by Jamie Knight
I took a moment just to appreciate it. Stroking her outer lips gently with my thumb, I made Macy hum and squirm with pleasure. She was already wet. I rewarded her with a finger, working lightly inside her, making her moan long and deep as I worked further into her pussy and started going a bit harder.
Just when she was about to cum, I stopped, pulling my finger out of her soft, tight little pussy hole. She cleared her throat, obviously disappointed and I thought she might actually cry. She clearly had no idea what I had in mind for her next.
“Be patient, my pet.”
“Yes, Master.”
Dropping my head between her quivering thighs, I ran my experienced tongue down the length of her pussy. She let out a long moan accordingly, her sounds only getting more intense as I picked up speed and slowly increased pressure as she got used to the feeling.
Macy squirmed and jerked and screamed under my tongue, reacting in unbridled ecstasy.
“Oh, my God, boss, you were right. I needed to be patient for this. It feels so good.”
I thought that if I went any harder, she might just pass out from sheer joy. It was clear she was a true virgin and had never been licked or fingered before and I was proud to be giving her her first experience.
This was a sentiment I didn’t usually go in for but I was feeling a lot of things with Macy that I had never felt before: a sort of protectiveness and affection that took me by surprise. I was always careful when playing, particularly with sensitive things like butt plugs, but there was an extra level of care I found myself taking with Macy.
It could have been because she was a virgin and was therefore more vulnerable. She really didn’t know what to expect and was trusting me entirely.
She also had the youth and innocence thing going, a factor I was trying very hard not to abuse, looking for any sign or reservation or pain when we were playing. But I had found none and she seemed to enjoy it as much as I did.
After she came, squirming and screaming, I waited for a moment for her to recover and then put her down on all fours on the floor, her beautiful, plump ass high in the air. Getting the lube bottle, I slathered the butt plug so I wouldn’t hurt her in a bad way. This was a clear distinction every ethical person involved in BDSM knew well.
“The safe word is quarantine,” I told her.
She nodded, looking as if she didn’t plan to use it.
Giving both her ass cheeks gentle strokes, mixed with gentle spanks to get her warmed up, I carefully parted her ass with one hand, while lightly pressing the tip of the butt plug to her asshole with the other, pushing it slowly in until only the base could be seen, Macy letting out a long, slow breath as her tight little ass hole was penetrated.
On impulse I reached down and fingered her pussy, knowing that the sensation would be even more intense with the anal stimulation, bringing her to the edge of orgasm before stopping, making her whimper out loud.
“Please. Please, boss,” she begged. “Please let me cum. Sir. Master. Please. I’ll do anything. I feel so close. I need it.”
“I make the rules,” I reminded her. “Wear it for six hours, while doing your work and then afterwards. Do not take it out until six hours are up. Then sanitize it and take a shower. Wash your pussy and then your ass. I want you squeaky clean for tomorrow, is that clear?”
“Yes, sir!” Macy replied, bursting with enthusiasm.
I felt a pang I didn’t recognize at first. On closer consideration I realized it was what most people would call love. It felt like I was falling for her.
That just wouldn’t do. I needed to stay grounded. Just because we were forced together by state order didn’t mean that I should break, or even bend, my rule about committed relationships.
I wasn’t a player or a man whore. I was just too busy with work to deal with the extra responsibilities of a relationship. I was very firm about keeping commitments and I only had the time and sanity for one at a time. Sex was really just an outlet that I did when I had the time. Something that applied to sleep and even food. There were bad guys to put away and there was no rest for the wicked or the good.
“We are probably going to win the case,” I told her, trying to get serious and professional. “The other side is being worn down being cooped up together and freaking out about the Coronavirus. The order should be lifted in a day or two, letting everyone go home. I hope you realize this will be over then. I can’t fall for you and you can’t fall for me. Clear?”
“Yes, sir,” she said, sounding like she was fighting tears and losing.
I helped her to her feet and gave her a gentle spank to send her on her way. I watched her ass wiggle as she left, impressed at how well she had learned how to walk with a butt plug buried in her ass.
It was a shame we couldn’t last longer than the lockdown. I knew I was going to love fucking her in every hole, filling her up with my thick hot cum while taking her virginity. But I also knew I would have to let her go after that.
We just couldn’t work out together long-term.
Chapter Eight - Macy
Day 5 of Lockdown
It hurt a lot. Not the butt plug. That had actually felt really good. I had no problem wearing it for six hours and would have left it in all day if he had told me too. If that was what anal sex was going to feel like, I could hardly wait!
What hurt was the teasing and the hot to cold switches Paul was doing. I knew part of it was due to a power exchange. I had given him control and he was teasing me. Like when he got me close to orgasm and then stopped suddenly. Only then he usually let me cum.
He was acting even more reserved now. Teasing me even more, almost cruelly.
I really wasn’t looking forward to having to leave. I loved what he was doing to me. I began to wonder if he was ever going to take my virginity. And if he wasn’t, why he kept making me wear the butt plug. Which strongly implied that he planned to fuck me in the ass at some point.
