Jail Bird free porn video

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Alistair find himself faced with a stark choice when sent to prison and men start to look at him in a different way. He can fight them. He can go into protective custody.. Or ... he can find himself a 'friend'. That means becoming a boy in a bra. Before long, that bra starts to feel just a little too comfortable. Darren's diary: It was Lou Reed who said "plucked his eyebrows on the way, shaved his legs and he was a she". Well, I think it happens at a slightly different time. When a boy starts plucking his eyebrows and shaving his legs, yes, that's a good indication that something is going on. But for me, when the first cock goes in, that's when he loses his manhood. That might be before or after the eyebrows and shaved legs. Or should I say, when he allows himself to be fucked. If it's forced on him, well, that's not his fault, is it? But when he opens his legs and is being shagged by a real man for the first time, there's no going back. Sometimes they think they can get it back by starting a fight, something like that. But it's like the boxer who's been knocked out. Whatever he, or in this case, she, does, everyone knows. You can't get it back. And whatever happens after that, when she starts mincing around in high heels, starts to fill out that bra, even gets the sort of downstairs tackle that make wearing Y-fronts a bit pointless, he was a she long before that happened. In here, I get plenty of pussy. That's what it like in prison. There are plenty of gays, but I don't consider myself gay. Sometimes one of them might be gagging to suck my cock, and on occasion I'll let them. But my ideal is getting my hands on a boy and starting his journey towards not being a boy any more. And I don't mean making a man of him. Like this one I have in here today. First time in prison. Teenager. Quite slight. Frightened to death of being raped. A little bit scared of being called a queer. He never knew it, but he's an absolutely prime candidate to be a she. He'd been inside a few weeks. We all immediately identified him as a potential turnout. A pretty boy. He resisted, of course. It took him being pushed up against the wall in the showers and told if he didn't cooperate he'd lose his teeth. All the better for giving blow-jobs, you see. It wasn't me who confronted him in the showers. I don't go in for that. As I say, I get all the pussy I can handle. And I prefer it when they offer themselves up to me. Much more fun. A mind fuck. As well as a physical fuck. The screws saved him that time, but they wouldn't be there all the time. Frightened out of his life, he discussed his alternatives with the 'girls'. There were three options. The first was fight. He might win. But there are people in here for life. They've already killed. They are not getting out. Start a fight with one of these, one of you will end up dead. The absolute best anyone could hope for was that one of them would end up scarred. The lifer doesn't care if it's him. Think about that. Second alternative, go on what we call Rule 43. Protective custody. With all the perverts and child killers. They tend not to be too popular in prison. They can end up with a knife in the back. At worst, they get out of here alive, but everyone knows they are nonces. That's a life-changing decision as well. The third alternative ... get yourself a nice strong fella. Start taking the pills. We can get hold of 'medication' which, after you've taken it, doesn't make it seem quite so bad. The third alternative is where I come in. This one came in here trying to negotiate a fourth alternative. There isn't one. He had muttered something about the two of us being friends. By that, he meant that I would look out for him, make sure that he wouldn't be raped. And in exchange, I'd have the honour of his friendship. We have a little scenario for people like this. You invite him into the cell. There's a cosh on the bed. He can see it, he can get to it. Then, I say: "Pick it up or drop 'em." Do I have to spell it out? Pick up the cosh and fight. You might win, in which case you are accepted as one of us. Cock of the walk. Quite literally. You're the one who calls the shots. But if you're thinking of the consequences, of going for the cosh and not getting there, or starting a fight and not winning it, then you're better off not picking it up in the first place. Drop your trousers and accept your fate. Which may well involve getting out of the habit of wearing trousers. It means acknowledging that you're not a real man. Never have been. It's only now they realise it. And that's what this one had to accept. That he needed a man to protect him. One he had to be 'nice' to. He decided to drop them. And moments later ... we are where we are now. He's taken his clothes off and he's lying on his back, about to start dreaming of England. It's a position he is going to have to get used to. And I want to see his face, and him to see mine. As we get better acquainted, I'll take him doggy style. It's good fun. You can get in that much further and after a while they like that. It's quite fun to double up. Get one of my pals to take his bird doggy-style, while I'm doing mine, and get them to face each other. Then they get to see each other's faces, that funny look, and the gentle rocking that is all part of being screwed. For them, it's like looking in the mirror because whatever is happening to the other bitch is happening to them too. But the first time, I want to see his face and I want him to see mine. And I want him to know that by the time we reach this position, there's nothing he can do. He's weak and powerless. And that's how it will continue. He has his legs on my shoulders. I do have a rule. If there's one thing I hate, it's hairy chicks. This one is quite clean but after I've fucked him, I'll have him plucked. No hair on the chest, no hair on the legs. Nice little patch of pubic hair is okay. His pathetic excuse for a cock is not going to be getting a lot of action anyway, so it doesn't really matter. But I want the rest of him as smooth as a billiard ball. Not that he knows it yet, but I'm not going to give him stockings if they're going to be put on hairy legs. Facial hair is a problem. It's obviously a no-no. The 'medication' we put them on will take care of it in the long run, but a heavy beard is a real turn-off. This one appears not to have too much trouble in that department. You can just see him, shaving away at home, before he got here, pretending he had to do it every day. Well, that's one of the things that's not going to be a problem for him any more. So this is the scene. A pretty little boy with his legs on my shoulders and my erect dick at his little hole. His objections to his current predicament have been treated with the scorn they deserve. A look on his face. Ah, if only I had the words to describe it. The wide-open, scared eyes. Those little boy nipples. When he came in and dropped his trousers, the first thing I did was go for the tit. It's a psychological thing. We'd just agreed to have sex, he'd accepted it, and he probably thinks I'm going to grab his balls. Those were his sexual organs up to now. By going for the tit, it just reinforces his changed circumstances. Just a little tweak. He jerked back. Now, a few minutes later, he's lost the clothes and it's about to happen. The look on his face. It's apprehension, for sure. Resigned apprehension. A little bit of fear, although he's trying not to show it. Fear of the pain, which is sweet, but fear of what is going to become of him, which is just too cute to be true. And this one had it all over him. The fear that when he walks out of here, he'll be different. People will look at him differently. Treat him differently. I teased his little hole with my cock. Just brushed up against it. He twitched. I almost came there and then. Just smelling his fear. Then I apply the lubricant. Cold and rough, on his spot and a finger right up him. He flinched. God, I love the little flinches of a virgin. I'm holding his arms down to increase the feeling of helplessness. That feeling that, whatever happens now, it's going to happen. He can't stop it, no matter what he does. He can't fight his way out of this