Into the Depths of Depravity

Anal

Into the Depths of Depravity

Warning: This story contains graphic scenes depicting humiliation and pain. It also depicts male submission. PLEASE, do not read this story if you are offended by any of these topics.

This is a work of fiction. Names, characters, businesses, places, merchandise, companies, events and incidents are either the products of the author’s imagination or used in a fictitious manner. Any resemblance to actual persons, living or dead, or actual events is purely coincidental. All characters are 18 years or older when in sexual situations.

This is Boxwood’s and Mistress SWP’s shared fantasy.

This story is another prequel to Jennifer’s Road to Submission.

Troy appears in that story and is described as a tall, muscular football player who had discovered his submissive tendencies.

Laney appears in that story and in The Vortex and is described as an All-American girl, blond, attractive, tall and lean whose innocent appearance conceals a submissive streak and a very dark side. This story begins in the summer after Troy’s first year of junior college and his first year of junior college football.

Thank you to Doc Magnus for the music selections.

Prologue

The floor of The Club was sticky, and in ways I was trying not to think about. I knew that because I was crawling on my hands and knees, with my palms and knees now discolored and covered with bits of paper, hair, dust and undoubtedly dried cum. I was the good looking young guy, 6-2 185, naked except for a magenta thong and a wide leather collar with the nameplate “SLUT” embossed on it and riveted to the collar. The blonde surfer girl holding the leash was my girlfriend Laney. She was the real slut wearing ultra-high heel black pumps with her frilly pale pink bra and panty set, and the same chain was attached to her collar as she walked me on the leash. Her collar bore the nameplate “WHORE.” Just two young Californians on their first trip to New York, strolling through The Club, probing into the depths of depravity for someone to take the place of our beloved Mistress Claire.

Chapter 1

I was crazy about Laney from that first time I saw her nude and hooded, kneeling in Mistress Claire’s house, waiting to serve. Young, blonde, beautiful, sexy, eager – – she was all of those things, but even with all of that there was an undeniable flatness to our relationship. The unsaid truth of it was that I wanted Mistress Claire more than anything and so did she. Yes, of course, Laney and I were both young and we loved to fuck, putting it bluntly, and it felt wonderful, but the heart-pounding passion was somewhere else.

We were two submissives at our core, and the greatest excitement for us both was seeing Mistress Claire, being on our knees before her, and being allowed to serve her and taste her. When I had to kneel naked and leashed, while watching Laney licking Mistress’ pussy, I wanted nothing more than to be in her place or to kiss her with the taste of our Mistress on her lips.

It was a heady three-way relationship, balanced around Mistress Claire’s domination, control, and training of the two of us. Neither of us had been dominated before, and the excitement for all of us was Mistress Claire’s testing of our limits for humiliation and pain as a precursor to our release. The excitement of testing our limits was the passion that was missing in the relationship between the two of us, and this was the drug that neither Laney nor I wanted to wean ourselves of. But like most college love affairs, this three-way relationship couldn’t last.

When I was in junior college in the San Fernando Valley, I had pretty good football skills and I found the college opportunity I was looking for when a Rutgers scout found me. As a Big East school, they were in the midst of a major push to build up their football program, with an expensive coach, a big new stadium, and scholarships for possible defensive safeties like me. Laney and I were both ready for a move and Mistress Claire encouraged me to go for it. When we told Mistress Claire about our opportunity to go East, she was supportive rather than angry.

“Troy, I do think you’re right, much as I enjoy seeing a big guy like you on his knees before me, football is a skill you need to develop and see where it will take you. If you think Rutgers is the place for you to finish college, you need to take the shot – – and I think they have a good biochem program for Laney too. I know, though, that submission is part of both your personalities, it’s a physical and mental addiction, not just a game you can switch on and off.”

“I know someone in New York that could be helpful to you. I used to go there a lot, and he knows these feelings too; see him when you get there and he can help you make some connections. And I expect to see you here when you get back to California!”

Mistress Claire laughed and cracked her flogger at our feet. We both knelt before her and worshipped her feet one last time. Even her feet were xslot beautiful, the graceful arch of her foot, the slender toes, the immaculate red toe nail polish, and the smooth skin with delicate blue veins visible underneath. I licked between each of her toes and then looked up under her short skirt, reminded again by the shadows between her legs of the treasures she bestowed on us, her loyal subjects.

