9 comments/ 37256 views/ 28 favorites Boys in the Attic By: Roustam Shortly before I began my junior year at SUNY Binghamton, I rented a room in a boarding house near the campus. I was tired of dorm life. The noise and the lack of privacy during my first two years at college had always been very annoying. My roommates were tolerable, but they tended to invite friends over at all hours for parties or long, dull bullshit sessions. I was in school to learn. My parents were paying for me to better myself; I intended to repay their generosity with academic excellence. The boarding house stood on a quiet street a couple of miles west of the city center. Binghamton was a still fairly thriving mid-sized city at that time. The northwestern quarter of town was filled with factories and machine shops. South of the main thoroughfare, in the "West Side," there were hundreds of private homes. Most of them were quite large. Many of them housed students who attended the State University. The campus was south of the city, across the Susquehanna River. The university had its own bus system to pick up students at no charge from all points of the town. I was fortunate to hit it off with my new landlady, Joan, at our first meeting. Joan taught high school English in a small town thirty miles west of Binghamton. She rented two of the four bedrooms in her two-story house. I was surprised by her height when I first saw her. At five-eleven, Joan was just a bit taller than me. She was slender with very long legs. I didn't find her particularly attractive, but she was very friendly and she put me at ease right away. The rent for the room fit within my budget, so I agreed to move in two weeks before my classes started. Joan gave me a tour of the house and explained that my rent would allow me use of all of the common rooms. The living room was quite large, as was the adjoining dining room. The kitchen was very spacious and sunny. A breakfast nook had took up one corner. The second floor held the four bedrooms. My room was larger than the dorm room I had had for the previous two years, and I was delighted to know that all of it would be mine. The room was furnished with a queen-size bed, a desk and chair, a large wooden wardrobe and a full length mirror. The closet was big enough to have been a room in itself. Jane explained that she shared the bathroom with her tenants. She had not rented the third bedroom yet (she kept the fourth one for her own guests), but when she did we would all get together and figure out a schedule for our daily shower times. Jane said that she always arose at five and was done with the bathroom by six. I assured her that I was rarely out of bed until seven at the earliest. Across the hall from the bathroom was a large wooden door. Jane told me that the door led to the attic. She didn't show the attic to me then, but said that it was nearly as large as the second floor. I was welcome to use it as a storage space for a few items, if needed. At that point I had very few possessions; I doubted that I would ever need more space than I would have in the bedroom. Moving day arrived and a friend of mine with a car helped me carry my possessions to my new digs. I treated him to pizza and beer afterward at a local sports bar. It was an unusual indulgence for me, as I lived on a fairly strict budget. Pizza was a luxury. I almost never drank. The post-moving meal was the least I could do in return for my friend's help, however, so I made an exception. Joan's new tenant moved into his room later that week. His name was Billy. He let us know fairly quickly that he preferred "Billy" over "Bill." He was a big, rangy local kid who had been accepted to the University on a full academic scholarship. To look at him, I would have guessed he was a hockey player. I later learned that he was fluent in Russian. He was studying Russian history and literature. Billy was a great conversationalist. He spent his first evening at the house in the living room, talking to Jane and me about every subject under the sun. The semester started. I returned to my long-held regimen of eight hours a day on campus followed by another four hours of study in my room. When I was at the the college I was either in the classroom or in the library. At home, it was very nice to be able to study in peace and quiet. Billy was much the same way. We would run into each other in the kitchen or the second floor landing, but that was about the extent of our interaction. Joan had the living room and the shared television set to herself in the evenings. On the weekends I would spend most of my time in the living room reading or getting to know Joan better. I was lucky not to have to work for extra cash. A few ordinary weeks went by. I settled into life at the house and managed to stay on top of all of the course work. I had five separate classes. Two of them required an extraordinary amount of reading each week. I often found myself up past midnight with my nose in a book. It wasn't particularly fun, but I hoped it would pay off someday. There wasn't much time left for fun. Shortly after Columbus Day I had a weekday free of classes. I decided to forget studying for a little while and enjoy myself. I wanted to take a walk down to the city center, visit a few stores and take a walk along the riverfront. As I left my room I stopped on the landing and looked at the attic door. I made an instant decision to