one, not a helpless little piece like this one. He could wriggle and fight all he wants, but he's still going to be taken. Penetrated. He's thinking of the moment when the positions were reversed, and he was screwing his girlfriend. I can tell, from the size of his cock, that would not have been an earth-moving experience for her. I, however, have no problems in that department. He's thinking perhaps it will be better from the other side of the fence. Well, he's about to find out. I tell him to relax, that this is nothing. People do this sort of thing all the time. That he had no alternative. It's what makes the world go around. I push the head of my cock just into his hole. It's in there, and he knows from the look on my face that it won't be coming out just yet. He thinks this is it, I'm being fucked. He's thinking, this is his worst nightmare. But he's not being fucked just yet. At this moment, they always do the same thing. They contract their muscles. Call it nerves, call it his masculinity putting up a bit of a fight. You simply can't get your cock in any further at this point. Very frustrating for me. Or at least it would be, if I didn't know exactly what to do. But of course he doesn't know this. He's never been fucked before, how could he? You wait. And wait and wait for your moment. He's holding his breath and thinking that this is it, this is all he has to do for now. But he can't hold his breath for ever. He can't keep those muscles contracted permanently. I have to get him to relax. All you have to do is get him to say something. Anything. I'll say to him, "Relax baby, and it won't hurt." He says "I'm trying ..." He doesn't get a chance to finish the sentence. As soon as he opened his mouth, let out some air, the muscles relaxed. The big push. And I was in. Right up to the hilt. And then his eyes bulge out with fear, pain and maybe already just a little touch of excitement. Or perhaps I should say her eyes. He has become she. One thrust and she's impaled on my cock. Spiked! Penetration has been achieved. It's a feeling she's going to get used to. But there's nothing quite like the first time. What a look on her cute little face. Those pretty eyes just popping out. What a memorable moment for both of us. Her first fuck. The first of many. A gasp of air. Then I pull out slowly and in again. Very slow. She's tight, too tight, but that will improve. It obviously hurts. I mean, I've never been fucked myself, but I would imagine having a broom handle like mine in your most intimate place would be something of a shock to the system. But she knows what's she got to do now. And then in and out, slowly gathering pace. Now, at last, she is being fucked. Well and truly. If being penetrated was a shock, which it was, being fucked, in and out, in and out, was off the register. Girls are fucked, not boys Now she can see my point. When the tip of cock was inside her, she wasn't being fucked. Only now, she can tell the difference. She's being given a good seeing-to. A man would never be in this position. And if he was, he'd do everything to fight it off. But a bitch like her ... when she dropped her trousers she was effectively asking me to do it. Before long she'll be enjoying it. You can almost read their minds. She can see the look on my face. Well, she could hardly miss it. I'm right in it, towering over her, showing her who's the boss. I think this one is going to like it. She can see how much I am enjoying this. My eyes are half-shut, I can't stop that smile. I roll my eyes. And I'm not faking it, this is really turning me on. I'm almost dribbling all over her. And she sees this and compares it to when she was a he, and when he fucked his girlfriend. And how it had been an extremely disappointing experience for both of them. And the wheels start to spin in that female mind of hers. It is starting to become a female mind now, and this is one of the first female thoughts to pass through it. That if she can give a man such pleasure, she must be pretty good at it. Her first experience of female pride. And she certainly is pleasuring me. At last she has found something she is good at. The old 'he' may not have been much of a success with the women, and he wasn't much of a criminal, but the new 'she' is certainly going to a success with the men. I can feel that pathetic cock of hers getting hard. It hardly gets in my way. Her cock is an irrelevance. I take my time. Again, a quickie is good, but a longie is even better. I slow down and speed up as necessary, keeping myself going. It also loosens her up. After about ten minutes of gentle fucking it won't hurt her any more. Her prostate is being teased, so I know she's getting off on it. That her own pathetic excuse for a cock, is hard, or at least as hard as it's ever going to get. I'm going faster now, pumping in and out. We both know I'm about to come. Another step on the journey she is taking, because there's a little bit of maleness that comes to the fore, and if I don't snip it off right here, who knows what will happen? You see, if I don't ejaculate inside her, she could probably tell herself she hasn't been fucked. She'd be lying to herself of course. Whatever else, she has been porked, there's no doubt about that. But that little male side of her might try to reassert herself. She might con herself into thinking it didn't happen. We can't have that. If I don't come, before long she'd be'd telling herself she fought me off, or that she wasn't a female. But once I come, once I fill her sweet little hole with my cum, once she can feel it dripping down her thighs, even she won't be able to deny she's been fucked. Well fucked. Once she finds herself with a man on top of her, with that look of satisfaction on his face, well, she feels a bit of pride. She did nothing to stop it. That's another of the killers to her wilting masculinity. If I'd had to take her forcefully, well, that would be bad enough, but to give herself willingly ... Well, only females do that. We can both tell that moment is coming ... And here it is. I'm right over her face, groaning with enjoyment. Again, that's not an accident. She needs to see her man enjoying her body so much he loses control. And with those involuntary jerking movements, I come like a shower. Tell that one to your mates down the pub, I think. An interesting story from prison. As she walks around for next few hours, she'll be able to feel it. That's enough. If a bloke looks at her in a lustful way, she'll think for a moment of playing the hard man and hitting him, then she'll feel the pain, remember the fact that she has just penetrated and she didn't do a damn thing about it. She'll remember the look on my face. She'll remember she's had all her hair plucked from her legs. Then she'll just smile sweetly at him and think that if she gets any trouble all she has to do is tell me. I'll sort him out if necessary, but it won't be. I pull out of her. I have that post-coital smile on my face. I kiss her. Get used to it darling. "That was amazing," I said. Popping her cherry was an amazing thing to do. She needs to start getting into the mindset that she can pleasure a man. As she gets up, you can tell that he is now definitely a she. You can't walk straight after you've been fucked, and everyone call tell. But she's only just started on that journey. There's still plenty of bloke left inside her. But her life has changed forever. When she gets out of this place, she might look at a pretty girl. And think for a second, she wouldn't mind fucking her. But only for a second. She'll look at the girl's boyfriend, and then wonder what it would be like to be fucked by him. I want her to view that woman as a rival. I want her to be looking at her clothes, her make-up, and thinking that she's better looking than this woman. But, as I keep on saying, one step at a time. As she gets up and puts her boy clothes back on, I give her arse a big pinch and remind her that it's mine; and I'll be enjoying it again before long. "Go and get yourself shaved, and then come back," I tell her. She fingers her face. "Not your face, you stupid tart. Your legs." You talk about conquests, well, she's been well and truly conquered. Polly's diary. Later that day. It was written all over his face. If it hadn't