Date: Wed, 14 Dec 2005 18:17:37 +0100 (CET)
From: Gillian Dupree <jilly_dupree@fsmail.net>
Subject: Spring Half-term Holiday - TG

This is really a story of what I did during the spring half-term holiday
but, in order to put it into context; I am going to start at the very
beginning.

My name is Gillian. It is not the name I was given at birth but it is how I
am known at home, at school and by my friends. I am sixteen years old and
go to a private, mixed school for 4 to 18 year olds near to my home in
Somerset. I live with my Mum and Dad and I have a sister, Jacqueline, who
is 18 and is at University in Scotland.

Two events have shaped my life: my first day at school and Christmas Day
1997. I can remember my first day at school as if it was yesterday. Jackie
and I were dressed in our uniforms and waiting for Mum to get the car out
of the garage. It was a cold day and it was raining. I was wearing grey
wool short trousers, long grey socks and a grey duffel coat. I was
thoroughly miserable as the wind and rain were getting in through the gaps
in my coat, my knees were bare and turning blue and my trousers had got
stiff with the rain and were chafing the backs of my legs. Jackie was
wearing red woollen tights under her skirt to keep her legs warm and had a
knee-length pink coat on with a fur trim round the hood and cuffs. She
looked as warm as toast and I thought "Why can't I wear tights and a
fur-trimmed coat?" Being 4 years old, I asked Mum why I couldn't and was
told not to be silly as they were only for girls. This was so unfair in my
mind and it stayed in my head.

Over the next few years, my sense of the unfairness of "girls' clothes"
grew and grew. Jackie could wear different coloured tights -- I had to wear
thick grey socks. Jackie wore short white socks and a light summer dress in
the summer -- I was still in thick grey socks, wool trousers and a
long-sleeved shirt. Jackie wore pretty black patent-leather shoes with a
strap -- I had heavy lace-up shoes which I had to polish. Basically, all
Jackie's clothes were bright and pretty and she got a say in what Mum
bought her while my clothes were all grey and ugly and my only contribution
was to stand in the shop while Mum made the choices. And, to top it all,
Jackie could dress like a boy any time she wanted! She was free to wear
jeans, sweatshirts and trainers unless she was going to school or we were
going out.

Matters came to a head on Christmas Day just before my 7th birthday. My
present from Mum and Dad was an Arsenal football kit -- boring! Jackie got a
new party dress in black silk with lace-trimmed puff sleeves and masses of
white lace petticoats underneath. She was already wearing a red party dress
with pink net petticoats that I secretly envied. It was so unfair and,
before I knew what was happening, I was in flood of tears and was sitting
on Mum's lap crying that I wanted a party dress and why couldn't I wear
skirts and blouses and soft tights and shiny shoes. When I had quietened
down and Mum and Dad were trying to think of something to say, Jackie asked
"Why can't Jon wear a dress if he wants to?"

After a moment of thought, Mum said that there was no reason except that I
didn't have any dresses to wear. Jackie replied that she had loads of
clothes that she didn't wear any more and, in an imperious manner, grabbed
me by the hand and took me upstairs to her bedroom. I passed the next hour
or two in a complete daze as she basically treated me like a doll -- she
took my outer clothes off me; decided that my underwear was wholly
unsuitable and took that off as well; got matching vest and knickers out of
a drawer and put them on me and then went through her drawers and
cupboards, pulling out clothes, holding them up to me and then either
putting them back or putting them on a pile on the floor. Then she tried
everything on me. Skirts, dresses, tops and jumpers that didn't fit were
rejected and different combinations of everything else were tried. She
finally settled on a pink party-dress with white felt bunny-rabbits on it,
sewn-in petticoats in white lace and a huge pink bow at the back. She added
a pink fluffy cardigan and a pair of white lacy tights. She couldn't find
any shoes or slippers small enough for me so she took me back down stairs
to be presented to Mum and Dad.

Jackie seemed very proud when she led me into the drawing room. "Isn't Jon
pretty?" she said. "I think the dress really shows off his complexion. He's
got a lot more stuff that we will have to put in his room but you'll have
to take us shopping to buy him some shoes. He can keep the vest and
knickers and tights he's wearing but you'll have to buy him some of his own
because I don't want to share with him. If you buy him some other stuff,
get it so I can wear it as well." And that was that. We had Christmas
dinner with me in the frock. Then, while Mum and Dad washed up, Jackie and
I went upstairs. We threw out all the clothes we thought I could get away
with and put Jackie's old clothes in their place. Then we went into her
room and read books until we were called down for supper. After that we
watched television until bedtime. Mum seemed surprised to see that I had
one of Jackie's nightdresses rather than pyjamas but she didn't say
anything.

On Boxing Day we visited our cousins, Laura and Tom. I can remember wearing
a denim skirt and a red jumper. Mum solved the shoes problem by stuffing
tissue paper in the toes of a pair of Jackie's shoes. Nobody seemed to
notice. They told me later that it seemed rude to point it out and as my
Mum and Dad weren't concerned, why should they be?

