As I look back on it, I realize the hardest and most satisfying moments of my introduction into the D/s life came during the late fall semester of my freshman orientation period.
After we had been screened and qualified, eight of us male plebes had signed an oath of confidentiality and submission as did 10 female candidates. What amuses me now is that all of us thought we were battle-tested at the time of our compliance ceremony. How wrong we were.
It was the week after the homecoming football game and orientation pleasure training was about to start. Over the weekend we had hosted several parties for the alums and their guests. All very proper and subservient but not much was learned that weekend. Our masters and mistresses made up for that over the course of the next three weeks.
By that week before O.P.T we were getting comfortable in our routine. The freshman plebes would be roused at 6:30 a.m. every weekday (8 a.m. on weekends) by our Junior Mistress leader who had made her way through the 20 foot long underground passageway from our sister sorority next door. No doubt, she would often exchange plans with the Junior Master who was headed to the sorority to start the girl plebes’ morning ritual.
We immediately dressed in our supplication outfits of hot pink tank tops and tight mesh shorts which confirmed the presence of our leather chastity harnesses. The harnesses were well constructed and allowed for partial erections only. Masturbation was impossible with these contraptions in place. In fact, urination was only possible if one wanted to soil the device and endure the humiliation and public punishment that would follow.
We stood in the inspection line waiting for the mistress to approve our condition and unlock the padlock at the tip of the sheath. If everyone passed inspection she led us to the restroom where we could take our morning piss before returning to the dining hall.
We gathered our breakfast from the 50something hall cook who had been with the fraternity from its inception. She was an incredible cook and very supportive to the first semester plebes. We all loved her despite the long leers she gave our bound cocks and the bemused looks she exchanged with the mistresses. Well, we loved her that first semester.
Fifteen minutes to eat breakfast and another 10 minutes to clean up.
We all re-assembled in the upstairs hall, removed our shorts and waited for the mistress to come and exchange our leather harnesses for the steel cock cages we wore throughout the day. These cages consisted of circular bands of steel attached to a metal strip and were adjustable to the point that no erection was achievable. A ½ inch wide suede-lined strap clamped around the base of the cock, underneath the balls and anchored the sheath in place. The sheath was riveted to a thick leather belt that buckled and locked with two small combination locks affixed on either hip. A thin second strap made of bungee cord material attached to the underside of the metal band nearest the cockhead, bisected the scrotum and returned thong-like to the back of the belt where it was secured with a third small combo lock. The contraption kept your cock pointed down and flaccid. It also had the effect of making it necessary to sit to piss and it meant that the tight pants we were required to wear would show a very large package. This would often cause a glance or two from unknowing co-eds. The stirrings those encounters would engender eventually became frustrating and, at times, very painful.
The chastity belt exchange would take about 20 minutes total, the entire time we were made to stand at attention while waiting our turn to be fitted. Plebes with 8 a.m. classes went first and would be allowed to dress first. Besides being required to wear form-fitting pants or shorts and not being allowed long shirts, we normally could dress however we liked.
During the day we were forced to go to all our classes and the time before and in between classes had to be utilized studying. The upper classmen from both houses were given the class schedules of all the plebes and the approved study locations so that they could monitor our compliance with this rule.
Being forced to make class and study during the day would ensure a few things. First, our grades would be good; therefore, parents and school officials would be much less inquisitive. Second, more time could be devoted at night to our “alternate schooling.” Thirdly, we would graduate high in our class, obtain prosperous employment and help fund the houses long after our graduation. In fact, our graduation rate was in the high 90 percentiles. We had some very affluent alumni, partly because of our training in this regard. And finally, it continued our training all day long, every day.
After our last class of the day, no matter what time that was, we were to report back to the house and to the study room. Everything you could possibly imagine you would need to study was in this room. It had computers, hard materials like pens and paper and… well, you get the message. Bookshelves lined two walls of the room. The room also had some extras.
When plebes got back to the house and reported to the study room all clothing was removed and each plebe was chained in place around a 16-foot oak study table.
The male plebes had a chain attached to the ring at the end of the cock sheath while the female plebes chain was attached to the hasp of their chastity belt. The other end was attached to the ring bolted into the floor under the wicker-seat hardwood chair. The chain was long enough so that you could move in the chair but not long enough so that you could actually get up out of the chair. There was space in the room for 20 students and at all times there was a junior or senior brother and sister to ensure the plebes were actually studying.
