Daring

A few friends of mine came to me one day. They were having an argument about who was the most daring of them all and they wanted me to decide who it was. I thought that if I played my cards right I could be in for some fun. I’m a guy, by the way.
I told them that I was prepared to be a sort of referee; however there were to be some ground rules. I wanted to be a witness to all challenges, or else I couldn’t be fair. Secondly I wanted to stay friends with all of them so I said that I was going to be fair, and that they shouldn’t get mad at me for making judgments. Thirdly– I wanted someone to be the most daring in at least 3 things, so it wouldn’t be chance. Fourth– I knew two of them had a phobia and I didn’t want any challenge concerning those things. Fifth– it shouldn’t be anything dangerous and last but not least, they should come up with the challenges, give them to me on paper and I’d declare the challenges on the appropriate time. They wanted to know why they should write them down and I said that way I could prove that I didn’t think up those challenges. They agreed, but since I was going to show the papers they wanted to print them. Now I had them where I wanted! I knew they would want it anonymous if I hinted in that direction and since they knew we didn’t have a computer they could print it out. Little did they know I had to baby–sit each night at the neighbors and could sit behind their computer whenever I liked.
I’m not going to bore you with the challenges they set for themselves; they were so boring and easy that it didn’t surprise me they couldn’t decide who was the most daring.
After a week I added a note saying they had to wear short skirts without panties to school. After all, I had to check…. I said I had a challenge I didn’t know what to do with and it was too much perhaps. They took the bait, nothing was too much, and chickens could drop out if they wanted to. Until now everyone had gone along with the challenges so it was still a tie, worst case it would remain a tie, best case as well. I told them the challenge and set the date for next Monday. That day I could feel my heartbeat in my throat when I went to school. To my delight one of my friends came walking to me in a very short skirt. She gave me a little mirror and told me I had to check them all at more point in the day randomly so no one would try to put panties on. I went behind the school and told her to meet me there before the lessons started with the other girls. When they arrived only three were wearing skirts the other two were wearing jeans. I wanted to say they had lost a point when they said they weren’t allowed to go to school like that. Fathers… They opened their schoolbags and got skirts out. They took their pants and panties off and I could see some pussy… The short skirts were put on and they were ready for the challenge. The other three showed they weren’t wearing panties by pulling up their skirts. Wow, their cunts were all beautiful, especially since they were the first cunts I had ever saw! After that they agreed on the mirror part, but discretely. During that day I saw a lot of pussy in the mirror. One time after a girl got off of the toilet and I could see the little droplets in her cunt–hair, it gave me a new idea.
Three boring challenges later I added one of my own. They had to piss behind the school. After all the classes were over we went behind the school. The first one had a skirt on, she raised it, shove her panties to one side, squatted and peed, the second had also a skirt but remained standing, shoved her panties aside and peed. The third took her panties off and stood without raising her skirt and peed. The other two were wearing jeans. They had to drop their jeans and panties to pee. I liked to see them pee, but saw more hair than pussy. That had to change…
After one and a half weeks I had a challenge of my own. It was a Friday, and before Monday at noon they should have shaved their cunts completely bald. No hair left whatsoever. That evening one of my friends came by to see what homework we had for math and when we got in my room she dropped her pants and panties and showed me her bald pussy. No hair whatsoever. Wow, that one was beautiful. When she was gone and I had cum twice over what I saw, another friend phoned. She didn’t dare to shave herself. Not that she was afraid of having a bald cunt; but she was afraid that she’d cut off her clitoris or something like that. I thought about it for some time and then told her the challenge was to have shaved their cunts, not to shave them. So she could have her mother (yeah, right…) shave her cunt and still make the challenge. She said there was no way that she could ask her mother, she would go crazy. After a silence a shy voice came over the phone “would you please do it?” Yes, of course I would…. “Thanks, you are a real friend!” If she only knew… We agreed she’d come to the house where I babysat and I would shave her there. (I had some of them over there sometimes, I was allowed to as long as I took care of the children and didn’t have sex when they were awake–I could do whatever I wanted). When she came over one of the children was playing a game on the computer and the computer got stuck. Luckily I don’t know anything about computers as far as these kids were concerned (my father called them the doomed things from hell and couldn’t work with them). So when the kid asked me to help I acted like I didn’t know anything about it and couldn’t fix the problem. In reality the game was frozen (Windows…) and should be closed with Ctrl Alt Del. But I didn’t know that then… My friend took over and closed the game, restarted it and told me later it was an easy problem; one I could deal with if I wanted. I told her my father would kill me if he knew I worked with computers. (In case anyone wonders how I knew about computers then, the people in this house had a lot of computer books and I taught myself everything I know now.) After an hour or two the kids were in bed and sound asleep. I told my friend I could do it now and we went into the kitchen. She got the shaving cream and razors out of her bag. She told me she was going to lie on the table, I could shave and she didn’t want to see it happen, she would just lay still. After she had taken her pants and panties off I carefully massaged shaving cream on her cunt–lips, making her moan a bit.