We went shopping the next day. Jackie was concerned that she had given me
three sets of underwear and tights but soon shut up when we got to the
local department store. We both went mad trying on dresses, tops, skirts
and, in Jackie's case, trousers. I also got a coat and a cape and two pairs
of gloves as well as a lot of underwear and tights. Mum must have spent a
fortune! Then we went to the shoe shop where Mum bought me a pair of black
patent-leather shoes with a strap (I hadn't forgotten) and a pair of bright
pink trainers.

Mum and Dad seemed totally cool about the whole thing. Jackie and I talked
about it and Jackie said that they thought I would soon get bored of the
game and, anyway, I would have to change back into boys' clothes when we
went back to school. I thought about this and decided that I really liked
wearing girls' clothes, I didn't like wearing boys' clothes and there was
no way I was ever going to wear grey shorts and socks again in my life. So
we went to talk to Mum and asked her when she was going to take me to the
outfitters to get me some school skirts and blouses. The conversation went
along the lines of "Everybody will laugh at you"; "I don't care" and "What
if you change your mind"; "I won't" and "What will you do about PE"; "I
don't like PE". Finally Mum saw it my way and I got three school skirts,
half a dozen blouses and a new blazer with the buttons on the left.

So along came the first day back at school. I was dressed in school uniform
with black tights, covered by my new cape with pink furry earmuffs and pink
fluffy gloves. It wasn't until I got out of the car that the enormity of
the whole thing hit me. I stood there absolutely petrified and I was going
to wet myself at any moment. Fortunately, Jackie spotted what was going on
and, taking me by the hand, she marched me over to a gang of her
friends. "Hello everybody. I got a new sister for Christmas. This is
Gillian and we've all got to be especially nice to her and play with her
and make sure nobody is nasty to her because she is my special Christmas
sister." When we went into classes, she went with me to my classroom and
said the same thing. And, do you know what? I never did have a problem. I
didn't do PE; I stopped playing football with the boys and played skipping
and generally hanging out with the girls instead. I can't remember anybody
being rude or unpleasant to me.

Phew! I've just re-read what I've written and realised that it only covers
2 weeks. I better get on a bit. The next 6 years passed by quickly and
without anything of note. I was, to all intents and purposes, a girl. I
spent all my time as a girl and with other girls and everybody, including
me, forgot that I had ever been anything else. Then came puberty! There
were the obvious physical issues -- all my friends were turning into women
and I was in daily dread of suddenly growing to 6 feet tall, sprouting hair
everywhere and my voice breaking.

The other problem was sexuality. When we were younger, boys were held in
contempt but suddenly, all the sexy clothes and makeup and hair styling was
to attract boys. I didn't want to attract a boy. I wanted to kiss my
girlfriends and just being with them and talking about what we were wearing
and how it looked was causing problems that were hard to hide in thin
knickers and a tight skirt. I was wanking off 3 times a day to keep my
willy under control (calling it a knob or dick doesn't seem right when its
less than 2 inches long and only 5 inches when hard).

Sooner or later I was going to get caught and one morning, just as I was
getting into my stroke, Jackie wandered into my bedroom to borrow
something. She was now 15 and developing a reputation as a slut. She had
been going out with boys for over a year, discovered that she liked sex and
her virginity was now a distant memory. She was smart, pretty and the best
sister anybody could have. Her first instinct was to ask if she could watch
but when she saw me burst into tears, this gave way to genuine interest and
concern for my problems.

She went into solution mode as soon as I finished explaining the
problem. "Don't worry about being tall. You're not 5 feet tall now so
you'll never grow as big as 6 feet. You never take any exercise so you
won't grow any muscles. If you take hormones you won't go hairy or get a
deep voice; you'll get a woman's body and you won't have to worry about
getting a stiffy. You won't need to get one anyway because only lezzies
might be interested in you and they prefer girls with fannies rather that
dicks."

As an aside, Jackie treated us to a 2 hour performance with the Head Girl
at a beach party that summer. They were all over each other like a rash
with fingers and tongues exploring everywhere and absolutely heaps of
groaning and panting. Her excuse was she had had too much to drink and
Morag Campbell was the butchest person at the party anyway. She had already
been knobbed by every boy at the party and none of them was worth a second
fuck.

"OK clevercloggs" I said. "It may well work but where do I get the hormones
from? I don't think I can just go into Boots, not even in Bristol, and buy
some."

"Easy" she replied. "You just go to the doctor. You tell her that you have
always wanted to be a girl and you will commit suicide if you can't be and
she will give you them. If you make an appointment for after school, I'll
come with you. If she sees you in your school uniform she'll have to
believe you."

Seeing the doctor was the easy bit. The doctor was very sympathetic but
explained that there was much more to it than handing over a prescription
for hormones. To cut a long story short, I had to go back with Mum and then
see physiatrists and endocrinologists and have loads of blood, urine and
other tests before I was given hormones. Then I had to keep going back for
more tests and adjustments to the dosage.

