Jerking off Lucky the Golf Pro Ch. 01

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He takes her to dinner in Hawaii.
4.8k words
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Part 1 of the 12 part series

Updated 10/11/2022
Created 03/31/2005
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My name is Diana and I'm a 23-year-old white woman now married to a famous black semi-pro golfer. His friends call him Lucky and he is. The first time I met him was a club, a country club who had a large number of pro golfers and hosts one of the best tournaments in the world annually. I was standing there drinking a glass of wine when the owner of the club introduced Lucky to me. He was very charming in a boyish sort of way. I could tell he had not known many white women and most likely played golf more than he dated.

We chatted for a little while and he seemed nice enough but still a little unsure of himself. Well his golfing wasn't and he came in second place being one of the youngest players to ever finished in the top three money paying positions.

At the party that evening I saw him again and we chatted for a longer period of time. He was very happy with the outcome of the tournament and told me he would win it all next year and move up to pro. I didn't argue since I watched him play and he was good. His part of the prize money for second place was $42,000. "Not bad for 3 days work doing something I love is it Diana", he said to me. He was now a golfing pro and on the circuit.

I told him I was happy for him and felt he would become a huge player one-day if he worked hard at it. That's when he asked me if I would like to dance and I told him yes.

We danced a few times that evening and I was sure people were talking about us. You know the young pretty white woman and the black man together, what's this country coming too. Then during one of the dances he asked me if I felt uncomfortable dancing with him?

I told him, "Why because you're black? No Lucky it's doesn't both me, but we do make a different type of couple than the usual country club pair."

We both laughed at that remark and as the evening came to a close, he asked me if I would go to dinner with him sometime? I said, "Are you asking me out on a date, date?"

He said, "Yes, I guess I am. So will you? How about Friday night?"

I didn't know what to say so I said, "Yes. Friday is good.6:30 PM?"

At dinner we talked for over two hours about my life and his golf carrier. After dinner we sat on a bench near the club and talked more until the club started to close. Lucky pulled up in front of my place and thanked me for a very nice evening. He sat there for a moment and then said, 'Diana I want to ask you something but I think you will think I'm nuts."

I told him he could ask me anything. Finally he said, 'Would you go out with me again?"

I said, "Sure tonight was fun. When would you like to go out again?"

He said, "Well.....there's another tournament next month and I was wondered if you would like to go with me. It's in Hawaii? And then we could have dinner over there?"

I was stunned and shocked I had known him for less than two weeks now, and he was inviting me to Hawaii!! But I didn't show it. I studdered and asked, "Hawaii for dinner and what else Lucky? And, for how long?"

He said, "We would fly out together on Wednesday and return the following Wednesday. And, then he said, "We would most likely only see each other for a few hours each day since I had to practice. But we would have all of the evenings to ourselves. Think about it Diana and when you decide call me. OK? We seem to get along well and I enjoy your company."

I had a million questions and he could se it in my face and eyes. He also knew I was wondering about the commitment. So he said, "Look! You can do anything you wanted while I'm playing golf. You can watch me or go shop or sit in the sun. I don't care as long as you will be my date in the evening. That is, when we will go some place involving the golf organization."

He continued saying that it would involve me wearing cocktail dresses and staying and walking around with him as his date. He just wanted me to be sure I was ready for the looks and whispers of him and I together. He would book two adjoining rooms and expected nothing more than I was will to give. He made sure I know he would place no pressure on me to sleep with him. In fact, the evenings would be over fairly early since he was in training and serious about being the best damn golfer in the world.

I said, "God!! Lucky that sounds very nice. Hawaii! I don't have to think about it. But I don't know if I can swing the money."

He said, "Money! No you don't understand, the trip is on me, all of it, the room, plane fare, any and all drinks, all the food, shopping anything you want, within reason Diana."

I said to myself, "Damn how could a girl turn that down?"

I smiled and told him, "OK! You got a date Lucky by the way what the hell is your real name?"

He laughed and said, "I won't tell you?"

I said, "What? Why not?"

He laughed and started to look darker, like he was blushing. Then he said, "It's Simon. Now do you see why everyone calls me Lucky!"

