Mistress Psyche's Feminization Fantasies


Sissy Girl Stories



A Pretty Boy

By Nina

Chapter One

In The Beginning

My parents had one child, a boy, me. Many times I overheard them talking about me and how they wished I was a girl. I always felt a twinge of pain when I heard them say that but they loved me, always treated me very well and never said anything to my face so I pretty much ignored it. When I think back maybe dad’s parents felt the same way since he was an only child also. In retrospect it would explain dad’s secret hobby, as he and mom called it. It was a secret, or so mom and he thought but I knew about it. I had discovered it when I was about four. One night back then I got up in the middle of the night for a glass of water. The parlor lamps were lit so I crept very quietly past the door. I did look in as I walked by. I was shocked, if a four year old by can be shocked. I saw two women kissing on the couch only one of them looked like dad. Dad was dressed like mom. Over the next few years I saw them many times.

Sometimes I would listen to their conversations. I learned that my grandmother, who was a widow, dressed dad as a fulltime girl until he was eighteen. This was not that unusual in the late 1800s. By then he had come to love being a girl but had to give it up to earn a living. He did dress in the privacy of his home, just as he was doing now only he didn’t have to hide it from a snoopy kid. As I grew older I began to notice his clothes more closely. I could see his waist was incredibly small, even compared to mom’s. A bit of snooping in his closet disclosed that he wore, what I was to learn were corsets. I eventually learned that he had worn them from the time he was eight. My curiosity continued and at some point became a fascination. Little did I realize that fascination can become reality.

Dad was always bringing home little magazines, London Life I believe was their title, that he and mom would read them aloud together when I was in bed (?). They always dealt with men, and boys, dressing as girls. Invariably they were forced to wear corsets. I found them interesting in a strange sort of way. When I was almost ten I overheard one about a Victorian mother who decided to transform her son into what they referred to as a pretty boy. Pretty boys were young lads who wore some girl’s things, particularly heavy makeup, stockings (usually black), high heel boots, very tight corsets and tight, almost transparent blouses to show off the corset lacing, but were still identifiable as boys with short pants and boys’ hair cuts. Short pants were a must in order to display the silk stockings. According to the stories it was a common thing to do in England during the late Eighteen Nineties and early Nineteen Hundreds. About a month later my life became complicated and has been so ever since. It all started right after my tenth birthday. The year was 1910. One night she read one of the pretty boy stories to me after tucking me into bed. As she read I thought to myself that it would have been terribly embarrassing. They would have been better of being completely dressed as girls. I couldn’t imagine why she was reading the story to me. I was to find out why a few days later. I dreamt about it that night and woke frequently with the story racing through my thoughts. I didn’t understand why, but the story strangely fascinated me.

Chapter Two

The Metamorphosis

It all started out, thinking back, on a low key. In fact, to a ten year old, it was imperceptible. In those days it wasn’t uncommon for a mother to bathe a ten year old son. After drying me she, for the first time dusted me with a pleasant, flowery scented powder, casually commenting that dad always used it and I was growing up. I soon came to like it. In 1910 all boys my age wore corduroy knee pants called knickers. Some wore short pants during the summer. I always had worn the former all year round since mom thought it saved a lot of scraped knees. I was surprised then, when school let out for summer vacation that a pair of short pants appeared on the bed one morning. Mom commented that they would be much cooler. I felt a little embarrassed the first time I went out in public wearing them with my legs showing. I soon got used to them and went on with life. I was too na´ve to suspect anything was afoot. I never connected the sudden appearance of the bath powder and the short pants in my wardrobe to the stories. By now my bedtime stories had become excerpts from books similar to the first one. I was being brain washed by my parents. Of course ten year old children are very gullible.

One day as I dressed for church I noticed my ankle socks were different. They were white and came to my upper calf. They even had a lacy trim around the top edge. I commented that they looked girlish but mom told me that they were just dressy. They looked a bit sissified but weren’t too noticeable so I put it out of my mind, one more notch in my undoing. A few weeks later another subtle change took place. I always wore boxer shorts. After I was bathed and powdered, that was a standard routine, my underwear changed. My boxer shorts were gone. On the bed was a pink item similar to one I had seen dad wearing. It was explained that this type of underwear healthier for my ‘boy parts’. I didn’t realize that they were actually ladies panties. When I put them on the soft silky feeling was very pleasant. As time went on I failed to notice that the ‘shorts’ were becoming snugger. If I had I probably would have ascribed it to them shrinking in the wash. Besides, I rather liked the sensation.

