Blog : I was 17, he was 50

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7/23/2019 9:08 am

I was 17, he was 50

He lived down the street from us… I used to pass his house on the way to school in the morning and on the way back home after school. I was in grade 12. Most of the time he was outside in the afternoon and would wave at me as I walked by. I always smiled and waved back, he was after all a neighbor.

I didn’t know how old he was, just that he was an older man… During the warm summer months he would wear shorts and a t-shirt, and he must have still worked out because he was in pretty good shape. He looked like he had had physical jobs all his life… his arms were big, his stomach flat, and his legs well defined. He was a tall man (in my eyes anyway) standing almost 6’ tall.

I just decided one day that I liked what I saw and decided to seduce him… 
After school I would purposefully walk on his side of the street so he could get a better look at how well proportioned I was. I never dressed very conservatively, but started wearing shirts that were a little too tight and left a couple too many buttons undone…

One day before I left school I removed my bra so I was only wearing my tight white t-shirt… That was the day I stopped to talk with him. I noticed as we chatted that his gaze kept dropping to look at my breasts and nipples. I was not an ugly girl, but my breasts were definitely my best asset and my nipples were, and still are. Almost always hard.

I was checking him out too, and noticed that he had quite a bulge in his shorts. I was trying to figure out what to say or do next, when he invited me in out of the hot sun for a cool drink. I accepted and we went inside.

Once inside he asked if I would prefer a glass of wine. I hadn’t had a drink of alcohol in my life, and am still not much of a drinker, but decided that might be nice. When he asked if I’d prefer red or white, I replied ‘whatever you are having will be fine.’

We sat in the back porch that was at the end of the house away from the sun. It only had a small loveseat and coffee table, so we sat fairly close to each other side by side and made small talk. He asked me how school was going and what I wanted to do with my life afterwards and did I have a boyfriend… He seemed almost shocked when I replied that I did not have a boyfriend.

I told him that I dated once in a while, but that the guys seemed so immature and I wanted to meet a more ‘mature’ man. The truth was that one guy could not satisfy my need for sex and I needed to sample as many different cocks as I could. I truly was a slut.

At one point during our conversation I looked at him and said ‘kiss me’. He looked surprised and I thought I had blown it, but then he leaned in and kissed me softly. I kissed him back, and when we parted I said ‘that was nice’, so he leaned in for a longer deeper kiss… This time when we parted, I asked him ‘Which way to the bedroom?’

He got up and took me by the hand and led me to his bedroom. He slowly undressed me and then disrobed himself. He was the most patient and caring man I had been with yet, and his main goal seemed to be pleasing me. He gave me several orgasms before cumming himself.

He asked me if I had ever tried anal, and I replied no I had not… He promised to be gentle and asked if he promised to stop if I said so, would I let him have anal with me… I said yes.

He was once again so gentle and caring, and it was the best sex I had had yet. To this day anal is still what I enjoy most, and in fact anal makes me squirt…
We met secretly about once a week for almost 3 years, and I think it is still the best sex I have ever had…

dilbertsdog 66M