CHERRY SLAVE GIRLS

BY JSMILES

[ part 4 ]

The First Step

He walked around to the front of his desk, and pulled out a cloth that he laid in front of me. I opened my eyes in fear and wonder as he unwrapped the linen cloth. “Julie, you are about to take your first step toward becoming my well trained assistant. I will respect your maidenhood virginity, but I will train you in all of the other ways that a woman can please a man. You will become my “cherry slave girl” and will do exactly everything that I ask of you. You will be trained and tested so that you will learn to please me in all ways.”

I thought about running away, since I now realized he wanted Jamie and me to be his “little sexual playthings”, and I didn’t know if my sister or I could endure that. To do what Sir Michael was planning to do to me would be so humiliating and strip me of all of my dignity. It would also require all of my willpower to perform for him, as he would expect me to. But he had excited me so much with his fingers earlier, being forced to perform for him and made to cumm under his masterful fingers. I knew I had no choice but to conform to his wishes and desires for me. He had said that this was the first step to becoming his slave, the first step of my truly submissive life with him. This would be a life for me that was so different then what I was used to, a life of sexual slavery. At 18, my sexual experiences were very limited, almost non-existent, and now I was on the verge of a life of total sexual submission to a man who held me in the palm of his hand. I was in awe of his power over me, and knew that he would make me conform to his desires.

“Are you willing to accept your place here and have me begin your training. Julie?” he asked, “Or do I have to spank you into submission?”

I considered my options, and realized that I really didn’t want to end up on the streets or in prison, so Jamie and I had little choice. I softly answered, "If that is what you require of me, Sir, then that is what I will do. But please don’t hurt me."

”That's my good girl,” He laughed, “I wouldn't hurt you, Julie. In fact, I have every intention of helping you to enjoy your learning lessons as I enjoy your whimpers while you give me pleasure. That is what makes my cock hard, Julie girl, your whimpers of pleasure for me."

I trembled at his words and I watched him as he began to take out a selection of items from the drawer and place them in a nice, neat line on the white linen cloth. Some I recognized, others I did not. There were tubes of lubricant, a long probe with rubber beads, a series of large plugs, appear shaped thing, a double balloon thing with an inflating bulb and hoses coming out from it, and a medical speculum, all laid out in a nice neat row. I feared what he was going to do to me with those instruments, but I feared being abandoned to the harsh cruel authorities in town even more. I had never had any of these things in my body before, and I was overwhelmingly frightened. He moved behind me and said, "You have a lovely body, Julie. Now don’t move sweetie. You need to learn to accept my touches."

His hands began stroking my crimson red buttocks. I clung to the desk, as his hands moved all over her bottom. “I’ll bet you are already enjoying this, aren’t you Julie? I’ll bet your pussy is almost dripping wet." His hand reached down between my legs, and his thick fingers curling up under my butt cheeks touched my dripping slit. “AAHHHhhhh yes, my dear girl. I can tell this is exciting you.”

"Spread your legs open wide, Julie! Hurry up, girl. I want to feel just how excited you really are." As my face turned red, his hand cupped all of my sex easily, and then a thumb popped inside of my anus. I squealed at the intrusion into my tight little bottom. “What is my thumb penetrating right now, Julie?, He demanded. I hesitated for a moment, until he rammed his thumb deeper and demanded, “Say it, Julie. Tell me all the words you know for this sweet little puckered opening that is mine.” His hand clenched and unclenched on my sex and moved into my anus, goosing my body, and making my hips wiggle seductively to try to escape his ravaging hand. SMACKKK. His hand shot out and hit my ass cheek hard. "I said, tell me." I stumbled for words, as he returned to goosing me between the legs, my hips involuntarily thrusting forward into his hand as he fondled my hot sex and clit, and probed my tight anal ring. “Aahhh, my anus, my asshole, my bottomhole, and my rosebud, Sir.”

"Very nice, Julie. You have such a beautiful ass, my dear, and I am going to enjoy training it so much. Have you ever had anything inside of your anus, before your examination today?”

