Daring To Tip

I had known Tammi Taylor for almost 10 years now. We had both come to EroTech at about the same time and had had assignments that required us to work together many times. I really liked Tammi. She was intelligent, hard working and had more than her share of competitive blood. A very attractive, fortyish, mid-level department head, she had developed a reputation for competence and honesty. Married with two children, she had amazingly managed to become upwardly mobile in the company without having to put out for every regional manager that she had been assigned to.

This is not to say that Ms. Taylor is a prude. I knew her well enough to know that she had a very healthy libido, but she never let it get her in trouble with anyone at EroTech. I made my run at her early on. However, my seemingly relentless assaults were met good humor and more than a little teasing. I wish I had $5 for every time I had left her office after hours or her hotel room on the road with a stiff aching cock, but somehow feeling good about her, and about myself. Eventually, we became good friends.

Last week, I got an unusual call from Tammi. I hadn't heard from her in a while, but I didn't think that was too unusual. She had just been promoted to Head of Accounting at our Little Rock Office. She had been sent there to "clean house" and I knew that she was going to be very busy for a while. When she called, she asked if I could meet with her over the weekend. I kidded around about what she might have in mind, but then I realized that she was pretty serious.

"I need your help, Sean," she said, "I'm finding some stuff here I don't like and I need someone I can trust to go over it with me. Sort of make sure I'm not seeing things, you know?"

"Sure, Tammi," I assured her, "I'll get a flight tomorrow afternoon."

"Thanks, Sean," she said noticeably relieved, "I really appreciate this. I owe you one. But, I'll come up there. I'll explain when I get there, OK?"

"Sure, no problem," I said, "Can I set up anything for you, hotel?"

"Yeah, can you get me a suite at the Hilton?" she said and then added, "with a Jacuzzi! I'm going to need all the comforts I can get."

"Sure thing, Madame Executive," I teased.

"And I'll be on Delta Flight 69 getting in there at 3:45," she said seriously, "Can you pick me up?"

"Sure thing," then thinking out loud, "You have your reservations already? Hmmm… The lady is pretty sure of herself, isn't she?"

She chuckled softly and then said quietly, "The Lady knows who her friends are, Sean. Thanks. See you tomorrow."

When I picked her up at the airport, she was even more attractive than the last time I had seen her. We hugged and she gave me a peck on the cheek. "You're looking mighty good for an "aging" executive, Sean" she teased squeezing my arm. Mmm… that remark went right to my cock!

"Well, than you, Ma'am," I said and then smiling at her, "You still do it to me, you know?"

She laughed and gently punched my arm. "You're incorrigible, you know that!" she said with mock incredulity. "Which reminds me, I'm not taking you away from Karen and the boys this weekend am I?"

"Karen is visiting her mother in Bakersfield for two weeks," I explained, "and both the boys are away at school. I've been a bachelor for a week now."

"Oh, great…" she said exasperated.

"What?"

"Nothing…" she replied flippantly.

"No, no. Come on! Don't do that nothing thing!" I said sounding too much like and irate spouse.

"Oh, OK. Well, Sean…" she said looking at me with that how-can-I say-this-without-you-getting-mad look, "It's just that I know how you get when you are, shall we say, 'deprived'?"

"Oh, that..." I conceded, "Look, Tammi, I know you came here for my help on something serious. There is no way I'd take advantage of that... or you, under these circumstances, OK?"

She looked into my eyes and smiled. "I'm sorry, Sean," she said and kissed me on the cheek again.

"Hey," I complained, "with all this kissing and that perfume you're wearing, you're not making it easy!"

"Down, Rover!" she said as she turned and headed for the taxis.

When we got to the hotel, she checked in and then we arranged for me to come back over to her room at 9:00 the next morning. She would spend the evening getting all the materials laid out to make it easier for us to review.

When I got to her room bright and early on Saturday morning, I couldn't believe how much paperwork she had laid out for us to review. But characteristically, she had it well organized and we started to work. The issues here involved the possibility of phony inventories and bills paid for services that we never rendered. The way we approached this, Tammi would present me with some irregularity that she had found and I would play the devil's advocate, trying to explain it away or minimize its importance. At first everything seemed normal, or at least explainable, but soon a very consistent pattern began to emerge. Whoever was doing this was very good, but not quite good enough.

