Howard wore jogging pants and a NY Raiders hat on his head when he stepped out of his house. It was 06:12 pm. He carried a gym bag slung over his shoulder which supposedly contained a towel, water flask, a bar of soap, and everything he might need when heading to the gym. Today, unbeknownst to April, Howard had other things in mind.
Howard strolled in the direction of the gym with a leisure bounce to his steps. He waited till he had gone a distance before making a call and got a response that made him smile as he continued his stroll. He arrived at the gym but did not walk inside. A car honked its horn from across the street that caught his attention. Howard recognised the car and approached it.
The passenger window slid down to reveal Charmaine smiling from behind the wheel. He was decked in a typical outlandish female outfit with a different hairdo this time; it was almost impossible from afar for anyone not to identify him for a woman.
"Hiya Howie. I got here way before you called."
Howie shook his manicured hand, taking care not to ruin his painted nails.
"I figured you would be. I just wanted to make sure."
"So, this where you come to get those cute muscles on you?" he gestured at the gym. "How nice. Are you ready?"
"Yeah, let's do this." Howard slipped into the passenger seat and threw his bag in the back after slamming the door shut. "Whatever we do, we'd best hurry. I've got two hours' worth of freedom time before April might get worried and start calling." He took off his Raider's hat and into the backseat it went as well.
"Sounds just about as much time we will need." Charmaine put the car into gear and drove off from the vicinity.
Charmaine lit a cigarette while he drove. He glanced at Howard and smiled charmingly while focusing on his driving as they cruised out of the neighbourhood.
"I thought you might have told her by now," Charmaine enquired.
"I know I should. Don't feel right letting her know right away, not when I'm just getting started. But let's see how things go. If it'll be something I'll want to try more often."
"You ought to quit kidding yourself thinking that hasn't already happened." Charmaine blew smoke out his window. "I already told you before that you're hooked. Only thing is be careful what you wish for."
Howard turned to him but did not say anything. He ruminated on his statement. Neither of them said anything for a while.
The drive was a long one going beyond the city limits. They pulled into a gas station two miles beyond the city for Charmaine to fill his tank before continuing. They made conversation along the way. Charmaine explained several lessons he had imbibed from serving Ms. Jenn and of the disciplinary tactics she employed when it came to setting her slaves in order.
"Is she always strict?" Howard asked.
"Whenever she wants to be, yes. But as a loyal servant, we all love her for it. If you watch her getting fucked you'd think she'd been a whore her whole life. I found out it was not until four years ago that she got her first Black cock taste. She was not what she was now back then."
"What was she then?"
"More of a society-type woman is what I know. She was married to hedge-fund guy but there was some scandal and things went bust. She disappeared for a while and then came back to what she is now. Not much to go on, I know, but you'd have to ask her yourself. If she's willing to tell."
"How did you get to know about her?"
"I was at some cosplay party and I heard some guys talking about her and the stuff she does. I hooked up with them to see what it's about and since then I've been a devoted servant."
"How many followers does she have?"
"Too many for me to even count. Some come and go and don't return for a while, but that's few in-between. You won't believe how many white boys out there that would do anything to worship a Mistress like her. They'd drink her piss if she demands it."
Charmaine drove off the interstate onto an exit that took them into what appeared to be a sleepy hamlet. The roads were wet with what was possibly rain showers. Howard had not asked where they were going, opting to trust that as long as it had to do with Ms. Jenn then he was fine with that. Charmaine drove like someone versatile with the area. They took a couple of turns before pulling into the parking lot of a shopping mall lot. Charmaine drove towards the east section of the lot and stopped near what appeared to be an adult shop. Other areas of the parking lot were empty except that facing the shop. They got out of the car and Howard noticed several vehicles bearing out of state license plates; he picked out a few that were from his city.
"Wow, Jeffery's here," Charmaine indicated a blue Chevy parked in front of them. "Jeff's a friend of mine. If he's here then that means it's going to be a great night today."
Howard got a better look at Charmaine's get-up which consisted of a sequined evening blouse, skirt and high heels with straps that wound all the way to his knees. He wrapped a shawl around his shoulders as they approached the adult shop.
People were milling aimlessly about the entrance; some gawked shamelessly at the shop's eccentric patrons. Charmaine looked just as happy to be there. Even as people gawked at what he wore, he appeared not to notice or care. He waved at a few bystanders and went and exchanged hugs and kisses with other trannies and cross-dressers strolling about the shop's walkway. He introduced Howard to several of them. They said their goodbyes then went up the short flight of stairs into the shop.
The shop was big but the size was surprisingly inconspicuous from outside. They entered a central lobby that had branching hallways leading to other outlets. Charmaine led Howard into one that was a porn shop.
