I suppose I should start this off by making it quite clear that I do not consider myself a pervert. Maybe 20-30 years ago I would have been, well perhaps not a pervert, but kinky, or weird.
I have a thing for older women. It began in school when like all the guys I fantasised about the leggy English teacher. I never really got past that stage. So far, so mundane right? I mean its kinda fashionable these days ain't it?! Cougar sex, milfs..... this is the era of the older gal with the young lover, Demi and Aston etc.
I'm quite a shy guy, I don't mind admitting it. I've not had a problem getting to know girls around my own age, but I've never been confident enough to walk up to someone older and chat them up. There's something unattainable about a classy, elegant older woman. Something mysterious and intimidating.
So, the best thing that ever happened to me was the internet! Not long after buying a pc for the first time, www.olderyounger.com was bookmarked. Here's my ad:
Young, athletic, smart guy. 23, 6'2, 185lb. Interested in meeting up with an elegant, stylish older woman.
Not particularly original but All true and by the way, very effective. I posted that with a couple of snaps of me at the beach and in the gym and boy did it pay off. It'd be crass to tell you how many women I slept with at that time, but in 2002 I could have won the toyboy of the year award. I became expert, not just at the obvious (massage, cunnilingus, intercourse) but things that woman also like: talking, listening, how to dress and how to act with a woman. A lot of the woman I dated were over 45, divorced with a lot to get off their chest. Some were alcoholics, some couldn't adjust to life post 40, I became a counsellor as well as a lover. I wasn't just having one night stands, I was regularly seeing 3 or 4 women at a time with no strings attached. I got to know them and like them as well as go to bed with them. I liked myself, I had the best of both worlds. But of course, whenever you're having your cake and eating it, something comes along to spoil things.
That thing was Anne. Anne was a beautiful 49 year old woman. The moment I came upon her profile I messaged her and the moment she got my message she replied. Everyone knows that you can't tell how you'll get on with someone when you meet offline, but sometimes the rapport on IM is so instant and strong you just KNOW you're going to have a good time together. She asked for a snap of me on a beach in Thailand for her phone, she sent me my favourite from her album. She was stood, a 5'9 Amazon of a woman, full breasts poking from the top of a tight pink cashmere sweater. Her brown eyes looked up saying "Come hither" from under a bundle of delightfully swept dusty blonde hair. Her figure was voluptuous and her face framed by high Slavic cheekbones. It was the first snap I saw of her online and I still remember how it gave me an instant erection.
We'd been chatting for two days, and then she asked if we could meet up. She invited me to hers.
She lived on the South Coast, it was a 70 minute train ride. I loved those journeys, the anticipation, adventure, new places and new women! She met me at the station looking sensational. She was more formal than in her pink sweatered photo. She wore a long brown suede jacket, a pair of pinstriped black trousers and sunglasses. She'd obviously had her hair done especially, it was full and shone silky smooth, and I immediately complimented her on it. I was wearing my tight wranglers and a light blue button down shirt. We embraced by way of greeting, it was a polite hello but her body was soft, warm and made me look forward to more. She kissed my cheek, a kiss full of desire.
"I thought we could go for a drink?" So she was that type. Maybe not an alcoholic, but a woman who enjoyed a daily drink to make the hours pass easier. We went to a trendy but not overly expensive place. I bought us both a JD and coke. In the mirror I caught sight of her checking out my ass and thighs as I stood at the bar. I walked back smiling. We touched glasses across the table, and then it began. The revelation.