Written by Kyle

25 Feb 2011

Hi. i am Kyle, i am 26, single but in a long term relationship. I would like to share an experience that I am currently in. I will try and keep it short and to the point so apologies if i tend to ramble on at times.

Couple of years ago I was by my employer if i was interested in a short term re-location working in another part of the country. Initially I was not too keen but I suppose with a financial incentive being waved in front of me I decided to accept the offer. Apart from the finance part it would also offer me a good career opportunity. The only draw back is that i would stay there in the week and return at weekends. At the beginning I enjoyed the experience but after a while became bored especially in the evenings. Staying in a small bed and breakfast was fairly restricting. And thats when I suddenly met Caroline, a 52 year old lady who was working as a PA for the company but if honest I rarely saw around the office as she was based on another floor. To be honest I never registered her a second look in the office, and even initially when we got chatting I only really exchange conversation out of politeness. She was aware of my situation and one day out of the blue she asked me whether I would like to accompany her to a local theatre production. She knew of my interest in arts and so to cure the boredom one evening I agreed. Apparently her husband normally went with her but on this occasion he could not make it.

I clearly remember meeting her in the theatre foyer and remembering how different she looked and this was due to more make up than usual. To be honest I was slightly nervous as I was already hoping that the evening be over, and its one thing talking to a work colleague in the office but somewhat different outside. Making small chat was not my thing. The next thing that took my breath away was when we went to sit down. She removed her coat and sat down crossing her legs, i remember almost staring at the incredible sight of her legs encased in sheer nylon. She was only wearing approx 2 inch heels but it was like a vision of sheer sexiness. Suddenly this woman who did not even register on the 'do i find her attractive scale' suddenly oozed sex appeal. I must be honest and admit I spent very little time watching the stage but had my eyes firmly on her beautiful legs. The dress she wore was 2 or 3 inches above her knee. Over the next 4 or 5 months Caroline and I saw more of each other and I was also invited to her home to meet her husband. I had to admit during this time I started to find Caroline very sexy and I admit to start thinking about her more than i should.

Whenever we went out I would take every opportunity to enjoy the view of her legs and quite often and i believe this to be very unintentional on her part but i would enjoy getting an eyeful of stocking top. Suddenly this woman who was old enough to be my mum I was having very dirty thoughts about. The weird thing was that I still did not find her overly attractive but I had grown to really like her company and she had a wonderful caring personality which I found to be very endearing. All this seemed to make her even more sexy coupled by the fact that her appearance most of the time was beginning to excite me more and more. The ineveitable eventually happened and we had yet again been to the theatre when on my return to my accomodation I invited Caroline in for a coffee. We seemed to talk for ages then eventually it was her who leant over to kiss me and i nervously responded to which she allowed. It was actually her whose hand moved up my trouser leg and started to rub my cock from the outside. I did not need any further encouragement and within seconds my hands were running up the inside of her leg and feeling the warm thigh above her stocking tops. Quickly removing her dress and my shirt and trousers removed we made our way to the bed, i insisting that she kept her stockings and suspenders on with her shoes and instantly i found myself positioned between her legs and my cock entering her pussy, pumping away at her with all my energy. What really shocked me and excited me greatly was that she became very vocal and kept on repeating for me to fuck her. I was gobsmacked, in all the time I knew her not once did she swear and suddenly this quiet and very gentle mannered lady was like an absolute slut.

Over the next few months Caroline and I fucked at every possible available time becoming more and more daring. I again have to admit it was a real education for me and Caroline really broadened my mind and my experiences. The strange thing was that Caroline told me that she had been completely faithful throughout her 20 years of marraige and she really did pertain to having fairly old fashioned and loyal values, which made her behaviour even more surreal. However I was not going to complain. The other thing I liked unlike the limited sexual relationships that I had been involved with, and girls of my age was that she loved to wear nice lingere. Something that I had always been very sexually attracted to and turned on by. Caroline made me feel very much at ease when talking about sex and what we each individually liked. She allowed my imagination to run riot and she always seemed keen to live out any fantasies I had. We both knew that at some stage in the future when my contract was to come to an end we would have to part but we were enjoying each others company and the fun and games we were getting up to.

Just before Christmas things took a more exciting turn of events. I noticed over a period of time that Caroline had suddenly become more dependent on me. Instead of her driving the relationship she had taken on a more submissive role in our sexual relationship. Even in our friendship she demonstrated a more submissive mature. She would have no boundaries in satisfying my wishes. By this stage I had become more confident in our relationship / friendship and throughout our adventures so to speak I had become very fond of Caroline, i started to care deeply about her and her happiness and care was paramount to me. However she had enlightened such a sexual energy passion for her that this side knew no boundaries. Knowing i had to return in March this year I decided to take on a more influential and domineering role. Whilst continuing to look after her and spoiling her with attention whilst in my company I decided to really open the boundaries.

Caroline seemed even more willing to satisfy me and even though out of character for me I decided to become alot more assertive in our sexual relationship. More shocking was that Caroline complied with all my wishes. Everytime we meet and on certain days at work it is I who decides what she wears, trousers are not allowed and I have treated her to a vast selection of dresses and skirts, silk blouses, worn with fine lingere, always stockings and suspenders and often without panties. She nows wears high heels on occasions which has actually caused a few male comments at the office. If only they knew who was behind it. I have actually heard her boss pass a very lurid remark about her to another colleague. I have really enjoyed dressing Caroline and making her more sexy for all the men in the office to see and also when we have been out. Many a time when we are out I will actively seek out an unsuspecting guy, maybe on a train for example whom we will position ourselves in front of so Caroline can cross her legs and get a reaction. Whilst driving i have pulled over to ask someone directions and as they peer in the car Caroline will be sitting in the passenger seat with her stocking tops on view. I have even answered an advertisement where a young guy wanted to meet a mature lady / couple. Whilst nothing happened during the 3 or 4 times we met he was honest enough to admit that just being in Carolines company was enough and that he enjoyed the evenings in the pub just being able to constantly look up Carolines skirt and see her stockings. He admitted to me that gave him enough excitement to constantly wank over her after he had left us. Unknown to Caroline I also gave him a gift of some of her stockings which he was thoroughly pleased with.

Naturally throughout all our adventures it was me that fucked Caroline at the end of the night. As we started Caroline knows that she must remain in her stockings and suspenders and heels and she even now loves to be tied to the bed and wanked over. By day in the office we tend to remain strangers and for most of the week we do not see each other. But on the nights or odd day we get together we live our lives indulging in the most wonderful sexually charged fantasies and cannot get enough of each other. Soon our time will be over and we are both aware this must be the case. Caroline has taught me almost everything I know about sex and how to be a good lover. I am not too sure what I have brought to her life but hopefully I have shown her a good time, good company and chance to also live out her fantasies. With only a month to go now our time is nearing the end and we have both agreed that it will finish then. I have certainly been a very lucky man in finding Caroline and she has been a true friend to whom I shall never forget.