Learning Ch. 02

"Prepare him." What in heaven's name did she mean by that?

"Come with me," ordered Priscilla.

Naked as a jaybird, I followed her down a hallway to a gigantic, ornate bathroom with white tiles, a marble tub, brass faucets, and unbelievably bright lighting. The bathroom was nearly as big as my poor little bedroom at home.

I knew Priscilla had sensed my nervousness, but she was enjoying her little part in this scene far too much to let me off the hook. "Please stand next to the bathtub while I get things ready."

She had just as stern a voice as Sarah, but at least she was kind enough to say "please," something Sarah had yet to say when commanding me to take an action. I stood next to the tub, my hands in front of private area, wondering why this room had been chosen for my "preparation."

Priscilla looked at me briefly. "Mr. Reynolds, I am sure Mistress will ask me about your behavior with me. I know she would be most disappointed to hear that you were covering your genitalia with your hands. Mistress expects you to keep yourself totally exposed while you are here in this house."

I moved my hands to my side and dutifully stood at attention while I watched the maid move to a cabinet beneath the sink. She bent over, her black skirt riding well up her bare, well-shaped, lightly tanned legs. She fumbled about the cabinet for a few seconds. When she straightened up she was holding an ominous-looking red enema bag with a long white hose. The smirk on her pretty face was obvious as she looked at the startled look on my face.

I knew immediately what was in store for me and my heart started beating a mile a minute. My face had never felt so flushed. I felt dumbstruck. Helpless. Bewildered.

"I know you would want to be totally clean for Mistress, especially back there," she said as she stole a glance at my ass, "and especially the first time she deflowers you."

I swallowed hard. "You want me to give myself an enema?" I asked incredulously.

She smiled broadly, her pretty white teeth glistening in the bright light. "Oh, no, Mr. Reynolds. I will be conducting this entire procedure. It's one of the services Mistress asks me to perform. Please don't feel so nervous, I've done this many times and if you cooperate fully we shall be out of here in no time and I'll be happy to take you to the deflowering room. I am sure you wish to please your Mistress, don't you?"

"I… I… Yes, of course," I stated quite honestly. Even at this early point in our relationship, there was no one in the world I wanted to please more. I was feeling more and more like a fly being drawn inexorably into a web, yet there was something inside me that was making me do whatever was necessary to please Sarah. In my heart of hearts, knowing that I would not want to displease her in any way was already becoming ingrained in my psyche. This feeling extended, of course, to Priscilla, her faithful servant who, in my judgment, spoke for Mistress Sarah.

"Good. Then when I am done preparing the enema solution, you shall get on your hands and knees, your head facing the tub. For now, you may watch and learn."

Priscilla placed the red bag on a table next to the sink, letting the hose hang down, its white plastic nozzle just inches from the tile. She reached back into the cabinet and retrieved a container of Epson Salt.

"The Epson Salt has a tendency to increase cramping, but, when combined with soap, helps to really clean the bowels," she said with an almost clinical voice. "The procedure is done twice, once with the soap and Epson solution, and once with clear warm water. When we are done, you shall be perfectly clean for Mistress."

I watched in almost total disbelief as Pricilla filled the sink with warm water, added about a tablespoon of the salt to it, and then lathered a bar of ivory soap in her hands, pausing from time to time to rinse her hands in the water which soon clouded from the mixed solution. She finally lowered the bag into the water and filled it. She completed all of her tasks with total efficiency and I got the distinct impression she had done this many times.

When she finished filling the bag, she turned her face toward me, surveying the length of my naked body, with my newly-shaved pubic and testicle areas on display. I looked away out of nervousness. She seemed to relish my humiliation.

"Kneel," she commanded.

I turned quickly and moved my hands and knees to the cold tile floor, presenting my naked backside to the maid who was about to cause me much embarrassment.

"Lean forward, on your forearms, so your ass is better presented."

I suddenly realized that the string from the Tampon Sarah had inserted into my nether region was hanging downward between my slightly opened legs, lightly touching my hairless sac. Priscilla noticed it, too, and, with a few slight tugs, pulled it out me. "We can replace this later," she said. "It would just get in the way now."

