I don’t remember my first months at the convent. They say it was trauma amnesia. I was 7 years old when I was left there after my parents were killed in a car accident. I can not complain about the life I had there. It was better then an orphanage. The sisters taught me everything that a girl should know. Cooking, cleaning, and traditional education. I grew up knowing I was loved. It was my eighteenth birthday when Mother Superior sat me down to explain that it was time for me to leave.
I could not grow to my full potential if I stayed at the convent. Arrangements had been made for me to stay with a man who had been friends of my parents.
I took a taxi to the airport and I was stunned at the changes in the world. I did not remember much but it seemed so fast paced and different from anything I had known. When my flight landed in Boston I was greeted by a chauffeur holding up a big sign that said Miss. Annie Raymond. The driver led me to collect my luggage and than to a huge black limo. He settled my luggage and me in the car and we began the drive to my new home.
After about ten minutes he rolled the divider window down and introduced himself as Rick. He looked at me in the rearview mirror with a look mother superior had warned me about. So that is Lust I thought. I knew I was pretty. I had lived without many luxuries but a mirror was not one of them . My hair was a copper red and it flowed past the middle of my back. I had large hazel eyes and what Sister Mary Agnes called a ski jump nose. I was petite. A fact Rick was not shy about pointing out.
“I never would have recognized you.” He said “I was expecting a women but you look no more than 15.”
He was right. At 5’1″ and 98 lbs. I did look like a teen-ager. I was thin all over and my breasts were small for my age. I was barely a B cup but I had large nipples. We chatted nervously for about half an hour and he then told me that I should just sit back and relax and watch some television. I was so excited. It was the one thing I had missed out on. I found the remote and began flipping through the channels. The reception was poor but I didn’t care. Rick also said there were movies and a VCR. For the rest of the two hour journey I sat transfixed by the images on the screen.
When we finally pulled up to the house I was in shock. It was no small house it was a palace. It seemed to go on forever. I looked even more the child as I straightened my braids and the blue plaid skirt Mother Superior had given me. We walked through the entranceway that was flanked on either side by a Gargoyle. As we entered the foyer we were greeted by a butler. His name was Reginald. The resemblance between Rick and Reggie, as he insisted I call him, was astounding. I had seen twins before but they were identical. In there mid thirties they both had caramel colored hair and eyes to match. They were about 6 feet tall and sturdily built. Rick passed my luggage to Reggie and bowed slightly to me. ” Miss. I shall see you around.” He said with a smile.
Reggie’s eyes scanned me the same way Rick’s had as he led me up a grand staircase to my suite. I was overwhelmed by its opulence. There was a huge bed with flowing white canopies and plush baby blue carpeting. There were fresh flowers everywhere. Reggie dropped my bags in the walk in closet and began to unpack my few things. He said that Rick would bring me shopping to get anything I might need .From there we walked to the library. As we walked through the door I was greeted by a striking man in his late 40’s. He had salt and pepper hair and goatee he was at least as tall as Reggie and maybe 20 lbs. Heavier. He was beautiful. He put one hand on each of my shoulders with tears in his eyes.
“My dear child” he said “you are the spirit an image of your mother.” He pulled me into his arms and I felt warm. The scent of him was intoxicating. I was not used to men and now I was surrounded by them. He stepped back and smiled, “God how rude of me to not introduce myself I am Jack. Welcome home.”
For the next three weeks I became adjusted to life on the outside. Spring was just beginning and I felt alive with its newness. Uncle Jack, as I now called him made me feel right at home. We spent afternoons shopping together and evenings by the fire talking about my parents. Rick and Reggie were also a big part of my adjustment. They were not just servants they seemed to be friends to both Uncle Jack and myself. I was intrigued by all these men around me. I had no sexual experience, I had never even masturbated. I guess it was a byproduct of being raised by nuns. But as the weeks wore on I felt my self awakening right along side all of the spring blossoms.
