I would like to personally thank the Hip and Knee Doc for all the help he gave me on editing this story and making it flow.
All right, I admit it; I'm a cheat and, a bastard of sorts. I'm unfaithful as the day is long, and about twenty other freaking adjectives, but if nothing else; I'm a man of my word. A little confused? Let me give you a little history so you can see where I'm coming from.
My name is Greg Moore and I'm a born and bred pussy- hound. Ever since I can remember, my dad, Dan, would tell me that a good looking guy with money in his pocket could get all the free pussy he ever wanted; that is, if he played his cards right. He should know, since he's sure had his share; along with two ex-wife's.
My family owns a small construction company in sunny Florida that has been around for about fifty years. All my dad ever wanted to do, was to build the best house he could, party on the weekends, and fuck every available pussy he could find. Along the way, he knocked up two women, hence me and my sister Tammy were born. If he got a girl pregnant, he married her, "You screw up, you've got to pay the piper," he told me.
The second thing he taught me was that when you gave someone your word, you stood by it no matter what the cost; "because a man's word is all he has when it comes right down to it." However, that never stopped him from fucking around, and that's why he has two ex-wife's.
I lost my virginity at fifteen to a woman that worked for my father. When I say woman, she was twenty-five and looking back, I'm sure he was screwing her. The two of us were sorting invoices and getting ready for the tax season, when my dad announced that we had to get the job finished by Saturday morning for the auditor.
"Come on dad, it's going to take us all night," I complained.
"And your point?" he asked. "The sooner you stop complaining the sooner you'll get it done," he told me. "Do you see Sherri complaining? She knows that sometimes you have to go that extra mile to get the job done. The sooner you learn that, the better off you'll be. I'll send over dinner for you two, and Sherri will give you a ride home when you're done. Have fun," he said as he walked out the door.
I complained a bit more and then got my ass in gear and it turned out that; it wasn't as bad as I had thought. We broke for dinner at about 7:00 and were winding it up by about 9:30, when something weird started happening. If I didn't know any better, I'd swear that Sherri was coming on to me. Mind you, I wasn't experienced, but I wasn't naive either; I knew when I was being hit on. It was subtle at first; a little innocent touching and brushing me with her breasts as she leaned over the table to grab an invoice; but it was enough to bring my dick to attention. I'm glad the table was there, because I was rock- hard and making a huge tent in my pants.
I made sure that I was always on the other side of the table to not embarrass myself by letting Sherri see my condition; but I got caught anyway.
"My, my, my," she said; as she looked at the bulge in my pants. "How can you work with that in your way?" she said now rubbing it with her hand. "We'll just have to get rid of it if we're ever going to finish our project." She dropped to her knees, pulled my dick out of my pants; and sucked it down in one motion.
"Oh my god," is all I could say as she worked on me. I would have exploded in twenty seconds if I had not thought about my English paper that was due Wednesday, the ugly troll in my second period class, and the nun I had in grade school. Regardless, I shot off in about thirty seconds.
Sherri's mouth never left my dick as I shot what must have been two gallons down her throat. Well, it felt like two gallons anyway. She just swallowed it all and cleaned me up with her mouth as I tried to get my head around what had just happened. "There, that should make it more comfortable for you," and then she told me; "let's finish this up shall we?" I raced to get everything sorted and packed up into file boxes, not knowing what was next on the agenda for me.
"See, that wasn't so bad" she said out loud. "It's only 10:15 and we're done," she said looking at her watch. "I told your dad that I'd have you home by 12:30, so we still have two hours to kill. Do you have any ideas?" she said unbuttoning her blouse.
The next three hours were something out of a teenager's wet dream. She started off giving me another blowjob, and; "I lasted two minutes this time," which I can say with pride. She then fucked me three times. Sherri showed me how a girl likes to be kissed, how not to paw at a girl's boobs, and how to flick a girl's clit with your tongue to get her off.
I slept in on Saturday morning, as I was completely exhausted. Mom was pissed that I'd stayed out past 1:00 am, but dad said it was a character-building tool, and how right he was. I wasn't sure if he'd set it up with Sherri, but later I heard through the grapevine; that she had gotten an early Christmas bonus for taking care of a personal matter for him.
