One of my grandmother's (Nan) friends was a lady called Monica. She was a small lady at five feet two inches tall and several years younger than Nan. She ran her own ladies clothing shop that did all sizes from skinny to way out sized stuff and all types of clothing from undies to dresses and coats. I was a full time student. At twenty I was always broke and and didn't have either time or money for a regular girlfriend. Nan used to slip me a little money from time to time and on one occasion suggested that Monica needed help in her shop. I felt a little uncomfortable the first time going into the shop seeing bras and pants on display as well as the bigger items. Monica greeted me and showed me several things that needed fixing and being in her fifties was having trouble with especially the heavy deliveries. She soon found me loads to do and I was working Saturdays and most evenings in the shop. I was surprised how quickly I became comfortable handling women's clothing and even seeing more of some of the women I was meant to. Monica made loads of hints that I should be out with girlfriends and I told her that I didn't have any. If there was something in the new clothing Monica liked, she would often nip into the changing area and try it on. Sometimes showing me and asking what I thought. For an older woman she was pretty stylish and she had definitely looked after herself and looked young for her age. She did a roaring trade and lots of the older women would tease Monica about her Toy Boy meaning me. Although she had limited space she would order different sizes and colours or patterns for people. This one evening I had swept most of the shop and turned most of the lights off. I thought Monica was in the toilet and walked straight into the changing area to sweep there. I don't know who was the more surprised, Monica or I as she was stood in just a pair of red and black silk panties and holding the matching bra. Well come in and shut the door she instructed me saying there was a draft. I did as instructe. Monica put the bra on and asked me to do up the clasp at the back. My hands were shaking and my cock was stirring as I did the bra up. Feel how soft and silky it feels she said taking my hand and running it over the cups and her boobs. My cock was now past stirring and was fighting to get out. Then she took the same hand and rubbed it over her crutch and then the arse area. Then she walked two steps forward and picked up a dress and put it on. I couldn't believe what had happened. I was left with a raging hard on. Then she told me it was time to go home. She lived on my way home so I often walked her home as I did that evening. That night I lay awake thinking about touching her most private areas even if it was over some silky material. I ended up wanking so I could get some sleep. The next few days, things were normal and I even wondered had I dreamed it and if it was just my imagination. Then on the Saturday Monica took several piles of clothes into the changing area near the end of the day. After the shop was closed Monica had me come into the changing area. She changed from outfit to outfit in front of me asking what I thought of each outfit. She saw my growing cock, and said that it wasn't as if I hadn't seen it all before. She was down to one last outfit and there was also a small pile of matching undies. Then she unhooked her bra and freed her tits and rubbed them. Then she was slipping out of her panties. I stood silent as I watched her totally naked selecting a set of undies. She put a lemon coloured set on and asked what I thought. I croaked that they were ok as I struggled with my aching cock. She took them back off and put a red set on. I was stood there with my cock battling against my jeans. She twirled around and modeled them for me. Then looking at the bulge in my pants she remarked that they seemed to be doing a good job. She was deliberately teasing me and I could take no more. I took my cock out and lifted her clean off the floor and pulled her panties to one side and lowered her onto my cock. Monica groaned loudly as my cock penetrated her pussy. She gasped that it had been too long. Monica was quite light and I walked a few steps to a wall and humped her against it. From the groans Monica was loving it and so was I. it was almost a year since my last bit of pussy. There was no thought to contraception as I pumped my cum into her pussy. Afterwards as I put my cock away Monica said she would buy the undies as they obviously worked. Afterwards I walked her home. Monday evening she acted as if nothing had ever happened until closing time that was, and then she practically dragged me into the changing area. This time she rode my cock as I sat on a bench. After this we fucked practically every closing time in the changing area. Several mates told me that there were rumors going around about me and Monica. I told them to ignore them. Then one Saturday she told me that she had a light out on the landing, in her house, and she wasn't able to reach it and it wasn't possible to use steps because of the stairs. She asked could I change it for her. After the shop closed we didn't fuck, instead I walked her home and sure enough the bulb had gone. It was tricky but I changed it and tried it. It worked. Then before I could go back