I knew it was all temporary. He had made that clear. I had been falling for him before he had said it was impossible. I didn’t feel any different about him but I tried to repress it so it would drive me crazy. I was frustrated enough with how long he was making me wait to finally fuck me.
The phone on my desk started to wait. I just stared at it for a moment, knowing that it was him, calling for our normal morning “meeting.” A part of me wanted to make him wait like he was making me wait. Finally, on the fifth ring, I picked up.
“Hello?”
“What took so long?”
“Sorry, sir. I was working.”
“You answer when I call you. Right away.”
“Yes, sir.”
“Come to my office fully clothed. Bring the butt plug.’
“Yes, boss,” I said, trembling with anticipation.
I got the cleansed butt plug from my desk drawer and headed to Paul’s office, my squeaky clean pussy already getting wet.
“Come here,” he said, as soon as I came through the door.
“Yes, Master.”
I went over and stood by his chair. Turning to face me, he took the butt plug from my hand, setting it down on the desk, not even looking at it as he did so. Taking me by my hips, he pulled me to him so that I was inches away. Sliding his hands down my bare legs, he slipped off my shoes, tossing them aside.
Stroking his way back up, I thought he might put his hands up my skirt. He surprised me by caressing up over my ass and undoing my skirt, letting it drop. I still wasn’t wearing panties. Luckily, I’d kept extra clothes in my bad for when I usually went to the gym. But I didn’t see the need to wear panties since Paul liked to see me naked anyway.
Taking a moment to give my aching pussy some love, he kept going, slipping off my suit jacket and then he started unbuttoning my shirt, removing that as well, leaving me in only my bra. A problem soon solved when he undid it in one smooth motion, with the flourish of a veteran magician.
Standing slowly, close enough that I could smell his aftershave, Paul took a hold of me
and guided me onto the desk and onto my back, my legs dangling over the edge. Lifting them over his shoulders, he sat back in his chair and started giving me long, light licks on my pussy. Relief and pleasure washed over me, helping me relax.
When I was ready, something Paul always seemed to know, he started going faster, lapping at me hard, mixing hard licks with gentle swirls on my clit. I got close to orgasm and he kept going, sliding a finger inside me working me until I came.
“Paul!” I screamed out. “Boss. Master. Sir. Oh, my God.”
“That’s right,” he said. “That’s my slutty little pet. Cum for me. Cum on my desk.”
Keeping my legs over his shoulders, he got out the bottle of lube, spreading a long line the length of my pussy. Putting the bottle aside, he gently worked it into my pussy with his fingers, not afraid to go in deep.
I was nervous to dare hope, but it seemed like he was getting me ready to finally take my virginity and let me feel his cock deep inside me. We didn’t have any condoms, but I didn’t really care. I wanted to feel him raw.
Slowly standing so his crotch was level with my pussy, Paul unzipped his pants, taking out his massive cock, which was already quite hard. Lubing up his cock as well, he put aside the bottle of lube and started stroking the warm head of his cock against my pussy lips.
“I’m going to take your virginity now,” he said. “And you’re going to let me, aren’t you, my pet?”
“Yes, sir,” I told him. “Thank you.”
Finally.
It felt amazing and I tried to prepare myself for what was to come.
It turned out I couldn’t. The feeling of Paul’s hard cock easing into my tight little pussy was unlike anything I had ever experienced and had no way to verbalize or describe it. All I could manage was a deep moan as he worked his way, inch by inch, up to my unpopped little cherry.
Stopping for a moment, he leaned down and kissed me tenderly while he pushed through to the other side.
The pain wasn’t too bad. Just a bit of a pinch and it didn’t last very long. His cock was so big it brushed against my clit as he pushed through so there was a good bit of pleasure mixed with the momentary pain, soon giving way to only pleasure.
Paul pulled back a bit so most of his cock was rubbing up against my clit and gently fucked me to my first orgasm with a real cock in me. He was freeing me of my innocence and introducing me to the sexual world.
Pulling out before he came, he fed me his delicious cock, unloading in my mouth which I was more than happy to accept, swallowing it all down.
Getting me into a sitting position, Paul kissed me while gently stroking my pussy, which was still tingling. Moving his way down my neck to my tits, he lightly sucked my nipples while he fingered me to another huge, earth shaking orgasm.
When I had cum, he got some wet wipes from a drawer in a desk and cleaned us both. When we were both clean, Paul turned me over, bending me over the desk, my ass in the air. I knew what was coming next even before I heard the snap of the cap.
Paul eased the butt plug inside me as deep as before, except the amazing sex had relaxed me enough that it went in easily.
“Wear it all day,” he said, closing the cap on the lube bottle, “tomorrow I’m going to take your anal virginity, too.”
Chapter Nine - Paul
Day 6 of Lockdown
I woke up with the sun, such was my excitement for the new day. I never would have guessed that being in lockdown at the office could be so much fun! Though Macy had everything to do with it.
Rising to my feet from the cramped confines of the couch, I put my suit back on, having folded it up and put it on the desk to keep it nice. It was one of my better ones and I saw no reason to risk ruining it just because it would be the end of all the clothes I would have to wear for a week.
At least I had chosen the one with a heavier, more durable material.
