Oz Beach Boy & Odessa Try Anal

NOTES: This is an entry in the Halloween Story Contest 2023, so I'd really appreciate it if you could take the time to vote. This story features my recurring character Matt (a muscular, well-hung, sex addicted male exhibitionist in his twenties) and his girlfriend Odessa Prince (a beautiful but shy Cosplay enthusiast) being inspired by the darkness of Halloween Night to have anal sex for the first time. This story features CFNM, some discussion of pegging, analingus, and consensual male-to-female anal sex. 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 (rear) entry: "Anal".

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On Halloween Night, Matt has a dark, sexy idea...

It was Halloween Night in Sydney, Australia. I stared with pure, unbridled lust at the wonderfully womanly, cutely curvaceous butt of my beautiful girlfriend, Odessa Prince. I'd never wanted to do anal so much in my entire life.

Odessa was at the sink of my apartment's kitchen fixing herself a drink. She was wearing a tight-fitting Tigra t-shirt and a pair of soft sweat-shorts that stretched taut across her backside and rode up so high that the very bottom of her butt was sexily visible. Though firm, Odessa's butt cheeks jiggled ever so slightly as she moved, and I watched them in quiet awe.

I was lying on my couch completely naked, and I was tempted to jerk myself off while taking in the glorious sight of my girlfriend's butt, but I managed to restrain myself. Odessa and I had been through a truly bizarre experience earlier that night [See Story: "Oz Beach Boy & Odessa...Trapped!"], and I didn't want to shock her further by indulging in a little impromptu on-display self-love. It would hardly, however, be out of character for me.

Though not officially diagnosed, I'm a raging sex addict. I'm a narcissistic Aussie male exhibitionist in my twenties who loves getting nude, preferably with women watching me. I spend hours training to get my body as ripped and muscular as I can, 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.

All of that, however, was well and truly parked as soon as the beautiful Odessa Prince and I embarked upon a relationship. She wanted us to be monogamous, and even though I knew it would be difficult, I agreed because I was so incredibly taken with her. [See Story: "Oz Beach Boy & Odessa Come Together"]

Thankfully, my girlfriend enjoys looking at me nude, and Odessa has happily indulged many of my kinky, unconventional sexual desires. [See Stories: "Oz Beach Boy & Odessa Nude Morning", "Oz Beach Boy & Odessa Nude Videos", "Oz Beach Boy & Odessa Nude Balcony", and "Oz Beach Boy & Odessa Caught Nude"]

I think I may have even awakened something of a domme in my girlfriend, which has been truly extraordinary to witness. Odessa not only enjoys watching me nude, but she has also taken great sexual pleasure from displaying me naked and teasing other women with me. [See Stories: "Oz Beach Boy & Odessa At Nude Beach", "Oz Beach Boy & Odessa Pool Prank" and "Oz Beach Boy Fronts Abbie Chatfield"]

Odessa had long expressed a desire to dress me up (or perhaps that should be, dress me down) in a loincloth and other sword-and-sorcery type garb, and we'd even had a lot of fun in the bedroom lately with a little raunchy Conan The Barbarian-style sexual role play. [See Story: "Oz Beach Boy & Odessa Role Play"]

On Halloween Night, however, my thoughts were very much on anal sex. Odessa and I had done all sorts of things sexually, and outside of group sex and serious bondage, that was the only territory into which we'd so far failed to stray. I'd masturbated frequently while fantasising about sinking my cock between my girlfriend's very sweet cheeks, but I'd been too nervous to bring it up with Odessa because I had no real idea where she stood on the subject of anal.

I stared again at Odessa's firm but wondrously curved butt, and thought again about how much I'd love to drive myself into it. Doggy-style was always a favourite position of Odessa's, so I fancied that she might actually like to take it one step further by allowing me to push myself into her butt-hole. I absent-mindedly fondled my cock just as Odessa turned around and walked back into the living room carrying a lemon, lime and soda.

"Oh, my god," Odessa said with a giggle. "Were you just about to start whacking off? Were you staring at my butt in the kitchen?"

"Yes...caught red-handed," I responded, and decided to take a chance by raising the subject of anal sex.

I pulled myself up off the couch, and slyly made fists of my hands to make my biceps bulge. I flexed the muscles of my bare torso, and tensed my glutes. Odessa enjoyed watching me flex and pose, so I hoped a little show might help smooth the way...right into my girlfriend's butt. I gave Odessa a sly smile, and she looked back at me a little uncertainly.

