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PLAYING IN THE BAND By R. Gold CHAPTER ONE: The Girls Across The Street As far back as eighth grade, I'd sit in class and daydream about what the girls in my class would look like undressed, or partially nude. Peeks and glances would fill me with passionate feelings that gave me constant erections throughout the school day. I couldn't wait to arrive home to an empty house to satisfy my lusting mind and body. At home, my roving mind soon sought out different ways to satisfy my masturbation fantasies. I began to use my mother's silky undergarments wrapped around my penis to send sensations through my entire body. Discovering orgasms was the highlight of my being. Before long, I found myself wearing full slips and laying on mom's side of the bed, burying my face in her pillow, breathing in her perfume, my hands running all over my thighs and ass, humping the sheets to achieve satisfaction. As the fall season passed, I moved to parading in front of her full-length mirror wearing wig, bra, panties, stocking, and slips to satisfy my consuming lust. Because both my parents worked, I had all afternoon to play. I didn't like the smells of make-up and the shoes never fit, but everything else fit my skinny, thirteen year old body. Two sisters lived across the street. Betsy was my age, short, smart, and my schoolmate. Her little sister, Jane, was as tall and skinny as me, and one year younger. I lusted for Jane, but tried to keep it a secret. Many afternoons, we'd sit around in their big bedroom and spend the time talking. Our conversations always led to sex, and who like whom at school. With just the two beds, I'd end up lying or sitting next to one of the girls. Sometimes, it was Jane, the center of my fantasy. Each day as we talked, both girls would tease me about going straight home and disappearing into my house for at least an hour before I came over. "I bet I know what you're doing," Betsy would say, knowingly. "Nah, you haven't a clue," I'd always respond. "What's he doing? Tell me, tell me!" Jane would yell, grabbing my arm playfully, trying to pull the truth out. The wrestling would always give me an erection that was impossible to hide. Betsy would never say what she was thinking, and I would never tell. But each day when we rode the bus together, I'd tell the girls I'd be over later to see them later and slip straight into my mom's room to relieve the sexual tension of the day. One day when I was fully outfitted, deep in the pleasure of yanking myself to orgasm, I looked away from the mirror to see both girls standing in the doorway. Betsy, grinning from ear to ear, yelled to Jane, "I told you so!" Jane was staring with wide eyes straight at my erect, pulsing penis. I stood frozen, one hand still holding myself. My heart felt like it was going to burst right out of my chest. They both charged into the room grinning and Betsy gave me a big hug. One of her hands slipped to my organ. "I knew it. I knew it. Now, let me help you finish the job." Without another word and to my astonishment, Betsy did a fair job of making me cum quickly. As I reached climax, I felt another set of hands caress my pantied bottom and lower back. Jane moved in from behind tucking up closely. I was sandwiched complete by my neighbors. As I felt loving kisses on the back of my neck, arms and shoulders, I moved backwards into my playmate Jane. Sensing my returning arousal, Betsy began to rub the cum from my penis all over my balls and stomach. Using both her hands, she began to help me grow firmly erect again. She smiled up at me. I returned her smile and gave her a kiss. "Mmm, you taste good," Betsy said to me. "You make me feel good", I stuttered, not quite digesting what had just happened. Jane continued to caress my back, her hands now exploring under my bra, rubbing my erect nipples. "Mmm, Let's go back to our house to play. We have nicer clothes than this and they'd fit better, too." I forget how many times I came that day, but I fell asleep that night with a big smile on my face wearing Jane's ruffled teddy. It wasn't long before our dressing and sex became a daily occurrence. While we didn't engage in intercourse, we did explore each other's genitals freeing and lovingly. Our explorations continued to gain ground as we licked and touched each other, talking the whole time about what felt good. I loved to lick Betsy's furry pussy, parting her lips and licking until she became swollen with passion. As my face became covered with her juices, she would grab my head and push me harder between her legs, holding me close. Her grip with her hands and her thighs was powerful. Gasping to catch her breath, she'd pull me out of her crotch and shudder. Then, she'd release her grip allowing me to dive back in again where I'd begin licking her genitals, flicking my tongue over her swollen clitoris. My mouth would encircle her, my tongue probing and tickling. Over and over again, we repeat this game until Betsy would scream with joy, partially blacking out from multiple orgasms. Jane loved to be kissed and have her neck sucked. We'd suck face for hours until we were both dizzy. Our hands would rub over each other, squeezing and probing. I'd feel her nipples stiffen under her tee shirt as I'd suck her neck. Our lovemaking was more rubbing and wrestling. My hands would rub her entire body, harder and harder until I'd feel her climax under me, grinding against my leg or my stiff member. The girls obviously had played with each other without me, but I became the connector between their passions. Often, we'd be intertwined, humping, rubbing, licking, stroking, without really considering who was doing what to whom. It always felt good. Sometimes two of us would playfully work one person over. When the girls did this to me, I'd erupt into the air, spraying cum all over. This became an excuse to rub the slippery substance all over each other to cool the heat of our bodies. As our explorations became bolder, the girls discovered my anus. We began with probing fingers and tongues. This had such a big effect on me that we began to experiment with warm water enemas in the bathroom. We'd fill up bag after bag and sit around giggling at who could last the longest, laughing as the splashing, stinking water would fill the toilet and the smell would fill the air. Later, after we were all cleaned out, we'd grease each other up and stick fingers and tongues up our cleaned out bottoms. With all this sexual play, both girls encouraged my dressing. They'd pull out clothes talking to each other as if I was a doll or play toy. They'd fuss over me, discussing what looked better, what showed off my figure or my skin tones. I enjoyed their silky clothing, hugging my still slender child sized body. I loved the fuss they made when they thought I looked cute. The more they praised, the more comfortable I felt dressed as a girl. My erections grew larger and more