Chapter 11 Pushing Boundaries

I was uncertain about how we would celebrate our second anniversary, considering we hadn't marked our first year together until after the date had passed. This was because Ben was stuck in Europe; it was mentioned in a video call that it had been over a year since his initial visit to my tiny house. Over the past six months, Ben had returned home on several occasions. However, due to ongoing quarantine protocols, our physical meetings were limited to a few short days each time. Thus, most of our interactions occurred during his available time for late-night phone calls (which coincided with his early mornings) and texts.

During our video calls, our conversations often took a risqué turn; with him sharing his laptop screen, we explored websites or watched videos together. Ben had introduced me to an entirely new realm--the profound depths of the BDSM community. He exposed me to explicit content, presenting pornographic videos that delved into experiences and concepts I had never conceived of before. It was a captivating, eye-opening journey into a world I had never imagined existed.

Curiously, Ben had made a deliberate decision to remove the television from my house. He believed that consuming news about the current state of the world was only causing me unnecessary anxiety. He strictly forbade me from reading about the pandemic or engaging with political content online. Instead, our interactions focused on exploring his interests and pushing my boundaries.

Unbeknownst to me, my world had gradually shrunk over time, narrowing down to the content that Ben fed me directly. I immersed myself in a bubble where my primary source of visual and textual consumption outside my work and my Kindle always revolved around his choices. Beyond the confines of the fictional books on my Kindle, everything I watched or read was carefully curated by Ben. Our shared moments were often filled with exploratory videos showcasing various bondage techniques, and he even involved me in online clothing shopping, valuing my opinion on his potential purchases.

As days turned weeks and weeks into months, this unconventional lifestyle and the desires Ben vividly described wanting to experience with me began to feel normal. In my limited sphere of information, it seemed as if "everyone" else was engaged in similar activities, fostering a sense of acceptance and belonging within this alternative realm. The boundaries of what I had once considered taboo gradually faded, replaced by a new understanding of what was typical, fueled solely by the information I absorbed from Ben.

I began to speculate whether my coworkers, whom I interacted with during various online meetings, were engaged in similar activities, concealing what lay beneath their clothing or beyond the view of their cameras. The thought crossed my mind that perhaps we were all mutually participating in these intimate endeavors, maintaining a veil of secrecy within the professional realm. It was intriguing, fueling my curiosity and continuing to read everything Ben sent me.

Having been wearing a chastity belt for over a year now, locking my pussy away, my secondary entrance was the only thing available when I was allowed to touch myself. Ben loved having video calls where he provided instructions and watched me play with myself or use one of the toys he sent for my sensitive hole. At the same time, my phone was placed on a stand near me so he had a closer view than he did with the cameras he initially had installed in my tiny house.

He had John install more cameras over time so he had better angles to see me. The newest ones were in my shower, Ben's favorite, as he loved the water running down me while I lathered myself with soap.

During one of the nightly video calls, Ben let me know he wanted me to practice deep-throating during my lunch breaks. Intrigued by the thought, I asked what he wanted me to do. Ben told me to open a package that arrived a few days ago.

Opening the box, I remove the longest dildo I have ever seen. It was huge, going from my elbow to past my fingertips and about the width of my wrist; there was no way this was going down my throat. The dildo had all the characteristics of a penis with a head, vanes, and balls with a suction cup at the base.

Ben told me he wanted me to be on my hands and knees in the shower daily during lunch until I could take the whole thing without gagging. If or when I completed this task, I would be allowed to play with my secondary hole. Until then, I was not allowed to do anything that had the possibility of causing me to cum.

The next day I logged off the computer during lunch and undressed in front of the camera in my bedroom. I slowly removed my lace bra, unclipped the hose from the garter belt, and removed the garter. Standing in front of my full-length mirror with only my chastity belt, I went into the shower and the daunting task ahead.

Turning on the warm water, I got on my hands and knees as Ben watched on the multiple cameras. I had already suctioned cup the dildo, so it lined up parallel to my body. Picking up the head of the dildo off the tile floor, I held it in with one hand while opening my jaw as wide as it would allow and rested it on my tongue.

I try to slide it further in my mouth, but it falls to the ground requiring me to pick it up again. I use one hand to help keep it in my mouth. Sliding the dildo back and forth, I went a little deeper before I gagged and quickly removed it. I tried again, and my gag reflex got triggered. Tears in my eyes, I try again without success.

My timer rings, letting me know my lunch is over and I must return to work. Getting dressed again, I felt defeated as I could only take a couple of inches.

Over the next week, I slowly took more of the large dildo before my gag reflex required me to withdraw quickly. During my nightly video calls with Ben, he lets me know he has been watching me and can't wait until I can take the whole thing, as it will be super easy to take all of him without the concern of gagging or teeth.

