Oz Beach Boy in Prisoner Role Play

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It was a balmy summer’s night in Sydney, Australia. Sexy 52-year-old dominatrix Allegra Von Brockhaus fixed me with a cool stare and a superior, wonderfully knowing smile. She had plans for me…very naughty, very kinky, and very imaginative plans.

“Does that sound like fun?” Allegra asked me quietly in her deep, sexily husky voice. “Do you want to do it?”

“Yeah…I think I do,” I replied quietly. “It sounds like fun…disturbing, but fun.”

Though Allegra Von Brockhaus had been taking me into intense new sexual territory, I’m hardly an innocent babe in the woods. Though not officially diagnosed, I’m a raging sex addict. I’m a 26-year-old narcissistic Aussie male exhibitionist who loves getting nude, preferably with women watching me. I spend hours training to get my body into intensely ripped and muscular shape, principally to attract as much female attention as possible.

I like to show off and put myself in potentially sexy situations whenever I can, particularly around Sydney’s many beaches and secluded coastal bays. I also frequently stroll around at night on busy weekends looking for action wherever I can find it.

I am constantly and rampagingly horny, and I’ve enjoyed a lot of very, very kinky hook-ups in my time. I enjoy being verbally ridiculed and objectified by women, and Allegra had been tapping right into that.

The beautiful older woman had made a habit of making me surrender my clothes whenever we met at her waterfront apartment, so I had sat completely nude in her luxurious living room while reading through the older beauty’s neatly typed description of her latest piece of intended BDSM role-play.

In this wonderfully wild scenario, I was to be Captain Matteo Lukovic, a hero of the resistance forces in a fictional, fascist-controlled European nation called Graveria. Allegra, meanwhile, was to be Chief Commandant Allegra Von Brockhaus, the head of both Graveria’s notorious National Internal Security Unit and also of its equally notorious National Information Unit, which handled all of the government’s propaganda.

As laid out in Allegra’s fascinating role-play story outline, Matteo and a small unit of his brave fellow resistance fighters have been captured while carrying out a daring raid on one of Graveria’s remote military outposts.

With the male and female members of Matteo’s team held in captivity elsewhere, the famed resistance leader has been placed into the terrifying custody of the legendary Chief Commandant Allegra Von Brockhaus.

Feared for her inventive brutality and psychological cruelty, it is The Chief Commandant’s intention to both torture Matteo for information on the whereabouts of the resistance army’s central base, and also to publicly broadcast his debasement as a vicious means to break the morale of the resistance, and thus slowly destabilise and weaken its forces.

As determined by the imaginative Allegra, the role-play would end with me as Matteo stripped naked, totally humiliated, demeaned, powerless, and debased, climaxing with the broken hero decrying the resistance and shifting his allegiance to The Chief Commandant and her brutal fascist leader, President Viktor Bartosz.

“Wow, you’ve got quite the imagination, Allegra,” I said with an impressed sigh. “That’s an elaborate set-up indeed.”

“I love role-play and scene creation,” Allegra said, smiling. “Sure, I could just strip you, chain you up, whip you, kick you in the balls, sodomise you, and do whatever, but this makes it so much more interesting, don’t you think? I love the use of costumes. I love raising the narrative stakes. It heightens the tension, and I just love getting dressed up! It really gets me off, you know?”

“Yeah, I kind of like it too,” I said with a smile. “I’d never really done it before meeting you, Allegra. That last role-play was fucking amazing.”

Though we’d enjoyed a couple of “straight” fucks in the interim (which all, of course, still involved me being stripped and bossed around in the bedroom), Allegra and I had engaged in some extremely hot gender-swap role-play prior to that.

This sexy session involved me dressing as a woman, and Allegra fucking me in the arse with a strap-on while she was dressed as a man. [See Story: “Oz Beach Boy…Oz Beach Girl?”] The whole experience totally blew my mind.

52-year-old Allegra Von Brockhaus was a friend of Dominique St. Clair, a beautiful fifty-year-old divorcee I was enjoying occasional casual sex with. When Dominique cheekily asked me if I’d like to be passed around amongst her friends, I hesitantly but enthusiastically agreed. [See Story: “Oz Beach Boy Meets Schoolgirl’s Mum”]

I’d already had fantastic sex with three of Dominique’s other lovely fifty-something friends before meeting with the commanding Allegra, who was undeniably the most beautiful and striking woman of the group. It was turning out to be a very sensual and enjoyable arrangement indeed.

