Jan, My "Mrs. Robinson"

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.

We finished with me eating her out and examining her in the most detailed and intimate way possible. She told me that no-one had ever examined her quite like it and she loved having me worship her in that way. In hindsight I can honestly say that she had the neatest, smoothest shaven vagina I've ever seen; she loved hearing me compliment her on her intimate appearance and I'd tease her that it reminded me of the pencil drawings in my school biology textbook -- a symmetrical slit, exquisitely shaped and sized labia, and an adorable clitoris nestling under its beautiful little hood.

Any thought of looking at the clock was forgotten and we spent several hours in bed, including a period where we fell asleep exhausted in each other's arms. I left her many hours after I'd arrived and drove home back down the motorway feeling as if I was floating on a cloud. I was completely satisfied sexually, but I came to realize with time that it had stirred something deep inside and I wanted more, like a drug.

We met again just a few weeks later. Jan wrapped her arms around my neck and slipped a thigh between my legs to press against my stiff cock as we stood in her hall on my arrival. Our emotions and our desires were at fever pitch and we consumed each other's faces with hungry mouths. We went straight to bed without coffee, this time she was wearing a black teddy and she took my hand and put it under her dress and straight to her crotch to undo the poppers; "you're getting better with them," she teased.

I'd arrived at 10am, the earliest I could sensibly get to her and we spent the morning in bed devouring each other. We had the whole day together; we went out for lunch and sat in the sun on our own in a quiet corner of the pub garden, away from anyone's gaze.

We sat next to each other and acted like two love-struck teenagers. While waiting for our food she took my hand and slipped it under her dress and into the leg of her panties, urging me silently to finger her pussy; she was sopping wet and I slipped two fingers in and curled them upwards. She bore down and pressed her g-spot onto them. After just a few minutes she turned and buried her face in my shoulder, her body shaking as she sobbed out her orgasm, struggling not to make any noise. I was dazed and still recovering from the impact of bringing a woman to a climax for the first time ever in a public place.

Being with someone with such a high sex-drive was so new to me but I managed to compose myself just as our server brought the food to the table. Having burned up so much energy that morning we dispatched the food quickly and with relish. As we finished our lunch and paid the bill Jan urged me to take her home for dessert and we spent the afternoon fucking around her flat, first on the kitchen table, then on her sofa and finally in the shower.

She might have been small but she more than made up for it in personality and with her outgoing, no-nonsense approach to life. I called her my pocket rocket but she showed me an essay she'd found on the internet that described the personalities of people born in 1962, the Chinese year of the Tiger and the year of her birth. I'm always skeptical about such things but it described Jan to a tee, and from then on I called her Tigger or Tiggs - it pretty much summed her up. I still have a pen engraved with the word Tiger that she gave me.

On only our 3rd date we crossed several lines in our relationship. I not only unpoppered her teddy but this time I encouraged her to let me take it off. She resisted at first, on the basis that she didn't want me to see her tummy. She was very conscious of her appearance but I told her straight that if she didn't let me see her buck-naked I'd be very unimpressed. I said it with a smile and reassured her that I didn't care how many wrinkles or marks she had, I wanted to see and feel her next to me with nothing on. She let me peel it off and subsequently told me it was a big step for her in our relationship. I've since experienced something similar with other women who felt they have body issues. Jan had stretch marks on her tummy, it was her only physical flaw, but I loved her all the more, it made her a normal mum and I made a fuss of loving her tummy until she became completely comfortable being naked with me.

The other line we crossed that day was to fuck bareback. Jan already knew I'd had the snip but otherwise nothing was said beforehand. There must have been some form of silent agreement between us that day and we just joined our bodies together without using a condom. Once fully inside her she hugged me and reassured me she was fine with it, whispering in my ear that it felt right and so much more intimate for her. That was a huge step for me, the most significant step I've ever made in my straying, and I climaxed quickly. Ejaculating in another woman was hugely powerful for me, a middle-aged married man playing away for the first time. As I came deep inside her she cried out how she loved feeling me flooding her with warm semen. It affected us both a lot and our emotions overcame us as we cuddled close after copulating so intensely.

Bareback fucking in this situation played strangely on my mind and while I knew there was no way Jan could get pregnant I still thought about the consequences of fathering a lovechild. I must have mentioned it because she would sometimes tease me about how she'd love to bear my child. She told me how turned on she got at the thought of being pregnant again after so many years, and speculated naughtily at what her friends would think. We'd talk about pregnant sex, about how I'd always loved fucking my wife while she was expecting each of the children, and Jan would turn me on with talk of her having a swollen tummy. It was a sort of fantasy at the time and thankfully no more than that.

Jan taught me how to share her enjoyment of semen once we started barebacking. She introduced me to the art of cleaning her up after sex, she showed me her love of having her body decorated with my cum and she encouraged me to eat my own semen and how to share it with her by snowballing. I'd never even heard of that but I was a quick learner, kept an open mind and managed to keep up with her.

