My Travels With Friar Harold
Chapter 1

Copyright© 2015 by harry lime

Erotica Sex Story: Chapter 1 - James the Jester is ready to become the good Friar Harold's assistant but first he must learn more about the real world from the Duchess of Colchester.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Fa/Fa   Mult   Consensual   Coercion   BiSexual   Heterosexual   Fiction   Historical   Spanking   Humiliation   Group Sex   Orgy   Oral Sex   Anal Sex   Masturbation   Petting   Sex Toys   Squirting   Exhibitionism   Voyeurism   Clergy   Public Sex   Violent   Royalty  

My name is James of Colchester.

I must confess that I am a jester of sorts but not amusing enough to be considered first rate by the educated upper-classes.

The paths of the astonishing Friar Harold and I crossed on a cold and blustery day when my garments were fair covered with snow and ice and I must have looked like an icicle ready to drop into the ditch at the side of the road. Please trust that I will not try to embellish my importance in this meeting which was both benign and insignificant and totally of a random nature.

At that particular juncture of my life, I was but a sprite of a lad, only eighteen and filled to my silly brim with excesses of spunk in need of safe harbor. Of course, I was focused on the hope that it would be inside some comely personage of the female gender with ample storage capacity in her trio of openings to absorb the flooding of my forceful juices. In all honesty, I must admit I would be willing to accept a female lacking some degree of charm and good looks providing she was sincerely appreciative of my efforts in stuffing her to her maximum limit. I was not a virgin by any stretch of the imagination having already acquainted my inquisitive pecker with sundry holes of opportunistic consummation. I can assure you that the young ladies in question were all of the age of majority and quite willing and of a submissive nature pleasing me beyond belief.

I am ashamed to admit that I was also accustomed to trading the use of my unsheathed sword to several married ladies of unhappy marital unions seeking the comfort of a younger lad with weakness of moral character and in need of funds to keep him in ample supply of vittles and drink. I have always found that the discovery of many nocturnal secrets was derived from concert with females of a more mature age with years of experience under their clothing. I am the first to state definitively that my reputed skills in bedroom sports and my vast variety of carnal pleasuring was learned from such age-challenged females and I was most attentive to their spirited tutoring.

A case in point would be the Duchess of Cambridge who was to be sure not blessed with facial perfection and somewhat long in tooth for youthful frolic. She was more rotund than curved and her curls were for daytime show and removed at night for safekeeping. I was invited to entertain the Duchess in her private bedrooms on a soft summer night with the windows thrown open to attract a hint of a cooling breeze to reduce the sheen of shiny sweat from all human bodies both male and female with little thought to appropriate behavior or rules of propriety.

I must apologize to you readers of my convoluted tale to have digressed into this discussion of the Duchess when I wanted to tell you about Friar Harold.

Please bear with me for the nonce and I will explain my verbal detour as quickly as possible.

Where was I?

Oh, yes, the Duchess was not much to look at in her thin nightshift on top of the luxurious bed that dated back several generations to more temptingly endowed maidens losing their cherries on their wedding night. There was no danger of the Duchess losing her cherry as she had been well exercised by most of the male staff of the castle and a goodly number of the military guard as well. In truth, she was a bit jaded what with sampling the familiar poking tools of the males under her authority and the sight of the fresh eighteen year old in front of her (me) was enough to bring the juices back to her well-worn slit and make her nipples stand upright once again.

I was in my tights that showed my masculine assembly in great detail and I in turn was able to see the dark patch of hair between the Duchess's legs that promised great fun with her legs perched high on my shoulders.

My original thought was modified when she turned over and presented me with her huge backside that was more a magnificent and imposing edifice than a normal shapely heart-shaped garden of paradise. Right away, I surmised she preferred to take her cock from the rear rather than in the traditional missionary style which was universally thought best for male control of the female copulation activities.

It was relatively simple to fling her flimsy nightshift to the side and address her flanks with serious intent. She was so accommodating that she reached around behind and pulled her great flabby slabs to the side allowing me ready access to both her brown tinged crinkle hole and her black haired slit of feminine delight. I could see the wetness and the pink readiness of her female folds and aimed with my customary skill for the vaginal entryway expecting that it would be loose and ready. Unfortunately, she had moved somewhat and my rock-hard member defeated her unmotivated sphincter instead and slid home inside her posterior portal with a squishing sound that struck concern into my youthful heart.

I was instantly fearful of her reaction expecting that she might consider parting my head from my body for my terrible mistake.

I remember distinctly that she began to quiver and shake like a mad-woman possessed and I was forced to hang on for dear life to keep from being flung off the bed and onto the hard stone floor. I did have some instant gratification because her back door of love making was unusually tight for a woman of her age and I assumed she had not used that entryway often. I desperately wanted to apologize for my poor aim but the poor woman was making a series of animal-like grunts and groans that was in perfect rhythm with the way she was thrusting her entire lower body back into my groin for deeper penetration. I was not certain if I should just stay there like a complicit wall of flesh for her to impale her flesh upon or to meet her halfway and try to ride her sturdy body to ultimate orgasm with some degree of comfortable fit and a modicum of dignity.

