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The Bet

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If you have read my previous stories, you know my experiences with a few guys that have seen me naked by accident at first but upon my discovering they were there, I just let them look. It still turns me on to think about the neighbor guys watching me sunbath naked and that day on the beach with Stu and Dan.

Stu and I eventually broke up amicably. I moved back to the city to finish my degree in finance. I bartend at Ric’s not too far off campus that has a casual atmosphere with a patron mix of graduate students and young professionals. I generally work only a few nights a weeks which allows me to go to school full time during the day. The money is pretty good and I have developed some regular customers.

The owner, Ric, does not care what we wear to work so I generally wear long pants or jeans with a shirt that will show just enough cleavage when I bend over to let a guy think he is seeing something he should not. I have 34Cs with ultra-sensitive nipples on a thin frame so I know how to play my boobs up if I want to.

Almost all of my regulars are guys so I know it does not hurt my tips to play the cleavage-card. I am also making contacts with people that may help me find a job after I get my degree so I am careful not let them think of me as some mindless twit with boobs.

Anyway, one of my regulars is a guy with whom I went to high school named Tim. I even used to baby-sit for his little brother, Bill, who Tim told me was now 18. I could not believe it. I had lost touch with Tim after high school when he moved out west to go to college and he worked in Phoenix for a couple of years. He was back in town now working for a local business consultant and would stop by the bar almost every night I worked.

Tim and I were friends but had a flirty relationship. Like the other guys, I would catch him looking down my shirt when I would lean over to get a beer or ice for a drink.

On his birthday recently, he came in alone early one night but was meeting some friends later. I was wearing a blouse with buttons all the way up the front. Since it was early, the bar was not very crowded. When he was not looking, I undid two extra buttons to below my lacey, push-up bra. It was cut pretty low to maximize cleavage so my nipples were only just covered. After letting him look for a few minutes, I feigned surprise on looking down at my unbuttoned condition.

“Did you get to see enough?” I asked in my best shocked tone as I buttoned up.

“No,” he answered with a laugh.

“Well,” I said changing back to flirty. “Consider that part of your birthday present then. Oh, and I am picking up your bar tab, too.”

“Wow, that is nice of you, Jen, but why don’t you unbutton again and let me get the tab,” he offered, only half-jokingly, I could tell.

I would see him at the bar and more often than not, we would flirt and tease with each other. I thought he was very handsome but since we had been friends so long, I never thought of him in a sexual way. He showed up almost every night I worked and from the way I caught him staring, it was apparent he had a thing for my tits.

It was not until the World Series rolled around that he got more overt with his desires.

I have always been a big New York Yankees fan. In the summer and fall, if there was a Yankee game on while I was working, a television I could see easily from the bar was going to have that game on. At this time, the Yankees had one the World Series three years in a row and were on their way to winning a fourth against up-starts that had only been a professional franchise for four years: the Arizona Diamondbacks.

On the night of Game One, I was working and Tim was there as usual. I was wearing my favorite Yankees pinstripe jersey which leaves a flap at the top when unbuttoned properly.

“You are a Yankee fan?” he asked staring and pointing at my chest.

Sticking my chest out and pointing a finger at my chest with both hands, I responded, “Yes. How did you guess?”

“Lucky guess,” he answered smiling crookedly. “When I was working in Phoenix, I had Diamondback season tickets for their first season before I moved back here.”

I looked at the scene of the park being shown on the television longingly.

“It looks like a great park. I haven’t been to a Yankees game since I snuck up to New York two summers ago for a three game home series. Man, I would love to be able to be there to watch them win their fourth world championship in a row.”

“I hate to tell you but the Yankees are going down this year,” he said mockingly.

“Wanna bet,” I responded without hesitating.

“Sure,” he responded just as quickly. “What do you want to lose?”

I was being challenged.

“My car is sure dirty,” I offered leaning on the bar to get my face closer to his. “How about you come over to my house after the Yankees win and wash it for me?”

He sat back before responding.

“Ok, but when you lose, you will come to my house in your skimpiest bikini and wash my car. Deal?”

“Oh, we are going that route, huh?” I said tauntingly. “Then you will be washing my car in a speedo!”

“I canlı bahis do not own a speedo,” he said smiling before taking a sip of his beer.

