Date: Tue, 3 Sep 2013 17:57:36 +0800
From: John
Subject: The Scoutmaster Took My Anal Cherry

For those who are likely to be offended by descriptions of underage gay sex
then now might be a good time to visit another article. This is my first
story.

The Scoutmaster took my anal cherry at 12.

I have enjoyed sex throughout my life with both male and female partners
and although it has had some bitter sweet moments I only ever regret the
things that I did not do where I was held back by my own inhibitions.

This episode tells of my first experience of sex when I was a young boy
with my teacher who was also my Scoutmaster. As background, I think that I
have always been blessed with natural good looks (usual disclaimers), dark
haired and a slim body with a bubble butt, a cheeky personality, a sense of
self confidence and a good sense of humour. Alas I was never well endowed
and my penis only matured to around 5 inches, not that this inhibited my
sex life much, but I did (and do) suffer from penis envy and perhaps this
contributed to my bi sexual tendencies.

I was born in the North of England from a working class family and at the
time of this story (around 1958) I had just started high school, I was
still in short pants and had virtually no body hair, much to my annoyance
at the time as all my classmates seemed to be sprouting hair everywhere!  I
was very small and under developed for my age and I had just learned to
masturbate but was really naive by today's standards. What I knew of sex
was learned from comments from other kids at school and I did not really
understand the mechanics of homosexuality- that was soon to change!

Having been in the Cubs at the junior school I joined the scouts when I
went to senior school. The Scoutmaster was a teacher at school and I
suppose he would have been in his late 30's and had served in an elite army
brigade during the second world war. I remember him as quite an
intimidating character, at least in the eyes of a young boy, medium height,
curly sandy coloured hair wiry and fit.

In the Scouts he always went out of his way to be friendly to me, laughing
and joking and always ready to put his hand on my shoulder and make a fuss
of me. I guess I looked up to him as a hero and lots of the other boys my
age were jealous that we got along so well together.

When the school (Boys only) put on a play it was suggested that I would be
ideal for the role of a teenage girl, I remember that the role consisted
mainly of a couple of speaking lines and a lot of high pitched girly
shrieking. Of course for the role I had to wear make -up, wig, a short
skirt and heels and a padded bra - to meet the expectations of the other
school boys. Ray, the scoutmaster was there to help me dress for the dress
rehearsal and he did a great job on the make-up and the wig by all
accounts, but it did not quite stop there.  All the boys were dressing for
their parts and there were quite a lot of people in the gym where we were
preparing and I was getting quite a lot of compliments for my dress up.

When I was just about ready I was shocked when Ray put his hands up my
skirt and pulled down my white cotton underpants and said that he had
something that was much better and pulled out a pair of white girls satin
panties and asked me to step into them, I complied without thinking and as
he pulled them up he adjusted them and grabbed hold of my little boy cock
which responded immediately. I confess that I had a mixture of feelings, I
certainly enjoyed Ray playing with me, I enjoyed the feel of the panties
but I was embarrassed because " Donk",the physics teacher was watching us.
Donk was in his mid forties, a potbellied guy with hair everywhere,
sticking out of his nose, out of his ears, just everywhere and at that time
I did not know where he got his nickname. I wriggled and tried to get away,
not because I did not like the feeling but it was just so public and I was
mbarassed. To make matters worse Donk got up from his chair and came over
to us and complimented me on being such a pretty little girl. He then
addressed Ray with a smile and asked if he could have me when he was
finished with me. None of this made any sense to me at the time but it
would become clear in the course of events.

Anyway the dress rehearsals went without a hitch, everyone made such a fuss
of me I felt really quite grown up ad I walked home with quite a buzz and
the memory of the "touch up" from Ray made me feel quite "sexy" and I
masturbated as soon as I got home at the memory of the silk panties and his
big hand on my dickette.

That weekend I was allowed to join a group of the Scouts who went away
walking the mountains and staying at a couple of Youth Hostels. Ray had
spoken to my parents and suggested that the fresh air and the exercise
would be good for developing my body, they were probably happy to see me go
as I was a bit of a handful and I guess they thought it would be good for
my adventurous streak.

