Michelle's Losing Bet

100% fiction!

My date and are sitting in the finest restaurant in the city, it’s French, it’s expensive and the food is delectable. We’ve just finished our meal and are sharing a plate of petit fours and a bottle of Sauterne for desert. And the challenge is about to begin.

My date, let me tell you about her. She’s 19 years old while I’m thirty-nine; some might call me a cradle robber but not so, I didn’t pursue her, she went after me, two years ago when she was only 18 and she got me. I love her with all my heart but then again, I always have.

She is beyond gorgeous, a willowy 5’10” tall with waist length flowing black hair, perfect 36C breasts riding high like the prow of a luxury liner a flat tummy and slim almost girlish hips but with an ass to die for, heart shaped and luscious. She is far and away the most beautiful woman I’ve ever seen and I’ve seen quite a lot.

My name is Michael Morrissey, like I said I’m thirty-nine. I’m 6’3” tall and still only carry a svelte 190 pounds. Like my date, her name is Michelle by the way, I have jet black hair and we both have high cheek bones and dark complexions. I’ve been a widower for 18 years and have dated frequently. Most women find me handsome and, of course it doesn’t hurt that I’m fairly affluent.

My date, she doesn’t like to be called my girlfriend, she’d prefer fiancée but that remains to be seen. Oh I’d love to be married to Michelle, I love her dearly, she’s the most entertaining conversationalist I’ve ever met, male or female and the sex is out of this world. Yes, I’d love to be married to Michelle but there’s one minor complication. You see, Michelle is my daughter.

I mentioned that I wasn’t a cradle robber, no, I wasn’t and I wasn’t a lecherous Daddy after his little girl either. I admired Michelle’s beauty, I loved to be around her, spend time with her, spar with her rapier wit; she was my perfect daughter, always a great student and never the rebellious teen that is so prevalent today; she loved me and I knew it. The only oddity I noticed was that Michelle didn’t date. The boys called, the boys asked her out but she refused them. I spoke to her about it, her reply,

“Daddy none of them interest them. I’d rather go to a museum or a play or the opera, heck; I’d rather go to a ball game with you than any of them.”

Now that certainly played to my ego. My daughter would rather spend time with me than with anyone else and I’d rather be with her. I did still date, a man has needs; Michelle was always jealous of any lady I brought home, even when was a little girl, she wasn’t surly to them she just ignored them. I quit bringing my dates home with me.

When Michelle turned sixteen two years ago we had a private party, I took her to a stage production and out to dinner afterwards.

I said, “sweet sixteen and beautiful, I love you Michelle, Happy Birthday.”

She replied, “Yes, sweet sixteen, now I can do some things I really want to do.”

“What do you want to do now that you couldn’t yesterday?” I asked.

“Oh get a driver’s license and stuff like that,” she answered but there was a wicked gleam in her eyes.

It shot through my mind; sixteen is the legal age of sexual consent in our state. It only shot through, Michelle wasn’t even dating. I needn’t be concerned in that regard.

We finished our meal, had dessert and went home. It was getting late.

Once in the house Michelle gave me a little kiss saying, “Thank you Daddy, you made my birthday wonderful.”

She went upstairs ahead of me. I heard her shower running when I went to my room.

I was tired; I just stripped and climbed into bed. I was asleep in moments.

Something awakened me, I knew it was late, I glanced at the clock it was nearly midnight, I’d awakened to the feel of a weight on the mattress, someone was in bed with me and there was only one other someone in the house.

She said, “Hi Daddy.”

I sat up pulling the sheet to cover my nakedness and said, “Michelle, what are you doing, why are you in my bed?”

“It’s not what I’m doing in your bed it’s what you’re going to do to me in your bed.”

“Oh and just what is that?” I asked incredulously.

“You’re going to make love to me; I’m legal now you know.”

“Michelle, you may be legal but you’re still my daughter, go back to bed and we’ll forget tonight happened, it’s incest.”

“Yep, it’s incest and I don’t care, you’re going to make love to me.”

“Michelle go back to bed, your bed and let me get some sleep.”

I thought, right, I’m going to get some sleep. I’d be awake all night wrestling with this.

