Sissy of the County

[Benjy]

This story happened over 50 years ago but I remember every detail like it was yesterday. Back then; the town of Stepping in Stepping County was a very rural place, with the main industry being farming and lumber. It was a sleepy little town where everyone knew everyone and if you were a bit different, you stuck out like a sore thumb.
But I digress. Let me tell you who I am. My name is Tommy Dawson. It’s best if I start the story right from the beginning.  I was the youngest sibling of 11, born the same year the Japs surrendered in 1945. I was the only boy and as a small child, I realized that my mother looked at me in a different way than she did the other kids. I was never ‘loved’ by her in the same way that she related to my sisters. She never laughed with me or played with me. At that tender age of infancy, there was an enormous part of my life missing. Later my Mother told me she never wanted boys, only girls and never really liked me as a child as I was a poorly, sickly infant, always whining and grouchy.
The reason I grew up as a teenager, and then into a young man still wearing diapers was her punishment for what I was. Mother just never bothered potty training me and told everyone it was impossible, as I couldn’t keep myself clean at all.
Mother ruled the household with an iron fist. She was strict with everyone, especially my father who would work dawn till dust at the flourmill and still come home to her sharp and spiteful tongue. On a regular basis, Mother would strike or beat me for each and every minor transgression, and even those that I had no control over. Even as a young child, I became a nervous wreak, wondering when the next spanking was coming. My sisters would be required to witness my chastisement, which I found very humiliating.
As a baby at home, I would look forward to my sisters coming home from school as I was there ‘best’ toy. I remember them asking Mother if they could play Mommy and Daddy with me as the baby.  It was only fun changing Baby’s diaper if it was wet and they would encourage me to pee as soon as a clean diaper had been put on. Those games were fun, as I would laugh with my sisters as they tickled and changed me. Clementine used to ask Mother if she could spank me and Mother would wink at her and say; ‘only if he’s naughty.’ Of course, they always found some sort of naughtiness and the game always ended in tears; my tears.
Post war the economy was very bad and there was not much money around in order to bring up such a large family. Mother was forever bickering at Dad about his ‘pathetic’ pay check and why he didn’t ‘man up’ and ask for more money. Food was very basic and new clothes and shoes were non-existent. Mother would beg for clothes from charity shops and family, occasionally buy stuff from 2nd. Hand shops but most of all us kids had to put up with hand-me-downs from the bigger sister to the smaller sister, and eventually to me. I didn’t know what boy’s clothes were until school kids starting teasing me in the playground.
“Sissy, Baby Sissy, Tommy is a Sissy” they would call, pushing me at the same time.  I would end up on the floor, crying my eyes out. Whenever anyone wanted to fight, I would run away and tell a teacher. Sometimes the bullies would take my clothes off until I was wearing only my rubber pants so that everyone could see what a big baby I was. ‘Yellow Sissy Baby’ or ‘Yellow Pissy Baby’, became a familiar phrase on the playground. I seemed to have gone my entire life running away from trouble and even now, hate confrontation. Among all the boys of my generation, I was known as ‘Yellow’ for my cowardly behaviour.
My older sisters, Josephine, Sally, Mary and Petra were kind and protective to me. When I first started at Middle School, they would safeguard me in the playground but each other started moving up the High School and soon I was by myself as my younger sisters found me very embarrassing and wanted nothing to do with me. Clementine, who is two years older than me was actively encouraging the bullies to torment me, which made me very sad.
Dear Reader, sorry to take so long with the background, but now you have a fair idea about my makeup.  Now I can introduce you to Becky, who I met first when I was seven.
Becky’s Mother was a social worker who turned up at our place to talk to my mother. I imagine it was about some sort of handout she had requested from the State public purse. I was playing by myself in the yard and remember this blond haired girl looking out of the car window as it pulled into our drive. Mother came out and greeted Mrs. Emily Bronson and asked me to play with Becky while the grown-ups talked inside.
“Why are you wearing diapers?” Becky had asked when we were alone. Mother wouldn’t let me wear my trousers in the yard as I would get them dirty and wear them out so I had to play in my hand-me-down pink girl’s blouse and my nappy and rubber pants.
Even at seven years old I was self-conscious of my infantile attire, so I had blushed and looked down.
“If I don’t have diapers, then I wet my pants and Mother is angry,” I said. It seemed to make sense to her and she nodded. I looked up at her.
“Why’ve you got a black eye?” I pointed at the bruising. Becky giggled.
“Got into a fight with the Gatlin Sisters. Mum is sore because they sent me home from school for fighting and my dress was torn.”
“They are such bullies. Did they hurt you?” I was frightened of the Gatlin Sisters. They always wanted to hurt me. Becky laughed.
“Not as much as I hurt them.” I looked at her and she wasn’t lying. Becky was a touch little nut in those days.
“What shall we do?” Becky asked.
“Let’s pick some flowers,” I offered. She nodded and smiled and we ran off to the nearby meadow. We must have had a lot of ‘seven year old’ talk and I don’t remember much but before she drove off again with her Mother, I gave her the daisy chain I had made, and her face had lit up with happiness. As the car pulled out of the drive, she waved from the back window, smiling and wearing the Daisy Chain like a crown.
I saw Becky the next day. She picked me out in the busy school yard at recess. Turned out she was in the next door classroom. As we were talking, the three Gatlin sisters turned up and started teasing me.
“Sissy Baby’s got a girlfriend.” They thought that was very funny. Mary-Lou pushed me and I fell over on my butt. Becky waved her clenched fist under her nose and pushed her back, telling them all to go away or she would get the teacher. Blanche and Dixie pulled their sister but didn’t leave without a farewell, ‘Yellow Sissy Baby poops his pants’ goading. Becky ran at them and they scarpered. I couldn’t help feeling the Gatlin Girls were wary of her then. Out of the three, Mary Lou was the oldest and the biggest, about 18 months older than Becky and myself and a head taller as well. Blanche was the same age as us and Dixie was the baby of the three, but just as dangerous.
“I hate those Gatlins. They are always looking for trouble.” Becky complained. She wiped my tears with a cotton handkerchief. “Don’t worry about them. I will protect you. You are my friend.”
At that moment, I loved Becky more than anything else in the world.

