The Bet Ch. 01

My wife and I began our relationship innocently enough. It started because she was a Yankees fan and I a Red Sox fan. Since we worked at the same company the exchanges started as friendly banter in various business encounters; eventually we began to bet on the outcome of games. Both of us were dark chocolate lovers, so the bets started out at a Godiva dark chocolate truffle for each win or loss, with a truffle awarded for every game - no sense in limiting the treats by offsetting wins and losses!

Since I went into the office early, Dana would come in to find her winnings in a little box on her desk. Mine were delivered by midday in person, usually accompanied by a snarky comment on what was always a "lucky" win. Looking back, it was mild but harmless flirting.

The flirting, such as it was, didn't progress for several reasons. We were both married at the time - that and the fact that we worked in the same company made anything more than casual flirting very risky. And, frankly, we weren't looking for more at that moment even though there was some chemistry there. I was 34 and she was 27; the seven-year difference accounted for me being higher up in the management structure, but Dana didn't work in my area so it wasn't an issue.

The betting in the first season was limited to truffles and, of course, talking smack depending on whose team won. In the second season we added lunch to the bet if one team or the other won a series. I found the lunches very enjoyable and I think Dana did too, but she always seemed a bit nervous. This was when I started to notice her more - she was already my type: long dark hair, nice figure, long legs. She was about 5'8" and I was 6' tall. I noticed and complimented her at lunch; her hair, nails and makeup always looked great, and it always seemed that she had just had them done. For me? I never considered that at the time.

By the start of the third season, we had both gotten divorced and were recovering from the emotions that came with that. We still bet truffles and lunch and agreed that whoever lost the season series would buy dinner as well. It happened that the Yankees won the season series that year, so I arranged dinner at a very nice restaurant in a nearby hotel. On the off chance that I might drink too much I got myself a room there.

We agreed to meet at the restaurant, Dana having gone home to change. I just added a tie and jacket to my business casual work outfit. I was waiting in a chair facing the front door in the lobby and saw this vision of a woman come through the door - long hair falling in dark waves over her shoulders, an elegant black cocktail dress that hugged her curves and showed a bit of cleavage, and long legs accentuated by 3-inch heels. It took a second for my mind to register that it was Dana! I was used to casual clothes and flats at work, not this goddess.

Leaping to my feet I walked over to greet her. "Dana, you....you look amazing," I managed to get out. I was rewarded with a brilliant smile.

"You like?" she asked. "I bought it just for tonight." Probably realizing what she might have implied she added, "This is a high-end hotel and restaurant, so I didn't want to look out of place. You didn't have to splurge like this you know."

"You couldn't look more in place," I told her, still taking in the transformation. Dana always looked attractive, but in an understated way. This - this was amazing.

"Why don't we see if they're ready for us," I suggested, taking her hand and walking to the restaurant. We checked in and were promptly taken to a table along the windows, looking out over the manicured hotel grounds and a fountain. Seated, I found myself looking at Dana and admiring her beauty, to the point where she looked down, making me realize what I was doing.

"I'm sorry," I told her. "I didn't mean to stare at you. It's just....you look so beautiful tonight. I mean.....you always look nice, but tonight you look especially amazing."

Dana blushed, a vivid pink going into her cheeks and neck, a marked contrast to her fair skin.

"Thank you," she said softly. "I hoped you would like the dress."

"The dress looks incredible on you," I told her. "You look incredible in it!" When I saw her blush again I knew I should stop complimenting her. "Let's check out the menu; I hope there's something on here worthy of your victory dinner," I joked.

"And let's see if there's humble pie for the Red Sox fan," she suggested.

That first dig of the night relaxed both of us and returned us to normal. We ordered drinks and a good bottle of red wine and reviewed the menu. Dana fretted about the expense - I told her not to worry, this would

happen only once every decade, so I had nine free meals to look forward to. I got a challenging look at that comment, reminding me that this vision of loveliness before me was indeed Dana.

The meal was excellent, and will forever be in my memory as one of the best few hours of my life. We got to know each other much more thoroughly than we had at work, and found that we had a lot in common. The chemistry that previously had been hinted at was building. By the end of the meal I found myself under the spell of this woman.

