The Breadth of SympathybyScumbagStyle©
(A completely selfish experiment in fusing erotica with legitimate literature. There's a good chance it will simply be the sex scene in a novel, if it fits. The point was to find catharsis in my own emotions, and apply them in an erotic way, since they link so often.)
The empty dorm rooms had been left unlocked for the summer so that housekeeping could have easy access, and when the party ended the group took advantage of the situation by housing their drunken friends on the bare mattresses. Jon was given a room, even though he was only moderately tipsy and probably would have made it home, two doors down from his hosts. He surveyed his surroundings -- empty desk, empty dresser -- before stripping to his boxers, which he left in case he was discovered squatting. Seconds after slipping under the quilt Andrew had donated, Jon fell into an easy sleep, assisted by the late hour and the gin.
He awoke about an hour later (there were no clocks in the Spartan cell) when he sensed movement in the room. He turned from the wall the bed was placed against to see a feminine silhouette disrobing. When she stepped, nude, into the moonlight, Jon's sleep hazed eyes identified her as Jessica, the partygoer he had spoken to briefly, and who lived two floors down. The slim brunette with the long fingers had large brown eyes that invited honesty, and had read like a billboard his desperation and sadness. Now it was his eyes that read her, all of her. She allowed his gaze to follow her pronounced collarbone to the vast plain of her chest, to the ample breasts that called stark contrast to her slim waist and tiny navel, and finally to her swelling triangle, lightly pronounced by wisps of thin hairs.
"What --?" he began, but she cut him off by gently turning him back toward the wall, wrapping her arms around him from behind. She tangled her beautiful fingers comfortingly in his chest hair and leaned in to breathe warmness into his ear.
"Shh," she was not about to let words kill her nervous momentum. She ran her manicured nails over his chest, and caressed the pebble of a nipple briefly. Jon had no idea what was happening, but decided to allow himself to be explored, as her fingers followed the line of hair down his stomach and gently raked the sensitive groove at his pelvic bone, making him shudder before hooking into the waistband of his boxers. He lifted his hips, and she gave him a mocking, knowing sigh at his anticipation before easing the material over his hips and left them pulled midway down his thighs. He made a move to finish his underwear's removal, but she grabbed his wrist and demanded in sultry tones, "Leave them." She continued to tease him, stroking his thigh, his pelvis, the patch of hair above his penis. It twitched toward her attentions but she left his genitals neglected, prompting a half frustrated moan from Jon.
Jessica gave his ass a gentle squeeze and lifted the covers from both of them. "Don't move," she whispered, pulling her nakedness from him and disappearing into the darkness of the room. In the darkness, and facing away from her, Jon could see nothing. That sense deprived him, he was left to consider how exposed he was, how no one but Andrea had seen him, this much of him, in three years, and he heard what sounded like the tinkle of a belt buckle behind him. He felt her weight return to the shabby, stained mattress and was relieved somewhat, until he felt the rubbery firmness on his back. He could not decide what it was, but it was certainly foreign. Jessica looked on the man laying next to her and sympathy washed over her in a wave, so hot and real it stung. The rugged American cowboy meets outdated grunge rockers had had his heart broken, and she knew what it felt like to be heart-broken. It took considerable strength not to break down and cry herself, to simply gather him up, hold him while they both bawled, but she knew she had to conserve what strength she had left, the strength Jon so desperately needed. She inclined her face into the crook of his shoulder and kissed him there at the base of his neck empathetically. "I know exactly what you need," she comforted him, eschewing any questions he might have about the semi-pliant cylinder that lay between them. He would soon have all of his questions answered.
Jon felt those exquisite fingernails move over his hip to stroke circles on the sensitive flesh of his ass. Jessica deftly used two of those fingers to deftly spread his cheeks and stroke the brown pucker that lay hidden there. The sensation causedhim to gasp, and when he felt a wet and cold substance (like jelly, or oil his spinning mind told him), being applied, he tensed. Jon had always been considered one of the dominant males in all of the circles he traveled in, and here Jessica, a woman, and one he barely knew, was taking liberties with his body he never would have allowed before. The finger ran circles around his hole as she whispered, "Shh, calm down. Trust me," and for some reason he knew he wanted to trust her, like a patient trusts a nurse to heal the deepest wounds. With a will, he let his muscles relax, and Jessica thought good boy to herself as she let what Jon now knew was a strap-on dildo slowly slip past his ring.
Jon felt his body trying to reject the foreign object, the pressure on his virgin asshole almost unbearable. Almost. Jessica understood his predicament all too well and used her free hand, propped on her elbow on the pillowless mattress, to stroke his hair at his temple, almost maternally easing the rubber member into him. When the head crested and the elastic hole closed around the top of his shaft, Jon's visually impaired eyes flared with what looked like the whitest fireworks, and he would have sworn he felt every nerve ending in his body quiver.
