The Fall and Rise of Sasha
By Amanda Moore
Two years ago I was just a normal straight guy. Late 20s, 5'9" tall,
slim, not very athletic and averagely attractive. I was single but had
my fair share of girlfriends, though nothing serious ever came of my
relationships and only two of my ex-girlfriends had been my lovers,
still never had I ever thought of having any form of sexual contact with
another man. Now the only girl in my life is Sasha, the girl I, Josh,
create from inside me. In fact I think of myself not as Josh but as
Sasha and Sasha as a girl is mainly heterosexual which means I have
boyfriends now not girlfriends. Men clearly think I am an accomplished
lover, I like to give myself to them and my well stretched, fisted anus
is as capable, pliable, useable and experienced at taking cock as most
pussies. I love cock and my anus is my badge of accomplishment. I love
that it gapes and through use has developed swollen lips around the
hole. I am no longer the fucker but the fuckee and tonight I am
preparing for my latest lover Matt who is going to take me dogging
again. He had only introduced me to it a month previously, on the night
we first met, but already I was hooked on the meaningless casual sex and
the thrill of being openly observed by other people as I exposed both my
transvestite's body and slutty nature to lusty strangers.
I met Matt through an internet dating site that catered for
transgendered people. He was a tv admirer who lived in a town about 15
miles distant from me. Describing himself as late 30s, balding, well
built and 6'1" tall I contacted him and asked him for a photo. He
looked okay when he replied so I arranged a meeting. I am always wary
of inviting people to my house when I first contact them and he shared a
house with his brother, so we arranged to meet one evening at a local
picnic spot. Matt had already told me that he did not want to take me
out for a drink or a romantic evening he just wanted to fuck me. He
also told me he wanted to show me off and slut me out to other men. This
kind of frank, brutal bluntness excited me which was why I agreed to
meet where I did. Perhaps you can tell I am not a shy, retiring kind of
pretend girl but a full on loud and proud transvestite tart.
It excited me to dress for Matt as cheaply and sexily as possible as
that is what he asked for. I had added a hair piece to my long
straightish bleached blonde hair. This allowed me to pile it up
slightly in a kind of early 60s style. I lathered on the make up to
give myself heavily kohled eyes and deep red moist and plump lips. The
make up was heavy but expertly applied as I had been trained well and
had lots of practice. Did I make a convincing girl well not a 100% but
I was undoubtedly a hot, sexy and ultra feminine transvestite. Oh yes I
know what I am, a male who dresses as a slutty female in part to attract
other men so I can have wild sex with them. I am a feminised total
faggot, an out gay transvestite, who likes nothing better than pleasing
men who adore tarty, ultra fem sheboy bottoms. I am a boy toy and cum
dump for any man who likes slutty girls with male bits between their
legs and I love everything about being this person.
My journey happened in stages from straight vanilla guy to what others
might regard as a sissy gay guy but what my boyfriend sees as a feminine
nympho slut, albeit one with a dick. I don't care what others think, I
like who I am. I may be a fairy faggot and a slut but I love my life as
a feminised boy toy. I love the change that has taken me far away from
the boring conventionalism of masculine heterosexuality. It began when
I met Helen. She was older than me, early 40s, and a powerful woman
both in personality and physically. Buxom and well built she was
nevertheless very fit as she was a part-time dance teacher and aerobics
instructor. Divorced she wanted only temporary relationships with
younger men. We met at a party and I was drawn to her strength and
assertiveness. She claimed she liked my laid-back nature and
willingness to please her. At the time though somewhat weedy I was
clearly unfit and had a little paunch developing. Helen quickly got me
fit through dance and better diet. She wanted me to stay lithe so the
exercises she devised for me were calculated to make me fitter and
leaner without building muscle and increasing strength. After a couple
of months, when I weighed only 141 lbs a whole 15lbs lighter than her,
she confided in me that she preferred smooth men and that as I was
toning up I would look good if I had my relatively sparse body and leg
hair removed. She convinced me to go for regular waxing, to have both
ears pierced and a small flying bird tattoo on my left shoulder. By
this time our relationship had developed to a point where she clearly
took the lead. Helen was undeniably the dominant partner and I was
enjoying a more passive and slightly subservient role. It felt good to
have someone else make decisions for me and I even enjoyed the feeling
of her being physically stronger than me.
