Jailbabe

byistanbulnoir©

Some readers will be familiar with websites on which prisoners can advertise for penpals. Some may even have met a nice pen pal through one of them. I have; two in fact. Both lifers; and both in for murdering their husbands. It's a bit weird, but the fact that they were killers turned me on. I was not looking for a girlfriend though, and I didn't want some ex-con turning up on my doorstep when she got out. One of my lifers used to write me very dirty letters and the other one wanted a more refined tone, so I gave then what they wanted, and each got the kind of correspondence she desired. With the dirty one it was all what we would do to each other if we had the chance, and with the refined one, it was books and life and all that.

It was all very nice and everyone was happy and none of us was doing any harm, but I loved those jail babes so much that I couldn't keep myself from surfing about on those websites until I found Delores. Delores; misery, and that's all she ever brought me; as well as the best fucking sex I ever had.

This was her ad:

Bad girl 34, lovely figure 36D, wants to find her good side, seeks nice generous, financially secure man 35-50 for long term relationship. Are you tough enough to tame me? Been in here a few times, but out again soon and don't want to come back. I was a professional dancer on the outside. I like playing pool, hanging out and having hot fun. Let me light your fire. The accompanying picture showed a rough and tough and beautiful lady, though with those hollowed out soul-less looking eyes and hardness of face that tough lives give to people. It was love at first sight.

I broke all my rules. She would be out in a year. She was incarcerated in a jail quite near where I lived. She had gone down for credit card theft and fraud; crimes of dishonesty. And you could tell just from looking at her, with all of those jailhouse tats down both her arms and round her neck that she was bad to the bone.

I wrote to her straight away, my usual letter of introduction, telling her all about myself, and of course talking myself up.

Actually I am a pretty shy sort of guy; 39, never married and not many girlfriends. Truth is, I'm a bit on the heavy side and not much to look at, and I have zero confidence when it comes to approaching women. I guess that's why I write to these kinds of women. I saw a shrink after the horrors of Delores; I was in such a mess, and he told me I have low self-esteem. He also got me talking about my attraction for these criminal women; why I like them and all that, but I don't want to say too much about that. I felt pretty disgusted with myself, learning about why I liked them. He said that even though they were tough and maybe even dangerous and nine times out of ten untrustworthy women; they were in jail, so it made me feel like I had the power. It's like going to the zoo and looking in the tiger cage and feeling scared, but knowing that they can't get you. Or maybe I should say cougar cage, because usually it's older ladies I go for. My two lifers are both older; 52 and 47. And the one women I ever had a real relationship with was 20 years my senior. So, I broke another rule when I wrote to a lady younger than me.

Anyway, I am sure that the shrink was right about the power thing; but that all changed when Dolores got out and I took up with her. I moved her into my flat and everything, and at first, for a couple of months it was good, but the signs of what were to come were there; it was just that I didn't want to see them, so I edited them out. But in the end, just as I couldn't keep away from those websites, she couldn't stay away from the drugs and the whoring (to get the money for the drugs) and that scumbag of a boyfriend (the one she promised me she had got rid of when she was still inside).

Of course, not even I am so naive as to not realise that 'professional dancer' meant stripper; but that was always what I liked about those women. I never guessed, though, that she was a prostitute too, and although I was a bit shocked at first, it was not long before the idea of that turned me on too. She had never mentioned anything about a drug habit, and I had never thought of it even in my darkest dreams.

So what was she like; the delectable Delores? Exactly what you would expect. You know the expression 'does exactly what it says on the tin?' Well, that was Delores. Trouble is; I didn't read what it said on the tin. Fact is; I didn't need to. I already knew; or guessed; but I just ignored what I knew or guessed. It wasn't that I was in love with her; not really, and she was pretty unlovable. It was irresistible, uncontrollable lust; that was that woman inspired in a man. Most men would have had the good sense to run a mile when they saw Delores coming; or better still pick her up in a bar, fuck the arse off of her and not even tell her their real name. And even if she wanted paying for it, she was well worth the rent money. She was as sexy as Satan, and a lot better looking, in her wrong side of the tracks, trailer trash way. Pick it up, fuck it and dump it quick. That's what women like Delores are for; unless you are as much of a degenerate as she is.

