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.