Often I would find myself studying next to 10 or more others. It was hard to concentrate, at times, when I sat chained to the floor by my cock while an attractive female plebe sat, naked, next to or across from me.
Only once did I let myself be caught daydreaming, though. Every upper class brother and sister was empowered with disciplining plebes who let their minds come off of their studies.
I was so engrossed in my daydream that once that I never saw her approach. Her face was just a foot from mine when she whispered out loud to me.
“What are you doing, plebe?”
I jumped about a foot out of my seat and stammered, “I was trying to understand this theory from philosophy class and…”
“Don’t lie, you pathetic piece of shit,” she announced to the room. “You were daydreaming about something. What was it?”
“It was, It was,” I lowered my gaze, “this girl in philosophy class who was staring at my…“
“This is the time to study, ass wipe, not to fantasize about some girl who you’ll never get to fuck. Especially, in your current condition,” she ridiculed with a quick nod to my caged cock.
I could hear the chuckling in the room as I swallowed hard and answered, “Yes, Big Sister.”
“Well, I think you’re in the need for some physical encouragement. Don’t you agree?”
“Yes, Big Sister”
She walked over to the bookcase wall, flipped open a couple of latches and pulled the case out and spun it around. Hanging from the other side of the bookcase was an assortment of discipline devices. Whips, paddles, switches, clamps, small gauge chains, a vast assortment of restraints and so many other implements I couldn’t then identify.
She lifted a small wooden box from the bottom shelf and dialed a combination to open it, retrieved an object from the box and walked over to me. I was curious when she reached a hand out in front me and said, “pick a card, any card.” She had fanned out in front of her a deck of playing cards. I looked at her quizzically.
“Don’t make me tell you again. Or you’ll be picking two cards.” I heard a giggle in the room.
I picked a card.
She opened her other hand to display a set of 5 dice.
“Now you need to take, lets see, I think maybe-“ the giggling girl yelled out “five,”
“No, not this early, let’s say --- two dice”
“Okay, roll the dice.”
I did. A two and a six.
“Now show me what card you pulled,” she commanded.
I turned the card over, but there were no suits on this card just one word printed in black ink in Old English type. TAWSE
“Okay, everybody who is not chained to the floor,” she announced to the room, “you get 8 swings of the tawse at this unfortunate plebe.”
Once I realized what she said, I quickly looked about the room. I was relieved to find that of the dozen or so people in the room there were only three others without chains attached to their genitals: two Big Brothers and one other Big Sister.
“Everyone who IS shackled, close your books and watch what will happen if you don’t keep your mind on your homework,” she commanded. I could hear two boys and maybe as many as four or five girls utter their compliance phrases.
I was unbuckled from the floor and led to the bookcase next to the implement rack. Leather shackles were attached to each wrist. A chain was clipped to each wrist and the chain was lead up to a hole on the underside to the bookshelf bracket where they were again clipped in place. My ankles were bound together with a leather thong. Big Sister then reached around me and clipped a long chain to the end of my cock sheath and forced her hand and chain through my thighs pulling the chain out the back. Because I was facing the bookcase I couldn’t see what she was doing with the other end of the chain but I heard a chair scrape across the floor followed by heel clicks as she apparently stood on the chair. She yanked on the chain pulling my body out from the bookcase.
I now had a choice. I could thrust my ass in the air and keep my toes on the floor near the bookcase or I could move my feet back, be strung out by my cock and have very little weight supported by my feet. I decided to stick my ass out. Big Sister chortled and took another two links away from me before clipping the chain in place.
My arms were stretched tight, my nose was literally in the books now, and it felt like my balls were about to detach from my body. And, oh yeah, my ass was now a perfect target.
“Okay, Toni, you’re first. Come get the tawse,” she said.
“Do you know what a tawse is, plebe?”
“It’s five half-inch wide fingers of nine-inch long English leather attached to a wooden handle. It’s what school masters and mistresses used in the 18th and 19th century to discipline unruly students.
“Do you think that might hurt a little?” she asked sarcastically.
“Yes, mistress, I believe it will, mistress,” I managed.
She prowled up to me putting her lips but a hair from my ear and whispered so that only I could hear her, “It’s gonna hurt like a motherfucker. You can’t stop me so why don’t you try taking it like the man you’ll never become.”
“Okay, Toni, you’re up. Why don’t we make this memorable?”
