Naked on the Internet

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I used to spend some time in the Internet playing games online. I mostly do this on lazy afternoons just after the midday relax and before the night clubbing. My favorite game is backgammon, since is simple and based on luck. I am quite good in this game, considering that I am not a college graduate and I never was good in math.

Anyway, before telling my story a few thing about me: I am a very sexy lady (178cm high, 51Kgr, 90-52-87), long black hair, black eyes, long legs and a tanned body, including tits since I always swim topless. I also have a shaved pussy. I have done some pretty wild things when I was younger. Please read my stories "Bar Made" and "Strip Basketball Game" here in Literotica to get an idea of how wild I used to be. I am still wild but since I grown up to my almost 30s I have relaxed a bit. Anyway I am 28 now (although I look younger and I often lie about my age). I live in Greece, I love to play beach volley and swim topless or nude. English is not my mother tongue, so excuse my mistakes and consider this story to be told with my funny, and hopefully erotic, accent.

Well, too much about me, let us get back on the story. I used to play backgammon against a guy from California. His name is John and our games were quite even. We have become friends and he knew about my stories in Literotica and what I like sexually, although our chat was never sexual; well perhaps jus a casual flirt. One day I was kicking his ass in backgammon and I started made jokes and telling him that if we play for money I would have won his house! Suddenly he told me:

- Do you want to play really for money?

Since I was broke as usually, the little earnings from my regular waitress job mostly go to cloths and accessories, I told him:

- Firstly I don't have any money, and how on earth we could play for money? This site does not offer such option.

- Well, then I could play for money and you could bet something else.

- Like what John?

- Remember your 'Bar Made' story?

- I am remembering John, but you are like 5000 miles away.

- Well you said that you have a web-camera. Don't you? So, what you say?

I know exactly what he meant, but I want to find exactly what the rules of the game will be. But the concept has started to interest me. Perhaps not just interesting but exiting me too! So I decided to play alone:

- So John, you propose a strip backgammon game, or something like this?

- Something like this, Helen. Every game I win you just have to take a cloth off.

- And what about every game I win? Need to remind you that today I won 7-0?

- Well, every game you win I will pay you. (Here John offered a number, which was very high. It was about the money I made with 2 days work, so in case I won, lets say, 15 games this could be a month's salary. I am not going to tell you my price *smile*, but lets say that the bet worth it!).

That took me by surprise. I know John was well off, but still that offer was quite generous. So I said:

- Let me figure this out. Every game you win I will have to take 1 cloth and every game I win you will pay me?

- Yes Helen, I will transfer the money using my web-bank account directly.

- Ok, John lets play! There are so many things that I would love to buy!

- Ok, Helen, but first decide what you will wear?

- I could wear anything I want? As many items as I like?

- Well be fair! Not as many as you like, just a reasonable amount of cloths.

-Ok John, I will go dressed and turn my web-camera on.

I started to dress sexy but also to wear many cloths. I knew that the more items I could wear the harder for John to strip me and the best chances to win a lot of money for me. I took of my panties and t-shirt that was the only items I had on this sunny afternoon and I chose the following:

A black g-string and on top of it some regular black panties and a bra to much.

A garter belt, a pair of stockings and my stiletto hills.

A red hot and sexy mini skirt and a black lace shirt and a red blouse on top.

Then I turn on my web-camera and connected with John. We still were on the backgammon room. After I get some enthusiastic comments from John about my attire, we started to play.

I won the fist game and John said:

- You won fair, I have already transferred your money, you may check your bank account if you like.

- I trust you John. Lets play another.

The second game John won it easily, so I had to remove one item of clothing. I took off my red blouse. It was quite hot anyway. John won the second game and the one that followed, so I had to remove both my stiletto hills. I was still quite modestly dressed and I didn't mind at all.

But then John won another game and then things started to become a little embarrassing. I wasn't expecting to lose so many games, so soon. After some though I took off my lace shirt which caused many enthusiastic remarks from John. I was standing in frond of my camera wearing my black lacy bra for the viewing pleasure of a guy that we had never met. I felt strange and exited.

- Last game you won, John.

- We will see Helen. Perhaps is my lucky day. Want to double the bet on next game?

- Sure John, if you want to pay me double the bet.

Unfortunately for me I lost this game as well. I didn't knew if this was luck or faith, or some force had decided that this was a good day for me to be humiliated but it seemed that my luck has stopped. I had to pay 2 cloths. The first was my skirt causing John to whistle and comment my garter belt and my stockings. After allowing some encouraging comments about my tanned legs I took off the garter belt staying only with my panties, bra and 2 stockings.

John offer to play double again, but I declined. Somehow I wasn't felt very confident that day. John won easily the next 2 games and my stockings were removed one by one. John told me that he was enjoying the show and that he was recording it. That made me felt strange but I was anticipated such a thing. Anyway I was hoping that things will change and I will not need to remove any more cloths.

Luck has seemed to change for me, since I was the next three games and John immediately pay me the bet. I have won a week's salary and a only had to be in my underwear. Things seemed to be quite good. Then John had made me an offer:

- Helen you made me very horny, so I have another offer, just to speed things up.

