Date: Wed, 17 Apr 2013 09:15:28 +0100 (BST)
From: penny cox <pennycox694@yahoo.co.uk>
Subject: The School Play

Simon loved being at his all-boys school, and now in the second year, was
well connected in the school mutual wanking society. Two or three times a
day, he'd go to the toilet block, out by the games track, and lock himself
in a cubicle with another boy. It was quiet out there, with very little
chance of being disturbed. How he loved the moment when his friends'
trousers would fall to the floor, and he could see him in just his
regulation underwear, white y-fronts, and then slipping his hand down
inside them, and fondling with the object of his desires. He was totally in
love with cock, and was becoming well-known for his love of giving hand
relief. Older boys had started to come and find him, and now the end far
end cubicle at the games track toilet was his favourite place to be.

However, at home Simon had a secret, he loved dressing up. His mother had
banned him from dressing up in any of her clothes, after coming home and
finding him dressed up and wanking himself off in front of the mirror in
her bedroom. Luckily for him, his slightly younger sister came to his
rescue. He had confided in her about his strong feminine feelings, which
got stronger when he dressed up. She suggested to him that maybe he should
bave been born a girl, and agreed to help him as long as it stayed a
secret. Simon was soon wearing her gym knickers most of the time at home,
and sometimes to school if he hadn't got PE. Then followed a bra and a
petticoat, which was a bit tight, but she let it out somehow. The wrap
around gym skirts were easy to adjust, and with a white blouse, Simon was
looking good as he looked in the mirror.

Then came an offer to star in the school play, playing the part of a
teenage girl. Simon said yes, but he hadn't got any clothes, lying to keep
his secret going. Two of the teachers with teenage daughters said they'd
help, and soon Simon had a locker full of lovely feminine wear, which he'd
try on after school, in the gym changing room. Simons' mother wasn't happy
about his part in the play, but agreed to give him some lessons in
make-up. Thinking he was alone in the gym changing rooms, he unlocked the
locker and got out all the clothes, laying them out along the benches. It
was 4.30 in the afternoon and everyone would have gone home by now, he
thought. He started to undress, and couldn't help gently carressing his
little cocklet as he looked down at the skirts, blouses, a bra, panties
from his sister, black tights and a pair of dainty black sling-back shoes
with a two inch heel.

Simon had an hard-on by now and, pulling on a pair of his sisters panties,
seemed to show it off, pushing the sheer material out at the front. Then
came the bra, fastened at the front, like his sister showed him, then
sliding it round him until the cups appeared at the front, and slipping his
arms into the staps. He looked in the mirror and fondled the cups for a
while. Then nice crisp white blouse, that let the bra show through, and a
pleated wrap-around gym skirt. Not wanting to hide the cock-filled panties,
Simon decicded not to put the tights on, but just slipped his small feet
into the lovely black sling-backs. Then he just posed, hands on hips, in
front of the mirror, swaying from side to side, lifting the skirt to
inspect his cocklet, which had stayed hard. Now for a walk, Simon thought,
and set off along the changing room, his shoes making those lovely
"Clip-clop" sound. Time and time again he walked up and down, stopping each
time at the
 locker end to look in the mirror. His mind was full of nice fluffy
feminine thoughts, of walking like a lady, swishing the skirt out as he
turned, to give anyone watching, a glimps of panties. "Shame there's no-one
looking" he thought to himself. His mind turned to boys, especially the
older boys that he was now servicing in the toilets. One had introduced him
to french kissing, which he liked straight away. Simon stepped forward and
kissed the mirror several times as his hand slipped under his skirt and
started to carress his lovely hard cocklet.

"You're lovely" someone said, breaking to silence. Simon spun round to see
old Reg, the assistant caretaker, standing in the open doorway to the
showers. "How long have you been there" Simon spluttered. "I was in the
shower room when you came in" Reg whispered "So I've been watching all the
time, and it's true, you are lovely.".............. After a pause Simon
said"I am in the school play as a teenage girl, so I am
rehearsing"......"Of course you are" Reg said, walking over towards
Simon. "And over in the sports field toilets, is that rehearsl to"? Simon
froze with fear. "Iv'e seen you in the end cubicle, with those boys,
kissing and wanking them off. I saw you by accident, when I was doing some
maintenance, but from then on I've followed you over there. At least twice
a day. You like it don't you"? Simon silently
nodded...................After a long silence, Simon whispered "Please
don't tell anyone Reg, please............................."Maybe" Reg
 sighed. "I only work two days a week, and I won't say anything if you meet
me in that toilet cubicle after work. That's 4.00pm Tuesday and
Friday.......ok"?

