Disclaimer: Do not continue reading if you are not 18 years old or you are offended by portrayals of male to male sex or the laws in your state or county forbid this type of material.
Copyright 2004 by the author. Do not reproduce or distribute this story without the author's permission.
Names, characters, locations and incidents are fictional. Any resemblance to actual events or locales, or persons, living or dead, is entirely coincidental.
The Prize
Jerry was a great Daddy. I loved serving him. I met him when I was just 19. He was 31. He took me under his wing and showed me the ropes. He took me into his home and helped me find a job. He took me out to clubs and we danced and had a great time. He taught me to play tennis, to judge fine wine, and to read poetry. He was gentle, caring, sophisticated and loving. And the sex, well! I loved nothing better than kneeling down and taking his long uncut dick in my mouth and sucking him off under it was rock hard. Then I'd turn around and pull my cheeks apart and he'd slip that thing into my ass, slowly but firmly, until his balls were banging on my ass. He was perfect.
I knew he had had two other `sons' before me. I figured he had grown tired of them. I determined to do all I could so that he wouldn't grow tired of me. I served him dutifully, keeping his home neat, getting his meals ready, cleaning his clothes. And I tried to keep our sex exciting and fresh.
So you can imagine how devastated I was when he told me he had been put in charge of operations in the Philippines and he was moving to Manila. He said there would be no work for me there, that it was better for me to stay in Boston and find someone else. He helped me get an apartment I could afford. I kissed him one last time when I saw his plane off, and thought my life had ended. I was 22.
For most of the first year, I just moped around my flat. I went to a few bars, picked up a few guys my own age, but it just wasn't the same. I kept thinking about Jerry. He no doubt had a little Filipino boy already pressing his clothes and sucking his dick. I was jealous of this phantom boy. I was angry at Jerry for leaving me. I was frustrated with myself. I wanted a daddy real bad. Someone to serve and look up to. Someone to treat me like the little boy I wanted to be. But frankly, I was scared. I didn't want to get saddled with an abusive man. I wanted someone kind and gentle, someone who could make my heart tremble and my asshole twitch. Someone like Jerry.
Then one Sunday, I got a call. Jerry was back in town for two weeks on business at the home office. When I heard his voice, I melted. I was his little boy again, and I was so happy to know he was back, even briefly. When he rang my doorbell later that night, I had soft music playing, candles burning, and a bottle of wine in the cooler. I was dressed in a satin robe which swished nicely as I did my little dance for him. I slowly unbuttoned his shirt and suckled his nipples. Then I knelt down and unbuckled his belt, opened his fly and went to town on his cock. In a short time, he pulled me up by my shoulders, carried me in his arms to my bed and fucked the daylights out of my long neglected asshole.
Over breakfast the next morning, he asked me why I was living by myself. I explained what I wanted - needed - and why I was wary. He told me to meet him after work at a bar we used to frequent a lot. That afternoon, we sat at a table near the entrance and he filled me in on life in Manila. I got the sense that he did have himself a new boy, but he didn't volunteer any information and I didn't ask. As we sat, he whispered to me to check out the bar stools. I glanced and there was an older gentleman sitting there watching us. He smiled at me. "He's checking you out, Son. If I wasn't here, he'd be hitting on you." I blushed.
"No, I mean it. A lot of guys my age are looking for a son just like you. They'd love to get in your pants if you gave them a chance. And why the fuck not! You have a great little body, tight little bubble butt, sweet boyish face. You're a real prize." Suddenly, Jerry stopped talking. I recognized the symptom. He had gotten an idea and he was digesting it. "OK, that's it. Before I go back to Manila, I'm going to make sure you're set up with a new Daddy. How do you like that?"
I was speechless. Of course, I wanted him, but we both knew that was impossible. So he was willing to help me find a replacement. He was the best. "C'mon let's go home," he ordered.
When we got to my apartment, he had me take off my shirt and then he snapped several digital pictures of me. He downloaded them on to my computer and he picked one that showed me smiling that included my bare shoulders, down to my tits.
Then Jerry set up a document. In the center he placed my picture. Above in 48 point letters he wrote DADDY CONTEST. Below my picture, he wrote The Prize. Then he added the details:
Applicants must be between the ages of 30 and 45, in good physical health, good looking, with sophisticated tastes and a kindly paternal nature. Applicants will participate in four competitions over seven days. The winner must be ready to take possession of the prize immediately after the last competition.
The prize is in excellent health, 22 years young, 5'7", 175#, 7" cut, tight hole, clean shaven over all, employed, experienced, and comes with a very good recommendation.
