Chapter 1: Getting into trouble

Even though at the time I didn't know any different, growing up in Caledonia weird and eventful. The island nation, around 50,000 square miles big, had understandably few allies in the region. The female supremacist ideals that governed the nation, insular approach to International relations and perceived low morals hindered any negotiations between other nations that found little in common with us.

The capital town, and principal port of Hamilton on the east coast is the hub of the island nation and with the agricultural lands towards the north and south of the island and industrial heartlands of the west providing, so that the country could prosper.

For myself, a male, life certainly wasn't easy. Over 400 years of tradition were kept alive by Queen Catherine IV, her daughters and the almost all-female Government. Some of these as a lecherous man I could quite enjoy. Hair below the neck was widely considered dirty and unsightly with every man and woman I know shaving daily. Stockings and short skirts were part of almost every official uniform while spankings (often bare-bottomed) were administered in both the school and workplace to punish misbehaviour.

Humiliation, and especially sexual humiliation played a large part in justice throughout the country. For example, a popular punishment for thieves was to tie them to a public rape bench blindfolded for a few hours, so that the good people of Caledonia could take liberties with them, in the same way the thief took the property of others. I remember, a friend of mine being ordered to spend two hours on the local rape bench for the attempted midnight raid on the college tuck shop and heartily enjoying the rather sloppy fuck that I got!

I was lucky as I grew up and attended mixed-sex schools. My town of Cadder, thirty miles to the south of Hamilton and surrounded by untouched woodland and farmers fields was one of the last to convert to single sex education. I was therefore treated, quite often to the sight of a classmate being half-stripped (or even completely stripped) and disciplined! Occasionally for really serious offences, the student in question was denied the right to wear clothes, and on a number of occasions I had a voluptuous naked girl sitting next me proudly displaying her wares for all to see. This made her horny and my break times were often a lot more interesting that the average teenager at school.

Like all everyone growing up, I was under a curfew from 8pm to 6am, which got lifted for the girls when they got to 12 and the guys when they got to 18. My parents both worked at the same food processing plant, my mother the manager and my dad a driver. Both of my older sisters used to take advantage of being home alone and entertain their friends and partners. My first taste of sex was, as a 14-year-old being "forced" to entertain my sisters' friend, Wendy, while my sibling was busy screwing her latest conquest. While I might not have lasted very long first, second or third time out, there was no substitute for my stamina and eagerness to learn. I remember the neighbours complaining to my parents about the amount of noise Wendy made one evening as I was fingering her and found her G-Spot. It was an epiphany for me, truly understanding and enjoying the delights of the female form that would shape the rest of my life. Both of my sisters were forced to apologise to the neighbours and were not prepared to admit that they were out on dates leaving me home-alone! They did get suitable revenge with a particularly sturdy whip and Wendy was asked to stop seeing me, which reluctantly she did when she started dating someone her own age.

After leaving education at sixteen, I hung around Cadder for awhile. The curfew that was still in place until I reached eighteen meant that I couldn't go far, and I was the wrong gender to try and strike out on my own at such a young age. My original plan was to move when I got to eighteen, but I had a stable job as a teaching assistant in my old school and then started dating the Baronesses youngest daughter, so things were starting to work out for me.

Caledonia has around forty baronesses, appointed by the monarch to oversee each town and its immediate vicinity. Baroness Helen Trent was well respected and much loved with conservative views, so I was not liked in her household. Virginia and I used to entertain each other at either my parents house, who obviously enjoyed the fact that we were dating, or local public places. In the back of mind, I knew Virginia was only dating me to rebel against her mother, but I didn't let it trouble me and enjoyed the constant sex and powerful drugs she would supply.

I know Virginia was far from faithful having a string of male and female partners in addition to me. Early on in our relationship, I resigned myself to her promiscuity and even began to embrace it. On several occasions she would arrive at my parents house, drag me to the bedroom and thrust herself on my face to eat her out, with lashings of cum dripping from her drenched pussy. Other times, I would find her kissing or screwing other people at parties, but she always came back to me. Despite having a multitude of partners, she openly admitted that no-one she found could eat pussy as well as myself and very few could find her G-Spot so easily and so despite my low social status and far from good looks, she was happy to stay with me.

In total, we dated for five years before her mother managed to find an eligible boyfriend for her that she would accept. The advances of Andrew, the nephew of Queen Catherine IV, were too alluring for Virginia, and even though she thought he was a vile human being who could not satisfy her in any way, they were married inside three months. ;Unsurprisingly, I was not invited to the wedding, but I managed to sneak in and I cuckolded her new husband within 30 minutes of the ceremony, devouring her clitoris and providing her with much needed release before spearing her with my rod and spewing my juice into her. I watched her return to her new husband from the gardeners shed with my cum seeping down her leg.