Oz Beach Boy Plays Strip Tennis

"You're a big talker, Horowitz," I smiled, enjoying Hanna's saucy trash talk and opting to get involved. "Let's see if you can back it up, huh? Or if I'll be getting a boob show...they look very, very nice."

"It's my court, so I'll serve," Hannah giggled. "We can get rid of your clothes quicker that way too. And there's no way you're seeing my tits, Matt."

Both laughing, we pocketed some balls, and got ourselves set on court. Hannah bounced her expensive, top-shelf yellow tennis ball a few times, and then nodded at me with a smile. I returned her smile and braced myself. Her serve would give me a proper idea of how good Hannah really was.

The 51-year-old divorcee tossed the ball, and then struck it with precise but furious power, sending the ball rocketing to the right of me with almost incredible speed. I ran and stretched out for it, but the ball sped past me and slammed into the metal fence surrounding the court. I heard Hannah shriek with laughter.

"Fuck, this is gonna be easy," the beautiful widow shouted. "You'll have your dick hanging out before we know it! Okay, Magic Mike...what's coming off first?"

"A fucking ace?" I mumbled and dropped my racquet gently on the ground. "Are you fucking serious? This is a hustle..."

I quickly slid my Tommy Hilfiger visor off my head and tossed it to the side of the court with a smile. I brushed my already damp, longish, sandy brown hair back off my face. Hannah frowned back at me, and then pointed right at my chest with her racquet.

"You're gonna make me wait to see those muscles, huh?" the older woman smirked. "You're such a tease, Matt. Fuck, I hope you're not wearing underpants! You look like a free-baller!"

Hannah then served again, but this time I was ready for how much power and speed she had, and I managed to get my racquet to the ball, sending it hurtling back over the net.

We then got into a nice rally for a couple of minutes before Hannah caught me at the base line, and then got me by slamming the ball into the court just over the net. I ran for it, but it bounced just before I got my racquet to it.

"Fuck," I cursed in frustration and disappointment.

"After losing another point, 25-year-old Matt is forced to remove another item of clothing," Hannah said in the hushed, extremely proper style of a British Wimbledon commentator. "If it wasn't humiliating enough losing another point to a woman twice his age, the youngster is now going to have to hand over his..."

Hannah then paused her mock commentary with a cheeky smile. I thought about playing it coy just to spite the sexy widow, and briefly considered taking off my shoes next, but quickly checked myself in the face of such a potentially dumb move.

I jokingly sneered and narrowed my eyes at Hannah dramatically, and then slowly peeled off my tight-fitting polo shirt, gradually revealing my heavily muscled bare torso inch by inch.

Open-mouthed, Hannah gawked at my slowly exposed bulging biceps, marbled chest, and ridged abdomen. Bare-chested, I balled up my polo shirt and threw it to the side of the court.

"Oh, yes!" Hannah howled. "I knew this would be worth it! Look at that fucking rig! Dominique said you had a body like a superhero...thank fuck you play tennis like a bitch!"

"This is highly inappropriate," I said in mock offence. "That kind of foul language is not befitting a tennis court. I'm appalled, young lady."

"Oh, shut up and play so I can take the rest of your clothes off you," Hannah giggled. "Come on...before I actually start to sweat. Something else is getting wet though, that's for fucking sure..."

We set ourselves again, and then Hannah sent another powerful serve rocketing just to the right of me. I back-handed it to her, and then we rallied again, running each other around the court in effort, sweat flying off both our brows in the hot sun.

Then, with deft precision, Hannah lobbed the ball right over me, and it landed infuriatingly just inside the base line, before rolling into the wire fence. I was having my arse well and truly handed to me by Hannah Horowitz.

An exhibitionist and narcissist, I obviously had no trouble stripping in front of the beautiful widow, but I was also hoping I might force her to drop a few items of clothing too.

I really wanted to see Hannah's surgically enhanced tits, and maybe even her cute butt. The sexy older woman's teasing talk of her manicured bush also got me very interested indeed. Hannah was hot, and I wanted to see more of her.

Though I'm not overly competitive, I also hoped this would actually be more of an even-sided match. Nudity aside, I didn't like the idea of losing every point in this game of strip tennis. That, however, is the way in which it appeared to be heading. Hannah had it all over me.

