Homeless Man

A couple of days later she lay in bed and could not fall asleep. She could not get the homeless guy out of her head. She had already masturbated, and it did not help. She wanted more. No, she needed more. She was twisting and turning in bed, and it was after midnight when she gave up. She felt she had no choice but to give in to her desire.

Quickly she peeled off her sleepwear and dressed. She already knew what she wanted to wear so it went quickly. She put on the same white blouse she had been having when she flashed him. She buttoned the top buttons and tied a knot with the loose ends like last time. Then she put on a pink pleated skirt that ended mid-thigh. Last she put on knee-high white socks and pink sneakers. No bra or panties. She felt strong. She felt good. She felt excited and the homeless guy was a nobody. She could do whatever she wanted with him. She was not afraid of him. Nothing he could do or say could hurt her. The familiar litany of diminishing thoughts about him went through her mind. It boosted her resolve and made her feel in control.

She left her house and walked through the sleeping residential area towards the mall. It was dark and deserted but she was not feeling scared. She only felt a mounting excitement. She did not even have her phone with her.

Her heart was beating hard as she got nearer the place when she knew the homeless guy slept. Everything looked different in the dark, but it did not deter her. The dark was her friend, it hid her and what she was doing from prying eyes. The homeless guy was going to see her, but he was a nobody and did not count. She was not afraid of him. Her thoughts repeated over and over in her mind.

She stepped into the narrow space between the two storage buildings. Her soft shoes did not make any sounds. She paused to let her eyes adjust to the darkness. Then she crept forward, and she heard the homeless guy breathing evenly in his sleep. Her nipples stiffened and became hard as she crept closer to the sleeping guy. Her pussy began throbbing for attention. But she wanted to get closer before touching herself.

Laura saw his legs first. He was lying on flattened cardboard boxes between two dumpsters. Even in the dim light between the two buildings, she could see they were dirty like him. She inched forward. He was on his side with his back towards the wall. She did not stop until she was standing about three feet from him.

She had never been this close to him before and for the first time, she could smell him. It was a distinct smell of unwashed body and grime. She wrinkled her nose from the potent mix of undesirable smells. In her mind, he was further reduced as a person for being so filthy. He had likely not washed in weeks or even months. His frayed clothes were stained and greasy and even in the dark, it was easy to tell they had never been washed. He had a sweater full of holes and it was so dirty it was difficult to tell that it had some time in the past been red. He had baggy cargo pants and they were so wrinkled and dirty it was impossible to tell what color they had once been. He had a pair of trainers so warn they looked to fall in pieces. He had taken them off and they stood next to him on the cardboard. His socks were dirty but looked surprisingly new compared to the rest of his clothes.

She stood looking down at him. He was breathing deep and even in his sleep. Her heart was beating hard with excitement. She was not afraid of him. In her mind was he a nobody. He had zero value and was worthless. Nothing more than a homeless bum who could not hurt her. The negative and diminishing thoughts about him were on autorepeat in her mind. They were making her feel that whatever she was doing to him had no meaning since he had no value as a person. The burning heat in the pit of her stomach was relentlessly propelling her forward. Whatever she did was going forever to be a secret. Since he was worthless, no one was going to believe anything he said.

She could not hold back longer and pulled up her short, pleated skirt. She plunged two fingers deep into her pussy. She was so wet and ready they sank inside to the knuckles. She moaned. She was so excited she was trembling. She was breaking all social expectations on how to behave. It felt so good. No decent girl should behave as she was doing right now. She hated that everybody expected her to be decent. Always ready to judge if she did wrong.

Laura worked her fingers and there were slick wet sounds as they went in and out of her pussy. The situation was far out of her normal comfort zone, but she was anyway so excited she was trembling. She spread her stance and edged closer to the guy. Roughly she manipulated her pussy. There was a fantastic orgasm brewing and she longed for release. She hunched down with her head and bit down on the hem of her short skirt so she could use both hands on her pussy. One hand worked on her clit and with the other, she continued working two fingers inside her gushing hole.

