Date: Mon, 2 Jul 2007 15:11:53 -0700 (PDT) From: Christina di Filippo Subject: Anna and I - part 1 WARNING! This text file contains sexually explicit material. If you do not wish to read this type of literature, or you are under age Eighteen, PLEASE STOP READING NOW!!!! This work is copyrighted to the author. Please, do not remove the author information or make any changes to this story. You may post freely to non-commercial "free" sites, or in the "free" area of commercial sites. I will be pleased to receive your comments. Please send them to christinadifilippo@yahoo.com ______________________________________________________________________ When I was 15 years old I went to a festival near home. This was a typical festival that occurs throughout Brazil in the month of June, with music, dance, shows, expositions, the works. When I visited the exposition room I saw a display of pencil drawings of young women, around my age. Though they were strictly "politically correct" there was something very sensual about those pictures. I was examining them with great interest when a lady that I had seen many times in the vicinity of my school came to me and said: "Hi! My name is Anna. Do you like my drawings?" "Very much so" I replied. "You seem to capture something special when you draw". "Thanks. What is your name?" "My name is Christina but everybody calls me Chris" "Would you like me to do a drawing of you, Chris?" she asked with a smile. "When? Now?" "Yes, just a quick sketch" I agreed and we went to a side of the exposition hall and I sat down. She sat in front of me and started drawing on a large pad. I was looking at Anna with great interest. She was early thirtyish, with a beautiful face and a body that was certainly exercised often (I had seen her jogging around the neighborhood before). She had ample breasts that seemed to be unencumbered by a bra though I could not be sure because she was wearing a heavy sweater. Despite being still a virgin, I was already into boys at that time. As it happens, I was also developing a parallel, non-exclusive interest in girls as well. I had not yet had any experiences with a girl but I would steal looks at my classmates at the changing room after phys-ed classes. We could not see each other showering - the stalls were closed - but to an attentive eye there were always many opportunities to steal a glance. I often thought about some of my favorite girls at night, and had masturbated fantasizing about them more than once. It was an interesting situation, therefore, to be posing to a beautiful older woman and being able to keep looking at her, without arising any suspicions. I got a little excited and perhaps, a little flushed. Anna seemed not to notice it and kept drawing for about twenty minutes. When she finished she handed the drawing to me and said, "This is a quick sketch. To make a better drawing I need more time". I looked at the drawing and was surprised. It did resemble me, but Anna had managed to draw my breasts slightly larger than they actually were, with the nipples standing out, which they were not until then and which they became from that moment on. The drawing made me look sexier than I thought I was. "It is beautiful Anna. You made me look very sexy". She smiled and said, "It is not as good as you deserve. Why don't you come to my place one of these days and I can draw you with greater care?" The invitation caught me off guard, I blushed, mumbled a few words and she gave me a card with her phone and address, "Give me a call, Chris. It will only take a couple of hours". That night I had great difficulty sleeping. I thought about my pointed nipples and my beautiful portrayer and masturbated twice. A few days later I had little homework to do and I called Anna. She was pleased with my call and asked me over. I had to control myself not to run to her house. She lived in a quiet street, not far from my school, in a lovely, small, detached house, with a beautiful little garden in the front. She invited me in and I entered a very feminine living room. Her studio was at the back, full of light, with a view to an enclosed patio covered with flower vases. She offered me tea, we chitchatted a little and then she asked me to sit in a reclining chair. The position of the chair looked as if she was forcing me to push my breasts out and I felt my nipples growing against the material of my thin bra. She drew for about 2 hours. She was wearing a short skirt, which gave me an ample view of her muscular thighs and, this time, though she was very composed, I was sure she was not wearing a bra. She drew and chatted. She asked me about boyfriends. I blushed and said I did not have a steady one. Just a few kisses and caresses in the back of a car, once with one my classmates and another time with one of my older brother's friends. I daringly asked her about boyfriends and she said she had had many but that she was "between boyfriends" just now. When she finished, the new drawing was even sexier than the first. It was drawn in greater detail, my nipples were again very hard and she drew me with a skirt shorter than the one I was wearing, with my thighs slightly open. I had not posed in that position, but I wished I had. "You make me look more beautiful than I am," I said. "That is the way I see you," she said with a smile. She offered me tea again, but this time she served it in the dining room. There were about two-dozen drawings of other girls hanging from the wall, the majority of them with their breasts exposed. I even recognized one girl that was two