frequent. Jane's clothes were much nicer than moms. They were cuter and fit better. As we continued our afternoon activities, both girls encouraged me to let my hair grow longer. Betsy helped keep it neat by trimming my lengthening locks into a pixie cut that gave me a more androgynous appeal. My parents didn't seem to notice anything new about my changing haircut because it still looked neatly trimmed. Before I'd leave the girls' house, I'd have a ritual of wetting it down and brushing it back. It looked like I was freshly showered and returning home from intramurals. My parents never suspected my after school exercise was not at school. By Christmas, I could back-brush my hair, fluffing it up and out. I'd use spray and gel and spike it out. A little lipstick and padded bra and I could pass. The biggest problem was my bulging erection. After coming several times, it could be restrained by a panty briefer that I stole from my mom's bedroom. I especially liked to wear dark tights, white socks and sneaks, and a long turtle necked sweater dress or a smock and tee shirt. Each afternoon, the three of us would lay together, sucking and probing until we were sore and satiated. The girls loved to nibble my adolescent penis and swallow my ejaculations. I equally enjoyed swallowing their juices as I buried my face between their legs, cupping both checks as hard as I could, while I occasionally stuck a finger in an asshole. Swathed in satin and tricot, I thought I was in heaven. CHAPTER TWO: The Dermatologist I turned fourteen and started to have a terrible time with acne. My mom took me to see a dermatologist. We'd have standing appointments each week to try to make my face stop breaking out, but nothing seemed to work. By the springtime, I was taking massive amounts of an antibiotic to try to stop the eruptions. This process monthly required blood tests to keep track of any possible liver damage. At one visit, the doctor mentioned that my testosterone levels were very high and probably causing the skin problems. He suggested that I temporarily take a blocker to let the medicines have a chance to heal my face. He explained that it would slow my maturation progress. I feinted concern, but was secretly pleased. I wanted to continue to pretend I was a beautiful, young girl just like Jane. The doctor's prescriptions were very efficient. The drug halted and slightly reversed my changing body. My skin started clearing up immediately. My pores shrunk and my skin gradually returned to being baby smooth. The girls commented that what little hair I had around my genitals seemed to thin and we all noticed that it took longer for me to cum. Neither sister seemed to mind as long as I brought them to orgasm. I still was able to retain an erection, but it didn't seem to be as hard or as large. As the year went by, most of the guys in my class began to grow bigger with muscles and heavier in weight. While I gradually grew taller, I remained skinny and developed no adult male characteristics. My whole body remained underdeveloped. I had little or no public hair. I had no hair on my face. and my voice still sounded childlike. By the end of the summer, the doctor was satisfied with the progress my skin had made. I was taken off the antibiotic, but kept on the testosterone blocker for a few more months to allow my skin to heal from the past eruptions. By my fifteenth birthday, my face looked completely clear and very youthful. It was obvious when we went swimming or had gym that I looked a year or two younger than my classmates. There were very few of us left who hadn't started becoming young men. I had kept growing my hair out. During the school day, I tied it back with a rubber band. Because I was a musician, everyone thought I wore it long to emulate the rock stars that everyone idolized. No one realised that my pleasure came after school, when I'd go across the street and become one of girls at Betsy's house. Both Jane and Betsy never tired of making me up and setting my hair. We'd all enjoy my transformations together. Our daily sessions always ended with orgasms in their pillowed beds. When Betsy got her license, we'd start to take buying trips to the Mall. I'd always dress up before we left and no one every realised that I wasn't a teenage girl as we'd walk around giggling, flirting, and shopping for sales. Whether I wore a skirt and blouse, jeans, or a dress, I felt very comfortable in my femininity. Because my voice hadn't started to change, I didn't have to put on and I could freely gab without fear of being found out. My only limitation was my skinny, underdeveloped body had no figure or curves, so my outfits de-emphasize any womanly shape. I had no bottom or hips to swing when I walked. I made no effort to wear heels, but I did purchase several pairs of shoes and sneaks that fit my size seven foot. With little body hair or muscle development, I could wear smocks, dresses, tight little tops, cut-offs or shorts. I just looked skinny! My favorite look was tights. These seemed to give my legs more shape and definition. With my genitals tucked securely in a panty girdle, I wore tight stirrup pants, leotards, or jeans without any problem. On the way home, I'd wet down my hair and brush out my curls, securing my long hair with a plain rubber band. Then I'd hop in the back seat and change into a t-shirt and jeans. Sometimes I'd leave one earring in, but never two. By the time we arrived home, I had my gym bag of girl clothes neatly folded to carry into my house. CHAPTER THREE: The Band At sixteen, the three of us started to find more activities to occupy our time. Betsy was involved with student council and service activities. Jane was a nimble athlete who played field hockey, volleyball, and ran track. I played keyboards and guitar in the school jazz band and was invited to join a rock band. The band played local swim club pool parties and the occasional school dances. Music was my first love. Over the years, I had taken lesson on the piano, guitar, and violin. Hearing a song on the radio, I could provide the key, chords, and arrange the music. My versatility and passion for music made my hours of practice fun. I was the youngest member in the band. At sixteen, I more or less took a back seat to the other four guys who had played together longer. One of my school friends, Chuck, had played lead guitar with them for two years. He was seventeen and my musical guru. I knew him from school jazz band. He had encouraged me to join when they had the opening. Terry played guitar and bass. He attended the local university and lived about fifteen minutes away. He drove the mini-van that we trucked all the equipment around in. Gary was the drummer. He had gone to the other high school in our ton and now went to college with Terry. The fifth player was our brass section. His name was Doug. He could play trumpet, sax, clarinet, and double on bass. He had grown up down the street from Gary