It was late one Friday evening that I awoke to see Uncle Jack standing in the doorway to my bedroom. He sat silent watching me sleep. I was curious at first and peeked ever so slightly, I did not want him to think he had woke me, I saw his form outlined by the lights in the hall. The feature that was most prominent was the bulge in his pants. I knew the facts of life so I knew what it was but I had never seen one before. I quickly closed my eyes and the next time I opened them he was gone. Over the next several weeks this scene had repeated itself without change until the Tuesday after the Memorial Day holiday. I waited for him now. I knew his routine. Just after midnight he would come to my door and this night was no different. Just past the chiming of the Grandfather clock he appeared. I knew something was different right away. He usually came in his regular clothes but that night he had changed into his night clothes. He wore burgundy silk pajamas and a matching robe. He stood for only a moment before entering my room he walked to the side of my bed and reached out to stroke my cheek. I could feel the warmth on my skin and smell his signature scent of L’Eau D’Issey. Just as quickly as he approached he retreated to his position at the door his ever present erection straining at the silk of his pajamas. I lay on my back with my head tilted softly towards him and my eyes just barely open.
He began rubbing chest as if wiping away imaginary lint but softer. His hands moving in slow circles down to the bulge that so attracted my attention. He rubbed for a few moments then pulled his hands away and began to leave. He stopped and returned to his place and began rubbing again. I did not stir. He removed one hand and unfastened the lone button on his pants. I almost gasped when I saw this, but I held my breath instead. He reached in and pulled his penis from the cloth. It was larger then any I had seen in my anatomy texts. I watched intently as he began stroking his member. Puling at it softly at first then harder and faster as time progressed. He had a look between pain and euphoria on his face. He stoked faster still with his right hand and with his left he began cupping his testicles. After just a few moments his knees began to buckle and he emitted a small groan. He pulled the robe over his penis to catch his ejaculate and shuddered. He stood for just one second more and walked away down the hall. I lay awake for quite sometime after he left. I had the strangest feeling between my legs. I reached down to just adjust myself and through my cotton panties I felt that I was wet. I pulled my hand quickly away and forced myself to go back to sleep. After that night the frequency of his visits increased. Each night the same thing. He would touch my cheek then masturbate. One especially warm evening I had my right foot and calf out from under the covers and he touched that instead. I felt electric at his touch. The next evening I pulled the covers away more exposing my thigh and he touched that. It became a game to me, an arm one time a leg the next. I was becoming aware of my own desire for him to touch me. I became more and more bold. Within two weeks I was planning things for my own pleasure. My boldness was increasing as well. It was mid July when I decided to sleep with the covers tossed completely aside. He touched me on my thigh and my stomach and just ever so slightly brushed my breast before he retreated to the door to masturbate. The next night I again left the covers off but I pulled my white nightgown up so that the end rested just above my panties. His hands seemed to shake as he approached me. He reached for the hem of the gown and in doing so slid his fingers across my panties. He seemed extra excited as he pleasured himself.
Just one week from that July visit I pulled the covers tightly around me and began to touch my breasts, my nipples became instantly alert. I was surprised at how quickly my body reacted. It was close to midnight and I knew Uncle Jack would be coming soon. It was as though the knowledge of his arrival was driving my body into a frenzy. The heat from between my thighs was unbearable. I pushed the covers away and lifted my night dress completely off my body. I placed my right hand over my breast squeezing my nipple between two fingers and ran my left hand down my stomach, under the elastic of my white cotton panties and began exploring myself. It was slick with my virgin excitement. The pure sensation of knowing I was touching myself gave me shivers. I began to feel my way around the parts of me I knew from Anatomy. The labia, vulva, and the clitoris. As my index finger rubbed against my clitoris and I began to shake. The clock struck midnight. I pulled my hand quickly away and pulled the covers up to cover one side of me. Leaving my panties and right breast exposed. I heard Jacks footsteps down the hall and another gush of wetness soaked my panties. He walked into the room and approached me slowly. I heard him gasp as he saw my breast bare before him. My nipple still firmly aroused. He did not walk away he pulled himself from his pants and began to quickly stoke. He moaned louder than before and covered himself in record time. I think he even surprised himself at how quick his orgasm came. He could not catch it all and one spurt landed right on my nipple. He reached down to wipe it away pausing to caress me. As he walked away I knew things would never be the same.