Applicants must apply by midnight Friday.
He then added my phone number, and ran off a dozen copies. "Tomorrow, right after you get off work, take these around to our favorite bars. Then hurry home, I need you to stay at the phone. I'll get here as soon as possible. Now, c'mon, let's have some hot sex."
I was so excited the next day, I could hardly keep my mind on my work. It was Tuesday. The entries had to be submitted in only three days. After work I sped around to the different bars, as well as two bookstores and the bath house, posting the contest flyer on all the bulletin boards. When I got home, sure enough, there were already three messages on my machine and the phone was ringing again. I wrote down all the names and phone numbers and tried to glean a little information, confirming that they at least met the age requirement. When Jerry got there, we began setting up a chart for Saturday. He had reserved the board room at his company's main office. We assigned each applicant a half hour time slot for an interview. By now, we had seven applicants. I called each one back and gave them their time slot, and the address. On Thursday, six more called, and two more on Friday. I think by then, most of the posters had been torn down by contestants who wanted to limit the competition. But from that pool of fifteen, we were confident that we would have a winner.
On Saturday, we drove down to Jerry's office. When I walked in, my jaw dropped. Jerry had taken the rest of the digital pictures from Monday and had them enlarged to poster size. They were hung all around the room. "It's important for the entrants to focus on the prize," he explained. He had also checked that the bar was well stocked with both expensive and lesser brands. "We'll see how well versed they are."
The first appointment arrived five minutes early. "Punctuality is a good sign," Jerry said, "It shows he's serious." After Jerry ushered Bob in, he put a sign on the door, Please be seated. We will call you. "If the next contestant comes early, I don't want him interrupting us."
I began to question the first contestant: Had he ever had a live-in son? What would he do with me? What kinds of sexual play did he like? Jerry offered Bob a choice of wines, and asked him what shows he had seen recently. Had he traveled? What books did he read? The grilling continued for about twenty minutes. Then we asked him to step out while Jerry and I checked our notes and conferred. Bob was just about Jerry's age, with salt and pepper hair. He had his own import business. He had never had a son before, but was tired of one night stands and was ready to settle down. We decided to let Bob continue to round two. We opened the door and told him to meet me at 9 that night at a restaurant downtown.
Each contestant was handled this way. Some were eliminated: they were late, or they were crude, or they were obviously lying. Some had no experience with sons. Some were already Daddies; I was not going to be part of someone's stable. Some did not want a live-in boy. Some were poorly dressed, illiterate, or devoid of taste. Some were disappointed that they couldn't have sex with me then and there. One guy came waltzing in with his cock hanging out waggling back and forth. Then there were a few guys that I just didn't feel any chemistry for. A few of the contestants asked a lot of questions themselves, finding out from Jerry what kind of son I was. I thought this was a good sign, showing that they were both confident of themselves and cautious. Jerry and I agreed on four finalists who met our criteria. I was to have a date with each one, one that night. One Sunday afternoon, one Sunday night, and one on Tuesday (he said he couldn't make it Monday).
It was a long day, even taking a hour out for lunch, we weren't finished with the last interview until near six. Then we had to take down the posters and get ourselves home. I had to be ready for my first date. At 9, I arrived by cab at the restaurant. Bob was there already, sitting at the bar. He offered me a drink and suggested a fine burgundy. When our table was ready, he brought me over, and even held my chair for me. He ordered for us both. Bob's tastes were impeccable. After dessert, he pulled out a small gift box. I opened it and saw a lovely 24k tie clip. I thanked him and gave him a kiss on his cheek. Outside the restaurant, his limo was waiting for us. As we drove back to my place, we cuddled in the back seat, kissed and petted. I felt his cock under his pants and he felt mine. But that's as far as we went. I told him to come to my place on Friday at 7 for an evening at home, and the winner would be announced then. Jerry met the limo at the curb, so there would be no question of Bob coming inside that night.
Bob's hand on my cock had stirred good feelings and so upstairs, I lost no time getting into a 69 with Jerry. After he plowed my hole missionary style, we discussed Bob's good points and bad. Jerry examined the tie clip carefully.
On Sunday afternoon, Philippe took me to a Degas exhibit at the museum. Philippe had grown up in France. He had had two other boys already, one while he was still a young man in Paris, and one here in Boston. He was about forty. He said he loved to spoil his boys and before we left the exhibit, he bought me an art book from the gift shop. He drove his own Peugeot so we couldn't cuddle, but in front of my apartment, he planted his lips on mine and lingered there until Jerry tapped on the window. I told Phil to come back on Friday at 7.
