Jail Time

I rolled away and slid out of her, caressing every part I could reach, she turned onto her back and I shuffled to one side. I risked further light kisses to her nipples, then her lips. I mumured,

"I hope that works for you both," and got up to dress. She lay there looking beautiful, only now did I look at her sex, she really had a gorgeous body. I sighed in admiration, she blew me a kiss and I walked back to my cell. Lynda is a really lucky lady.

It was a couple of months later when Lynda carefully carried a box file into the cell, holding it horizontally. She stood there looking like a drunken sculptor had stacked a pile of wet clay, which was now being slowly shaped by gravity. It wasn't doing her any favours. I leaned up on one elbow,

"What's in the File box?"

"A cake to celebrate Belle getting pregnant."

"There's a twist, a file with a cake in it."

"Kitchen cons said they were making one for a warder and made two. It cost a lot of smokes, so don't go shouting it about."

"My lips are sealed, especially if sweaty Bill, the fat 'chef' had anything to do with it. The mixture probably started dry and he just dripped in moisture as he stirred."

"For Fuck's sake don't start saying things like that near Belle," she riled.

"Why, doesn't she like too much salt in her diet? Is that why she won't suck cocks?"

"You didn't try that with her did you? You perverted Tranny, I'd rip you a new ass hole, only you'd probably get twice as much pleasure."

"I'm just messing with you, do I get a bit of cake, then?"

We went to Belle's cell, she was due to be released in a couple of months but Lynda still had another six to go for breaking her bail terms. At least if she keeps her nose clean she'll be out for the birth. It ought to be clean, there she goes again wiping it on her sleeve, adding one more silvery trail to the collection decorating her prison shirt.

Of all the guys in here, there's only one guy I'd fancy to fuck. He gives me the eye but never speaks, one day I finally spoke to him. He was the shyest guy I'd ever met, we talked and I flirted, obviously, soon he was soon like putty in my hands. Aparently he had never had a girlfriend and although he seemed keen on me, he raised objections about the type of guys I'd been with. I told him that everyonee wears a condom and in fact I get checked out regularly. He relaxed at that and walked me to his cell, it must have been the neatest in the whole prison. He stood there, seeming to be at a loss, so I plonked myself down on a bunk and patted it beside me. He sat almost primly, his knees and feet together.

Jim was his name, I told him my name was Candy and that I was transgender, that didn't seem to faze him, so word had got around. I leaned in for a kiss, he kissed me tentatively at first but then relaxed into it. I felt his hand on my breast, I moved to give him access and soon both my tits were being squeezed. I sat back from the kiss, he was blushing, his face a firery red, his hands dropped away, bashfully. I rolled up the hem of my top, baring my flat stomach, my navel glinting with a belly ring. Putting his hand in the wake of my hem, he lightly stroked my belly, then gained confidence, pushing my top up until my breasts came into view.

He gaspsed, both hands circled those firm globes, his fingers brushing my nipples causing them to harden. He seemed transfixed, both hands probably feeling soft womanly flesh for the first time. The sound of his breath grew louder as he leaned in, planting a light kiss to one nipple. I puffed my chest out, the light feathery touch of his lips was so delicate, not the usual rough sucking that I normally get. His attention switched to the other breast, one finger toying with the now, wet nipple, as he kissed his way over the other areole. I crossed my arms and grabbed my top to take it off. He sat back as the material dragged up my body, lifting my tits as it went, only for them to drop and bounce. He leaned towards me, to kiss his way over over my naked flesh, my hand slid along his leg to test the bulge in his trousers.

The material was tight where his cock was straining to get free, I eased both hands down his elasticated waistband and pushed it down. He lifted up and I slid the trousers down past his knees. A lovely cock stood proudly in his lap, it was big and long, and to think, mostly unused! I could soon alter that. I kissed my way down his belly not going straight for the main prize, simply allowing my hand to brush by his balls as I again kissed his lips. His kisses were more ardent now, it seemed the right time to gently take his cock in my hand, The solid, weighty feel of it was enough to get me excited and, by the feel of things, he wasn't too far behind.

