Andy's Summer Vacation free porn video

Andy's Summer Vacation By Alyssa Davis It was a cloudy June afternoon, one week out of school on summer vacation, and already all my friends were out of town. Boredom took me to my mother's bedroom to talk to her. Unnoticed, I stood watching her at her dressing table applying her makeup. I always enjoyed watching her apply all the her beauty aids and found it fascinating. She did it with such artistry. The transformation from a plain housewife to a very fashionable lady was always amazing to me. Finally she noticed me watching, "Hi Andy," she said, brushing on a dark coat of mascara. I approached closer, intrigued with what I saw, "Hi mom, are you going out somewhere?" She smiled, turning back to the mirror, forming her lips to receive the dark red lipstick she rotated up from the gold tube, "Oh, I'm just going to the mall, shopping. There's some good sales going on. Want to come along?" I was distracted, closely watching her apply the slick coating of color, slowly but carefully outlining her lips before filling in. Then pursing her lips to spread the color evenly. She noticed me watching intently, her eyebrows raising in question. "What does that taste like?" I asked. I was really curious...thinking maybe someday I'll sneak in and try some. "Oh, it has no real taste I can describe, just a smooth, slick feel, I guess." She looked me in the eye, her mind evaluating the innocence of my request and my tone of voice, "Would you like to find out for yourself?" I nodded slowly, afraid of what she might think, but the lure of trying it, especially trying it with her watching outweighed my fears. I moved closer, now standing against her, the contact of our touching thighs sending a chill down my spine. She was attired in a slip and hose. I could feel the silkiness of the two fabrics sliding against my leg. Holding my face steady with one hand, she reached over and carefully painted my lips as I cooperated with my mouth slightly open. The feeling was exquisite, more than I had imagined. When she finished, I turned to the mirror. Pretty red lips were there for me to see. I licked them, savoring the strange taste, actually no taste, but as she had said, a feeling of waxiness. I was getting hard, glad that my baggy pants covered the growing lump, entranced by my expressive lips, each gesture or delicate lick of them looking so seductive and sexy. Mom's voice brought me back down to earth, my fear being that I would have to go and wash it off. "Gee, you look so pretty with your red lips...I'd like to try a few more things.... Are you game?" "What do you mean?" I asked, trying to be casual, my heart beating triple time...Did she mean what I thought she did? Was this what I had dreamed of? "Let's see how you'd look if you were a girl....with full makeup." This was too good to be true...she was going to put makeup on me! The lipstick had given me the idea to do it myself sometime when she was away, but this would be even better. As I nodded my head in what I hoped wouldn't be too quick a response, I also wondered how I would look and feel as a girl, especially after watching mom get dressed so many times. I just knew I had to try it. "OK, If you want...," I replied, trying to seem casual. "First, we've got to do something with your hair. That's where it all begins," she said. We switched places with me now sitting on her makeup bench. I had sat here before, but now it was different. I tingled with expectation as I waited. She took her brush and made the first pass through my hair, the bristles massaging my scalp in a delightful way. I could feel the change coming over me as she brushed it till it was smooth, then teased my hair up and back into a feminine style. Being well overdue for a haircut, it was long enough for her to work her magic. A little hair spray with a delightful fragrance held it in place as she curled and twisted it all to her satisfaction. She trimmed the front into bangs covering my forehead. I watched her perform her miracle in the mirror paying close attention. Amazing what she could do, I thought, wondering if I could do it on my own. Next, she applied a little light brown eye shadow to my eyelids, and mascara to the lashes. For the first time I actually could see my lashes as I blinked my eyes. I felt odd, dreamy. The big, very soft brush whisked a slight bit of blush to the hollows of my cheeks. My young skin fairly glowed. I didn't need anything else. A pair of clip-on earrings snapped into place, "To finish the look." Mom said. I turned back to the mirror to be greeted by a beautiful young lady! I was spellbound, locked into the vision of her loveliness.... I am pretty! My mother hung over my shoulder, her eyes glistening, "Look at you" she bubbled, "you look just like me...I always wondered how you'd look as a girl. There's no doubt you could be my daughter Andrea! How would you like to be Andrea for today? You know, we could make believe! It would be great fun! Oh please!" her enthusiasm buoying me along, making me forget that boys don't wear makeup or try on their mother's clothes. She was so happy I just had to go along with it. "Sure...I don't mind." She clapped her hands, her eyes sparkling, "Let's try on some of my clothes...I know they'll fit you, we're about the same size...it will complete the image, you know." "Yes," I replied without hesitation, my pretty face breaking into a dazzling smile. I had always thought about it, been tempted, yes, even wanted to, but now she was suggesting it! "Take off your things while I choose your new outfit." "What should I take off?" I asked innocently, hoping for all. "Why, everything, of course !" she said, her tone indicating it a silly question. I felt odd, shy, sure that my excitement would show. Turning my back, I quickly stripped naked, grabbing the items she handed me and using them to cover myself. First, a pair of white nylon panties. They felt wonderful against my skin, so wonderful that I had trouble getting them on over my growing hard on. Next, I held my breath while she fit upon me a matching white, rayon bra, hooking the back for me and stuffing the cups, each one with a soft pair of panties. Already I was admiring the shapely girl that looked back at me from the mirror. It felt strange to be wearing a bra, but, like the makeup and hair, I liked it too. "That looks about right for a girl your age. But we'll have to do something about your friend down there." We both looked down to the unladylike bulge that was straining at my new panties. "Mom, I..." but she put a finger to my red lips, her voice low and secretive. "Honey, that just means that you're enjoying yourself, don't worry about it, just tuck it back and under so it doesn't show." Turning my back again, I wrestled the straining member to where only a little showed in front. "We may have to get you something for that." she said, hinting that