Date: Tue, 20 Dec 2005 12:26:42 +0100 (CET)
From: Elaine Wainwright <elaine.wainwright@fsmail.net>
Subject: Elaine's First Time - TG

Hello Everybody,

My name is Elaine and, although I was born a male, I was promised as a maid
to my cousin Amanda when I was born and so was raised as a girl. As I grew
up in the same house as Amanda and her mother, I practiced being a maid
from when I was a little girl. I properly became her maid on my 16th
birthday when I had finished my training. I was married to Amanda on the
same day to show that she now owned me totally. It was the happiest day of
my life.

I am now 20 years old. I am 5'6" tall with long dark brown hair and blue
eyes. I am quite pretty but it is more "girl next door" than model. I have
large breasts (don't ask me how big as I have never worn a bra, always a
corset). They are certainly larger than my mistress's and she is a 36C. My
natural waist is 22 inches but it is laced down to 17 inches. My hips
measure 36 inches. This is all the result of an artificial female puberty
that was induced by hormone therapy when I was 12. I have a little penis
but no testicles. They were removed 2 years ago as they had atrophied and
were making me ill.

One day, if I have the time, I will write and tell you my whole life. For
now, I will just write about my latest experience. I bring my mistress and
her current boyfriend, Piers, a cup of tea in bed at 9 O'clock each
Saturday morning. A few months ago, when I woke them up, Piers remarked
that he was feeling randy. My mistress does not like sex first thing in the
morning and told him so. While he was having a pout over not being able to
have sex, my mistress said "Why don't you fuck Elaine?"

I blushed deep red. I was accustomed to preparing my mistress and her
boyfriend for sex with my lips and tongue but she had never suggested that
I be used in this way. However, I have always understood that my duties
were infinite so I quickly said "it would be my honour to accommodate you
sir."

"Right Elaine," he said. "You better get me good and wet first" and
promptly produced his penis for me. This was something I knew how to do and
really enjoyed. I sucked my first dick while in training and loved both the
feel of it in my mouth and throat and also the lovely taste and texture of
cum in my mouth. I quickly set to my task. Piers has a big penis. It must
be 9 inches long and almost as thick as my wrist. It tasted slightly of old
cum and my mistress's juices and smelt of old urine but it was lovely being
able to suck it.

All too soon he pulled it out of my mouth. "That's enough of that. I want
to stick it in you, not have you suck me off. Now go and bend over the
dressing table and get your knickers down." I did as I was told, apart from
the knickers. I haven't worn knickers since my mistress caught me wearing
her dirty ones. For the next 2 weeks she would go to the toilet without
pulling them down before her evening bath. When they were sopping wet and
full of her shit, she would make me slip them off her and then wear them
for the next 24 hours. She still soils them every evening but now I don't
have to wear them. I can suck them clean instead.

Anyway, back to the main event. I bent over the dressing table, lifted my
skirt and petticoat up over my hips and watched Piers through the looking
glass. Holding his penis in his hand, he walked across the room, lined it
up with my anus and pushed hard. Ow! Ow! Ow! I thought but managed not to
cry out. It really hurt. I felt as if I was being split in two. I was sure
I could feel my bum tearing. However, when he had given me about 6 or 7
good strokes, my sphincter began to relax and I was able to enjoy the
sensation. Piers was not trying to turn me on; it was his pleasure, not
mine that counted. His hands rested lightly on my hips and he just pounded
away at my bum. I was loving it. I could feel this huge, hard lump of meat
ramming into me and stimulating parts of my insides that had never
experienced anything like it before. My legs were feeling wobbly and I
looked at my mistress through the looking glass. She was sitting up in bed,
drinking tea and idly fiddling with one of her nipples while watching her
husband (sort of) being fucked by her boyfriend. I thought that if being
fucked in the pussy felt anything being fucked in the bum, there would be
no way I would have turned it down.

All too soon I felt Piers' penis getting even bigger, his strokes became
even deeper and more insistent and then he was pumping his cum into my
rectum. When he had finished and pulled out of me, my mistress began to
applaud. "Well done Elaine. Piers won't feel randy for a couple of hours
now (she told me that once he had fucked her 9 times in one day). Now, how
do you show how grateful you are?"

I turned to face Piers and bobbed a curtsey. "Thank you for cumming in me
sir" I said. "May I lick you clean?" Piers responded by waggling his now
flaccid penis in my face. I gently licked it clean from end to end. It
tasted mainly of his cum (yummy) but there was also an earthy taste which I
assumed was my shit (ugh!). When he was completely clean, Piers got into
bed and picked up his cup of tea while I went about my duties for the day.

I went shopping in town that morning. I also met Janice and Chloe, two
friends from school, and we went for a coffee. While we were chatting I had
a coughing fit. This forced all Piers' cum out of my bottom and, when I
stood up to leave, you could see it glistening on my chair. My friends both
recognised what it was immediately and ribbed me mercilessly about not
washing my pussy out after getting fucked and not wearing knickers –
especially when wandering around town with a cunt full of cum. They don't
know that I'm not a real girl and assumed that I'd had a morning session
with my boyfriend.

That might have been the end of the matter but, on Monday evening, when she
had returned from work, my Mistress called me into her study. "I was very
pleased with your behaviour on Saturday morning" she told me. "Piers would
like to fuck you every morning. This suits me as I don't like sex before my
bath. My pussy is dirty from the night before and I want you to have got it
clean and fresh smelling before I fuck again.

