20/06/2026
My name is Hildy and I hope you read the posts by my husband Hank about the marriage retreat we went to years ago that not only saved our marriage but totally changed our lives about sex. Well, my youngest sister, Jane, who my other sister, Anne and I have referred to her as our spinster sister because unlike Anne and me, she was not attractive and consequently never dated for decades. Things have changed for her and after talking to her and directing her to this site where she has read Hank’s posts along with others, she decided to write her story. She sent it to me and asked if we would post it in segments. Here is Jane’s story and I want you to know that it is a true story of my little sister.
I am the true epitome of the term ‘Plain Jane’. My name is Jane and I am as plain as plain can be. I’ not pretty nor am I ugly. I’m not tall and I’m not short. I’m not slender nor am I overweight. My hair is plain. My face is plain. My figure is plain. My voice is plain. I am so plain, that no boy ever asked me out or to anything, all through high school and college nor graduate school. I’ve tried dressing sexy and what I thought was seductive and gone out to bars, but have never been picked up by anyone. Don’t get me wrong, I have always been interested in men and wanted to date, but, to no avail. It’s been 24 years since my Master’s degree and I’m still plain Jane. In the sense that I had never been with a man, then yes, I was still a virgin, but in the physical sense, I was not. In high school, the handle on my hairbrush was my best friend. In college and since, I have acquired a few toys and use them regularly, but always wondering what the real thing would feel like.
My sisters call me a spinster as at age 48, I was single and never dated, that is until last year, but they don’t know that. My oldest sister, Hildy, whom you have read about and my next oldest sister, Anne, were both very pretty girls and had no problems attracting the boys. My brother Robert was also very good looking and had his pick of the girls. In my teens growing up, I had a crush on Robert and often fantasized that he accidentally walked in on me while I was in the shower or getting dressed. In the fantasies, he would see me naked and then would touch me, play with my breasts and finger my pussy, but they were only fantasies that never came true. No, for years, all plain Jane could do was fantasize.
A year ago, it was hot and when I got in my car to drive home from work, it felt like an oven, so I discretely took off my bra. I was wearing a white blouse and dark skirt. As I started to drive home, the sky opened up and began pouring rain and I mean pouring. About half way home, I got a flat tire. I knew how to change a tire so I got out in the pouring rain, went to the trunk and discovered that my car, like so many newer cars, did not have a spare tire, so there I was, standing in the pouring rain staring at an empty trunk when a car pulled over behind me. An older gentleman got out and asked if he could help and as he did, I noticed his eyes drop to me soaked and now somewhat transparent blouse. I felt my nipples get hard realizing that this was the very first man to ever look at me this way. I explained the flat tire and he told me to get my purse and stuff out of my car and that he would take me home so I could call for help. I thanked him, grabbed my things and climbed into his car. I told him where I lived and on the way, I told him that I had no idea of who to call for help. He said no problem and change of plans.
He drove me to his house, a very nice. He showed me a bedroom with a closet full of ladies clothes, explaining they belonged to his late wife. He told me to help myself, but that I needed to get out of the wet clothes and he politely left room. I took off the wet clothes, dried myself and my hair as best I could and found some clothes. They were about a size too big, but they were dry. I had remembered to grab my bra from my car and put it on and then finished getting dressed, I picked up the wet clothes and went out to the bigger room.
Jules had also changed out of his wet clothes and was waiting for me. He told me to leave my wet clothes in the laundry room for now. He asked if he could fix me something to drink – hot or cold and I said water and thanked him again. He told me that while I was changing, he called to have my car towed to his mechanic’s shop where they would fix my flat...