[Fiction] Diana’s Daring Ways

[DrakeSebastian]

Note: This is my first story of this type. I happen to have the great ability to start many writings and then never finish them. I appreciate comments and constructive criticisms. I would also like to know if there is any interest for this story and if I should continue.

Chapter One


(Part: 1 Day: 1)


Diana’s parents were away for five days, on one of the countless business trips that required them to leave for dull, long and boring meetings that left Diana on her own for extended periods of time. Enough time for her to get extremely bored and left to her own wills, a tad bit horny. On one such occasion she created a game where she would randomly pick a sweet tart from a box, the color of the sweet tart would decide what kind of dare she would do and then to ‘agree’ to the dare she would eat the sweet tart, making sort of a pact with herself to carry out the sometimes very risk and nerve-wracking dare. Her game could only end when she pulled out ether a blue sweet tart, which represents difficult (and sometimes very messy) ‘home’ dares, or a red(which some call pink) sweet tart, which represents public dares for the most part. The game could also end when she had taken five or more dares, though if she was feeling up to it she could continue on taking dares well after she had met the requirements that ‘ended’ her horny game of dares.

In a dimly lit room Diana slipped her panties down her slender legs and onto her feet. With a gentle kick she flicks the panties off, tossing them into a small pile of clothes. Her hands then quickly untie her bra and let it fall off of her body. A small quiver of excitement traveled through her body. She went to her mirror and twirled about, admiring herself. Her skin was fair and evenly tan. Even with small imperfections that only she seemed to notice she was pleased with her look, even the small freckle near the tip of her nose. Her short black hair and dark brown eyes made her appear daring. She found this quite fitting considering she was about to play her game of dares. With a quick bound she hopped on her bed and picked up a box of sweet tarts. Closing her eyes she reached her hand in and selected one at random. When her eyes opened she found in her hand a green sweet tart.

“An easy start,” She thought to herself as she placed the sweet tart on the tip of her tongue. For a brief second she savored the flavor and then ate the sweet treat, sealing the deal.

After she had made the ‘pact’ Diana rolled over so her chest was against the bed and her head facing the edge of the bed. She then leaned over the bed and took a small cardboard box out from under her bed. She opened the box to reveal six set of cards, each set of card a different color; red, blue, yellow, green, orange, and purple. Diana took the green set of cards out of the box and shuffled them.

After Diana was satisfied that the deck was truly shuffled she pulled the first card from the deck of cards. “Green, an easy dare or is it?” She asked herself with a devilish grin before she began to read what the card had written on it aloud in whispered suspense.

“I dare my future and most likely horny self to step out on the balcony wearing absolutely nothing (though you should already be nude). Also to make things more interesting, future self, you must have one foot on top of the railing and one foot firmly on the floor, allowing you to show off that well shaven pussy you have kept hidden away. Roll two dice and add them together plus five, this will be how many minutes you have to stay out there. P.S No covering up what so ever, though I wouldn’t be surprised if your hands are too busy keeping you from falling over.”

Diana grinned, thinking how evil her past self was. Diana quickly found two dice and rolled them. The first one landed on five and the second one on six. Sixteen minutes was how long she must stay out on the balcony.

She gently rubbed her clit, already feeling aroused, as she looked at the time. It was seven thirty four pm. After she had written the time down she opened up the sliding door to the balcony and stepped out.

It was already dark outside and the stars were visible. A soft cold breeze was in the air, sending shivers of excitement racing up her naked body. The breeze made it even more apparent to herself that she was nude for all to see. Nervously she placed her left foot on top of the side railing, presenting herself with as much dignity as she could muster, facing the empty street, one story below.

Within less than a minute a car was headed down the side of the road nearest to her with its headlights on. Diana held her breath as it neared. Light fell upon her only for mere seconds as the car past, but it was enough for her nipples to harden, and the embarrassing feeling of being seen entered her body. Even though there was little chance that they looked up and saw her, she felt a shrill of daring excitement electrify her body.

In the time she was out a total of eight cars went by, three of which she thought had spotted her, but never the less she felt the rush of excitement was well worth a few peering eyes. When she went inside she found out that she had stayed out two more minutes than she needed to, as she got back on her bed her naked body shivering slightly getting accustomed to the warm room.

