Note: This story was dynamically reformatted for online reading convenience. WARNING.. THIS FILE CONTAINS SEXUALLY EXPLICIT MATERIAL AND IS NOT SUITABLE FOR CHILDREN.. IF YOU ARE UNDERAGE OR OFFENDED BY THIS TYPE OF MATERIAL PLEASE DELETE NOW. This story is copyrighted to Matelot21. Provided you do not change in any way you may copy this story to any FREE website. This story contains pasages of unprotected sex between men, please take all precautions in your own sexlife. Friendly emails to me at cherrylossat15@yahoo.com.au are welcome, particularly if they contain details of your own seduction or first time. Please remember that ASSTR exists only by way of donations! GAOL TIME BANGED UP as A BROAD WELL, I AM FINALLY a free man after doing five years of a four to six stretch for so called white collar crime. I was an accountant who managed to embezzle ninetyfive grand from a stupid old client, and got caught. I managed to hide most of it and I was able to make the powers that be think I'd gambled it all away. Not that there is much more than half left now. I did my time in our State Pen and what a surprise and education that turned out to be! The day I arrived I was taken to the Warden and I was surprised when he told me he had been waiting for someone just like me. He added that he was depending on me to do the right thing and assist in his new program which he said was going to keep the gaol a lot more peaceful. He told me then to keep my mouth shut and not ask any questions. I was then taken to the infirmary where I had to strip off and I was subjected to a very careful physical inspection. I was surprised that my cock and balls and all around my crotch area was closely examined, I was told that I was being checked for herpes or genital warts. Blood samples were taken for HIV and other viral diseases, I was surprised. My mouth and teeth were checked over too. I even had to submit to my arsehole and rectum being checked for tears or fissures. Then I was led through the cell block, I noticed that front of the cells were just all bars and open so that I could see the inmates, two to a cell, but when I arrived at the cell where I was going to live I found the front had been enclosed with metal sheeting attached to the bars. I was not very happy to find I was sharing with two rather big and nasty looking bikers. They were both doing ten to fourteen for bank robberies so they said. The cell had one double bunk and one single bunk and I was surprised when one of the bikers, named Billy, told me I would be having the single bunk which he referred to as the "Fuck Truck". This made me worry. I was a fairly small guy then, a lot plumper now though, and I had no experience in dealing with any nasty situations. After the evening meal of that first day, I was standing in the cell when Peter, the other biker suddenly said to me 'Get your pants down honey.' I was alarmed and decided to ignore him and then all of a sudden he spun around and punched me incredibly hard just below my rib cage. The pain was incredible, I doubled over and began to retch. In my pain I realised Billy had quickly put a massive arm around my shoulders and led me to the washbasin. As I stood there, bent over, vomiting into the basin, I felt my pants being pulled down to my ankles, quickly followed by my underpants. Billy was still holding me tightly and I felt my buttocks being pulled wide apart by Peter. My nausea was subsiding, I felt really scared and then I realised Peter had just spat a huge dollop of his saliva against my exposed anus, which was quickly followed by a thick finger which forced it's way into my tight ring, moved in and out and around and was then removed. It hurt a bit, and I felt outraged at being violated like that. I said something like 'Hey, cut that out' and was rewarded by Billy's heel stomping on the instep of one of my feet. That was incredible agony, I was wearing sneakers and I had never known just how painful something like that could be. While I was recovering from the pain, Billy turned me around and held me as Peter then grasped my limp cock and stripped it down with one of his big hands as if I had just cum and he was trying to get the last drop of semen out of the end of it. He bent down and had a good long look at the eye of my cock and then all over my cock and ball bag, I felt like a fly caught in a spider's web. 'How is she; okay?' Billy said. 'Yep, she's nice and healthy I reckon, otherwise the Warden wouldn't have sent her down to us' Peter replied with a chuckle. Billy let go of me and I managed to stand by myself. I reached down to pull up my underpants, but stopped when I heard Peter say menacingly 'No honey, no underpants, just your pants for now. You won't be wearing any underpants from now on, not that sort anyway' I was still in a lot of pain so I stepped out of my pants and underpants, and then just pulled my pants up. 'You're nice and tight honey, a virgin I reckon,' Peter said to me, and then he laughed as Billy said 'Yeah, for now anyway.' They then told me they knew all about me, what I'd been convicted for and also they knew that I had a lot of the cash stashed. It soon became apparent that security was very slack, the guards turned a blind eye to all sorts of things. Both of my cellmates lit up big fat grass cigarettes and when I declined to take part they let me know I would either do as they said at any time or I would really learn how much pain I could be in. I had never smoked grass and it had a big effect on me. After a while both of them stood up and told me to undress them, I didn't want to of course, but after one more threat I did as I was told. 'Have you sucked cock before ?' Billy asked me. 'No, and I don't want to,' I replied. Billy quickly grabbed me. I held my breath as Peter made a huge fist. 'Last time was only gentle, now you are really going to learn what it can feel like,' he said. I gave in. I felt terrible. 