been, I could tell from the way he was walking that it would be difficult for Alistair to sit down for a while. And there was only one reason for that. "Well," I said, "he didn't waste any time did he?" It was true. Often in these situations, someone like Alistair would be given some time to think about his decision, to make sure he was going into his new circumstances with his eyes open. But Darren had clearly decided there was no time like the present. That was his right. It was sad in a way, because when Alistair had gone in to see Darren, he had been full of bravado. How the two of them would sit down and have a chat, man to man. That Alistair would tell him that people were threatening him, and he needed a 'friend'. Alistair had told me that there wouldn't be anything gay going on, that would simply ask him to look out for him. That if anything funny was suggested, Alistair was quite happy to fight Darren. Take him on. Well this was the result. He'd left the cell full of bravado. Half an hour later, his requests had been ignored and he'd been fucked in the arse. There were tears in his eyes. I hugged him. "Oh Alistair. It's not so bad. You're not the first and you won't be the last." After all, it had happened to me. It had happened to all of us and the first time always is a shock. Everything changes so suddenly. In a flash you're on the other side of the fence. You never look at a man quite the same once one of them has had you. And I mean had you. I've been had, and now Alistair has been had. I told him to sit down. He said he couldn't. I told him he needed to have a shower, just to clean up and start afresh. So I took him to the shower block. That made him nervous, in that he'd nearly been attacked there before, but I told him that now Darren was his boyfriend, he didn't have anything to worry about. He winced at the word 'boyfriend'. He'll get used to it. No one was going to bother him now. There was one particular part of the shower area that we went to. The 'ladies' room' they called it. The prison 'bulls' don't go there. An area where if you went to the toilet, you sat down, if you know what I mean. Alistair would be doing that from now on. If you went in the ladies' room, everyone knew not to bother you. When we got there, I helped him out of those old clothes. He certainly was a pretty boy. t Darren would have been as stiff as a rock. Alistair's legs just seemed to go on forever. I didn't say it, but I knew now it was just a matter of time before pretty Alistair was encasing them in delicate stockings. He muttered something about being told to shave his legs. The poor little darling. We don't shave legs in here. Darren should know that. But what do you expect a man to know about feminine hygiene? I sprayed on the hair removal cream. All over his legs, arms, bum. He looked a bit silly, but when I turned the shower on him, the hair just fell off. As I helped him wash, it was obvious there wouldn't be any trouble hiding that penis and the balls out of the way. Before today, having a small penis would have been a big problem for Alistair. Not any more. It was a positive advantage. As he turned around to go in the shower, I had a look at his bum. Not that I needed confirmation, but there it was. I'd seen worse. Clearly, Darren had been gentle and used lubrication, which was sweet of him. There was a bit of bruising. I couldn't see any blood. Just a bit red and sore, and still dripping with cum. I knew quite well that all Alistair could think about was that feeling in his bum, what had been in there. Alistair just looked confused. I could see him look at me, and wonder if he would end up like me. The answer is yes. He'll end up liking it. Everybody does. And if Darren gets out before him, he won't be thinking his nightmare is now over and he can get back to normal. He'll be fluttering his eyebrows and trying to catch someone's eye. Those thoughts were going through his mind. Was he going to start enjoying it? What did that say about him? Alastair spent ages in the shower and I got some clothes ready for him. He knew what was coming. You know in prison, the trustees wear an armband, the screws wear uniforms? So everyone can tell who they are? Well, it's not just them who wear a uniform. Us 'girls' are readily identifiable as well. With me, it's obvious ? you wouldn't mistake someone like me for one of the prison hardmen. Alistair probably wasn't quite ready for that yet. He was about to become what we call a 'boy in a bra'. It's what we call someone who has just been turned out. Not been in prison long, thought about fighting to survive, but very quickly decided to get a boyfriend and let him be the man. Well that's fine but you don't start to enjoy cock overnight. It takes time. Alistair wasn't a fool, he knew he'd lost his manhood. He'd taken the first all- important step on the path he was taking, but no more than that. For now, he was just accepting that he was no longer the one who would be doing the fucking, but would be the one who would be being fucked. He wasn't going to enjoy it. He had hardly been broken in yet. He wasn't going to wake up in the morning and wonder whether he should wear a dress or a skirt. He wasn't going to sit down with me or the other girls and talk about nail polish, the best way to give head, or that all important subject, shoes. Not yet. For the moment he was probably still 90 per cent male. He still wanted to talk about football. But the female side of him had been accessed. It would grow. The other prisoners needed to know his status, so he needed to wear an item of clothing that would identify him. Not necessarily something on the outside. Something that would rub up against his skin and remind him who he was. It could be an item of underwear. Alistair was about to become a boy in a bra. As I helped pat him dry, I gave him his first dose of medication. "Take these," I said. "They'll make you feel better." He didn't question me. One good thing about the modern youth, I suppose. The one thing they won't turn down is pills that make you feel better. I did think of a sports bra, or a very plain one, but I decided that at the end of a day a bra is a bra. They don't make them in men's sizes. And if you have to wear one, it might as well be a feminine one. So I chose a nice pretty white one for him, with lace on the cups and a little bow in the middle. It's amazing how a bra transforms a boy. You don't have to stuff socks in it or anything like that. As for doing manly things, like fighting, like sitting round and drinking, smoking, you don't do that in a bra. If Alistair were ever to find himself in trouble, cornered somewhere, all he would have to do was undo his shirt, and show that he was a boy in a bra. We have a code in here. No one attacks the boys in bras. People in prison might be a lot of things but there are rules. You don't hit chicks. The first thing to go is your male pride. Pride in the size of your dick, all that sort of thing. That doesn't last long, male pride. Pretty soon, having a huge cock thrusting in and out of you doesn't hurt quite that much. Then, he starts to like it. Just a little. A very guilty pleasure, but that's where someone like me comes in. Make them feel a little less guilty. After all, what choice does he have? May as well eat what's on your plate. And then, he's a boy in a bra no more. When a bloke looks at you lustfully, and you look back at him, wondering what his cock is like, you're no longer a boy in a bra. When you lick your lips and lower your eyes as you look at him, you're no longer a boy in a bra. When you're standing in a crowd, with your man behind you, and you can feel his cock pushing into your bum, and you wiggle a bit, rub up against him, get him going, you're no longer a boy in a bra. But one step at a time for Alistair. I helped him dry and just quietly tried to help him into the bra. "What the hell do you think you are doing?" he screamed, throwing it across the room. I picked it up. "I'm afraid you have to, Alistair." I said. "I am not wearing that!" he screamed. "Why not?" I asked. "Everyone else does. It's the rule. Someone in your ... position ... has to." "Why on earth would I want to wear that?" he said. "Look at this way," I said. "You've got yourself