there may be more of this in the future. "I want you to wear this full slip...be careful you don't muss your hair, putting it on." I carefully placed it over my head and slowly pulled it down over my body. It felt wonderfully smooth and silky. Watching myself dress in the mirror, I was in love with what I saw, in love with this delightful girl. It felt so natural and very comfortable. Mom was watching me admire myself and smiled. I think she knew what I was thinking, and for some strange reason she approved. She handed my a pair of dark shaded nylon stockings which I easily rolled up my legs. The elastic tops needed no garters. "Hmm, my goodness, Andy, you put those on perfectly...are you sure you haven't had practice?" I blushed, "No," I whispered, "but I've watched you many times." She could hear the envy in my voice. "Oh my, really! I've noticed you watching me, but I didn't think you really paid that much attention," she said smiling. "Did you ever want to try anything else on?" The hose felt heavenly on my legs, and made them look so shapely. I extended my legs to get a better view of them. "Well, yes, but I couldn't ask ... you would have thought I was...." "Different? I've always known you were different, but only in the nicest way." She paused, reaching into her closet, searching for just the right thing. "I wish I had known...but that's behind us now...lets see, for your outfit, put these on for now," she said handing me a white silk blouse with a lacy front, and a blue full skirt which came down to 4" below my knees. She zipped it behind me and fixed the button. Reaching under, she straightened the slip and tucked in the blouse. I had never worn a skirt before. It was sensual. I liked the way it brushed against my stockings when I moved, reminding me that I was wearing a skirt! The lack of trousers between my legs was something I could get used to. And, best of all, the fullness of the skirt hid my evident excitement. "Try these shoes...you shouldn't have trouble walking, the heels are only two inches" she said, putting a pair of black pumps in front of me. I could only stare. Heels had always been special for me, caught my eye on each passing lady. Now I would walk in them...my shoes. I slipped them on, sitting and crossing my legs at the knee, very ladylike. I stood carefully, my steps measured, my balance on my toes. She was right...and after only a few steps I was already comfortable walking in them. They felt and looked great! I walked around the room, twirling to make my skirt flair. Mom clapped her hands and laughed, sharing my magic moment. "You're beautiful! I think you make a perfect girl. Do you like it?" " Well, I do feel kind of girlish" I replied, not wanting to admit it that I totally loved it. "Gee, I always wanted a daughter. In fact, I must admit I had hoped that you would have been born a girl. Now I can have a son and a daughter too." She stopped, her excitement carrying us along. " So, Andrea, would you like to go shopping with me at the mall this afternoon?" Mom asked. "Andrea...?" "It's the feminine version of Andrew...I think it sounds sweet. Don't you?" I smiled, too overwhelmed by all that's happened to do more than nod. "How about it, Honey? Let's show you off." And then it hit! The realization of what she has been saying. "You want me to go like THIS?" I said alarmingly. I liked being dressed as a girl, but to go out in public is something else. "What if someone I know sees me?" The thought was scary. She waved away my concerns with a long nailed hand, "Hush! You look like a pretty, young lady...why worry? Nobody will think any differently and for sure, nobody will recognize you if that's what you're thinking. I'll give you some pointers on how to act like a girl as we go along. You'll have no problem, believe me. I think you're a natural." I hesitate, unsure of this new opportunity. "Well, OK, I'll try. It's something to do," I said, trying to be cool. It would be exciting, and while it would be scary, I really did want to show off the way I looked and felt. I knew I could get used to this. Something I really wanted. "Ready?" she asked, taking my hand, "Oh, your nails need some work. A pretty girl like you can't have such ragged looking nails. Let's do them real quick. We can spend more time on them later." She came back to me with a small bottle of polish to match my lipstick. I was licking my lips nervously, still tasting the gloss that had started this all. "But will I be able to take it off later?" I asked. "I don't really think that's going to be a problem, it'll be up to you." she replied, with a wink. Fanning my hand out, she carefully painted each finger. The heady scent of the enamel filled my lungs with a sweet perfume. They felt cool as they dried, the dark red surface shining with each movement of my hands. While we drove to the shopping center, we chatted like mother and daughter. Mom gave me some brief pointers on how to sit and how to walk. "Remember, when you sit, smooth your skirt under you so it doesn't wrinkle, and cross your legs or your ankles, or, at least, be sure you keep your legs together," she advised. "A lady never sits with her legs apart. And be sure to keep your skirt down over your knees at all times." "Also, walk with short steps...a long stride will make you swagger like a boy. We don't want that, do we?" she asked smiling. "No ma'am," I said mockingly. "And when you talk, speak softly and smile a lot...try to be perky." "Oh, I'm excited...we're going to have fun," Mom said. Arriving at the mall, Mom parked the car about half way back, a long walk for me for my first time out. Now that we were here the butterflies in my stomach were back. It had gone from a family game to real all too quickly. She waited while I finally slid from the seat, my eyes searching for pointing fingers and shouts of "it's a boy", but we were alone. We walked to the main entrance, our high heels clicking on the tiled walkways, through the massive doors and into the largest store. Looking around, I found few people giving me a second look except for a couple of young men. They kept looking at me. With great courage I looked back...thankfully it was nobody I knew! At first, it frightened me...what if they noticed I was really a boy! But they weren't laughing...In fact it actually seemed like they were flirting! The more I peeked back at them, the more brazen they became at trying to get my attention. They were actually admiring me! Me, a boy dressed in girl's clothes. The thought got me so excited I was afraid it would show in the front of my dress. I was sure Mom could see my blushing We headed right into the women's clothing department. I tried to remember Mom's advice and took short steps. Mom checked over the items on sale. "Look at these prices! This is great...I think I can get us each a few things," Mom exclaimed. She picked a few dresses, skirts, and sweaters