To cut a long story short, I am now a happy, well adjusted girl. I passed
10 GCSEs at A+. I am studying 5 AS levels in the sixth form and I hope to
go the Oxford to read PPE when I leave school. I'm 5'5" tall and measure
34B-22-36. I also have a girlfriend -- Carol. We were both in Monsoon trying
on clothes one Saturday. It has a communal changing room and she brushed
against me while taking her trousers off and noticed the bump in my
knickers. My reaction was to burst into tears (I'm good at crying) as I
thought she would tell everybody. Her reaction was more surprising. She
started to kiss my tears and cuddle me and told me that now she knew why
she fancied me but no other girl and did I fancy her and could we go out? I
had always fancied her but not in a really physical way as the hormones
seemed to reduce the interest along with the ability. Anyway, I said that I
wanted to go out with her but I wouldn't be able to do anything with her
because of the hormones.

I was wrong about the hormones. If you stop taking them until you can get a
stiffy and then start again as soon as you can there isn't a problem. Once
you start being unable to get one again you stop until you can. I reckon
that I don't take them for about 4 weeks every 3 months. My willy might be
smaller and a bit softer that it could have been but Carol hasn't
complained and we've been fucking for almost nine months. The really
brilliant bit is that Carol's Mum and Dad think I'm a normal girl so they
let me sleep over at Carol's every couple of weeks and she's got a double
bed that we share. Carol's Dad is a bit of a pervert. He's always hanging
around when I'm going to and from the bathroom and he comes into the
bedroom really early in the morning hoping to catch a look at me. I know
because if I wake up before he comes in then I arrange for one of my boobs
to poke out of my nightie then I pretend to be asleep when he comes in. He
will stand and watch until I pretend to stir then he makes a big show of
knocking on the door and coming in.

In fact, I think I get more sex than if I was a boy. When Jackie found out
I was going out with Carol (we try to keep it a secret), she started to
take the piss asking if I had to use a dildo to satisfy her. I told her
that I could satisfy her with my willy because I could get a stiffy and she
asked me to prove it. We were sitting in her bedroom so I slipped down my
tights and knickers and pulled my willy from under my skirt and started to
wank it. The next thing I knew, Jackie's hand was over mine and she was
whispering in my ear to let her do it while diddled her. One thing led to
another and I ended up on my back with my skirt around my waist with Jackie
bouncing up and down on me like mad. When we finished she said that she
understood how I kept Carol happy. I might not have the biggest willy in
the world but it took forever for me to cum and she had cum three times. We
fuck about once a month now. I know incest is wrong but Jackie has lots of
other partners and I think that its just a way of being close together as
sisters.

The other girl is Tracy who works in the beauty salon and waxes my legs. I
have been having my legs waxed for a couple of years and Tracy has known my
secret ever since she first did my bikini line (It might not be big but
it's hard to hide in semi-transparent nylon knickers). A lot of my friends
were having Brazilians done and I eventually asked Tracy if she could do
mine in a Brazilian. She explained that it would look silly without having
a pussy but she would be happy to wax me smooth. Tracy is about 25 or 26
with curly blonde hair and really big boobs that are always rubbing against
you while she is working. She always wears Miss Dior perfume which is one
of my favourites. Anyway, having this sexy-smelling woman rubbing her tits
against me while fiddling with my willy and balls (I'm sure they didn't
need as much re-arranging as they were getting) soon had me standing to
attention. I asked her to give me a minute to calm down but her response
was to wrap her mouth around my willy and start to slide it in and
out. Pretty soon I was in a position I am starting to get used to -- laying
on my back with a woman bouncing up and down on my willy. We do it every
time I go and get waxed. Tracy says it's my reward for being a brave girl
and not making any noise when she waxes the tender bits.

Oh my God! I have just realised that I've written 5 pages and still not got
round to the pint of this. Right, here goes. Last Spring we had a 4 week
break between the end of lessons at school and the start of our GCSE
exams. After 2 weeks I was bored out of my mind. I had revised everything
twice and new it all backwards. Mum and I were starting to fall out and
then Jackie came to my rescue. Why didn't I come up to St Andrews and stay
with her for a week. Brilliant! Even Mum thought it was a good idea and the
next day she dropped me at the Railway Station with £250 in my purse - £150
for the train and £100 to spend. However, I wanted to hit the shops in
Edinburgh so I had no intention of wasting my money on train fare -- I would
hitch hike. I was wearing a tennis skirt with a halter top, high-heeled
strappy shoes and no bra. I reckoned anybody would love to stop for a sweet
little sugarbabe like me. Soon I was standing at the M5 junction with my
thumb out and my cutest possible expression.

After about 5 minutes a huge green lorry pulled up. It took ages to climb
up into it. The driver was smartly dressed in a green uniform. He was
oldish -- at least 30 with beautiful wavy golden hair and the strongest
northern accent I'd ever heard. He spoke to me about five times before I
realised that he was asking me where I was going. When I told him that I
was going to Scotland he told me that he was in luck as he was going back
to his depot in Carlisle and you could spit into Scotland from there. So
that was me sorted.

