Ashley

I watched Rachel climb into her car from my front window where I stood nude. Our shower together had been relaxing and had been a great curtain call to the previous day’s events. Still, there was a part of me that was missing her as she drove away. My Master pushed it from my mind, there were more important things for me to be focused on.

I strolled through my living room picking up the matching butt plug that I had put in Rachel before she left. Once I had it I headed back upstairs to grab some clothes. Sadly I would still have to go to work and earn money. When I got upstairs I looked at the time on my phone. The old me would have panicked at what time it was, but I couldn’t have cared less.

I went to my closet and was grabbing a pair of slacks and a button-up shirt when I stopped myself. There was no reason I had to wear that to work today. Instead, I pulled out a white blouse, a knee-length pencil skirt, a pair of black nylons, and black heels. I tossed them onto my bed next to where I had put the butt plug.

I crawled onto the empty side of my bed still nude. While still on my knees I lowered my head until it and my chest was resting on the mattress. I arched my back while I grabbed my ankles. My sex was on full display and it did nothing but excite me.

“Master, please bestow upon me your gift. I want you to be a part of me.”

It took a matter of seconds before I felt two tentacles wrapping around my wrists holding my arms tight to my legs. I wasn’t able to move at all now. I’m not sure if it was out of instinct or me trying to entice my Master but I began to shake my ass that was in the air. I could feel the cool air on my love entrance.

The next tentacle wrapped itself around my throat lightly squeezing before directing its tip to my mouth. I eagerly opened my mouth accepting my Master inside. He slowly thrust his tentacle in and out of my mouth. With each push of his appendage into my mouth, he would tighten the length around my neck a little more.

I swirled my tongue around the thick member in my mouth, licking off some of its slime with each movement. My body began to respond to its effects, the sexual heat and arousal spreading throughout my body. Being held there in my own bed completely helpless and at my Master’s mercy was all that I needed.

Then came what I had been expecting. A different tentacle had arrived, hovering above my exposed pussy and ass. This one came within six inches of my ass and a slit at the tip opened up. It twitched and slightly expanded as something traveled down its length. I could then feel the hot strings of slime ejaculating from the tip coating both of my holes.

That tentacle was replaced with another and I soon felt it rubbing its tip against my now-coated asshole. I took in a deep breath as I felt it begin to enter this virgin hole. Rachel had always been more adventurous than me and I had never attempted anal even though she talked it up so much. But now this was for my Master and I would do anything for him.

I felt a length push inside of me and my body responded naturally by trying to clench. The tentacle let itself rest at the depth, allowing my body to acclimate to this new intrusion and experience. As I continued to suck on the tentacle in my mouth the muscles in my rear relaxed. This relaxation was met with a withdrawal followed immediately by a new deeper push.

The sensation was unique and as the slime soaked into me it was becoming more pleasurable. My Master must have determined that I was ready as he began a steady rhythm into me. I started to moan and wanted to rub my clit or finger myself but my hands were held tight to my legs. It was being made clear to me that the only way I would orgasm would be from anal if I even could.

After a few minutes of thrusting it stopped abruptly.

“Your body must learn to accept me. It must be taught and trained.”

As the words resounded through my head I could feel the tentacle buried in my ass grow thicker. It pressed more against my anal walls and elicited a pleasure that I never would have thought could be had solely from this. My body did not take as long to adjust to the new size and I was soon being thrust into again.

“You are doing well. Not as well as Rachel, but I will sculpt you to my pleasure and your body will be conditioned to me. Only two more adjustments and you should be good for now.”

His words went through my mind but I was focused on the sensations in my rear. I was moaning excitedly as each inch pleased me. This continued until he once again increased the thickness of the tentacle inside me. I could feel the size of the appendage grow within me applying more pressure.

This continued for a few minutes more until the final size adjustment was made for the tentacle. I had no idea how thick it was now and I didn’t care. A few more minutes of thrusting at this final size had me at the very edge of an orgasm. The orgasm was unlike my normal orgasms.

My legs shook against their restraints and I felt the orgasm hit hard. It definitely hit much harder than a vaginal orgasm. I clenched and spasmed against the length inside of me and my mouth went slack. The muscles running through my legs and ass tightened and relaxed in quick succession.