Simon thought for a moment, the embarrassment if it got out, the dicipline,
the shame. "Ok, and you won't tell"?  Reg was in his early 60's, a plump
balding man, not Simons' ideal toilet cubicle date. Reg stepped right up to
Simon, and slid his arm around Simons waist, and pulled him close. "Let's
start with some of that kissing I've seen" Reg tilted his head, and Simon
knew he had to do it. "I can't stay long" he managed to say as Regs lips
met his. Four or five little kisses followed, with Regs' hand working up
Simons' back, stopping at the bra clasp, which he played with for a
while. "I'm going to call you Sissy Boi" Reg whispered "And you're going to
be my Girlfriend on a Tuesdays and Fridays. Now just relax, no-one is going
to see us, I've locked all the outer doors. You're all mine". Regs' head
tilted and another kiss came. Simon felt bristles for the first time, from
Regs chin and top lip. Simons' other toilet cubicle friends didn't have any
 whiskers. Regs' orther arm slid around Simons' waist, and he was pulled
very close. He became aware of something pressing against him......Oh, Reg
must have a hard-on.....Then a tongue......Simon knew about french kissing,
so he automatically opened his mouth. Reg made a noise in his throat, as if
he was enjoying the snog, and Simon felt tongue as well as whiskers.

At the end of the second long kiss, Regs' hands were trying to undo the
blouse buttons. Simon looked down, and saw Reg struggling. "Here, let me"
Simon whispered in Regs' ear. Reg took a step back and watched as Simon
undid the blouse and slipped it off his shoulders. Simon was beginning to
enjoy teasing a man. As the blouse fell to the floor, Simon asked "Do you
like my bra, it's my Mums. Do you want to feel it"? HHHmmm more teasing,
Simon could get used to this. As Regs' hands ran over each cup, Simon
suggested "Maybe you could lend me a few pairs of your underpants to pad
the cups"? Reg nodded and pulled Simon close again, for more kissing. "Why
don't you take those overalls off Reg" Reg instantly steeped back and began
to unbutton them. Simon found he enjoyed watching a man undressing. As the
boiler suit fell to the floor and Reg stepped out of it, Simon looked him
up and down. He was standing there in y-fronts and a vest. The y-fronts
were
 bulging out, and Simons' feminine thoughts were getting stronger. "Now the
vest" Simon said out loud, and Reg obeyed, easing it up over his
head. Simon looked at Reg, stripped to the waist, with a pale podgy belly
overhanging the waistband of his pants. Reg stepped forward, arms around
Simons waist again, pulling them together. More kissing, more tongue. Simon
felt a natuarl urge to cuddle Reg back,so he slipped his arms around Regs'
waist, and lowered his hands onto his bottom. As they kissed, Simon began
to carress Regs' bottom cheeks through the pants. Reg began to grind his
hard-on against Simon......it felt nice.

"What time have you got to be home" Reg asked between kisses. "Not yet"
Simon sighed, easing his hands down the back of Regs' pants. They slipped
down a bit as Simon pushed his hands down further. "Let me take them off"
Reg suggested, and Simon took a step back to see the y-fronts sliding
down. "OOOOhhhhhhh" Simon gasped as he saw Regs' cock for the first
time. "Do you like it"? Reg asked as he stroked it, pulling the foreskin
back and forth. Simon nodded and undid the gym skirt. It fell to the
floor. "Panties" Reg said, and Simon obeyed, easing them off and, holding
them up said "Do you like my little panties Mr Caretaker"? Reg stepped up,
took Simons hand and held it to his cock. Simon began to wank it for
him. It seemed bigger, thicker and with so much curly hair....More
kisses...just like being in the toilet cubicle..., but much better. Between
kisses, Simon looked down at his hand, working on a much nicer
cock...."OOOhhhhhh Reg, it's lovely" Simon
 sighed as he looked down. "Do you really like it"? Reg asked....Simon
nodded. "Then sit on the bench for me" Reg said. Simon obeyed, plonking his
bare bottom on the wooden bench. Reg took hold of his cock, and stepped
forward, slowly wanking it, until it touched Simons face. Clear juices were
ouzing out of the tip as Reg wiped it all over Simons face. Round and round
it went, then across his lips. Simon poked his tongue out...it tasted
nice. He looked up at Reg and whispered "That tastes nice" and opened his
mouth slightly. Regs' helmet was pressed to his lips. Simon knew what was
expected of him, and with eyes wide open, parted his lips enough to allow
Reg to slip his big purple helmet inside. Simon saw the foreskin had rolled
back, and enjoyed having this big thing in his mouth.

"OOOhh, that's my Sissy-Boi....suck it" More of Regs' cock was being pushed
into Simons mouth, then Reg got a rythm going, easing it in and out. Simon
was in heaven, a mans cock in his mouth for the first time. He ran his
hands up the back of Regs legs and grabbed his bottom cheeks, gripping onto
them, feeling the rythm as they pumped in and out. On and on Reg went,
making love to Simons' young mouth, moans of joy coming from his throat, as
he felt curly hairs tickling his nose. Simon knew that he had all of Regs'
cock in his mouth now, and how he was loving it. Quite suddenly Simon felt
something new. Regs' cock was sort of jerking.....then an unmistakeable big
spurt... oooohhhh Simon knew what was happening.  "Take my cum Sissy boi"
he heard, and was happy to, feeling each spurt slowly filling his mouth.

End of Part One