years my senior at school. I stopped wide mouthed looking at those beautiful half-naked girls and she asked: "Do you like them?" "They are beautiful," I said, trying to hide the tremor in my voice. I was captured by the sensuality of the room and started feeling a wet sensation between my thighs. "Do you draw them naked?" I asked, almost without thinking. She gave me a mischievous smile and said: "Yes, of course. These girls were naked from their waist up when I drew them". I said nothing, she poured some tea and we started chatting again. I could not take my eyes from the drawings and she asked, "Would you like to pose like that one day, Chris?" I blushed and said "Well, I have never been naked in front of other people, except my mother and my doctor". "And what about your boy friends?" I went from red to crimson and stammered "Well, I ... I let them touch my breasts but not pull them out" "But did you let them touch you inside your bra?" I don't know which is the next color after crimson, but I got there, "Yes but ..." "You don't need to be ashamed. Sex is a good thing and I am glad you are capable of enjoying it". She changed the direction of the chat, which much relieved me, and I decided to leave. At the door she said: "If you ever decide to pose again, give me a call" "I will" I said and run home. When I got to my room I stripped naked and looked at my breasts in the mirror. I masturbated wildly for what seemed two hours. My decision to go back to Anna's place and pose naked from the waist up was quickly taken. Mustering the courage to do it was another story. It took me about a month to call her again. She was warm and inviting and said that I should come whenever I wanted. The following day I was there. She kissed me on the cheeks when I came in. We went through the tea ceremony in the dining room again and she asked "Are you comfortable with this, Chris? You don't have to do anything, you know?" A voice that was not controlled by my brain said: "Sure, I am looking forward to it". She smiled and caressed my cheek, "In order to make you less uncomfortable I will also strip from the waist up. This way you will not be at a disadvantage" I could not believe my ears. She was going to show me her breasts! We went to the studio and she came to me, unbuttoned my blouse and unclasped my bra. She turned, laid them carefully over a chair and removed her blouse. She was not wearing a bra. This time, if she drew me with hard nipples, she would be more realistic than in the previous occasions. She looked at me, smiled and said, "You have beautiful breasts". I blushed and said, "They are so small compared to yours". She continued smiling and said, "They will grow, but even if they don't, they are beautiful. Your pink aureoles and your pointed nipples are very charming. Are they sensitive? Did you enjoy being touched by the boys?" I was past crimson again. She laughed and asked me to sit on the same reclining chair. "Do you mind pulling your skirt a little up? The result will be sexier". I did, but she was not satisfied. She came by chair and adjusted my skirt in such a way that, I was certain she could see my panties from her chair. I felt a mixture of shame and excitement that quickly reflected in my crotch area. She sat and started drawing. I was mesmerized by her beautiful breasts and a wet spot started developing in my panties. She must have noticed it, but did not make any comments. She started drawing in silence and suddenly she said, "The breast is the most feminine part of a woman. It is beautiful and is a source of great pleasure" I did not know what to say and she went on, "Often, when I masturbate, I come by just caressing my breasts. Does the same happen to you?" I blushed yet again and said, "I have never tried." She stopped drawing and looked at me very surprised, "You don't masturbate, honey?" By then I could not to blush any harder, "Oh yes, I do. I never tried caressing my nipples the way you said." She looked at me, placed the drawing pad on her desk and said, "I do it like that" and started to do a circular movement around her aureole, pinching her nipples every so often. "Why don't you try?" I was lost for words and terribly excited. This beautiful woman was caressing her breasts for me to see and wanted me to do likewise. My panties were now rather soaked and I could smell it. I feared she could too! Very shyly I started to copy her movements and the excitement in me stared to grow. Caressing myself and looking at that gorgeous woman was too much of an experience. My breath started to become faster and my face was flush with pleasure. Anna turned to me and said, "It seems that you are quite excited honey. Don't hold your orgasm back. Feel free if you want to come". And I did. I had a shattering orgasm, my first in front of another person. And a woman at that! Wow! When I finished she said, "Freeze in that position" and kept drawing for another twenty minutes. The final result was fantastic. The drawing showed me as a sensual, spent woman, with my breasts exposed and a huge wet patch on my panties. Anna said. "It is best if you do not take this drawing with you, don't you think?" I promptly agreed. I did not want my Mom or, worse of all, my brother seeing it. She continued "Perhaps you want to wash yourself. The bathroom is through there." She pointed. "If you wish I can lend you a fresh pair of panties" I thought it might be a good idea. I had come buckets. When I was in the bathroom she knocked and I open the door a little. She gave me a beautiful pair of lacy panties