SexStory1 » A Sissy Is Born





This story is dedicated to the Lovely Lady Sarah, my Goddess, and my Mistress.  She is truly the Woman I worship.  The characters in this story are all fictional.  Any resemblance to any real people is totally coincidental – or is it?





The day was Tuesday, September 5.  The year was 1966.  I remember it vividly, because it was the day that my life changed forever.  It is a day that I shall always cherish, yet at the same time, it is a day that I shall always reflect on, wondering how my life would have developed had events not been what they were, for that was the day that I first set eyes on the most beautiful and enchanting woman I had ever seen.


It was the first day of school, right after Labour Day.  I was 17, a senior in high school, and walking right in front of me, was the girl who would change my life and set me on a path which I would follow eternally.  I later found out that her name was Sherry Humphries, a 16 year old student, new to the school.  You could tell from her walk that she was special.  She had an air of confidence that I have never seen in a woman, let alone a young lady of her age.  She didn’t just walk, but she glided across the grounds, smiling at everyone she saw. 


She must have been very smart, because even though I was a year older than her, she was in the same grade as me; in fact, it turned out we were actually in the same home room, and shared several of the same classes.  It was that day that I first gazed at her face to face, and that was all it took.  I was mesmerized by her stature, her self-confidence, the superior way that she carried herself.  I looked into her sky blue eyes, and I was hooked.  It was as if she had hypnotized me with her intense stare, and she knew it.  I just stood there, almost paralyzed, looking into those magical eyes, my knees turning to jelly, and my head spinning.  I could see a small smile emanating from her mouth, and it was then, that she knew I was hers.  “Hi she said, my name is Sherry, Sherry Humphries”.  “What’s your name?”  Stuttering like a complete idiot, I said, “My name is D-D-Donald Mackenzie.  “I noticed you staring at my legs, and chest,” she boldly stated.  I couldn’t answer her, I just froze and stood in front of her silently, lowering my head submissively, and looking at the ground in humble shame.  I could feel my cheeks turning bright red in a hot flush, and I could tell Sherry noticed, because her smile grew, almost stretching from ear to ear.


“It is okay she said proudly.  Lots of boys stare at me, and I know I have nice legs and a healthy looking bust, and I don’t mind you looking.”  “In fact,” she replied, “if I think you are worthy, I might even let you do more than look,” and she laughed in my face, and continued on her way to class.  I stood there frozen to the floor, not knowing whether to go to class, or let loose with the pee which had built up in my bladder.  Pulling myself together, I went to the little boy’s room where I let out a stream of urine that seemed to go on for ever, and then proceded on to class.


All that day I kept staring at this regal goddess, and she knew it, smiling at me frequently as if she was saying to me, “Look baby, it’s alright, because soon you will be mine.”  I made up my mind right then and there, that I would do anything it takes, to get into her good books, and if that meant groveling at her feet, or kissing her ass, then so be it.


The first week went by fast, and I couldn’t concentrate on my school work.  All I kept thinking about, was Sherry Humphries, the beautiful, sexy, and teasing Sherry Humphries.  Whenever she caught me staring at her or looking her way, she always did something to drive me mad – things like lifting her skirt to adjust her nylons, or touching up her lipstick knowing that I was going crazy with desire.  I couldn’t get enough of her, and finally, at the end of classes one day, I approached her and offered to carry her books home for her.  Her reply shocked me somewhat, as she said, “Well, it’s about time you asked, I was beginning to think you were gay or something.”  “Not that that would bother me, because I am bi-sexual myself.”  Once again I was speechless, and didn’t know what to say.  She looked at me and said, “Here, you may carry these for me, and while you are so friendly, you might as well carry my purse for me as well,” and she laughed handing me her books and purse.   With a gleam in her eye, and a smile on her face, she showed me the proper way to carry a woman’s purse, and I, just like a puppy, followed her instructions to the tee.


When we got to her house, she said I did that very well, and she was very pleased with me.  She told me if I wanted to please her, I could carry her books home for her every day.  Needless to say, I jumped at the chance to do so.  She then blew me a kiss, and went inside, while I went home to reflect on what happened.  All that night, I kept thinking of Sherry, and had a huge erection which I couldn’t seem to satiate, no matter how many times I masturbated to orgasm.  Ten minutes after each ejaculation, I was ready to jerk off all over again, breaking out into a heavy sweat each time.





