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Midnight Mischief

Will middle aged Sharon give in to 16 year old Jake's sexual desires?
My name is Jake, I'm sixteen years old and last week I had one of the most amazing experiences of my life.

It was Friday afternoon and school had just finished. Usually I would just play computer games at the weekend but this weekend I was having a sleep over at my friend Ross's house. We had been good friends since we both started the school five years ago and often went around each other’s houses.

At 3:45, Ross's mum was here to pick us both up. She is in her early forties, her name is Sharon and she has beautiful blue eyes. However, her best feature is most definitely her strawberry blonde hair cut at shoulder length. She is fairly curvy and has perfect breasts - I would guess about a C or D cup. She is not the best looking woman in the world but there is just something about her that makes me feel tingly inside every time I set eyes on her.

Anyway, we threw our bags in the boot if the car, Ross got in the front next to his mum and I climbed in the back. She did the usual mum after school talk - have you had a good day at school? What have you been up to? Then it all went pretty quiet so she turned on the radio. We were half way home when I realised that the rear-view mirror in the car was perfectly positioned for me to stare at Sharon. I sat there for a while looking at her, then my eyes trailed down to her breasts. It was a warm day so she only had a vest top on and I could see the tip of her pink floral bra sticking out the top of it. As I sat there staring, I suddenly realised that she had seen me. We made eye contact, she smiled and I smiled awkwardly back, trying my best not to turn a deep shade of red.

We got home and she asked us what we wanted for dinner. She put it in the oven and then said she was going to go get dressed into something a bit warmer, as the weather had now cooled down a bit. This gave me a brilliant idea and it took a lot of courage, but five minutes later I told Ross that I needed to go to the toilet.

I left Ross watching T.V. and tip-toed up the stairs as quietly as I could. The house had a funny layout as most of the bedrooms were downstairs, but I knew that both the bathroom and Ross's parents' room were both upstairs. Even better, I knew that Ross's dad work away on weekends so Sharon would be the only one up there. I walked past the bathroom and to the room next door. I breathed in nervously and then swung the door wide open.

"Arghh!" Sharon screamed in surprise as I had caught her in her underwear. I had actually wanted to catch her fully naked but this was good enough for me.

"I'm so sorry," I replied, "I thought this was the bathroom." Then I took a step forward. She didn't move, so I took another step forward and grabbed one of her breasts. I looked up at her to see what her reaction would be and thankfully, she was smiling.

"Kiss me," she said.

We embraced in a passionate kiss. Our lips made slapping noises as they met, and I licked her face with my tongue as I did so. I moved my hand down her body and was about to slide it into her knickers, but she pulled away.

"No Jake, I can't have sex with you, you are too young."

"Please Sharon, let me fuck you," I replied, trying to persuade her with dirty talk.

She paused for a moment, looked at me and grinned.

"Sneak into my room tonight and we can arrange something."

I returned the smile, turned around and walked out of the room. I couldn't believe it; I had actually pulled a milf!

Sharon never said anything about the event for the rest of the evening, although she had a pretty red face throughout it and there were some awkward glances at the dinner table. At 10 o'clock we said good night to her and went to Ross's room (which is downstairs) to watch a movie. Throughout the movie, all I could think about was Sharon's naked body. Her curves had looked great and she was wearing a frilly pair of thongs that matched her floral bra. What surprised me most was that she had her belly button pierced and had a small playboy bunny tattoo emerging from her bikini area.

The movie finished and the credits started rolling. I asked Ross if he was going to turn it off but got no reply. I soon realised that he was fast asleep, so got up and switched the T.V. off myself. Through the gap in the door, I could see the stairs that lead up to Sharon's room. I was wondering whether or not she was serious about us having sex, but then I realised it was a once in a life time opportunity so decided I would take the chance. I decided I would sneak up to her at 1:00 am to make sure everyone was fast asleep. I got into bed but couldn't sleep. I looked at the clock; it had just gone midnight now. I rolled over a few more times, and then looked at the clock again, it was 12:10. This was ridiculous; I was never going to be able to wait until 1:00. I looked at Ross and he was now snoring quite loudly. I once again took in a nervous deep breath, got up, widened the crack in the door, and walked out.

I tip-toed back up the stairs again and stood outside Sharon's door. I put my ear against it and heard the gentle breathing patterns of her sleeping, so I gently opened the door and walked in. As I shut it behind me again, it creaked quite loudly. She moved but didn't wake up. I snuck up next to her double bed and lifted the duvet at the end she wasn't sleeping. Then I climbed in.

It was a great feeling to be laying there next to the woman I had secretly had a crush on for years, and now I just had to make sure things kept going well. I gently moved my finger down her back. No bra strap! Then I let it carry on further down. To my delight, I soon had it sliding into the crack between her cheeks, proof that she was completely naked. I decided to join her and pulled of my boxers and threw them on the floor. Now came the real test.