I laughed kissed him once and went inside as he drove away. A week later off we flew to Hawaii and a week of him playing golf and me enjoying the sun and everything that comes with being his date. And he was true to his word. I did whatever I wanted during the day. That involved mostly sunning myself on the beautiful beach, or going to the sauna or spa almost everyday to have a beauty treatment. Or, I was having a cool frozen drink while the sun beat down tanning my skin or a massage for an hour daily.

We dinned at some of the best places and met some great people in golf and all of this was on Lucky. He must have spent $5,000 on me that week not including my room or the food. And he enjoyed it, telling me everyday, "Do something today Diana while I'm gone. You don't have to worry about not spending my money if I didn't want you to, I wouldn't have invited you!"

And, so I didn't pay a cent while we were there. At night he was the perfect gentleman and didn't ask for much except having me by his side and letting him put his arm around me as we did the touring circuit with the other golfers and wives or girlfriends. When we went back to our rooms he kissed me goodnight after the third evening and it was I who kissed him.

During the day, I got to know Sandy one of the other women there with a golfer name Todd. She and I became very friendly. So friendly that one-day about 4 days into this wonderful vacation, she ask me point blank, "So Diana what's it like fucking a black man? Is Lucky big down there like the rumors all say?"

I blushed and if it weren't for the deep dark tan I now had I think she would have said something about it. I said, "Well to be very honest Sandy I don't know. We....we never had sex.."

She looked at me like I was either nuts or not telling her the truth. Then she said, "You're full of it! A black man takes you to Hawaii and let's you run wild on his money and he hasn't fucked you yet! Bullshit! Come on stop fucking around with me. What's he like down there?"

I said, "Honest to God. If it's any of your business Sandy, which it's not, Lucky and I are just good friends and enjoy each other's company. He likes me with him when he's not playing golf but we haven't had sex and that's the truth."

She kept pushing and prying and finally I took my towel and told her not to talk with me again. I left and went from the beach to the pool. About an hour later Lucky came down looking for me and saw I was alone. He asked about Sandy and I told him we had a fight. He wanted to know about what and I told him I would tell him later in the room. He stood there and said he was going for a rub down and would see me back in the room in about an hour.

I went back to the room showered and put a robe on and waited until later to fix myself up for the evening I sat out on the balcony in only my robe and watched the surfers and swimmers. Oceanfront in Hawaii is the only way to stay there. Finally about an hour later Lucky came back to the room. He went into his room and knocked before coming into my part. He came out on the balcony with me and handed me a special drink the one I always liked so much. It was called a Blue Whale. He sat down and said, "So what did Sandy say to piss you off?"

I told him as gentle as I could and then said, "It's just no one's business what we do or don't do Lucky."

H smiled and said, 'Right. It's not that I wouldn't want to Diana. I mean you are extremely beautiful. It's just that the time and place didn't seem right and well you never seem to be that interested or pushed it, so I just figured you weren't into that sort of thing with me. I told you I wouldn't press you. But as beautiful as you are, I have to say I would like to take it to another level if you want too."

I could tell by the way he talked and acted, he was more nervous than I was. I thanked him for going slow and being gentlemen. I also told him, while I wasn't a virgin, I didn't just go to bed with a man regardless of the amount of only he sent on me. If that was what he was thinking when he invited me here, well I would had home as soon as I could.

He told me that wasn't the reason and apologized to me! I told him I was sorry for blowing p like that and blamed it on Sandy again. He left my room and we dressed for cocktails and dinner with the group. I just stayed out of Sandy's way and sat at a different table. We mingled as usual and finally around 10:00PM we headed back to our rooms. He stopped me before I went into my room and said, "Diana I would like to kiss you goodnight."

I moved into him and he held me as our lips met and we had a first real passionate kiss. We usually kissed goodnight and tonight was just like usual except Lucky held me tighter than normal and the kiss was longer than usual. Finally I said, "Well Lucky thank you for another very nice evening again! This has been so much fun and enjoyable, I wish it could just keep going on and on."

He said, "After tomorrow we can spend a few extra days here if you would like Diana. I don't have to be back until Saturday. What do you think?"