Diana closed her eyes reached into the sweet tart box. When she opened her eyes she found a red sweet tart resting in her hand. She ate the sweet tart and then quickly pulled out the red card deck in anticipation. She shuffled the deck and took the top card.

“You my dear friend and future self are very unlucky or perhaps very lucky if things go well. Your dare can be found inside the daring box on a piece of paper titled ‘Number 22’ Good luck. I bet you are going to really enjoy this dare. If not, well you can only really blame yourself.”

[jklivin]

I like this little game she has with herself.

[kmacroxs]

So far, so good. Please continue writing this.

[DrakeSebastian]

Thanks for the comments. I’ll try to get another post up tomorrow or the next day, but I’ll make no promises. Feedback is greatly appreciated. Thanks.

(Part: 2 Day: 1)


Diana spent little time finding the paper titled ‘Number 22’. “This will be a very eventful day” Diana though to herself as her eyes quickly began to read the paper and almost at once she regretted reading it and remembered her evil past self writing Number 22.

“You, my future self, are going to have a guest over. You must invite a boy that is near your age over and play a game with him of his choosing and then precede to change the game’s rules to have dares added. Basically something close to Truth or Dare and the very game you are playing right now.
To make sure that this dare is far from boring future me, you must remove an item of clothing every so often as well as rubbing your naughty clit every so often, keeping yourself as horny as ever. Also, to invite the boy over you must walk to his house, so I hope you know someone close by.
P.S. About that clothing bit, you may only have at max two items of clothing on at the end of this. Because I am in an evil mood right now I shall name the two items now.”

Diana’s face went bright red as she read the next two words.

“Your socks.”

Diana gulped a breath of air. She knew she had accepted the dare with the ‘Pact’ she had made and so it must be completed or else her game would have no chance or risk. She knew she could decide not to do the dare, her logic from her gut told her to give up the game, and it’s not worth the uncertainty, while other parts of her body were thrilled with excitement. She unconsciously began to pleasure herself while two forces in her mind battled. Eventually Diana’s hormones won out.

“I’m going to do this,” Diana finally stated, reaffirming her decision. Her mind then went to finding a way to accomplish the dare.

There was only one boy of seventeen years of age that Diana knew lived close by. His name was Leonardo, Leo for short. He and his family moved in the middle of this summer, perhaps only a month ago. She hardly knew what he was like, in fact they had only met when her parents wanted and advertisement made for their business that they had contracted from his father who worked for a large advertisement agency. After finding out that the two of them both liked strategy games they had played one game of Risk while they waited for their parents to finish up with the long and dull talks of business and advertising.

It had been only a week since then and she had been tempted to invite him over for another round of Risk, in which she fully intended to beat him. She wasn’t quite sure how he would take to the idea of adding Truth or dare type rules as well as the card game she had created herself to the game of Risk, but there was really only one way to find out. Diana quickly got dressed putting on a black bra and panties. Diana blushed as she put on her favorite pair of red knee high, knowing that they would be the last items of clothing she would be wearing. She finished by throwing on her blue jeans, a bright green t-shirt and a pair of light blue tennis shoes.

She left right away even though the back of her mind told her to stay home. She walked at a brisk pace to the Leo’s house, about one and a half blocks away. It had only taken her roughly twelve minutes to get to his place from hers at her pace, but with her being nervous it felt like an hour. When she arrived only one light was on in the house and the car was gone. She rang the doorbell and waited a moment.

“Damn, I didn’t think that he wouldn’t be here.” She thought to herself as she rang the doorbell once more, hoping he was there. She was about to turn around and leave when the door opened up.

Leo looked surprised to see her. “Hi, um, Diana. That’s your name right? So what brings you here?”

“I… I was bored,” Diana blushed slightly as she stuttered to come up with words, “and wondered if you wanted to go to my place and play a board game or something, maybe a round of Risk?” Diana replied. She was skipping around the rule she had created and she knew it, but she wanted to beat him this time.

“Well my parents are gone. I guess I could leave them a note or something. Sure I’d like to beat you at Risk again,” He grinned.

Almost at once Diana’s nervous expression changed, having always been ready for a good ‘fight’ Diana grinned back as she replied, “I almost was the victor if you hadn’t had gotten lucky with those dice rolls, Leo, I would have won.”

“What can I say? I am surrounded by good luck.” Leo teased.

