The History Of Anna free porn video

The History Of Anna - Part One How about a quick trip down memory lane. I'd like to let you in on how I got started. I have a sister and one day when I was about 13 and she was 18, I was pissing her off as much as I could. She made the comment that she wished she had a sister instead of a brother and became quite upset with me. I told her that she was stuck with me, so she had better get used to it. She, on the other hand, had different ideas. It was Friday and my parents had just left for a business trip to the states, so we where all alone. Roxanne, my sister, (Hence the name Anna), decided that I need to be taught a lesson. On Saturday I awoke to my sister sitting on my bed. In her hand was a list of all of the chores I had to do that day. I told her no way, and she said that if I didn't do them, she would tell Mom and Dad that I had been pure hell all weekend. I decided it was better to have a little pain, then the gain would be from my parents. So I agreed to do them. I was in the kitchen starting on the dishes, when my sister tossed me an apron and told me to put it on. It was a frilly kind that my Mom used when she was in the kitchen. I protested but put it on anyway. As I was washing, my sister made the comment that she had thought about it and she was going to have her sister after all. I told her she was nuts. How was she ever going to have a sister. She said that since I made such a rotten brother, I would probably make a better sister. I was a little unsure of what she wanted so I just listened. Roxanne said that I was going to find out what it was like to have manners and she said that I was already on my way to being her maid for a day. I started to protest again but she told me to keep my mouth shut and to listen and obey her commands. If I complained one more time, that was it. Mom and Dad would think I had nuked the world. I decided that from here on in, I would have to go along with my sisters wishes. After finishing the dishes, my sister gave me a list of things I had to do. I was quite shocked at what it said. It read sort of like this: "Since you have failed to be a good brother to me, I will give you a chance to be a good sister. And if you are going to be my sister, you will have to look like one. First, shave all of your body hair off. This includes your chest, armpits, legs and pubic hair. Second, fill the bath tub up with water and add some bath oil to it. Soak for half an hour. When done, go into my bedroom and use the items on my dresser. Paint your toenails and fingernails. Pluck your eyebrows at the corners. On my bed you will find clothes to wear. Put them on in the order they are laid out. I am going to do some shopping and will be back in three hours. You had better be ready or else!" I was very confused, but another side of me was curious. I had watched Roxanne apply her makeup on several occasions and it always amazed me how well she could do it and how much better she looked when she was finished. She also had a rather large wardrobe, with all types of clothes. Since this was the start of the DISCO era, there was quite a few shorter skirts and some spandex items. I also thought it unfair that girls always got the soft, colorful clothes to wear, while we "GUYS" had to wear the rough and tough stuff. And last, but not least, I had wondered a few times what it would be like to be a good looking girl and have guys falling all over me. I had seen a picture layout of she males in one of my Dad's Playboys, and it had gotten me quite excited. The best of both worlds! So it was with some apprehension and tons of excitement, that I started on my first road to transformation. And I wasn't going to let on to Roxy that I just might enjoy this adventure. After a few close calls with the razor, I succeeded in shaving my entire body. The tough part was pubic hair and anal region. I had a hard time seeing if I was shaving, or about to cut off my manhood. I don't think my sister would have cared if I did. After I was done, I filled up the tub and poured a little too much bath oil in it. I just about slipped and killed myself getting in. I could see the headlines now " Nude and Totally shaved 13 year old boy slips and kills himself trying to appease his sister!" The soak did feel quite good and I just about forgot about the time. I jumped out of the tub and covered my entire body with some perfumed cream my sister had left in the bathroom. This was starting to feel really nice and I couldn't help getting into it. I wandered into my sisters bedroom and on the bed were, even by my standards, some pretty sexy clothes. Where did she get this stuff??? I started off by putting on a full cup pink bra and panty. I had a little trouble with the bra, but figured it out eventually. I thought I looked a little flat and then noticed two balloons filled with water on the bed. I guess these were to be my boobs. I popped them into the bra and they fit nice and snug. Then came the pantyhose. There were sheer navy blue and I think I got tangled up in them three or four times before I finally got them on straight. They felt wonderful against my freshly shaven legs and I think I was starting to get a bit excited. I looked over into my sisters closet door mirror and was a little surprised to see how well I was starting to look. I have always been a small person, and at this age I think I weighed about 115 pounds. My waist size at the time was 24 inches and I was only 5' 4" tall. I turned my attention back to the bed full of stuff as my three hours where just about up. Next, I put on a frilly pink blouse that had a V-Neck. It took me a minute to realize that women button there clothes up on the opposite side. Next came a black skirt that stopped just above my knee. After tucking the blouse in, I finished off my outer apparel with a black wide elastic belt and then turned my attention to the shoes. They were about my size, black and had a three inch heel on them. I sat down on the bed and slipped them on. Standing up was a different story and finally walking in them was almost impossible. I practiced back and forth around the bedroom until I got the hang of it. I walked over to the mirror and was pleasantly rewarded with my reflection. I must admit, I had a pretty good figure and my legs looked wonderful with the heels, pantyhose and skirt framing them. I thought that I should get back to work, so off I went to start dusting the living-room. My sister arrived shortly after and was very pleased with my novice attempt. She had quite a few bags with her and I was a little more than curious as to what she had bought. She told me to come into her bedroom and sit on the bed with her. She said that this is how sisters got along. I followed her in to the bedroom and we sat down on the bed. She corrected me on my posture and showed me how a proper lady crosses her legs. She then had me stand up and walk around her room. I did quite well and I could tell she was pleased. After I had modeled for her, she told me to sit down as she had a few presents for me for being such a good sister. I think the first bag was the best. Inside was a long blond wig with flip up bangs. It was curly on the bottom and I was a little excited about trying it on. Roxanne lead me over to her vanity and told me she was going to teach me how to be a complete girl. She combed out the wig and then positioned it on my head. In the next bag was an assortment of cosmetics. She gave me step by step instructions on applying my makeup. When I was finished, I could not believe my eyes. Sitting in front of me in the mirror was a very attractive looking girl. I was impressed with what Roxanne had done and told her so. She said that the best was left for last. As we walked back over to the bed, I was a little more than curious as to what was