When I was young, my best friend's mum, Janice, was my favourite fantasy figure. She was in her mid-40s, shoulder-length brown hair, nice face, very curvy body with nice big boobs and bum. I thought about her so often while I was masturbating as a teenager.
One rainy afternoon, I was out delivering newspapers, and got soaked to the skin. My last delivery was to one of Janice's neighbours in the same block she lived in. I was about to leave the building after delivering the paper when I bumped into Janice coming into the building. I said hello, she said 'oh, you're soaked, come in for a cup of tea and get dried off', so I agreed, glad to get somewhere warm and dry.
My friend was out at college, and wouldn't be back for some time, Janice told me to go into his room and take my jeans off, she handed me a dressing gown belonging, I presume, either to my friend or his older brother. I took off my shirt, just as Janice came into the room, saying 'give me your jeans and I'll hang them up to dry off for a while'. I stopped, suddenly nervous about taking off my trousers in front of this woman I'd fantasized about so often. 'Come on,' she said, 'do you want me to look away?'.
'No, it's fine,' I gulped, and undid my buttons. I started slipping my jeans down when an idea struck me. Despite being suddenly terrified, I pulled my jeans down but made sure they 'accidentally' dragged my boxers down with them. I pretended not to notice at first as I took my jeans off completely then stood up straight, and pretended to suddenly notice that my boxers were half way down my thighs, exposing my penis to Janice. It was just in the first stages of erection, when it's not hard or sticking up, but grown slightly, and the helmet become more prominent. 'Oh, I'm sorry,' I said, yanking my boxers up, clumsily flicking my cock up with the waistband as I did so. I looked Janice in the face, she was smiling slightly and still gazing at my boxers, where the bulge of my now hard cock stuck out towards her. She took my jeans and, still smiling, left the room.
I was so aroused that I had to pull my cock out and wank, coming quickly and copiously, which I cleaned up with a paper hankie from the box next to my friend's bed.
I pulled the dressing gown on and went through to the front room where Janice was sitting, her legs tucked up beneath her on the couch, the glossy shine of her black tights turning me on again. We made some small talk for a while until Janice said 'you'll have to get home, your folks will be wondering where you are' and stood up to get my jeans from the dryer. As she stood up, she swung her legs round and planted them on the floor very wide apart, her dress had ridden up a bit and I could feel my penis twitching as I looked at her nylon tight-clad thighs and the alluring darkness up her skirt, although I couldn't see anything.
Nothing else happened, except that as I left, I thanked Janice and she kissed me lightly on the cheek and said 'thank you too.'
That night I masturbated furiously, several times, thinking of Joyce in her black tights staring at my semi-hard cock. I ejaculated huge strings of cum picturing her.
About five years later, I did eventually fulfil one of my lifetime's ambitions and have sex with Janice, finally seeing those boobs and pussy I dreamed about so often, but that's another story!
Janice has moved away from the area now, but I'd love to bump into her again and relive old memories.