I lay there on the bed feeling the waves work their way through my body. I couldn’t believe that I had just had an anal orgasm the first time I attempted it. Of course, I would have, though - my Master had given it to me. The tentacle pulled itself from my ass with a plop noise.

The first thing I noticed was how empty my ass now felt without anything in it. I hadn’t noticed that the tentacle in my mouth and around my neck was gone as well. The tentacles holding my wrists to my legs were still there. I saw a tentacle wrap around the butt plug that had been on the bed.

It twisted its length around the plug coating it in slime before withdrawing it from my field of vision towards my backside. It wasn’t long before I felt its pressure against my anus. After the fucking it had just received there was barely any resistance as the plug slid into my ass. I felt it reach the flared base and the slight pressure the end gave against my opening told me it was there.

Once the butt plug was inside of me the tentacles holding me in place retreated back to the mirrors they had come from. It felt good to once again have something filling my ass and could understand Rachel’s love for this. We would have to experiment with this once she came back over. I pushed myself off the bed and headed for my underwear drawer but stopped on my way.

Fuck that, I don’t need any today. I went back to the bed grabbed the nylons and pulled them up my legs. I then slipped on my pencil skirt grabbing a white blouse and a lacy white bra. I left the top few buttons of my blouse undone. Looking at myself in the mirror I couldn’t help but be surprised by how good I looked.

I made my way to my kitchen grabbing two protein bars on my way to my car. I started my car and began my commute to work even though it was well past my normal departure time. The commute was boring but went by quickly enough. I pulled into a parking spot and headed to work.

I took the elevator in the lobby to my work floor. Exiting the elevator I could hear my heels clicking against the wood flooring in the lobby. I made my way to my desk and dropped my purse on it. Before I could even sit down Stan had popped out of his office and made his way to my desk.

“Ashely, where have you been? I need to speak with you in my office right now.”

Judging by his tone and expression he was less than pleased with my absence and lack of communication. I followed him to his office noticing the many eyes on me as I went. Once we were in his office Stan closed the door and walked back to his desk motioning for me to take the chair across from it. I sat down in the chair crossing my legs and gave the best inquiring look I could.

“What the hell is going on Ashley? You went home sick and then I don’t hear from you. Then you show up after missing work and are very late. This isn’t like you and this behavior isn’t acceptable.”

He was clearly upset and I was wondering if my job was at genuine risk. I suppose I didn’t actually care if it was or wasn’t. I couldn’t help but notice that Stan’s eyes weren’t solely focused on my face. This elicited a small smirk from me.

“You are absolutely right. I wasn’t feeling well and I went home and have been resting and trying to get better. Luckily I was able to find something that has really helped me and made me feel so much better. I was planning on being in today but I overslept a bit.”

His expression softened a bit seeing that I was clearly remorseful for not updating him. There was no reason that I had to beg for this man’s forgiveness. The only person that mattered was my Master and I need not care about anyone else.

“Well, I’m um glad that you are feeling better. You are certainly looking better. I like you Ashley, but you know that I am going to have to write you up for this.”

“I completely understand that it is not up to you and I’m not upset by it. This was completely on me.”

“That is very mature of you. Now that that is out of the way, I have a question.”

“Yes?”

“You left your coffee mug at your desk the day you went home sick. I wanted to be nice so I tried to clean it out for you.”

I stood from the chair and crossed the room to the glass wall of Stan’s office. I pulled the cord on the blinds closing them and blocking the office.

I couldn’t hold back the smile that spread across my face. This might be easier than I thought it would be. Stan stood from his desk and walked over to me.

“Yes?”

“When I was cleaning it, there was something in it. I was washing it out and my hands touched something.”

I moved in closer to Stan, closing the gap between us. He had cleaned my mug that had slime from my Master in it.

“Oh, and how did it make you feel?” I said breathily.

“My hand started to, uh tingle. Then it started to get so warm, but it wasn’t just heat I felt. It was like my nerves were being charged.”