I shall not go into all of the lurid details of the two enemas Priscilla administered that fateful evening, but suffice it to say the humiliation was like nothing I had even known. When she pried my ass cheeks part and lubricated my soon to be de-virginized anus with some cold gel and gently eased the plastic nozzle into me, I felt like crawling inside the tiles and disappearing from the face of the earth. I cramped terribly from the first soapy solution. At least Priscilla was kind enough to leave the room while I relieved myself. I tolerated the second, plain warm-water enema much better physically, but the mental aspect left my mind reeling. Again, thankfully, she left me alone to expel the water from my bowels.

When she returned I was standing next to tub, hands dutifully at my sides, my face as red as a beet. She smiled. "We are almost done, Mr. Reynolds. You have done well." I considered thanking her for the compliment, but thought the better of it. There was little of which to be proud, if the truth be known. "You may assume the same position. I need to complete the lubrication process for your deflowering."

I knelt again, my ass raised up and well proffered. Priscilla knelt behind me, spread my cheeks once more, and stared for what I felt was an inordinately long time at the view of my anus before her. I could almost feel her eyes on my most private area. Then she applied a copious amount of the now familiar cold gel to my asshole. Suddenly, without warning, she stealthily slid her index finger through the gel into my anus and wiggled it against the soft walls of my rectum. I didn't groan until she introduced a second finger. I was glad she decided to stop at two.

"Easy," she said in a whisper-soft voice, "it is best not to fight it. Just relax and let it happen. You will be much better prepared for when Mistress takes you. You will be much happier that we are doing this now."

I relaxed as best as I could, but with two fingers busily toying with my rectal orifice, relaxation was the last thing on my mind. She applied more gel on her exploring fingers, adding the final amount of lubrication that would ease the path for Sarah to have her way with me. Seconds turned into minutes as she delved into me, moving her fingers back and forth with varying speeds. She seemed to enjoy her endeavors completely. When she was done, she helped me rise to a standing position and, quite surprisingly, took my hand in hers as she led me to my fate.

On the way down the hall to the "Deflowering Room," Priscilla gleefully told me that Mistress seldom used her sexual prowess in this way during the first session, that apparently I was considered "special" and that I should be honored. I didn't know how to respond to her comment, so I remained nervously quiet as she opened the door to a new room I had not yet seen. The room contained only one piece of furniture—a red velvet- covered hassock, perhaps two feet high, with a bright spotlight shining directly upon it. I was about to become the center of attention.

Holding the door open for me, Priscilla said, "You are to bend over the cushion with your belly over the top of it." I walked slowly to the hassock and bent over it. The velvet was smooth and warm beneath my body. "Bring the sides of your knees to the outside of the legs and grip the front legs with your hands."

Once assumed, the position left my backside totally open and vulnerable. "You are expected to remain completely quiet unless Mistress asks for you to speak. The more relaxed you feel, the easier it will be for you."

Such motherly advice…

Priscilla left the room, closing the door quietly behind her. Suddenly I was there, naked and alone and completely exposed, awaiting my fate. Minutes went by. The torment of waiting was just as scary as knowing that at some point in the not too distant future Sarah would do something to me I had never even dreamed would happen. My mind was buzzing with thoughts of how totally scared I felt.

Finally, I heard the door open. I dared not look. I heard light footsteps to my side. Soon someone was standing directly in front of me. "You may look up, Mr. Reynolds."

I lifted my head. To my amazement, Sarah was standing only a few feet from me, totally naked except for an ominous-looking black harness, from the middle of which was a long, pink-colored cock, perhaps eight inches in length, that jutted out almost perpendicular to her body. Seeing her breasts for the first time started my heart beating wildly. They were gorgeous, not very large, but almost conical in shape with pink nipples that were hard as rocks, surrounded by equally pink, silver-dollar sized areola. Her breasts were exquisite.

She smiled. "I see Priscilla has prepared you."

I nodded, afraid to speak.

"You have permission to speak, Mr. Reynolds. This is a special occasion indeed and we want you to feel special."

"Thank you, ma'am."

