Note: This story was dynamically reformatted for online reading convenience. At times, my girlfriend Beth would have to work on Saturdays and she would ask me to stay over on Friday night so that I could babysit with her nine year old daughter, Cathy. Cathy and I got along very well. We would usually play board games, watch tv or sometimes go out to a burger place for lunch. She was a really sweet girl but occasionally she would get bored and cranky. A couple of times one of her friends would come to visit and that would keep her entertained. Cathy was a pretty girl but was small for her age. Like her mother, she had dark brunette hair, brown eyes and dark, creamy complexion. She was quite comfortable with me and she didn't think anything about me seeing her in her tee shirt and panties. Sometimes she would lie on the couch next to me and I could see the slit of her little pussy through her panties. I tried my best not to look but, being the pervert that I am, I would dream of licking her little cunt. One rainy Saturday morning when Beth was at work, Cathy and I had breakfast and watched cartoons on tv. She was in a bit of a mood that morning and went to her room to play with her dolls. About an hour later she came back to the living room. "I'm bored. I want to do something." "What would you like to do? Do you want to play a game? How about a game of Clue? Or Operation?" "No. Those aren't fun." I thought about it for a few minutes and was at a loss. Then I remembered that I had a deck of playing cards in my overnight bag. "Do you want to learn to play cards?" "Old Maid?" she asked. "No not Old Maid. We can play a game called blackjack. I will teach you something bad. I will teach you how to gamble. How about that?" "Okay," she said. I could tell she was interested in the "bad" part as only children can be. I knew her Mom had a jar full of pennies so I took out 20 pennies and found the deck of cards in my bag. We sat down in the living room, she on the sofa and I on the floor so that we could use the coffe table as our playing table. I divided the pennies between us and shuffled the cards. I then dealt out two hands and started to explain the simple way of playing blackjack. We played a few practice hands and then we started to bet a penny per hand. We played about thirty five hands before I had all of her pennies and declared my self the winner. She wasn't happy about losing and wanted to get even. "How are you gonna continue? I already have all of your money. What do you have to bet?" "I don't know! Nothing!" Then I saw a golden opportunity to have some real fun. But it would be risky and I could get in big trouble. But I was confident that she would go along. "Have you ever heard of a game called strip poker?" I asked. "No. What is that?" "Well, its a real fun game. You usually play another game called poker but it's hard to play. We can play strip blackjack instead." "How do you play?" she asked. "You play exactly like we have been playing except that, instead of betting pennies, we bet a piece of our clothes. The one who loses all his clothes is the loser. Would you like to try?" She looked a little shocked and confused. "I don't know. Do we take off our clothes?" "Yep. Each hand we bet one piece of clothes until somebody loses everything. It will be fun. Do you want to try? It can be our secret game and we won't tell anyone else about it." I could tell she was thinking it over. She had a glimpse of me naked before in another incident and she knew that her friend Bailey and I had a private game that we played without our clothes in the bedroom whenever Bailey would visit. "What do you think? It will be fun," I urged her to agree. "Okay. I guess it will be okay." "Good. Let's make sure we both have the same amount of clothes to bet and then we will play." We checked to see that we had equal clothing. She had on a blue teeshirt and her undershirt. she had on her shorts and panties and a pair of socks. I had to add a shirt and socks to even out the ante. Then I dealt out the first hand. I could have won the first game but I intentionally lost so that I would lose the first piece of clothing. I gave up my shirt. "There you go. You are good at this game so you will probably win," I told her. I dealt again and this time I won one of her socks. Another game brought another of her socks. On the third game I lost a sock. The next game she had to give up her blue teeshirt. Then again another of my socks. We were running even now. We had both lost equal amounts and we were starting to get to the interesting part. "This is fun, isn't it? You are doing really good." I said, encouraging her to continue. "Yes. It's okay, I guess." I dealt the next hand and she went bust. She didn't hesitate to remove her shorts. At that point she realized that she might be about to lose something important to her modesty. "I don't want to play anymore," she announced. "Darn,"I thought. I really wanted to see all of her. And my cock was already starting to stir. "Why do you want to quit? You might be the winner. Don't you want to be the winner?" "No. I don't know," she said with a shrug. "Are you afraid that you might see something you haven't seen before? I have already seen your boobies and you have seen mine, so you won't be seeing anything new," I said, hoping to break through her modesty. "Wouldn't you like to see what Bailey has been seeing?" Her eleven year-old friend Bailey had become a regular visitor after I introduced her to the wonders of playing with a cock. Since our first encounter, I had taught Bailey to suck cock and I could give her multiple orgasms by licking her clit. Anytime that Cathy's mother was away at work Bailey would show up for a mutual cum session. Today was the first time in a month that she hadn't showed up to play. Cathy said she had gone out of town with her mother. "Does Bailey tell you what we do when we go in the bedroom?" "Yes, she told me some. She told to not tell Mom or she wouldn't be my friend." "Well our game can be our secret, too. We won't tell Bailey or your Mom." "I don't know. I don't want to." "What if I make the game better for you? What if I give you a dollar to keep playing? Or would five dollars be better?" This caught her attention. She was silent for several seconds while she thought about it. "Even if I see everything, it won't be the first time I have seen you naked,"I said, which was a bit of a lie."I saw you in the tub once. I