Howard gawked at aisles upon aisles of adult DVDs and cassette tapes stacked and arranged based on their sexual variety; their exotic covers screamed at Howard to come take a peek. The walls were adorned by adult movie posters, racks housing adult magazines, an assortment of sex toys and sex dolls of whatever make and type. Howard had visited porn shops before but that was back in his college days. Being in one now felt like a novel experience for him. He slowed his steps to sample a collection of high-prices sex toys hanging on a rack. He admired an anal dildo, the looks of which scared him just imagining using it on April. Other people in the shop admired the various contraptions hanging off a wall like they were art exhibits.
"Oh shit, I just remembered I need to buy one of these for Lisa," Charmaine tapped his arm before grabbing a sex device off a rack that was a co-joined dildo and anal butt plug. "Her last one fizzled out a week ago and I keep forgetting to get her a new one. Would be damn cheaper ordering it online, but might as well get it while we're here before I forget again. You see anything you like for yourself, Howie? Or maybe get something for April while you can."
Howard shook his head in dismay as he continued viewing the racks around him. "There's so many stuff I can't decide what. I'm supposed to be at the gym, remember? Anyway, shouldn't we be hurrying about what we came here for?"
"We arrived early; we still have little time. Look, why not pick her up a dildo. I'll get one I think is right for you. You can pay me back later."
Charmaine went perusing around the aisle that was the dildo section; Howard did not make any attempt to stop him. Charmaine came back holding a package in his other arm which he presented to Howard. It was a smooth black twelve-inch dildo.
"Charmaine, you shouldn't."
"I know, but it's my gift to you and April, so shut up and take it. You can always sneak it on her and tell her it's you bought days before. Trust me, she won't know the difference."
Charmaine took both items to the cashier counter. Howard continued perusing the DVD section as other people too were doing. He stopped at the aisle designated for interracial and picked a case that showed a buxom white woman in a skimpy outfit leaning against a black man who looked just as happy to have his arms around her. He returned the DVD and looked over at Charmaine still dealing with the cashier. Howard grumbled and continued checking out the movies while wishing for him to hurry the fuck up.
"Okay, Jo. See ya later," Charmaine waved goodbye to the cashier and came to Howard with both packages in his arm.
They left the porn shop and returned to the hallway. Howard saw one of the trannies Charmaine had conversed with earlier hurrying into a doorway down the hall. Howard noticed other men joining him as well. Charmaine tapped his arm and they followed in the same direction.
"Looks like things are about to get started," Charmaine said. "Come on, let's fall in line. Ms. Jenn usually doesn't like anyone coming a minute later or minute early," he added.
They joined the influx of the crowd pushing into the room.
Howard had heard about Glory Hole booths before. He had glimpsed what they looked like in porn clips showing women venturing into enclosed spaces strictly to blow whichever penis they saw sticking out of holes in the walls. Though never did he reckon a day would come when he would find himself in one.
There was Ms. Jenn sitting like a regal authority on a high stool in a latex leather outfit glaring at them; she wielded her infamous riding crop in her hand. Charmaine and the numerous trannies there including other seemingly heterosexual males like Howard in the room aligned themselves against each other's shoulder as they stopped a few feet from her awaiting her command with eager attention. Howard looked behind his shoulder and saw the door was shut behind them. They might as well be cut off from the world.
"Welcome my pathetic pieces of amphibian shits," Ms. Jenn addressed her slaves. "Are you all ready for your Glory Hole exercise?"
"Yes, we are," they responded in near unison. Howard remained quiet and watchful.
"All first-timers, fall out right now."
Howard watched as several men stepped away from the crowd to stand at a separate corner; there was no any fuss about it. Charmaine tapped his arm and gestured at him to make like them. Howard pushed past the men blocking his view and went and stood with the first-timers. Ms. Jenn looked at him as he walked by but gave no instance of recognition. Howard almost expected her to utter a word and felt somewhat disappointed when she returned her gaze to her other slaves.
"You know the drill, my insects. Assume the position behind any hole of your choice."
Charmaine and the others scrambled about the room like roaches seeking the nearest exit. Each person knelt before whichever apparent cut-out hole in the wall they could find and waited. Seconds later erect black penises inched out of the holes. No way Howard and the others could tell whoever the penises belonged to as the walls were blank and unrevealing.
Charmaine and every other tranny, cross-dresser and male that was on their knees did not need to wait for a pistol shot to start them off as they got busy blowing the cocks that stuck at their faces. Within seconds the room was filled with the sound of slurping and smacking and mouth-drooling cocks being sucked. Some of the trannies hiked up their skirts to expose their rump. Ms. Jenn had her eyes on everyone like a hawk. Now and then she snapped at someone who did not appear to be doing a good job and that would set them back in the right mode.