As we left Mistress Claire’s house for the last time I felt as if a piece of my heart had been ripped out of my chest. As we pulled away in my car Laney was openly sobbing and I was fighting back tears. It would be our quest to fill that gaping void.

We moved a few days later to New Jersey and settled into a typical college apartment in part of an old house on Easton Avenue in New Brunswick, a few blocks from campus. I had my football practice and my Accounting and Marketing course in the Sports Management program. Laney was taking a Sociology course and waitressing part time at Hansel ‘n Griddle (really), a cafe nearby.

“Young Love,” college version, you might think, but after our training with Mistress Claire everything felt boring and uninteresting. Both of us craved the extra intensity and adrenaline rush of submission and control, and neither of us felt real in the dominating role. With a whole town brimming with enthusiastic but vanilla college sex, Laney and I wanted something more, and something we were not likely to find on a college campus.

Once we made the move and got settled in New Jersey, I called the number Mistress Claire had given us, not knowing what to expect.

“Hello, I’m calling for Maurice Tellman …”

“Yes, Tellman here, what is this about?” He sounded older and gruff.

“Ahh, my name is Troy Marchand, my girlfriend Laney Collins and I are, umm, friends of Mistress Claire in Los Angeles, and she suggested I call you …”

“Sir. If you are one of Claire’s subs you will call me Sir. I’m sure she trained you better than that. But it’s unlike her to bother with male subs anyway.”

“Yes, Sir. Actually Laney was her sub, then I met them both, and …”

“I didn’t ask for the book-length version of your love story. Claire is an old friend, and more than that really, so of course I will meet with you. I can’t take you on, but I may know some contacts you can make. I know what you need. Come over on Friday at 9 p.m.” He gave me the address in Hoboken and then abruptly terminated the conversation without waiting for my reply.

I was still holding my phone, puzzled. “Laney, what do you think? Maurice was very curt with me. This sounds like a favor to Mistress Claire rather than a genuine desire to help us.”

“Troy, I was her sub long before you showed up, this Maurice sounds like exactly the sort of Dom she would know. We need to try anyhow.”

So, there we were on Friday night, finding our way from the Hoboken train station through surprisingly vibrant street crowds. It was a neighborhood of restored brick row houses, interspersed with bars overflowing with patrons, international restaurants and quirky boutiques. Tellman’s address was a four story brick house facing a tall apartment tower. We had tried to dress casually but submissively, so I was wearing dark jeans with a soft gray shirt and simple black sports shoes; Laney wore a black hoodie with the hood down, showing just a hint of her short blonde hair, with a short simple gray skirt, low heels and stockings, and as always she looked great even in simple clothes.

We went up the steps to the two tall wooden doors and stepped into the vestibule. I was expecting apartment mailboxes and buzzers, but there was only one bell to push. I realized that Tellman must be very wealthy to own a full private house. We rang, and waited. And waited, unsure if we should ring again.

The door finally opened, held by a slender young man dressed in casual but fashionable black clothing and his face adorned with a gold nose ring. His wavy dark hair flopped over his forehead, and his mouth twisted into a scowl when he saw us.

“Wait, don’t tell me, the young lovers from La La Land. Perfect. Yes, Sir Maurice is expecting you. This way,” he said in a haughty tone of voice. He turned and arrogantly assumed we would follow him into the house. Laney and I exchanged glances at the ice cold reception we received at the door. It was a restored, high-ceilinged mansion, with mostly dark rooms and old furnishings. The hallway we were led down was lined with oil paintings in elaborate gold gilded frames. He took us to the back of the narrow house. The lights were on in what seemed to be a library, with book shelves brimming with books and tall multi-paned windows facing a rear illuminated garden. The Oriental rug and large leather chair featured in the center of the library reminded me of Claire’s house. Sir Maurice was sitting in the large leather chair and turned his head as we entered his lair.

“Sir Maurice, your visitors, Laney and Troy.” The slightly built man took a small side chair; I was surprised he knew our xslot Giriş names. Sir Maurice was a slender gray-haired older man with a pointed beard and piercing blue eyes. He was dressed as the stereotypical Dom, with a black leather motorcycle vest over a silk shirt and leather pants and clunky motorcycle boots. There were no other chairs, and no one was offering us a drink.

“I’m Maurice Tellman. I spoke with my friend Claire after you called. We can talk about what you need, or at least about what you are wishing for, but let’s get the basics over with first. Names?”