Since there were probably two glasses of wine left in the bottle I suggested we go up to my room to enjoy it before the evening ended. Dana was surprised that I had booked a room, but I explained that I didn't know how long the evening would last, or how much I would drink, so it seemed to make sense. No ulterior motives here! She accepted my invitation and we went up to the room.

Pouring the wine I handed her a glass and toasted her triumph once more.

"Thank you kind sir," she replied. "And thank you for a wonderful dinner. Luckily, I won't have to try to match it next year." That with a smirk.

"We will see," I responded. "But I enjoyed this evening so much that I don't want to wait a year to repeat it."

"Are you asking me out on a date?" Dana said with mock shock.

"I suppose I am," I admitted.

"After all this time," she commented. "Did you decide we might be compatible after tonight?"

"I would say that tonight has been very enjoyable and that I'd like to spend more time with you," I told her. "So, yes, I think we're compatible. But I never thought otherwise. The only question is, are we compatible beyond just baseball and talking?"

"OK, I assume you mean physical compatibility," she said, taking a sip of wine. "How do we find that out?"

"I suggest a kiss," I said. When her eyebrows went up I said, "Just one kiss, to see if there's chemistry between us. I'm willing to chance it - if there isn't, then we won't waste our time."

"And if there is?" Dana asked, a skeptical look on her face.

"Then we know we have something worth continuing," I concluded.

"Now I'm wondering again if you lured me up here," Dana said suspiciously.

"Innocent of all charges," I pleaded. "I'm just pursuing the question of us dating."

She seemed to make up her mind and set her wine glass on a side table. I did the same and went in front of her. "I didn't plan to lure you up here," I assured her. "But I'm very glad you're here." I moved closer and held her at her waist as I drew her toward me. Dana's hands went to my arms and we looked into each other's eyes as we moved to kiss. Hers were curious (?) and then my eyes closed as our lips touched.

The kiss was a light one at first, just the feel of her lips on mine, but it felt....right! We melted into each other, no awkwardness at all, like we were meant to fit together. Passion built as the kiss went on, my hands going to her back to hold her to me, her arms moving up to go around my neck. Now we were kissing deeply, our bodies melded together. I was overwhelmed with the sensation of kissing her, the scent of her, the feel of her on my hands, her breasts pressing against my chest. This was a kiss for the ages!

It was minutes before we reluctantly took our lips away from each other, still holding each other tightly.

"That was quite a kiss," I whispered, looking into her eyes, which were now very much alive with emotion.

"Yes, but inconclusive, I think," she said softly. And then her lips were against mine again and we dove back into one another. As our passion built my hands moved over her back, holding her to me to feel the firmness of her. Her belly pressed into my erection and her breasts into my chest, as if we could melt into one another.

Still standing, we parted for a moment and Dana took my sports coat off over my shoulders, letting it fall to the floor. We joined again as it fell; this time one of my hands was on her arm, stroking her there. I dared to move it between us to cup a full breast, covered by that incredible dress, and Dana moaned softly as I moved my hand over the firm mound. She kissed me harder and pressed into my hand as I caressed her.

When our lips parted again she whispered, "Dave, what are we doing?"

"Finding out how compatible we are," I replied softly and kissed her again. I felt one of her hands leave my neck and go between us, covering my hand on her breast - not to move it but to hold it there. Then her hand slid onto my shirt and began to work at the button at my neck, undoing it and moving down to the next. I took that as my signal to use my free hand to unzip her dress.

Pulling the zipper down Dana's back I slipped my hand inside the dress to feel her smooth, warm flesh. She had undone all the buttons on my shirt and we parted so she could slip it over my shoulders. I did the same with her dress, which slid to the floor, revealing her lovely body, now covered by a sheer black lace bra, black panties that were not quite a thong and black thigh-high stockings. She pulled my undershirt up from my waist and I helped her take it over my head, leaving me naked from the waist up. She started to undo my belt, but I pulled her into me and kissed her once more, my hands now caressing her bare back and running over the lovely cheeks of her rear.