postpone the walk and take a look upstairs. No one else was at home - not that it mattered. Joan had told me I was welcome to use the attic if I needed to. I opened the door and saw a flight of bare wooden steps. One pair of woman's shoes sat at the edge of each step. I found that odd, but amusing. I made my way up the steps. The stairs turned to the left and then left again. There were about a dozen, in all. A strong, pleasant aroma of cedar intensified as I ascended. I flipped on a light switch on the wall. When I reached the top of the stairs I was astonished at the size of the attic. The walls were angled inward, but the center portion of the room had a ten foot ceiling. There were windows on all sides. Smooth, unfinished planks formed the flooring. I realized that they were all cedar. Joan had covered most of them with area rugs. I saw an old sofa and a cot with a twin mattress along one wall. The real surprise were the wheeled clothes racks that took up nearly half of the room. There must have been eight of them. They were all loaded with dresses and jackets and other items of clothing. I couldn't guess how many separate items there were. I walked over to one of the racks and started going through Joan's old things. I immediately noticed that some of the dresses had to have been from the 60s. They looked exactly like the ones my mother had worn when I was a small boy. I laughed at the memories. Other memories emerged. Memories of my secret visits to my parents' room when I was younger. Recollections of the all of the times I had carefully taken my mom's underthings out of her drawers and tried them on. Memories of my first sexual stirrings, attained while wearing mom's pantyhose. I thought of my first ejaculation. It had occurred while I was rubbing one of mom's slips against myself on her bed. I thought that I had "cured"myself of those desires over the intervening years, but here they were again. Joan's clothes appeared to be in near-perfect condition. They all smelled wonderful. Each piece seemed to have its own scent. I lifted one after the other and held them to my nose. I could close my eyes and return to my childhood, when the smell of my mother's perfume on her things would intoxicate me. Mom never knew what I did with her clothing when she was away. Or, if she did, she never confronted me with the knowledge. I was very careful about putting everything back neatly when I was done. I lifted one of the dresses from the rack. It was a gown of some sort, in scarlet. It had long, loose sleeves and reached just below my knees when I held it against me. I didn't know what sort of fabric it was made of. It was quite light. For a second I imagined myself wearing it. I quickly placed the gown back on the rack and snapped out of my reverie. Another discovery occurred just moments later. I noticed a partially hidden chest beyond the racks. It was tucked under the angled ceiling. I walked back to it. The chest was an antique; it had the "stressed" wood and the iron bands around its body. The lid had a lock, but it opened easily when I gave it a pull. I felt a surge of excitement when I saw the chest's contents. It was full of lingerie. There seemed to be an endless number of panties and stockings and bras in the chest. Garter belts and folded nighties and balled up pantyhose of all colors. Everything smelled of the chest's cedar lining. I dug one arm deeply into the underthings and quickly realized that there had to be dozens of pairs of everything there. They were not really organized in any way, just jumbled together. I could not imagine how many years of purchases were contained there. I wondered why Joan would save everything for so long. I checked my watch. I had spent the better part of an hour in the attic. I worried that Joan or Billy might return and wonder why I was up there. I closed the lid of the chest and checked to make sure that the hanging clothing appeared to be undisturbed. It was only then that I noticed all of the shoes that had been arranged along the wall beyond the chest. There were several dozen pairs. I returned to my room and went over the details of the day's discovery. I was painfully erect by then. My old cross-dressing interest was completely revived. Unable to stop myself, I lowered my jeans and shorts and relieved myself of the pressure. I did so while picturing myself in the red gown. I felt ashamed afterward. I didn't consider myself a transvestite. I hadn't dressed in five or six years. It was a tendency that I had consciously fought to suppress. Now it was back, stronger than ever. The first trip to the attic was the only one for quite some time. I simply didn't have much time to spare for pastimes, given all of the academic work I had to complete each week. I was reading three or four dense books a week and writing papers constantly. Many a night I was up until late typing or filling out three-by-five cards with notes. I looked forward to the days when I could simply work for a living and have at least a little free time for myself. During Thanksgiving week, both Billy and Joan took trips to visit relatives in other states. My parents had left that Monday for a trip to New York City. Mom had always wanted to see the Macy's parade. They offered to take me with them, but I declined. I looked forward to having Joan's house to myself for a few days. My classes ended on Tuesday and I hurried home. As soon as I