Charles Briggs thought over what had occurred as he drove home. He’d always been attracted to Emily, and was looking forward to growing his relationship with the sweet, intelligent woman who had so willingly exposed herself to him this evening. He licked his lips, still tasting her lipstick, and feeling the way her skin had yielded against his hands and his teeth.
He thought of all the delights he wanted to show her, to corrupt her a little. To gently - then not so gently - violate that sweet nature. To make her his. He wondered what she would think of the item in that box. Her answer to his rather pointed question made him think that she’d be mortified but curious, and that made him smile. Whether she’d do as the enclosed card requested is something he’d have to wait until tomorrow to find out.
The thought that she would, made him have to adjust his cock in his pants. God, she had such an incredible ass. Heart-shaped, with creamy cheeks he longed to mark with his hand prints, and later, with sterner implements.
He had wanted her from the moment he’d interviewed her. But her despicable boyfriend had always been in the way. He’d met the man at an office party, and realized what an insecure boor he was, when he’d taken Charles aside, and basically warned him to keep his hands off Emily, then later on was seen flirting with another attractive female employee, while a humiliated Emily looked on.
When he’d heard through the office gossip pool that they’d broken up, he’d understood the reason she was upset, but had wanted to hear it from her. While he felt a bit guilty for pursuing her so soon after the breakup, while she was still so vulnerable, it was that vulnerability that turned him on.
He pulled into his driveway, and parked the car in the garage. Entering his house, he headed to the liquor cabinet, and poured himself a Scotch. He turned the oven on to preheat it for dinner, and went to the bedroom to change. He came back out, found the oven hot, and popped in one of the prepared meals his housekeeper had left for him. Grabbing his drink, he went into the den. He sat down on the overstuffed sofa and sipped his drink as he thought of thought of Emily on her knees in front of him, slowly pulling down his sweatpants to free him, and using her pretty mouth and tongue to worship his cock.
He reached his hand inside his pants and gripped his rapidly hardening cock, stroking it in time with the imagined bobs of her head as she slowly worked his cock down her throat. He wondered if she was trained in that particular skill. He almost hoped not, wanting to be the one to do it. He imagined her crawling up on top of him, straddling his body, and slowly sliding her pussy along his length before raising herself up, and slowly sliding him into her. Gyrating her hips, putting on a show. The strength of this fantasy had him coming just as the timer went off on the oven.
He padded into the kitchen, and grabbing a hand towel, he wet it in the sink and cleaned himself off. He threw the towel into the laundry room, and took his dinner out of the oven. He smiled as he tucked into the delicious food, amused at the effect the thoughts of her were having on him. He couldn’t wait to have her for real.
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Emily’s legs still felt a bit unsteady as she walked down the stairs to the subway station. Her train arrived, and she got on and sat down gratefully. She turned the small box around in her hands, wondering what was inside. Mr. Briggs had said to wait until she got home to open it, but she was so curious. She looked around the train car, and as no one was really around her, she undid the ribbon holding it closed, and took off the lid.
Nestled inside the satin lining was a shiny silver butt plug with a purple crystal decorating the base of it, and a small envelope. She blushed at the sight of it, took out the card, and hastily closed the box. She slid her finger under the flap of the envelope, releasing it, and pulled out the card inside.
“I want this inside you tomorrow.” was all it said. She bit her lip...she’d never had anything bigger than a finger up her ass before, and while this plug wasn’t overly large, it was certainly larger than anything she was used to. When her train got to her stop she got off, and once she reached street level, headed toward the nearby drugstore. If she was going to try it, she knew she’d need some lube. Thankfully she needed a couple of other things too.
She walked in, and grabbed a shopping basket. She picked up the items she needed, then headed toward the feminine needs aisle. She found a small bottle of lube, and tucked it in with the rest of her purchases. Thankfully there was a woman at the cashier’s counter, and she didn’t look twice at what Emily was buying, and rang her up quickly.
After she paid and left, she headed toward her apartment. She was too wound up to cook, so she stopped and got a burger and fries to go from the fast food place on the way home. Once inside she sat down and ate her dinner. After she cleaned up, she slid the box from her bag, grabbed the bottle of lube, and went to the couch.
Emily took out the plug, and contemplated it. It was perfectly smooth, with a rounded tip. The bulb of it was pear shaped, the neck of it very narrow until it flared out at the base. The gem at the end wasn’t cheap plastic...it was cool to the touch, and felt like real lead crystal. It was beautiful in its own way, like a piece of jewelry. She smiled...purple was a favorite color of hers, and she wore it often. It was obvious from the color of the gem that he’d noticed.