“No, Sir!” I whispered. “Well get used to it, Julie, because you and I are going to become very intimate. I am going to let you remain a virgin, but I am going to make use of your other two orifices so that you may pleasure me whenever I desire. You have already learned a lesson on how to suck me with your mouth, and now we are going to work on your tight little anal rose.” I trembled at his words, and suddenly I realized what he was going to do. He wanted to stretch open my tight little asshole. That’s what he meant before about exercising and stretching my little hole. I was sure it would hurt, but I knew that I didn’t have much choice and must submit.

I turned red in embarrassment, as his hands moved over my bum and tickled me between my cheeks. Just like a little girl, with my ass revealed as if I was going to be punished with a spanking or something by my Daddy.

"You are such a good girl, Julie, and I like that." His hands continued to stroke my hot ass cheeks, feeling the taut flesh. I clenched my ass cheeks tightly in fear. I was hoping to stop him from playing with me, or at least detour his other intentions.

His hands continued to grab my young ass flesh, rubbing my cheeks, still allowing me to tighten them whenever he got close to my tight anal ring. "Don't you like my touches there, Julie? I didn’t know what to say, but finally breathed out, “I’m afraid, Sir!”

He grinned and said, ”Yes my dear girl, I’m sure you are a little fearful, but you know that I desire you, and that you have promised to abide by my wishes. I promised to take care of you and you in turn are going to yield to me your tightest little hole, aren't you Julie? You know that I am doing all this to help prepare you for me, later. In fact you are going to help me to exercise your tight little nether hole. I am going to use many things inside your tiny asshole, and I will have to stretch it much wider for you to be able to take my manhood, later. You saw all these lovely little instruments, some of them are very small and some are very big. All of them will be used to stretch and “exercise” your tight little anus, until you are ready for me. When you are ready to yield your tight anal virginity to me, then I will accept your gift of your anal virginity, and take you with a lover’s passion. Until then, I will keep you as my protected ward, and make sure that your hands and mouth will get plenty of use as you relieve my pent up stress." I shivered at his words, while his hands continued to play with my bare flesh, massaging and rubbing my ass cheeks.

I quivered in fear as I realized that my tight little bottomhole was going to be someday plundered and penetrated by his big cock. I had never ever really considered that a man would want to penetrate a girl’s tight little bottomhole, but Sir Michael was determined to stretch mine with his toys and then his thick manhood. I considered all my alternate possibilities, and then trembling, I said, "I will do whatever you want, Sir Michael. I want to please you, Sir. You have been very kind to my sister and myself, and we do owe you some gratitude for that. Just please, Sir Michael, don't hurt me too much. Please be gentle with me and even though I know it will probably hurt and I probably won’t like it, I’ll do whatever you desire for me. I will yield myself to you, Sir, but I beg you to please be gentle with me. It just felts so strange to have something in me back there."

"Shush, my little girl,” Sir Michael said. “I will take good care of you. I will lubricate your tight little asshole real good with my finger, real deep inside, so you are very wet and slippery. You want me to lubricate you, don't you Julie? You don't want me to do it to you dry? Tell me what you want me to do, Julie."

I began to sob, while his hands were still pawing all over my flesh like he owned me. "Yes," I replied.

"Yes what, Julie. Do you want me to penetrate you dry? Is that what you want?"

"No,” I squealed loudly, “I want you to lubricate me…., I mean lubricate my anus with your finger, Sir." I replied, humiliated at what he required me to say.

"OK Julie, I’ll do that for you, but first, I'm going to feel your pussy, Julie. I know you like that! I am going to put my fingers into your smooth little pussy and see how wet you already are. While I do that, I want you to loosen up your ass cheeks. I can't feel your anus if you keep your cheeks so tightly clenched. OK, Julie? Can you spread your legs and your cheeks a little wider for me, just a little wider so I have better access." His voice was so commanding, as he ordered me to perform for him.

Then I felt his cold fingers slip around into my pussy, tickling my pink folds. His other hand slipped between my cheeks, and his finger encircled my tight anal ring. I shuddered as he touched me there, while his other hand slipped around between the lips of her pussy. They were already dripping wet with my juices and from the weird excitement that I felt as a result of his intense desire for me. He was such a powerful man, and I knew he wanted me. I bowed out my legs, giving him greater freedom to my pussy, but also leaving my tiny anus unprotected from his fat finger that he soon pushed between my spread cheeks.