Even this close I could easily see the erection that was now being pitched in his pants. He was going to be soft putty in my hands. His will would not withstand my Master’s might.

“How were you feeling charged?” I said as I reached my right hand forward gently grasping his hard dick.

Being this close I could easily see Stan’s pupils dilate and a small gasp as he felt my hand on his member. There was no resistance to my touch and his body was very clear in its desire. A part of me wondered how many times he has thought about having his way with me.

Did he ever sit at his desk fantasizing about me, thinking about calling me into his office and dominating me? Has he ever jerked himself off thinking of me or imagining my uncontrollable desire for him? Or maybe I slipped into his mind while he was fucking his wife at night, closing his eyes and picturing me in her place.

“It felt like I was sexually charged. I was just full of this lustful energy that came out of nowhere. I couldn’t help myself, I had to take care of myself.”

“Well now Stan, it sounds like you were a very naughty boy. Playing with yourself at work hardly seems appropriate.”

I began to slowly rub my hand up and down his length through his pants. My other hand went to his belt and undid it. With a twisting of my fingers, his pants button was undone followed by his zipper. Stan didn’t even seem to mind in the slightest. The only thing keeping his pants up was my hand resting on his dick.

“You liked how it made you feel, didn’t you? You want to feel it again?”

“Yes, I’ve never felt like that before. I, uh, it was amazing. I need more of it.”

With that, I withdrew my hand allowing his pants to fall to the floor. With them out of the way I brought my hand to the top of his boxers. I slid my hand down until I felt his warm and hard rod in my hands. I began to lightly stroke his dick slowly and deliberately.

“It was really that amazing for you, huh? Can you imagine if you were able to have even more?”

Clearly, that was enticing to him. I imagine if I told him to beg for more he would.

“Undo my blouse.”

Stan was frozen there for a moment almost as if he was struggling to process what I had just told him to do. A light squeeze on his dick seemed to snap him out of it and his hand flew to my chest as button after button was undone.

“That’s a good boy.”

Stan was looking at me expectantly, his focus struggling to stay focused on what he wanted and not my body. I felt so powerful at that moment, bending him to my will and desire. All of this was possible because of my Master.

He was so focused on me and my chest that he didn’t notice the movement in my pencil skirt. A tentacle had emerged through the mirrored butt plug and was extending to the bottom of the skirt. Once it reached the bottom it curled back up and began heading upwards.

“Look me in the eyes and do not break eye contact. Do you understand me?”

He nodded in agreement as his eyes darted to mine and remained there. The tentacle curled its way upwards until it reached my elbow at which point it became to coil itself around my arm as it traveled toward my hand.

“What would you do to feel it again?”

“I would do anything, I just want more of it.”

“And how do I know that you are serious about this?”

“What do you want me to do to prove it to you? I will do whatever you want.”

I continued to pump his length as the tentacle reached my hand. I slid my hand away as the slime-coated tentacle replaced my hand. It wrapped a coil around his dick and began to stroke its length coating it in its slime.

The reaction on Stan’s face was immediate as he could feel the effects on his dick. I had to give him credit though, he did not break his eye contact. The tentacle continued to stroke his dick, his legs quivering with each motion. There I stood in his office in an open blouse, a bra, and a skirt with a tentacle trailing itself out of a butt plug in my ass that was stroking my boss.

“Kneel down.”

Stan dropped to his knees as quickly as he could while maintaining eye contact. The tentacle followed his motion downwards.

“Listen closely because this is going to be how it is. From now on you are going to cover for me here. I’m basically done working, but I expect my paychecks to keep showing up. You can divvy my work up amongst the others but I have far more important matters to attend to now. Is that understood?”

There was a moment of delay and a look of disagreement on his face. The tentacle tightened itself on his erection and it was clear that he understood the message.

“Okay, yes I can do that,” he said and the tentacle resumed its lazy travel up and down his length.

“Good, now I assume you understand that you aren’t going to tell anyone about what has happened here, correct?”

A quick nod from him confirmed it.

“That is a good boy. Now there is one final matter. Do you surrender yourself to my Master? All of yourself and to serve him as he sees fit?”