With the head of her artificial cock firmly lodged inside of Jon, Jessica's left hand was free to roam. She moved it up to his hip to gently pin him to the bare mattress so her pelvic thrust could do the rest of the work without chance of his pulling away. Jon breathed deeply, the firm pressure of her hand comforting his swirling thoughts and pressing doubts concerning his violation. Jessica let her hips push forward, infuriatingly slowly, feeling every millimeter of resistance Jon's tunnel had to offer. Jon's breath, so steady seconds ago, caught in his throat as he felt sensitive flesh tear away, and with it any sense of profound misery he selfishly harbored, making room for her positive and penetrating presence. Every inch he took of veined phallus dialed a notch down on his self pity, focused all of his attention on the present: the bittersweet agony of deflowering, the terrible and wonderful confusion of his arousal, the heft of Jessica's breasts pressed to his back.
"That's it. That's all of it." Jon's attentions had been on his own emotional state he hadn't noticed Jessica had bottomed out, her hips flush with his ass, and he imagined the sexily satisfied grin she must be wearing behind him. She strengthened her hold on his hip and slowly withdrew, allowing him to feel every second of his bowels' relief, until only the head remained. Jon suddenly felt very empty, and his sense of abandonment swept back to his heart, stronger than ever. He felt a perverted relief when she pressed forward again, and again he parted to allow her erotic battering ram to plunder him. Methodically, she made love to him, and Jon began to realize that no one had really made love to him before, always it was him that poured his emotion into others. Jessica was masturbating his sense of loss, and he began to believe what she had said about knowing what he needed. With every retraction of the dildo, the sadness of betrayal assaulted him, always more powerful than the last time, and with every filling, invading thrust those feelings were replaced with the assurance that everything would be alright. Jessica seemed to appreciate the real importance of facing every emotion head on in order to acclimate oneself to it. And he was doing just that, becoming dependant on the conquering comfort, and whenever she pulled out, he found himself ashamed but unwilling to not push back, impaling himself.
Jessica smiled. Jon was responding perfectly, involving himself in his loss of innocence rather than laying passively. She admired his manly confidence, even with a dick in his ass, he had the presence of masculinity to claim what he wanted from a woman. She felt a thrill of butterflies knowing it was she who had helped him, reminded him that he still had much to be confident in. What she had seen at the party, in his eyes, was the despair of a man who had thought he had known himself, his lover, but could not be sure of anything again. He was beginning to get it back, but this was only the first step.
Jon was beginning to acclimate to the pain, his muscles were relaxing, and his semi-rape was giving him a feeling of spiritual fullness he never imagined existed. The pleasant knot in his stomach told him he was truly filled to capacity. He felt the familiar fingers tracing his pelvis again, and his dick responded accordingly, surprisingly. This time she did not disappoint him, and touched him, lightly to begin with, running her finger tips over his shaft, alternately caressing his balls. His reaction did not disappoint, his cock stiffening at her ministrations. She wrapped her petroleum-slicked palm around his penis and slowly began to pump it. He felt a telepathy with her he'd never known, as if he could read her thoughts. This new gift, a firm but gentle reminder that he was still a man, that his cock was still a formidable tool, that his life did not end with a relationship. She picked up the pace, fucking his ass with new relish, while she masturbated him.
With every thrust, the clit stimulator in the harness pressed into Jessica's womanhood. When she bottomed out, and hit his prostate, the thrill of control, of giving him shudders of delight, of the nub rubbing her clit, her arousal flared to almost unbearable levels. It was time to remind Jon he was not as useless to women as he thought he was. She slowed the hand at his cock to a tantalizingly inadequate pace, and breathed, "You don't cum until I do. I'm going to use your hot ass to get myself off." With added vigor, she focused on fitting every inch of cock into him with faster, more urgent thrusts. Her vision blurred, and she gave him what she promised, giving over to her passions. The itch in her cunt was being gloriously scratched, the not so helpless man next to her meeting each thrust admirably, urging her to use him for her pleasure while she stroked him. Jon felt her nails digging urgently into the triangle of flesh bordering his cock, tugging at the hairs there. It hurt, but not unbearably, and the added sensations were welcome.