She shifted closer and bent her knees, thighs spread open. She was leaning over him and looked down at his sleeping face beneath her wet pussy. He was old and ugly, and this was by far the lewdest and kinkiest thing she had ever done. She was breathing heavy with excitement and shifted even closer to him. The heady smell wafting up from him assaulted her nose. The strong feeling of revulsion and desire melded into a powerful mix. She moaned, feeling how her tremendous orgasm was getting closer. The ugly old homeless man beneath her was in her mind reduced to a tool for her pleasure. She could degrade him as much as she wanted.

Laura shifted her stance again. She had one foot on one of the cardboard boxes he was lying on. Unintentionally she dragged the box along with her foot. The homeless man shook in his sleep from her rocking him and he grunted. His slow deep breathing stopped, and he shifted on the uncomfortable boxes. Her heart almost stopped. But she was far too excited and close to an orgasm to make herself stop working on her pussy. She whimpered, so close to coming. The guy mumbled something and shifted again. She stepped even closer, so she was standing over him. Her feet were wide apart and both hands working on her pussy. The smell of him became even stronger and she wanted to defile him. Laura wanted to make him as dirty as she felt for doing the lewd thing she was doing. She was drooling on the hem of her skirt in her mouth, and it gave her an idea. She let go of it and leaned forward over the guy. She opened her mouth and let her drool fall into his greasy hair. Most of all she wanted to spit him in the face, but she was afraid she was waking him up if she did that. She worked her jaw and drooled more into his hair. It was so dirty. She was so dirty. She came hard. It was so strong her knees almost gave out and she would fall on the dirty old guy beneath her. Somehow, she managed to remain standing. She moaned and the guy shifted again. She staggered backward, her knees barely supporting her and her whole body felt on fire. Her back hit the other storage house with a thud and she sank along the wall down on her ass.

It felt like her mind came out of a dream. Laura was unsure how long she had been sitting facing the homeless guy. Her knees were up and spread wide open. She had her skirt bunched up around her waist and her pussy was on display. Her heart was still beating a mile a minute and her nipples were so hard they ached. She could not hear the guy breathing and she did not know if he was sleeping or awake, but she was too dazed to care.

She felt her pussy. It was swollen and sopping wet. Her slick juices were everywhere. It was one of her best orgasms ever and she felt exhilarated. This was by far the kinkiest and most daring thing she had ever done. She had done weird things with her dildo. But masturbating standing over a sleeping homeless guy was off the charts.

The burning insisting sensation returned almost immediately. Even if she had had an orgasm. She settled in better leaning against the wall behind her back. Her fingers began getting her insisting pussy up to speed again. It had been quick and intense standing over the guy. This time she sat comfortably, and she could take all the time she wanted.

It was quiet between the two buildings. She could not hear any sounds from the guy. The only sounds were wet noises coming from her pussy where her fingers were busy. She took it slow. She wanted this time to last before she came again. She watched the dark form lying in front of her on the dirty cardboard boxes. The smell of him was not as strong when she was sitting down.

A long while later she saw him move. He shifted his arm, so his hand came to his crotch. She could not see so well because his crotch was in the shade. After a while, she thought she saw faint movements by his crotch like he was rubbing himself. She began suspecting he was awake. A while later Laura was sure he was rubbing himself. He was awake and watching her while she sat facing him with her legs wide open and masturbated. She looked at his face, but it was too dark to tell if his eyes were open or closed. He was awake and was watching her masturbating. He was in the dark, but she was sitting in the middle of faint light angling in between the two buildings. She had problems seeing him, but he had no problems seeing her and what she was doing. The heat between her legs felt twice as strong and she let her fingers sink inside to the last knuckle.

Minutes passed and she got the impression he was rubbing his crotch harder. She was convinced he was awake and watching her masturbating. She realized that he might be afraid she was going to stop and run away if he scared her. She still thought of him as her tool for getting off and she was not afraid he had woken up. He rubbed himself harder and harder. She got the impression he understood she knew he had woken up and it had not scared her.

