Oz Beach Boy Plays Strip Tennis

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MILF challenges Matt to strip tennis...he loses!
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NOTES: This is a CFNM story featuring a confident, dominant woman in her early fifties and a slightly submissive, muscular, well-hung 25-year-old man. It features male nudity, female-of-male body worship, humiliation, verbal ridicule, mild femdom, spanking, butt-play, and an outdoor sex scene. All characters featured and mentioned are over eighteen. This is a complete work of fiction.

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It was a hot, bright, sunny day in Sydney, Australia. I stood nervously outside the impressive palatial home of Hannah Horowitz, a sexy 51-year-old widow I'd never met in person before.

The very intriguing-sounding Hannah Horowitz was a friend of Dominique St. Clair, a beautiful fifty-year-old divorcee I'd been enjoying a very casual sexual affair with. Dominique and I had first made love when the wealthy lawyer walked in on me in nothing but a towel beside her luxurious backyard swimming pool.

Dominique was the mother of the equally beautiful Mia, an absolutely enchanting eighteen-year-old schoolgirl with whom I'd formed a very kinky, highly inappropriate bond, considering our age difference.

I'd been swimming nude for the prurient entertainment of the school-dodging Mia and her also eighteen-year-old and beautiful friend Iris, who then had some very, very sordid fun with me by the pool. [See Story: "Oz Beach Boy Poked By Schoolgirls"]

Once Dominique had sent the hugely embarrassed girls scurrying back to school, the beautiful divorcee ripped off my towel, and we then enjoyed a highly arousing afternoon of hot, torrid, uninhibited sex on her expensive silk bedsheets in the bedroom of her stylish home. [See Story: "Oz Beach Boy Meets Schoolgirl's Mum"]

Though not clinically diagnosed, I'm a raging sex addict, and I just can't get enough women. I'm a 25-year-old, narcissistic Aussie male exhibitionist, and I get my kicks from stripping off my gear for ladies that like to look.

I spend hours running, swimming and training in the gym to get my body as ripped and muscular as I possibly can. I also keep my perennially summer-ready rig waxed, smooth and almost completely free of hair, principally to up my appeal for the females of the species.

Though I love all kinds of heterosexual sex, I also have decidedly submissive tendencies, and I enjoy being bossed around by powerful women in the bedroom, especially when they're fully clothed and I'm in the nude.

Dominique got extremely excited when I posed nude for her enjoyment, and then strutted around with my enormous cock and big, heavy ball-sack dangling free. My constant nudity was a major turn-on for the sexy divorcee.

On that first afternoon of hot sex, Dominique asked if I'd enjoy being passed around amongst her also fifty-something friends. I love older women -- actually, I love pretty much all kinds of women, of all ages, and all shapes, colours and sizes -- and I answered in the affirmative, but with a little hesitation.

As one of my few rules, I don't get involved with married women, and though I have submissive tendencies, I don't like being hurt, roughed up, or horribly compromised during sex.

Dominique smilingly assured me she'd only set me up with divorcees, widows and singles that wouldn't physically torture me or put me in any overly precarious situations. That put my mind at ease.

I was mildly uncomfortable about becoming a sexual plaything to be laughingly passed around by a group of wealthy women twice my age, almost like a male prostitute, but without the pay.

There was, however, also a deep, rich vein of excitement running through that sense of concern. The whole idea was luridly fascinating to me, and it would obviously provide me with instant, no-strings sex, which was a huge appeal.

Always eagerly enjoying each other's bodies, Dominique and I had fucked a few more times after that first tryst at her luxurious coastal home, breathlessly pushing each other to roaring orgasms in the gorgeous divorcee's huge bed, on her kitchen floor, in the backseat of her car, and even in her swimming pool.

Dominique's daughter Mia had left for a year of post-school travel overseas (which she was loving, according to Dominique), and her other two children were adults now living on their own out of home, which meant there were no interruptions during our sexual escapades. The house was ours, and we used it.

That also meant that I could spend my entire time with the beautiful divorcee completely nude. In fact, Dominique would often make me surrender all my clothes upon entering her house. I was her personal nude toy-boy, and I loved it.

"I told my friend Hannah Horowitz about you," Dominique said while running her fingers through my man-scaped pubic hair after we'd had wonderful sex one grey, rainy afternoon. "I told her how you strip naked for me and then do what you're told in the bedroom. She said you sound like her kind of guy. She'd like to meet you."

"She likes younger men?" I asked.

