Jail Time

It was a sweltering hot day at the county correctional facility. I lay sweating on my bunk wearing my tiniest bikini panties, my bra less breasts trickling sweat onto the rough bed sheet. My cell mate, Lynda, threw back the door as she entered,

"God Candy, by all that's small and dangly, it's bloody hot."

She always makes her references about me, I'm a transgender guy but still retain my dick. I owe my coffee complexion and good looks to my Mom. My father never gave me so much as his name. Lynda's an old, wrinkly lesbian dyke. A month ago she me asked how come I was in a 'gender neutral' cell, thats rich, she's about as neutral as Ghengis Khan. I told her they called me 'gender fluid' and she demanded I don't pump any fluid her way. With her saggy tits and skinny, wrinkly ass I'd find it difficult to even get a hard on. I try not to look between her legs but I hear her scraping away with a razor because her girlfriend likes her to be 'fresh and clean'. I'd never seen Belle, Lynda kept her a closely guarded secret, for all I knew Belle was not even her real name. Surprise, surprise, prisoners have been known to lie.

The way Lynda was dripping water on the floor I gather she had showered and preferred to drip dry, she stood there scratching away under one boob, the other hand having to hold it up to gain access. I sighed, she was more a man than most men of the men in here, whereas I was more of a lady but because of my dick she thought I was disgusting. I know she liked my tits though, a firm 'C' cup - aided by silicone. I would catch her looking, so just to piss her off I'd walk around stripped to the waist, that just winds her up.

I shave my body and kept my hair long, it ensures I get my share of wolf whistles as I walk to the mess hall but I always shower, discretely, with the girls. Most completely ignored me, some are openly hostile but so far they haven't attacked me. The men, however, liked me even the guards looked in the cell door whenever they passed. I have several guys on the go, visiting them in their cell. All have big cocks, some are gentle as they fuck me, others a bit more forceful. Others just preferred mutual wanking and and sucking.

I was going to the exercise yard when a guy who had shagged me some time previously blocked my way.

"How much for another fuck?" he asked. I tried to dodge around him,

"Same as always, two packs of smokes."

"Yeah, but I only lasted a few minutes last time."

"I can't help it if you find me irresistable, lover boy, it still the same price", I said flippantly.

He grabbed me by the arm, he was a big black bugger and his grip was hurting me.

"Don't spoil the merchandise," I snarled. But he just dragged me into his cell. Usually the cell mate would arrange to be out but his was waiting for me. Standing naked behind the door, he was a fat, white guy. Grabbing my other arm, they flung me over a bunk and pulled my arms forward. A shank was pressed to my face, I saw it briefly as the white guy brought it up to press under my eye. It was a toothbrush with a sharp blade melted into it.

"No noise or you'll be 'keeping an eye out for cock' for the rest of your life!"

Although silent I still struggled, the naked, hairy cell mate sat on my arms facing me. The shank pressed harder to my lower eyelid. He shuffled forward, his hard cock wagging as he brought it closer to my mouth. The implication was there, if I so much as bit him it would be my last act as a fully sighted person. He pressed his cock head to my lips, I opened up, allowing him to invade my mouth. The black guy was stripping off my few clothes, fondling my body as it was revealed. His fondling became a rougher manhandling of me as he drew my panties down, pulling my dick one way and my balls the other. He gripped my ballsack directly under my dick and stretched down - hard. I screamed around the cock forcing it's way into the back of my throat.

"Lovely," said whitey, "Make her do it again, I slipped into her throat then."

His cell mate didn't need any encouraging and pulled my balls so hard I thought he might pull them off! I would have screamed even louder but my wide open throat, allowed no sound to escape. Hot tears were rolling down my cheeks, my was nose running and it was hard to even breathe. The violation made my head swim, my lungs were bursting and the whole of my lower body felt like it was on fire. The black guy was pulling my dick out like he wanted to pull it off, using it to position my body to receive him.

I sensed him behind me, my naked ass feeling his rough prison trousers being dragged down. I hadn't lubricated myself before leaving the cell and I'm sure he wasn't going to use a condom, even though some had spilled from my pocket as my trousers were torn from me. I heard him spit and he pressed his cock into me. I could feel the big cock head pushing past my sphinter and sliding in. The sheer size of him was pushing my ass cheeks apart. He grunted, pressing harder against me, forcing his way in. I was terrified he was going to tear me.