“Daddy I’m staying right here until you make love to me. I don’t care if you shout at me or even spank me. I’m staying.”

I thought, from my daughter’s lips to my ears, so Mickey take that! Yell at her; hell I might have done that once or twice in 18 years and spank her; I’d never touched her; never would although it didn’t seem like a real bad idea at this moment.

“Michelle, please,” I pleaded.

She was wearing a pair of baby doll pajamas, she said, “Daddy undress me and make love to me.”

“Why Michelle, why me, you’re a beautiful young lady. Lots of boys want to date you, you could have your choice, why me.”

“Daddy I’m glad you think I can have my choice. You see, I choose you. I love you and I desire you. I’ve been planning tonight since I was twelve and began to realize what sex was. So, you have been chosen to make love to this beautiful young lady, as you put it. Now undress me.”

She snuggled up beside me and took my hand. She placed it on her nightie over her breast and whispered, “Please Daddy.”

I acquiesced, gave in, surrendered, and I couldn’t deny, I was flattered and I was getting aroused, I lay down beside her and massaged her breasts.

“Michelle, this is a big step, I want you to think about it,” I said.

“Daddy, I have thought about it, I’ve thought about it a lot in the last four years. It’s you I want, it’s you I want to take my virginity and you will, won’t you?”

“Michelle sweetheart, I’ll hurt you but if you want me to I will.”

“Daddy I know I’ll hurt after all I’m a virgin but I want you, I want you tonight.”

I slid my hand under her PJs and massaged her breasts, I said,

“Let me help you out of this as I raised the top. I lifted it over her head and beheld her breasts for the very first time. They were superb, still erect even in her prone position. I kissed her then took a nipple in my mouth.

Michelle’s reaction was immediate. She sounded a soulful little moan and her nipples hardened. I sucked one while I played with the other, gently twisting and tugging at it pinching lightly while I nibbled on the other.

Michelle’s voice was low and raspy when she said, “That feels nice Daddy, that feels so, so nice.”

I spent some more time on her breasts then moved down her body, licking and kissing along her sides and onto her tummy, she had a cute little innie belly button, I tickled it with my tongue then I took the fabric of her PJ bottoms and saying,

“Lift your hips Sweetheart,” I took then off.

I gazed at her mons veneris, she was lightly covered with black hair, not the dense pelt she’d eventually develop still, there was no question she was a budding woman. I teased her there with my tongue and tugged at her with my lips.

She said, “Daddy, oh Daddy, I love you.” She was squirming under my touch.

I parted her lips with my tongue and snaked along her slit. Her vagina was tight, just a small hole that I probed with the tip of my tongue, she shivered. Further, further down, at the end of her vulva I tasted her, piercing her rosebud with the tip of my tongue.

She moaned, “Oooh Daddy, yesss Daddy.”

I worked my way back up, nipping and tugging on her labia with my lips as I sought her love button. Her clitoris was waiting for me, for my attention, swollen and red; I took it between my lips and sucked her into my mouth. For a few moments I just sucked. She was trembling, she was nearly ready, I batted the sensitive tip of her clit with my tongue, teasing it, twirling it.

I caressed her tummy, I could feel her orgasm building, her muscles were rippling like a washboard, she nearly came off the bed she wriggled so much, I held her down and sucked. She screamed incoherently when she climaxed, I could feel the contractions and spasms as they washed through her, her hips were pounding my face when she released, orgasm after orgasm flowed through her, she was screaming,

“No more, no more,” she pled but her legs were wrapped around my head and she was pounding my face with her pussy.

Finally she relaxed, releasing me. I licked along her slit, tasting her succulent flavor. She was exquisite. This would be my first, last and only chance to taste her as a virgin and I reveled in it. Her fragrance was mild; she hadn’t yet developed the scent of a woman. In the dim light I could see that her slit and inner lips were a light coral shade, she was beautiful, alluring, and waiting.

I knelt between her thighs and reached toward my night stand, there were condoms there.

She said, “Daddy you don’t need that, I went to the school nurse when I was fourteen and she got me on birth control pills. I didn’t know if I could wait and I wanted to be ready. Now, I’m ready, I want you in me. I want your cum in me.”