"Your pussy is so sweet and so wet. Someday you will make a great fuck for some lucky man.," he said. Then his fingers slipped deeper between her pussy lips, seeking out the barrier in my vagina. His other finger, the one circling my rear hole, tickled my anus and made it wiggle and wink. Wiggle your ass for me, Julie. I want you to show me that you are enjoying having me touch your virgin pussy and your tiny asshole. You want me to do this, don't you Julie? You want me to tickle your asshole, and massage your pussy like this, don't you?" he asked, teasing me. I shivered and felt so funny as he touched me and circled my tight little ring. I actually was enjoying his attentions, and so I said, “Yes, Sir! I do!”

He chuckled for a second, and then Michael stopped his fondling of me and moved behind me. He bent down so he would have an unobstructed view when I exposed my asshole to him.

"Now be a good girl, Julie, and reach back with both hands and spread your cheeks apart." Hesitantly I grabbed my youthful globes in my two small hands and with my fingers only inches from my asshole, I began to peel back the fleshy globes. "A little farther, Julie!” he asked. “Spread them real wide for me, Julie. Can you feel your tiny little rosebud puckering as it awaits my touch. It’s so cute! Imagine how much I will enjoy sliding my thick manhood between those pretty cheeks, and how big it will have to stretch to take my thick 8” cock."

He watched my expression of shame as I exposed my most intimate opening to his gaze. He blew on it, making me shiver in fear. Then he took his finger and tickled the rim of my anal ring. I wiggled my ass as he tickled me. He slapped my ass and he laughed as he continued to stimulate my tight little rosebud. Then he commanded to me, "Stretch yourself back over my desk, Julie, and hold on."

As soon as I had stretched myself out, gripping the edge of the other side, He pushed down on my back, forcing me down onto the surface. "Push your ass up now! Good girl, Julie! Then he stepped in front of me and wrapped a wrist cuff around each wrist, and secured then around the front legs on his desk. I was stretched over his desk, and held in place for him to do with me as he willed. He looked into the eyes, and said, “I'm going to lubricate your asshole, first, Julie. Then you will be given an enema to clean you out. After you are totally clean, I will begin probing it with various instruments. All of them will all measure the elasticity of the sphincter in your asshole and help to prepare you for me."

I lay secured across his desk, my head resting on the hard surface, totally exposed to him. I saw him take a container from the table, and heard him unscrewing the metal cap. I knew that it was some form of lubricating jelly. I just waited for the touch of Sir Michael's hands rubbing between my ass cheeks and the lubrication he had promised to me.. I was secured and helpless as Sir Michael took liberties with me that I never would of dreamed of letting anyone do to me. His hands continued rubbed and massaging my cheeks and tickling my anal rosebud.

Then he said, "Now relax, Julie, this is going to feel cold and strange." He placed his fingers on both sides of my asshole, stretching the little bud apart. His finger and the cold jelly on it touched my shriveled little rosebud. My body jerked in response as I knew my moment of anal training was about to begin. "Relax Julie,” He said, “It’s only a little cool lubricant. Take a deep breath and relax your asshole. Now push your little anal rose out for me," He ordered.

He felt the tiny mouth push out and he took that opportunity to push in with his finger. His finger slid in effortlessly, helped by the slick jelly, while my asshole stretched tight around his knuckle. He heard me suck in a breath and gasp, as he began fingering my tight asshole. He twisted his finger inside of me, feeling me deeply, while his knuckle stretched my anus inward and outward to accommodate his plunging finger.

"Another deep breath, Julie," He said, as his finger pushed in harder. I felt every centimeter of his finger sliding along my anal tract on the slick jelly until his knuckles banged against the inner linings of my stretched asshole.

I felt violated and very exposed, while my sphincter tried to relax on the plunging finger inside of me. I felt my sphincter spasming, gripping his fat finger, hugging it tightly. Then I heard him open the top of the lubricant jar again.

"I’m going to rub it around inside this time, Julie. So relax your asshole again." His finger began moving out, then back in again, corkscrewing around inside of me. I knew he was lubricating me for bigger things, namely his 8” cock. He pulled his finger out and I heard him push it inside the jar again, a sloshing sound as he coated it again. "Now two fingers, Julie. Are you doing all right?"

