I walked to my car proudly wearing my collar and the lipstick Mistress had branded me with. It took a few moments to adjust the chastity cage inside my pants when I sat down in order to allow me to drive with some level of comfort.
I was tired. My body was throbbing and humming and numb all at the same time. My initial thought was to get home, have some food and figure out how to live in a collar and a cage.
While I drove, I recalled the last two days. As I went through all the things I joyously endured to please my Mistress, my pride grew. I was a few blocks from home when I realized I wanted to advertise my pride in being owned by Mistress Raven. I turned into the neighborhood grocery store parking lot and went in. I roamed the aisles slowly. Some people didn't see me, being shrouded within their own world. Others looked away in awe, possibly in fear and possibly in shame for me. Others struggled with staring and avoidance. This last group was the most fun to follow and get close to. I did grab some groceries. The cashier, who was familiar to me, spoke to me and found herself in that last group, wanting to look and take in everything but also not wanting to know what all she saw might mean.
I returned to the car and took a selfie showing the bags of groceries, making sure my collar and lipstick were visible, planning to later share it with Mistress.
I smiled and laughed to myself driving the last few blocks home. I was about to send the grocery store picture to Mistress after putting away my groceries, unable to stop smiling, when another idea hit me.
I went upstairs and put on my tightest jeans, confirming in the mirror that the cage was making an exaggerated bulge in my crotch. I took another picture, then walked the two blocks to the local variety store.
I was obviously a site to behold. There were countless double takes by neighbors, men and women alike, and the owner of the variety store was unable to find a place to look when I stood at the counter asking for several items. I didn't really need anything, I only wanted to extend my stay in their presence. I took a few pictures when they had turned their back.
I sent the photos to Mistress when I got back home, thanking her for making me so proud. She simply said, "Good boy."
My sleep was fitful trying to get used to wearing a cage. In the morning I showered then spent a little more time than usual trying to find clothes that wouldn't loudly advertise my predicament to my co-workers.
At 9:50 I received a text message from Mistress.
"Go to the bathroom. Strip and send me a picture so I know you are complying with my rules. I want the picture in the next 15 minutes or you will pay on your next visit if it takes longer."
I had 10 minutes before my next meeting. Grabbing what I needed for that meeting I rushed into the bathroom, stripped and sent the photos. I received no reply from Mistress and was 2 minutes late for my meeting.
I received the same request at 2:50 and 4:50. I accepted Mistress' timing to account for the possibility I was in a meeting. I appreciated that.
Tuesday morning when I woke up I had a text message from Mistress. "Wear tight underwear today and snug pants. Send me photos before you leave for work. You need my approval before leaving. You must also send me a video of you peeing at a urinal sometime today."
So much for not advertising my cock in a cage situation at work. I selected pants a little tighter than may have been required but I didn't really have time to go through several changes before leaving. Mistress approved the first set of photos I sent to her.
I did get several looks from people at on the train and at work. Some in disgust, some might have been women expressing interest in a characteristic of me they hadn't noticed before. I didn't understand the significance of the tight underwear at first, but once I had to sit down and move about, I realized the tight underwear didn't allow me to easily adjust the position of the cage.
I sent two sets of photos during the day showing my cage pressing against my pants and naked. The urinal video took some time to set up, trying to hold my phone, my caged cock outside my pants not splashing all over me and not having my pants fall to the floor. I will admit, I did splash some urine on my trousers and shoes. It was nothing some paper towel couldn't tidy up.
Tuesday night at 8:00pm I started preparing for my visit to Mistress Raven. After picking out the clothes I would wear, I packed a bag with work clothes for Wednesday in case Mistress made me to stay overnight.
I went through my standard cleaning ritual before flushing my ass with the enemas. I stopped after 4 and showered once more to make sure I was ready for my Mistress.
After my second shower, I saw I had a text message. It was from Mistress, telling me to wait in my car until she texted me in case her session ran long. I affixed my collar just before leaving my house.
I arrived 10 minutes early and waited in my car for Mistress' text message. I had trouble containing my excitement. Her message arrived at 9:37.
"Come in now. Knock lightly when you arrive. Step inside my door and strip without uttering a word. I will inspect you before you are allowed any further into my home."
"Yes Mistress. Coming now Mistress." I replied.
I was so filled with anticipation and excitement that my cock was already pushing against the cage. I knocked on Mistress Raven's door. I stepped inside and set down my bag when it opened. I immediately started undressing.
"You're much too slow. Next time you will undress in the hall before you knock on the door. What's in the bag?"
"Yes Mistress. Clothes for work tomorrow in case you need me to stay overnight."
"Wise. If you stay it will be to work or if I want you in the morning. If you stay, you will sleep in the cage, not in my bed."
"Yes Mistress."
"Come."
I followed Mistress into her dungeon. The bench was in the middle of the room, a stop watch next to peg 7, lube beside peg 1.
"Bring me the watch and get started. Your time had better improve. I am too tired to have to punish you for a poor time. I will if I must but it will not be pleasant for either of us."
