By @CPEnthusiast (t)

A Compulsory Caning 

Nanny told me that tomorrow I would report to Miss Tahlia for a compulsory caning.  She said that as I had grown into a young man, I must be able to take the cane from Miss Tahlia on a regular basis.  Nanny said that she would still spank me every day, but from now on I would report to Miss Tahlia once a week to be thoroughly caned.

Miss Tahlia believed strongly in frequent, compulsory canings for a young man.  She liked to “separate the men from the boys” and Nanny said it was in my best interests to bend over for Miss Tahlia and take it like a man from her.

Nanny was to attend my first caning and we would go together to Miss Tahlia’s office in the morning.  Nanny promised me a good long spanking first, as it was better to get the cane on a nice warm bottom.  Even so, Nanny said that Miss Tahlia would give me a very sore bottom indeed.  After answering a few more questions about Miss Tahlia’s compulsory canings, Nanny gave me my nightly spanking and put me to bed.

Nanny came to my room after breakfast the next day to prepare me for the caning.  Miss Tahlia insisted that a young man be properly presented and attired for the cane.  I undressed completely and Nanny bound up my testicles with an old silk stocking, then wound another stocking round and round my erection as tight as possible.  I always got an erection as soon as Nanny touched me.  She said Miss Tahlia liked a boy to be “on edge” before a caning. After Nanny had expertly trussed me up, I had to put on a pair of soft, silky caning shorts.  Miss Tahlia liked to have a young man in soft, feminine underwear for a caning, as, in her opinion, it enhanced the experience for all involved.

As a final preparation, Nanny got her hairbrush, took me over her warm and sumptuous lap and spanked me soundly.  It was wonderful to feel the sting of Nanny’s hairbrush through the tight, silky caning shorts and I wondered how Miss Tahlia’s cane would feel and how hard she would cane me.  After a few minutes my bottom was warm and throbbing and my erection had grown further in the tight silken sheath in which it was encased.

Miss Tahlia was sitting on her desk holding a cane when Nanny and I entered her office.  Miss Tahlia drew attention to the bulge in the front of my shorts with her cane and commended Nanny on bringing me to her in a state of such heightened anticipation.  Nanny continued to pat my bottom as Miss Tahlia explained the need for compulsory canings and asked whether I was going to be a brave boy and take it like a man for her.  I agreed I would try my best for her.

Miss Tahlia stood up.  She looked magnificently strict and sexy in her short skirt, stockings and heels and the fire of the enthusiastic caner glowed in her eyes.  She flexed and swished her cane and said that as it was my first caning from her, she would allow me the comfort of Nanny’s lap.  Nanny sat on the desk and I went right over her lap, with my bottom pushed up into the air, so that Miss Tahlia could take a proper swing at me.

Miss Tahlia started with six “swishes” to get us started, while Nanny acted as “erection monitor”.  When Nanny reported that I had twitched at every stroke and that I was as hard as before, Miss Tahlia seemed pleased with this turn of events and decided on six “stingers” to follow, which were followed by six more.  These really stung even through the shorts that were drawn drum-tight across my bottom.

Miss Tahlia was, indeed, a skilful and enthusiastic caner.  Her cane made a tremendous sound as it swished through the air and landed with a crisply satisfying crack, beautifully across both cheeks of my bottom. Throughout the caning I was aware of her slim, athletic figure, and flowing movements as she administered the cane and worked her disciplinary magic.   After two dozen of Miss Tahlia’s best, I no longer felt the each stroke as a separate burning line across my bottom, but as a general suffusion of heat across a larger area.

I held myself still for her and didn’t cry out, but only gasped when she caught me with her best strokes, which were some real beauties.  Miss Tahlia occasionally encouraged me by saying “good boy”, when she saw me endure a particularly juicy stroke.

Miss Tahlia eventually decided that forty-eight strokes of the cane were sufficient for a first compulsory caning.  Miss Tahlia had given me three dozen over Nanny’s lap, then had me bending over her desk for the final two sets of “six of the best”, while Nanny looked on.

After the caning, I remained bent over Miss Tahlia’s desk while my shorts were pulled down and the two ladies took a closer look at my well-caned bottom.  Nanny fetched some soothing cream and applied it to the welts on my bottom, while Miss Tahlia, looking slightly flushed, sat at her desk.  Looking me in the eye, she mused on the excellence of the caning she had given me and anticipated the compulsory canings that lay ahead of us.