Things began to change the very next day. That morning at breakfast when Uncle Jack hugged me he held the embrace for a moment longer than usual. To anyone else it would seem nothing but to me and my awakening sexuality it was a sign. As I readied myself that night for bed there was a tentative knock at the door. Uncle Jack peeked his head through and said “Annie, I think it is time we had a talk.” I nodded and motioned for him to sit on the bed with me.
“I am not sure how much the nuns spoke to you of sex, but as your guardian I feel it is my place to make sure you are aware of the realities of human sexuality.” He said calmly.
I blushed at his openness and replied “I know the fundamentals. I took biology and anatomy.”
“There is so much more than that,” he began ” The human being is more than the sum of its parts. We are made to experience not only the mechanics of reproduction but the sublime ecstasy that making love can bring to people. Have you explored your own sexuality at all?” He asked.
Again I blushed and was at a loss for words. He seemed to understand my thoughts without any words from me.
“There is no shame in self love. Masturbation is a normal, healthy part of maturation. It teaches you what feels good and what does not. I myself masturbate frequently” He added. I glanced down to his groin as he spoke those words. I could see that he was partially erect.
“Have you ever seen a penis?” He asked
I quickly responded “No, never a real one just in books.”
“Would you like to see mine?” he said in almost a whisper. His voice still strong.
I pulled back a little but still from somewhere inside me came the simple word “Please.”
He looked to the door to make sure we were alone and reached down and drew his penis from his silken pajamas. I was shocked at how quickly it had grown to its full size of about eight inches long and quite thick. The head was slightly purple with the pressure of his arousal. The veins on the shaft seemed to move on their own pulsing with each beat of his heart.
I reached out to touch it and he said “Not now, meet me in the library tomorrow at midnight. Then all your curiosities will be satisfied. ”
The next day I was aroused all day long. I seemed to be a little off and Reggie and Rick both questioned me as to what was wrong. Each time I replied with “Oh, nothing.” And a sigh. At ten o’clock I excused myself from a late supper with Uncle Jack, the boys and Marie, a friend of Jacks. I went to shower and ready myself for the events I was hoping would follow. I lingered as I washed my breasts and genitals. But not too long. I wanted to save my excitement for that evening. I agonized over what to wear. I was torn between wearing my simple white nightie that had spaghetti straps and fell about mid thigh or my usual uniform from the convent of a plaid skirt and white blouse. I was still deciding when Marie entered my room.
“Jack asked me to check on you.” She said. I blushed at my half nudity. And pulled my robe tightly around me. “Are you having a problem?” she asked softly reaching out to touch my hair that was held back in two braids. I told her I was to be talking with my Uncle later and that I was unsure what to wear. She reached out and held each outfit against my body. First the skirt then the nightie. She fingered the flimsy white cotton. “This is perfect.” She said. “Jack will love it.”
“He helped me pick it out,” I offered.
“I can see Jack doing that.” She lingered over the soft cotton and handed it to me. “You must hurry, you don’t want to keep Jack waiting.” She smiled and let her lips brush my cheek. “Child, you are very special and Jack loves you very much. Take my one piece of advice. Be honest and trust him.”
I mused her words as I finished dressing. I pulled the nightie over my head. Looked at myself in the mirror and just as the clock began to chime twelve I walked out the door and headed to the library.
I knocked on the heavy oak door of the library. I jumped back slightly as it was opened. Uncle jack stood before me wearing his regular soft silk pajamas with a matching robe. He greeted me with a smile and motioned for me to sit on the sofa. As I walked into the room I noticed all the lights were off except for two. One at either end of the sofa. I sat at one end of the sofa and Jack joined me. He sat just inches away from me. I could feel the electricity between our bodies. He put his hand on my bare knee and began,
” As I mentioned I feel responsible for your sexual education. I want you to know that I would never hurt you but sometimes growth may seem frightening. Do not be frightened. You are safe with me. We talked yesterday about the penis and I sensed you were not being truthful with me. I want only honesty from you. Do you understand young lady?” I nodded. ” I will ask you again, Have you ever seen a penis before last night?”