One Sunday morning, after we had been together for about five months, as
I returned naked from having a shower Helen looked at me appraisingly
and smiling her dazzlingly attractive smile said, "You know honey with
your delicate bone structure, thin body and smooth skin you look almost
feminine."
I laughed and said, "Sure accept my face."
Her reply surprised me. "Oh I don't know your nose is smallish, not too
broad and quite cute, your lips are well shaped and full and your cheek
bones high. Your chin is not large though a little square, but with
make up your face would be transformed not only into a girl's face but
into a pretty one too."
"Mmm whatever."
"Really I mean it honey. I think you would look cute."
"Yeah right and what about my hair, lack of boobs, facial fuzz etc."
"Oh come on Josh, a close shave, a different hairstyle and a push up bra
with gel inserts will address all that. You know the more I think about
it the more I want to transform you. Go on let me please it will be
fun."
I was not excited by the thought but I was not bothered by it either and
as we had a free day and I did find it difficult to resist or deny Helen
I agreed. Clapping her hands in glee she told me to give my self the
closest shave I had ever had. Afterwards sat at her vanity she began by
tidying up my eyebrows. She explained that she was only thinning them
to an acceptable female shape but one that would be okay for male mode
too. Helen did not have a wig, but as my hair was shoulder length she
felt she could cut and style it into a gamine female style that with
hair gel could be made into a rakishly fashionable male style for work
on Monday. She worked on me for about an hour and a half before letting
me look in the mirror. The transformation was startling. Gone was the
averagely attractive slightly wimpy guy's face and in its place was a
well made up attractive woman's face of about 30. The face was framed
by my light brown hair cut and teased into an undeniably feminine style.
Cut around my ears it was long on the neck and feathered with longer
strands in front of my ears and a spiky fringe across my forehead.
"Wow that is amazing," was all I could say.
"See I told you sweetie that you would make a hot chick."
I was not so sure about that but I was certainly impressed and more than
willing to explore Helen's game further. She had very few items of
clothing that would fit me, being shorter but better built and having a
well built woman's figure rather than a weedy boys. So she took my
measurements whilst I was naked and they turned out to be a pathetic 36"
chest, 29" waist and 34" hips. Then she put me into a long satin purple
nightie that was too small for her and that came with a matching
negligee and told me to sit tight whilst she went shopping for a couple
of hours. Before she left she painted my finger and toenails with a
plum nail varnish and spritzed me with Extravagance perfume.
Left to my own devices for a couple of hours I wandered around the
house. I marvelled at my new facial look, the sudden prettiness of my
hands and feet with their varnished nails and the glorious feeling of
satin on my hairless body. Two things began to happen to me
simultaneously. Firstly, I felt a growing feeling of what I can only
describe as girlishness descending over me, I wanted to move, sit and
behave in a girly way. I practiced these movements and also speaking
and giggling in a feminine manner. The second thing that happened was
that I felt incredibly sexually stimulated so that all my girlishness
was somewhat spoiled by the 6" boner that tented the front of the
nightie.
My excitement was enhanced by the feeling of the satin swishing across
the tip of my penis. These two happenings together overwhelmed me as I
had never felt so incredible in all my life. Before Helen's return I
sensed I was already hooked on dressing as a girl and trying to act as
one. I sensed other even stronger compulsions brewing under the surface
but I did not understand them yet. Eventually as I kept gazing in the
mirror at my feminized reflection and experiencing the glorious sensual
feeling of the satin, I found my hand gripping my appendage through the
nightie and I began to masturbate in front of the wardrobe mirror. I
became lost in the erotic sensations and the new feminine feelings to
such an extent that I did not hear Helen return and I was close to
climax when she walked in on me. Embarrassed I tried to cover up.
"Don't worry honey I think you look sexy and by the state of your
arousal so do you," Helen said. "Go on sweetheart finish yourself off I
want to see you cum. But don't get it on your pretty nightie catch it
in your hand."
"What?"
"You heard me now do it, blow your load for me."
I continued to stroke my cock, bending my legs and arching my back as I
neared orgasm again. Helen urged me on asking me if I was imagining the
penis in my hand was another guys. No I told her but then she argued
that it must be as pretty girls don't have cocks. She came up behind me
and fondled my buttocks and back through the satin of the nightie all
the time asking if I was a pretty girl. Finally I said yes. Then she
asked if I was a pretty girl bringing a guy off and was his cock going
to spout cummies for me. As she said this so her hand disappeared up the
back of my nightie and a fingernail touched my anal rosebud. As she did
this I finally came spurting into my hand gasping "yes" as I did so.
