Proving the Bet

I let out a hearty laugh. "Nothin' like a little pressure," I chuckled.

"So what are Gerry and I supposed to do after you've measured us?"

"I haven't thought that far ahead. But like I said, I want you there with me. My safety net."

"Speaking of net, I'm about to pop through this damn swimsuit. How are we going to make it to their cabin without people staring at my bulge?"

"Here's a towel, sport," she laughed, tossing one at me from the table between our deck chairs. "My wrap is taken -- I need it to hide the wet spot on my swimsuit panties."

"Let's go," I said, wondering what we were in for next.

* * * * *

I was relieved that Dan was willing to play along. God, he was a good man. The best.

I knocked tentatively at Deborah and Gerry's cabin door. "Come in, welcome," Gerry greeted as he opened the door. He wore a tee shirt and some loose-fitting orange swim trunks. No hint of a boner -- it was impossible to tell whether Deborah was exaggerating in her description of his proportions.

Dan stood aside for me to enter first, then followed in behind me. Deborah called from the bathroom, "I'll be right out."

Gerry flipped the TV off, his video game having been interrupted. Dan spoke up, "So your wife has roped you into this bet, too?"

"Yep," he replied, "no sweat, mate. It's for their benefit, not ours. At least -- not that Deb's made me aware of."

My pussy began to tingle again. What was Gerry hinting at? I looked at Dan. He seemed relieved that there was no pressure, but as his eye caught mine, there was obviously something more on his mind. A quizzical look, as if...

Deborah stepped out of the bathroom. She was still wearing her black-and-silver striped bikini. "Sorry about that," she quipped, "I just needed to finish masturbating. That was a hot little escapade we pulled up on Deck 11. You couldn't just walk away and do nothing about it, could you, Christine?"

"Ummm, Deb," Gerry grimaced, "remember how we talked about TMI? 'Too Much Information'?"

"Oh, loosen up, love," she taunted, "they wouldn't be here if they weren't sexual creatures."

"So did everything cum out all right?" I dared to ask, feeling emboldened, my pussy juices now flowing freely. "I mean, are you satisfied? Does this mean you've got nothing left?" Truth be told, I desperately needed release after our antics on the "clothing optional" deck. My libido was on auto-pilot; I was afraid my juices would begin to run down my leg.

"Plenty left -- for you, my little boxlicker," she challenged. "Gerry, show her your goods so she can get started pleasing me."

Gerry wasted no time in pulling down his trunks. Deborah picked up a ruler from the countertop and handed it to me. "Why are you giving this to me?" I asked, genuinely surprised.

"I figure it increases my chance of winning," smiled Deborah, "his cock will get longer from having a fresh face checking it out."

I gulped. I thought to myself, "This isn't part of the deal, is it?" Then I looked at Dan's face. I'd come to know him well enough over the years to recognize that look -- pure wanton lust. He nodded absent-mindedly in my direction as my juices began to pool in my briefs...

* * * * *

So this was the next step. My raging boner was threatening to escape my briefs. It was such a rush, watching Christine's eyes as she realized what Deborah was asking her to do. There was no way she was going to be able to measure Gerry's dick without touching it. I wanted her to want to, and then I saw it -- that little curling smile of satisfaction on the edges of her lips. She had made her decision.

"Okay, big boy," she announced as she kneeled in front of him, "let's see what you've got!" With that, she grasped Gerry's suddenly massive cock and held the ruler gently against it.

Squinting with one eye, the other eye closed, she pushed the end of the ruler against his lower abdomen, at the base of his shaft, then said, "Eight and a quarter inches, fully erect. At least, I think it's fully erect..."

"We'll see about that in a minute," replied Deborah, turning to me. "Now it's your turn. Give me the ruler, Christine."

I was in ecstasy. This self-assertive Amazon was going to hold my cock in her hand. I hadn't been touched by a woman other than Christine for over 20 years. Deborah's eyes were fixed on mine as she walked toward me, ruler in hand.

"Drop 'em," she commanded.

"Yes, ma'am," I smiled, shucking my swim shorts in one fell swoop.

As I stepped away from them, Deborah growled, "Where ya goin', tiger?" She pulled me back in front of her by yanking (ever so carefully) the obvious appendage.

"Um, nowhere," I replied weakly.

Her hand began to subtly stroke my rod. It was heavenly, but I worried about losing the bet for Christine. "Hey, play fair -- you'll make me cum doing that," I complained, "no way I can measure up if that happens."

