[Story] A Rough And Gentle Night (18+)

[Story] A Rough And Gentle Night (18+)

A lonely man and a bartender decide that tonight is their night, after days of flirting. Jay, a drifter with a large domination/sadism kink, decides to treat Anne with respect. Anne spends her night with Jay, losing her virginity to the mysterious man.
Jay had always been interested in the woman.

Despite her job, working as a bartender at Husk’s Head Bar, she seemed to be interesting enough. He often visited the bar, due to a alcoholic addiction, and she would serve him every time. The visits became more and more frequent.

He found his eyes tracing her curves, or the way the plaid shirt folded around her breasts. It wasn’t like Jay to be so attracted to a woman, for he had always been somewhat afraid of himself during sex. He was sadistic, abusive, and dominate. He treated his partners like scum. But this woman, Anne Blooming, she seemed so kind. Almost like a flower, that Jay could never damage.

It was a late tuesday, and Jay sat alone at the counter. He was slouched over, his head fuzzy and pounding as he downed another shot. The man wasn’t drunk- no, not yet. But he was determined to be.

Anne passed him, waving her hips in such a fashion that she seemed to be flaunting her ass. Jay couldn’t help but notice. He felt a shiver down his spine, imagining what he could do to that ass.

Amidst his day dreaming, Anne was watching him. She saw this strange, haggard young man daily, always looking so lost. All she wanted was to show him a good time, but she was a shy woman, and had never done such a thing.

Jay decided to take it upon himself to speak to her. If he wanted to, he could be quite a convincing young man. With the will of a his quiet, almost seductive voice, he could succumb woman to give into his wishes.

“Ma’am” Jay summoned, waving her over. Anne had a large platter of drinks in her hand. She set it down for the men sitting in a booth, and trotted over to Jay.

“I hope I’m not out of line asking this- but are you free tonight?” Jay surprised himself, being so forward.

Anne held a flutter of excited anticipation in her chest. She didn’t want to seem too excited, but she had been waiting for this man to ask her out for the past week or so.

“Oh, yes, I am. I’ll be off in a half hour, is that okay? I’m Anne by the way” Anne laughed nervously, extending her arm.
James smiled, but his eyes remained somewhat troubled. He obliged, shaking her small hand with his cold one “My pleasure. I am Jay.”

“Hello Jay. I-I have to get back to work- uhm, meet me in the back?”

Jay nodded, smiling “Sounds good.”

It was rather a quick and awkward exchange, but both of their intentions were clear. Jay wanted to fuck a beautiful woman, and Anne wanted to make love to a mysterious man.

Forty five minutes later, James leaned up against a wall, smoking. It was cold outside, and all he had was a brown leather jacket. He was a tall, thin man who had been traveling on foot for about a month. Often he would prey upon whores or desperate and bored woman, and practically kill them after filling his desires. He was a lost man, who was more focused on hurting others than healing himself. His hair was black and somewhat unruly, and he had cold grey eyes that held so much pain people couldn’t look him in the eye.

He blew a plume of smoke into the air and sighed heavily, wondering where Anne was. As if summoned by his thought, she came rushing out of the back door, wearing a thick wool sweater.

“I’m so sorry! John made me wash the-”

“It’s alright. My place or yours?”

“Oh, um, yours I guess” Anne smiled, nervously running a hand through her long curly black hair.

Jay drove in his beat up truck he had rented a few days ago. He had mostly been traveling on foot, so a car was a blessing. It smelled like horrid air fresheners, but Anne didn’t mind.

Jay’s home was very empty, she thought to herself. He had recently moved in, but didn’t have much furniture nor boxes in it at all.

Anne’s intentions became clear to Jay when she took of her top, and tossed it on his bed. They had just arrived, and Anne, being a nervous mess, didn’t know to proceed. So, she just threw off her plaid shirt, exposing her large breasts and lacey bra. Jay stood inthe bedroom entrance, surprised.