"Yes what honey?" she asked. "Yes you are a pretty girl bringing off a
guy with her pretty hand?"
"Yes," I replied.
"I thought so. Well you better eat your man's seed cos that's what
girls do for their men."
"No I can't," I panted.
"Yes you can and you will," Helen sternly demanded. "What your jiz is
good enough for me but not you is that it?"
"No of course not."
"Well I have swallowed plenty of the stuff so it's about time you did
too or we can forget this dressing up game right now."
I had just had the best orgasm of my life so I was in no position to
argue. Also I could not stand the threat of an end to the dressing so
soon. I was having too much fun to stop and the thought of eating my
own cum had a perverse thrill for me even though I was a bit grossed out
by it. I licked the large gob of jiz off my hand and swallowed quickly
before I could taste it properly. It was warm and gloopy but if I did
not think what it was it was okay. Then Helen told me to lick off all
of it from my hand. Now I could not avoid tasting it and it was a
little salty and musty but not too bad. Not only did I find I could eat
it without feeling sick I found that the thought of what I was doing
continued to turn me on.
Helen was delighted in my performance and kissed me long and deeply
trying to capture some of the taste. "Well so my little girl has had
her first taste of cum, what didya think."
"It was okay."
"Well it wont be your last if you want to keep playing these games. Do
you?"
"Yes, I think so."
"Right well if you are gonna dress like a girl we better give you a
girl's name. Any preferences?"
"No you choose. After all you kinda created me," I laughed nervously.
What was I doing and where was this going. I only knew I felt more
excited than at anytime in my life.
Helen studied me closely. "Sasha that is what we will call you, Sasha."
I liked the name and being given a girl's name increased the buzzy
feeling I felt inside. Happy with my acceptance of this new role, Helen
began to treat me like her rather simple kid sister as she went through
the items she had bought for me. Firstly she showed me the small
silicon boobs she had got which she said would be fixed to my chest with
surgical glue. She explained that small would suit my frame but that my
cleavage would be increased by the push up and silicone filled bras she
had bought. She also laid out five pairs of panties, tights, including
a footless semi-opaque pair, and hold up stockings. The panties
included two pairs that were reinforced and padded and especially
intended to give cross dressers a better shape. The rest of the bags
contained items mainly from cheap fashion stores or Charity shops and
with the exception of one short dress and some cardigans, consisted
largely of little tops, and short skirts. It was all very feminine and
revealing. There were also two jackets, a short brown suede jacket with
large gold buttons and a fake leather black coat that would come to just
above the knee. It was not fashionable but I thought it looked a bit
French and very sexy. Finally, Helen told me there was a shoe sale on
and there were a number of pairs of size 8's on offer so she bought me
some. The footwear consisted of a low heeled pair of round toe black
slipper like shoes with beaded decoration, a closed toe 4"high stack
heeled mid brown shoe with a t-bar, a 3" high stiletto heeled open toed,
shiny red strappy sandal with an ankle strap and a tight 4" high
stiletto heeled, tight fitting, black knee boot.
"I didn't get any jewellery cos I have loads of old stuff you can have
and tons of make up I can pass on to you that will do until we go to a
beauticians," explained Helen excitedly.
"Whoa, I thought this was only for the day and no way am I going to a
beauticians."
Speaking to me as if I was a child and a not very bright one, Helen
pointed out that I was clearly enjoying doing this and that I would
obviously want to do it more, which I reluctantly conceded was probably
true. She reminded me that she was bisexual and that she had decided
that her boyfriend was going to be her girlfriend for a while. She
believed I would enjoy it and if I cared for her at all I would agree to
do it. I felt compelled to agree. She knew I was excited both by what
we were doing and the slight element of coercion. It was all part of
her gentle domination of me.