“I will find one for you.”

“I can probably find my own suit but I do not think it will come to that.”

“Deal!” I exclaimed holding my hand out to shake. “I look forward to watching you wash my car.”

He laughed as I handed him another beer. “Dream on!”

The Yankees started out poorly, losing the first two games on the road in Phoenix by a combined 13-1. They even got shut out in the second game, 4-0.

Tim had been really rubbing it in being up two games to nothing. I told him I had absolutely no doubt the three time World Champions would find their stride back in Yankee Stadium.

Back in New York, the Yankees did not look great but they played well enough to win 2-1. Down only a game, I felt confident that this was the beginning of the end for the Diamondbacks. I was really starting to look forward to watching some eye candy while my car got washed. I had started wondering about what Tim’s body would look like barely covered.

Tim dutifully showed up the night of game 4 and our trash talking continued.

He had a couple of shots before the game coverage began which was not normal for him.

As game time approached, he looked at me a little unsteadily.

“How confident are you the Yankees are going to win the series?”

“Absolutely confident,” I answered.

“Confident enough to change the bet from washing my car in your bikini to just wearing a wet t-shirt and bikini bottoms?” he whispered exaggeratedly as he leaned closer towards me and the bar.

I was a bit shocked at his suggestion but did not want it to show.

“Yes, I am that confident. Are you confident enough in Arizona to wear only some tighty-whitey underwear while you wash my car?”

“Yes, I am that confident,” he said mocking me. We shook hands on it.

Game 4 was a nail biter. I was really nervous as the Diamondbacks were one out away from winning in the ninth inning before the Yankees tied it up to force extra innings. Then the Yankees pulled it out to tie the series at two a piece as Derek Jeeter hit a single run homer in the tenth inning with 2 outs to win the game, 4-3. The series was tied again.

Game 5 was much the same except the Diamondbacks’ pitching closer, only one out away from winning the game, allowed the Yankees to score and win, 3-2. New York was now only one game away from winning it all again for the fourth time in a row. I knew nothing would stop them. I was ecstatic.

Neither Tim nor I had mentioned the new bet with the greater exposure since right after Game 4 ended. I was not worried at all about the Yankees losing but I guessed Tim was nervous about Phoenix’ prospects.

I was absolutely confident the Yankees would handle Phoenix in game six and I was starting to get a bit turned on by the specter of Tim wearing only skimpy white underwear, all wet on my driveway. I was starting to have some really dirty thoughts about him. I was looking forward to seeing what he was packing.

That would have to wait as the Diamondbacks came on strong in Game 6 to win, 15-2. I was in shock. The series was tied going into Game 7. It all came down to this one game. I could not fathom the Yankees losing to this up-start team from the dessert.

Tim showed up as usual at Ric’s for the decisive game. He looked nervous.

As I walked back over to him after serving another customer, he said, “I really want to see you in a wet t-shirt.”

I blushed a little at his honesty and I could feel my nipples hardening. As he stared at the twin bumps growing at the peaks of my tits, I wished I had worn a thicker bra than the lacey black one I had on.

“To bad since you are going to be washing my car in your underwear sometime after tonight.”

It was another tough fought game but as Phoenix prepared to take the field in the bottom of the ninth, they were down to my Yankees, 2-1. I was so ready for them to win and for me to win, too.

Before the Yankees got back on the mound, Tim leaned onto the bar and motioned me to lean in close to him. As I did, he did not even try to hide the fact he was looking straight down my shirt.

“Hey,” I said, tapping him on his chin with one finger. “Up here.”

“Yeh, sorry.”

“Look, I know it does not look good for my team so how would you like to up the stakes?” he asked staring now straight into my eyes not two feet away.

I smiled the smile of a predator looking at cornered game.

“What do you propose?”

“If Phoenix does not pull this game out, I will wash your car naked.” He said flatly still staring me straight in the eye. “You can even invite a couple of your closest friends, if you wish, to keep you company.”

I was excited at the prospect and I think I let it show with my growing smile. He was really getting to me and I really wanted to see him naked. I tried not to let it show but it was difficult.

“I am glad to see you like the idea so far. Now should the Diamondbacks end up winning this game, bahis siteleri as I expect, I want you to play pool with me against a couple of my friends one night here at Ric’s.”

