Oz Beach Boy Pegged by Cougar

NOTES: This is a direct continuation of my previous story "Oz Beach Boy Chained By Cougar." It can (hopefully) still be read as a stand-alone story, but reading this previous entry is suggested. This is a CFNM story featuring female-of-male domination, humiliation, ridicule, mid-level pain infliction, confinement, ball-busting, butt-play and pegging, but no intercourse. It is considerably "rougher" than my previous stories. Though there are schoolgirl characters mentioned, they are all over eighteen. This is a work of complete fiction. This story takes place months before my recent holiday-themed entries.

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It was a wet, windy, blustery night in Sydney, Australia. I was completely naked and handcuffed to a metal bed rail with my sweat-streaked face to the wall and my enormous 23cm cock hanging limply and hopelessly between my muscled thighs.

I had been blackmailed into submitting to the depraved sexual desires of Ms. Jacqueline Chabrol, a fortysomething, eye-patch-wearing French schoolteacher who had discovered a kinky wank video that I had made with five of her eighteen-year-old students. [See Story: "Oz Beach Boy Schoolgirls Wank Video"]

If I didn't do as she commanded, she would tell the parents of the girls involved, and then upload the video onto the web. In short, I was well and truly fucked. [See Story: "Oz Beach Boy Vid And French Cougar"]

The French schoolteacher had constrained me to her bed with two pairs of sex shop handcuffs, and then put me through the physical, sexual and emotional wringer. [See Story: "Oz Beach Boy Chained By Cougar"]

With glee and loud peals of laughter, Ms. Jacqueline Chabrol had ridiculed and verbally abused me; kissed and licked me from head to toe; lashed me violently with a leather belt; ripped out my pubic hair; squeezed my nuts multiple times with merciless force; briefly sucked my cock; and then crudely slapped my massive 31cm erection from side to side with the back of her hand.

I'm a sex addicted 25-year-old exhibitionist who enjoys mild humiliation and light domination, but this bizarre experience had my head spinning.

I was excited and aroused by some aspects of Jacqueline's treatment, but agonised and scared by others.

The woman was strange and unstable, and my mind whirled in response to what she'd been doing to me. Her levels of gleeful cruelty were shocking.

After theatrically musing on what steps she could take to now completely and utterly debase me (short of actual castration), Jacqueline had left the bedroom, but was now back, the smell of both her perfume and sweat lingering in the warm air of the small room.

"Mathieu, have you ever been fucked by a woman...like a woman?" Jacqueline asked with a very slight quiver in her voice, belying her own excitement and nervousness.

I looked back over my shoulder with trepidation, and was immediately greeted by a striking, sexy but frightening image that sent shivers of both fear and arousal pulsing through my body like an electric charge.

Obviously carefully devising the kinky visual tableaux of my domination, the lithe and lean Ms. Jacqueline Chabrol wore a black PVC cat-suit and leather high-heel boots.

Her long brown hair was slicked back from her face with gel, and she wore thick, black eye make-up and red lipstick.

With the heady mix of her unusual beauty, bizarre outfit, and striking black eye-patch already combining to create the look of a comic book villainess, Ms. Jacqueline Chabrol had returned to the room after now adjusting her image to that of a true sexual dominator.

Craning my neck to look over my shoulder at her, I saw that Jacqueline now had a black plastic dildo strapped to her crotch with a studded leather belt system that wrapped around her inner thighs and waist.

"Oh my god," I said quietly, and looked down at the foreboding strap-on. "You're not going to do this, are you?"

"Yes, Mathieu," Jacqueline smiled. "I am going to do this. You will now learn what it feels like to be fucked. You're a big, muscular stud obviously used to ramming your enormous appendage into women. Let's see how powerful you feel when you're the one being penetrated...when you're the one on the bottom. You won't feel so strong then, will you?"

"Oh my god," I muttered. "For fuck's sake..."

"I have slowly diminished your power step by step this evening," Jacqueline said. "I have taken everything from you. I have taken your clothes, your power, and your own personal agency. It has been a true joy. This has been one of the best nights of my life. Now I will render you utterly pathetic and impotent. You will be the one getting fucked now. I have the power in this relationship, mon cher. You are nothing."

I rested my forehead against the cool wall, beads of sweat dripping down my face.