I enjoyed the hard physical exercise and the company of Ray who went out of
his way to be kind and considerate, I was probably a bit cheeky in parts
but nothing particularly memorable but he did make a couple of comments
that cheeky boys got smacked bottoms. I gave it no further thought and we
arrived at the Youth hostel where we were all staying in a common
dormitory.

After we had had cleaned up and dressed in our pajamas we were all sitting
in the dormitory singing Scout songs and having a great time. Ray then
announced to all that there was some punishment to be handed out and a few
of the older boys smiled as they obviously knew what was coming. Before I
knew what was happening Ray had picked me up, pulled down my pajamas pants
and walked me around the room where each of the other boys took turns in
smacking my bare bum. This made me squeal and brought tears to my eyes and
everyone thought it was great fun but I did not enjoy it at all and was
embarrassed.

Ray said I should not be such a cry baby and should not be so cheeky to him
next time. Everyone else went back to what they were doing before the
"entertainment" started, leaving me with my pants down and big red hand
marks on my bum, absolutely humiliating! Ray took pity on me (I thought)
and told me to stand next to him and he would put some lotion on my bum to
take away the pain. So he then applied a cold soothing lotion to my bum
which felt much better and he massaged it in to the red weals and I could
also feel it running down my bum crack. His finger followed the lotion down
and before I knew what was happening he was circling my bum hole and I was
not complaining at this stage. However when he inserted his finger into my
bum I squealed and said "no fingers in bums!" and of course all the other
boys turned to see what was going on. Ray got really mad and slapped my bum
really hard and told me, in a loud voice, not to be stupid and childish and
to go to bed. I went to bed and cried myself to sleep, long after the pain
had gone I cried because I had upset Ray who I wanted to be my friend.

The next day we hiked further across the mountains and Ray hardly had a
word for me, or when he did it was in an angry voice and I felt really
sorry that I had made him so angry. The rest of the walk was a nightmare
for me. The next days at school were the same and I blamed myself for
disappointing him.

By the middle of the week I felt that I had to apologise to him, in
hindsight of course this makes no sense whatsoever but I guess that I had
feelings for him and I wanted to please him. So when I walked up to him
after school I said that I was sorry that I had upset him and that I was
very sorry. He was still very cold to me but told me to come to his house
the next afternoon after school and we would discuss it further, he then
just turned on his heel and walked away, leaving me uncertain as to whether
I could ever be his friend again.

I could hardly sleep that night and at 5 the next afternoon I walked up to
the front door of his house, which was only a short distance from the
school. His home was a Victorian 3 storey house in a terrace and when I ran
on the door bell I really did not know what I was going to say. His sister
answered the door and I said that I was there to see Ray, she smiled and
asked if I was one of Ray's special friends? I said that I supposed so as,
at that time, I was unaware of the innuendo. She lived on the second floor,
Ray lived on the top floor and the ground floor was a common area
comprising the parlour, kitchen, dining room etcetera.

She knocked on the door, said "have a good time" and left me waiting for
Ray to answer. He certainly took his time and when he did answer he was
just dressed in a white toweling dressing gown. He looked very stern and
ushered me inside the room, looked me up and down and asked me what I
wanted to say to him.  With tears in my eyes I said that I was sorry if I
had upset him as I wanted to be his friend. To my great relief he put his
arms around me and held me to him and said that it was OK but did I really
want to please him and did I know what he wanted? would I do what he told
me to do? Well I guess that having played with my cockette and stuck his
finger up my bum I knew he wanted me sexually but at that age and with my
naivety I was not at all clear on what that actually meant in physical
terms.  He was however making it very clear to me that it was all about his
pleasure and my role to provide it to him.

I said that yes I did want to please him, yes I could keep secrets but I
did not know how to please him. He laughed in a kindly way and said that I
should trust him and that he would not do anything that I did not want him
to do and that he would teach me all about sex and make me a "grown up" and
I would become his very special friend. He then held me close, looked me in
the eyes and was then quite explicit. He said that I would suck his dick
and he would be sticking his dick up my bum, that it would hurt a little
bit but then I would learn to enjoy it. He offered me the opportunity to
leave but said that if I stayed I would have to absolutely do as I was
told. I enjoyed being held closely by him and I chose to stay, without much
hesitation I might add.