She heard him undo his belt and unzip his pants. Her heart was beating hard. He was awake and looking at her sitting with her legs wide open and fingering her pussy. It had by far been the lewdest thing she had ever done standing over him masturbating. Now it was even worse. Her thighs tremble with desire. She shifted her feet apart some more to expose herself better to the homeless guy. She was so wet her pussy felt like a faucet.

Her throat caught when she saw his cock. It was long, thick, and pale. She could not tell for sure in the hazy light, but it looked thicker than her dildo. His dirty hand closed around the pale shaft. He jacked it while staring at her exposed pussy and how she was masturbating. Her mind reeled. Leaving the house had she never imagined it could come to this point. She sat exposing herself to the old homeless guy and let him watch her masturbating. She could not make out his expression, but she was sure he was loving every second.

She worked her fingers in and out of her pussy while watching the homeless guy. He was running his dirty hand up and down his hard cock. She was less conscious about the smell coming from him. Neither one of them uttered a word.

Laura felt completely exposed to him. She was defying all social norms and expectations on her to be a good and decent girl. It felt so liberating to break all unwritten rules on how she was supposed to behave. She wanted to rebel. She wanted to be more.

She stopped caressing her pussy and began undoing the buttons in her blouse. She undid all buttons above the knot and then she pulled apart the two halves, baring her boobs. The guy gasped. She felt so lewd. It was the first time she showed her boobs, and it was to an old homeless guy. They were full and had a perfect shape. She was proud of them. She pulled on her hard nipples and then cupped her boobs. Presenting them to the guy's eager gaze. She could see that his hand was moving faster along his shaft but otherwise he did not say or do anything. A shiver ran down her spine. It was the first time she saw a cock in real life. She stared and tried to get a good look at it, but the light was poor, and his moving hand was blocking it. She wished he would hold it up and display it to her in the same way as she was presenting her boobs to him.

Her pussy was screaming for attention again. She slipped her hand down and began rubbing herself. She could not see where he was looking but she arched her back, so her boobs looked as big and inviting as possible.

She lost track of how long they masturbated while watching each other. Standing over him and jerking off while he was sleeping was kinky, but this was far worse. Her forbidden behavior made her so hot she was trembling. The homeless guy was tugging faster on his cock. He began breathing heavily, and she was almost panting. She was close.

She moaned when she came again. It was every bit as strong an orgasm as the previous time. Not long after the guy groaned and thick ropes of cum shot out far. It sounded like raindrops splashing on the dirty cardboard between them.

She felt drained and out of breath. She sat with her back against the wall and legs wide open. The homeless guy let go of his cock. She could finally see it clearly, but it was shrinking. She did not know how long they remained without moving but after some time she felt it was time to leave. She closed her blouse over her bobs and buttoned up. Then she closed her legs that had remained spread wide all the time. She leaned forward to get up. For the first time, the homeless guy made a move for her. He reached forward and took hold of her ankle as she stood up. He did not grab hard, but the gesture was like he wanted to keep her from leaving. She did not get scared but jerked her leg to shake him loose. She stood on unsteady legs. The homeless guy remained on his dirty cardboard boxes looking up at her. He did not make a move for her again.

Without a backward glance, she left him and walked home.

Laura felt exhilarated as she stripped off her clothes and got in bed. Never had she imagined she could be so lewd when she had decided to go and look for the homeless guy. She had not planned anything, but it had felt so right what she had done. It was crazy inappropriate, but it had felt so good. She caressed her pussy while replaying over and over in her mind what she had done. She had stood over him and masturbated. Then she had flashed everything and let him watch her when she masturbated to orgasm. The most intimate and private thing possible. She had been having her legs spread wide open so he could see everything. He was old, filthy, and ugly. She had been so excited showing him her perfect tight body and delicate pussy. She felt emotionally drained from the strong experience. She drifted off to sleep without realizing it.

She felt charged for days. Everything felt better. Including school and the annoying people there. Especially boys who were rooting for her attention. She was hot and popular. Strangely enough did she not think of the homeless guy. Previously he had been on her mind every day and her sole masturbation fantasy. She could not explain why she was not thinking of him.

