by Nikki Wild
Say yes, Chloe, I reminded myself. That’s the promise I made to myself earlier and if there ever were one of those things that I might regret not doing later, this was it.
I had a slightly panicked thought as I wondered how I was going to get it out later, but I pushed the thought away. I wasn’t the first person in the world to wear one of them, surely it couldn’t be that hard.
At least I hoped not. A quick flash of myself at the emergency room complaining of a trapped bedazzled My Little Pony butt plug in my ass shot through my head and I opened my mouth to protest again.
“Sit down,” he demanded. I hesitated, wondering if that was even possible. I went slower this time, much slower, wobbling over to his desk like a penguin.
“Do I really need to sit?” I asked.
He smiled softly and nodded.
“You’ll be okay. Trust me.” Trust him, huh? He wasn’t the one with a unicorn up his butt.
I nodded, sitting gently in the chair in front of his desk, barely perching my ass on the edge. I sighed with relief when I realized it didn’t hurt. In fact, I only felt it when I moved in certain ways and there was something mischievously forbidden about it. I sat down fully on it and my eyes shot open as the feeling went right to my clit again.
It felt so deep, so hard, and I knew I wouldn’t be able to think about anything else the entire day.
“That’s my girl. I knew you’d like it,” Bear winked. “I have something else to give to you,” he said, sliding a gold credit card across to me. I leaned over carefully, picking it up. It had my name on it.
“What’s this?” I said, breathlessly.
“It’s yours. Spend whatever you need to spend.”
“On what?” I asked, shifting gingerly in my seat.
“On whatever you need, darling. Clothes, furniture, anything.”
“Why are you doing this?” I asked, squirming.
“Doing what, Chloe?” he asked, his eyes smoldering as they stared deeply into mine. He was so serious, so casual about this whole thing.
“Everything, Bear. The apartment. This credit card. The job, whatever it is…”
He cocked his head, staring at me thoughtfully before replying. The tension hung thick and heavy in the air between us.
I’d let this man touch me in places I’d never let anyone else touch. And he’d given me things I’d never imagined. And yet, I had no idea why in the world any of this was happening to me.
“The limo is waiting downstairs,” he whispered, his low, smoky voice sliding over my ears like velvet. “Go shopping. Buy clothes. Lingerie, lots of it. Black is my favorite, and it would be in your best interest to please me, Chloe.”
“You didn’t answer my question,” I prodded, swallowing hard with nervousness.
“No, I didn’t,” he smiled, standing up and walking over to me. “Tell you what. At dinner tonight, you can ask me anything you want, okay?”
“We’re going to dinner?” I asked.
“Yes, didn’t you hear me tell Sarah to make reservations? It’s a very upscale place, so make sure you buy something appropriate. I’ll pick you up at seven.”
“Okay,” I said, my head spinning. “But what about my job?”
“Chloe, this is your job.”
“What is?”
“Beautiful,” he said, leaning down and brushing a kiss across my lips. “Don’t you see? It’s your job to please me.”
“So, I’m a glorified prostitute?” I asked, brazenly. A little too brazenly for someone with a sparkly pink butt plug shoved up their ass, actually. Bear wasn’t fazed by it though. Instead, my boldness seemed to amuse him.
He smirked. “Of course not. I’m not paying to fuck you.”
“Then what are you paying me for?”
“I’m not paying you. I’m taking care of you. Haven’t you ever had anyone take care of you before, Chloe?”
“Not like this,” I replied.
“Have you ever had a boyfriend, Chloe?” he asked.
“Yes,” I replied, Harlan’s face flashing in my head. I hadn’t thought of him at all since I’d arrived. Hell, I hadn’t really thought much of him at all since I met Bear. “He was awful.”
“That’s what I thought. He treated you badly, correct?”
“He was selfish and arrogant,” I replied.
“Ah, a man after my own heart,” he laughed. “Well, you see, Chloe, I want to give you more than that. Do I have my own selfish reasons for making you happy? Of course I do, I won’t deny that. But it seems you need me as much as I need you.”