"Is it going to hurt?" I whimpered. I braced myself, and then a sudden plunge back inside of me. His fingers were stretching my little hole wider and wider. It hurt as they turned and twisted around inside of me, not stopping until they were embedded deep, past his knuckles.

"OOOH," I cried out as Michael spread his fingers inside of me, stretching my anal tract to accommodate them.

He pulled his fingers from my asshole, watching as my little rosebud closed and winked at him, with the lubricating jelly making my tiny hole glisten. Then he walked in front of me and took the pear shaped double balloon shaped plug with the hand pump and hoses attached. I had never seen anything like this before, and didn’t realize what a wicked little device it really was. I had no idea what I was in for. He moved behind me and spread my cheeks wide, and said. “This is called a double balloon butt plug, Julie. And it is used to administer an enema to you.”

Suddenly I felt something nosing itself into my rectal opening and felt the cool rubber tip slide inside of me. Sir Michael slowly inched all of the balloon into my anus, and then began to pump it up. My anus expanded, as one balloon inside and one balloon outside of my rectum expanded my tight little hole. I soon felt strangely full back there. He then went over to the sink and brought back a large red bag filled with some kind of fluid. He attached the bag to one of the hoses, and suddenly I felt a rush of warm fluids fill the insides of my bottomhole. Plugged as I was and securely fastened over his desk, I had no other option than to suffer the indignities of having an enema. I knew what it was, because Papa had given me a few of them, but he didn’t use a double balloon plug, or secure me down. The fluid quickly filled my rectal cavity to bursting, and the cramps soon arrived. Plugged and restrained as I was, I could only whimper and plead for Sir Michael’s mercy.

As I sobbed and whimpered in pain for him, he reminded me, “Julie, you may squeal and cry all you want, but this is required for your own good and to clean out your colon. If I didn’t do this first, you couldn’t stand the training methods. Now just relax and hold it a bit more, and then I’ll let you void it.

I tried to be strong and tried to be brave, but it hurt so much! Finally, as I sobbed from the cramps and water pressure inside of my colon, I felt his hand on my bottom as he released some of the pressure inside of the balloon. He moved a basin behind me and gently pulled the plug out. My bowels gushed out their contents and soon I felt relief. Sir Michael gave me one more quick enema to rinse me, and then he gently cleaned and prepared me for my anal stretching exercises.

After he had cleansed my bottom, he picked up a long anal rubber probe. The device had to be over 14 inches long, with a pull ring on the end. The probe tip was skinny, barely the size of my little finger, but every two inches was a bead, about the size of a plum. The probe was used to test depths, the beads only purpose was to expand my anal tract as it moved in. He showed it to me, and said, "I'm going to see how deep this will go, Julie. It is going to feel very strange the deeper it goes. It will probably cause some cramping inside you, Julie, but you will be fine. I want you to lie still while I do it. Can you do that, Julie?" I nodded and said, “Yes, Sir, I’ll try!”

It looked so long and menacing. How was he ever going to get something that long inside me. I began breathing rapidly as I waited, unable to do anything but tremble in fear. Then I felt the probe at my anus and it slowly began to slide inside of me. I felt the pressure as it moved deeper inside of me, the first bead stretching my anus open before popping inside of me. Sir Michael continued to press the probe forward so the second bead now passing through my anus. My tight little rectum clamping down on the beads as they passed through. Two beads were now inside of me, stretching my anus open and then hugging them as they passed.

Michael watched carefully as over ten inches of the probe was pushed inside of my tight little asshole. Then the next bead stretched my asshole wider to accept it. He allowed it to enter before he began to move it, watching me as I moved my feet and danced as the probe was very uncomfortable by now. He began to pull it out, slowing down as the third bead was pulled loose. I gasped loudly as my asshole convulsed and had to shift to allow its passage. He pulled another bead from my asshole with a slight pop sound that could be heard throughout the room.

My body just shivered and trembled as I endured a trial the likes of which I had never previously known. It felt like my guts were being pulled from me. Finally he pulled the last bead out and my anus began spasming wildly. My asshole felt hot and then empty as the last bead was pulled out. The little rubbery ring of my anus closed after the last bead in me popped free. He asked me, “Now that wasn’t so bad, was it, Julie?”