"Odessa, um," I said nervously, swinging my hips slightly to make my cock swing. "We've never talked about it...but I was wondering where you stood on, um...anal sex?"

"Oh, my god," Odessa responded, dropped her head, and giggled. "I'm surprised it's taken you this long to ask."

"I hope you're not offended," I said quickly.

"No, it's okay," Odessa said, smiling and looking at my exposed cock. "We've been together for more than a few months now. It's okay to talk about it, that's okay."

"What do you think?" I asked, flexing my muscles again.

"Well," Odessa said, and then paused, "I've never done it before...but I've certainly thought about it. And I admit that, yeah...I have definitely fantasised about you fucking me up the bum...even before we got together. Your dick is so big that the thought of it up my bum is really exciting. You've fucked girls in the bum before, yeah?"

"Yes, I have," I replied. "I've done it several times, yeah. It's great. I really like it."

"Okay...I'm in," Odessa said with a smile. "I want you to fuck me up the bum."

"Wow," I responded. "Do you want to do it...tonight?"

"It's Halloween Night," Odessa replied. "I've always thought of anal as something dirty and naughty, so that would be perfect...losing my anal virginity on Halloween Night...that feels so wrong and so right at the same time."

"It would be so dark and sexy," I said with a smile. "It's a bit outlaw...the perfect thing for Halloween Night. And after what we've just been through, it wouldn't even feel that strange."

"That's true, fuck...I'm still nervous about it though," Odessa said. "It's pretty out there, isn't it? Taking it in the arsehole?"

"It's not that weird," I said reassuringly. "It's cool. It's okay."

"Oh, it's okay for you," Odessa said with a big, raucous laugh. "You're not the one being fucked in the butt! You'll never know what it's like! How can you say it's okay?"

"Well," I said, and paused...for way too long.

When we first got together, Odessa accepted my sex addiction, but made me promise that I wouldn't cheat on her, and then also made me promise that I would always be completely honest with her. I'd been wholly and happily faithful to Odessa, and I'd also given her honest answers whenever she asked me about my very sordid sexual history. I could sense that I was about to be put on the rack.

"Wait a minute," Odessa said quickly. "You told me you haven't had any gay experiences! And now you're saying you've been fucked in the butt? Have you been with guys? I'm cool with it, but I asked you, and you said you hadn't."

"Odessa," I said, and smiled cheekily, "you don't need a guy to get fucked in the butt. I've been pegged, Odessa...by women...quite a few times."

Odessa's eyes widened and her mouth hung open in surprise. I then told her about Allegra Von Brockhaus, the fifty-something strap-on-wielding dominatrix who had been training me as her sub just before Odessa and I got together. [See Stories: "Oz Beach Boy And The Dominatrix", "Oz Beach Boy...Oz Beach Girl?" and "Oz Beach Boy In Prisoner Role Play"]

Though I didn't exactly give her a play-by-play, I certainly provided Odessa with a fairly vivid picture of what Allegra and I had gotten up to, including my pegging and one-time cross-dressing. Odessa listened in shock and obvious distaste. I could tell that of all the sordid sexual experiences I'd admitted to, this was obviously the most disturbing to the very open-minded Odessa.

Picturing her boyfriend getting butt-fucked by a woman twice his age was clearly a little much for Odessa...as it would be for most women. I sensibly opted not to tell Odessa, however, about my pegging experience with Jacqueline Chabrol, a slightly deranged French art teacher with whom I'd shared a truly bizarre relationship. [See Stories: "Oz Beach Boy Vid And French Cougar", "Oz Beach Boy Chained By Cougar", "Oz Beach Boy Pegged By Cougar" and "Oz Beach Boy Flips French Cougar"]

That tale would have completely blown my girlfriend's mind, so I decided to keep that in the vault for the time being. Odessa and I stood in silence for a few moments, and then quietly sat down on the couch, my huge cock and balls swaying ridiculously as I moved. I put my hand gently on Odessa's shoulder, and we smiled at each other.

"Sorry, Matt," Odessa said quietly, "I know you're a sex addict and you've done a lot of weird shit, but that's really...intense. Thanks for always being so honest with me, but sometimes it's just a lot to absorb. I never imagined that you would have been fucked in the butt, um, by a woman."

"I know...I know," I responded.