'Take your clothes of, honey,' Peter said, 'We like to do everything properly now.' I took my shirt off and then my pants, trying not to look at their big cocks hanging over their big ballbags. Peter lay down on his back on the single bunk, I looked at his big cock lying limply over his hairy balls. I hesitated. Billy got behind me, I could feel his cock and balls pressing against my bum, I tried to resist but quickly gave in as he made me bend down so that my face was over Peter's cock. 'Come on honey, there it is , you are going to get used to doing this darling, we've made a deal with the Warden that a nice sexy Yummy Mummy is going to live with us for all of her time, and we are going to make sure that this joint is nice and quiet, you're lucky we're both healthy so it's not going to hurt you.' I wet my lips and thought, 'Well I have to do it,' and I licked my lips and slowly placed them over the tip of a big hard knob for the very first time. I kept my buttocks closed tightly, and then I heard Billy say with a laugh 'It's okay honey, we're not going to fuck you tonight, you can relax this lovely tight ass. We have to wait for your test results first sweetheart.' I had always lived quietly, I always felt very insignificant around girls and had never had any sex at all. I have to admit I had sometimes looked at cock porn on the net, usually cum shots, but I had never ever really imagined I would be sliding my lips down over a hard knob. I was surprised how smooth it was and I was quickly brought into reality when Peter growled at me for letting my teeth rub over his knob. I slid my lips down further, carefully keeping them over my teeth. I had seen men being sucked on the net and I had a fair idea of what to do. Then I realised to my shame that my own cock was starting to get hard. I tried to think of other things, like going to my stamp collectors club, but my cock kept getting harder. Then to make it worse for me, I felt Billy's hand slip around my hips and wrap around my cock. 'Hey' I heard him say with delight, 'Her little cock is getting hard Petey, that means she likes it!' 'You little slut,' Peter said, 'Now come on, suck me good.' I sucked at him, it wasn't so bad I realised, as his precum seemed to plate all around inside my mouth, making it feel slippery. My mouth was making lots of saliva and I used my tongue in the groove under his knob when he told me, and then I felt his big hand grasping over my head an I realised he was about to cum. 'Keep sucking, bitch,' he roared, his hips jerking and lifting up from the bunk as spurt after spurt of his semen pumped into my mouth. I had to swallow as I felt it begin to flood up inside the back of my nose. I was surprised at just how much he had cum, I realised it didn't taste much different from his precum, and not really all that unpleasant. I kept on sucking at him until he told me to stop. Then it was Billy's turn, he gave me instructions as to what he liked, and it wasn't long before I was swallowing his large load of cum too. I was so ashamed but also strangely excited, I was even thinking it would be nice if one of them wanked me, but I soon learned that that wasn't going to happen. I was told not to get my hopes up, that I was only going to be allowed to cum when they said so, and if they ever found out I had wanked myself I would be severely punished. I then found out just how much they had known about when I was due to arrive, when I was forced to swallow a large yellow tablet. I didn't know what to think when I was told it was female hormones and that I was going to swallow one every evening after supper and that I was also going to get a weekly injection of the hormones too when the drugs arrived. They had also had time to arrange my new clothing, as a pair of white satin panties was displayed to me and then I was told to put them on. 'White, as you can see honey, for your virginal little ass, and we've got red ones for you to wear, but that will be in a few days yet, sweetheart.' I had to stand there as they both fondled my ass in the tight white panties, then feeling the shape of my cock, still hard, and my balls in my crotch. That night I lay in my bunk, I couldn't sleep for a long time, thinking about what these two guys were intending to do to me. Strangely, I couldn't stop from feeling an unusual excitement, my cock was hard inside my panties, I would have loved to masturbate but the thought of the pain I had already experienced made that unlikely. The next morning started with them both taking turns to pull and twist my nipples, it was really painful but I was powerless to stop them. Then they both played with my cock and balls for a while. Then they called a guard and again it was obvious just how well they controlled things when he led the three of us along to the showers. The other inmates made a few comments as we walked along, but not too loudly I noticed, and I realised that my two cellmates had put the frighteners on them too. I had to undress them and then myself, and then we showered, after which they both shaved all of my pubic hair away, the lot, front, ballbag, and around my arsehole. Again I felt excited and couldn't stop myself from getting hard which amused them. They stroked my hard cock for a while and then shaved under my arms. I didn't have much chest hair but they shaved there too. 