Every day after classes, I would approach Sherry, and ask her if it was okay if I carried her books home for her, just like a little puppy dog.  It got to the point that I felt like I was begging her for the privilege of doing it, and she loved it.  “Of course you can silly,” she’d reply, and she would flash me a big smile.  And just like a trained pet, I would take her books and her purse, and walk her home, feeling proud that such a pretty girl would have anything at all to do with me.


Sherry was very charismatic, and it didn’t take long before she made lots of friends at school, mostly girls.  The boys longed for her, but most were too shy to approach her, so she chummed around with her new found girlfriends, and me.  Soon we walked home together as a small group, laughing and talking about things that happened in class that day.  As we got to know each other a bit better, the girls began to have some fun with me, and teased me about carrying Sherry’s purse.  They would say things like, “Oh Donald, the colour of that purse really suits you”, and they would all giggle and laugh at my blushing cheeks.  Sherry seemed to laugh the loudest, and seemed more amused than the others.  On an impulse, she said to me, “Donald, you are carrying my books all wrong”.  “I want you to carry my books against your chest instead of under your arms.”  Without thinking, I immediately moved her books from under my arm, and brought them up against my chest.  “That’s much better,” Sherry remarked.  “Now remember that, and make sure you carry them that way every day.”  “Yes, Sherry,” I answered, and all the girls burst out laughing.


One day, when we had no homework, there were no books to carry.  Still, Sherry insisted that I carry her purse for her, and, seeking to please her, I did.  Her friends all thought that was cute, and commented that carrying a purse comes so natural to me, that I should get my own and bring it to school every day.  Of course everyone chuckled at this but me.


A few minutes later, we came across some boys, one being the captain of the football team.  Sherry quickly perked up and got all excited, as she desperately wanted to meet him.  “Quick Donald, reach into my purse and hand me my lipstick.”  “I want to look good when we go past the boys.”  Embarrassed as I was, I opened Sherry’s purse, and could not find the lipstick because of all the things she had in there.  Finally, after removing half the contents of the purse, I found the lipstick and handed it to Sherry.  She then asked me to hold her compact mirror in front of her so she could apply the lipstick without making a mess.  I did this, and Sherry put on a fresh coat of lipstick, with me holding her mirror for her, while the girls chuckled and giggled.  What I didn’t realize was, as I was fumbling in Sherry’s purse to get her lipstick, I dropped something on the ground.  Karen, one of the girls, noticed, and exclaimed, “Oh Donna dear, you dropped your tampon,” and all the girls broke out into a loud belly laugh.  I bent down and picked the object up, not knowing exactly what it was or what it was for.  I was naïve for a 17 year old boy, as I lived a pretty sheltered life, having had very little female companionship.  I held it up as if to say what is this, and the girls all dropped their jaws in disbelief.  “And by the way,” I said in a not so kind tone, “My name is Donald, not Donna.”


Sherry, upset with my ungentlemanly like manner, slapped my face hard, and said, “If me or my friends want to call you Donna, then you will be Donna.”  “Do you understand?”  Standing there stunned, and not wishing to get struck again, I replied in the affirmative to her.  “And are you trying to tell us that you, a 17 year old boy, who does not know what a tampon is, or what it is used for?”  “Well then missy, you have a lot to learn, and we are just the girls to teach you.”  Both Karen and Linda both cheered, and yelled out, “Yes, we certainly are.”