arrived at the house I made sure that no one else was around. All of the rooms were empty. None of us had locked doors; we lived by the honor system and it worked well. I trusted Joan and Billy not to snoop or steal. I did take a brief look into both of their rooms, but I didn't touch anything. I walked up to the attic. It was quite cold. Late November in Binghamton was a gray, wintry time. I took a quick look out of all of the windows to make sure no one was around outside. I then turned my attention to the clothes racks. I felt as though I was in a department store with an unlimited credit card. I found the scarlet gown and carefully placed it over my left forearm. I went to the chest and opened it. I picked out a pair of red pantyhose and a red satin bra. It took me a moment to find matching panties. I placed everything on top of the gown. I looked at the shoes and spotted a pair of red pumps that appeared to be made of suede. They had a red ribbon at the toe. I couldn't help but pick them up. As quickly as I could I returned to my bedroom. I laid the lady's items on the bed. My clothes were off in seconds. I was, of course, hard as a rock. I sat down and lifted the panties. All of the old sensations I'd known as a cross-dressing child returned. The panties felt electrified in my hands. I slipped my feet through and pulled them upward. I gasped. I stood and smoothed the panties over my butt and my groin. I nearly came at that moment. It took a supreme act of will power not to. The bra and the pantyhose followed after the panties. I hooked the bra in front and turned it around. I nearly came again as I tugged the pantyhose up both legs. They were a bit large, but I folded down the upper two inches and tucked them inside the panties. My legs felt as if they were embraced by an angel. It really was heavenly. I ran my hands over every inch of them. This was a dream come true. I had not thought to select a slip, but the gown fell easily over my skinny frame. I was able to zip it up most of the way and adjust it correctly. The hem reached the top of my calves. It was miraculous that Joan was almost the same size as me. It was even better that I was slightly smaller. I took a deep breath and smoothed the gown over my body. My god, I was aroused! My appearance in the full length mirror was startling. With my longish dark hair and my slender body, I looked quite like a natural woman. I took a brush from my wardrobe and pulled my locks forward to form bangs that fell over my eyes. I was not muscular at all; even my skinny arms appeared feminine. I made a mental note to look for gloves the next time I explored the contents of the chest. I swayed and turned and made seductive looks at myself. I was cute! To my great surprise and satisfaction, Joan's pumps were also a near-perfect fit. They slipped on without effort and did not slip or fall off as I made my first halting, tentative steps around the room. I had never worn heels before. Mom preferred flats and, as a boy, they were too large for me. Now, I discovered the ways in which heels affect the muscles of the legs and body. It was exquisite! I needed to keep one hand against a wall at all times. I stumbled three or four times before I got the hang of it. I certainly didn't master walking in heels, but I reached the point of feeling somewhat safe in them. My mirror image was so much nicer with my added height and the appearance of my ankles and calves atop the pumps. I twirled as fast as I could to see the dress swirl around me. After more walking practice I sat down on the bed. My pulsing member needed attention badly. Somewhat regretfully, I lifted the dress and gathered it around my waist. I scooted back on the bed and lay down. I pulled down the pantyhose and panties to mid-thigh. My heels rested on the bed covers. My fantasy in the following minutes had me there in Joan's clothes, welcoming a handsome young man into my embrace. He was a composite of boys I had known and secretly admired in high school. I had never so much as kissed a boy in real life, but in my fantasies I had gone much further. Now, I closed my eyes and envisioned my man mounting me. I folded my legs around his back and welcomed his thrust. My body shuddered as an earthquake of an orgasm overwhelmed my senses. It took a while to regain my composure. I might even have fallen asleep for a few moments. A puddle of cum cooled on my lower belly. I smeared it into my skin. After a short interval I pulled up the panties and hose and stood up. I needed to look at myself again. My hair was slightly mussed and my face was still flush with the afterglow of the orgasm. I looked like a young woman who had just been ravished. That pleased me. I wanted to stay dressed that way for hours. Unfortunately, I realized that I had to return Joan's clothes to the attic. I debated keeping them in my room until her return, but that seemed too much of a risk. There might always come a day when she would find a need to enter my room in my absence. It was best to play it safe. I undressed and put on my own clothing. It felt nearly painful to do so. I carried the feminine garments to their assigned places and made sure to double-check everything. I looked forward to my next session with them. I returned to the attic at least once a day until the end of the holiday weekend. I followed the same procedure: the selection of clothing, the return to the bedroom and