and they were best friends. Since my parents were never home, we kept our amplifiers and p.a. system in our basement. We'd practice each night during the week and play jobs on Fridays and Saturdays. It wasn't unusual for Betsy and Jane to hang around the band during rehearsals and gigs. They enjoyed the music and the drugs, too. At sixteen, I was the youngest member and learned an lot my first year. The band had a lot of influence at fraternity parties at our local university and we played regularly. These parties were a real eye opener for me. The beer and drugs flowed. Sex was common, especially when there were toga or pajama parties. It was great to watch everyone get drunk and rub against each other in the darkened rooms. Sometimes, they got so drunk, we could play the whole first set over again by midnight and no one seemed to care. The band had a real following. Between fraternities and the local teen dance club, they had a reputation that guaranteed business and ticket sales. This meant steady bookings and good pocket money for me. Between paying off my parents for a larger amplifier, a second keyboard, and my share of the p.a., I was still making enough to continue buying clothing on my en-fem shopping expeditions with Betsy and Jane. Some of the people who followed the band liked to turn us on to drugs. I sampled many things. I met a lot of older guys who would hang with the band because they could pick up the girls who showed when we played. Terry had a close friend, Michael, who liked the band and hung with us. He was a pharmacist. He gladly provided us with any prescription drugs we wanted. We had access to benzedrine, qualudes, percodan, and anything else we desired. One day, I asked Michael if he could fill a prescription for the testosterone blocker I had been taking. "Sure, but why would you take that?" He was curious. I explained my relationship with the dermatologist. I told him I liked what the drug did and he smiled. "That's a real Peter Pan drug. Generally, female gymnasts use it to keep their size and weight down. It's no problem to get you as much as you want. It's not even a classified drug like that others I supply to Terry. This made me feel confident and secure about my body now. I had recently stopped seeing the dermatologist who assumed that my body would regain the ground I lost over the eighteen-month period that I had taken the blockers, but I had other plans. Michael said he could get me samples and laughed when I told him I wanted a lifetime supply. "Let me bring you six months worth to start. You don't want to be overstocked with something that has an expiration date on it. He asked me if I could meet him at his apartment on Tuesday, his day off, to pick them up. CHAPTER FOUR: My First Visit To Michaels That Tuesday, I borrowed Betsy's car and followed the instructions Michael had written out to his place. I found the apartment easily and was impressed with how nice it was. He greeted me at the door and invited me in. There on the kitchen table was a cardboard box with several large bottles of my blockers. I thanked him and went to reach for them. Michael smiled and placed his hand gently on top of mine. He grinned and said, "I want to ask you a favor, too." I felt a little uncomfortable with his hand covering mine, but I really wanted the pills. "Sure, whatever you want. You're doing me a big favor." "I want to see the effects the blockers have had on you already. Take your clothes off and show me." Staring at Michael's eye, I didn't feel any fear as I pulled of my tee shirt. "I'm interested in seeing how your development has been delayed. Being a pharmacist is similar to a doctor. We take a lot of anatomy courses and I have a personal interest, too." Michael smiled. I shivered as I finished undressing down to my briefs and socks. Michael motioned me to pivot around and began to gently touch different spots on my shoulders, neck, and arms. His fingers were thick and large but very gentle. "I'm looking at muscle tone and development. You really seemed to have stopped your growth at about a twelve year old point." His strong fingers ran across my shoulders, lifting up my arms and probing my armpits and my neck. "There's no real sign of development at all except for your height and size. How much do you weigh?" "I really don't know." His touch was very soothing and reassuring. It felt just like a doctor's exam and I found it easy to relax. "Well, how about your genitals? Are they stunted as well? Let's take a look." He motioned me to drop my shorts. As I did, I felt a blush coming over my body. At this point I started to grow embarrassed. As I went to one leg to pull off my shorts, Michael moved closer and reached for my penis and firmly grasped it and my testicle sack. "Your penis and testicles seem to be normal in size, but you have very little public hair. He began to manipulate my balls, checking their size. He then stretched my penis out and asked, "Can you achieve an erection and ejaculate?" I began to explain my relationship with my two friends, Betsy and Jane. I told him about my daily sexual encounters and how recently it took longer to get an erection and sustain one. While I was talking, my penis had begun to grow erect from Michael's exam and recalling my sexual exploits. I heard a drawer open and watched Michael getting out a rubber glove and a tube of what looked like ointment. "I want to feel your prostate and see have far it has enlarged." I had had this done before during exams so I knew what was to come. Michael asked me to bend over and put my hands on the kitchen table. I did and he gently inserted his finger in my rectum. "Does that hurt?" he asked. I told him it didn't and began to describe my exploits with the enema bag. Michael chuckled at the story and continued to probe my prostate. I was rather erect and a few drops of liquid dripped out of my penis and fell to his kitchen floor with a splat. I quickly apologized for making a mess and felt sheepish. "Do you like the way this feels?" Michael asked in his doctor-like tone. "Does this stimulate you sexually?" Between deep breaths and gasps, I readily agreed that it felt very good. I gripped the table harder, spread my feet for a better grip and pushed backwards into his now undulating finger. His thick, strong finger was entering me deeper than I had ever been probed and it sent waves of pleasure through my body. It was hard to catch my breath and my mouth hung open like a fish as I gasped and rocked against his hand. Within a minute, I started to moan with pleasure as Michael gently manipulated my balls. His face was close to my neck and I could feel his warm breath quicken as I moved to a rocking frenzy. I turned to face him and he kissed my lips and moved his tongue into my gasping, open mouth. Our tongues entwined as I sucked deeply. As we kissed, he used his left hand to reach and grab my now hardening cock. He gripped it hard and