"All women do," Dominique smiled. "Even the ones that say they don't really do. And who wouldn't like you? You've got the face of a movie star, the body of a Greek god, and the penis of a racehorse...what's not to like?"

"Your friend Hannah isn't married, I hope?" I smiled. "That's one of my few rules when it comes to sex...and she has to be over eighteen too."

"Yes, she's way over eighteen," Dominique howled. "She's 51, and she's a widow. Her husband passed away ten years ago. Hannah zipped her pussy up for five years when Grant died, but for the past five years, she's just been having fun...lots of fun. She and Grant ran a very successful string of high-end furniture stores together. She's very wealthy and has a beautiful home."

"How do you know Hannah?" I asked.

"I did some legal work for her and Grant years and years ago, when we were all starting out," Dominique replied. "We've been very close friends ever since."

"I'm guessing she's nice then, yeah?" I asked. "Is she as gorgeous as you though, Dominique?"

"Hannah is very, very attractive," Dominique replied. "She's cheeky and funny too...very naughty. She likes to get up to mischief. She's much raunchier than me. You'll have a lot of fun together. I'll give her your email address and I'll leave you to it."

"Sure thing," I smiled. "Go for it, Dominique...I'd love to meet Hannah."

The very next morning, Hannah got in touch with me. After a few days of email back-and-forth banter, we arranged a hook-up. The 51-year-old widow also sent through a couple of disappointingly non-nude photos of herself, and Dominique thankfully wasn't massaging the truth: Hannah was very attractive indeed.

In her final email communication, Hannah provided me with her home address, and asked me to come over to her house a few days later at 10:00am on the dot. I was excited about meeting this beautiful older woman and finding out what she had in store for me.

"Dominique has told me all about your hot body and your massive dick," Hannah wrote. "Dress for tennis, Matt. There's a court on my property. I want to get you on there...and I want to make it interesting."

I got hot just reading Hannah's final email, which was a saucy, entertaining pointer to how naughty this attractive widow very likely was. What did she have planned for me on her tennis court? I giggled at Hannah's final email sign-off.

"I've got racquets, towels, and all the equipment," Hannah wrote. "The only balls you need to bring are the big ones hanging between your legs."

Right on 10:00am a few days later, I was dressed in a tight-fitting white polo shirt, navy blue shorts, Asics trainers and a white Tommy Hilfiger visor. I play tennis occasionally with my best friend and one-time foster sister Darby Hamilton, so I had all the on-court gear ready to go.

Despite looking the part, however, I was far, far from top-tier on the court. I could certainly play, and I was extremely fit and agile, but something told me Hannah Horowitz was going to be far better with a racquet than I was.

I nervously reached out and pressed the doorbell to Hannah's large, beautiful home, which was located in a high-end Sydney harbour-side suburb. I heard the bell peal out through the house, and a few moments later, its big ornate door swung inwards.

"Hi, Hannah," I smiled. "I'm Matt...it's nice to finally meet you in the flesh."

"Well, helloooooo, Matt," Hannah Horowitz replied with a salacious smile, and looked me up and down hungrily. "Fuck me, look at you! Holy fucking shit, Dominique was not lying...you are quite the hunk! Get your sexy tush in here before my female neighbours start fingering themselves over you!"

I laughed loudly and walked into Hannah's expansive, luxuriously appointed home. Grand and stylish, it was quite the pad...and Hannah was quite the woman. Obviously very cheeky and very funny, the 51-year-old widow was also a real looker.

"Follow me, sexy," Hannah said and walked briskly through the house. "Get your dick and balls in here, mate. Let's go outside."

The hilariously foul-mouthed Hannah Horowitz was tall and lean with long, wavy, caramel-coloured hair and rich brown eyes. Her nose was charmingly and sexily hooked, which gave her a slightly exotic appearance.

The entertainingly confident and uninhibited widow had a wonderfully knowing smile, perfectly shaped mid-sized breasts, and long, toned legs. She looked fit, healthy, and very, very happy.

Casually glamorous, Hannah had obviously paid a few visits to the plastic surgeon and the Botox clinic, but she still looked winningly fresh and natural. The 51-year-old widow was very easy on the eye, and she looked great in her obviously expensive tennis gear, which fit her perfectly.

Hannah sported a sleeveless white Nike t-shirt which showed off her nicely toned arms, teamed with a beautifully leg-baring short pleated tennis skirt, also in white and emblazoned with the Nike logo. On Hannah's feet were high-end Nike sneakers, while her wavy hair was kept in check by a black Serena Williams-branded cap.

