My Erotic Education - A Journal 03

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Need necessitates a trip to a tailor and more education.
4.1k words
4.74
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Part 3 of the 10 part series

Updated 06/08/2023
Created 09/08/2017
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rae121452
rae121452
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The next morning, I awoke disoriented not only to place but also situation. I was in my uncle's bed and as I came to consciousness lying on my side I became aware first of my uncle's body pressed against my back and his arm draped over me, his hand firmly wrapped even in his sleep around my throbbing morning erection. Also the feeling of his big erect cock slotted between my legs and his cock head poking my ball sack from behind. Altogether it was a most satisfactory way to start the day.

What had awakened me, I soon discovered, was the sound of Will coming upstairs with a heavily laden tray. He came into the room, sat the tray on a nearby table and approached the bed. Seeing that I was already awake he winked one eye at me, grabbed hold of the covers and pulled them off the bed while crowing, "Wake up, you lazy sluggards. Time for a piss and breakfast is served."

My uncle, roused so rudely, snuggled against my back while squeezing my erect member and said, "You can always tell it's going to be a good day when one is waked by such a charming, sunny servant."

"I get paid for my labor, not my attitude. A pleasant disposition will cost you more in wages." Will replied.

He observed my uncle's hand, still clutching my cock and walked to the bed side and grasped my uncle's wrist.

"Let the young man's privates remain private for the time being." he said, pulling his hand away from my cock. "We have a lot to do today and no time for play."

He grabbed me by the arm and levered me upright.

"We'll have a morning piss and then I'll serve your majesties breakfast" he told my uncle, who had rolled over and covered his head with a pillow.

He herded me across the hall before him, my erect cock swaying in front of me, and into the bathroom. I took my place before the toilet to urinate. Will came up behind me, pressed himself against my back and grasped the shaft of my penis and pulled by my foreskin while looking over my shoulder.

"Let me help you with that." he said, pointing my cock at the bowl. I let forth with a strong stream of piss, churning up a yellow froth in the bowl.

"You do piss a gusher. " Will stated. "I've seen racehorses whose flow was less strong." He shook my cock to clear the last few drops from the tip.

"You seem quite interested in my pissing." I said. "I noticed you observing me last night, too."

"I admit I am." Will said. "It has always been strangely exciting to me to watch as a big cock sprays the golden liquid."

"We have plenty of room at the bowl for two." I said. "I was intrigued by watching you yesterday on our trip when you emptied your bladder. I suspect that you wanted me to be. So, step beside me and let's observe each other."

Will stood beside me and unbuttoned his flies, then drew out his big cock with the hand not holding my own.

"Let me offer the same assistance you provided me." I said and grasping his thick shaft, pointed his cock into the bowl. He let loose a long stream that I could feel vibrating through his member. When he was drained I shook his cock to free it of any drips and felt it starting to stiffen.

"Please feel free to ask for my help at any time." I said, cradling his heavy member in my palm.

"You are a valuable addition to the household, sir." he said and lifted his hand that had been grasping my cock to his mouth, licking up the splatters of liquid that had moistened his fingers.

"I had better tuck myself away before desire overcomes prudence." he said and returned his cock to his trousers.

I felt his other hand slowly creeping between the cheeks of my ass, stroking and fingering at my puckered hole.

"And how are we doing here?" he asked. "Any irritation or razor burn after my barbering last night?"

"While I can't say I've noticed any ill effects, I certainly seem more sensitive there as you may be able to judge from the renewed hardness of my cock."

"Let's just make sure there's no chance of rash or itch." he said.

He motioned me over to stand beside the tub while he removed a small jar from a nearby cabinet.

Sinking to his knees behind me he said, "Just prop you leg up as you did when I shaved you and I'll take care of all back here."

I did as he instructed and bent at the waist; I grabbed my hanging ball sack and pulled it up so that I could see Will's face between my spread legs. He was staring into my wide spread ass with a look of almost reverence.

"You do have a beautiful little hole, sir." he said. "It looks good enough to eat. Let's get you set up for the day, though."