"And then your little boxlicker wife will have to pleasure me," she retorted, "you okay with that?"

I looked over at Christine. She had stood up from in front of Gerry and was watching Deborah handle my penis. Christine was silently nodding, while her right hand was massaging her right tit through her swimsuit top.

Seeing Christine's arousal affirmed my resolve. "I'm okay with Christine going down on you," I said, "but I have my pride at stake here. I don't want to measure out at 2 or 3 inches after you've made me shoot my wad."

"I think I'll make you cum, all right -- but not just yet," she smiled, her eyes twinkling merrily. My god, the woman was simultaneously brazen and entrancing! I could see why Christine was both frightened and infatuated by her.

She bent down from the waist to measure me, her luscious boobs cleaving together with the force of gravity. She chewed a bit on her lip, a look of consternation forming on her brow.

"Um, eight and a quarter inches, fully erect."

"Tie goes to the baserunner," I joked, recalling my baseball playing days.

"I have a way to break the tie," stated Deborah, "I'm not sure either of you is 'fully erect.' There's always room for more excitement to add to a man's length."

With that, she knelt down in front of me and leaned forward toward my crotch. I looked up to see Christine's reaction. Rather than being perturbed, she appeared to enjoy what was transpiring. I felt Deborah's warm tongue on the tip of my cock head, and saw Christine's fingers begin massaging her right breast more vigorously.

As the warm inner flesh of Deborah's mouth encouraged my prick to grow, Christine's left hand moved up her own thigh and surreptitiously began rubbing her snatch through her swimsuit. I caught sight of Gerry gazing at Christine's now-blatant masturbation. He began to stroke his cock.

As Deborah continued to suck and lick my rod, alternately withdrawing teasingly and then swallowing me deeper, I felt the semen begin to surge from my balls. "Not yet, dammit," I exhaled, "you need to measure first."

Smiling a cheshire cat grin, Deborah released my erection from her mouth and placed the ruler back up against me. "Eight and a half inches!" she proclaimed, "come on, Christine, you can make Gerry do better than that!"

"Me -- suck your husband's dick?" Christine queried incredulously.

"It smacks of necessary symmetry," Deborah replied, "what's fair is fair."

Christine looked to me for permission. "Go ahead, babe -- what's fair is fair," I conceded.

She knelt in front of Gerry once again. Somewhat tentatively, she grasped his penis near the base and began to stroke. Then, leaning over his bulging shaft, she licked her lips in a display of intense concentration. Secretly, I was cheering her on. "Suck him, baby!" my mind was screaming.

And suddenly, she did just that. Opening her mouth wide, she took half his shaft inside, adjusting her sucking rhythm to the rhythm of her hand further down toward his balls. I saw her eyes close in silent ecstasy as her head bobbed up and down on his prick.

After a minute or two, Deborah interrupted, "Okay, okay. Don't make him cum -- yet. And not with your mouth..."

Christine's eyes flew open. I saw the question in her eyes. My cock began to twitch as my mind began to wander.

"Here's the ruler," Deborah declared, handing it to Christine, who had just released Gerry's cock from her mouth. "What's the word?"

Again aligning her line of sight with one eye closed and one eye squinting, Christine checked and double-checked Gerry's length. "Eight and a half inches," she announced, "tied again."

"Only one way to break it," stated Deborah. "Overall size was part of the bet -- length and thickness. But since we have here two irregular shapes," she mocked, "not even a geometry major would be able to determine the volume based on outward measurements. We need a more subjective measure."

"Subjective? What do you mean?"

"I mean you subjectively know what Dan's size feels like inside you. I subjectively know what Gerry's feels like inside me. So-o-o..."

"So what?" Christine demanded, her cheeks becoming flushed.

"So, you need to feel Gerry's prick inside you -- for comparative purposes. And I need to feel Dan's inside me. It's the only way to break the tie."

"Oh, shit!" Christine exclaimed.

"Not exactly what I had in mind," laughed Deborah, "rather something in the other hole, and coming in rather than going out."

"TMI, Deb!" interjected Gerry.

I watched Christine's left eyebrow raise in perplexity.

* * * * *

I couldn't believe my ears. I looked to Dan for affirmation. I couldn't speak, but pleaded with my eyes. What should I do? I attempted to convey the question in whatever body language I could muster.

The fact was that Deborah wanted me to fuck her husband. And she wanted to fuck my husband. And she was fucking with my mind again.