“Yes, of course. I just want this please.” he fired back without even a second of thought.

A wicked smile spread across my face.

“That is very good,” I said as I patted his head and the tentacle around his dick increased its intensity.

Stan began to moan in response to the pleasure that my Master was giving him. While I didn’t care about the noise, we were still in the office with a single pane of glass separating us from several people. It simply would do no good if someone were to start a rumor or come check in on us.

“You are being far too loud. Why don’t you put that mouth to use instead?” I said as I walked over to his desk and leaned against it.

He clearly understood what I meant and from his kneeling position moved his hand to pull up my skirt. The tentacle unlooped from his dick as he leaned into my pussy and took it within his mouth. His tongue immediately began licking away at my folds and was slowly making his way toward my clit.

The tentacle unwound itself from my arm and repositioned itself so that it was now coming straight from the butt plug. Its length then extended forward wrapping itself around Stan’s neck tightly before tracing down his chest and forming a lazy loop around his penis.

“You have done very well, my slave. He will serve me well. Consider his pleasuring of you a reward for this. He will stay there as long as you desire.”

The attention my pussy was getting along with my Master’s voice in my head was intoxicating. I leaned my head back basking in the surprisingly skillful tongue work that Stan was displaying. I lifted both of my legs and let my thighs rest on his shoulders as I tightened my thighs against his head. I grabbed a handful of his hair and could feel him wince at my rough touch, but if he wanted to serve our Master he would accept that price.

With my free hand, I swiped the surface of the desk behind me clean knocking papers and various office supplies to the ground. I couldn’t care, I was enjoying my Master’s reward. I leaned back on the now cleared space of the desk and let Stan continue pleasuring me.

“Stan, you’re going to have to do a lot better if you are going to want anything more from our Master.”

With me saying that, the tentacle around his dick loosened its grip to the point where it was barely touching it. The stroking also slowed to an excruciatingly slow speed for him. I was a tool for my Master’s will and he was rewarding me.

With his own pleasure now decreased Stan tried to bring his own hand towards his dick. Whether to stroke himself or try and grab the tentacle loop and force it to continue I was not sure. Our Master made it clear though that would not be acceptable. Another tentacle came forth from the butt plug and quickly wrapped itself around his hand and held it in place far from his erection.

“You will pleasure my slave. You will be pleasured only when my slave is satisfied and only then will I give you a fraction of the bliss she receives.”

I could feel his head slightly move side to side between my thighs as our Master spoke to him for the first time. He was clearly alarmed but it was not something he seemed to care about. After all his dick was in the grasp of a tentacle from a creature from God knows where and he seems pretty fine with that as long as he gets to cum.

I pull his face tighter to my waiting opening and increase my grip on his hair. He gets the message and begins a renewed effort to receive his own reward. He brings his free hand up and slipped a single finger and then two fingers inside of me. I gasped at the welcome intrusion and lay back knowing that Stan is as much working hard for my orgasm as he is his own.

I am once again surprised at Stan’s skill as his tongue and fingers work in unison bringing me pleasure I would have never expected. As his tongue works itself over my clit he arched his finger within me and was rubbing my g-spot. Damn, this was so good. I had never expected this when I had come into the office today.

Before I knew it I could feel my orgasm building, wave after wave of pleasure building against the floodgates holding it back. I couldn’t hold off any longer, I felt my toes curl and I opened my mouth in a silent gasp. The orgasm shook my body and I could feel my thighs clamp down tightly on Stan’s head, who dutifully continues to pleasure me as I orgasm. I hold onto his head with my hand as if I were riding a bucking bronco.

Finally, my orgasm subsides and I loosen my legs' death grip on his head. As I let go of his hair he pulls away and sucks in several deep breaths. The lower half of his face is covered in my wetness and it is an incredibly arousing scene to see him kneeling before me.

Looking down I can see that he is still erect and by the looks of it is probably the hardest he’s ever been in his life. The lone tentacle barely wrapped around its girth is still lazily traveling along it.

“Did my new slave pleasure you enough? Does he deserve a mere pittance of pleasure?”