After a while I made myself start shaving, I had to or it would become suspicious. I took my time, carefully shaving her hairs off. After I was done I washed the cream off and cooled her cunt down a bit. Then I massaged some baby lotion on her cunt–lips to prevent them becoming sore. She didn’t stop me and I kept massaging lotion in. Slowly I got closer and closer to her clitoris and when I finally briefly touched it she had an immense orgasm. She was shaking so hard she almost fell off of the table. She looked me in the eye and blew me a kiss. “You can shave my cunt anytime you feel like it if you keep doing that” she whispered. “What was that?” Apparently she had never had an orgasm before, so I explained to her what it was and how she could get them. She preferred me doing it for her as she thought mother would kick her out of the house if she caught her. She dressed and we talked for some time until she had to go home. The next day two other girls came by my house to show their bald cunts, the other two came to me in school. The first walked with me around the school and dropped her pants to show me her bald cunt; the other one gave me a mirror and let me look under her skirt. She had a bald cunt as well, and no panties, she went to the toilet to put them back on and they had all passed this challenge as well.
I never expected to get this far, so decided to lay low for a while not to spoil this great opportunity.
After two weeks I couldn’t resist any longer and added a new challenge. They had to come to school wearing short skirts and weren’t allowed to go to the toilet all day, after school they had to show their panties were still dry and then piss through them while the others watched their panties get wet. The challenge was met with a lot of disbelieve and protest, but the next day all came to school in skirts or changed at school into skirts. I never saw any of them go into the toilets or heard any protesting that someone did go into the toilets. After the classes were over we met behind the school. Now everyone around them knew about the challenge, there was a lot of squirming and sighing. I expected it would take a while until the first would be willing to start, but they almost started fighting over who could do it first, they had to go that bad. I took control and said the person on the left could start and we would go clockwise from there. I decided on the left person since that was the girl I shaved and I felt kind of connected to her.
She quickly showed her panties, they were dry, and she started to pee as soon as I told her she could. She didn’t have any difficulty starting, one moment her panties were dry, the next moment a thick river poured out of her panties. She pissed full power all the way, and the look of relief on her face, well I never will forget that. It was immensely erotic! When she finished peeing there was only a small wet spot on her panties. She had wet with such a force the urine had just burst trough, virtually not wetting her panties at all. The next girl had more problems starting, she was still dry and when I told her to go she just couldn’t, she couldn’t get the flow started. A small wet spot did appear and grew slowly since she wet herself in small dribbles. After about three minutes her panties were completely soaked and she started to dribble on the ground. Suddenly she sighed, as her stream got bigger. She had lost all control and though her stream wasn’t as big as the first girls’ stream she pissed for all she was worth now. The other girls were squirming even harder now and after I went to the third they asked if I could check their dryness, since they thought they would start wetting themselves soon, even if they weren’t allowed to go with all the sound of falling piss around them. I checked and they were all dry, and since they were in agony I told them they could go in their panties together. Now it truly was a piss festival, four girls peeing their panties for all they were worth, I almost came in my pants.