"Losing another point to a player that most would have assumed to be his inferior, 25-year-old Matt now has to make a big choice," Hannah said, returning to the hushed style of a British Wimbledon commentator. "Will the handsome hunk sacrifice his modesty by removing his shorts, or will he cling to his dignity by surrendering his shoes first? Those watching, however, have only one question: is Matt wearing underpants?"

"For fuck's sake," I muttered, and undid the button of my shorts. "Come on, Hannah..."

"To the delight of everyone in the crowd, Matt has opted to remove his shorts before his shoes," Hannah continued in commentary mode as I unzipped my shorts. "But to their disappointment, this in all likelihood also confirms that the muscular hunk is, indeed, wearing underpants. The crowd will have to wait a little longer to gaze upon his still hidden manhood."

I slid my shorts down over my muscled legs, and then clumsily wrenched them over my feet, catching them on my sneakers and nearly falling over sideways as I struggled to maintain my balance. I briefly hopped up and down on one leg while pulling at my embarrassingly errant shorts. Hannah giggled loudly as I made a complete fool of myself.

"Are you okay, Matt?" the sexy widow said with mock, theatrical sweetness. "Do you need me to help you take off your pants? Did you dress yourself today? I'll give you a hand, sweetie..."

"That's okay," I huffed, and finally got my shorts off over my sneakers. "I can manage, thank you very much."

I threw my shorts over with my discarded shirt and visor, and stood with my bare arms raised at my sides, giving Hannah a good look at me. I was wearing a tight pair of fitted black boxer shorts that showed off my taut butt and enormous crotch bulge.

I was completely confident about my toned, tanned, waxed, extremely muscular body, but there was no avoiding the fact that any man looks stupid when wearing his underwear teamed with just sneakers and socks. I felt like a complete idiot, and surely looked like one too.

Hannah surprisingly stared at me briefly in silence, looking me up and down continuously, raking her eyes over every inch of my nearly nude body. Then, with a dramatic flourish, the beautiful widow slowly, purposefully licked her lips, and then alluringly flicked her tongue up and down.

"Look at you," Hannah groaned. "Fuck, look at that body..."

"I can't believe you're objectifying me like this," I said in mock indignation. "I feel like a commodity...this is so humiliating."

"Oh, shut the fuck up," Hannah giggled. "Don't be such a whiny little bitch. Let's get those panties off. I don't get care about your fucking feelings. One more point, and that's game. Goodbye panties!"

Hannah then let rip with another powerful serve, which slammed past me at her now familiar pace. I got my racquet to it, but the ball bounced off it awkwardly, and then went hurtling over the sideline and into the wire fence. I sighed with disappointment.

"And that is game," Hannah whooped. "Okay, Matt, what's coming off next? Come on, drop the knickers! Stop making me wait to see it! I can already see you've got nothing to be ashamed of! It's almost poking out of your cute little under-panties!"

I thought long and hard, and opted to take off my shoes. I knew this would put me at a disadvantage, but the thought of running around the court in just my sneakers and socks was too humiliating, even for me. I would look too stupid, and I didn't want Hannah to lose respect for me completely. I still wanted to fuck her desperately. I couldn't turn myself into a total joke.

Plus, it was a new game, and I'd get the chance to serve, which would give me more of an advantage in terms of getting Hannah to take something off. I was happy to settle for anything.

"Come on, bitch!" Hannah yelled. "Make up your mind! Sneakers or panties?"

I set my racquet on the ground and then bent down to untie my shoelaces. I then kicked my sneakers off and flung them over with the rest of my surrendered clothing. I gave Hannah a smirk and a cheeky wink.

"Oh, you're torturing me!" Hannah bellowed. "I should have just ripped your clothes off when you walked in the door! Fuck, I wanna see that salami!"

"Good things come to those who wait," I giggled, bouncing my ball to get set for serve. "I've been very patient, Hannah. I haven't seen a fucking thing of yours!"

"Bring it on, Matt," Hannah whooped. "I'm finishing this match with everything on! Fully clothed, bitch!"

Slightly pissed off, determined, and horny, I tossed my ball into the air and then slammed it with everything I had. Hannah was obviously taken by surprise, and the ball went dashing by her, hitting the court just before the baseline and then crashing into the fence with a loud bang. I'd aced Hannah, and it felt fucking great.

"In a surprising move, the powerhouse veteran has been aced by the inexperienced youngster," I said, copying Hannah's Wimbledon-style commentary gag. "Hannah Horowitz must now remove her first piece of clothing. The sensible money is on her Serena Williams cap, though all the men in the crowd are likely praying for some kind of brain-snap that prompts the renowned beauty to take off her t-shirt and reveal her sports bra."