the transformation. I wore several different dresses and pairs of shoes. I tried on garter belts and stockings for the first time, to my utter delight. Nothing had ever felt so good! I even tried descending the attic steps in heels, and did so successfully. I gained confidence in Joan's clothes. I believed I might even be able to pass as a woman in them. I had no intention to try, but I was very happy to see how good I looked as a female. The weekend ended too quickly. Joan and Billy returned Sunday evening. Joan was first, and we talked about her travels as she relaxed in the living room. Billy arrived much later and went straight to bed. He said that he had been stuck in traffic for hours and was worn out entirely. I was inwardly depressed at the knowledge that I might not have the house to myself for quite some time. Monday brought the first week of the remaining portion of the fall semester. There were three more weeks of classes until the semester finals and the winter break. I had two long term papers to complete and five exams to prepare for. Those weeks were a blur of reading, typing and endless hours in the university library. I was too tired each night to pleasure myself! At last, the winter break began. Christmas was just a week away. Joan had a few days at her school remaining, after which she planned to fly to Rome for the holidays. She loved to travel. Billy looked forward to a trip to California, where his sister owned a small horse ranch. He wouldn't be back until late January. If I stayed in Binghamton, I'd be alone in the house for at least two weeks. It was a tempting thought! I compromised with myself: I made plans to spend one week at home with mom and dad, then return to the boarding house before New Year's Eve. My parents were glad to see me, and it was nice to be back in my boyhood home. Being free from my academic workload was wonderful, as well. My hard work had paid off; I had a 4.0 GPA for the semester. I was fairly proud of myself, and my parents were ecstatic. They gave me five hundred dollars as a gift for getting such good grades. I admit that I cried at that. We all enjoyed a wonderful Christmas dinner and talked for hours every day. I returned to Binghamton on the day before New year's Eve. I told my folks that I had studying to do for the new semester, to get a lead on the upcoming courses. That was partly true, but mainly an excuse for me to have time alone in Joan's house. The bus ride back was interminable! I imagined what I would do and what I would wear. I could imagine the brush of silk and lace against my skin. My hair had grown longer over the past two months and I had not had it cut. I really wanted to try styling it, but I didn't have a clue how to do it. When I arrived at Joan's house I raced upstairs with my bags and threw my coat on my bed. I immediately checked the other rooms for any signs of activity. There were none. I went to the attic and shivered in the frigid air up there. I suppose I shivered, as well, from the sexual tension that was building within me. I picked out two complete outfits and took them to the bedroom. The first was all in white. White undergarments, stockings and pumps. A white dress with a leather belt, probably from the mid-60s. The belt had a large, round plastic buckle. The hem was well above my knees. The stockings sparkled as I turned before the mirror. I loved the retro look! I posed every which way and winked and kissed at my reflection. The second outfit was entirely black. It seemed to turn me into an entirely different sort of woman. I could feel the difference. I think I preferred the white, but both were heavenly to wear. I finished the dress-up session with another earth-shattering orgasm. I remained dressed during a long, deep nap. Boys in the Attic The few days that followed were blissful. I dressed as often as I liked. I "relieved" myself as often as I could. My walking in heels improved. I was convinced I was hot. My fantasies of being "taken" by other guys grew more elaborate and stimulating. I had one explosive ejaculation after another. I slept very well at night, especially when I was wearing a lace teddy and stockings. Joan returned in the second week of January. My idyllic mini vacation was over. I nearly cried when I saw her car pull into the driveway. Once she was unpacked and settled, Joan talked for a few hours about where she had been and what she had done. I was fascinated. I wanted very badly to spend a year abroad, but I didn't have the time nor the cash to do it. Joan's stories and photos were the next best thing. Joan went back to work, Billy returned and the spring semester got underway. I dove headfirst into the new round of study and writing. I wanted to repeat my success of the last semester. I spent more hours in studying on the weekends. Even though I still had most of the money my folks had given me at Christmas time, I avoided spending it on dining out or drinking. I kept my nose to the grindstone. Spring break rolled around much faster than I had imagined. The bitter cold of the winter receded and we had a few nice days in a row every week. It was great to be able to open the windows and air out the house. Joan's Easter break from her school coincided with the university's break. Joan told me that she was going to Florida for several days and asked me if I could watch the house. I immediately, happily agreed! Billy said that he was