Mistress Psyche's Feminization Fantasies


Sissy Girl Stories



A Boy Lost

By Nina

It all started at the turn of the century.  The St. Louis Worlds Fair was in full swing.  My name was Ken.  I had just turned thirteen and was a feisty lad I have to admit.  Incorrigible might have been a better description.  That proved to be a key element in changing my life.  Mom had died when I was six.  Dad, my sister Jane, a year my senior, and I had lived alone ever since. Now dad was not a manly man.  In retrospect I would call him a Mr. Milktoast type, easy to push around.  He was very lonely however.  One day he brought home a lady and announced that they were to be engaged.  I learned she was wealthy in her own right.   Dad was well fixed and couldn’t have cared whether she was rich or poor.  I resented her for no real reason and didn’t care much for her.  She was just the opposite of dad, rather forceful.  When I was introduced to her she acted pleasant enough although she stared at me with a strange look in her eye for the longest time.  If I could have read her mind I would have run away but I couldn’t and didn’t and am glad I didn’t.  A few months later they were married and she moved in. She and Jane seemed to hit it off.   We were instructed to call her mother.  I also resented that but said nothing.  Jane didn’t seem to care. 

After a few days she became aware of my feistiness and announced she would hire a governess to, as she put it, quiet me down a notch or two. The governess was a fiftyish woman, who wore nothing but long formfitting black dresses.  All women over twelve wore long tight corsets. She was no exception.  In spite of her age she had the shape of a teenager.  She must have worn a dandy.  I learned she was also a qualified tutor, meaning that our school days were over.  I was to call her Madam Gayle.  Madam was a normal title of address for a governess at the turn of the century.  My life was pleasant enough in spite of the fact that I was getting a lot of discipline.  My feisty streak was not easy to break however.  Even an occasional caning by madam didn’t seem to help.  Mother would often say, following one of my unruly periods, that if I were her daughter she could quiet me down.  I wondered how she could quiet a girl and not a boy.  I would soon find out, the hard way.

One day following one of my episodes and after a long talk with dad, she pulled me aside and said merely, “It always works with girls, there’s no reason it won’t work with you,” and walked away.  I was on pins and needles wondering what she had in mind.  The next day she went shopping with madam.  They returned with a lone package.  “We bought a surprise for you, I’m sure you will come to like it eventually, most boys have,” mother said. “We’ll start tomorrow, when you get up.”  Now I was worried.  All that evening Jane would giggle whenever we met.  What did she know?  Finally, just before bed, Jane whispered, “We girls love them, you will to,” and walked away laughing. I barely slept all night.  I arose and washed up.  When I returned to my room, mother and madam were waiting for me.  My eyes fell on an open package on the bed.   A felling of terror crept over me.  I recognized it because I had seen Jane wearing one.  It was a corset but it wasn’t at all like hers.  She normally wore a fairly short waist cincher.  This one was very long, almost two feet it appeared.  I was informed that it was mine.  I was to wear it until I settled down.  The term used was petticoat punishment. 

I protested loudly,  “I won’t wear girl’s things, especially one of those.”  “You’re only making it worse for yourself and you will wear it.”  She picked it up and moved toward me.  I was ready to run when madam stepped up and held me.  She was much stronger than a thirteen year old boy and I gave in.  In seconds it was wrapped around me.  It was a new style I was informed.  It covered me from my shoulders to below my crotch.  It had cups that covered my chest and shoulder straps.  A steel clasp about a foot long, called a busk, fastened the front together.  Several hooks and eyes fastened the corset together above and below the busk.  Vertical steel strips, located every couple of inches apart were sewn around the corset.  This was to be my prison.  Madam held me as mother started tightening the back laces.  She had barely started and it was already becoming uncomfortable.  Soon I felt like I couldn’t breath, but she continued tightening the laces.  Just when it reached the point of pain she stopped.  “That will do it for now.  There’s plenty of slack left.  As soon as he get used to the feeling we’ll do some serious lacing.  Serious lacing? I thought, what do you call this?  I was immobilized. I couldn’t bend and I knew even walking wouldn’t be easy.  Mother stuffed some pieces of cloth into the breast cups and tightened the shoulder straps.  I looked in the mirror.  I had the shape of a girl but not an ordinary girl.  The corset was the new ‘S’ shape style giving me a sway-backed appearance.