I pulled up my bag, shut the door and settled into the seat by the door --
furthest from the driver. "Ye'll after sitoop bimee t'ear mee" he
said. What was that? Oh! "You'll have to sit up by me to hear me." I
shuffled over next to him and settled down for the ride. He started to ask
me questions as we went along - Why wasn't I at school? How old was I? Did
I like school? What music did I like? What was my favourite film? I found
that by leaning up close to his mouth and really concentrating I could
understand him. My answers were pretty monosyllabic to start with but he
was really friendly and I like to talk about my favourite subject -- me so
soon I was chattering away like a good one.

Then, after a couple of hours he made me stop in my tracks. "Have you ever
given a bloke a blow-job?" he asked. I flushed deep red and sat there
opening and closing my mouth like a goldfish. "I'm sorry" he said. "It was
in my mind and just sort of slipped out. You're a pretty young lass and
your mouth is just about perfect for sucking. Please, just take it as a
compliment and forget I said anything. I'll drop you at the next service
area if you're worried."

"No, it's OK" I found myself saying. "And in answer to your question, no,
I've never given a bloke a blow job. Why, would you like one?"

"I would love one" he said. "I've been sitting here with you blowing in my
ear and every time I turn to look at you I can see right down your
top. Resting your hand on my thigh and the way your skirt's ridden up to
show me your pink knickers doesn't help either. I've got a raging hard-on
and I'd rather you sucked it than I wanked it."

"Well I'm not sure that you would want a blow job off me. I'm not quite
what I appear on the outside." Then I told him that I was transgendered
(not that I think I am really) and that he should drop me off at the next
junction. He told me that he didn't care if I was a man, woman or monkey. I
looked as sexy as fuck and he'd love to have me hanging off the end of his
knob. Put like that it seemed rude to refuse so, with more than a little
trepidation, I reached down, unzipped his trousers and reached inside. Oh
my God! His knob was about 10 inches long and so thick I needed both hands
to hold it. It had thick veins all over it and a huge purple end. I slowly
lowered my head to it and, parting my lips, let the end pop into my
mouth. Then I just stayed there for a moment, tasting it. I expected it to
taste of stale piss but it didn't taste of anything. It was just big, hot
and very, very smooth. I started to run my tongue over it, enjoying the
smooth slipperiness of it. It was exactly like rubbing your boobs through a
silk top, indescribably sensual and I was starting to think I could happily
keep my head in his lap and his knob-end in my mouth until we got to
Carlisle. What I didn't realise was that it was driving him mad. I found
out when my head was suddenly shoved under the steering wheel and I had
about 6 inches of very thick knob down my throat which was trying to
increase to the full 10 inches.

After a couple of seconds, which felt like minutes as my whole life started
to pass in front of my eyes, he pulled me up again and pulled his knob out
of my mouth. "You can't do that to a bloke" he said. "It's far too
intense. It's Ok to lick it on every stroke but not all the time. Just
slide it in and out of your mouth. Imagine that it's a dick going in and
out of a pussy. Go nice and slow and don't worry about getting it all in --
even my missus can't manage that". So I settled back down and started to
let it go in and out about 3 inches. I pushed my tongue against it as it
was on the way in and sucked my cheeks together on the way out. Whatever I
was doing seemed to work OK because pretty soon I was rewarded by a madly
swelling, twitching knob, promptly followed by a mouth completely filled
with cum. Swallowing desperately so that I didn't get any on my clothes, I
managed to catch it all. God! How much was he going to produce? It seemed
like a pint. Finally, he came to an end and I had a moment to savour what
was in my mouth. I didn't think that it was something I was likely to do
again so I wanted to get all I could from the experience. I still had a
mouthful so I swished it around inside my mouth and around my tongue -- just
like my Dad when he's drinking posh wine or whisky. It was weird. It tasted
a bit like caviar but not as fishy. It was sticky and slippery at the same
time and, ugh a bit gross, it had little lumps in it like Tartar
sauce. Hmm. Different; not something I would want every day for breakfast
but not bad for a change.

I carefully tidied his knob away and zipped up his trousers. Then I looked
up at him and smiled. "Thank you" I said. "I really enjoyed that."

"Not as much as I did" he replied. "You were bloody marvellous. You can
suck me off any time you want". To be honest, I wasn't in too much of a
rush to do it again. Maybe when we got near Carlisle. The main problem was
that while he had cum, I hadn't and I was feeling bloody hot! I suspected
that he wouldn't be keen on returning the compliment on me and I was sure
that I wasn't about to wank off in front of him.

After I had removed my head from his lap and repaired my makeup (it plays
the very devil with your lippy), I settled back down next to him and we
began to chat again. I found out that his name was Dave (yes, I know it
would have been polite to have been introduced before I tried swallowing
his knob); he was 32 years old; he had been married for 12 years to a woman
called Charmaine who was 38; they had a 16 year old daughter called Elspeth
and enjoyed an open marriage because they were both sex-mad and Dave was
away from home for at least half of every week.

