I woke on Saturday morning and immediately bent over to inspect the damage done to my poor bottom. Seven stripes were clearly visible and although the pain had faded, they were still painful to touch. I ran my fingers along the marks and became aroused at the memory of the previous evening. Vivien was the dominant woman of my dreams. My mind wandered forward to next week would I be made to sit on the stool of shame, and would she use a strap-on? Fear, shame, and excitement all competed for my attention.
The rest of the weekend passed with my mind constantly thinking about Vivien. It was extremely hard to concentrate on anything. On Sunday evening I received an e-mail from Fiona breaking off our relationship. I was surprised she did not have the courage to do this in person but not surprised that it had ended. An hour later I received an e-mail from Vivien telling me she still expected to see me on Friday, even though my relationship with her daughter had ended. She reminded me that I would not like Fiona to know what she had seen me doing when she had caught me spanking my bottom and sniffing her daughters’ dirty panties. Although she was right, I would not have wanted Fiona to know our secret. I would have visited Vivien in any case, despite my fear, there was also considerable excitement.
The week dragged by, and work was a chore and I found it hard to concentrate but Friday finally arrived. On Friday I received a text from Vivien, reminding me not to be late but also that I needed to bring a condom with me. The thought of what the condom was to be used for filled me with dread. I have toyed with my anus on occasion and do enjoy the feeling, but that is as far as it has ever gone. Having seen the phallus attached to the stool of shame last week I could not imagine what it would feel like being inserted into my back passage. Would she also use a strap-on as she had promised? What would that feel like? I did however go to the pharmacy at lunchtime and buy a packet of condoms.
I left work early and went home to bathe, shave, and make myself presentable. I spent longer than usual making sure the whole of my backside was clean. I left in plenty of time, I did not want to be late. Fear was taking over my emotions as I drove across town.
I knocked on her front door at five to seven and was met by Vivien. “I do like punctuality; it does show respect.”
I was let into the hall. “Go into the office and remove all your clothing, place the condom on the desk, then stand facing the desk and wait for me.”
I entered the office and the first thing I saw was the stool of shame, it had a bright red phallus attached. This was smaller than the one I had seen last week; it was about four inches long with a reasonable girth. I did not think my heart rate could increase, I was wrong, my heart was hammering in my chest. I undressed quickly and stood as requested. There was a towel neatly folded on the desk I placed the condom on this as instructed. My penis was starting to get erect; I would be lying if I said none of this was exciting.
Vivien entered and took her seat.
“This seems to excite you, am I right?”
“I am both terrified and excited at the same time,” I answered honestly.
“What did I say was going to happen here today?” I was asked.
“You are going to complete my caning.”
“Is that all? I thought I had mentioned other things or was I mistaken?”
“You also said I was to sit on the stool of shame and that you would use a strap-on.” My cock twitched.
Vivien noticed this and smiled. “Has anything like this happened to you previously?”
“No, nothing of the sort.” My mouth and throat were getting dry.
“But you would like it too, am I correct?”
“I have been thinking about it all week.”
“Let us begin. I would like you to put the condom on the phallus this is the first step to prepare it for entry.”
With shaking hands, I picked up the condom and removed it from the packet. I stepped over to the phallus and knelt to do as I had been told. Up close it was very realistic, it had a large head and a veined shaft. I could only imagine what this would feel like entering me. I peeled the condom over the crown of the phallus and rolled it down to cover the full length.
“You may like to use this,” Vivien said. She was holding a white plastic container. “It is lube, if you want to coat the dildo it will ease its passage.”
I took the bottle squeezed a generous handful and coated the phallus.
“Stand before the desk and bend over and rest your chest on its surface.” I did as requested. Vivien took a pair of black PVC gloves from her top drawer. She slowly put these on taking her time over each finger to ensure a snug fit. I was fascinated by what she was doing. “Do you like my hands in these?”
“Yes,” I answered honestly.
“That is the right answer, now reach behind and hold your buttocks open for me.
I did as I was asked. I was feeling very exposed holding myself like this. Vivien stood and walked behind me.
“I need to lubricate you.” With this, I felt the bottle of lube at the top of my crack, and then I felt the lube running down the valley between my buttocks. As the flow reached my anus, Vivien’s finger pushed against my back passage. I clenched to resist her probing. “You will relax,” Vivien said in a tone that suggested I had better do as instructed. Her finger slowly entered me, I breathed out and tried to get used to the feeling. She pushed her finger right up my rear passage and then finger fucked my arse. This was not unpleasant once I got over the shock.
