When I left school, I started work in a small office. The staff consisted of the owner and four other ladies. I have changed all names to protect their privacy.
I was the sole male worker and very much younger than the others. One of the reasons I got the job was that the owner wanted a man for the heavier tasks, in addition to the usual office duties.
I was so proud on my first day but very apprehensive. One of the ladies, Mary, was assigned as my mentor. She was in her 40s, with blonde hair and very beautiful. She loved to flirt and wore tight, short skirts and low-cut blouses. I was in my element and thoroughly enjoying myself.
After the first initial few weeks, I found the ladies got cheekier and made more comments about me. Nothing nasty, just rather risqué at times. Shirley, another worker, would frequently pat my bottom if I went past her and make cheeky comments. Mary loved making remarks about my manhood and what she would love to do with it. Only one lady, Jackie, seemed less involved – she was in her 20 and single. She sometimes apologised privately to me when I was obviously embarrassed.
After a couple of months, my 17th birthday came around. One of the ladies produced a cake, and I thought everything was great until the end of the day.
At five o’clock, Mary grabbed me and before I knew it the women had debagged me and I was over Mary’s knee and clamped between her legs. I could feel my penis stiffen and Mary obviously noticed. Then she started – one smack on the left buttock, followed by one on the right. She continued at a steady pace and despite my trying to fidget, she had me trapped. Eventually she stopped and everyone sang happy birthday to me. I was then embarrassed completely, as each of the ladies gave me a birthday kiss.
The day finished and I went out to meet my mates in the local pub. Even though I was only 17, the landlord had a habit of turning a blind eye. Indeed, I had even been here while at school during lunch break and got caught once, resulting in six of the best with the cane.
I didn’t mention my birthday spanking to my mates, and the evening was going well until a lady tapped me on the shoulder. To my surprise it was one of my former teachers, Miss Archer, looking gorgeous in a short tight skirt, clingy blouse and high heels, obviously not her school attire.
She smiled and remarked that I would have got caned for drinking if I was still at school. I pointed out that I wasn’t, so had done nothing wrong. However, she was quick to point out that I was still under-age. Cheekily, I remarked: “You’d better cane me, then, miss!” She merely smiled. “Come back to me to my flat and I’ll be happy to oblige.” My manhood immediately stirred and I was hooked. I made my excuses to my mates and walked out with my former teacher.
Her flat was close by and we were soon there. She opened the door and invited me in. I was so excited, as she was a looker and one of my favourite teachers, even though she had sent me for a caning at school. She told me to get ready while she found a cane, and returned quite quickly with one, very long and whippy, with a traditional crook handle. She played with it in her hands and my trousers clearly bulged as I stared at her, deliberately playing with my emotions.
Finally, Miss Archer pulled the curtains to stop any prying eyes. “Peter, you will receive six strokes of the cane on your bare bottom. Now, take down your trousers and pants.” I did as she instructed and my erection was soon on view.
I bent over the table carefully and waited for the discipline to begin. Miss Archer slowly came alongside me and carefully rolled up my shirt to properly bare my bottom. As she did so, she observed the reddening on my rump from my earlier spanking.
“Been a naughty boy already, have we?” “It…it was my birthday, Miss.” “Yes, I know – I heard your mates talking about it back in the pub.”
I felt the cane touching my bare bottom and Miss Archer tapped it playfully a few times against my buttocks. Before I knew it, the cane swished down hard. It produced more pain than Mrs Halsall’s senior cane had at school. Four more times she repeated the dose, almost bringing me to tears. The final stroke was whipped down hard and low, causing me to jump up. When I turned around, she had a smug grin on her face. “That’ll be an extra stroke for standing up, Peter.” Obediently, I slowly bent back over and she applied the cane hard.
I stayed down this time. Miss Archer slowly felt up my bottom and seemed to be admiring her handiwork. Finally, she told me to stand up and I faced her, revealing a throbbing erection standing fully to attention. Miss Archer smiled again: “Well, someone obviously enjoyed themselves,” she said.
She suggested I should stay for a drink and I carefully eased myself down into an armchair, not even bothering to dress. She disappeared briefly and came back with two glasses of wine. She sat opposite me, teasing me by crossing her legs several times, making her skirt ride up.
We soon finished our wine but disappointing, she indicated that I should get dressed and go back to my mates. Reluctantly, I did so but I hinted at a ‘rematch’. Miss Archer grinned: “Same time next week, then?” Feeling the hormones raging through my body, I quickly agreed and even dared to give her a quick peck on the cheek as I took my leave.
When I returned to the pub, my mates asked me what happened. I bigged up the occasion, and told them Miss Archer she had given me a handjob for my birthday. They laughed and made various, predictable crude comments.
I visited Miss Archer the following week and for several weeks after that. We got closer over time and sex soon followed. These liaisons continued for several months until she said they had to stop, as she was now in a relationship with a man nearer her age. Whoever he was, he was a very lucky man!