I didn't know whether to be insulted or flattered. I looked at Gerry's massive cock, now standing at full attention. "Is that because of me?" I wondered silently, "Am I still attractive enough to excite a stranger like that?" Somewhere deep inside I began to wonder what Gerry's length would feel like inside me. "What am I thinking -- I'm a married woman!" my brain shouted.

I looked at Dan again. I saw the familiar grin, the slight nod. Fuck -- he wanted to see this!

I turned back to Gerry. "What do you want?" I asked.

"Let me show you," he replied. He leaned down and kissed me on the lips. His lips were so soft, felt so good. Before I knew it, I was opening my mouth in invitation. His tongue danced with mine. His breath carried a hint of peppermint. "God, you taste good," I said as I came up for air.

By this point, my pussy was throbbing with need. I grasped Gerry's cock with my hand while we kissed, and rubbed it up against my bikini briefs. He slipped his hand down the back of my swimsuit and began to gently rub my ass cheeks. God, he felt good.

I wrapped my free arm around his shoulders. He wrapped his free arm around my back and began to loosen the tie at the back of my floral print top. As he finished his task and released my breasts from their constraint, he stood back to admire my naked flesh.

I took the opportunity to pull his tee shirt over his head and toss it on the floor. He was now completely naked. I, on the other hand, needed to get rid of my swimsuit panties. I could tell that Gerry was waiting for me to make that move rather than imposing it on me.

"No turning back now," I thought to myself as I slid my panties down to my knees. I stopped long enough to tease him briefly, and I could see the wounded look on his face. I grabbed his hand that had been on my ass and moved it to my pubic mound. "Oh, my GAWD!" I moaned as he immediately found my soaked clit and began to rub.

I pulled my swimsuit panties all the way down and off. We were now both totally naked. Gerry began to nuzzle my face once again, and our tongues returned to their mutual amorous combat.

His hand that had freed my top was now working on my left breast, which was totally engorged with lust. He was stoking the fires of my innermost femininity with his other hand.

I felt his hands move to the backs of both of my thighs, just above the knees. I let out a mew of dejection at his abandonment of my clit. Then I felt him lift me in the air, as he began walking toward the bed. He pulled the sheets back and lay me down, gazing lovingly at my naked and heated body. He lay down next to me. "Are you sure you want this -- all for a silly bet?" he asked.

"Screw the bet. I want this -- period," I replied.

"You can screw my husband, but the bet still stands," piped up Deborah.

I couldn't contain a giggle. "I'm about to prove that your husband isn't as big as mine, so you just line up there and get ready to lick his cum out of my snatch when he's done, my little cream-pie girl," I retorted.

Gerry smiled as he rolled over and positioned himself adjacent to me. "Girl on top?" he asked.

"Sure," I replied, "it's one of Dan's favourite positions, so it's a good basis for comparison."

I was brimming over with libido. It had been over 20 years since I had any man besides Dan inside me. Despite my ardor, I wanted to be sure Dan was okay, to let him know that I loved him and was thinking of him. I looked over into Dan's eyes and flashed a sign at him, extending my hand: index and pinky pointed up, thumb extended out -- the classic "I love you" from sign language.

I straddled Gerry's legs as I prepared to receive his cock in my previously monogamous pussy. I looked back at Dan again -- he smiled and flashed the "I love you" sign back to me. Grasping Gerry's burgeoning dick, I rubbed his cock head on the juices around my sopping snatch. God, I was on fire, and as slippery as I've ever been.

I closed my eyes, feeling Gerry's hands massaging both my tits, feeling his cock pushing up against my womanhood. I eased my weight down, feeling his prick beginning to part my labia...

* * * * *

Watching Christine spreading her legs wide, about to have her pussy penetrated by another man, was the hottest thing I've ever witnessed in my life. God, I was about to explode in orgasmic ecstasy right then and there.

The moment seemed to hang like a "freeze frame" on a video. Only this was no porn show, it was real life. And my wife was really going through with this. It was too late to stop now.

And then it happened: Gerry's dick disappeared in my wife's willing cunt. The scene was enthralling... captivating... frightening...

I saw the look of ecstasy on her face as he massaged her heaving breasts and began pumping inside her. Her erect nipples and desperate pelvic thrusting told me all I needed to know. She was in an ecstatic frenzy. My hand lazily began stroking my own turgid shaft.

"No-no-no, love," said Deborah as she saw what I was doing. "No getting yourself off while there's still a bet to be won."

I'm sure my face must have shown the bitter disappointment in my heart and my loins. I desperately needed relief as my excitement began to boil over. She seemed to understand, saying, "Nothing says I can't be measuring you at the same time Christine's measuring Gerry..."