When we got to Sherry’s house, we went inside and up to her room.  Her parents were at work, so we had the whole house to ourselves until they returned at 7:00 p.m.  This gave us three hours to do anything we wanted, and what the girls wanted right now, was to teach me some manners, as well as other things.  Sherry smacked my face again, and told me sternly to strip off my pants and underwear.  When I didn’t reply fast enough, she undid my belt buckle, and in one swift motion, pulled both my pants and my underwear down to my ankles.  I screamed, but was quickly met with another smack across the face.  “I won’t tell you again,” she exclaimed.  “Now step out of those pants, and come lie over my lap.”  Fearing her sudden violent mood, I quickly did as she said, and placed myself belly down, and naked, over Sherry’s lap.  She was wearing a short taffeta dress that day, and the feeling of the feminine material was causing some stirring in loins.  At that point, Sherry began to spank my ass with her bare hand, and not so gentle either.  One after another, harder and harder, as if she wanted to make a point, which I guess, is exactly what she wanted to do.  She informed me that if she wanted it to be, that my name would be Donna, and asked me if I understood.  Well, it didn’t take long until the tears began to flow down my cheeks, and when Sherry saw this, she smiled and asked me.  “Now, little girl, what is your name?”  “My name is Donna” I answered in a very weak voice.  “I can’t hear you she screamed.”  “My name is Donna” I reiterated this time in a loud but shaky voice.  “That’s better dear.”  “Now, while you are still lying here, we will show you what a tampon is, and what it is used for.”  Asking Linda to pass her one of Sherry’s tampons, she opened the wrapper, and held it up for me to see.  “Girls use this when they get their period Donna,” she said.  “They put it in their pussy to absorb the blood.”  “Here, Donna, let me show you,” and she gently touched my anus with the plastic tip, pushing it into my ass slowly, but firmly, pushing and pushing until it was all the way in.  Then she pressed what seemed to be a plunger, and the plastic came away, leaving something hard inside my ass.  I squirmed uncomfortably, while all the girls laughed and cheered.  “Do you like that Donna?” Sherry asked, poking the tampon with her finger, and pushing it in deeper while wiggling her finger in my ass making sure there was lots of pressure on my prostate gland.  “Does it feel good?”  “No, it doesn’t feel good, and I don’t like it,” I yelled.  “You are fibbing Donna, your cock is giving you away.”  “It is hard as a rock, and it is pressing against my thighs.”  “Now, I ask you again Donna, do you like having a tampon in your ass?”  With tears rolling down my face, I slowly nodded my head yes, and said, “There is something stimulating as it presses on my prostate.”  “Good girl” Sherry said, “That’s just the answer I wanted to hear,” and she lovingly rubbed the palm of her hand against my damp cheek.  “Now, I want you to keep this in your anus so you can get the feel of it, and I want you to change it every four hours for the next 5 days,” and she handed me a box clearly marked Tampons on it.  She told me that when I remove it, I was to pull the little string at the end and flush it down the toilet, and then insert a new one.  “Now for being such a good girl, I will give you a reward,”   Sherry then went to her lingerie drawer, and pulled out a sheer pair of nylon stockings.  She held them up against my face, dangling them back and forth, all the while saying to me, “Aren’t these just heavenly?” and she smiled that wicked smile of hers.  Then, without warning, she wrapped the nylons around my throbbing penis, and begin to stroke it back and forth, all the time cooing in my ear saying things like, “You like this don’t you sissy boy?’  “You like the feel of my nylons rubbing along the shaft of your big hard cock don’t you girl?”  I couldn’t help myself, and I nodded yes.  Then suddenly, I spurted my seed all over her sexy stockings, rope after rope of cum squirting like I have never squirted before, and all this while the tampon was invading my ass.  Sherry smiled her warmest smile at me, and told me I was a good girl for responding so enthusiastically into her silky sheer stockings, while Karen and Linda applauded expressing their approval.  Sherry then gave me the stockings, and told me to wash them by hand when I got home, and to wear them to school the next day.  She also gave me an open bottom girdle with six garters on it, and told me to attach the stockings to the garters and wear it over my tampon.  She said that the girdle will not only give me nice girly hips, but will help keep the tampon inside of me.  She told me to stand up, and slipped the girdle over my naked groin pulling it up over my tummy, giving my tummy some well needed support.  It actually felt good, and was quite comfortable.  At this point, all the girls hugged me and said how nice and girly I looked, and told me that I was truly one of the girls now, and laughed aloud. 


Sherry then told me to get dressed now, and to go home, and not to forget to wear the stockings, girdle and tampon to school for the next 5 days.  She also said that she would be checking as would Karen and Linda.  I nodded yes, dressed, and girlishly wiggled out of the house listening all the while to the laughter behind me.