Fortunately I didn’t. When they were done pissing we went away. I had to get my coat from my locker and the first girl as well. The others went to their houses immediately so we were alone. After I got my coat she asked me to come to the back of the school with her. She got my hand, put it on her crotch and asked me to help her cum, I started to massage her clit and she moaned so loud I had to kiss her to silence her a bit. Suddenly my hand got wetter as she started to wet herself again, closely followed by cumming on my hand. She thanked me for helping her out and pushed me to the wall. She got my dick out and masturbated me until I came all over the wall. “Now we are even,” she winked at me and went home. After I recuperated a bit I went home as well, walking on air. It had become the most wonderful day in my life thus far. And I hoped it wasn’t finished yet…
Life continued almost like before, the only thing that had changed until now was that I sometimes helped one of my friends have an orgasm and she returned one to me every once in a while. After two weeks or so she came to me asking if I would like to shave her again that evening. The hair had started to grow back and she liked it bald better. Of course I wanted to do that, so she came over. After I got her hairs all off and had massaged some oil on her cunt I couldn’t resist. When I noticed she was close to cumming I licked her split (oh, wow, she tasted good) and took her clit in my mouth. She came instantly, and held my head on her cunt, so I kept licking until she came again. After that she let my head go, sighing, “that was nice” and tried to get off the table. She couldn’t, her legs were too weak to support her. I had to help her get dressed and than got to the couch in the main room. She told me that she had never cum that hard, and she needed time to recuperate. She leaned to me and I let her rest on my shoulder. She wanted to lie down for a while and lay down in my lap. My dick, still alive from what had happened sprang to attention. She felt my dick against her cheek and giggled. She massaged it trough my pants with her hand but stopped before I could cum. Suddenly she opened my pants and took the head of my dick in her mouth. She used her hand on the shaft while licking the opening of my dick. I came almost immediately, making her swallow it all. After I calmed down she smiled at me, sperm on teeth, asking if it was as good for me as it was for her. I told her it was, if not better. After that she had energy again and went home a little while later.
The challenges the girls themselves came up with were getting more daring now as well. It seemed I gave them a good example, and the girls all wanted to out–challenge the one that was challenging them to go so far. I was very surprised to find this challenge, but no less delighted. The challenge said they had to get completely nude behind the school during class break. I told them it was a big risk, a risk I was prepared to take, but it would be to noticeable if six girls and a guy went behind the school and stayed there for a long time during school. They were to come alone or in twos and undress there. I was behind the school as soon as I could and was waited upon by two girls, who couldn’t wait to get out of their clothes, or rather, get it over with. One went on the outlook, the other quickly undressed. I saw her completely nude now, she still had a bald cunt, so she must have shaved again. After about ten seconds and twirling around she got her clothes back on and changed places with the other girl. The same thing as the first girl, she had a bald cunt as well. She gave me a longer stare but got dressed quickly two. When they were gone I could feel my dick ready to burst out of my pants. Then two other girls came, undressed at the same time and twirled around. One even massaged her breast and the other bent over with her back to me. If you never saw a bald pussy from behind when a girl bends over, you haven’t lived and don’t know the show I got there. They dressed quickly and disappeared. I didn’t even have time to recuperate as the fifth girl came around the corner, already undressing. She wanted to get it over with and came topless around the corner. She undressed, stayed nude for a second and started to dress again. When she was completely dressed a teacher came around the corner to see where we were all going, and wanted to know if I was selling drugs or something to these girls. He frisked me, but didn’t find anything, drugs or money and left us. We now knew however we had to be more careful. Finally the last girl came around the corner. She was wearing a long black dress. This was the girl I shaved and exchanged orgasms with. She simply pulled the dress over her head and stepped out of her shoes and was nude, she wasn’t wearing anything underneath it. She came to me and put my hand on her very wet cunt, I knew what was expected of me and made her cum. After that she got on her knees, got my dick out and sucked it twice before I came in her mouth. She dressed, swallowed (yes in that order) and whispered in my ear she hoped I liked the show she had arranged for me, her favorite friend, who could made her cum so good. I told her I certainly did. She asked if she could come over the next day, to my baby–sitting address, and I told her she was more than welcome.
The next day she came even before I went over to the neighbors. We were chatting a bit until we went there. The kids were very pleased I brought a girl along and chatted a while with her until they dragged her to the computer to play with them. I watched some TV while she was playing with the kids and she sent them to bed when it was time for them. She watched some TV with me and when the kids were sleeping she took me to the computer.
