Babysitting Oliver by Christina. Christina has presented her story for posting to the blog, hopefully she will be able to continue it. Don't forget that feedback is important in motivating authors.

I thoroughly enjoy reading the accounts of older boys kept in short trousers and subject to early bedtimes while having to wear childish style pyjamas. It is a pity that more boys are not kept in short trousers through their teenage years to remind them they are still little boys and not young adults. Most boys are far more immature than girls of the same age and this should be reflected in how they are dressed and treated by their parents.

I am also in favour of a younger girl having authority over an older boy should the circumstances be warranted. I attended an all girls’ school where the best friend in my class, a girl called Lucy, was given parental authority on her fifteenth birthday over her especially childish, eighteen-year- old brother.

He was expected to obey her without question and she could punish him with very early bedtimes, mouth soapings, and corner time. She also made him wear short trousers at weekends and would smack his legs to add to his humiliation. I was a frequent visitor to her home and was most impressed with the way she strictly controlled her older sibling who was obviously in awe of his authoritarian younger sister. I also have to admit I was somewhat envious.

In the early eighties, when I was seventeen, my parents bought a large mansion flat in Marylebone where our next door neighbours were a married couple and their schoolboy son Oliver, who looked about thirteen. He was always very smartly dressed in complete school uniform which included short grey trousers, grey knee socks turned down at the top, a pale pink blazer, and matching pink cap. His trousers were very short, enough to be almost completely covered by his blazer revealing an expanse of hairless thigh.

I imagined he attended a private Preparatory School where short trousers were still a compulsory part of the uniform. Whenever we met he seemed shy and would blush, an endearing, childish embarrassment with the opposite sex I assumed. Although he could not have been more than five feet three inches tall and had a small frame, he looked just a little too old to still be in short trousers.

We rarely saw the father but my mother and I soon become friends with Oliver’s mother who was an elegant middle-aged lady whom, we soon discovered, had firm old fashioned ideas about how to raise children. Over afternoon tea in our drawing room she revealed that Oliver was, in fact, nineteen, he had been returned to short trousers the year before after being expelled from school for cheating in exams. Now studying for his A Levels by means of private tutors he was expected to wear his school uniform at all times including weekends.  I was shocked but also fascinated that a boy of this age was still dressed and treated as a small child.

Although Oliver was taken out by his mother to visit his tutors he was also taught at home so mummy and I would often see him when we were invited to tea by his mother who talked to him as though he was a mere five-year-old. He would be instructed to make the tea having to wear a pretty white frilled edged pinafore to protect his school uniform. The knee length pinafore, wrapped around his body and was tied in a wide bow at the rear completely hiding his short trousers so giving the impression he was actually wearing a dress, which was no doubt his mother’s intention especially in front of visitors.

I could not resist telling him how sweet he looked and how fortunate he was to have a mummy who dressed him in such lovely clothes. His face would turn crimson with shame but he was sufficiently well trained to politely thank me for the compliment. After serving tea he had to sit quietly cross-legged on the floor next to his mother, who would pat him condescendingly on the head while reminding him that little boys were to be seen and not heard and he should only speak if spoken to first. She also informed us that since he was a child he should always sit on the floor in the presence of visitors.

His mother also informed us that Oliver had a lady babysitter when his parents went out in the evening whose role was to ensure he was dressed in his pretty, infantile pyjamas and in bed by half past seven with lights out within fifteen minutes. A few weeks later I was surprised but delighted to be asked if I would act as his babysitter as the usual lady was unable to attend.

I immediately accepted and was later briefed by his mother on how he should be treated, what pyjamas he should wear, and shown a leather strap hanging up in the kitchen that I should use on his legs and, if necessary, his bare bottom if there was the slightest trouble.

I was about to babysit a boy two years my senior.

I have to confess I was very excited when I entered their flat at six o’clock on the designated evening. Oliver’s parents were smartly dressed and attending a formal dinner and would not be home until late. His mother reminded me in front of Oliver, who was wearing short trousers and schoolboy uniform that if there was the merest whiff of disobedience I should slap the backs of his bare legs hard with the strap.  He had to be in bed with lights out by eight o’clock at the latest.

Once they had left I ordered Oliver to stand to attention in the hallway so I could inspect that he was properly dressed. He looked very nervous but nothing was out of place as I carefully looked at his front and back. I noticed he was wearing a pair of rather girlish, pretty pink T-strap sandals which perfectly matched his pink blazer and cap and told him how sweet he looked in them. He blushed when I told him they were what I would expect a little girl to wear.