“Sir Maurice, I am Laney Collins.” She stood quietly and bowed her head.

“Umm, Sir Maurice, I’m Troy Marchand.” I nodded and bowed my head as well. I had no idea what to expect. It was such a strange juxtaposition; Mistress Claire, the casually dressed Domme, youthful in appearance and radiating sexual power, and Sir Maurice, the traditionally dressed Dom, older in appearance and radiating none of the energy that would fill that aching cavern in my heart.

“Both of you strip. Laney, you first.” Maurice crossed his arms over his chest, and his sub by the wall was watching closely.

Laney’s face colored a bit, then she took a step forward and tugged the hoodie off over her head, exposing her black lace half cup bra. She shook her hair in that way that exuded pure sex. She lifted her arms to reach back and unhook her bra, then pulled it off and folded it neatly on the floor with the hoodie. I never tired of seeing Laney’s naked body. Her pert breasts and hard nipples made my cock rise as I watched but the others did not react. Laney unhooked her skirt and let it drop, then slid her panties down and off to show her us her neatly trimmed pussy.

“You can leave the shoes and stockings – – present yourself.”

Laney knelt on the rug, with her legs wide and space below her, and her hands palm up on the thighs and her mouth open in an “O.”

I stepped forward and unbuttoned and removed my shirt, and then slipped off my shoes. As I pushed down my jeans and stepped out if them, I saw Maurice and his sub paying closer attention. My body was aching from the two-a-day pre-season football practices and I knew I was in good shape. I pushed down my boxers and folded them, with my cock hard from seeing Laney strip. Kneeling legs apart like Laney, my cock and balls were off the floor and exposed.

Laney and I knelt, naked and eyes down, as Maurice got up and walked around us. From the corner of my eye, I saw him stroke Laney’s face and ruffle her short hair, then bend down to cup her breast and heft it, feeling its weight then letting it drop and bounce. She shivered but held still. He walked closer to me and I felt his cold hand on my shoulder, then feeling my bicep and stroking my chest. The sub on the side chair watched with dull annoyance. The sub perked up when Sir Maurice leaned over, cupping my balls and then stroking the length of my cock.

“So tell me, Troy, what you two have learned and what you are looking for?”

I had to wet my lips. “Sir, Laney has more experience than I do but we’ve both felt the power of submission, trading control for more intense feelings. Mistress Claire taught us to think about these feelings, and about why we needed to be dominated and punished and oftentimes humiliated. And we loved her for it.”

“Are you wannabee subs playing at this, or did you come to love Claire and serving her more than each other?”

It was Laney who spoke first. ” Yes Sir, I loved and desired Mistress Claire more than I do Troy, and I think he feels the same way. We are not looking for play, we are seeking a new owner we can have that sort of connection with.”

“It’s not me, kids, but I know the New York area scene and I can introduce you to a few of the better Dommes – – seems clear that a strong woman is what both of you need. First, though, I need to see how real you are, lots of people just play at submission. Sound reasonable?”

“Yes, Sir.” We both spoke up, it was that or leave in defeat.

“Troy, on the floor on your back now, hands behind your head, legs apart.”

I got into position, more embarrassed now by my hard cock jutting up, fully exposed to two strangers.

“Laney, kneel over his face and get your mouth on his cock. I want to see one good orgasm from both of you, but no hands.”

We had done this as lovers, but it was humiliating to perform on command with Maurice and the younger man watching. My tongue fluttered against Laney’s pussy as I nibbled the swelling labia and sucked at her clit and worked to thrust my tongue deeper. Her hanging breasts rubbed against my body as her warm mouth enveloped me and her tongue swirled around my cock. I closed my eyes and despite the audience and the uncomfortable environment felt myself going over the edge. I felt myself reflexively arch my back and spurt cum into her mouth as her lips clamped around me. I licked and sucked harder and faster, trying to ignore the pleasure of my cock in her mouth, until I felt her shudder and her thighs xslot Güncel Giriş gripped my face harder. She rolled off me and we lay side by side on the rug, sweaty and used.

In a soft voice Maurice leaned over and whispered in Laney’s ear. “Kiss him Laney, feed him his cum.” She leaned over me and we kissed deeply as I gulped down my own cream from her mouth. I forgot Maurice for a moment, and smiled at Laney, my lover. Memories of Mistress Claire flooded back into my mind, these cum filled kisses inextricably associated with our training sessions.