I let out a sigh of relief. "OOhhh Sir, it hurt terribly, and it gave me cramps when it was in so deep. I'm glad it's over," I said.

Sir Michael dipped the probe back in the jelly, "It's not over yet, Julie! I need to do it one more time, only this time deeper. I need to see how much your asshole can accept. After all, I am a very well endowed man, and I don’t want to hurt you when I plunge to your depths as I take your anal virginity. Now take a deep breath and relax again, like a good girl," Suddenly, I felt the probe push against my asshole. This time he didn’t wait for my response. Sir Michael pushed it all in with one continuous push. Restrained as I was, I screamed wildly and kicked out, as it hurt so much more, the deeper it went. I panted and gasped, in between sobs, as he pushed the anal balls in deeper.

It felt like a huge snake, as it continued to go inside of me, banging painfully against my anal tract as the balls expanded my rectal walls. I bowed my legs out, hoping to relieve some of the pain and cramping, but Sir Michael continued to press in even deeper. I could feel the beads go inside of me, now over 12 inches of thick rubber pressing upward into my previously unpenetrated colon. "AAAgghhhhh, PLEASE! OOOwwww, Sir, please hurry and get it over with," I cried out, “It really hurts!” as the probe continuing the deeper exploration of my anal tract.

Finally Sir Michael hit the limit of the probe. Any farther and I was sure he would cause serious damage to my anal tract for me. "You have it all, Julie, all fourteen inches of it. How does it feel?"

"OOOhhhh, GOD! PLEASE, take it out quick,” I squealed in panic, “The cramps are terrible."

I was dancing around on my toes, spreading my legs to try to stop the spasming cramps. Sir Michael took his time, pulling it out, then pushing it back in again, fucking my ass with the plunging probe.

"OOOhhh, Hurry," I begged. I finally felt it being reluctantly dragged from my plundered asshole. I slumped down on the table, glad to have it over with.

"We’re not done yet, Julie! Now I'm going to inspect inside your asshole." I groaned in dispair, as he pulled out a rectal speculum. It was over 6 ½ inches long, with three long prongs. It was built to spread an anal opening over three inches wide. The three prongs allowed maximum stretching and had a scissor like locking mechanism, allowing it to lock open at various widths.

My body went tense again when I saw the device. I knew it would hurt me when I was spread that wide. I heard the jar opening again, knowing what was coming. I watched as Sir Michael liberally put the jelly on the three prongs. "Must you do that, Sir? I beg you, please don't!" I sobbed, with tears running down my face and falling onto the table.

Sir Michael stroked my ass cheeks, and said, "Now, now Julie, I must inspect you properly. This makes it very easier for me to hold you open. Now just relax your asshole, or it will hurt worse if you fight it. Trust me, Julie! I’ve opened a number of young girls bottoms to the pleasures of anal sex. In fact, my cousin, Doctor Brown and I have published a book on “Anal Sex Training” and have done this numerous times to young girls in our employment. This is for your own good, believe me!" He said.

I paused for a moment, “The Doctor is your cousin?”

Before I got an answer, I felt the cold metal instrument touch my asshole. I tensed up and felt the three probes running over my exposed anus before they finally started to enter me. It did not hurt very much as it went in, for which I was very thankful. Then Sir Michael twisted it a little bit to move the arms deeper into my rectum. I felt a little stretched, but the spread between them was only about an inch wide. Then HE reached for the tube of lubricant.

“Julie, I need to examine how your inner rectal tract responds to this ointment. I will probably use some of it to help lubricate your bottomhole when I take you. You would like me to lubricate you, wouldn’t you? Knowing I had no choice, I said, “YES, Sir! Please lubricate me good!”.

“I know you can stand a little more stretching, and it will give you an idea of how wide your anus will stretch to accommodate me." HE began to squeeze the scissors grip, watching as the three prongs began to expand my little hole. HE pulled the prongs a bit out until the outer flange locked on the lips of my anus. HE then slowly squeezed it again, satisfied that the prongs were secure, watching as my anus gaped widely before him.