I saw Jan many times over almost 2 years and inevitably fell heavily for her. She told me she wanted to be a courtesan not an escort, nor a lover for me. After a while she refused to take payment and preferred gifts instead, saying it was different with me. She was still an escort for other men; she claimed she met 2 or 3 per week on average and she insisted on setting high standards in her escorting and didn't suffer fools, nor did she do anything she considered tawdry or risky.

She was the first woman other than my wife that I spent a night with, which was another huge step for me. The first night we spent together we held each other a lot and she cried a bit, told me she regarded me differently to other men she had sex with and that I'd helped her gain confidence. I teased her about that as she had bags of personality, but she insisted that she put on a lot of bravado and that I was someone she felt safe and secure with and that she could let her guard down with me. It pulled at the heart strings having a gorgeous woman, way more gorgeous than I'd ever imagined being with, curl up in my arms naked and tell me she felt safe and secure and comfortable with me.

She was an amazing lady; bright, sharp, vivacious, vibrant, quick tempered (not a woman to be wronged - god help you!) and with a huge sexual appetite, but I always knew there was a lot more to her than met the eye and I knew that any man who took her on would have his hands full.

She loved retro lingerie and fully-fashioned nylons, another huge weakness of mine. I bought her loads of lovely things and adored seeing her wearing it in public, knowing I'd be fucking her in it later. She loved keeping it all on for sex and then having me peel it off her. We once stayed in London overnight, and I took her to a nice restaurant in Chelsea across the road from the hotel. She turned a lot of heads in the dining room and I felt very proud. She wore sheer seamed nylons in a chocolate brown shade, and white co-coordinating lingerie with a deep lacy 6-strap suspender belt. Back in the bedroom she just took off her dress, bra and pants and I fucked her while she still wore her heels, stockings and suspenders.

She regularly worked out at the gym and could get her knees right back by her ears when on her back, her gorgeous shapely legs pointing straight towards the ceiling in her FFNs and 4" fuck-me heels. Seeing her in that position, dressed like that, and the sight of my cock sliding in and out of her beautiful cunt was a total delight for me. It become our favorite way of fucking, her dressed in gorgeous lingerie and hosiery. By the time we'd been hard at it and changed positions several times her seams would no longer be straight. She would get us back into missionary, her legs straight up in front of my chest, a pillow under her bum and me on my haunches buried inside her. She'd get me to straighten her seams and adjust her suspender clips while sliding my cock slowly in and out of her.

She also taught me how to remove her stockings without snagging them, peeling them down her legs and off her exquisite little feet. She taught me so much about sex and I gained a lot of confidence and technique. That night in London I ended up cuming all over her stocking tops, the first time I'd ever done it. I made a huge mess and it turned us both on even more. It became a fetish for us and I had a lovely picture collection of her wearing expensive seamed stockings decorated with my cum.

During the months we were with each other we spent several nights together, we helped each other over some difficult emotional issues in our lives and I confess that there were some fleeting moments of madness when I considered leaving my wife for her. Thankfully I came to my senses, and Jan kept me on the straight and narrow regarding my marriage. She was perceptive to know that I was deeply in love with my wife and she urged me to work on my marriage. She always told me to regard her solely as a courtesan - "don't you dare fall for me, you place is with your wife" she'd tell me.

She was always in charge and thankfully she was a skilled operator, otherwise I might have made a complete fool of myself. She told me I'd been repressed sexually for much of my life and that her role was to open my eyes and educate me, so that I'd go back to my wife a more imaginative and accomplished lover. She was very perceptive and I was so lucky to have had her.

Jan was open about her aspirations and told me she was eager to settle down with the right man, though she admitted that if circumstances had been different she would have found me tempting. But it was clear to me that she really wanted a man who'd be a bit more edgy than me, she actually said as much. Her personality was such that she suited the 'bad boy' type, even though it would probably all end in tears again. She was convinced she'd never meet the right man, "all the good ones are married" she'd complain.

She would get very down about it at time, she wasn't programmed to be a single woman despite her feistiness, and I would reassure her that she was one hell of a catch and that one day she would meet her charming prince. Eventually she met a guy who her daughter had set her up with on a blind date. He sounded like a rough and ready type, not at all like me, but apparently genuine enough and able to give Jan what she needed. They hooked up together and got married, after which we stopped corresponding. I later discovered them on a swingers website as a couple but I never wanted to meet up with them. I'd moved on by then.

On what would be our last date, we spent an afternoon in a hotel. By now she was going out with her new man and felt uncomfortable having me at her place. We had sex but nowhere near as intense as previously. The spark had gone now that she was with her new man. Thankfully we parted on good terms, knowing that the day was always going to arrive. It still took me a long time to get over her but it was a price worth paying.