off the rack with a saleslady's help, took my hand, and said, "lets go try these on." Try on! I didn't know what to say, so I went along. In the fitting room, in the presence of the saleslady, I took off my skirt and blouse and tried on the first dress. It was a perfect fit for my slender body, with a full skirt and buttons in the front so I didn't need any help. Even the saleslady commented that it was cute on me. Somehow, I didn't feel shy about modeling in front of her. I was rapidly getting adjusted to my new femininity, floating on a cloud and not wanting to come down. Mom moved close, "This is why I gave you a full slip to wear...makes it easier to try on things, " she whispered. And then it suddenly occurred to me that this must have been planned. "You planned this all along didn't you?" I asked. "Well, sort of," she replied. "I've felt for a while that you were a little "different," and the way you went along with trying on the makeup and the girl's clothes, I didn't think you'd resist too much. Was I wrong?" I thought about her question. It was more than just about dressing up once. "No, I guess not," I responded slowly, "You were planning to buy these things. Does that mean you'd let me...want me to wear them again?" I asked. "Hon, you can wear them anytime you want, and, in fact, I hope you'll want to wear them all the time. I love the way you look in them, even the people around you have been giving you compliments. This is just the beginning, if you like it, you could try remaining as a girl all summer. It'd be great fun. I'll help you any way I can. It could be just the two of us girls from now on. That's why we're here. You need clothes for a girl your age." I didn't know what to say. My entire body tingled with the feeling of the new clothes and makeup. The idea sounded like fun on the one hand, but scary too. What was I getting into? But the question was already answered. Deep down I knew I had a strong desire to see what it's like to be a girl.or actually BE a girl. The fact that it seemed like it would please Mom was just the icing on the cake. She hadn't been too happy since Dad left. This was the first time I'd seen her so happy in a long while. "Think about it, dear." she wandered back to the rack to pick out more things for me. I finished trying on the other items with Mom's help and the saleslady. I even heard her tell Mom what a pretty daughter she had. Strange, but I felt good about that. Any worry about being detected as a boy was gone. Mom made the purchases in the dress department for all of the items. Then to my surprise and delight we went to the lingerie section. "You need some under things of your own," she said. I wanted to dig in, to pick out the frilliest and laciest things there, but I didn't want to seem over eager, so I let her do it. She picked out nylon panties and half-slips in various colors, padded bra's with front hooks, thigh-high stockings and pantyhose in different shades, and some lace trimmed socks. "This should take care of you for a while," she said. I could tell from the amount she bought that she assumed that I would go along with her plan. I smiled with her, any resistance I'd had now gone. Then as we approached the cash register she also selected a couple of frilly night-gowns. "Is that for me, too?" I asked hoping for the affirmative. She smiled, nodded, and winked at me. "Just to keep you in the mood," she said. Oh, I was in the mood. I was so in the mood I was ready to cum in my new panties. And we rushed on. Next, on to the ladies shoe department where she bought me some shoes befitting a teenage girl. Canvas shoes, a pair of dress pumps with 3" heels, and a pair of flat dress shoes. I really like the heels because of how they make my legs look and the way they make me walk in short steps, a constant reminder of my new gender. I tried some higher heels and liked them too, but Mom said no, they're too old for me. We stopped for dinner before going home. We talked about the clothes we bought and where they could be worn...just a lot of girl talk. What her plans were for me, how I'd enjoy being a girl. I sensed Mom's attitude toward me was different than ever before. She was more talkative and relaxed...we seemed to have more to talk about....more in common. And the lessons continued. After the meal, she asked if I needed to use the ladies room. "The LADIES ROOM?" , it had never occurred to me. "Of course," she said, "you cant use the men's room now, can you?" Another new experience, but then, why not? Who's going to know...I'm a lady now. "Don't forget to sit down," she whispered to me. "We don't want any shoes pointing the wrong way under the doors," Mom joked. Entering the rest room, I found an empty stall, lifted my skirt, dropped my panties, sat down, and listened to the sound of my water bubbling in the bowl. It was musical, delighting my soul. Reversing the process, I tucked myself back together, making sure my skirt wasn't caught in my panties, washed my hands and left the ladies restroom. No problem, I thought. This is getting easier all the time. Arriving home, I wanted to change into my new clothes right away. Mom said it was OK. I put on the new dress with the frilly front and buttons and full skirt, and my new 3" pumps. "Oh yes, much better. Now you look like a teenage girl," Mom said, as I twirled around modeling for her. She was beaming. She hugged and kissed me, something she hasn't done in a long time. "Andrea, you're lovely," she gushed. I felt lovely....I accepted my new look. The thought of going back to boy's jockey shorts, tee shirts, and jeans didn't appeal to me anymore. I felt so relaxed and comfortable in these clothes, and I especially like the way my mother was treating me. I'm glad Mom "teased" me into dressing up. I would never have asked her to do that, although I always wanted to. Soon, it was time for bed. I removed my makeup, and washed my face and hair. My lips were still red from the lipstick (she must have used a semi-permanent kind) but I didn't care, I'd be putting more on, tomorrow anyway. I like wearing lipstick. And, of course, my nail polish was still bright and shiny...I was glad to see that. I undressed, hung up my clothes, and slipped into my new frilly nightgown with my new panties underneath. I had to work them over my bulge, the day's excitement still not having dissipated. Mom was sitting on the sofa watching TV. I snuggled in next to her. She smiled and kissed me on the forehead and held my hand. I looked at her and said, "Mom, can I be a girl again tomorrow?" It was a moot question. "Oh Andrea, I love you so much! Of course you can...I hope you decide to spend your summer vacation as a young lady." The month of June passed quickly. I did decide to learn to be a young lady and worked hard at it. I wore skirts and dresses constantly to get used to the technique of sitting and walking as a girl until it felt