- Hmmm John, what you have in mind?

- You wear two cloths, right? Panties and bra?

- No John, 3 cloths! I wear bra, panties and a g-string.

- Wow. Ok here is my offer. We will play just one game. If you win I will pay you 3 times the money you have already won. This is like you won 9 games and you will have nothing to show.

- And if I lose, John?

- If you lose then you will have to strip for me, slowly for my pleasure.

I was quite exited and I could feel that my pussy starting to wet. The entire situation have made me horny, so I knew that I couldn't say no. Besides it was my chance to win a lot of money. I could picture some sexy panties, a dress, some jewelry that I could buy. So I said yes.

Unfortunately John won the game, so I had to strip. I turn my back on my web-camera and started to remove my panties. I still wear the g-string, so I wasn't like naked, but John had a great view of my naked ass. I know that he was enjoying the show because his voice became deeper and started breath heavily. After teasing him for a while I turn to face him and tried to unbutton my bra. But I was hesitated. It felt exited, but I also felt that this was too much for me. I felt kind of dirty, kind of humiliated. You know that sometimes is easy to do something extremely wild and sometimes is so hard to do something simple. This is was happen to me. I used to swim topless in Greece, it is legal and custom to most beaches, but I just couldn't took off my bra, so although I have done wildest things I felt that I could do this.

John realized that I was reluctant to strip, so he made me another offer:

- Listen Helen, perhaps you want another chance?

- What you mean John?

- Well, lets play another game. If you win, I will just pay you the money and we will forget about it. If you lose I will still pay you the money and you will decide what you want to show me.

That was an amazing offer, so we started to play immediately. While the game was in progress, John informed me that he had transfer the money to my account. I was very excited that I 'won' all that money, but I felt excited for another reason too. As the game progress, my mood changed. In the begging of the game I was hoping to win, but after a while I was hoping to lose. I found myself hoping that I will lose and I will have to pay the bet.

The game turned out to be very close. I was ahead and I picked up 2 out of my last 3 checkers. John needed only 44 55 or 66 to win in his last roll. Any other roll and I win. I was practically holding my breath; secretly wishing that John will make the winning roll. And finally the computer screen showed 55s followed by "Game won John". John immediately said:

- Sorry Helen, I was lucky last roll.

- That's OK John. You were lucky all this afternoon, but that's OK.

- Helen, you don't need to undress if you don't.

- But you want me to undress John?

- Are you crazy? I d love to see you naked! I will do anything to see you, but only if you wish.

- Ok John, then please do me a favor. Please turn off your camera but leave the audio on. I want to hear you but not see you. It will help me do the stripping.

- Ok Helen, this will allow me to do some stripping too.

- Lol John!

John turned off his camera. My mood was complexly changed. Although in first I didn't wanted to strip, now I was eager to strip in frond of John and do even more. So I asked him to excuse me for a minute wend in my bedroom and returned. John couldn't see what I was holding under my back.

Then I started to dance for him, teasing him by shaking my ass and bending in frond of the camera. I knew that my naked butt was quite a spectacle for him. He had stop talking and was breathing heavily. Then I faced the camera and slowly I removed my bra. I start to play with my tits, pinching my nipples, squeezing, licking my nipples and feeling as sexy as I could. Suddenly John said:

- Oh, Helen I am sorry! I am still recording this. Please let me stop the recording.

I knew that another guy may say that he stop the recording and kept recording but John always kept his word. So I said to him:

- No John, please record this. I know that you will keep it only for you.

Saying this, I stood up and slowly removed my final clothing, my g-string. Then I sat on my chair, lifted both my legs and allowed him a perfect view of my excited pussy. I gave him the grand tour, by splitting my outer lips and spreading my legs, so he could see everything. Then I showed to him my 'surprise'. It was my large dildo that I have brought from my bedroom. I lick it pretending that I am doing a blowjob and then slowly started to fuck my self in frond of him. My pussy was very wet and welcomed the large dildo that slide in.

I played a little moving the dildo in and out of my pussy, but soon I realized that I was too turned on to hold on and broke to an exploding orgasm. The shy girl that a few moments was reluctant to show her tits now was fucking herself using a large dildo. But I was in heaven. I didn't care that he enjoy me and I was actually turned on by the fact that he was watching me.

From the sounds from John's audio I realized that I wasn't the only one that reach orgasm, but I didn't say anything.

John and I continue to chat over the net. John had his chance to see me naked many times after that night. Some times I used to leave my web-camera connected to John's PC and walk around my room naked, or sleep naked. I spend some of the money I 'won' to buy a gift for John and the rest for cloths and panties. John was the first that saw me model all these cloths for him. Our relation grow further when he visited Greece for 2 weeks last summer. We did many wild things in these 2 weeks but we both promise not to share with anyone. After these two weeks we both decided to stop communicated. We knew that this was a perfect way to keep the best memories from each other. John has hundreds of my videos but I know he will never share or show them to anyone. He is engaged to be married on September. I, on the other hand, am still free spirit and still looking for adventures. Some over the net, some in real life. Who knows what my next bet will be?