Oz Beach Boy... Oz Beach Girl?

I put my hands on my hips again, held my knees together, and turned slightly to the side, giving Allegra my best womanly pose. In just my padded bra, lacy underpants, high heels, long blonde wig, and make-up, I indeed felt like a sexy woman. I became increasingly excited by the look of feverish lust in Allegra's icy grey-blue eyes.

"Oh, you slut," Allegra cooed. "You sexy, sexy slut. You are a beautiful, sexy young woman. You're so hot, Matty-Sue...you're a bad, bad girl too. You can try and hide it, but I can see it...I can smell it on you...you're a bad, bad girl, Matty-Sue."

"Oh, my god...this is so hot," I whispered. "I feel so sexy. I...I...I want you inside me, Jack!"

"Okay, you go and bend over the back of the sofa, Matty-Sue," Allegra commanded firmly. "I'm gonna do you the way I do all bad girls...doggy-style."

"Yes, Jack," I said. "Fuck me...please."

I walked slowly behind the sofa, and instantly noticed that Allegra had neatly laid out two large, fluffy white towels over the thick, luxurious carpet, obviously to catch any bodily spillages that might occur during our tryst.

I was instantly and intensely excited. During our last session, Allegra had edged me and refused me the pleasure of release until she allowed it. This time, however, it looked like she might actually let me come on my own terms.

Growing increasingly confident in my high heels, I bent over the back of the sofa, and stuck my butt out sexily. I sincerely hoped that Allegra would like what she saw. I ran my hands over my butt, feeling the silk of my new knickers with my fingers and putting on a lurid display for the beautiful older woman.

"That's the way, Matty-Sue...stick that pretty little butt out for me," Allegra said quietly, and then moved behind me. "Look at those long, sexy legs...look at those high heels...look at that arse. You could be a stripper. You're a very hot little slut, Matty-Sue."

Bent over the back of the sofa, I felt Allegra's strap-on brush gently against my legs and butt, and the older woman then gently put her hands on the sides of my lacy panties. My erect cock bobbled, bounced and then slammed into the back of the sofa when my panties were raked over it as they were pulled down.

Allegra slowly slid my panties down over my muscled butt and continued to push them right down until they were at my ankles. I felt the lacy material drop quietly around my feet, and then partially onto the soft, plush carpet beneath them

"Take the panties right off," Allegra commanded, and I carefully stepped out of my silky knickers, and then flicked them away with the pointed toe of my right high heeled shoe. "That's it, Matty-Sue...my little slut."

I felt Allegra's hands running across my smoothly waxed butt cheeks. She seemed to be enjoying the tightness of my glutes. The sexy older woman gently tugged and pulled at the taut flesh of my butt, clearly getting off on dominating me so completely, merely through her touch and the tone of her words.

I then heard a loud squirting noise. Allegra's hand suddenly dove aggressively between my arse cheeks, and I was suddenly hit by the cool, surprising feeling of what was obviously lube being slopped all over me. Allegra worked the cold gel right into my exposed butt-hole, and then all around the outside and inside of my butt cheeks until I was well and truly lubed up.

"Oh, yeah, your little pussy is so wet," Allegra cooed. "You really want this, don't you, slut? You're sopping wet. I can feel how excited you are...your pussy feels amazing...so tight and sweet."

"Thank...you...Jack," I said breathlessly. "I'm glad you like my sweet little pussy. It's all yours now."

There was a pause, and I heard squirting noises again. I was certain that Allegra was also applying the lube to the ingenious hinged strap-on. The older woman had done that the last time she butt-fucked me, and I was certain she would extend me the same courtesy again.

I loved being sodomised by Allegra during our previous bondage session, and my butt-hole pinched and tensed with excitement in anticipation of being penetrated again. Allegra was about to arse-pound me for the second time, and the sweet threat of violation and supreme humiliation was intoxicating.

"Get ready to get fucked, Matty-Sue," Allegra said with a derisive laugh. "Kiss your virginity goodbye!"

"Oh, my god," I gasped, and stuck my butt out even further while clutching the sofa in front of me. "Please...yes...take it from me!"

With a cruel snort from Allegra, I felt the tip of the strap-on dildo pushing against my butt cheeks. I gleefully spread my legs apart even more, opening up my butt-hole further. I then felt my sphincter starting to pull apart as Allegra pushed her dildo right into me. My butt-hole felt like it was exploding as Allegra drove herself further and further inside me.

"How does that feel, Matty-Sue?" Allegra asked quietly. "My cock in your pussy?"

"It feels amazing," I said breathlessly. "It feels so good."

I let out a loud gasp as I felt Allegra's hinged strap-on dildo being pushed right into me, all the way to the hilt. Allegra was going balls-deep into my lubed up butt-hole, and the feeling of being owned and manipulated skyrocketed as the strap-on dildo was jammed further and further up my ready and willing rectum.

My body slammed back and forth into the sofa as Allegra rode me hard and with obvious excitement. The older woman worked her hips, sliding her strap-on dildo in and out of my arse, and pushing into me with obvious energy and excitement.