Chapter Three

A Big Change

Over the summer mom was very fussy with my hair. She made sure it never got very long. Besides, I really didn’t care. Just before school was to start, I fell off my bike and wrenched my back. In those days people only went to doctors if they couldn’t stop the bleeding. Dad checked me out and except for a bit of pain I seemed all right. After a few days I had trouble walking upright and it still ached. As a result, one morning after my bath (everything seemed to take place after my bath) mom brought in what I recognized as a corset. “It’s one of mine," she explained. It will do wonders for your back. You’re just about my size and it is adjustable.” I looked at it closely. It was quite formidable looking. It had a lot of heavy strips running up and down its length and a row of laces down the back. Before I could say a word she had it wrapped around me and fastened the front clasp. I was turned around and the laces were tightened. “I won’t tighten it as I do when I wear it. You just need support not a new shape.” She tighten it until it felt pleasantly snug and my back felt better almost immediately. I reached from about two inches above my waist to part way down my thighs. I immediately liked the sensation of its firm stiff grip. Then I noticed some things hanging down from the bottom of the corset. There were four on each side of the corset. Mom saw me looking at them. “Those garters are a problem but I don’t want to cut them off since I will have to sew them back on when you’re through with your back problem.” We left it at that and I finished dressing. Since the corset wasn’t especially tight at the waist my clothes still fit. The garters hanging loosely in my pant (short) legs were annoying however. They jiggled and rubbed back and forth with every step. Before the day was over I was enjoying the secure feeling the corset gave me and my back did feel better. However, the dangling garters remained annoying. The only real problem was bending, but with my back I couldn’t do much of that anyway. Besides, it would only be for a few days, I thought. I would have to wear it to bed. Mom explained that it would help my back correct itself much faster. Since I was anxious to get better and be able to go out and play I went along with the idea.

 Each morning mom would tighten the corset a tiny bit tighter, so little that I actually didn’t notice it. However, the garters remained a nuisance. Every morning I complained about them. Mom was adamant. Finally the third or fourth morning Mom finished my lacing and went to her room. She returned with a pair of silk stockings: nylon hadn’t been invented yet. “Since the garters annoy you and I don’t want to cut them off you can try wearing these. They are very thin and flesh colored so no one will notice you are wearing them. They’ll keep the garters in place and you might even come to like the way they pull on your legs when you walk. Besides, your knee socks will cover almost all of them.” I protested mildly as she drew them up my legs. I stood so she could fasten the garters. I took a few steps and immediately I knew I liked them. They hugged my legs and, as mom said, they pulled as I walked and gave me a pleasant feeling.

A few days later I had become fully adjusted to my strange undergarments and felt lost when they were removed for my bath. A young mind can be easily confused and mine was becoming just that. I knew in a few more days I would shed mom’s corset, my back was feeling much better. For some strange reason I seemed to dread the idea. I was in a quandary. I couldn’t tell mom I wanted to wear her corset. Boys didn’t wear girls’ clothes although I do recall seeing boys who were dressed in an effeminate manner. Maybe the stories she read to me were true. Of course there was my dad. Little did I know then? I could pretend my back pains were coming back. At best that might give me another week but inevitably I would lose. As I mentioned earlier mom had been gradually tightening the corset. After two weeks my waist was smaller to the point where my pants almost fell off as I walked. I glanced in the mirror one night as I got ready for bed and noticed that I was acquitting a girl’s waistline. The next day mom measured my waist and later returned from the store with new pants. These fit my new waist perfectly. It did seem strange that she would spend money when she could have taken in the waist temporarily.

Finally it was decided that my back was healed and I would return to my uncorseted self. The first day was a nightmare. I was so acclimated to the corset that I could hardly stand when I got out of bed. A hot bath helped a lot. I was dried and dusted as usual. When I returned to the bedroom to dress I hoped that my corset would be lying on the bed, but no such luck. I was bitterly disappointed. It never occurred to my ten year old mind that I should regret having to give up wearing a woman’s corset. After all, dad wore one. By the second day I missed the secure and pleasant feelings it had given me more than I could have imagined. I heard it said many years later that wearing a corset was habit forming; some even called it an addiction. Mom had hatched her little plot carefully. Actually the back problem gave her an opportunity that she might have had to wait weeks or months to find. Without the back excuse, I might even have protested wearing it. Instead I fell into her plan, literally. The constant reading at bedtime of the unusual stories probably helped warp my thinking. I had come to like the stories. In fact I found them fascinating. I was going to become her pretty boy without realizing it. Mom had been watching me and noted my displeasure. She knew why I was upset.

One afternoon a day or two later she called me aside. “You seem to be walking strangely, does your back bother you?” Like a hungry fish I took the bait. I wanted to wear the corset and she, still unbeknown to me, wanted me in corsets. With my tongue in cheek I lied and said yes. Within minutes I was back in the corset and stockings. She laced me tighter than usual saying, “This may help.” I don’t know if it would have helped but it sure felt good. I had another problem. School was about to start. I could hardly wear a corset and silk stockings, even with the knee socks, to school. I would be close to the other kids and kids notice everything. A few of the boys wore corsets. It was not unusual for boys to wear corsets in those days but they were looked at as having ‘strange’ parents. For the several weeks I had been wearing the corset, silk stockings and knee socks my contact with other people was casual, on the street, shopping and church. Besides, I would never see most of those people again. The church was dimly lit so discovery was improbable. Mom had all the answers. She had been a teacher until I was born. It was decided that she would home school me for a while. While I secretly hoped I could wear a corset forever I expected that the back thing would come to an end in a few weeks and my corseted days would end forever. Besides, fall, with its cooler weather, was on the way and the short pants and sissy knee socks would also have to go. By October I would be back in school sans corset. My hair was kept boyishly short. “We wouldn’t want anyone to think you were a girl, would we?”, Mom frequently commented. By October the kids would be kidding me about trying to look like a girl. I would have preferred looking like a girl long hair and all. I probably would have been ignored.