[Benjy]

Time went by and things got worse at home. I was very unhappy. When I was 10, Father died as did his pay check. Mother sent the three eldest daughters out to work in order to help the household. I was made well aware by Mother and some of the siblings that I was a pathetic useless burden on the family and Clementine even said it would be better if I was dead.
Still Mother was determined to keep me in diapers. She would often refer to me as, ‘useless male, just like your father’. I was in the yard one day and felt a bowel movement coming on. Guiltily looking around, I snuck into the empty outhouse, pulled down my diapers and rubber pants and sat down. Unfortunately, I had been seen by Clementine who gleefully ran and told Mother. I got the shock of my life when Mother tore open the outhouse door and pulled me out by an ear with my diaper and rubber pants still around my ankles.
She assembled all the family and paddled my ass in front of them all.
“You are a boy, and therefore you belong in diapers.” She said, still holding me firmly over her knee. “You are never to use the outhouse, do you understand?” Her words were punctuated with sharp slaps from the wooden paddle. “The Outhouse is only for girls, not dirty pathetic boys, do you understand?”
After that, I gave up all ideas of potty training myself and resigned myself to using my diapers. I definitely wasn’t a rebel. The school never questioned it, the Nurse routinely changed me whenever needed it. The school didn’t like the way I turned up wearing girl’s clothes, but they turned a blind eye, as they did to most of the bullying I received from my peers, especially the Gatlin girls. I think they were hoping I would leave school. Some days I would run out of the playground being chased by bullies and not come back to school. My teachers never reported this and happily continued the education of the rest of the class.