I'd enjoyed arse-play in the past, with various women sexily driving up my arousal levels by sleazily and naughtily sticking their fingers into my butt-hole. [See Story: "Oz Beach Boy Poked By Schoolgirls"]

I'd also relished the feelings of violation and submissiveness that arse-play provoked, but being fucked in the butt with a dildo was something else entirely. I was undeniably scared.

"As you can see," Jacqueline giggled, "my phallus is nowhere near as big as yours. I could have procured a much, much larger one, but I don't want to cause you any lasting damage. But you will still feel what it's like to be utterly powerless. You really are my bitch now...my pathetic little bitch. You will be sodomised, Mathieu, by a woman. How truly humiliating that must be for a man..."

I craned my neck to look over my shoulder at Jacqueline. She was smiling wickedly.

I looked down at the dildo and noticed that it was indeed about the size of the average erect male penis.

It wasn't huge, but I would certainly still feel it plunging into me...that was without question.

I also noticed that Jacqueline held a very large plastic bottle of baby oil in her right hand.

I seriously hoped that was going to be applied to either Jacqueline's newly positioned dildo or directly into my butt-hole. I didn't want that thing going in dry.

Craning my neck, I saw Jacqueline place the baby oil on her bedside table, above the drawer in which she'd placed the scissors that she had previously used to cut off my t-shirt.

She then looked around the room excitedly. Obviously spotting what she was looking for, Jacqueline smiled and moved to the other side of the bed.

She hurriedly bent down to pick up what I quickly realised was the thick black leather belt that she had used to lash me with.

"Mmmm," the French schoolteacher murmured theatrically, and I turned my head to again face the wall, "before I drive myself into your flesh, I might need to tenderise it first. I think it's time for my little bitch to enjoy another flogging. Are you ready, young lady?"

Jacqueline laughed wildly and I heard a slicing sound as the belt sailed through the air.

I then felt a massive stinging, painful sensation as the hard leather bit down forcefully into the muscled flesh of my back.

Once again, Jacqueline had folded the belt over to make it as painful as she could.

I screamed and jerked, and Jacqueline mercilessly lashed me again, and then again, and then again, and then one more time. She grunted and squealed with each cruel lashing.

I slumped down, my back flooded with pain. There was a pause, and I optimistically thought it was over.

But then I heard a stirring in the fetid air, and the belt whipped harshly across my bare butt.

The horrible flood of pain was staggering. It rattled right through to my pendulous nuts and upper thighs.

I moaned in agony, and hoped Jacqueline was satisfied. After one more stinging lash across my arse, she thankfully stopped.

I could hear the French schoolteacher sucking in deep breaths, obviously tired from meting out these further humiliating punishments.

"Mathieu, my beautiful whipped slave," Jacqueline said, irritatingly persisting in referring to me in French, effectively even taking my name away from me along with my manhood.

"You were so beautifully oiled in the masturbation video that I took such great delight in viewing," she continued. [See Story: "Oz Beach Boy Vid And French Cougar"] "I will let you in on a little secret, Mathieu. I have actually pleasured myself several times while watching your video. I have already been using you as my sexual plaything."

I looked over my shoulder at Ms. Jacqueline Chabrol's strangely beautiful face, which appeared to be overcome with feelings of joy and happiness. She truly appeared to be enjoying every moment of this.

I had never encountered anyone as profoundly strange as this fortysomething French woman.

"You looked so amazing covered in that oil...I realised that I could accentuate your musculature in the same way while I fuck you," Jacqueline continued. "You will look even sexier. I will oil you up now...like a gladiator before entering the ring. But your opponent will be me and my new phallus...and you will certainly lose. Are you ready to be oiled? Would you like that, bitch? It will help with the lashing that I have just given you too. I'm so kind to you, mon cher. You are such a lucky, lucky boy to be under my patronage, Mathieu."

"Yeah, whatever," I spat, "but you'll fuck up your fancy bedsheets if you drip oil all over them."

"Oh, it will be worth it," Jacqueline giggled, and I heard her squeezing the oil into her hand.

I then felt her greasy palms on my back, and she began to smear the oil all over me.

Jacqueline's hands circled over my shoulder blades and worked into my muscles.

"Having your muscles further pronounced while I enter your rectum will add to my pleasure even more," Jacqueline sneered. "My domination of the big, strong man will be even more powerfully defined."

From behind, Jacqueline reached up under my arms and smeared the oil all over my chest and abdomen, and then teasingly ran her fingers through my now even smaller thatch of man-scaped pubic hair. She giggled the whole time.

