This happened when I was 14, about 10 years ago.
My parents were going out of town overnight and even though they knew I would be fine, they still had to worry about my younger brother (he was 8 at the time). So they hired Maggie, the usual sitter, to stay overnight.
Maggie was 17 at the time and very well developed. She was a busty (easily 34DD), curly blond haired girl who had these adorable freckles on her cheeks and nose with sky blue eyes. We were pretty good friends, considering we'd know each other for years. Usually we would stay up playing board games and watching TV whenever my parents hired her.
I was up in my room, working on an essay for school on Monday when she strolled in and plopped onto my bed.
'Whatcha' doin'?' she asked.
I turned to look at her, she was astounding. She was wearing overalls with a light blue shirt on underneath. 'Just some homework.'
'Boring! Cmon, I just put your brother to bed, let's go on the deck and chill out,' she said.
So we went out on the deck, relaxing on a couple chairs and looking up at the stars. 'So how's school going?' she asked me as she turned on her side to look at me.
'It's ok, we've been learning about some weird stuff.'
'Really? What kind of weird stuff?'
'Um, like the sex ed stuff, that kind of thing.'
'Sex ed isn't weird, Tony, it's fun.'
'It's like you have all these girls around you and you're getting instructions on how to use them properly....kind of like driver's ed.'
I laughed, 'I guess.'
A pause came between us, she was looking at me hesitantly and then said, 'So have you got to practice yet? Using what you learned?'
'On who, myself?'
She nodded, 'Yeah.'
I wasn't sure what she meant. 'You mean like masturbate?' Another nod, this one with a smile. I shook my head, 'No, I haven't tried it yet. It seems dirty.'
She smiled and laughed a bit. 'Dirty?' Her hand disappeared down the side of her overalls and she made an 'ohhh' sound as she looked at me, 'does this seem dirty?'
I wasn't sure what was going on, I look confused I guess because she stood up and unhooked the overall straps. They fell in a heap at her feet and she stepped out of them. She had on no panties and she had a finger working her clit just slightly as she looked at me.
'You like what you see, I guess,' she said nodding at my shorts. I looked down and they were fully tented. 'Here, let me help you out.' She knelt down beside me and slid my shorts down. I shuddered a bit, nervous about what was happening, but Maggie gasped. 'Holy shit. You're pretty huge.' My dick has always been eight and a half inches, ever since I hit puberty. Until that moment, I always thought it was a bad thing.
Maggie brought her hand away from her soaked pussy and started stroking my hard cock with it. She was so delicate and gentle, her juices warm on my dick as she worked it. 'Gonna' cum for Maggie, Tony?' she teased as stroked away.
'It feels weird.'
'Don't worry, it's natural. You're gonna' feel great here in a few moments.' She took my hand and guided it to her soft mound. I felt the smooth patch of hair just above her slit. 'Show me what you learned,' she said and I rubbed two fingers up and down her slit before resting on her clit.
Our soft moans filled the night as we worked each other over. I must have doing something right because Maggie would frequently say things like 'that feel so good' and 'right there, I'm so wet'. Before long, I felt scared as my body started to tingle and I looked worriedly at Maggie.
She smiled and moved down to kiss my lips as I felt my dick seize up and shoot four hot jets right on Maggie's side. She moaned into my mouth as her hand met mine on her pussy and she slipped my two fingers into her pussy as she came.
Breaking the kiss, she pulled away and held up my hand covered in her cum. I licked a bit off, savored it and then had a bit more. 'You like it, I guess,' she said with a smile and then leaned in close, 'that was amazing.' She sucked my fingers clean of her cum and then kissed me hard, her sweet cum taste still on her tongue.
That began a secret relationship that lasted until the next year when she went away to college. We had lots of fun together.