By JosephineMay
Copyright 2026 by JosephineMay, all rights reserved
[1,248 words]
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This
story is intended for adults only. It contains depictions of forced
nudity,
spanking, and sexual activity of preteen and young teen children for
the
purpose of punishment. None of the behaviors in this story should be
attempted
in real life, as that would be harmful and/or illegal. If you are not
of legal age in your community to read or
view
such material, please leave now.
A Sissy Boy Growing Up - Part 1
by JosephineMay
My name is Steven and I was born in 1989 to my single mother who
already had two daughters and no husband. None of us ever met our
fathers and we were dependent upon Mum who worked as a secretary during
the day and supplemented her income as an escort in the evening. My
sisters and I knew to be out of the way by 8.30 in the evening when
Mum’s gentlemen friends called when I was looked after by my
sisters. Mum had not expected a boy so my upbringing was that of a girl
wearing my sisters’ hand me down clothes and attending
nursery as Steph in female attire. I thought of myself as a girl and it
came as a shock when I had to convert to being a boy at 5 years of age
for school. The 5 year old Steven was in no way masculine and unready
for the rough ways of a boy being more attuned to the gentle, girly
ways of the girls in the school. I was aware that I was different but
had only been told that girls did not have the dangly bit that was
between my legs and that they sat down to wee. I had never
seen a girl naked although several had seen me weeing at nursery.
My best friend at school was Sylvia who looked after me and protected
me from the bullies. She was 6 months older than me and supervised my
daily life including taking me to the toilet and ensuring that I
changed for swimming and gym correctly. She was familiar with every
inch of my body whilst I had only seen her fully dressed. She took me
to her house after school where I spent a couple of hours before Mum
was home and I returned to my own house. During this time Sylvia washed
and groomed me so that Mum did not have to. She also watched me do my
foreskin exercises and often took over if I was not showing enough
enthusiasm. She also washed my private parts to maintain their hygiene.
I asked her what girls looked like without their clothes and she said
that she would show me when I was 7.
At home I reverted to being Steph and happily lived this double life
permanently under female supervision. I actually found this comfortable
and very soon had accepted that as a boy I was quite properly inferior
to my female mentors. Sylvia not only checked my cock daily but also
let her girl friends both watch and help. It reached the state where as
many as 6 girls were seeing me naked on a regular basis and I was still
ignorant about their bodies.
On my 7th birthday Sylvia took me to her house as usual and after
completing my ablutions said that she was going to show me what a
girl’s bottom looked like. I sat naked in the chair as she
lifted her skirt to reveal her tight white knickers. She then lowered
them at the back and I saw a pair of buttocks not dissimilar to my
owned. She then turned around and lowered them at the front and
introduced me to her front bottom which was a one inch vertical slit,
smooth and neat, with a button at the top where the two lips met. I was
invited to go closer and caught a new aroma of a sickly sweet, musky
kind that she said was how girls smelt. I found it heady and attractive
as I marveled at this whole new world. She then produced a pot into
which she was going to wee. Her legs parted to show an opening that was
darker than the exterior and from which emanated a stream of urine
which splashed into the pot, following which she dabbed herself with a
tissue prior to pulling up her knickers. I was spellbound by the whole
experience and she said that we were now as good as engaged, and we
would in future be totally open with each other and by my next birthday
I would be invited to touch what she affectionately called her pussy.
At school I had failed to make the football team and was sent to play
netball with the girls. I played at centre and was very good so much so
that the sports mistress wanted me to play in the school team.
Permission was refused as only girls could be in the team prompting the
teacher to suggest that I might impersonate a girl for representative
games. The other girls brought netball clothes and a school dress and
with my delicate features, long hair and slim smooth legs I was
convincing enough to blend in. I became a regular and the best player.
I also gained access to the girls’ changing room where I saw
a lot of my teammates and their opponents undressing and casually
walking about naked. I was so accepted that they soon forgot that I was
different and viewing bums and pussies became a regular treat, whilst I
made sure that my cock was never there exposed.
By my 8th birthday I had become familiar with several dozen pussies at
netball and at Sylvia’s house. Sylvia’s friends
were more relaxed with me and I saw them as well as her. In return I
was totally open with them and often let them remove all my clothes and
touch me which I found to be very exciting. On my actual
birthday Sylvia and I were alone and we both undressed and climbed into
her bed. She lay on her back with legs open and put my hand onto her
moist pussy. I explored both the outer lips and interior with my
fingers as she caressed me, after which she pressed the end of my cock
between her labia and squeezed me for half an hour. We both uncoupled
feeling wet and excited before kissing passionately.
This continued for 2 years on a weekly basis during which we both
agreed that we were free to pursue any opportunities that arose as long
as we confessed them to each other. I had a few liaisons whilst she was
at it every week and excited me with lurid descriptions of the many
cocks that she had encountered. I found her reports as
exciting as her handling of me and she was equally turned on by my
exploits with the netball team. By the time we were 11 we both
considered ourselves sexual beings when she broke the news that our
engagement had to be ended. Her mother had told her that she was
entering puberty when her whole body and mind would change and she was
not to have anything to do with boys until she was 13. The boys also
needed to concentrate on their own development during which their
transformation would be as drastic as that of the girls.
I was bereft and took refuge in my other persona as Steph. I went to a
secondary school in a different town where Mum had managed to register
me as a girl, and resolved to go through puberty with the other girls.
I would be a chaste virgin and not seek liaisons with either sex whilst
observing how all my friends coped with this new challenge. It did not
quite work out like that, but that is another story.