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 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, 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?"