I look down at my boss, kneeling there his eyes clearly begging me for release. I could leave him here without any release until I next decide he should have one. That wasn’t right though, he would have plenty of work to do in covering for me now and serving our Master. He deserves a release now and based on my orgasm he did honestly earn it.

“He does deserve it, but I have a specific idea on how he may receive it,” I say only to my Master.

The wave of satisfaction that rolls through my body makes it clear that he approves of my idea. I tell Stan to stand up and he quickly obeys. The tentacle around his member retreats from it leaving it bare. He’s standing there with his massive erection glistening in the harsh fluorescent lights waiting on my command so that he can cum.

I leaned back again on his desk, spreading my legs wide. I guess not wearing any underwear today had paid off. I begin to slowly rub myself, my hand slick with my juices and his saliva. I gently rub my clit while Stan stands there like an obedient dog. I give myself a few more minutes of pleasure before I decide it is his turn.

From my laid-back position, I prop myself up and give him the universal finger-curling motion to come to me. The excitement in his eyes is unmistakable as he quickly closes the gap between us. His rod is clearly aimed directly at my pussy and it is clear that is his target. Before it can find a warm home inside me, my right leg extends, and my heel presses against his chest.

He is stopped right in his tracks as I hold him at leg length. He seems to be both confused and disappointed. To his credit, he doesn’t push any further or try to get any closer.

“Oh, did you think you earned me? How foolishly bold of you,” I said as I pressed my heel into his chest with slightly more force.

“You don’t deserve me and you certainly shall not be having me in any way. Do you understand?”

He shook his head in acknowledgment and looked quite disappointed. I pressed my heel a little more into his chest and then let up. I brought my leg down and rested my foot on the ground again.

“Good, now that is settled you can begin by taking off my skirt.”

He eagerly advances and finds the zipper for my pencil skirt and pulls on it. Next, he pulls down my skirt and it rests around my ankles. That simply wouldn’t do.

“You’re not going to just leave that laying there, are you? I ask.

Realizing his error he quickly picks up the skirt and neatly folds it before putting it on one of the chairs in his office. Maybe there was some hope for Stan after all. He was at least a quick learner.

“That’s a good boy. Now come here and stand between my legs. Don’t you dare let your dick touch my pussy in even the slightest manner. If it does I will make sure that you never orgasm again.”

The look of worry made it clear that he understood and walked between my spread legs. His erect dick hovered a mere few inches above my slick pussy. It twitched in excitement bobbing up and down and getting close to touching me, but luckily for Stan did not.

The tentacle emerged again from my butt plug and curled itself upwards, sliding along my moist slit as it went. The tentacle then formed a coiled cylinder directly above my pussy. Its slick length rubbed my clit as its length expanded and contracted.

Stan clearly understood the situation and eagerly stepped forward and slid his dick inside the tentacle cacoon that was placed right above my vagina. He quickly bottomed out inside the cacoon and pulled his length out to again plunge back in. With each thrust into the tentacle, its surface rubbed me more and I got some enjoyment from it.

The tentacle cacoon was undulating as it twisted, pulsed, expanded, and contracted around Stan’s rock-hard cock. Slime dripped from between the coils and fell down onto me. The humping had turned into a more manic affair as his length entered and exited the cacoon as quickly as he could. He was clearly lost in the bliss of it all.

Unfortunately, this level of bliss is always accompanied by noise. Stan could clearly not contain himself and his soft grunts turned into much more. As soon as he began moaning I knew this could spell trouble. Thankfully my Master knows best. I could feel another tentacle push its way out from between my butt cheeks and shoot its way up.

The tentacle first looped around Stan’s neck before plunging into his mouth. I could see that the skin on his neck around the tentacle was being pressed lightly. The end of the tentacle which was in his mouth now filled it completely and muffled any further noise that he could possibly make. He didn’t seem to mind in the slightest as he continued to hump away.

I felt a third tentacle protrude from between my cheeks and it found its way to my opening and pressed itself in. My body took a moment to adjust to its size before it was withdrawn from me and then entered again. The speed and depth of each thrust increased and I quickly noticed that it matched Stan’s motions.