Some time later we stopped at a service area for petrol (do lorries use
petrol?) and to get something to eat. Dave was really sweet and insisted on
paying for my lunch. He was surprised to find out that I was a
vegetarian. Honestly, the way he went on about it. It was as if he regarded
a boy dressing as a girl as perfectly normal in comparison. When we went
back to the lorry he gave me a hand up into the cab. As he was pushing me
up he slipped his hand under my skirt and gave my bum a squeeze. It felt
pretty good having a big strong hand squeezing there so, instead of pulling
away and jumping up into the cab, I pushed back against his hand and
enjoyed the feeling of having my cheeks squeezed and then a strong finger
running against my crack. Finally he gave me an extra push and I
reluctantly got up into my seat.

When he got into the cab, instead of starting the engine, he turned to look
at me. "Do you fancy a fuck?" he asked.

"Duh! In case you'd forgotten, I don't have a pussy. So even if I wanted,
and I'm not saying I do, there's nowhere to put your knob" I replied. At
the same time I was thinking that it was a pity because I was really
enjoying the naughtiness of the situation and I was remembering a
conversation I had had with Carol a couple of weeks ago. She was in the
middle of her period and was feeling sorry for herself and a bit catty. He
had complained that I was a cheat girl and was only getting the good side
of being a girl -- no periods; no fear of having to give birth which,
according to her Mum was like shitting a breeze block; and never having to
put up with having a big sweaty man lying on top of you shoving his meat in
you for all he was worth.

"Maybe you don't have a pussy but you do have a hole. My Charmaine loves it
up the arse. I reckon I shag her bum at least twice a week" Dave said. I
thought about it for a bit. I didn't have to worry about periods or getting
pregnant but I could experience the big sweaty man bit -- not that I would
dare let Carol know.

"Won't it hurt?" I asked, worrying about the size of his knob.

"Charmaine said it hurt when I first shoved it in but, once she relaxed
around it, it was fantastic. We'll need some lubrication though. Go on,
what do you think?"

"OK then but promise you'll stop if it hurts me too much. What will we do
for lubricant?"

"That's easy. If you give yourself a wank then you can spread the cum up
the crack and into your hole" Dave replied. So knickers down to my knees,
skirt up and away I went. It took no time to get a stiffy, the conversation
we were having and the earlier blow-job had left me desperately randy and I
could have fucked the Crack of Doom. He immediately noticed my waxed
crotch. "My missus shaves down there as well" he said. "She says she has to
because she often wears rubber knickers. Do you know what she did the other
week? She told be to be in the sex-shop near us by 11 O'clock and to say
nothing. So, there I was with all the perverts in their thick glasses and
raincoats when in she walks. She walked straight up to the counter and
asked, very loudly, for a pair of rubber knickers, size medium, with two
dildos in them; one for her cunt and one for her arse. Of course, all the
perverts were paying attention now. The bloke behind the counter found her
a pair and handed them over. She made a big performance of inspecting them
and holding the dildos to make sure they were big enough. When she had paid
for them she asked if there was anywhere she could put them on because she
was desperate. Everybody in the shop was staring at her now and I had a
huge hard-on. She was shown to the store-room.

She re-appeared about 5 minutes later with the knickers in her hand but no
skirt or knickers on; just her stocking, suspenders and her heels. "I'm too
dry to get the one up my arse" she said. "Can one of you blokes help me
out?" She walked up to this old bloke of about 50 and pulled him
forward. "Please?" she said. "Just fuck my cunt for a bit to get your knob
wet and then finish off up my arse." She then bent over a display cabinet
full of dildos and vibrators and shoved her arse in the air.

The old bloke walked up behind her, got his knob out, and shoved it in her
twat. After about 5 or 6 strokes he pulled it out and slid it up her
arse. Then he pounded away for all he was worth until he came. When he
pulled out, Charmaine's hole was still open. She calmly reached over for
the rubber knickers, slid them up her legs, lined the dildos up with her
pussy and arsehole, and pulled them up tight. She smiled sweetly at the
bloke who had fucked her, thanked him and told him he could fuck her any
time, put on her skirt and walked out of the shop. She told me that she
then went shopping for clothes but there was nobody in any of the changing
rooms to see her knickers so she went to the swimming pool where she
freaked out a couple of birds when she took her knickers off and they could
see two dildos slide out of her."

As Dave was talking and I was wanking, my mind was working overtime. I
could imagine myself as Charmaine, bent over the display cabinet with loads
of strangers watching me being buggered and I could imagine myself as the
bloke doing it and I could imagine myself in the changing rooms -- stripping
off to reveal rubber rather than cotton or nylon knickers then pulling them
down to show that I had had a dildo up me. My mind returned just as I was
about to come and I remembered to catch my cum in my hand. Then I spread it
up the crack of my bum and worked it into my bum-hole.

Then I knelt down on the seat and shoved my bum as far in the air as I
could. Dave leant over me and started to squeeze my boobs and stroke my
bum. Then I could feel his knob sliding up and down in the cum in my crack
until it came to a stop resting against my bum-hole. His hands returned to
my boobs and then he pushed.

