Written by wadskil

15 Oct 2007

I read a lot of the stories and a lot of them seem more like fantasies than actual events. When I was in my early twenties me and a friend used to wonder what it would be like to have an older women, whether we would go through with it if we had the chance or whether it would remain a horny fantasy. When I enrolled at a residential college in Oxford I got the chance to find out.

The women who ran the canteen and did the cleaning were a bawdy lot, always making suggestive remarks to us guys. Some of them were very sexy. The woman who cleaned my room was called Lily. She was not as bawdy as the others but she was the sexiest, in my opinion. She was in her early fifties with curly dark hair flecked with grey, a nice, friendly face. She was, I suppose, plump but curvy with a nice, round bum. Her breasts were beautiful for a woman her age, nicely curved. I always made her a coffee and chatted when she turned up. I thought nothing of it till one day I came into my room when she had the hoover going. She didn’t hear me come in. She was on her knees hoovering a corner. Her skirt had ridden up to the top of her hold-ups and I found myself faced with an amazing sight. The fat bulge of her fanny was clearly visible through blue lacy knickers, little black hairs escaping from the sides. My cock stiffened instantly.

I waited a moment then closed the door hard. She jumped and straightened her skirt. She looked so embarrassed, I said nothing. Later that day I had a tremendous wank on the basis of that wonderful sight, imagining what it would be like to pull aside the crotch of her knickers as she kneeled and slide between those soft fat fanny lips. I realised that in reality I would love to fuck her, but had no idea how to go about it, or whether she was amenable. Despite what happens in stories, propositioning a woman isn’t something that pops up in conversation easily. We continued to chat over coffee and I continued to wank and fantasise.

Two sets of circumstances changed all that. Just before the Christmas break I picked up a girl at the swimming pool and got her back to my room. She was gorgeous and had a fantastic body. Everything was, as they say, as it should be. But the sex was crap. She was shy and unadventurous, more than a little ‘up herself’. Anyway, she stayed over. The next morning I had her sitting in the armchair, her long legs draped over the side, licking her out like my life depended on it. I had just raised myself up to get inside her, my cock jutting out, rigid with a morning erection, when the door opened. It was Lily, come to do the cleaning. She gasped as I kneeled there, there was a pause, then she closed the door. The girl was mortified, she got dressed and left.

In the days that followed, Lily stayed for a coffee and a chat, but made no reference to that day. Finally the last day of term arrived. As we chatted over coffee I told her I was going home that evening, then an idea popped into my head. I asked her what time she finished work. She told me two in the afternoon. I suggested she drop by for a festive glass of wine before going home. She agreed and told me she’d come by after she’d had a shower and got changed. At this stage all I planned to do was flirt with her over a drink, just to be mischievous.

Was I in for a surprise.