going to take a road trip to California. I was secretly ecstatic that I would again have another week in which to indulge my secret self. As soon as my housemates were gone I rushed up to the attic. The temperature up there was perfect. Rather than make several trips up and down the attic stairway, I undressed in the attic and put on my female outfit there. I used the sofa for sitting as I dressed. It was clean and in decent shape. I wondered why Joan had left it there. I selected red again for my first session. Red undergarments and shoes. A red cocktail dress that felt wonderfully light on me. It had a bit of fringe along the hem that seemed very sexy to me. I loved red on women. I loved it on myself! I tried dancing; nothing fancy: just a few moves moves I knew that were manageable in heels. I started singing a pop tune that was then at the top of the charts. I giggled at the sound of my own voice. The sound of clapping froze the laugh in my throat. I turned to see a young man standing on the stairway. His chest and shoulders were just above the level of the attic floor. Of course I was shocked and humiliated, but I did notice that he was quite good looking. I scrambled to think of an explanation. "Don't let me interrupt," he said with a laugh. "That was very entertaining." My face must have been as red as my outfit. "Who are you?" I asked. "I'm Jerry. Joan's nephew. Didn't she tell you about me?" Jerry ascended the rest of the steps and stood just a few feet from me. He was taller than Joan. I guessed he was six-four. I also guessed that he was a football player or on a hockey team. He was powerfully built. I was doubly humiliated to be dressed in front of a much larger guy. "No, she didn't," I said. "How did you get in?" Jerry took a set of keys from his pocket. "I've always had a house key. I stay here in the summer's and help Aunt Joan with her gardening. Right now I'm studying up at Buffalo, but now I'm on my break. Are you Dale?" I was so embarrassed. I had to nod, but I started crying as I did. The shame was just too much. My body stooped as I bawled. Jerry closed the space between us and gave me a hug. I felt as though a grizzly bear had taken me in its arms. Without thinking, I rested my head against his rock hard chest. "It's okay," Jerry said. "I'm sorry I surprised you. I was passing through town on my way to the city, and I had asked Aunt Joan if I could stop by here for a rest. I guess she didn't tell you." I shook my head and croaked "No. She didn't. Please..." Jerry patted me on the back. "Don't worry. I won't tell anybody." He pushed me back slightly and looked at my face. "You know, you look really nice in those things." I couldn't meet his eyes. "I'll change. Just give me a minute." I started to turn, but Jerry held on to me. "Why change? You're doing what you like to do. Don't let me stop you." He kept a soft grip on my biceps. How could this have happened? I thought I had always been so careful. I was naive. I had allowed myself to become too distracted to pay any attention to the world outside the attic. A marching band could have walked through the first floor and I wouldn't have noticed. Now, my secret was a secret no longer. I wanted to disappear into a puff of smoke. After a few moments I looked at Jerry's face. He had a kind, empathetic smile. "Jerry, I can't stay dressed like this. It's too embarrassing. If you'll just give me a few minutes, I'll meet you downstairs in my real clothes. Okay?" Jerry answered by moving me back to the sofa. I felt helpless to stop him. At his unspoken request I sat down. He sat quite close to me. Our knees touched. Jerry put his right arm on the back of the sofa. A slight thrill raced through every part of me. Jerry's voice soothed my frayed nerves. "Look, I'm not out to get you into trouble, okay? I won't say a word to anybody. What you do up here is your own business. It's not for me to stop you, or to expose you." I shook my head. "I don't know why I do it. This really isn't me. It was just that one day I was up here and I saw the clothes. I couldn't help myself. I only do it when nobody else is around." I felt Jerry's hand around my right shoulder. It felt good, I have to say. I felt the fabric of the dress between his skin and mine. In fact, every bit of clothing I had on at that moment seemed to come alive and excite me. It scared me a little. "Do you have a female name, Dale?" Jerry asked. It had never occurred to me to name my other self. I shook my head. "You know, Dale can go either way." Jerry maintained his kind smile. "But maybe you'd like something that's totally different." He placed his left hand fingertips against my left leg. I nearly jumped! "Um," I began, "I really can't think of anything off the top of my head." I hoped that Jerry wouldn't spot the little tent in my dress. Jerry looked away for a second. "Let's see," he mused. "How about...Tracy?" He looked at me for my reaction. I liked it! I also liked that I didn't have to spend any more time looking like an air headed girl. "Tracy's nice," I said. "Good! Tracy it is. Let me hold your hand, Tracy." Jerry lifted his left hand slightly. I gave him a wary look, then placed my left hand in his. Again I had the feeling of a bear's claw encircling my too-small hand. But it was wonderful! He was so handsome, and he smelled like he had just stepped out of a hot shower. I lowered my head and giggled! "How old are