Things progressed rapidly from that point on.  Each day, at Sherry’s house, I was given instructions on how to dress and act in a more feminine manner, and given more female clothes to wear.  I did as Sherry told me to, and wore the stockings, girdle and tampon for the next five days, all the time getting used to the feeling in my ass, and even beginning to enjoy it.  Of course the sheer nylons and girdle helped bring about these sensuous feelings, and soon I was anxious for more clothes, and more training from the girls.  In fact, I actually found myself asking, no, begging for more, and the girls happily obliged.


My tutelage into womanhood continued for the next several weeks, and I was responding favourably to my new status in life, that being a sissy boy.  Sherry decided to take things to the next level, so one day she told me that I looked pale, and wanted me to take some vitamins to keep me healthy.  Where she got them from I don’t know, but the next day, she produced two vitamin pills for me, and instructed me to take them with orange juice.  One was a small white pill, and the other was a bigger purple pill.  I took these vitamins religiously just like Sherry wanted me to, and soon found that I had a very docile and relaxed feeling, very calm and satisfied.  I lost any desire I had to be actively involved with sports, or with any of my old boyfriends, but I didn’t miss any of it at all.  I was content to allow Sherry to tell me what to do and how to do it, and it felt very good.  I also noticed that Sherry spoke to me in a very low and sensuous tone, and kept telling how much I liked being her obedient sissy.  She kept putting suggestions into my head, telling me that I enjoyed wearing women’s lingerie, and acting like a girl.  She told me that I wanted to experience my feminine side more intensely, and I found myself agreeing with her, and looking forward to learning more about being girly.  For some strange reason, I couldn’t disagree with anything Sherry said to me.  It was like I was being hypnotized by her to want to live like a woman.  She showed me how to put on makeup, and told me how much I loved wearing it.  I of course agreed, and I found myself craving to wear makeup every day.  She was pleased with me and often kissed me on the lips, lipstick to lipstick, causing me to swoon with love.  That’s right, with each passing day, I found myself falling deeper and deeper in love with Sherry, and the more in love I was with her, the more feminine I felt.  It wasn’t long before there was absolutely no resistance left in me to hang on to my maleness, and I let go and followed all of Sherry’s wishes completely.


This went on week after week, and I enjoyed every minute of my learning.  I seemed to be learning everything there was to learn about being a woman, and soon Sherry had me walking like a pro in stiletto heels 5 inches high.  I got so good at walking in heels, that I found myself addicted to them and wearing them every chance I got.  This pleased Sherry immensely, and she encouraged me to continue, saying she would show me the way of my future, and hinted that one day we might even be married.  I was so happy to hear this, that at that moment, I would have done anything for her, short of murder, and I’m not even sure about that.


A couple of days later, after taking a shower, I noticed a strange tingling in my nipples.  They were very sensitive, and when I touched them, they felt kind of sore.  The more I touched them, the more I liked the feeling, until it became a daily ritual with me to tease and tweak my nipples.  Was it my imagination, or were my nipples getting bigger?  Come to think of it, my breasts seemed to be swelling as well, and when I cupped my breasts, they actually felt like women’s tits.  Anyway, when I told Sherry about it, she calmly suggested that I try wearing a bra.  She said the bra will prevent my breasts from rubbing against my blouses and shirts causing me discomfort, and it will also give my breasts some well needed support.  She even laughed and said that I should be happy because wearing a brassiere will give my bust a more feminine shape, and asking me rhetorically, “And isn’t that what you really want?”  I stared in the mirror and shook my head yes, not realizing what I was saying yes to.  So on and on it went until I had become totally familiar with looking, acting, walking, and wanting to be a woman, just what Sherry wanted.






Things continued unchanged for a couple of months, when a tragedy struck.  Mr. and Mrs. Humphries, Sherry’s parents, were both killed in an automobile accident, and Sherry was left alone with no parents, and no siblings to console her.  It was at this time that I became very close to Sherry, and did every thing I could to make her life easy.  She liked the attention, and was particularly fond of my obedience and subservience to her.  We cuddled a lot, and she enjoyed stroking my growing breasts, and kept telling me she hoped they got bigger, and she would enjoy playing with them and sucking them.  This excited me and my nipples stiffened immediately, and Sherry took notice and smiled.  “I see you like that idea,” she said.  I just smiled and gave her a warm kiss on the lips.