Dana's hands were on my back as well, running over my skin, heightening my need for her. I undid the clasp of her bra and moved to kiss her jaw and then neck as I slipped the straps over her shoulders. Her head rolled in pleasure as I nuzzled her and slid the bra down her arms, revealing her beautiful breasts. She gasped as I cupped the fullness of her right breast and lowered my mouth to her taut nipple. As I nursed at the spectacular globe her hands went to the back of my head, pulling me into her. She finally guided me upward to her face so we could kiss again. Before we did, I murmured "Dana, you're a goddess." She blushed brightly at my praise; instead of kissing me she reached for my belt and began to undo it. I helped her and we succeeded in getting my trousers to fall down, leaving me in briefs tented with my arousal.

"I think we should move to the bed," I suggested, slipping out of my shoes and stepping out of my trousers. Dana stepped out of her dress and I took her hand as we moved to the side of the bed. I quickly pulled the bedspread down and guided her onto the bed. As she lay back I reached for her hips and guided her panties down her long legs. Now nude except for her black stockings she was truly a goddess lying there. I skinned my own briefs down my legs before I joined her.

My hands went to her calves and began a journey of caresses up her long legs. Dana's legs were shaped beautifully - legs a model would die for - and I trailed my hands with soft kisses on her stockings. She shifted, I hoped in pleasure, as I caressed her and moved up her legs. I reached the top of the stockings and was rewarded with the smooth skin of her upper thighs. My hands went under her legs to lift them to my mouth and I trailed my lips along her soft flesh, reveling in the feel of her on my hands and mouth.

Dana twisted in pleasure as I explored her like this, slowly moving higher and higher up her long legs. I sensed her holding her breath in anticipation, but I was taking my time, enjoying the feel and taste and scent of her, so she would have to breathe sometime. I guided her legs apart as I traveled up those beautiful thighs, and Dana cooperated by shifting to open herself to me. She was breathing again, more quickly now as her arousal grew. My arousal had grown as well, and my cock was rock-hard under me as I kissed and licked her.

I reached the juncture of her legs and I could see the dampness of her arousal in the bare lips of her pussy. I ran my tongue lightly over her, tasting her excitement, and her hips lifted toward my mouth. I licked more deeply at that response and her breath caught as my tongue trailed over her opening and then her clitoris. She moaned softly as I explored her with my tongue, her arousal growing rapidly. Just as I was deciding to make her orgasm with my tongue I felt her hands on my head, pulling me up to her.

I left her soaking pussy reluctantly but comforted myself by trailing my tongue over her heaving belly and upward to her breasts. I resisted her pulling at me long enough to linger at her breasts, sucking gently on each hard nipple in turn. Dana moaned again and lifted me up farther, and then we kissed again. Our bodies were pressed against each other, my hard cock lying on her pussy, pressing against her clit. I rocked gently against her, the sensation of gliding along her dampness hardening me even more, if that was possible. Dana started subtle movements of her own as we continued to kiss, until our mutual need became irresistible.

I moved my hips to slide my cock lower, until it slipped between her legs. Dana moved to position me at her opening and, as we looked into each other's eyes, I slowly entered her. The feel of her surrounding my cock as I slipped into her was incredible, indescribable. It was as if we were always meant to be coupled like this, that this moment had been coming all my life.

"Oh Dana." I murmured as we joined.

"Dave," she whispered back.

And then it was as if we were one being, brought together by an irresistible primal attraction. I began to move slowly, absorbing the pleasure of feeling her on my body, and Dana responded with her own movements. We made love deliberately, enjoying each other as our mutual arousal grew. Dana's hips lifted to increase the feel of me on her clitoris and I changed my movements to put more pressure there. My strokes into her lengthened as we rocked together and both of us began breathing harder and quicker, building toward our climaxes. I leaned down to kiss her as we coupled and felt the beginnings of my climax as we kissed. I somehow held off until Dana's breathing became ragged, her orgasm nearing. As she moaned into my mouth I let myself go, and managed to explode into her just as she peaked.

We pulled back from the kiss as our bodies eased down from the exquisite sensation of our mutual climax. I looked into Dana's eyes, full of softness and wonder, and felt the same amazement at how good we were together. I slowly rolled off her, my cock slipping out of her, and lay beside her, holding her, caressing her flat stomach. Dana rolled toward me so we could kiss again and we lay like that on our sides, holding each other while we kissed. The magic of finding each other like this, just knowing it was perfect, kept us from parting for a long while.