"I can see why Dominique's been letting you suck her snatch," Hannah giggled. "She's not usually into toy-boys, but you are a fucking stud, Matt. A stone cold motherfucking stud."

"Um, thanks," I stuttered in shock at Hannah's increasingly ribald forwardness. "Dominique's a great lady. We have lots of fun."

I followed Hannah through the house eagerly, and we eventually ended up in the outdoor grounds, which boasted manicured lawns, a huge swimming pool and spa, and a grandly arranged, fenced-off, concrete-base tennis court.

Hannah led me through the gate and to a large table positioned by the court. The sexy widow handed me a tall glass of water with a warm smile. She grabbed a drink herself and we stood looking each other up and down for a few sexually charged minutes. Hannah stared directly at my crotch and smiled.

"You really fill out those shorts nicely, Matt," the glamorous 51-year-old smirked. "And you're practically bursting out of that fucking polo shirt. It looks like it's gonna rip apart at any minute! Fucking please! Those muscles...you spend a lot of time in the gym, yeah?"

"Yes, I do," I replied. "I like to stay in shape. And so do you, Hannah, that's obvious...you've got a great body."

"Well, thank you, Matt," Hannah smiled. "I'm a 51-year-old woman with two adult children...I don't get too many compliments from 25-year-old men. I'll fucking take it though, I tell you! Tell me how cute my butt is! I won't be offended."

"Oh, it's cute alright," I chortled. "You look wonderful in that little skirt."

"You're a sweetheart, Matt," Hannah giggled. "It takes a lot of hard work -- and a bit of money too -- to look this good at my age. You'll see what happens when you get older...your nuts will be bouncing off your toes and you won't be able to get it up. Your cock will turn into a limp noodle and you'll be chugging Viagra like Tic-Tacs. Make the most of your youth, Matt!"

Laughing wildly, we sat down and chatted for about ten minutes by the tennis court, enjoying the sunshine. We flirted openly and enthusiastically with each other and constantly checked out each other's bodies.

I asked about Hannah's successful furniture retail business, and she enquired about my work. It was a nice, friendly chat, and the sexual tension was broiling and bubbling away beautifully between us.

We both obviously wanted to cut the talk and get naughty, however, and Hannah eventually brought the conversation right back to where we both obviously wanted it to go. The beautiful widow took a long gulp of water and gave me a wonderfully dirty smile.

"Dominique has told me all about you...in very explicit detail," Hannah said naughtily. "She's told me everything...and I mean everything. I know about your huge dick...I know you like to fuck and eat pussy...I know you like to make a woman purr. You like to have fun, yeah?"

"I do," I smiled. "I love women and I love to have fun. I'm very free with my body. I like to have sex as much as I can. We could have a good time, Hannah."

"That's great," Hannah said. "That's really great. I'm sure we could. Yes, Dominique told me you're very comfortable with your body."

"She takes my clothes off me when I come to her house," I said flirtatiously. "She only gives them back when I leave."

"That's perfect," Hannah smiled naughtily. "That's perfect, Matt. Right, let's get to it then. I'd like to challenge you to a game of tennis, Matt...a game of strip tennis."

"What?" I giggled. "Strip tennis? Are you serious? Out here in the open?"

"Yes, Matt," Hannah smiled. "Nobody can see into the grounds here. This will be fun. Whoever loses a point has to take off an item of clothing. Shoes count as one item. Socks count as one item. The underwear comes off too. Whoever ends up completely nude has to then play two more points with absolutely nothing on...not a fucking stitch."

"Oh my god," I shook my head. "This is crazy. Running around the court naked?"

"Oh, yes...and after playing two points in the nude," Hannah said with an almost evil smile, "the loser then has to bend over the net and take five licks on their bare butt from the winner's racquet."

"Oh, my god...Hannah, you are quite the woman," I smiled. "I can see that already...you are very, very naughty. Oh, my god..."

"Are you in?" Hannah grinned. "Surely you can beat a girl at tennis? A big, muscly guy like you? You'd like to see my titties, wouldn't you? They cost a lot of money, Matt. And I like to keep my front garden nicely groomed...you'd like to see that, wouldn't you? You'd like to get my knickers off, yeah?"

"I certainly would," I smiled. "But something tells me you're a much, much better tennis player than you're letting on, Hannah. I have a hunch it might be my clothes in a pile by the side of the court, and not yours."

"Let's find out, handsome," Hannah smiled. "What do you say, big guy? Are you in? Are you ready for a spot of tennis, my new friend? Or are you a big scaredy cat? A big fucking pussy? Are you a man or a mouse? What do you say, Matt? Are we on?"