I smiled and he knew my answer. He kissed me again and I moved into his arms circling his neck with my arms. This time I pressed my body harder to his. And he responded by slowly moving his hand towards my breasts. But he stopped as his palms were pressing against the sides of both of my breasts. I looked at him and then moved as I took his hands and placed them over my breasts. He looked at me with those innocent eyes and I said, "Come in my room with me Lucky and let's talk a little while."

We went into my bedroom and I told him, "Look Lucky I like you a lot and really enjoy our time together but I'm not ready to have sex with you. You are not going to fuck me understand?"

He told me he understood and said something about the difference between us. I said, "Well yes, the color is one thing. It seems to be a problem for both sides' black and white. But that's not the only reason. I have only had sex with two guys before. One was in high school after my senior prom and I lost my virginity and it was terrible. The second time was at a frat party in college and I was pretty drunk at the time. But that time was much better because the guy actually cared for me and I cared for him. The relationship and sex lasted about 2 years and ended about 8 months ago. I haven't been with anyone since then. I want you to know and understand I'm not the type of woman who fucks every man she goes out with. Even if he brings her to Hawaii for a week."

Lucky was completely different with me than when he was on the course. When he was out there hitting the ball he was a lion. All he did was attack, attack, and attack. But, here with me he was meek and mild and almost submissive. He let me rule the relationship and I did. Nothing evil or nasty, I just told him what we would and wouldn't do. He accepted it completely like a boy does with his mother.

I smiled and so did he, Then he said, "I knew that Diana that's why I enjoy your company. You're not a groupie or gold diggers you're a breath of fresh air from the usual women on the circuit, like for instance Sandy. She is the typical whore who comes to these events. I'm sure almost everyone who sees us together thinks I'm screwing you every night! It's just what seems to be the way things are these days. Beautiful women try to get some of the money from the players. But hell you're so damn different, I have to almost make you spend my money."

I smiled and asked; "Do you think I'm beautiful Lucky?"

He said, "God yes Diana. You are beautiful, and nice and fun to be with. I really enjoy your company."

He smiled and I told him, "I wouldn't have sex with you Lucky, or anyone else for that matter. Not, unless we were married or had been together for a long time. I'm not ready for that type of relationship again right now and neither are you. But if I was truly in love, I might do it if the time, place, person and mood were all right."

I told him, "It's very complicated with me. But then I told him, "But Lucky, that doesn't mean I wouldn't like to make out with you sometime."

He smiled at that and said, "OK. Fair enough. Only as far as you're willing to go Diana, that's what I told you and that's what I meant."

I said, "I am wondering about you and what Sandy asked me."

He looked like he didn't understand and said, "What was that?"

I blushed and he smiled. He said, "It's OK. Ask me anything."

So I took a deep breath and asked him if he had ever been with a woman before. He said he had a few times but they were all hookers like Sandy.

So I decide to help him out tonight. I wasn't going to fuck him but I would jerk him off. I was also wondering about his equipment. According to Sandy most black guys were big, 6 to 9 inches, some even more. But she was a whore and never told the truth.

So I decide I would give him some enjoyment off the course. I slowly started to take off his clothes as he stood there watching me. I said, "Don't say anything Simon. Let me do all the talking. OK?"

He said, "OK Diana. Just remember as far as you feel like you want to go."

Once I had him down to just his shorts, I smiled as I saw the front pushing out against the material of his underwear. I started to undo my blouse. When it fell to the floor I looked at my bra and saw him lick his lips. I said, "You do it. Take it off for me Lucky."

His smiled was huge and those white teeth looked even bigger against his black skin. As he worked the front clasp, I had to help him. I stood there with about 3 feet between us, and my hands on each of his hips. Finally, he got it unhooked and it fell to the floor off my arms. I was topless. I stood there watching him looking at my un-taned breasts with the nipples getting harder and harder. I said, "What do you think? To small or to big?"

He sighed and said, "They are the most beautiful breasts I have ever seen."

I said, "Well I love your words but how many have you actually seen close up that were white Lucky?"