The game was about to start again but I knew he was leaving something out so I asked, “That is it? Play pool?”

“Well, no,” he responded and as he looked down at my tits again, he added, “I will be picking out some lingerie for you to wear while we play.”

“There is no way I am going to be paraded around the place I work nearly naked with Ric and everybody else here,” I whispered quickly to him not wanting anyone else to hear but showing my annoyance.

As he looked back at me and then the television as New York jogged out onto the field, he responded.

“First, we will do this one night when you are closing alone and locking up. Two, you will be wearing lingerie of my choosing and viewed only by me and the two people we will be playing pool against. And three, Ms. Yankee Die-hard, your boys are winning in the bottom of the ninth so you are probably going to see me naked way before I ever get to view your luscious lingerie-clad body!”

I knew he was gaming me but he was right. The Yankees were going to win and I was going to have him naked that weekend. I could not wait to tell my friends Beth and Amy to come over for the show.

“You are on,” I said, feeling an adrenaline rush.

I was so into the game, I stopped serving drinks. Nobody complained.

The first Diamondback batter reached base. Others were getting hits and with only one out, the Yankees had allowed one runner to reach second base. I did not want this to go to extra innings. Then Phoenix bunted the runner to third base. I was yelling at the TV.

Then there was a dreadful “crack” sound as a Phoenix batter solidly connected to a New York pitch. It was out of the park.

The Phoenix Diamondbacks had hit a two-run homer in the bottom of the ninth inning to defeat the New York Yankees in Game 7 and win the series, 4-3. It is one of the biggest underdog wins in sports history.

Like lots of other fans, I was in shock but not just because New York lost. I lost a rather significant bet.

After a while, Tim turned towards me smiling but not gloating.

“Are you working tomorrow?”

“Yes,” I answered dazedly.

“Are you closing?”

I popped out of my daze as the significance of the question hit me.


“Want to stay a little late and play some pool, if we can?” he asked with a beaming smile.

“Might as well pay my debt as soon as possible,” I said, still in disbelief my Yankees had not won. “Can you give me any hint as to the get-up you are going to have me in? Please, not too exposed.”

“Well I do not want to give away too much,” he responded. “It will not be see-through and it will offer support.” “My, you have put some thought into this,” I quipped.

“For a long time,” he answered giggling. “You will look great.”

He paid his tab and left me a good tip.

“See you tomorrow,” he said after we hugged goodbye. I swear I detected an erection.

I could barely sleep that night and I skipped my only class of the day. I was nervous of the unknown. I had no idea what he was going to have me wear but I guessed it would not cover much.

“He said it would not be see-through. That is hard to believe,” I thought. “He isn’t going to just have me get naked, is he?”

My mind wondered over the unknown.

“No, he said it would have some support. A bra?”

With all this wondering about how exposed I was going to be, I was getting that flutter in my stomach that has caused me to do crazy things in the past. I started to think back about Tom and John watching me lay out naked. And the time on the beach with Stu and Dan. I was getting turned on. I was so worked up with nervous energy, I fingered myself to quick climax in the shower before work.

I was not sure what to wear to work or what I would be allowed to wear after work, if anything, with my lingerie. So I wore my favorite blue, push-up bra and panty set just in case.

I concentrated on work and about an hour before closing time, Tim walked in carrying a small black gym bag.

“That must contain my outfit for the night,” I thought as he sat down.

He had a beer and we talked about the usual things avoiding the elephant in the room. I had a couple of shots to calm me down but Tim seemed calm and to be sipping on his beer rather slowly.

As I announced last call to the other patrons, he broached THE subject.

“How about that World Series? Unbelievable, huh?”

“Yes,” I honestly agreed. “Unbelievable. I thought you would show up with our pool buddies. You haven’t had second thoughts and are going to let me out of this, are you?”

“I cannot believe for a minute you would allow me to let you welsh on a bet,” he said challenging me. “They will be along after closing.”

Everyone finally left and clean-up went faster than usual as Tim helped me. Finally, I made sure to turn off lights and lock the door so the place looked closed. I turned on the exterior alarm so bahis şirketleri nobody could sneak in without me knowing it, even with a key.