Then a very embarrassing thing happened.   I had my first erection.  The older boys in school had kidded about getting erections and now I had one.  The corset was so long it was barely noticeable but it was there.  The two women said nothing but went on dressing me.  A pair of silk stockings were drawn up my legs and fastened to the four garters on each leg that hung from the bottom of the corset.  By now the pain was easing and I found the feeling of wearing a corset to be somewhat pleasant, although I would never have admitted it.  The stockings tugged on the garters as I moved, giving me another rather pleasant sensation.  If I were a girl I would have loved it. As a boy I had mixed emotions.  As if to add insult to injury madam called to Janet. “Come and see your brother, he has just as nice a figure as you have.”  She came running.  When she saw me she felt my body and exclaimed, “ If I had a corset like that I would have a better figure than him.”  I didn’t just blush, I was crimson.  For the present, I was allowed to wear my regular clothes.  My pants were totally loose at the waist and my shirt plainly showed two prominences where my chest had been flat the last time I wore a shirt.  The ‘S’ curved shape of the corset certainly didn’t help either.   Mother then commented, “Maybe we should reconsider the tutoring and send him back to school.  His classmates will enjoy seeing him.”  Thankfully she was only kidding me, yet I took it as a veiled threat. 

I had hoped that when dad came home from work he would put his foot down and stop this.  I couldn’t believe my ears when he saw my exaggerated shape and said,   “With a figure like that it’s a shame to hide it under a boy’s outfit.”  He was in league with mother and madam.  Now I had to worry about them taking him up on his hint.  To add to my torment I was advised that Madam Gayle would attend to my corsets every morning.  If she was busy, Jane was to take over.  Madam lacing me was bad enough but the thought of my sister performing such an intimate act was inconceivable.  I would rather have had a daily caning.  I had no idea how long this travesty was going to last.  I decided that if I behaved it would end soon.  At that time I didn’t realize that my behavior had nothing to do with my predicament.   It merely started a chain of events. 

Days turned into weeks, which turned into months.  I was now accustomed to wearing my corset.  Little by little the laces had been tightened until there was no slack left.  I was rapidly acquiring a wasp waist.  I had come to accept my corset and was starting to find the tight-laced sensation to be very pleasurable.  I loved the way it embraced my body and pressed against sensitive areas.  I had almost a constant erection.  Wearing a corset was rapidly becoming a way of life.  No mention was made of stopping my punishment although my behavior had been above reproach.  Actually, laced as tightly as I was, it was difficult to be anything but good.  I regretted that I couldn’t go out to play.  It was summer and without a coat it was too embarrassing to go anywhere.  My shape was very stylish and beautiful but not for a boy.  Being corseted I became aware of others wearing corsets on the rare occasions when I was forced to leave the house.  I saw a small number of boys and young men who had exaggerated shapes like mine.  At least I wasn’t alone in the world.  I was now in my third month when mother announced that it would be better for my shape if I wore my corset to bed.  If this was further punishment it wasn’t going to work.  I was hooked on corsets and looked forward to wearing them all the time.  I was just into puberty and found that being corseted at night inspired some ‘nice’ dreams.