“I don’t need anybody,” I said, raising my chin defiantly.
“You need experiences, Chloe,” he said. “You need to live, don’t you?”
“Yes, but —,” I began.
“—then give me a chance,” he interrupted. “Give me a chance to show you things you’ve never seen before. Give me a chance to show you what your body can do, to guide you into a world that you can only dream of. All you have to do is trust me.”
He paused, smiling down at me confidently. He was so fucking handsome, so incredibly sexy, and maybe that’s what it was, or maybe it was the fact that he’d already taken me to places I didn’t even know existed within myself, but I couldn’t help myself.
“You do trust me, don’t you, Chloe?” he asked, his eyes peering so deeply into mine I thought I might never come up for air.
“Yes,” I whispered. “I do.” I had no idea why I trusted him, but I did.
The smile that he beamed down at me left me breathless.
“Wonderful!” he exclaimed, reaching for my hands and pulling me up from my chair. “You’ll see, Chloe. This may not be what you expected, but it will be so rewarding in the end.”
I nodded, speechless, still lost.
He kissed me again, pulling me close in a firm embrace before gently pushing me away.
“Now, go. You’re making me hard again and I have a meeting in five minutes.”
“Okay,” I nodded. “But I can really ask you anything tonight?”
“Anything, beauty, I’m an open book,” he said.
I took a deep breath, squaring my shoulders and nodding.
“Alright,” I agreed. “I guess I’m off to go shopping.”
“Good girl,” he said. “Max can give you suggestions on where to shop. Buy anything you want.”
“Thank you,” I said, walking towards the door, the plug rubbing deep inside of me with every step.
“Oh, Chloe?” he said as I reached the door. I turned back, drinking in his sexiness one last time.
“Yes?” I smiled.
“Don’t bother buying panties, darling. You won’t be needing them.”
My mouth opened in surprise and was met with his laughter.
“See you at seven!” he exclaimed, his eyes twinkling.
I turned away, shaking my head. I walked out to the reception area, avoiding Sarah’s eyes the entire time, sure that she must know exactly what was going on under my skirt and doing my damnedest not to blush.
It didn’t work.
Chapter 9
I walked out onto the cold New York streets, the wind and snow whipping around me, the frenzied rush of people speeding by so fast that I struggled to make it across the sidewalk to the waiting limo.
“Ms. McDonnell,” Max nodded at me as he opened the door.
“Max,” I said, turning to him before he closed the door behind me. “I need to go shopping, but I don’t have any idea where to go. Somewhere upscale,” I said, parroting Bear’s words.
“For clothes, ma’am?”
“Yes,” I replied.
“I know just the place,” he smiled, before closing the door and running around to the driver’s side. We pulled away from the curb and I leaned back in the seat.
My body had adjusted to the plug by now and the intensity of the sensation had lessened enough that with a little luck, I wouldn’t make a fool out of myself. I couldn’t believe I was doing this—going out in
public like this. The entire situation was surreal.
I jumped when I felt my phone buzzing in my suit pocket. When I saw it was Marie, I smiled. She was exactly the person I needed to talk to.
“So?” she asked, not bothering with a greeting at all, just like always. “How’s New York?”
“It’s incredible. Bear’s given me my own apartment, just off Central Park!”
“You aren’t staying with Matilda?”
“Well, I thought I was going to, but no. Bear gave me my own place.”
“How’s everything going with him? Did he tell you what your job is?”
“Um…,” I hesitated. “Well….”
“You fucked him again, didn’t you?”
“Oh my god, Marie,” I said, my words rushing out of me like a river, as I lowered my voice. I wasn’t sure how much Max could hear through the glass panel separating us. “He’s amazing.”
“I’ll take that as a yes?”
“Yes. Twice.” She squealed and I pulled the phone away from my ear.
“I can’t believe you’re fucking your boss!”