My back was never mentioned again. I just kept on wearing the corset and stockings. I was sent back to school late in October. The faculty was skeptical but they had seen just about everything over the years. They were paid to teach, not criticize so they accepted their pretty boy. At first I was the laughing stock of the school. I was mortified. The girls were more sympathetic and more than just curious. The boys finally let up and more or less accepted me as a product of a strange mother. They realized that there was nothing I could do and finally actually felt sorry for me.

 My corset was laced progressively tighter, a little at a time until the back laces met. I had yet another new set of short pants to accommodate my shrinking waistline. It had been done so gradually that I didn’t realize it or have any discomfort; just an indescribably pleasant feeling of well being. I was much too young to realize that the sensations would someday have sexual connotations. For now it just felt good. For reasons I didn’t know, my knee socks were replaced with even fancier lacy ankle socks or anklets, showing more of my stockings. Since the latter were very thin and flesh colored they were hardly noticeable. I must have been incredibly na´ve not to have connected the pretty boy stories with my own situation. But then ten year old boys aren’t too swift. I was becoming a pretty boy and didn’t realize it.

It wasn’t long before mom decided that my corset was no longer suitable. Of course she didn’t want me to know that I was going to have my waist reduced even more so she just said that she wanted her corset back and mine would be replaced. I never wondered why she just didn’t take it and drop the whole corset idea. The next day we took the trolley downtown. I was to have a custom corset fitted at a corset shop. On the way mom explained that the new one would fit much better because it would be designed for a boy shape. That of course was a white lie. She knew I was going to have a woman’s corset of proportions I couldn’t imagine. A sign in front read, “JOANNE’S CORSET SALON”. I was embarrassed going in but then again any passersby probably assumed that my mother was the customer and I was being dragged along. We were expected. The receptionist greeted us saying, “Is this the young man who is to be fitted for his first corset?” I wished the floor would have opened up and swallowed me. While I had come to love wearing a corset I didn’t want the world to know. We were led into the fitting room where we met Joanne. She was a pleasant looking younger woman who, by the stiffness of her movements, obviously wore a very tight corset, even to a young boy’s eyes. I was told to remove all my clothes and put on a short slip. I had never worn a slip and the silky feeling against my body was more than pleasant. I felt a strange feeling in my lower area that I had never felt before. When I was suitably attired Joanne proceeded to take many measurements. I could understand the lower ones but was perplexed by the ones above my waist. Finally she finished and I was relaced into mom’s corset. Joanne mentioned that it didn’t do a thing for me but the new one would make a big difference. My new corsets, mom ordered two, would be ready in a week. As we made our appointment the receptionist commented, “His new corsets will be so much better. I’m sure he will love it.” I was on pins and needles all week wondering why the new one would be better. I assumed it would just be a little smaller.

Finally my big day arrived. We were greeted by the receptionist who reiterated her comment from last week, adding, “It’s a work of art. I ordered one like it for myself.” I was instructed to disrobe. Since I would be wearing the new corset home the slip was not used. Joanne held up the new corset. I was amazed, terrified and confused when I saw it. Mom said, “It just like I wanted,” meaning her not me. It looked incredibly long. It was designed to cover my upper chest and back, dropping low enough on the sides to clear my armpits. The front clasp was at least a foot long with small hooks above and below it. It had full length back lacing. Five garters dangled from each side. Two cups covered the upper chest. I would soon find out what they were for. I noticed that the waist appeared much smaller than mom’s corset. The heavy strips (I learned were called stays) were about an inch apart. I loved wearing a corset but this thing looked impossible. I commented on it. Joanne said you’ll get used to it in time just like the old one. It was soon fastened around me and all the clasps were secured. I felt like I was wearing a suit of armor. It extended from almost the top of my breastbone to three inches below my groin. Mom looked at it and commented that we will have to get some shorter stockings. Before the lacing began I could hardly bend in it. As Joanne began the lacing I felt a strange stirring. Suddenly my boyhood became hard. The length of the corset prevented it from becoming too noticeable but Joanne caught sight of it. “He’s a bit young for that but it usually happens to all the young boys when I lace them into their first corset. You are not the first one.” Suddenly she looked very pretty.

She ignored it and went about tightening the laces. I really knew I was wearing a corset now. I felt like I was cast in concrete, yet it felt wonderful. Joanne stopped tightening the laces before any discomfort was felt. “There is plenty of room for tightening as he gets used to it. I suggest not over a quarter of an inch a week. When a corset is tight even a small amount of tightening can be painful.” I didn’t understand why it was necessary to reduce my waist. She tied off the laces. From her desk drawer she removed two cone shaped pieces of fabric filled with something to give them shape. Now I found out what the chest cups were for. She unfastened the upper hooks on my corset, inserted the things into the cups and refastened the hooks. I couldn’t believe it when I looked in the mirror. I had a female shape. Just by accident (?) Joanne had a pair of short stockings that were drawn up my legs and secured to the garters. To my horror they were black. They stood out like a sore thumb. There I stood. A boy with the shape of a girl with the tip of his first erection peaking out beneath the bottom of his corset. I was speechless. I came to my senses when Joanne called in the young receptionist to survey her creation. Her comment was, “He makes a perfect girl except for one thing,” having noted IT peaking out. I was beet red. Again, by coincidence (?) Mom had a pair of short pants with a much smaller waist and a silky, almost girlish blouse with more chest room. The blouse was very thin, almost transparent, and very tight. My corset stays and lacings were plainly visible.