I ran my cock along her slit until I found her vagina. She was so small I feared that I wouldn’t be able to get in.

I pushed forward; the head stretched her and slid in. When I met her hymen I stopped.

“Go ahead Daddy, I’m ready,” Michelle said.

I thrust, I felt her tear, her cherry was shredded as I entered her.

Michelle gasped and winced from the pain, it was sharp, the rending of flesh, the bursting of a thin membrane, and then I was in.

I stopped for a moment, just gazing at her beautiful face, wreathed with her raven hair, then she opened her eyes and smiled at me, a wan smile, tinged with pain but a smile.

“I’m yours now Daddy, I’m all yours.”

Slowly I started to stroke her, I wanted to be gentle this first time; there’d be other opportunities for wild raucous sex in the future but this time I wanted to be slow and gentle.

With long languid strokes I filled her. She was cooing contentedly, she’d gotten what she wanted; she’d gotten me. Unquestionable, she’d gotten me. I already loved her more than life itself as my elegant, comely daughter; now I loved her as my paramour.

We finished as we began, slowly, gently. When I came it flowed into her, I didn’t pound her, I didn’t stroke deep, I didn’t even speed up. She felt my flow and smiled again.

“Thank you Daddy for making it nice for me.”

I lay beside her and took her into my arms, “You’re not sorry Kitten?” I asked. Kitten had been my pet name for her when she was younger.

“Never Daddy, I’ll never be sorry. Please kiss me and tell me I’m your girl.”

“Forsaking all others, you’re my girl,” I answered as I kissed her as a lover.

She’s not slept in her bed since that night.

And God the girl’s insatiable. When we woke up the next morning she wouldn’t let me out of bed until I’d filled her again. At night she wanted to go to sleep with me behind her, holding her to me while I filled her.

She loved to jump on and ride me like she was a cowgirl, her on top just pounding away and hooting. I liked that too, her pert breasts bouncing, I’d slip a hand under her and help her along, let her clit ride my fingers.

The second morning we were together I was wakened to a most sensual experience. She had me between her lips, sucking me. I was ramrod stiff, she was bobbing I tried to tell her I was gonna cum; she nodded yes and bobbed faster. God, I raised my hips and blasted into her throat. She swallowed and swallowed, gagging just a little but she got it all, well, almost all. When she looked up at me dribbles were coming from each side of her smile. She swirled her tongue and they were gone.

“Good morning Daddy,” she said.

“Kitten, you’re killing the old man.”

“Pooh,”she scoffed, “We haven’t even started.

God, she meant it. Her sexual appetite was amazing. She had to have me in her, on her however she could get me several times a day.

I think her favorite position is me behind her, Doggie. She says I go deeper, I think it’s because I play with her little rosebud, she likes me to rub her there and she likes the feel of a finger in her while I’m pumping her. She even likes it when I kiss her there and snake the tip of my tongue through her tight little pucker.

It was St. Valentine’s Day; I’d taken her out to dinner and a show. When we got home a pound of chocolate truffles from Kipschildt Chocolatier was waiting with a big red bow. Although it is American made it’s the most expensive chocolate in the world; my Kitten’s worth it.

She popped out to our pantry, there was a hundred bottle wine cooler in there; and came out with a bottle of champagne to enjoy with our truffles. I saw the label; it was a Bollinger Blanc de Noirs Vieilles Vignes Francaises (1997). I thought, Christ I’d paid $650.00 for that bottle, I only had three and they were for special occasions. Then I thought, hell the truffles were $2600 and I was sharing with my beautiful nymph of a daughter, what occasion could be more special.

We were in a playful mood when we’d finished our treats and Michelle took me by the hand saying,

“Come on Daddy, your Valentine’s Day gift is upstairs.”

When we got there she said, “Get undressed, you gotta be naked to get my gift, “as she walked into the bathroom.

I’d hung up my clothes and thrown my socks and underwear into the hamper I was still in the middle of the room when she came out. She, too was naked but she had something in her hand.

She tossed whatever she was holding to me saying, “Catch, you’ll need it for your Valentine’s Day gift.”