I worked for my father on weekends and every summer. He started me off at the bottom and I had to work my up through the company. In the course of four years, I had a new car, money in the bank, and a finely chiseled body thanks to my dad. Try carrying 50-pound bundles of shingles up two-story ladders along with 4x8 sheets of roofing plywood, and; you got into shape or you died, one of the two.
My sister had it a lot easier. Tammy went to college and got a degree in accounting. She controlled the purse strings when she took over six years later; and boy, was she tight with the money. I can remember when I told her one- day to ease up a little, and that I needed another nail gun, just for a spare in case one broke.
She looked me straight in the eye and exclaimed; "All right, if you want it that damn bad, you can have it, but I'm deducting it from your pay-check on Friday."
We never got that stinking nail gun, especially not with my money anyway. Life went on.
I wasn't all blue collar though. My dad sent me to college to get a degree in business because as he put it, "You need to know what has to be done, how to do it, and how to be smart enough to instruct someone else on how to do it for you." So I graduated from Florida State and went to work for the family business full- time.
I was still quite a pussy- hound though. I dated and screwed every girl who was decent looking or still breathing. I always did it covered, as I didn't want to end up like dear old dad, and I never got an STD or any other gift from any of my bed partners. I would date a girl until she started to get serious or wanted to take it to the next level, and then I would end it and move on.
However, after a few years it got pretty old. I could still find a multitude of women to take to bed, but they all blended into one another after a while. I tasted white, black, red, and yellow, pussy and in the dark they were all basically the same. I started going out with my buddies in groups, so that I didn't have to be with just one woman. My vendors were always throwing parties and the groups at my local Home Depot were always looking to unwind after work.
That's where I met Gail. She'd had worked at the local Home Depot in building materials when I first met her. She took care of the contractor's accounts and was one tough cookie. She was nice looking, had an average body and knew how to handle herself around blue-collar construction workers.
"Hey Gail," I shouted at her one day. "When are we going out?" I ribbed her.
"Gee Greg, you wouldn't know what to do with a real woman," she replied. "I'm not like one of your china dolls, and you wouldn't last twenty minutes," she said with a laugh and then walked away. The guys gave me a hard time for two days after that exchange.
I got to know Gail pretty well over the next couple of months. I only let her handle my orders, which had its advantages because she was determined to move up in the company. One day I told her that I would give her all the lumber business for my next five houses if she would guarantee that there would be no slip- ups. Beaming; she said, "Give me that chance and we'll prove to you that we can match anyone's price and beat their delivery by at least two days." She got the order.
The material for the first two houses went forward without a hitch; but the third one was a complete disaster. The order was missing items and a lot of the wood looked like seconds. I got on the phone and ripped her apart.
"Send the truck back, and I'll have it back on the job-site tomorrow morning, I promise," she told me. So the truck went back, and true to her word, it hit the site at 7:00 the next morning, and was perfect. I found out later, that she canned two of the employees that had initially pulled the order and off- loaded the truck herself. Three people stayed over and helped Gail pull and load the new order, and she made sure the driver came in an hour early so it would be on the job-site before 7:00.
The next time I saw her at the store, I gave her a thumbs up. I told her that if she ever wanted to leave Home Depot, she'd always have a job waiting for her at my company; and I meant it.
After that, Gail was always a part of our after hours group. However, after a while the group started to dwindle down. At first, there were about eight of us, then there were six, then two more transferred to different stores, which finally left Gail and myself.
Because of my work with Habitat For Humanity, I was invited to their yearly dinner and charity auction. Gail and I had been somewhat going out for about a month. We hit the movies most Saturday nights, and usually met after work for dinner and drinks twice a week; so I asked her if she'd like to go with me. "The dinner is semi-formal," I told her, "and I'll pick you up around 7:00."
"Thank god I decided to lose a few pounds," she told me, "or I'd have never fit into the only dress I've got for such an occasion."
Up to that point, I'd seen Gail in jeans, T-shirts and a few plain blouses, so I didn't really know what to expect. Gail you see isn't a raving beauty. On a scale of 1 to 10, she was about a seven. She's about 5'6" tall, has medium length brown hair, pretty hazel eyes, and her weight, well; your guess was as good as mine.
