I was very nervous as I walked up the steps to her house. Jenny had invited me over to her house earlier that day. I was nervous because of what I had started in motion. Let me give you some history.
Jenny Johnson and I both have kids at the local elementary school. She is a great person and I have always liked her. My wife teases me because she thinks Jenny really likes me. I told my wife that it wasn't unusual as we both had kids in the same school and often walked our kids to school together.
I have to admit Jenny is very funny with a dry sense of humor. She is from the midwest and has a certain charm about her that is very sexy. I know she really likes me, but my wife thinks that she REALLY likes me. Both my wife and I know that Jenny's marriage is not great and her husband is a jerk, but I never thought about Jenny in THAT way until my wife brought it up. Come to think about it, Jenny always speaks to me a lot at parties or at casual get-togethers and if she is driving a car she pulls over to spark up a conversation.
Anyway, one time Jenny told me that she had just lost her job and she was bummed out. I really felt sorry for her and could see this really affected her. We spoke for some time and I got the impression that she was worried about being really lonely without her job and the relationships it came with. For some reason, this situation, combined with my wife insisting that she likes me as more than a friend, sparked a fantasy about what it would be like to have sex with her. This came on quite suddenly.
She is quite good looking at 5'9" tall, thin with small breasts and a perfect butt. She has a great smile and long black hair that she always ties up in a pony tail. Jenny and I are both around 50, and she looks great for a mother of two.
Well time went on and I still had fantasies about her. There was no way I could ever directly approach her about my desires, but I can and often do write down my fantasies I have about people. I began to think of a really sexy fantasy about her and wrote down, in great detail, all of the things I would love to do with her.
I got very turned on by this and would reading it self-pleasuring myself again and again. Then I started to thinking about how I could get her to read this fantasy of mine without her knowing that it came from me. I would include just enough detail so that she could guess that just maybe I wrote it. I would have to be careful, because even though I know her marriage is not going that well, she may just flip her lid and tell my wife. I had to infer only enough so that I could deny that it was me if things fell apart.
I setup an email under a fake name, but with a name that would spark her interest so she would not delete it. I sent her my fantasy.
I have done this in the past when I was much younger to friends and I thought that they really just wanted to read a good sex story. It was more than a year later, after sending one to a friend, that she called me and confessed to loving my story. She was now single and wanted to see me. It was great and a lot of fun as we acted out the story as written.
She told me there was just something about reading a sex story from someone you knew that really got her juices flowing.
But now the stakes are much higher. I am married with kids and Jenny knows my wife. We all live in the same community and word of mouth travels fast. I have a feeling though that she would go for it. I know Jenny likes me and always is very nice, even suggestive sometimes, in her mid-western way. Behind that smile and polite demeanor is a woman waiting for a sexual thrill.
She may outright hate my letter or think she does initially, but she may hold onto it and read it and slowly realize that it turns her on. I hope this is the case. I am quite descriptive on what I want to do to her in the letter and I wrote it based on her personality and what I think that she would be into and enjoy. I think that under her controlling exterior that there is a secret submissive side to her. I know this because of the way she treats her husband and others. This is a common fantasy and I could be very wrong, but that is why I am taking the route of letter writing. Her reading the letter would give her time to absorb it and then hopefully she would come to realise that it does indeed turn her on. The next step would be for her to figure out who it is who wrote it. Either way time would tell.
Jenny
I got home from my walk to school with Mike and the kids. I started my usual routine of exercise and then took a shower.
I was not too happy these days, but I was thankful to have Mike to talk to about my job situation. The job search was very frustrating as I thought it would be a lot easier to find one in this job market. The worst part was the boredom.
I found myself masturbating a lot more than I ever had before because it felt really good and it took the edge off my anxiety. I got excited and wet just thinking about sex, although my husband I and have not had sex for a very long time. Usually, I thought about my favorite movie stars like Tom Cruise or Leonardo DiCaprio when playing with myself in bed.
Sometimes I would also think about Mike. This seems so wrong to me that I usually don't hold Mike's image in my head all the way through to climaxing. Anyway I was again very horny so I headed toward my bedroom and brought my laptop with me. I had never been into internet porn before and found most of it quite disturbing, but I surprised myself when I started to browsing the BDSM sites. I used to laugh at the thought of people getting off on this sort stuff but now found it quite stimulating.