"Yes Mistress."
"HURRY!" Mistress Raven screamed at me.
I ran retrieving the stop watch and racing back to the first peg. Mistress must not have enjoyed her client.
I lightly greased the first peg and my ass. Down. I only felt a small ouch at the initial penetration. Up, down. Mistress called out 'one'. I was rushing. The cage was crushing my balls whenever I bottomed out on the bench. Up, down, two. Fuck this anal stimulation was again filling my cock making the cage tug on my testicles. Up, in my haste the peg came out of my ass.
"FUCK! WHAT AM I GOING TO DO WITH YOU? DID YOU NOT HEAR ME SAY I'M TIRED! YOU HAVE TWO MINUTES STARTING NOW TO GET PEG 4 IN YOU ASS AND THREE COUNTS OR YOUR NIGHT WILL BE LONGER THAN YOU CAN IMAGINE!"
"Yes Mistress. Sorry Mistress."
Now I really focused on keeping the peg in my ass but moving quickly and still getting at least half the peg out on each trip up its length.
Up, Down, Zero. Up Down One. I squeezed lube onto my hand and greased the second peg. Up Down Two. Up Down Three.
I sat down on peg number 2 not caring about it's additional girth. Up Down One. Up down two. I squirted more lube into my hand. A huge glob came out. Much more than I wanted.
"1 minute" I heard Mistress announce.
Up Down Three, while I was greasing peg 3 trying to save some of the lube for peg four, I stood up, the bottle of lube slipped out of my hand and rolled about five steps away. I would retrieve it after I was done riding the fourth peg.
Up Down One. I reached for the fourth peg to use up some of the lube I was still holding in my hands. Up down two.
"30 seconds. You've done so well on these pegs, you're only getting an additional 2 minutes for the last three. Don't make me have to punish you. I'm tired and when I'm tired, I get cruel and I don't like being cruel."
"Yes Mistress. Thank you Mistress."
Up Down Three. I looked at the bottle of lube. Five steps there, five steps back. No time. I sat down on the fourth peg and essentially fucked it, riding up and down three times in the last 20 seconds.
Two minutes. Three huge pegs. I stripped whatever lube I could from pegs 3 and 4 as I stood up, running my hands down the next two pegs.
"Ugh." I grunted, sitting down on the fifth peg. My balls stirred and throbbed. My ass stung. My cock ached, bent and scrunched inside the cage. Holy fuck. Up Down. No count. I grimaced. I leaned forward putting both hands on the bench. I made peg 5 a lover, riding it for three fast pumps. One. Two. Three. Mistress counted for me.
I grabbed peg 5 while I stepped to peg 6 but couldn't find any lube to speak of for the last peg. I stripped what I could from peg 6 before starting my journey down.
"Ahhhhhhh" I half moaned, half screamed when the peg first penetrated me. Fuck it was thick and long. My ass wavered between pain and joy while I slid down to the bottom. My first trip up was slow and the trip back down even slower. One.
"One minute left."
Fuck. I wasn't half way through the last three pegs. I closed my eyes and bit my lower lip.
"HMMMM." I grunted on trip two.
Two.
"HMMMMMMMMM". A longer grunt on trip three. But no count.
"MMMMMMMMMM!" I pushed up until I felt the tip about to leave my anus then let go allowing gravity to haul me back down forsaking all control of my descent.
"Three."
I was off peg 6 and just getting onto the all but dry peg 7 when Mistress called out "30 seconds."
I did not want to disappoint Mistress. I had less than 8 seconds per slide on peg 7. The first one down never counted for anything.
Peg 7 stretched and filled me. My ass was sore having gone so quickly on the first six pegs, not having given my anus time to adjust to the widening girths. It felt like a long time sliding 7 into me. I went to town fucking peg 7 with reckless abandonment.
"One. Two. Remain sitting there when you're done. Three." My mistress called out.
I sat there with peg 7 buried inside me. I had broken out in a cold sweat from the stress and discomfort. My anus pulsated around the peg unable to eject it, trying to embrace it. Mistress moved about the room. I didn't watch what she was doing.
"You dropped this", Mistress Raven said, handing me the bottle of lube. "That is the only thing I will help you clean up tonight."
"Thank you Mistress". I said, taking the bottle from her, unsure what I was supposed to with it.
"You were 4 seconds over your time. You surprised me. I didn't think you would get close to completing in the time I gave you."
"I tried Mistress. I did not want to disappoint you. You said you are tired. I did not want you to have spend energy punishing me."
"You did well. Your Mistress is pleased, but I still must punish you some for going over your time. Your nipples have been ignored tonight. Sit up straight so I can attach these."
Before I got completely straight, Mistress grabbed my right nipple, pinching it hard and attaching a clamp. My nipples had been awakened fucking the pegs. I wasn't aware that had happened until Mistress Raven touched me. I whimpered. Before the pain had eased my left nipple was in the grasp of the other clamp.