"All right, time to change over," she slapped her crop against her stool.
Her slaves quit their cock-sucking exercise and rose to their feet. Howard assumed that was the conclusion of the exercise. He watched as Charmaine and other trannies hike up their skirt and push down their panties while others unbuckled their jeans and pushed it down their ankles.
Charmaine was way ahead of the pack as with others like him that appeared ready. His back was to the wall and he bent to touch his knees with his buttock pressed against the hole. His face was plain at first, then curled into a slight frown with his mouth opened wide as he reached between his legs to grasp at the penis that was then jammed inside him. The same thing was happening to others beside him, all looking like they were doing half-squats with their panties or clothes bunched around their shin. They were all starting to pant harder. Their features glowered with lust as they thrust backward at the wall, getting stretched from behind. Howard and the rest of the first-timers watched mesmerised. Charmaine and the others kept fucking back for what seemed like a long time till several dropped back to their knees to suck off the penises till they spurted cum in their mouths. They jerked each penis of whatever ounce of cum they could clean off whilst they continued their sucking and mouth-smacking frenzy.
"All right, slaves!" Ms. Jenn smacked her riding crop once again. The report was sharp. "Get back to your former places. Now!"
Howard and the newbies watched as the old timers came away from the wall and wore back their clothes. Some turned to each other to daintily wipe specks of cum off their lips and chin, chuckling their evening's accomplishment while joining the others.
"As for you grunts," Ms. Jenn addressed Howard and the other newbies who stared at her with rapt attention. "I hope you were taking notes as to what's expected of you. All of you take their positions now." She pointed at the Glory Hole wall where Charmaine and the others had been moments ago.
Howard got ruffled as others cut across his path to get to the wall. He went to a cut-out hole and dropped to his knees.
"Not one of you slug bastards dare make a move until I give the word, got it?"
Howard glanced at the man kneeling beside him. He looked to be in his forties, thinning blonde hair and wearing a faded t-shirt and jeans. His eyes darted as he too glanced furtively at Howard then at the other first-timers around. Like Howard, he was just as well in awe of the moment.
Howard turned his head in time to see a black cock stick its mushroom-shaped head out the hole at him. He looked back at the nervous man and saw similar black cock sticking out four inches from his face. The man gasped and involuntarily jerked backward as if in surprise. A rumbling murmur travelled across the room. Howard looked behind at the old-timers group standing behind the Mistress. He picked out Charmaine who at the moment was chattering with another tranny to be concerned about him.
"Turn your head around and face front!" Ms. Jenn barked at Howard who immediately did as ordered.
"At the count of three, I want you slugs to open your pathetic gutters and start sucking the superior cock that's out in front of you. And don't neither of you bastards quit till it cums in your mouth. When that happens, I want you to suck and swallow every drop of it and don't spill none. Anyone who does that will answer to me. Is that clear?"
"Yes, Ms. Jenn!" they answered in unison; Howard included.
"On my count. One . . . Two . . . Three . . . START SUCKING, BITCHES!"
* * *
Charmaine pulled to a stop three houses from Howard's home as Howard told him to. The time was 9:42 pm. Howard had been contemplating what lie to tell April once she enquired whatever brought him home late from the gym.
"How about you and I went out of town to a fancy adult shop and you watched me suck a black cock then afterwards joined in too," Charmaine threw back his head, breaking into a gale of laughter.
"Ha, ha, not funny," Howard said.
"Maybe not, but sounds glorious," Charmaine got in a few chuckles before turning serious. "Look, quit trying to delude yourself, Howie. You're more addicted than you want to admit to yourself and to April. It'll make your lives a whole lot better once you do."
"Was it ever like this for you the first time you started? I mean, did you ever experience any sort of epiphany or whatever that just got you to keep on?"
"To tell the truth, I don't much remember how I was before all this. Best not think about what could have been; stick with the now is the best option."
"That's something I'll have to work on. Damn, my ass still feels rough though."
"How did that cock feel when it got inside you?"
"Unlike nothing I've experienced before. I can't think of a right word for it."
"Oh, don't go forgetting this," Charmaine reached in the backseat for the gift bag with the items he had purchased at the adult shop. He took out his own item then gave the bag containing the black dildo to Howard, laughing while he did. "April's gonna love that dildo, I'll bet you that. And don't forget your knapsack also."
Howard gathered everything that was his before getting out of the car.
"I'll holler at you later, Howie babe," Charmaine waved at him. He started his car and pulled into a reverse and drove off.
Howard unzipped his knapsack bag and inside went the dildo. He wore back his Raider's hat then walked towards his home.