---*---

In my early teens, I still would still see Becky, after all, she only lived 15 minutes away. We were both at High School then, but she had been fast tracked into a high performing class and was academically doing very well but she was still getting into trouble for fighting, being the type of girl who would never back down. Later I was to understand that much of the trouble was caused while she was defended her relationship with me. I was proud of her but didn’t get to see her that much. I would really miss her.
Academically, I was useless and remained in the bottom stream of the school but in woodwork class, I excelled and really enjoyed making things with my hands. Turns out the owner of the lumber mill, Reed Weller, who had also started a furniture making business offered me an apprenticeship when I left school.
Tired of the bullying and the negative attitude from the teachers, I asked the Head if I could leave school at 14 and he agreed. Probably pleased to see the back of me and all my ‘problems’.
Reed Wellar gave me my first work coveralls. I was so proud that no one could see my rubber pants now. On Mother’s insistence, he also agreed that his wife, or his secretary would change my diapers when at work.  Mother made it very clear I was not to use the toilet. Mind you, by then the damage had been done. I was totally incontinent by then.
The only light in all that darkness at home was Becky. She was doing well at High School but still found time to come around home to see me.  Surprisingly, Mother liked her and was nice and pleasant when she showed up. Becky never ever questioned why I was in diapers. To her, it was the most normal thing in the world. I know she had ‘private’ conversations with Mother and I am sure the diapers were discussed. She would often attend when I was having my diapers changed by Mother or one of my elder sisters and it wasn’t long before she started volunteering to do the job herself.  I still remember the first time Mother invited her to watch me having my diaper changed.  Looking back, I think Mother was testing her, to see if she had a propensity for my care and a willingness to continue it. The fact that I was poopy at the time and stank to high heaven didn’t phase Becky one bit.  She held my hand and smiled down at me while Mother cleaned my bottom and re-diapered me.

---*---

At 16, I was so good at the joinery work that Reed took me on full time and gave me a proper wage. Not enough to move away from home, but a start. Mother took 75% of my wage to pay for my keep.
I was seeing more of Becky. We both admitted it was more of a relationship now; holding hands and kissing when we could get alone. There was a change in the power ratio now between us and more and more, Becky was leading and I was following. I noted that she was beginning to ‘baby’ me very gradually. She would call me ‘Baby’ in front of Mother and when we were alone. There was this one time when we were alone in the house and Becky was deep into some homework that I told her I needed a diaper change.
“You’ll have to wait, I must finish this chapter.” I was soaking and irritable.
“I could change myself,” I tentatively mentioned. Becky didn’t even look up but her tone changed.
“No, you know you are not allowed. Just wait.” I then knew that Becky was taking over as ‘Mother’ slowly and I welcomed it. Later, when she was changing me, she asked.
“You don’t change yourself, do you?” I shook my head, looking guilty. Reproachfully she also asked; “And of course, you don’t ever use the Outhouse or the Toilet, do you?”
“No, of course not.” Smiling, she kissed me while pinning up the Birdseye cloth diaper.
“Because if you did, I would be very sad and would have to tell your Mother. And you know what that would mean, don’t you?” The threat hung in the air and my face burned with shame.

We were talking more about sex now. Becky knew I liked to cross dress and I had told her I fantasised about wearing nylon stock sings and a suspended belt. One afternoon Becky was drying me after a bath and said that she had a special treat. From a packet, she pulled out a pair of new stockings. She had me lie on the changing table where she rolled the stockings into place. Next followed the belt. I remember being so excited, my swollen pen-is was dribbling with desire.
“Masturbate for me Tommy, will you?” I did not need a second invitation. Within 15 seconds I was spraying semen all over my chest. Becky watched intently. It did become a ritual after that. She made me promise not to masturbate by myself but always with her watching. Sometimes she provided the hand, but not often.
It was a bit one sided then. My body held no surprises for Becky as she changed me whenever we were together. Often, if I had been soiled, then she would bath me as well. Unfortunately, Becky’s body stayed very much off limits but she did say when we both reached 18 years old, things would change.