"Some females like to totally feminize their slaves. I prefer more subtle approaches, shall we say, just enough of a feminization to give you an idea of what a woman goes through in life. Ours is not an easy lot. We are always the victims of sexual assault, though you would have been a 'victim' had you not volunteered to give your virginity to me as a gift. We have our periods. Our moods. Most men treat us like shit. You will learn to treat all women with such complete respect that they will understand immediately how much you desire their happiness. Your mission in life, from this point forward, is make me, or Priscilla, or any other woman I desire to bring here, as happy as possible. Sometimes our happiness will be found in punishing you, sometimes quite severely. Through it all, you shall remember, above all else, that I am your Mistress. You are my slave. As long as you remember that, all will be fine. Do you understand?"

Seeing her naked for the first time only built the fires in my loins and the engendered more love in my heart for her. She was woman personified, everything a man could hope for. I don't know why, but I would do anything Sarah, Mistress Sarah, wanted. Anything at all.

"Yes, Ma'am, I understand."

Sarah grasped the pink pseudo-cock in the palm of her hand and held it tightly, pointing it skyward. "This will be your pleasure this evening, Mr. Reynolds. This will be your pleasure on many evenings, in fact. Tonight you will know in a small but telling way how a woman feels when she is being fucked. Do you like the idea of learning feminine ways?"

"If you desire, Mistress."

"Good. Before your next visit, I want you to go the mall and pick out seven pairs of women's panties. One for each day of the week. Whites and pastels are just fine. Silks and rayons are preferable. Wearing panties with a modicum of lace, Mr. Reynolds, will only gain my utmost admiration, so choose them wisely. And you will wear a pair of pretty new panties every day. When you are summoned to visit me, you will wear your favorite pair. Make me proud, Mr. Reynolds."

Blushing profusely, I said, "Yes, ma'am. As you wish."

"Good. Now, I do trust that Priscilla prepared you properly for me."

"I gave him two enemas and oiled the entrance well, Mistress. He tolerated everything surprisingly well."

I had no idea Priscilla was in the room to watch all this. It only served to enhance my humiliation.

"Then I believe we shall proceed. Are you ready, Mr. Reynolds?"

I gulped. "Yes, ma'am."

Mistress Sarah moved behind me and I lowered my head, waiting stoically to lose my virginity. "Put some K-Y on my 'cock' Priscilla. This very first time we shall be exceedingly kind to him."

I heard movement behind me and could only imagine in my mind Priscilla's fingers around the hard, pink cock, coating it for what I knew was about to be an entry into my proffered ass. My heart was beating so hard I thought it would leap right out of my chest. The humiliation I felt was even greater knowing that Priscilla was right there, watching everything, about to witness something I could never have imagined would happen, not even in my wildest dreams.

"Open him up," said Sarah.

Priscilla moved her body over my hips and straddled me, facing Sarah. I felt a pair of soft hands on my buttocks, spreading them wide apart. I could only imagine the sight I was presenting to both of these women. Suddenly I felt something cold and wet and hard pressing against my anus. I closed my eyes.

"He has such a nice, fuckable ass, don't you think?" asked Sarah.

"Indeed. Made to be fucked, ma'am."

The head of the pseudo-cock pressed harder, moving into me slowly but inexorably, breaking through the sphincter with much more ease than I would have believed. I relaxed as much as I could, just as Priscilla had suggested. I felt it going deeper and deeper, expanding the soft walls of my rectum. I grunted out loud when Sarah gave the cock a good shove. Before I knew it, I felt her thighs against my ass and realized she was in to the hilt.

A virgin no more. Somehow I had the distinct feeling that, in time, I could learn to like what she was doing to me. When Sarah started to move her cock in and out, it actually felt good. When she withdrew it almost all the way out and rammed it back in, I lurched forward. It was only slightly painful. In fact, on a plus and minus scale, it was far more pleasurable than painful. Slowly but surely I was getting used to being taken by my Mistress.

My breathing become more ragged, more labored. She was now pumping me harder and my cock was becoming erect between my legs. Sarah sensed my enjoyment. "Don't even think about coming, Mr. Reynolds! If you come without permission, I will beat your ass raw!"

The whole deflowering lasted at least ten minutes, and when she pulled out of me, I felt literally limp, washed out. This was one of those moments in life where I felt like time had frozen. I felt a bead of sweat fall from my forehead to the floor. Priscilla unstraddled herself from my hips and moved behind me. It felt like my asshole was stretched to the limit, but swarms of pleasure ran all the way up my spine and shot straight into heretofore unknown nerves in my brain.