Sherry’s parents left her a sizable inheritance, along with the house, and after awhile, Sherry insisted I move in with her, but there were some rules that I would have to follow.  I almost jumped right out of my skin at the opportunity, but I listened to her rules, and quickly agreed.  The first was that from now on, I was to call her Mistress, Mistress Sherry, or Goddess at all times, regardless of who was with us or where we were.  She also said that I was to live as a girly boy while living with her, and was to appear completely dressed and made up as a woman at all times.  By this time, I was so full of hypnotic suggestions from Sherry, excuse me, Mistress Sherry, that I couldn’t live any other way.  That’s right, Mistress finally admitted to me that the little white vitamin pill she had me take, was really a mild hypnotic, that made me receptive to all her suggestions.  Putting two and two together, I assumed that the purple “vitamin” pill, was actually estrogen given to me to make my breasts grow, and keep my skin soft and smooth.  Mistress agreed with my surmise, and now I knew why everything happened the way they did.  By this time, I was a B cup, and was in need of wearing a bra full time regardless of my preference.  Mistress Sherry also pointed out that I would do all her bidding for her, and be her sissy sub girly slut, and obey her every wish, regardless of my feelings.  She also insisted that I continue to take my vitamin pills, until she gave me permission to stop.  I thought long and hard, but finally agreed to Mistress’s wishes, and that weekend I moved in with her. 


The first thing Mistress did was to get rid of all my male clothes, and replace them with nothing but the prettiest, sexiest female clothes.  I had lacy bras, slips, blouses, dresses, high heels, nylons, girdles, tight stretchy Capri pants, and lots and lots of makeup.  It was a woman’s paradise, and I embellished my future life with both happiness and pride.


Mistress kept me nice and feminine, and took me to beauty parlours, having the attendants give me facials, haircuts (feminine ones of course), manicures and pedicures.  She insisted that my toe nails be painted at all times, and especially at the pool.  She also had the women give me laser hair removal treatments, which included my arms, my legs, my face, my underarms and my genitals.  It took several treatments, but finally there was not one hair left on my body, that’s right, I was completely devoid of any body hair or facial hair.  Once that was accomplished, Mistress Sherry took me to a tattoo place, and had the words “Mistress Sherry’s Property” tattooed in large block letters right over my penis.  Without hair growing there again, it would be obvious to all that saw me what my position was with Mistress Sherry – a possession, a sub, a toy, a slave, a servant, a maid, a girly boy, and nothing more.  It was too late to back out now, as the changes that were made to my body were now permanent, and would stay with me for the rest of my life.








With the passing of time, my breasts continued to grow, and I became more docile.  The more feminine and docile I got, the happier Mistress was with me.  She treated me kindly but firmly, and when I misbehaved, I was spanked soundly with her bare hand, until tears trickled down my face, and I begged for her forgiveness.


It was now time to service Mistress, and when she asked me if I ever gave a woman oral pleasure, I balked, turned my nose up, and said, “No”.  “Well, that will soon change my dear, as I will train you until you are not only an expert at it, but you will beg for the opportunity to eat your Mistress out”.  She then went into the other room and made a phone call which I couldn’t hear.  For the rest of the evening, Mistress planted more suggestions into my head, telling me how much I would love to have my ears pierced, and how I crave to have long dangly sexy earrings.  I agreed, that would be lovely, and I suddenly felt a strong urge to wear sexy girly earrings.  I kept asking Mistress, “When can I get some Mistress?”  She replied, “Soon my sweet, soon”.


Two days later, Mistress took me to a jeweller, who quickly and painlessly pierced my ears.  I was told how to maintain the holes, and the jeweller gave Mistress a large box, in which I presumed was a large pair of girl’s earrings.  My heart skipped a beat at the thought of me wearing these feminine trinkets, and my craving for them increased to fever pitch.  It was two weeks later, when Mistress declared my holes healed, and I was to put on my new earrings and wear them proudly.  She took them out of the box and promptly installed them in my ears.  They were made of silver, and were the largest hoop earrings I have ever seen.  The diameter must have measured 10 inches, and they felt very heavy as they dangled from my earlobes, stretching the holes to twice their size.  “These are trainer earrings my dear, and soon you will see how they work.”  She told me just to get used to them for now, and later my “training” will begin.