Jerry and I only had time for a quick bj before I had to shower and get ready for my date with Bruce. At 45, Bruce was the oldest of the finalists. I had recognized him as the man who was checking me out at the bar last Monday. Bruce had never been a daddy, but as a young man, he had been a `son.' He said he was so grateful for what his daddy had taught him, that now he wanted to pass on the favor to someone else. After a couple beers, he took me to the beach in his Land Rover. He had packed a fantastic picnic, which we ate leisurely in the dunes. I nearly devoured a whole can of Russian caviar by myself. Then Bruce suggested a skinny dip. I said, "Hell, why not," and quickly doffed my clothes. I was quick but Bruce was quicker and beat me to the water. It was freezing cold but Bruce held me tight in the surf like a father and it felt good. When I told Jerry about it later, he was surprised at Bruce's daring move but nodded approvingly. It seemed a more original tactic than the gifts from Bob and Philippe.
I felt like I had been on a whirlwind, but on Monday night, without a date, I could rest at home with Jerry. I pulled up the contest flyer on the computer screen. I thought about the sentence: Applicants will participate in four competitions. "Jerry, the interview was a competition, the date is another, and the last competition I know will be the showdown at 7 on Friday. But you wrote four competitions."
"That's right, Son. And the next one is extremely important, but none of the finalists know about it yet. It will take place on Wednesday and Thursday." A mystery. I was excited.
On Tuesday night, Josh met me in the theater district. He took a cab. Josh was just 30. He had been in a LTR for ten years with his best friend from school. But they had grown their different ways. His friend still wanted to do the club scene, get stoned, and fool around like they did in college, but Josh wanted to take on a more mature role in life. He felt he was ready to accept the responsibility of fatherhood. After talking briefly at a small cafe, he produced two tickets to La Boheme. It was a glorious production. Josh hummed along with the music, seeming to know the entire score. I judged he sang baritone. After the final curtain, he pulled out two tickets for La Traviata two weeks later. "I'd like to take you, Son, even if I'm not the winner." I smiled and said I'd have to get my Daddy's permission. We both laughed. He told me he was looking forward to Friday. That he felt sure he had a good chance.
Jerry picked me up after work on Wednesday in a rental car. We drove to an expensive suburb north of the city. He pulled into a driveway in a very exclusive neighborhood, and stopped the car. I was about to ask Jerry whose house this was, but as we got out of the car, I saw the Peugeot in the driveway. "Philippe."
"Yes, Philippe, and he has no idea we're coming."
"This is the surprise competition?"
"Yep, I think it's important to check out where you might be living."
Philippe opened the door for us and looked surprised but pleased to see us. "Does this mean I won?"
"You'll find out at the party Friday night. Show the boy where he's going to sleep."
Philippe took us upstairs and showed me the room that would be mine. Large and comfortable with a balcony and a great view of the pool. I figured his last boy must have used this room, but Philippe had emptied the closet for me. When we went back downstairs, Jerry went into the kitchen without asking. I felt we were intruding. I didn't want to spy on my own (possible) Daddy. But Jerry felt no such compunctions. When he went back to Manila, he wanted the assurance that he had left me in a good situation. Jerry opened the refrigerator and the cupboards. "Looks like you could probably rustle up a fair meal here, Son." I nodded.
We thanked Philippe for his hospitality and headed back to the car. We drove to the shorefront and found Bruce's home. I should have guessed Bruce lived on the water. This time my room' was an alcove attached to Bruce's room. "I never had a boy live here, but this is kind of like the arrangement I had when I had a daddy," he explained. In the kitchen cupboard, Jerry discovered six cans of Russian caviar. "I figured I better stock up cause I know how much you like that stuff, Son." We laughed. If nothing else, Bruce was certainly confident.
On Thursday we drove to a high rise downtown where Bob had a co-op apartment. When Jerry asked him about my bedroom, Bob frowned and showed us his own huge king sized bed. "I wouldn't think of making my son sleep all by himself. He will share my bed, just as he will share my table and everything else I have." Bob was really a very sweet old man.
Finally, we went to Josh's apartment. The building had a doorman who had to call up before he let us in. When we got to Josh's door, we heard quite a commotion inside. When Josh opened up, we realized a party was going on. Jerry apologized "I'm sorry, we came at a bad time."
"Nonsense," said Josh. "These are a few of my friends. The boy might as well meet them now. I was planning to show him off next week anyway!" I blushed. "Friends, this is the lad I was telling you about, the one who had such an appreciation for La Boheme." I smiled. Several men shook my hand. Josh seemed positive he would win the contest, even exposing his vulnerability in front of his friends. They did seem like awfully nice guys.