"Arise, Mr. Reynolds."

I stood up, now embarrassed by the fact that my cock was standing as straight as I was, a fact not unnoticed by Mistress Sarah.

"I think we have found a wonderful new play-toy, Priscilla. The young man didn't protest at all. In fact, he obviously enjoyed being deflowered far too much. Look how he embarrasses us with his erection. Shameful! Get me a cock whip."

A cock whip????!!!!

In seconds Priscilla was at Sarah's side, handing her a short, multi-stranded, leather whip. Sarah moved in front of me, holding the wooden handle of the whip in her right hand, its tentacles hanging down. She was now totally naked, having removed the harness from her hips. Her pussy lips were thick and puffy. Peaking out very prominently was her engorged clit that I had licked a few moments ago. I was careful not to let her see me sneaking peeks at her wonderful nakedness.

"Play with your cock and make it even harder, Mr. Reynolds!'

I gulped. I looked down at my almost completely erect member and took it my right hand. I pumped it several times and closed my eyes, thinking over and over how beautiful my Mistress looked without clothes. I became rock-hard in seconds, but Sarah let me continue to play with myself while she watched in enjoyment.

"Enough! Hold your cock at the base and present it for the whip."

With my heart beating a mile a minute, I pointed my member right at her, grasping my hairless balls and encircling the base of the cock with my thumb and index finger. I closed my eyes.

There was a faint sound of leather meeting skin before, almost without warning, a flash of total pain seared deeply into my mind. I had never known a pain so intense. It was blinding, horribly intense. It gripped me totally. I screamed out, loudly, the sound reverberating around the room. My knees immediately felt rubbery and I felt my legs almost give out from under me. How I remained standing, still holding my aching cock, I'll never know. In an instant, my once hard member was now totally limp. I was sweating profusely, breathing rapidly. Flashes of lightning crackled in my brain. I had never known such pain.

"That will be a lesson to you, Mr. Reynolds. You are not here for your pleasure, you are here for mine. And Priscilla's. And anyone else I desire for you to give pleasure to. Because of your insolence, I am dismissing you for the evening. Priscilla will re-insert a Tampon. You may not remove the Tampon until tomorrow morning. You must understand, during your future visits, that erections are a luxury that will be awarded only with permission. The next time you get a disgusting hard-on like that, there will be quite a few more strokes from my little cock-stinger. I gave you only one tonight to teach you a lesson. Ten strokes, minimum, next time. Maybe even with a nastier whip. No mercy. No forgiveness. Do you understand?"

My poor cock was still stinging with unbelievable pain. Words came with much difficulty over that pain. "Yes, ma'am," I finally blurted.

"Get a Tampon, Priscilla."

I continued to stand there, holding my aching, flaccid member in my hand, head down, eyes closed. Priscilla returned in a few minutes and moved behind me. Once again I felt her opening me backside. The way in for the thin Tampon was still greased, and it entered me easily. She used her index finger to push it deeply into me. She held the finger there for an agonizingly long time, as if she relished the idea of using her finger there.

"Do you have any questions, Mr. Reynolds?"

"I… I wonder when I may see you again, Mistress."

"I will call you. You are not to call me. Do you remember what else you are going to do before you are invited here again?"

"Yes, ma'am. I am going to buy seven pairs of women's panties and wear a new pair every day, all day long."

I could almost feel Sarah's smile. "Very good. When you wear them here, they are called 'punishment panties,' but they are worn for your pleasure the rest of the time. You may get dressed now. Priscilla will bring you your clothes."

Sarah turned and left. Priscilla followed her. The pain in my cock was slowly subsiding, but the memory of sting her whip had caused was indelibly etched in my mind forever. When Priscilla returned, she was holding the clothes I had worn this evening. I immediately noticed she had carried everything except my underpants. She smiled. "Mistress desires that you get used to women's panties immediately."

I was even more startled when I watched her pull her skirt up to her hips, revealing a pair of pure silky-white panties with a thin band of embroidered lace around the top. In one smooth motion, she lowered the panties down her legs, exposing for a wonderfully fleeting instant a beautiful patch of jet-black pubic hair before the law of gravity brought the skirt back down.