a boyfriend, and the two of you already have, if you don't mind me saying, a healthy sex life. You've already lost your body hair. What's the problem with wearing an item of clothing? No one can see it with the your clothes over the top. I know Darren will like it. I know he will expect it." I hugged him again, working my hand round to his nipple, just brushing against it. He winced, just slightly. "Hello!" I said, just joking. "Bit sensitive already?" "I won't do it!" he shouted. I'd had enough of this. "You stupid, silly, little ... girl," I said. "Look at you. Think you're a tough guy? Think you're a hard man? Think you can walk around here as if nothing has happened? Take a reality check. You've let a man fuck you. You weren't raped. It wasn't against your will. A big hairy man wanted to stick his cock in you and all you did was open your legs. You didn't do a thing about it. You had a choice. Look at Darren. Look at the others. Don't you think they were threatened? Well, a man, a real man, doesn't allow himself to be threatened. A real man ? and I know I'm not one ? would rather die that allow himself to be screwed. Think about that, darling. Dress it up how you like, but you gave yourself to a man. That has consequences. You can't undo it. Everybody on the wing will know by now. If you don't follow the rules, and put your bra on, they'll all be on you. But it isn't that bad. So stop being a stupid little tart and put your bra on right now. That's an order." I didn't like to talk to him like that. Not after what he has been through today. But he needed it. He was crying again, this time quite freely. I picked up the bra and threw it at him and told him to stop pissing about. This time, through, he caught it, looked at it, sorted out the straps, and put it on. He was crying. He even managed to fasten it at the back, which not many blokes can do first time. I wonder if it was the first time he'd ever put a bra on. It certainly wouldn't be the last. "Now that's better. That didn't hurt did it?" I said, adjusting the bra straps for him. He'd be allowed to wear his normal prison clothes over the top. That meant the usual white T-shirt and dungarees. But everyone would know. Those who hadn't found out on the bush telegraph would be able to see the outline of his bra through the T-shirt. I sorted it out so it was nice and comfy. The fight had gone from him completely. I said: "Stops your nipples itching against your shirt. Before long, you won't even know you've got it on." "Yes," he sniffled. "You might as well finish it off with these," I said. I handed him a pair of panties. Not a pair of ridiculously small knickers, but lacy white knickers nevertheless. The G-string would come later. But if he's got a bra on, he can hardly go marching round in a pair of boxer shorts. He seemed to accept the logic of that and slipped the knickers on. I was about to show him how to hide that useless excuse for a prick out the way, so it wouldn't leave an unseemly bump, but he worked it out for himself. I gave him a hug. "Let's just sort out this hair". He had lovely hair, shoulder-length, thick. I brushed it, pushed it into shape, finishing off with a pretty little pink barette to hold it in place. He didn't object. The fight had gone out of him now. What a day. I did feel sorry for him. He'd started off expecting to fight for his life and ended up shorn of all his body hair, fucked and sitting there crying like a girl in a bra and panties. If it wasn't for that little erection tenting in his panties, I would have been worried for him. One last thing. Sexual attraction. It's all about smell, they tell me. Pheremones. The smell of a man. A nice shower with my special soap had got rid of that. One more thing needed. As he sat there feeling sorry for himself I gave him a nice spray of perfume. He winced. But there we are. He certainly didn't look too much of a bloke any more and now he didn't smell like one. "I think you'd better go back to Darren, now, love. He'll be ready for you." Daniella's diary. The next day. It was relaxation hour. The blokes were over in the corner playing pool. But us girls, we sit in our own corner and chat. We have a new member of our little witch's coven today. He looked so pretty sitting there. Nice clean white t-shirt, denim dungarees. Just like all the other prisoners. Bra on underneath, of course. You could tell he was in the process of being broken in. A boy in a bra. We could all hear him lose his masculinity last night. I think it was four times we heard it. Yesterday, he might have been over in the corner playing pool with the blokes. Now, he sits with us. There are five of us sitting there. I decide to have a little joke. "Hands up anyone who's not wearing a bra!" The girls titter. No one puts their hand up. We've all got bras on. We all look at the new boy. He doesn't put his hand up either. "Hands up anyone who hasn't had sex with their boyfriend today!" They all laugh. Apart from the new boy. He doesn't put his hand up. "Leave him alone," says Polly. "Alice," I say to him, "I think your boyfriend Darren is a real hunk. I am so jealous!" He wonders who I am talking about when I call him Alice. But it's a fairly clear I must be talking about him. Alistair, he was until yesterday. But the male name doesn't suit him any more. Believe it or not, I was once a trainee bricklayer named Dan. Now if someone calls out for 'Dan', I wouldn't even know who they are talking about. I'm not Dan any more. I only answer to Daniella. If someone comes to visit me, and calls me Danny, I know it's really Danni. But I prefere Daniella. So Alice is sort of short for Alistair. He could think it is spelt Alis, which we all know it isn't, but hell, at first we all told ourselves this wasn't happening. I don't know if the name will stick. I've heard rumours he might end up Lucy. It's always a thing, the name. Do you feminise the male name, or go straight for a girlie name? No answer really. There was a chick in here not so long ago called Adrian. He was a laugh, Adrian. Thought he was going to be the daddy of the wing. What he wasn't going to do to the hard men in here wasn't worth talking about. Until they actually walked in the room. Then he wasn't so tough. One glance at the fist that was about to go into his stomach and Adrian was Adrienne. She was on her knees sucking cock before you could say blow job. Took to it like a duck to water. Had a visit from a girlfriend once. Former girlfriend. She was certainly a former girlfriend after she had seen Adrienne. First couple of visits, Adrienne wiped off her make-up and tried to act like a man in the visiting room. Told this girlfriend that 'he' had handled himself okay inside. Soon as the girlfriend was gone she was back to her normal self. Off with the trousers, on with the miniskirt. But after a while even she could see the ridiculousness of that and sort of accidentally on purpose went in to the visiting room with nail varnish on. You should have seen the former girlfriend's face. 'Adrian' said there had been a fancy dress party. Yeah right. That's exactly the sort of thing you have in prisons. The girlfriend didn't believe a word, and Adrienne eventually admitted she had taken to sucking cock. And quite liked it. The girlfriend, she was okay about it. She ended up bringing in stockings and lingerie for Adrienne. Which was well appreciated by all. Especially Adrienne's boyfriend. Anyway, my point was names. When she got out, Adrienne got a job as a lap dancer and told everyone her name was Mandy. She took the view that by the time she had gone far beyond being a femininsed male, so she needed a chick's name. So Randy Mandy it was. The blokes in here have got all sorts of cruel mental tricks they play on the boys in bras. If the boy gives a hell of a lot of trouble, the blokes actually like it. It makes them feel strong when they crush their poor victim. So you'll get some tough little character, let's say his name is Steve or Paul. He'll insist for weeks that that's his name. Then, one day, he'll have to tell everyone that they should now call him something else. If he hadn't put up so much resistance, he might have got away with Stephanie or Paula, but his fella has decided to teach him a lesson. We've got one