Jerry began to look around. This home was more modest than the others, but very tastefully decorated. There were many playbills on the coffee table. Josh took my hand. "Come, Son, let me show you your room." He led me down the hall to what was probably his boy friend's room. Then he pointed across the hall to his room. "Of course, you can visit me any time. I sure plan on visiting you a lot." Josh's friends laughed.
"I'll see you tomorrow at 5, Josh," I said as we were leaving. "You bet. I'll be there bright eyed and bushy tailed."
I left work early on Friday and Jerry's schedule was light, his last work day before flying back to Manila. So we had time to prepare for the party. Candles, balloons, streamers, music, really festive. And good food and wine. I was in the shower when the four guests arrived. Jerry greeted them and they settled down for some snacks and some wary conversation. They probably didn't feel much like talking to each other, but they were determined to prove themselves civil. None of them had seen the competition before, except that last Saturday Josh had passed Philippe in the waiting room.
I got myself into a comfortable sexy little outfit while I heard Jerry making a little speech:
This boy is very special to me. He has given me love, a great deal of comfort, and tremendous satisfaction. It is important to me to know I will be leaving him in good hands. You have all proven yourselves worthy competitors, knowledgeable, wise, refined. Each of your homes is a place where he could feel comfortable and welcome. So as of now, none of you have been eliminated.
But now we want to see if there is a special sexual bond between the boy and one special man here, a chemistry, an attraction. So that is what tonight is all about.
Jerry hit the play button on the CD player and I came out and performed my little dance for all these finalists. They stood around me, as I teased with them, slowly dropping my shirt off one shoulder, letting my shoes come off. Bruce removed his tie. Bob unbuttoned his shirt. By the time I was down to just my g string, all four men had begun to loosen up. Philippe, in typical French fashion, copped himself a feel of my package. Josh was the first one to get his cock out of his pants. When I knelt down and took it in my mouth, the other three lost no time in getting theirs out. As I sucked each cock in turn, I helped the man remove his pants and shirt until they were all naked. Then I handed Jerry my g string. He smiled. He knew something good was going to come out of this night. He threw a handful of condoms on the coffee table and then sat back to stroke himself as he watched the orgy.
I was still kneeling, sucking on Bruce when I felt something on my ass. Bob had gotten down on the floor and was licking my crack. Then Philippe knelt down and lovingly kissed my ear. I released Bruce and started on Josh's cock. Bruce got down and joined the writhing masses on the floor until he was sucking away on my cock. Bob grabbed one of the Trojans and rolled it on to his cock, and then whispered into my ear that he was going to be the first to fuck my ass that night. I nodded and assumed the doggy position. Bob plowed into my tight little bubble butt as Josh continued to fuck my face. "That's it, Bob," kidded Bruce "you get his hole ready for my big cock." After Bob pulled back and sprayed his jizz all over my back, Bruce laid me down on the table and fucked me missionary. The others jerked off over my face, making sure I got a good view of their unforgettable equipment. After Bruce cummed, Josh took my place on the table and somehow convinced Bob and Bruce to hold me by my shoulders and knees and lower me down on his erect gloved cock. Finally Philippe was the most acrobatic of them all, standing up and holding me against his chest , my legs wrapped around his waist so he could french kiss me and fuck me at the same time. Each had now fucked me once, but they were all going to fuck me again several times each before the night was over. We used every conceivable position, on every conceivable piece of furniture. Jerry kept bringing out more condoms. At one time, Bob and Josh managed to double fuck my asshole, which had been well stretched by then. In all the excitement, Bruce must have recalled the days when he himself was a son, for he allowed Josh to fuck his ass. At that point, Jerry too couldn't stay on the sidelines any longer and began fucking Philippe. I didn't mind. It kept everyone occupied while they were waiting their turn at my asshole.
After a couple of hours, there was jizz all over my body and most of my furniture. My hungry asshole was sore but quite well fed. My four suitors were resting, just jerking themselves, me , Jerry and each other to see if any of the spigots still had some juice left. The answer seemed to be negative.
I stood up, walked into the bathroom, splashed my face with some water and refreshed myself. Than I came out and stood in front of them. "Well, men. You were all wonderful. I almost want to make you all my daddies, but that cannot be. You played this game fairly and with great spirit. But only one of you can win the prize. I think Jerry will agree with me, that the one who is the perfect Daddy for me, the one who will take me home, the one I will serve dutifully and faithfully, just as I served Jerry, that one is....