Just wanted to say thanks to the authors of the 'sex confession' type stories on this site. I prefer the stories based on what really happened, with all the details as to why it was memorable...
I am interested in your feedback, so please give your comments and thoughts on my story.
The following encounter happened to me 10 years ago in Mexico. It was my first experience of bedding a MILF, and I think it was her combination of initial primness and subsequent dirtiness that stuck in my mind.
I had just turned 30 and was backpacking alone in the Yucatan peninsular. It was part of a bigger trip I'd wanted to take for many years, but since my girlfriend had dumped me some months earlier I was travelling alone. This part of southern Mexico has a wonderful climate in December, and lots of colonial Spanish towns and Mayan ruins to visit. You can get around by bus easily and it's cheap to eat and get a room in small guesthouses. I had purposely avoided the big coastal resort of Cancun, popular with package tourists and conferences etc. I just wanted to see part of the real Mexico.
It was whilst waiting for a bus south towards Belize that I met Amy, a 40-something divorcee from the US. She'd been attending a conference in Cancun, and was spending a week seeing the Mayan Riviera before heading back home to Boston. I didn't immediately fancy Amy at first sight, she looked a bit tired and dusty with the heat, in T-shirt and shorts, but she had a bubbly friendly personality and seemed smitten with my English accent. She was pretty, but beginning to struggle with her weight a little.
I'm no Brad Pitt so I'm not being mean...just saying how it was. On the bus and later that evening I began to see her more favourably. She scrubbed up well, and her jeans were amply-filled, straining the material tight across her arse. I love it when any clothing is stretched taught and wrinkles in that certain way that says there's a curvy woman inside. She had a cheeky smile and was quite tactile. Her attention was most welcome...
Later that evening we had a 'moment' after eating in a restaurant near our 'dive' of a guest house where we both had rooms. I'd had a few beers and kissed her on the beachfront on a whim. It was a little awkward as I was horny as hell, my erection awkwardly unrestrained in my boxers. I was somewhat surprised by the whole situation as she was more than 10 years older than me, but she seemed keen. I ran my hands over her back, feeling her soft warm skin below her T-shirt. My cock jerked when my fingers found a hint of cool satin panty protruding above her jeans-clad arse. Amy moaned slightly as I teasingly tugged at the smooth panties. Her tongue pushed deeper into my mouth, deliciously filling it and exploring. She said I was making her feel like a teenager again.
We got back to her room and she said I could come in if I promised to behave myself. She told me she always kept her clothes on a first date, and that she wasn't a slut. I nodded earnestly. Frankly I would have agreed to anything to get into Amy's room. I was expecting a fairly chaste snog after this talk, and in some ways it was pretty innocent. After a dry period, I was super-sensitive to this woman's touch, and feeling her weight on me was magic. As we kissed her hands were all over my clothed body, caressing my chest, stroking my stomach, cupping my crotch through my trousers, fiddling with the zipper, rubbing my cock, and squeezing my arse. Later I was on top of her, running my hands over her full tits beneath her bra and top. I was lying between her legs, grinding my crotch into hers, feeling the sweaty heat between us, as she raised her pelvis off the bed in time to my thrusts, moaning quietly. Her hands massaged my bum through my trousers, and periodically her fingers probed the material into my arsehole. I told her I was in danger of creaming my pants and she giggled and told me she hoped she was having that effect. I jokingly told her she would have to clean up the mess if she made me come in my dressed state. I told her how hot she was, apologised for how turned-on I was, and lied that I wasn't normally in danger of ejaculating just from heavy petting.
Amy admitted I was making her desperate for cock, and that she badly needed her pussy filling, but she wasn't a bad girl and wanted to take it slowly.