As we left the shop I felt like a freak. There I was, a ten year old boy with a very pronounced girlish figure walking along wearing a sissy blouse, short pants, black silk stockings and girls’ white ankle socks which emphasized the black stockings. I was the point of interest all the way home. Everyone we passed stared in amazement. Worst of all was the trolley ride home. Walking, I was observed by passersby and then they were gone. On the trolley however I had to sit, which I could barely do with my stiff corset, and have them stare at me for the whole ride home. Some men looked as though they wanted to laugh. Young women smiled and giggled. Some old ladies frowned while a few others gave approving smiles. I was never so glad to get there. Dad met us at the door. “You look very nice,” He said and nonchalantly walked away. It was decided that I would wear the new corset to bed to hasten my getting used to it. If I had a girlish shape now, what would I look like when the lacing was closed? As mom read my nightly pretty boy story it suddenly dawned on me. I was THEIR Pretty Boy and I only had myself to blame for not seeing it and going along with their plans. I was hopelessly trapped in a situation that I couldn’t get out of, but more importantly, didn’t really want to leave. I had come to love all my things, especially my new corset, tight and stiff as it was. That new sensation I had at the corset fitting was particularly wonderful and would repeat itself I was sure. Even at my young age I wondered, where will it end?

Chapter Four

A Pretty Boy Is Born

As expected, my corset was tightened little by little until I had a twenty two inch waist by December when the laces met at the waist. I secretly hoped that more waist reduction would be attempted. I loved the feeling but the appearance was unnatural. Not even young girls had a shape like mine. Mom tailored all my clothes to fit very tightly over my corset. All my shirts had been replaced by semitransparent girls’ silk blouses. The stays and lacings of my corset were plainly visible. Some of the kids at school still made comments from time to time, particularly in regard to my small waist and obvious breasts. Mom was following the stories to the letter. I used to wonder if the stories were true or just someone’s imagination. Mine was true. I was constantly embarrassed when we went out of the house. My feminine shape was plainly visible. Fortunately with the cold weather my tightly tailored jackets, while displaying my shape, hid the glimpses of my corsetry. Of course once inside, at a restaurant or church my jacket came off and my body restraints were there for all to see. Those who saw me regularly, neighbors and parishioners soon learned to ignore me or felt sorry for the boy in corsets. People in the streets either laughed or frowned at my plight.

While my waist reduction was going, other changes were being made. I was powerless to stop them. I couldn’t rebel. I couldn’t run away and I had no relatives to turn too. I was taken to a hair salon and had my boyish hair waved. The shop girls went out of their way to please the ‘different’ boy. I was introduced to lipstick, rouge and nail polish. I even acquired a pair of elbow length black patent leather gloves. I now wore girls’ shoes with high heels. Buying them was an embarrassing moment in my life. I’ll never forget being ushered into a woman’s shoe store. My short pants and hair made it obvious I was a boy although my other trappings were all girl. When the clerk, a young man of about twenty approached, Mom said, “My son is interested in seeing some girls shoes.” The clerk grinned and walked to the stockroom, pausing briefly to point me out to another male clerk. The warmth in the store and my anxiety made me start to perspire. Mom noticed it and told me to take off my coat. Now they could have a good look at the boy in corsets. I had to stand and walk around the store with every pair I tried on. By the time we had made our selection every clerk and customer had seen me. I ended up with several pair with two and three inch heels. She also bought a pair of black patent leather laced up knee length boots with four inch heels. Every time the clerk fitted me with each pair of shoes he gently rubbed my silk stockinged leg. The clerk asked rather sarcastically if I wanted to wear a pair home instead of my boy shoes. Mom jumped at the idea saying, “He will wear the boots. The extra support will make it easier to walk in them.” She couldn’t help adding, “I’m sure he would rather wear even higher heels but they might be too high for a starter.” As we checked out, the young lady at the register gave me a smile and said, “I think you look nice.” Then she added, “Things could be worse.” I wasn’t too sure about that. As I stepped outside on my wobbly feet I couldn’t help thinking, “It’s just like the story, now I really am a pretty boy.” I wished that she would buy me dresses and get it over with. In dresses I would look like a girl and there would be no embarrassment. I still wanted to be a boy in my heart but with only two apparent choices, pretty boy or girl. I would prefer girl. Such was not my lot.

As I tottered along in my wobbly new boots it wasn’t long before mom led me into a jewelry store. She spoke briefly to a young girl clerk who led me to chair not unlike barber’s. She couldn’t stop starring at me, no doubt wondering what I was; boy or girl. I was sure that she realized that I was a pretty boy since they weren’t uncommon in 1910 England. She did comment on how pretty I looked as she placed a smock over my shoulders and had me sit down. What happened next shocked me. She proceeded to pierce my ears. I was horrified. Now I would be marked for life. She commented, “You’ll come to like them. They won’t keep falling off like the clip on ones do. Mom bought several sets, one of which I wore home. Now I was even more embarrassed. Mom’s pretty boy was about as completely feminized as I could be without wearing a dress.

