tagRomanceMary's Bet

Mary's Bet


Part 1 – The Game

"Who ever wins, the other one has to be a sex slave for a day."

Those words had rattled around in my mind all day. Mary loved to bet on things, and we loved competing – from silly things like online games, to racing to get somewhere, anything. The bets were frequently trivial – taking out the trash, doing the dishes, cooking dinner. Every now and then we'd bet something sexual, but this one was a biggie. Not that I was worried about losing (or course, neither was she).

As she tried to up the ante and convince me to agree, she said, "Imagine all the things that you can have me do that I've never done. Imagine all the things that you could do to me." I could imagine the mischievous glint in her eyes, and I melted. Since I travel a lot for work, we'd been indulging our competitive instinct by competing with each other in this online card game, so we decided that the next morning we'd play for one hour, and whomever got the most points would win. Simple. Of course, we both knew there would be lots of heckling during the game.

The phone in my hotel room rang at 6am, right on time. "Good morning," came her voice, "are you ready to lose?"

I laughed and said, "I'm ready for a lot of things, but losing to you with this much at stake isn't one of them."

I walked over to the desk and opened my laptop. I had the game already open and was ready to play. Mary was already online and in the game room.

I said, "So, you're going to do ANYTHING I want as my slave?"

She laughed and said, "I would, but I'm not gonna be your slave. I'm not gonna lose. YOU'RE gonna do anything I want as MY slave."

We both laughed and I said, "Ok, then. Game on!"

I got off to a terrible start. Losing several hands of the solitaire game before making any progress. I could see the first increments of her score hitting the scoreboard.

She IM'd me. "So where are you?"

"Oh, I'm having a leisurely start with the first round so that it'll be all the more crushing for you when I come from behind and win."

"LOL. Off to a bad start, eh? Well, I'll be nice to you when you're my slave."

I got into a groove. Sometimes the game just works right and it feels like the game wants you to win. I started racking up points. I also knew that I generally played faster than Mary did, so I wasn't too concerned. But she was still in the lead.

With about 15 minutes to go, we were neck and neck. Then the game turned against her. She got stuck. I managed to lap her through the game, and I was up by about 600 points. As the clock ticked down, I knew I was going to win, but I wasn't going to let up, just in case.

At 6:55, with 5 minutes to go, she IM'd to ask if I wanted to extend it for half an hour. She was still down by about 500 points.

"So," I wrote, "you're about to lose and you want an extension at the buzzer to try to take my prize away from me?"

"Ummm...yep." Came the response.

"What's the benefit to me?" I asked.

"Hmmm....If you still win, I'll make it worth your while. I promise. You'll just have to trust me."

Since Mary's the most honorable person I know, I was willing to take that. "Ok. The game goes until 7:30."

Her luck didn't change. By 7:30 she was down by about 1100 points. I was practically dancing in my chair with excitement. And, of course, a little gloating was in order. I called her cell phone and as she answered I sang into it, "You're gonna be my sex slave. You're gonna be my sex slave."

Mary hates to lose. At anything. And I could hear it in her voice as she said, "Yes. You win. Good job. 2 out of 3?"

I laughed and said, "Nope. You got your chance with that extension. No you have to figure out how to adjust the terms of the bet to give me credit for that."

"Don't worry," she said, "You'll be glad."

"Alright. I've got to get to work, and I'll be going straight to the airport from there. Tonight's going to be a long night. So, when I arrive in the morning, I'll meet you for breakfast and we can start your servitude." I laughed.

She laughed with me and said, "Ok. Come to my house. I'll have breakfast waiting. I'm going to be in meetings all day, today, too, so I may not talk to you today. You know how these negotiations can go. But, I'll be thinking about you. I love you."

"I love you, too."

"I love you more."

"I love you as much." And with that, we hung up.

Part 2 – The Flight

The days' meetings followed by the cab ride to the airport were uneventful, and I started to relax in anticipation of the flight. The redeye from San Francisco was tough. It leaves at midnight and the five hour flight gets in at 8am Eastern time. But 5 hours on a plane doesn't make for a lot of restful sleep, so I generally don't bother to try.