"No fucking way," Hannah laughed, and then tossed her Serena Williams cap over the sideline, releasing her thick, wavy hair. "Don't get used to winning, Matt. It's just temporary."

I served again, with slightly less force this time, and Hannah slammed it back at me. I returned it, and we then had a lengthy hard-fought rally, pounding the ball all over the court. I could feel the heat of the ground through my socks, and I was at a major disadvantage. I was, however, desperate to score another point.

After our rally, Hannah rushed the net and got the ball deep on the right, but I managed to hit it back over the beautiful widow's head. Hannah reached for it, but the ball bounced and then tumbled into the fence. I'd gotten her again.

"Okay, Hannah...you're finally gonna have to take off something that matters," I smiled. "Let's get a better look at those tits, huh? Let's see them jiggle in your sports bra!"

Hannah gave me the middle finger salute, obviously thought deeply for a moment, and then gave me a broad, decidedly smug smile. With a throaty laugh, the beautiful widow reached up under her skirt with both hands, and then slowly slid her underwear down her long, lithe, spray-tanned legs.

Hannah let the sensible, grey, boy-leg sports pants puddle at her ankles, and then daintily picked them off with her fingers. She gave the underpants a quick twirl on her right index finger and then flung them over the sideline with her hat. Hannah had expertly and discreetly pantsed herself, and I hadn't seen so much as a pubic hair.

"They're wet anyway," Hannah smirked. "They're drenched from me looking at your bare chest and crotch bulge. I feel better with them off. Fuck you, Matt."

"With her panties removed, the men in the crowd are now clearly hoping for a strong summer breeze to come along and lift up the mini-skirt of the beautiful Hannah Horowitz," I said, again copying Hannah's Wimbledon-style commentary gag. "Though she has been dominating her younger opponent, Hannah Horowitz now knows how it feels to surrender your clothing on a tennis court."

"You're gonna have to get used to peeling again, Matt," Hannah howled with laughter. "I'm not losing another point. You're getting cheeky now too...a bit too cocky...I'm gonna enjoy spanking you even more, young man. I'm gonna be your mama!"

I delivered another strong serve, and we rallied again, racing all over the court. The movement made Hannah's skirt lift slightly, and I got several delirium-inducing partial peeks at her gloriously toned backside.

I even thought I may have seen a flash of dark pubic hair when Hannah reached out for a back-hand, but I might have been hallucinating. Either way, Hannah without panties was an even more exciting prospect.

After embarrassingly losing two points, Hannah refocused expertly, and easily had my measure. I tried hard, but the beautiful widow got me again, landing the ball just over the net, and just out of my underwear-clad reach.

"Got ya!" Hannah bellowed. "Alright, take off the stupid fucking socks! It's so close now...I can practically see that dick swinging! I can practically smell your sweaty balls!"

"Hannah, really," I said as I yanked off my filthy, no-longer-white-soled tennis socks, and threw them over the sideline. "Come on..."

"Sorry, Matt," Hannah giggled, "that was a bit gross. I actually apologise for that one."

"Thank you, Hannah," I smiled. "My balls aren't sweaty...ad they don't smell either."

"Though determined and committed, young up and comer Matt has now been stripped almost completely naked," Hannah returned to her Wimbledon-style commentary. "Humiliatingly dominated by his older female opponent, Matt's dignity will be stolen from him if he loses the next point...and the prayers of the females in the crowd will finally be answered with this young stud's total nudity."

"For fuck's sake," I muttered. "Geez..."

"Per the pre-arranged rules of this horribly one-sided game of strip tennis," Hannah continued with a devilish smile, "Matt will not only have to remove his panties, he will then have to play two points completely nude, before being bent over the net and then spanked five times by his opponent with her racquet. This will bring painful new meaning to the term 'humiliating loss.' This cocky youngster is about to learn what a cruel game tennis can be."

Embarrassed and with a bruised ego, but still hot and horny as all get-out, I tossed my ball in the air, and then swung at it aggressively. It was a solid serve, but Hannah returned it with skilful precision. The beautiful widow was all over me in the following rally, and I knew my underpants were coming off.

My bare feet burned from the hot concrete of the court, and I could literally feel my cock and balls swimming around hopelessly in my tight fitted boxer shorts. My near-nude body was slicked with sweat, and was starting to tire from the on-court punishment Hannah was serving up.

