11/22/1999 New Girl in Town
Where to begin? Summer was here and I had nothing to do. One more year of high school and then I would have to decide what I was going to do with myself. School for me has not been a pleasant experience. I do not have a lot going for me. I am not a great student or athlete. The only thing I am remotely good at is swimming. I have been told I have a swimmers body, lean and although I am only 5'8", I look taller because I am lean.
Since both my parents work, I am alone in the house all day and all I have done this first week of holidays is mope around. A few times I have gone out in the back yard and spotted my next door neighbor, Susan, in her yard watering her garden and puttering around. I have never really had a long talk with her since I am quite shy. We just say hello and that is it. The one day I saw her, she came over to the fence and continued our conversation. I found her very easy to talk to. She did not make me feel at all uncomfortable or self conscience. The time went by so quickly as we talked and before I knew it an hour had gone by. We Discussed school and girls and what my plans were for the summer. I told her that I had no plans at the moment, I was taking the summer a day at a time. I think she knew without me saying that girls were not even in the picture for me. The next day, I made a point of going into the yard, hoping to see her. Peeking over the fence I could see she was not in the yard and as I turned to walk back into my house I noticed her coming out of her patio doors in her swim suit. Susan waved and said hello to me, saying she would like to have a talk with me. I could not keep my eyes off her. She was not what you would call gorgeous but I think her attitude contributed to her appeal. She was a few inches taller than me and had shoulder length dark hair and she was not very big breasted, but her legs were her best feature as far as I was concerned. There was not an ounce of fat on her. Moving back to the fence so we could talk, Susan told me that she had discussed my situation with her husband and he suggested that maybe I could help her around their house. She wanted to get some painting and wallpapering done, but he has been so busy at work that they haven't been able to accomplish it. I told Susan that I had never done any wallpapering before but she said I could be the extra pair of hands for her. Besides, I could earn some money and we would get to know each other better. If I were interested, we would start on Monday morning after everyone had left for work and that would give her the weekend to purchase all that was required. Monday morning arrived and I went over to their house and Susan was waiting for me. Everything was laid out in preparation for painting. Susan said that the wallpapering would not be started until near the end of the week, which would allow for the paint to dry. Over the next few days, Susan and I talked about everything. More than once I found myself looking at her when she bent over or climbed up the ladder and I am sure a few times I was caught by her staring at her legs or breasts as she bent over but she never tried to hide anything. One day Susan was up the ladder and her hands were all covered in paint, so she asked me to go to the laundry room and get the clothes from the dryer and fold them for her. Pulling the clothes from the dryer I saw they were all her underwear and hose. I inspected every panty and bra before they went into the basket. Most were either bikini or thong style. I loved the feel and the look of them. I held a bikini up to my cheek, to feel the smoothness and softness. Just then Susan walked in and surprised me by saying, "You like those do you?" I didn't know what to say. She smiled and turned and walked out of the laundry room. I stood there not knowing what to do, I was totally embarrassed. I picked up the basket of clothes and went into the other room. Susan was back at work on the ladder and asked me to spread the clothes on her bed to let them cool off before putting them in the drawer. But first I wanted to apologize to her and she told me there was no reason to, that it was just probably curiosity on my part. Walking into Susan's room, I noticed other lingerie on the bed and while I laid the freshly washed ones out on the bed to cool off, I inspected the others that were there. I felt strangely excited looking at and touching Susan's lingerie and without really thinking I picked up a black thong and held it up to me. I felt myself getting an erection. Susan came in the room and noticed the state I was in and said why don't you try it on? I must admit I wanted to but I still felt very uncomfortable even though she seemed to be okay with it. The rest of the day was spent cleaning up the paintbrushes, trays and removing the painters tape and then I left with the promise to be back the next day. Bright and early the next morning as soon as everyone had left for work I went to