About a week later she saw him when she went to the mall. He was standing at his usual spot and their eyes met when she came close to him. He did not say anything, but she could tell he recognized her. Her pussy quaked and wanted attention. She continued walking past him like nothing was happening between her legs.

When she was returning home again, she hesitated if she should go to the bathroom and take off her bra. She wanted him to see her without a bra. Meeting him had made her realize she wanted to visit him again at night. Going back home she could see desire on his old face when he looked at her. She nodded in affirmation when their eyes met. He smiled at her, showing his ugly yellow teeth. She felt disgusted by his ugly look, but she let her hips sway a bit extra when she walked past him. She had yoga pants and she knew he was checking out her ass.

Two nights later she stood naked in front of her full-length mirror and admired herself. She could not put it off any longer. Her burning desire was too much, and she knew what she had to do to calm it down. It was about midnight, and it was a fitting time. She brushed her hair until it shone. She did not put makeup on since it was not going to be visible in the dark. She sprayed perfume between her boobs and on top of her mound. The homeless guy reeked but she wanted to smell good. After hesitating for a while, she took the same clothes as last time. Blouse buttoned halfway and tied together at the bottom. Then a pleated short skirt, socks, and sneakers. No bra or panties. It did not show she was without, and they were only going to be in the way.

Laura made her way towards the mall and the parking lot. It was dark but it did not scare her. The darkness hid her illicit activities and made her feel secure. She paused at the entrance between the two buildings. She felt her pussy starting to throb in anticipation. She waited for her eyes to adjust to the relative darkness. She treads quietly forwards. She could hear the slow and even breathe of the sleeping homeless man. She inches forward until she was standing next to him. He was lying in the same position as last time. On his side on top of dirty cardboard boxes with his back towards the wall. His broken shoes were next to him as the previous time. He was filthy and smelled bad. The litany of diminishing and degrading thoughts about him started over in her mind. He was a disgusting nobody, and she could do whatever she liked. Her negative thoughts about him justified whatever she wanted to do to him. She moved in closer and leaned over him and dribbled spit into his hair. Her hand went in under her short skirt to her pussy. It was throbbing and demanded attention. She spits more into his hair, wanting to soil him. Making him even further unclean than what he already was. Most of all she wanted to spit him in the face, but she did not want him to wake up. At least not yet.

His socks were looking to be the cleanest part of him, and she moved down and spat on them. She wanted them to be as filthy as the rest of him. There were holes in his pants, and she tried to dribble spit into them, so he got her spit on his skin. It felt so kinky to degrade him. Moving up she spat into holes on his sweater. Being so close made her gag from the strong smell of his unwashed body and filthy clothes. She spat more, feeling she could do whatever she wanted with him. He was only an old bum. She moved her face near his. She was so close her long hair fell on his grimy chest. He was sleeping with his mouth slightly open, and she managed to hit with a big glob of spit straight into his mouth. She gagged from his bad breath, but it was so hot and kinky. She had two fingers knuckle deep inside her throbbing pussy.

He reacted to her spit in his mouth. He closed his mouth and his breathing changed. He shifted position. Her heart leaped in her chest. She was so excited she was trembling. She had been as excited the previous time but now it felt different. He was a nobody and worth less than trash. Like last time she wanted to treat him like garbage and debase and diminish him to her heart's content. But this time she felt she wanted more. She felt she wanted something from him, but she could not exactly tell what. It had been her most amazing experience ever when she had masturbated while he had been watching her. Instinctively she knew there was more she could get from him.

His lips parted again, and she worked her jaws and leaned down close over him. She held her breath so she would not gag from his bad breath. Her mouth was full of spit, and she dribbled a long, slow stream into his mouth. He reacted stronger this time. Shifting around in discomfort. He was working his mouth and she imagined her spit spreading inside his foul mouth. He stopped moving and she believed he was going to continue sleeping. Impulsively she reached out and squeezed his shoulder. It was the first time she touched him. He woke with a start, and she saw in the dim light the white of his eyes gleaming as he looked up at her. She felt scared but most of all her burning desire.