This continued for several minutes as I lay back and enjoyed my Master fucking me. Judging by the energetic thrusts of the tentacle within me, Stan was enjoying himself immensely. I could hear his dick sliding in and out of the warm and slimy cocoon.

My next orgasm was upon me and I cried out as it hit me. Thankfully I had enough forethought to cover my mouth and mute it before it escaped my lips. I shook on the desk as I let it ripple through me. Stan didn’t stop his thrusting and thus the tentacle within me had not stopped either nor had its length rubbing against my clit.

My hand fell to my side and I let out a deep breath relaxing on the desk. My Master knew that I had finished and I praised him for this release. The tentacle deep inside me withdrew itself and retreated back between my buttcheeks into the plug’s mirrored surface.

I could still feel Stan’s frantic thrusts above my pussy and judging by them he was at the edge. Suddenly he gave a few quick twitches and I realized he was orgasming. With a flurry of motion, Stan was pulled backward by the tentacle around his neck and the cocoon left the space above my mound.

As Stan leaned away from me the cocoon unraveled the top of itself exposing the head of the dick contained within. His hips shook as the head of his cock twitched and rope after rope of his own cum shot onto his own chest. I hadn’t realized that at some point he had lost his dress shirt.

No sooner had the final dribble of cum come out of his dick, the tentacles holding him released. The one in his mouth vacated and unwound from his throat. The slimy coil cocoon unwound itself dripping slime as it did. They both then pulled themselves back through my cheeks and the plug leaving just Stan and me in his office.

He lay there on the ground gasping and sucking in deep breaths of air. I let him catch his breath and recover some as I sat on his desk with my legs crossed. I can only imagine what a sight this would be for anyone walking in on this.

When he finally had his breath he pushed himself up onto his elbows while still laying on his office floor. This must have been quite the experience for him.

“I don’t know what you’re doing over there but this won’t clean itself,” I said while snapping my fingers.

Stan crawled his way over to where I sat on his desk. Once he arrived I unfolded my legs and spread them wide for him. Without prompting he dove into my crotch and began licking up any juices, wetness, or slime that was still on my skin. His tongue lapped away at my skin and I couldn’t help but feel my arousal growing, but that need would have to wait.

“Good boy. Now get me dressed, I can’t be looking like this.”

As he hurried off to the office chair that he had placed my skirt on I stood up. I gave a long stretch through my body and couldn’t have felt more alive. Soon Stan was back at my feet holding my skirt open ready for me.

I placed one heeled foot into the skirt followed by the other. Once my feet were in Stan pulled the skirt back up my legs to my waist. He grabbed the sides of my blouse and began buttoning them back up. His rapt attention on my breasts was unmistakable but there was no harm I supposed as long as he behaved.

With my blouse buttoned back up, Stan tucked it into my pencil skirt and zipped the skirt closed. I looked down at him kneeling there on the ground before me. It was hard to believe that just a short while ago he had called me into his office to reprimand me. How things had changed for him.

I made my way across his office towards the door. I paused at the door with my hand resting on the knob. I looked back at Stan kneeling there next to his desk.

“Look at how messy you are. Sitting there covered in your own cum. Clean yourself up and make yourself presentable, this is a professional working environment as you know.”

With that I twisted the door knob and exited Stan’s office, leaving him in there alone. I looked out at the cubicle farm before me and other than a glance here or there no one really looked up at me. That was good news, at least no one had heard anything to pique their interest.

As I walked back to my desk I was filled with such happiness and pride. I had added another slave to my Master’s ranks. Hopefully, Rachel had been as successful as I had been, and based on how my Master felt I believe she had.

I grabbed my purse from my desk and started heading for the exit. One of my coworkers bumped into me on my way out.

“Hey Ashley, sorry. Was Stan available? I saw you just popped out of his office.”

“Oh, I don’t think he so. He seemed pretty exhausted and drained. Guess he rode me a little too hard,” I said without a hint of a smile on my face.

With that, I turned away and headed back for the door. A short ride home and then I would be rejoined by Rachel. I couldn’t wait to hear about how her endeavor went. I left work feeling light and so very happy that I couldn’t wipe my wicked smile from my face.