“Neither can I,” I said, smiling. “He’s quite a gentleman, actually. When he’s not fucking me, that is.”
“He isn’t a gentleman when he’s fucking you?”
“Hardly,” I scoffed. “More like a fuck machine. He's so dirty, Marie! He made me give him head while his assistant was in the room!”
“What!” she yelled.
“I know!” I said. “And… he gave me a gift.”
“What kind of gift?”
“Marie, you won’t believe this,” I said, squirming as the plug sent jolts of pleasure through me.
“What is it?”
“Have you ever used a butt plug?”
Her laughter roared through the phone like a tornado.
“What! Sure I have,” she said.
“Of course you have,” I said. “I forgot who I was talking to.”
“So he gave you a butt plug? What the fuck kind of gift is that? He’s a billionaire, he should have given you diamonds!
“It does have diamonds. Pink ones, on the outside.”
Her laughter was contagious and I couldn’t help but chuckle.
“I’m wearing it right now,” I whispered, hoping to hell that Max couldn’t hear me.
“Now?” she cried. “What the hell? Where are you?”
“I’m in the back of Bear’s limo on my way to go shopping. He also gave me my own credit card.”
“Holy shit, Chloe! You hit the fucking jackpot!”
“I guess so,” I replied.
“Why aren’t you more excited?” she asked.
“I don’t know,” I sighed. “He’s just such a mystery. He won’t really answer any of my questions. I guess I don’t have a real job, not that I can tell so far, except fucking him and doing what he tells me to, apparently.”
“Look, I saw this man’s picture, remember? Fucking him can’t be that bad.”
“It’s not bad at all,” I replied. “It’s just not what I’m used to.”
“Speaking of what you’re used to, Harlan called me looking for you.”
“Did you tell him I moved?”
“No. I didn’t answer his call. He left a voice mail asking for information about you.”
“Don’t tell him anything. I’m avoiding him completely.”
“I would, too, if I had a rich new sugar daddy,” she laughed.
“Don’t call him that!” I said.
“What should I call him, then? Your boyfriend?”
“No, I don’t think that’s appropriate either. I have no idea what to call him.”
“Does he make you call him Daddy?” she laughed.
“Shut up! No, he doesn’t,” I said, laughing with her. “I just call him Bear.”
“Well, whatever, I call him ‘hot’,” she said. “He must be a total freak in bed.”
“That’s an understatement,” I said.
“So, wait a minute…you’re going shopping right now and he’s making you wear a butt plug the entire time? That’s so…perverted.”
“I know,” I admitted.
“Does it feel good?” she asked.
“In more ways than one,” I replied.
“Take a picture and send it to me!” she said.
“What! No, are you insane?” I asked. The car slowed to a stop and I looked out the window and saw that Max had brought me to Bergdorf Goodman’s. “Marie, I have to go, I’m at Bergdorf’s now.”
“Bergdorf’s! You bitch!” she teased.
“Eat your heart out,” I said, so happy she’d called. Her laughter was the best medicine.
“Alright, alright. Look, Chloe, you deserve this. Let go. Enjoy everything. You only live once, you know. Don’t be such a prude.”
“I don’t think being prude is an option at this point,” I said.
“Good!” she replied. “Keep me posted. And um, Chloe?”
“Yes?”
“I wear a size seven in Louboutin’s. Christmas is right around the corner,” she reminded me.
I laughed and shook my head.
“Yeah, yeah,” I said. “I’ll call you soon. Love you!”
“Love you, too! Size seven!”
I hung up the phone feeling lighter than I had since I’d arrived in town. Marie always had that effect on me. Her perspective was always a little skewed but she managed to see the bright side of things most of the time.
I walked into the store, my step a little lighter, despite the pink ring pop stuffed inside of my butt. Another shiver of pleasure shot through my body as I gazed at the huge, golden Christmas tree shimmering at the entrance to the store.