That evening, Mistress bid me to come into her bedroom, and sit down directly in front of her.  She was stark naked, and the sight would have given me an instant erection, had my testicles not shrunk from the hormones.  I did as Mistress Sherry commanded, and she told me to move my head right into her lap.  I did this, and quickly, Mistress inserted both her feet into my hoop earrings, and pulled them snugly right up to the tops of her thighs.  At this point, I could not move my head and I was locked into this position.  Now, Mistress informed me, that my training had begun.  “Your head is locked into my pussy, and the only way out is for you to rip your earlobes to shreds, and that would be very painful and bloody, so I suggest you do what comes natural in your position.”  Now, I knew what the earrings were all about.  They were to keep my head in Mistress’s pussy, and the only thing I could do, was to put my tongue inside her love nest, and wiggle it around, so I did what was expected of me.  I licked her clit, and pushed my tongue as far into her pussy as it would go, and wiggled it furiously.  At the same time, I found if I nibbled on Mistress’s clit with my teeth, she would make sounds that were very pleasurable to her.  Well, needless to say, that after several weeks of this training, I became very fluent in the art of cunnilingus, and learned that if I tongued, bit, and stroked her nipples with my hands, all at the same time, I was able to give Mistress several very intense orgasms, which caused her quiver and cry out loudly in sexual fulfillment.  I even got to like it, and as Mistress had predicted, I did soon beg for the opportunity to eat her cunt.  She couldn’t have been any more pleased with me, and often stroked my “clit” (as she now called it) with some silky feminine garment, until I oozed cum into the item.  She would them compliment me saying, “Good girl.” And I thanked her for her compliment on my cum.


The next evening, Mistress Sherry called me into her bedroom again, and commanded me to strip.  Feeling the need to obey her, I quickly took off all my clothes.  She told me to lie down on the bed, with my ass facing the ceiling.  She then went to a drawer, and put something around her waist.  After putting a dab of oil onto her middle finger, she inserted it into my butt hole, and massaged the inside thoroughly.  I knew this day would come sooner or later, but was hoping that Mistress would not teach me this part of my feminization.  Anyway, I braced myself, as Goddess slowly and gently inserted what appeared to feel like a penis into my bottom hole.  It was of course her very large and realistic looking strap-on dildo.  She pushed gently at first, asking me if Donna liked that.  I shivered and told her it hurt, and I did not like it.  She merely laughed, and said I would learn to like it, and pushed the dildo harder and deeper into my ass hole.  I screamed at first from the severe pain, but found it soon subsided as the dildo pushed its way deeper into my pussy.  Eventually, when Mistress was ready, she pushed it all the way in and slowly pulled it part way out, then reinserted it again.  Reluctantly I felt the pleasurable sensations of this anal play, and soon began to enjoy the stimulating pulses.  It wasn’t long before Mistress Sherry got herself into a rhythm, and was fucking my ass like there was no tomorrow.  I couldn’t help responding, and I quickly got into the reciprocal rhythm and bucked backward as she thrust her tool forward, and pulled away when she pulled out a bit.  We were in such rhythm, that after 15 minutes, I heard Mistress scream in orgasmic joy, and I soon joined her in the throes of my own passion and cummy.  She left her dildo in my pussy while we both collected ourselves.  “You are such a slut,” she stated, “And I love my pretty girly slut.”