[Benjy]

At 17, I started saving little bits of money here and there and learning how to buy female clothes in my size. I soon discovered ‘mail order’ and Post Box No’s in order to keep my ‘kink’ a secret. I had a secret ‘trunk’ under my bed, which was locked. Here, I kept my meagre stock of woman’s clothes and underwear.  I had brought a mail order wig from a costume supply company as I couldn’t afford the high prices of a real wig. The quality was so bad that even I thought I looked silly in it, let alone a 3rd. party stranger.
I kept the trunk secret from Becky, as I knew she wouldn’t approve. She didn’t mind me having the underwear; items like stockings, bra, panties (as long as they were worn over the diaper, and not instead of) but didn’t want me wearing skirts, blouses and dresses as she believed (rightly) that I would go out in public and get into trouble.
It was one Saturday that my world came crashing down around me due to my stupidity. I had dressed up in high heels, stockings, wig and dress and went for a walk in the town center. Everyone, but everyone stared at me. Some laughed, some looked shocked. Mothers shielded their kids away from my path and many, whether they knew me or not, called out derogatory names. ‘Pervert’, ‘twisted’ and ‘Yellow sissy’ were some examples.
As if something snapped in my brain, I panicked and wanted to be home, in the safety on my bedroom, in Becky’s arms. Anywhere but here. I knew a quiet passageway off the Town Square where I hoped I could discreetly leave the Center and get away from the crowds.
Then it happened. 40 yards inside the passage, the back door of  Lacy’s crashed open and Mary Lou Gatlin and her sister Blanche came charging out, laughing and clutching two large plastic bags.
“Too easy!” Mary Lou shouted.  “They are fast asleep!” Mary Lou had changed big time since she was 12 years old. Fast food had swelled her size to about 200 lbs. Like the others in the Center, Mary Lou and Blanche stopped and stared at me for a moment before they both burst out laughing.
“Sissy Baby, is that you?” They surrounded me and backed me into the passageway wall. Blanche reached down and pulled up the hem of my dress, exposing my diapers.
“Oh how sweet,” she said. “Yellow Sissy Baby is wearing his diapers and rubber pants and his lovely female outfits. God.. you are a pervert!” Hands were all over me and Mary Lou wrenched my handbag off me and opened it.
“Please give that back Mary Lou?” I sobbed.
“fuc-k off!” She slapped me hard across the side of the head, dazing me. As my knees collapsed, there was a shout of ‘Hey!! Stop!!’ I heard the Gatlin girls running fast the passage way.
Next thing I know the Lacy Security Guard is kneeling beside me and lightly tapping my cheek.

---*---

“Who were those girls?” Sheriff Taylor asked me. “And don’t tell me you don’t know. I know you know!” he growled.
“I am sorry Sheriff, but I don’t know them.” He slapped his hand loudly on the table in front of me.. I was in an interview room at the police station and I was trembling with this large sweaty man making threatening moves. He grabbed me and threw me face down over the desk.
“Then I will beat it out of you,” he said, unbuckling his belt and pulling it clear of his waist. Twisting my left arm up the small of my back, he pulled up the hem of my dress and wrenched down the diaper and rubber pants. I howled with pain as the belt struck, biting into the moist skin of my buttocks.
“Stop, Stop!” I sobbed. “It was the Gatlin Girls, Mary Lou and Blanche.” Sheriff Taylor released my arm and returned his belt to his trouser loops.
“Thank You Tommy, you can go now.” As I reached the door he added. “Oh, one thing Yellow. Stop dressing up like that, you could get arrested.”
When I got home, fortunately, Mother wasn’t there but Becky was. She couldn’t get me on the phone so had come around to the house. Her face fell when she saw what I was wearing. She noticed the bruised face and the torn and bloody stockings.
“What happened to you,” she asked. I burst into tears and sat on the sofa next to her. Becky hugged me. “There, there,” she said softly. “Start from the beginning.” I told her everything, including the beating I had received at the police station. Becky sighed.
“The Gatlins won’t forgive us for giving them up to the police.  There might be trouble up ahead.”
Becky took me upstairs to change my diaper, spreading a soothing salve on the welt across my bottom. Afterwards, she made me carry my female clothes out to the yard and dump them in the incinerator.
“It’s for the best,” Becky squeezed my arm as I watched my precious clothes go up in smoke.
Nothing was said to Mother when she got home and I loved Becky even more for that.