I looked around at all the people rushing past me and grinned at my private secret.
I spent the rest of the day shopping, silently thrilled at my secret adventure, my body tingling with pleasure as Bear’s face stayed front and center in my mind with each step, thanks to the plug.
By the time I made it back home to my apartment, I was exhausted and I’d put a serious dent in Bear’s credit card.
I’d had five separate orgasms, in five separate dressing rooms.
Trying on clothes had never felt so fucking good.
Chapter 10
The view from my terrace was stunning. I sat at the little table out there, sipping wine and staring down at the tops of the trees in Central Park. Lights glittered around the city, sparkling like little diamonds adorning all the shops and cars and buildings. My neighborhood was bustling with activity and the energy that sizzled through it was exciting, but exhausting at the same time.
Bear was picking me up in an hour for our date and I was incredibly nervous. All of our interactions up till now had been quick and rushed. Sitting down with him over dinner was going to be a completely different experience. It would be intimate, in an entirely different way than having sex with him had been.
He’d texted me shortly after I’d gotten home today, giving me permission to remove the plug. I’d been so relived after wandering around with it all day and wondering just how long he would force me to wear it. Getting it out proved to be an adventure all its own but I’d finally succeeded after a few bungled attempts.
I’d gotten so excited taking it out, that I’d collapsed on my bed afterwards, my fingers bringing me to orgasm again. I’d been coming all day.
It was all too much. Too much physically, too much mentally. He’d managed to mind fuck me all day and he wasn’t even there.
It was the most erotic thing I’d ever experienced. He’d crawled into my mind without me realizing it.
And yet, here I was, still going along with his games like an obedient puppy. If I had a tail, I’d be wagging it just as excitedly as any puppy would be, too.
It was obvious that Bear loved games. And now, it was apparent that I loved Bear’s games just as much. The fact that he’d warned me that we were just getting started only added to the excitement.
I took a sip
of my wine, the ruby liquid doing nothing to quell the nervousness running through my veins as I tried to imagine what Bear had in store for us tonight. Somehow, I knew he wasn’t going to just stop at having a nice dinner together. So far, he’d been full of surprises at every turn.
My phone buzzed and I glanced down, sighing when I saw it was my Mother calling. I’d managed to get through the entire day without talking to her.
“Hey, Mom,” I answered.
“Chloe, how was your day?” she asked.
“It was okay,” I said, glad she wasn’t here to see the blush that crept up my neck.
“What did you do?” she asked.
“Just a little shopping. What did you do?”
“I had the longest meeting of my life with the Board of Directors. Then, I went back to the office and met with my assistant for the rest of the afternoon to get things in order for the rest of the week. I’m giving a presentation on my proposals for the company on Friday. It’s going to be a long, busy week.”
“Sounds like you’re right in your element,” I replied.
“That’s true,” she laughed. “I loved every minute of it.”
“I’m glad you’re happy, Mom,” I said.
“I am. Although, I have to admit, I’m not really happy with our living situation. It would have been much better to come home to you.”
“I like my apartment. It’s best we have our own space, Mom,” I replied.
“I suppose so,” she sighed. “But we have to promise to see each other as often as possible, okay?”
“Sure,” I replied.
“How about tonight? Let’s go find someplace to have dinner.”
“Oh, I can’t, Mom,” I replied. “I’m having dinner with Bear.”
“With Bear?” she replied. I could almost see her eyebrow raise through the phone.
“Yes, um…,” I hesitated. “To talk about the position he has for me,” I lied. The only positions I expected Bear to have for me included missionary and doggie.
“Oh, I see,” she said. “Well, that’s good. I hope it’s something where you can use that degree of yours. I’d hate to see your talents go to waste.”
“I wouldn’t worry, Mom,” I replied, blushing again as I thought about the new talents I was acquiring. Not everyone has the skills to wear a butt plug all day and I figured that had to count for something valuable later in life. “It’s not like I’m going to work for him forever, whatever it is.”