encircled it. My movement through his hand created a stroking effect that I controlled. His probing finger in my ass quickens and I began to feel wave after wave of delight pass through my body. My erect penis shot a load of cum across his kitchen floor. We continued to kiss passionately as Michael slid his finger out of me. I wanted his finger to remain in my ass, but it didn't seem like a proper thing to request. I turned around and faced him, putting my arms up and around his neck. I drew him closer, pulled his face down, and kissed. His hands caressed my ass, which dripped with the ointment he had used to penetrate "I have never been so turned on before in my life," I said smiling and continuing to kiss his wonderful face. Michael lifted me up, carrying me to a large chair in the nearby living room. I sat in his lap as we continued to cuddle and kiss. I could feel his erection pushing against my naked hip and encouraged him to take off his clothes. As he pulled down his pants, I gasped. His engorged member was thick and very hard. It glistened with fluids coming out of the tip. I began to massage his prick, spreading it with fluids. Stroking the head, and brushing the underside made it grow enormous. I knew it felt good for him as he closed his eyes and groaned. I licked my sticky hand and liked the taste. I slipped off his lap and onto the floor, where I could kneel between his legs. I lowered my head to his pulsating rod and began to lick and suck. It was hot and delicious. I felt him respond to my every touch. My hot, wet butt wiggled with delight against his living room carpet, as I began to grow hard. I grew weak with delight as I tried to take his whole shaft into my mouth. He pinched my nipples, grabbed my neck, and stroked the back of my head. "Please untie your hair," Michael whispered. Staring into his eyes, I released the rubber band and shook my head to fluff out my shoulder length hair. Michael ran his fingers through it and began to stroke my hair as I continued to slurp his beautiful cock. I licked, swallowed, and sucked him fiercely. As I massaged his tightening balls, I could feel his body begin to thrust forward. I was so turned on that I wanted something back inside my tail. His wet, hot cock seemed perfect. Smiling and looking straight into his eyes, I crawled back into his lap and raised up to my knees straddling his stiff member. With Michael's help I lowered my hole down on his shaft, using my well-oiled opening to grasp his cock and consume it. Slowly I began to pump up and down, using the muscles in my ass to continue to masturbate him. The friction sent waves of delight through my entire body. I had to grip the arms of the chair for fear I would blackout as the blood pulsed to my brain. I increased my pace, knowing that my tightening muscles were bringing him to a climax. Michael licked my face and sucked my neck. Grabbing me under my arms, he supported my weight as I plunged up and down on this shaft. Finally, he began to grunt and snort and I could feel him ready to cum. I squeezed my muscles as tight as possible and felt his body begin to spasm. His cock rubbed against my prostate and my penis spurted along with his. He grabbed me tightly and pulled close to him as he made the final stroke inside my ass. I moaned and felt myself blacking out. Returning to my senses, Michael was holding me and kissing me gently all over my face. I snuggled close to his heated chest, enjoying the feeling of being totally consumed by an orgasm. I tucked inside his arms, curled up, and let him gently caress me. I think we both fell asleep. A little while later, I awoke to find him still holding and caressing me. He was rocking me gently, gazing at me. "You are lovely," he whispered as he kissed me gently. "You are so soft and tender and young and steaming hot!" I laughed aloud with glee and kissed him back. "I'm cold and I'm hungry." I stood up and started to reach for my clothes. I was dizzy and a little nauseous. I felt sweaty and sticky all over. My butt felt rubbed raw and my insides were on fire. Michael helped steady me and insisted I use his bathroom to freshen up. He generously made sure I had clean towels and his big bathrobe as he started the shower. I encouraged him to join me I encouraged him to join me and it felt wonderful as he scrubbed me clean. After I washed my hair, I returned the favor. I felt like a geisha as I washed his wonderfully, muscled body. It was fun soaping his beautiful organ that had just brought me so much pleasure. After our showers, I used a blow dryer to help dry my hair and it fluffed up and waved beautifully. When Michael complimented my delicate form and beautiful wavy hair, I revealed my love of cross-dressing. "Would you dress for me the next time we have sex? I'd love to see you in satin and lace." With these words, it was all I could do to hold back tears of joy as I kissed him deeply and held him as tight as I could. Chapter Five: More of Michael We agreed that it would be awkward for Michael to call my house, so I began the practice of calling him each evening just to talk. We agreed on a late date Friday after the band finished playing. I simply told my parents I'd be staying with one of the band members and wouldn't be returning home. They didn't seem concerned or suspect that I would get to sleep with my new lover. Of course, I told Betsy and Anne all about my experience and all we did was chatter about sex. They both wanted to know what it was like to be fucked. This led to more sex, where I used my penis to please both girls anally and vaginally. Since I had been on the blocker, I found that I would get hard without any problem as long as I had my hands or mouth on either girl's sex. I had a tough time staying hard on the top position, but when Anne or Betsy were on top, I could stay hard and satisfy them. Our sex was great and both girls glowed with newfound pleasure, but I didn't get off as much as I did with Michael. His physically larger anatomy seemed to take me further than either of the girls could. After Michael and I planned my overnight together, the girls and I went to the mall to buy new outfits for both Friday night and Saturday. Michael had promised to take Saturday off and we would spend it together. I bought a new little black dress, matching shoes, and stockings that fit Jane and me nicely. Jane lent me a beautiful lacy bra and panty set that was way out of my budget. Fortunately, the little dress was lined and I didn't need to buy a slip. I did waste a few dollars on a dark burgundy teddy for Friday night. It fit beautifully and looked great. Saturday would be jeans and a matching blouse and sweater set for the day. I had a pretty pastel bra and french cut panties to wear underneath. Jane lent me a beautiful tangerine color silk dress, slip, and underwear for a late lunch on Saturday. I bought a matching set of heels and another pair of stockings. We stored all the clothes