“Not tonight you aren’t. I’m going to rid you of your army and rule the world!” Diana said with higher spirits than she had since she had read Dare number 22.

“We’ll see about that, but first I need to write a note for my parents and then we will be on our way.” Leo said already headed inside. Less than a minute later he was back outside. “So how far away is your house?” he asked

“Only a block and a half away.” She states as the two both begin to walk to her house.

“And I didn’t know about it?” He asked teasing her. He made himself look horribly dismayed.

“I only knew about it because my parents took me here.” Diana awkwardly laughed as she looks at his ‘upset’ face.

“Cheater” He replied with a grin. His face of dismay deteriorated.

Diana only responded with a giggle. She turned around to face Leo. “I’ll race you the rest of the way,” she said and ran to her house.

“I don’t even know where you live,” Leo yelled to Diana. Then with a shrug he ran after her, intent on keeping up with her at the very least.

They quickly made their way back to her house and she swung the door open and entered. She arrived only a second ahead of Leo. They were both panting, trying to catch their breath as they leapt onto the nearest sofa and ended up almost landing on top of one another. Their odd position soon turned into a miniature battle of its own with the two battling it for ‘rulership’ of the sofa.

“I clam this sofa in the name of the Leo Empire!” Leo exclaimed as he halfheartedly tried to shove Diana off the couch.

“I clam rightful ownership of this couch and shall throw off the thief that seeks take ownership of it himself,” Diana replied, battling back.

After a few minutes of teasing and joking Diana jumped off the couch, “I’ll go get the game Risk so we can truly find out who is the better strategist.” She stuck her tongue out at Leo and then raced up the stairs to her room.

“Hey!” Leo called after her as she dashed to her room.

“Be down in a second!” Diana yelled back as she opened the door to her room. She had almost forgotten about the dare and her nerves when she opened up the door to her room and saw her box of cards resting in the center of the bed. Immediately remembering the dare her evil past self had given herself she slipped off her shoes, revealing her red knee-high socks.

“Let’s hope this ends well,” Diana said to herself.

As she looked around her room to find Risk her hand went under her clothing until she had made contact to her pussy. She then pleasured herself until her pussy became the slightest damp and her nipples hard, keeping herself as horny as ever. Her heart and mind were racing, not believing what she was planning to do. Her body shivered nervously.

Leo startled her when he yelled from the living room, “Need help?”

“Just found it!” she called back. She then spent a quick ten seconds more rubbing her clit before she grabbed the board game and made her way to the living room. She made sure to place the board game firmly in front of Leo.

[jklivin]

This is a very nice start set up real well I will be following daily.

[DrakeSebastian]

This took a little bit longer as it mostly setting up the 'plot'. Comments and suggestions are greatly appreciated. Thanks.


(Part: 3 Day: 1)

“Here is as good as place as any to set up the board game,” Diana said as she cleared the coffee table that rested in front of the couch. Leo pitched in as well and they quickly began to clear the table.

“You do realize that I am going to defeat you at risk again,” Leo said with a grin as he took a several news papers and set them off to the side.

Diana responded by mildly punching him in the side. She then went on to state, “I bet that I will be the victor. My Royal Empire shall be the demise of the Leo Empire!”

Leo grinned in response, “I’ll take you up on that bet. It will be my pleasure to send your armies to their doom”

“In that case maybe we should add some extra rules to this game of Risk,” Diana said, seeing an opportunity and taking it. She was now well underway in accomplishing her dare. She almost couldn’t believe it was working so well or that it was happening at all. She had never tried a dare that directly involved someone to the extent she was about to.

“Uh, sure. What kind of rules were you thinking, something to make the game more difficult and interesting?” Leo asked with curiosity.

“You could say that,” Diana replied, her tone getting daring, “I was more thinking about how the bet that we just made could be settled.”

“Ah. So you’re going to make the bet a serious one?” Leo asked with intense interest.

“Why not? Besides it might be fun,” Diana answered as she placed down the board game on the coffee table. An empty small world, divided into territories, was soon going to be taken over by either of the two, Leo or Diana.

Leo took a few seconds to think before he answered sounding slightly uncertain, “Sure, just as long as it’s nothing crazy it’s fine with me.”

