[stockinglover21]

I am in my 60s and I have worked in London all my life. I have had four wonderful secretaries over the last 30 years and I thought I would write about them to remind myself of the good times and to share with others what I cannot share with family or friends.

I will give an overview here but will start new threads for each one as there is too much to say to keep in one thread. I will post links to each thread here.

Secretary 1 was “old school”. She was 10 years older than me at the time. Fit and fun. She believed it was the job of a secretary to please her boss. She dressed to please, short skirts, stockings and suspenders and blouses with many buttons undone. In return she expected time off for lunch with friends, to get her hair done and pussy waxed (unheard of back then) and just to shop. She also expected presents of lingerie and baubles and of course big bonuses, Christmas and birthday presents.

Two memorable insights. I was the new guy, just promoted to the level which deserved your own secretary. She had worked at the firm for years and had previously worked for another boss who had retired the day I was promoted. On her first day working for me she handed me the post book with her worn knickers inside and told me I was welcome to explore to see that they were this morning’s pair and also told me that if she made a mistake she expected me to spank her bare ass to punish her. Nowadays that would be unbelievable but to a secretary from the 70s it was fairly common – at least in my first firm. I had heard rumours and her “availability” had been strongly hinted at but I did not expect that. By 10:00 am I had explored her bare pussy with my fingers, by 11:00 am she had had her third orgasm and by noon she had made me cum twice, the first by her mouth and the second taken from behind over my desk. She left at 12:30 for lunch and did not come back until 4pm by which time she bent over my knee because she had been naughty being back so late and deserved to be spanked. This was my first time spanking anybody. It did not do much for me but she loved it and she sucked me dry before she left for the day.

Secretary 2 after an initial “nothing” period became an exhibitionist and tease. She would flash me boobs or pussy every day and sometimes many times a day. She would kiss passionately and would allow me to finger her to orgasm as many times as I cared to do it but she would rub me repeatedly through my trousers during these times but the most she ever did was wank me off a few days a week. They were world class handjobs and sometimes I thought better than sex but no oral or intercourse because she was a virgin and saving herself for her husband (not that she even had a long term boyfriend at that time).

Secretary 3 was somewhat lazy, and would find any excuse not to work. As this would often mean sucking or fucking me rather than doing work I did not mind. She had a husband who ignored her and she craved attention which I was happy to give. In return, lots of sex. I once had to go to the doctor with a very sore penis thinking she had given me a STD but it was just damage from too much sex, she liked quickies when she was insufficiently wet to start so she would be so tight and my doctor, who knew my wife, just said that he wished he could have so much sex with someone that his penis would end up like mine. He ordered 2 weeks rest and she said nonsense and refused to go a day without making me cum with her mouth.

Secretary 4 is my current secretary and my favourite. It is unconventional. She was 19 when she started (I was nearly 3 times her age) is married and money is involved so more of a commercial arrangement than the others but the way it has developed and how she has grown is a real story and I am having the time of my life.

Some people may say my track record is unbelievable and the stories are fiction but I know they are true and I do not care what anyone thinks. If you think they are fiction do not read them. Nobody is forcing you to.

They were all willing participants. Secretary 1 clearly expected sex and had done it before and probably offered sex to the guy after me. Secretary 4 needed the money and having had the experiences I had had with the previous secretaries I was keen to help her financially and benefit. Secretaries 2 and 3 are harder to explain. I found both attractive and hired them in part because of that and because I thought something might happen. Secretary 3 was the classic bored housewife who wanted attention and gave sex in return. Secretary 2 is the hardest to explain. I am not sure whether my experience with secretary 1 meant I expected something with secretary 2 and perhaps instigated something I would not have otherwise done.

I am not in touch with secretary 1. Once I had left the firm and started my own business she did not want to remain in contact. I am in regular contact with secretaries 2 and 3. Secretary 2 invited me to her wedding and we swap Christmas presents and her and her husband and me and my wife meet up a few times a year. Neither her husband or my wife have any idea how intimate we were and yes she remained a virgin for her wedding night. Secretary 3 and I meet up for lunch a few times a year (no sex just friends) and we have a platonic good time. She is in a long term relationship with another woman. She says she is not bi or a lesbian she just loves this person who happens to be a woman. Her new partner does not know about us and neither does my wife.

I will do individual threads and I will probably start with secretary 4 because it is current and so freshest in my mind. If the consensus is that I should write them in order I will consider that. It will take me a while. There will be erotic content but these are true stories and the background and context is important.