was wearing a scanty white lace bra and panty set. She was kneeling with her ankles cuffed together and her arms tied behind her back with rope, quite skillfully and artfully it appeared, with a bright red ball-gag plugged in her drooling mouth.

I was stunned. Man, did she look sexy! But what aroused me most was the look in her eyes: a blank look of dumb acceptance, almost as if her conscious mind were outside of her body, or that she was having a purely physical experience, like an orgasm.

She looked like I felt when I was being fucked, like I was only there for another's pleasure.

"Wow!" I said.

"Scroll through," Rex replied, "there are five more."

I swiped. I gasped. The next one showed her with her breasts exposed, sporting painful-looking nipple clamps connected by a light a chain. And in the following picture, the chain was being pulled, extending her nipples and forcing her tits to stretch out from her torso. The look in her eyes was hard to read; it could have been pain or intense pleasure.

In the fourth picture, Cathy was clearly in pain. Whoever was puling on the nipple clamps was also caning her breasts with a long, thin stick. Her poor boobs were sticking straight out with the tops of their milky white flesh decorated with bright red stripes. Her mascara had streaked her tear-stained cheeks.

These images were so lewd! My caged cock was straining and aching in its cage and my plugged ass-pussy was beginning to spasm.

The final photo was entirely different. It showed a pretty Asian woman, seated facing the camera with a haughty smile of satisfaction on her face. She was holding Cathy's head between her legs by a large handful of her lustrous brown hair, and forcing her face hard into her crotch.

Was she eating pussy? It sure looked like it! If so, it would have been for the first time.

"Ohmygod, Rex!" I exclaimed. "Who took these pictures?"

"I did. They're good aren't they? I took about forty. They'll be going up on social media tonight."

"Really?" I have to admit that the thought of hordes of anonymous men masturbating to pictures of my wife incredibly exciting.

"Does Cathy know that?" I asked after a moment's reflection. I was suddenly anxious about her feelings. She was a very private person, with no social media accounts at all.

Rex smirked. "Not yet, she doesn't," he replied.