There was one pool table hidden by a wall from any exterior window. I manually turned the light back on over that table . I had never noticed how bright these lights were as it seemed to really illuminate everything around the table in the otherwise dark room. I was getting nervous and walked back to the bar for another shot and to grab two beers for Tim and I. I dutifully wrote the drinks down on my tab as Ric had always asked us to do.

Back at the table, I handed Tim his second beer of the night and took a big sip of mine.

“Where are your friends, and by the way, what did you tell them about tonight? I should have never agreed to any of this, much less to do it in front of anyone other than you,” I argued.

Tim looked at his watch before answering.

“Honestly, I was a little drunk when I made that bet or I never would have offered to get naked myself while my team is down in the ninth to the Yankees,” he said sincerely.

He continued.

“This morning I mentioned only that I had won a bet on the Diamondbacks with you so you were going to have to play pool with me in the lingerie of my choice. These guys are actually not the two I had originally thought I was going to ask to join us.”

“What?” I interjected. “You are telling everyone about this. I do not want rumors going around about this. I don’t know if I can go through with this, Tim. Can’t we work something out?”

“Look,” he said calmly. “They are the only other people that know about this and they are totally discreet. I don’t know if it will make you feel any better but you know them.”

“Who are they,” I asked.

You will know them when you see them,” he answered. “And honestly, they will be more discreet than my roommate Don and friend Pete I was thinking of originally.”

“I am so glad you did not ask them,” I responded with a sigh of relief. “I have a class with Pete and Don goes out with one of my best friends. I don’t know if I could face any of them again. Please, tell me how I know these other guys? You are making me very nervous.”

“Relax. You do not work with them. You do not go to school with them. You have never seen them –I don’t think– in this bar,” he stated mechanically. “You might be surprised at first but I think you will realize they will never tell anyone and even if they did, nobody would believe them.”

“What do you mean?”

“Will you relax? You will understand soon enough,” he responded. “I told them to swing by about 1 o’clock figuring you would be nervous and to allow us time to warm up our game. I think you will distract them enough with the attire I have picked out for you that there is no way they will be able to hit a straight shot. Just in case, let’s practice.”

“Show me what I am going to be wearing,” I said looking back at the gym bag on the chair.

“Soon but for now, why don’t you get down to your underwear and let’s play a game first,” he answered with a smile.

“Why not?” I asked myself since the underwear I had chosen was satin and opaque. I had bikinis much skimpier than this.

I took off my shoes and socks. Then I shimmied out of my jeans leaving only my silky black shirt covering my blue bra and thong panties. I looked at Tim and then down as I slowly unbuttoned one and then another of the buttons until finally my shirt hung undone. I turned my back to Tim and shrugged the shirt off my shoulders to the ground.

As I looked over my shoulder, Tim, who was staring at my ass said, “Damn.”

I turned around and his eyes went straight to my breasts, wondrously pushed up by my Wonderbra.

Spontaneously, he said while staring, “You know I have always had a thing for your tits, huh?”

“I kind of figured it out since you are always trying to look down my shirt when I lean over in here.”

“Woops. Guilty as charged,” he answered looking at my face briefly and then back to my body. “You may have to carry our game, too, as you are really distracting. You have a great body, Jen.”

“Thanks,” I said grinning, starting to enjoy the attention.

“We have about 20 minutes before they should be here so let’s play a game.”

It was a little awkward at first playing pool where I work wearing only my underwear but I knew it was probably going to get weirder soon. The first time I leaned way over the table with Tim behind me, I stood back up and looked at him. From the look on his face, he obviously had seen the satin in bright light spread tightly across my pussy leaving very little to his imagination.

Just before 1 o’clock, Tim asked me if I was ready to get dressed. Without a word, I put down my cue and took the bag he offered from his hand.

Once in the ladies room, I put the bag on the sink and took off my bra and panties. Staring into the mirror, I knew I looked good. Long legs with shapely thighs; a little brown landing strip; flat stomach; and firm 34C boobs that looked bigger on my 5’6″ frame. I could not find a place to lay out topless in the city so my tits looked even bigger because of the untanned portion. My fading tan lines passed just above my quarter-size areolas and my nipples which, as usual, were also sticking straight out about an inch.

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