She promised me she would never let my dad or anyone else know she was going to teach me how to work a computer worked, but she thought I needed to know anyway, as we would both be in college the following year. In this day and age you needed to know how to work a computer. I made her swear not to tell anyone, and confessed that I had taught myself some computing. She gave me a diskette and told me to open a Word document on that diskette, without the use of Word itself. When I tried to open it in Window’s Explorer the diskette appeared damaged. My friend took over but couldn’t access the diskette as well. She almost started to cry, apparently there was something very important on the diskette. I had no choice; I had to show what I could do, in order to save the diskette. I started to do magic on the computer and managed to access the diskette in such a way I could open the document on the diskette. I opened it as a loose set of codes and managed to convert it to a Word document without the layout she made. I saved it to a working diskette and wanted to close the document. She told me to read it while she went to the toilet. I read it and understood why it was so important for her. It was a letter to me, a letter in which she told me that she was in love with me. She had discussed it with the rest of my friends and they were okay with her pursuing me. This meant the challenging had to stop for I would be in favor of her if I wanted to be her boyfriend. If I didn’t the friendship would be damaged and the challenging better stop anyway. Last comment in the letter was the girls had decided they were all more daring than they had expected of themselves, and declared themselves all winners. But if I wanted the challenging would continue for they found it a real turn–on, as long as I continued my challenges. They hadn’t figured out how I managed to have printed challenges, but they had talked about the challenges and found out there were a few no one had thought up and must have come from me.
“What do you think” a shy voice came from behind me. “Did I ruin our friendship? Or…” I looked at her with a love I had never felt before. “I certainly do not hope so. I hope we can go out, be boyfriend and girlfriend and still be friends.” I smiled at her. She started to cry from relief and threw her arms around my neck. “At least now we know how you got those notes on paper. You are a computer genius! Oh I’m so happy I can just wet myself, you know what, I think I will!” I put my hand on the crotch of her jeans and felt them get wet. This time she wet slowly, getting the entire crotch of her jeans wet and her legs as well. When she finished peeing she was very wet and I was horny as hell. She felt my stiff dick through my jeans, “I already thought so! It makes you horny too. I’m horny as well. I need to come, please put your hands in my jeans; I want to cum in my wet pants.” I massaged her clit and soon she had cum four or five times. “Now it’s your turn” she said, got on her knees and started to give me a blowjob. I came quickly again, only lasting a minute or so. She swallowed my come as usual.
Everything made sense now. “You did dare to shave yourself, didn’t you? You just hoped it would lead to this?” “I admit it. It was my intention to get to you like that. It worked too– you made me cum. The second time you shaved me I decided you needed to cum as well, in my mouth. I have had orgasms before, you know.” I had figured as much. We agreed we would make challenges together from now on, but they would have to be outside school, since teachers were starting to notice.
I made many challenges, a lot I have forgotten, but just for your imagination here are a few. I made the girls eat each other out (it was a big thrill seeing my girlfriend eating out another girl and being eaten by another girl.) She came a lot of times in that challenge, and she discovered she was bi–sexual then. Another challenge for them was to witness me deflower my girlfriend, and later one by one to get deflowered by me. I have deflowered six girls in six days. It turned my girlfriend on to see me fuck another girl, and I ended up eating her out on more than one occasion while deflowering and fucking a friend of hers. Those challenges combined led to this challenge: have threesomes with us. One time I never forget. We were in a big room, undressed and put the lights out. In pitch–dark we screwed and licked and sucked and later it seemed I fucked them all. The wetting challenges I made: I made them wet their panties at school; they were not allowed to take their panties off on the toilet. Once I made theme wet their panties and keep doing that for a week (same panties!). I made them wet cut–offs both before and after school. I even once made them wet their jeans standing with their legs closed (wetting down their legs) before school. After that we saw more wetting and wet jeans. It became hip in our school to wet your pants. A few weeks all girls just wet their pants, only going to the toilets to shit, but the director threatened to expel anyone who did it so it stopped a bit. But it still was an accepted and even popular thing to do. Last but not least I one made them pee over each other through their clothes, making a big wet mess.
My girlfriend and I are still together, enjoying wetting and sex. The other five girls come by regularly to wet and have sex, since their partners do not understand the beauty of wetting and having sex together, as we do…
There is one more thing I need to tell you; last week a mad father came to my house. My son had challenged a girl at school to wet her panties under her skirt, and she had done so. Apparently he resembles me a lot.
JJ ( email is welcome… JJ is male )