tagToys & MasturbationA Happy Mistake

A Happy Mistake

byQuenton2123©

Kevin smiled as he dropped his backpack in the front entrance of his home on a Friday afternoon after school. With his parents gone to the cabin for the weekend he had the house to himself for roughly the next two days. This meant that he could do whatever he wanted, whether it was having friends over, walking around naked at all hours of the day, or even watching porn on his laptop with the sound on high.

Taking a deep breath in through his nose, and kicking his shoes off he walked into his home. He loved weekends in the late spring and summer, they provided such freedom. Smiling to himself he grabbed his laptop on the way to the kitchen, plugged it in and set it up on the island counter in the middle of the room, while prepping a pot of boiling water for some noodles. He booted it up, and logged on to Yahoo Messenger before returning to stir the butter and noodles into the water, which by now was bubbling furiously.

Kevin's attention was drawn back to his laptop when he noticed he had received a message from Kate, a girl he often chatted with. They began to chat for a while before the conversation changed, as it always did, towards playing what Kevin usually referred to as The Game. It was essentially just a sexual version of twenty questions.

"How big is your dick?" Kate's words scrolled across Kevin's screen.

"When I'm hard, like I am right now, it's about eight inches," Kevin replied with a smile, while reaching down to lightly touch his dick through his jeans.

"Oh, I'd like to see it one day," came Kate's reply. "Now it's your turn, ask me something".

Kevin paused a moment, thinking about what he wanted his question to be. He then typed, "Do you ever masturbate? And how often do you do it if you do?"

There was a short pause before Kate's response popped up on the screen. "Of course I do :P, and I do it almost every day, usually after school. There was this one time though, where I was so horny that I couldn't help myself; I wound up doing it at school, in the hall. I sat cross legged with my jacket over my legs. I came so hard," Kate said. "I don't think anyone saw me though, which is good. Mmm, this is making me horny. Here's my question: What is the hottest costume you think a girl can wear? Also can we do dares too, along with our questions?"

Kevin quickly strained the now cooked noodles, added the milk, and powdered cheese before returning to type out the answer to Kate's question. "Sexiest costume--- Hmm, that's a hard one. It would probably be school girl or cowgirl. Something about the skirts is so sexy :P," Kevin stated, very turned on at this point. "Sure, we can add dares. In fact, I dare you to go on the webcam topless".

"Only if you agree to go on in only your boxers," came the almost immediate response along with an invite to a webcam conversation.

"Alright," Kevin replied, immediately stripping his clothes off down to his boxers and accepting the request. This caused a large video link screen to pop up, showing Kate, sitting in what Kevin imagined was her bedroom, naked from the waist up. Her curly red hair hung down around her cute face to her shoulders. She smiled slyly and reached one hand up to cup one of her medium sized pale tits, whose bright pink nipples were standing at full attention. "Wow," Kevin breathed, "You have a fantastic body".

"Thank you," Kate replied with a broad smile, her shyness apparently melting away in light of his appreciation of her body. "Your body is pretty great too," she continued, her eyes obviously roaming up and down the digital version of Kevin on her screen. Kate then said, "Hmm, I want my dare to be something crazy," raising her eyes to the ceiling in mock thoughtfulness. "Oh, I know! I dare you to text a random girl on your phone asking for a topless pic, and you have to show it to prove that you did it," she finished with a mischievous smile.

"Alright," Kevin said, picking up his phone, and flipped it open to reveal the keyboard. He quickly typed, "Hey, I'm playing a game of truth or dare, and I got dared to text a girl asking her to send me a topless picture. Any chance I could get one of you? I'll owe you one if you do send it to me. Oh, and keep your head out of the picture in case they make me show it". He then sifted through the contact's list of his phone until he reached his friend Anne's name. Anne had been his close friend since elementary, and they had shared everything together, including their first time, which they had wanted to be with someone they knew they could trust.

He knew it wasn't exactly a random contact, but at least this way he didn't run the chance of being embarrassed. However, as he was pushing down the button to select Anne on his contacts list his thumb slipped and moved the highlighted name up to Ainsley. She was Anne's twenty-five year old sister. Kevin realized this as he was hitting the send button, and as a result the soft click of the button being pushed was associated with the silent sound of the bottom of his stomach dropping out.

"What's up? Was the girl super ugly? Does she have a third nipple? You look like you've just seen a ghost!" Kate's curious voice drifted through Kevin's laptop's speakers.

"Huh? Oh no, I just don't know the girl I asked very well," Kevin responded. In truth he knew Nicole fairly well, and had always harbored a bit of a crush on her. This wasn't surprising considering she was a drop-dead gorgeous woman, who was as smart as she was attractive and who had opened and ran her own successful small business at the age of twenty five. He now feared that when she looked at her phone she would think he was a giant pervert.