By 2:00 in the afternoon we had proven the fraud and narrowed the suspects down to three people, but it wasn't until about 6:30 that I could say to her, "It's Thompson, your warehouse manager. See here, he's been double billing these service accounts, probably with their cooperation, and ordering inventory through a dummy corporation, pretending to take delivery and then billing Erotech."

"You're kidding!, she said, "Can he do that?"

"He's doing it, Tammi!" I explained, "It's all right here."

"Wow," she said still dazed, "All the time, I was looking for errors from sloppy accounting practices, which, by the way, was very common when first got to Little Rock. But, Hell, this is fraud!"

"As a rough guess, I'd say he's taken in about $500,000 so far this year."

As I looked at Tammi, I could see that she was very visibly relieved. She had been carrying all this inside, not knowing how it would turn out. It was still bad, but it was not her fault and she could now begin to deal with the problem. She got up, came over to me and gave me a big hug. "Thank you, my friend," she said quietly, "Thank you so much!"

"Hey, what are friends for?" I said smiling. "Listen, I don't know about you, but I'm getting hungry. What do you say about some dinner?"

"Sure," she agreed, "Where's a good place?"

"Actually, I was thinking of Piazza," I said casually.

"Piazza de Roma?" she gasped, "Are you kidding? I've only heard about it, but it's supposed to be incredible!"

"It's nice," I said calmly.

"Nice? Sean!" she exclaimed, "It's… it's expensive… and it's late! We don't have reservations!"

"Yes we do," I said smiling.

"We do?" she smiled, then, "Damn! I don't have anything to wear…"

"Nothing?

"Well, I've got a nice red and black blazer and a short black skirt?" she complained.

"Perfect!" I said.

"You think?" she smiled.

"Shower and shave and meet me down at the bar in 45 minutes," I said.

"45 minutes!" she exclaimed, "I can't…"

"Tammi…" I said quietly.

"Yes?"

"Just do it!" I said smiling.

"Yes, my Captain!" she said giving me a mock salute and heading quickly for the bathroom.

When she came down, exactly 53 minutes later (women!), she looked amazing. I knew that I had promised not to take advantage of the situation, but this was going to be a real test. When we got to Piazza, the maitre d' took us through the main dining room to a small private room in the rear of the restaurant. I could tell that Tammi was already pleased with Piazza. It was obvious that she liked the décor, the ambience and… the looks she was getting from the male clientele.

When our waiter, Leonardo, came in, we each ordered the veal scaloppini and a bottle of 1993 Chianti Classico. The meal was excellent in all the little things that only fine restaurants can provide. Tammi and I really relaxed and chatted pleasantly. I could tell that she was really enjoying herself. She was attracted to the Piazza and, as I was rapidly becoming aware, to our waiter Leonardo. I had always been fascinated by the difference between Ms. Taylor the executive and Tammi the woman. This was just another small mystery revealed.

She saw me looking at her and she reached over and put her hand on mine. "Sean, this has been an absolutely incredible day for me," she said "And I really owe it all to you. I really owe you!"

"Tammi," I explained, "First of all you are my friend and helping a friend always makes me feel good. But…" I said breaking into a devilish grin, "you really do owe me, don't you?"

"Oh no…" she said wearily putting her hand to my cheek, "Listen Sean, darling, you are a wonderfully attractive and sexy man. You may not know it, but over the last ten years, I have been severely tempted several times to take advantage of you. I know how your hormones react to me, and it would have been easy…so easy. But in the morning, I wouldn't have been able to look either myself or Karen in the eye ever again. So, my sweet, I am not going to fuck you, tonight or any other night. Do you understand?"

"Wow!" I said amazed.

"Wow?" she said amused, "That's it?"

"Well… yes," I stammered, "I mean, no. I mean I guess I always knew that, Tammi. I don't think I'll ever be able to turn off my hormones when it comes to you, but you are a special friend and a special person. Besides, I think you are a much better friend than you would be as a one night stand."

"Hmmm…" she said smiling, "I guess I should take that as a compliment?"

"You know what I mean," I said.

She leaned over and whispered, "Yes, I do!" and kissed my cheek.

I looked at her and broke out into a big grin.

She smiled quizzically and said, "What?"

"You still owe me," I said smiling, "And just for the record, I wasn't really thinking of having you pay me off that way. But, you really shouldn't walk around owing me either. I think you should pay off tonight."