As I mentioned there was no slack left in the laces and that fact was duly noted by madam and mother.  One morning I was told we were going shopping.  I dreaded going out because of my shape.  Fortunately it was a rainy day and I wore a mackintosh that hid my figure.  Any girl would have loved my shape and I was secretly learning to do so, but not in public.  I had no idea where we were going until I was ushered into a corset shop.  I wanted to die.  Within minutes I had several new corsets.  My old one had a twenty-four inch waist.  The new ones were twenty-one.  “These should hold him for a while” the shopkeeper commented, “ there’s plenty of adjustment left.” I had come to like my corset but further tightening frightened me.   I was going to become a freak of nature.   There was no way my trousers could ever fit with such a tiny waist.  That was soon to cease to be a problem.  Before we left the shop mother engaged in an extended conversation with the owner, a forty something, attractive woman named Sally.  When we reached home she dropped a bomb on me.  It seems mother and madam had decided that I should have something to do in my spare time.  It seemed Sally told mother that I looked so nice as a tight-laced boy that it would be good for business for people to see what a corset can do for a boy’s normally unattractive shape.  I was going to work a few hours a week as a manikin in her shop.  The newest styles and finest corsets would be at my disposal.  I was appalled. I protested to no avail.  I was already hired.  What further indignities had they planned for me?  Working in a woman’s corset shop modeling corsets for all to see was too much and I broke down and cried.  If any of my friends heard about it I would be the laughing stock of the neighborhood.  Then again, I hadn’t seen any of them since I was put into corsets but they would remember “the corset model” when this was all over.   As I pondered my fate I suddenly thought it might not be so bad being laced into a variety of corsets. 

Promptly at two o’clock my tutoring ended and I was informed that madam would escort me to the corset shop.  I was also informed that my earnings would be donated to a charity.  It was still summer and I was escorted, without a coat to the shop.  My diminutive waist, now at twenty-one inches along with my ‘S’ shaped figure was the subject of much ridicule from passersby.  I cringed when I saw the sign in the shop window. In large blazing letters it read:



As soon as I entered the shop I was told to remove all my clothes.  I was instructed to put on a panty in case I had a ‘problem.   I was then laced into a corset selected by Sally as the special of the day.  I was handed a peignoir, stockings and high-heeled boots and told to put them on.  Minutes later I stood in the shop for the entire world to see.  My hair was long, most boys had long hair then, so the Sally decided that, as she put it, I would look more feminine with a pretty Grecian style headband.  A touch of makeup was applied.  I looked more like a girl than a boy.  I was confused but for some reason I liked what I saw.  The rest of each day was spent modeling a variety of corsets.  When not actually modeling for a customer I had to stand in the window next to the sign.  I was terrified that one of my friends might see me.  The customer would select a corset style and I would go behind a screen where an attendant would lace me into it.  I would then parade in front of the customer without my peignoir. The lady customers thought it was cute to use a young boy for a model.  The young girls, some getting their first corset, were amazed at what their prospective corset could do for a boy and dreamed of what it would do for them.  Some kidded me.  Over the next few weeks I was surprised at the number of boys who were brought in for corsets.  Some were upset. Others seemed to relish the idea or wearing a corset.  Most of them were put at ease on seeing a boy modeling the corset they would soon be wearing.  My appearance definitely stimulated sales.  Sally was well pleased with her idea.  Some of the corsets were absolutely beautiful.  Many were unbelievably restrictive.  I came to love the attention I received.  I was actually looking forward to my ‘job’ by now.  If I had to wear a corset constantly, why not donate a few hours a week to charity?  I even got used to the embarrassing walk to work.

