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Carol's First Anal

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

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Old 07-21-2010, 02:23 AM   #1
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Join Date: Oct 2009
Age: 31
Posts: 13
Default Carol's First Anal

This is my 3rd story about Carol. She lives a few houses down from me and across the street. I am 27(just turned), 5'10, 200 pounds, brown hair, brown eyes, 6" member. Carol is 57, 5'9, 150 pounds, jet black hair(dyed), green eyes, I would guess 36 C (fake), shaved most of the time. I've told two stories about her so far. We have hooked up a couple of other times, but the two stories were the best most intense times. We got a little too intimate so we backed off. Most of the other times we have hooked up have been her calling me drunk after a night out with her girls or me running over for a quickie in the morning. This story is about a week old.

I had not talked to Carol in about two weeks. I got a text from her asking if I wanted to get together. It's the summer so I'm working 50-60 hours per week to build up savings. I'm in grad school. I pretty much sleep, work, and eat. Since I moved to a new town I've really only made two friends. A girl named Rachael and a guy I work with. They have nothing to do with this story so I'll move on.

We text back and forth while I'm at work looking for a time to get together. We decide on a night and continue texting. She tells me she wants to try new things. She wants to fuck in every room of her house, she wants to use toys on herself while I watch, but the one that got me was anal sex. She is 57 and has never had anal sex. So I tell her I'm down.

The day arrives for us to meet up. I had lube at my house so I grabbed it and walked over. When I got there she answered the door in nothing but a short robe. We are very comfortable with each other and know this is only about sex so its the norm. We talked for a few minutes and had a glass of wine. She asked if I brought the lube. I showed it to her and then she grabbed my hand to lead me up to her bedroom.

When we got up to her room she undid her robe and we started to kiss. Soon my shirt and pants were off. She had nothing on under her robe. After a few minuted of kissing and hand play she told me to sit on the end of the bed. As I did that she opened the bedside table and pulled out a dildo. It was a pretty big one. It startled me since even my 6" cock was too much for her sometimes. I would guess it was 8 inches long. It looked like a penis. She began sucking it, rubbing it on her tits, and working it down to her pussy. She started to fuck herself with it. It was a big turn on. I took of my boxer briefs and started to stroke myself.

She fucked herself for 5-10 minutes as I slowly stroked myself. After that 5-10 minutes she got up on her hands and knees and started to suck me. I didn't last more than 4-5 minutes. After I came I took her robe the rest of the way off and went down on her for less than a minute before she said "get the lube."

I had only had anal sex a few times and it was always me entering from behind. She wanted to be laying on her back. So she laid on her back and brought her ass way in the air. I covered my cock and her asshole in lube and slowly started to insert. I never lost my erection after I came. It's nice being young. I could see the pain on her face as I got deeper. I first got the head in and the let out a sigh. I asked if she wanted me to stop but she said to keep going. I went in another inch or so and pulled out, then back in, slowly getting deeper every time. Soon we had a good rhythm down. I was never in all the way. Probably only 3-5 inches. She still had a very painful look on her face. It actually made it less enjoyable for me. I tried to keep focus but her sighs were odd sounding. I noticed the dildo was still there. I was holding her legs up with one hand and guiding my cock with the other. Since I was going good I decided I could use one hand to grab the dildo and fuck her pussy with it.

As soon as I inserted the dildo into her pussy she went nuts. She started thrusting back into the dildo and my cock in her ass. I can't explain the noises she was making. I could tell now she was really into it. I just kept thrusting into her hard and moving the dildo in and out of her pussy with the occasional tap on her clit. We had been in this position for 15-20 minutes at this point. I could not tell you how many times she came. One of her orgasms was so intense she actually bucked me out of her. After that we had to reposition. I put her on all fours and stuck it in her ass. No dildo this time. I thrust hard and deeper than before. Five minuted of that and I was cumming. I blasted it right into her very deep. She came as I was leaking the last few drops inside of her. I had only been there for an hour and I was spent. We rolled over and tried to catch our breath. The room was muggy and we were both very sweaty. She started to laugh and said she could not believe she was double penetrated, but she also said that was the most intense orgasm she had ever had. I think anal sex will be a regular thing for us now. It was only 9PM. We took a couple hour nap and showered together when we woke up. We had sex on the bathroom floor. It was regular vaginal sex. Nothing special. When we were done with that we got dressed, headed downstairs, talked for a few minutes and I walked home.

If anything more comes up with Carol I will be sure to share.

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Old 07-21-2010, 02:25 AM   #2
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Join Date: Oct 2009
Age: 31
Posts: 13

The other Carol stores are Much Older Neighbor and Much Older Neighbor II
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Old 07-21-2010, 02:47 PM   #3
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Join Date: Jan 2010
Age: 55
Posts: 512
Default Bang Bang Bang her ass Big John..

Older women in particular love anal as you now know. I just discovered for myself a 63 year old neighbor that loves anal and plan on doing her whenever her husband is on the road like he is now.
Give it to her again from behind..they go crazy with a hard cock pummeling their
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