The following day he said he would call during my lunch to talk to me while I practice. Putting my waterproof earbuds in, I once again undress and make my way into the shower. As I turn the hot water on, my phone rings, which I answer via my headphones.

"Get on your hands and knees."

"Pick up my penis and slide it into your mouth."

"Do you like feeling me going down your throat?"

"In and out, take more of me, suck me further down."

"Slide me out and lick the tip, now suck me, taking in all you can."

Getting turned on with Ben's instructions, I can get more of the dildo than I ever had before.

"Come out and back in."

"Look up at the camera and swallow as much as possible."

I make eye contact with the camera that is waist height above me and take the whole dildo to its base. The long shaft going down my throat is taking away my ability to breathe, but I remain calm as Ben watches me, as I want to make him proud.

"Lick the balls with your tongue, that's it. Good girl"

Licking the Latex balls and imagining they are Ben's excites me in ways I had never experienced before.

"You are such a good girl; dry off. I have a present for you."

I sit back on my ankles while the dildo slowly leaves my throat. Almost at the tip, I take it in my hand while staring at the camera and lick it like a Lolly Pop.

"I miss you so much; hurry up if you want to play with your present today."

Looking at the clock, I still have 30 minutes of lunch before returning.

"Open the package that came in yesterday."

I open it, and it's another long dildo, but instead of a wide shaft, it's tapered, starting off the width of my pinky and then to almost the size of my wrist at the base.

"One for each hole; stick it to the wall behind you in the shower."

Returning to the shower quickly, I turn the water back on and stick the suction cup behind me.

"Hold the dildo in your mouth without using teeth and tease yourself with the other."

I put the dildo back in my mouth and was able to rest it on my tongue without any gagging. I then reach for the other dildo and rub it around my only available opening.

"Put the head in while putting the other one further down your throat."

As he instructed, I pushed the dildo into my waiting hole and simultaneously sucked more of the dildo down my throat. I moan over the dildo as it acts as a gag preventing me from speaking.

"This will be tricky. I want you to get yourself in the middle of both toys so you can move back and forth without them bending. I also want you to look at the camera the entire time as if I were there."

My shower was not very big, with me on my hands and knees. There was maybe a foot in front and behind me. Leaving 6-7 inches of dildo that could be inside both my holes.

Sliding back, I go front and back to see how much I could take in my back entrance, with each bit causing me to get wetter and wetter, which being in the shower, was a bit amusing when I had gone far enough back so I only had the tip in my mouth I moved forward so the long toy went down my throat. I stared at the camera as if Ben was in that exact spot watching.

"I want you to fuck both dildos as if they were me standing in front and behind you. Fully swallow me and go as deep in the pretty pink ass as possible."

With the water running down my back, I rock back and forth between the two dildos staring at the cameras. I move forward until I can swallow the whole thing and lick the balls, then slam into the dildo behind me to fill me up.

"You are not allowed to cum until I give you permission."

Going faster, I continue to go back and forth and feel the orgasm building inside me as the feeling of being filled from both ends is causing a fantasy to come true that I didn't know I imagined.

"Faster, come on faster."

I move back and forth, sliding the dildo as far as it can go each time, learning how to control my breathing as my air is cut off when the dildo is entirely down my throat.

I'm trying to hold back the orgasm, but it's building quickly. I feel like I will explode when the timer on my phone goes off.

"Stop; we will try again tomorrow."

Stopping mid-motion, I stare at the camera, pleading to let me continue.

"Remove both dildos now."

I slowly move forward enough so it falls out of my backside, then back up to remove the other from my mouth.

"Get cleaned up and wash the toys; if I see you playing with yourself, the punishment will be brutal."

With that, I put all ideas out of my head and started cleaning up, picking up both toys, thankfully different colors, from the tile to clean in the kitchen.

"Good girl"

And with that, he hangs up the phone.

I looked forward to lunches after that, though after a few more sessions, Ben would only let me do this if he was available so he could watch live and instruct me. So maybe once a week.

Thinking of Ben, one of his most generous attributes, with his physical absence from me, was checking in on me regularly, ensuring I was doing okay and enjoying our shared experiences. My main goal was to please him, which brought me immense satisfaction and a deep longing to do even more, to be his perfect submissive. I had never felt as loved, cared for, and understood by a partner before. A level of connection and communication exceeded anything I had ever experienced. I felt a profound sense of belonging and acceptance in his presence, bringing me an indescribable sense of fulfillment and contentment.

A few weeks before our second anniversary, he told me he would be home for the entire weekend and wanted us to celebrate together. He suggested that John come over and assist in giving me an enema so we might explore serious anal play when he saw me.

Instantly, my automatic response was to decline. Involving John in such an intimate act filled me with deep embarrassment and vulnerability. The thought of exposing myself in that manner was a boundary I couldn't bring myself to cross. It was a position that struck at the very core of my inhibitions.