you, Tracy?" Jerry started stroking my palm with his fingertip as he spoke. "Twenty-one." I whispered. "I'm eighteen," he said. "I'm still a freshman. I guess that makes you an older woman?" I laughed softly. "I guess it does." What the hell was happening? Was he really trying to seduce me? I didn't know how to get myself out of this predicament. "Do you mind that I'm older?" Jerry chuckled. "Not at all. I like older women. You know what?" I shook my head. "No?" "I like older men, too." Jerry's gaze transfixed me. I was speechless. My mind raced through all of the possibilities. He was gay? Bisexual? Was he really serious now? I must have had a look of sheer panic. Jerry released my hand and placed his palm along my right cheek. He leaned in toward me. Oh no. No. His lips touched mine. I closed my eyes. Yes, dear readers, it was my first kiss. Laugh if you must. I was THE high school geek. College geek. Geek of all pocket protector geeks. I had had crushes on girls from puberty onward, but I had never been able to summon the courage to actually ask one out on a date. As I have mentioned, I also had boy crushes on some of my classmates. Doing anything about it was unthinkable. I had always believed that my first kiss would be mine to deliver; delivered to the lips of a sweet young girl who would eventually become my bride. And now this. Not that it was bad! I found myself quickly opening my lips to receive Jerry's probing tongue. We licked at each other and took playful bites at each others' lips. I noticed that his right hand was completely around my right side. The warmth of his other hand against my cheek was delicious. Nothing I had ever experienced in the past felt anywhere near as good. Jerry pulled back just far enough to give me a broad smile. "You're a great kisser," he said. He caressed my forehead with his thumb. "Lots of practice with coeds?" I whispered "No. You're my first." I hated myself for admitting it, but this gorgeous hunk of a young man had me under his spell. "Are you serious?" Jerry said it without making me feel bad. "I would have never guessed." I had to feel his lips again. I leaned up and resumed our kissing. Jerry moved me back a little and brought my legs up over his lap. He held me with his right arm and caressed my lower legs with his other hand. This was too good to be true! Shock waves traveled from every place where his hand met my nylon covered legs. He had me. I would do anything for him. Any hesitation I had ever felt about being with a guy was gone. If I was to lose my virginity to a man, so be it. Jerry pulled back his right arm slowly and allowed me to rest against the arm of the sofa. I lifted my legs as he stood up and started taking off his shirt. I was entranced. His upper body was perfectly formed. He had abs to die for. Jerry's arms were heavily muscled. This was the first time I had realized just how sexy a male body could be. Jerry kicked off his loafers and pulled off his socks. His jeans dropped and I saw the outline of his cock against his briefs. It wasn't huge, but it made a nice bulge. After he stepped out his jeans, I sat up on the sofa and motioned for him to stop. "Let me do the rest," I said in my best sultry voice. Jerry grinned and stepped forward. I started by running my palms over his chest and stomach. It was as if he were made of polished marble. I traced the bulges and the crevices. I stopped when I reached the waistband of his briefs. I looked up. "Are you sure?" Jerry didn't speak. He just winked and nodded. He caressed my hair with his giant hand. I continued. I hooked my fingertips under the waistband and pulled down. The front of the shorts caught on his cock. I pulled them forward and saw my prize spring up just inches from my face. It was thick and possessed a large, perfectly formed head. I was giddy. I don't think I fully understood what I was getting into, but it seemed like a good idea! I took his cock in my right hand and cooed at its feel. Jerry moaned. You may find all of this very hard to believe. I had arisen that morning as a straight, part-time cross-dresser as square as any other geek on earth. All I had wanted to do was to dress up and masturbate, now that I had the means and opportunity to do so. But now, just a few hours later, I was about to perform my first blow job. I suppose stranger things have happened, but I can't think of any. You just have to believe that I - in that moment - was completely taken in by Jerry's charms and his self-confidence. His size, as well. I thought of myself as a pretty cheerleader to his alpha-male quarterback. My lips touched the head of his cock. I opened my mouth and licked the spongy head. It was wonderful! Before long I was bathing every bit of his tool with my tongue. It was in and out of my mouth, as were his balls. I stroked him and tickled the underside of his cock with my fingertip. Every so often I would look up and delight in his smile. Then I would look down at my red shoes and red-tinted legs. This could not possibly be real! But it was. When Jerry was about to come I felt his cock swell a bit. He grunted and I prepared myself for the semen spray. Several spurts of cum hit the top of my mouth as I licked the bottom of the head. I kept all of the semen in my mouth. I wasn't crazy about the flavor, but I didn't gag. I swallowed it and licked his cock as it slowly shrank. Jerry panted and collapsed on the couch. I giggled. "Was