His hobby was photography and he had his own darkroom next to his
bedroom. He took me by the hand, kissed me on the forehead and told me to
sit on the settee and he would show me some of his pictures. They were all
in black and white and all featured young boys dressed up as girls- in fact
I thought I recognized one of the older boys at the school. The photos were
all of fully clothed boys in girls clothes but some showed them lifting up
their skirts to show their panties. So I understood that I was not the
first but I was not really jealous as I was happy that he had chosen me.
He told me that his sister helped him take the photos as he was also
featured in some of them.

He showed me the clothes that were for my part in the school play,
including the white satin panties and he said that he would take some
photos of me when I was dressed in them, but that first I had to learn to
prepare myself, how to make myself look attractive to him. He did stress
that it was up to me to make myself attractive but that he would show me
how and that we would start in the bathroom.

He lead me into the bathroom and undressed me, of course my cockette was
standing at attention and he bent down and took it all in his mouth, I
nearly fainted as it felt so good, remember this was the first time anyone
had done this to me and it was something I definitely wanted to
repeat. Unfortunately he stopped and said that it was now his turn, he
opened his dressing gown and there was this beautiful, half hard man dick
and I needed absolutely needed no encouragement to get on my knees and try
to suck it. I suppose that in hindsight it would have been around 6 or 7
inches long but it just seemed so attractive to me that I think my mouth
was watering.  I never quite got the sucking right straight away and he
said that I was being too enthusiastic and my teeth were getting in the
way, but he would show me how to do it properly later. He took it away from
me which was a shame as I wanted to go further without delay. He then
stripped off his dressing gown and let me see his beautiful man body, not
an ounce of fat, a light dusting of body hair and a toned physique, so
beautiful.

Ray said that as his special little girl (yes those were his words) I
should always be very clean and have no hair. Not having much hair was not
much of an issue as I only had a few wisps of hair around my bum and the
base of my penis and under my arms- which he whipped off smartly with a
razor. This was a shame as I had been cultivating those hairs as a sign of
impending manhood. We were now both naked in the shower and he was soaping
me all over and his soapy finger was finding itself up my bum, which was
very uncomfortable at the time. I could feel his rock hard dick in the
middle of my back.

At this point he explained the importance of inner cleanliness and that it
was not attractive to get his dick covered in poo when he entered me and
that I should first have an enema to make sure that I was absolutely clean
to receive him. This lesson made me understand how important this cleaning
ritual was and to this day I try to make sure of my cleanliness. He
instructed me in the use of the enema and said that I was to use it at
least twice and then to come out of the bathroom and he would dress me up
and put on my make up before he took some photos of me.

Skipping past the smelly details of the enema I came out of the bathroom
clean, smelling sweetly and with not a pubic hair to be seen, ready to be
dressed and photographed as a little girl.

At this stage Ray had on his dressing gown again, a shame really as I loved
the look and feel of his dick. But he quickly dressed me, put on make-up,
lipstick, a wig, thigh length stockings, shoes etc and by this time I was
truly transformed and looked like an exquisite little girl. Looking in the
mirror I could hardly believe it was me.

Pronouncing me ready for the photo shoot he shouted down the stairs to his
sister to bring some special lemonade. Minutes later she entered the room
with a tray of lemonade and cake and said that it was her very special home
made lemonade and that I would enjoy it and it would help me to relax. Well
she was certainly right about that!

Ray asked her to stay and help with the photo shoot and so they fussed
around with putting me into various poses, some showing my panties and
others just trying to look coquettish, lying on the sofa, head on hands,
pouting and so forth. Ray was showing me some of his photos to try and get
me to replicate the poses, childishly I felt quite proud of myself during
this exercise and no doubt "hammed it up" and tried to make myself look
sexy.

As this was going on I found that I was becoming very relaxed and when I
mentioned this to Ray he said that this was the "special lemonade" which
would help me to relax when he fucked me later, well at least he left me in
no doubt about his intentions!

His sister was a bit strange as she was clearly aware of Ray's penchant for
young boys and was clearly complicit in their seduction. Years later I
wondered if she was actually a woman or if she was a transsexual, one of
life's mysteries to me.

