I inserted the internet remote controlled Hush butt plug as she had instructed. It was not the largest plug the company made, but it was larger enough that it took me fifteen to twenty minutes to insert it in my tight asshole the first time I used it. Initially I had to lie down on my side to get the plug in. Lately, the weeks of anal training were paying off and the insertion process went much quicker and smoother. Once the largest girth was inside me, the thinner stem did not make my sphincter ache. The plug’s vibrations could be operated by an application that Mistress Wilma had installed on her phone.
“It is in, Mistress.” I texted her.
“Good slave.” She texted back.
The vibration began immediately, and my phone showed that it was a twenty-minute pattern that she had initiated. The intensity gradually became stronger and then ebbed, radiating quivering sensations throughout my buttocks and causing my cock to drip pre-cum. Mistress Wilma had instructed me that I was not allowed to cum unless she explicitly instructed me to do so. My cock tried to swell up in the confined space of its rubber cage, the meat of the shaft trying to bulge through the small air holes along the device.
I writhed my ass against the Lazy-boy chair seat, trying to accommodate the vibrations and the feeling of fullness against my prostate. After a while, my writing became more rhythmic and I was humping the chair with the part of the plug that was external, making the vibrating portion inside of me swirl around and rub my colon and my organs internally. The vibrations would occasionally reach a crescendo and cause me to jostle and wriggle.
Mistress Wilma had been training me ever since I had asked her if she would be my keyholder. We had met online via a BDSM “dating” website, and I had approached her to see if she might be interested in using me for her amusement. She had a long-term plan in mind: after suitably training me and having me prove me devotion and worthiness, she would allow me to be her servant and driver for a local outdoor festival for her birthday. She told me that since I lived several hours drive away from her, that I would be allowed to stay overnight the night before the festival and would be allowed to participate in a play party she was having the night before the fest. She told me that I would have to be chained to the bed in her dungeon when she went to bed, and text her as soon as I woke up. I would be expected to wear the butt plug while serving her and her guests and allow them to use the remote whenever they felt it would be fun.
The vibrations in my ass faded and then stopped, and a check on my phone showed that the pattern she had sent was complete.
“The pattern completed, Mistress.” I texted her.
“Good boi.” She texted back. Another pattern was sent, this one more intense and sustained. I checked and saw that it was for ten minutes.
I tried to watch the “Game of Thrones” series that I was binging. I could follow the story for a little while when the vibrations let up, but as soon as they went wild, so did my concentration. My cock was making a puddle that leaked from the end of my cock cage. The cage had a hole in it at the end to allow one to pee (sitting down, of course) and this also provided a conduit for leaky cum emissions.
“I am leaking, Mistress” I hesitantly texted her.
“Scoop it up with your finger and eat it, boi!” She replied.
I did as she instructed and was getting used to the taste after so many sessions. She had me use the plug for an hour every other day. I appreciated her attention and the promptness with which she kept track of the time and would tell me to remove the plug after the hour had elapsed. I also loved that she would do random spot checks on me and send her a picture on the chat application we used.
The woman i had lived with for several years was on another of her several month excursions away from the house, under the pretense that she was fixing up the house she owned in her home state. I had no reason to suspect that she was seeing other men, though the time she spent away was adding up and my interest in finding a true Domme to serve was moving in my mind from a fantasy to a possibility. I had contacted several Dommes who showed interest in having me serve them and had set up introductory interviews with two of them. One of them was a Domme who had trained me to eat my own cum, but that is another story.
The other was Mistress Wilma, who lived several hours driving time away from me, so She decided to allow me to do my anal training remotely and kept track that I was wearing my chastity device for her as instructed. She would periodically have me send a picture of the plastic numbered lock to ensure that I had not taken it off without Her permission. Every few days She would allow me to remove the device for cleaning and instructed me how many times I should edge before putting it back on.
