The Wager

Sarah bent down to prepare my cock for the anal experience, removing the condom and sucking my shaft, moistening it for the inevitable intrusion into her twin sister's rectum. Marissa meanwhile, tiring of sucking on Sarah's juicy pussy, slid out from under her sister and began fingering her own asshole, preparing for my anal invasion. She had two fingers inside her own ass when I moved to replace them with my shaft.

"Put it in," she begged, now using the same two fingers to massage her swollen clit, emerging like a pink pearl from her labia and the protective hood. As I slid my hardness deep in her backdoor, Marissa pulled me towards her face, kissing me deeply, but subtly urgent in her needs. I fondled her breasts, running my fingers over her sensitive skin, teasing them and exciting the erogenous areas.

Her passion played itself out, and she lay back, hanging off my neck with her one hand and rubbing herself with the other as I continued thrusting my hardness deep into her ass. The tight fit did nothing to diminish her pleasure, though, and she moaned her excitement. Before long, she was cumming again, the exquisite pleasure of her clenching rectum lost on my mostly numb member.

When she was finished, she slid her groin away from mine, and then swung down under me, knowing what was required of her. With my scrotum resting on her breasts, she sucked the tip of my dick into her mouth. Gradually, her mouth enveloped more and more of my shaft until she had licked it clean from the last vestiges of her beautiful ass. She continued to jerk my cock as she slid further underneath me, sucking my balls into her eager, wet mouth. I groaned my pleasure.

Soon, though, I began to worry, as I noted that the feeling was seeping back into my dick, and I still had Alana, the youngest, and probably the tightest of the five. At eighteen, she was barely a woman, and I had to fuck her mouth and ass as well.

But the nubile virgin had a surprise for me as well. As Marissa continued to suck my sack, Alana came over and began sucking my cock, washing it with her saliva and running her tongue down the length of it. When she straightened up to kiss me, I felt my lips rapidly go numb, and an icy cold descend upon my tongue. Suddenly, I realized how the clever girl had rescued me once more. She had somehow managed to covertly get the anesthetic into her mouth before she sucked my dick, returning the numbing sensation to my genitals.

"Hope you like that," she whispered into my ear, but from the sound of it, she was having trouble with her tongue, losing feeling because of the gel.

"Thanks," I whispered back.

"You're welcome," came the final whisper. Then aloud, she said, "I think you'd better fuck me. Daddy dearly wants to see his little angel take it, doesn't he?"

With the effects of the alcohol still inhibiting their good judgment, the two parents didn't notice the slurred words coming out of her mouth, but I saw the questioning glance pass between Keri, Joanna and the twins. Nevertheless, they maintained their silence, watching as I prepared to take their little sister orally, anally and vaginally. In the meantime, Katheryn wanted to inspect the twins to make sure that I hadn't cum in them, and using her tongue, swiftly determined that I had not.

Once more wrapped in a latex condom, I rubbed my unfeeling erection across Alana's vaginal lips, picking up her natural lubricant and coating the whole of my shaft. When it was read, her pussy oozed juice, and the going would have been easy, except for her tightness. My god! It was as tight as any of the other girls' butts, and even though she was only a year younger that the twins, she was that much less experienced. I surmised that the older girls had been experimenting with whatever was available: candles, maybe carrots, and probably each other’s fingers. But Alana was unspoiled. I did find, however, that the strenuous work of farm life had already caused her hymen to tear on it's own, so I was spared the task of inflicting that delicate pain.

Although my penis was the first object to penetrate her innocent pussy, she stretched to fit my length and girth. Nevertheless, she enjoyed the experience fully, and the thrusting motion of my pelvis stimulated her in ways she couldn't imagine possible before, filling her in new ways. When I was fully inside her, with my weight on top of her delicate blond frame, she cooed her satisfaction, and when I pulled out, leaving only the tip of my penis inside her, she gasped at the emptiness. She wanted the whole length deep inside her.

Fortunately, her body knew what to do, even though she was a novice, and her hips began to thrust back towards mine. Her eyes were locked on mine, and she bit her lip, a look of wonder on her face. We fell into an easy rhythm; the sensation of my cock sliding in and out of her tight snatch was enough to build her towards her first sexual climax ever. Soon, she couldn't hold back anymore, and the tidal wave of an orgasm washed over her. She sighed long and hard as the pleasure crescendoed with her first climax. Then she smiled.