He didn't answer me but instead reached for them and I let him. As he squeezed then I knew he was very new to this. So, I started to instruct him on what a woman likes when having her breasts stimulated not mauled. He worked the nipples and made them harder and longer. I placed my hand on the back of his head and said, "Suck them gently Lucky! Suck each one, not hard but gentle. Use your tongue too. Yes that's right babe! Just like that! Yes that's very nice. Umm Lucky that's feel so good!"

He was a good listener and followed my directions completely. I held his head against my breasts as he played and sucked then for over a half an hour. He didn't try to go any further. I smiled wondering if this was his first time touching and sucking on a white tit?

I let him play with my breasts and then felt his erection touching my thigh. I looked down and knew he was super hard. I told him, "Sit down here with me. We're not going to have intercourse Lucky. But I will give you some release."

I was very excited about seeing my first black cock. I sat next to him and put my hand on his bulging lump in his shorts. To my surprise, it wasn't super hard and it felt like it was maybe 6-inches long. I smiled at him as he watched my hand wiggle into the opening in the front of his shorts. He opened his legs and I heard him take a deep breath as my fingers circled his cock. I moved the shaft out into the like of the room and saw it for the first time. It was very average, maybe a little below average. I smiled at him and said to myself, "What the hell did I know, I wasn't that experienced with black cocks, or any color cock for that matter."

I realized that Lucky wasn't as large as the two white males I had fucked. In fact Lucky wasn't as big as any of the other males I have been with in my life. Now, there weren't that many guys, maybe 5 or 7 in total. But a girl remembers the cocks of those guys she had seen and been with. Lucky wasn't that lucky when it came to cock size. Sandy was wrong as usual. All black men are not , I repeat NOT hung!

This back man wasn't hung . Lucky wasn't very large at all. In fact he was somewhat small. As my hand held it, only about half of the cock head was still sticking out the top of my fist. Lucky was just over 5 inches long. I smiled at him and slowly began to jerk him off. I said, "You have a nice cock Lucky it's so dark and big."

I wasn't telling him the truth but it was throbbing in my hand and he was really enjoying what I was doing to him. As I worked his cock, I was also convincing myself I owned him this for the good time I was having. I mean after all, most of the golfers were getting laid every night by the whores that they took with them. After all the money he spent on me this week, I figured I could at least jerk him off and make him cum. He moaned and I said, "Lay back baby and enjoy this!"

He said, No Diana I want to look at your body as you play with me. May I touch your legs too?"

No Lucky just lay there and let me do this for you."

He didn't ask again. So, I opened my legs for him and then sat cross leg in front of him. He looked down between my legs and saw the little wet spot in the center of my panties. He moaned again as I moved my hand faster now up and down his shaft. I pushed down at the base of his cock and stretched the skin around the head as tight as it could get without hurting him. This made his cock as long and hard as it could get. As I held him at the base I jerked him with two fingers and my thumb just under the swollen cock head. He told me how good it felt and I smiled at him. I knew he could see the small bulge in my panties at the center of my sex. I have a nice fat pussy and as I continued to jerk him off it got puffier.

Finally I said, "Look at me Simon. Touch my breasts again."

He did and I felt his black cock harden and thicken in my hands. I knew he was going to cum. As I jerk him off faster and faster now I smiled into his eyes. They looked as if they were in a dream. He began to hump up and down now fucking my hand as I made love to his cock. I took my other hand and covered the head gently. He could feel the direct stimulation of his mushroom shaped cock head and he arched his hips up off the sofa. He moaned loudly and began to cum pumping it into my hand that was covering the head of his dick. I squeezed and jerked his shaft milking him. I continued to pump and squeezed the hard shaft until he was completely finished. He lifting his hips and ass up off the sofa one last time and moaned and grunted as he finished his orgasm and a few drops of cum ran down his shaft between my fingers. As his hips came down again on to the sofa, I kissed him and asked, "So did you enjoy that Simon?"

He moaned and reached for me. I let him hold me and lick and squeeze my breasts until his cock was completely soft. Then I rubbed his cum on my breasts and pulled his black face between my tits and covered it with his cum. He pulled back and I said, "Suck them!"

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