in Jane's bedroom. Betsy insisted that she do something with my hair and I allowed her to layer it and trim my bangs. It still tied back, but was much more feminine when brushed out. I even allowed her to shape my brows a little bit. No one at school or home said anything, so I guessed I still went unnoticed. But the truth is I wouldn't have known. I really floated through the rest of the week. I was in love with Michael's body. The band was working Saturday night, so our romance together would be limited to less than twenty-four hours. The good news was that the gig was for three weeks and we didn't have to move our equipment so I could split right after our last set. After all our equipment was in place on Friday, we did a sound check and took off for dinner. During dinner, Terry whispered that he had talked to Michael that week and had heard about our afternoon. My stomach dropped several notches until Terry told me that he and Michael had also been lovers a few years ago. I never knew that Terry went both ways, but he assured me that he was happy for me and wished he had been there on Tuesday. Terry and I spent the rest of the meal whispering and laughing. Betsy and Jane both came to our teen club gig. The girls enjoyed themselves dancing with other band followers. By the end of the evening, it was obvious that they had both been partying pretty heavily. When I went to transfer my overnight bag to Michael's car, both girls were there to give me kisses goodbye and to kiss Michael, too. As I climbed in Michael's car, I only hoped they made it home safely. "What do you want to do first?" Michael started up his car and drove out of the lot. "I want to go to your place to get a shower and clean up. Then I'd like to dress for you, get something to eat, and go dancing." "Aye, aye, you're the boss. I know a great after-hours club with good music and great food." As we drove in the car, Michael complimented the band and all the new cover material we had been playing. He was impressed with my arrangements and how well we sounded. When we got to his place, Michael carried up my overnight bag and followed me into his bedroom. "Can I watch the transition? I love to watch your tall, slender body." He sat back on his bed. I leaned over and kissed him deeply. "You're the boss." I said as I lightly rubbed his obvious erection. I stripped my sweaty band clothes off quickly. There was nothing very romantic about my black tee shirt and tan chinos. Naked, I leaned over, kissing him again. His arms embraced me and stroked my ass. "Whoa, Let me get all cleaned up first," I said as I grabbed my case and walked into his bathroom. I scrubbed off all of the evening's smoke and sweat and scrubbed myself through and through. I shaved my legs and armpits smooth even though it really wasn't necessary. I brought along an enema to clean out my colon from tonight's meal I ate with the band. I wanted to be fresh and clean for the evening ahead. Freshly scrubbed and smelling better, I opened the bathroom door and invited Michael to join me. I applied perfume and put on Jane's bra and panty set. I used foam pads to fill out my bra. Michael came up behind me and told me how nice I smelled. After finishing with my hair and makeup, Michael helped me zip up and fasten my pearls around my neck. I did my earrings and twirled around for his approval. He reached under the dress to stroke my cock and balls. I moved into his hand and pushed lightly. I slowly ground my crotch into his large palm. He reached around with his other arm and pulled me tight. I looked up to meet his mouth and we began to kiss in earnest. I continued to grind close to him and felt my cock filling with the heat of his hand and growing hard. I ran my hands down his chest and cupped his crotch through his pants. "You are a doll," he said. "I would never know that you were a sixteen year old boy." I returned his compliment with a second kiss and picked up my purse as we walked to the door. "I can't wait to have you in my arms tonight." It was a great evening. The disc jockey played the best dance numbers and a lot of romantic slow songs. Throughout the evening, Michael was the perfect date. No one could have paid more attention to me. He did his best to make the evening perfect. We ate and danced until about four o'clock in the morning, then returned to his place. As we got ready for bed, I slipped on the burgundy teddy and pulled my naked lover into bed with me. He took out a tube of ky-jelly and we both lubricated his prick together. Using several pillows, Michael raised my rear to meet his cock. Grasping my legs and spreading them, he entered me slowly. I was in heaven. His large member slid in, filling me completely. I gasped with the pressure and stretched to take him in all the way. Then he stopped the forward motion and slowly withdrew. Right before the head of his cock was completely out he pushed back in. Time and time again he entered me until I was oblivious to the pain of my legs being pushed up so far. All I could feel was his member rubbing my insides, sending waves of pleasure throughout my body. I folded my legs flat along my sides and gradually brought my legs around him. My own penis stayed flaccid, but felt good from the contact of Michael riding me. Eventually, I was back on top, riding Michael, straddling, thrusting myself back into his shaft. I loved the feelings of his strong hands spreading my rear, guiding me repeatedly into him. I moaned with pleasure as I sucked his tongue. When I knew he was going to cum, I slid off and started to lick the pulsing head of his cock. I pushed my ass into his face and he gladly fingered me and licked the rim of my asshole. As I felt him start to erupt, I completely swallowed his cock. As he convulsed, I felt the cum shoot filling my mouth. I swallowed every drop, moaning with pleasure. I rolled to my side, still holding his cock in my mouth, as I lay on his side. As I lay there, he swallowed up both my cock and balls, still fingering my rear. Filled at both ends, I began to feel an orgasm building deep inside. As I came, Michael drank me up. We held each other tightly until I was completely spent. I moved around to face him and be held in his arms. As I kissed him, I licked my cum from his mouth and his chin. As we both fell asleep, I pushed my rear into his crotch, reaching for his perfect cock. It was still semi-erect and I gripped it tightly with my ass and legs. With Michael's arms holding me, we fell asleep. He still hard cock was between my legs and in my hand, as I slept through the rest of the night and into the morning. As I awoke, we were still embracing each other. I grasped Michael's cock and felt its hardness. I backed into it and slid it deep into my rectum. Within minutes, Michael was humping me doggy style and filling me deeper that I had ever been fucked. This was not a tender, loving moment but the frenzy of two bodies racing together. I was