next. In the next bag was an assortment of lingerie. A beautiful black bra with lace on the cups, a garter belt and matching thong style panty. There were also two pairs of sheer silk nylons. One black and one dark beige. The last item was a waist clincher that laced up in the back. Roxanne explained that these items were for later but would not tell me why or what for. The next bag contained a feminine douching bag with a long slender attachment. I was starting to become a little more then curious. There was also a set of false nails and some perfume. The last bag held some things I had never seen before. The first item was a long pole that Roxanne called a dildo. It was eight inches long and I was going to ask her what it was for, but thought she would probably be getting around to descriptions later. The next item was what she called a butt plug. I didn't have to be a genius to figure that one out. The next item was another dildo, but it was a lot longer and had two heads. The last item was something in a tube called K-Y jelly. My curiosity had peeked by now so I asked Roxanne what she was going to do with all of this stuff. She smiled and said it wasn't what she was going to do with it, it was what I was going to do with it. Now it was time to really wonder what my sister was up to, but before I cold say anything, she told me that it was time for me to start dinner. Cook??? I had never cooked before. That was why we had women. She reminded me that since I was now a woman, I would be doing the things that women did. So off to the kitchen I went to prepare dinner. Roxanne said that she was going to have a bath and relax. I was just starting to peel the potatoes when I heard my sister come out of the bathroom. She said that she was going to get dressed and would join me in a couple of minutes. I was standing at the sink for about five minutes wondering how a girl could wear these high heels for so long when Roxanne came up behind me. She slipped her hands around my waist and I could feel her move her hips against my bum. She said that I was the perfect sister and she wanted to reward me. I turned around and just about didn't recognize her. She was wearing a skin tight leotard top with an even tighter skirt and boy was it short. She had on black nylons and at least 5 inch heels. Now my sister is a very good looking woman, but she had really outdone herself this time. Her blond hair was all teased up and she smelled wonderful. She asked me if I liked the way she looked and I said she looked great. She then pulled me very close to her and kissed me full on the lips. I was shocked, but aroused at the same time. I could feel my penis start to grow and I think she could to. As we kissed, Roxanne ran her hands over my ass and then up under my skirt. Just as I was beginning to get used to all of this, she broke away and said that dinner could wait. She lead me back into her bedroom and told me to sit down on the bed. She then removed my shoes, lifted my skirt and took off my pantyhose and panties. While she was doing this, she explained to me that she had discovered when she was fourteen that she was bi-sexual. It had happened on a camping trip with a friend of hers. I guess they had slept in the same tent together and one thing lead to another and presto! My sister had diverse interests. She had been with quite a few other woman since that time and had even been involved in a few three-somes, another woman and a man. She explained that in her mind, making love was a beautiful and exciting thing and it did not matter who you were with as long as the outcome was pleasurable. It made sense to me, but I still could not figure out what she was up to. It was all to become quite clear over the course of the next few hours. After she had finished talking, I was still unclear as to what was next and asked her what we were going to do. She told me to take of the rest of my clothes except for my bra and wig and to put my heels back on. Then we went to the bathroom and Roxanne told me to face the tub, bend over and spread my lags apart. She said that this was phase one of becoming a total girl. I couldn't help feeling a little embarrassed and quite submissive at having my ass, cock and balls fully exposed. She ran her hand between my legs and started to caress my cock, which was starting to get really big. Bigger then I had ever seen it. Roxanne said that she was going to flush me out so that I would be nice and clean. With that in mind, she filled up the douching bag with some warm water, inserted the slender attachment into the end of it and put a little of the K-Y jelly on the tip. She said that it might be uncomfortable at first, but that I would get used to it and more then likely really enjoy. She also told me to hold on for as long as possible before I had to go to the bathroom. Now up to this point, I had gone along with everything she had said, but this was starting to sound extra weird. I turned to Roxanne and said that I was very nervous about all of this. She smiled and told me to relax and not go away. She disappeared for a minute or so and came back with a joint. I had never smoked drugs up to this point so I was unsure of what I was in for. Roxanne gave me two puffs off the joint, told me to hold it in for as long as I could, and finished the rest herself. My head started to float and my whole body became one big nerve ending. She told me to bend back over and I couldn't help my giggles. I was thinking about the fact that my body was starting to feel a little numb, and didn't even notice Roxanne inserting the douching apparatus until she squeezed the bulb. The feeling of the water rushing into my anal track was wonderful and before I new it, she had another bag full for me. I think I was able to keep three bags full of water in me until I couldn't hold it anymore. I quickly spun around, plopped down on the toilet and expelled my entire bowel. We repeated this maneuver about eight time before Roxanne said that I was fully flushed out. I felt great and was ready for whatever else she had in mind. She then said that since I was leaning how to be a girl, I had to be loose and ready for anything. On that note, phase two started. The butt-plug was produced and gently inserted into my anus. I marveled at how good it felt and the way my bum could grip it at the base. I told my sister that I had never imagined having something up my ass good feel this good. She quickly corrected me, saying that I could not think that way anymore. She said that from now on, my ass was my cunt and my penis was my clit. She also told me to pick a girls name that she would call me. I thought it over for a minute and then said I liked Anna because it reminded me of her. I guess she was pleased with my choice and said that we could now go on to phase three. We went back to her bedroom and she told me to sit down on the chair in front of the vanity. She then re-did my makeup, a lot more this time, and applied the false nails to my fingers. All this time, my butt plug was working itself around inside of me and my clit was beginning to get big again. My sister could not help noticing this and said that it would not do for a girl to have a bulge under her dress. On that note she knelt down in front of me and started to lick and suck me. I could not believe how good it felt and came into her mouth quickly. She stood up, leaned over and kissed me. I could feel her tongue pushing my cum into my mouth. The taste was different from anything I had ever had before and found I quite enjoyed it. Licking her lips, Roxanne finished doing my nails, painted them, painted my toenails and covered my entire body with perfume. She gave me some clip-on earrings, a gold necklace and bracelet and two of her rings to put on. After she was done, she said I looked great but now it was time