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New Girl in Prison?

Category: Anal Sex
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I am a 34 year old divorced woman. I have recently moved from the small town where I spent my whole life to a larger city, to re-start my life.

My ex-husband had little or no interest in sex. Sometimes it would be months between feeble attempts. There was never anything interesting or creative. No oral, or anal, which I was craving.

I have tried to figure out where my anal-erotic feelings came from. I think I know how it happened. When I was twelve, my Mother gave me an enema one day. It was strictly therapeutic as far as she was concerned, but it aroused some erotic feelings in me.

She only did it that one time, but after that I would sneak into the closet where the enema kit was stored, and take out the tip.

I would lay on my bed with my pants pulled down, and insert the enema tip up my asshole. I was just beginning to learn how to masturbate, and I would tickle my little clit while I fucked myself with the enema tube. I would always wash it to make sure it was clean before I returned it.

I got more adventurous, and instead of stealing the rectal tube, I would take the larger feminine hygiene tip. It was much longer, and it had a sexy look. After some experimenting, I was able to get the whole thing up my asshole. By the time I was thirteen, I would have a very satisfying orgasm that way.

My Mother caught me in the act of returning it one day, and that was the end of my enema tube sex. It was not the end of my masturbating, however. My masturbation fantasies always included being fucked in the ass by an imaginary guy. His imaginary cock was huge, and his imaginary load of semen felt wonderful as I made myself come.

Through my teenage years, my boyfriends would finger my pussy during a petting session, but they would never touch my asshole. It was frustrating.

I got married at nineteen, and I found that my new husband was clumsy and not too thoughtful when we had sex. As I mentioned at the beginning of my story, there was never anything interesting or creative.

I would read letters in the sex magazines, from women who enjoyed anal sex. I thought I was the only woman in the country my age with a virgin asshole.

Years went by, and I tried to be a good wife. After twelve years of marriage, I had enough. I wanted to live my life.

There were other problems in the marriage as well, and we ended it. I moved here and set myself up with a job and an apartment, and after that I began to feel ready to look for a relationship.

I met a man who was the direct opposite of my ex, and that made him seem perfect. We have a good sexual relationship, in and out of bed. We can talk about sex seriously, or joke and kid around.

I haven’t said anything about his cock yet, but it is nice and long. Some cocks are curved upward; some are curved to one side or the other. His is straight as an arrow, with a thick and heavy feel.

He is circumcised, and the head is always exposed. I love to suck him off, and make him cum in my mouth. I know some women find it unpleasant, but not me.

I wanted his cock up my ass, but I didn’t know how to let him know. When he would lick my pussy, I would lift up and his tongue would touch my asshole. Once he just sort of accidentally brushed up against my asshole with a finger. I couldn’t stand it, and I pushed against it, and his finger went in a little.

Afterwards, he looked at me with a curious expression. He didn’t know if I wanted him to explore my ass, or if it was just coincidental. I am pretty sure he was getting the message.

I like him very much, and I wanted him to like and respect me. I suppressed my anal longings, even though I still wanted it very much. I did not want him to think I was a pervert, so I never brought up anal sex.

Thankfully, he finally brought it up.

One evening he asked me if I would be willing to play a game he called “new boy in prison”, and he laughed. He has a great sense of humor. I said yes, but only if he did not beat me up and I did not have to wear a prison uniform. I was joking too, but not about the “yes” part.

We went into my bedroom, and we were soon naked. I got on the bed on my back, with my butt on the edge of the bed, and my legs raised as far as I could. I chose this position because I wanted to see everything that happened. Lying face down or on your knees doggy-style leaves you looking at the bedspread.

We were both not sure if the message he sent was clear. I was looking at him, wondering if he meant it, and he was looking at me, wondering if I understood it.

He put his cock up my pussy, and fucked me for a few minutes. I think it was just foreplay, and maybe he wanted the lubrication from my wet pussy.

I encouraged him, I said “Get it real hard, and slippery.”

“Just to be perfectly clear”, I said, “I want you to fuck me in the ass. I want you to shove it all the way up my asshole.” He pulled it out of me, and took it in his hand and lowered his aim about an inch.

I was quivering with anticipation, because I was finally going to have a hard cock up my asshole. I had been fantasizing and dreaming about it all of my adult life. He looked at me to see if I approved, which I did.

I felt his cock touching my anus, and I concentrated on trying to relax my asshole to let him in. I don’t know if that worked, or if it was the pussy lubrication, but it went right in.

I have read stories where it is difficult to get it in the first time. The guy has to push hard, and it slides in an inch at a time. The woman is grunting and squealing, as her asshole is stretched open.

I wanted it up my ass so much that my body just obeyed me. He pushed it in with one long, steady shove, and it was all the way up my ass. There was just the wonderful feeling of being full of cock.

I could feel every detail of his cock in me, including the head. I could feel it much more this way, because your rectum is much more sensitive than the inside of your vagina.

I know that your plumbing twists and turns in your belly, and I always worried that a really long cock would hit a roadblock, and I would not be able to take it all. That would have been very disappointing, but it did not happen.

His balls pressed up against me. I was so hot I think steam was coming off of me. My pussy was soaking wet, and my love-juice ran down onto his cock as it slid up in me. It was excellent lubrication.

He fucked me lovingly, not violently, so it was not at all like a prison rape. He deposited his semen way up inside me, and it was as satisfying as I had dreamed it would be.

When a man comes in your wet vagina, you just feel wetter. When he comes in your asshole, you can feel his cock twitch, and you feel each warm spurt of cum go into you. It is the most intimate feeling in the world.

Now we do not have to kid around anymore. If I want it up my ass, I just ask him for it. If he wants to fuck my asshole, he just says so. One or the other of us always seems to ask for it that way. My pussy feels neglected. I do not care.

My sex life is finally perfect. Sometimes we take turns orally. We still do it the so-called correct way, vaginally. At least three or four times a week I get it in my ass. When I am being fucked in the ass, I get in the same dreamy, hypnotic state that I did as a little girl, play-fucking myself with an enema tube.

We have tried it in every position we can think of. Hands and knees, lying face down, lying on my side, whatever. My goal is to find the position where his cock goes in the deepest. One time he asked me where I wanted to feel it, and I said “Up between my shoulder blades!” Like I said, we joke and kid around a lot.

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