saw everything. And I know you have seen me too." "No you didn't. When?"she demanded. "On your birthday,"I fibbed. "No, you didn't." She paused and fidgeted around on the sofa for a few long seconds. "Five dollars?"she asked. "Yes. Five dollars, if you win the game or lose. I will give you five. And you can spend it anyway you like. We will tell your mother that I gave it to you for helping me clean house. Is that okay?" "Okay, but you don't tell anyone. Don't tell Bailey,"she said, almost whispering the words. "Okay, great. Then I will deal the next hand." My dick was really starting to get hard now as I dealt the hand. I was hoping to manipulate the hands to get the results I wanted. The first hand went my way, my nineteen beat her seventeen. She hesitated for a moment, then pulled her undershirt over her head. Her areolas were a light tan color and were still very small but were starting to get a little puffed up. Her little nipples though were quite erect. Maybe she felt cold or was actually getting a little horny. Her only defense now was her blue and white cotton panties. Now my cock was trying to push its way out of the opening in my briefs. I had to push it back into place. "You have such a pretty body, Cathy. You don't have any reason to be embarrassed." She just smiled and looked at the table. I then dealt the next hand. I could have won that hand and got her panties off, but I wanted the game to turn out differently. I intentionally busted the hand and then took off my teeshirt. I could see that her face was starting to look a little flushed. Her cheeks were a light pink and her eyes were looking at the coffee table. She knew the next hand was going to mean someone would be naked. Would it be her or me? "Okay. This is the big hand. Somebody is gonna be the winner after this hand. Are you ready?" she didn't reply so I dealt out the next hand. I couldn't believe my good luck. She had a natural blackjack, a ten and a black jack. She was the "winner". "Looks like you beat me, fair and square. Are you ready for the payoff? She just looked at me with those big, brown eyes. I stretched my legs out and got up from my sitting position. I could see her eyes glance at the bulge in my shorts and then look back down at the table. I reached into my shorts and pulled the foreskin back from the head of my dick. I wanted her to see the real thing. It was already stiff but I stroked it a couple of times and stepped toward the sofa. Her eyes were almost parallel to my crotch. I reached over with my left hand and stroked her hair, then twisted her head toward me as I pulled my cock out of my shorts. She gasped and closed her eyes. I pushed my shorts down to expose my balls too. "Look at it, honey. This is your prize." She opened her eyes and looked at my stiff penis and my furry balls. Her eyes were big and she was silent. "Cathy, would you like to touch it? It's your prize, you can touch it if you like. Bailey loves to touch it and make it grow." "No, I don't want to touch it,"she said. "Would you like to kiss it?" "NO, I don't want to kiss it? That's gross!" "Bailey loves to kiss it. She likes to put it in her mouth and lick it. Would you like to do that?" I continued to stroke it and move it around in front of her. I pulled her head close and rubbed the glans against her soft pink lips. She tried to turn her head away but I held it tight and close, rubbing her lips again. There was already some pre-cum on the slit and it smeared across her lips. "I want you to do something for me. It's real easy to do and I promise you will like it." "No, I don't want to." She was starting to whimper a little. "Come here,baby. Lay here on the floor." I moved my hand to the back of her neck and pulled her off the sofa. I then pushed her down to the floor and straddled her as she lay there naked as the day she was born. She tried to raise her legs but I sat down on them and held her upper body down with my left hand. I started stroking my cock with purpose. I just had to cum, my balls wouldn't hold all the sperm that was being produced there. I stroked my cock faster and with a longer stroke until I knew I couldn't hold back any longer. I leaned forward and aimed my cum stick at the space between her tiny breasts. She was lying still now with her eyes closed. When the first spurt of hot sperm hit her chest, she opened her eyes and got to see the next two shots of jism. The second shot all the way to her chin, leaving a stream of cum from her chin to her chest. The next went just as far. A couple of more short spurts and then the cum began to just pour out. I made sure it leaked out on her nipples and it looked like they got even stiffer. I was breathless after the eruption and she lay there totally silent. When I got my wits about me, I dipped my fingers into the pool of sperm on her nipples and then rubbed my fingers on her lips. She tried to turn her head, and I smeared it all over her cheeks. I then got another big wad on my fingers, held her head and shoved my fingers into her mouth. Amazingly she didn't try to bite me. So I did it again. She was sticking her tongue out, trying to get the cum off of her tongue and making a face like she had been sucking a lemon. I fed her a couple of more finger loads of cum, then I leaned forward and kissed her on the lips. "That was so great, cathy. You did so good. You made me feel so good. I love you, Cathy. You are such a wonderful girl." I got off of her and helped her to get up from the floor. She had some tears on her cheeks, so I sat her on my knee and wiped away the tears. I kissed her cheek and then kissed her lips again. "Don't be upset, sweetheart. Every girl and boy has to learn about sex in one way or another. Now you know what makes a boy feel good. I'm so proud of you. Now let's take you to the bathroom and you can get a good shower and take a nap. Your Mom will be home pretty soon and we will have a nice dinner together." I led her to the bath and got the shower water running for her, then watched as she washed the cum off of her body. She soaped up her little body until it was white with foam. How I got away with that I will never know. But after the shower, I gave her a ten dollar bill and she smiled and said thanks. Several times after that I made sure that she was rewarded for small achievements or chores. I know I am bound for hell because of the things I have done to these girls but I guess the Devil needs company too.