to make me look sexy. Back to the bed we went to start my final dressing. Roxanne showed me how to put on the lingerie correctly. First the waist clincher, then the garter belt. I pulled on the black stockings and rolled them up my leg. The feeling was incredible. After I had attached them to the garter belt, next came the panties and bra. Roxanne showed me how to tuck my balls up into there sockets and pull my clit back. After the panties were snugly in place, I took off the pink bra and replaced it with the black one. I refilled it with the balloons and Roxanne told me it was time to pick out my party clothes. She opened up her closet and told me the best part of being a girl was attracting other people. And if I was going to do that, I would have to dress so that I would be noticed. She then said it was up to me as to how much I wanted to be noticed. I had a hard time deciding what to wear. Doesn't every girl!! I finally picked out a black mini dress with a dark blue collar. I slipped it on and then had to pick what shoes I wanted to wear. I decided on a pair of four inch open toe heels with a sling back. I put these on and my sister handed me the belt I had been wearing before. Having finished my transformation, I could not help looking at myself in the mirror. What I saw was a very sexy looking girl with great legs, if I do say so myself. My sister said that she couldn't be more pleased with my look and that I was turning her on. She then looked at the time and said we had better hurry up or we were going to be late. I couldn't help being nervous. Late for what, I said. She then informed me that phase four was about to begin. We were going out to a club that she liked that catered to people with different ideas. How different, I said. Roxanne explained that there were a few bars/clubs in town that were setup for gay and bi people. She said that it was the perfect place to start if I was going to see if I could pass in public. I reminded her of my age, but she just laughed. She said I looked older and people didn't really care anyway. I thought what the hell, I've come this far, might as well go all the way. I borrowed Roxanne's black trench-coat and purse and she wore a white fun fur jacket. As we drove to the bar, the name of which escapes me, Roxanne explained that she was going to introduce me to some of her friends. They all knew it was my coming out and decided that it should be special. Now I was getting really excited. We smoked another joint on the way and by the time I got there I was ready for just about anything. Roxanne said that I would have to be careful around other people in the bar as there would be some straight folks who went there. She also said not to talk to much or to loud as my voice, though rather high, was not feminine enough. What I did with myself the rest of the time was up to me. She said that there was only one stipulation to the evening. I had to go home with her. I said no problem! We had to park about half a block from the club and I think it was the longest walk I have ever taken. It was around nine p.m. and we passed several people on the way. We had a couple of guys say Hi and I think I melted. Roxanne just smiled and kept walking. I was relieved to get to the door, but not knowing what to expect, was still really nervous. We walked inside and the doorman new my sister. They talked for a minute and then she introduced me as Anna, her sister. He smiled said hello took my hand and kissed it. It felt wonderful to have all of this attention, but all I could do was to say hello under my breath as we gave him our coats. Inside, the music was pounding. The light show over the dance floor was the best I had ever seen and the place was packed. As we made our way over to a table full of Roxanne's friends, I felt hands on my bum twice. The music, the lights, the butt plug, the smoke and now strange hands groping me increased my excited state. All I wanted was more of the same. At the table I was introduced around. I was quite surprised that the women were very attractive and all dressed quite sexy. I got to sit in the middle of two of the best looking ones and had to remember to cross my legs. Old habits die hard!! . On my right was a girl named Rachel and on my left was a girl named Connie. I only remember their names as I could barely hear the others around me. Both seemed very nice and they talked to me about how I felt that night. I told them both that at first, I wasn't too crazy about the idea, but that now I was loving every minute of it. Connie asked me if I had a special friend inside of me. I guess I looked a little taken back and she said that Roxanne had told her what she had bought for me. I shyly admitted that I had a butt plug stuffed up my cunt and she laughed. She said that if I liked it, she would see if she could find something else to replace it with. I wasn't to sure what she had in mind but smiled anyway. As the second round of drinks appeared, I was starting to feel a little tipsy. Connie had her hand on my leg and was rubbing the inside of my thigh. My clit was starting to strain from the delicious feelings I was experiencing, and I whispered this fact to Connie. She said that if I wanted a rest, was there anything I would like to do, like maybe I could caress her leg. I looked at her and did find myself attracted to her. She had shoulder length blond hair, blue eyes and was wearing a short black leather skirt and a black silk blouse. She had fishnet stockings on and the highest heels that I had ever seen. I said that I would like to return the favor and she took my hand and placed it on her knee. The table had a long table cloth on it and the lights were fairly dim so I knew nobody would know what we were up to. I moved my hand gently along her thigh, back and forth. She seemed to like it and then took her hand and moved my hand up under her skirt. It was very exciting as I reached the tops of her stockings and then felt her panties. They had soft lace on them and Connie seemed to enjoy my touch. As I was getting used to all of this, she asked me to remove my hand for a moment while she went to the bathroom. I had a few sips of my drink and waited for her to come back. She was only gone a few minutes and when she sat back down she said to me that she had to go and remove her panties as they were starting to creep up on her. I was happy to have her back and again proceeded to run my hand under her skirt. Waiting for me this time was something quite hard. It took a moment for it to register, and then I realized that this was a penis, or clit, or whatever the hell we were calling them that night. I started to withdraw my hand but Connie put hers on mine. She asked me if I thought she was any less attractive now that I knew her secret. I said not really. She then said that she found me attractive and she wanted to get to know me better. She said that girls like us had to stick together. By this time, I couldn't disagree so I moved my hand back to her clit. I started to move up and down the shaft and Connie purred in my ear how wonderful it felt. I was starting to get into it when she asked me to stop. She said it wouldn't be very lady like for her to have cum running down her leg. She then asked me if I would like the same done to me. I quickly agreed and she took me by the hand and lead me off to the bathroom. As I was getting up my sister looked over and asked me if I was having a good time. I said I think I was, and she just winked at me. I just about walked into the men's washroom and it was a good thing Connie was with me. Once inside the bathroom, she turned and locked the door. She then told me to take off my panties and to remove my butt-plug. After depositing everything onto the counter, Connie told me to bend forward onto the sink and to spread my legs. She commented