 When spring arrived I was still a pretty boy. I regularly wore a delightfully frilly tight white, thin silk blouse, very snug black satin short pants and black silk stockings without the usual lace trimmed white ankle socks to church on Easter. I wore rouge and lipstick. It was very warm so a jacket would have been out of place. The pants were extremely short, almost to my stocking tops. Another inch and I would have shown my garters. By this time she had bought me a black corset. The white blouse was all but transparent, displaying my tightly laced corset and its structure. I had begged mom to give me a slip but she said it would spoil the effect. I even had to wear a little ‘pill box’ hat that was a popular item with the girls back then. Mom had arranged my hair to suit the hat. I wore a lovely floral corsage. A real girl would have loved to be dressed as I was, with a skirt of course. I was the talk of the church congregation.

Chapter Five

Pretty Boy Adapts

In some perverse way I was beginning to enjoy the attention I was receiving. Pretty boy was on display. Somehow I was beginning to like the sensation of being feminized but most of all I had come to love the feel of my corset and heels. As a now twelve year old boy I wouldn’t have received a second glance. Much of the attention was negative but there was enough positive attention to offset it. Clerks in stores and waitresses in restaurants would stare enviously at my delightfully small corseted waist. Young girls particularly seemed fascinated with me. Some would even speak, telling me I was pretty, or cheer me up if I looked sad. Several even commented that they wished their pesky brothers were dressed as I was. Others were amazed at my figure and would try to examine my corset through my blouse. A few actually asked to touch my waist. They would ask how I could stand to be strapped in so tightly. My response was simply, “You get used to it over time.” Little boys and girls usually just looked in amazement. The most puzzling ones were young men. And older men, who rather, than making fun of me, seemed genuinely interested. An occasional one would fondle my corset. Any touch, boy or girl, always caused an erection. A couple of older boys, not realizing my age, quietly asked me to go out. At the time I didn’t understand why a boy would want to date an oddly dressed obvious boy. I found out a few years later. I wondered though, if I was older would I have accepted?

One aspect of my public appearances was more unusual than my pretty boy look. My underclothes had been modified in an unusual manner. I had been fitted with a sheath that held my penis. Straps from the tip of it were fastened to the side garters of my corset. As I walked the straps caused my penis to move from side to side causing me to be constantly aroused. My short pants, while generally skin tight to show the cut of my corset, were cut rather full in the crotch area allowing the contour and movement of my rigid penis to be observed. Since I was well endowed, as mom said, it was quite obvious. Being a pretty boy wasn’t really all that bad. I had long since discovered the pleasures associated with my ‘problem’. I always took a towel to bed. Besides I loved wearing a corset and all the girl things. If only I could wear a skirt or dress my young life would be complete.

I spent the next two years as a pretty boy and was completely taken by it. I no longer cared what people said about me. I resolved that this was my life style at least until I was of age at twenty-one so I would make the best of it. When I was fourteen we move to a new house in the suburbs. Of course I was the talk of the neighborhood. After the neighbors found out I was just a harmless nut, as some of them put it, I received some degree of acceptance. Perhaps it would be more accurate to say I was tolerated. After we moved I got the surprise of my life. When I returned home from the store I found a strange lady talking to mom. I move closer and was shocked to recognize dad as the lady. After all these years he decided to give up his little secret. He was embarrassed when I spoke to him. He explained that considering the condition of his son it was pointless to hide his other life from me. I wondered why he waited so long? From then on he became a woman as soon as he returned home in the evening. He never ventured out of the house as a woman however. In spite of everything that had transpired I was not allowed to be a girl. I was always referred to by my given name, Andrew or as he, never she. By this time I was sure however, that when/if the opportunity arose I would chose to spend my life as a female.

When I was fifteen a new family moved in next door. They had twins, a boy and a girl about my age. The parents weren’t even surprised to find a ‘strange’ boy living next door. The twins, Leslie, a boy, and Lynn, a girl, seemed curiously attracted to me. I had expected otherwise, especially with the boy, Leslie. Lynn of course wore a corset, as did all young girls. It was obvious that Leslie wore one also, a bit strange but then who was I to judge? We became friends. I noticed the twins were the same height and build. They even looked alike, a bit unusual for fraternal twins. I was happy with this turn of events. Now I had two people I could talk to, no more lonely days.

I now usually wore boots and shoes with four-inch heels. I’m sure that I looked ridiculous as a boy prancing around in short pants and spike heels but I had come to love every minute of it. My new friends accepted my idiosyncrasies and me so what did I care. Besides, the heels did wonders for my legs. I was proud of them and hoped to show them peeking out from under a skirt someday. Even with things the way they were I frequently got whistles and catcalls of approval. By now I knew why some boys and men found me attractive. As my friendship developed with Leslie and Lynn I noticed that from time to time there were subtle day to day changes in their personalities but rather than trying to figure it out I let it go. One day an invitation came in the mail. Their parents were having a get together dinner for my parents to get better acquainted. Apparently they accepted my lifestyle and me. I had only met them casually when visiting with the twins and they always seemed unperturbed by my appearance.