He unscrewed the jar lid and dipped his fingers in, then brought out a creamy substance that smelled of roses which he proceeded to massage into my ass crack. The feeling was indescribable and I felt my cock swell and buck when he stroked the area around my sensitive puckered hole. He seemed to take special care in coating that area, even allowing his finger to press some of the cream inside my hole.

"I could spend all day at that task but time you had some breakfast." he said, rising to his feet and reluctantly removing his hands from my smooth ass crack.

Turning around, I noticed a sizable erection tenting out from the crotch of his loose trousers and he noticed me noticing but nothing was remarked.

He shepherded my back across the hall to the bedroom where my uncle still remained stretched out upon the bed, eyes closed. Approaching him, Will said, "Out of bed, lazybones! If you don't get up I'll be forced to drag you out by your feet."

My uncle opened his eyes and I saw him take in the wilting but still highly evident growth in Will's trousers and my own erect and swollen cock.

He said, "Only because I fear for my poor orphaned nephew's honor at the hands of a vile ruffian like you.", then swung his legs off the bed and stood up. Once on his feet, it was obvious that he'd begun to attain a state of erection himself.

"Go have your piss and I'll lay out the breakfast, you vile ruffian yourself." said Will and he began to set out the items on the tray and then pulled up three chairs around the table.

We all sat down when my uncle returned, he and I in a state of unembarrassed nudity while Will, fully dressed, served us all. I found myself ravenously hungry and it was some minutes before I paused eating long enough to converse with my table mates.

"My uncle gave me a first lesson in self abuse last night." I said to Will

.

He looked at me, his eyes wide and replied, "I'm sure that's always useful knowledge to have."

"I would never have guessed it could be so gratifying." I said. "Do you ever practice self abuse, Will?"

"I do indeed." replied Will. "Quite frequently, as a matter of fact. All men, whether they admit so or not, do."

"Usually during what are supposed to be his working hours, no doubt." my uncle muttered.

I ignored my uncle's comment and continued speaking to Will.

"The reason I ask is because I'm curious which method you use. Perhaps one day soon we can practice it together and you can demonstrate your preference for me?"

"And Will's day has now been made." my uncle again muttered in a low voice.

Will paid no more attention than I had. "I'd be delighted, sir." Will said. "The sooner the better, I'd say. One must embrace knowledge wherever one finds it."

"And if this conversation becomes any more sick making I'll be forced to spend the rest of the day recovering in bed. I see that breakfast is finished for all concerned so I trust Will to find some decent clothing for my nephew to wear on our excursion to the tailor."

Will began stacking the used dishes back onto the tray and when he had loaded them all, he lifted it and carried it to the doorway.

"And, Will, no self abuse until your chores are done." my uncle said to his retreating back.

Will turned around at the doorway and replied, "Being a lowly servant, my hands are always full as you can see. Besides, I may find myself in a situation where someone else would rather do the abuse than me, today." He then stuck his tongue out at my uncle, blew a raspberry and retreated.

"I don't know how I'd ever get along without him." my uncle said, smiling fondly.

Will soon returned, both arms draped with articles of clothing. He helped my uncle to don his outfit, buttoning buttons and tying laces whenever required. Dressing me turned out to be another matter.

Although my uncle and I seemed roughly the same size I was broader in the shoulders and chest, thicker in the waist and fuller in the hips. None of my uncle's garments would fit me.

"I suppose I'll be forced to accompany you dressed in your rough farm hand clothing." my uncle said. "Will, if you would be so kind as to retrieve those items and bring them here? Oh, and also my largest overcoat. We can at least disguise his outfit."

Will did as instructed and soon was handing me my scorned clothing.

"There is one small problem." he said. "I was unable to locate the unusual suit of underwear that you came to us wearing."

"Oh, well, I guess you'll simply have to go without. I'm sure you won't even notice."

Will helped me on with the garments over my nude body and while the feeling wasn't uncomfortable, there was an obvious problem. The knit fabric of my union suit had always bound my sexual organs to my body. Without the suit, my organs were not only visible beneath my trousers but, swinging free and loose, I soon became aroused again and even more obvious.

"Just keep the coat tightly closed while we're in public and you may not frighten the horses." my uncle said, staring at my crotch.

Will trotted off and soon met us in front of the house with the carriage. My uncle and I mounted and we were soon traveling through the city. I was so engrossed in the new sights surrounding me that I wasn't even aware that we had arrived at our destination until the carriage came to a standstill.