on my beautiful ass and slowly lifted my dress up. As I leaned forward more, Connie took a hold of my clit in one hand and started to finger my cunt with the other. My knees just about collapsed from the intense sexual feelings I was having. She inserted one, then two, then three fingers into me and pumped them in and out in time to her other hand. I cried out as I exploded all over her hand and the counter. After I was finished, Connie told me to clean up, fix my hair put my butt plug back in and my panties on. She said that she would meet me back at the table. I could hardly stand and the feeling of the plug going back into me was almost to much. I did make it back to the table and had two more drinks. We spent about another hour or so talking and Roxanne decided that we should get back home. Connie told me that she would like to see me again and said that she would phone Roxanne when she was free. I said sure and asked her to call me instead. I confessed that I liked her and wanted to see her again, too, She smiled, gave me a kiss on the cheek and said that she would love for me to come over to her apartment and spend the night doing girls things. We said our good-byes and walked back to the car. Roxanne asked me what I thought of Connie and I said she was something else. She said that we had a lot in common. Connie was a virgin to anything bi and this had been her first night out. Rachel was her Mistress and had been preparing Connie for this night. I was surprised that she was a novice but Roxanne told me that Rachel had taught Connie a trick or two. We arrived home and I was getting a little tired. Roxanne told me to go into her bedroom because I was going to sleep with her tonight. She told me to take off my dress and panties, remove my butt plug and to slip on her black dressing gown. I came back from the bathroom and Roxanne was lying on the bed wearing her white garter belt and stockings along with a pink teddy. The crotch of the teddy was snapped open and she was softly playing with herself. As I approached the bed she asked me if I thought she looked sexy. She looked more than sexy and I told her so. She then asked me if I wanted to fuck her. Or would I rather have her fuck me. I couldn't make up my mind, so I said yes to both. She asked me to take off my shoes and lay and the bed next to her. She asked me how I had felt about the night and quite honestly, I had really had a good time and told her so. She asked me what I thought of Connie and I said that I was amazed that she was a he. Roxanne said that Connie had told her that I was very cute and sexy and she wanted to have some time alone with me. She said that I would be the first "Girl" that Connie had ever been with. How did I feel? Well, I said I was sort of honored that she (or he) thought me attractive and admitted that I loved what she (I guess) had done to me in the bathroom. Roxanne asked what that was, so I explained my adventure. As I talked about it, she kept rubbing her crotch and fingering herself. When I got to the part about Connie putting her fingers in my cunt, Roxanne started to moan softly. I finished my story and I think Roxanne was starting to cum. She was sliding her fingers in and out of her now very wet slit and between her moans she asked me to lick her where her fingers were. Since I was new to all of this, I had some help from Roxanne as to wear to lick and how hard and soft. I found her clit with my lips and started to suck her gently. A moment later her hips griped around my head and she screamed out. I thought I had hurt her but she just laughed and said that it was just the opposite. Then she said it was my turn. The final phase of learning about being a girl. I was instructed to kneel facing the headboard, grip it with my hands and spread my knees as far apart as they would go. Roxanne started to stroke my clit and tell me what a good girl I was. She said that my ass looked so sexy but lonely and I should have a nice big cock in me. She asked me if I wanted a cock inside of me and all I could say was yes. She then inserted two of her fingers and started to play with me. I tried to move my bum back so that they would penetrate deeper and I knew that Roxanne knew that I was enjoying myself. She then pulled her fingers out and asked me if I was ready to become a full woman. I said yes again but this time much louder. With that, I could feel the tip of the dildo against my cunt and then before I knew it, up and inside of me. I cried out as she pushed it in, deeper and deeper with each stroke but all I could think of was spreading my knees further apart so that I could take more. She asked me if I liked being fucked and I said yes, over and over again. She told me that I was being such a sexy little slut, but that she wanted to be fucked to. With that, she told me to turn over and lay on the bed. I could feel the dildo, all eight inches, deep inside of me and thought for sure I was going to cum. Roxanne moved over top of me, took my no very hard clit, and guided me into her wet warm vagina. The feeling was electric and as she pressed her full weight against me, the dildo hit home. We both came at the same time and screamed so loud I thought we would wake the neighbors. I was so exhausted that all I could do was lay there and shake. Roxanne purred and moved off of me, removed the dildo from my now very tired cunt and said that from here on in, I was going to be her sister when we were alone. I didn't have any objections and we feel asleep snuggled up to each other. The next day I awoke and thought the whole thing had been a dream. One look at my body and trying to get my long hair out of my face convinced me otherwise. That was the start of many wonderful and highly sexual times that my sister and I shared. My sister has since moved out of the country, but we see each other at least twice a year. I did meet with Connie a few times, but will same those adventures for letters to come. As you can see, my start into the world of TVism was greatly helped by a few other people. I have never regretted a minute of it and just about all of my experiences have been wonderful. I say just about, because there have been a few times when I was just about discovered, but later on this topic. History of Anna - Part Two As I said last time, the first night I had gone out as Anna, I met another TV named Connie. She had expressed an interest in me, that was, to say the least, a little more then friends. Roxanne had told me that Connie wanted to get together with me, just me, for a night of girl fun. I was starting to catch on quick as to what "Girl Fun" was all about. On Wednesday of the following week, I came home from school and had a rather burning desire to dress again. Roxanne and I had not really talked about it as she was working a late shift and we seemed to pass each other in and out. I really did want to try being a girl again and when I came home that day, Roxanne had already left for work. I decided that since I was all alone in the house, I could experiment all I wanted. Roxanne had already told me that the middle drawer in her dresser was for my things and that I could borrow her clothes anytime I wanted to. After having my bath and shaving myself totally again, I decided to try the douching part on my own. I must have spent an hour filling myself up and cleaning myself out. Once I had started, I didn't want to quit. It really does feel wonderful and you should try it sometime, sweetheart. The big test was to see how much water I could hold inside and for how long. After I was done, I went to my sisters bedroom and started to prepare myself. I decided not to wear my butt-plug and went straight to applying my makeup. After a few trials and errors, I succeeded in coming close to repeating what my sister had accomplished on the weekend. I then