So moving on from photos of just me in seductive poses they started to
involve Ray in the photos, wrapping his arms around me from behind, me
looking up at him with stars in my eyes. The last photo which his sister
took was one where he was stood behind me in his dressing gown, I could
feel his hard man dick pressed against my bum and he took my hand from my
side and brought it behind my back to wrap my fingers around his dick. She
was watching with a smile and said that she would leave us to play and then
went downstairs. By this time my knees were feeling weak and I was feeling
very receptive to the idea of him penetrating me, but of course I was not
aware of exactly what this entailed.

He turned me around to face him and opened his dressing gown to expose this
beautiful man dick which was rock hard by this time, showing some pre-cum
on the tip and it seemed to be coated in baby oil or something
slippy. Pushing me to my knees (not much effort required there!) he told me
to hold his dick and Lord but it felt so good, hard but soft at the same
time and slippy, circumcised with purple veins and an upward curve, I
remember it like yesterday. The image and the sensation was burnt into my
memory banks forever, I can get hard now just at the memory.  At this stage
I think he made the decision that now was the time to press ahead, he
clearly had me pegged as a sissy boy and of course he was right. He lifted
me up as though I weighed nothing and carried me to his bedroom and laid me
out on his bed, at this stage I was still fully dressed but with a growing
wet spot on the front of my silk panties. He pulled my panties off and bent
down and started to suck my dickette, within seconds I was nearly climaxing
and he stopped and gripped the base tightly saying that I had to take my
time and wait. Damn!

He turned around so that I could suck his dick while he played with mine, I
loved the feeling of having his an dick in my face and I tried really hard
not to scratch him with my teeth. In the meanwhile he was nibbling at me to
keep me interested and his finger reached between my legs to circle my bum,
this was heaven. He had clearly lubricated his finger as it soon penetrated
by bum into the now clean insides. I have to admit it felt uncomfortable at
first but within a couple of moments I started to relax, one finger was
soon replaced by two as the loosening up/preparation process
began. Lubricant and finger work together with the pleasure of having my
dickette sucked were preparing me for the main event. In hindsight I
suppose I should be pleased that Ray had done this all before and used
plenty of lubricant. I was feeling really relaxed and receptive, no doubt
assisted by the "special" lemonade.

He stopped for a moment and told me that he was now going to fuck me, no
question in the tone of voice, just sublime self confidence that brooked no
doubt as to the outcome. He did tell me that it would hurt a little but to
trust him and that the pain would soon pass and that I would enjoy it. With
that he rolled me onto my back at the edge of the bed and asked me to bend
my legs up to give him access. I was all for this until the tip reached my
bum when I tensed up. Ray bent over me and tried to kiss me which I thought
was gross, in my mind sex was OK but kissing ..ugh! especially as he was
bristly and his breath smelt of cigarette smoke. I suppose that this
influenced me towards tobacco and I never did take up smoking.  I had liked
Ray nibbling on my ears and kissing my neck but trying to kiss my lips was
a step to far. Well alpha male Ray was having none of my resistance, he
slapped my cheek and told me that I was going to kiss him and that I would
come to like it once I got used to the feeling and that was that. He kissed
me and I did not resist a second time, his tongue was soon in my mouth and
I did find myself relaxing and returning his kiss. All the while the tip of
his dick was pushing gently at my bum and I was becoming progressively more
relaxed, how much of that was due to the kissing and how much of it was due
to the "special lemonade" I cannot say but there was only going to be one
conclusion. Ray broke off from the kissing to say how beautiful I was, how
much he loved me, how he appreciated what I was doing to please him and
how, when I was ready for him to enter me that I should just push out as
though I was going to the loo and that when he entered me he would be
gentle until I was used to the feeling but that I would definitely enjoy
it.

 Well sure enough the kissing continued, my relaxation continued and the
pressure of his dick, covered in lubricant reached the point where I pushed
out and the tip of his hard dick slipped past the sphincter, but Lordy it
did hurt! I am sure I cried out at this time but he soothed me, muttering
about what a beautiful girl I was. He kept his hard dick still until I
became accustomed to the feeling. As the seconds ticked by I did start to
accommodate him inside me and as I relaxed he gently started to move inside
me and I started to move my legs around his back as I gained more
confidence. All the while he was telling me what a beautiful little girl I
was and how I was his special friend. Ray's movements started to increase
as he drove his dick deeper inside me and then withdrew it to the edge, I
felt so full and it felt so right that he was deep inside me, the initial
pain was now fading.