"Stop PLEASE!," I screamed, as I felt my rubbery anal ring stretching wide open. The stretching of my sphincter muscles burned like fire and I feared that HE would tear my tight little bottomhole. It felt terrible, my asshole opening up wider than ever before. Then I felt the cool air of the room entering my opening that was so widely expanded. "No more PLEASE!" I begged, “It REALLY HURTS!” I screamed. I was deathly afraid that HE would tear my anus and that I would bleed to death.

Sir Michael continued as my anus now was spread almost two inches wide, exposing a large pink gaping hole. HE ran HIS finger around the inside of my sphincter ring, letting me feel how open I was for HIM.

"A little more, Julie," HE announced as HE spread my anus a little more. Another squeeze and it was over two inches, with my inner tract exposed to HIS gaze. HE could actually see deep inside of my anal opening.

My tears were flowing freely from my eyes as my anus burned from the stretching. I felt his fingers encircle the rim of my stretched anus. Suddenly a sharp pain erupted from inside of my asshole, and I cried, as my rectum began to spasm. I heard his voice, telling me that it was almost open two and a half inches wide. The burning pain from my asshole radiated throughout my whole body, and I just sobbed, wanting the pain to stop. I jerked in pain as Sir Michael locked the speculum open, a sudden pain shooting out from my painfully spread anus. "OOOOWWWW, PLEASSSSSE" I cried, as I could really feel the pain from my terribly dilated anus.

I looked back through my tears, and Sir Michael had a look of awe about him as if he had never seen an asshole so spread as mine. It left me open wide for HIS pleasure, with very little interference from the speculum. Then HE took a little dab of the ointment and placed a little bit around the rim of my anus. Playfully HE ran his finger around the outside of my anal pucker, continually feeling me squirm as my tender anal ring suddenly began burning from the ointment.

"OOOWWWW, MY GOD, Sir. What is that stuff? It burns so much!," I cried.

Sir Michael showed me a tube of Ben-Gay liniment and said, "I warmed up your anus with a little bit of this warming ointment, Julie. Now lay still, my sweet girl, while I rub a little bit of crème around inside of your asshole."

"No please, NOT that," I cried, as I had already felt the pain from the heat of the Ben-Gay on my anal rim, and now he wanted to rub it on the inside of my anal tract. This would be much worse on the inside of my tender anal tract, and I couldn’t believe that he was doing this terrible thing to me. I know I had been naughty before, but this was just painfully cruel. I cried loudly, but despite my pleas, he applied the crème around the mouth of my anus and then rubbed some down inside. At first it felt cool, but then suddenly I jerked and squealed out loudly, "AAAGGGhhhhh GOD! OOOhhhhhh, PLEASE, SIR! OOhhh, it burns terribly. OOOhhhh, PLEASE wipe it off." Cuffed as I was, I could do nothing but wiggle and move my ass around, as the Ben-Gay burned on my sensitive exposed and tender inner flesh. It felt like fire in my hole, and I was sure that it would permanently harm me.

Sir Michael laughed, and then released the speculum, watching as my asshole slowly decreased in size and spasmed from the heat of the Ben-Gay. After a few minutes it was still open over a half an inch, refusing to shrink back to its tiny former self, while the Ben-Gay still burned on my sensitive anal rosebud and inner tissues. I felt my anus gaping open and knew that little rosebud would never be the same again. I also knew that soon it would be stretched to my limit, as it would be wrapped around Sir Michael’s massive 8” cock. I shivered with fear as a burning ache lingered from the Ben-Gay on my tender anus opening.

Sir Michael walked around the desk and lifted my face and kissed me on the lips. I felt a rush of passion inside of me for this man. I knew he was hurting me, but yet I wanted him to love me. I was willing to suffer a little for him, but I needed to know why he wanted to hurt me. “Why?” I asked.

He lifted my pretty face and kissed me again, and said, “You know why, Julie. I am training you to accept anything that I desire from you. I desired to see you whimper and wiggle for me with the Ben-Gay burning your anus. It causes no permanent harm, but trains you to be accepting of my desires. Now relax, Julie, and feel the warmth that I have for you. You please me very much and you did a wonderful job of passing the first step, and I’m proud of you!”