"Okay. My ass is next, right?" She said, ever eager to expand her sexual horizons.

"Sure," I casually returned, knowing that the anesthetic could afford me some time. I would have to get her ass used to having something in it, and gradually work up to my eight-inch cock. So I started with my tongue. I licked all over her rear entrance, and up to her pussy, giving her some oral stimulation on her sensitive bud. Then it was back down to her ass. As she loosened up, I slipped one finger inside, just the tip. As I returned my attentions to her clitoris, her ass slowly relaxed, allowing me to slip my finger in further.

After spending some time loosening her up and preparing her for what was to come, I finally lined the tip of my cock up with the ring of her anus. I pushed in. Alana seemed to know instinctively what to do, and she relaxed against the intrusion. Sooner than I had anticipated, I was balls deep in her backdoor, and sliding my cock out.

"All the way," Alana said, "go all the way in and out." Not one to argue, I began sliding the length of my cock in and out of her ass, going from all eight inches inside her to just the mushroom head. Her eyes rolled back in her head with the ecstasy, and she moaned deeply as I moved my hard cock inside her tightest of holes. I placed her hands on her breasts, kneading them, and she carried on the motion, tweaking her nipples and learning what her own body wanted as I thrust n and out of her. My fingers parted her pussy lips, seeking her pleasure button, and when I found her little clit, I played with it until the clenching of her ass told me she was going to cum. She looked at me with a look of sheer rapture as the second orgasm rolled over her, and when it had subsided, instead of stopping, Alana just kept thrusting her ass back at me, wanting more. With the numbing gel still having its effect on my penis, I didn't argue, but kept going, pleasuring the 18 year old until her third climax drained her strength.

As I pulled out of her ass, she barely managed to move herself down to where she could clean the result of her pleasure from my still-throbbing member. When she had finished lapping at my cock, I presented it to Katheryn for inspection, and she dropped to her knees and engulfed it in her experienced mouth. Her one hand played with her pussy while the other hefted my balls, determining them to still be full of sperm.

She quickly inspected the orifices of her youngest, making sure that they too were void of my semen. Satisfied, Katheryn looked over at her husband and informed him that I had won the wager.

"Wait!" he said. "You already have my wife as yours and my house as yours. I'll wager that you can't make my wife cum before she gets you to cum. If she can, I get it all back."

"And if you lose?" The numbing gel gave me a measure of confidence.

"My daughters are yours."

I figured that they already were, but since he seemed so desperate, I decided to concede the point. Besides, I sensed that the gel would last me long enough to give Katheryn the ride of her life. Besides, I could tell from the look in her eyes that she wanted a chance to ride my eight inches, having seen what I could do with her daughters, and having taken the length of it in her mouth. She was game for it. Besides, I really didn't stand to lose anything.

"How do you want it baby?" I asked her.

"Seeing as this is a farm, I'm going to ride you like a cowgirl." She returned, with a nasty smile on her face. She pushed me down to the floor, and straddled my hips, grabbing my eight inches firmly and lining it up with her eager pussy. As she sunk down on the length of it, she groaned her satisfaction. When my hard on was fully inside of her, she began to ride it like there was no tomorrow. She was grinding and swaying, twisting, doing everything in her power to make me shoot my load inside her hungry snatch, but to no avail. The anesthetic was still not wearing off.

I was tempted to just stretch out and enjoy the sight of her tits bouncing as she rode my pole, but I thought I should bring her pleasure faster. I began grinding my pubic bone up into her every time she sank down on my shaft, and reached up to play with her breasts. Katheryn moaned as I teased her sensitive nipples. But she wasn't finished yet. Her hand ran down behind her ass and began to play with my balls. Since they weren't numbed, I could feel the pleasure. But as good as that felt, I knew it wasn't enough, not with my dick insensitive to the ministrations of her experienced cunt.

The wager, this contest of pleasure, would be mine. I pulled Katheryn to me, her chest against mine and her breasts dragging across my hard muscles with every thrust. I put one hand on each of her ass cheeks, kneading and groping the curve of her butt. Soon, one finger trailed towards her ass, and when I hit it, when I began to tease her nether opening, Katheryn whimpered, knowing that the game was over. She bucked and swayed on my erection, and then gasped out her pleasure as she orgasmed.

