Oz Beach Boy... Oz Beach Girl?

NOTES: This story features my recurring character Matt (a muscular, well-hung, sex addicted 26-year-old male exhibitionist) exploring his feminine side with an older female dominatrix. This is a consensual cross-dressing role-play story featuring CFNM, humiliation, verbal ridicule, spanking, and pegging. There is no transgender element to this story, solely cross-dressing and gender-swap role-play. This is a work of complete fiction. All characters are over eighteen. I am endeavouring to write a CFNM "Oz Beach Boy" story in every Literotica category. This entry: "Transgender & Crossdressers".

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It was a warm summer's evening in Sydney, Australia. I looked down in surprise at my alarming new outfit.

On the bed in front of me was a pair of red-and-black lace-and-silk full-backed underpants, and a matching, heavily padded brassiere. Alongside them were a pink satin blouse and a stylish grey pencil skirt. On the floor in front of the outfit was a pair of black high heel shoes. Spread out teasingly across the bed was a long, thick, blonde wig.

"You're going to make a beautiful young lady, Matt," Allegra Von Brockhaus said with a wicked smile. "You're so tall and muscular, but I know we can make this work. And you're already waxed, so we don't have to take you to the beautician. I'm sure the staff at my salon would have enjoyed it if I paraded you around though. Those women would fight each other to wax off your pubic hair!"

"I still can't believe I'm doing this," I said with a sigh. "I've never done anything like this before. I've never dressed like a woman in my life. I'll look ridiculous. I'm 6"2, for god's sake! I spend nearly every waking hour in the gym! I'm too big... everywhere!"

"We're not trying to win any contests here, Matt," Allegra said helpfully, and put a warm hand on my shoulder. "We're not trying to trick anyone. This is about fantasy and role-play...we have to suspend disbelief. I won't convince anyone that I'm a man either. We just have to give in to it...we have to live the fantasy for an hour or so. We're not transgender...we're just cross-dressing for a little sexy fun."

"Okay, okay," I said, with a laugh. "This is a turn-on, that's for sure. I've done a lot of crazy, fucked up shit in my time, but this is really outside my comfort zone."

Bizarre sexual experiences are a regular part of my decidedly lascivious existence. 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 horny, and I've enjoyed a lot of kinky hook-ups in my time. I also love being verbally ridiculed and objectified by women.

52-year-old Allegra Von Brockhaus was a friend of Dominique St. Clair, a beautiful fifty-year-old divorcee who 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"] 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. Engaging with my 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"]

At the end of our first night together in Allegra's purpose-built torture chamber (which she'd ingeniously created in her apartment's underground lock-up storage space), the beautiful older woman suggested that we meet again and engage in some cross-dressing and sexual role-play. I hesitantly agreed. Like my night of highly arousing bondage, cross-dressing was totally new to me. I was excited, aroused and curious, but also decidedly nervous.

"You'll make a cute young lady, Matt," Allegra said with a naughty smile. "I'll make you feel like a natural woman. Do you like the clothes I bought for you? I had to go to a shop that specialises in clothing for bigger women, so the range was limited."

"They're very nice...elegant and understated," I replied. "You've got good taste, Allegra."

"Can we apply your make-up now, Matt?" Allegra asked with obvious excitement. "Shall we go into the bathroom?"

We left the plush, beautifully decorated bedroom of Allegra's stylish harbour-side apartment, and moved into the large, spacious, white-tiled bathroom. A successful project manager for a big-name financial firm, Allegra was wealthy, and it showed in every luxurious inch of her obviously very, very expensive apartment.

Statuesque at about 5"9, Allegra Von Brockhaus was a strikingly beautiful woman. She had lustrous auburn hair, smooth 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. Allegra Von Brockhaus was a very hot 52-year-old woman...and an inventive dominatrix.

When we got into the bathroom, Allegra stopped and then turned to look me up and down. Her ice-blue eyes raked up and down my body. Dressed casually in a pair of jeans, Nike slides, and a vintage Bikini Kill t-shirt, Allegra still exuded a quiet sense of power. She smiled at me with a wicked, knowing sense of intent.