at the moment. He was given the usual dilemma: pick it up or drop 'em. He decided to pick it up. Now he's called Melons. And yes, he has. Or will have. It's not about fucking your arse, it's fucking your mind. Well, both. Here's another trick they like to play: A boy in a bra is given some ridiculously old-fashioned name. Hilda, Edith, Agatha, something like that. The boy in the bra objects, as anyone would. The bloke then offers him the chance of choosing his own name. He's not a fool, he knows it's got to be a female name. Let's say he goes for Karen. Pretty name for a pretty boy. He was always going to be called something like that. No one wants a girlfriend called Agatha. But this way, he chose it himself. See what I mean? It's all about getting the boy to make the decision to be feminised himself. I've seen the same thing done with clothes. This is done on a boy who has a cute arse and a small dick. The boy in a bra is going to wear something really sexy for his fella. Only he doesn't know that yet. He knows it's going to be something that a woman would wear. He's given some monstrous conservative Maggie Thatcher type old ladies' dress. You know the type. Below the knee, baggy, and with horrible thick tights to go with it. 'Sensible' girls' shoes. That's the deal, he knows occasionally he's going to have wear a dress. Like any respectable person, he refuses to wear it. He insists he wants to wear trousers. Well, how about a compromise, he is asked. We might be able to find a pair of shorts. Would he wear those? A pair of shorts and some boots. Of course he would. No argument on the shorts, though, he's told, he's got to wear whatever they find. Five minutes later, he's in a pair of spangly shorty shorts. Very tight. Wouldn't be out of place on Kylie Minogue. And they were his choice. The boyfriend knew from the start that he wanted that babe in hot pants. And the boots? You've guessed it. Stilettos. Something similar happened to me. I'd been through the usual stages: telling myself I was going to fight off all the male advances. Then, when it became inevitable, it was either that or a knife in my back, I told myself I wasn't gay, but that I had no choice. Then the bastards actually gave me a choice. I was told to pick one of four blokes to have sex with. If I didn't pick one, they'd all have me. No choice at all, really, although it didn't seem that way. So I did pick one. Then, suddenly, he's 'my type', the sort of bloke I always go for. That I was the one who fancied him. Up until then, I fancied girls, I was as straight as anyone, but all of a sudden I'm selecting a bloke. Did I just make a random selection, or did I actually fancy him? Even if it was subconscious? That's what they kept telling me, that's what I kept wondering about. Next thing I knew, here I am in knickers. And I do fancy blokes. And, I do have a type. When that first boyfriend was released from the nick, I wasn't short of offers from blokes. Who did I pick? Dark hair, unshaven, muscular. Just like the first one. It's no wonder I only answer to Daniella these days. Anyway, Alice is a pretty little name and it'll do for him. He's a cutie. Weak as a kitten. Certainly had no chance in here as a man. You can tell he's got a bra on. Polly, who's looking after him, insisted that he sit with his legs crossed at the thigh, rather than in that horrible male way at the knee. Doesn't look like he's got much to crush. Polly, there's another name. She started off as Paul. Then it was Paulie. You should have heard her object to being called Paulie by her first boyfriend. Then it was Pretty Paulie and then just a small leap to Pretty Polly. It's amazing what a few months of serious dick action will do to you. Anyway, our little witch's coven, we sit there chatting as the men play pool. Obviously, there's only one subject of conversation. I sidle up to Alice. "Tell me what Darren's cock is like," I ask. "Daniella!" shouts Polly. "How could you! Don't be such a bitch!" I didn't mind being called a bitch. I can be very bitchy at times. I love it. I can be a right cow. It's good fun. And, to be quite honest about it, aren't we all bitches? If Alice hasn't found out yet, people are already calling him Darren's bitch. "Oh come on, I want to know. Has he been cut?" Alice just looks down. "Oh come on Alice," I say, "you might as well say. My fella's only six inches and not very thick. What's Darren's like. Has he been cut?" Alice looks at me. "He hasn't been circumcised, if that's what you mean." This is great. It was only a short sentence, and it was like getting blood out of a stone, but it was significant. It means he's already talking about his boyfriend's cock. Polly looks at me with a little smile. It's her job to ease Alice's transition, so she can be proud that Alice has already accepted he has a boyfriend, and can mention his cock. Some of them, the boys in bras, it takes weeks to get to that point. Alice has got there in a day. "And how big?" I ask. "I don't know," he says, flicking a hair out of his face in a way that while not being totally girlie, is certainly not masculine. Polly has done a good job on his hair. The raw material was good ? nice thick blond hair and quite long. Alice is lucky. But some very talented work with scissors and the addition of a cute little pink hair clip, and his whole face is transformed. She's been a busy girl, our Polly. Done his eyebrows as well. Polly does my hair. I think she's going to work in a salon when she gets out of here. "Come on, how big?" I repeat. He again says he doesn't know. "Well how thick, then?" "Quite thick," he replies. Out of all the dicks he has seen, it's on the thick side. Mmmm. What does that mean? It's thicker than his own pathetic specimen? Or did he like looking at dicks even before he got in here? I don't know the answer. He'll soon have plenty to compare it with. I think he's ready for the next step. I look back at Polly. "Shall we?" I say. But she doesn't know what I mean. I look at Alice. Yes, pretty, but something missing. Something that can be rectified in seconds. I take something out of my pocket and hold it up. Alice asks what it is. I take the top off and hold I up. He's embarrassed, and looks round at the other girls. We all smile, encouraging him to try it. He doesn't know what to do. I offer it to him. Lipstick. Nice pink lippy. I thought about the red but for now it has to be pink. It looks so much better when it's wrapped around a man's cock. There's a pause as we all look at Alice. He looks at the lipstick. He's got a very nice complexion. Very smooth, so he's not going to need much make-up. But it all starts somewhere. He carries on looking at it, and then glances around at the rest of us, who are, of course, fully made up. Polly says: "You might as well. What else are you going to do?" Alice looked longingly over to the pool table, where the blokes were. But his place was with us now. Very slowly, Alice picks up the lipstick and tries to put it on his lips. It's ridiculous, he gets it all over the place but we're immediately all over him, wiping it off, offering him our make-up mirrors and showing him how to do it. Three or four attempts, and his still boyish face is highlighted by full pink lips. Cute. I say he can keep it. Polly says she'll give him his own make-up mirror later. There's a thing about wearing lipstick. You can't help but lick your lips. It tastes nice in a girly sort of way. That's what he was tasting. You just naturally purse your lips together and hold your mouth in a way that a man never would. You even hold your eyes slightly differently. Alice did all this. I know men wear lipstick from time to time. Certain sorts of men. But in prison, only the girls do. In percentage terms, I'd say Alice just lost another 10 per cent of his masculinity when he put that lipstick on. Just as Alice is getting used to the nice feel of wearing lippy, Darren wanders over, pool cue in hand. "Hello girls," he says. We all smile at him and say hello, apart from Alice, who just looks down. Of course he notices, and looks straight at him. "I said, hello girls." Alice has to look straight up at him. "One last time," says Darren. "Hello girls." "Hello," says Alice. "Hello what," says Darren. "Hello Darren," says