I left a little early to drive to Gail's apartment because I'd never been there and didn't want to be late. I looked good, if I do say so myself. I was sporting a new haircut, was clean-shaven and was wearing a tux I'd borrowed from my dad; I looked hot. However, when she opened the door, my mouth dropped. If I was hot, she was smoking.
I almost didn't recognize her. She had on a slinky black number that you could barely see the straps that went over her shoulders. The front was low enough so that you could see plenty of cleavage, but the back was cut down to her waist; "Hot damn" was all I could say. In my books, she went from a 7 to at least a 12, if that was possible.
"From the way your tongue is hanging out, I think you approve of the way I look," Gail said with a laugh. "And you don't look half- bad yourself," she told me, "You cleanup pretty well," she said as she pulled me into her apartment.
"It's just that I've never seen you in a dress and ...," I started to say when Gail cut me off.
"You really mean that you never thought that I'd look this good dressed up," she told me. "Do I look like one of your china dolls?" she asked.
"Better, much better," I replied. "Brains and good looks, does it get any better?" I said in trying to recover.
She said, "well, don't get any ideas buster. This body is off limits. Do you read me loud and clear?"
"Yes sir," I joked. "Your carriage awaits, my lady," I said with a deep bow.
"I have a feeling this is going to be one hell of an evening," she said grabbing her purse; it most certainly was one of the best evenings of my life.
Everyone, and I do mean everyone, including my dad, wanted to know who the new girl with me was. No one believed she worked for Home Depot in the construction department.
We had a great time. We ate, danced, and drank up a storm. When the auction started, my dad told me that he wanted to spend at least $4 to - 5,000.00; because it was a good cause and I should buy whatever I wanted. Most of the stuff was donated and I'd either owned it, or couldn't care less about it. I did win a dinner for four, for over New Years Eve at the Ritz Carleton, which included two suites at a cost of $1,250.00, and a complete set of kitchen- ware, including pots and pans for another $750.00, which was; something that I needed for myself. I finally found an item that I really wanted. It was a five-day stay at the Sandals Resort in Jamaica. I had never been out of the country and really wanted to go.
"If I win, will you come with me?" I asked a surprised Gail.
"What do you mean, go with you? I can't afford that," she replied.
"It'll cost you nothing. It's an all- inclusive resort and our company will be buying the tickets," I told her.
"In that case, why not?" she said as I noticed that she was getting excited.
The bidding was hot and heavy for the package. It looked like there were three of us who wanted it, and after three minutes it was down to two of us. I bumped the bid by $500.00 and then another $500.00 before the other guy folded. Gail was screaming, and jumping up and down as everyone congratulated me on my winning bid. It cost me $2,950.00, which was more than the trip was even worth, but I had won.
My dad and his date came by and asked if I planned on using the tickets. "Hell yes," I told him. "And I planned on taking this lovely lady with me," I said motioning to Gail.
"If you change your mind, I'll take them off your hands," dad said with a laugh. "Also, ease up on the booze tonight, since I can't afford you getting a DWI," he said with a concerned look on his face knowing how heavy I'd been hitting it tonight.
"Don't worry Mr. Moore; I'll make sure he doesn't drive drunk," Gail told him. "If I have to, I'll drive him home myself," she assured him.
"Thank you, as my insurance carrier would cancel me if another person on my policy got a DWI," he told Gail. "Well, enjoy the rest of the evening and nice meeting you," he said walking away with his arm candy.
Gail was enjoying herself immensely. She had a thing for Greg, but wasn't about to tell him. "He looks so hot tonight," she thought to herself. "I wish he felt the same way about me as I do about him," but Gail believed that Greg was out of her league.
We danced for the last forty-five minutes of the dinner. I had started to sober up and was getting more than a little friendly with her. If I wasn't holding her hand, I would have my hand on her arm or knee; and what was great, she let me. During the last slow dance, I caressed her entire back and shoulders, and she could feel my hot breath on her cheek as we glided across the floor. She was more than perspiring at the end of that number.
