This story was told to me by my sister-in-law Susan, about her awakening to love. If you have read my first story about how we met, "Menage a Quatre", you'll know something about her already.
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Susan's Story
When I was a very little girl, we were well-off. I mean that we had money and lived in a nice house. When I was a little older, we were what you'd call pretty rich. And now we're filthy rich, all because my granddad and his sons built up a little shipping company into a big multinational powerhouse. You've probably heard the quote from F. Scott Fitzgerald about how the very rich are different from you and me. Well it's true. After my uncle and aunt died in a plane crash when I was five, Granddad and Dad became very protective of me and my brother Paul. Dad and Mom adopted my cousin Ron, and we three kids lived in a protective cocoon.
Ron and Paul are the same age, four years older than I. We didn't associate with lots of other kids outside of school, so we spent lots of time together. I've always had a crush on both of them. As a pre-teen, I was a big pest. But they always were nice to me, even when they didn't want me around.
We all went to the same private academy in Connecticut. Our parents were always away working or visiting far-off countries or the like, and we were left in the hands of a succession of nannies and bodyguards, all of whom we hated and conspired against. In return, we were never allowed to go to other kids' houses or have sleepovers or the other fun things normal kids like to do. Each day after school, we were picked up by the chauffeur/bodyguards and driven back to our fenced estate. We called it "Stalag 14."
When I was eleven, the boys were sent to a boarding school. We saw each other on school holidays, but never on weekends. Each time they came home after months away, I was thrilled to see how they had grown up. Both were athletes. Ron was on the track team, and Paul was a wrestler. With the training they did, they developed muscular physiques. I thought they were the most handsome boys I had ever seen.
At the age of fourteen, I too was sent to a tony boarding school for girls, and only came home for school holidays. I was not a good student except for French and art, both of which I loved. I planned to become an artist and live in a garret in Paris and have bohemian lovers.
By then I had developed physically so that my breasts filled out my sweaters and my pussy was covered in soft brown fur. When I discovered masturbation, an entire fantasy world opened up to me. At night lying in bed, I would play with myself for hours imagining that some handsome man or other was fucking my wet slit and kissing my nipples. All of the girls had private rooms at school, so I never had to worry about roommates discovering my nocturnal activities. Although I tried to suppress my thoughts, the man I pictured the most often was my brother Paul.
We had occasional dances at the school arranged with neighboring boys schools of the proper social level, but I never met anyone at these affairs who attracted me in a serious way. In any case, we were too carefully guarded to let anything serious happen. So I remained virginal all through my years at school.
At the age of eighteen, I was a junior. Each of the dorm floors had senior girls who were designated as "monitors" and were tasked with supervising the younger ones. Our monitor was named Cynthia. She and I had been casual acquaintances for years because she had been attending the school since primary. One night I was lying in my bed with my nightgown hiked up around my hips and my fingers busily exploring my inner depths. I had been giving myself one after another particularly strong orgasm, and although I am normally pretty non-vocal, this session was exceptional. As I gasped and let out little moans, Cynthia heard me as she was passing my room.
I opened my eyes to see Cynthia standing in my doorway. How long she had been watching I don't know. She was dressed in a long sheer nightgown, and her long straight brown hair hung down over her shoulders practically to her waist. With the hall light behind her, I could see the outline of her legs through the gown. She was leaning on the door frame with one hand between her legs.
I gasped in alarm as I simultaneously struggled to pull down my gown and cover myself with the sheets. Cynthia closed the door and walked over to me and sat down on the side of the bed.
"Don't worry about it," she assured me. "I do the same thing all the time. I just try to keep quiet."
"Really?" I asked naively. "I thought I must be the only one. It seems so dirty. But it feels so good."
"Are you still a virgin?" she asked gently.
"Of course I am," I came back. "Aren't you?"
She laughed at that sally. "Not for quite a while. Do you like being one?"
"I'm saving myself for my wedding." It now seems quite amazing to me what a little prude I was then.
"That didn't answer my question." Cynthia bent down over me and kissed me on the lips. This was quite a shock! Although we had often kissed on the cheeks as greetings, this was different. She turned on my bedside lamp and looked down at me. Although I had pulled the hem of my nightgown over me, the juices from my pussy had soaked through the front, and the odor of my sex was heavy in the air.
