Fbailey story number 350
Teenage Poker Winnings
With all of the poker available on television, in the movies, and on the Internet it wasn’t long before I started a weekly poker game. I became pretty popular with the other guys. You see my parents are never home on a Friday night and I have the whole house to myself. That’s because my sister is usually out getting screwed.
For a fifteen-year-old I was considered one of the ‘in crowd’ at school. I had quite a list of kids that wanted to come to my poker game on Friday nights. I broke them down into the beginner cheapskates, the fairly good players, and the guys with good-looking sisters. You see I had become a little more daring and I wanted some extra incentive so I set up a special poker game where the winner gets the loser’s sisters for the night and the next day. It would be a twenty-four hour celebration. It was definitely the game of the year and there was a hundred dollars buy in. One lucky winner would be five hundred dollars richer and have the use of five other girls besides his own sister. I don’t know about the other guys but I paid my sister another hundred dollars to be my entry fee.
Friday the guys arrived and I set them up in various areas of the house. The cheapskates were downstairs in the family room. The fairly good players were in several rooms on the main floor. However, my private game was upstairs in my bedroom. The six girls were in my sister’s bedroom watching chick flicks and drinking wine. Margaret was in charge of them and got them all to sign a piece of paper that said that the winner of the game would get to spend twenty-four hours with them, that they would be completely naked the whole time, and that he could have sex with them all as often as he could in that time period.
The signed piece of paper was then placed in the lock box along with the six hundred dollars that we all put in. I handed out the hundred dollars worth of poker chips to everyone and the game began…winner take all.
Well to make a long story short I didn’t win the game. However, I went down to the main floor and managed to win my two hundred dollars back before the end of the big game. The kid that won was really on a lucky streak because he had never played that good before.
Saturday evening after the twenty-four hours were up he came out of my sister’s bedroom smiling and bragging about what a stud he was.
He hadn’t told me the truth either. According to Margaret he fucked her because she had the biggest tits and then he fucked his own sister and fell asleep. Sometime around noon he fucked Margaret again and then two other girls before his time ran up and Margaret threw him out of her room. He never did get around to fucking the two girls with little tits, and they were both virgins too.
She had talked the other girls into spending another night with her and invited me in to have a talk with them.
When Margaret had me strip naked and then took me back into her bedroom, the other girls just smiled at my erection.
The girls had not liked the way that the twenty-fours had gone and apparently I was there to correct the problem. My sister told them that I liked girls of all sizes and ages.
I was introduced to the winner’s sister Joyce. She was fourteen years old and kind of cute. Her breasts were nice and her tush was rounded. Her brother was only her second fuck and she was happy that he hadn’t been her first because he was pretty bad at it. Margaret laughed and said that he was the worse of the six boys that had fucked her.
Karen and Lauren were both fifteen and agreed that he was bad even though they only had two or three other boys to compare him to.
Mickie and Nancy were the virgins. They were both fourteen years old and had tiny tits but they sure were cute little tits. They were both relieved and disappointed that he hadn’t fucked them. They were excited in the beginning that someone unknown would win them and that they would loose their cherries in a special way. Instead they were pleased that he hadn’t been their first and ruined them for life.
My sister told me her thoughts on the subject. Two girls should work on each virgin with me then I should fuck them and make their first time very special. My sister knew that I was still a virgin but she let on that I knew what I was doing.
While the other girls were giving the two virgins a nice long hot bath I was getting some training by my sister. She kissed me, she had me play with her tits, and then she had me suck her nipples. She had me look at her pussy closely to see where her hole was and where her clit was. She let me play around down there and then she had me slip my cock into her. It was great and I lost my virginity to my own sister. She would not let me cum in her because I needed to save that for my first virgin.
Nancy talked Mickie into letting her go first. She was offered like Sleeping Beauty for me to kiss. So I kissed her like my sister had kissed me and Nancy liked it. She liked the attention that I paid her titties. Then she started to orgasm as I started to play with her pussy. The other girls certainly had her excited. I gave her pussy a little lick and found that she was so clean that there was hardly any taste to her, but shortly I started to get her fresh deposit of cum on my tongue. It was great. As I started inching my way up Nancy’s body Margaret kissed her pussy and my cock before they met. My hard cock slipped right into Nancy. It was a slow tight fit but it was wonderful for both of us. Fucking into her was nice and for my first real fuck it was memorable. It was not too long for either one of us. When I cum in her Nancy didn’t want me to take it out so I didn’t. Eventually it went soft and her pussy spit it out.
Mickie waited an hour because my sister said that I needed that length of time to fully recover. No one argued with her. Mickie was just as nice to play with and fuck as Nancy had been and again we both loved it. My sister kissed Mickie’s virgin pussy goodbye and my cock as she had for Nancy.
With my sister’s help I managed to cum in each girl once. Margaret had me put my cock in every girl before picking the one that I wanted to fuck and cum in. That way every girl got a taste of my cock in her pussy every couple of hours or so. Margaret saved herself until the end just in case I didn’t have anything left to give her. After all being my sister she could let me fuck her anytime.
My Friday night poker game continued but never again did we make our sisters part of the bet. Margaret was always there for me but it was Nancy that I fell in love with.
The End
Teenage Poker Winnings
350