"Uh-oh," she said skeptically, "What exactly did you have in mind then?"

"A dare," I said, "Just a dare."

"Oh God, Sean," she said laughing, "We haven't done those in years!" Then, looking at me, "You're serious aren't you?

"Yes, I am," I said smiling.

"Same rules?" she asked.

"Yup," I assured her, "Can't involve money or anything of material value and can't hurt anyone."

"I think I'm going to regret this," she said, "but, OK, I'll take the dare."

"Good!" I smiled, "Here it is. I am, of course going to take care of the dinner. It is, after all, a legitimate business expense. However, I dare you to leave the tip."

"Why, Sean!" she smiled in mock amazement, "I thought you would come up with something more challenging than that. I mean, this is an expensive restaurant, but I'm sure I can afford the tip!"

"I'm sure you could too," I agreed, "but remember the rules… no money. You know, I'm not exactly blind. I see the chemistry going on between you and our Leonardo, Ms. Taylor."

"Oh, Sean!" she blushed furiously, "For God sakes!"

"I wouldn't exactly call that a denial," I smiled. "Look, this waiter, Lee-Oh-Nar-Do, has been very good. He really knows what he's doing, wouldn't you say?" She nodded warily and started to blush again. "Well, you know how waiters usually have to split their tips with the other waiters?" She nodded. "That would really be a shame in this case, wouldn't it?" I said with a big Cheshire cat grin. "You know the rules, his tip cannot be money or anything of exchange value, thus he won't have to share it with the other workers. It has to be something that he cannot take out of this room with him tonight."

She look surprised and a little confused. "Well, what then… a kiss?" she said coyly.

"Hmmm, how to put this," I mused, "Tammi, judging by the way he has been looking at you tonight, and that rather prominent bulge I saw in his trousers when he was serving you…"

Poor Tammi was beet red now, indicated that she had indeed notice the same thing.

"I don't think a kiss would cover the appetizer," I said smiling at her obvious discomfort.

"Well, what then?" she asked. But no sooner were the words out of her mouth than it dawned on her where I was headed with this. "Oh, no!" she said emphatically, "Are you crazy? Absolutely not!"

"You know you want to, Tammi," I said smiling.

"Oh, for God sakes, Sean!" she said, blushing furiously. "I can't just..."

"Are you chickening out?" I said, taunting her.

"I'm not chickening out of anything," you say a little irritated, "But this…"

"Cluck, cluck, cluck..." I said giving my best barnyard imitation.

If looks could kill! "You bastard!" she said seething, "You think you finally have me now, don't you? The payback is me chickening out of a dare for the first time. You think I won't do it!"
"Tammi, my dear, you are a wonderful, very competent, intelligent woman," I assured her, "But there is no way in hell you are going to do this," I smiled confidently, "I've got you this time, my dear!"
Just then the waiter came in with the bill in a leather folder. I saw her looking at him intently and then back at me. She was so "not smiling." I checked the bill, slipped my credit card into the folder and gave it to Leonardo. When he had gone I said to her, "It's really a shame, you know. He's worked very hard tonight, but I'm not going to leave him a tip. That's your job." I don't think I have ever seen Tammi that upset. Her pride and competitive spirit were really taking a beating. I felt sort of bad then, but a game is a game and someone has to win.

When Leonardo returned, I could sense her tension. She didn't look at him this time. He handed me the folder with the credit card receipt for my signature. I added the total of the bill, but no tip, and then signed it. I knew she was watching me. When I put the slip in the folder and started to hand it to the waiter, she suddenly reached out and took it from me. She glared at me and the intensity in her eyes gave me a chill. Then, seeing my surprise, she gave a very wicked grin.

Smiling pleasantly up at Leonardo, she held the folder out to him, but as he reached for I, she drew it back, just out of his reach. He smiled a little nervously and when she held it up a second time, he reached for it again. This time he leaned over her to reach further and she put her other hand right up against his crotch to hold him back.

"Not so fast, young man," she purred, smiling up at him. "Did you know that this cheapskate I'm with tonight didn't even leave you a tip?" she said holding open the folder for him to see. At first he was surprised, but then he turned and gave me a dirty look. "You were so good tonight, Leonardo," she purred seductively, "I really don't feel right just leaving without giving you... something."