soon covered with sweat and cum, lying in a sticky pool, gasping for breath. "That's some wake-me-up," I gasped. "You are too much." "I can't remember the last time I had so much fun." Michael whispered as he kissed me all over my back and neck. We showered and dressed for a late lunch. There were still a few hours left before I had to play and Michael wanted to take me shopping. We went to the Mall and I spent hours modeling for him. He purchased everything I wanted and insisted I get more. Michael wanted me to dress for our band tonight en-fem and there I drew the line. "I'm not ready to confront people I know. I really don't want to make them uncomfortable. And besides, everyone from school comes to the club and what would they say? Michael agreed with my logic, but said I needed new clothes to wear tonight. We compromised and I picked out a pair of tan pair of woman's tailored, pleated pants that showed off my thin figure. I bought a pair of navy stockings and a pair of woman's navy blue loafers. Michael insisted I wear a tiny, tight navy top with my new outfit. It was sleeveless and had spaghetti straps. I didn't argue and even left my hair flowing when I showed up for our sound check. CHAPTER SIX: Playing In The Band When I met the band for the sound check, the guys let out wolf whistles and hoots of pleasure. I had never realised what good friends they had become as they supported my transition to femininity. I had on a touch of eye make-up but no lipstick. I gave each one a big smile and Terry gave me a hug and a kiss. "You smell delicious, kid," he whispered. I had never felt more comfortable as we covered a few rough spots from last night and I introduced a few new songs off the radio. We played for about an hour and broke for dinner. The evening went by in a dream. Kids from school said hi and everyone complimented my hair, girls and guys alike. No one said anything disrespectful and I was beaming inside and out. Between my swelled head and well-fucked ass, I was in heaven. The only sad part was the evening ended and I kissed Michael good night in the parking lot. I told him I wished I could sleep with him tonight. Jane and Betsy gave me a ride home, talking all the way. When we got home, they helped me unload my bags and carry them into my room. I had asked Michael to store a lot of my new clothes, rather than set myself up for problems with my parents. I fell asleep that night and slept half the day Sunday. It had been a big weekend. My sixteenth year fell into a routine- school all week, cheering for Jane's sports teams after school, helping Betsy with Student Council, a little homework, rehearsals, playing weekends with the band and staying with Michael, sometimes through Saturday night and Sundays. It was as busy as could be and really pleasureful. My parents said little or nothing about my new hairstyle and my gradual change in clothing styles. I never wore makeup or dresses around them but my clothes were obviously more feminine. We really didn't spend much time together and nothing was ever said. Since I did my own laundry, mom never commented on my changing undergarments, but it felt good to go to school wearing cotton french cut briefs and spaghetti strap teddies on rather than boys underwear. Occasionally, I'd wear a little mascara or blush to school, but I tried not to over do it and really remained understated. Michael was the best friend I could have asked for and I counted the minutes until each weekend. Even though there was ten years difference in our ages, we were quite compatible. We'd talk on the phone each night for hours and I loved to feel his arms around me each weekend. One Saturday at lunch, Michael suggested that I change my prescriptions. "Why? Everything is doing fine." "Well, you're close to seventeen and you need to decide what you want to do. You can't delay your decision forever." "What decision? I don't want to grow up and become a man. I'd rather die than change." "No one is saying become a man. Why not grow up and become a woman? You could start taking hormones and grow up with a woman's body." Michael and I talked for a long while. I realised that he knew me and what I wanted as much as I did. We both agreed I'd start a female hormone and see what happened. We also both agreed that it shouldn't be too strong and remove my sex drive. I enjoyed my genitals and didn't want to loose the pleasure I got from sex. When I announced my decision to the girls, both Betsy and Jane agreed and we celebrated one day after school in their bedroom. It was like old times, laying together and bringing each other to orgasms, time after time. Betsy got out her mom's Polaroid camera and we took some pictures of my underdeveloped body. I weighed myself and used their tape measure to record my measurements. Jane decided we needed to keep a log of the changes in my body shape as a record. CHAPTER SEVEN: Changes I started the hormones close to my seventeenth birthday and they had some immediate effects. My appetite increased and I began to gain weight. Most of the weight gain was centered in my bottom and legs. I also started to grow taller the change was in my legs. Over a period of a year, I recorded a two-inch growth in my inseam measurement. By the time I reached my eighteenth birthday, I was 5'9" tall and weighed 125 pounds. My breasts changed too. My nipples grew overnight and became painfully tender. They became enlarged and the areas around them grew, too. I even thought they got pinker in color. The area around my nipples continued to change. They got larger and so did the nipples. In about three months, they really looked feminine. Any change in temperature made them stiff and rock hard. Slowly my entire breast started to change shape and grow. Within six months, my breasts started to protruded and formed two little cones on my chest. This made my nipples protrude noticeably and without a sports bra, it was obvious what was happening. Throughout the year my breasts filled out and continued to develop. While my arms didn't seem to change, I knew I was gaining some muscle, but not as much as the guys in the band. My real strength was in my legs. I enjoyed getting outside and walking. During this period, I felt a real change in my personality. I started to feel more emotional than ever before. If I didn't know better, I would say that my brain was also becoming more feminine. The dumbest stuff would make me laugh or start crying. During this time, I started to become more dependent on my friends and especially Michael. Home life became a daily evasion of my mother's growing curiosity. I knew she suspected something was happening, but never came right out and said anything. Many times, she would knock and want to catch me undressed to inspect my obviously changing body, but was too polite to invade my privacy. I had to purchase new clothing twice that year to adjust to my rapidly changing shape. Underwear and pants had