Days Off with Lindsay - Megan Pt. 03

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The game gets more intense, and a little personal.
7.5k words
4.74
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8

Part 3 of the 4 part series

Updated 06/10/2023
Created 02/10/2021
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Chapter 8

Megan

We went on like that over the next few months. We had a routine now.

His rules were simple. Every morning, I was to text him when I woke up. I had to drink 2 cups of water every day. I had to eat at least two meals a day. I had to edge nightly, at least once. I had to text him goodnight. If he asked for a photo, I'd send him one. Then there was the weekly task.

Every Monday, he would give me a task. A new rule to follow. I would be released from it on Saturday. The first one had been no alcohol at the bar the days that I went. I'd had to ask Noah to make me a regular tea instead of a spiked one, and he raised an eyebrow at me, but didn't argue. The next week was no chocolate. That one had been hard. Each week it was something small, just a little something so that every time I had the urge, I had to remember that I was saying no, because he told me to.

We played on Saturdays. I learned he loved to see me struggle to resist my orgasm, which part of me hated because I hated denial, but I did my damndest. I broke after our fifth session when he was relentlessly fingering that spot at the back of my pussy and sucking on my clit. He'd found the secret combo that I couldn't resist against, and after over a month of denial, I'd come so hard I almost passed out.

The session after that had been hell. Not the most intense impact I'd ever experienced, not by far, but the hardest part about submitting to a beating for me was not being able to see his face. I wanted to see him enjoy it, and I couldn't. Still, afterwards he'd held me against his chest as I'd cried softly, rubbing cool lotion into my skin, kissing my neck, and telling me I was amazing.

"I want to see you," I'd confessed. "I want to see you enjoy me."

"Oh, Megan. I absolutely adore you." He'd taken my hand and put it against his chest, and I could feel his heart beat fast. He let go, letting me hold my hand there, and I let it trail down to his crotch, where he was hard and twitching. Eager to please and redeem myself, I'd given him the best damn blowjob I could muster, drawing it out as long as I could before I made him cum. I showed him his cum in my mouth before I swallowed. He'd laughed and kissed my forehead.

And every time I went, he left me a gift.

It was usually something small. Once it was a tiny little ring for my pinky finger, with a heart on it. It wasn't big, but it was a little something I could wear. Another time I found a barrette for my hair. Often it was new panties, pretty little thongs or lacy boy shorts or silky briefs to replace the ones he'd confiscate from me every week.

Twice he'd bought me clothes. The first time was the dress, but another time he bought me a beautiful shirt that was nearly completely backless. He really likes my back, I thought, as I'd put it on to leave. It hung on me beautifully and, for once, for a second, I looked in the mirror and believed him when he called me "pretty girl." That was his name for me. I loved it.

Once it was a WeVibe, the kind you control from your phone. That week he had me wear it every weekday evening from seven o'clock until I went to bed. I had been so horny by the time Saturday rolled around, I begged him for a beating instead of his teasing, and he'd graciously agreed, giving me the much-needed release I'd needed in a way I didn't truly want, but needed because he wasn't going to let me cum. "I'm sorry," I cried. "I wish I could. But I know I can't. I know I'll fail."

"Never apologize for being honest with me, Megan. That's rule one, remember?"

Another time, it was a journal. A pretty, leather-bound journal with an elegant cursive M pressed into it. Inside was a note, telling me to record my edging sessions, and my fantasies inside. "Be detailed, pretty girl. Don't hold back from me."

That had been the hardest challenge. I wrote several pages, honestly pouring myself out about how I didn't want to disobey him, how I wanted to please him and not ask about his true identity, but that I felt like I was missing half of him, that he was holding back from me because he could see me and I couldn't see him. I wrote about how hard it was that he relentlessly edged and teased and denied me, and how much I hated denial.

Four pages in, I realized it sounded like whining and complaining, and I apologized profusely, begging him to forgive me and insisting that I wanted nothing more than to obey. "Whatever that takes. For as long as you want. If that is really what you want."

That Saturday during our play, he'd asked me to kneel by him while he read the journal, quietly turning the pages.

"You gave up?" He asked.

"Sir?"

"You gave up trying to figure it out."

"Months ago, sir."

"Why?"