While I was looking down at what she’d thrown me she’d climbed onto the bed where she waited on her knees with her face buried in her pillow.

What I was holding was a small tube of strawberry scented gel, a sexual lubricant. I looked over at her and saw her pose.

I said, “No way Kitten, I’ll tear you up.”

“Daddy,” she whined, “Isn’t it St. Valentine’s Day?”

“Yes Kitten, it’s St Valentine’s Day, what’s your point?”

“And don’t you say my ass looks like a heart?”

Letting the small crudity pass I answered, “Yes, I say that, still, what’s your point.”

“Damnit Daddy, it’s Valentine’s Day, I have a heart, you say so, so I have a heart that needs to be pierced just like with St. Valentine’s arrow only I want your arrow. Now get me ready.”

How can one argue with that convoluted logic? I lubricated her and me.

“You’re sure?” I asked.

“Pierce my heart you big Daddy you.”

When I popped in I know she was happy for the pillow, she wailed when I entered her and she sobbed as I pushed deeper into her. I rested a little when I was half way in.

I let her settle down. I knew she was ready for more when she said,

“Daddy, I asked for an arrow, I think that was a spear.”

I gored deeper into her until I was at my maximum. Then I started to pump her, hard rhythmic thrusts, through her anus, filling her rectum she grunted as I pushed into her, not ladylike sounds, but,

“Ungh, ungh, ungh,” I know it’s perverse of my but I delighted in her sound.

She probably wasn’t gonna cum, I could have helped, a couple of fingers under her but I didn’t. This was my Valentine’s Day gift and I was going to enjoy it to its fullest. I could give her some oral later.

I gripped her hips and fucked her like there was no tomorrow. God her ass was tight, sliding through her sphincter was like entering the gates of heaven and slipping up her inviting chute was like gliding through warm mercury, hot, slick and if treated wrong dangerous. I fucked her like she was my bitch. Feet outside the width of her hips, knees bent for maximum leverage, I rode her deeper and deeper. She was wailing into her pillow as I pounded her, deep, fierce rapid thrusts, distending her, stretching her, her little ass was mine. God, I exploded, I saw stars, I screamed like a wounded animal as I poured into her thrust after thrust delivering pulse after pulse of my scalding cum deep in her guts, filling her, flooding her, I collapsed over her back. I rode her to the mattress, my cock still in her, I was spent, wrung out, exhausted.

What happened, she used her tight little asshole to squeeze the last remaining fluid out of me and said, “Happy Valentine’s Day Daddy.”

Next she got into toys; we had a drawer full of them. She liked them for herself, for self-gratification, for me to use on her and for her to use on me. We had butterflies, rabbits, a whole damned menagerie of toys, up my ass, in her pussy, if it was made, she had it and she used it; cock rings, anal probes, motorized vibrators, you name it.

She says she’s tried and done everything, and I can’t really argue with her. She’s only been sexually active for two years but what a two years. We’ve done things even the authors of the Kama Sutra hadn’t imagined.

So back to the challenged I mentioned to start this story. She and I have a little bet, no money, it’s really only who gets top tonight but the prize in and of itself isn’t important, the winning is.

You see, she thinks she’s done it all. There’s really nothing she can’t handle and I’ve bet that I can make her beg for one of two things, either it will be “Daddy, please stop” or “Daddy, let’s go, I gotta have you in me.” Either one of those and I win.

Before we left for the restaurant I’d fitted Michelle with a little device I’d discovered totally by accident, it was at an on-line sex toy site and it caught my attention. It tried to meet all needs and I’d bought it. I’d said that I thought it might be a little more that she could handle and the challenge was on.

The devise in and of itself was a lot to deal with. It had an anal probe which I lubed and fitted in her bottom, a vaginal penetrator that I slid into her and a butterfly device that covered her clit. It all strapped on, around the thighs and around the hips.

Under her panties Michelle had it on. She’d squirmed some tonight, the anal probe going deep with her sitting on it but she was sure she’d win; she’d been wearing it for over two hours and wasn’t even close to begging.

She didn’t know how it worked. Each of the inserted devices was also a vibrator. I had a three way remote control in my pocket and three speeds on each of them.