 For some reason I had been asked to arrive early. I dressed in my best things and walked over, enjoying the sound of my boot heels clicking on the walk. My knock on the door was answered by two young ladies. One was Lynn. I looked again. Both were Lynn. Then it dawned on me. One was Leslie. He was a crossdresser. But which one was which? They looked and dressed exactly alike. That was why I had sensed a personality difference on occasions. They were having fun with me by switching positions. I was so glad to meet kindred spirits that I hugged them. They were wearing corsets like mine. They admitted later that they loved wearing them. The reason for having me arrive early it turned out was to give me time to grasp the situation. We sat and talked. As we did I received another surprise. They were twins all right. They were identical twin boys. There was no sister. They just took turns playing sister for the fun of it. I sat speechless until my parents arrived. They couldn’t believe their eyes. No wonder their parents accepted me. I was one of their kind. Much later I was to find out that there was even more to it. I was mildly disappointed that Lynn was a boy. I had hoped to find a girl who could accept me for whatever I was. Both Lynn and Leslie were great friends and I was sure we would find many interests in the days to come. The rest of the evening was uneventful. Mom and dad became good friends with the twins’ parents, Ed and Elaine Richards. Pretty boy was happy. He finally had some real friends.

Chapter Six

Pretty Boy Really Adapts

We “girls” started visiting regularly. Whenever it got late the visitor or visitors would stay overnight. Since both families had plenty of room there was no problem of sleeping arrangements. At home the twins shared a large bedroom decorated in feminine motif. I had the guest bedroom. At my house the twins shared the guest bedroom. Our parents seemed eager for us to have sleepovers. One night as I was about to go to sleep, Lynn and Leslie came into my room. They had decided to say goodnight again. This time it was with a kiss. It was not an ordinary goodnight kiss. These were full on the mouth with a little tongue. When they finished Lynn, or was it Leslie gave my now rigid member a gentle squeeze and left. I was confused. I had never been kissed by a girl let alone a boy. It should have been repulsive but it wasn’t. After all, they looked like pretty young girls. In my aroused state I enjoyed it. I spent a restless night dreaming of fondling and kissing the twins. The next morning we had breakfast as usual and I returned home where I would have a bathe and change corsets. Mom no longer bathed me but she did lace my corset. I was always aroused as she laced me but ignored it, although one time she did comment on my generous endowment. “Some day you’ll make some lucky girl, or boy happy”, she whispered slyly. I couldn’t believe she was condoning a relationship with a boy. But then again, why else was I kept dressed this way?

 A month or so later my parents took a short vacation. I would be staying with Lynn and Leslie. As usual they kissed me goodnight, French style and left. The first morning after my bathe they offered to lace my corset. Whenever Mom laced me I always had an erection and was naturally embarrassed. I knew before we started that I would have the same reaction. They came into my room wearing only their under things; corsets, stockings, heels and peignoirs. The sight of two lovely boys in corsets and skimpy attire immediately excited me. I already had my corset wrapped around me. My erection poked out below my corset edge and they were quick to notice it. It was obvious they were having a similar problem. The sight of them made my nerves tingle. I had never seen another male organ let alone an erect one. Yet here were two right in front of me. For a moment I had the strangest desire to touch one. They lost no time in lacing me. Putting on stockings when tightly laced was always a problem. Lynn offered to help me. As he fastened the garters he purposely brushed the tip of my erection. I shuddered at the touch. No one had ever touched it, except me of course.

When they finished lacing me Leslie suddenly kissed me as Lynn reached under the edge of my long corset and gently fondled me. Just then their mother called them for breakfast. I wondered what they, and I, would have done next. We quickly pulled on heavy panties to hide our excitement, finished dressing and went downstairs. Their mom had a little smile on her face as she asked us what took us so long. We considered it a rhetorical question and sat down to eat. To my amazement the twins never let up. All day long they were feeling and pawing me. It kept me in an extreme state of excitement all day. On occasion they would break off and ‘play’ with each other. I wondered what kind of a relationship they had with each other in their shared bedroom? It wouldn’t be long and I would find out. I had trouble eating lunch and dinner that day. In my wildest imagination I never dreamed that a pretty boy could feel so excited. If I had been dressed as a girl I was sure there would have been many hands up my skirt that day. I secretly wished there had been. I had never kissed or even touched a girl so I had no idea of how a girl could excite me. I did know that a boy could.

After spending a whole day sexually excited I was tired and anxious to relieve myself, so I retired to bed. Shortly after I turned down my bedroom lamp I heard my door opened and the twins entered wearing only their corsets and stockings. Within seconds they were in my bed, one on each side and were fondling me. I was in no mood to resist anything; in fact I welcomed their advances. One of them started kissing me as the other continued fondling me. The feeling of a tongue in my mouth was exciting. In a moment my tongue was in his. Soon they had the lower hooks on my corset unfastened allowing my erection to stand out. I felt a hand wrap around it and start stroking it. It felt wonderful. Almost as a reflex I reached for one of them and took hold of his penis. As I did a shudder ran over my body. I had never touched one other than mine. It was a tremendous thrill. Because of the day’s activities I was already very excited. Within seconds, or at least that’s the way it seemed. I pumped my load like never before.