Before us at the sidewalk's edge was a discreet store front, the sign hanging above announcing "H. STEINGERG-GENTLEMEN'S TAILOR". The front windows were covered inside with heavy fabric and I thought for a moment that the shop must be closed until it dawned on me that this was a convention to preserve the privacy of the customers once inside. We alighted from the carriage and my uncle led us over and through the shop door.

Inside, we were greeted by a gentleman about the same age as my uncle who was wearing a smock of dark fabric. He had a full beard but his head was hairless and he was wearing some sort of little flat cap on top of his bald pate. I judged him to be very handsome even though he wore small wire rimmed glasses.

"Mr. Steinberg, may I present my nephew. He has only arrived from his life in the country last night and I need a complete new wardrobe for him at your swiftest invention."

I shook Mr. Steinberg's hand and my uncle said, "Take off your coat and show him what he has to work with."

I shook off the coat and laid it on a nearby chair, then turned to face the tailor. He started looking down my body from my shoulders, seeming to plan in his mind what he would make for me. I noticed that his gaze stopped and froze when he reached my indiscreet groin.

"Unfortunately, we were unable to locate his usual undergarments." my uncle said. "He's a very healthy and vigorous young man, as you can see, so I'm hoping you can also fabricate some small clothing for him which will make him less attention getting."

"I think I can supply every service that this young man might need." the tailor said, speaking for the first time.

He crossed to the shop door and locked it after putting up a small sign that said "We will be closed until further notice" and then made sure that the windows were solidly covered.

"Right." he said. "I assume that you've never had a tailor serve you before?"

I acknowledged this was so.

"It's a very simple, though some find tedious, process. I will need to take a number of measurements on your body to know what sizes to make your various items. First, if you'd be so kind as to remove your clothing and step up onto this riser." he said.

Will helped me to remove the few items I wore and I stepped up onto the box, totally nude. My uncle and Will took chairs in front of me to observe and the tailor stepped before me, a measuring tape looped around his neck. He again raked my body with an appraising stare, coming to rest on my partially erect genitals.

"It will be a pleasure to serve such a lovely young man." he said and my uncle replied, "I knew that you would be sure to extend every service when you saw what we have to work with."

The tailor grasped his tape and began to take his measurements. First, he measured the circumference of my neck, then he measured my arms from shoulder to wrist, the size of my biceps and then each wrist, jotting down numbers at each interval. He wrapped the tape around my chest over my nipples, which suddenly seemed extra sensitive. The pleasant feelings aroused in each transmitted down to my cock which I felt start its usual habit of lengthening and thickening at the slightest provocation. The tailor then moved his tape down to around my waist and I saw his gaze resting on my growing penis.

"I see that you have already adopted the current fashion of a barbered pubis." he said.

"Yes, Will was kind enough to style me last evening."

"I'm sure that Will was more than happy to oblige." he said, turning to smile at Will. Will responded with a mock salute.

"You can see why we need some special undergarments." my uncle said. "My nephew was raised in the strictest environment and he has really no perception of worldly things. The slightest sensation causes his cock to grow fully erect and, as you can see, it is of a size that makes itself extremely obvious. I don't want him to be embarrassed in public."

"Some would argue that there is nothing requiring embarrassment here." the tailor said and his hand grasped my now fully erect and upright penis.

"Yes, that is undoubtedly true." my uncle said. "But, my nephew has led such a sheltered life that he wasn't even familiar with the custom of self abuse until I enlightened him last evening."

"Can this be true?" the tailor replied. "It's shameful how civilization is slipping. To think that such a handsome and well endowed young man has lived to this age in utter innocence." He fondled my hard cock, squeezing and pumping it with his fist to my utter enjoyment.

"Will and I have taken his education in hand, as it were." my uncle said. "By your next fitting appointment I hope that he will be well advanced in the ways of men together and will have some tales to tell you. In the meantime, we must keep him as is until I complete each lesson."

"I understand perfectly." the tailor replied, somewhat reluctantly releasing my cock from his grasp. "We still have some measurements to take, though. Would you turn your back to me, please?"

