Jan was the first woman I strayed with. I was 49 at the time, she was 48, and she proved to be a significant influence in my life. I wrote this piece a couple of years after we stopped seeing each other, once I'd got over her and could put things in perspective. I owe her a lot.
Call it a mid-life crisis; I'm happily married to a wife I love, but her menopause and my strong sex-drive were the only ingredients needed for me to stray and seek pleasures I'd long fantasized about. I was eager to experiment before life left me behind. I met Jan on the internet, she was an escort and her on-line profile attracted me immediately. She'd written it well, it was the words rather than just her pictures that turned me on. She came across as genuine, down-to-earth, highly sexual and with the promise of a far greater bedroom repertoire than I'd ever experienced. She lived in the Midlands, and getting to her meant an hour and a half drive, so she clearly had a lot that attracted me enough to stray so far from home. That was part of the excitement though, and whenever I arranged to see her the journey helped to settle me and allow the sexual tension to rising steadily as I drove up the M5. Whenever I drive that section of motorway now I think of those times.
Jan was unattached, having been divorced twice. She had just started escorting and I was only the third or fourth man she'd escorted. We met at her nice flat on the edge of town. We swapped a few emails and spoke on the phone beforehand but I was still a bit nervous when I rang her doorbell. Thankfully she answered the door immediately and I later learned she'd been watching me approach from behind the vertical blinds. She lived in a discrete little close and didn't want the neighbors wondering about strange men on her doorstep.
I was utterly bowled over by her. Despite her diminutive stature, about 5'4" and very petite, she had a presence that captivated me. I put it down to her raven looks, her shoulder length jet-black hair, and steely blue-grey eyes that bore straight into me. I'd never seen such a strikingly attractive woman at close quarters before. She had an almost gypsy appearance, but she was dressed in a gorgeous black dress, black heels and her bare legs were beautifully tanned. I thanked my stars that hours of research on the internet had paid off and that I'd chosen well.
We'd agreed in advance to act out a simple role-play; I pretended to be a new neighbor with an envelope addressed to her that had been incorrectly put in my letterbox. The envelope contained her fee, thus avoiding the awkward transactional aspect of escorting, and the scenario meant she could invite me in for a coffee to reciprocate the good turn. As she greeted me at the door, I introduced myself and she invited me in. She then immediately blew it by introducing herself with her real first name, not her escorting name! She instantly realized her mistake, got a bit flustered and allowed me to give her a friendly hug by way of reassurance. We both dissolved into giggles at the rather ludicrous situation us two older people found ourselves in. Looking back, we later agreed that the moment effectively set us up for what became a very close relationship. Her innocent error endeared her to me immediately and we often had a laugh about it subsequently.
She later told me she'd never done any role-play before, was still nervous about inviting new men into her home and had been trying hard to come across as a seasoned professional. I came to learn just what a perfectionist she was and how very driven in everything she did. Later in our relationship she told me that she was struck by the confident way I'd introduced myself on that first date, and that it felt so normal, like meeting in any non-sexual context, that she'd just forgotten herself and used her real name. It got us off to the best possible start, we abandoned the role-play and she took me into the kitchen and made coffee while we chatted normally about ourselves. We couldn't get the words out quickly enough, we readily accepted each other's little physical touches as non-sexual contact as we drank our coffee and talked 19 to the dozen.
I've never met anyone like her, before or since. After 30 mins or so she took our mugs and place them on the table, looked straight into my eyes, placed her cool hands either side of my face and kissed me softly on the lips. My heart melted; I've never ever fallen for a woman so quickly. I can't describe the chemistry; it was all so new to me. She took my hands in hers, asked me if I was good with them, and before I could answer she stood and led me into her bedroom.
She proceeded to have her way with me, there's no point pretending otherwise, I was completely under her spell. Until that day no woman had ever knelt at my feet, undone my clothing and taken my stiffening penis into her mouth to fellate me with such passion. She took me to another world and I lost track of time, I was putty in her hands as she pleasured me, first orally, then guiding me gently back onto the bed and impaling herself on my slick erection. She looked at me, groaned that she'd not had cock for over a week and that she'd been gagging for me to arrive all morning. She proceeded to hump me and I'd never felt so used, but in the best possible way. She knew what she wanted and she took it, but in a way that showed my pleasure was hugely important to her. She was the consummate lover, dedicated to giving her man pleasure and reveling in being a 'man's woman'. She had a way of being very demanding in bed, tarty but classy in one, and highly imaginative. I've never come across such a passionate and accomplished seductress.
I'll always remember her lingerie on that first date. She was wearing a white lacy teddy with poppers at the crotch. I was being a bit inept at undoing them and she guided my fingers and helped me. She was sodden, and I'll never forget how she looked and felt as she fitted her vagina onto my erection, she was so hot and syrupy inside. She was obviously far more sexually experienced than me, I'd never met a woman with such a voracious appetite, and had never been taken in hand in the way she did. Once she'd climaxed several times I started to gain my confidence with her. I gradually took over the lead and brought her to several more orgasms in succession before changing position and giving her a frightful pounding on her back, her regular gym visits enabling her to be extremely supple with her legs. I never knew multi-orgasmic women really existed until I met Jan.
I was desperate to have her from behind on that first date, something that was not often on offer at home. She gasped that it was one of her favorite positions. I adored the sight of Jan on her knees, her narrow back and lovely round bottom flaring out in front of me as I guided my erection into her pussy. I loved seeing her dark hair on the pillow, the sound of her groans and cries as she gripped the bedding with her hands. I took in the view of the gorgeously feminine tattoo at the base of her spine, the first I'd ever seen close up and I realized what a turn-on some tattoos can be on a woman. Jan had several very discrete works of art on her body and I loved tracing them with my tongue. Her vagina felt so different in doggy; she had amazing pelvic muscles that squeezed my cock and I could feel every ridge and bump inside her as I slid the full length in and out. She became even more liquid in this position and fanny farted copiously on my cock without any embarrassment. I loved worrying her neat, wet little anus with the pad of my thumb, enjoying the feel of her puckered ring and the view of my penis sliding slickly in and out of her cunt beneath.