“There cannot be many boys of nineteen who are still dressed in short trousers and school uniform by their parents. Are you still dressed by mummy?” I asked, examining his attire.

He looked embarrassedly at the floor but remained silent.

“I asked you a question, little boy”.  He blushed again and mumbled a half-hearted “yes”

“Yes, MISS” I admonished. “Little boys like you must always be respectful when addressing an adult. Say it again and answer the question fully”. He gave a nervous swallow.

Yes, Miss. Mummy dresses me every morning and undresses me for bed at night. I am very sorry Miss that I forgot to address you correctly.”

Leaving him standing I went to the kitchen and collected the leather strap. “I think a few slaps with this might help you remember in future. Put your hands on your head”.

He obeyed and I administered five stinging strokes on the back of each leg. He managed to avoid crying out but I knew it must have hurt as his legs were soon a deep red.

“Say thank you for being slapped”

“Thank you very much, Miss, for slapping my legs and giving me the punishment I fully deserve”. I knew that his mother treated him this way and that he knew the answers he had to give so I ordered him to stand in the corner facing the wall with his hands remaining on his head.

I went into the drawing room to read a magazine and left him for fifteen minutes before summoning him to my presence.

“Oliver.  Come here. I want you to make me a pot of tea as you do it so well for your mummy and her friends. Fetch your pretty white pinny so I can put it on you. We do not want you getting your school uniform dirty, do we? Mummy would be most cross.”

“Yes, Miss.” He mumbled and disappeared into the kitchen and returned holding the pinny which he respectfully handed to me. “Please, Miss will you put me in my pretty pinafore like Mummy does”.

I enjoyed putting his pinny on for him and tied it into a large flouncy bow behind him. He looked like a sweet little girl and very embarrassed at his appearance, but he knew he had to behave.

“Thank you, Miss.”

He returned with the tea on a tray and carefully placed it on the low table adjacent to my chair.

“You will stand there until I tell you to pour it”. I think you could make a rather good housemaid. Would you like to be a housemaid, Oliver, if you ever grow up?” There was hesitation as he was obviously unsure how to reply.

“I am not sure, Miss. I do not think I would be very good around the house”

“Oh, I don’t believe it. Your mummy says you are very good at housework and serving guests especially when you are wearing your pretty pinny. You do love wearing your pretty pinafore, don’t you Oliver?”

The crimson cheeks returned as he attempted a coherent response. “Yes, Miss. I think so.......” He trailed off not knowing what more to say.

“Well, I will suggest to your mummy that she buys you a maid’s uniform so you could be trained properly.  It would be a change from wearing short trousers and being a schoolboy all the time”.

I ordered him to pour my tea and had him remove the tray. Later, and still, in his pinafore, we went to his bedroom so I could select which pyjamas he would wear. He had several outfits which were all very childish with white lace collars and cuffs and adorned with fairies and dolls patterns. I chose a pink pair with pixies and elves. “I will dress you in these for bed tonight”. Actually, we had better get you undressed and changed now”

I had not planned to undress him but his mother had told me to get him ready for bed so it seemed as though I had her authority. His submissive childlike nature also encouraged me to treat him accordingly. I sat on the bed and with him standing in front of me removed his pinafore, his socks, sandals, and school blazer, before unbuttoning his grey short trousers and allowing them to drop to his ankles. Without hesitation, I then pulled down his white underpants revealing a hairless crotch and a small flaccid organ.

“My word isn’t it tiny, but then you are still only a little boy, aren’t  you Oliver?”

“Yes Miss, I am still only a little boy which is why I am so small”

“Well, I hope you are a good little boy and do not touch yourself down there” I gently held his penis in my hand but his obvious extreme nervousness and acute embarrassment meant it remained but a small tassel. I gave it a mischievous squeeze which caused him to cry out and then completed the disrobing and slipped on his pink pyjamas.

As soon as I had tied the small pink bow on his white lace collar he began sucking his thumb which I had been told about by his mother. Evidently, it was an automatic reaction when put into his pyjamas. I perused his collection of dolls and teddy bears that were perched on his dressing table and selected a doll wearing a pink baby sleeping suit, similar to his own, put it into his arms and had him sit on the bed.