Helen explained that she wanted me to spend the rest of the day with her
en femme. That Sunday I tried on all the clothes she had bought for me
and she instructed me in make up and how to more convincingly do a
feminine voice. I hugely enjoyed the experience it was both fun and
sexy. Every night for the following two weeks, as well as for the
whole of the following weekend she insisted I dressed as a girl. I even
feigned illness for three days while she took some owed time in lieu to
speed up my progress. She only ever called me Sasha. We did not go
anywhere and stayed in so I could perfect my new persona. I practiced
my voice, make up and accessorizing clothes and developing a fashionable
but distinctive style. I was instructed in how to move, use my hands,
sit, get out of cars, bend down all in an ultra feminine manner. Helen
made me practice walking in heels with a girly swish until I was not
only perfectly competent in 4" high stilettos but had a natural sexy
sway to my hips and bum. She taught me how to listen more in
conversation, how to make direct but not challenging eye contact and how
to use my hands expressively including the use of touch to emphasise
points. She pushed me hard until I was often very tired and had sore
feet, but I did not complain. I liked being told what to do, I liked
being forced to dress as a girl, in fact I increasingly just enjoyed
dressing as a girl without the domination.
Throughout this period Helen kept me on a strict diet and made me
exercise through dance regularly which also improved my deportment and
elegance. My weight dropped to 135lbs and my waist shrank to 28." For
relaxation I was made to read women's magazines, girly romances and look
at female porn. Sex was frequent and fun but totally controlled by
Helen. I was introduced to anal play with butt plugs, dildos and
vibrators. I was denied penetration of Helen, though I did use toys on
her and was often asked to orally stimulate her. My own orgasms were
secondary to her pleasure and focused entirely on association with anal
stimulation, the stimuli provided by silk and satin fabrics and my own
self-generated excitement at my feminised image. On the Saturday two
weeks after my feminisation began, as I sat at the breakfast table in a
red silk short nightie and matching wrap, Helen informed me that we were
going out and that she had booked me into the beauticians. At first I
tried to argue but she told me to shut up and do what I was told
"Remember the rules honey, you either show cleavage or lots of leg but
never both unless you are a complete slapper. And since you don't have
tits I think you should show lots of leg. And you do have great legs,"
Helen said to me as she ushered me upstairs to get ready. After a
shower and ensuring I was perfectly smooth and hairless, I put on pretty
pink matching bra and panties. The former filled out with small
silicone inserts. I put on a pair of very fine 10 denier nearly nude
coloured tights over which I wore a short skirt in a pink and white
plaid pattern. A dusky pink angora short sleeved cardigan with fake
pearl buttons completed my outer clothes. Around my neck was a string
of white beads which progressively increased to the biggest size bead
which nestled above my little cleavage.
On my wrist I wore an old silver charm bracelet of Helen's for which she
had provided some new extra charms, a pair of handcuffs, a lipstick and
a ballerina. All appropriate to my new role she claimed. My fingers
were bedecked with silver rings, mostly small and delicate but one on
the central finger of my right hand larger with a large pearlescent
stone. I had discovered I loved rings and was more than happy to wear
more than was strictly normal. In my ears were some pearl studs in the
rear holes and large silver hoops in the front piercings. My make up I
did lightly, a smooth and light base foundation, a touch of blush, a
light pink eyeshadow with the lid highlighted in silver and the lips
made moist with a natural pink shiny lip gloss. On my feet I decided to
wear my pair of 4"high stack heeled mid brown shoes with t-bars. The
look was young, preppy and cute and I knew that so long as I was
confident and acted feminine I would pass okay.
After publicly parading me through the shopping mall Helen took me to
Amanda's her beauticians. Amanda was a short plump red headed woman in
her late 30s with a chubby but pretty and expertly made up face. Amanda
and Helen kissed on the lips. "So this is your new prot?g?," she said
indicating me. "Yep, meet Sasha," Amanda hugged me, "well sweetie you
look very girly, quite pretty and almost passable but we can make you
stunning." To my surprise I felt a thrill of anticipation at the
prospect. I was worked over for three hours. Acrylic nails were added
to mine giving me undeniably feminine nails that even clear varnished
for the week, as Amanda suggested, were still going to be noticeable to
my work mates. My hairstyle was spruced in a way that made it all but
impossible to pass off as a funky male style and it was dyed strawberry
blond. My eyebrows were worked on but could no longer be considered as
just being tidied up but were formed into obvious, fairly thin feminine
arches. Before my make over I had all make up removed and looking back
at me from the mirror was the most effeminate looking male I had ever
seen. After the expert make over, however, it was the face of a highly
attractive woman who had just a hint of masculinity about her features.
I could not help myself, I loved the image and I knew I was going to
love becoming this new feminine person. When we walked back from the
beauticians, with my bag of make up hand picked as best suited to my
complexion, I walked with my head up unafraid to be seen, making Helen
smile with joy at me.