I good?" I asked. Jerry took my hand and kissed it. "Unbelievable," he answered. "My god, that was good!" He pulled me over for a kiss. We played dueling tongues for a bit. Jerry's hands were all over my body. When he touched my privates I squealed. At last, I stood and twirled for him. Jerry's grin said it all. "Take it off," Jerry growled. I played dumb. "Who, me?" "Who else? Come on. I want to see what's underneath that dress." I felt a moment of insecurity. "Jerry, I'm happy just to do stuff for you. To you." Jerry shook his head. "Nope. We've just started. Turn around." I obeyed. I felt Jerry unzip the dress. I let it drop. His hands cupped my ass cheeks. I squealed again. He turned me around to face him. My lace panties and garter belt felt even better as they were exposed to his examination. Jerry pulled me forward and kissed my tummy. I giggled. He surprised me by standing and lifting me into his massive arms. What did he have in mind? Jerry answered my unspoken question by carrying me down to the second floor. I was a doll in his arms. I felt weightless. He opened Joan's bedroom door and laid me down on her king-sized bed. I felt an added sense of naughtiness for being in there, but I was not about to object. Jerry opened a drawer of Joan's night table and took out a small packet. He put it on the bed next to us. "For later," he said. Jerry then laid himself down next to me and covered my body with caresses and kisses. He took off my bra and kissed my nipples. He kissed my neck and my ear lobes. He stroked my legs and thighs. Jerry removed my panties and freed my straining little penis. He took it in his bear paw and nearly killed me with pleasure. As Jerry kissed me, he stroked me until I came all over his hand. I hugged him tightly and moaned into this mouth. Jerry kissed my face and my neck as I recovered from my orgasm. I really was on a cloud at that point. Nothing existed beyond my arm's reach. My man was all. Jerry smiled at me and stroked my hair. He was so sweet! Every kiss of his convinced me that I was madly in love with this stud. Before long, I once again felt Jerry's hard cock in my hand. He raised himself onto this knees and picked up the packet. He tore it open and poured a small amount of lubricant onto his cock. Was he...? Was this it? I was suddenly afraid. "Don't worry," Jerry said. "Just relax and let me guide you. I promise it will be the best thing you've ever felt." I was somewhat comforted by his words. Still... Jerry remained on his knees as he pulled my legs around his waist. I scooted down until I felt his cock head against my asshole. Jerry spread a dollop of lubricant against my opening. I jumped and gasped. Jerry chuckled. "Ready?" he asked. I bit my lip and nodded. Jerry was a master at deflowering me. There was quite a lot of pain at first, but he kept talking softly to me and assured me that the pain would pass. It did. An incredibly powerful feeling of sexual pleasure took its place. I can't do justice in words to how good it felt. My legs locked against Jerry's back and I felt my heels click together with each of his thrusts. This was my most treasured fantasy come true. My prince was taking me as his woman. He was going to satisfy himself in me, and I would enjoy every second of it. He grunted and I moaned in unison. When Jerry came I felt the most wonderful sensation of warmth and fullness in me. I imagined myself being impregnated by his release. That thought pushed me right over the edge. I sprayed a few spurts of cum against his belly. We shared a many kisses in the minutes that followed. Jerry rolled to my side and I threw a leg over his. We laughed. I think we did all of the normal things any couple would do after such a passionate act. I was too happy and spent to worry about what I had just done. Then a stray, discouraging thought entered my mind. I raised myself on one elbow and brushed my hair from my eyes. "Hey," I said, "don't you have to go to the city?" Jerry chuckled. "Not really. I'd rather stay here." "But I thought -" Jerry cut me off by placing a fingertip on my lips. "Don't worry, doll. I was just going down there to see if I could meet a guy for some fun. I found a girl, instead." I playfully slapped his arm. "Hey!" I said in as deep a voice as I could manage. We both broke up at that. "Listen," Jerry said, "Why don't I call Aunt Joan and tell her I'm going to stay here for a few days? I'll tell her the truth: I met you and we hit it off. Besides, I'll save a hell of a lot of money on hotels this way. Sound good?" "Are you kidding me? You mean you want to stay with me?" I was over the moon! "Of course! Why not? I think we might have a little fun." Jerry squeezed my butt cheek with that remark. "Yes!" I squealed, followed by a big wet kiss on his lips. "Just don't tell Joan what we're doing." Jerry rolled his eyes. "First, she wouldn't care. Believe me. She knows I'm bi and it doesn't make a damn bit of difference to her. Second: as long as you want to keep it a secret, it's a secret. I'm not interested in hurting you in any way. Okay?" "Alright," I replied. I kissed him again. "It'll just be a while - if ever - before I can even think of telling anybody else." he nodded. I laid my head on his chest and drew circles on his skin. Before long, we were both asleep. The week that followed was the happiest of my life. I spent nearly all of it in Joan's old outfits. Every day was a