• Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • Boys in the Attic

Boys in the Attic

123

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.

123
  • Index
  • /
  • Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • Boys in the Attic

All contents © Copyright 1996-2023. Literotica is a registered trademark.

Desktop versionT.O.S.PrivacyReport a ProblemSupport

Version ⁨1.0.2+795cd7d.adb84bd⁩

We are testing a new version of this page. It was made in 17 milliseconds