Soon Ray was taking full strokes and his balls were banging against me and
he was grunting with pleasure and reassuring me all the time. At this time
I realized that I was no longer a virgin, that, even though I was only 12
years old that I was pleasuring a man and I was also becoming a grown up
and I felt quite proud of myself as I held my arms around his neck and his
back.

Of course it still hurt a little, but now more of a dull pain that was
being replaced with, if not exactly pleasure, satisfaction. My dickette
that had wilted during the initial invasion started to recover a little and
Ray's pleasure was my pleasure, my legs gripped him tighter and I found
myself rising to meet his thrusts. In truth it was not long before he
groaned and I felt him splash inside me and his strokes became slower until
he eventually popped out with a loud sigh of satisfaction. I loved the look
of his semi hard dick, covered in lubricant and semen and reached out to
touch it and held it tenderly. What was the most satisfying for me was that
I had succeeded in pleasing him and that he was happy with my performance,
surely I would now be his special (girl) friend?

Having been satisfied by my anal cherry Ray now took hold of my dickette in
his hand, held it next to his own and rubbed the big and the small together
to spread the lubricant and then proceeded to wank me and suck me until I
came, which did not take long at all! By this time the special lemonade had
done its work in relaxing me and I was nearly asleep, Ray was lying on his
back, naked with a smile on his face and he pulled me close to him and I
laid my head on his shoulder and had my hand on his now flaccid cock. Ray's
semen was running out of my bum and I was nervous about getting it on my
nice dress, I was going to get cleaned up but Ray said to leave it and I
was so tired anyway I just wanted to sleep. Within moments I was asleep and
I must have slept for about 30 minutes.

When I woke up Ray was spooning me and was starting to penetrate me from
the back, he was holding me closely in his arms and nibbling my ear and
telling me how special I was. My dickette was soon rock hard again (the
joys of youth) although my bum was definitely starting to feel a little
tender.

What with the previous lubrication and loosening up of the previous
session, there were no problems with Ray rapidly penetrating me and driving
hard into me, this time he could play with my dickette while he hammered
home. Again he splashed inside of me and finished me off with a blow job
where I came in his mouth. Another first for me which was my reward for
being a good "girl" and it was much appreciated, I thought I would die from
the pleasure. I confess that by the time he finished with me I was sore but
proud that again I had pleased him.

After that session I sat on his knee as he cuddled me and we watched
television together. As it was starting to be time for me to go home he
took off all my girly clothes, removed all traces of make up and promised
me that next time that I came around that I could try some of his other
sexy clothes. I was more interested in the possibility of coming around
again than the clothes which although they were nice, probably did more for
him than me. He rubbed some soothing cream in my bum and placed a tissue in
my underpants so that it did not mark my underpants and raise questions
with my parents. He had thought of everything!

Before I left we agreed that he would give me extra "tuition" on Tuesdays,
Thursday evenings and Saturday mornings. As his sister let me out the front
door she asked me if I had a good time, I was a bit embarrassed of course
as I supposed she knew what we had been up to, but I mumbled yes. Her
parting comment was that I would probably not need her special lemonade the
next time I came around. Hmmm!

Looking back and with the benefit of hindsight I can see that I had been
seduced by a smooth, serial pedophile, but it had not been unpleasant, in
fact I actually enjoyed the initiation into sex. It opened up a whole new
chapter in my young life. Later I was to learn more about the character of
Ray and his friends.

Of course I can now see that the whole episode was morally reprehensible, a
figure of authority taking advantage of an innocent young boy but, unlike
some, it did not noticeably damage me later in life.  I felt that the sex
was consensual and had delivered more pleasure than pain but I can
definitely understand how some people are traumatized and damaged,
particularly where their experience verges on rape.

But on that particular day as I walked home I was a mixture of emotions.
Probably above all was the feeling of satisfaction at being able to please
Ray and that I was now definitely his special friend and that we shared a
secret. The remnants of his semen were still dribbling out of my somewhat
sore bum but I was definitely looking forward to returning and learning how
to suck his cock to please him even more. The next day at school he was all
smiles and kind touches...heaven!... I was back in favour.

I was looking forward to my continued training at his house.

To be continued...