natural. Besides, I liked the feeling against my legs. Mom was constantly coaching me in feminine manners, mannerisms, and voice after her work and weekends. How to talk, act, look, and behave as a lady. I really wanted to learn, although I'm not sure why. I felt driven. And she was a very willing teacher, like she was making up for lost time. My hair was getting longer all the time, long enough to style a variety of ways now, and Mom had taken me to a beauty shop for a young girl's hairdo and a manicure. Then, to my horror, they even plucked my eyebrows to make them more feminine. I hadn't been ready for that, but once they got started there was no way I could tell them that I was a boy and have to return to that when school starts. After that, piercing my ears for earrings seemed a snap. Since then, I've been doing my own hair and nails. I even have been doing Mom's hair and nails for practice, much to her liking. She even bought me some regular forms for my bras. I'm proud of my breasts and she's got me taking hormones and doing exercises to enlarge them. I'm almost up to a B-cup now, and growing. Even my nipples have enlarged and become sensitive. My daily tasks became an adventure, and I helped Mom do more of the "women's" work around the house. I had broken off ties with all of my male friends, telling them on the telephone that I wouldn't be around all summer. Even going to the grocery store and other places was always a challenge, knowing inside that everyone accepted me as a girl, but there was always the danger of detection, however slight. Mom has been especially happy with me doing the chores around the house while she's away such as cleaning and laundry, something I fought against before...without her asking...I surprise even myself...but in this role, I feel I want to do it. And after all, I must take special care of my lingerie...they're not rugged like boy's cotton things. I even find myself reading girls magazines, looking at fashions and hairstyles. Suddenly, they take on a new meaning since I now wear those clothes and do my hair. I think I've forgotten how to be a boy. But then, Mom seems to like me better this way....soft and dainty and feminine. It began at the end of summer. While grocery shopping, a good looking stock boy caught my eye. I had been watching him every time I came to shop here. But this time he came over. "Hi, I've seen you around here a lot..." and our conversation went from there. He seemed friendly and very interested in me, and for some reason I felt confident enough to talk to him. I found myself checking him over in a way I never looked at a boy before....he was tall, handsome, well built. Nice eyes, nice lips, nice tush. I've never before paid attention to those things in a boy! Might be the hormones at work. He looked me up and down too, and apparently liked what he saw. We made small talk, I learned his name was Bob, and before long, he asked me to go to the July 4th picnic with him, and I surprised myself by accepting! It didn't occur to me until I was walking home what had happened. What have I done! What was I thinking? I had become comfortable being a girl around the house, or even in some stores, but I cant possibly date a boy! I hurried home and told Mom, expecting her to call and cancel for me. Here was my second surprise of the summer. She wasn't a bit upset and, in fact, seemed pleased. "Why not? You're ready. You're a pretty, young lady. Why shouldn't you go on a date?" she said. "But mother, what if he kisses me? What if finds out I'm a boy?" I asked frantically. "Do you feel like a boy?" she asked. Standing in front of her in my mini-skirt, hose, and heels I had to admit, "No....no, I don't." "Then just relax and do what you feel is natural...you'll be fine," she assured me. "We should be more concerned about what you'll wear. It's only a couple days away." In her mind she knew that I had truly become Andrea, and with that commitment to being a girl it's time I move ahead in the female role...'The experience will do her good as long as she doesn't go too far and get into trouble.' but she wanted the excitement and pleasure to be there for me as well. The time flew by, and on the afternoon of the 4th, Bob came to the house to pick me up. I watched him arrive from my upstairs window. Cold chills ran down my spine, I was scared and excited all at once. Scared because I was a boy dating a boy and he mustn't find out, and excited because I realized that I felt like a girl and he was handsome and I wanted to go with him. What would it be like? What will he do? What should I let him do? Are these the things girls worry about on their first date? Well, mother said to just be natural, and let it all take it's own course so we'll see. I was wearing a thin cotton blouse, sort of see-thru with a lacy bra, (no pads, now) and a long full cotton skirt, a lace trimmed half-slip, white sox and tennis shoes. Oh yes, my laciest panties, just to make me feel more feminine. I had very light make-up on with a bright pink lipstick and my hair was in a pony tail held with a ribbon. And with the dangling earrings, Mom said I looked like a teeny-bopper. Bob was very polite and got along well with Mom. He also seemed pleased at what he saw...he couldn't take his eyes off of me. Finally, taking my hand, he led me to his car and watched my legs as I swung them into his car...good thing I had shaved them this morning. I liked the way he was treating me. His grip was very gentle, and yet in control. The afternoon was a lot of fun. We went on carnival rides, and we talked...girl-boy talk...I felt very relaxed in his company...I felt very much a lady. So what was I worried about? In the evening, there was a dance. I'm not a dancer so we sat for the fast ones, but he convinced me to dance the slow ones. Bob taught me the steps. It felt strangely wonderful being in his arms, another new feeling, being in the arms of a boy. He held me close and led me around the dance floor. After the second or third dance I could feel his manhood , hot and hard. (Mine was tucked safely away) I didn't mind that a bit, in fact it was exciting, and I felt quite comfortable knowing it was for me. He was warm and strong, and I wanted to be held by him. He was taller than me so I rested my head on his shoulder, and he nibbled on my ear and jiggled my earring with his tongue, playfully. I think he liked the perfume I was wearing 'cuz he kept nuzzling into my neck and breathing deeply. After the dance, we went to his car for the ride home. Arriving at my house, I thanked Bob for the lovely time. He was so gentlemanly. With a smile, he leaned over and gave me a gentle goodnight kiss on my cheek. It was warm, tender and harmless, but I wanted more. We looked into each other's eyes for a moment, and I found myself leaning in to kiss him on the lips! The touch was electric, making each of us jump as we closed our