He questioned the distinction between involving John in the proposed intimate act and the previous instances where John had waxed me. He also mentioned John measuring me for the new chastity belts, where he had to come over several times to ensure the holes were lining up correctly. Blushing, I found myself at a loss for a solid argument. Time had seemingly flown by, and John had become surprisingly skilled at his duties. His attention to detail in all his assignments sometimes overshadowed the fact that a person was attached to them. Strangely, this meticulousness brought me a certain level of comfort. However, despite this, John still evoked an unsettling feeling within me--a feeling I struggled to define or pinpoint.

I informed Ben that I needed some time to consider his proposition, and for the moment, he seemed satisfied with that response. A few days later, during one of our conversations, he broached the topic of our upcoming anniversary and what gift I would like. I was taken aback, admitting I had no idea what I desired since he had already given me more gifts than I could fathom receiving in a lifetime.

Undeterred, he posed a different question: What was the one item, unrelated to our intimate experiences, that would enhance my quality of life and bring me happiness? I pondered this briefly, reflecting on my daily routines and aspirations. Eventually, I responded, expressing a desire for a new exercise bike. The one I currently owned was a secondhand purchase from a sports store at the onset of the pandemic, but it lacked the comfort and capability to push myself. I longed for a bike that would allow me to exert myself fully and comfortably, enabling me to achieve more significant fitness goals. Without hesitation, Ben embraced the idea, promising to acquire the latest model of the Peloton bike, which would not only meet my fitness needs but also provide access to various classes for added motivation and guidance.

Delighted that I had proposed something Ben approved of, I eagerly inquired about what he desired for our anniversary, feeling somewhat perplexed about what to get for a man who seemingly had everything. To my surprise, he responded swiftly, indicating that he had been waiting for me to ask the question, as he already had a specific request in mind.

With a hint of excitement, he explained that he wanted to engage in a kink scene with me, exploring new rope techniques that had captured much of our recent online discussions. Furthermore, he described a scenario where he would drive me around in the back seat of his four-door pickup truck, simulate a kidnapping, and do anything he wanted to me.

The idea of embarking on such a new and adventurous experience caught me off guard, as we had never explored such rough scenarios before. However, witnessing the eagerness on Ben's face and considering the harmless nature of hiding in a backseat, I agreed to his proposal. This decision elicited a joyful response from him, who expressed how deeply happy I made him and eagerly anticipated the moments when he could dominate me fully.

As the days dwindled until his return, we were engrossed in viewing BDSM erotica pages together. One particular story depicted a Master tying up his Submissive and using various toys to prepare her for anal penetration. According to the narrative, a clean enema was necessary to perform the act without messy complications.

Usually, Ben would read these stories aloud to me while I sat in the open position he preferred, but he requested that I read them aloud to him on this occasion. In my reading, I became immersed in the tale, becoming invested in the outcome, which involved the Submissive requesting an enema to ensure cleanliness and allow for a more intense experience.

As I finished reading the story aloud, a surge of arousal coursed through me, causing wetness to escape and trickle down into the confines of my chastity belt. Ben, noticing my reaction, asked if we could explore something similar when he arrived in town in a few days. Nodding in agreement, I expressed my excitement at the prospect of him engaging with my rear in a pleasurable manner. His enthusiasm was evident as he mentioned that John would visit on Friday early afternoon before I drove to his house, ensuring we wouldn't waste any precious time together. Caught off guard by this sudden arrangement, I nodded, feeling a mix of anticipation and uncertainty. Ben swiftly shifted the conversation to a dress he had ordered for me, diverting my attention to the upcoming weekend.

As Friday arrived, nervous anticipation gripped me tightly. However, as always, John approached the situation with a professional demeanor. He communicated instructions through American Sign Language (ASL), efficiently carrying out his assigned tasks. John precisely conducted the waxing procedure, ensuring a smooth and hairless canvas. Following that, he attentively administered the necessary enemas, addressing the requirements of the upcoming intimate encounters. Once his responsibilities were fulfilled, John packed up his belongings and departed. He maintained a respectful and considerate approach throughout the process, prioritizing my comfort and minimizing potential discomfort or embarrassment.

As the sound of John's departing footsteps echoed in the background, my phone buzzed with an incoming call from Ben. Answering eagerly, I heard Ben's voice on the other end, filled with excitement as he shared the news of his safe arrival and expressed his anticipation to see me. His words reaffirmed my role as a devoted and obedient submissive, and the pride in his voice brought a genuine smile to my face. I ended the call and basked in the warmth of bringing him such happiness.

With a renewed sense of purpose and eagerness, I completed my preparations, ensuring everything was in order before embarking on the two-hour drive to Ben's house.