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Stories about Sex with Older Women

235. Man's Story: Canadian MILF (7/6/04)

I just moved to Canada when this happened. I was 19 years old and they put me with a host family for the first 2 weeks until I found a place of my own. When I first moved in with the host family, I appreciated how beautiful Canadian women are. This lady is married to a guy twice my size and had two kids.

Even though I liked her so much, I did not think I had a chance. During the day the husband goes to work and she stays home. About three days into my stay, she asked if I need any thing and I told her I need to buy a few things from the supermarket. We went together and had lunch and during our shopping trip, our bodies rubbed and she saw me trying some clothes and she told me when something looks good on me, etc. During lunch she "accidentally" touched my legs, about 4 times.

The next day, while I was coming out of the shower, she asked me to join her for breakfast and I said, after I put something on. She said you looked good the way you are. Being the little dick I am I agreed to come join her - no underwear, nothing but the bathrobe and the towel. She was wearing nothing under her clothes it became apparent later!

I helped her prepare breakfast and my dick was so hard, she noticed him and made a comment about how huge it was. That did it for me and I was about to drop my robe when she came from behind and gave me a hug and reached with her hand and massaged my stiff cock. I turned around kissed her and started the whole thing!

I'll tell she was a PRO. she sucked me and asked me not to blow my load in her mouth...and I didn't! All the time she held my dick with her hands and said how big it was. She asked me to eat her pussy, but I think I was terrible and that is why she pulled me up. She took me by the hand to the living room and rode me like I never thought it was possible. I came right away.

She played with me some more and soon after my dick was hard again and she asked me to fuck her in different positions. I was able to last a lot longer than the first time. She was screaming and talking to me while we fucked. She asked me to put my hands on her boobs, but I was not very impressed with how they felt, because they were saggy. I was disappointed because they looked firm when she was wearing clothes, but it turned out that she uses tight bras.

Her pussy was not tight, but she gave out a lot of juice. I came in her pussy so many times and I fucked her every day for two weeks, but I was very afraid of her husband.

I was happy to leave that house even though I enjoyed the fucking. I said to myself, this house is built on mistrust and fucking behind each others' backs. I was very sure that the man was fucking around too.

One thing though, I asked the woman, Why do you have sex with me when you have a husband? She said she loves her husband and they have sex almost every night, but she wanted more and she likes my big and young cock.

191. Man's Story: In Praise of Older Women (11/24/03)

My first time having sex was one of the best sexual experiences I've ever had. The reason it was so good was because the girl I was with was 5 years older than me and knew what she was doing. Some friends and I were away for the weekend and we met a group of really hot but slightly older girls who were also on holiday. We all got drunk and I ended up spending the night on the beach with this one girl. The first night we just kissed and petted all night, just on top of our clothes nothing too serious. The next night we all got drunk again, but as the party got going she dragged me off to an empty bedroom. She pulled all my clothes off and I did the same thing to her. The foreplay didn't last long, as she was still all worked up from the night before and she knew what she wanted. She pushed me onto my back and sat on top of me. She then started rubbing her crotch against mine and skillfully slid herself onto my cock. She started to rock back and forth on me, and even though I could feel myself going in and out of her I was new to this and wanted to make sure. It was dark so I couldn't see anything. I reached down and used my fingers to feel around her pussy. The realization that this was actually happening to me washed over me and I decided to just relax and enjoy the experience. We met up with each other a couple of times a week just for sex for the next few months. I told her I wanted more than just sex and then we stopped seeing each other. Now that I have more experience I realize that she was fantastic in bed and it was her love of sex that made her so good. My advice for other guy's first times: get yourself an older woman who knows what she is doing.


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