I settled into my seat, somewhat frustrated that I didn't get upgraded to first class, but at least the flight was fairly empty and I had my three seats to myself.

After flight attendants had finished their recitations of the safety precautions and we'd taken off, they asked everyone to turn off the lights so that people who wanted to could sleep. Since I definitely wasn't going to sleep in a coach seat, I settled into my book.

A tap on my shoulder pulled me away from the adventures of Harry Potter. I looked up, expecting to find a flight attendant, and instead looked into a mischievous and beautiful smile.

Mary has waist-length brown hair, petite and very nicely curvy with a perfect 34D chest. She keeps incredibly fit and loves to ride. Because of all the lifting, running and riding, she is in fantastic shape and has absolutely incredible legs. She has absolutely spectacular eyes. I could get lost in them forever.

"Hi, " she said, "I told you I'd make it worth your while. I thought you might like some company on this trip." While I sat there, stunned, she reached down to undo my seat belt, running her hand across my lap, feeling me already staring to get hard with the excitement of being with her. "Ahh... I think we can find a good use for this. Why don't you slide over to the window seat so I can sit down?"

As I slid over, I asked, "How long have you been in San Francisco? When did you arrive? Why didn't you tell me you were here?"

She laughed and said, "I've been planning this little bet for a while, and I thought that a plane ride together would be a good place to start. Naturally, I wasn't planning to LOSE the bet, but a deal's a deal. I was at LaGuardia with my laptop when we were playing this morning, then I got on a flight to come here – which is why I couldn't talk to you today."

"Mary, that's amazing. Have I told you recently how much I love you and how absolutely incredible you are?"

She smiled and said, "Yes, but feel free to show me, too."

She pulled a blanket up off the floor, folded up the armrests between the seats. She reached under the blanket. I felt the warmth of her hand as she moved it under the cover and let it rest on my thigh. My heart was racing, another smile crossed her face and those eyes danced as they captured mine once again.

Without a word being spoken I pushed my seat back and pulled the blanket over my lap and then placed my hand on hers. I guided it up to feel how hard my cock was. Our eyes still glued on one another, I said, "Does this give you some idea?"

I watched her smile and trace her lips with her tongue before leaning in to press her mouth against mine. Our tongues darted in and out of each other's mouths. I heard a muffled whimper escape her lips as I pressed my mouth more eagerly onto hers.

Her hands cradled my face as she raised my chin and pressed her mouth against mine. She kissed my nose then my forehead as I leaned my head back and she began to nuzzle my neck while still rubbing my cock through my pants. I could feel her hair on my shoulder and cheeks as her tongue circled my ear then bit my neck, stifling my moans as I tried not to wake anyone. I could feel her hot breath in my ear as she whispered, "Wanna join the Mile High Club?"

We made our way down the aisle to the bathroom....seeing sleeping people snuggled in their blankets, arms hanging out in the aisles, snoring coming from pillows that were jumbled at the head of the seats.

She opened the door to the bathroom and entered as I stood outside and kept guard. Within a minute she opened the door again and grabbed my hand pulling me in.

She was sitting on the toilet as I squeezed into the tiny space. My back was against the door as I entered, and she stood, pressing me against the door. My cock was pressing against her stomach between us. She reached behind me to lock the door as I moved my hands down her back then up and under her t-shirt, pulling it over her head. I slid the straps of her bra off her shoulders and gently pulled her breasts out of it. Cupping one in my hand, I leaned down to suck on a hardening nipple. I could feel her moan in her chest.

Pulling away, she sat back down on the toilet, unbuckled my belt and slid my pants and boxers down. She took my cock and rubbed it on her cheek – the soft, warm skin sending shivers of pleasure through me.

Her hands moved gently caressing my thighs, exposed abdomen, my balls, and the base of my shaft. She kept my skin guessing where the pleasure would come from next. Her fingertips settled on different spots only long enough to set off nerves and moved to stimulate elsewhere.

All her motions orbited the action of her lips moving up and down on my cock. Occasionally she'd put her hands on my cock, stroking and use her tongue somewhere else. I was eight miles high and in Heaven.