I stroked him lightly, pulling the flesh up and releasing it, then pushing the loose skin down to reveal his cock head. Uncircumcised, it bent slightly as I pushed down harder, held by the frenulum it bowed to my ministrations. A rigid member, formerly in a club of one, I'd like to introduce it to a 'hole' new venue but first I want my way with him. Moistening my hand with saliva, I slowly wanked him, he seemed at a loss of what to do and toyed with my breasts. I leant down and kissed my way down his length, he leaned back, that's a good sign, he was more relaxed. Pushing his foreskin down, I uncovered his cock head and gently kissed it, his thighs closed, as if unconciously trying to cover himself. Taking it easy, I blew on the straining manhood, he sighed, my cue I thought to place my lips on it. He was still relaxed, so I opened my mouth and engulfed his cock.

Not a particularly easy feat, because he was so big. With my mouth full I went further down on him, but probably no more than half way. I eased him onto his back, I lay alongside him, pulling the back of my trousers down and used my feet to take them off. I kissed his lips again, arching my body to keep my cock from nudging him. Slowly I allowed my tits to rest gently on his chest, the hard nipples grazing across the dark hair matting him. He held me in a warm embrace, kissing me fervently, my leg made contact with the solid bar that was his sex. He moaned as I slowly rubbed my body on his, careful still, to keep my sex from intruding. I reached down and slipped a condom on him, holding him firmly whilst I turned my back to him. His arm draped over me and I felt his hand slowly caress my breast.

Carefully I pressed my ass into his belly, then maneouvered myself so his cock slid along the crease of my ass. I was feeling the rigid head of him slide toward my anus and relaxed, allowing it to press hard against me. He moaned once more, I pressed back, he pushed against me and, suddenly, was in. Everything stopped, our movement, our breathing, even it seemed, my heart. The steady pressure between us and the heat of my desire allowed me to feel his cock, slowly sliding in. His thighs touched mine and we relaxed. He held me tight, pressing his body to me until he was fully home.

I moved my hips away from him slightly and he got the message. His cock started to slip out of me, then returned. Again he started to pull out, only to return with vigour. The rythym and pace stepped up as he got into it. We fucked gently, all the while he played with my breasts and kissed my neck. Then his hand slid down to my hip, now as he lunged forward, so he pulled my body back to him. The pace increased, his hand now grabbed my ass cheek, squeezing and fondling it. Still his pace increased, his hand around my belly, pulling me towards him as his cock slammed into my ass. This was wonderful, his hand went up higher, under my arm and grasping my neck. His body rolled onto me, I straightened my legs and laid on my front. His other hand slid under my other arm and clasped my neck also.

Now he was on top of me, holding my body, pushing down on my neck, thrusting urgently into me. I wasn't able to push back at him but didn't need to, he was nearly there. Humping me like there was no tomorrow, his ass was like a jack hammer, I was close to orgasm myself. It didn't take long, he thrust in me as far as humanly possible and I felt the pressure as he spurted like a geyser. Although I couldn't feel the cum like a powerful jet inside me, the familiar heat and pressure as it forced the condom to balloon, was enough for me to know. Subsequent cramping of his body told of more cum being pumped from his balls. We lay there, tightly together, him gasping in my ear and I, happy we had had such beautiful sex. I was in no hurry to leave but, like most guys, he soon pulled from me.

Again, he seemed at loss and I stood and dressed, leaning over to kiss him, saying,

"Here's to the next time."

His smile made my day.

When I had showered and returned to my cell Lynda gave me a baleful look, snarling,

"It's all your fault."

"What is?"

"Belle won't let me near her in case I upset the 'delicate balance' of her hormones."

"I haven't got a clue what you're on about."