"It's part of the game," I shrugged. "I like the game."

"You just wrote earlier that you want to know."

"Well yes, but I want you to tell me. I don't want to figure it out by accident."

He chuckled, closed the journal, and took my hand, guiding me to stand. He had me sit on the couch next to him, and lay my head back, my arms extending over the edge of the couch, my back across his legs, and my legs towards the other end. He began delicately exploring my body, brushing fingers across me in all the ways and places he knew I liked.

"Why don't you tell me who you think I could be."

I blushed, but began working through my options. I said all the reasons he could be some people, and not others.

"You're not one of Lindsay's friends. They left town and haven't been back. Michael Black hasn't been here consistently because of work. Noah and Jack are both working almost every day, and I doubt either of them could break away from the bar for an hour of sex on their busiest day... Jack has a really unique voice and he's about my height, but you're taller. Noah and Jackson don't have any tattoos, but I saw tattoos on your arms and hands in the video. So I have a feeling you weren't actually in the room that first night I was blindfolded."

"Interesting."

"Plus, none of them sound like you. Your voice is... different."

He was trying to distract me by massaging my clit and gently working a finger inside me. With the way I was laying on him, my hips tilted, he was massaging my g-spot expertly.

"But I know you're here at the bar somewhere, because... well, I don't know I just... ah. Oh... fuck." while one hand played with my pussy, the other hand had inched its way up to my breast, playing and squeezing. I loved that he wasn't afraid to really squeeze me.

"I'm also a little surprised at your concern of this game changing unexpectedly," he said, his voice gruff and full of lust by now. He pulled his fingers out of me and I could hear him sucking my wetness off of them. He slid them back in, dripping wet with his spit, and I shivered in pleasure.

"What?" I gasped, barely able to focus.

I heard him take the notebook in one hand and lay it on my chest. He continued to finger me as he read.

"Sir, you have to understand, I love our game. But it's so different than anything I've ever done. You have to understand the intensity I was brought in on, being Mr. Weston's live-in slave. Although it was emotionally fulfilling, it was a constant roller-coaster of humiliation, pain, and rough sex. It's not like this. This is fun. It's easy. It's hot as hell. You make me feel special and pretty. And you make me feel like a slut without feeling like a piece of furniture. It's new and different, and I love it. But I keep waiting for the ball to drop. I keep waiting for it to change. I keep expecting to fuck it up and for a sadistic switch to flip in you. I keep expecting to disappoint you. And what happens if I figure it out? What happens when you tell me? What will the game change into? I don't want to lose this."

I bit my lip. My words and worries spoken out loud in his gruff, warm, sexy voice sounded absurd. He sighed and shut the journal, and kissed my stomach, then my chest, right between my breasts, and then peppered my collarbone and neck with little kisses.

"I told you, Megan. All I want you to do is obey, and play the game. You're not going to fuck it up."

"Yes sir."

"Is it too hard?"

"No sir... I almost feel like it's too easy. It's always been easy."

"Is that bad?"

I tried to think while he tried to distract me. Finally I found the words I was looking for. "Doesn't it take away from my submission if I just... hand it over? You just walked into a room and I submitted to you. It was easy. Simple. Doesn't that make you feel like..."

"Like it was thoughtless? A meaningless gift?"

I sighed. "Yes. That's what I meant."

"Megan, you don't know me. You were given no information, no guidance, no warning, and you gave yourself to me like it was your job. You did that because you trust that I am not going to hurt you, despite the fact that you don't know me. That is very special to me."

"Reuben wouldn't set me up with someone he didn't trust."

"And you trust me only because you trust him?"

"Well... I did at first. But you've proven to me that I can trust you as well."

"And you've proven to me that you will do as I say, no matter how hard it is for you. Do you know why I make you wear a blindfold, and change my voice when I'm around you?"

I felt my eyes widen and blink under my blindfold. "You-you change your voice?"

He laughed. "Of course. Otherwise we couldn't play the game."

"I... oh."

"I do it because you told Reuben the thing you were missing in those other relationships was the connection. You didn't want it to just be submission. You wanted the connection. You like rough sex. You like getting fucked. You like cuming multiple times until you're spent. And I have been nothing but gentle, and I am keeping from you everything you want, and haven't given you permission to cum in nearly four months, and you are choosing to submit to me anyway. Isn't that sadistic enough for you?"