eyes. Then he took the initiative and followed with a long deep kiss. Our lips were mashed together and I could taste him and smell his cologne. A new pleasure as his lips opened and then his tongue was in my mouth touching mine. I knew I should stop, but the day had been too magical and perfect that I just submitted completely and resigned myself to enjoying it. I was kissing a boy! But then I reasoned, why not, I'm a girl! And I'm just acting natural The kiss lasted a long time. We paused, then continued again. But the kisses were effecting more that just my mind. My penis was getting hard and tugging at it's lacy bondage. Luckily, the paneled skirt kept it concealed. Did Mom anticipate this too? Bob's hand reached for and found my breast, now amply enlarged from my exercises and the hormones, inside my padded bra...and I wanted it there...maybe not as much to fondle as some girls my age but enough....he didn't seem to mind. He was gently rubbing my nipple until it got hard and it felt so, so good. Then, without even thinking, I reached down and touched his manhood...it was huge. I'd never felt another man's penis. Once there, I knew I had to continue, so I slowly rubbed it a little and Bob positioned himself so I could reach it better. I don't why, but I unzipped his fly and reached inside his shorts and touched his soft, hot skin. It sent a fever through me, filling me with a longing to make him feel as good as he was making me. I rubbed his cock up and down gently with my palm and sucked on his tongue. He began to moan and I gently wrapped my fingers around his shaft and rubbed and stroked faster like I've done to myself many times until it gushed. He was lost in the intensity of his orgasm, his moans starting high and then slowing as it came to an end. I knew exactly how he felt. His jockey shorts got all wet, my hand was all sticky, and our kiss continued, long and passionate. I had feelings for this boy, unlike anything I ever felt before. I wanted to make him feel good. I wanted to be with him...I wanted to be naked in bed with him. I wanted his cum inside of me...I wanted to be his woman. Finally realizing the time, we straightened ourselves out. He excused himself for not walking me to the door, which I could understand. Thanking me for a great day, he said he'd call me, and I stepped into my house. Mom was waiting for me. "Well, did you have a good time on your first date?" she asked. "Oh mother, it was fun, and he's such a nice guy. You were right, I worried for nothing. I feel like a woman!" A look appeared on her face. She had read between the lines, "A woman? What happened to my little girl?" Mom asked, her tone demanding a truthful answer. "Well, Bob kissed me, and I returned his kiss, and I liked it!" I said, trying for some and now all. "And?" Mom asked, looking pleased but knowing more. "We sort of got carried away..." I paused, unsure of how to say it, "I...I touched him, I rubbed his penis and it gushed in my hand," I explained shyly, the embarrassment erasing the fun of the day. I felt I could keep no secrets from my mother. After all, we were two women now, and I needed some guidance. "Did he touch yours?" she asked, a little worried. "No, he didn't even try. I'm sure he thought I am really a girl." "You were lucky this time, young lady, but you must be very careful...don't start something you cant finish, although it does sound like you "finished" this." she said with a smirk, "You don't know what could happen if he found out you're not a female. I can see you're starting to develop some real, deep seated feminine emotions. That's OK but I'm going to have to coach you on that." She paused, looking directly at me, " Are you going to see him again?" My cheeks blushed crimson, "I hope so," I responded. Mom smiled. "Well then, we've got to get you a panty girdle" Bob called the next week and asked me out for Saturday night. We went to a movie and for a hamburger after that. I was so glad to be with him. On the way home, we stopped in a secluded spot for a kiss. I responded to him instantly, after all, I was his girl. Things moved quickly. After the first few long, wet kisses and some heavy petting, Bob opened his fly and exposed his hard member. I gently placed my fingers around the hot shaft, the feel of it in my hand making me instantly excited. The expansion in my new panty girdle caused both pain and pleasure. He said, "It felt so good last time. Did you like it?" I didn't know what the right response was, but I didn't want to lose what we had started, so I nodded my head and smiled. " Would you like to kiss your friend?...please?" With a light squeeze to his shaft, I slowly and willingly leaned down and gently kissed the tip of his manhood working my way around the head. I wanted him, I wanted him so badly. I ran my tongue around it. The tip was starting to get wet. Bob was starting to breath heavily. My mind made up, gradually I opened my mouth and covered the head with my lips while licking the tip clean of his sparkling essence. The shaft went deeper and deeper into my mouth. I could feel every molecule of it as it contacted the surfaces of my mouth. The hard hot surface slipped smoothly in and out. This is it! I thought, I'm taking him all the way inside me. I really wanted to do this. I am a woman! I am FEMALE! Up and down I went, sucking and licking, faster and faster. Then, suddenly, Bob tensed up. His penis started to throb and gush again, I knew I should pull away, but I also knew I could not. I wanted his juices, wanted his precious fluid to come in my mouth. I swallowed every drop. Now I had his seed inside of me. I could smell it too. It smelled just like my cum when I masturbated. I had known the pleasure, but now I also knew what it tasted like. I was totally satisfied....I love this man and I'm his woman. I tingled all over and felt a glow. I was feeling an orgasm without coming. Bob gently lifted up my head and kissed me on the lips coated with his cum. And he held me tight...I was completely his. He put his hand under my skirt between my legs and began to rub. I instinctively spread my legs but, thanks to Mom's preparations I was wearing the tight panty girdle and a sanitary napkin so he could feel nothing. My organ was hard but well concealed. "Not yet," I whispered as I pulled away. I gently removed his hand, kissed it, and straightened myself up and freshened my lipstick. We headed home. This time I didn't tell Mom what happened. But I felt warm and feminine. Maybe she saw the glow. We're together again. The last Saturday of the summer, and Bob and I slipped away to his parents cabin for the day. We were supposed to go fishing, but he had other ideas I soon discovered. We were alone, kissing, Bob's hands were all over me. We were both panting like marathon runners. I was kneading his prick through his pants, sure that I would soon feel his bare flesh on my body. Bob