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Jail GIRL gets it in the ass

General Sex Stories (Written By MEN)


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Old 07-15-2010, 11:44 AM   #1
OutForFun2010
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Default Jail GIRL gets it in the ass

So, I have admitted in the past and will admit here that I have a real weakness for the "trashy" or "bad girl" type. I don't know what it is but these women that just can't seem to get their shit together really turn me on. Maybe it's because they tend to be all hardcore on the outside but VERY submissive sexually. That's my experience anyway.

A few years ago I had met a girl through a telephone chat line of all things. Andy was 19 when I met her, but this story took place a couple of years later. She was involved with some other young punk-ish types and ended up being involved in a car theft. I really didn't bother to get the whole story but it ended up that she went to some kind of jail or prison or whatever for about 10-12months. She called me collect a few times, I didn't really think too much of it. She asked me if I'd be waiting for her when she got out etc...I said no, I'm not your bf, but she kept calling. We had fucked a few times before this so that's why she was calling I guess. Eventually, she was released to what I guess would be called a halfway house. She was able to get out during the day and tried to get me to meet her but I was always busy or dis-interested. It seemed like a dodgy situation. After a few weeks of being "out" she stopped calling so I got on with life. Then out of the clear blue one day I get a call at work from Andy. She goes on to tell me that she has been set up with her own bachelor apartment blah blah blah and she wants to see me. I agreed.

We made arrangements to get together one Saturday after I was done work so I met her at her place. We got to talking about things and what she had been up to since getting out of jail. Eventually I just asked her, have you gotten fucked yet? She said yes, that her and a friend had fucked her friend's bf! Crazy chicks. So I'm starting to get turned on a little thinking about what freak Andy is. She is(was) about 150lbs, 5'3 or 5'4, strong legs, a little bit of a tummy and thick. Almost like a BBW. She does have gorgeous almond shaped eyes that look innocent and sexy at once, and full lips that only have one purpose....

We start kissing a little, making out and because I know she likes it a little rough I start giving little tugs on her hair and bites on her neck. She starts melting and moaning letting me control her. I start whispering to her "Did you miss my big cock, do you want me to pound you with it? Or go slow?" She responds "Pound me."

Me: "Did ___''s bf pound you?"
Her: "Yes, but not like you"
"Not like me?"
"He didn't spank me or pull my hair"
"You want that"
"Yesss"
"Missed it?"
"Yesss"

By this time I had already taken my cock out and was making her stroke it while I sat beside her on the couch. I pushed her head down and she leaned over and started sucking me. Every once in a while I'd push her head down and thrust upwards to make her gag on it. I love that sound that girls make, LOL. Then I told her to stand and strip, when she was naked I put a pillow on the floor and motioned for her to get on her knees. There is nothing better in the world then sittng on a chair or sofa, legs spread while some willing girl throats your cock. You get to just sit back and watch while she pleases you. It always gets me going. Eventually she pulled up and said she wanted me to fuck her, so I had her sit on the couch and then I pushed her legs up so she was folded almost in half and pushed my cock in her nice and deep and just put all my weight on her and moved my hips around in grinding motion. That really seemed to get her going. So I pulled all the way out and plunged down to repeat this action. We settled into a nice deep hard fuck, then I start with the dirty talk:

"Did he fuck you like this"
"Yes, while ___ licked his balls"
"Was she jealous"
"I think so, because I told him to fuck me hard"

At this point I don't know if she's making this up, but what the hell. So I start pounding her.

"You like that?" I said.
"Fuck yes"
"What else did he do to you?"
"He shot cum in my face"
"Really? Was he fucking you like this when he came?"
"No"
"What was he doing to you?"
"Fucking my ass"

HOLD IT!! I had fucked Andy before but never in the ass. She had always said she didn't like it and that she was afraid my cock might be too big. I actually got a little upset. So I asked:

"Did you like it? Did he ask you first?"
"No, he had be bent over and made me take it"
"I've never fucked your ass"
"You're big, and rough, it will hurt"
"Do I own you?" (A little game we always played)
"Yes"
"Do I own your pretty little mouth?"
"Yes"
Do I own your pussy?"
"Yesss"
"Well now I'm going to own your asshole you little tramp!"
"It'll hurt"
"You'll like it...you know it."

So then I pulled out and took the cushions off the couch and put them on the floor. Then I told her to lie flat on her tummy. At first, she was n't going to, but then complied. I mounted her from behind and started fucking her pussy again, telling her how I was going to take her ass and make it mine. She made whimpering sounds but never said no. So I pulled my cock out, wet from her pussy and placed the head to her rear entrance and pushed just the head in:

"OWWW!!"
"Does it hurt?" I asked?
"A little"
"You want me to stop?"
"No"

So I started to push a little more in at a time, allowing her to get used to it. But I did keep her pinned down with one hand until I was all the way balls deep. Then I started to fuck her ass nice and slow, she starts moaning, she likes it. As I sense she's more used to it I start to fuck her harder until after about 2 mins I'm really giving it to her and she's taking it like a champ!! Meanwhile, she's playing with her pussy and I hear breathing pick up and then she's cumming, and moaning and grunting so I bury my cock in her ass and don't move just let her ride out her orgasm. By this time I can't hold on much longer so I start pumping and after about 5-10 strokes I feel a huge orgasm welling up and without pulling out I just start shooting a huge load up her ass.

We fucked a couple of more times that Saturday night, and I took Andy's ass one more time the next day. But that was the first time I fucked her in the ass, not the last. I have a ton of crazy stories about Andy I could share, the girl was(and I presume still is) a real sex freak.
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Old 07-15-2010, 09:17 PM   #2
sleekride
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Watch out now! Them damn jail chicks will whip your ass! I bet she was glad to get some dick for a change after being in jail for a year carpet munching!
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