I never had a chance to get soft. I felt a pair of lips encircle me and a tongue began licking my shaft. I immediately grabbed my other partner and began stroking him. He suddenly moved and positioned himself over my face. His penis touched my lips. I knew what he wanted and in my moment of passion opened my mouth and let him enter. It tasted salty but not unpleasant. Following the example of what was being done to me I started licking and sucking as my lover bucked his hips and drove it deeper into my now eager mouth. I managed to reach my other partner and began stroking his shaft. Within a few minutes all three of us exploded almost at the same time. My mouth was flooded as I swallowed trying to keep up with my partners’ pulsations of pleasure. Not a word had been spoken. We kissed goodnight and they went off to their room, to do what I could only imagine. If sex with boys was that exciting what must it be like with a girl? Somehow I couldn’t imagine it being more pleasurable. Within a few short minutes I had been transformed from a boy into ?

In the ensuing weeks I became insatiable. We would sleepover as often as possible. Did our parents know what was going on? Maybe it was part of a plan. I learned that the twins had been having sex together ever since they were able to. I also learned that their parents condoned it. That was why they slept in the same room when their house had several bedrooms. They had been dressing as girls since they were babies. They had been corseted since they were eight. Except when playing ‘pranks’ they never wore boys’ clothing. How I wished that I could wear a dress. It was a shame. Constant tight lacing had given me a lovely female shape, yet I was still a now nearly sixteen-year-old pretty boy. The twins had taught me how to be a girl and I wanted to look like one. During our sessions I had been introduced to more sex episodes than I imagined existed.

Chapter Seven

Pretty Boy Becomes a Woman

One evening during one of our love making sessions, Lynn suggested that I remove my corset. I couldn’t figure out why. I loved to wear it. There is no sensation more sexually exciting that feeling a tight, stiff corset squeezing one’s body. The feel of it seemed to make sex more thrilling. I reluctantly did as he asked however. Leslie turned off the lights. “We have a surprise for you, we do this all of the time,” he said softly. I was told to lie face down on two pillows placed under my hips. I couldn’t imagine what was to come next. Then I felt a greased finger enter my anus. A slight twinge of pain was followed by one of pleasure. After a few in and out motions he inserted a second finger and then a third. Then he withdrew them. I would love to have had them remain inserted all night, but what followed was infinitely better. I felt Leslie crawl on top of me. As he did Lynn remarked with a giggle, “You hog all the fun.” In an instant Leslie placed his member against me and proceeded to insert it slowly. I was beside myself as he moved back and forth. Every nerve in my body tingled. Lynn began stroking my penis as Leslie increased the tempo of his thrusts. Lynn then had me turn my head sideways as he positioned his member in front of my face. I eagerly accepted him in my mouth. The position was a bit awkward but acceptable. I was now being screwed in both orifices at the same time. If this was the way women felt, I envied them. Just as I thought I would go out of my mind with pleasure Lynn and Leslie came almost simultaneously. I came without having anyone touch my member. I was no longer a virgin. Our previous episodes had been wonderful. This one was indescribable. As I rolled on my back I had semen running out both ends of me. As I laid in bed reveling in my ecstasy I heard Lynn say, “Now it’s my turn.” At that point I didn’t care what they did. Within seconds I was on my stomach again and feeling Lynn enter my body. Leslie presented his member to my waiting mouth and the whole episode was repeated. Since this was the second time for us it took much longer to climax, to my great delight. It was quite a night. Even now, fifty years later I can still relive that experience. They made a woman of me. The following night I had the pleasure of playing the boy with both of the twins. It too was a wonderful experience although it didn’t compare with playing the girl. I was almost sixteen and just had my first experiences. How I envied Lynn and Leslie for the years of enjoyment they had experienced.

After several months of our sexual reverie I turned sweet sixteen. The rest of the saying, “And never been kissed” was a mockery. I had been kissed every way it was possible. Of course way back then a sixteen-year-old girl was always (?) still a virgin. Anyway, the twins and their parents celebrated my birthday with my parents and me. When it came time to open the presents I started with those from mom and dad. I could have fainted. The first box contained a lovely dress. I was no longer a pretty boy; I was to become the girl of my dreams. There were other dresses and petticoats and a variety of real girl’s things. I was so happy I cried. I excused my self and ran off to my room carrying a pale yellow dress and matching shoes. It was a perfect fit and showed off my twenty-inch waist delightfully. I freshened my makeup and returned to the party. As I entered the room I twirled around allowing my skirt to fly above my stocking tops. My parents and guests smiled and applauded. This is what I had wanted for six years and now my dream had come true. Pretty boy was gone. Andrea was born. As time passed I sometimes regretted giving up my pretty boy experiences. I had come to like, in a perverse way, the attention I received as a pretty boy. As a girl I only received glances from passing boys.