He was now looking down as her hand roamed over his crotch, searching and then... finding. "Would you mind terribly if..." she said quietly. The soft sound of a zipper invaded the dead silence. "...I gave you your tip tonight, Leonardo?" Leonardo was standing there totally dumbfounded, but did manage to slowly shake his head from side to side. She looked him right in the eyes, smiled and licked her lips. "Good!" she said softly.

I sat there in total shock! This conservative, proper business executive colleague of mine, this beautiful middle class wife and mother, was acting like a common whore. At first I was more than a little irritated and, yes, jealous. Here she was giving this Italian waiter the attention that I had fantasized about for years. Lost somewhere in my rationale was the fact that I had done everything in my power to force her into this. Then I realized that somehow, despite my irritation and righteous indignation, I had spawned a raging hard-on!

Tammi now had Leonardo's very healthy cock out of his trousers and was gently stroking it. Then, smiling up at him, she licked up a drop of pre-cum off the tip of his cock and said, "Mmmm... I'm so glad I saved some room for dessert." She then opened wide and took at least half of his large cock deep into her mouth. Leonardo moaned and grabbed onto the chair for support. "Mmmmm..." she purred, looking up at him and slowly taking him out of her mouth, "I hope your dessert has cream filling." Then she took him deep again and wiggled her head drawing and agonizing moan of pleasure from Leonardo. This time his cock came out of her mouth with a very audible slurp. "I'm just a sucker for cream, you know," she said smiling up at him.

That did it! I couldn't take it any more! I unzipped my fly and pull out my cock to relieve the agonizing pressure. Then, I stood up with my cock in my hand to get a better view. Tammi's eyes had glazed over now there was no more repartee. She was now concentrating on serious cock sucking. Her head was bobbing faster now and both were moaning loudly. Finally, this erotic duet neared its finale. Leonardo grabbed the back of her head, stood up on his tiptoes and let loose his torrent of cum into Tammi's eager mouth. I could see her concentrating, trying not to lose any of his rampant seed. Then, with his cock still in her mouth, she groaned loudly, grabbed his trouser pockets and began to wiggle furiously in her seat. When she finally finished cumming I was sure that I would have to go and get her coat so that she could exit the restaurant without embarrassment.

After a moment, she released Leonardo's dwindling manhood and wiped him off carefully with a napkin. Then, smiling up at him, she carefully packed him away and zipped him up. He then seemed to come out of his trance but all he could say was "Grazie, grazie.." In a second, he is gone.

She then carefully took the napkin, folded it to a point and, looking at me with a victorious smile, daintily dabbed the few drops of Leonardo's cum from her lips and chin. Then, she got up and came over to me. Smiling at me, she put one hand around my neck and the other around my cock, and pulled me down for a kiss. Her lips were warm and swollen and our kiss was incredible passionate. As she ground her body against me, I felt the tip of her tongue lightly probing and slipping between my lips. As I open to my long awaited fantasy lover, her hands on my neck and cock close like a vise. Before I could react, Tammi has filled my mouth with Leonardo's cum. This was such an unexpected and nasty surprise that I came instantly... all over the Piazza's fine lace table cloth.

We rode back to the hotel in silence. At the hotel, I offered to take Tammi to her room and she nodded her approval. When we got to her door, she turned and surprised me with a warm smile and put her arms around my waist. "Sean, my dear friend," she began, "this has truly been one of the most exciting and memorable days of my life and I have you to thank for all of it." She reached up and gave me one of the most passionate kisses I have ever experienced. When we finally came up for air, we were both breathing very hard and my burgeoning erection was pressing against Tammi's belly. "Just in case you're wondering," she said softly, "yes, I could feel that all the way down to my tippytoes. And, no."

"No?" I asked.

"No, I'm not going to fuck you, Sean, my dear," she said tenderly, "Tonight or ever, understood?"

"Yes, Ms. Taylor," I said, I understand."

"Oh, Sean," she said tenderly, "one more thing.."

"Yes, Tammi?" I said.

She reached down and grabbed me by the balls causing me considerable pain. "If anyone we know finds out about my little Piazza dare, I will personally cut these off and feed them to a junk yard dog, you hear me?" I tried to answer, but only a groan came out. "I'll take that as a "Yes, Ms. Taylor" she said releasing her death grip. Then she softly kissed my cheek, said, "Goodnight, my friend," and disappeared into her room.