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On The Train [overtheunder1993 and ShortSighted]

S

ShortSighted

Star
Joined
Dec 20, 2009
Essie James had had a very long and stressful day at work. She was tied and just wanted to get home, crawl in front of her tv and get all cozy and relaxed. Sighing, she glanced at her watch and waited for the train to come. And when it finally did, she sighed seeing how packed it was. She didn't like crowded trains. She liked to sit down and relax, not stand up and be sandwiched between people. In the end she decided to just get on the train. It would be another hour before the next train and she just wanted to go home.

The doors opened and with the other flood of people also trying to get on, she managed to push past people and get herself into a gap where she was holding the pole when the train moved. Not that she'd fall or lose her balance when it did because she found herself quickly sandwiched from every side. She was pushed tightly up against the pole, her shirt covered, 36C breasts pushed either side and her left hand pinned by her stomach. Her other arm was pinned by the guy to her right.

She had her headphones in her ears and couldn't even pull them out to hear herself talk like she wanted to, so she could shuffle and tell people to back off. Then she felt someone pushing behind her and getting up close and personal. She could feel what she was sure was someone's crotch and in the end stopped wiggling to save embarrassment. Despite having come from work, she only had a short black skirt on and the thin piece of red material that was her thong, that parted her cheeks. Just one hour on the train and her journey would be over.

Essie didn't realise she was so wrong. That she wasn't going to be going home any time soon.
 
Mark had been feeling lonely and frustrated with women lately. It seemed that every girl he met had something wrong with them. With every failed first date, every mismatched blind date his friends set him up on, every night spent alone, he became more and more fed up. Then he saw her.

He had already been on the train for almost half an hour when she boarded. First he noticed her long flowing hair and the smell of her perfume as she squeezed past a crowd of people and wound up right in front of him. He looked up and down her body. Her sexy curves drove him wild. He could feel his hardening cock pressing against the fabric of his pants. Then he looked down to his favorite part of a woman's body. She was wearing a black skirt but he could still see that her ass was pure perfection. He imagined the way it would curve, its roundness, the way it must jiggle slightly as she walks. A thought raced through his head. The train was extremely cramped and he knew she would not be able to fight back. And with that, he reached out and placed his hand on her backside. He squeezed slightly. It was firm. and he could feel his finger tips were slightly between the cheeks. She was obviously uncomfortable and he felt her cleching her ass cheeks at his touch. "This is going to be fun," he thought.
 
Essie had settled in for the cramped train journey home. She should just wait an hour and get the next one, but the thought of getting home even later than normal really didn't appeal to her. It was starting to appeal more and more currently though. She could feel a man pressing himself up against her. She could feel his erection - his hands groping her. It was sickening. And then he grabbed her ass cheeks - his fingers worming their way in between the two despite clenching them together in a pathetic attempt to keep him out.

She was an anal virgin. She'd heard of anal but had never done anything like it before and planned never to do it. Struggling, she tried to move away but she was pinned in by the sea of people and the pole in front of her. "Stop." She whimpered, though she couldn't hear herself with the headphones in her ears that linked to her ipod, and she wasn't sure he heard her with the noises on the train. Essie was terrified and been violated on a train. Her pathetic struggles going unnoticed.
 
Mark felt her trying to squirm away but knew she had nowhere to go. He lifted up her skirt and placed his hand on her bare ass cheek. She was wearing a thong. This classy looking girl was obviously more than what she appeared.

Her skin was soft and smooth, and felt good under his fingers. He massaged her cheeks with his fingers far a long time. He didn't want to rush into this. It wasn't his style. He wanted her to picture what was to come as his finger tips tickled her backside. He wanted her to think about the pain and pleasure she was about to experience.

He slowly inched one finger between her cheeks and moved the fabric of her thong aside. Using just his fingertip, he grazed against her tight puckered virgin asshole, tickling it slightly. She tensed up at his touch and he grinned, pressing his finger more firmly against her sacred hole.
 
Essie cried as she felt him touching her ass cheeks. She thought that he was just getting a good grope while he could, but that changed when she felt his finger pushing at her small backdoor. She hadn't thought he'd be daring enough to do something like that on a jam packed train. She struggled and shifted, trying to move away from the prying finger, but she couldn't.

"Please stop." She whimpered. "Please. It hurts."

She tensed as he just pushed harder against the small hole. Her hole clamped up, but it had no effect to the intruding finger. With the pressure, her asshole soon opened up and a little popping noise was felt as his finger was swallowed up. Essie cried out, though not loud enough to alert anyone as she wiggled her ass on his finger, trying to push the digit out. It didn't work though, her walls just clamped onto his fingers like a glove, rippling against it and trying to bring more inside, not expel it.
 
Mark felt his finger entering her sacred hole. It was tighter than he expected. That was when he knew she was an anal virgin. The walls of her anus rippled and pulsed against his finger as he pushed his finger in deeper. He made sure to go very slowly for two reasons. First of all, he didn't want her to cry out and call attention to them. But also he wanted her to feel every single moment of this clearly, each detail, curve, crevice, and scar on his finger as he plunged it deeper and deeper into her tight forbidden hole.