Not a nice to say about another human being, I know, and of course she was not born evil; she had a truly horrific upbringing and her adult life had not been much better, but I am not really the socially concerned type. I didn't think I could reform her or redeem her. I never really thought about that. I think I just wanted to live out a sex fantasy and didn't give much thought to the consequences. Well, that's the lie I told myself anyway. I was lonely. A bit of a loser maybe. One way or another, I brought it on myself, and you know something; there are times when I think it was worth it. I lost almost everything I had thanks to Delores, but the sex...it was fucking fantastic.

She wrote back to me pretty quickly. I got her letter less than three weeks after I wrote mine to her. It was mixture of pop psychology self-help slogans, some vague stuff about herself and a few fairly obvious sexual come-ons. She had also included a photograph of herself, topless at some beach. She had lovely boobs and looking at the picture made me hard.

So far so good. I wrote back, she replied again; more self-help slogans, more vague details of her life, a few questions about me and more sexual come-ons; and another photo, this time with a bit of pussy on show. Sexy, but not pornographic.

And so it went on, until after we had exchanged three or four letters each, and then she asked me if I would visit her. I didn't hesitate. She had told me when the visiting times were and I picked one and told her that I would come then.

The day arrived and I drove over to the jail where she was doing her time. It was about an hour's drive. I was a bit nervous, but I was looking forward to meeting her. I got there, went through all the checks and I was directed, along with all the other visitors, to a large hall. It was full of tables about two metres long and one wide, uniformly aligned. Her crime was pretty low level and she was not considered dangerous (she sould have been), so she was allowed to meet visitors here, rather in some more secure place. There were guards patrolling about to make sure nothing contraband was passed over, but you were allowed to touch, as I discovered.

I got there before she did. She would recognize me, because I had sent her a photograph of hmyself. I sat waiting as the room filled up more and more with inmates and their visitors, and she was one of the last to arrive. She knew well the value of making an entrance. Finally she came. She was easily the most attractive of the female prisoners who emerged and pretty much everyone in the room craned around to get a look at her as she slithered down the aisle between the tables towards me.

My cock leapt at the sight of her, and I swear it, I almost spunked my load in my pants when she looked at me as she was sitting down.

'Hi,' she said in her gravelly, drawling sink estate accent.

She must have spent hours preparing for my visit, and I wondered how she can have managed to get hold of so much make up in there. But Dolores had her ways. She looked like the woman who came first in the annual beauty contest at the local working men's club, in the over-40's category. Gutter glamour; that's what you'd call it. Way more sexy than the average model bimbo, because she was real.

I liked her immediately. I had been lusting after her ever since I had seen her picture on that website, but now, after only a couple of minutes chat, I liked her too. She had charm; in spades, and she had charisma; she could turn it on like the proverbial tap, and even though you knew you were being charmed and sweet talked and led up whatever garden path she fancied leading you up; you went anyway, because she was just so damned good at it and so fucking sexy. And she knew it. She could seduce a man in seconds, and she had turned the trick a thousand times.

Visiting time lasted for an hour, and we just chatted for the first twenty minutes or so, during which she chain smoked, rolling her cigarette gently between her fingers and pursing her red lips suggestively every time she took a pull. The she let one of her manicured hands; her fingernails were like great red talons, fall onto the table and held it open and looked at me, half invitingly, half almost imploringly; and purred through the skeins of smoke that tumbled and drifted about her head that

'We can hold hands. That's allowed.'

'So I placed my hand in hers. Immediately, I felt her finger caressing my palm. She stared straight into my eyes and said frankly

'Do you like that?'

'Yes!' I mumbled nervously.

She just smiled knowingly.

The guard who was nearby noticed that she was up to something, but after a careful look, moved on without speaking to her.