Decked out in my suit of power, I headed out of the office and down to the receptionist lounge, something special secreted in my briefcase. I whistled a happy tune as I went, in no way hampered by my massive hardon.
“Good news,” I said to Macy, who was sitting at her post like the good girl she was.
“What’s that, sir?”
“I just got a text from the other side. They are willing to settle without the need for a trial. They are also doing a complete recall.”
“Oh, good!” she said, knowing I had been hoping to heck he would win the case and strike a blow for justice.
“There is no more work to do, my little pet,” I said, changing my tone.
“Oh.”
“Just fun,” I said, coming up behind her and stroking the back of her neck.
She shuddered with what I recognized as pleasure.
“Yes, sir.”
“I thought we could celebrate.”
“How so, boss?”
“Well, first, I am going to fuck you rough. You are broken in now and should be able to handle it. Then, I am going to pop your anal cherry.”
I could feel her stiffen at the mention of her anal cherry. I could tell that she really wanted it. I did too, which was why I had put her through such rigorous ass training. So I wouldn’t hurt her when the big day finally came.
“I also have another surprise,” I said, putting my case on the desk.
“Oh, what’s that, sir?”
I opened the case and showed her the ropes— silk, of course— that I was going to use to tie her down to her desk while I had my way with her.
“Strip,” I ordered.
Quick as you please, Macy was completely naked, waiting for what I wanted her to do next. I went over and inspected her thoroughly. She had clearly had another shower. Her pussy and her ass were squeaky clean.
“Good girl,” I said, gently cupping her pussy.
Guiding her around to the other side of the desk by pulling on her pussy lips, I bent her over it. When she was in position, I took her by one ankle and then the other, spreading her legs as wide as they would comfortably go before tying her ankle to the front legs of the desk.
Running my hand up her bare back, I moved around to the other side of the desk and did the same with her arms, securing her by the wrists to the back of her legs. I took a moment just to admire the beauty of her position. I really did have her right where I wanted her: tied up, spread wide and ready for me to have my way with her.
I got the butt plug from the drawer where she kept it while not wearing it and the bottle of lube too. Kneeling behind her, I slowly licked her pussy, going all the way up over her asshole with each long, tender lap of my tongue.
When she was ready, I lubed up both Macy and the but plug, sliding it carefully into her prepared asshole, encountering a lot less resistance than I had before. The anal training clearly having done its job.
Working the butt plug into place, I stood up behind Macy, dripping my pants. Working her pussy a bit more with my fingers, I worked my cock into her tight little pussy. She wasn’t a virgin anymore, but she was still super tight and tender. I was tempted to go all the way in but then thought better of it, stopping at halfway.
Giving her a moment to get used to being so full, I started to move, taking her firmly by the hips, holding her absolutely still as I pumped her sweet little cunt, Macy moaning loudly as I did so.
Her moans turned to screams as I picked up the pace, fucking her harder and harder until I was slamming her up against the desk, using one of my hands to carefully pull back on her ponytail.
A lot of people didn’t really appreciate how difficult proper hair pulling was. Not only could it hurt in a bad way, there was also as serious risk of neck injury if done too hard or in the wrong way. I had been in the BDSM lifestyle for a good three years before I even attempted it. Macy seemed to appreciate my dedication, shouting even louder as I pummeled her.
“You like that, Pet?”
“Yes, sir!” she screamed.
I loved it too. It was by far the best sex I had ever had and I w
anted so much more, even after the lockdown was lifted. I wanted to tell her but couldn’t find a way that didn’t feel weak. Every way I could think to say it seemed so pathetic.
“You want it harder?”
“Yes!”
“Yes what?” I demanded spanking her hard enough to leave a handprint.
“Yes, sir!” she screamed, her voice going raw.
I fucked her even harder, marveling at how much she could take. She really was a tough little cookie and seemed to honestly enjoy what I was doing to her. I had never seen someone take to the life so quickly or completely.
I could feel her tighten and knew she was about to cum. I wasn’t far myself so I squeezed the base of my cock to keep hard until she came, screaming and gushing all over the place. I barely got my cock into her mouth before unleashing a flood of cum, which she swallowed down like a pro.
My little pet was so perfect that I wasn’t sure how I would be able to give her up.
Chapter Ten - Macy
It was the best orgasm I’d ever had. Way better than the ones I’d ever had by myself. I really had no idea what I had been missing. It was, somehow, even better than when he had so gently taken my pussy virginity.
A lot of it had to do with the butt plug, the anal sensation amping things up even more. I also apparently really liked rough sex. Like, a lot.
I could understand why he had been gentle before. It being my first time at all. He didn’t want to hurt me. Not in a bad way, so he was really gentle. Gentle was good too but since I was broken in, I really liked being fuck hard and ravaged, no matter how tight I might still be. If anything, it made it better.
I barely had time to catch my breath before I heard another siren and the crackle of a loudspeaker preluding another announcement.
“Attention citizens. The mandatory lockdown is now lifted. Everyone has exactly one day to get home and quarantine there. That is all.”
The loudspeaker cut out, leaving us in silence again. Neither of us spoke for a while as we processed the meaning of what had just happened.