I lowered my eyes and for some reason they began to swell with tears. “Do not be afraid” He reassured me.
I took a deep breath and began telling him how I had witnessed his excursions to my bedroom. He seemed to smile in a very self satisfied way. “Ah, so you have had an introduction to men masturbating then, ” He laughed. He then got serious. “How did it make you feel to see me pleasuring myself?” I began to shiver as I remembered the image of his long thick penis. The sensation of his sperm on my breast.
“It made me feel funny.” I said quietly.
“Funny how?” he inquired
“Between my legs” I whispered.
“Did you become aroused?” He asked in a throaty voice.
“Yes.” I mumbled.
“How were you aroused,?” He continued
“I became wet between my legs. My nipples became hard.”
“Did you see me ejaculate” he asked.
“Once” I confessed
“I wanted you inside me. I wanted to feel your penis. Touch it, caress it.” I ventured.
I reached for him and he blocked my hand. “You are not ready yet you are going to learn many things tonight and one of them is the pleasure of watching.”
From a darkened corner of the room appeared Reggie and Rick. Both of them were wearing just robes. Their long lean bodies barely covered. I knew not to be afraid. They approached Uncle Jack and myself. They both petted my head and stood in front of Jack. He removed their robes they were gorgeous. Identical in every way. They both had huge penises and hard bodies. “Welcome my pets,” Jack said. “Are you ready to teach my beloved niece how to enjoy watching?’ They nodded in unison. They moved to sit on the sofa opposite us. I looked confused. Uncle Jack explained. “Sexuality is not only between man and woman. It is between any people who love one another. I share my sexuality with both men and women and if you are wise you will do the same. It offers the most rewarding experience.”
I turned my eyes to watch Reggie and Rick. I was fiercely aroused at their presence and when they began to touch each other I got so wet I reached to contain myself. “Yes, my dear” Jack said. “Touch yourself explore your body.” He moved closer to me and removed his penis from his trousers . The boys were already groping at each other with their hands and mouths. Uncle Jack pointed out the pre cum glistening on their cocks. As he called them. The thrill of the words ran trough me. I whispered “Cock.” Jack smiled. “What a good girl. You will learn many new words.” I asked him what to call my genitals and he said he was fond of the words Pussy and Cunt. I repeated them both to him and he smiled. Reggie and Rick were putting on quite a show. They were really getting hot. Then Reggie moved down to his knees and took Rick’s cock in his mouth. I moaned as I ran my fingers over my clitoris. He licked and sucked him and I wanted to do it too. I wanted to lick all the men in the room. My finger entered my pussy. It was dripping and accepted my finger like a hungry mouth devouring it up to the knuckle. Soon both boys were on the floor licking and sucking each other. Their hands explore each others bodies with no inhibitions. They touched each other boldly and with passion. They were fingering each others anus. They moaned loudly and I saw spurts of sperm slipping out of their mouths. I could no longer contain myself and began furiously ramming my finger into me. I wanted more I needed more. Uncle Jack put his hand on my arm and said “Slow down angel. It is a long night and you will get yours soon.”
The boys remained on the floor wrapped in each others arms. “Did you enjoy that” Uncle asked and I moaned “yes.”
In the after glow of Reggie and Rick’s passion. They moved to the couch in each others arms. Uncle Jack looked at me. My finger still buried in me. “Has anyone ever touched you before?” Uncle Jack asked.
“No.” I murmured.
He motioned for me to sit on his lap. I pulled my lithe frame onto his lap. His hard cock still exposed. I sat facing the boys and shivered in anticipation of what was to come. Uncle Jack slowly lifted my night dress off of me. Exposing my small but firm breasts. I leaned back against him and let my legs fall open.
“Do you want me to touch you” he asked
“Please,” I begged. Craving his touch.
“Where do you want me to touch you?” He teased.
“Between my legs. Uncle, Touch me between my legs.” I pleaded.
“Why should I touch you? Have you been a good little girl?” He taunted me.
“Please Uncle I will be the best little girl. I will do anything you want me to.”