 All this time my father remained silent.  He was either in full accord with what was going on or he was afraid to say anything.  My new mother was very assertive, one might say overbearing.  One afternoon she and my dad walked into the shop. I naturally assumed that she either wanted to see me or needed a new corset.  It was the first time she had seen me at ‘work’ and seemed pleased at what she saw.   She examined the display corsets and finally selected one that made my corset look like child’s play.  It was very long.  The lower part from the crotch down resembled pant legs and extended to a few inches above the knees.  Each ‘leg’ had a set of full-length laces.  The upper section was similar to mine in that it had cups over the chest and heavy shoulder straps.  An attendant selected one in my size and we stepped behind the privacy screen.  It took about twenty minutes to get it on me and laced.  I felt like I was in a prison.  I couldn’t sit.  Walking was difficult.  I then paraded in front of my parents as best I could.  Finally mother nodded her head in approval.  I couldn’t figure out why she would want to wear such a constrictive corset.  Was she going to entrap me in one of them?  I hoped not, but then again?  Then I received the shock of my life. She spoke privately to the attendant who walked over to my father and measured him.  The corset was for dad.  I pitied him, yet he didn’t look at all concerned. In fact I thought I saw a faint smile cross his face.  It was obvious that mother ruled the roost.  Dad was to wear a corset.  He might even have asked for it.  No wonder he remained silent when she started me on a corset regimen.  A corset like that, with the legs separately laced could and, I was sure, would be worn underneath his business suit.  A half hour later dad and mother walked, or rather she walked, dad sort of shuffled out of the shop. It was closing time so I left with them.  What an odd sight we must have been.  A weird looking boy obviously very tightly corseted, a woman and a man barely able to walk.

Like me, dad wore his corset constantly.  He had one advantage.  Upper class men always wore a suit so his corset was concealed.  I, on the other hand was obviously tight-laced to everyone who saw me.  I had become used to the hoots and cat- calls I received walking to work.  At my ‘job’ however I was admired and fussed over.  As an ordinary boy I never would have received the attention I was getting. And I came to love it.  It was quite an ego boost to hear the admiring comments from the customers.  Some na´ve ones even wondered how a mere boy could stand being so tightly laced.  One afternoon in early fall I was preparing to leave for work.  Mother and madam came into my room carrying some boxes.   They contained a full set of lady’s garments.  Mother explained, “You’re growing up. You really shouldn’t appear in public as a corseted boy.  From now on you will wear these things when you go to your ‘job’ and anywhere else in public.”  “What irony” I thought.  “All summer I was exposed to ridicule.  Now that coat and hat weather was here I would be wearing dresses and looking more like a girl.”  I had grown accustomed to wearing corsets, stockings and high heels over the last three months and, strangely, now enjoyed the tightly lace feeling.  Somehow the prospect of wearing a dress didn’t seem repulsive, as it would have been before I was introduced to corsets.  Now with my hair fixed, a dainty hat and a little makeup I could go anywhere as a young girl without the fear of ridicule.  I could live with it.  I tried not to appear eager as I was outfitted in my pretty new things.  I didn’t want to give mother and madam the satisfaction of knowing they had won.  I knew they had won.  I found myself secretly wishing that I could wear them all the time.


 Madam intensified my studies so that I could spend more time as a model.  I now started at noon.  I frequently spent my Saturdays at the shop.  It was something to do and I was now vain enough to thrive on the attention.  It had long since become obvious that I would wear corsets for a very long time.  By the time I reached majority (21) when I could leave home and return to a normal life I would have spent eight years in corsets.  By then I probably wouldn’t want to stop.  I wasn’t sure I wanted to even now.  By the time I was fourteen I was wearing dresses and heels almost all the time.  Working in a corset shop I had access to the latest styles.  I always received a discount and sometimes Sally gave me one that attracted my fancy.  One day I had a close call.  Close for whom I wasn’t quite sure.  A former buddy, one I hadn’t seen since my corseting began, and his mother entered the shop. At first I thought that he and his mother were out shopping and she decided to stop in.   He was obviously embarrassed judging by the color of his cheeks.  He did eye me carefully bit didn’t recognize me.  How could he?  My hair was fixed like a girl’s.  I wore makeup and was wearing a lovely corset.  The later seemed to catch his attention.  In that era all men and boys were fascinated with corsets, usually to look at (and dream?).  Without that distraction he might have recognized me.  Sally presented a variety to his mother.  She selected one and within a few minutes I emerged from the privacy screen.  She examined me for a moment and nodded her approval.  “Will madam be wearing it home?” Sally inquired.  “No” replied my friend’s mother, “ Wrap it up.  He will get dressed at home.”  My buddy turned a bright red. However the expressions on his face told me that he didn’t object.  He was just embarrassed.  After they left it occurred to me that even if he had recognized me it wouldn’t have mattered, he had just joined the club.  Now I might renew my friendship and have someone with a common interest to compare notes.