"She wants to give every chance of your sperm making our baby." She slumped in a chair, legs akimbo, like a discarded rag doll. "If it means you don't have to shag her any more, then I'm all for it."

"Yeah, you look happy."

She slung a book at me, "Get fucked."

"Just have." I replied sweetly and got out while the going was good.

A week or so later I carefully applied my make-up and took ages over my hair. I was going to see Jim only what I had in mind probably wouldn't have ocurred to him. I wanted to fuck him, a new feeling for me but one I've been dreaming about for some while. He was glad to see me, and why not, he had enjoyed himself last time. We kissed as soon as we entered his cell, his hands were fondling me, eager to relight the passion that we experienced before. We sat on his bunk and our desire took over, the kissing and touching more spontaneous, the removal of clothes a mere prelude to the sex we remembered. He lay back as before, my hands stroked his thighs and I slipped between them kissing my way to his erect cock.

As my mouth encompassed his turgid tool, so I slid my shoulders under his thighs, encouraging him to raise them. As I sucked at his cock, so my shoulders pressed forward and his bent legs rose. My mouth was still working it's magic, sucking and nipping at his rigid weapon. He groaned, I needed to keep him focussed, as my hands caressed his ass cheeks, rolling him further onto his back, bringing his anus into view. My lips left his cock and kissed their way around his ass, my hand just holding his throbbing apendage, just keeping it tittilated while I kissed and licked at his sphincter. His legs were on my shoulders, my saliva lubricated fingers probing his ass. I furtively reached for some lube and coated my fingers, pressing them gently to his weakening ring of muscle.

I was taking things easy but my lust was threatening to take over, I eased back his foreskin, giving his cock a thrill as a third lubed finger joined the other two. I needed him to relax to allow me to fuck him. My shoulders squared up, pushing his thighs higher, my cock nearing his ass hole. I awkwardly slipped on a condom, lubed fingers making it more difficult. My cock pressed at his tight entrance, the teat of the slippery condom slipping this way and that. By now, I was worried he might 'come off the boil' losing the wanton desire that I was relying on to have my way with him. There, my cock pushed into his ring, I lined myself up to press it home.

Pushing a little harder I felt him give way, we rested. I took my time, using one hand on his throbbing cock to keep up his interest . Finally I pushed fully in, he was tight and hot, I could feel his whole body holding still, not knowing what was about to happen. Gently I eased out a little, then just as gently back in. My cock felt as if it was soon about to cum, I had to take it slowly for my sake as well as his. It would spoil everything if I came prematurely, he must be the one to cum first. My thoughts turned away from our present situation, anything to keep from stoking my excitement, holding back the imminent climax.

Gradually the urge diminished and I could slide easily and harder within him, hoping he was getting pleasure from our love making. He was groaning but then so was I, the pair of us sighing and grunting and our bodies making the wet slapping sound that only sweating flesh can make. He gave a protracted moan now and then and I believe I had the angle of penetration just right to massage his prostate. His pace picked up matching mine, for some while now I was 'holding back' trying not to cum but I couldn't hold on much longer. I was driving my cock into him like there was no tomorrow, desparately trying to diminish the sensation I was feeling.

The pace was relentless, I don't know how much longer I could hold out, I could feel my orgasm approaching. We fucked just a little longer and then the dam burst for me, I thrust upwards in a kind of rictus, my back arched, thrusting my cock up as far as I could. I fountained inside him, feeling the cum gather around my cock, trapped in a latex bubble. He bucked underneath me, surely not - his cock spurted against my belly, he had cum at the same time, a feat I had rarely accomplished.

We both just lay there panting, eventually I had breath enough to kiss him. I withdrew, carefully keeping my condom in place and letting him know that I had. I hoped it was just one of many times I would visit him, next time he could have me again, I was looking forward to it. I might even let him ride me bareback, to feel him shooting his load deep inside of me. Now there's somehing to look forward to.