"You don't have to challenge my masculinity...sure...we're on," I smiled. "Let's do it. I'll play strip tennis with you, Hannah Horowitz."

"Oh, you're the one that's gonna get played with, Matt," Hannah giggled. "Get your tush on centre court, young man! Pronto!"

Gazing at Hannah's long, obviously spray-tanned legs as she stood up from the table, I saucily imagined them wrapped around my waist, and then even more saucily wrapped around my head. After likely losing my clothes to Hannah on the tennis court, I desperately hoped we'd fuck too. I wanted this 51-year-old widow bad.

I love having sex with older women. I'd thoroughly enjoyed all my dalliances with Dominique, and I'd also had a wonderfully sloppy, boozy threesome in Byron Bay a while back with two very thirsty women in their early sixties which had completely blown my mind. [See Story: "Oz Beach Boy And Byron Bay Oldies"]

I was also enjoying very occasional, no-strings sex with Monica Halsey, the gorgeous forty-something mum of a very ill child who I had met while volunteering at a hospital over Christmas. [See Story: "Oz Beach Boy's Xmas Hospital Strip"]

I truly love just about everything that older women have to offer, and I really wanted to sample the mature delights of the very sexy and highly entertaining Hannah Horowitz too.

As I got up out of my chair, I felt my cock stiffen slightly. I am very easily aroused, but I was hopeful I'd be able to sexually please the very forthright Hannah Horowitz. I suspected if I didn't, the beautiful 51-year-old would make an absolute mockery of me.

I'm horribly and disappointingly prone to premature ejaculation, and I've humiliated myself on many occasions, but I'd already very sensibly jerked off twice that morning, which would hopefully help me last longer for Hannah.

My jerk-off fantasy that morning was enjoyably close to home. The previous evening, I'd happily crossed paths with a young woman I'd developed a very hot, lustful crush on.

A new resident in my apartment complex, I'd spotted the beautiful brunette first at the buildings' shared outdoor swimming pool. My new neighbour was tall and fit-looking with big breasts; long, thick, dark hair; and sparkling blue eyes.

I'd already masturbated several times while fantasising about the young woman, pumping my cock while imagining the many sleazy things I'd like to do to her.

As I was heading out for my evening run the day before my meeting with Hannah, the young woman walked into the complex from the street, wearing a very sexy netball uniform. She had a short skirt which showed off her long, toned, pale legs, a sleeveless t-shirt, and a blue bib emblazoned with the letters GS.

Obviously not knowing her name, I immediately nicknamed the young woman Goal Shooter, in honour of the netball position denoted by her blue bib. The vague sexual connotations of the term also fit nicely.

"Hello, Goal Shooter," I thought to myself stupidly. "I wouldn't mind scoring with you."

Goal Shooter and I smiled warmly as we passed each other, and I immediately sensed something between us. I'm positive Goal Shooter looked me up and down as we passed, shamelessly checking me out. I desperately tried not to stare too obviously at her big tits, or openly ogle her butt and legs.

Naked on my bed that morning, I replayed my brief encounter with Goal Shooter from the evening before, and then imagined peeling off her netball uniform and licking her pussy.

Suitably aroused, I then furiously slammed my stiff cock up and down until I finally came, slopping jism all over my bare chest and abdomen in just a few delightful minutes.

Just before I left my apartment to drive to Hannah's house, I sensibly opted to jerk off again as an added precaution, this time ducking into the bathroom for a quick pull while watching Cardi B and Megan Thee Stallion's hot "WAP" music video on my phone.

I desperately wanted to please the sexy 51-year-old widow Hannah Horowitz, and I again internally applauded myself for taking such sensible prior wack-off measures. I knew I'd need all my energy -- and all my jism -- to make this woman happy. I was good to go.

Smiling from ear to ear, I walked over to the tennis court, happily gazing once again at Hannah Horowitz's fit, lean body, long legs, and sexy butt. The beautiful widow handed me an obviously expensive Wilson tennis racquet, and then practically skipped to the opposite end of the court.

"Is this thing rigged, Hannah?" I smiled. "Are the strings gonna slip? I know you're hustling me...are you gonna cheat too?"

"Cheat?" Hannah howled with laughter. "I don't need to cheat! I'm gonna kick your arse, Matt...and then I'm gonna spank it with this fucking racquet. You're in this now, Matt! You're gonna have red, sore, checked butt cheeks and a sunburnt dick by the time this is over, young man!"