She was smiling, victory was at hand, exalting, “I get top, I get top.”

I switched on the butterfly clitoral vibrator, lowest setting, just to give her a feel.

Michelle’s eyes got big a saucers, she looked at me saying, “Daddy?”

I switched on the middle one, again on the lowest setting; it was buried in her, in contact with her “G” spot.

Michelle was wiggling in her seat, burying the anal probe deeper. I wasn’t ready to use it yet. I increased the vaginal dildo to the second setting. She could only look at me. She wasn’t going to concede defeat, but her breathing was getting a little ragged.

“Do I win,” I asked.

“No, no way I’m gonna beg,” she breathed.

“Oh, I think you will,” I said as I raised the intensity of the clitoral stimulator to its second setting.

Michelle was starting to pant, quick little breaths, she said, “Damn it, I’m not giving in.”

I kicked the middle switch to maximum, two steps up. I knew I had her then.

She leaned on the table supporting herself, trying to relieve some of the pressure.

Her face was a mask of concentration with her effort to retain control.

“Ready to go home yet Kitten,” I asked

She grimaced at me and uttered, “You cheat.”

“I don’t think so, the only rules I remember are that you ask me to stop or you ask me to take you home and meet your desires. Want me to stop or do you want me to take you home?” I asked as I increased the clitoral butterfly to its third and highest setting.
She moaned and began to tremble. I asked, “Kitten you seem to be quivering, are you cold?”

Her voice was weak and raspy when she said, “Cold, no Daddy’ I’m not cold. I’m sitting in a hot puddle of me, I’m flowing like and artesian well, this seat is soaked but I’m not going to give in, damn it.”

“You’re sure? We’ll see.”

I turned the anal stimulator on.

Michelle ground her bottom down into the seat; she was trying to work it deeper into her. I knew she was lubricating, drenching her chair and now her bottom was crying for attention.

“Ready to submit yet?” I asked.

She just shook her head no.

I gave it one more speed.

Michelle was beyond speech, when I asked her to submit she just groaned but shook her head no.

“Kitten, are you sure?” She already looked like a rape victim sitting across from me, her face was sweaty, rivulets running down her cheeks, her eyes were leaking and her eye shadow was running, blackening her already dark eyes. Even her hair was getting sweat matted.

“No damn it, no, I won’t quit,” she rasped.

I thought, girl you’re a toughie but I’m gonna win. I kicked the anal probe to max and sat back to watch the show. I wondered how long she could take the intense stimulation, her clit; her “G” spot and her bottom were being ravaged.

I sat back and watched her tremble. Speechless she sat, fluid pouring from her, soaking her panties, her bottom and her chair, while her clit was abuzz and her bottom was aquiver; I watched for nearly ten minutes before she simply fell forward onto the table, her eyes rolled back in her head just before she said,

“Take me home Daddy.”

It was all she could get out before she collapsed. I shut off all of the devices and left a fifty on the table for the waiter. The dinner would go on my monthly tab.

I helped Michelle to her feet and, with my arm around her waist supporting her I walked her outside. The brisk air helped to revive her; she was able to stand unsupported by the time the valet returned with my car. I helped her in.

When she was finally able to talk she said, “Daddy, you cheated, I didn’t know what this thing I’m wearing could do.”

I switched the anal probe on low and asked, “Want a little more?”

“Ah Daddy, you win. You’ve got top. How do you want me?

Her voice was pouty, I thought, damn, she’s a sore loser. Oh well, I said,

“Tell you what, since I’ve got top you choose what we’ll do, fair enough?”

She was quiet for a few minutes thinking, considering her options then she said, “I really want you in my bottom. I want to be over the chair arm and I want you hard and deep but I’m a little afraid about what might happen. That thing of yours has really stirred up my bowels, I don’t know if I’d have complete control.”

‘When we get home I’ll deal with that for you. Get undressed then meet me at our bed.”

I was waiting for her, sitting on the edge of the bed when she came into the room. She still kept her clothes in her old bedroom. She’d hung them up and tossed her soiled lingerie into the dirty clothes.

“Come here Kitten,” I asked.

She came to me. I took her hand and pulled her closer, guiding her over my lap.

