Inadequate - Cover

Inadequate

Copyright© 2024 by yfnsp

Chapter 5: Much to Learn

Erotica Sex Story: Chapter 5: Much to Learn - A journey from head of family to servant sissy slut. Feelings of inadequacy lead John to embrace an effeminate persona. When he becomes obsessed by Big Cock, he subjects his whole family to degradation and becomes submissive to all.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Fa/Fa   Ma/Ma   Mult   Consensual   Romantic   Slavery   Gay   Lesbian   BiSexual   Heterosexual   CrossDressing   Fiction   Cuckold   Slut Wife   Wimp Husband   Incest   Mother   Father   Daughter   Grand Parent   InLaws   BDSM   DomSub   MaleDom   FemaleDom   Humiliation   Light Bond   Group Sex   Interracial   Black Male   Black Female   White Male   White Female   White Couple   Anal Sex   Analingus   Cream Pie   Double Penetration   Exhibitionism   Masturbation   Oral Sex   Pegging   Pregnancy   Menstrual Play   Public Sex   Size   Prostitution  

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.”

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