fashion show for Jerry's amusement and arousal. We made love as often as we could, limited only by our stamina. Jerry proved to be a very thoughtful and gallant boyfriend. He even bought makeup for me! I would have died sooner than buy it for myself, but he walked right into the drug store and got me everything I needed to pretty myself up nicely. He explained that no one ever pays as much attention to us as we think. I couldn't agree, but I was thankful that he believed it. I practiced all day long with the brushes and applicators until I looked fairly good. I rewarded Jerry with all sorts of treats. When the week came to a close I was heartbroken. I knew that I had fallen deeply in love with Jerry. I didn't say it, but I'm sure he knew it. We spent our last hour together just holding hands and talking. Jerry said that he would be back as often as he could manage it. I was so tempted to drop everything and move up to Buffalo with him, but I retained my desire to finish my undergrad work at Binghamton and get a scholarship to grad school. I explained this to him and he agreed fully. We parted, and tears coursed down my cheeks as I watched his car disappear down the road. I was back in my male clothes, having returned all of Joan's clothes to their rightful place. It took hours for me to recover from my grief and focus my mind on my studies. Joan returned that night and asked me all about Jerry's stay. I didn't say much. It was so hard to get back into the routine of classes and study. I managed it, but my heart was no longer fully in it. Most of my heart had been carried up to Buffalo. I longed for Jerry's touch during every waking moment. I knew that I had to get over him. First loves, I had heard, are always the hardest. Boys in the Attic By Friday of that week I was marginally over the initial grief at Jerry's leaving. I still thought of him constantly, but I believed I might just be able to move on and keep our week together as a fond memory. When I returned to the house from the university that evening, Joan handed me a large, stiff envelope. It was addressed to me and had no return address. I had no clue who it might be from. I took it to my bedroom and opened it. Tears flooded my eyes as I pulled out a card with a giant heart on the cover. There was no writing on it, but I knew who it was from. More tears followed when I opened the card and saw, in giant, hand written letters, "I LOVE YOU!" Just underneath that was a large "J." I covered my mouth with my hand and let out a shriek of joy. When I had cried myself dry I ran downstairs and told Joan everything. I apologized profusely for wearing her clothes without her permission, but she laughed and said that she was thinking of donating them to good will, anyway. I offered to pay her for the ones I had worn, but she told not to be silly. We hugged and cried and I spilled out all of the pent-up emotions and thoughts I had carried for years. Joan assured me that she was fine with me being who I was. She promised me that it would be okay for Jerry to visit and spend time with me. Needless to say, I started spending my weekends in Buffalo! I would take the bus to the city and book a inexpensive hotel room for a night so that I could have time alone with Jerry. He had to live on campus as a freshman, and his dorm was never an option for us. Jerry paid for many of our weekends, as well. It turned out that his parents were quite wealthy. In addition to time spent up there, Jerry visited me in Binghamton many times. Joan was happy to see him, and Billy hit it off with Jerry right away. If Billy ever figured out our secret, he never mentioned it to me. My skill at all of the feminine "arts" grew, largely because of Joan's support and assistance. She would take me into her room and go over all of the tips and tricks she knew. I became completely passable as a female. Joan even bought me everything I needed or wanted for my wardrobe, often at her own expense. She said that, being childless, it delighted her to have a "daughter" at last. I grudgingly accepted her generosity. My grades suffered a bit due to my new, extracurricular activities, but I still made the dean's list when I graduated from Binghamton. Jerry spent the summer between my junior and senior year with Joan and me in her house. Billy moved out that May to study abroad. Joan gave Billy's room to Jerry and me as a love nest, of sorts. It was a wonderful arrangement. My lover and I spent day after day as boyfriend and girlfriend. I took a couple of courses during the days to add credits, and to justify my staying in Bighamton to my parents. It all worked out perfectly. This spring will mark my 30th year as Jerry's partner. I went on to grad school at Binghamton and eventually earned my doctorate. I wound up teaching there. Jerry left college after his sophomore year, but soon became a highly successful salesman for a tool and die firm. His family's connections played no small part in that. I would never have guessed back then that we would be together this long, but the spark between us during that first encounter grew into a passionate love that still excites and amazes both of us. I have remained a man during the day, or in company, but when I'm alone with Jerry I'm Tracy. Every now and then we go out as man and wife, and no one is any the wiser. Thank you so much for sharing your time with me. I wish all of you all the love in the world.