Playing a Part

Playing a Part

Delicious office sex, oral training, cock warming, riding, desk sex, high rise window sex, and a hint at the character 'playing a part' and tricking the office guy into thinking she is something she is not....This one was fun, very Pretty Woman like

Playing a part

It was lunchtime, and Ruby was bored, she had popped into the new restaurant down the road, unaware that it was mainly used by the workers from the office in the tall building it was housed in the ground floor of. There were fully suited folk everywhere, and she felt a little under dressed in her jeans, knee high boots and t-shirt. She had planned to meet a friend at the station and go horse riding, but her friend dropped out.

She had been really hungry, and this restaurant looked good, and smelled amazing from the street, so here she was. The building was clearly purpose built for the big company above, and she felt a little like she was intruding, but the waitress was kind, and the food was great.

She went to the bathroom and as she walked out, she walked into a handsome businessman, He had thick dark hair, dark almond shaped eyes that gave him a cat like look she found highly attractive, and a slight smile that put her at ease. Ruby was 40, but she put this man at about a young-looking fifties, only a few strands of silver in his hair.

He nodded an apology, and very smoothly gave her a once over with those pitch-dark eyes. She gave a little bow, and stepped around him. He asked if she was one of Momo's and she looked at him with confusion. He studied her face and then apologized, but her curiosity won out, and she asked him what he meant. He said was she new at the agency? She flicked her eyes at the slight widening of his pupils, and the noticeable bulge in his tailored trousers. She put two and two together and smiled, deciding to see where this went.

He obviously thought she was part of some kind of escort agency, she had heard this was very common to see in hotel bars and restaurants, and always wanted to know what it must feel like, to be a bought girl for the night, though she guessed the reality was far less hot and more often with less than attractive and rude men. He was so handsome and well-mannered she couldn't NOT try to see if she could trick her way into his pants.

She tilted her head coyly saying she was new, and just looking around to see where she would be often meet clients when she started. He seemed to take it in stride, and was about to pic up his phone, supposedly to call Momo's and book her. He said he would love to be her first here.

She made up excuses that she couldn't possibly, as her paperwork was still going through and she wouldn't be available to book until weeks from now. He was hooked, staring at her heavy breasts beneath her t shirt as she said she wasn't dressed for company either.

He spoke gently to her, saying not to worry, he could pay her in person, just this once, and then if they had fun he would book her often in future. She bit her lip, playing at reticence and he put a hand on her arm. She nodded with a soft shy smile.

In the elevator up she realized what she had gotten herself into, her ex was a woman, and she had only slept with two men before. Never having experienced some things with men as she had been tipsy when with them. Now she was impersonating a high-class escort, who would surely be trained in the many ways of pleasuring a man or woman. She bit her lip again, but a thrill of excitement ran though her.

Offices had always turned her on, something about the professional environment and the idea of being fucked over a desk, or conference table. It had played on her fantasies for years, but other than a brief tryst in a small home office, she had never had the chance to indulge.

Ruby was a busty redhead, a big curvy size 18, with a bubble butt she knew lots of people stared at, and she had a confidence that made her green eyes sparkle. Her hips swayed as they want to one of the upper floors, and walked through busy teams to a big corner office. He wasn't a CEO, but a team manager, high enough up the food chain he had a private office with a big window. It had a huge cherry wood desk looking over the city, and the other high rise to one side, also offices it looked like.

She turned to see him with a slight flush on his cheeks, and she smiled and leaned on the desk, asking him how he would like to do this and calling him Sir. He locked his door, sat at his big swivel chair and nodded at the floor. She gulped, giving a man oral was new, she had barely kissed and licked the tip of one of the guys she had fucked years ago, he too eager to get inside her pussy instead.

But her mouth watered, she had seen some videos, where she loved seeing girls drive men wild sucking cock, sometimes choking or having their mouth fucked. She wasn't sure she was up for advanced stuff like that, but she wanted to try. So she fell to her knees, and let her ass sway as she crawled a few steps, sat under the desk and crooked her finger. She explained she had not been trained yet and he eagerly said he would help.

He stroked her hair as she pulled out his cock, dusky and thick, a touch bigger than average but nothing huge, she was thankful. He pulled and pushed her head as he taught her how and where to lick, kiss and stroke. His quite moans were music to her ears, and she loved looking up to see the pleasure on his face. He thrust a little and her eyes watered, she did as she said and tried to relax her throat but she still gagged a few times and he pulled back soothing her. He gripped her hair as he thrust shallowly and she drooled around his cock and stroked his balls. Sooner than expected he came down her throat and she swallowed, wiping her mouth as he pulled back.

He gave her water and she rested against his legs, which is when the door knocked, she stayed hidden, thankfully the front of the desk was a board of wood, so she was unseen if they stayed in the doorway. They did, and she stayed still, as the woman talked and left she took Tom, as she learned his name was, soft cock back in her mouth, she lay her head against his leg and enjoyed the feel of his soft cock in her mouth. He smiled down and stroked her hair, saying she was a fast learner, and to keep him warm. It satisfied her more submissive side, and she sat there in a warm daze.

When he started to harden again, he pulled her up, pushing her over the desk and pulling off her boots and jeans, he stroked her pussy, licking her briefly and fingering her as he moaned praise. Then he sat back and pulled her back, she worried about her weight and his on the chair, but it was solid as she slid onto his cock, leaning forward slightly and bracing her hands on the desk as she rode him. He stroked her ass, and grabbed handfuls of it as she fucked him. It felt so damn good, and she tilted her hips to hit where she wanted, his cock throbbing as he thrust up and she pushed back.

He groaned, leaning back, hands behind his head as she looked back and smirked. He slapped her ass, and after awhile he pulled out and pushed her up, pulling out her tits to palm them as he pushed her against the huge floor length window. He grabbed her hips and fucked back inside her as she moaned. Then she looked up, at first only seeing his reflection as he moaned fucking her. But then noticing a man in a big office at the building opposite, he sat in his chair and watched, she could not see his features, but it was clear he was watching when he pulled out his cock and stroked it as she moaned at being fucked so well.

She felt sucking hot, her cheek against the cold window as Tom fucked her, spanked her ass, and praised her tight, hot pussy. She came hard, biting back a scream as he carried on jack hammering into her like a rabbit. She came a second time, as he came into the condom and held

tight to her hips, nipping at her neck.

He chuckled as he noticed the man in the opposite building and fondled her breasts to show him. She was messy haired, red cheeked and so wet as she slumped on eh window. He told her she could use the attached private bathroom and she did, tidying herself up, but her voice was raw and husky, and the scent of sex thick around her, as she determined to go back to her hotel and shower. That had been just as hot as she had expected.

He never tried to kiss her thankfully, but he stroked her hips as he thanked her, slipping an envelope into her bag. He also gave her a business card, saying maybe the company could make her an exclusive deal to work there instead of the agency, she agreed to think it over. With a flick of her long hair and a sweetly seductive smile she left his office, ignored the glances as she walked out, and when she was back in her hotel room, she pulled out the thick envelope.

She had no idea if the amount was normal or not, but she laughed and threw it in the air, she had fulfilled one of her bucket list fantasies, and made a hell of a lot of money in just a couple of hours.

She was only in this city a month, but she considered his offer, imagine, making this much money, and enjoying regular hot sex straight from her fantasies. But she would have to check more details, would she only fuck him? Would she be fair game for any of the managers?

Who knew, but her imagination run wild, and she couldn't wait for the next time she set foot in that high rise office!