It was if a switch had been flipped; we had gone from fellow employees who flirted a bit over baseball teams to almost newlyweds. That chemistry that bubbled beneath the surface of our flirtation had exploded into something close to love in one evening.

Pulling back from one of our wonderful kisses I stroked her hair lovingly, brushing stray strands from her face.

"I'm going to go with compatible," I said, half as a joke, half dead serious.

"It appears so," Dana said in a voice filled with emotion. "Despite the fact that you're a Red Sox fan!" she said with a brilliant smile that entranced me.

"I have many other fine qualities, as I hope you will discover," I told her. I leaned in and kissed her again, and felt the same magic as before.

When we parted I said, "I hope you can stay here tonight. I'd hate for this to end."

Dana hesitated, finally answering, "I would love to," she said. "But I have no toiletries, no clothes for tomorrow."

"I'm sure we can figure something out," I assured her. "I can go to the front desk or shop and get a toothbrush..."

Dana thought about it. "I have a workout bag in my car with things for the gym," she offered. "Though I'm not sure I'm ready for you to see me in yoga pants and a sweatshirt, without makeup!"

"I hope to mostly see you nude," I told her. "And you underestimate how beautiful you are." That earned me another smile.

"Fine," Dana said, her decision made. "If you would please fetch the bag - it's in the trunk. My keys are in my purse. I'm parked in the second row, a blue...."

"I know your car," I told her, hopping out of bed. I set the world record for throwing clothes on and getting to her car and back with her bag. I stripped off my clothes and eased into bed beside her.

"Miss me?" I joked.

"I did, actually," she confessed.

We made love again that evening, this time with Dana riding me, her lovely breasts readily accessible by my hands and mouth. I discovered that she was multi-orgasmic, and was more than happy to give her as many climaxes as I could. We slept with her spooned into me, the scent of her washing over me as I drifted off to sleep. We made love again the next morning and then enjoyed a sumptuous breakfast in the room, both of us in hotel robes as we ate ravenously, sipped coffee and tea and talked. Would it have happened without the bet? I like to think so, but one will never know. The bet started our flirtation; after that nature took its course.

Fast forwarding 11 months, Dana and I were engaged, the wedding scheduled for the following June. The bet continued even though our relationship had changed dramatically, perhaps in recognition of its role in bringing us together. Dana had announced at the beginning of the season that she wanted the year-end bet to be a weekend at a resort in the Poconos in Pennsylvania if she won. She chose that because I wasn't a fan of weekend trips, preferring to relax at home. After thinking hard about my side of the bet I told her we would go even if I won, but I would get to pick what she wore for dinner Saturday night.

"Don't you like what I wear?" she asked, a bit indignantly.

"Of course I do," I told her. "I just would like to see you wear something a little more risque sometimes."

"How risque are we talking?"

"Nothing slutty, I promise," I assured her. "I'll even let you help me choose. So, is it a bet?"

The season won/loss between the teams went down to the wire, with the Yankees up one win for the season going into a final three game set in Fenway. The Sox had to win all three for me to win the bet. If the Yankees won one they were assured of a tie, two wins meant Dana won the bet. Let's go Sox!

My boys won the first game easily, 8-3, tying the team vs team season record. It was looking more and like we would end in a tie but there was still hope. The second game was in doubt, Sox trailing going into the eighth, but they came up with three runs that inning and the closer hung on to save the win. Now I was ahead - all Dana could hope for was a tie, which would cancel the bet.

As the second game ended I looked at my unhappy fiance and decided to forego gloating. But an inspiration struck me - I could sweeten the bet!

"Tough loss dear," I said carefully. Dana did not like losses. "Since the best you can do is a tie, let me suggest a 'double or nothing' bet."

"What would that be?" she asked suspiciously.

I put on my most sympathetic face. "Well, right now, if I win we go to the resort but you have to wear a dress of my choice. If we tie, everything is off. What I propose....what I propose is that if we tie we go to the resort just as if I had won. But if I win we go with the added proviso that you have to go braless at dinner."