She rubbed the back of my thigh with her right hand while her left hand gripped the base of my cock. She gently took the head from her lips and worked her hand slowly up and down the shaft, while she looked up into my eyes. Smiling, she put the tip of her tongue onto my balls, and licked upwards following her hand. She ran her tongue upwards in light, flicking strokes. She switched hands, and while her left hand was playing up and down my lower back, over my ass and thighs with carefully placed touch after touch, her right hand stood my cock up so that she could run her tongue on the underside of the crown where I was most sensitive; first clockwise then counter-clockwise.

She took my shaft back into her mouth and I wondered how much more I could stand.

The next time the tongue-sequence began; she sucked my balls, while lightly scratching her nails over them, as well.

I ran my fingers through her hair and caressed her face. She tilted her head back to look at up at me.

She sucked my cock into her mouth, again and again. After every five strokes, she stopped at the bottom and made a swallowing motion that bobbed her head and cause her to take a little more of the shaft into her each time. She was gradually getting my cock deeper and deeper inside her. I'd never felt anything like this – having such an incredibly beautiful and sexy woman making my pleasure her complete focus. Each time she paused, she hummed a little around my cock, sending ripples of pleasure down it.

Five more strokes, she stopped, taking in a little more, humming.

Five more strokes again, up and down. She released my shaft from her mouth, reached down to lick me from balls to the tip of my cock. Her tongue struck out of her mouth in a sudden motion flicking the head.

One tongue thrust.


After the third, she licked me from balls to the tip, again, then impaled her mouth on my shaft. I felt more than saw her reach down between her legs. I felt her unzip her jeans and slide her hand inside. I could feel the rhythm of her arm as she played with herself while sucking my cock.

She returned to her earlier rhythm, but there were only three strokes before she did the swallowing that was driving my cock deeper into her mouth. Finally, as I thought my whole body would explode, she touched bottom. She rested there, humming on my cock. My whole body was shaking on the edge of an orgasm. I had no idea how she could breathe, but it felt so amazing that I just wanted it to go on forever. I could feel her body starting to quiver as her fingers were having their effect on her. I knew that she didn't usually cum from just her fingers, but I hoped that the situation and my involvement was helping push her over the edge.

Suddenly, I felt her entire body tighten. The muscles in her thighs contracted, her back arched, and she pulled me hard against her face tightly and then released.

She moaned around my cock as she rode her orgasm down its pleasant spiral.

She moved her head around with a rotating, almost corkscrew motion, unwinding her mouth from me, lashing my cock with her tongue, pausing, and then taking it fully into her mouth, again; again and again. My knees were getting weak as my whole body was trembling.

And then she stopped.

Holding my cock in her hand, she smile up and me and said, "You don't join the Mile High Club that way."

Shifting in the cramped space, she stood up and slid her jeans down. She turned towards the wall, bent over and said, "I want you to fuck me. I want to feel you inside me."

I reached down between her thighs and slid one finger into her, then two causing her to moan and gasp as my other hand roamed up to her nipple, grasping it, gently cupping her breast and flicking the nipple with my fingers.

I pulled my fingers out causing a disappointed sigh to escape her lips, my hand was pressing my cock into her, sliding into the hot tightness of her pussy. I wrapped my arm tightly around her waist, pulling her against me.

Pulling myself almost all the way out, slowly, I thrust hard back inside her. I felt her shudder and push back against me. We moved in a rhythm, slow out, hard in, slow out, hard in. I could feel every muscle pulsating inside her as I moved, her breathing deepening and my thrusts getting harder, faster, pushing deeper into her.

Tremors began rushing through my body as her muscles began to grip and release my cock, clenching around it. I bent forward and pulled her up so my mouth was on her neck – licking and nibbling. I reached down with my hand to play with her clit and felt her body shiver as I found it.

She bent forwards, again, whispering "Cum for me, John". She arched her back and pressed her ass out against my thrusts as she whispered the words over and over. My hands on her hips as I stroked deeper and deeper inside her. "Cum for me, John" she whispered again. As she reached down to play with her clit, I heard a very raspy whisper "Cum with me. Oh, god, cum with me now!"

As though she had commanded our bodies to peak...we began to merge into one intense orgasm.

I shot inside her, my body tense and quivering, both of us gritting our teeth trying to be quiet as spasm after spasm shook our bodies.

