Shannon, the Next Step

A few weeks had passed since Shannon had given me some pictures to repay me for the hundred dollars she borrowed and could not pay back. The problem was I wanted more, the pictures she sent me all very sexy. We're not explicit enough for my taste. I didn't say much about myself in the beginning story so let me say a little bit here. I am a 53-year-old widow, I've been single for about three years now. I have some fetishes and some kinks. One of them is I love hairy pussy, and hairy under arms on women. I'm a voyeur, I love to watch people that don't know they're being watched. I have a panty fetish, as long as I know the person the panties came from. I'm not into strangers panties since I don't trust people and they're cleanliness. Having said all of that, my mind and my fantasies have been running wild since Shannon had given me those pictures. Did she need more money? Would I get more pictures? Would I ever see her naked? Would I ever get to touch her, or would she ever touch me? All of these questions will be answered in the upcoming stories, including this one. I know many people say it, but this is a true story, as well as the first story I wrote, and as the rest of them will be.

It was a Tuesday morning about two weeks after Shannon had sent me those pictures. Almost nightly I had masturbated to them. There was just something about her. That absolutely drove me crazy and I could not put my finger on it. Yes she was "natural" which is something that I like. She had a really nice ass which again is something that I like. So there were several physical things about her, pride come across many women that had the same features, and they did not intrigue me the way she did. Anyway, Shannon came up to me and asked if there was anyway that I would be willing to lend her some more money. She said it in a very shy manner and then slowly looked away. I asked her how much and again she said $100. I told her I could help her into that. She said OK but this time I'm going to pay you back. I said well you paid me back last time. She just smiled and said OK. I'm glad we got that out of the way. I gave her the hundred dollars at the end of the day and she gave me a kiss on the cheek. As she walked away, she intentionally lifted the shirt that was covering most of her ass and gave me a beautiful view of her gorgeous ass in those tight legging pants. I just moaned out loud and said nice, she stopped and turned before she walked out the door, smiled and winked. The rest of the week went fairly normal. I did get a few good looks at her ass. That in my opinion were definitely intentional. I also got a a few good, looks down the front of her shirt, and one extended look down her sleeve at her hairy armpit. Other than that, nothing much was said between us outside of normal work talk. That is until Friday.

Shannon came in Friday morning and had on a pair of white leggings with a long tan shirt covering her retire ass and crotch. The minute I seen her my mind immediately went to overdrive thinking what that beautiful ass must look like in those pants! We went to lunch and there was only three of us out there, myself, Shannon and another Worker. Tony was sitting at one of the table and I was at the other and Shannon was in the middle. Tony was busy scrolling on his phone and Shannon turned her chair facing me. At first, I didn't pay any attention. Then I noticed she kept looking at me and then looking down. As I followed her eyes down, I almost spit out my lunch. Not only was she wearing a pair of paper thin white leggings, but she had no panties on. I could clearly see the outline of her very large pussy lips, I could also see her very hairy bush just as clearly. I looked back up at her and smiled and mouthed the words " holy shit thats hot" and then I licked my lips. She just giggled closed her legs got up from the table and left.

After lunch, I went back to my office to fill out the paperwork for the week before going back out on the floor. As I was sitting down at my desk. Shannon walked, shut the door behind her and asked me if I enjoyed the show. To which I told her very much so. She reminded me that she had never done anything like this before, but her financial situation was terrible and since she knew me that maybe we could work something out like this until she got on her feet. She then said we cannot sleep together or touch each other that would destroy our friendship, but we could flirt and have some fun and I could give you "help" since you're single! I just looked at her and smiled and said well I'm not happy about the no touching part, but I think we could work something out. With that she smiled, turned around, picked up her shirt, giving me an obstructed view of her incredible ass and walked out of my office.

Later that evening, I got a text message from Shannon that asked if I was alone. I told her I was that I was heading home from getting something to eat. The next text message I got from her was a picture of her in a pair of white satin panties and bra. She was standing in front of a mirror and took a picture. Several of them from the front and several from the back. I could clearly see her pubic hair sticking out from the panties and several clear pics of her underarms. Her huge pussy lips were beautifully outlined in the thin satin material, I think she had them pulled up tight on purpose! I text her back and told her she has a gorgeous body! She replied, asking if I had a problem with her stomach, that her boyfriend said she was getting chubby. I told her I definitely did not. She was the mother of two children, and in my opinion the little bit of extra she had on her stomach added to her appeal.

I again spent the weekend jerking off to her pictures. It was like a perverted dream come true. I got to look at explicit pictures of this incredibly sexy woman who had all the things that I liked in a woman, plus it appealed to my voyeur side. I cannot tell you how many times I jerked off to pictures of her in a pair of panties in a bra. I could not get the thought of her huge pussy lips out of my mind, I don't know if she realized what an incredible view I had at lunch on Friday. I am jerking off right now as I write this story thinking back on it. I guess we'll see where the next hundred dollars takes us?