She lay there but she was trembling, “Daddy are you going to spank me,” she asked, I could hear the fear in her voice.

I massaged her bottom and rubbed her back.

“No, nothing like that, this won’t hurt but it will solve your bowel problem. I’m going to give you a little enema to clean you out then you can take a bath, it should help you relax and settle down, ok?”

Actually she was going to get two, one right after the other. They were Fleet enemas and only about a pint each. He’d already lubricated the tubes. He opened her cheeks, rubbed in a little of the gel and slid the first one in. It drained into her quickly; I picked up the second and squirted in into her. Then I just let her lie across my lap until she said,

“Daddy, I’ve gotta go.”

I let her up and she raced to the bathroom.

After about ten minutes I heard her bath water running.

I got everything ready. I put a pillow in the seat of the chair and got the strawberry scented lube. Michelle had purchased it from a sex shop. It tasted like strawberries, too. I knew, I’d had the pleasure of tasting it many times. She’d be fresh and clean and I did like the taste of her rosebud. I decided she’d have a little tongue before she got any cock.

When she finally came out she was wearing a pair of frilly panties. I knew she wanted me to take them off; there was no other reason to have them on.

“Cute panties,” I said.

“You like them on or off?” She asked.

“On while I’m looking at them, off when I’m looking at you,” I said as I led her to the chair.

I bent her over the arm and pushed her forward so that her head rested on her pillow then I rolled her panties down over her hips. I knelt behind her and spread her cheeks, inhaling her scent. She was fresh and clean smelling. I smoothed on a little of the gel then enjoyed the taste of strawberries. There was a sharp intake of breath from Michelle when my tongue slipped into her. I added more lube to her and to me then stood behind her.

I had one hand on her the small of her back, the other I used to guide my penis to her waiting brown eye. I lined up and pushed in. Michelle gasped and moaned when I penetrated her. This was hardly the first time I’d been here but I was a little more forceful that usual.

The hand on her back was to hold her down if she’s tried to get up. She hadn’t so I took both hands, gripped her hips and forced my way in, sliding smoothly into her velvet chute. I wanted her, I wanted her badly, my little torture games at the restaurant had aroused me. My God, I could smell her clear across the booth. Her juices and even her bottom, her scents that were so familiar to me. I’d had a hard on for over half the meal. And yes, I’d enjoyed watching her squirm as I increased the intensity of my toys.

Michelle truly did have a lovely bottom, heart shaped, rounded and full. If there ever was, this was an ass to die for. I pumped her. Long hard thrusts, forcing her forward on the chair arm, eliciting grunts and moans from her as I powered into her. Her slim hips were under my control, I was pulling her back to meet me each time I drove into her. I decided she should have some pleasure, I certainly was. I slipped a hand under her and let her ride my fingers as I rode her.

Michelle was grinding her pussy against my hand, my fingers held her clit, pulling it, masturbating her at the same pace as I was filling her. She was moaning in pain and excitement.

She started to quiver under me wailing, “Daddy man, oh Daddy man, oh yes, Daddy yes.”

I was slamming her, my cock was swelling, stretching her further, going deeper. She screamed as she climaxed and I was there with her. I roared like a wild animal as my cum poured from me, my legs were outside her slim hips and I was pounding her, maximum leverage and maximum penetration when I came. I was still pounding her when she went limp under me. I slowed and stroked out, draining myself into her. She lay unmoving. I stepped back.

“Kitten, are you ok?” I asked.

She didn’t answer. I looked at her face, her eyes were closed and her breathing was shallow. I rubbed her back.

“Baby, are you ok?” I asked. “Talk to me Kitten, please talk to me.”

Finally her eyes opened, she said,

“Help me to bed Daddy, please help me to bed, I don’t think my legs will hold me. My knees are weak and I’m sore.”

I walked her to the bed, helped her to her back and lay beside her. I turned her toward me and held her in a tight embrace while I kissed her.

“Kitten I’m sorry I hurt you.”

“That’s ok Daddy, you won the bet, and I paid. Next time I’ll beat you.”

She rolled over in my arms, snuggled against me and drifted off to sleep, exhausted.