With a powerful back-hand, Hannah sent the ball right into the corner once again, and I scurried desperately to catch it, but knew it was futile. I watched with disdain as the perfectly placed ball bounced gently up and down, almost as if it was mocking me for failing to return it.

Hannah finally had me, and I was about to be humiliated beyond belief. Yes, I was mildly submissive, and yes, I had no problem with a beautiful woman seeing my huge cock, but the mocking, jocular nature of this embarrassment was something different altogether. Even though I enjoyed it, Hannah's ridicule definitely stung me.

"Alright!" Hannah dropped to her knees in celebration, and then pointed her racquet right at me with scathing delight while thrusting her hips. "Take those fucking things off! Now! Strip! Get buck fucking naked, bitch! Show me your fucking dick! Let those nuts dangle! The Full Monty!"

"Oh, my god," I muttered, and dropped my racket gently to the ground. "I can't believe this."

"Believe it, bitch...you lose!" Hannah continued. "Peel your panties now! Get rid of those things! Flop that cock!"

"You're merciless, Hannah Horowitz," I muttered. "Geez..."

"This is the easy part, Matt," Hannah laughed. "Going nude is nothing...I can't wait to run you around the court naked and then spank your sweet arse! Now, that's gonna be humiliating!"

I dramatically hooked my thumbs into the sides of my fitted boxers, and then paused for effect. Hannah smiled wickedly, obviously delighted and feeling truly superior now that I was actually forced to strip right in front of her.

As Hannah licked her lips pruriently, I slowly peeled down my underpants, sliding them off sexily. Though pissed off and embarrassed, I still wanted to get the enjoyably malevolent Hannah aroused. The sexy widow watched my every move, not taking her lively eyes off me.

My small thatch of trimmed pubic hair was first revealed, and then the thick, heavy, densely veined ropiness of my cock as my underpants continued their sleazy downward journey.

My big, swinging, uncircumcised cock finally slung out and then swung back and forth absurdly as the tight elastic waistband of my underwear finally cleared it.

Humiliated but undeniably excited, I pulled my boxers down my calves and then off my bare feet quickly, prompting my enormous cock and pendulous nut-sack to sway and jiggle around even more with the movement of my body.

With a smile, I stood naked in front of the hilariously open-mouthed Hannah Horowitz, who for the first time seemed to actually be lost for words. As my bare feet sizzled on the court and the hot sun beat down on my freshly exposed cock and balls, Hannah shook her head slowly.

To add to the bizarre spectacle of my enforced tennis court strip, I slowly spun my removed underpants around on my right index finger with a theatrical flourish, trying to prove that I was taking it all in my naked stride. I then flung my underpants over the sideline, where they flopped down humiliatingly with all the other gear I'd had to surrender.

As I stood nude, desperately trying to maintain my masculinity and some semblance of power, Hannah suddenly threw her head back and shrieked with wild, almost manic laughter.

The beautiful widow doubled over, hysterically clutching at her mid-section. Hannah laughed and laughed and laughed, tears rolling down her cheeks as she continually pointed her racquet at me.

Hannah continued to laugh for nearly five minutes while I stood there with my cock and balls hanging. Most women have an extreme reaction upon seeing my ridiculously outsized penis, but I'd never been laughed at like this before. Finally, it ended, and the red-eyed Hannah eventually collected herself with much effort.

"Oh, Matt, I'm so sorry," Hannah giggled softly. "I just can't believe how big it is. Dominique described your body in explicit detail, and we talked about you in the way that only two old female friends can talk about a man...but I'm still shocked."

"It's okay," I smiled meekly. "Most women have a strong response when I drop my pants."

"And oi vey," Hannah said in an over-the-top New York-style Jewish accent. "You've got a foreskin at the end of your big schvantze! I'm a Jew and I mainly date and fuck Jewish guys, so I don't see many foreskins. It just dangles there! It's like your schvantze needs a little trim."

"Hannah," I started, but the beautiful widow just kept cackling. "Really..."

"Don't worry, goy, it's certainly not a deal-breaker...I mean, your dick is nearly down to your knees...that certainly makes up for your weird foreskin," Hannah gasped. "Your cock's thick too...and those balls! They're enormous. You must blow gallons of jizz! My god, maybe if you'd used your dick instead of your tennis racquet, you might have won the match!"

"You're certainly not making this easy, Hannah," I said quietly. "You like to make fun of a guy, huh?"