I felt my mouth quirk into a smile. He was right. He was giving me some of the best pleasure and worst pain I'd ever had, and I was loving it, and was desperate for the rest, and he was keeping it from me, stringing me along. Would I ever get it? "I never said I wanted you to be sadistic."

"You dated one for three years."

"Exactly. Will you... will you ever tell me who you are?"

He leaned forward and kissed me softly. "Of course I will, pretty girl. But not yet. I'm having too much fun. Aren't you?"

I smiled and whispered, "yes sir," against his mouth and kissed him back. A whole new level of understanding had settled onto me, and I basqued in that little hit of my favorite buzz of submission. If he wanted to keep this from me, so be it. All I had to do was do as I was told.

"You know another thing you wrote in your notebook, is that we haven't really fucked." I felt giddy when he said it. Was he finally going to fuck me? I'd had his cock in my mouth several times now, and I desperately wanted to feel him fill me up.

"Will you please fuck me, sir," I whispered quietly. I felt myself clench at the thought, and tighten around his fingers. I ached for release.

"Don't worry, pretty girl. You'll get yours."

He edged and teased and denied me for another decade, or so it felt. I was getting so close, but I managed to hold off by the skin of my teeth. Finally he eased his fingers out of me, and gently held them up to my mouth. I sucked them off, relishing the feeling of his fingers in my mouth and on my tongue.

That day, he didn't leave me a gift. I felt a little confused, and a little hurt. Had I said something? Or done something wrong? But I left the playroom and went out to the bar, and ordered a drink.

"Hey, you okay?" Jack asked me as I sat at one of the stools. I didn't really want to sit with my friends until I had gotten my head back on straight.

"Yeah, I'm fine. Just need to clear my head."

Jack made my drink a little stronger than normal. I watched as he expertly poured out the liquor, knowing exactly how much to pour into the glass from the years spent measuring, and then looked at me and gave me another few splashes. I laughed.

As I watched him, I noticed his hands. They were definitely big, and he had some muscle tone to his arms. I tried to remember if I'd ever seen his forearms without his long whitesleeved button-down shirt. I was sure he'd worn his sleeves rolled up before, but lately, both of the bartenders had been wearing their sleeves down. Had my Sir asked them to do so? Or was it one of them?

I sipped my drink and scrolled my phone, not really seeing or absorbing anything I was looking at, so I noticed right away when I got a text from him.

Sir: Close your eyes.

My stomach clenched and I set my phone down, folded my hands in my lap, and closed my eyes, keeping my head facing forward. I felt it when he came up behind me, and placed his hands on my shoulders.

"Did you think I forgot something?"

"I... no sir, I didn't think you forgot."

"But I didn't leave you a gift today."

"No sir."

"Why not." It wasn't his usual playful tone, it was more serious, and it wasn't a question. Think, he was telling me.

I bit my lip, but took a steadying breath and said the words I didn't want to say. "I didn't earn it." The words hurt because I wasn't sure what I'd done. Where had I messed up?

"Oh, Megan." his lips brushed my ears. "You don't earn gifts. They're given." His hands left my shoulders and he straightened, but didn't leave. "Listen. Breathe."

I listened. At first it all just sounded like background noise, but as I focused, I could hear the voices of my friends. I could pick out each one of their voices and see their faces. I could hear the clinking of glasses, and the soft moans of Jenna and Sarah in the corner, one of them being pleasured quietly under her skirt. I could hear the bartenders and a waiter or waitress behind the bar, mixing and stirring.

I could hear his breathing. I could feel his breath rustle my hair and brush against my neck.

I could hear my own shaky breathing. I focused on it, relaxing and letting it even out.

Then I heard him move. I couldn't tell what he was doing, but I felt his hands near me. And then something cold against my neck.

Oh. Oh my god. I gasped a little and my eyes fluttered, but I clamped them shut. There was a mirror on the other side of the bar. If I opened them... But I'd promised I'd wait. I wanted the game. So I kept them glued shut.

He was buckling a collar around my neck. "Do you know what you've done to earn this?" he said softly.

I could hear the blood rushing in my ears. "No sir. I don't." I felt like I'd barely done anything.