to go, or they would overemphasize my changing hips and bottom. I never grew voluptuous, but it was obvious that I now had a teen-age figure. I could wear an A cup bra when I chose. I wore sports bras to school to flatten my chest. It was hard enough to deal with everyday life as a teen. I wasn't ready to confront an entire school full of questioning people. Occasionally, I would wear my hair untied, and once in a while wear a pair of earrings instead of just one ear, but generally I chose to quickly fade into the masses. My hair began to grow much more rapidly, requiring me to get it cut regularly. The texture seemed fuller and finer. At first, Betsy would trim it, but eventually she recommended a real hairdresser. My visits became really fun to see what cuts would flatter my face, but could still be pulled back for school. As my hair grew longer, it became a fun to try out different styles. I looked forward to curling it for Michael on our special weekends. I started to grow hair in my armpits and on my legs. These I shaved in the shower and that's how I got into a intimate discussion with my mom. One day she asked me why I kept turning the water off and on while I was showering. I admitted I was shaving in the hot, humid water. I guess I blushed when she examined my face up close. "Honey, I can't see what you're shaving. You don't have any beard growth at all." I started to laugh and decided it was time for our talk. We sat at the kitchen table for almost thirty minutes while I talked about my life and the drugs I was taking. It ended better than I expected, with tears and hugs and a trip to the bedroom where I gave her the full tour of my naked self. Her only comment was I needed to shave a better bikini line and trim my public hair. She said it shouldn't show out the sides of my underwear. I modeled some of the clothes and we decided to go shopping that evening after dinner. It was a great night and we talked together more that night than we had done in years. The only thing that mom wanted was for me to start seeing a proper doctor who would supervise my transition. I readily agreed and felt that would be a good idea since things with Michael had not been going well. I had felt a sense of loss with Michael and when we talked about it, he kept insisting that it was nothing and I shouldn't worry. But one night, when we were making love, Michael had trouble sustaining an erection. Regardless of how much I tried, I couldn't keep him hard. Since my little penis had not gotten really hard in months, we ended up cuddling and talking. Before long, Michael admitted that my changing body didn't stimulate him anymore. He preferred boys, not girls. My small cock didn't get him excited anymore. "All those times you'd dress for me, I knew there was a boy's lean body and a tender cock and balls inside waiting. I loved to spread those hard cheeks and probe your tight ass. But now, when we fuck, I'm fucking a woman and it's different." I knew that it had been different in the past few months and that we had come to the point that we wouldn't stay lovers. I couldn't be what Michael wanted. I didn't want to be a young boy anymore and I was excited about the steps I was taking to change my body. That didn't make what we had any less meaningful. Michael was truly was angel and I would always love him. I understood his needs and wanted him to be as happy as I was. We promised to remain close and did our best to satisfy each other that night. Michael continued to be a great friend and helper. He did anything I asked and continued to follow the band. Now, it was interesting to watch him court his next young lover as we played for the crowds. CHAPTER EIGHT: Summer In The City & The Fall At College The band was doing well and we were asked to cut a demo in the city. We all piled into the van and went to the recording studio. We played for about an hour and ran through a lot of tunes we had perfected. Everyone agreed that we sounded tight musically, but without original tunes we were just another cover band. As we packed up, one of the engineers sought me out and offered me work as a studio musician. From then on, I'd take the train into the city each day after school and read the music and play what ever they asked. I joined the union and was paid scale, which was more than I was making on the weekends in the band. I agreed to work full time for the studio for the summer. This meant a daily salary and steady work. I told the band that I would be available to play any night and no one seemed to object. Studio work kept me busy. I helped with arrangements and played a number of instruments. When there wasn't recording work to do, I helped the engineers on the recording end. Everyone agreed I had a good ear and set the balance levels well. It was fun and exciting. The studio had no problem with me coming out as a woman anytime I chose. Most of the days, I dressed simply in jeans, but wore makeup and a conventional bra. On the hotter days, I started to wear dresses without stockings. Some days, I'd even wear a tube top, tee shirt and shorts. The summer went by quickly. I guess I set aside my love life after Michael and buried myself in work. The guys in the studio were older and did not attract me. There were offers, but I think they were being polite and testing me out rather than interested in me seriously. On the weekends, I dressed very neutrally. I didn't flaunt my transition, but it was obvious that I wasn't a boy anymore. The crowd didn't seem to care and being surrounded by four other big guys protected me from any rude drunks who wanted to see the "faggot" or "fairy". That fall, I turned eighteen. I was accepted at two different music schools, but, working in the studio had changed my perspective and I decided to continue to work and take courses in electrical engineering at our state college. I would minor in music studies. At this point, I was busier than I had ever been, working, studying, and playing. As I promised my mom, I had been seeing a real doctor for six months. She readily agreed that Michael's prescriptions were accurate and after some tests decided to increase the dosages slightly to compensate for my increased weight and height. She also had me visiting a psychologist for twice monthly sessions. Since I was not interested in sexual reassignment surgery, there was no pressure from either doctor. Changes continued to occur to my body. My bone structure seemed to be more woman-like, with my hip and pelvic bones growing slightly larger. I thickened out more below my waist and my legs started to fill out and become more shapely. I was still pretty androgynous looking, but I could now fill a b-cup with a little help. I could even show cleavage with a push-up bra. Jane and I decided to rent a two-bedroom apartment and room together. Since I had spent so much time in the studio and the band, she had caught up with me and had enough credits to start