I was now fourteen; seven years to my majority but I didn’t care anymore.  Continuous corseting and wearing women’s dresses had warped my mind to the point that I didn’t want to give them up.  Physically I was a boy.  Emotionally I was a girl.  My life wasn’t too bad.  I had everything I wanted.  Of course my deportment had long since become beyond reproach.  After all, teenage girls are supposed to be perfect ladies at all times and I was.   My hair was now stylishly long.  I even went to a hairdresser occasionally.  One day in a moment of whatever I told them I was a boy.   They were nonplussed. “You’re not the only one,” one attendant remarked.  I was always treated just like I now looked, a girl.  I enjoyed the finest dresses and dainty things.  Jane and I were like sisters.  We would frequently lace each other’s corsets when madam wasn’t available.   Lacing a pretty girl, even if it is your sister can be unnerving.  The golden rule is ‘hands off’.  She had given up her short corsets for the stylishly long ‘S’ line ones that I, and most young women of the time wore.  Laced, we were the same dress size and we would frequently swap clothes.  I continued at Sally’s shop.  I wouldn’t give it up for anything. It was exciting spending afternoons and Saturdays parading around in front of women, especially pretty ones wearing only a corset and stockings.  It didn’t seem to matter that I was a boy.  They would feel the way the corsets were constructed and fit as if I were a girl and I loved it.   Frequently I couldn’t wait for my classes to end so I could hurry to the shop.  Madam rarely accompanied me.  They knew I loved going to work and didn’t need an escort to force me to go.


I resumed my friendship with my corseted buddy. I went to his house one Sunday after church.  When his mother answered the door she glanced at me and assumed I was his girl friend. I liked the sound of the word girlfriend.  It made me feel all cozy and warm inside. She called him.  Joe was his name.  He didn’t recognize me except as the pretty model from Sally’s.  Though confused, he invited me in.  He knew I recognized him and blushed.  As we walked I noticed that he was wearing the corset I had modeled for him.  I learned later he corseted all the time but usually wore girl’s things only at home.  He had just returned from church and hadn’t had time to put on a dress.  It fascinated me to know that another boy was wearing a corset that I had personally worn.  The corset that had embraced my body now embraced his.  I felt a bond between us.  He couldn’t take his eyes off of me.  I was a very pretty young lady.  We sat down and his mother brought us some milk and cookies.  As she set them down she asked, “Aren’t you the manikin from Sally’s?” I nodded.  “But you’re a boy, or so the sign said.”  Then the truth sank in on Joe.  “That’s right, you are supposed to be a boy.  What brings you here?”   You couldn’t possibly remember your old friend Ken from a while back,” I said.  “You can’t be Ken.  You must be a girl playing a trick on me.”  After repeated assurances I finally convinced him that I was Ken.  He was dumbfounded.  His mother couldn’t believe it.  She was convinced that the manikin at Sally’s was actually a girl (She hadn’t seen me when I first started, only after I was fully converted).  She had thought that the sign was only an advertising gimmick.   “No boy can look like that and yet here you are. It’s amazing.  How long have you been this way?” “A couple of years” I answered.  Did your parents force you?” “They did at first but now this is a way of life.”  I was bombarded with questions before I could answer them.  I was amazed that I could speak so freely with strangers about my lifestyle.  We spent the rest of the afternoon talking about ourselves and Joe’s and my feelings.  When he was dressed he was Josy. We ended the afternoon as friends once again; only this time we had a common and intimate interest.  His mother still couldn’t believe I was a boy.