Over the next few months Helen introduced increasingly extreme elements
into my enforced feminisation and domination. As she quickly realised
that I was more than willing to at first dress as a girl at home and
then appear and act like a girl in public, new elements had to be
introduced to humiliate me and make me accept things against my will.
She made me undergo laser depilation and electrolysis to remove my
slight beard, chest and stomach hair. This was torture and I hated it
but I did begin to appreciate the smoothness after a couple of months,
though the regular visits for hair removal I initially found
humiliating. The effects on my body hair were accentuated by taking
female hormones and testosterone blockers which I did at a full dosage
for a sex change for four months but afterwards at a lower level which
maintained the changes to my skin, hair and fat distribution but without
threatening my ability to have erections or lead to me fully growing
boobs, though my nipples increased in size and I developed a little
breast tissue. This scared me a lot at first as I thought I would be
chemically castrated. I visited Amanda's weekly for waxing, pedicures,
manicures, nail extensions and eyebrow shaping. After three visits
eyelash extensions were added so that in public I had noticeably long
and feminine eyelashes. At work from the very beginning of my
feminisation I was made to wear panties and gradually over a few months
replaced my male outer wear with female equivalents.
Helen also insisted on behavioural modification. Once I had perfected
my female voice she insisted I used it all the time with her. She
wanted me to use it in work too but I resisted. Yet persistent use of
my female voice gradually made it the natural way to speak I found I
increasingly lapsed into it in work so that I gave in eventually. My
new way of speaking was not commented on by my colleagues presumably
because it suited the way I looked and acted. Helen forced me to walk
and move in the most extravagantly female way so that a feminine way of
moving also became natural. I was chastised if I was ever heavy or
manly or even insufficiently swishy. My hand movements and ass sway
became womanly when dressed as a girl and extremely camp when I was not.
All the time she encouraged me to participate in girly activities
including ogling and appreciating men. At first I hated it and then I
became embarrassed by being able sometimes to see the attraction of some
guys. Perhaps it was being surrounded by femininity or the conditioning
Helen subjected me to but I even felt a little tingle for a few male
images. After five months of feminisation as I lay beneath her licking
her quim she announced that she wanted to see me fucked by a guy to
confirm that I was truly her little sissy. I pulled away from her and
screamed no way that no matter what had happened between us I was not a
fag. She slapped me hard across the face telling me never to scream at
her again, but I did and she slapped me again. Overpowering me she
placed me across her lap and spanked me so hard I began to cry. What a
sissy I had become powerless against my girlfriend. She told me to stop
struggling and calm down and she would stop spanking me.
When I had she asked me to do this for her as she would find it a huge
turn on. Again I said no, that I would do most things for her but not
this. She continued to cajole me, beg me and then threaten me. Finally
she screamed, "right get out. If you can't be my sissy properly I am
not interested in you, so you can fuck off." I did not think she was
serious but when her temper mounted further and she began throwing my
clothes in a suitcase I was convinced she was. Cold fear gripped my
guts. After all I had gone through. All the changes I was still
experiencing how could I be rejected to face the world on my own as a
heterosexual but now exceedingly effeminate boy. Suddenly I realised I
could not go backwards to who I had been I had to go on. I could not
loose Helen so I reluctantly agreed to have my last vestige of
masculinity corrupted if not driven from me. I convinced myself my
decision was the best of two unpalatable choices but deep down I knew I
had a spark of interest and excitement about Helen's desire and I
desperately wanted to know more.
Helen made all the arrangements. She took special sexy pictures of me
and placed them on the internet. In them I looked as good as most
professional tv escorts and as I was advertising myself for free there
were soon many takers. Helen weeded out the obvious time wasters and
freaks and reduced the list to five who she emailed. She forced me to
comment on each one and say which one I preferred and why. The five
emailed resulted in webcam conversations with four of them. Phone
numbers were exchanged with three of them and meetings arranged where we
met for a drink at our favourite club, which though a straight place was
tranny accepting. I had very little involvement in the meeting with
Helen doing most of the talking. All the guys wanted to participate
with me in scenarios where I dressed up as their fantasy, little girl,
school girl, hooker, mistress, bridesmaid or sexy secretary.