He was captivated by her swelling breasts, barely contained by her bra. Without speaking, he approached her, and looked deep into her hazel eyes. Silently, he bent down and let his cold fingers stroke her face. Their lips met, and James gently bit in the kiss.

Anne felt rush of blood go down to her labia, and she resisted the urge to fling herself upon the tall man. Jay grabbed the back of her head, pushing her closer to him. He was rough and demanding in the action, and Anne wondered if she was in over her head.

With nimble fingers, he undid her bra and let it fall to the floor. He nipples brushed up against his shirt, hardening in the cold room. While his lips remained against hers, his fingers fondled the breasts, a hard on rising slowly in his pants. Her skin was soft and warm, almost like a child’s.

James found himself running his teeth along her neck, in a animalistic manner. He pushed the woman down onto the bed, crouched over her, rubbing his crotch upon hers. This turned Anne on immensely, and she resisted the urge to stroke
him out of apprehension and anxiety. Jay thrusted upon her, taking her nipple in his mouth. He twilred his tongue around her tit, making her moan.

As he did so, he undid her pants, and she wriggled them down to her ankles. The woman’s pink panties were damp, and she squeaked as James gently stroked the soft bulge of her labia. As he did so, he smiled slightly to himself, watching her moan and twist at the mere command of his fingers.

Anne was surprised when their steady pace took a rapid turn. Jay was suddenly biting at her neck, his fingers slipping past her paintes, and borrowing deep within her folds. His hardon was raging, pressing tightly against his jeans. He thrusted slightly as he fingered her, rapidly moving his finger deep inside her. Her neck ached as he bit, the metallic taste
of blood faintly stroking his tongue.

Right before Anne was about it climax, Jay withdrew. Anne looked at him with confusion, but that confusion melted away when he undid his zipper. His member was rather large, but not overwhelming. It was throbbing, already dripping with precum.

He panted, grinning slightly like a madman.

“Suck it” He said with a growl. Anne had never done such a thing, but she had certainly day dreamed about it. She gave him a small nod, and pressed her lips against the head.

It was warmer than she was expecting, and tasted slightly salty. Slowly, she began to move her head back and forth, and James smiled. She was a beginner, no more experienced than a teenager. He decided to show her how to really suck.

“I’m going to thrust, is that alright?” Jay never usually asked for permission, but he decided to be a gentleman in this fling.

“Mhhm” Anne nodded. He began to rotate his hips back and forth, thrusting into her mouth. He slowly crescendoed, till be was gripping her head, and pushing himself to the back of her throat. She gagged, but that only excited Jay more. Anne had tears in her eyes, as she looked up at Jay, but it wasn’t out of fear, it was out of pleasure. Part of her enjoyed being used like this. She wanted to make the man feel good.

Before Jay got too carried away, he quickly retreated and ordered her the bend over the bed. Anne obliged, sticking out her round ass for Jay’s appreciation.

He slapped her a few times, watching the red mark of his had briefly show before fading. He rubbed her pussy a little, stirring the juices around to act as a lube, for he lacked one at the moment.

Entering her vagina made him moan roughly. She whimpered, so Jay took it slow. He carefully moved in and out of her, her pussy flexing to his will.

“Oh Jay” She whispered, her voice thick with lust. His thrusting became more and more intense as he reached a climax. It felt so good that it hurt, but it was pleasant pain.

He dug his fingers into the flesh of her ass, holding on her her body as he violated it.

“Oh my! I-I’m going to!” He voice was cut off by a large moan as she reached her
breaking point. Simultaneously, so did Jay, hot cum spewing into her pussy. Her groaned, his member twitching as it released semen into her body.

After the orgasms, James slid his slightly limp cock from her, dripping with fluid. Sweat beaded across both of their foreheads as they panted, both amazed by the night.

“Thank you, Jay” Anne whispered as she laid, wrapped up in his arms. Jay kissed the top of her head with a smile