"I still want you to fuck me in the arse though," Odessa said with a wonderfully wicked smile. "All this talk of butt sex has got me hot. I think I'm turning into a perve too."

"You don't have to do it to satisfy the freak in me," I said quickly. "I only want to do it if you really want to."

"Oh, I do, Matt," Odessa responded, again smiling wickedly, "but I want to do it at my place...and I want to set it all up."

"Do you have a full tube of lube?" I asked. "We'll need it."

"Yep, I do," Odessa replied. "Yes, I do."

With another naughty smile, Odessa got up off the couch, and then walked to the front door. She paused and shook her butt cheeks for me, making them jiggle and bounce in a truly sexy display, the soft fabric of her sweat shorts flipping and swaying with the movement, revealing the milky flesh of her lower arse. Odessa then looked at me over her shoulder and winked.

"Be at my place in half an hour," Odessa said breathily. "I want you in nothing but your underwear. My butt will be waiting for you, lover."

On Halloween Night, Odessa mentally prepares to surrender her anal virginity...

In the cool night air walking from Matt's building to hers just across the way in The Mapreza apartment complex (they'd been neighbours before becoming lovers), Odessa desperately tried to process the information she'd just been hit with. Her thick, dark mane of hair swaying and her light-blue eyes wide with surprise, Odessa had once again been knocked sideways by Matt's bizarre sex life.

Being in a relationship with a sex addict was certainly exciting and sexually satisfying, but it was also shocking. Odessa just couldn't get the image of Matt on all-fours being fucked in the butt by a woman with a strap-on out of her head. It was freaky and weird...but also slightly arousing. And that disturbed Odessa even more.

Though she was incredibly fond of Matt, and they had a really lovely time together, Odessa was constantly unsettled by her own responses to his very salacious and unconventional sexual desires. Matt was awakening things in Odessa that she wasn't really sure she wanted to have awakened. She still couldn't believe that she'd actually let him jerk off in front of three excited women on a nudist beach. And then stripped him nude at their apartment complex's swimming pool. What kind of girlfriend does that?

Matt and Odessa's relationship was getting increasingly kinky and strange, and the beautiful brunette wasn't really sure if that's what she wanted. She feared where it might end up, terrified of eventually finding herself caught up in some kind of Fifty Shades Of Grey situation. Odessa shivered at the very thought as she made her way up to her apartment in the elevator. She was certainly excited to experiment with a little anal penetration, but Matt's sexual adventurousness was slowly, surely becoming a cause for concern for Odessa.

Odessa opened the door of her apartment, and quickly moved inside. She stripped off her t-shirt and bra, her big, heavy but firm breasts releasing with a thud, their dark nipples and areolae slightly erect with anticipation.

As quickly as she could, Odessa peeled off her soft gray sweat shorts and pink Harley Quinn underpants, and then ran the shower. She let the hot water run over her curvy but fit body, and then went to work on her butt-crack and vulva with large globs of scented body wash, cleaning herself up as best as she possibly could.

Odessa worked the body wash right into her butt-hole, and then all around her butt-crack and cheeks, vigorously scrubbing in preparation for what was to come. Odessa didn't just want Matt to fuck her in the butt-hole...she wanted him to lick it too. She wanted Matt to lick her arsehole. Odessa wanted the whole anal experience.

Though many of Odessa's previous boyfriends had suggested anal, she'd always resisted it. Wary of possible pain and physical damage, as well as the naughty, "bad girl" aspect of it, Odessa had politely refused to offer up her butt-hole for penetration. She had always, however, been very, very curious about it...and she knew that she would do it one day.

Odessa had never liked any of her previous lovers as much as she liked Matt, so he seemed like the right guy to lose her anal virginity to. Matt had done it with other girls too, so Odessa assumed that he'd be a good guide when it came to anal. And despite his huge cock and heavily muscled body, Matt was also a very sensitive lover, so Odessa knew he wouldn't go too crazy on her arse. He would take care of her...Matt would be gentle, and he'd take it slow.

After carefully washing her butt and vulva, Odessa turned off the water, got out of the shower, and toweled off. She grabbed the large tube of lube from her bathroom cabinet, and walked naked into her bedroom, which she intended to turn into the perfect Halloween Night Anal Sex Parlour.

Odessa Prince was ready to give up her anal virginity...and she was satisfied that her boyfriend Matt was the right guy to take it from her.

On Halloween Night, Matt makes the very short trip to Odessa's apartment...