One guy to my knowledge was selected by Helen, though unknown to me she
had arranged for the other two to meet with me at separate times. I was
told the guy chosen to deflower me was Mike, a 28 year old white
experienced tranny lover. 6'1" tall he was slim and athletic with a
craggy reasonably handsome face and so he said a 9" circumcised
moderately thick erect penis. I was not attracted to him but I was
turned on by the thought of having to let him fuck me because Helen was
forcing me to do so. The evening came when he was to visit. Helen had
set up a video camera and opened a bottle of wine, chill out music came
from the CD player and I was dressed as every pervert's dream school
girl. Amanda had made me up to the nines earlier in the day, fully
aware of what Helen had planned for me. She had used pink and peach to
make me cute but sexy and dyed my hair a streaked strawberry blonde. I
was wearing a white blouse with a school tie, grey tight mini skirt
which showed my barely black stocking tops and suspender tabs and 4"
stiletto heeled black patent court shoes. As usual I indulged my
passion for rings and in my ears were my largest silver hoops. Mike
wanted a scenario where he was the young teacher who gets off with the
5th form slut and I was the slut. I was so apprehensive I had soon
drunk half the bottle of wine in two large glasses and Helen had poured
me a third. When the doorbell rang Helen sent me to open it and told me
to remember to chew the bubble gum she had given me.
I drained my third glass of wine, began to chew some bubble gum and went
to the door. I was still not a willing participant but seeing myself in
the school uniform had been a turn on as I looked like a tranny chaser's
wet dream which made me feel very sexy and the wine had relaxed me a
little. Mike came in at my invitation kissed me on the cheek and gave
me a bunch of flowers. This helped to increase my feminine feelings and
made the planned evening seem a little more acceptable. Helen gave him
a scotch and poured a large one for me too. I blew a bubble as cutely
as I could for Mike then deposited the gum and took a deep slug of
whisky to steady my nerves, realising as I did so that I was feeling a
little tipsy.
"How old are you Sasha?" Mike asked.
"Fifteen sir," I dutifully replied.
"Mmm you are very naughty drinking so young. Do you do lots of naughty
things Sasha?"
"No sir."
"Oh I think you do. Your school grades are dreadful aren't they?"
"yes sir."
"And that is because you never do any work but are always off partying,
drinking and getting off with boys, isnt it?"
"I guess so."
"Okay Sasha come and sit by me," Mike demanded indicating the sofa next
to him.
I sat down with my knees clamped together and a small gap between us
which Mike closed immediately. "Drink up Sasha because I want to show
you what trouble young girls can get into when they booze and mess with
boys. I think it will be a valuable lesson don't you?" I spluttered a
sort of agreement as I downed the scotch. It was easier for me to down
it quite quickly as I hated the stuff. This Helen knew so she smirked
at me from across the room. Mike and Helen chatted inconsequentially as
I quickly sank my second scotch and I began to relax. I began to enjoy
Mike's company and the game of pretend we were playing, though I was
finding it difficult to focus or think clearly. As I drank the third
whisky Mike's arm went round my shoulders and he whispered in my ear
that I was very sexy and that he wanted me to snuggle into him. It was
warm and secure so I thought why not it feels quite nice. With his arm
wrapped around me and his hand caressing my shoulder, which also felt
nice, Mike asked what naughty things I did with the boys?
"Kiss them surr," I replied whoozily.
"Are you a bit of a slut Sasha? Do you kiss them with your tongue and
do you let their tongues into your mouth?"
"Sometimes sir." I giggled.
"What you sometimes let them kiss you with their tongues or you are
sometimes a slut?"
Confused I said, "umm sometimes I let them put their tongues in my
mouth."
"Which makes you a bit of a slut doesn't it."
"I dunno."
"Did you know that kissing like that is called french kissing."
"No sir," I said as wide eyed as possible as I was beginning to enjoy
the role play.
"Show me how you french kiss the boys Sasha."
I gulped hard and then swallowed my third drink, but still hesitated.
Momentarily I was scared again.
"Here have a sniff of this Sasha," said Mike passing a small vial of
amyl nitrate under my nose. The fumes made my head spin but I also felt
a quickening of my pulse and a mounting excitement in my chest.