broke a long kiss and whispered to me, "I want this to be right, to be special tonight. Are you willing?" "What do you mean?" I asked, my skin suddenly itching at what I knew he meant. "We're alone here, let's go to bed. I want to make you feel good too," he replied. "You do make me feel good...you're a great kisser..." But his shaking head cut through my words. "No, I want to do more than just feel your breasts and kiss you, I want to have you feel me inside you, to make you come the way you do me!" My mind blanches at the thought, but I realize that now is the time...I must take the chance. "OK, my love. But the bedroom must be dark...and I've never done this before, so let me take it slow, OK?" I asked. "All right, Sweetheart...anything for my shy little girl." Bob darkened the room and I watched as he got undressed and into bed. Now, under his gaze, I stripped down to my panties, the shadows rippling over my bare body, making my small breasts seem to have a deeper cleft, the nipples standing out against my pale skin. I crawled under the cover and lay next to him. Our arms pulled us together and we kissed a long wet, passionate kiss, our lips rolling and pressing for more. He trailed a line of kisses down my neck and then to my breasts. the hot, wetness of his mouth made me moan as he sucked and licked my nipples, the ends getting hard and long. And although my developing breasts were small, there were no complaints, Bob suspecting nothing. I was carried away by the heat of the moment, starting to kiss and nibble his neck and shoulders and worked my way down to his cock, the long shaft of it pressing against the hot skin of my cheek. My mouth opened and with soft lips I started to once again kiss the shaft that I loved, working my way higher, up to it's head. Bob was delirious, moaning with ecstasy. In his passion he reached down between my legs, looking for the hot quick of my pussy, expecting to touch lace and hair. But the hidden treasure of my hot, hard penis was his only find. His fingers continued to dig through my thin panties as I held my breath. What would he do? What would he say? I felt I had betrayed him completely. "What's this? My shy little girl is hiding something extra !" he exclaimed, his voice hoarse with passion. I remained motionless, my hand still encircling his massive cock. He moved slowly, prolonging the agony I was sure would follow. Rising on his haunches, he peeled the delicate panties from his new find. His face was blank until he suddenly leaned over me, gently taking my captive cock from it's lace enclosure and covered it with his lips, lips so soft it felt like molten lava. He worked his tongue around and over it, flicking it just under the cap. I was moaning, ready to pass out with the delicious sensations he was creating! He was accepting me, loving me! We continued to suck and lick in a 69 position until we both came. It was heaven! The rest of the afternoon, we laid in each other's arms and talked, occasionally pausing our discussion to again taste one another. Bob said he was really surprised to find out I was a male but he considered me a girl and would always treat me that way. He was glad he could do for me what I did for him. In fact, he enjoyed. It was then that I decided that I wanted to remain a girl forever. His girl. We agreed to go steady. Sunday morning, at breakfast, Mom and I had a long talk. I didn't tell her all the details of my day at the cabin with Bob. Just that we were going steady, at least for the rest of the summer. But I did tell her I reached a decision about my life. "Mother," I want to remain as a girl. I don't ever want to go back to being a boy." "I sort of expected this, Andrea," she replied. "You've gotten too committed to being a girl. It would be a problem to change back. Your features and mannerisms are so feminine, why you've even developed breasts! You really worked at the transformation. So, I've been doing some planning on my own. I've accepted a job transfer to another branch which means we'll have to move to another city, actually not to far away. You can enroll into your new school as a girl and finish the next two years of your education. I've talked to the school authorities there and a doctor about your sex change and they've agreed to go along with it. When you finish high school, you'll be 18 and you can start the final transition to becoming female. The doctor will enhance your hormones to give you more female characteristics. Is that OK?" she asked. "As for Bob, you can keep in touch by mail, and visit occasionally. I'm sure you will meet other boys, too" "Oh Mother, yes! I love you!" "And I love you too, my dearest Andrea," Mom replied. "You know, I think I always wanted to be a girl," I admitted. "And I think I always knew that. I saw how you used to watch me dress, fondle my clothes and admire them." she said winking. "Your attention was more than usual. And you took to dressing in girl's clothes very naturally. I had never seen you so happy as you were the first time you dressed as a girl. Now I have the daughter I always wanted. I'll finally get to be the 'Mother of the Bride'." Chapter 2 by Caitlin Rose. ********************* This is a copyrighted work of Caitlin Rose. All persons and situations are fictional. Any resemblance to anything real is a coincidence. Contains no sex, but plenty of crossdressing. If you're offended by that, read something else. I accepted Alyssa's invitation to add a chapter. ********************** So much had happened so quickly. Here I was, in a new town, about to begin in a new school, and in a way, in a new life. When we moved I felt like I had left Andy behind in our old house. Andrea had moved to our new home. My new room was just right for a 16 year old girl. Mother ( I rarely said, or even thought, "Mom" anymore) had decorated it in a kind of warm, romantic style that made me feel so feminine. The colors were delicate pinks and ivories. The bedspread and curtains had ruffles. There was a spacious glass-topped vanity table with a lighted 3-panel mirror. The room was bigger than my old one had been. There was room to twirl in front of the large mirror and watch as my skirt flared around me. There was plenty of closet space. In that room, I didn't just feel like a girl, I felt like a glamorous movie star. We had given almost all of my old "Andy" clothes to a thrift store. I was glad to be rid of them. Mother had insisted that I keep some loose tee shirts, 2 sweatshirts, a pull over sweater, and a warm Woolrich shirt. She said that most young women sometimes like to wear loose fitting men's things, for lounging around the house, washing the car, things like that. Only two days after we moved in, I had to show up for an "Interview and Orientation" at Blanchard High School, where I would be attending for the next two years. I wanted to be dressed properly for the appointment. I would be meeting