placed my wig on my head and decided to style it a bit differently. To this day, I still wear my bangs combed to the side. I think it makes me look a little more sexy. What do you think?? After my hair was in place, I went to my drawer and picked out my lingerie. I dressed slowly, loving the feel of the undergarments and especially the stockings. Again, the big question was what to wear. I picked out a very frilly white blouse and decided to wear my sisters short black leather mini skirt. It hugged my hips and really showed off my legs. Then I slipped on Roxanne's 5 inch heels. They felt wonderful on and pushed my hips forward. I walked around the room, became used to them and then stood back from the mirror to admire myself. I thought I looked pretty damn sexy and started to run my hands up and down my body. This did a lot to arouse my clit and I decided to cool down a bit and watch some TV. About 8 o'clock the phone rang. I answered and this sexy voice on the other end asked if Anna was in. For a minute, I was petrified. I couldn't speak, so I just mumbled that I thought they had the wrong number. The voice paused and then said was I sure and that it was Connie calling. I immediately snapped out of my haze and said yes, she had the right number and that she was talking to Anna. Connie laughed and said that she was sorry for startling me. I said it was okay and that I'm sure I would get used to it. She then asked me what I was up to that night. I told her about getting dressed and she said that she had done the same. Would I like to come over to her house? Again, a frozen state came over me and I didn't know what to say. There was a long pause on the other end of the telephone and finally Connie said that she could pick me up and would promise not to keep me out to late. I decided, what the hell, and told her sure, why not. She sounded pleased and said that she would be over in an hour. After I hung up, I frantically ran around the house, trying to fix my makeup, decide if what I was wearing was okay and about a million other things. I eventually calmed down, only to hear the doorbell ring. My heart stopped and it was all I could do to peek out the back window. Thank God it was Connie. I thought that maybe friends of my parents or sisters had come over. As I let her in, I could not help noticing how good she looked. She was wearing a short coat and under it a short black lace up dress. She had black stockings on and those wicked high heels. Her hair seemed longer and I asked if it was different from the weekend. She said yes, and that she had five wigs, four blond and one brunette. She then said that I was welcome to try any of them on. I asked her if she wanted something to drink but she mentioned that if I was going to be home on time, we had better be going. I grabbed one of my sisters coats and a purse and off we went. Connie lived in an apartment building downtown, so we parked in the basement and took the elevator. I didn't think about it much until it stopped on the main level. I freaked when I realized that somebody was going to get on. Connie noticed my panic and moved closer to me. The doors opened and in stepped an older gentleman. He smiled at us and said good evening ladies. Connie smiled back and I just waited out the longest elevator ride of my life. As it was, our floor was first on the stops. We left the elevator and I could hardly walk. This was the first time I had ever been that close to somebody who did not know who I was. In a way, it was quite thrilling. Once inside Connie's apartment, I started to relax. She made us drinks and it was the first time I had tasted rum and coke. She told me to sit down on the coach next to her and tell her all about how I felt being a girl. We talked for quite a while and eventually the topic turned to sex. Now how did it get there I wonder??? The conversation changed when Connie asked me if I thought she passed as a woman. I had to admit that she made a very fine looking girl and told her that. She then said that she had been dressing for quite a while, but had never really had the guts to go out in public. She was very submissive by nature and her mistress and turned her on to dressing up. She said that the only thing she had not done as a girl was have sex. She then asked me if I had. I told her that up until last weekend, I had been a virgin to anything and that my sister had taken my cherry as far as my clit was concerned. Connie seemed very interested as to what had happened between my sister and my self. She asked me to explain our night. I told her about getting into bed and making love to her, and then her making love to me. I knew this was turning Connie on so I went into graphic detail as to the night. Connie started to play with my legs and then pulled me very close to her. She kissed me full on the lips and then I felt her tongue in my mouth. We kept on kissing as we moved hands over each other bodies. My clit was starting to strain under my leather skirt and I knew Connie could see it. She moved off the coach onto her knees, lifted up my skirt and start to lick me. Her mouth felt so good and it was all I could do to keep from coming. She looked up at me and asked if something was wrong. I laughed and said, what could be wrong. She said that I was holding back and she really did want me to come. I decided that okay, if she wanted it, she was going to get it. As she started to suck me again, she inserted one of her fingers into my cunt. That was it. I couldn't hold out any longer and came so hard my toes cramped. I think Connie was happy, but I really didn't notice anything else. After my orgasm had subsided, Connie came back up onto the coach. I could see that her clit was hard as it was framed against her dress. I asked her if she wanted me to do the same to her and she moaned yes. I got down on my knees in front of her and she lifted up her dress and spread her legs. It was the biggest clit I had ever seen and thought for sure I was going to choke to death. Connie guided me to her and taught me how to suck her slowly so that I could open my throat and take her deeper. After a couple of minutes, I got the hang of it and could swallow her almost all the way. This kept up for a lot longer than I did, and she kept moaning and squirming around. I thought for sure she was going to cum, but she never got there. As my mouth was getting tired I stopped for a moment and told her that she was not letting go, just like I had tried to do. She said that she just wanted the feeling to last, and then said that she would rather cum deep inside of me instead of in my mouth. She then asked me if it would be all right to make love to me. I wasn't to sure about this, but Connie said that she would wear protection so that everybody stayed nice and clean. I decided that if I was going to learn how to be a girl fully, this was the final test. So I said yes, and Connie got up and lead me into the bedroom. She asked me to take off my skirt but to leave everything else on including my shoes. She then lead me to the bed and asked me to lay down. As I lay there she again started to suck me and before long my clit was rock hard. She kept saying how beautiful my clit was and how she was loved to suck it. I was feeling no pain and just lay there moaning. Then she turned me over so that I was on all fours. I could feel her fingers against my cunt and then felt the KY jelly being inserted. Connie paused and took from the night table a condom. I could hear it rip open and then I felt her clit against my cunt. It was very slippery and I was unsure if she was going to put it in or just tease me. Then I felt it start to go in. And boy, did I feel it!!! She was huge and I thought I was going to be torn open, but the feeling of pain lasted for only a moment. Then she was inside of me and it was