"Oh my God! Oh my God! Oh my God!" I cried. Let me offer you a piece of
advice: if you get fucked up the bum for the first time, choose a bloke
whose knob is smaller than 10 inches. It hurt like hell. "Dave, take it
out, its agony."

"That's what Charmaine said when I first went up her" replied Dave. "I'll
keep still and if you just relax, the pain will stop. Let me know when
you're ready for the fucking of your life?" Fucking of my life! The way I
felt I thought it would be the end of my life. I stayed very still and,
pretty soon, the pain had subsided. It hadn't gone completely but I could
now feel this huge hot lump in me and, know what, it felt pretty good. Very
slowly, I pulled my bum back about an inch and then pushed back to
re-impale myself completely. Ummm that was nice. I did it again. Nice
again. Then I pulled back about 3 inches and pushed back hard. I swear I
saw stars but it didn't hurt any more than before. I did it a second
time. Wow, this was unbelievable. There are no words to describe the
feeling; it's too fantastic.

"OK Dave, shag my brains out." Oh boy did he? 10 minutes of a 10 inch knob
being shoved all the way up and then all the way back. Just as you are
about to catch your breath its being rammed back in again. I couldn't
believe the feelings coursing through me. Finally, his knob got even bigger
and he thrust it in so hard I thought it would come out of my mouth and
then he was coming. I've been told that your insides don't have the right
nerves to feel hot cum being splashed into them. Don't believe it -- you can
and it's brilliant.

When he pulled out of me I felt like all my bones had been removed. I fell
over onto my side and curled up into a ball. Dave carefully slid my
knickers off my legs and used them to wipe the cum off my bum and his
knob. Then he put himself away, pulled my skirt down over my bum and sat me
up in the seat. Then he started the lorry and we set off again.

We talked as we drove along. "Would you like to do it again?" Dave asked.

"Not right now. I still very sore and I can feel your cum trickling out" I
replied.

"Of course not right now Silly. But in a while when I'm ready again."

"I'd like to Dave, it felt bloody brilliant but I don't think my bum's big
enough for you." Dave thought about this for a while.

"I reckon I've shagged Charmaine up the arse at least a thousand times" he
said. "God know how many other blokes have been up her. Now I can slide in
as easy as going into her quim. I reckon you need a bit of stretching then
you'll really enjoy it." I liked the idea of really enjoying it and told
him so. Then we talked about my plans and if I really needed to see
Jackie. I could spend the week with him and get fucked senseless 4 or 5
times a day. He would drop me off near where I lived on Friday and he would
take me shopping in Edinburgh. So, while he went shopping for "something to
help me stretch", I phoned Jackie from Stoke on Trent and got her to cover
for me. I didn't tell her I was with a bloke. I let her think I'd been
picked up by an older woman and was giving the benefit of what I hid in my
knickers. Jackie was as good as gold about it.

When we got back to the lorry, Dave handed me a brown paper bag. Inside was
a huge pink dildo. It was bigger than Dave's knob and had thick veins
sculpted all the way up it and a big, perfectly shaped bell end. It also
had a sucker on the other end. Dave told me that it was the exact copy of
some porn star's knob. He told me to lick the sucker and use it to stick
the dildo on the seat. Then he told me to lick the bell-end to get it
really wet and then sit on it. It took me about 5 minutes to get all the
way down so that my bum was taking my weight and it really hurt while it
was going up me but, once I was down, it didn't feel any more painful than
when Dave was shagging me. Dave started the lorry and off we went again. I
could feel the engine's vibrations coming up through the dildo which felt
pleasant rather than horny and it seemed to help my insides to rearrange
themselves around it and for my sphincter to relax and get used to this
whopping thing in it.

After about an hour, we pulled into a truck stop and Dave said we were
going for a cup of tea. I gently lifted myself off the dildo and turned to
jump out of the lorry. Dave told me to bring it with me. The thing wouldn't
fit in my handbag so I had to walk along past all the other lorries with 3
inches of bright pink dildo sticking out of the top of it.

When we got to the building, Dave told me to go into the Ladies and wash
the dildo. He would go into the canteen and get us both some tea. When I
got into the canteen, Dave was sitting at a table. He seemed to know
everybody in there and was happily chatting away. I started to sit
down. Dave asked me why I thought I had to bring my "stretcher" with me. As
I was turning bright red he told me to stick it to the chair and use
it. So, red with embarrassment, I took the dildo out of my handbag, licked
the base, stuck it onto the chair, gave the bell-end a quick lick and eased
myself onto it. Once I had got all the way down I opened my eyes and looked
around. Everybody was staring at me. Suddenly, I didn't care. I felt a
complete slut. Nobody knew me and they wouldn't see me again and I bet that
they all felt really jealous of Dave having such a sexy little chick with
him. Dave certainly was beaming with what looked like pride. He reached
over and patted the top of my head. "I thought you'd be up for it when I
first picked you up. We're going to have a great week love."