"Yes you do. Text me when you figure out how to say it... maybe soon you'll earn the lock." He kissed the back of my neck, and then my cheek, and then the very corner of my lips, and then he was gone. I waited for some time, making sure he was really out of sight before I let my eyes flutter open. I could feel the smile on my face, but it didn't truly register until I looked across from me in the mirror of the bar and saw that gorgeous collar around my neck.

It was about an inch thick, dark red leather with small loops on it that held a brushed black chain that wove through the loops, rivets holding it in place. I felt my fingers brush against the chain links and the soft shiny leather. The buckle on the back had small D-rings attached so it could be locked shut.

I saw Julia come up behind me and hug me, grinning wildly. "It looks so good on you," she giggled.

"I knew it was one of yours," I said.

"Can I take a picture of you wearing it? It looks so good against your chain tattoo. Man he had the right idea with that black brushed steel."

I agreed and moved my hair off my back, and let her take a few photos of me. She sent them to me so I had them. Becca also came over and congratulated me, giving me a quick peck on the forehead. "I'm so excited for you," she said. "Have you figured it out yet?"

"I'm not going to," I said, and then I realized what he had meant when he said I knew what I'd done to earn it. I had given up, chosen not to look, not to try, not to keep wondering. I had chosen to forgo knowing his true identity simply because he had chosen to keep it from me. And I'd chosen to submit to him even though he was keeping everything I wanted from me.

Peace settled over me, and I sent him a text.

Megan: I get it. I'm playing the game the way you want me to play it. Thank you, sir. I love my collar. And I love this. And I think, maybe, I kind of love you a little.

Sir: I think I kind of love you a little, too, pretty girl.

Then I took my drink, waived to the boys behind the bar, and went to the couches to sit by my friends.

Chapter 9

Megan

Saturdays were my favorite day of the week anyway, but any day I went to Reuben's and got to sit with my friends, knowing maybe my Sir was watching me, filled me with excitement. It was better than a secret admirer. It was a secret lover that everyone seemed to know except me.

It was too cold to wear my pretty burgundy dress, but we were having a Christmas party in the Lounge, and it was his favorite piece, so I wanted to wear it that night. I wore a pair of black floral fishnets underneath and a pair of black suede ankle boots, and my heavy double-breasted coat on top to keep me warm. He'd given me a scarf last week as a gift. It wasn't anything fancy, but it was soft and warm and looked so pretty with my black wool coat. Part of me wondered if we would play that night since the party would start at seven and probably go all night.

That evening, there was a lot of booze, a lot of laughter, and a lot of swearing. There was also a lot of sex. Jenna came out of nowhere wearing a strapon and holding a hitachi and chased Abigail around the room, finally being aided by Paul and Becca as she was caught, held still, and royally fucked. Tanya wore the hottest latex corset and skirt I'd ever seen, the black material glistening under the light as she danced and gyrated on a pole that had been installed, putting herself in a position that would allow anyone to come up behind her and have access to her. Sam was tied up and suspended just high enough off the ground that he could be used as a coffee table, and use him we did.

Jack and Noah both wore different colored shirts that day instead of their normal white; Jack wore dark green and Noah wore red. Jack looked like an elf with his long straight black hair pulled up into a bun, his ears just slightly pointed at the tip. He also wore a green santa hat. Although he looked festive, he looked proudly and purposefully ridiculous, like he was doing his best to look as absurd as possible. Noah's red shirt was almost a wine color, and he wore a set of reindeer antlers with bells that made him look absurd. I giggled hysterically when he shook his head side to side and jokingly pranced around. He reached up to adjust his antlers, and I saw his sleeve ride up on his left wrist just a little. No celtic knot tattoo, I realized. I'd already known neither of the bartenders were my Sir, but the lack of the tattoo was further confirmation.

There was also a beautiful Christmas tree in the corner of the room, lit up with a thousand lights and beautiful black and red ornaments. People had brought gifts for each other, and although he wasn't there that night, almost every member of the club had received a small gift from Mr. Weston, and he'd allowed for a certain number of free drinks and food for us that night as well. We sat around the tree close to eleven o'clock and exchanged gifts, the bar boys coming to sit with us as well for a few minutes to rest and have fun.