all pleasure. I bucked my hips back to meet her thrusts and she started to ride me. Slow at first, and then faster. Each time she pushed into me, I felt her get deeper, until I thought I was going to pass out from the delicious feelings that were raking my body. I was moaning for her to fuck me harder and she was moaning that I felt so good. As she started to reach her climax, she grabbed my clit and started to stroke it. This was too much for me, and I came into her hand and onto the bed. The fact that I was coming triggered Connie and she yelled out as she bucked one last time. I was a little dazed and rolled over on the bed. Connie curled up beside me and started to stroke my thighs as she whispered that I was everything she had dreamed of. I was certainly impressed with her and we lay in bed for about half an hour before I realized what time it was. I told Connie that I had better get home or Roxanne would have a fit. We jumped out of bed, dressed and she drove me home. I was having a hard time walking after my encounter and just about slipped coming up the stairs. When I walked through the door Roxanne was in the kitchen. And so was a girlfriend of hers from work. I tried to go downstairs, but Roxanne called out that Anna should be a good sister and come and meet her co-worker. I was a little embarrassed but walked into the kitchen anyway. The girl from work was nice and commented on the way I was dressed. She asked if I had been out at a party and I just shook my head. My sister excused me from the room and said that since I had school tomorrow, I had better get to bed. She said that since last weekend, her sister was a different girl. Her friend just nodded knowingly and I went to my bedroom. It was the start of many wonderful times with my sister, Connie and a few other special people. More on these times in my next story! History Of Anna - Part 3 Like I said before, I did have a few other times with my sister and some of her friends. After my first introduction to dressing and subsequent visit with Connie, things in the female department for me slowed down. My parents had only been gone for a week, so by the next weekend, life was pretty much back to normal. I, however, still tried to dress as much as I could, but it wasn't much. About four months later, my sister decided that she was going to move out. There were many heated decisions with my parents on her living with roommates, and my Dad was not thrilled with her choice of people. One guy and one girl. He however gave in after my sister let him pay for their first six months of rent, insuring that they moved into a very nice townhouse in the better part of town. The guy and the girl were boyfriend and girlfriend so this at least appeased my parents. They did not know that this couple and Roxanne had been sexual partners for a while and if they did, I'm sure they would have both had coronaries. I was very sad to see my sister leave, but she promised that I could visit as much as I wanted and since the townhouse had three bedrooms, I could have one all to myself. She said that it would be Anna's room and I could fill it with all the clothes and girl things that I wanted. This was so exciting that I forgot about the fact that she was leaving and started to plan out my new room. Of course, I helped Roxanne to move and finally got to meet her roomies. They were both very nice and I liked them from the start. Gail was 22 and worked as a waitress while she went to university taking her nursing. She was good looking, long brown hair and always wore tight jeans. So tight, in fact, I could see her pussy lips etched in the fabric. Matt, her boyfriend, was 24 and working as an Engineer with a large oil company. He was also very good looking, reddish brown hair and deep green eyes, about 6 feet and 170 pounds. He worked out a lot and had a very muscular body. After we finished moving Roxanne in, she told me to come up to "My" bedroom. In it was a twin bed, vanity with mirror and a six drawer chest. There was frilly pink curtains on the window and a full length mirror on the closet door. She had told Mom and Dad that she needed the furniture because her friends from out of town would stay over sometimes. I guess Dad thought that it was better to have whoever sleep in another bed then with his daughter. It was exciting having a place just for me and my sister saw that I was pleased. She told me to open the drawers and the closet. In the top drawer I found an assortment of pantyhose, nylons and a pair of fishnet stockings. The second drawer contained four or five pairs of panties and three bras. The third drawer held two full slips and a half slip. In the forth drawer was my original lingerie that Roxanne had bought for me. The fifth drawer contained my original wig and a new one that was long and black. The final drawer held my dildo, my butt plug, the douching apparatus and a new 10 inch dildo that looked exactly like a cock. In the vanity was a wide assortment of make-up, false nails, nail polish and some perfume. The closet was the best. A wide variety blouses, skirts, pants, dresses and two new pairs of high heels greeted me. I was, to say the least, floored by all of the clothes. I thanked Roxanne for all of the stuff, but told her that she shouldn't have spent so much money on me. She said that she and purchased some of the things, like the wig and dildo, but the other things were hand me downs from herself and Gail. I looked at her and asked her if she had told Gail that I was her part-time sister and she said yes. She had told both Gail and Matt and they were excited to see me dressed. I blushed and got embarrassed but Roxanne assured me that both Gail and Matt understood everything and that the three of them had been lovers for quite some time. I relaxed a little, but was still unsure about all of this. My sister left me alone to set up my room the way I wanted to and after about fifteen minutes, I joined the three of them in the living room. They were planning a house warming party for the next weekend and Roxanne told me that I was invited. She said that I could spend the whole weekend with them and had already told Mom and Dad that she needed my help to get organized. It sounded like fun and Matt and Gail told me to come to the party as Anna. They said that there would be a lot of people coming over and it would be a great time. Matt said that since Roxanne had told them about me, they were very curious to meet this Anna girl and from the look in Matt's eyes, I think him more so than Gail. Roxanne said that Connie was coming along with a few other TV's, so I would not be alone as far as that was concerned. What could I say, except yes. From the first time I had dressed, I just wanted to do it more and more. It was so thrilling to be able to become an attractive female that I had found myself fantasizing about what it would be like to be with a man. I planned to have my chance on the following weekend and all during the week, I thought of nothing else. I kept my body shaved and wore my butt plug everyday. As the weekend approached, I thought I was going to burst with excitement. On the Friday night, I packed my things for the weekend and Roxanne came over and picked me up. We went shopping and bought a bunch of food for the next night. We also went to the drugstore and picked up some condoms, bubble bath, a fresh tube of K-Y Jelly and a couple of Fashion magazines. Roxanne said that the next day was all mine to get ready but that she and Gail would need help that night to prepare the food. When we arrived at her house, Matt came out to help unload the groceries. After we were done, I went to bed early. It was going to be a long day and night tomorrow, so I wanted to get plenty of sleep. The next day I awoke and went down to the kitchen. I was surprised to see Gail making