I repeated the performance when we got back to the lorry and, unless I had
Dave's knob up me, I was sitting on the dildo whenever I was awake for the
next 4 days. By Wednesday, Dave could slide up me really easily and I
didn't hurt at all. We had bought some KY jelly so I didn't have to wank
before I got fucked. Dave wouldn't touch my willy (something about not
being gay) but I could wank myself while he was fucking me. We did it at
least 4 times every day but I can't manage more than once a day because of
the hormones. I won't bore you with the details because it all gets a bit
repetitive.

Dave took me to Edinburgh and I got a Chanel "little black dress"; a pair
of Jimmy Choo shoes -- plain black courts with a 4 and a half inch stiletto
heel -- very sexy and hell to walk in; and the most gorgeous Scottish formal
dress -- in red tartan with a full long skirt, long bell sleeves, a deep
plunge neckline on a fitted bodice and a white cotton and lace petticoat to
wear under it. It will be perfect for Christmas with a shawl and brooch.

We stayed for one night at Dave's house. They are severely weird. Charmaine
was exactly as I pictured her -- a pretty brunette with short, well styled
hair slightly running to fat. Skirts a bit short for her age but she
carries it well. Elspeth is a typical Chav but nice enough. She's quite
pretty under all the makeup and could be a real stunner if you could get
her into some decent clothes, just a little makeup to enhance rather than
obliterate her features and get all the gel washed out of her hair. They
were incredibly friendly; especially when you think I had just been shagged
by the man of the house (we did it in the back of his car on his drive just
before we went into the house. I was saying "Hello Charmaine, it's really
good to meet you" while Dave's cum was running out of my bum and down my
legs).

Charmaine and Elspeth took me upstairs for a bath while Dave went down to
the pub for a drink. I was about to suggest a little privacy when
Charmaine's hand shot up my skirt and encountered no knickers. "Oh, who's a
lucky girl to have a bit extra? Elspeth love, come and look at this. I bet
you've never seen such a pretty one before?"

"Ooh Mum, it looks lovely. Can I touch it Jilly?" Both of them had a play
and Elspeth had a suck but, although I got a bit of a stiffy, they couldn't
make me cum. Bloody hormones! Then they put me into the bath and gave me a
good wash all over, paying particular attention to my willy and balls, bum
and boobs. I hadn't been bathed since I was about seven and certainly not
in such a lascivious way and there was something really comforting about
it. Once they had got me out of the bath and dried me down I got dressed in
bra, knickers and tights for the first time since I had left home. Then I
put on my one decent dress (I didn't think the Chanel was appropriate and I
thought that they would feel I was taking the piss) and went down stairs to
chat to them in their living room.

Charmaine asked me if I had had a nice trip with Dave. I was just mumbling
some anodyne reply when Elspeth said "Hasn't he got a big cock? It's easily
the biggest I've ever had. It's even bigger than Sean McEvoy's and he
thinks his is a whopper." I didn't know what to say. Ok, I fuck with Jackie
but we're sort of sisters so it doesn't count. I couldn't imagine going to
bed with Mum or Dad but, thinking about it, I bet Jackie could. Anyway, the
conversation turned rapidly downhill for a while as we discussed Dave's
attributes and how good he was at using them. Eventually, I managed to drag
the conversation onto less torrid ground by mentioning that I had been
shopping in Edinburgh. I showed them the clothes and shoes and gave them a
little fashion show. I was very aware of their eyes on me when I was
changing from dress to dress but they were very complimentary about the
clothes.

Charmaine gave us all supper when Dave came back from the pub. It was
Lancashire hot-pot. This has lamb in it so, ordinarily, I wouldn't eat it
but I really didn't want to upset Charmaine by telling her that I was a
vegetarian. I could feel Dave's eyes on me as Charmaine passed me a full
plate of the stuff. I put my finger to my lips to tell him not to say
anything and his face spit into a massive grin of unalloyed delight.

After supper and once the washing up was done, Dave said that it was time
for bed. Suddenly, for the first time since we had met, he seemed a little
unsure of himself. After shuffling his feet for about a minute he finally
asked if I wanted to sleep on my own. Elspeth's bed would be free (how?)
but I was welcome and he would regard it an honour if I slept with
them. How could I possibly say no? So up to bed we went. The first surprise
was the bed. Dave had bolted 2 double beds together so there was one bed
that could accommodate about 5 people. The second surprise was that Elspeth
came into the bedroom with us. OK, I knew that Dave had knobbed her but I
had assumed that it was in private. We all took it in turns to have a wash
and brush our teeth and then it was clothes off and into the bed. I just
couldn't take my eyes off Charmaine's nipples. They were huge, the aureoles
were the size of saucers and the nipples themselves were about 3 inches
long and thicker than my thumb. "Do you fancy a suck on them love?"
Charmaine asked. I didn't need a second invitation and I was clamped onto
one of her boobs in less time than it takes to say it.