“Um, how about we start with this rule, when one player takes a territory belonging to the other then that player can ask the person, who lost the territory, a question and the person in question must answer truthfully? Maybe we start with this and add more as we go or something?” Diana suggested. Her cheeks were faintly red as she spoke, unsure as to how he would react.

Leo noticed her slightly blushing and thought, “She wants to use this to get to know me better. Though she could also want to find out my plans of attack and stop them,” Leo thought with a devilish grin, liking Diana’s devious way of thinking.

Leo then spoke his reply to Diana, “Sure, I don’t see any harm with this rule. We could add more rules later on in the game to make the game more interesting or maybe change some of the rules we create later on. That is if it’s fine with you.”

“I think what you just said is perfectly fine. How about an addition to the rule,” Diana said, getting more daring and confident with herself. “Instead of just being truths how about dares? The person who loses territory can only pick truth every other time,” Diana’s face was deep red when she finished. She had not planned to make it so obvious of what she had intended, but the words poured out of her.

Leo was surprised by the idea. For the most part he though Truth or Dare as a childish game. This time however his mind thought of just a few possibilities of many and he quickly took a liking to it, “Adding Truth or Dare to Risk would be very interesting. Just as long as it stays in this house and does not become too crazy then it is fine with me.”

“Great! Now let’s get this game started so I can defeat you quicker,” Diana said enthusiastically.

“I think you misspoke for it will be the Leo Empire that wins the day and you will be singing the about the glory of my Empire” Leo corrected.

“We will find out shortly,” Diana replied with an evil smile.

Diana and Leo divided up the units. It was decided that Diana would have control over red and grey units while Leo would command blue and green units. They then began to divvy up the territory by taking turns placing a single unit on a piece of unclaimed territory. Both of them tried to consolidate their territory as well as stopping the other from doing so. In the end the map was speckled with their troops as well as neutral units. Both of them were not controlling any real staging point.

Diana had taken Greenland as one of her regions, allowing her to attack four different locations and to be attack by them as well. Thankfully she controlled two of the four already. She hoped that she could use Greenland to quickly take over the five territories in North America that she currently did not possess. At the same time she would use Greenland to stop Leo from gaining control of Europe. She only held two of the seven regions in Europe, worst yet was that they did not connect to each other. South America and Africa were mostly controlled by neutral units that would sit around and do nothing unless they were attacked. She did however have all but one of the territories in Australia.

After they had each claimed their fourteen territories and the neutral had taken the remaining fourteen they placed down their remaining twenty six units on territories that they owned. The map was now set and it was time to begin.

Leo took his turn first. Immediately he attacked one of Diana’s lesser defended territories and took it over with only one of his units lost.

Leo grinned, “Want to keep that extra rule still?”

“Yes,” Diana stated defiantly. “And for this one I chose Truth”

“What is your plan of attack?” Leo asked, starting off simple.

“I plan on quickly taking over North America and Australia as well as keeping you from taking Europe and Asia,” Diana replied truthfully.

“What about South America and Africa?” Leo inquired.

“That’s another question. Ask next time,” Diana said slyly.

“I might just do that. Now I’ll attack again,” Leo was already rolling his three dice, aiming to take out one of Diana’s regions in Asia. After losing two units and opening a weakness that Diana could later take advantage of he took over the territory.

“Looks like you have to take a dare this time. Hmm what shall you do,” Leo said in a mischievous tone. He thought for a minute before he spoke again, “I dare you to remove one item of clothing of your choosing.”

“So this is how the game is going to be played?” Diana asked with a wicked smile on her face.

Leo replied with a one word answer, “Yep.”

Diana surprised him by agreeing to the dare so easily; in fact he thought she would not agree to it at all. Instead Diana stood up from the couch and slid off her blue jeans. With a quick hop she stepped out of them and pushed them off to the side with her feet. She had fully revealed her red knee high socks as well as her plain black panties and long slender legs.

Diana was happily surprised that the dare coincided with one she had made earlier, thought it still didn’t change the fact that Leo was guaranteed to see her wearing just her socks and nothing else. The thought sent nervous thrills throughout her body.

Leo looked at Diana and knew that tonight was going to be most interesting. “I think I’ll end my turn here.” With that said Leo looked down at the board again moved some of his units to nearby territories he controlled.

While Leo was not looking Diana gently rubbed her pussy. Even without her pleasuring herself her nipples were fully erect with excitement and thankfully still hidden under clothing.