On our first date, Allegra Von Brockhaus revealed to me that she was, in fact, a veteran dominatrix who loved putting men in their place. Allegra had even ingeniously converted her apartment’s downstairs storage room into an ersatz torture chamber.

Engaging with my constantly percolating submissive side, I bowed to my new friend and enjoyed a night of highly arousing but admittedly confusing domination under the stiletto heel of Allegra’s PVC boot. [See Story: “Oz Beach Boy And The Dominatrix”] We’d subsequently enjoyed each other’s company a few times since that first date.

“This new role-play sounds pretty intense, Allegra,” I said with mild concern. “You know I still don’t want to be brutalised too much?”

Though I certainly have submissive qualities, I don’t like to be badly hurt, and Allegra had taken this into account during our previous sessions. The beautiful older woman had certainly debased me, pegged me, and humiliated me, but I had always emerged relatively unscathed…if not a little sore, particularly around the balls and butt-hole.

“Yes, Matt, I’ll pull my punches again,” Allegra said with a reassuring smile. “I will be using some electrical implements this time, but I won’t set them too high. You’ll be okay, I promise. I won’t injure you. I’ll stay within the limits. You have my word. This is all about consent. Is your safe word still Darby?”

“Yes, it is,” I replied, once again using the name of Darby Hamilton, my best friend and one-time foster sister, as a verbal handbrake to immediately stop Allegra if things got too much for me, either emotionally or physically. “My safe word is still Darby…it’s always Darby.”

“Okay, excellent…now, Matt, I’m going down to the chamber to change,” Allegra explained. “Your outfit is in my bedroom. Please get dressed in there, wait fifteen minutes, come downstairs, and then knock on the chamber door. As soon as I open the door, the role-play begins. From that moment on, you are prisoner-of-war Captain Matteo Lukovic, and I am The Chief Commandant. Sound good?”

“That sounds great,” I replied. “It sounds hot. I can’t wait to see you in your outfit. I love a woman in uniform.”

Allegra laughed and then moved in close to me. The beautiful older woman embraced me tightly, and then gave me a warm, passionate kiss on the lips, which I returned enthusiastically. The fact that I was naked made the exchange even sexier. Allegra smelled and tasted amazing. She was a truly fascinating woman, and I felt my enormous cock starting to slowly stiffen.

Standing tall at about 5″9, Allegra Von Brockhaus was strikingly beautiful. She had lustrous auburn hair, smooth, pale skin, and large breasts, but it was her eyes that made her truly stand out. Large and round, they were a stunning, pale, blue-grey colour, almost like ice, and they were hypnotic in their sense of mystery and quiet power.

With those incredible eyes sparkling, Allegra opened the front door of her apartment, and walked outside. The beautiful dominatrix gave me a sly wink and headed down to her storage room turned torture chamber, where our twisted, dark-hued evening of fun would begin.

Completely nude, I quietly walked into Allegra’s bedroom, my huge cock and pendulous nut-sack swinging as I moved. Running my right hand over my heavily muscled bare chest, I looked down at Allegra’s large bed, where my outfit was carefully laid out. I smiled at the dominatrix’s commitment to this fantastical role-play scenario.

On the bed was a white t-shirt, a pair of white boxer shorts, and what looked like a green military flight suit. The one-piece coverall-like outfit was adorned with military badges, and had a zipper running from the waist right up to the neck. On the floor in front of the suit was a pair of black combat boots.

Sitting next to the underwear and flight suit on the bed was a pair of handcuffs, which were accompanied by a white, type-written sheet of paper. “Put these on just before you enter the chamber,” read the message. “I have the key.”

Standing nude in front of my new outfit, I was becoming increasingly aroused. I considered jerking off, but decided against it. I pulled on my underwear, and then stepped into the flight suit, which surprisingly fit my muscular 6″2 frame perfectly.

I sat on the bed to put on my black combat boots, stood up, and then looked at myself in the full-length mirror of Allegra’s built-in wardrobe. I was now Captain Matteo Lukovic, hero of the resistance forces…and I looked pretty dashing, I must say.