Soon he felt the tightness of her asshole wrapped around his whole finger. It was all inside her now. He could feel that she was nervous by the way she was clenching his finger. He begin to push it in and out, giving her a taste of what was to come when he put something much bigger in there.
 
Essie's body trembled as he opened up her tiny back door. She was whimpering, squirming, and crying against the pole and his finger. This was horrible, uncomfortable and painful. Nothing was supposed to go up there. It was created to expel things. Yet she didn't believe (naively) that he was preparing her for anal. She didn't think he'd risk doing such a thing on a train packed full of people. He was just getting his free grope and pleasure while he could. How wrong she was.

"Oh God, please have mercy. Please make it stop." She begged out loud though only the intruder behind her would most likely hear her words. She was too embarrassed to get anyone's help and bit her lip as she wiggled in an attempt to stop him once again. It was failing miserably. His finger was still planted in her asshole. And now he was moving it in and out slowly, much to her shock.

"Please stop." She begged loud enough for only him to hear. "Please."
 
He could just barely hear her voice as she whimpered and begged him to stop, but he couldn't pass up this opportunity. A nice firm ass right in front of him just waiting to be used.

He slowly forced another finger into her rear and plunged them in deep, even deeper than before. He could feel the extremem tightness of her virgin asshole squeezing his fingers hard. He was getting more and more turned on with each passing moment. As he slid his two fingers in and out of her butt and placed his other hand between his own legs, slowly rubbing and pulling on his cock through his pants. He was harder than he'd ever been, feeling the warmth and tightness of this girl's perfect ass.

He pushed his fingers in and out, spreading them slightly to open her up more. God, she was tight... so tight.
 
Essie bit her lip so hard that it bleed as she felt him stretching her ass wider as he forced another finger inside. She was crying harder now, struggling and quivering around his fingers. Her ass was clenching them hard, the mucsles rippling around the digits in pain. As he started to stretch her open by spreading his fingers, she let out a small yelp and whimper.

"Please stop." She begged again. "Please. It hurts. Your hurting me." She mumbled in a blubbering mess. She wasn't sure if she should be pleased that no one could see this disgraceful act that was been forced on her. It was disgusting. But there he was continuing to finger her asshole as they stood on a jam packed train like they were all alone. She just hoped that his stop was soon - and that he'd get off alone.
 
He heard her whimpering for him to stop but he didn't listen. He plunged his fingers deeper into her forbidden hole, spreading her wider, but this was nothing compared to what was to come for her. He slowly withdrew his fingers and gave her ass a good squeeze and a light spank, his way of saying thank you.

When her ass was finally empty again, he pushed up against her, his crotch against her backside, allowing her to feel how hard he'd grown, allowing her to feel his immense length and girth against her tight, firm little ass. He was worried he might stretch her virgin hole too far, but that wasn't going to stop him.

He unzipped his pants and released his massive erection as he lifted her skirt up slowly. He felt her ass one more time with his hands, getting more excited. Her butt was perfect. He slowly wedged the tip of his cock between her cheeks. He went as slowly as he could. He wanted to savor every moment, he wanted her to dread what was coming. He wasn't even inside her yet and he was almost ready to cum from excitement. Then he felt his cock hit her anus. He pushed playfully against it without entering her yet. Her cheeks clenched around him and he smiled. This was going to be fun...
 
Essie calmed down once his fingers left. She thought that he had finished. That he had had his fun. And she stopped struggling in relief - until he started pressing his erection to her ass. It had closed up. And the she felt the head of his suddenly naked erection teasing the hole between her cheeks. She cried harder and fought against the pole as if she could push it a way and escape. But she couldn't.

"Please don't. Please. It's too big. Nothing that big has been in me. Please don't put it in." She begged. But she could already feel the pressure building against her tiny puckered hole. Her struggling and crying did nothing.
 
He slowly pushed harder and harder against her tight little asshole, struggling to get inside. She was right. It probably was too big. But that wasn't going to stop him.

With one final push he felt the tip of his cock slide past the opening of her forbidden hole, and she was an anal virgin no longer.

He pushed in deeper, deeper, deeper. God, she was tight... so tight. He looked down. His entire length was inside her. He couldn't believe it. Oh god, the pleasure was intense. He began to move slowly back and forth, feeling her extreme tightness around him. He'd never felt anything so good. He closed his eyes as the rumble of the train only added to the excitement he was feeling.
 
She let out a yelp as his head pushed into her anus. She was trying to push him out but her attempts only seemed to help him enter her deeper. She bit hard on her lip to stop herself screaming, completely humiliated over what was happening to her on a train in front of people.

Now that he was inside her there was no begging, only crying as her asshole continueously rippled and massaged his dick from the pain of been forced open so wide.

She would have used her arms to fight but one was pinned holding the pole by her body and his. The other was pinned against her clothed pussy and the pole which she couldn't wiggle free.
 
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