Without saying a word, Toni, swung the tawse and caught my right ass cheek with a glancing blow.
“A little out of practice, are we,” Big Sister asked, “well you got seven more to improve your aim.”
Swing number two hit the same cheek right on top of the same spot as the first blow only this time I could feel the full length of the fingers. Strike three was placed higher on the same cheek and the fourth swing landed vertically criss-crossing the other blows. Quickly, the blows came from and to the other side. When I had counted eight hits my ass stung but I certainly wouldn’t have put it in motherfucker territory.
“Okay, I’m going last so why don’t the two men go next,” she said. “Leave me some room guys, but do have at it.”
In my state I couldn’t remember who the Big Brothers were but I expected they could and would swing harder than Toni. Now I began to sweat.
I had no idea that the first blow was coming and when it hit I didn’t know what hit me. The tawse struck me across both cheeks, very high on my ass. There’s no way I could take 7 more of those. Luckily, only three of the blows punched that hard as he deftly altered the intensity of the beating. The second brother approached things differently. I never knew where the leather was going to land. He really surprised me when two blows on either buttock wrapped around my ass and reddened the outside of my hip.
And then it was Big Sisters turn.
“I think he’s had enough, look how red his ass is. Let’s take him down,” she said.
What a relief.
Just as I began to relax, she had swung the tawse with a vengeance striking the tops of my thighs just under the turn of my ass. She caught both thighs and the pain was intense.
“Just kidding,” she laughed, “your ass is red enough but those white thighs clashed.”
She peppered my thighs with the next three blows and I squirmed involuntarily in my bondage. But I was proud of the fact that I had not screamed or complained. Yet.
“I think it might be starting to hurt, Bethany,” Toni said to her friend.
“I think you’re right, but you know me,” Big Sister said, “I like to end with a bang.”
And did she ever.
The next blow went right at the crease between my ass and thigh, but it didn’t stop there as at least two leather fingers flicked across my stretched and exposed left testicle.
Now, I screamed.
“Shut up,” she screamed back. And another landed in the same place. I choked out another scream.
“I would have guessed you had no balls but it looks like you have one more that needs attention,” she said loud enough for all to hear.
“I am going to slap you on the other side just the same way. You have two strokes coming, however, if you scream even a little bit you will get another and another until you learn to take your punishment quietly.”
I could hear her walk to my other side and I waited for the sound of the approaching leather. And I waited. And I waited. Just when I relaxed for a moment she said, “isn’t the anticipation delightful?”
“Uh, yes, mistress.”
“Tell me when you’re ready,” she told me.
I took a couple deep breaths and said, “I’m ready, now, Mistress.”
“Wrong answer,” she said. “Try again.”
I thought for a moment.
“I’m ready whenever you want, Mistress.”
“That’s better,” she chuckled, “very good, you got that much quicker than my last quarry. I’ll only add one stroke to your sentence. That is, if you don’t scream.”
The three strokes came in rapid fire order, all three hitting me at my ass/thigh crease and stinging my exposed right ball.
I’m proud to say I didn’t scream. Out loud. But it hurt like a motherfucker.
Again she came up to me to whisper in my ear, “Don’t ever lie to me again, boy.”
She backed away from me, threw the tawse on the table and said, “I’m mildly impressed, plebe. What’s your name?”
“I have not been given a name yet, mistress.”
“That’s right, that doesn’t come until after O.P.T. I’ll look for you then.”
She went over to the table, released the two other boy plebes from the floor chain and told them, “take him down, clean the equipment and put it away. When I come back in here I expect everything to be back to normal, including him in his chair studying and all of you shackled in your chairs. We have a half an hour until dinner call. Do you understand?”
“Yes, Mistress,” they answered immediately and in unison.
“God, I wish they were through O.P.T. She looked at the two Big Brothers and said, “You guys want to go upstairs?”
My fellow plebes unbound me and together we cleaned the equipment and put it away.
Big Sister Toni locked my brothers to the floor in their chairs and came over to put me in my place.
When I sat down the fire ignited again in my ass and balls and I went to stand up. Both of my future brothers stared hard at me until I forced myself into my seat. Big Sister Toni attached my chain to the floor about 4 inches shorter than before to make sure I couldn’t rise from my seat. It was one of the most intense feelings of pain, pleasure and humiliation I’ve ever felt. Just, one of the most, you see, for orientation pleasure training was just around the corner.