16th February 2013 - 11:26 | Bristol UK, Bristol
Over the years I have managed to have quite a few sexual encounters with women via online classified ads. I'm an attractive guy in my twenties and quite able to attract women in real life but for some reason I find the feeling of finding a stranger online for sex a uniquely appealing thrill. It is something I would never admit to anyone I know, but something I keep doing regardless. I thought I would share a few stories of my experiences...
My first online experience!
The first time I met with a stranger I found online was when I was 24. It was through the old Gumtree dating section - I used to love reading the ads posted there, which were often quite sordid but mainly real and posted by "typical" people who read Gumtree for accommodation or to buy/sell things. I never posted my own ads (which I later found out was the best way to meet people!), but would occasionally reply to ads put up my women looking for sex.
The first reply I made that ever got a response was to a simple ad that I thought was probably not even genuine, by a woman who said she was a bored housewife, 39 years old, who wanted a younger man to use her. She responded and it quickly became apparent she was real - she said she was married but every so often she would have a man over to do whatever he wanted with her, with her husbands permission. I was at work at the time, but she said if I came over at 8pm she would meet me at the backdoor, and I was to kiss and fondle her on the doorstep - she said the thrill of being seen turned her on. Then she said she would give me a blowjob. (Coincidently it turned out she lived literally a 5 minute walk down the road from me)
I was nervous as hell as I walked up her driveway that night, unsure if she was real or this was all a wind up. I realised it was definitely real when she opened the door in a dressing gown, which she dropped when she saw it was me, to reveal she was wearing only stockings underneath (no bra or pants). She stepped out onto the steps, which were fairly concealed to prying eyes, and kissed me - I fondling her breasts and squeezing her ass for a couple of minutes before she pulled me inside. Inside she dropped to her knees and started undoing my belt. I was not quite hard yet and a bit worried about it, since the whole thing was pretty nervewarcking. I had time to look at her properly as she was unfastening me - she was curvy but had an attractive body, with a tattoo on one breast. She did look a bit rough, perhaps a little hardened by life, but on the otherhand had great breasts and was very willing! She took me in her mouth and started sucking - at first I stayed only half erect but she stopped for a moment to tell me to fuck her face. Her simply saying this turned me on hugely and I started gently, and then more roughly, sliding my cock in and out of her mouth until I came, and made her swallow.
I left pretty much immediately, and as I left I thanked her. At home we exchanged more messages, and she said I should not have thanked her as she simply wanted to be used and didn't deserve thanks. She also said she wanted to be my fucktoy to practise on until I found a girlfriend, and it was convenient since I lived so close. In the end, the whole thing weirded me out, due to my inexperience, and I did not meet her again. If I had this situation now I certainly would have used her but at least I will always have the memory though of the housewife I facefucked!
Hope you enjoyed the story - it is completely true. Feel free to get in touch to tell me what you think.
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