Not wanting to make a dry fuck worse, I relaxed as much as I could. It obviously wasn't enough, I could feel his girth wedging open my tight ring. Nothing I could do would make my ass stretch more. A resounding slap to my ass cheek made me tremble, it began to sting, a second later the other the other caught a stinging blow. I was wriggling in pain. He spat on me, the cold, saliva slithered over my anus as he forced it wider. His cock slid drily into my rectum. A greater fire arose tore at my ring as it stretched to it's utmost. Surely I haven't been fucked by him before, perhaps it was shortly after a smaller cock had 'oiled the slipway'.

He was grunting as he shoved forward, I cried out in pain, muffled by whitey as he grunted, pounding to and fro in my mouth. The black cock was trying to split me in two, I sagged down, my strength dissapating. He pulled out a little and slapped my ass, again, hard. I leapt up and almost off his cock it hurt so bad. Another slap on the other cheek had the whole of my bum hurting even more, the pain was spreading through me. Whitey grabbed hold of my head and was virtually wanking himself with it, my neck was being stretched and it wasn't even in time with the cock plowing my ass. They were using my body for their pleasure, I was just a lump of meat to them, a cum bucket to fill in any way they wanted.

And cum they did, whitey pulled my head so hard I thought my neck would break but that seemed nothing to his cock forcing it's way down my throat. His cock spasmed, spurting load after load almost directly into my stomach. His thighs gripping my shoulders tightened as he shot his wad, my breathing became even more of a problem. The black guy had stepped up his pace and was piling into me as if he would cum into my throat by way of my ass. His thighs were slapping my sore cheeks, my sore nuts were swinging to and fro, banging against his, adding to my pain.

He thrust into me, his arms around my hips, pulling me back as he drove in. Until suddenly, he stopped. With a really hard upwards thrust, he came long and forcefully inside me. Once, twice, three times he painted the walls of my rectum with his orgasm. Whitey pushed my head away, disgustedly, the black guy pulled out of me and pushed me sideways to the floor. I lay there trying to breathe, scared witless that I might be infected with some sort of sexual disease. They pulled their trousers on and walked out of the cell, it probably wasn't even theirs. I numbly gathered my clothes, pulling my blouse on and doing up the few buttons that remained. My skirt was a shapeless mess in one corner, I stepped into it and held it closed with one hand as I stumbled panty less back to my cell.

Lynda spun round surprised to see me back so soon,

"What the fuck happened to you?"

I must have looked terrible, make-up smeared across my tearful face, snot dripping, clothes hanging from me. I sobbed as I told of my rape. She knew one or two of the big guys I 'dated' and said I should set them on these two rapists. I shook my head, No, our relationship was purely a business one, I couldn't start asking them to act as minders. I painfully leaned over to collect some clothes and went to the showers. Standing under the cool jets I tried to soothe the burning pains in my genitals. My nuts were already turning black and blue as I directed cold water to my ravaged asshole.

I heard later that the two guys had been involved in a little 'accident'. When I told Lynda she said it's surprising how word gets around in prison and smirked. I was about to ask whether she had told about my rape but she rolled on to one cheek and farted saying,

"There's vitamins in the air."

That kinda put our relationship back on it's usual footing. Changing the subject, she said,

"Candy I need a favour," Her whole demeanor suggested it was in return for the one she had done me.

"Belle, wants us to have a baby."

She must have seen the surprised look on my face. Then my jaw dropped when she asked,

"Does your dick still work?"

"Of course it still works but there's no way I'm going to have the responsibility of becoming a father. There's loads of guys in here who would shag her, even if she looks like you."

She bridled at that but continued,

"You're probably the most intelligent person I know and Belle doesn't want some loser fathering her baby. At least you were caught in some clever Stock manipulation thingy."

Lynda most have been desperate, saying she liked anything about me. Normally I'm the butt of her coarse epithets.

"Candy I don't want you to shag her or anything like that, just have a wank and give me some of those little wrigglies that you keep wasting."

"That would still make me the father. Anyway, transferring sperm from my hand to yours before you finger her, I doubt you'd get her pregnant."

"Yuck! I'm not having it in my hand, you queer pervert!"