The feeling of humiliation was profoundly exciting and unsettling. To add to my excitement levels, my erect cock was positioned in such a way that I could easily and pleasurably rub it against the cloth fabric of the back of the sofa.

"You love it, you slut," Allegra laughed breathlessly, still riding me hard. "You're a woman now, Matty-Sue. Your days as a virgin are over!"

"That feels great," I grunted as my body was slammed back and forth. "You're such a good lover, Jack!"

Grunting, moaning and groaning, Allegra fucked me with the strap-on, sliding in and out of me, and almost exhausting me completely. The whole time, I rubbed my erect cock against the back of the sofa, getting a lot of enjoyable friction going, and gleefully, sneakily working myself desperately toward an orgasm.

"Oh, you slut," Allegra moaned, almost like a sensual mantra. "You dirty slut. You love it."

I rubbed my cock against the back of the sofa even harder as Allegra continued to slide the strap-on dildo in and out of me. I was getting close to coming already, my predilection toward premature ejaculation once again rearing its ugly head.

Though I'd received successful coaching on how to slow and control my orgasms -- from a famous TV sexologist, no less [See Story: "Oz Beach Boy & Alessandra Rampolla"] -- I was just too excited and highly aroused, and I really, really wanted to come.

I'd jerked off earlier in the day while fantasising about fucking my beautiful, big-breasted neighbour, Odessa Prince, but that wasn't enough to stop the train from easily getting to the station. I was getting closer and closer to coming with every thrust of Allegra's powerful hips and every rub of my cock against the back of the sofa. I was getting there...I was definitely getting there.

"Are you coming?" Allegra asked breathlessly, still enthusiastically arse-pounding me. "Is your pussy gonna blow?"

"Yes," I whispered with excitement. "Yes...yes...yes..."

I thrust my own hips and rubbed my cock harder against the fabric of the sofa. I moaned loudly, like a woman in a porno. I was nearly there. I bucked my hips wildly and pumped away rhythmically with Allegra driving into me from behind. I slowed my pumping and tried to arrest my oncoming climax, but it was too late. I was there.

"Oh, my god," I howled. "I'm coming..."

I'd lasted a little longer than I did when I jerked off for Allegra during our last session, but I'd still come fairly quickly. The orgasm roared through me like a powerful force. I moaned and groaned. I quickly grabbed my cock and pointed it downward as semen spurted out of me.

The first thick, milky bolt thankfully landed right in the middle of the fluffy white towel at my high heeled feet. Two more gluggy bolts of jizz erupted from me, and landed right next to the puddle of the first pearly stream.

Wholly exhausted, I sucked in deep breath after deep breath, and rested my abdomen against the back of the sofa. I hung limp and horribly spent. I'd come while being fucked in the arse...the feeling was nothing short of extraordinary.

"You slut," Allegra said with a sneer. "Grinding against me like the true dirty slut you are...you don't fuck like a virgin, Matty-Sue."

Obviously finished with me, Allegra slowly drew back from me, pulling the strap-on dildo out of my violated butt-hole inch by sensual inch. My thoroughly lube-embossed arsehole pleasurably slid shut as Allegra's lifelike, flesh-coloured dildo was finally removed completely. I groaned and whimpered with pure joy.

I then felt a sharp, stinging, surprising pain in my right butt cheek as Allegra struck me hard with the open palm of her hand, connecting with skin and muscle with a loud, silence-shattering crack. She then slapped me again, this time causing my left butt-cheek to explode in pain.

"You naughty little slut," Allegra said with a growl. "You filthy slut!"

Allegra slapped me with her open palm six more times, alternating between my butt-cheeks until they both felt sore and red raw. I sizzled and jumped in pain, still bent over the back of the sofa. Allegra finally ended her rain of cruel post-coital slaps on my bare butt, and I breathed a sigh of relief.

"You fucking slut," Allegra muttered. "You whore..."

I then felt Allegra's hot breath on my face as she bent down to whisper into my ear. The beautiful older woman licked at my face while rubbing my bruised butt with her right hand, soothing its sore flesh while also moving in a decidedly sinister manner, threatening that another spanking wasn't out of the question if I didn't behave.

"I'm done with you now, slut," Allegra whispered. "Matty-Sue, this stays between you and me, got it? This is our dirty little secret, right?"

"Yes, Jack...this is just between you and me," I replied. "I won't tell anyone...I'd be too embarrassed anyway."

"That's good, young lady," Allegra cooed. "Now you stay there with your sweet, little well-fucked pussy sticking up in the air until you hear me leave. Understand?"

"Yes...yes," I replied, and gripped the fabric of the sofa in front of me, still teetering on my high heels. "Thank you, Jack...that was incredible."

"It sure was," Allegra said as she walked away from me and toward the front door. "You're a great lay for a virgin. You should chase that flasher down next time, grab him by the bollocks, and fuck the living daylights out of him. It would do you both some good. Bye, Matty-Sue."