From her perspective, she was so damm hot, that she wanted to rip his clothes off and screw his brains out right there on the dance floor; but she knew that it wasn't going to happen tonight. At least she didn't think it would.
"Gail, I had a great time tonight," I told her. "You're someone I'm comfortable with and feel that I can talk to you about anything," I told her as we were walking to my truck. When we arrived at her apartment, I walked her to the door and then followed a pregnant pause.
"Screw it," Gail thought to herself. She reached up and put a full- lip lock on Greg. "If he's not going to make the first move, damm it, then I will," and she did.
I didn't fight it as we made out for about five minutes at her front door. Still a little apprehensive, and more than a little horny, I told her that I had to go, and that I would call her tomorrow. We kissed once more, with tongue this time, and she walked into her apartment, alone.
"I guess I'm not up to his standards," she said angrily to herself, as she got undressed. "I guess he's still hung up on those delicate china dolls and I'm not good enough for him," she thought and got even angrier. "Screw him, I don't need a spoiled brat sniffing around me," but she did. She really had the hots for Greg, since the first time she had layed eyes on him. She reminded herself that he was out of her league, but she wouldn't have kicked him out of bed tonight if he had been willing.
I drove home with a raging hard on. "Why the hell didn't I just take her to bed tonight, as she was more than willing?" I asked myself out loud. "She looked fantastic tonight and hell, I'd already asked her to go to Jamaica with me, so what was the problem?" I already knew the answer to that question, though; I was used to using women and then discarding them without a second thought, but I really liked Gail, and that was troubling me.
The following morning, my dad asked me about Gail and what my intentions were; I lied. "She's a worker- bee dad, but I'd sure like to bed the bitch," I said with a fake smile. "Maybe we can double- date on New Year's Eve for dinner?" I asked my dad. "We'll have two adjoining suites, so at least we won't have to drive home in all that craziness."
Dan knew his son better than Greg knew himself and knew that he was giving him a line. "Then it's all set," he told his son. "But, I'm going to see if I can get another room, so Tammy and her boyfriend can join us, and then it'll be like a family outing," he told me.
For the next two days Greg fought with himself. He liked Gail that much he knew for sure; but he also didn't want to settle down just yet. By Monday he'd decided to just go with the flow and see what happen; "no commitments," he told himself.
Gail was pissed that the evening didn't end the way she wanted it to. "I wonder if he even remembers asking me to go to Jamaica with him," she asked herself. "He never called the next day like he said he would, so that probably means I didn't live up to his expectations," she thought as she was getting herself even more worked up on Monday morning. "Screw him," she said to herself as she started reviewing the day's deliveries.
Gail never saw Greg walking up to the order desk, but everyone else did. Everyone was trying to stay out of her way, because she could be a miserable bitch when she got her dander up.
"Morning Gail, and how's my favorite girl today?" I opened with. Gail shot him a look that could have frozen water at thirty paces. "Looks like someone got up on the wrong side of the bed this morning," I told her trying to make light of her mood. "Ok, I screwed up and forgot to call you, I'm sorry, so shoot me," I said with a big smile on my face with my arms out stretched.
"Greg, what do you want?" she replied. "I've got a ton of work today and two sorry assholes called in sick on me."
"Look, why don't we talk over dinner tonight? I'll pick you up at 7:00 and we catch up then," I told her.
"8:00 please make it 8:00 tonight; I don't get off until 7:00 and I'll need to go home and take a shower," she replied. "Let's make it somewhere simple and casual, because I don't want to get all dressed up tonight."
"Got it; 8:00, something casual, See you then," I said walking away.
"Gail's got a boy friend, Gail's got a boy friend," one of her workers sang to her.
"Listen pea brains; if you don't want me to work you to death, I think I'd shut the hell up right now. "Do I make myself clear?" she said in a tone that dripped with sarcasm.
Dinner started quietly until Greg broke the ice. "If you're available, I'd like to know if you want to have dinner with me on New Year's Eve? I know it's short notice with it being only three weeks away, but if you don't have any plans, I'd like you to come. Anyway; we still have to pick a date for our vacation," I told her. "We're shut down between Christmas and New Year's because it's so slow, or we could go right before, or right after the holidays. Do you have any vacation time available?" I asked.