"All the condoms are covered in spermicide, so that won't leave you with any viable sperm."

(I didn't like to say that after years of taking female hormones, I'm left with very little ejaculate).

I pointed out,

"Without a turkey baster and a means of keeping it at blood heat, you're bound to fail."

"There must be a way."

"Forget it."

Lynda stomped out, no doubt to give Belle the bad news. A photograph lay on her bed, it showed a cute 20 year old girl. Was this Belle? How old is the photo? In it she had her bare ass turned to the camera, her lovely face peeking coyly over one shoulder. Her ass was to die for, perhaps if I could arrange to shag her face down, cock in her ass, then shoot over her sex, Lynda could massage it to where it needed to be. After a evening of arguing, Lynda said she would ask Belle whether she would agree. I honestly thought that would be the end of it, the whole idea would be a non starter.

Half way through the next morning, Lynda stood inside the open door, scratching her armpit, morosely looking at the floor.

"Belle said, 'Alright'. But no kissing, no touching her up and you have get checked by the medics that morning."

"I get checked regularly, especially after . . . you know. But I have a proviso, there's no way you're going to watch."

"I don't want to watch your gay humping, you dirty shit shoveler, just take it easy with my girlfriend."

The photograph didn't do Belle justice. It couldn't capture the bubbly vivaciousness of the girl. Why she would want a wrinkly old mother figure like Lynda was beyond me but that's their business.

It felt awkward, it wasn't like any liason I'd had before, I'd never interacted with girls. When I looked in the mirror I looked like a girl myself, but hold on, she likes girls. Why not just play on that and ease into the rest of it. We needed to kiss, without that introductory stimulus I might just as well stick my cock through a hole in the wall, just like Lynda had suggested, the night before. We sat nervously, knowing what was about to happen but trying not to think too far ahead. Had she ever had anything up her ass before? Would it be possible without hurting her? Could I even get a hard on with a girl?

I put my arm around her, whispering gently,

"You don't have to do anything you don't want to do, don't forget, you will always be in control."

She nodded, probably not trusting herself to speak, I leaned closer.

"Your lips are so soft it would be a shame not to kiss you." She turned her face to mine, perhaps seeing me properly for the first time. Her eyes widened, she leaned in and we kissed. Soft lips, none of the scratchy top lip that I was used to, her body relaxed as we cuddled together. Although we broke the kiss it was she who kissed me next, a fervent pressure of her mouth against mine, her tongue darting between my lips. We kissed for ages, I kissed all over her soft face, down her neck and eased her top off one shoulder as I kissed my way over one breast. My hand was caressing the firm, heavy weight of it as she clung tightly to me. I placed her hand on my breast, it didn't take her long to move her hands under my top.

Belle stroked the underside of my tits, giving no indication that they were not all real. The soft tissue had a silicone support underneath and I was self concious about it. My free hand slid under her top, lightly brushing the swell of her other breast, teasing the nub of a nipple, causing it to stand out proud. She sighed, I knew how she felt, I loved my tits stroked and could caress the top half of Belle with some confidence. Her hand moved slightly on my thigh, whether due to giving me access to her or a questing advance to my groin I didn't know. I sought her lips once more, kissing her deeply as both my hands slid up her body to lift her top up to her neck, stopping our kiss only to lift the garment away.

I kissed her arm, holding it out, giving her a little time to get adjusted to her breasts being on display. My kisses moved upward, then neared her breast. Only then did I look at it properly, I sighed, she was absolutely gorgeous, how I would love breasts like hers. I kissed each of her nipples in turn, my hands helping to keep the turgid nubs, hard. She was doing the same to me, as my hands then went to the waistband of her trousers, easing them down and rolling her to one side lifting up each cheek of her cute ass to allow me to take them off. Again I kissed her neck and nibbled her ear, not overtly looking at her naked body, giving her time to be comfortable with her nudity. She had taken off my top but I think she was a bit reluctant to remove my trousers.

I eased them over my hips and slid them down my legs. Now both naked and fondling each other, our kisses were stoking our desires, both of us busy caressing each other, I felt her hand slide up my thigh. I could feel my half hard cock was rising to the occasion, happy that this gorgeous girl was encouraging it's tumescence. Her fingertips touched the head of it and she stopped. I stroked her body and encouraged her to lie on one side, looking away from me. Easing her uppermost leg to bend, keeping her in place and allowing me access to her beautiful ass. Her spine and the cute dimples at her lower back swept with majestic beauty to the full curves of her cheeks. I lay behind her, stroking her body, kissing those sweet mounds. I continued, stroking along her thigh, then back again, sliding my hand both to the rear and front of her..