Three months later, I was in court. I was threatened with contempt if I did not properly identify the defendants who had stolen my purse. The Lacy Security Guard had already given evidence relating to the shop-lifting and also stated that he had seen the girls stealing from my handbag. My purse was later recovered from the Gatlin residence, further ruining my chances of evading giving evidence. The judge gave them both18 months in the County Jail. On the way out, Dixie Gatlin came up to me and pressed a note in my hand.  Becky reached over and took the note, quickly reading it then hiding it in her pocket.
“What did it say,” I asked anxiously. Becky smiled grimly and squeezed my hand.
“Nothing for you to worry about my Darling.” She squeezed the padding on my bottom. “Are you wet?” I nodded. “Then let’s get you home for a change, eh?”

[Benjy]

When I reached 18, I began to get a bit more daring with my cross-dressing. I was blind to the promises I had made to Becky and to myself.  Since the last time, I had started collecting clothes and accessories again. This cross-dressing was part of my make up and I couldn’t get away from it.
As with the last time, it was another Saturday afternoon and I was experiencing the same reaction from the public. Within 20 minutes, a squad car pulled up next to me.

I was arrested and charged with Indecency and Mother had to come to the Police Station to take me home. I had been in a cell for 5 hours and my diaper was long overdue for a change. Sheriff Taylor had suggested to Mother that she ‘tan my ass’ to knock in some sense.
“Don’t worry,” Mother had said. “By the time his fiancĂ©e and myself have finished, he won’t be able to sit for a week!” The Sheriff laughed. He knew all about Becky and her right hand or fist. “I wouldn’t want to be in his shoes then.”

This was news to me. Fiancée? Becky and Mother must have discussed this. I knew nothing. When we got home, Mother pointed up the stairs.
“Go to your room and stay there. Do not come out for any reason.” I knew better to disobey Mother in the current atmosphere. I could hear her on the phone and she was talking to Becky. I took off my ridiculous clothes and waited in just my diaper and rubber pants.
Becky arrived 15 minutes later and I could hear her talking to Mother below. Much later, Becky opened the door, carrying a tray with a glass of milk and a sandwich. I tried to kiss her but she pushed me away.
“Now you have made me sad.” She pointed at the changing table. “Your Mother said you would need a change.” I was mortified that I had upset her and started crying. Becky got angry.
“Stop crying Baby, you have nothing to cry about. I am the one who should be crying, not you.”
When she had removed the drenched diaper, she examined my thighs.
“You foolish boy,” she scolded. “You have a diaper rash now.” I winced as she treated the raw skin with cream. She had me turn over onto my stomach so that she could cream my buttocks.
“I will leave your diaper off for an hour or so.” Becky laid a towel on the bed. “Come and sit here. We need to talk.” I settled on the towel, slightly self-conscious that Becky was fully clothed and I was completely naked.
“Your Mother wanted to beat you, but I talked her out of it. I said you were my responsibility.” I looked relieved.
“Thanks Becky.” I tried to kiss her but again, she pushed me away. Dolefully, I looked up at her. “At the Police Station she told the Desk Sheriff that you were my FiancĂ©e, what did she mean?”
Becky shrugged. “Later, now I want to talk about your behaviour in town today? What were you thinking of?” I started crying again.
“I am so sorry, sometimes I get these urges to dress up.” Becky looked cross.
“Urges? Don’t I take care of those ‘urges’ when you are on the changing table?” She watched me snivelling for a while. “Now you tell me what we need to do to stop this?  The police are going to let you off with a caution, but next time you will do some time in the County Jail, and we both know that you don’t want that.” I wailed louder and gripped Becky’s hand tighter.
“Help me Becky, I don’t want to screw up again.” Becky leant forward and planted a kiss on my lips.
“OK. Then we will get married. Only then will I be able to protect you.” It wasn’t a proposal, just a statement.