with a Mrs. Hall, a guidance counselor. I really didn't know what to wear, so I asked for help. Mother suggested that I wear a simple pale green dress that I had worn on one of my first dates with Bob. It had half sleeves and a white lace trimmed round collar. It had three little buttons in the back, leaving the lines of the dress to drape smoothly across my chest. The shape of my developing breasts was clearly apparent. On the date I had worn it with sandals and painted toenails, but Mother thought I needed white pantyhose and white 2" pumps for this occasion. We got both at the shoe store. Mother lent me a small white purse too. I got a lesson on "understated make-up" on the morning of the interview. "Dear, your face must match the mood of the occasion. In this case, that means well groomed, but demure. A light touch, and soft shades work best in a situation like this." I did my hair in one of the styles I had been wearing on and off through the summer. It had soft waves around my cheeks. I had learned how to do it with hot rollers, so it took only about 15 minutes from start to finish. Mother drove me to the school, but waited outside in the parking lot. I was on my own. My stomach was doing back flips. I was never comfortable in the presence of school administrators as a boy. It wasn't any better as a girl. Mrs. Hall greeted me warmly. She was wearing a dark blue dress, with a sparkling white collar. The sleeves were trimmed with white too. Her rich brown hair was probably much longer than mine, but it was pulled back into an elaborate braided bun. Her makeup was soft, but definitely present. She had used brown and plum shades to compliment her well-tanned complexion. The interview lasted almost an hour. Mrs. Hall was really a dear. She must have known all about my new gender. After all, she was alternately looking at me, in pretty dress, heels and "demure" makeup, and looking at my record card from my old school! Still, she did her best to put me at ease. We talked about my interests, my program and all the extra curricular activities available at Blanchard. "Andrea, are you interested in the arts at all? Blanchard is considered very strong in music and drama." "I've always wanted to be involved in drama, but I'm shy about appearing on stage." "You might want to participate as a member of the stage crew, or perhaps work on costumes, as a start." Mrs. Hall went through details about schedules, school busses, lockers, and homerooms. It was pretty much like my old school but there were little differences I'd have to get used to. Finally, the interview drew to a close. "Andrea, do you have any questions?" "Mrs. Hall this may sound silly, but may I ask you about clothes?" Her face broke into a wide smile, and her eyes twinkled. "Of course dear. I should have known what would be on a young ladies mind." "I guess the girls here usually dress like they.er we. did at my old school, but at Blanchard, do girls dress up for the first day of school?" "Some do, for a day or two. But by the end of the first week, if you see a skirt or a dress, it is probably on a teacher. Even so, there are some girls who prefer to avoid slacks. Look around and choose a style that you are comfortable with." She looked at me from head to toe. "You'll do fine. You seem to have nice taste." "Thank you, Mrs. Hall." She rose from behind the desk and extended her hand. I took it in a gentle grasp. "Good luck at Blanchard High" "Thank you. Have a nice day." I got my wardrobe ready for the start of school, realizing that most of my classmates wouldn't be wearing skirts or dresses most of the time. They'd be wearing some form of pants. Choice of tops would range from tight turtlenecks to light weight shells. I really wanted to stay with dresses or skirts. I loved the feel of a skirt as it brushed my smooth legs. I almost wished my new school had an old fashioned dress code, or even those cute plaid skirt uniforms for girls, but no such luck. I would have to learn to look and feel feminine, in what was essentially, a borrowed masculine clothing style. The irony wasn't lost on me. I wasn't going through all this to become a tomboy! Mother helped me shop for school clothes. We drove to a local mall. Under my pale yellow sleeveless dress, I wore a white bra and my panty girdle. I knew I'd be trying on jeans and the like, so I didn't wear a slip. At the store, I selected the tightest jeans I could get into. Mother wasn't particularly happy with them, but I refused to have anything to do with clothes that were remotely unisex. "Andrea, I know you want to look feminine and attractive, but remember, you want to look like a young lady too. Please don't cheapen yourself" I was becoming very frustrated. "Mother, this is too confusing. Dresses are too snobby. Tight jeans look cheap. I really don't know what to buy." I just stood there near the dressing room, holding the jeans that my mother didn't want me to have. I knew they weren't really appropriate, but at least they were unmistakably feminine. Suddenly, tears were flowing down my cheeks. "Oh Mother, please help me with this" She looked puzzled for a second, then something flashed across her face. "Andrea, don't worry. It's natural to be emotional. We all go through it. Come here darling." She held me in a tight hug until the tears stopped. She offered me a tissue from her purse. It was like I was a little girl, and Mommy was taking care of me. We put the tight jeans back and left the store arm in arm. We bought a fall back-to-school fashion magazine leafed through it, over coffee in the food court. When we returned to the store, I felt much better. We left with two pairs of pretty Capri length print pants, a pair of aqua denim jeans, with flower appliqu s on the rear pockets, and two pairs of black slacks. One pair was silky and flowing, the other pair was tighter, but not too tight. I also had three new long sleeve blouses, so I was ready for cool weather. I did dress up for the first day of school. I wore a dark red, actually burgundy, dress with puffy sleeves. Mother had picked it out for me, to wear to her going away party at work, just after her transfer came through. I wore it with panties, a full slip, tan stockings and black pumps. I did my make up a little bolder than I had for my interview. Even though I was still writing to Bob every week, I missed attention from a boy and wanted to be noticed, at least a bit. I spent more time on my hair than usual. After all, hair is a girl's "crowning glory." I tried about four styles until I was satisfied. I made my bangs as smooth as possible, and brushed the rest of my hair back. I gave the top some volume with a curling iron. I was even able to put a little gold barrette on one side. I would have preferred to be able to wear an updo with this dress, but I didn't have the length for one yet. I was pretty nervous that first day. I noticed one boy in