"Take off your clothes, Matt," Allegra said with a smile. "It would be more sensual and exciting if you were totally nude while I did your make-up."

"Even my underwear?" I asked. "Everything?"

"Yes, Matt...everything," Allegra replied. "I'll watch while you disrobe. Strip for me..."

"Of course, Allegra" I said with a smile, and practically ripped off my shirt. "I'm always happy to get naked...especially for you."

Now bare-chested, I made fists of my hands, causing my large biceps to bulge even more impressively, and tensed the muscles in my chest and abdomen. A slight smile played across Allegra's lips as she stared at my bare torso, her eyes scanning up and down my body.

"Oh, my god...you're so ripped, Matt," the sexy older woman said while chewing on a fingernail. "You train a lot, yeah?"

"Thanks, Allegra, that's very nice," I replied. "I'm at the gym all the time. I've also converted my apartment's underground storage space into a home gym. I like to train in the nude down there."

"You are a naughty boy, aren't you?" Allegra said with a giggle. "God, I'm picturing that now...you lifting weights with your bare glutes tensed and your willy swinging...geez, hurry up and get the rest of those clothes off!"

I quickly kicked off my shoes, and then hastily peeled off my socks. Per Allegra's instruction, I moved with far greater pace than I normally would. Even though this sexy older woman had already seen me naked the last time we met, I was still excited about exposing myself to her again.

I unbuckled my belt, and then unbuttoned and unzipped my jeans. I quickly pulled them apart, and I saw Allegra's eyes widen in anticipation. I slid my jeans down over my muscled thighs and calves, and then pulled them over my bare feet without a hitch. With a cheeky smile, I folded my jeans and placed them carefully with my shirt on the bathroom bench behind me.

I stood in front of Allegra Von Brockhaus in just my fitted Calvin Klein trunks, and I noticed a smile play across the sexy older woman's full red lips, this time as she sneakily glanced at the bulge of my crotch. I ran my hands over my marbled pecs and rock-hard six-pack, and then smiled cheekily at Allegra.

"Come on, Matt," Allegra cooed quietly. "Stop being such a pussy-tease! I've seen that meat swinger before, and I want to see it again! Take off your undies!"

With no hesitation, I hooked my thumbs into the sides of my Calvins, and then slid them down over my crotch and thighs, first revealing my small thatch of man-scaped, sandy brown pubic hair. My long, thick, vein-crossed, uncircumcised cock then flopped up and down as my Calvins finally slid over it.

Pendulous and heavy, my unnaturally huge member dangled enormously over my equally outsized nut-sack as I stepped out of my underpants. I placed my Calvins on the bench with the rest of my clothes.

Allegra smiled, obviously happy to once again be looking at me in the nude. I flexed the muscles in my bare torso, and made tight fists of my hands again to make my arms bulge impressively. I twitched my enormous, low-swinging cock to make it jump a little.

"You, young man, are in possession of the biggest penis I've ever seen," Allegra said with a whistle. "It's quite astounding...and beautiful. You have a very pretty cock, Matt."

"Last time you saw it, you called me a freak and said I belonged in a circus!" I said with exasperation. "You made fun of me!"

"I was debasing you in my torture chamber, Matt," Allegra responded with a frown. "Everything is different when we're down there. It's about power and humiliation."

"Oh, okay," I said with a smile. "I get it. You don't necessarily mean everything you say."

"No woman could deny that you have a truly extraordinary body, Matt," Allegra said with a warm smile. "You're like a Greek god...but with a bigger dick! You're a very, very pretty boy."

"Wow," I said quietly, incredibly flattered. "Thank you, Allegra. You're very beautiful yourself."

"Right...let's get you all made up," Allegra said with a smile. "I could stare at you in the nude all day, but let's take this up a notch. Have a seat."

With my cock and balls swinging ridiculously, I walked over to a small chair which sat in front of a large, custom-lit make-up mirror. I adjusted my cock as I sat down, letting it dangle over the edge of the chair. Allegra looked down at my absurd appendage and giggled.