and I gave her my wet cotton ones. She smiled and went away. During our chat, when we had our second cup of tea, she told me that she was very glad that she had taught me new way of reaching an orgasm. I blushed. She then asked me if I wanted to see a sexier set of her drawings. I eagerly agreed and she showed me some drawings of girls, this time completely naked. Many of them had their legs open, showing their pussies in detail, others had their hands between their legs, as if they were masturbating. I could not believe my eyes. She asked, "Do you like them?" That same voice that was not controlled by my brain said "They are beautiful. And very exciting as well" "Would you like to pose like that one day?" I moaned and made "Yes" with my head. My return to Anna's studio did not take long. In a few days I managed to escape my school chores and called her. That same afternoon I was ringing her bell with a much accelerated heartbeat. Anna was, as always, very charming and very warm. This time she embraced me closely and I could feel her breasts crushing against mine. She kissed me on both cheeks and I made a gigantic effort to stifle a moan. We went through the tea ceremony once again and she asked me a lot of unrelated questions about school, friends, home etc. My pulse was coming back to normal when she asked if I really wanted to do that drawing. Once again that voice that was not controlled by my brain took the better of me and agreed, with a coy smile. As I had hoped, she said that she would make me more comfortable by also striping naked. I could not contain my excitement. We went to the studio and she unbuttoned my blouse, unclasped my bra and pulled it out with a light caress on my breasts. She then sat me in the reclining chair and removed my sneakers and socks and caressed my feet. I could not help moaning. She then undid the button and the zipper of my jeans and pulled them out. My panties were already wet. She introduced one hand under the elastic on each side of my body and pulled them down, running her hands along my thighs and legs. I had gooseflesh all over my body. There I was, completely naked in front of a lovely woman. I had little shame and lots of excitement. Anna looked at each detail of my body, my breasts, my thighs, my light brown bush and, turning me around, at my bottom. She had an approving smile and said "You have a lovely body. The boys must be all over you all the time." As if boys were among my worries at that moment! She then rose, opened her arms slightly and said, "Do you want to do it?" It took me more than five seconds to understand that this gorgeous woman wanted me to strip her. I did it with my hands trembling. I opened her blouse and saw her delicious unencumbered breasts come free inches from my eyes. I took her sandals off and massaged her delicate feet. I released her skirt hooks and let it drop to the floor. Finally, I introduced my hands on each side of her panties, the same way she had done to me, and pulled them down. I was hypnotized. She smelled of lavender. She had long muscular legs, perfectly shaped, that met at a practically bare pussy. There was a small patch of trimmed blond hairs on top of it and that was all. She turned around, the same way she had made me do, and asked, "Like it?" "You are wonderful!" I stammered. She smiled and winked at me. She took me to the reclining chair and sat me, studying the pose. She opened my legs slightly, exposing my already wet pussy, then closed them again, then placed my hand on my pussy, pulled it out, and played with my willing body for a couple of minutes until she found the position she liked, with my left leg over the arm of the chair, exposing my pussy in the most shameless manner. I was trembling with excitement. She asked, "Are you comfortable? Do you want to change your pose?" I asked, "Am I not too exposed?" "No, by all means! You have a most delicious body and I want you to show it!" Having said that she pinched each of my nipples with great tenderness to ensure they were erect - as if it was needed! - and sat down. She then crossed her legs man style, in an absent-minded sort of way, giving me a front row view of her lovely pussy. She started drawing and, for fifteen minutes we were both silent. I was in heaven, enjoying each moment of it. Her questions coming from nowhere always surprised me. I was lost in my dream when she asked "Are you still a virgin, Chris?" There I was, becoming crimson again, "Yes, certainly. I am only fifteen." "I lost my virginity when I was fourteen" she said. "I went camping with a friend and her brother talked me into it." She stayed quiet for a few seconds while I could not find anything to say. "How close have you got? With such a gorgeous sexy body, the boys must be trying hard." I was so confused with her questions that I could not find what to say. She looked up from her drawing, smiled, and said, "If you don't like to talk about that, we can change subjects." "It is not that" I said, "It is that I have little experience. The most I have done is kissing, letting the boys feel my breasts and once I let Mark, that is my brother's friend, touch my panties. That's all". I thought she would let me off the hook but she asked, "And how do you relieve your sexual tension? I can see that you are a sexually mature girl that can get aroused very easily. I saw your panties the other day and I see your shiny pussy now. Do you masturbate often?" She really had knack to force me to reveal my most secret secrets. Almost without blushing I said, "Yes, I do. I do