It was like firing a starting pistol. Everybody grabbed a bit of me and in
seconds I was being transported into a world of unremitting pleasure. I
could feel somebody rubbing my nipples while another hand was exploring my
bum and a mouth was wrapping itself round my willy. My neck, waist and legs
were being stroked. It was heaven. Slowly, we all parted and reformed and
reformed and reformed. At one point, Charmaine was fucking my bum with one
of her nipples while I was shagging Elspeth in the bum and she was sucking
Dave off. I couldn't see where Dave's head was but, judging by the noise
Charmaine was making, either he or Elspeth was attending to her pussy.

When we were all spent, Charmaine got out of bed and got 3 pairs of rubber
knickers out of a drawer and gave one pair to Elspeth and the other to
me. I watched, on the verge of sleep as they pulled them on, realising
drowsily that they were the same as the ones Dave had described to me with
2 dildos in them -- one for each hole. Slowly, they both slid them up their
legs, slipped the front dildos into their pussies then the rear ones into
their bum holes then, finally pulled them up tight.

I looked at the pair that I had. Yes, 2 dildos. I pulled them on and up my
legs. Then I pushed the front dildo to the front and tried to get the back
one up to my bum. I couldn't manage as the front dildo kept getting in the
way. Dave reached over and pulled them back down. Then he took a penknife
from a bedside cabinet and sliced the front dildo off. Charmaine and
Elspeth rolled me onto my back and lifted my legs up. They pulled the
rubber knickers down my legs and one of them guided the remaining dildo up
to my bum hole. Then they both gave a tug. Ooh that full up feeling. That
done, somebody switched the light out and we all snuggled up together like
a litter of puppies and went to sleep.

When I woke up, the 2 women were sitting in chairs by the bed, still in the
rubber knickers that they had gone to sleep in. I was still wearing mine
but, as the dildo in them was comparatively small, and it had been in all
night, I could hardly feel it up my bum. Dave was stoking my boobs. Without
saying a word he slowly pulled the knickers down and off my legs. I started
to roll over onto my tummy but he gently pushed me back onto my back. He
lifted my legs up and apart and then, for the first time, he entered me
from the front. It was brilliant. It felt really good being knobbed by this
guy while his wife and daughter watched. I could kiss him and lick his
chest. Best of all, I could grab hold of his buttocks and encourage him to
go harder into me. After last night there was no was I could get a stiffy
but I did have a sort of orgasm. I started off feeling hot and twitchy
inside. Then I could feel all my insides melting and then it was as if I
had been given an injection of pleasure drug right in the middle of my
abdomen. It was utterly fantastic.

Once we were all up, dressed and washed and had breakfast (just cornflakes
and a cup of tea- no sugar), it was time for Dave and I to set off. I went
to give Charmaine her rubber knickers back but, as she pointed out, they
weren't a lot of use to her with a dildo missing so I could keep them as a
souvenir. Her advice was to remember to wash the dildo thoroughly every
time I pulled it out of my bum so that I didn't get an infection. Then it
was kisses all round and off we went.

That pretty much covers my half-term holiday. Dave dropped me about a mile
from home. We had a quick fuck in the grass by the side of the road before
he left. I promised that I would come and visit him and his family and that
I would try to bring Jackie with me as I guessed she would enjoy it.

There is a bit of a footnote. I sometimes wear the rubber knickers to
school but only if I know that Carol won't be in. Could you imagine the
embarrassment if she found out? I keep them in the back of my makeup drawer
with the big pink dildo as I know that Mum and Dad never look in that
drawer. I still use the dildo regularly. After all, you never know when
your going to meet a guy who isn't bothered by the extra bits and who wants
their sex ruined by pain? Whenever I'm up in my room studying, out it comes
and up it goes. It can be a bit of a challenge if Mum or Dad comes in to
talk and, when I first started, I used to just pull my knickers down and
hop on but, one evening, Mum came in to ask about my plans for the weekend
and noticed them around my knees. I had to tell her that I was just very
hot. She obviously didn't believe me but she didn't push it. Now I take my
knickers and tights off and hide them under my pillow first.

It took Jackie 2 days to find it when she came home for the summer. I came
in from school and went up to my bedroom and there she was with it in her
hand. She asked me if I was turning gay or was it something I used on
Carol. I told her that I'd bought it for a dare (where around here could
you buy one?) but, yes, I had tried it and it was cool. She wanted to see
how I used it so I showed her. Then she stuck it on the edge of my dressing
table and rubbed herself off with it. She wanted to know what it was like
having something up your bum so I offered to show her and ended up shagging
her bum hole.

Anyway, I'm supposed to be writing an essay on "Elastic and In-elastic
Demand Curves" for Economics and I've come to the end of my story. I'm glad
that I found your website to send it to as I've wanted to tell somebody for
ages. Please e-mail me to let me know if you have enjoyed it. If you have I
might write again about the gaps I've left and about my (few) and Jackie's
(many) adventures including the end of the summer when we had a weekend in
Carlisle. (Dave was very discreet and didn't let on that it was him that
had been shagging me for a week. Jackie thinks he picked me up on the way
home and we just got talking.)

Lots of love,

Byeeeeee

Jilly
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jilly_dupree@fsmail.net