“That is nice and ready, please bring the stool over and set it before the desk.”
She withdrew her finger and wiped her hands on the towel. I placed the stool as requested and stood awaiting my fate.
“Holding your buttocks apart lower yourself so you are positioned just above the dildo.”
I lowered myself and felt the head of the phallus just next to my anus. Vivien positioned the head of the penis at my entrance. “Now if you relax it will be easier for you. I will guide its entry.”
I took a deep breath and tried to relax. I lowered myself and felt the head pushing for entry and gradually I stretched to accommodate it. Once the head had breached my entrance the rest slid in easily. I was seated on the stool and the phallus was inside me.
Vivien sat back at her desk, and we faced each other.
“Comfy?”
“No, not really, it feels huge back there.”
“It is part of your punishment; you can stay in position for five minutes.”
We settled into an uneasy silence for a couple of minutes. Vivien then stood and I watched her walk over to the bookcase and retrieve the cane. She flexed it between her hands and swished it through the air. I tensed on the dildo imagining the cane contacting my bottom.
“Will I need to gag you again?”
“I think that would be best.”
Vivien reached behind herself to unzip her skirt and delicately stepped out of the garment. She was wearing white stockings supported by a white garter belt. Her panties were a white satin which she drew down and wiped her crotch with them. “Open wide.”
I did and her panties filled my mouth, I could taste her arousal.
“It is time for the cane. Bend over the desk again, six strokes coming up. Please stay still or this number will increase.”
I eased myself off the dildo and felt immediate relief once I stood. Fear of the caning now filled my thoughts. I could not believe how much the cane had hurt last week and I knew enough about Vivien to know I would receive no mercy this week.
“Bottom right out, I need a good target for the cane to be most effective.”
I pushed my bottom out. The cane tapped and I shuddered. I watched Vivien in the mirror as she withdrew the cane and brought it down hard for the first stroke. A line of fire was ignited, and I shouted into my gag. I did however manage to stay in position.
“Well done,” this was high praise indeed from Vivien. “Next one coming up.”
The rest of the caning proceeded with me getting increasingly desperate to stay in position and tears rolled down my face. I barely coped with my punishment, but I did get through the ordeal. My bottom was on fire at the end.
Vivien removed my gag and said. “I would like you to service my pussy. Please stand.”
I did as a was told and Vivien stood before me. She leaned back onto the desk and opened her legs, “kneel and you may begin.”
I knelt and was faced with her pussy, neatly trimmed and I could tell she was very aroused. I went about my task with pleasure and quickly found Vivien’s hotspots with my tongue. Soon she was pushing herself into my face and she quickly achieved her peak.
When she came down, she said. “You do have potential.” Again, I took this as high praise. “You may stand.”
I stood and Vivien walked around the desk and opened one of the drawers. She took out a strap-on, this time with a black phallus. “The final part of your punishment.” I stood and watched as she stepped into the harness and adjusted herself so that the penis was firmly in place. She then returned to stand in front of me.
“Have you ever sucked a cock?”
“No,” I replied.
“Well, there is a first time for everything, you may kneel and worship my cock.”
I was much more reluctant to comply, but I did kneel and tentatively took hold of the penis and put my lips against its head. I opened my mouth and swallowed the penis, it filled my mouth and felt very strange. I would never have thought so but it was strangely exciting being made to do this.
“Worship me properly.”
I withdrew the phallus from my mouth and started to fuck my mouth with the penis. After a couple of minutes. Vivien spoke. “Let’s finish the job shall we, lie on your back on top of the desk. Draw your knees onto your chest and hold them apart for me.”
I got myself into the position required and saw Vivien reapplying lube to her fingers before she invaded my rear passage again.
“I want you nice and ready.”
Once she was satisfied, she addressed the top of the penis to my small opening.
“If you relax it will be easier for you.”
I tried but it was exceedingly difficult. I felt the tip of the penis push at my opening then it gradually invaded my rectum, it was only about four inches long, but it felt enormous inside me. Vivien slowly inserted the entire length inside. She then paused and said. “That is all for this week, next week if you take twelve cane strokes and a five-minute strap-on fuck I will reward you by letting you fuck me. Would you like that?”
Even with my knees on my chest and my bottom on fire both inside and out. I could only reply. “Yes, absolutely that would be wonderful.”
Vivien withdrew from me.
“Right, you may shower and make yourself presentable. I will see you next Friday at seven.”
With this still wearing her strap-on, she left the room. I did not see her again before I left.
The End.