college. Jane wanted to study physical education and sports medicine. She was as excited as I was to start the year. We unpacked and went to the orientations together. She insisted that I dress for each meeting. "Don't confuse people. Dress just how you feel, but dress like a woman. Be you. You don't need to be ashamed that you enjoy being feminine." Jane made a lot of sense. At eighteen, I really had my own life to lead and dressing helped me feel complete. From then on, I never looked back. I didn't hide my new body anymore. I didn't feel comfortable strutting, but I like to wear skirts and blouses, jeans and tight knit tops, little tees and micro skirts, tights and stirrup pants. My studio work salary disappeared quickly buying a new wardrobe. Jane enjoyed shopping with me and we were able to share most of my clothes. She was a few pounds heavier and an inch shorter, but we could share just about anything. Speaking of sharing, we still enjoyed sleeping together. While we each had a bedroom, we spent most of our nights in the same bed. Sleeping with her was a dream come true. Jane had a wonderful body. Her breasts were lush and full while mine were still growing. I loved to bury my head on her chest and nurse while she stroked my hair. My hands would drift between her legs and playfully bring her to orgasm after orgasm. My penis continued to grow with my body, but my testicles remained tiny and shrunken. I could be stimulated to an erection, but it was very hard to sustain it and unless I was on the bottom, Jane couldn't be completely satisfied with my member. When I was on top, I went soft after a few minutes of humping. At first this was frustrating, but as long as we both had orgasms, it didn't seem important. The sensitivity in my breasts continued to grow and I could achieve an orgasm just by being sucked and manipulated. Jane could bring me to climax by concentrating on my nipples and slowly stoking my dick. Right before I would cum, it would get enlarged and very hard, but after ejaculation, it would shrink back to nearly invisible. Normally I didn't even need to tuck it away. Thong or bikini underwear held me firmly in place. My tiny little balls made it easy to keep my feminine appearance even when changing in a department store dressing room. The fall flew by. When I wasn't in class or studying, I worked at the studio in engineering, mixing, or recording as one of the house musicians. The experience was great and I learned a lot. With the extra money, I splurged and got a new cut and perm. My hairdresser took time and added highlights to my sun-lightened brown locks. I felt like a million dollars. The guys in the band were more than encouraging. They wanted me to dress up for our gigs and insisted that I be treated like a lady. I didn't argue and enjoyed the flattery and attention. Jane tagged along at most of the jobs and I knew that everyone lusted for her, except for Terry who now admitted to everyone that he was definitely gay. CHAPTER NINE: Playing With The Band On band nights, I enjoyed dressing a little slutty and showing off. Many times I went braless. I stuck to tiny spaghetti strap tee shirts, lacy teddies, and transparent tops and complimented them with micro skirts, tights, or spandex jeans. Sometimes I'd wear my red cowboy boots, high heels, or sneaks depending on my mood. Playing under the lights was sweaty work and I never wore too much makeup for fear it would run and I'd blind myself every time I towelled off between numbers. Mostly, I'd stick to lipstick and the minimum amount of eyeliner and mascara. After each gig, we'd all go out to eat at our favorite all- night-diner. Sitting around one night, the conversation turned to sex. The guys wanted to know if sex as a woman was better than as a man. I laughed and admitted that I wasn't very experienced with either. Blushing, I said I could count my lovers on one hand and still give them the bird. We all laughed, continued drinking more beers, deciding to all go back to our apartment and get high. Terry had quite a stash that Michael had given him that night. In the mini-van on the way over, we were smoking, popping pills, and snorting cocaine. By the time we were up in our apartment, we were pretty loaded. Jane set the tone by hugging and kissing everyone as she welcomed them into our apartment, saving the biggest kiss for me. Before I knew it, Gary was taking off his shirt and pants and undressing Jane right in front of us. I felt hands turn me around and Chuck started rubbing my breasts and kissing me. A second set of hands belonging to Doug unzipped my skirt and began to pull it off. I enjoyed the groping hands and started to undress one band member at a time. I was pleased to see their erections spring free and hard. As I manipulated Chuck's penis and balls, I felt Doug take my dick into his mouth. He swallowed up my penis and balls and began to stroke my ass cheeks. Chuck pulled me up for a deep kiss and I felt another set of hands replace mine on his penis. Terry had got on his knees and was sucking on Chuck. The four of us collapsed on the floor and continued to slurp all over each others bodies. I had never had a cock in my ass and my mouth at once and now I had two more to rub on my tits. I lay there and closed my eyes. Using my hands, I felt the first load of cum spurt on my chest and neck. Rubbing it in, I used it to slide the second cock harder between my breasts. Someone came in my ass and I grew hard and came, too. I swallowed Doug and felt him cum in my throat. The entire time this was happening, we could hear Gary and Jane wearing each other out. Their wild monkey love frenzy was impressing us all as I crawled over and licked Jane's dripping cunt as she climaxed repeatedly. Doug started to take me doggie style and I raised my butt high to receive his delicious member. While I was being plowed from the rear, Chuck gave me his cock to swallow. Soon, Jane had slid under me and was swallowing my cock and balls as I fingered her pussy. She started another orgasm and turned around and reached up to grasp my now enlarged dick and slips it inside her. As she began to cum, I could feel my dick spurting along inside her. As I rolled over exhausted, there were more guys to satisfy. We snorted cocaine and fucked all night. Drinking beer, smoking joints, we screwed our way into the dawn. When no one had anything left to give, we flopped in bed together and slept through the day. By Sunday afternoon, I woke and showered. About a minute after I had stepped in the water, Jane joined me. We embraced and kissed under the hot spray, then lovingly lathered each other's bodies clean. I was still sore all over from the night's debauchery, but hugging her soap-covered body renewed my love of the girl next door. The band didn't repeat that amazing evening ever again. But, people agreed that we sounded much tighter now, especially adding Jane as our backup singer. We were quite a group.