"Bye, Jack," I said quietly, and then heard the front door to Allegra's apartment close.

With Allegra gone, I slowly pushed myself up from over the back of the sofa, and stood up straight on my sexy high heels. I assumed that the gender-reversal role-play was over, and that Allegra had gone back down to the storage space to get changed back into her female clothes.

I folded up the semen-caked towel from the floor and walked back into the bathroom with it, dropping it on top of a large, lidded laundry basket. I then walked back to Allegra's bedroom, my high heels clacking loudly on the white tiled floor of the bathroom as I left.

Once back in Allegra's bedroom, I grabbed my big, dangling cock and then swung it backwards between my legs, which I then pushed together tightly. I turned to look at myself in the full-length mirror of Allegra's built-in wardrobe.

My long blonde wig hung down over my bare shoulders, tumbling toward my red-and-black lacy padded bra. My legs looked long and beautifully shaped from the high heels, while my small thatch of man-scaped pubic hair looked just like an alluring landing strip with my legs pushed tightly together, hiding my massive appendage. I smiled at my female self with a mix of arousal and confusion.

Once again at the urging of the dominatrix Allegra Von Brockhaus, I had enjoyed a brain-scrambling, identity-blurring, emotionally confronting and wholly confusing sexual experience that I would never forget. I'd been fucked like a woman, and it felt amazing. I didn't even know who I was anymore. My sexual experimentation had gone into staggering new territory once again.

I was still excited and quivering from the highly imaginative and erotic manner in which Allegra had ingeniously re-invented my butt-hole as a vagina for the purposes of our role-play. It made me feel even more womanly, and pushed my arousal levels even higher. I was in the hands of a true professional.

While watching myself in the mirror, I pulled off my long, blonde wig, unclasped my padded bra from behind, and then bent to unbuckle the straps of my black high heel shoes. Still with the unbuckled high heels on, I stood up, and then let my big cock unfurl from between my muscled thighs. I had to admit that my nude, heavily muscled, deeply tanned body looked even better in heels.

With a little regret, I finally kicked off the shoes, and then walked nude into the living area of Allegra's luxurious apartment, where I gathered up my discarded pink blouse, grey pencil skirt, and panties.

My cock and balls swinging wildly, I walked back into the bathroom, and regretfully laid my enjoyably and sexily feminine outfit next to the jizz-splattered towel on top of the laundry basket.

I hurriedly scrubbed Allegra's wonderfully applied make-up off my face with a soap-and-water soaked hand towel, slowly shedding my temporary female skin, and returning layer by layer to my masculine self.

I pushed my hair back off my face, and wiped down my sweat-sheened bare torso with a fluffy towel that I pulled off a nearby wall-rack. I looked at my nude body in the bathroom mirror and decided to amusingly remain in my birthday suit until Allegra returned.

I stood in the middle of the bathroom and absent mindedly fondled my cock and balls until I heard the front door open. After a few moments, Allegra walked smiling into the bathroom. She was once again dressed in her jeans, slides and t-shirt, and the stubble make-up had been washed off her face. The silly Fonzie wig was gone, and the beautiful older woman's lustrous auburn hair hung pleasingly loose over her shoulders again.

"There you are!" Allegra said with a warm smile. "You're in the nude! Matty-Sue is gone! Look at that hot body! Look at that dick! I love it! How are you feeling, Matt?"

"I feel incredible," I replied, smiling broadly. "That was an amazing experience. You made for a great tough cop, Allegra."

"And you made for a surprisingly great innocent virgin," Allegra said with a giggle. "Your butt was so sweet when I fucked it, and you really got into it. That was so much fun."

"It was great," I said. "That was really hot."

"Did you like my dick and balls?" Allegra asked, cocking her head. "They're cute, huh?"

"Yes, they were amazing!" I said enthusiastically. "You even got a hard-on! Where did you get that hinged strap-on?"

"I got it online from a specialist dealer," Allegra said with a smile. "You can get just about anything on the internet, Matt."

"Well, that was incredible," I said with a big smile. "Really incredible...it looked so real...and the hairy balls too!"

"And how's your tight little pussy?" Allegra asked with a giggle. "Are you sore down there? Do you have any of that anal ointment left from the last time I sodomised you?"

"I'm a little stretched, but there's not much pain," I replied. "I've got some of that ointment left at home if I need it. Thanks, Allegra, you're very sweet. You don't just fuck me and throw me out...I like that."

"You're too sweet for me to do that, Matt...and speaking of fucking," Allegra said with a naughty smile, and then sexily unbuttoned her jeans and kicked off her slides. "What do you say we have a nice, long fuck in the shower?"

"Oh, my god," I said in shock and with delighted surprise. "Oh, my god...yes, please. Oh, yes...that would be amazing. Oh, Allegra..."

"And you know what?" Allegra said with one of the naughtiest, cheekiest, dirtiest smiles I've ever seen. "I'll even let you be the man this time."

Thanks for reading!