home-room looking at me. He was well-built and very self confident, in a quiet sort of way. Not a braggart type at all. He was also in my English class. He sounded intelligent when he spoke. On the second day, I was less dressed up, but still avoiding pants. I wore a blue skirt and pink, ruffled blouse. The boy introduced himself at lunch. His name was Will. I saw him sign up for the track team at the lunchroom bulletin board. I was really becoming attracted to this guy. I felt guilty about it. I wanted to be close to him, but I didn't want to hurt Bob. On Wednesday, the lunchroom bulletin board held a new sign-up sheet. "Cheerleaders Wanted, Squads Forming For All Sports Cheer For Your Favorite Athletes" Chapter 3 by Donna Allyson. ********************* This is a chapter is the copyrighted work of Donna Allyson. All persons and situations are fictional. Any resemblance to actual persons or places coincidental. Contains no sex but does reference some sexual activity and attached appliances. If you're offended by that, read something else. I accepted Alyssa's invitation to add a chapter and following Caitlin Rose's lead in chapter 2 offer the following continuation. ********************* I really had not given much thought to participating in any sporting events when I had started the semester but when I read the lunchroom bulletin about cheerleader squads being formed my interest was piqued. What better way to be noticed by the boys than to join the cheerleaders. The Bulletin had stated that there were six openings on the team and that the first tryout would be on Saturday morning at the gymnasium. I was in a quandary all afternoon. I knew that I love the chance to participate in the ultimate of female high school activities and all day I pictured myself in the purple and white cheerleader uniform chanting cheers and performing routines for the guys on the field. On the other hand I did not know how I would pull it off. Yes it was true that the administrators knew of my real gender and of my intentions for later change but would they allow me to actually mix this closely with the other girls. I just was not sure if I was reaching to high at this point. That evening I sat at home in the downstairs family room. The TV was on some mundane program. I did not even notice when Mother came in to the room so engrossed was I in my own thoughts about the tryouts on Saturday. She must have known that I had something on my mind as I was always aware of her presence when she came into a room and never failed to at least say something to her. "Andrea. Andrea are you ok dear" She asked bringing me out of my trance. "Huh? Oh, I Mother. I didn't hear you come in." "Yes Dear that is quite obvious. You were off in another world. Especially when I saw that the TV was on CNN. You never watch that. Is something wrong?" As always I could not hide anything from her. She had been so helpful and supportive to me in my transition that I just felt that I had to tell her how I felt all the time. "Well yes and no. Yes I have a problem and no, it is nothing serious. Well.... It's, it's just that I would like to join the cheerleader squad but I don't know if they will let me." " And why do you think they won't let you dear?" She asked gently but with a sense of concern in her voice for my feelings. "Mother. I may look like a girl and act like one but underneath I am still a boy. How will I ever be able to hide...you know...especially in the showers after practice?" "Aahhh is that all? She said with emphasis. That little problem can be easily remedied. I know just the thing. I saw something advertised on one of the Internet sites for transsexuals like yourself.. I can have it here by Friday. Probably something I should have gotten for you months ago." "What is that?" I asked. My interest piqued. "You wait and see. Then afterwards you answer for me if you think you can join the squad then. I think you will be greatly surprised as to what it can do for you. Andrea, do you trust me on this?" Knowing what mother had done for me so far and how she had been right each time I had reached a crisis point I could only nod my head in agreement. "Good. Now stop worrying. I won't let you be disappointed when you feel so strongly about this." I got up and went over to her and threw my arms around her neck and hugged her tightly. "Thank you Mother. Whatever it is you have in mind, I trust you." The following afternoon I signed up for tryouts. I could not wait to see what Mother had in mind and on Friday after school I got the biggest surprise of my life. At least as a girl I did. Sitting on my bed was a small box. I opened it and removed two panties. But these were not just any panties these were special. They were flesh toned latex and were perfect reproductions of a girl's genitalia. As I sat on the edge of the bed reading the instructions and being totally amazed, Mother came into my bedroom. "What do you think?" She asked me, smiling. "I read the instructions Mother but I still can't figure out how it works." I replied. "Well lets give it a try. It will be uncomfortable for awhile until you get used to it but it should solve your problem and maybe even help you feel even more like the girl you want to be." It took some time to get it right but when I finally got the panty on I was amazed. It was tight all-right. The contraption had what was left of my testicles pushed up inside of me and my small penis was tucked flat between my legs. In their place was a small triangle of soft pubic hair that just barely hid the soft folds on my "new" labia and vagina. Mother had carefully applied the clear adhesive to the side tabs and when she was there was no trace of anything except a female. "This will be good for a week and then you must change them. I bought to so that one can be cleaned while you wear the other. You can even shower with them on and no one will be able to tell you from any other girl. So what do you think young lady? Will this solve your problem? You can even have sex with those. But don't try it girl. Mother said with mock sternness. I said nothing but the hugs and tears that I gave her said it all." I was now a girl. At least as far as anyone could tell. On Saturday I tried out for the squad and was selected. On Monday those that had made the squad were issued their uniforms. They were as far as I was concerned beautiful. The white sweater with the large purple B and the purple and white pleated mini skirt with it's attached purple panties was for me the confirmation that I was really now a school girl in every sense of the word. I asked Mother to take a picture of me and the other girls at our first game and sent it to Bob. A week later I got a reply that he was coming to visit and stay for the Thanksgiving day game. It was later that I found out that Mother had invited him. The End ?? Lets hope not. Any other authors want to make a contribution??