Jessica had quit the whispering routine, moaning audibly, reveling in the friction of Jon's tight tunnel, and spewing muted vulgarities and abandoned language. "Ungh, take my cock," she growled into his ear, twisting and pulling his scrotum, pressing her palm hard into his dick. Were she honest with herself, her passion might have pushed her to more intense violence, but her task tonight was not to frighten him, rather to reassure him that he was far from useless. She responded to his willing participation positively, praising him, "God, you're a good fuck. You're going to make me cum!" A few more minutes of grinding her clit against the phallus, against his deepest insides, and she delivered. He felt her shudder, heard her cry her release into the silent room, felt the tempo of his rape slow. She recovered as she ground the last bits of sensation out of the clit stimulator, a death grip on his breast, the last shivers of orgasm making her limbs twitch. She may have slowed her fucking but she did not stop, and when her breath had mostly returned to her, she returned to fondling his genitals.
She found his cock hard, and if she asked Jon would have told her that he was painfully solid, and had not been that hard ever with Andrea. And Jessica had left him untouched for minutes. Jon's arousal at her sexual abandon was a new experience, and every part of him screamed alternately for more and for an end to the exhaustion. She gripped him firmly, and pumped his ass and cock in alternating rhythm, and leaned in to lick his ear lobe. "Thanks, stud. Your turn," she crooned.
It wouldn't take long, Jon's lust was already cresting. He felt comfortable and wanted and the beauty of the woman assaulting him did not escape his attention. He felt used, but not indignant, and pitied, but not weak. Nothing stirs the male ego more than feeling like the man, and Jon was masculinity's captive audience. Her fingers barely fit around his arousal, and they stroked him with more authority and expertise than he had himself, his intimate knowledge of the way he liked it dwarfed by her cunning manipulation. His asshole burned pleasantly, and his prostate felt sore and well used, and she never let up, pushing him farther and farther over the edge. For fifteen minutes she stimulated and punished him, every second feeling like it could be the one, lasting for an eternity, traveling light years in universes of lust, shame, degradation, filth, and most of all pleasure.
She did it on purpose. She knew if she made it last long enough she would cum again, too. She felt her orgasm building and sped her jacking to match her lust. When Jon felt her hand lose tempo, felt her breasts quiver against his back, he knew she had cum again. The idea was finally too much to handle and he exploded. His roar was like that of a beast, a grizzly or a lion or somewhere in between, and the entire building must have heard it. Jessica found her presence of mind enough to continue her attentions, from front and behind. The muscles in Jon's ass contracted violently around the monster that occupied it, and he felt every spasm, every rumble in his body that he had missed in all of the orgasms in all of the girls, for all of his sexual existence. The sensations overwhelmed him, and involuntarily he went fetal from the power of his unloading, spewing thick ropes of jizz onto his stomach, his chest, and the mattress they shared.
When he settled back, breathing heavily, his eyes unseeing, barely aware that the strap-on still rested firmly inside of him, Jessica kissed his shoulders with something like love, but more or less, something delicately alien. She gently stroked his deflating cock with the care she had introduced herself with. When Jon's breath finally returned to normal, she used her impeccable fingers to scoop a gob of the mess from his stomach, and brought the fingers to his mouth, wiping some on his lips before urging him to open for the offering. A half second of hesitation, and he took it unquestioningly, allowing her to feed him his sperm, even sucking them clean. He could think of no reason not to trust her after everything she'd done for him, and she scooped every bit up, feeding it to him as a slave feeds grapes to gods. He suckled a finger and pushed back onto her phallus with an expression of gratitude and respect, and the kind of Anagnorisis induced love that only chance epiphanies can produce. As she withdrew from him finally, he realized the emptiness was not always so terrible, it would be filled again, when he was ready. He had used anal sex with women in the past as an expression of power, and ownership, and it had rarely failed him. But Jessica had shown him that so much more can be accomplished with the inclusion of simple human sympathy.
Jessica stood and removed the harness, completely naked again. She climbed onto the bed, where Jon had settled on his back, and straddled his head, resting on her knees. She settled her vagina inches above his face, and the evidence of her orgasm became apparent. Her cum coated her sparse hair in thick dew, and ran down her thigh, and dripped like a slow faucet on his nose. It was the product of a night that changed his life, and both of them knew it could not be wasted. Jon lifted his head and lapped at her pussy, her sweet mingling indiscriminately with his bitter. He cleaned her thoroughly and happily, her lips, and deep into her tunnel where some had refused the moonlight. Jessica placed her hands on the back of his head, and unable to resist, ground herself into his lips, his tongue. When she released him, and fell next to him onto the bed, allowing him to spoon her, the man again, his goatee glistened with her scent. His satisfied cock found its resting place in the gentle valley between her ass cheeks, and he fell asleep to her gentle breathing and the memories of the night drying on his upper lip. When he awoke, she had left, but had already given him everything he needed.