"However, Piers thinks that your bottom is too tight for his complete
pleasure. While you will obviously stretch down there from repeated use,
neither of us have the patience. I have considered getting you a sex change
but I want to have the only cunt in this household. I have also thought
about having your sphincter removed but, remembering how ill you were after
your castration, I have decided against that as well. Instead, we'll use
this on you."

She produced a smooth plastic ring about 2 inches in diameter with the
outside edges about a quarter of an inch bigger than the middle. She then
reached into her briefcase and brought out what I now know to be an
inflatable dildo. She slid the ring over the dildo and inflated it until it
was bulging on both sides of the ring. She told me to turn around and bend
over. Then she inserted the dildo in my bottom (more pain but it is my
honour to do as my Mistress wishes). Once the ring was lined up with my
sphincter, she deflated the dildo and withdrew it. The ring stayed in
place, holding my bottom open. It was uncomfortable but not really
painful. It was certainly worth it if I was going to get a daily fucking
from Piers.

"We'll leave it in for a week" said my Mistress. "Piers can give you a fuck
when we take it out and tell me if you are now suitable. You will soon get
used to it and it won't stop you going to the toilet. Now, pull your dress
down and get on with your duties."

I was hardly aware of the stretching ring in my bum by the next morning. I
went shopping in town that afternoon. While I was on the bus home I started
to feel that I wanted to have a shit. It struck me that I wouldn't be able
to stop it if it came so I quickly pulled my skirt under my bottom to avoid
a mess if the worst happened. It did and it was messy and smelly. Luckily,
nobody was sitting near me to notice what was happening but I did have to
walk home from the bus stop with my shit running down my legs.

Naturally, that evening I told my Mistress that evening what had
happened. Her first reaction was to burst out laughing but when she saw the
tears rolling down my cheeks her attitude changed to one of sympathy. She
took me on her knee and gave me a cuddle while kissing my tears away. "You
poor little thing" she said. "We can't let that happen again. Just let me
think of a solution."

I thought of one immediately. "I could wear incontinence pants,
Mistress. They would catch all the mess and then I could just rinse them
out."

"But Elaine, you know that the only knickers you can wear are my soiled
ones. Let me think some more." She paused and then said "I know. You must
buy yourself an enema kit tomorrow. If you give yourself a good wash out
every morning I don't think you will have another problem."

So, the next morning found me in the local Chemist's shop. I waited until
there were plenty of people in the shop before approaching the Chemist. "I
would like to buy an enema kit" I said very loudly so that everybody would
hear.

"Certainly madam" he replied. He produced a large box from the store room
behind the counter. "Do you know how to use it? "He asked. "Will it be for
heath use?"

"No, it is to add variety in sex play" I said. "I am very excited by the
idea of being fucked while my abdomen is full of water. The idea of walking
around with a couple of pints of water in my belly also excites me." This
wasn't true but my Mistress likes me to act in this way in front of
strangers and would want me to recount my experiences that evening. She was
absolutely delighted with me when I told her and let me spend the whole
night with my head between her legs.

The Chemist then explained that, rather than placing the nozzle just inside
my bum before releasing the liquid, I should work about a foot of the tube
up my bum first. With care and practice I should be able to get 3 pints
into my belly and he had read of a lady who could keep it inside her for
over an hour before she had to release it. I must confess that I was really
enjoying this conversation and I leaned over and quietly whispered in his
ear, asking him if he would like a blow job for his kind advice. I sucked
him off in the store room while the shop was shut for lunch. It was lovely.

Anyway, I set it up in my bathroom when I got home and followed the
instructions that came with it and the Chemist's advice. The first few
times that I used it were quite messy and I still had the occasional
accident but now I give myself a 2 pint enema of warm water and glycerine
every morning. I keep it in me for half an hour before releasing it. I then
give myself another pint of rosewater, keep it in for 15 minutes and then
I'm safe for the rest of the day. Obviously, I can't spare 45 minutes lying
down with a load of water up me so I have to get on with my duties while my
belly is distended with water.

The big day came on Tuesday. That morning, Piers and my Mistress came into
the dining room as I was setting out their breakfast. She had the
inflatable dildo in her hand. She bent me over. Then, as Piers shoved his
dick in my mouth, she rammed the dildo into me and pumped it up. When she
pulled it out the ring came with it. Piers immediately spun me round so
that I could brace myself on the sideboard and shoved his dick into my
bum. I got all the pleasure of the first time but none of the pain. It was
brilliant! However, when Piers had squirted his cum up me and pulled out
and I had cleaned him up and tucked his dick back into his underpants, he
said that I was still too tight. My Mistress had expected nothing less and
had already positioned a larger ring on the dildo. In it went and I was
told that they would try me again in another week.

This went on for another month. The final ring was 4 inches in diameter and
I actually felt my sphincter give up the struggle when it went into
place. I can no longer close my bottom and, when I wipe my bum, my whole
hand just slides up. I make great efforts to keep it loose and ready at all
times. After my enema, I carefully wipe it clean and then rub in lots of
coconut milk body lotion to keep it soft and well lubricated. Piers fucks
me every morning, without fail. I love it and wish he could fuck me more
often. My Mistress caught me deliberately rubbing the front of his trousers
with my bum while getting his shoes. She was very cross and made me clean
the toilet with my tongue after she had had a shit and then wear court
shoes with 5 inch heels for the next week.

When my Mistress went away on business to New York for a week, Piers took
me into his bed every night. He fucked me at least 5 times every day and
kissed and cuddled me in bed until I went to sleep. It loved every minute
but I was glad when my Mistress came home because I love her and I had
missed her dreadfully.

That is the end of my story. Please let me know if you have enjoyed it? If
so, I will write and tell my whole story when I have time.

All my love,

Elaine