Susan's and knocked on the door and then walked in. Susan was at the kitchen table having a coffee and offered me one. She told me she was in no hurry to start today because we were ahead of schedule so we could start later. The discussion eventually turned to what had happened the day before and she admitted that it kind of turned her on to see me so interested in her lingerie. It was all she could think of for the rest of the day. I wanted to tell her the same thing, but I didn't. However, I think she knew what I was thinking anyway, the beginnings of an erection gave me away. Susan then said she had an idea and getting up she took hold of my hand and led me into her bedroom. There on her bed was a selection of lingerie laid out in sets, along with matching hosiery. Looking at me, Susan took both my hands in hers and said that if I wanted to I could try on anything I wanted and the secrete would just be ours, No one else would know and since we were about the same size there would be no problem with fit. I could tell by the look in her eyes she was sincere but I was still a little reluctant. Leading me over to the bed she picked up a white set and held it up to me. That was all I needed, I reached out and took the panties in my hand. With her help I had the outfit on in no time, along with a pair of her pumps. I loved the feel of the material next to my skin and the way it hugged my body, but with my erection, the panties didn't fit too well. Susan led me to the mirror so I could see myself. I was a little confused since I felt like a girl but looked like a man in woman's clothes. Susan could see my expression and agreed with me. She told me there was only one way to resolve the problem and that would be to make me look like the woman I felt like. Not knowing what she meant I asked her to explain. She said in order for me to look like a woman I would have to get rid of the body hair, apply makeup and have something done with my hair and if I was willing, she would help me, but I had to do as she told me. Susan then helped me remove the under garments and she led me to the bathroom where she applied hair remover to my entire body, trimmed up my pubic hair into a little heart shaped patch. While this was going on I had a continuous erection that would not go away but it didn't seem to bother Susan at all, she just worked around it. I was aching for release. After about half an hour Susan placed me in the shower and all my body hair was washed down the drain. Even my skin felt softer without the hair. Once I was dried off, Susan helped me dress again, sliding the panties up into place was a little difficult because of my erection and Susan muttered something about having to look after that problem. Sitting on the edge of the bed, she had rolled up the nylons and slid them over my feet and up my legs and into place. Next came the bra and she stuffed it with flesh toned nylons to fill out the cups. Now that I was covered Susan led me to the makeup table where I sat down facing away from the mirror. On the table were all of Susan's makeup items and she went to work on me, but I had to promise that I would not look until she was finished and when she told me to close my eyes, I must do it. Once the makeup was applied, she told me to close my eyes tight and not to open them until she said to. She would be right back. Susan was gone for what seemed like a few minutes and when she returned she placed a wig on my head and made the adjustments to it. When she was satisfied with the look, she had me face the mirror and told me I could open my eyes. I could not believe the person I saw in the mirror was I. I looked like a girl. With clothes, light makeup and wig, I was transformed into a beautiful teenage girl, that could compete with the better-looking girls at school. Standing in front of the mirror I saw a girl with shoulder length auburn hair, a white bra and thong set with matching garter belt, nylons and pumps with a heel of about 4". The only problem was, I also had an erection. Susan noticed as well and told me not to worry and she pulled the thong aside and holding my erection in one hand she gave the base of it a hard tap and it was gone. I was lucky I didn't explode when she touched me. I had never been touched by a woman before but it was over so quickly I didn't have a chance. Next she went to her closet and came back with a light blue dress that was, I found out later called a sheath dress. It fit very tightly and I must admit I looked very sexy in it. I felt wonderful walking around the bedroom all dressed up. Susan told me I could stay dressed all day if I wanted, since it took so much work to get this way it would be a shame to waste it by undressing now. I could not believe this was happening. The rest of the day went by in a blur. I was so happy and I could not believe the affect it had on Susan. She was hugging me every chance she could and commenting on how sexy I looked just walking around