Then suddenly I felt her foot rubbing gently against my ankle. She must have eased off her shoe, because it was a bare foot I could feel. She smiled conspiratorially and brought a finger up to her lips and held it perpendicular to her mouth to indicate to me that I should stay silent.

Slowly her foot made its way up the inside of my leg and automatically I opened my legs for her. She eased forward on her chair a little, to enable herself to reach. Everyone around was too busy conversing with their imprisoned loves ones, making the most of the precious hour, to notice what Delores was up to. The guard saw her though, but instead of coming over and stopping her; and probably carting her back to her cell too; he stopped and turned his back on us and stood between us and the rest of the room, so that no one would be able to see what she was doing. Like I said, Delores had her ways. No doubt he was getting more than just a foot job for his pains.

After what seemed like an age, her foot was finally running up and down and side to side over the bulge of my crotch. I had been rock hard since she had sat down, and I am sure that she had known that. When she had been able to confirm it to herself with her foot, she said

'You like Delores, then?'

I was so excited I couldn't speak.

She carried on rubbing her foot over my erect and now throbbing cock and she kept that up for a few minutes and she said

'Careful baby, not yet.'

What were we waiting for, I thought to myself? Then I found out. With her toes she pulled down my zip, and then her big toe nuzzled its way through my fly, managed to open the hole in my boxer shorts and arrive at its destination. Contact! Her toe was touching my cock; flesh against flesh.

I was never going to last long with that going on. She ran her big toe up and down my shaft; still inside my trousers and boxers, and she seemed to know instinctively when I was going to shoot, because she placed the underside of her toes above my helmet at exactly the right moment. All the while she looked me straight in the eye, partly for the pleasure of it and partly warning me to stay quiet.

I noticed that she flinched, almost imperceptibly, when I shot and my cum hit her toes, and then she smiled broadly in triumph. She withdrew her foot and then, when it was back where it was supposed to have been all along, her hand reached down below the table, lingered there for a long moment, and then re-emerged. As she raised it towards her mouth, she turned it momentarily towards me, and I saw a generous smear of my semen on her fingertips. Her hand reached her mouth and she slid her fingers between her lips and sucked them avidly. She even poked her tongue out to show me a drop of the pearly oil on its tip.

'Was that nice?' she asked.

'If you can do that in a place like this, in these conditions, what can you do in the privacy of a locked room?' I asked.

She just smiled and said 'you'll find out. I'll be out of here in eight months.'

The thought of it excited me; and scared me too.

'You know the guard saw us,' she said.

'I think he helped us too,' I said.

'Yes,' she said, 'I have my ways. But I will have to pay my dues later. That's how it is in here.'

'I suppose so,' I said, trying to seem cool, but a sharp pang of jealousy was cutting through me.

As if she knew it, she said, 'it's only sex.'

Only sex, I thought. Only sex that made me write. Only sex that brought me here. Only sex that makes me do things that will only hurt me in the end. Only sex!

Visiting hour over, it was time to go. I promised her I would come again and that I would write her a letter that very evening. I was as good as my word. That evening letter writing was punctuated with breaks to masturbate over Delores' photographs and the memory of what she had done.

I visited her once a fortnight and wrote a couple of times a week, and the weeks and months rolled by. Life is nicest when you have something to look forward to, and even though I still had reservations, I looked forward to her release, and even though I feared her more than a little, it became part of the thrill, and I admitted to myself that if she was up for it, a full on relationship would begin as soon as she was out.

Looking back, the first couple of months after her release were great, but as I said, the signs of what was coming were there even then, when it all seemed so wonderful, so now I think that it was really those last few months when she was still inside that were the best. Through my visits, and even more through our letters, we really got to know each other. I poured out my soul to her, and her letters changed too. She dropped the fake self-help claptrap and even the sexy come-ons; she didn't need those anymore; I mean, I had come on her toes a few times by then. She told me about her life, and it was a miserable story, and knowing her story I could understand how she had ended up where she was. Orphaned, abused, raped by an uncle when she was 18, no education to speak of, she had started working as a stripper. She was honest, up to a point. At least, she didn't tell any lies in those letters, but at the same time, she did not tell the whole of the truth. She never mentioned the whoring or the drugs, or the guys she had ripped off along the way. Well, she wouldn't, would she? And I still find it hard to condemn her, even now. I learned all about that at the trial later.