I laid down on my bed naked and spread my legs wide and started to stroke my inner thighs as I browsed for a good site. I found a nice set of images showing a middle aged woman being spanked by a gorgeous man. Her ass was red and she was fighting a losing battle protesting as her ass was being worked over. I had a nice climax while scrolling through this set of images. I lay back in bed for a while relaxing from by orgasm. I then sat up and realized that I had better check by email for any responses to my job search. I was saddened that I saw nothing but email from family and friends, which I like, but I really wanted a response to the multiple emails I had send to employers. Frustrated, I was going to shut my laptop then I noticed an email from someone I did not know. My spam filter must have screwed up I thought and I was just about to delete it when I read the subject line of the email.
From a Secret, Admirer-You know me, Jenny!
This intrigued me, so open it up, even though I thought that it certainly must have been spam. It read:
Dear Jenny:
I have liked you for a long time. You know me but I am afraid that this letter might upset you so I am sending it anonymously. Attached is a fantasy about you that I wrote. If you read it and find it frightening or in anyway upsetting know that all you have to do is reply to this email and tell me to never contact you again. If you like it and want to know more just try and guess who would write to you and then let me know. I have to do it this way to give myself some level of protection. If you are appalled for frightened, I am very sorry, this is not my intent. I think you are going to know who I am and even though I am taking a great risk, I think that you will realize that maybe you might find pleasure in making some of my dreams come true and maybe these dreams might also be yours. So read the attached letter and if it peaks your interest respond to me in person or over email.
Your true friend
Mike
It had been over a month since I sent the letter. I eventually began thinking that my email to her with my letter got caught up in her spam filter because she did not show any real change in her interactions with me.
Then very slowly I started to notice a change.
"Oh well, nothing ventured nothing gained", I thought as I left to walk my kid to school in the morning. It was only five blocks to the elementary school. I had not seen Jenny on walks to school for a couple of weeks. She sometimes had to change her schedule because of work, but now that she was out of work I found it strange.
"Hey Mike," Jenny said, as she came up behind me.
"Hey Jenny, long time no see," I said looking her up and down. I usually never scan women so obviously, but she took me by surprise. I saw her notice my roving eyes. She just smiled.
I was a little shocked at her lack of clothing. She usually wore very conservative pants and tom-boy style shirts that drove my impression of her as innocent and sweet, but wow did she look sexy now! She was wearing a knee high blue pleated skirt and spaghetti strap blouse. I could just see the top of her A cup breasts in her low cut blouse. Also, she was wearing her hair down for a change. She had long black hair with large bouncy curls with streaks of gray showing her age. I thought it looked very sexy. What a change! I felt my blood rushing to my nether region.
"Ya, I have been taking it easy over the last month," she said as she joined me on the walk to school with her daughter.
I delayed responding to her for a second because I was realized suddenly that this was similar to how I had her dress in my fantasy. It got me very nervous!
"Well is good to see you, how have you been?" I asked, trying to steady myself.
We chatted back and forth all the way to school about the kids, family and her job situation. She complained like normal about her husband and then talked about her job search, which is not going well. She is a very intelligent person with excellent job skills in marketing which is her industry, but I guess the job market was just not hiring in her position. It frustrated her. She also said that she is having a hard time with boredom and having to deal with her husband more than usual as she had no job to keep her busy.
"I am really sorry about that," I said sympathizing with her. We continued to talk about her job situation all the way to school. I think I helped her feel better, but I was distracted by the change in clothing. Boy what have I done, I thought.
We reached the school and dropped off the kids. I hugged my child and wished him a good day. Jenny did the same with her child.
We walked back together and spoke more about family and friends. As we came to the block where I go right and she goes straight she turned to leave and then, seemingly as an afterthought she said, "Can you stop by sometime this afternoon?"
"Sure," I said, "what's up?"
"Oh, nothing big just wanted to pick you brain about some things." She said.
"Sure, I'll be over later", I said and we went our separate ways.
Fast forward from the beginning to why I was so nervous...
I walked up the stairs to her house and rang the doorbell. I was very nervous but I decided that I needed to know just what she wanted. This was the do or die moment. She was either going to yell at me and tell me to go to hell or...
She opened the door and looked at me without smiling.
"Come in Mike," she said. She had a neutral expression and a flat tone in her voice. I could not tell what she was thinking.