or when I sat down and exposed the tops of my nylons. Unfortunately the time came when I had to get back into my own clothes and go home. Susan seeing my sadness remarked that we could do this every day if I wanted, but I would have to get used to helping her dressed as a girl. Without hesitation I agreed with a promise to see her tomorrow. The next morning when I showed up, Susan had the clothes chosen for me already and laid out on her bed. She told me to go on in and to call her when I was finished. Today I was to wear a flesh colored bra and panty set with taupe nylons, black pumps, black mini skirt and a beige silk blouse. Before I put the clothes on, I applied the makeup and wig as best as I could remember how Susan had done it. Sitting on the edge of the bed I pulled the stockings up my legs and attached them to the garter belt and then pulled the panties up over my erection. After I had the blouse and skirt on, I called Susan into the room. Once she came in she commented on the good job I had done with my makeup and said I would get better the more I did it. She also noticed the bulge in the front of my skirt. Coming over to me we both sat on the bed and she put her arm around me and gave me a kiss, just brushing my cheek at first then on the lips. I didn't know what to do. Next thing her tongue was inside my mouth and darting everywhere. Her hand rested on my thigh and made its way up under my skirt and she started rubbing my erection through the panties. Breaking off our kiss, she asked me if I liked the name Nicole. I nodded yes and she said from now on I was Nicole. She told me she had always wondered what it would be like to make love to a girl. With that she got up and went across the room to the armchair and sat down, pulled up her skirt and placed each leg over an arm of the chair revealing she had no underwear on. With that, she called me over to her as she casually played with herself. As I stood before her, she told me to kneel before her and use my tongue to please her. I have never done this and I wasn't quite sure what to do but Susan said I would know what to do by her reactions. Sliding my hands under her for support I moved my face closer to her. I could see her wetness and smell her womanly lust. I could feel her pubic hair on my cheeks as I stuck out my tongue to lick up her juices. I could feel her hands on the back of my head, pulling me into her. I probed and licked with my tongue, licking and sucking up her juices. I plunged my tongue into her repeatedly retrieving and swallowing them as much as I could. Susan put her legs over my shoulders and began to squeeze my head and pull it in tight to her; I could hardly breath as I used my tongue and lips on her. She began to spasm and she ground herself into my face, then she begged me to stop as she tightened her grip on my head with her legs. After a few minutes, she lifted her legs from my shoulders, pushed me to the floor. And raised my knees to my chest. She crawled between my legs and kissed me deeply for a long time then told me she was going to make me feel like a woman. Susan moved her way down my body and pulled aside my panties, took hold of my erection and squeezed it real tight, I thought I was going to burst. Lowering her head she kissed the tip and swirled around it with her tongue and at the same time she slowly pumped with her hand. I had never felt sensations like this before. Then she took all of me into her mouth and at the same time shoved her finger up me. As her finger moved in and out of me, her hand moved up and down as her mouth sucked and her tongue licked, I could feel contractions throughout my body. Within a few minutes I just about fainted as Susan was milking every drop from me. I had never had anything up me before and I could not believe the great feeling it was. The remainder of the day was spent rushing around the house trying to get back on schedule and then it was time for me to get changed to go home. The next few days were much of the same routine. Susan kept finding more and more things for me to do, such as doing the laundry, vacuuming, dusting the furniture and cleaning the bathrooms. The following Monday morning, I arrived as usual to the house and Susan said she had a surprise for me. Leading me into the bedroom, she said she had a new outfit for me and she was dying for me to try it on. From the box on the bed she removed a pair of black pumps with straps and a buckle hanging from each shoe and the highest heel I have ever seen. Next came the lingerie, black garter belt, seamed nylons, black lace bra and matching thong panties. Then she pulled a dress from the box and I knew it was a maid's outfit right away. I had seen them in magazines. It was beautiful. I could hardly wait to try it on. But first Susan wanted me to remove my body hair and have a shower. I was back in no time and Susan helped me with my makeup, it was going to be perfect. Before I started to get dressed, Susan