Mistress was very happy with me, and wanted to show me how a woman feels to be pleasured by a man, so she invited a male friend over one evening, and told him what she wanted.  He looked at me and smiled, pulling his zipper down and telling Mistress that he is ready.  Mistress then told me to take Fred’s penis out from his pants, and fondle it till it became hard.  She told me that I would love it, and that I would beg for cock often once I got a taste of it.  I quickly did as I was told, and began to fondle Fred’s huge cock.  It must have been about 9 inches when it quit growing, and I found myself staring at it in awe.  I could see a huge smile on Mistress Sherry’s face, and as she watched my fascination with Fred’s joy-stick, she told me to go ahead and take it in my mouth, and suck on it.  I complied, and soon found myself making strange little sucking noises.  The cock kept getting harder and bigger, and I almost choked on it, but I continued to suck and stroked the underside of Fred’s penis with my tongue.  Soon I learned what made him feel good, and I adjusted my mouthings according to his moans and groans.  I sucked harder and faster, until I felt him shutter, and I knew my mouth would be splashed full of man-juice, and if size were an indicator, my mouth will be overflowing with his cum.  It didn’t take long, and I soon felt the first spasms of his pleasure strike the back of my mouth.  Strand after strand of cum splashed its way into my mouth, and I found I had to keep swallowing to avoid choking.  It was salty, but not too untasteful, and after two or so swallowings, I actually came to like the taste.  In fact, I found the entire experience exciting, and my nipples hardened and swelled into two pointed peaks.  I couldn’t help myself, so I started stroking my titties, and teasing my nipples, while massaging my breasts.  When I became fully developed from the hormones, I found myself needing breast and nipple stimulation in order to experience a bit of orgasmic oozing.  This was what my climaxes were made of now – little oozings, but still they sure did feel good. 


Mistress patted me on the back, and told me I did a wonderful job.  She also told me that she knew I would enjoy it, and would want to do it often in the future.  While Fred was re-cooperating his strength, Goddess informed me that there were just two more things that she wanted of me, and then she would decide where our future would go.  She told me that I made a very pretty girl, and that I learned my lessons well.  That made me very happy.


It was when Fred recovered from his orgasm, that Mistress informed me what the next step was to be.  She wanted me to feel the pleasure of a man’s seed being squirted inside my pussy.  She wanted me to experience what it was like to be fucked by a man.  What a woman feels when her stud fucks the ass off of her.  This act would seal my fate, and I would be considered a woman for life when it was over.  She said that this act would make her very proud of me.  She told me to use my mouth to get Fred hard again, and to suck with vigor.  I took his cock in my mouth, and followed Mistress’s instructions carefully.  I felt his manhood swell and get hard, and I must admit that I was enjoying this feminine act; that of sucking cock.


Mistress told me to apply some jelly to Fred’s cock, and to rub it in good all over the shaft.  She then came around to me, and lubed my girly pussy with her finger using the same jelly.  Now, it was up to Fred to act as a man, and he undertook the task with vim and vigor.  He had me assume the position, and entered my backside with his manly cock.  He pushed and pulled and pushed again, until he felt me relax and begin to moan in pleasure.  He fucked me with love, and truly wanted for me to enjoy my first real fucking.  Within minutes, I was joining him and following his lead by finding my own pace to follow.  Up and down we both moved in unison, and before long, I was mentally considered to be a complete woman, and a member of the fairer and gentler sex.  Fred made a woman out of me, and I loved it.  I knew from this day on, I would embrace my new life of femininity and look forward to my womanly duties.  Mistress just smiled that knowing smile of hers, and said, “Well done girl, well done.”




The years passed quickly.  I was now 24 and Goddess was 23, and well on her way to becoming a doctor.  I on the other hand, remained as her full time live-in maid and sissy girl, doing whatever Mistress’s heart so desired.  I was living full time as a woman, and could never revert to my old life even if I wanted to.  My body had undergone too many permanent changes to ever be male again, so I accepted things as they were.  I was still not permitted to have sex with Mistress, at least not intercourse, but then again, my cock and balls had shrunken so much, that I wouldn’t be able to perform in any event.  I was servicing my Goddess orally on a regular schedule, eating her pussy and becoming extremely proficient at it, driving her over the edge at just the right moment, just the way she likes it.  When Mistress wanted a man, she would invite one over, and had me prepare him by giving him a blow job to get him hard for Mistress’s pussy.  This became so enjoyable to me, that on several occasions, I would deliberately go too far, and make her lover explode in my mouth.  I would swallow his whole load of cum, and smack my lips savouring the flavour.  Mistress would get angry at me for spoiling her fun, but then she would laugh, and tell me she understands how much I enjoy giving blow jobs, and it was after all, one of my regular duties as Madam’s personal maid and sissy girl.  Sometimes she would spank me for being so insolent, but never very hard, just hard enough to remind me that she was in charge, and that I was still her property, to do with as she pleased.  There were times when she was extremely pleased with me, that she allowed her man friends to fuck me in my pussy, just like a woman gets to be fucked.    I liked it so much, that I often looked forward to a good fucking whenever I knew one of her male friends was coming over to visit.