My caress was moving closer to her sex, the soft slit didn't excite me like a firm cock would have done. I glided my hand close but didn't touch her, she may have thought it inappropriate and I might lose my hard on. I teased the soft area at the top of each leg, working over her ass, a little pressure causing her to roll further onto her front. Her delicious derriere took my breath away, it soon became the sole object of my attention. My hand trembled as I stroked the smooth skin, the flesh soft over firm musculature. The sweet smell of her was so different to what I normally encountered, her ass seemed to be softer, more pliable. I moved up to kiss her lower back, planting sweet kisses on the dimples each side of her spine, trailing those kisses to the beginnings of the swell of her ass. Those sweet cheeks were a veritable feast for the eyes, the smooth curves dividing into a deep cleft and there, jewel like, the pinkest, tightest sphincter I had ever seen.

Oh, God how could I possibly get in there? My heart sank, it seemed for all the world to resemble a pencil sharpener. I wanted to fuck her ass more than anything I'd ever wanted before but even my small cock would have a battle on it's hands. I sighed, more kisses to those gorgeous cheeks saw me travelling over them, my eyes on the tight goal. I was determined not to notice her bald sex, not wishing to decrease the hardness in my cock. I licked a finger and kissed my way up to her anus, my tongue flicking here and there, using it to test the strength of her sphincter. The ring of muscle seemed impenetrable, I traced a finger around it, probing gently hoping it would give way a little. My wet tongue pushed at the tight portal, seeking the slightest relaxation of her, a finger poised to take any advantage should she relax. There, slight ingress with my tongue, my finger pressed the spot, whilst my tongue probed deeper.

Again, just a little less resistance, my finger slipped in, my other hand stroking her ass cheeks. I sucked my thumb, it took quite a while to eventually get it into her. The awkward bit was to maintain the widened anus and use plenty of lubricant on her. More lube on my cock and it seemed to want to slip into her pussy. Using my hand, I guided to her ass hole and, removing my thumb, pressed gently. Her sphincter still gave some resistance to my entry but with greater pressure, I could feel a gradual widening. Gentle pushing slowly gained me entry. I was trying my utmost not to hurt her, the lubrication was working but how did she feel about me pressing into her ass?

I lay alongside her, kissing her shoulder, her neck, all the while trying to get the head of my dick to firmly lodged within her. I held my cock straight with one hand, aligning it correctly and pressing relentlessly. There, more relaxation on her part and I was in. Just half of me was being gripped tightly, I was all too aware I could slip out easily. A further push and I was more firmly in. We were both panting, my breathy kisses were on her shoulder, my hands caressing her breasts, which she was almost laying on. I gave her a few moments to relax and pressed home both my advantage and my cock.

Again we rested, I pulled out a little before pressing back in, she moaned a little. A rest, and I repeated the sliding motion, the lube did it's job, allowing us to move to and fro. I didn't push in too far, after all I needed to pull out in plenty of time to cum over her sex. Surprisingly my desire was for her and not just her ass, I loved the warm touch of her, the way she smelt, everything I'd never found in a sex partner before. All those things I never realised existed. The sensation in my cock was growing, I was kissing her neck, in fact anywhere I could reach, I couldn't get enough of her. I'd never really thought about a girl before, now, I was close to climax and wanted nothing more than to love this beauty. This was a warm closeness that I hadn't considered previously. I pulled out thinking just a few strokes, but no, as I shoved my cock beneath her perinueum, the slight friction was just what I needed to orgasm.

I drove forward, my cock feeling a sudden wetness and I was inside her once more. Not the tight embrace of her ass but of her wet pussy. The realisation took hold just as I spurted deep inside her, it felt wonderful. Her ass was snug in my lap, my cock bathed in a silky embrace and I'd just experienced a wonderful orgasm with a girl. I thought I would find it abhorrant but no, it was just great. I lay there grateful that this opportunity had arisen, I realised I wasn't Gay, even in a Transexual way, I was Bisexual.