"Well maybe I can take your mind off it," Kate replied, standing up and turning around to reveal her tight ass which was a the moment neatly contained within a pair of equally tight jeans. Kevin watched her hands working on the front of her body. He couldn't see what see was doing until suddenly her jeans loosened considerably and she slowly started sliding them and her underwear down her body. Kate did this while simultaneously bending at the waist. Her smooth pale ass cheeks quickly came into view, which were quickly followed by a glimpse of her tight puckered asshole, and then her neatly shaved pussy which was glistening with wetness.

She then slid her hands up the insides of her thighs and, trailing two fingers across her pussy, buried them slowly between its lips. From there she turned around and sat down. Kate pushed her chair back so that Kevin could see her entire body, from her tits which rose and fell hypnotically with each deep breath, to her milky thighs which were currently spread as wide as they could be, to finally her wet glistening pussy into which Kate was currently slowly sliding her two fingers. "Take your boxers off. I want to see you play with yourself while I do this," Kate stated, her voice hoarse with her pleasure.

Kevin responded by immediately stripping his boxers off, revealing his rock hard cock which he promptly grasped in his right hand and began to stroke. "Mmm, rub your cock for me," Kate smiled. Her fingers starting to move faster, while her other hand slid up her body to her left tit and began to furiously tweak and pull on her erect nipple. "Do you like it when I finger myself?" she asked, her two digits now simply a blur on Kevin's laptop screen.

"Oh yeah," Kevin managed to grunt out in response, his hand now stroking his erect cock as fast as it could. As he jerked himself off for Kate, he could already feel himself building up.

"Ooh!" Kate moaned, sliding her wet fingers out of her pussy and up to her clit, which she began to rub, one finger on each side. "Mmmm, ooh yes," she gasped, leaning her head back onto the headrest of her chair. Her eyes locked on the image on her screen of Kevin's hand racing up and down his dick. She then lifted her one leg up and placed it on the top of her desk. Kate slid her other hand down her side and under her raised thigh and began to play with her pussy.

She slid her fingers into it, and drawing the juices down, began to play with her puckered asshole. After she had her tight rosebud glistening with her own juices she began to push her middle finger up into her ass, slowly at first and then faster. Her moans getting louder and louder as she rubbed her clit with more and more ferocity. She began to thrust her hips slightly, trying to drive her finger deeper and deeper into her hole.

"Ooh yes, I'm gonna cum Kevin!" she shouted, her body tightening up in expectation before she was hit with a wave of pleasure. Her orgasm ripped through her body, reverberating up from her pussy to the ends of each of her extremities. Her gasps and moans tore out of her throat as she was gripped in wave after wave of pleasure.

This was too much for Kevin, and he started to cum. His eyes locked on Kate's writhing form, her fingers still darting across her pussy and driving into her tight glistening asshole. He felt his balls tighten up in expectation and then release, firing load after load onto the floor of his kitchen as he came harder than he had in a long time. His breathing was heavy and hoarse as every nerve in his body pulsed with pleasure.

It was several minutes before they had both come down and cleaned up enough to continue talking. "Oh my god, that was so hot," said Kate. "I don't think I've ever come that hard". She was still slightly hoarse and out of breath from earlier.

"Same," replied Kevin, his eyes traveling up and down the digital image of Kate's naked form, her skin flushed pink and shiny with sweat.

"Hey, did that girl ever respond to your message?" Kate asked, sitting up slightly with a bit of an exhausted but curious smile on her face.

"I don't know; I'll look," responded Kevin, feeling slightly apprehensive as he picked up his phone and noticed he had a new message. He quickly opened it and read the text: "Oh, I'm flattered you thought of me! Here are two pics, one for your friend and one for you for later. Also you should totally come to dinner tomorrow at Anne's. I'll be there!"

Scrolling down on the text Kevin saw two photos of Ainsley. Both were apparently taken from behind a desk in an office with a large glass window behind it. The first showed only a pair of large perky breasts framed by an unbuttoned black shirt and a bra which had obviously been pulled down. The skin on her breasts was pale, but with slight tan lines from a bikini and dark pink nipples which were obviously erect. The second photo was much the same except that instead of being revealed from beneath a shirt, Ainsley's ample tits were peaking out from a dark blue blazer under which she was obviously wearing nothing. This photo also included her face, which bore a broad, slightly hungry smile and a very obvious wink.

Report Story

byQuenton2123© 1 comments/ 18636 views/ 4 favorites

Share the love

Tags For This Story

Report a Bug

1 Pages:1

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

heartnerdword, teana and 2 other people favorited this story! 

Recent
Comments
by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.

There are no recent comments (1 older comments) - Click here to add a comment to this story or Show more comments or Read All User Comments (1)

Add a
Comment

Post a public comment on this submission (click here to send private anonymous feedback to the author instead).

Post comment as (click to select):

You may also listen to a recording of the characters.

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar:

   Cancel