Alice. "That's better," he says. He plonks himself down next to Alice, and slaps his huge hand on Alice's thigh. He strokes it, as if he owns it and lets his hand rub across Alice's groin. Alice doesn't do a damn thing. Doesn't like it course, but is too scared to push him away or punch him or anything like that. Which is the way it is. Genetics. If Alice didn't want him to do it, he would have to fight him. One of them would probably get killed. And as Alice didn't want it to be him, he let Darren touch him wherever he wanted. Alice looks straight at Darren and forces a smile, a humble, shy submissive smile, but a smile nevertheless. Of course it shows Darren his lovely pink lips. "Well who's a pretty girl then?" he says. Again Alice looks down and licks her lips, which is very cute. "I said, who's a pretty girl?" His hand grips Alice's thigh. It's possessive, it's sexual but it's also a threat ? it looks like he's squeezing quite hard. "I am." Mutters Alice. "What are you?" he asks. He takes his hand from Alice's thigh and pushes a strand of hair out of his face, and strokes his smooth chin. "You're a pretty little girl. What are you?" "I'm a ..." He can't say it. Darren says: "You're a pretty little girl, what are you?" "A pretty girl," Alice mutters. "No. A pretty little girl. What are you?" Finally Alice gives in. "I'm a pretty little girl." "Indeed you are," he says. "Your girlfriends been giving you make-up tips?" "Suppose so." "Very kind of them. Give us a kiss, then." How humiliating. He can't refuse. He kisses Darren on the cheek. Leaves an imprint of his lipstick. It's another step down that one-way street for Alice. It's even worse than Darren kissing him, he's got to kiss Darren. "Has she got her lipstick all over me?" Darren asks the rest of us. We laugh in affirmation. "Well wipe if off, doll," he says to Alice. He does. Sorry, I mean she does. That's another of our little traditions. We tend to call the boys in bras 'he' and 'him' until their boyfriends call them 'she' and 'her. Now Alice is a she. Anyway, with that he kisses Alice. Really kisses her pretty little bright pink lips. Tongues. When he's finished, he pulls back and looks at her hungrily, as if he is going to devour her later on. He puts his arm around her and lets his hand alight on his breast. He fiddles it with his fingers. "Hello, what have we got here?" he says as he continues to twiddle. Alice winces and folds up, trying to wriggle away because the nipple is so sensitive. She can't get away. You don't often see someone's nipples become so sensitive only a day after they've started the pills. Alice is a natural. Perhaps she'll end up with massive great boobs. That would be funny. It's all right getting hold of a boy, and turning him into a girly type thing, but you don't imagine they'll end up a buxom piece, sticking their boobs out for all to see. "Don't," says Alice. "Don't what?" says Darren, trying to work his hands inside Alice's bra. Alice goes red, as if she's got blusher on his cheeks. Which she will have soon. "So," says Darren looking round the table, "how do you like my new girlfriend? She's nice, isn't she?" "Alice is a lovely girl," I say. "Oh, it's Alice, is it?" says Darren. By now, they're sitting there very much the couple. He's got his arm around her, casually fingering her bra straps and tweaking her nipples when he can. Alice may not like it, but she is not resisting. A boy in a bra. Darren stands up, and beckons Alice to take his hand. Which she does. They walk back to the cell, hand in hand. I don't have to tell you what they were going to do. Prison officer's report. Two weeks later. Integration report on Prisoner 4843403. Prisoner 4843403 arrived at Scottsville Prison one month ago ago. As was noted at the time, Prisoner 4843403 was considered to be at risk. He is 19 years old, small and not well muscled. It was noted he would undoubtedly attract attention from bigger prisoners. He was advised prison officers would not be able to look after him at all times. Segregation was offered, but refused. Prisoner 4843403 was unofficially advised to make friends among the prison populace and stay out of trouble. Prisoner 4843403 appears to have made friends with two others, prisoners 9983419 and 8405026. 8405026 is considered one of the 'alpha' prisoners on the wing with a reputation for violence. 9983419 is small and frail, like Prisoner 4843403, and at first they were put in the cell so 9982419 could advise 4843403 as to the best tactics for survival. After a week of incarceration, Prisoner 4843403 asked to moved into a cell with 9983419. It appeared Prisoner 4843403 had made friends with 9982419 and had accepted his protection. This move was granted by the wing governer. Prisoner 4843403 then spent most of his time with 998419, who was noticed putting his hand on Prisoner 4843403's bottom. It was assumed Prisoner 4843403 was granting sexual favours to 9983419. Prisoner 4843403 appeared to be depressed about this situation and was again offered segretation, but refused. Last night, during a routine check of cells, the following was observed. 9983419 was sitting on the edge of his bed, leaning back. Prisoner 4843403 was on his knees in front of him, with his mouth in 9983419's groin area. 9983419 was groaning and holding Prisoner 4843403's head in place with his hands. It was clear a sexual encounter was taking place. It appeared 9983419 had placed his penis in Prisoner 4843403's mouth. Prisoner 4843403 was providing sexual stimulation with the tongue and mouth. 9983419 was wearing his normal prison clothes, albeit with his trousers and underpants around his ankles. Prisoner 4843403 was wearing a small and tight pair of white underpants, which appeared to be designed for a female. He was also wearing a white brassiere (female). He also appears to have lightened his hair colouring. It was decided not to stop this action as it appeared consensual on both parts. Despite the presence of an officer, neither party stopped their actions. Later Prisoner 4843403 was called to the wing warden's office. He was dressed in normal prison clothing but did appear to be wearing a brassiere. He was asked to explain his actions in the cell with 9983419. Prisoner 4843403 was not communicative but he confirmed 9983419 had not forced himself on him. He was again offered segregation but said it was 'far too late for that now'. Prisoner 4843403 was asked why he was wearing a brassiere. He said he had experienced some tenderness in that area and that the garment offered some protection. He was asked to remove his shirt and the garment. He appeared reluctant to do so, and even when he had removed them both, his put his arms across his chest to prevent the officers viewing the area. When he finally put his arms down, there did appear to be some swelling around the nipple area, which was itself enlarged. While the officers were inspecting Prisoner 4843403's chest area, Prisoner 4843403 said: "Get a good eyeful boys." Upon close examination by an officer, the nipple area was found to be extremely sensitive to touch. It has been decided to leave Prisoner 4843403 where he is, in the cell with 9983419. While not condoning homosexual acts, the prison authorities realise that it is inevitable some will take place in an all-male grouping. Indeed, there is a natural order to matters, with prisoners like 9983419 at the top of the order, with Prisoner 4843403 and people like him further down. The state of affairs that appears to exist between them means that a violent inmate like 9983419 is kept reasonably quiet as he is sexually satisfied and Prisoner 4843403 is spared attacks from other inmates. Prisoner 4843403 did request permission to keep wearing the brassiere until the swelling had subsided, which was granted. He also appears to have had his navel pierced. Alice's diary. Two months later. The first few times I had to put it in my mouth it was disgusting. But now, and I hate to admit it, I'm getting used to it. I don't know how that makes me feel. The smell is something I hadn't experienced before. Very male, very predatory. You never notice it on yourself, but things are different now. Now, I've got used to the smell. There are worse things you can do than put another man's penis in your