I then felt her hands gliding over my legs, the oil being worked into the backs and fronts of my upper thighs vigorously. Jacqueline's nimble fingers prodded into my flesh with obvious delight.

I felt her hands on my butt and shivered with pleasure at their touch. Her fingers worked the muscles firmly.

All the while, I heard naughty, mischievous giggling from the French schoolteacher.

"Look at this derriere," Jacqueline cooed almost kindly. "The musculature is so sculpted and perfectly formed. You must spend hours working on your body...such commitment and effort. Thank you, Mathieu. To be able to gaze at you and fondle you while you are completely nude provides me with such pleasure. This is such a joy for me."

Almost out of habit, and prompted by the kindness in Jacqueline's voice, I slightly parted my legs in my kneeling position.

I guiltily hoped that Jacqueline might actually oil up my cock too. The French schoolteacher, however, remained focused on my firm, steely butt.

"It is a work of art," Jacqueline sighed. "The male form in perfection displayed for the enjoyment of a powerful woman...just as things should be."

Lulled into a momentary sense of pleasure by Jacqueline's erotic murmurings and expertly applied oily massage, I yelled in shock when the French schoolteacher reached violently between my legs from behind and once again grabbed my balls.

"God, I'd love to chop these off," Jacqueline howled maniacally, the temporary kindness in her voice now gone, and squeezed down mercilessly on my nuts. "Your phallus too! I'd love to take it all! But I don't want to end up in prison so I'll have to make do with squeezing them instead, mon cher. It's a satisfying consolation!"

With that, the French fortysomething gave my nuts another firm, painful squeeze, more than enough to make me yelp and pull away.

Jacqueline then embarrassingly yanked down hard on my flaccid dick from behind with a harsh tug, almost like she was milking a recalcitrant cow.

She gave it a few further tugs and then released it with a fling. The French schoolteacher laughed loudly again, and then slapped me cruelly across my already sore butt, the loud crack splitting the silence in the room.

"I always liked to destroy my toys," Jacqueline giggled, and then slapped my bare butt again with even greater force. "Why should you be any different? My big, helpless plaything..."

I then felt Jacqueline's hands on each of my obviously reddening butt cheeks, which were then violently pulled apart.

I could literally feel the warm air of the room on my crudely and cruelly exposed butt-hole.

I could also sense Jacqueline bending down behind me to humiliatingly look right into my widely and painfully spread arse-crack.

"Well, well, well," the French fortysomething giggled. "Clean as a whistle! No hair at all...that's beautiful, Mathieu. I must get your beautician's details!"

Jacqueline let forth with a huge laugh, obviously entertained by her joke. She continued to embarrassingly peer directly into my luridly exposed butt crack.

"You preening peacock...yes, you're like a woman," the French schoolteacher giggled. "So clean and smooth! Do you get your nails done while you're there, mon cher? And a facial too? I'm surprised I didn't find you wearing women's panties when I stripped you of your trousers! You little bitch..."

"Very funny," I sneered in reply. "Very fucking funny..."

"You are funny, Mathieu," Jacqueline spat back at me. "You are hilarious...chained and humiliated...my own personal sex slave for the evening. You can curse me all you like, Mathieu, but you're still a bitch...a bitch that's about to get sodomised!"

I looked back over my shoulder to see Jacqueline smiling while peering between my open arse cheeks.

I then felt her long-nailed fingers prodding around right near my butt-hole, followed by a liberal squirt of the baby oil.

Jacqueline's finger slid up and down teasingly over the outside of my oiled-up butt-hole. It stroked and teased the tender flesh.

But I knew there was going to be a lot more than just a finger going in there, and I shivered again in anticipation.

"I think you are ready now," Jacqueline said firmly. "You are sufficiently oiled up. The time has come for the mare to mount the stallion...although you probably feel more like a gelding now."

Jacqueline climbed onto the bed, and I felt her hands on my muscled, tensed-up shoulders.

She roughly prodded my legs further apart with her knee, and moved her hands to my hips.

The French fortysomething wrenched my butt back toward her, and I gripped the metal bed rail with both cuffed hands.

My movement was restricted by two large metal spheres at the ends of the bed rail which prevented the handcuffs sliding off and effectively constrained me.