It wasn’t long before mother had dad in dresses and high heels whenever he was at home.   With a wig and makeup he looked like an average forty something woman.  He had not been in public as a woman but he did wear his corset to work every day. I used to wonder how he explained his manner of walking.  He probably blamed it on a bad back or something.  I was shocked to learn that mother had delegated the responsibility of lacing his corset to madam.  That is a rather intimate operation.  Take it from someone who knows.  Madam wasn’t a bad looking woman.  It was her style of dress that turned men off.  She always wore what looked like the same dress.  It wasn’t.   She had a whole wardrobe of identical plain black velvet dresses.  The only thing going for her was that they fit like a glove over her corset.  As I said earlier she was laced to the proportions of a young girl.   In spite of her plain appearance I suppose some men would consider her appealing, especially if they admired tight corseting.   Every morning as I passed his door I could hear him grunting as she laced the last breathless inch off his body.  I wondered if she and dad might develop “feelings” for each other.  It is difficult to have a woman lace your corset and not feel emotional toward her.  Even I, just a boy, would have liked to have madam fondle me.   Her age was no deterrent.  She never made any overtures to me and I certainly wasn’t about to be suggestive to an older woman.  Dad’s situation was different. I had never been touched by a girl or woman and frequently wondered what it would be like.  I often dreamt about the attendants and customers and sometimes madam doing so.   Dreams rarely come true.


Joe and I visited back and forth, sometimes to have lunch or just talk.  Our visits were limited to Sundays and evenings due to my work.   He always dressed for the occasion when I called on him.  He was very attractive.  With a little help he could be very pretty.  Sometimes during a visit I would fix his hair and make him up.  Those Grecian headbands do wonders for a ‘girl’ with short hair. I finally convinced him to take evening walks with me.  Sometimes we would go to one of those new nickelodeons that were popping up all over town.  The movies weren’t very good but it got him out of his house.  He was pleased at the admiring looks he would receive.  He finally got up enough nerve to go out on Sundays, even to church.   We took long walks in the parks and on the avenues.  He admitted he liked flirting with the boys.  Finally he got up enough nerve to walk to my home by himself.  Girls, and boys like us, were considered children until we were sixteen and wore knee length dresses and knee boots on the street.  I enjoyed my fleeting peeks at his knees as we walked along, as I was sure he did mine.   We always made sure that when we sat on a park bench or anywhere in public that we showed some knees to passersby.  In a few months I would be sixteen and stuck in ankle length adult dresses for the rest of my life.  It was strange that I phrased it that way.  I seemed to have forgotten about the age of majority thing.  I now felt I was destined to be a girl, perhaps forever.  Josy would have to give up his short skirts soon also. 


He unfortunately had to wear his male clothes to school and leave his corset off.  I didn’t know how he could stand it. I couldn’t leave my corset off for more that absolutely necessary for bathing and a nature call, a few minutes at most.  Of course I had been wearing one a lot longer and continuously.  An idea dawned on me.  Maybe I could talk mother and madam into taking on another pupil.  Jane was about through with her tutoring so it wouldn’t be extra work for madam when Jane stopped.  If I could pull it off we could spend more time together.  I felt at ease talking to him.  We had a lot in common.  He was almost like another sister.  I talked to mother about it.  I felt a lot closer now and she to me.  After all she introduced me to this lifestyle, which I liked and she transformed me into her daughter, which is what she wanted from day one.  We were both happy that we had what we wanted.  Why not be friends?  I no longer felt resentment about calling her mother.  That’s what she had become.  I didn’t even have to ask twice.  She liked Josy and thought it was a good idea.  Besides I needed a close friend.  Madam, who I now liked also, agreed.  Josy and his mother were pleased with the idea.  Josy could be a fulltime girl and his mother would have a full time daughter.  It never occurred to me to wonder why so many women were preoccupied with transforming sons into daughters.  Years later I decided that it was because they disliked boys.  But then, why did fathers go along with it?  The average man wanted a boy namesake to carry on the family heritage.  I also questioned why many boys and men enjoy wearing corsets and women’s clothes.  I never got an answer.