coffee, with nothing on except for a skimpy robe which barely covered her bum. It was open quite a bit at the front and I could not help looking at her breasts. She greeted me and noticed my stares and smiled. She asked if I thought she had a nice body and I said yes, and as I did, Matt walked in with nothing on and a huge hard on. He grabbed Gail and said that she had better come back to bed as he was horny as hell. They both left the kitchen and I found myself quite excited by all of this. After having breakfast with Roxanne, she asked me what I had planned for the day. I told her that I was going to read through the magazines we had bought and spend time on myself, getting ready for the party. Roxanne was off to do some more shopping so she would see me later. She handed me a bag and told me not to open it until after she had left. After doing up the dishes, I retired back to my bedroom and could hear Gail and Matt still going at it. He was calling her all kinds of names and she didn't seem to mind it at all. She kept moaning and groaning and before long their love making came to a head, so to speak. I heard them get up, shower, get dressed and leave. Before they left, Gail poked her head into my bedroom and said that they would be gone for about four hours, so they would see me later. She was wearing another pair of those tight jeans and a very skimpy halter top. One very fine looking lady and I thought Matt was quite lucky to have her as a girlfriend. After they had left, I remembered the bag that Roxanne had given me. I opened it up and found two magazines about TV's. I'll never forget the name of them. "Chicks With Dicks"! Very poetic. It featured all sorts of TV's in different poses and with different clothes on. I was getting very horny looking at the pictures, so I turned my attention to the third item in the bag. It was sort of an instruction book on how to be a TV with information from applying makeup to tucking your balls correctly and pulling back your penis to give you the look of having a vagina. I read the whole book and learned and incredible amount of information on dressing, especially since it was geared to men looking like women. After finishing the book, I looked over at the clock and it was already 3 p.m. I decided to shave my body, douche myself and then take a long bubble bath. When I shaved this time, I shaved off all my pubic hair, something I had learned from the book. To be quite honest with you girl, I will never do this again. It feels wonderful for the first day, but unless you keep it up, it itches like hell while it grows back!!! I have never completely shaved my pubic hair since. I was getting out of the bath when everybody started to get home. Roxanne came up to see how I was doing and told me to take off my robe so that she could check me out. She was very pleased with my shave job and fondled my balls lightly. She then told me to bend over and checked out my rear. As she caressed my bum, she said that I had a very pretty cunt and that hopefully it would not go unnoticed that night. I secretly hopped so, too. After Roxanne left, I started to get ready. I inserted my butt plug, tucked up my balls into their sockets and pulled back my penis like I had seen in the book. I put on the black bra and waist cincher, followed by my garter belt and the fishnet stockings. I put on a pair of tight panties, and it worked. My crotch area looked just like Gail's, with full lips and all. I filled the bra cups with the water filled balloons and went to the vanity to start my makeup. After finishing my face, I sprayed my body with perfume including a quick spritz in my crotch and one behind the backs of each of my knees. The tough part was what to wear as far as clothes. I didn't really know what everybody else was wearing, so I decided that I would go all out. I picked out a pretty party dress that was bright pink taffeta, the bottom of it stopping just above my knees. It had a back zip and I had quite the time trying to get it done up. It had a side slit and I was pleased to see that my leg showed through almost to the top of my nylons. The shoes I picked where new, pink to match the dress, and of silk material. They had a four inch heel and looked wonderful on my feet. I combed out my blond wig and set it in place. I finished off my transformation with earrings, a gold necklace and an ankle bracelet. After putting on the false nails and painting them, I was ready for the party. I stood back from the mirror and was pleased and excited with my look. I hopped it wouldn't go unnoticed. I walked down stairs and met Gail and Roxanne in the kitchen making trays of food. They were both wearing dresses, so I felt a little more at ease. Roxanne commented on my excellent choice of clothes and Gail said that if she hadn't seen me, she would have never have believed it. As we talked and prepared the food, Matt came in. He stopped and for a moment stared at me. He then turned to Gail and asked her who her friend was. We laughed and Roxanne told him to say hello to her sister. He looked at me again and gave me a wonderful wolf whistle. He then told me to turn around and model for him. After I was finished, he said to Gail that the dress and shoes looked better on me then it had ever looked on Gail. I thought for sure she would be mad, but she smiled and said that he was right, and she had a bunch of other clothes that would fit me. I was thrilled that I was so appealing to both male and female and happy about getting more clothes. We spent the next hour getting the house ready for the guests, and around eight o'clock the first people started to arrive. I played maid for the first little while, fetching people drinks and putting out the food. Roxanne introduced me to everybody as her sister, and I even met her boss and his wife. I was sure that nobody knew who I really was and the party was in full swing when Connie arrived. She looked great and we talked in the kitchen for a while. I told her all about my own bedroom and the clothes and stuff and she was very happy for me. I promised her a tour later and she pinched my bum and said it was a deal, as long as it was an intense tour of my bed. By about eleven, I think around fifty people had showed up. The place was packed and for the first time that night, Matt came over to me and asked me how I was doing. I said fine and told him I was getting a little drunk from the wine. He then looked at me and said that the only way you could clear your head, was to give head. I laughed and said in a teasing way, why, whatever do you mean??? He just took my hand and lead me from the room and up the stairs to his bedroom. I could see Gail watching us, but she smiled and waved good-by. When we got to Matt's room, he turned and closed the door. I asked him if we should lock it and he said that nobody would come in. He then placed his arms on my hips and drew me closer. He told me that I made one hell of a fine looking woman and he had been hoping to get me alone all night. I asked him about Gail and he said that he had already told her what he wanted to do to me and she had said that it was fine with her. As we talked, Matt pulled me closer until I could feel his cock against my tummy. I asked him in a whisper what he wanted me to do and said that he wanted my lips around his cock and then he wanted to fuck me. I pulled away from him and told him to wait a moment, as I had to go to the bathroom. I bolted from the room, went to the bathroom and removed my butt plug. I checked my makeup and then walked back to the bedroom. Once inside, I found Matt on the bed with his pants and shorts off. His cock was huge and stood straight up in the air. I decided to tease him a little, so I crawled onto the bed and asked him what I should do with this thing. He told me that he wanted me to suck him