During one conversation with my absent housemate, in the interest of honesty, I told her about the fact that I had been talking to Dommes in hopes of serving them. She was surprised and asked me why I had not told her earlier about wanting to be a full-time submissive. I told her that I thought she would be repulsed and leave me. She responded that I could try out these other Dommes for now, but when she got back, she would show me that she knows a thing or two about being a strong Domme. She and I wrenched our souls through the rest of the conversation and the following weeks appeared that she might not come back at all.
My reverence of Mistress Wilma’s power, skill at being a Domme, and my devotion to Her desires and excitement every time She contacted me was growing daily. The collar of the chastity device felt like having Her thumb and forefinger wrapped around the base of my shaft and served as a constant reminder of Her increasing control over me. She would occasionally tell me which color panties she wanted me to wear to work under my suit trousers. The feel of the lace and silky panties rubbed the skin that was exposed from the chastity device, randomly causing a wickedly intense tickling sensation in my confined penis when the fabric would find a way to brush against the skin under one of the ventilation holes in the shaft of the device.
During one of my remote-control anal training sessions, Mistress Wilma had passed Her phone around at a Femdom munch and allowed several different Dommes to use my ass for their entertainment. She said that they had laughed and found it to be a lot of fun.
As the day approached for my trip to serve Her and Her friends for the event, I became more and more excited. I had managed to be able to wear the vibrating butt plug for several hours at a time and had used larger and larger plugs to gradually open up my anus to accept them. I would worship Her pictures on Her profile. She would periodically tease me with new pictures of Her feet, or Her tanning naked by Her pool.
The day of my trip to meet Her finally arrived and I packed up a small knapsack with some clothes, including the button-down shirt, khakis, and panties She instructed me to bring as my uniform for the festival. I also brought my plugs, several tubes of lube, some cock rings, and a face gag with a phallus that She could ride if She so desired. I was still locked in my chastity device and pulled off the highway when I was about an hour away from Her house to insert the vibrating plug to wear for the remainder of the ride.
My heart was racing as I got out of my car and opened Her back gate and saw Her sitting on Her back porch. I had been texting Her to let Her know how close I was getting to Her house along the way, so She was expecting me as I entered Her yard. I closed the gate worried that perhaps I would not meet with Her approval in person, and She might send me home. She beckoned me into the porch and had me kneel down in front of Her to begin the interview. I set my knapsack aside and focused on Her bare feet.
“Well barney boi, tell me about yourself, and how you see yourself meeting my expectations,” She began, “Why do deserve to serve Me?” she asked.
Relieved to be allowed to speak, I told her of my past experiences, my training, my situation with my housemate. I poured my heart our to Her, expressing my complete and total devotion to Her, and listed the things that She had told me She enjoyed or expected and told Her of how I could best do my part to fulfil those expectations. The conversation went on for twenty to thirty minutes while She vetted me to make sure I wasn’t a psycho or an unhinged person. After She was comfortable that I was truly there to attend to Her wants and desires and nothing else, She led me inside and had me put my knapsack in the attic dungeon and come directly back downstairs. I complied with her command and took a quick look around the dungeon as I dropped off my stuff.
The dungeon walls were painted red, and a large St. Andrews cross took up on wall. There were several couches and chairs placed around the room, and a spanking/pegging bench occupied a section of the layout. A short fight of few stairs led up to a closed door. I hurried back downstairs quickly and awaited my next instructions.
“Take these cleaning supplies and trash bags and go clean out my van,” She told me, “Since you will be the chauffer tomorrow, it is your responsibility to make sure that the van is cleaned out. And when you are done, come tell me so I can inspect how well you did the job I have given you.” I was adequately motivated to do the best job I could to avoid warranting Her wrath or worse, being dismissed.
After cleaning the van for forty-five minutes, I had cleared out the trash, vacuumed the interior, wiped, and shined all the upholstery, and carried the ice chests and bags of picnic blankets, cups, and paper plates out to the van. Mistress Wilma had been occasionally activating the internet remote control of the butt-plug to distract me and entertain Her as I worked. When I had finished, I went back inside and let Mistress Wilma know that I had completed the task and asked Her to inspect my work to see if it met with Her approval.