Leo looked back up at Diana causing her to move her hand to the side and hope that he did not notice what she was doing.

“It’s your turn now, here are the dice.” Leo said as he passed them over to her.

It was now Diana’s turn to take the offensive. She quickly took out one of Leo’s territories in America, trading one of her units for two of his.

Leo immediately spoke up, “I choose truth.”

“How do you plan to win this game?” Diana asked.

“I plan on first taking over Europe and Africa and then securing Asia. After that it should be game over.”

“Don’t think for a second that it will be easy to accomplish,” Diana said as she pointed out a new target in Australia that she was attacking and rolled the dice. She lost two units in the attack, but she had gained all of Australia.

“You have to take a dare now as well,” Diana smiled.

Leo’s face was covered in mocked terror.

“I dare you to…” Diana began.

[archie21]

I think you should write more, it makes a change from the school dares slave stuff.....

[jklivin]

I really enjoy reading this story, it appears it is about to take off. Great story.

[JosephDaftPunk]

This is a very exhilarating story! Keep it up!

[Sanpow]

wow, a realy nice written story. got realy horny while reading and would realy like if you continue soon ;-)

[Xxxdressxxx]

I'm liking the story so far

[iceman713]

I am very much enjoying this story. You are a very good writer and I hope to see this story continue.

[DrakeSebastian]

This is the 'Old Part Four' which will be replaced by a (hopefully) much better version at a later date in a new post. I thought part three was very slow for progress and then it went too fast with part four and was hardly up to standing with the other three parts of the story and so have decided to rewrite it. You will however still be able to read the old part four if you wish.

Spoiler:

[B](Part: 4 Day: 1)[/B]

“I dare you to… remove two items of clothing of your choosing and then,” Diana paused for a second as her cheeks reddened. “Masturbate every so often, keeping your cock hard,” Diana finally finished. She decided on this dare as it would give her more equal footing to Leo, almost mirroring Dare Number 22 her past self had given her.

“Sort of like you are doing then, trying to hid the fact that your hand was playing with your pussy while you thought I was looking away,” Leo teased Diana.

Diana’s face turned bright red, “You saw me then?” Diana cupped her both her hands over her black panties in embarrassment.

Leo laughed kindly. He liked how cute Diana’s face looked as she blushed. “Yes. At first I thought you were just fidgeting around, that is, until I looked over and you jerked your hand out from underneath your panties. If you hadn’t done that I might not have noticed.”

Diana’s cheeks turned an even brighter red. “I guess I walked into that one,” Diana replied.

Diana’s reply was met with another chuckle from Leo. In response Diana elbowed him in side.

“Ouch!” Leo said with a grin, only to be elbowed again. Leo raised his hands in surrender, “Alright, Alright I’ll stop laughing at how silly you look when you are embarrassed!”

This caused Diana’s angry face to blush and Leo had to restrain himself from laughing again. “So are you going to do the dare I gave you?” Diana said changing the subject to Leo.

“Under one condition, you must keep yourself horny as well and you cannot hide the fact when you are masturbating. Basically you get to stop being sneaky about it,” Leo said with a sly grin on his face.

Diana gently rubbed her hands up and down her panties. The idea of this new prospect was exhilarating for her body. The now horny Diana then replied with her decision, “Sure, just as long as you do the same.”

“Agreed,” Leo answered quickly. He was looking forward to the new spectacle of her masturbating in front of him. He was unsure about how he felt about him doing the same, but he thought it was a fair trade.

In compliance to the dare Leo took off his shoes as one of the items and then removed his shirt as the second item. His chest was skinny and hardly appeared muscular, but Diana liked the look as it seemed to fit with his face. Even without him being muscular Diana thought at the very least that he was cute and maybe just a tad bit handsome.

Leo for the first time was now the one to have red cheeks as he did the second part of the dare. Leo put his hand under his pants and quickly began masturbating. He up looked at Diana to see her suppressing a giggle. Leo’s face turned deep red as he looked at her body, secretly wishing that she wore less clothing and in his upcoming turn he could accomplish his wish. With little encouragement he got his cock hard and then quickly stopped.

After he was done Diana giggled, “You looked so foolish with your bright red face while masturbating.”