I felt her body as the orgasm took over, my arms holding her tight as a rush of pleasure raced through her. I moved my hand back down to her pussy, I could feel the sticky mixture of my cum and hers as I slowly moved in and out of her, both of our bodies twitching and jerking with post-orgasmic spasms.

I pulled her up, and we rotated so that I could sit down, and I pulled her into my lap, wrapping my arms around her as we caught our breath and laughed.

We sat for a few minutes, relishing the afterglow, my hands were working their way up and down her sides, then down between her thighs and back up again brushing over her breasts as I continued to kiss the back of her neck. Her hands reached up and she tangled her fingers in my hair. She turned her head and pulled me close and kissed my lips. I loved feeling the warmth of her body on me.

I heard a little giggle as she said, "Welcome to the Mile High Club. I love you, John."

"I love you, too. We'll have to do this again sometime. "

She laughed and stood up. "Any time and for the rest of our lives." We started repairing our clothes. She checked herself in the small mirror over the sink, running her fingers through her hair, half straightening it, half letting it just fall wherever. She turned and kissed me deeply before opening the door and stepping out, closing the door behind her.

I finished getting dressed, and stepped out, too. The flight attendant standing in the aisle gave me a knowing smile, and then shook his finger at me and said, "Tsk. Tsk." I smiled and said, "Well, since we didn't get upgraded into first class, I had to make the flight worthwhile," and I stepped past him to go back to my seat.

She was waiting for me when I got there. She pulled up her legs so I could slide past her into the window seat. She leaned into me, pressing her breasts against my arm. "We'll have to do that again some time. Now we should get some sleep. We've got a big day tomorrow." She kissed me, and slid down my body so that her head was in my lap.

I stroked her hair, an innocent touch without necessarily being sexual. It worked to calm my body; focusing my attention on the feel of her hair instead of my lap where inches away a beautiful mouth I wanted kissing my skin and surrounding my dick was smiling as she went to sleep.

I couldn't ask for anything more perfect and wonderful than having her asleep in my lap. There's something so special and beautiful about having someone fall asleep in a position like that. It makes you want to stay up and watch over them – protect them. I loved her for trusting me like that. I closed my eyes, stroked her cheek and fell asleep.

I woke to realize that she was sucking my cock. I cracked my eyes open to see that the blanket was covering her head and my lap. There was no sign of motion, but she was flicking the head of my cock with her tongue, then gently wrapping her lips around the head. Her hand was gently stroking lightly up and down the shaft. It was almost electric. Even though I had just woken up, I knew I wasn't going to last long.

She shifted slightly, so that her hand was cupping my balls. My hips started to buck involuntarily, even though I was trying to show as little reaction as possible. I pressed her head as my cock started to twitch and I came in her mouth. She sucked the head of my cock, cleaning the cum from it, then sat up from under the blanket, smiling at me. "Is that how a sex slave should wake you up?" she whispered.

On that note, the captain announced that we were beginning our final descent, and the flight attendant came through telling everyone to put their seats up, tray tables up, etc. He got to us and said, "I know you two had a good flight. Please don't do that again." And, with that, he was gone. We just looked at each other and laughed.

Part 3 – The Car

Leaving the airport, Mary steered me away from the cab line towards where the limos were parked. I looked at her and she said, "I wanted this say to be very special. Like I said, I wasn't planning to LOSE!" We walked up to one of them, and a driver got out. "Ms. O'." He came around to open the door, and I climbed in behind Mary (admiring her ass as she bent over to get in).

She pressed the button to raise the glass between us and the driver.

"Sweetheart, although I'm enjoying the idea of having you as my sex slave, I want you to know that you can tell me if I've gone too far or there's something that you don't want to do."

She took my hands in hers and stared into my eyes for a second before responding. "You know that I would do anything for you, and that I want you to do anything you want to me today. When I said that I would be your slave, I was telling you how much I trust you, and the fact that you are concerned about my feelings just tells me that my trust is well placed. I trust you to judge what you want, and what I will do. Today, I'm your slave. You will own my body and it will be yours to do with what you will." She paused, and laughed, "And, of course, I'll get to have paybacks when you lose the next bet, so I think we'll be fine."

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