“”Tell me where you want me to touch you.” He said
“Please,” I begged “between my legs”
“Where.” He continued.
“between my legs. My cunt. Touch my cunt Uncle. Please I want you to be the first man to touch my virgin pussy.”
He began slowly feeling up my legs. Looking at me and then the boys who were masturbating watching the scene before them. That pleased me knowing that I was giving them pleasure. Made me squirm more. Uncle Jacks fingers finally reached the edge of my white cotton panties. He began whispering in my ear.
“How bad do you want it? Do you need it? You need to be touched don’t you? Spread you legs wider my little one. Let me feel you stretch those virgin pussy lips wide”. He taunted me in a husky whisper. I spread my legs wider exposing as much of my pussy as I could. I could feel his already hard cock throbbing beneath me.
I watched Reggie and Rick get more excited as Jack lightly stroked my lips. The boys again moved to the floor, not to each other but to me. They pushed them selves together between my thighs and I moaned. I could not even imagine the sensation that was to follow.
“Do you want them to touch you” Jack taunted… I could only whimper and nod.
Before I could fathom what was happening their velvety tongues were on me. Lapping up all the juice that had gathered on my lips. My clit was swelling with each tongue stroke and one of them took it between his lips and began to suck. While the other nestled below, began tonguing my hole. I began to shake, after a moment I felt like I was going to explode. Jack said “STOP.” And the boys pulled back and began stroking each other again.
“You have learned the intensity of pleasure” jack uttered “but you must learn to give pleasure as well.” On that cue Marie entered from the shadows. She was naked. Her breasts were huge. Her pussy outlined in the finest downy fur. I jumped from Jacks lap and dropped at her feet. Her pussy lips right in front of my face. She sat on the sofa near jack and said “do you want to touch me…learn to pleasure me like the boys pleasured you?” My only answer was to bury my head between her thighs. The taste of her cunt was unreal, I could not get enough. I lapped at her like a hungry dog. Nibbling her lips and clit as she began to moan beneath my tongue. Her shaking voice directed me to all the right spots. Soon she was pushing my head into her more grinding her pussy against my face. She thrust once, then again and a flow of the sweetest thing I ever tasted dripped from inside her. Jack instructed me to lick it all up. Taste every drop of her cum. I did as I was instructed and my reward was to be soon.
After a moment of rest Jack pulled me to him. He put my hand on his throbbing cock and told me to stroke him. I did . He was so excited it was just a moment before he came. Shooting his hot cum all his belly.
“Are you ready for your greatest lesson ” he asked.
Desperate and nervous, but craving his touch…”Yes…” I begged.
He laid me on the floor, a soft Oriental rug beneath me. He slowly pushed my legs apart and said “I think this will hurt, but know that it will also give you amazing pleasure.” With that he lay between my legs and slid the tip of his cock against my slit. Pushing ever so gently against the pressure of my tight virgin hole. I moaned as he entered me fully. I was so excited I did not feel pain only the pleasure of being filled. It was not long before I could feel the ecstasy building up in me. His thrusts were soft but powerful. Each one drawing me up to him then pushing me down.. Jack was moaning. Marie and the boys looked on as I approached my first ever orgasm. I shuddered and I think blacked out. As I became aware of my surroundings Jack was still thrusting gently…Whispering in my ear. “That’s my girl…what a good girl you are. Did you come for me?”
I nuzzled into him and he said “That is only the beginning” He pulled his cock out of me still very hard. Looked to the boys and asked “Whose next.”
Before I knew what hit me I was being filled again. Reggie on his back, me on top of him. Jack was behind me and I felt his cock push against my ass. I was a quick learner and I did not need to ask what he was doing. He was going to take my virginity for the second time that night. And I could not have been happier. He entered my tight ass and began to thrust in rhythm with Reggie. I felt amazing. It was then that I looked back and saw that Rick had entered Jack just as Jack entered me. Marie stood watching for just a moment then came and squatted in front of me offering me her dripping cunt as a prize for taking on all of them.
It is a prize I treasured and earned on many nights to follow.