mouth. Getting yourself stabbed, that would be one of them. I know that one of the things that turns him on is when he sees his willy inside my mouth, making my cheek stick out. And when I look up at him and stare into his eyes when it's sticking my cheek out. I have to wear women's make-up. Lipstick and mascara, particularly, but the full lot. He gets off on seeing pink lips around his cock, and made-up eyes looking up at him. He moans when I do that. I disgust myself, but I have to do it. Obviously being a man myself, or whatever, I know the places I liked to have it touched. I was never lucky enough to have a woman perform a blow job on me, but I do know the places that are the most sensitive. I start with a lick or a kiss underneath, just at the start of the head. Even if he's already hard, and he always is, that makes him superhard with a jerk. You can see the veins sticking out. So you keep doing that for a while, until he starts to get frustrated and takes hold of my head. Then you actually put it in your mouth, just the tip at first. I don't know why it's called a blow job. I don't do any blowing. Then you just sort of rub your lips up and down it a bit, making sure it is nice and wet. If I'm doing it right, he just sort of strokes my hair. If I'm doing it wrong, and that is less often now, he just firmly holds my head in the place he wants it to be. But I learnt pretty quickly. Sometimes he will play with my bra straps. Then, using your tongue on that spot underneath the head, you lick that as you take the whole cock into your mouth. At first, you gag on it but you soon get used to it. As I say, at first the taste was, well it reminded you of what you were doing. But you do get used to the taste, as well as the smell. Then comes that moment when you look up at him. And he sees me, all helpless and with his cock making my cheek stick out. Sometimes he come right there and then, depending on how many times we've already done it. Other times you have to lick and move your lips up and down. I can get it right down my throat. Once in a while he pulls it out and fucks me, but most of the time he comes in my mouth. First time of course, I gagged, and he laughed like a drain. Now I swallow. You do actually feel quite powerful when you are doing it. That's the funny thing. I would have thought it was the ultimate degradation but seeing the look on his face, and the thought that I'm doing it to him, does give you a feeling of power. Obviously, when I get out of here, the nightmare will be over. There's no way I've turned gay. It's just I have no options. I'm not worried about the changes. When I get out, I'll stop taking the pills. Goes without saying. But one thing about being in prison, you need all the drugs you can get to get you through the day. So I take these pills, the 'girly pills' as they call them. And it doesn't seem that bad. Of course, there are side effects. I've lost quite a lot of weight. And that which I have, seems to have redistributed itself. Before I got in here, I was actually quite a good runner. Now when we have our exercise sessions, it's ridiculous if I try to run. My bum sort of moves about of its own accord. And I have to hold my chest to prevent that wobbling all over the place. But that's all reversible once I stop taking the pills. And the other thing, I don't really like to talk about, but ... I haven't got hard down there for ages. At first I thought it was the shock of all that had happened. But when he touches me down there, I still feel ... excited. Just not hard. I'm not saying I was ever all that big down there but now, the little fella appears to have given up the ghost. But that will all come back. I suppose you're wondering about these pills I'm taking, and how the authorities allow all this to go on. Well, it works like this. Everyone knows that men need sex. In prison as much as anywhere else. And when there are no natural women around, someone is going to do the fucking and someone is going to be fucked. That's nature. The governer knows this, and he allows it. The governer has fucked all of the 'girls'. Me as well. As I'm new, he seems to want to do it with me all the time. There's not much Darren can do about it, in fact he's okay with it because it increases his influence. So a couple of times a week, we're all whisked into the governer's office. We are paraded in front of him in our bras and knickers, and he chooses one to fuck. Sort of like a harem. In the last five weeks, I suppose we've been in there 10 times, and I've been chosen six times. Danielle is the next most popular, with two. Says something, I suppose. Don't know what though. The ridiculous thing is the girls are actually jealous of me. How pathetic can you get. As if I want to be there. But there are a few perks associated with being the governer's favourite. A pair of knickers, some make-up. Which is a perk for Darren, not me. But I might get a drink when I'm with the governer. So I suppose in some ways it's not so bad. The other thing is the girly pills. It's true, if you take them, you don't feel so bad about what's happening. I hate to admit it but if I take some, and then I have to be fucked by Darren, or the governer, I can sort of see what women get out of sex. I can't believe I just said that. My nipples are more than just nipples now. Don't tell anyone, but it's much more comfortable with a bra on. I didn't know what the pills were at first. I just took them. I took as many pills as I could on the outside, so I was always going to do the same in here. I don't care what kind of pills they were. Now I've stopped getting stiffies, and the shaving stopped, at least the shaving on the face. But by then I was hooked. After a few weeks, you just look forward to taking the next girly pill. They are very addictive. Then, and I suppose this happens with all addicts, they stopped giving me the girly pills. Polly said if I wanted any more, I'd have to go the doctor and get him to prescribe some. Also, if I played my cards right, I could get him to put me a light job, like in the sewing room. I didn't exactly know what 'playing your cards' right meant. She said I'd think of something. I went in there in my usual clothing, dungarees, with bra and knickers underneath. He probably suspected I was a boy in a bra but he couldn't see. He asked me what appeared to be the problem. Just on the spur of the moment I told him I'd been getting this terribly itchy chest. He said I was to go behind the screen, take my clothes off and put a gown on. There'd be gowns, there, he said. When I got behind the screen, I saw a pile of medical gowns, plus one other item of clothing. The others had been right. I immediately knew what to do. If I was a genuine patient, all I had to do was put the medical gown on, and no more would be said. But of course I didn't put the medical gown on. You have to laugh at what happens in this place. Otherwise, I don't know what I'd do. When I came out from behind the screen, I was wearing a babydoll nightie. It was the first time I'd ever worn anything like that. But I wanted those pills. A big smile on his face, of course You can imagine him, when every prisoner goes in there, asking them to go behind the screen and put the gown on. Ninety-nine out of a hundred come out in the surgical gown. I could see his erection, straight off. Then all he did was inspect my itchy and swollen chest. Extremely thoroughly. I go back once every two weeks for a new batch of pills. Without fail, I end up in a nightie, or whatever he's left for me. Every time, he does a very intense examination of the itchy chest. But it doesn't seem to be getting any better. In fact, every time I go back it's more and more swollen. The doc seems quite happy with this. He doesn't do much to me. I might have to give him a blow job if he's in the mood. But I've got a job in the sewing room and don't have to go outside busting up rocks, or whatever the blokes do. Polly's diary. A month later. Alice had been coping quite well with the change in her status. But she was still a boy in a bra. We called her a girl, she had a girl's name, was referred to as she and her, she had a boyfriend and of course she wore a bra, but there was still quite a lot of boy in there. She was