Two things Mistress especially enjoyed doing, was to play with my now C cup breasts, tweaking my nipples till I swooned with delight, and cupping and squeezing my now shrunken balls and penis, sorry, my clitoris.  It was during one of these play episodes when she was toying with my balls, that her eyes suddenly lit up, and I could see the wheels spinning in her head.  She said she just got a brilliant idea, one that was to make me very happy, and make my tight Capri pants fit better in the crotch.  I shook with fear thinking the worst.  “Please Mistress,” I begged, “Please don’t take my balls.”  She laughed seeing the fear in my eyes, and replied, “Don’t worry my little princess.”  “I would never take away your precious balls, but I do plan on doing some remodeling.”  I could not understand what Mistress was referring to if she was not going to take my testicles away, but I was glad she wasn’t.


Next morning, after making a couple of phone calls, Mistress came to me with a new pill, and told me to take it.  Not asking what is was for, I swallowed the pill with some water, and went about my regular cleaning chores.  About an hour later, I became very sleepy, and couldn’t hold my head up.  Mistress told me that is was alright, and I was to lie down in her bed, while the sleeping pill worked.  I looked up at her quizzingly, but she just smiled and said everything will be alright, and told me to relax, so I did.  Before I fell into a deep sleep, I remember hearing the doorbell ring, and heard strange voices as Mistress let some people in. I vaguely remember someone sticking a syringe into my arm, and then blackness fell upon me.


When I awoke, I had no idea how long I was out for, or what was done to me.  My first thought, was to check below for what used to be my manhood.  I breathed a sigh of relief when I felt my “clit’ still in tact, but strangely enough, I felt a large bandage over my testicle area.  “My God No,” I screamed.  She gave me her word she wasn’t going to take away my balls, yet here I was knowing that something was missing from down below.  I also felt some new earrings hanging from my ears.  They seemed heavy, but my implanted desire for earrings made me forget my lost testicles, and made me happy for the new jewellery dangling from my ears.  I just couldn’t wait to see what they looked like.


A short time later, Mistress walked into the room, smiling at me saying she was glad I was awake now.  She informed me that I was asleep for three days, and that soon I would be a very happy young woman.  I told her she lied to me when she said she would never take my balls away from me, and she just looked at me and said that she did not take away my balls.  She kissed me lovingly, and said she did not take them away, she just moved them to another spot.  I looked puzzled so she explained what had happened.  She arranged to have my shrunken balls removed from my genital area, had the jeweller dip them in gold, and make earrings out of them.  She said that she then had the jeweller permanently attached the golden testicles to my ears, so they could never be removed.  Now she said, my tight sexy Capri pants will look and feel great on me, and I still had my precious balls.  Over and over I imagined the jokes people would say about me.  Jokes like, what’s the difference between a man and Donald?  A man wears his balls in his scrotum, and Donald wears his balls in his ears.  I cried, and cried, until she again kissed me and told me not to worry.  “Now I have some good news for you.”  She stated that two weeks from today, she is going to take me for her wife.  “Isn’t that wonderful sweetie?”  I looked at her in shock and said, “You mean you are going to marry me?”  “Yes”, she replied.  “Does that make you happy?”  Tears of joy flowed down my face, and I cried like a baby for a full hour.  “Yes, Mistress, I am very happy,” and we hugged each other passionately.


Two weeks later, there was a small ceremony with only a few close friends in attendance, I found myself strutting down the aisle wearing a long white wedding gown, and sporting my new dangling gold earrings.  Tears of joy were flowing freely, making my mascara run, and ruining my flawless makeup, but I didn’t care.  No, I didn’t care one little bit.


The day was Tuesday, September 5.  The year was 1966.  I remember it vividly, because it is a date that is branded into my memory for eternity.  It is the day my life changed forever.





Categories SexStory1 Date 03/06/2011