The Duchess and I became fast friends after that mishap because she had taken a liking to me and my obliging ways. It was because of her that I met the good Friar Harold because she had sent me on a silly errand into the market to find some hair brushes that could easily serve for the brushing of hair and the administering of corrections to her maids in waiting who were often clumsy in their work and not attentive to orders. I had already become friendly with a pair of them who were uncommon familiar with my anatomy despite never having met me before. I often mixed them up because they had the same color hair and sounded quite alike because they came from the same village and their accents were identical. I must admit I only remember one of their names because it was several years past. I know for a fact that the one with the lovely big boobs was called Emma and the one with the air of a person far above her station was called Jane. I tended to like Emma better because she was generous with her favors but Jane had that certain air of mystery that I found irresistible from an intellectual point of view not that I was above average in intelligence. I felt certain that Miss Jane was quite intelligent because she used words most unfamiliar and I spent a great deal of time thumbing through the family book of words to discover its true meaning. Sometimes I could guess at the meaning because of the way she used it in a sentence or just the look in her flashing eyes but I wanted to be certain about things and I was more often wrong than right.

It was quite the eye-opener for me when the Duchess instructed me in no uncertain terms to test the new brushes on pretty Miss Jane's flanks and not to cease my testing until I was positive which one was the most effective.

I must admit the design of Miss Jane's delicious buttocks was a source of supreme speculation that forced me into a number of happy erections that I pressed upon the flesh of my female mentor with frenzied enthusiasm. The sounds of the squeals escaping from the lips of the Duchess were not lost on her ladies-in-waiting and I could hear them giggling in the adjoining room knowing that she was in confirmed dalliance with my ardent cock. Now I was to be treated to not only a close up and personal viewing of the construction of said posterior of the virginal Miss Jane, but I was to put it through a complicated test of endurance and physical distress.

I knew that part of the process would be to apply the soothing salve to calm down the reddened skin and that I would probably make little detours from the curved cheeks down inside the hidden depths of her crack finding the entry to both her private rear entry and her female slit with wet promise of anticipated reward. All in all, it was the culmination of my long period of frustrated desire and I welcomed the opportunity to avail myself of the pleasure.

The delicate placement of Miss Jane's bare cheeks face up on my lap was accomplished with a great deal of giggles and laughter from the watching spectators. I saw that the poor child was dreadfully mortified because her previous corrections were in the privacy of the closed door seclusion of the Duchess's bedroom chambers.

I was fully aware that my formidable erection was pressing up relentlessly into the well brought-up girl's fanny but I had no control over it at that point. Her weight pressed down on my groin with a desperate trigger of unrequited lust. I had no choice but to pass my greedy hands all over her upraised cheeks making her realize her entire backside was now under my supervision and soon to be reddened to a rich shade of red that would become the focus of everybody's attention. She was a private person and one not accustomed to such a display of her hidden assets.

It was a perfect opportunity for my fingers to dip inside her cleft and explore her feminine folds confirming to me that she was in a wet state of readiness for the fast approaching festivities. I took the over-sized pearl handled hairbrush and rubbed it over her cheeks and even moved the handle down inside her legs to tickle her slit with devilish intent of arousing her female libido.

Her gasp of surprise delighted the onlookers and I swiftly moved to the first heavy blow from the brush right on the bottom curve of her left buttock. She jerked and bounced forcing some of my pre-cum to soak right through my trousers and right into the dampened area of her love-nest. I loved the way she was squirming and bouncing and if she didn't calm down I was certain I would be forced to shoot my load prematurely like some schoolboy with his first taste of pussy.

The sharp red outline of the hairbrush on her delicate white skin was glorious in its presentation. I instructed the poor girl to begin counting and not to miss a single beat or we would have to start all over again. She tearfully promised to obey my instructions faithfully and her attention to detail was most commendatory.

Out of the corner of my eye I saw that the Duchess had pressed Emma's head under her lifted skirt and was humping the captive girl's face with her demanding royal quim. The rest of those present pretended not to notice her public display of corrupt lewdness. I was amused because I felt that the stuck-up Emma needed to be taken down a peg or two and put in her place under the thumb of the person who paid all the bills.

I got back to my duties with Miss Jane and after about twenty swings she was screaming bloody murder and her snatch was spraying my legs with her female juices. Her backside was an encouraging shade of red and I moved quickly to my ministrations with the salve learning her intimate posterior geography in unforgettable terms and finding those special places that seemed to make her purr with delight.

I helped Miss Jane restore her panties and other clothing to normal display and she dried her tears doing her best to look natural and unflustered by her ordeal. We sat together watching the Duchess and the others engage in a most shameful orgy with perverted fetishes that drove us to laugh in great amusement.

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