Lynn and Leslie remained friends and we spent many pleasant and exciting times as sex partners. Still I longed for the touch of a girl. Since that seemed impossible I decided to enjoy their attentions. The three of us were enrolled in a private girls’ high school. There was no problem with this. In the early 1900s England voluminous clothing and rigidly enforced privacy precluded our discovery. Of course we shared a room at school. At eighteen we graduated. The head mistress planned a graduation party together with a nearby boys’ school. Our parents went to great lengths to ensure we were the best-dressed, prettiest girls at the party. I was corseted to nineteen inches in my new corset for the occasion. It was even longer and stiffer than my previous ones and felt delightful. My only regret was, as with all my corsets, the corset covered my breasts. Years of uplifting corsets and mother’s regular massage had given me a lovely pair. Of course the corset covered them so my dress had to have a high neckline. Mom suggested a short corset but the delightful sensations of wearing a restrictive full body corset was more than I was willing to give up just to display my features. The twins felt the same way.

Chapter Eight

The Party

The night of the party we were rigidly laced from armpits to mid thighs in our new corsets after which we donned our lovely white satin formal gowns. They fit like a glove. The outline of every corset stay and the lacings were quite visible. Leslie remarked, “Boys love corseted girls and it pays to advertise.” No other girls could hold a candle to our corseted figures that night. One could read the envy on their faces and the lust in the boys’ eyes. We were inundated with suitors. As I danced I could feel my escorts pressing their manhood against my thighs. I found the sensation thrilling. As I became bolder I started grinding my thighs against them. The feeling along with their hands groping my corseted body was very stimulating sexually. After a few dances I selected one lad, Larry, who I found to be particularly attractive. A glance at Leslie and Lynn revealed that they did the same thing. During the orchestra breaks we would wander out into the garden area.

With each trip the petting grew more intense. Fortunately our long corsets hid our erections that were more or less continuous since the first dance. Just as with my experiences with the twins I knew my dance partner expected something more than a mouth full of tongue. I had never experienced anyone except the twins and was dying to have an experience with a stranger. Larry was soon groping under my skirt with his hands as his tongue probed my mouth. I knew that before long he would reach my manhood and my secret would be lost. To dissuade him I unbuttoned his fly (no zippers back then), took out his manhood and proceeded to stroke it as I had done to the twins many times. He soon lost interest in fondling me as I dropped to my knees and orally brought him to a tremendous orgasm. He flooded my mouth. It was probably his first with a “girl”. As the evening progressed we had another tryst. Since our lovemaking was one sided I didn’t enjoy it as much as I did with the twins.

Toward the end of the evening Larry went off to the men’s room. To my surprise and amazement a young lady, named Helen, one of my classmates, walked up to me and asked me to dance with her. Halfway through the dance she guided me off the floor into a small alcove. She smiled sweetly at me as she said, “You sure believe in tight lacing, especially for a boy.” I was shocked and speechless. She continued, “You have fooled everyone except me. I’ve watched you in school for a long time. My father is a crossdresser and I can spot one a mile away. You and your two friends are very good. Don’t worry; your secret is safe with me on one condition. You three must become my friends. I have been fascinated with the thought of meeting a crossdresser ever since I found out about my dad. Three at one time is unreal.” I had always wanted to meet a girl who would accept me so I willingly agree. I was sure that the twins would have no objection; after all, did they have a choice? I pointed out that they were only interested in boys she asked about my preferences. I admitted that all of my experiences were with boys but only because meeting an accepting girl seemed highly improbable. She assured me that I had just found one. Our friendship grew and we began dating frequently.

Chapter Nine

A Way Of Life

Her father, I found out was indeed a crossdresser. He also owned a business. She apprised him of my true identity, which he willingly accepted, and offered me a job as his secretary. One of my duties was to spend a few minutes under his desk occasionally. Helen had no objection and neither did I. In today’s jargon I was (and am) bisexual. We became engaged at which time, reluctantly, my relationship with the twins became more one of friendship although Helen condoned an occasional tryst with them. A year later Helen and I were married by and old pastor and friend of her father. The twins were Helen’s bridesmaids. We set up a household as sisters to the outside world. Her father’s business grew and I eventually became the president. Periodic sessions under the desk, when her father stopped by, reminded me of whom I really was. Some of the older employees silently objected to a “lady” president but so be it.

Eventually we became parents to twin boys. We put them into dresses at an early age. After all it made it easier for them to understand that the other woman in their lives was their father. They went to school as boys. At home they became pretty boys after school, weekends and holidays. During these sessions they were strictly corseted and wore makeup and trappings similar to those I wore at that age. Outside exposure was not considered since we were now well into the twentieth century and pretty boys were no longer accepted. After a few months they begged to wear their corsets full time and go outside but we refused to let them. We did allow them to wear corsets and dress as girls whenever we went away on vacations. At home they wore corsets day and night and were our pretty boys.

Today, many years later, Andrea (I) still wears the old style corsets and dresses as a woman. After all, I have a business to run. I am still happily married to an accepting wife (Helen) and family. Perhaps my boys accept dad because he controls the purse strings but I don’t think so. My twin sons have become avid crossdressers. They in turn have introduced their boys, my grandsons, to the pleasures of wearing corsets and feminine things. Will it yet pass to another generation? It is said that the older one gets the more it becomes an obsession. There is no doubt about that. I have yet in my lifetime, since I was ten, to wear trousers, socks, a starched shirt or heels less than three inches. I still corset 24/7.

The End

(Or is it just the beginning?)


Sissy Girl Stories