I was now splayed in the doggy-style position, with my legs spread embarrassingly wide and my muscled butt sticking out. I was ready to be fucked.

Powerful feelings of fear and humiliation surged through me, but they were matched equally by outpourings of excitement and arousal.

I felt extremely small and embarrassed by my predicament, and it undeniably turned me on.

I'd always been curious about what it would feel like to be fucked in the arse, and thanks to this blackmailing, humiliating crazy French schoolteacher, I was about to find out.

Confusingly, I actually felt my limp cock beginning to slowly stir in response, growing in length and width.

"Your journey into womanhood is about to begin," Jacqueline giggled, "my perverted little bitch. You will be a changed man after this, mon cher...if you can indeed still call yourself a man at all."

There was much that I could have said in response to Jacqueline's debasing torrent of threatening abuse, but I opted to keep my mouth shut. She was on an emotional knife's edge, and I didn't want to tip her over.

Jacqueline held firmly onto my hips, and I felt the hard plastic of the dildo pushing against my butt cheeks.

They spread apart as Jacqueline pushed forward, and then I felt the dildo edging into my thankfully well lubricated butt-hole.

With one big, violent thrust, Jacqueline then drove it into me. With its passage smoothed by the copious amounts of baby oil, the dildo slid into my tight butt.

My sphincter was wrenched apart. I felt myself opening up, and groaned loudly with the intensity of the physical sensation.

"Take that, bitch," Jacqueline howled, and then pushed forward. "Your butt is mine! You little bitch...fucked like a woman!"

The French schoolteacher continued to push, and the entire dildo rammed into my butt-hole.

Jacqueline was inside me. There was an incredible feeling of overpowering fullness in my butt.

Jacqueline laughed loudly, and then began to pound back and forth, slamming into me with her hips.

I felt the PVC of her cat-suit against my bare butt-cheeks, while the metal studs of the strap-on's belt bit into my tender skin.

I lurched back and forth, quickly falling into Jacqueline's rhythm as she powered in and out of me.

The French schoolteacher still clutched the leather belt in her right hand, and proceeded to slap it violently against my thigh as she drove herself into me, as if she was a horsewoman trying to get her steed to increase its pace.

"Yeeee hah," Jacqueline laughed mockingly. "The ride of a lifetime! My beautiful stallion!"

The physical sensation of having the plastic dildo in my butt was highly arousing, while I was mentally and emotionally turned on by the feeling of being so completely controlled.

My submissive tendencies bubbled to the surface with Jacqueline's relentless domination of me.

I'd always been excited by the idea of being dominated, and had often fantasised about it.

This became a highly erotic and disturbing reality during a bizarre sexual encounter in which I lost my virginity on my eighteenth birthday.

Still relatively young and completely inexperienced, this humiliating but highly arousing experience changed everything for me, and led me onto my current path of sex addiction and exhibitionism.

I'd enjoyed flashing groups of women ever since, but my kinky desires had been ratcheted up fairly recently.

In one single day, I was publicly stripped, molested and fucked by four female Russian tourists [See Story: "Oz Boy Owned By Russian Tourists"], and then pantsed and ridiculed by three female joggers [See Story: "Oz Beach Boy Pantsed By Joggers"] in a public park only minutes later.

This extraordinary day had shaken me to my very core. I'd been highly aroused by the domination and humiliation that I experienced during these two game-changing encounters, and I'd been seeking out more of it ever since.

I continually put myself in situations where I'd be at the mercy of sexually audacious women. I was hooked.

Though I had not been clinically diagnosed as a sex addict, I thought of sex constantly, and was pretty sure that it was an apt description.

Nearly every waking hour was consumed with both thoughts of sex and plans of how I would next attain it.

I could still function normally, and held down a good job, but sex played an inappropriately huge role in my life.

Under Ms. Jacqueline Chabrol's salacious control, I enjoyed being sodomised even more than I thought I would.

As she pounded away into me with the strap-on, I admitted to myself that my submissive tendencies were truly intense. I didn't like being hurt, but I did like being put on the bottom.

Against my will, I became increasingly aroused by Jacqueline riding me. My cock slowly began to stiffen.

I tried desperately to suppress it, but I felt the flesh of my member tightening and hardening.

Jacqueline had reacted violently whenever I showed signs of enjoyment during this experience, and I was terrified about what she would do if she saw me getting an erection while she seemingly tortured and debased me by fucking me in the arse.