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Mature Women / Cougars / MILF Stories (Written By MEN)

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Old 03-05-2010, 11:20 AM   #1
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Default Mom's Friend

This is the first story I want to share because it was the beginning of a lot for my sex life. My first older woman, and she is what made me realize that sex really isn't all that hard to find. Prior to this experience sex came sparingly. Ever since this time, I've been on a mission, but anyway... onto the story.

A couple of years ago, I was 18 years old and fell in a small hole. I moved out of my parents house almost immediately after turning 18 because of college, and that I just wanted to move out asap. Not that I hate my parents, I actually have a healthy relationship with them, I guess it's just the whole independence thing. But then came summertime. Instead of hitting up the beach or the many parties out there like most my age would do, I was busy trying to find a place to stay and keeping financially stable. My roommate and I had to move out of our apartment because I lost my crappy job and thus I wasn't able to hold onto my side of the rent.

Only about 6 months removed from my parents house, I had no choice but to move back. My mom's friend was also staying over for reasons unknown to me. It never really did make sense as to me why she stood over, growing up I would always overhear both my mom and dad complaining and saying something bad about her, but I never bothered to ask anyone why. Whatever the reason though, I'm glad she was staying over. She's average height, 5'4 I'd say. Average build, probably around the 105-110 lbs. range. Nice light brown skin, dark hair, brown eyes, nothing really special about her attributes, small tits, and not much of an ass to speak of. She was one of those with a cute face though, and looks pretty young for a woman of 45+ years of age. Looks to be in her early to mid 30s.

Anyway, this is what a typical summer's day was like in my parents household. Both of my parents work all week from morning 'till dinner time so they were always out. My little brother was going to summer school, so he was out from around 7:30 'till 12:30. It would just be me and my mom's friend home along for that span of time. If I wasn't out lethargically looking for a job, I was just at home playing video games or watching tv. I never really did make contact with my mother's friend, only a "hey, how are you today?" every time we pass by each other on the staircase, or in the kitchen when she's doing something like washing dishes or laundry. Always small talk, nothing serious.

About two weeks in with my stay back, it was morning, around 10am, and I had just woken up. I went downstairs to get some breakfast. She was in the kitchen washing dishes. I walked in and poured a bowl of cereal down for myself and ate while making the usual small talk. She asked me why it was that I hardly ever went out, and if I had a girlfriend. I told her that I appreciate the freedom, and that everyone else is busy doing something. Then out of the blue she asked me something like, "really? a cute boy like you doesn't have a girlfriend? Come on." I'm a pretty modest guy, I tried to keep on a straight face, hide the blushing, and simply said something like "No, I just don't really want to bother with one right now." To which she said, "Oh, so you're a player." I didn't even know what to say. I was kind of embarrassed. I responded with, "No, what makes you think that?" and that's when things started to escalate. She kept telling me that there's no way that I don't get around because I'm a cute guy with smarts. I was getting the message, but I was also hesitant because she is my mother's friend. I figured I already knew why, but I then asked why she kept asking such personal questions so suddenly. She then stopped washing the dishes, walked towards me, put her hand down on the table and said, "what do you think?" all flirtatiously and with a smile. I found myself stuttering, speaking fluent idiot with words such as umm, err, and uhh. Suddenly she grabbed my crotch, complimented my size, and when she did do that it's like a switch just flipped and in my mind I was thinking, fuck it, let's go. I told her not there in the kitchen, and we made our way to the guest room where she was staying. I laid on the bed, took my boxers off, and she immediately went to work. It was at the time the best blowjob I have ever gotten in my life. While she looked younger , her age became evident as all the experience was there. She sucked, deepthroated, and stroked me for about 10-15 minutes before she stopped to ask me what it was I wanted to do. I honestly have no idea how I lasted that long, but all I wanted to do was fuck her relentlessly. I made her get on all fours, stuck two fingers in her pussy and my god she was dripping wet. I couldn't wait any longer, I stuck myself in her, grabbed her hips, and fucked her as fast and hard as I could. She was going crazy, she buried her face in the sheets, constantly grabbing, moaning, and screaming, and all it did was make me go faster and harder. After a few minutes she propped herself up and begged me to stop with yells of "Oh my god I'm cumming! I'm cumming!" I never stopped, it only turned me on even more while she kept on jerking around as I kept on pounding. After she came I stopped, as she laid there breathless and exhausted. It took her over a good minute for her to catch her breath and say "What are you doing? Put it back in me!" I smiled and was only more than happy to oblige. I flipped her onto her back and just continued on my relentless fuck. I enjoyed this much more as I grabbed her titties and sucked on her nipples as I kept on fucking her. I was in a state of euphoria, everything was incredible, her legs flopping in the air as she constantly grasped onto the sheets and grasped for air. Finally I came inside her, and it was the best feeling in the world, it was the first time I've ever cummed in any woman, and I didn't even ask her, but she never complained. I laid down next to her exhausted. After she caught her breath she wrapped her arms around me, cuddled me, and whispered a thank you to me. We both just laid there until I noticed it was time to go pick up my brother from summer school. For the next month and a half until I finally got another job and moved out again, we constantly fucked during the week every morning while my brother was at school. We did good at hiding it because while everyone else was around we'd always act like we did before, just simple small talk, the only thing keeping us together was our awesome fuck sessions.

The one thing I really regret was that before I moved out was that I never established a way of communication with her because I haven't seen her since I moved back out. I visited my parents again some time later and asked my mom where she moved to, but she doesn't know. I didn't want to ask too much because I didn't want her to find out that something went between us. Oh well, I may never see her again, but I'll definitely never forget her.
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Old 03-06-2010, 02:14 AM   #2
El Suave
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Wow.. you got pretty lucky there.. Awesome story man!
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Old 03-06-2010, 07:09 AM   #3
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hahaha great great!!!
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Old 03-06-2010, 12:56 PM   #4
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Excellent, Mk4. Hope you find her again. Sounds like a good one to keep in your hip pocket. Mature women are awesome.
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Old 05-24-2010, 08:46 AM   #5
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That is great wish I had that when I was 18
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