I pulled the duvet slowly completely off the bed. At first, she began moving around looking for it in her sleep, but then she settled back down. She was now lying on her side so I gently pulled her shoulder so that she was lying on her back. As I did this, her legs spread open, giving me the perfect view of her pussy. To my surprise, it was fully shaven and the bunny tattoo was now in full view. My own private part was now harder than it had ever been before and I couldn't wait to get it to work. I knelt down between her legs on my knees and then leapt on top of her. Her naked boobs squashed against my chest and my hand quickly covered her mouth as her eyes shot wide open and she started grunting loudly and squirming around.

"Shhhh. I'm not going to hurt you," I reassured her. "You remember our deal, right?"

She nodded so I removed my hand from her mouth and sat up.

"Jake, I'm not sure that I should be doing this?"

"Please Sharon, I just really, really want to fuck you," I replied.

"But I'm forty two and you're only sixteen!"

"Please, you're so hot."

"No, Jake I'm sorry but I've changed my mind. Now please put some clothes on and get out or I'll have to call your mum to come and get you."

I panicked, "Fine, but if you refuse to sleep with me I will tell your husband that you kissed me when I saw you getting undressed earlier on."

"Are you crazy? That would ruin our relationship!"

"Your choice," I replied bluntly. She looked at me for a while, and then said, "I will let you touch me for a bit but nothing else."

"No, I want to do more than just touch you. Say yes or you may as well file for divorce now!"

"How about just a blowjob?" she replied. I didn't reply, but she could see the determined look on my face.

She gulped and nodded, "Well I don't see how I've got much choice then, but I'm very ashamed of you for making me do this."

"You'll enjoy it, trust me. Now spread your legs!"

Sharon obeyed and I lay down between her thighs. For somebody who didn't want to do this, her pussy was very wet. Infact she had already created quite a considerable moist patch on the blue sheets. I began to tickle her clit with my tongue and then slid in a finger. I could see that she was trying her best not to show any enjoyment but every now and then she let a groan slip and then eventually her whole body spasmed and her pussy was thrusted upwards where it spurted warm liquid all over me.

"So how was that?" I asked.

"Please just get this over and done with," she replied. She was consistent, I'll give her that.

I told her to get on her knees and suck me off. She tutted but once again quite quickly obeyed. Her wet lips wrapped around my firm manhood and I felt her tongue licking the tip. Her teeth nibbled me and she began thrusting her heading back and forth on my shaft, the rhythm getting increasingly faster. I held her red hair and pushed my hip into her face so that she deep throated me. She started gagging and tried to pull away but I held a firm grip. She was turning a funny shade of red just as I release my load down the back of her throat. She flopped onto the bed, gasping for breath.

"Okay, so how was that then?"

"Hmmmm, better," she replied as she swallowed the last of my cum. I could have sworn I saw a slight smile too.

We lay next to each other for a little while on the bed, while we got our energy back. After a few moments silence she said:

"You know you are surprisingly good at eating a girl out!"

"Thanks, you are surprisingly good at sucking a guy off!"

Then she definitely smiled. I leaned over her and kissed her. She pulled away. As if in a movie, we looked into each other’s eyes and then kissed passionately for the second time that day. Ours tongues twisted around each other and I nibbled on her nose. Then I licked her chin, and down her neck, until I ended up at her breasts. They were beautifully shaped, with only a little sagging. Her nipples were small and lovely to suck on.

I got Sharon onto all fours and leant over the top of her. Then I guided my refuelled cock into her warm pocket of moisture. The thrusting started slowly but then gradually built up.

"Oh yes Jake, fuck me hard. Fuck me hard!"

This was just the kind of talk I needed to get me going and we were eventually going at it quite rapidly. Her tits that once hung nicely down from her body by the force of gravity were now making loud noises as they slapped against her chest. I felt her muscles tighten around my cock as she gasped and flopped onto her elbows. As I felt her moisture it set me off, and I released deep inside of her.

"Oh wow, I have never had an orgasm like that before," she gasped.

"Me neither," I said, and then I kissed her on the cheek.

We lay down next to each other again and she told me she was going to the bathroom to get cleaned up and that I should go back to bed now.

"Ok, but can I take these as a souvenir?" I asked, holding up the pair of floral thongs that she had been wearing earlier.

She smirked and nodded, and I spanked her ass as she got up to go to the bathroom. I got one last eyeful of her curvy body and then snuck back downstairs to bed.

At breakfast, the following morning I couldn't take my eyes off Sharon and we both kept smiling to each other. Luckily, I think Ross had slept through all of last night’s events, but I think I'll definitely be coming here for a sleep over again!

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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