The beautiful older woman opened up a large make-up bag and went to work. First, Allegra used a small brush on my eyelids, coating them with a subtle but still vivid skin-tone eyeshadow, her attentions gentle and focused.

Allegra applied eyeliner next, expertly using a black pencil to give me some definition and a sense of mystery, apparently. Allegra's big breasts pushed alluringly against my bare, heavily muscled arms as she worked, which sent a pleasurable shiver up my spine.

"I'm trying to be subtle here," Allegra said. "In our role-play, you're something of an innocent young woman, and I want your clothes and make-up to suggest that. I don't want you to look like a tart."

"Good," I said with a laugh. "I might be that kind of guy, but I'm not that kind of girl."

Clutching the pencil like a seasoned pro, the giggling Allegra got in close, inspecting her work as she went along. I moaned quietly at the understated eroticism of it all as her body kept touching mine. Allegra gave me a very odd smile.

"Oooh, that looks great," Allegra said, admiring her handiwork. "I'll just put on a little blush now to give your cheeks some colour. You've got great skin, Matt, so we don't need any foundation."

Allegra worked some powder onto a big, fluffy make-up brush, and then dusted it lightly over my cheeks, humming while she happily played make-up artist. Having Allegra's undivided attention while she fussed around my nude body was getting me increasingly excited. I felt my cock stiffen slightly.

"Very nice," Allegra said, standing back from me to get a good look at my newly made-up face. "Oh, my god, Matt...are you getting erect?"

"Yes, I am...I'm sorry," I said with pure embarrassment. "This just feels...nice. It's a turn-on...all of the touching. It's sexy...I can't help it. I get hard really easily."

"That's okay, Matt," Allegra said with an understanding smile. "Enjoy it. Don't start playing with yourself though, okay? Let's save all that for when we get started."

"Okay...no jerking off, I promise," I said, smiling naughtily. "It won't be easy though..."

"You'll be right," Allegra said, and pulled some red lipstick from her make-up box. "This will make you look very cute."

Allegra bent down and then applied the dark red lipstick, smearing it gently and carefully over my mouth. Once she was done, I puckered up, which prompted a warm smile from the beautiful older woman.

"Who's a pretty girl then?" Allegra said with a whistle. "You look so sweet and alluring! You could be on the cover of a magazine!"

"Come on," I responded with a laugh. "I must look ridiculous."

"You look gorgeous...Matt, I'm going downstairs to the chamber now to change...literally," Allegra said, smiling. "Can you put on your wig and your outfit please? Your underwear too?"

"Yes, I can," I replied, and Allegra handed me a type-written sheet of clean, white paper.

"Please read that, Matt," Allegra said. "Those are the details of our role-play. Please read it carefully. Is your safe word still Darby?"

"Yes, it is," I said, referring to my best friend and one-time foster sister, Darby Hamilton, whose name was my instant choice for a safe word during my first bondage session with Allegra. "Will I need it?"

"There won't be any constraints or any real use of implements like last time," Allegra said seriously, "and there will be no substantial pain at all, but this is still about submission, and about you relinquishing your power to me. You have to surrender to me. I am a powerful, authoritative man, and you are an innocent young woman."

"Right, I see," I said and nodded my head. "Got it..."

"Though I won't be chaining you up this time, I will be completely dominating you," Allegra explained. "You have to weaken yourself as part of the role-play. We really have to commit to it to get the premium enjoyment."

"Right, right," I said, listening intently.

"We might look silly, but as I said, this will be much better if we suspend disbelief and wholly accept the gender-swap concept," Allegra continued. "We need to use our imaginations and really give in to it. Become the woman, Matt...become her."

"Okay...this sounds crazy...but fun," I said with a smile. "I'm so intrigued and turned on...I've never done anything like this before. This is new ground for me."

"Well, if at any point it becomes too intense or uncomfortable, either physically or emotionally, just say your safe word, and we'll stop, okay?" Allegra offered with a warm smile.

"Yep, I will," I responded. "Definitely..."

"One man I did this with just broke down in the middle of our role-play," Allegra continued. "He couldn't handle being the woman anymore. It was too much for him. He was a real wimp...I hope you can go a lot further, Matt. It's not easy being a woman...but I think you're man enough to do it."

