I remembered how he looked the first time I seen him. His name was Jack. He was wearing faded jeans and a black t-shirt, his arm muscles were bulging as he lifted the boxes and carried them into the house next door. He looked like a movie hunk to me. He had dark hair, overly long, that fell over his green eyes, big arms, flat stomach, tight buns and a face that belonged on the big screen. He must have been about thirty five then which would make him about forty five now to my twenty three. Him, his wife and two kids moved in the summer I turned thirteen. I had just become officially boy crazy as my mother liked to say.
His wife was beautiful with her blond hair and blue eyes, the rubber stamp cheerleader type with big boobs and tiny waist. Her name was Jessica, of course. She was evil. Well, that's how I saw her anyway. Probably because she was married to the man that, at thirteen, I just knew I was in love with. Even though I didn't know his name yet and had only seen him from my bedroom window.
They had two sons, Dillon and Jake, fifteen and thirteen respectively. Dillon didn't interest me as he wasn't cute and at that age, it's all about being cute you know. Jake on the other hand was my age and a real cutie. We became fast friends and eventually dated from sixteen to eighteen. We were each others first everything. First kiss, first peek down the pants and up the skirt, first curiosity touch, and first lovers. We stayed together until graduation, when he went off to college out in California, but that's a whole other story.
The five years I lived next to Jack, I got to know him like you would any neighbor and father of your friend and boyfriend. He was always nice to me and always told me what a pretty girl I was. He would tease me about being able to do so much better than Jake. The crush died down but apparently it stayed hidden inside me just waiting to come to life again. During my senior year in high school my parents divorced and I moved with my mother across town to an apartment complex. I hadn't seen Jack since graduation.
Two days ago, I was coming out of the Java Hut, a little café a block from the office where I worked as an office manager, when I heard a deep voice call my name. I turned and looked and sitting at one of the little sidewalk tables was Jack. He stood and said, "I thought that was you in there, how have you been?"
I walked over to where he was, "Mr. Miller, it's so nice to see you. I'm fine, how are you?" I sounded cool and collected and pleasantly surprised, but inside I was thinking, ‘holy shit he is still gorgeous', and my heart was beating a mile a minute. He asked me to sit down. I did and we chatted for about half an hour about my mother, his family, how Jake was doing in California, that kind of thing. Just catching up. It was very nice, but there was something about the way he looked at me that had my heart doing flip flops. I wasn't sure if it was just the old crush acting up or if he really was checking me out like it seemed. I did notice his eyes straying to the cleavage that was showing. I have good breasts, they are firm and nicely shaped, not overly huge but a nice size and real. I like showcasing them. He told me he had to run but ask me if I'd like to join him again tomorrow for another coffee. I said I would and he left.
The next day I joined him again at the set time. I wasn't sure why I did it, but I took extra care with my appearance that morning. I liked what looked back at me from the mirror. I won't call myself beautiful. People tell me I have a pretty face. My hair is black and wavy, coming to rest just below my shoulders. I have brown eyes and a long neck. I think my figure is my best asset. I'm not skinny, I have some padding but it must be in all the right places because I get my share of looks and offers. As I mentioned my breasts are very nice, my waist isn't tiny but it's small. My hips have some meat on them. I guess you could say I have an hourglass figure. My legs are long and lean, my last lover said they were dancers legs. I wore a red blouse with the top three buttons open to show my cleavage, a black skirt that came about three inches above the knee, dark stockings and black pumps. I noticed that he looked me up and down several times as I approached him.
We chatted for a few minutes as we drank our coffee. Then he reached out and covered my hand with his. He said, "Jilly, I have to tell you, you are a very beautiful young woman. I always thought you were pretty, but you have matured into a beautiful woman."
I could feel myself blushing and I didn't know what to say. I just said "Thank you."
He laughed, "I didn't mean to make you blush Jilly."
The way he said my name made my heart skip a beat. That old crush was alive and well. He still looked great. His hair had a touch of gray now and was cut short, there were laugh lines around his eyes. His body looked to be still in good shape, though I couldn't see much since he was wearing a suit. I could tell he had a little bit of a tummy though.
He sighed and said, "Jilly, can I ask you a personal question?"
"Sure, go ahead." I said.
He looked at me for a few seconds then asked, "Were you and Jake ever lovers?"
I was shocked at first but then I answered him honestly and told him that we were. He began asking me more specific questions like, how old were we, what did we do, where did we do it, that sort of thing. The whole time he was asking me, his fingers were rubbing the back of my hand. It was strange to be ask these things by my ex-boyfriends father but in a way, it was exciting to be talking of sex to this man that I had a crush on years before. I was glad that he had picked a table that was not too close to the others. He finally asked me, "Was it good for you with him? I mean…", his hand closed around mine and held it now, "…did he make you cum?"
I just looked at him for a few seconds then said, "Jack why are you asking me all these questions? It's a little weird. You are Jakes father."
"I know, but there is a reason. Can you tell me please? Did he give you orgasms?" he asked again.
I bit my lip and answered him, "Twice."
"Tell me about them please. How did it happen? Was it from oral sex or while fucking? Excuse my language." He went on. "I need to know for a reason Jilly. I want to get your sexual past with my son out in the open so that the next thing I tell you wont be as strange for you."
I pulled my hand away but he grabbed it again. "Relax sweetheart", he told me.
I looked into his eyes and while I sort of expected to see the eyes of a perverted old man getting off on hearing about his sons sex life, that's not what I seen. Instead I seen a rather kind smile and what appeared to be desire. It was like some sort of spell was being cast over me. It immediately relaxed me and I began to talk. "Well, we were seventeen when we first began as I told you, so we didn't know a whole lot. Most of what we did was me giving him blowjobs in the beginning. The first time I had an orgasm, was while I was blowing him. We were in his room one day after school, he was sitting against the headboard and I was lying across the bed with my head in his lap sucking him. He pushed up my skirt and put his hand inside my panties and was sliding his fingers in and out of me and rubbing my clit with the heel of his hand. That was when I had my first one." He didn't say a word just kept looking at me so I continued.