and I played dumb and said that I didn't think I was that kind of girl. He sat up and said that if I wasn't that kind of girl, why was I back in the bedroom with him. Hard question to argue, so I leaned forward and kissed him on the lips. He returned my kiss and soon we were rolling on the bed, kissing and touching each other. In the process, Matt wrestled my panties off and started to finger me as we continued to kiss. I felt so good to have him slide his fingers in and out of my wet cunt and I could feel my clit getting really hard. As he licked my ear, he whispered to me that he really wanted me to suck his cock and that was about all the encouragement I needed. I moved to his crotch and swallowed him whole. As I was sucking him, I heard the bedroom door open. I froze, with my mouth on he end of his cock and made sure my dress was pulled down over my exposed clit. As I waited to hear something, I felt somebody get on the bed. For a moment, I was stunned. Then I heard Gail's voice tell me not to stop and could feel her hands move up the backs of my legs and under my dress. She took hold of my clit and said that I was a beautiful girl with a beautiful clit and that she wanted to taste it. Matt's hand came down onto the back of my head and pushed it so that I swallowed him again and I could feel Gail slide under my dress. Before I knew it, she was sucking me as I sucked Matt. I came at once and Gail sucked up all of my juices. Matt was so big and hard, I thought he was going to cum but he told Gail to move up beside him. She lay down on the bed and Matt rolled off. He told me that Gail really liked to be licked and would I want to taste her pussy. I whispered yes and Gail lifted her dress and spread her legs. I put my face back down into her crotch and found her clit with my tongue. The moment I touched it, she let out a small cry and said that she wanted my tongue in her cunt. I moved it in and out and Gail thrust her hips into my face and almost smothered me. As I worked on Gail, Matt slowly moved my dress up to expose my ass. He lifted my hips and before I knew it, worked three of his fingers into me. It felt so good and I moaned out loud in appreciation. This spurred Matt on and soon he had four fingers working in and out of my now very wet cunt. The slurping sounds only made me hotter and I started to beg him to fuck me. Matt removed his fingers and suddenly plunged his cock into me. The first thrust hurt like hell, but quickly went away. The pain was replaced with an intense pleasure as he fucked me from behind and the harder he fucked me, the harder I licked and sucked Gail. During all of this, Matt kept calling me a little slut and asked Gail how her cunt licker was doing. She just moaned but didn't say much of anything else. Her clit, by this time, was like a little cock and I could feel her body start to tremble with her oncoming orgasm. During all of this, my own clit hard returned to its rock hard state. Mostly because while Matt was fucking me, he was also stroking me. I could not keep track of the times Gail came and finally Matt lifted me up by my breasts and started to kiss my neck. He whispered in my ear that I should fuck Gail with my beautiful hard clit and I started to move toward her. As I did, Matt kept his cock firmly imbedded in my cunt. As I moved even with Gail, she wasted no time in grabbing my clit and forcing me inside of her. As I slid into her soaking wet cunt, Matt brought all of his weight down on us and rammed his cock home one last time. I think we all came at once, but I'm not sure. I'm not really sure why I came. It was either Matt's cock or Gail's cunt or the combination of both. All I know is that it was quite a while before any of us moved. Matt was first off and I quickly got off of Gail and started to organize myself as best as possible. As I was standing, Matt sat back down on the bed and started to finger Gail. She moaned that she wanted to be fucked again. I said that Matt was on his own as I was still trying to recover. I left them on the bed with Matt starting to lick Gail all over again. I'm sure they were both part rabbit. As I made my way to the bathroom, I met Connie and Roxanne in the hallway. I'm sure I looked like hell, and Connie remarked that I had better change my fishnets as they had a huge run in them. Roxanne then asked me what I thought of Matt Gail and all I could say was that she was very lucky to have them as roommates. Connie was curious as to what had gone on and I told her that as soon as I cleaned up, I would get back to her. Once in the bathroom, I re-did my makeup and brushed out my hair. I went to my bedroom and swapped my fishnets for a fresh pair of nylons. As I hooked my garters on them, I kept thinking about the events that had just transpired and vowed that I was going to have more times with Matt and Gail. When I was finished putting myself back together, I proceeded to go down stairs, but stopped outside of Roxanne's room. The door was slightly ajar and I could hear her voice inside. I pushed open the door and found her on the bed with Connie between her legs. As I started to turn around, Roxanne asked me to come in and watch. It was a little awkward, but my curiosity got the better of me. As I approached the bed, Connie looked up and asked me if I would like to join her. I wasn't sure if all three of us would fit on the bed, but Connie answered my question by moving over and making room for me. As I lay down, Roxanne purred that she was really horny after hearing all about my adventures with Connie. She then asked me to show her how I made Connie happy. I was more than willing and Connie lifted up her skirt and pulled down her panties. I moved down and took her stiff clit between my lips and started to pump up and down, drawing her deep into my throat. What happened after that? Well, I think you know by now! Until next time! History of Anna - Part Four I started to live part-time on weekends at Roxanne's and worked quite hard on perfecting my image. As I added to my clothes collection, my sense of style grew considerably. I found I tended to gravitate more to the flashy mode of dress and, with the help of Roxanne, Gail and Connie, acquired some very sexy outfits. I also discovered Frederick's Of Hollywood and a few other mail order outlets. This, combined with a lot of TV magazines and books, helped in establishing my look that has stayed with me for years. When I turned sixteen, I received my first car. Freedom at last. It wasn't anything special, an old 72 Volkswagen, but it was mine and I could now come and go as I pleased. The first weekend I had my drivers license, I drove over to Roxanne's and showed it off. She was pleased that I had a car, since she was the one who normally would have to drive me around. I decided to stay over and phoned Connie to see what she was up to. She said that she was busy on the Friday night but did I want to come over on the Saturday. We could go out for a drive in my new car and maybe hit a club or two. I was only to eager to see her and to show her my car. I stayed over at Roxanne's and on Saturday decided to get up early and spend the day as Anna. I had the house to myself as everybody was out for the day to the country for a picnic and dance. After my shower I put on my sexiest bra and panties set, a low cut blue silk blouse, a pair of navy pantyhose and a pair of Gail's old jeans. They were the kind she always wore, Fancy Ass, I believe. I had tucked my balls up into their sockets so that when I put the jeans on and pulled them tight around my waist, I looked like I had my own pussy lips. They felt and looked great and I slipped on a pair of high heels with a sling back to complete my dressing. I put on my long black wig and brushed it out. After doing my make-up, which by this time I was getting quite good a