Clad in just a butt-hugging pair of black Calvin Klein fitted boxers, I clutched both my apartment keys and the spare set of Odessa's that I kept at my place. I walked quickly from my building to Odessa's, not wanting to get caught walking around in my underwear.

I was excited about trying anal sex with Odessa for the first time, and I could feel my cock starting to swell slightly as I pushed open the front door and moved into the foyer of Odessa's building. With a real spring in my step, I walked toward the elevator, my muscles rippling as I moved.

Just as I reached out my hand to hit the button for the elevator, the doors slid open, and I was greeted by the truly wondrous sight of Lizet, a very attractive twenty-something South American woman who frequented The Mapreza's communal swimming pool. Lizet liked to show off her gorgeously shaped, but heavily pimpled, butt in a revealing g-string...and she also liked to check me out in my Speedos.

Looking extraordinarily sexy and obviously dressed for Halloween, Lizet wore a pair of red devil's horns atop her dark-maned head, which she'd teamed with a bright red mini-dress. It had a sexily plunging neckline, which displayed a gorgeous slice of olive-skinned cleavage. In Lizet's hand was a red, plastic pitchfork.

Lizet looked at me in my fitted boxers, and her lively brown eyes widened in obvious appreciation as she looked me up and down excitedly. Lizet had already seen me naked [See Story: "Oz Beach Boy & Odessa Pool Prank"], and she looked at my near-nude body with a very knowing and very naughty smile.

"Hola, Matt," Lizet said warmly in her thick accent, and stepped out of the elevator. "Are you out doing the trick or treat on Halloween? I hope you only knock on your girlfriend's door like that, ci? Maybe you the treat, huh, papi?"

"Yes, I'm going to Odessa's...I was hoping I could sneak in with nobody seeing me," I said sheepishly as Lizet moved past me. "You caught me."

"Oh, I catch you...I see you," Lizet responded with a giggle. "I always happy to see you, Matt. I never forget Odessa pulling off your towel at the pool...aye, papi! You sexy, sexy man...if you ever break up with Odessa, you come see Lizet. My home is 8A...you knock, I answer for you. I let you do whatever you want to me...anything, papi."

"Okay...I'll keep that in mind," I said quietly, and felt my cock stiffening even more.

"You give Odessa some from me," Lizet said with a laugh and then lewdly pumped her arms and thrust her hips back and forth. "You have fun! Adios, Matt! See you round, papi!"

"Thanks, Lizet," I responded, and then stepped into the elevator. "Have fun out there. Happy Halloween!"

On Halloween Night, Odessa is deliriously and desperately ready to get her butt fucked...

Totally nude, Odessa carefully positioned ten black candles around her bedroom. Her big breasts swaying as she moved, Odessa then lit each one with a silver Zippo lighter, her bedroom instantly transformed into a lightly glowing boudoir ready for sex.

To further the dark but cheeky mood, there was a small, plastic glowing Halloween pumpkin on each of the room's bedside tables. Odessa lightly placed the large tube of lube on the table to the bed's right, in easy reach. She smiled as she looked around her bedroom, which shimmered in the light of the black candles.

Odessa opened her large built-in wardrobe, scanned her eyes across its contents, and then reached inside. Odessa pulled out a black PVC zip-up corset, held it up on its hanger and smiled. She removed it, and then wrapped it around her big, heavy breasts, instantly pushing them upwards and creating some truly dramatic cleavage. Matt loved her big tits, and Odessa knew that hiding them from him in the corset would drive her boyfriend wonderfully wild with lust and desire.

Furthering the mood, Odessa found Grieg's wonderfully creepy "In The Hall Of The Mountain King" on her Spotify, and cued it up for Matt's arrival. She zipped up her corset in the back, and looked down at the naked bottom half of her body. Odessa smiled at her thin strip of black pubic hair and the generous curve of her hips. Drops of water glistened on her skin, and she was satisfied that her butt-hole was sufficiently clean to be licked and fucked.

Half-naked, Odessa carefully climbed up onto her bed. She then got on all-fours, with her bare butt positioned right in the doorway of her bedroom. Odessa then spread her legs wide, opening up her pale, creamy butt-cheeks, and providing a clear, lurid view of her puckered pink anus, which twitched slightly in anticipation of what was to come. Odessa wanted her butt-hole to be the first thing Matt would see when he walked into her bedroom.