gave me something to put on called a gaff. It goes on under the thong and holds the penis in so there is no bulge showing. Once I had the bra, garter belt, nylons and thong on, she helped me put on the shoes. The straps buckled around the ankle and looked very sexy in the mirror. Then she helped me with the outfit and once it was on I felt so feminine I never wanted to take it off. Susan knew what I was feeling and she told me what I wanted to hear. It was mine as long as I was with her and it was my responsibility to always keep it clean and fresh. From now on I was to wear it every day unless told by her I was to wear something else. Then she told me there was one more part of the outfit that I had to wear. She told me to go over to the dresser, pull down my thong, bend over and lean on the dresser. Susan came up behind me and kneeled down. Reaching between my legs, she grabbed hold of me and started to rub me. I spread my legs more to give her better access and then I felt her fingering my butt. A few seconds later, I felt something larger trying to get in and eventually after a little resistance and pain it filled me up. I did not know what it was. Susan stood up and said for me to turn around. I felt a little uncomfortable but it was also making me feel sexy This she said, was a butt plug and I must wear it all the time, every day. Over the next couple of weeks, I was in heaven. I wore the outfit every day and I found myself wanting to please Susan any way I could. Sometimes I would go two or three days without Susan telling me to service her. This was done orally or with my hand, we never had intercourse and on the rare occasion she would stimulate me to orgasm just when I seemed to be at the bursting point. I always seemed to be in a constant state of arousal, but Susan had warned me never to pleasure myself. The days went by and we eventually had the house redecorated and there seemed nothing else to be done but Susan had me doing all the daily chores and I had a routine that I followed. This allowed Susan to pursue other interests. I got to the point I was so comfortable, I would answer the door when someone was there and take a message for her. I was always proper and I knew my place. One evening, my parents told me some bad news. My Father was being transferred to another city and my mother was able to move her position to the city as well. I was devastated. I still had one more year of high school and naturally I didn't want to leave the school and especially Susan and our arrangement. I couldn't sleep all night and the next morning I told Susan the bad news. At first she was upset then she regained her control and told me not to worry that maybe something could be arranged but in the meantime I had things to do, so I better get started. At he end of the day, Susan came into the room when I was preparing to go home and she told me she would talk to her husband and see if they could come up with a solution to the problem of me having to leave. The next day as I was dusting the living room, Susan called me into the bedroom. I had never seen her dressed like this before. She was wearing black half-cup bra, black garter belt and hose and shoes identical to mine. She was standing by the bed and as I entered the room, she told me to stand before her. I noticed in her hand she had a short black leather stick that looked like a riding crop. Very sternly she told me I had been too lax lately and was not performing my duties the way I should be and as a result I would have to be punished. She told me to lean over onto the bed and as I did so, my outfit rode up exposing my rear to her. Then I felt a sharp pain as the crop came down on my butt. I don't know what I did to deserve this. I received about six strokes and I was very sore. Susan then told me to get on my knees before her and lick her shoes and when I received a whack on the butt I was to start moving up her legs very slowly, being very careful not to run her nylons. After a few minutes of licking and kissing her feet, I felt another sharp pain and I began to kiss and lick my way up her legs. Eventually I reached the tops of her nylons and the soft skin of her upper thigh. I could see her wetness and I wanted to taste it with my tongue. As I was about to lick her, she told me to stand up and kiss her nipples which were exposed in her half-cup bra and sticking way out. I leaned my head in towards her and took a nipple into my mouth, sucked it in and circled it with my tongue then gently nibbled it. In the mean time Susan had taken hold of me and was rubbing me as I took her other nipple into my mouth and nibbled it before sucking it into my hungry mouth. Just as I was about to come, Susan stopped rubbing me and told me to lean over on the bed once more. She began to rub me again and I was ready to explode, I felt her one hand behind me grasp the but plug and pull it out of me. This was done so suddenly that my insides felt like they were