downstairs Monica dragged me into her bedroom. It was way more comfortable fucking her in a bed rather than the changing area. Afterwards I went down on her pussy and licked and kissed her. It had Monica squealing and moaning. It got me excited and we fucked a second time. As we lay together Monica said in all her sixty four years nobody had ever done that to her before. I asked her about sucking cocks and she said she had tried one or two times, but she had been brought up to be religious and had been led to believe it was dirty. It told her we would try it next time. Then I had to run as I was late getting home and my dinner would be on the table and my mom wondering where I was. Monday night I walked Monica home and we were again in her bedroom. I was soon licking her pussy and Monica cautiously sucked my cock head. Slowly she started to suck a little more in her mouth. Her lack of experience reminded me of the first girl that had ever sucked my cock. Then we were fucking. Afterwards she asked how she had done sucking my cock. I told her she was fine and with a little more practice she would be great. After that she often sucked my cock while I licked and sucked her pussy. Our affair went on for a further seven years and then sadly she caught pneumonia in the cold winter and died. I went with my Nan to the funeral. I knew quiet a few of the older customers who attended. During the wake I spoke to some of them and listened to others talking about Monica. What I overheard shocked me. One of the older ladies was telling another that my grandfather had a long running affair with Monica, and even hinted that Nan knew and turned a blind eye to it. Supposedly he would go around the shop on the pretense of doing odd job and maintenance. At the wake one of her Brothers told me that I needed to attend her solicitors on Friday morning as I was in her will. Friday I felt uncomfortable sitting around the solicitors oval table along with four of Monica's relatives. The solicitor read the formal part of the will and then got to the nitty gritty. I never knew but Monica was extremely wealthy and had inherited a lot of money from her father. In fact she really didn't need to work or run her shop at all. The first sister was left £1.2 million pounds, the brother the same and the the two cousins £750 thousand each. They all looked fairly pleased and then the solicitor got to her properties. The shop and business, plus her house were left to me. I was stunned as was the relatives. One started an argument with the solicitor. He clapped his hands and called an end to her arguments telling her the will was just six months old and had been witnessed and signed in front of him by two living witnesses. Then he went on about two other houses that she owned. I had no idea she owned them and they was split equally between the four of them. I had to return a few days later to sign various bits of paperwork. The solicitor spoke with me afterwards. It appeared Monica had spoken with him at length. She had told him of our affair. I asked about his fees. He smiled when he told me that Monica had more than settled any bills with him some while back. I wondered what that meant and asked had he had an affair with her. He was a nice kindly type of man and quietly and calmly he told me that he had, but it had been over at least ten years back, but he was still very fond of her. Then he said as was my grandfather. I quizzed him and he told me that my grand father had been her on and off lover from teenage until he died. Then he told me he had his affair with her. He thought that I was probably her third and final lover. I got in a manageress to run the business as I felt that a woman assisting a woman in choice of clothes would be better received. In the main I was right, but there was a group of women that wanted a man's perspective. I was surprised how many were prepared for me to see them in undies and comment on them and tell them if they should buy them. I discovered that I liked the older women and I'll confess that I slept with more than one or two of them. I am now retired and live with one of my former customer. I sold the shop and moved my lover in with me, in the house Monica left me. My lover is older than me as you may have guessed. Monica shaped my life in many ways. I was even fortunate enough to have a frank talk with my Nan. I asked her about my grandfather and Monica. Nan told me that it was true that he had a long running affair with Monica. I asked wasn't she upset over the affair. Nan said no. Her and Monica were always the best of friends and if anyone should have been upset it should have been Monica as she had pulled him away from her. Nan had got pregnant and my grandfather did the honorable thing and married her. My dad was conceived out of wedlock and my Nan was happy to share my grandad with Monica. Monica never married as my Nan had the only man she ever wanted to marry. Nan told me that she was aware of my relationship with Monica and was pleased that I had brought her some pleasure at the end of her life. Then she ribbed me saying she see that I still liked the older ladies referring to my current partner. Sadly Nan passed away and when she was buried with Grandad I noticed that Monica is still with them as her grave is just two away from theirs.