“OK, enough fun for you, now I want you two sluts on your knees.”

We looked up, to see Sir Maurice and the young man standing now, unbuckling their belts to lower their leather pants over their boots. Maurice had a thick, short cock with a bush of pubic hair, his sub had been shaved and had a thinner, curved cock jutting out. He was smiling for the first time now.

“Troy, I am guessing this is your first cock sucking, so Billy will be easy on you. Laney, you seem to have skills and experience, come over here.”

I looked at Laney, and we knew that once again it was time for her to submit to someone stronger. She went to kneel before Maurice, and I had to watch as he gripped her hair and pushed into her open mouth.

I knelt in front of Billy, who was thinner and weaker than me, and kept my eyes lowered as I opened my mouth in an “O.” I felt the velvety head of his cock against my cheek, then he was laughing as he pushed it in, and I tried not to gag on it.

Laney’s face was red with exertion as she had fought to receive his full length in her mouth. She voluntarily placed her hands behind Sir Maurice in her attempt to force his cock down her throat. Sir Maurice pulled out of Laney’s mouth, panting at the pleasure her mouth, tongue and throat brought to his cock, but momentarily suppressing his orgasm. Laney’s spit and his pre-cum were hanging lewdly from her chin. I expected to be jealous but I wasn’t. I was happy for Laney. Perhaps this was our entrée into that dark world that we both craved, a world marked by acts of depravity such as this one.

“Laney. You’ve been trained well in sucking a cock. But to be truly submissive, and to put your submission above your obvious affection for Troy, I’m going to ask you to tell me what I should do next.”

Laney pondered the question, on her knees, lips puffy with use, and with the thick stream of her spittle now freely running off of her chin and dripping onto her leg.

“All of our holes are available for Sir’s pleasure. I would think Sir would want to use one of Troy’s holes to show that I value your pleasure first.”

“And what do you consider Troy to be.”

“A fuckhole for Sir’s pleasure.”

“Very good slut. Troy, come over here and accept your Master’s cum. Which hole would you like me to use?”

That question took no thought at all. My submissive tendencies overruled all other instincts. “My asshole Sir. I want to be degraded by Sir and offering my ass is my submission to you.”

“Very well, spread the cheeks of your ass.”

I reached back. I’d been fucked numerous times by Mistress Claire’s harnessed dildo but not by a real cock. Thankfully Sir wasn’t too big. He spit on his hand. I could feel him press the tip of his cock at my anus. He waited. I knew what he wanted. I pushed back against him – – hard. I felt the tip of his cock penetrate my anal ring and quickly slide in until I could feel his balls and pubic hair against my ass. The pain was momentarily searing, then quickly subsided and gave way to a feeling of overwhelming fullness. My cock stirred at this rough anal stimulation. Laney, bless her heart, got on her back and slid underneath us so she could lick Sir’s balls as he was fucking me.

Sir grunted as he reached his edge. I took that as my cue to push back harder and to flex the muscles in my anus. He stopped pushing and I knew he was cumming in my ass. I wanted to feel that rush and exhilaration of submission, but all I got was a warm feeling no different than when I fucked Laney. The magic simply wasn’t there. I felt used and somewhat disappointed.

“Billy, here, now,” barked Sir.

Billy scrambled over to kneel behind me. In the process he rudely pushed Laney to the side.

“All of my cum belongs to Billy. He’s a bit possessive.”

I felt his hands spreading the cheeks of my ass and his tongue probing deeply within it. A satisfied sigh escaped Billy’s lips as he retrieved the leavings of his Master. Again, my cock stirred as I felt Billy’s velvety soft lips on my asshole and the warm wetness of his tongue as he probed inside me, digging out his Master’s cum. But again nothing but a pleasant feeling of satisfaction and no hint of that raw razor sharp edge that I always felt I was skirting when I was with Mistress Claire.

There were few words spoken as Laney and I put our clothes on. Sir wrote down the name and phone number of some of his contacts and also of a club in New York City and pressed the piece of paper in my palm. “You’re good kids. You’ll find what you want but it may take you time. This world’s filled with people that aren’t interested in your welfare. I know that Mistress Claire was a tough taskmaster, but also earned your love and respect. Be careful out there. They’re not all like her.”