"As I've said, I've done a lot of weird shit," I said, smiling, "and I think I can handle this. I can be a woman. Bring it on, Allegra."

"Okay, Matt, I'll be about half an hour getting ready downstairs," Allegra explained. "When I knock at the apartment door, our role-play begins. When you open the door, you refer to me by my male character name immediately, do you understand?"

"Yes, I do," I replied. "I'll go through the scenario and get into the right mind-set. I really want this to work and be fun too."

"Thanks, Matt," Allegra said, and then winked at me naughtily. "I've got a good feeling about this...we're going to have a great time."

With that, Allegra turned and left the bathroom. She retrieved a large suit bag and a small sports satchel from her bedroom, and then headed out the front door of her apartment, turning to look at my completely nude body one more time. With a smile, the beautiful older woman was gone, the scent of her perfume still sweet and fragrant in the air.

With my cock and balls hanging, I read over Allegra's provided role-play scenario with great interest. As I got further and further down the typewritten page, I got more and more excited. What the beautiful older woman had devised for us played right into my kink for being dominated, objectified and ridiculed. A broad smile played across my brightly painted lips.

I was to be the amusingly named Matty-Sue Cherry, a twenty-year-old female virgin studying economics at university. I was to be reserved, shy, conservative, and unsure about my body, while also unaware of how attractive I was to men. In short, I was a sweet young woman ripe for the picking.

Allegra, meanwhile, was to be reborn as Detective Jack "The Hammer" Von Brockhaus, a former homicide cop busted down to Local Area Command after brutalising too many criminals and, even worse, too many merely suspected criminals as well. Detective Jack "The Hammer" Von Brockhaus was a tough, menacing cop from the violent "old school" of Australian policing.

Matty-Sue and Detective Von Brockhaus meet after the young woman phones in a formal complaint about being flashed by a naked male pervert while bringing groceries into her apartment from her car outside. Detective Von Brockhaus knocks on the door of Matty-Sue's apartment to take her complaint in person, get a physical description of the nude offender, and ask some questions so he can open an investigation.

In her typewritten scenario, Allegra advised me to remain meek, mild and fearful while an increasingly intimidating and inappropriate Detective Von Brockhaus gets more emotionally aggressive and overtly sexual in his approach toward me.

Allegra advised me to follow her lead, and to find the wallflower virgin buried deep, deep within myself. As "The Hammer", Allegra would then bring out the slut in me. I was very, very excited indeed, and happy to further push my sense of sexual experimentation.

With my cock slightly engorged, I resisted the urge to jerk off as I walked nude and fully made-up from the bathroom to the bedroom. Once inside the softly lit room, I looked down again at my long, blonde wig and stylishly conservative outfit. It was time for me to become, well, a woman.

I gingerly picked up the pair of red-and-black lace-and-silk underpants from the bed, and slid them on over my muscled calves and then up my smooth, fully waxed legs. The expensive silk felt soft and luxurious against my cock and balls as I pulled the panties up completely.

I positioned my enormous member across my hip in the knickers, not wanting to tuck it between my legs just in case Allegra wanted easy, unobstructed access to my butt-hole...which I certainly hoped she would.

I slid the matching, heavily padded brassiere up my strong forearms and over my bulging biceps, and then reached behind my back to clasp it into place. Allegra told me that the bra had been especially padded for women who had had double mastectomies, and it did indeed give me at least some of the feeling of what it must be like to have medium-sized breasts.

In my newly positioned and surprisingly comfortable bra and panties, I sat down carefully on Allegra's bed and pulled on the black high heel shoes that the beautiful older woman had generously

provided for me.

Almost subconsciously, I was sitting like a woman, with my knees pushed firmly together and bent at the sides. I was mildly disturbed by how quickly I had embraced my feminine side.

I pulled together the small buckles of the high heel shoes, and then stood up with some uncertainty, lifting myself gingerly off the bed. I slowly got my balance, and then eventually stood up straight with my large hands placed on my highly toned hips.