“Hey! You should have seen yourself when I told you I saw you trying to be sneaky while masturbating. Your face was almost solid red. I couldn’t stop myself from laughing. Though I do admit that you look cute while embarrassed,” Leo said, defending himself.

“I do not look cute. I look like a tomboy with my short cut hair,” Diana replied.

“Then you are a cute tomboy, either way you are cute,” Leo responded with a smile. He had planned to tease her as much as possible and he was doing just that.

“You’re hopeless!” Diana said. She picked up a small pillow off the couch they both sat on and threw it at him.

“I am at that” Leo agreed grinning, “Now how about you finish your turn so I can destroy your armies faster?”

“If you are so ready to lose then I shall comply and quickly finish my turn,” Diana slyly grinned as she looked again once more at the battle at hand. Right away she began her attack on a territory in North America, the last one that Leo controlled there. However she would not gain North America by kicking his unit out as three neutral territories were stacked with units and would ultimately stop her from taking North America for several turns.

In the first roll of attack she killed two of Leo’s units while losing none of her own units. The second roll she lost one unit but successfully took over the territory.

Diana turned to Leo, “So what’s it going to be? Truth or dare?”

“I think I’ll pick truth this time,” Leo answered.

Diana childishly stuck her tongue out at Leo, “You’re not any fun. Here is your question; why didn’t you speak up right away when you spotted me try to be ‘sneaky’, as you called it, as I masturbated?”

“Well, uh.. I,” Leo’s cheeks turned a faint red as he was put on the spot,” I guess I just didn’t think it would be right.”

“And?” Diana pressed the matter. She stood up and looked at Leo who still sat on the couch.

“I.. sort of.. liked watching you do it, and it sort of turned me on..” Leo finally answered.

“So something like this turned you on then?” Diana asked deviously as her hand went under her black panties and began to gently finger herself. She was pleasuring herself as much as she was teasing him.

“Yes,” Leo replied as his somewhat limp cock began to erect again.

Diana noticed the mound in the middle of Leo’s pants grow. She laughed when Leo tried to hide the fact that he was truly turned on by Diana and so crossed his legs. She knew Leo would most likely soon see her in only her socks, but she didn’t feel as nervous about it. Instead she thought of it more as a possibly interesting adventure and even then she still blushed at the thought of Leo seeing her only processing two items of clothing on her body, her favorite pair of red knee high socks.

Diana stopped after at least a good forty five seconds of pleasuring herself before stopping and returning her attention to the game at hand, which she admitted was getting harder and harder to do. She took out one neutral unit and then ended her turn after she had moved her troops around.

“It’s my turn now I see,” Leo grinned as he looked at the lands he controlled and the four new troops he was about to set down on the battlefield. Quickly finding good placements for them he set them down and without delay attacked one of the territories Diana controlled.
He took on Diana’s last territory in Asia. He ended up losing two units to take it over and set him one territory closer to taking Asia.

Diana looked at the board for a second before she made her choice. “I think I shall choose dare to start with.”

Leo grinned when he heard her answer. “Then to continue the trend of dares, I dare you to remove one item of clothing of your choosing and only pick dare from this point onward.”

“Paybacks are hell,” Diana winked at Leo as she stood up from the couch once more and slid her ‘slightly’ damp panties off her slender legs and surprised herself when she picked them up and causally threw them at Leo’s face. Diana was nice and allowed Leo to enjoy the sight of her well shaven for a few seconds before she sat down on the sofa once more.

“I have no doubt that they will be, but right now it is still my turn,” Leo grinned as he once more rolled the dice. He picked up Diana’s panties and placed them in his pants pocket. “You know I think I might start collecting these from you,” Leo teased her as a new battle began.

“We shall see,” Diana said, still having a few plans up her sleeves, even in the event that she had no shirt to hide them in.

[DrakeSebastian]

No comments? No one liked or disliked the newest post? If or when I cross a line that should not be crossed, please tell me, as this is my first undertaking of a story of this nature and so do not know how far or in which direction that I can ‘safely’ take the story and have it still be good.

[Sanpow]

last time i was here (reading the new part) i was... uhm... "busy" ;-)

I still like the story and realy want you to continue. But this part got much faster than the last ones. She took of her undies, he's masturbating for her (and she for him)... Last time it was something "special" if she took of an item of clothes.
Dont want to say it's bad, but it's not as perfekt as before ;-)