it every day, sometimes more than once." "And do you come every time?" "Yes, I tend to come a lot. I do it in the toilet to avoid wetting my bed. My mother could see or smell it!" "Don't you talk about sex with your mother?" "It is not that she is strict or forbids me from talking about sex. I sometimes believe it doesn't cross her mind that I am a woman now. I may be wrong but I think she would be less comfortable than I would if I were to draw the subject." I was quite relaxed now. I could talk about anything with Anna. "Mothers, mothers. What are your fantasies when you masturbate?" There she comes again. When I thought I was relaxed, bang! she throws a new bomb. I really had to concentrate now. "I think about sexy things." "Boys?" I hesitated a little too long. "Girls?" There I was, blushing and confused all over again. I almost cried, "Both, I think." "Hey! There isn't anything wrong about that. Girls are every bit as desirable as boys, sometimes even more. Do you remember that friend of mine whose brother took my virginity? I had sex with her that same weekend. It was delicious. Do you have a girlfriend? One that you have had sex with?" "No!" "Any that you would care to?" I hesitated and she continued pulling it out without mercy, "A classmate, perhaps." "Yes." I blurted out. "I have fantasized about Isabel more than once. She is a classmate with the most lovely breasts I have seen" "Have you ever touched them?" "I wish I did but I just brushed on them accidentally on purpose, you know?" She smiled and resumed drawing. My heart was pumping fast and my excitement was very, very high. "Do you feel comfortable talking about sex with me?" Anna asked, out of the blue again. "I have never talked about sex with anybody this way before!" "Does it excite you? Talking about sex with another woman, both of us naked and all?" "Yes, it does." "The other day, when we were both bare breasted did you feel like masturbating?" "Yessssssss. You made me come, when you taught me how to caress my nipples and, after I went home, I masturbated for a long time." "And what did you fantasize about?" That voice uncontrolled by my brain was quicker than my good sense, "About you" She stopped drawing and looked at me with a warm smile, "About me? How lovely. Do you know I masturbated thinking about you as well?" I was lost for words. This gorgeous woman that could have any man or woman she might have wished had masturbated fantasizing about me! "I had quite a good orgasm remembering the way you got excited when you learned to caress your breasts and the quiet but intense orgasm you had. And I came again when I smelled your panties which I have kept for that moment" I was flattered, scared, confused and excited, all at the same time. She then came to me and looked straight into my eyes and asked, "Do you want to masturbate now, Chris? We could masturbate together looking at each other, what do you think?" "Yesssssss. That would be lovely" My brain could not control that voice but who cared? She brought her chair near to the reclining chair, put one leg over it and spread the other, showing me her glistening pussy. Very delicately she started to touch herself. I was in heaven. I attacked my own pussy and felt the smell of female desire in the air but could not tell whether it was hers or mine. It was a dream vision. This stunning woman caressing her breast with one hand and her clitoris with the other! I could not contain myself. I started panting and she looked at me, smiled sweetly, introduced one then two fingers into her pussy and started pumping in and out. I was on the verge of coming and she sensed it because she came nearer and whispered "Come Chris, come for me. Let me see you orgasm looking into my eyes." With that prompting I exploded in a delicious, loooooooong, shattering orgasm. I lied back completely spent. She looked at me and said "Some orgasm!" I smiled faintly and she took my hand and said "Let me feel your smell." She the smelled my fingers and, to my surprise, licked then one by one. "You not only smell delicious but taste delicious as well." I lied there, happy, under her amused look. I asked, "Did you also have a delicious orgasm?" Anna said "No!" I raised my eyebrows and she went on, "Not yet, but I will. If you would help me" "What do I have to do?" I asked eagerly. "Come with me" she said. I followed her, both of us completely naked, to her room. It was a wonderful room, with a large bed and a very feminine decoration with lace curtains and satin sheets on the bed. The air smelled lightly of incense. Rosemary incense. She asked me to lie in her bed, which was a delicious sensation, feeling my naked body against the satin sheets. She sat beside me, caressed my face and asked, "Will you help me to reach as delicious an orgasm as the one you just had?" "Yes, I'll do whatever I can" She the opened a drawer in her bedside table and pulled out two toys and a little jar. I had never actually seen sexual toys before, but it was not difficult to imagine what they were. One was exactly like a penis. Not that I was an expert on the subject, but I had seen both the real thing and the toys in some porno mags that circulated secretly between the girls at my school. The other one was smooth and much thinner, about the diameter of my thumb. Anna climbed on the bed beside me on all fours and asked me to kneel behind her. That in itself was a turn-on. Her spread ass, her shapely thighs, her little hairless asshole and her beautiful pussy, shiny with lust, with her clit standing in attention is the