She hastily undressed, and knelt on the cushions with her legs spread, gripping the back of the couch. She was still wet from earlier, and newly turned on. She stroked her pussy, delving her fingers inside. When they were good and slick, she slid one of them into her ass. She gasped as she moved it in and out, fantasizing that it was Mr. Briggs behind her, that it was his finger. As she got used to the feeling, she added another finger, stretching her rosebud, and trying to relax it.
She reached down with her other hand for the lube and the plug, and put them on the back of the couch. She grabbed the lube, and unscrewed the lid with her teeth, then reached back and drizzled some down her ass crack. With her fingers nice and slippery, she found herself beginning to ride her fingers, feeling her juices start to slide down her thighs. It began to feel more comfortable, and somewhat amazing. She slid her other hand down her front, and began to stroke her clit as her fingers worked her ass.
Emily imagined Mr. Briggs behind her, leaning over her, plundering her ass with his thick fingers as he whispered in her ear how much he wanted to fuck her ass...to pound his cock inside her until her legs got so weak she couldn’t stand.
She came with a shout, startled at the feeling of her ass contracting around her fingers. She withdrew them slowly, and in a bit of a daze went to the kitchen to wash her hands, and clean herself up a bit. Taking a towel with her, she then went back to the couch and resumed her previous position. She lubed up the plug, and again teased her back hole with her fingers for a bit, noting the angle they were inside her. Taking them out, she wiped them on the towel, then taking the plug she put the tip against the ring of muscle, and slowly worked it inside. It was easy at first, but as the plug widened, she felt herself contract. She forced herself to relax, and took in a deep breath. As she blew it out slowly, she pressed the base of it again, and it suddenly all went inside, until just the jeweled base nestled between her cheeks.
She sat up a bit...it felt so strange inside her. She stood up slowly, and took a few steps, wondering if it would be something she could wear all day. She took a lap around the living room, and while the feeling that it was going to come out finally subsided, she was still very aware that it was there. She imagined having it in all day would leave her in quite a state, which she assumed was the point.
She decided to leave it in until bedtime, and went about her usual evening routine. But no matter what she did, she was constantly aware of it. When it was time for her to go to bed, she was almost relieved. She took it out carefully, washed it thoroughly, and put it on the sink to dry.
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When Charles walked in the office the next morning and went past Emily’s desk, he was amused to see her in a purple blouse, with pretty amethyst earrings peeking out from behind the tendrils of her updo. She glanced up at him and gave him a shy smile as he passed, but didn’t say a word.
Their day went as normal. As she was in and out of his office, he tried to guess from the way she moved if she had the plug in, but he couldn’t quite tell if she did or not. It made waiting for the end of the day - and his cock - that much harder.
When five o’clock came around, and the office emptied, he waited impatiently at his desk for ten minutes before buzzing her phone. When she answered, he gave a curt command for her to come to his office. When she came to the doorway, he gazed at her admiringly. She was so stunning, with her jet black hair and blue eyes, and the purple blouse set off her coloring so well. He waved her in, and she closed and locked the door behind her.
“Close the blinds, too,” he murmured.
She did as he requested, and came back to stand in front of his desk.
He leaned back in his chair, “Undress...and take down your hair.”
Emily’s face was serious as she removed her blouse and skirt, and draped them over a chair. She removed the black lace bra, and before removing her panties, took the combs out of her hair and let it fall in black waves down her chest and back. As she hooked her thumbs in the waist of her panties, he stopped her.
“Not yet. Turn around first.”
She gave a knowing smile, and did as he asked. She slid them teasingly down her ass, and bent over to pull them down further, showing that she did indeed have the plug in. He inhaled sharply as it was exposed. Like a shot, he stood up and was around the desk. He spun Emily around, and bent her over the desk, kicking her legs apart. He delved his fingers between her legs, and moaned as he felt how wet she was. He ran his hands up her back, then down to cup her buttocks, marveling at the feel of her silky skin against his palms.
He bent over, and put has hand around her neck, his lips close to her ear, “I want to turn this ass of yours a lovely shade of red. Would let me do this?”
Her breath hitched as she replied, “Yes, Sir.”
He stood up, and expertly smacked her left cheek. She raised up on her tip-toes, letting out a small cry. He smoothed his hand over that spot, feeling the skin begin to warm. He then repeated these actions on her right cheek. He gave her ten spanks, scattering them across her ass, until it was covered in a rosy blush.
He leaned over again, “Before we continue, I need a safe word.”
She let out a ragged breath, “Violet.”
“Noted. I’d like to give you ten more, would that be too much?”
Emily shook her head, “No Sir. Please...I want more.”