Holy fuck! The Amazon was asking me to fuck her on the spot!

I must have looked like a goofy kid in a candy store. "I-I'm sure I could accommodate," I stammered.

She pushed me toward the easy chair in the corner. "Sit," she ordered.

I sat down in the leather chair, which was a bit uncomfortable on my now-sweaty ass. As Deborah began shucking her swimsuit, my thoughts of comfort turned more to carnal desires. I glanced over at the twosome fucking on the bed. They had reverted to the missionary position, and Christine's hips were thrusting in perfect rhythm to Gerry's.

"Hey, you're doing more than measuring over there," I accused teasingly. I rapidly returned my focus to the sexy type-A bitch who was unwrapping her treasures for me.

As her top dropped to the floor, I witnessed the most magnificent rack that I had ever seen in the flesh. I momentarily wondered whether she had some sort of silicone enhancement, but then decided I didn't care as I reached out to gently squeeze them.

Deborah maintained eye contact with me as she slipped her swimsuit panties off. It was as if she were looking into my soul. Somehow I felt there was a deeper connection between us. I badly wanted to look down at her snatch, but her transfixing eye contact silently commanded me to wait for her orders. My hands continued to knead her naked breasts.

"Lick me before I sit on you," she ordered. Granted this permission to look (and do more) down below, I moved my hands down her body, briefly giving her ass cheeks a hug as I pressed my nose into her twat. My tongue soon followed.

"Hey, I'm supposed to get that first!" Christine called from the bed. Gerry was still pistoning in and out of her soaked love tunnel, but she was watching what was going on with us!

"So, you're planning to lose the bet?" Deborah taunted Christine.

"Ummm... well, this -- hubby -- of -- yours -- is freakin' -- filling -- me up," Christine admitted with ragged breaths. I noticed her breasts bouncing to the rhythm of their mutual coital thrusts.

"So -- you concede?"

I was momentarily panic-struck. "Please, please, don't take this opportunity away from me," I thought, trying to send my brainwaves over to Christine.

"Fuck, no," responded Christine, "maybe -- your -- 'fresh meat' -- will -- inspire Dan -- just like -- I'm inspiring Gerry."

Thank God! My sweet, darling Christine!

With that, Deborah put two fingers on my shoulder to push my face away from her mound. "You ready?" she asked.

"You bet!" I replied.

"That's what got me into this in the first place!" she deadpanned.

I couldn't help but let out a peal of laughter. Despite my mirth, my cock was still dead serious.

"For comparative purposes in measuring your lovely little -- and I do mean little -- tool," she joked, laying on her British brogue thickly, "reverse straddle will be the ideal position. Gerry's favourite." She turned away from me and bent slightly forward. Her ass was simply luscious. I squeezed each cheek as if it were a fruit I was checking for ripeness at the grocery store.

Her vulva was framed by genuine blonde wisps of pubic hair, her pink labia pulsing as they begged for more attention. A strand of my saliva was dripping from her clit.

Deborah straddled my legs, hovering over my dick, which was standing at attention. Pumping my shaft a few times with her hand, she placed my cock head in perfect position for penetration of her pussy.

As she eased her slit down on my shaft, her silky slickness enveloped me. God, she was incredible! My hands moved up to massage her shoulders, and then slipped around to the front to rub her breasts from behind.

I felt like rising up off the chair to thrust into her, but I didn't want to let go of her tits, so I had no leverage. My cock was straining inside her warm depths. I was sure I had to be bigger than I'd ever been. Surely, I'd make her think twice about claiming victory on the bet.

As if reading my mind, Deborah suddenly puffed, "Dan, my sweet little Dan, you're not so little after all..."

Suddenly, I heard a wail from over on the bed. "Ger-ry! Can you cum?"

"Inside you?" he had the sensitivity -- or stupidity -- to ask.

"Y-y-yes," she moaned, "God, yes!"

Still in their missionary position, I saw Gerry's hand move down to Christine's snatch, frigging her clit.

"Oh, my GAWD!" screamed Christine. Her hips were bucking wildly. I saw Gerry's thigh muscles convulse with his final thrusts before ejaculation. "Fuck me so good!" begged Christine, "fill me with your jism!"

I could see the moment they reached mutual orgasm. The "freeze frames" of their contortions and spasms remain locked in my mind. Gerry's pumping slowed, as did hers, and he leaned into her for an extended kiss. Her body was shivering with release, as she cupped his head between her hands and returned the kiss.