Josy was a good student and got along fine with madam.  She did have a thing about making sure his corset was laced properly.  She laced mine every day and knew it was as tight as possible.   Josy learned to accept her corset checks as he called them and I think, secretly loved the attention.   I liked having him as a school companion. I loved my job at Sally’s shop but it did interfere with our time together.  As I grew older women seemed more fascinated by the boy manikin. There seemed to be a lot more hands feeling my corseted body than previously.  As a boy I was cute.  As an almost man in corsets I was very sensuous.  Some women couldn’t understand why a man would take a job like that.  They thought it was degrading. Others were intrigued by the idea that a grown boy actually enjoyed wearing a corset.  If business was slow ladies and older girls would just stop by and talk to the beautiful boy.  Judging by their reactions I would guess that many left with ideas about their husbands and boyfriends.   Some thought that all men should wear corsets.  From time to time a regular customer would show up with her husband in tow and introduce him to me.  Many returned a day or two later with their husbands and bought corsets for them.


 Occasionally a husband would return alone and on the pretext of ordering one to try to date me.  That idea fascinated me but I always refused.  Even a lady customer would from time to time try to seduce me.  I would love to have become her corseted lover but common sense prevailed and I graciously declined, frequently using a veiled suggestion that I was more interested in male companionship.  Frankly, at sixteen I didn’t know what I was interested in.  I had been a girl through puberty and never had a girl friend.  I liked girls and still hoped to marry some day.  I wouldn’t know where to begin.  First I would have to give up my lifestyle.  I could never leave my corsets and delegate the heavenly feeling of being tightly lace to the past.  I loved my other pretty clothes and the wonderful rustling and swishing sounds they made as I walked in them.  I had come to relish the approving and sometimes lustful looks men gave me as I passed by.  A male customer’s touch at the shop or a stare by an especially handsome man would sometimes actually arouse me.  That I knew was abnormal.  In the shop I would frequently be aroused by a female customer who just happened to say an admiring word that struck my fancy.  A touch when examining a corset I was wearing had the same effect.  That I knew was normal.  Normal or abnormal either sex excited me.  Would I have had the same reactions if I never wore a corset or dressed as a lady?  That I would never know.  It seemed I could be happy with either sex.  I had a private talk with Josy one evening.  He felt the same way.  Of course he never had the opportunities availed to me at the corset shop but he did experience strong feelings when men look longingly at him.

One evening a day or so later as we sat chatting, my leg happened to accidentally bump his leg.   A chill ran up my back.  I noticed that he appeared to have a minor reaction also.   I mentioned it.  We decided to experiment.  We touched hands with the same result.  I put my hand on his leg and toyed with his garter.  We both trembled.  He did the same with a similar result.  It had to have something to do with the way we were dressed.  One night he stayed overnight.   The next morning after we bathed madam laced my corset.  She was busy and declined to lace his so the task was mine.  We were two boys so I didn’t bother with modesty.  When he saw me in only in my corset and stockings he became aroused.  As I laced his corset I became aroused.  If madam hadn’t called to us that class would start in five minutes I’m not sure what might have happened but with two boys, dressed in corsets aroused and standing inches apart I had no trouble imagining what might have happened next.  I tied off his laces and we finished dressing.  I would love to have had a similar experience with a girl.  What would the reaction have been?  Then again for some unknown reason a boy in corsets seemed more sensuous than a girl; perhaps because there were millions of girls and women in corsets and only a few men and boys.  There was however only one Josy. I had strong feelings for him but I deep down I still wanted a girl.

Our feelings for one another were increasing although we both knew they were wrong.  As days went by we our experimentation was increasing.  First it was just touching and holding hands.  Them we would embrace and caress each other.  The embraces led to kissing which grew progressively more intense. The evening when we held each other’s erection in our hands we finally decided that it was wrong.  Just because we dressed as girls and were always stimulated be the sensations of frilly clothes, tight corsets and the sight of each other as pretty girls didn’t change the fact that we were still two boys.  Boys love pretty girls.  When I looked at him the boy in me saw a pretty girl.  He looked at me and saw a pretty girl.  We didn’t see the real each other.  When we came down to earth we agreed that we were two dear friends with a common interest and would always be just that.  Oh, once in while we would hug and kiss because we had no one else, but that’s as far as we ever went.   I’m not saying there weren’t times when we had other thoughts, but common sense prevailed.  We continued to dress and remained friends for life.