'This is only until we get the hair remover, honey,' Peter said, 'It's on order, don't worry.' When we got back to the cell I had to undress them and myself again and they made me give them both a full body massage. I was wondering if they would make me suck them again, but after I dressed them and myself, me in my white panties as before, it was time to go out to the yard. I saw the other crims giving me the once over, there were plenty of smiles and winks, but no comments. I knew what they were all thinking and I tried not to think about what my new position in life was now. The next day a guard brought down a parcel to the cell. I was told to open it and there they were, two electric breast pumps used by lactating mothers to express their breast milk for their babies. I was made to lie on my back on my bunk and the guys fitted one to each of my nipples, plugged them into the power and turned them on. I could see through the clear plastic funnels as my nipples were sucked up, they stung as they got bigger and bigger. Peter and Billy chuckled as they watched, and pulled down my panties and played with my hardening cock. I was told that I was going to have my little tits sucked for at least one hour every day by the machines. After a while the guys took them off me, it was surprising how much bigger my nipples were, they had fun for a while sucking at them. Then, after a week of me sucking their cocks daily and having my nipples expanded, the day came when a grinning guard brought the news that the guys had been waiting for -- my blood test results were back, I was totally healthy. Our shower time was a bit longer that evening, they shaved my pubes again, and spent a bit of time fingering my soapy arsehole, playing with my cock and hard nipples. Back in the cell I was told to choose which of them was going to be the lucky guy to take my tight little virginal cherry. I didn't know what to do, I was scared that I would always be getting a bad time from the one who wasn't first. I was also very scared about how it would feel, how much it would hurt, I had heard stories from the boys at school. I thought quickly and came up with an idea. I suggested that they decide quietly between them which side of a coin they would choose, without telling me, and I would toss the coin up and whichever side of the coin was uppermost would be the guy to fuck me first. They both agreed and I tossed the coin. Billy won, I was secretly pleased as his cock was slightly smaller than Peter's, and I thought maybe it would hurt me a bit less. They got me on my bunk, and I had to suck each of them for a while while the other one wiped lots of KY all over my cock and balls and little tits and pushed the top of the tube up inside my bum and squeezed a lot of it inside me, it felt cold. Peter then got me to lie on my back with my knees up near my face and he held me as Billy put lots of KY on his cock and got on the bunk. I lay there, holding my breath as I felt the hard tip of big knob center right in the middle of my tight little virginal ring. 'Just relax honey, you are really going to get to like this, you mightn't think so now, but you will, believe me.' Billy said thickly. My cock had been hard but I could feel it going soft as I lay there waiting. I tried to relax but I could feel my arsehole was clenched tight. I felt the tip of his cock slowly opening me, forcing it's way into my body, it wasn't hurting so far. Still more slowly it opened me, I could feel my ring stretching, a little more each time as Billy pushed, I realised my ring was as big as it had ever been when I crapped, but still it was stretching wider and wider. It was starting to hurt and I moaned as a sharp pain shot out like lightning into my thighs. Billy stopped his pushing and we both stayed still, my arsehole stretched wider than it had ever been, Billy's big purple knob jammed in the opening. I felt like I had a telegraph pole in my bum. Then strangely, I felt my arsehole relaxing a little bit and the pain almost went away. Billy chuckled "That's it darling, just relax, I'm almost inside your lovely tight arse," and he gave another push. I felt his knob open me a bit more and the pain returned. He waited, and again I felt my ring relax a bit, and again he pushed and got inside me a bit more. It seemed to go on like this for a while and finally I felt the ridge of his knob suddenly move a lot more and I could feel it rubbing backwards against what seemed like two rings of muscle in my arsehole and then I realised his whole knob had slipped inside me. It still felt like I had a big pole up me but a different sort of pain. I felt my distended ring was able to close a little around the shaft of his hard cock. "Fuck you're tight," Billy grunted as he lay still, and then started to force his cock up inside my rectum. I could feel his cock entering me in little jerks, like pulling on a wet sock, it hurt me lot but I managed to relax a little as I realised that it wasn't going to get any worse than it was. Still his cock went further up inside me, I wondered when it was going to get all in me, and then I could feel his wiry pubic hair being pressed all around my arsehole and I realised I had now taken the lot. Billy lay there grunting for a minute or so and then began to work his cock inside me, in and out just a little, I could feel my arsehole clinging to his shaft each time he withdrew and I could feel the hard kerb around his knob deep inside me. I was in pain but gradually getting used to it, and I found I was wondering if I would feel it when he would cum up me. 'Come on Billy, for fuck's sake, I can't wait much longer' Peter said loudly. Billy began to quicken his thrusts in me, each thrust a little longer until he was fucking me in out about what seemed four or five inches each stroke. I felt my rectum relaxing a little as he fucked me, it was starting to feel not so bad and then he groaned and growled and started to shudder, I could feel his cock inside me convulsing and I realised he was pumping his semen into my body. He shoved his cock up me as hard as he could for the final spasms, lay still for a minute as he breathed heavily, and then slowly withdrew his still hard cock. It seemed to be a foot long as he slowly pulled it all of the way out me me. I looked at, shining wetly, it seemed incredible to me that I had been able to take that monstrous weapon all the way inside my body. I tried to picture what all of his semen would look like up right up inside my bum. To be continued ....