I did as he asked and waited while he studied my back and ass. I felt his tape on my back as he measured my shoulders from side to side, then the tape as he placed one end at my neck and ran the length of spine to my waist. After this, he placed the end of the tape at my waist and I felt him run it down the cleft in my buttocks until his hand came to rest between my cheeks, his exploring fingers caressing my hole. He slowly brought his hand back up the valley between my ass cheeks and I felt his warm hands fondling my meaty globes.

"My goodness, you are a luscious sight from every angle, aren't you." he said.

He sank to his knees and encircled my hips with his tape, first reaching around in front and moving my erect cock out of his way while squeezing it. When he had written down this figure he instructed me to turn back forward. As I did so, my erect cock collided with the side of his face with a dull thud.

"A bit harder with that big truncheon and I'd probably be unconscious. "he said.

"But you'd enjoy the beating." Will remarked.

"I can affirm that I would." the tailor replied. "Now, I need to measure your inseam. Could you spread your feet a little wider?"

My cock hovered inches from his face as he placed the end of the tape at my instep and the ran it up my leg, coming to rest in the warm valley between my legs and with my heavy ball sack draped over his hand and wrist. He moved to my other leg and repeated the movement, allowing his hand to linger in my crotch, bouncing my balls against his hand.

"Since you are so large here, I should probably take additional measurements to insure sufficient room in your trousers." he said.

"I'd be happy if you did." I replied.

He grasped my heavy ball sack in his hand and seemed to weigh it, and then he wrapped his tape around the center and measured. When satisfied, he moved the tape down and measured the pair of orbs in the sack together, then each one separately. My cock was pulsing and throbbing from the feeling of my balls being fondled and he watched each wave of sensation ride up and flare the swollen head. My cock was so hard that my piss hole was distended open and clear fluid leaked out and ran down the shaft. The tailor used one finger to scoop up the fluid along the shaft and then popped it into his mouth.

"Delicious. "he pronounced.

He then began measuring the cock itself, wrapping it around the thick base, moving it up to mid shaft and then measuring the flared corona of the exposed head. Next, he measured the length using the same method that Will had used the night before.

"8 and ½." he announced.

"I've grown since last night." I said. "Will measured me at 8 and¼."

"A tailor's measurements are always the correct ones." he said. "Perhaps I shall give Will a lesson on measuring one day."

"I will look forward to it." Will said.

"One more measurement and we're done, I think. Could you turn around again so that I can measure the length of the seam in your seat? Will, can you assist?"

Will came forward and the tailor had him hold me steady and supply a footrest as I raised my leg high, spreading my ass open and the tailor crawled under me to measure my spread cleft from end to end. He spent an inordinate amount of time in this endeavor and I frequently felt his fingers fumbling at my hole.

"I had a full breakfast just a few hours ago but suddenly I find my self famished." he said as he resurfaced.

"Did Will also help with your self abuse lesson?" the tailor asked.

"No, but he has promised to display his favored technique for me. I wasn't aware there were so many."

"Let me demonstrate my preferred grip, with your uncle's permission." the tailor suggested.

"Please do, if my nephew agrees."

"I like to point the cock straight out, rather than straight up, grasp the shaft low near the base and use the other hand to stroke the shaft." He demonstrated his technique on my swollen cock, stroking fiercely on my hard meat.

"That's an excellent method." I said. "I feel that I may ejaculate if you persist."

"Please do!" the tailor replied." After all, that is the object of the exercise. Tell me when you feel the cum starting to climb your shaft."

I looked down and watched his stroking hand on my cock, reveling in the wonderful feeling. I soon felt the familiar sensation of my puckered ass hole burning and tremors of pleasure radiating out from it.

"It's happening!" I cried. "My juice is ready to fly."

The tailor pulled his face close to my cock and opened his mouth just as the pearly liquid began to blast out of my piss hole. I watched as my fluid flew past his lips and landed on his tongue. After my cock had stopped spurting, he closed his mouth and savored the flavor of the goo on his tongue before swallowing it in one gulp.

"Did it taste good?" I asked. A splash of my fluid decorated one of his bearded cheeks and I used a finger to scoop it into his mouth to follow the rest.

rae121452
rae121452
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