sort of view I want to see every day of my life. She handed me the bigger toy and said "Please, insert it very gently in my pussy, honey." I straddled her leg to get a better position but my hands were trembling. She said, "Open my lips with the other hand so you can slip it in more easily." And so I did, touching another woman's pussy for the first time in my life. It was smooth and beautiful, and my own pussy was getting moist again. It took me a few tries to find the proper angle but I managed to insert it. Anna moaned and asked me to push it gently all the way in. It was an incredibly erotic experience. When I got it entirely inside her pussy she moaned again and gave me the thinner toy and the jar. She asked me to open the jar, which contained a jelly like substance, "Deep the tip of the toy in the jar and coat it with a generous amount of the jelly", which I did. Anna then said, "Chris dear, I want you to insert it very gently up my bum. Can you do that?" And she immediately spread her ass using both hands, showing me her puckered hairless asshole. I could not believe my luck. I did as she told, with great tenderness, and managed to stick the entire toy up her ass. I was glad it had a flat part at the other end that prevented it from disappearing up her delicious bum. I was so excited that I lowered my body so that I could rub my pussy on her leg. "Yes honey, rub yourself on my leg. I can feel how hot you are. Are you enjoying your task?" "Yes Anna" I managed to moan. "Now I want you to start pushing the toy in my pussy in and out with one hand, while you caress my clit with the other. Can you do that?" "Yes I can," I said eagerly. I started following my instructions and was surprised to feel how big and hard her clit was. I was crazy with lust and she raised her leg a little so that I could rub my pussy on it. I could feel her pussy area getting more and more wet. "Now switch the vibrator on. That pink button" I did just that and the toy started buzzing inside her. She moaned loudly and said "Push the toy in my ass in and out, homey. Make me come." I was delirious. I never imagined that sex could be that exciting, and I never imagined that sex with a woman could be so fun. I continued to fuck her asshole and caress her clit while the vibrator did its job in her pussy. All the time I was rubbing my pussy against her leg, which by now was wet with my pussy juice. We kept at it for a couple of minutes and then she started to pant and moan and pant louder and moan even louder. I knew she was on the verge of coming and I was on the verge of coming to. When she started crying "Ohmygod, Ohmygod. Fuck me, sweet! Make me come, pleeeeease" She had an orgasm and I started coming at the same time. It lasted forever and I feared our joint moans could be heard for miles. It was my first simultaneous orgasm ever. I was learning a lot in a single day! A After she came, she asked me to remove the toys, which I did very gently. She then turned on her back and pulled me over her. My breasts were crushed against hers and her left leg was between mine in such a way that I could feel her clit against my thigh and she could feel mine. She kissed my cheeks and said, "Thank you Chris honey. You made me come like I hadn't done for a long time." I smiled proudly at her and she kissed my lips, and I felt a woman's tongue in my mouth for the first time. We stayed embraced until our respirations came back to normal. She looked at me and said, "It is a pity you are a virgin. I would not like to take your cherry. Not yet, at least. Otherwise I would make you feel the joy of playing with my toys." That voice that was uncontrolled by my brain said "Can't we try in the back?" She looked at me with an amused expression and brought her hand around to my ass and started passing her finger along the crack. "My little girl wants to feel a toy up her ass, does she" I nodded and she said "You have to ask me, honey." I was past blushing at that stage. I said, "Please Anna, fuck my butt with your toy, please?" She smiled and pushed me aside. She kissed me and said "Doggy stile, honey." I quickly got on all fours. She said, "I will have to prepare you, OK?" "Whatever it takes, my love" She knelt behind me and started kissing my ass, the back of my thighs, approaching my pussy, spreading my lips with her fingers and pushing her tongue inside me, getting her lips around my clit and sucking gently but firmly, licking my pussy again and finally licking my asshole. I came continuously. I am not sure whether I had a one hundred-second orgasm or one hundred one second orgasms. I simply could not stop. Then I felt her finger massage my asshole with the jelly. She went round it and the gently inserted her finger in. I was in heaven. She removed her finger and started to push the thin toy in. I was being fucked! "Please Anna, fuck my ass! Make me come yet again! This is the happiest day in my life" She left the bed suddenly and squeezed herself back, in such a way that her head was near my pussy and her pussy was near my head. She then said, "Do to me the same I'll do to you, honey." And she started to lick my pussy again. I lowered my head and started licking her pussy. The honey that came from her was sweeter than any bee's. We licked and fucked each other until we were exhausted. We then showered together, generously lathering each other pussies. We got dressed, combed and perfumed. She took me to the door", French kissed me and sent me away with a pat in the bum, "You must come back tomorrow so that we can finish that drawing!"