Ben was incredulous. "That's impossible. Katheryn can get me off in seconds if she sets her mind to it. Okay, double or nothing if you'll do her ass."

I looked at him, "Double what? You have another five daughters somewhere? I have your house, your wife, and your daughters. All of them won fairly. What else do you have?"

"My farm?"

"Fair enough." I said, knowing I could win that too. "If Katheryn can get me to cum in her ass, you get it all back. If I get her to, then I'll take the farm, leaving you with nothing."

Katheryn slipped off of my still-hard cock and removed the condom. Then she squatted over it with her tight butt hole lined up with my eight-inch erection. As she lowered herself down, I began to play with her clit. Katheryn closed her eyes and sighed. She slowly rose up and sank back down again. Over and over, she bobbed on my cock while I massaged slow circles on her clitoris.

I knew she was getting close to another orgasm when she started speeding up. Then, to my growing awareness, I realized that I could feel her sphincter squeezing and contracting, trying to milk my dick for its creamy cum. The gel was wearing off. I doubled my tempo on her labia, and before feeling was completely restored to my cock, I was rewarded with her moans of ecstasy as the biggest orgasm of her life cascaded over her loins. Katheryn threw her head backwards, gasping at the ceiling and shaking with the pleasure. Exhausted, she collapsed on the floor, her lust satiated and her husband's wager lost.

Suddenly, I noticed a dangerous glare in Ben's eyes.

"You cheated me,” he said, "You cheated me out of everything."

I put my hands up in front of me, "Whoa. Whoa. You made a bet, and I won it. We raised the stakes a few times, and I still won it. How can you say I cheated?"

"I just watched as you fucked all five of my daughters, in their pussies, asses and mouths, and now my wife, who has never failed to satisfy me, can't even get you to cum. That's just impossible. The only way is if you weren't able to cum. So then you cheated because you couldn't cum."

"That's not true," I countered. "I am perfectly able to cum. I just had a good reason not to." It was kind of a lie, but I figured that if he hadn't worked out about the anesthetic gel, that his accusations of cheating were false anyway.

"Well if you can, then prove it. Wait. Let's make a wager. I'll bet that you can't cum. Katheryn will give you a blowjob, and if you cum on her, then I'll stay on the farm and do all the work."

All the feeling had returned to my big dick, so I knew that it wouldn't take much to get me to shoot my load. The sensations that it had missed while anesthetized were lost, but the knowledge that I had fucked all of these women thoroughly and given them the orgasms of a lifetime were enough to get my hard cock twitching. Katheryn sat up, and I led my erection lead me to her mouth, which she swiftly swallowed, one hand on my balls. She sucked and licked the shaft, and then focused her attention on the sensitive head of my raging boner. With the full sensations restored to my groin, it didn't take long for her ministrations to have the desired effect. I pulled away from her mouth, jerked my cock a couple of times, and then long streaming ropes of my pearly cum splashed out, landing across Katheryn's face, breasts and stomach. Some spurts landed in her open mouth, and a couple sprayed into her red hair, matting it together with the milky fluid.

"Well, I'll be damned." Ben said, finally realizing that the tables had been turned on him due to his gambling nature. What had started out with me in a desperate position at the end of his shotgun left him as a slave on the farm while I was able to have my way with the six women of his household.

Four months later, I'm still living there. I barely ever leave the house, since I have six horny women desiring my company all day long. Katheryn tells me she's glad I won the wager, since Ben's little five inches hardly ever pleasured her.

Funny how fortunes can change so quickly when gambling is involved. When I first arrived, there was no room for me in the house, and I had to sleep in the barn. Now that's where Ben stays when he isn't about the many chores the farm has for him. We aren't completely heartless, though. We put an electric heater out n the barn for him to stay warm. And now and then, we leave a curtain open so Ben can still have the pleasure of watching me fuck the women, just like on that first fateful night.

Oh, and one more thing. That toothache that started the whole thing? Mysteriously, it vanished that night. Or maybe I'm just too busy having sex all the time to think about it. Either way, I don't use the anesthetic gel anymore. But I always keep it in the pocket of my jeans. You just never know…