going to come with it and I lost my urge to come. With that, Susan lay on the bed and told me to kneel between her legs and service her. On my hands and knees I lowered my face to her and began to lick her juices from her inner thighs, working my way into her, lapping them up and probing with my tongue. I loved her smell and taste and I could do this for hours. As I began to circle her clit with my tongue she held my head back, telling me to lick and probe some more as she held my head firmly in place. Suddenly I felt someone grab me from behind. I knew it wasn't Susan since she wouldn't have been able to reach me. Susan held my head firmly in place and I could not turn to see who was there and as I was being rubbed and pumped I felt something probing me from behind. It soon found its target and was slowly working its way into me. I felt both pain and pleasure at the same time. I was trying to concentrate on pleasing Susan but at the same time I was experiencing something new and pleasurable. With each pump it was going in deeper and I thought it would never stop, it just kept coming in and then I could feel the fullness in me and something slapping the backs of my thighs as he went in all the way. This must be how a woman feels when she is being made love to and I now truly felt like a woman. I could feel Susan approaching orgasm as she began to tense up and I concentrated on her clit. At the same time, whoever was in me was getting harder it seemed and was pumping more rapidly and on the verge of cuming. Both started moaning almost at the same time and it almost felt like I could feel his cum spurting inside me. I myself began to spurt without even being touched and the sensation was so intense that we collapsed on the bed. The person remained inside of me and I felt so sexy lying there knowing I had pleased both of these people. When he withdrew from me, only then did I realize it was Susan's husband Dave. Susan then noticed the time and told me it was time for me to get ready to go home. Without a word Dave left the room with Susan and I was left alone with my thoughts as I cleaned up. Soon this would be over, the happiest time of my life and I would have to go somewhere strange and start over. Two days later I came over in the morning as usual and Dave was in the kitchen having coffee with Susan. This was the first time he had been there in the morning and I didn't know what I should do. Susan told me to continue on as usual and when I was dressed to come back to the kitchen because they wanted to talk to me. Once I was dressed and made up, I returned to the kitchen and stood before Susan and Dave. Both were looking at me and smiling. Susan spoke first. She said that Dave had talked to my parents and explained how I felt about having to move during my last year of high school. It would be very difficult for me to adapt to a new school and people, after having lived for so long in this area. My parents agreed that it would be difficult for me, however, they could not think of an alternative and they did not want to give up the opportunity of advancing their careers by not taking the transfer. Dave proposed that I could live with them and it would not be an inconvenience. If my parents were to sign over guardianship to him and Susan, then all my needs would be looked after and if a medical emergency arose, then they would have the right to sign for what ever was needed. My parents hearing this, saw a way out of the glitch I was causing and agreed to it right away. Hearing this I was so happy, I would not have to leave. Susan then said that because they were now my guardians, they would put me on hormones and I would develop the breasts I had always wanted. Everything was falling into place. Susan told me I should thank Dave for all his work on my behalf and I knew she was right. Looking up at Dave, I walked towards him as he undid his zipper on his pants. I went to my knees before him and removed him from his underwear and grasped him in my hands. I was so happy!! I kissed the head and laid it on my tongue to catch the drop of pre cum, he tasted wonderful. As my mouth enclosed him I could feel him getting harder. He grasped the back of my head and pumped. With each stroke he got harder and bigger. I was finding it difficult not to gag as he hit the back of my throat, but eventually I became accustomed to it and gag reflex disappeared. I was now able to enjoy the pleasure I was providing him. He started to breath harder and I pumped with my hand and sucked harder, rubbing the head with my tongue before it plunged again to the back of my throat. I could feel him tense and moan and he exploded in me as he was at the back of my throat. I could feel the cum as it spurt out. As he withdrew from my mouth, I held on to him and cleaned up every drop with my tongue before I would let him go. Smiling to myself, I knew this is where I wanted to be and I knew there would be a new girl at school this fall!