He started using his tongue, slowly at first, and licked down the entire length of her crevice. His intentions were to be gentle, but she ground her softly fleshed buttocks even closer against him in a desperate effort to screw back on the hotly flicking tongue that licked without mercy around her anus. He blew his warm breath softly against her behind and then, suddenly, stabbed his tongue straight into the tight fleshy ring.
"Ooooooh," she whimpered as goose bumps rippled across her upraised young buttocks and down the backs of her excitedly trembling thighs.
He lifted his head, his mind churning with amazement at her lewdly heated reactions. Then he moved carefully, still expecting her to suddenly protest and burst the dream like a delicate bubble, and placed the tip of his outstretched middle finger against the entrance of her tightly puckered rectum. She didn't flinch, and the gang leader decided that she was unaware of the penetration that was coming. He probed for a moment on the outer edges of the elastic little orifice and then pushed forward gently, sinking the finger slowly up to the first knuckle. This time she did jerk and moan softly, but it seemed to be more from surprise than pain because she relaxed again almost immediately.
He pushed the finger all the way in, then planted the palm of his hand on the small of her back and pushed down tight, trapping her between his hand and the mattress. Ellen groaned and made a slight cringing movement when a second finger was inserted, then relaxed again as the fingers dug firmly in the tight narrow passage, widening it and preparing it for the greater entry to come.
The convict couldn't stand it any more. As quickly as he had shoved the fingers in he pulled them back out of her. Besides, he knew he had to hurry now if he was going to get his long hard cock into her before she slipped out of this dreamy pliant condition.
"Kneel up higher," he commanded softly and then, when she did, quickly bent his head and moistened the tiny hole again with his tongue in preparation for the coming assault.
He levered himself up, his thighs pressed tightly against her hips, positioning his rock-hard maledom directly over the wet little opening of her ass, then he pushed. He groaned as he looked down and saw the unrelenting staff pop suddenly through the tight restricting ring of flesh. He watched with open mouth, tongue hanging loosely from his lips, as the tiny stretched opening slipped over and clasped the lust-swollen tip of his cock like a rubber band. All his plans of gentleness were forgotten now in the driving anguish of his own desire as he grinned above her like a conquering devil and thrust his hips hard down until his thick, heatedly pulsating penis sank halfway to the hilt. The warm sponginess of the young girl's tight anal channel enveloped his wildly pulsing shaft, and the feel of her tightly clasping rectum sent a long shudder of delight throughout his body.
"Oh! Nooooooo!" he heard a sudden groan escape from her at the unexpected pain.
"Shut up," he whispered in a hoarse low voice. "It'll only hurt for a minute." Then he added, gently, "I promise it'll feel better in a minute… just relax."
She whimpered and then groaned again, but he was no longer listening to anything, and didn't hear. All his attention focused on his blunt intruding cock that pushed ever deeper into the depths of her nether being, shoving the soft rubbery flesh inside the widely-stretched passage before it in great waves. He felt the coarse hair of his loins smack heavily into the softness of her defenselessly upturned buttocks when he sank the fleshy thickness to the hilt, filling her backside. She cried out in pain now, and twisted, but the darkly handsome convict was unconscious of anything except the bucking of her nakedly voluptuous young body that only served to skewer his long hard cock inch by inch deeper, ever deeper into her.
Billy ground his teeth tightly together and began fucking into her with long smooth strokes, stretching her little anal opening with almost demonic fury. He watched his hardened white shaft pull tiny ridges of her pinkly clasping rectum on each withdrawal stroke, and the lewd sight excited him beyond measure. The young blonde hostage was hopelessly locked in the kneeling position, painfully bent like an errant slave before its cruel master. Her lushly naked body jerked and quivered, and she grunted finally in a long moan of submission. Her thighs released, her resistance broken now, and then convulsed again in groaning protest as his next extra hard thrust pushed far up into her rectum. On and on the merciless sodomizing went as the gang leader skewered into her from behind like a wild man, too excited by his own delirious pleasure to think of anything but her soft rubbery flesh pulling and sucking on his throbbing cudgel.
And then the impossible happened. Through the daze of his own excitement, he slowly heard the low whining moans of pain change, almost imperceptibly at first, and then to a tone that left no room for doubt. It was a low whimper of passionate pleading. She was beginning to enjoy it! Ellen worked and ground back into him, her long blonde hair falling over her face and around her neck and back while she squirmed lewdly in front of him. Her face rolled from side to side on the mattress. He could see it flushing red from the intensity of her effort, her eyes wide in unseeing entrapment in the quest for some kind of fulfillment.
A strange kind of sadistic joy began to throb through his thighs as her warmly fleshed hips began to move backwards to meet the upthrust of his plunging cock ramming into her rectum. She wantonly bucked and churned her naked young body beneath him, encouraging and pleading with the lewdly inviting motions of her buttocks for him to end it and fill her behind with the hot sperm of his orgasm which she prayed would trigger her own release.
Perhaps it was the lewdness of her position under him or the sadistic thought of fucking her helplessly kneeling form half to death. Whatever it was, the pressure was building in his sperm-churning balls and his excitedly jerking cock seemed to lengthen and expand until it was larger than it had ever been before.
And then suddenly Billy stopped.
The convict leader fell forward and pressed the whole of his powerful body onto her back, the thick full length of his cock still wedged deep up in her rectum. Then he gritted his teeth and pulled back, sliding his hardness wetly out of the tight throbbing channel until the tip slipped out of the puckered hole with an obscene wet sucking sound. He hated to pull it out, he was so close to cumming in her rectum that he didn't want to stop, but he wanted more to wring from her the kind of orgasm that would make her his forever.
He rolled her over, the anguish of his near climax still jerking in his throbbing cock, until she lay under him on her back with all the soft hollows and indentations of her succulent young body presented up to him all his and his alone. In one painful gasp, he realized that it was worth the sacrifice when she looked up at him with smoky desire-ridden eyes. His body shook and he almost spilled his load in mid-air when she spoke.
"Fuck me, Billy," she pled in a desperate whisper of unfulfilled torment.
The surprised convict wasted no time as he lifted his body higher over the uplifted pussy between her widely spread thighs. His fully erect instrument lowered quickly and came to rest in direct contact with the tightly resisting entry to her barely used vagina. Still, there was no need for care now, her pussy lay wet and spread open in invitation, the small elastic vaginal mouth already throbbing around the blunt blood-engorged head of his cock as though she, too, were about to explode if he didn't thrust it into her immediately. And so he did, feeling her sparse wetly matted blonde pubic hair part as his mammoth cock head slowly slid into her warmth and kept sliding with one long smooth stroke all the way to her cervix. There was no resistance now, and the smooth slippery walls of her tight little cunt throbbed against his thick hardness in a wetly clasping motion that almost drove him insane with joy.