probably thinking that when she got out of prison, it would all be over. But she was changing. When she got a look from a man, she would no longer avoid his eyes and hurry away. She'd started to look a man straight in the eye in a way a boy never would. "Try them on," I said. "No way," she laughed. But I knew she wanted to. I knew what had happened of course. It's just another little bit of the old male inside us giving up the ghost. She must have discovered that sex from the female side is not as gut-wrenching as it at first seems. Indeed, once you accept the inevitable, you realise it's actually a whole lot better. It's the fella who's got to do all the work. Put on the performance. There's nothing quite like just giving yourself to your sexual partner, to be unable to stop him even if you wanted to. You soon start not wanting to stop him. You soon start to dream about him holding you down as he has his way with you. I could tell Alice was starting to feel like this, even if she wouldn't admit it to herself. "You know you want to. Try them on." I said. She smiled at me. We were talking about a pair of shoes. A pair of high heels. Very classy. Nice, understated black court shoes, with a three-inch heel. Alice had been looking at them for hours. And I knew perfectly well what had been going through her mind. What they would look like on her. She was in her boy in a bra outfit. Dungarees, white t-shirt. We all knew what she had on underneath. "I do not want to try them on," she said. "Oh yes you do." "I do not!" she squealed. "Oh yes you do. And so you should. You've got lovely legs. Made to be perched on high heels. I know Darren thinks that." "What? What did he say?" she asked. "Try them on. They're your size," I said. "No. What did Darren say?" she quizzed. See what I mean? Why would a bloke, who has been backed into a corner and forced to do something that he doesn't like, want to know what the person who is terrorising him, has to say about his victim? He wouldn't. Neither would a boy in bra. He wouldn't be thinking about high heels. He'll wear his bra, he'll suck his boyfriend's cock, take his pills, but only because he has to. Was that a girly thought that just went through her mind? I'd had enough of her silly little girly games. "Please yourself. Try them on or not. What difference does it make to me?" "But I can't wear high heels. I'll fall over," she said. "Then don't. I don't care. Get yourself a pair of Doc Martens. See if I care." "Well I'm not going to do that," she laughed, as if her wearing men's boots was the most ridiculous thought in the world. Which it was. There was more silence. I just the idea grow in her head. She flicked her hair behind her ear. Totally cute. "When I get out of here, all this ends," she said. "I've realised. All the time I wasted. I'm going to shag every bird I can find." "Yeah right," I said. I think we both knew what would happen when she got out of here. Some women would like to have sex with her. That's for sure. But a whole lot more men would love the thought of sticking their hand up her skirt, ripping her knickers off and having her right there on the floor. And that thought was starting to excite Alice. I'd had enough talking. I think we all know what she was really thinking. What she was really saying. I picked up the shoes. I held them up and dangled them in front of her face. "I think they'll fit you," I said. "I've just always wondered what it would be like to wear them," she said. As if every bloke wonders what it would be like to wear high heels. "Now's you chance." "Well, just to see what it feels like." She took the shoes and put them down. She took off the trainers and socks. She crossed her legs, at the thigh, I noticed, girl-style, and started to put one on. I was impressed by the way she crossed her legs. It meant there wasn't too much to get squashed. "What do you think you're doing?" I said. "What?" she replied. "You think you can wear those with trousers?" "I'm not wearing a skirt." Like that question really needed an answer. "Take your trousers off." She did. She left the t-shirt on, and the knickers, obviously. Alice clearly didn't have a problem wearing a bra, so the only item of clothing that could possibly have been worn by a bloke was the t-shirt. Bearing in mind there were two distinctly un-manlike bumps in her chest, she didn't look all that masculine. Once she'd got the trousers off, she sat back down again, crossed the legs and put on the shoes. It was the first time her toes had been squeezed into a pair of heels but there you go, welcome to the world of womanhood. She didn't say anything but she seemed delighted. She crossed her legs tighter at the thigh, and looked down at them. Then she stuck one leg forward to get another view. They did look good. She had the ankles for it. Beautifully slender. Even less masculine. "Stand up then," I said. "Oh I couldn't possibly stand up. I just wanted to feel what it was like." This was getting pathetic. Who was she trying to kid? I went over, took her hand and pulled her to her feet. She didn't exactly resist. "Now," I said. "Walk to the other side of the room, turn around and come back." She was still smiling. She took her first step. The ankle wobbled. Nothing wrong with that. Now, I've seen a lot of boys wearing heels. In here, it tends to happen quite a lot. 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Jailhouse Spades

It was a quiet Friday evening at the Prescott County Jail. The inmates had already been fed dinner and were in the rec area watching TV, playing cards or dominoes, conversing, or just relaxing. At one table a group of Blacks was playing spades. The game was close and this final hand would determine the winning team of this round – even though they’d probably rematch right after this. All of them arrived due to various Class-A misdemeanor offenses. On one team was Errol, known as ‘E’, and...

2 years ago
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Enjailed Chapter 1 Road Trip

..............-Well didn’t you know that driving drunk is breaking the law?-his question sounded too hasty and scared me even more.-Yes,….well…yea but…I didn’t think….that…..-I couldn’t speak, I was terrified, this couldn’t have been happening. Now I could see, that the other cop was looking at my ass with hungry eyes and I could swear I saw him grabbing his cock. I tried to close my eyes and make myself believe, that I was imagining it, I was gay after all, I have seen this in movies, it must...

1 year ago
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JAILHOUSE COCK

It happened one summer when I was 26 I did something stupid and wound up in jail awaiting court I had no money for bail so I was just trying to tough it out! The cell block I was on was mostly good guys there were a few assholes of course but thats to be expected...The guy in the cell next to mine was named Freddy he was a really nice black dude kinda short but not too smart fella too but he did something stupid too! Hey shit happens you know nothing you can do but try not to make the same...

2 years ago
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jailhouse lesbians

I trembled with anticipation as I removed my shirt and pants and then my bra and panties which I stuffed under my blanket in the cell I shared with Kya. I was both nervous and excited. I didn't want to make the wrong move by saying or doing anything that might turn her off, yet the burning desire I felt just had to be sated. As it was, I could already feel my clit throbbing with red hot need. My pussy was warm and moist.Calm down, I told myself, or you'll cum in your pants just from wanting...

2 years ago
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Jailbreak

Jailbreak Megan Roman Inspired by the picture "Jailbreak" found on Prinny77's deviantart site (http://prinny77.deviantart.com/) Steffie knew she hadn't lived a perfect life. For 21 years, she had spent pretty much every day indoors, either watching TV, reading, or playing videogames. She had no friends, no money, and no social life, and meeting her end by accidentally touching a broken power strip did nothing to change her activity level. Hell didn't seem like a logical...

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