Finally, the day arrived and I went to meet her as she left the prison. All she had was a single weekend suitcase, her whole life in it. We had never actually discussed it, but she had told me she had no place to go, so it was natural to ask her to stay with me for a time, while she put together a life outside. But I knew she would not be moving out any time soon and I didn't want her to. That day I was happy, and so was she.

All through those months I had thought that the day she got out, a soon as I got her back to my place, we would be on each other like a pair of wild animals. Since I had met her, I had not had any sex, except the foot games she had played with me on some of those visiting days, and I hadn't had much for a long time before that either. She had had to service that guard, and probably others too, to get her little perks, but I told myself that she hadn't enjoyed it, so it didn't matter. Later she told me that she was bi-sexual and that she had had flings with other inmates, and how they stole tools from the workshop and used them as dildoes on each other. Her stories turned me on, and she used to tell them to me as we lay in my bed, in between fucks.

As it turned out, when we got home, we sat chatting for a few hours and shared a bottle of whisky. It was only after that that we got down to it, and that first time, it was gentle, almost loving; quite the opposite from what I had been expecting.

The rougher, hungrier and more fervent fucking that I had anticipated for so long came soon enough though. We must have done it ten times a day, and another ten a night in that first fortnight. I had taken the two weeks off work, and there was nothing to do besides eat and drink and fuck and watch television while we rested between bouts.

Each time, the sex got dirtier and she got tougher and more aggressive and dominant. It was like a sixth sense with her. She just knew instinctively how I wanted her to be in the bedroom, and she knew what I wanted from her sexually even before I did. She also discerned quickly that not only was I shy; I was also inexperienced and timid. She would have to lead, but she saw quickly that I liked it that way, and anyway setting the pace in bed came naturally to her.

The first step we took beyond the vanilla was one afternoon, on about the fifth day. I was lying back on the sofa and she was riding me fast and hard. Her lovely tight shaved cunt was giving my cock a very thorough workout as she bounced up and down on it, and looked straight down at me and told me how much her cunt loved my cock and how her cunt was going to suck all of the spunk out of balls, and how when the fuck was over she was going to suck me off and drink even more of my spunk. She was fantastic, and the word 'inhibition' just did not exist in her lexicon and under her tutelage, I was rapidly losing my inhibitions and my shyness too. Delores made me feel like Superman; I could walk up to any woman in the world and get her number within a minute and have her in my bed that very night.

So, Delores' cunt was sliding up and down my pole and suddenly with one bounce, a little higher than the others, and a minute shift forward; when she came down, it was not her pussy that my cock disappeared into, but her arsehole. It was unbelievable; the skill with which she did it. The move was seamless; graceful even, if something as lewd and filthy as arse fucking can be called graceful. She sat all the way down, so that her spread buttocks were resting on my hips, and my full seven inches were embedded in her rectum. She looked down at me and laughed and asked me

'You ever been up a lady's arsehole before?'

I hadn't, and it was heaven to be there now. She reached down and peeled open her cunt lips and I could see the fiery red flesh of her inner cunt walls as her tight arsehole hugged my shaft, and I felt the tightness of her ring around the base of my cock and the soft and oily-feeling flesh of her of her rectal canal caressing the sensitive flesh of my cock. She began to ride me with her arsehole, slowly at first, and then faster and faster. Her fingers worked her pussy and her clit as she rode me, and she flailed around on me more and more wildly until her whole body clenched. When she came, she squirted; really squirted, and the clear, viscous, salty woman juice shot all over my chest. I only wished it had reached my mouth. A moment later, my cock erupted in her anus and I pumped her rectal canal full of hot spunk. Afterwards she squatted and opened up her arsehole and let me watch her drip dry.

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byistanbulnoir© 2 comments/ 21271 views/ 0 favorites

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