He stood up straight, and grabbed her hair, wrapped it in his left hand, and pulled slightly, causing her to arch her back, and lift her ass even higher. He rained down ten more swats, feeling her hot skin, damp with sweat. Her body was trembling, and his fingers explored between her legs again, stroking her clit. She bucked back against him, and he growled, “Stay still.”
She did as he asked, and when he felt her body tense, he stopped. Emily let out a sob...she was taut as a violin string in his hands, and desperate to come. He reached for the base of the plug, and pulled on it gently. She bucked back again, and he gave her ass a hard smack. She moaned, and tried to settle. He moved between the plug and her clit...playing first with one, and then the other.
“What do you want, Emily?” he asked.
“Please, Sir...I want you to fuck me,” she replied breathlessly.
“You don’t want to come?” he teased.
“Yes, Sir! I want to come too!” she cried.
“You’ll have to earn it. Turn around and get on your knees.”
She did as he asked, but instead of feeding her his cock as she was expecting, he sat down in the chair, and undid his pants. Pulling out his cock, he began to stroke it. “Play with yourself. I want you to edge yourself three times. If you can do that without coming, I’ll give you the fucking you’re craving so badly.”
He watched in fascination as she stroked herself, pinching her nipples, and fingering her pussy. Three times she got right to the brink, and he watched raptly to see if she’d climax, but she always stopped just before that happened. Part of him was disappointed. He would have loved to have had her suck him off, and then leave her hanging...desperate, plugged, and dripping. But the other part was thrilled that he’d finally get to own that cunt of hers.
He gripped her arm and hauled her up, once again draping her over the desk. Leaving her there for a moment, he went behind his desk and rummaged in his top drawer, taking out one of the condoms, and some lube that he’d stashed there this morning. He slid the condom on, and dripped a few drops of lube around her back entrance, spinning the plug, and getting it nice and slick. Without warning, he shoved his cock into her pussy, causing her to cry out. And this time when she bucked back against him, he let her. With the plug in, she was so tight, and felt so full.
And she was so very wet. He wrapped his arm around her neck, and pulled her up against him. “Come on my cock,” he ordered as he hammered into her, his fingers stroking her clit. She came almost instantaneously, contracting along his length, and around the plug. He continued to pound her mercilessly, and her hands came up and wrapped around his arm, holding on for dear life. She came a second time, crying out, and he felt her legs start to wobble. He eased her back down onto the desk, and slowed his thrusts. He gripped the base of the plug, and worked her holes. As his cock went in, he pulled the plug partially out. When he pulled his cock out, the plug slid back in.
Emily went boneless, overwhelmed with feeling of being double penetrated, and sobbed tears of joy and pain. When Charles pulled the plug out and put it aside, she assumed he was going to fuck her ass, and she found she was desperate for him to do so. She reached back and spread her cheeks in invitation, but he just chuckled, “Not today, my dear...this was just a preview.”
He picked up his movements again, driving into her, until he came with a groan. He collapsed on top of her, and rested there a moment, relishing the feel of her against him. He kissed down her back as he pulled out of her and stood. He opened the office door and peeked out...all was clear so he went to the men’s room and neatened up. He wet some paper towels, and went back to his office.
Emily was still resting on the desk. She jumped slightly as the damp, slightly rough towels touched her sensitive mound. Charles cleaned her up a bit, and helped her stand. He turned her around, and wrapped her up tightly in his arms. Overwhelmed, she shook as she cried a little. She was suddenly exhausted.
Charles sat her down in the chair, and helped her get dressed. He kissed her gently, “Get freshened up...we’ll go get dinner.” She gathered up her things, and went to the ladies room. She washed the plug, and wrapped it in some paper towels so she could put it in her purse, straightened her clothes, put her hair back up, and touched up her makeup as best as she could. She met him in the hall, and they walked to her desk to get her things. As they got the elevator down, he kept his hand gently on her lower back, and led her to his car once they reached his level of the parking garage.
They went to dinner at a small and intimate place he knew of. The food was simple but good, and they shared a bottle of wine as they ate. They chatted amiably and easily, getting to know each other better. He managed to finally get her to call him by his first name, and by the end of their meal they were laughing and talking openly about many topics. He was charmed by her wit, her innocence and beauty, and felt disappointment at having to take her home.
But he drove her back to her place, and walked her up to her apartment. They stood in the hall, she leaning against her door, him standing close to her, and said their good nights. Before she went in, she looked at him with a little twinkle in her eye, “There is no Benedict Proposal, is there Charles?”
He laughed, and gave her a lusty kiss, “No, there isn’t. Are you OK with that?”
She smiled brightly, “Absolutely. Good night, Sir.”
“Good night, darling. Sleep well.”