[Benjy]

We were married ten days after on a Sunday. All my Sisters were there and even Mother wore a best frock and smiled a lot. I do believe she was happy to be ‘moving me on’ to another.  Becky was close to me that day; lots of touching, hugging and kissing and I loved her more than ever.
We moved into Becky’s house that same day. I only had one suitcase with me; the sum total of all my possessions as an 18 year old. Becky showed me into the spare bedroom next to hers.
“Aren’t I sleeping in with you,” I asked, disappointed. Becky kissed me.
“You will make lovely husband one day, but we still have to get there, don’ you think?” She said cryptically. I didn’t understand then but nodded glumly. I so wanted to be in Becky’s arms that night.
Becky’s mother wanted me to call her Emily and I was happy to do so. I liked her; she was kind and warm.
“I think its bedtime,” Becky announced. I was surprised. It was only 7 pm. She started undressing me while Emily fitted a rubber sheet on the bed. I tried to object but she just hushed me with a finger on the lips.
“Remember Baby, you are my responsibility now and I will keep you on the straight and narrow.”
“But, your Mother
” I whispered. Becky laughed while pulling down my trousers.
“Mother’s going to be looking after you when I am at school so she is going to be well used to seeing you naked. Stop being silly.”

I laid down on the freshly made bed for the diaper change while Emily looked on. Becky calmed me with her soothing words.
“My Mother will be looking after you when I am not here so she is learning how to change a diaper on such a big baby.”
“I am not a baby,” I said reproachfully. Becky laughed and kissed me on the nose.
“You are my big baby, my special baby.”

Becky came to me in the night and checked my diaper. I woke as she pulled the covers back. Her hand felt inside the waistband of the waterproof pants.
“You are soaking.” I lifted my hips as she tugged down the rubber pants. In the warm evening air, she was wearing only a thin nightdress and I could see the outline of her breasts. By the time she’d unpinned the wet diaper, my swollen pen-is greeted her but she ignored it as she pinned a dry diaper on and pulled up the rubber pants.
Becky sat up against the headboard and unbuttoned her nightdress.  I watched with fascination as she exposed her breasts to me. She had never done that before. She patted her lap.
“Lay your head here baby.” I nestled into her warm body. With her arm, she lifted my mouth to her breast. My lips latched on and I suc-kled gently. Becky was purring with pleasure above me.
“Mommy loves that,” she sighed. Her fingers wormed their way under the waist seal of the rubber pants and into my warm diaper, gripping my pen-is. Just the touch was enough. I shuddered and jerked in her arms, ejaculating powerfully into her palm.
“Good Boy,” she murmured. “Mommy will take care of all Baby’s urges, won’t she?” It was comforting to be babied by Becky. She was calling herself Mommy now and it seemed expected that I do the same.
“Mommy?”
“Yes Baby?” Becky pulled her hand out from my diaper. Her hand glistened with the result of my discharge.
“Can I sleep with you Mommy? Like a Husband?” Becky held a sticky finger to my lips. Compliantly, I opened and suc-kled, tasting my own semen. In silence I cleaned all her fingers, then the palm of her hand until it was all gone.
“Good Boy,” she said. “Listen, I need to talk to you about us.” I tried to sit up but she held me to her chest. “Relax, and listen. You are safe in my arms Baby.”
“Yes Mommy,” I said.
“Darling Boy, we are married where we promised to love, honour and cherish each other and also you promised to obey me, remember?” I nodded.  Becky patted my bulky diaper on my rump. “We are not the same as some other husbands and wives Baby and that is good. We don’t fight or argue with each other, and you don’t have to worry about clothes or food or money or other nasty grown-up things. Mommy is going to take care of all of that.” Becky kissed me on the forehead.
“But you do understand Mommy has studies to do and needs a good night’s sleep so that’s why she needs her own room. Mommy does not want to wake up in a wet bed, or smelling a poopy bottom, otherwise she will get cross, and we both don’t want that, do we?” Becky smiled down at me and scratched my nose. I looked downhearted and started sulking.
“Now, now,” Becky scolded. “We are married now but if you are naughty, I will send you back to your Mother!” She joked and then kissed me. “I am always here for you but our relationship will not be Wife and Husband, but Mom and Baby, you know that don’t you?”
“Yes Mommy,” I admitted to myself that she was right; Becky was always right.