I felt helpless to react as she raised the hem of my gown to expose my sex to her gaze.
"Let me show you," she said in a husky whisper, lowering her mouth to my stomach.
She kissed my belly button and then with tiny kisses her lips descended my abdomen until they touched the moist hair above my pussy. She gently parted my legs with one hand as she moved lower, until her tongue made electric contact with my erect button. As she slowly licked around my sensitive clit, she pushed one then two fingers into me. I was so wet that they entered easily. I felt myself become even more wet as the fingers fucked me and her mouth gave me more pleasure than I'd ever been able to give to myself. I opened my legs as wide as I could to give her access as my hands squeezed by breasts and my hard, almost painful nipples. When I looked down, her eyes were boring into mine as her lips and fingers worked their magic. I can't say how many times I came before she raised her face from my between my legs. Perhaps it was one continuous orgasm. At the end I fell back on my pillow, covered with sweat and flushed all over my body.
Cynthia sat beside me looking down with a strange expression. "For a beginner you really freaked out there," she said. "My first time I was so nervous I didn't feel anything except the need to pee. If I hadn't felt your hymen just now, I would have never guessed that you're a virgin."
I was now a bit recovered, and made some vague effort to cover my breasts and legs with my gown. "I don't know what to say. I'm not a lesbian. How did you make me do that?"
"I didn't make you do anything you didn't want to do. You don't have to be a lesbian to like someone's mouth on your cunt. When there's no men available, we have to make do with what's available. Now! You've had your fun, it's my turn."
"What do you mean? You want me to do that to you? That's disgusting!"
Of course it wasn't disgusting, as my recent experiences had just demonstrated. So I regretted that outburst almost immediately. Besides, Cynthia had climbed onto my bed and straddled my chest. She pulled her gown over her head, revealing herself in total nudity. She had a magnificent pair of breasts whose nipples stuck out hard and full pointing in separate directions. Her long hair fell over her shoulders and onto my face as she leaned over to kiss me full on the lips. I knew immediately that the musky smell on her face came from my juices, and this was strangely exciting. She moved up to straddle my face so that her pussy was just over my mouth. Her labia were swollen and her large clitoris stuck out like a little penis engorged with blood. I reached up gingerly and parted her outer lips while I let a finger trail up to touch her button.
"You don't need to be so gentle," she whispered. I found her vaginal opening and was able to easily fit three fingers inside. Her cunt was warm and moist and muscular.
"Fuck me hard," she commanded. I moved my hand up and down rapidly as she asked. It entered up to the knuckles. "Harder, Harder!" I got all four fingers in and was really pounding into her. On the upstroke, I made my thumb bump into her clit. She was supporting herself on the bed's headboard bucking on my hand, forcing herself down to meet my strokes, so that I was afraid she would break my wrist. Her juices were pouring out of her and running down my hand and wrist. With my free hand, I reached up to tweak her nipples. When she came, I could feel the muscles of her cunt squeeze hard on my hand.
She slumped down so that her matted hairs were pushed against my chin. Her smell was strangely exciting, and I felt my own juices begin to moisten my slit again. I moved her gently so that I could probe her with my tongue. She tasted different from me, but not unpleasantly so. As I lapped between her lips and up to her clit, still engorged and erect, she pressed her cunt down on my face so that my tongue was able to enter more deeply into her tunnel. My mouth was covered with a fresh flood of juice, and I was able to breathe only through my nose. Both of us were letting out little grunts and squeals as she came a second time.
She slowly lowered herself onto the bed next to me and we fell asleep in each others arms. Only when daylight brightened the room through the curtains did she rise silently, put on her gown, and disappear through the door.
After that night, Cynthia and I became best friends. Needless to say, we slept together almost every night when we thought we would not risk being discovered. She taught me to lots of new things I had never imagined in my earlier pubescent fantasies. She would come to my room with her vibrator and have me fuck her with it. She could get multiple orgasms with it every time. She would use the tip to stimulate my clitoris, but she would never put it into my cunt. "We need to keep you a virgin for your husband," she laughed.
However, she did share the pleasures of anal fucking with the vibrator. With it buzzing in my asshole and her lips and tongue pleasuring my cunt, I had guaranteed orgasms whenever I wanted.
"Did you ever let a guy fuck you back there?" I asked after the first time we did it.
