Pirates of Caledonia I : a Journey Into the Unknown
Chapter 1: Getting into trouble
Caution: This BDSM Sex Story contains strong sexual content, including Ma/Fa, Fa/Fa, Consensual, NonConsensual, Lesbian, Heterosexual, Fiction, Historical, FemaleDom, Spanking, Oral Sex, Anal Sex, Sex Toys, Military,
Desc: BDSM Sex Story: Chapter 1: Getting into trouble - On a land where the women are dominant, a young man finds that curiosity can lead him into trouble, as he stumbles across a pirate ship and has the adventure of a lifetime being a Cabin Boy to a dominant captain amid forty horny women.
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.
Having had such a serious relationship with one of the most of eligible sphincters in the area did wonders for my status and I entered into a string of failed relationships. I could never find any girl that I liked enough to stay faithful to, and after a few weeks of dating, none of my new partners really wanted to date a teaching assistant and so finally, at the age of 24, I did something I wanted to do at 18. I left home for headed to Hamilton.
I arrived in Hamilton in early March and using some meagre resources of what I had saved from my teaching job, I found a small room to rent with a husband and wife for three months not far from the Docks. Even though I all my job interviews were unsuccessful, I was enjoying Hamilton with a string of one-night stands with married women. I was however fast running out of money and even though I managed to extend my stay at the house by another month for providing the wife with the oral service her husband couldn't when he wasn't around, I was preparing for the nightmare of returning home before the end of the July.
I managed a further stay of execution when the Mark, the husband, had to go away for a couple of weeks to help look after his sick mother, who lived over 100 miles away. He asked me to make sure that no harm came to his wife while he was away, but in truth we spent little time out of the bedroom. Lucy was insatiable, demanding satisfaction several times a day, and even when she said she couldn't take any more multiple orgasms, I would continue massaging her G-Spot and feasting on her slit to bring her to untold levels of pleasure. In all the time I was in Hamilton, I only had full intercourse once. I learnt relatively quickly that my sexual technique and penis size are average and I could best please my partners by relentlessly devouring and probing their slits. It often left me feeling slightly unfulfilled, but as the years went on, I sought my pleasure through others and a hand-job after hours of heavenly pussy-eating would always leave me incredibly satisfied.
All good things must come to an end, and Mark returned home unexpectedly one lunchtime as his loving wife was bobbing up and down on my face. Humiliated and angry, I was told to leave and didn't hang around long enough to hear Lucy confess to him all her past infidelities with myself, and others before me and the reason why. Packing my bags in record time, I said my goodbyes and headed into Hamilton, with no money to return home and nowhere to go.
I remembered that one of the wives I had slept with repeatedly in my early days in Hamilton, lived on the Docks as her husband worked on the passenger ship while she worked at the freight terminal. She was well-connected and would certainly be able to arrange for me to get back to Cadder in exchange for a little fun. I had spent little time at the Docks in daylight, and vast areas of it were restricted to authorised personnel only. I remembered her house, one of a block of ten or so, was at the opposite end of the Docks to the ferry terminal and walked along the main road going South.
Machinery whirred almost everywhere as people hurried pushing huge trolleys laden with goods. As I walked further away from the passenger terminal, the amount of people thinned until I was almost on my own. Looking round, I thought I spotted the block of houses in the distance and walked towards them, oblivious to the surroundings. By the time I reached it, it became clear that it was a disused office building, and I looked around unsure of where I was. Behind me was a military guardhouse that was surprisingly unmanned, and coming towards it (and me), no more than 75metres away, were two squadrons of naval personnel marching along the quayside. Realising that I was in a restricted military area, and would be arrested, I scampered to my right, in between the disused office building into an alleyway that lead inland. Hoping that this offered another way out of the docks, I walked gingerly up it. I had walls 12ft high on both sides of me, and it can't have been more than a couple of metres wide but turned left sharply and began to follow the coast again.
After a few minutes, it opened out into a small abandoned plaza. A galleon with a gangway to the plaza was moored to my left, while a large building, currently closed and slightly derelict was to my right with no other way out of the plaza. I turned around to saunter back down the alleyway when I heard voices. Female voices and more than just a few. Panicking, I ran into the plaza, and with nowhere to go, ran across the gangway and crouched down on the ship, peering over the edge. Desperate to relieve myself, I found an abandoned cup and filled it to the brim before emptying it overboard
About thirty girls – the majority no older than me - walked into the building, and just when I was about to make a break for it, a handful of them started a football game in the plaza. People came out onto the plaza all afternoon and offered me no window of escape and by the time dusk fell the square was silent and the light from the drab building became the only source of illumination for the area. I was shivering with cold and fear, but realising that the plaza was finally empty, and that I had to make my escape now, I began to board the gangway to return to shore. My heart beating furiously against my T-Shirt I ran across the gangway to the plaza in the half-light.
I hadn't even made it a quarter of the way across the gangway when a female voice shouted me to 'STOP' and emerged from the shadows of the building. Running towards the ship with a weapon, I turned on my heels, and threw myself down the nearest hatch, tripping over my bag as I did. I heard the hatch click behind me in the darkness and last thing I remembered was hitting my head on a beam and the world going darker than it already was.