The End


I continued working at the shop until Sally retired.  One day long before that when I was eighteen I had just finished modeling a corset for a mother with a nine year-old boy.  I thought; “He has a life to look forward to.”   At that point a young girl my age walked in.  It would be a pleasure modeling for her.  She walked up to me and introduced herself as Linda saying, “I just can’t believe that you are a man.  You’re absolutely beautiful.  I don’t care too much for men but I could go for someone like you.” With that she ran her hands over my corseted body sending wave after wave of tingles through me.  Finally she got down to the business she came in for.  It seems she would order five different corsets but only if she could lace me into each one.  Both Sally and I were dumbfounded.  In my six years as a corset manikin nothing like this had ever happened before.  Several times someone had suggested it but it never came to anything.   She was adamant.  I had no objection. In fact I like the thought of being laced by a lovely girl.  Sally could see a big sale and agreed.

The girl selected the first one.   We went behind the screen.  She loosened my laces allowing my corset to fall to the floor.   I stood there wearing only the panties I always wore just in case.  This was a just in case, case.  Even with the panty in place she could see I was aroused. She smiled and said, “You really are a man and I can tell you like me.  Most boys who wear corsets seem to like men.”  In a few minutes she had me laced and we returned to the showroom.  She had me parade back and for at least ten minutes as she repeatedly fondled the corset before she announced she would take it.  This was repeated for the other four corsets.  When my parade was over she insisted on lacing me into my stock corset.  As she finished she reached under the corset bottom and massaged me through my panty.  When I had just about all I could stand she stopped and said, “I want you. You will be my ‘sissy boy’”.  I thought the name was cute.  “I’ll stay until you close. Then we will have dinner and you will tell me your life story.” I was aroused, confused and excited like I had never been before as I said, “Yes!”  After dinner I recounted my life as a ‘sissy boy’.  “I want to see you again but only as you are now.”  I assured her that these were the only clothes I ever wore or even owned.   She later explained that a few months back a boyfriend had betrayed her and she swore she would never see another ordinary man again.   She had been looking for one like me.  Her thinking was that a “sissy boy’ would be far less inclined to cheat.  We finally became engaged.  She promised me I could stay at Sally’s as long as I wanted as long as I didn’t play with the ladies.  I in turn promised her that I would never dress as a man.  That was the easiest promise I ever made. 

A few months later an old Justice of the Peace friend of Mother’s married us discreetly. Josy was the maid of honor and my father and sister were the bridesmaids.   Sally hadn’t retired yet and I was still working at the shop when our son Phillip was eight.  One morning Linda walked in with Phillip.  I knew when I saw them that his name would very soon be Phyllis.  She selected a corset for him.  As you might suspect it was very long and rigid.  She insisted that I model one in a larger size so he could see his future, as she put it.   Phyllis protested some when the attendant laced it on him. He quieted down when Linda reminded him that daddy always wore tight corsets, and didn’t he want to grow up and be just like daddy? She whispered to me, “ His wife won’t have to worry about him cheating.”  I thought, “At least not with a woman.”  Within a week, Phillip ceased to exist. Our ‘daughter’ Phyllis will celebrate her tenth birthday tomorrow.  She is lovely, the image of her mother and she adores her ‘daddy girl’ as she calls me,

Linda had a friend Alyce with similar tastes in men. She introduced him to Josy and they were married shortly after us..   I was the maid of honor.  They and their son Charles, also eight have an appointment at Sally’s shop next week.  It looks like Phyllis will have a new girl friend, Charleen, to play with.


23 JANUARY 2004


Sissy Girl Stories