"Go on Sasha show Mike or I will let him spank your bottom hard," Helen
said. I could not focus and felt detached from my surroundings but also
I was feeling very warm and comfortable. I looked at Mike tilting my
head slightly and as I parted my lips to speak and prolong the
inevitable, Mike took my action as all the invitation he needed and he
crushed my sissy lips to his. I was too shocked to struggle but then
through the whisky fug I realised that I was not repulsed by what Mike
was doing. That he so obviously desired me made me feel desirable as a
woman and accepting of the attentions of a man. Physically it was quite
nice and he was a good kisser, by now unconsciously my tongue was
responding to his, but what was really interesting was how utterly
feminine it made me feel being in a guy's arms. When we surfaced for
air Helen refilled my glass and Mike held some more amyl nitrate under
my nose. The buzz made my tummy tingle. Mike now had a hand on my knee
and was causing me to shiver nicely as he moved it a little up the
inside of my thigh with me unresistingly parting my legs slightly for
him.
"You kiss like a slut Sasha and I bet you let the boy's feel you up like
this, don't they?"
"Shumtimes," I gasped.
"She is a fibber Mike," said Helen, "she is always letting the boys cop
a feel and she likes to play with their cocks."
"Oh you really are a slag aren't you, a right little tart. Now you
didn't answer me before so this time tell me truthfully are you a slut?"
Mike asked as he put the whisky to my lips and forced me to take another
slug.
"Yesh shurr I am a slut," I slurred and spontaneously initiated another
round of tongue tag. I was feeling very horny by this time and any
inhibitions had been drowned in scotch. Helen had erected her camcorder
and was filming my antics. I smiled into the lens as Mike gave me
another snort of amyl nitrate and with a giggle I drained my fourth
scotch. "That I think is enough young lady," Helen said removing my
tumbler.
"Awww shpoil sport," I giggled. Mike's hand had parted my legs fully by
now and had stroked its way to my crotch. "Nice clit," he said as he
felt my member stiffen to his touch. I rubbed his groin in automatic
response, "niesh cock," I countered. "Take it out and play with it
baby," Helen urged her hand now inside her panties.
"Okay cos I am a shlut and thas whass shluts does."
"Thats right honey you are," Helen cooed.
I was a little disappointed when I released it from Mike's slacks, this
was no 9 incher, 7 at best. Inwardly I giggled that I was disappointed
by the size of another man's cock but I was not worried, I was so way
past worrying, especially as Mike was giving me more poppers. I skinned
his cock a few times as I kissed him deeply, really getting into the
role of a teenage slag when he broke the kiss and hoarsely said, "kiss
my dick Sasha then I want you to lick it and suck it, like the naughty
little slut you are."
"Yeshh shurr," I replied no longer really aware what planet I was on and
quite content to lick the precum from the tip of Mike's penis. Vaguely
I thought it tasted okay. I opened my mouth and let Mike's cock in.
Using my experience gained on Helen's dildos I went to work appreciating
that this warmer and more responsive phallus was much more fun than a
dildo. Meanwhile Helen had taken out a vibrator and was thrusting it
into herself as I sucked rhythmically on Mike's cock. Mike told Helen
how good I was and she shut her eyes with orgasmic bliss. When she
started down from her climax she took the vibe out and hitching my skirt
up as my head was in Mike's lap, Helen pulled aside my panties and lubed
my anus before plunging in the vibe coated in her juices. I went into
sensory overload and was moaning with ecstasy as Mike began to face fuck
me. This went on for some time before Mike pulled away and said to
Helen, "Is she ready for fucking." Helen had no doubt that I was.
"Yessh pleashh Mikey," I said as he positioned me on the sofa on all
fours. It felt incredibly exciting, but even in my drunken state I began
to feel anxious inside. I had never been with a man before and so fear
began to well inside me. It was banished when he tip of Mike's tongue
suddenly slid into my anus. It felt wonderful. Mike then forced open my
legs and his powerful body rose up over me. I began to tremble. "Fuck
your shlut shurr," I encouraged as I felt Mike's penis press against my
rosebud. With ease he pushed into me and the feeling was fantastic but
that was the last I remember of the night as the sexual stimulus, scotch
and poppers took their toll.
I did not blackout but my memory of the rest of the night was completely
gone the next morning as I battled through the hangover from hell. By
the evening I had recovered and Helen who had teased me all day about
how much I seemed to enjoy the previous night told me we were going to
watch the video of the previous evening's proceedings. I sat next to
Helen on the sofa wearing a short pink nightie and matching chemise. At
first the film just showed Mike and I making out as I hazily remembered.
I was clearly drunk but also obviously enjoying the experience of being
with a guy. I remembered both these feelings, but I did not remember
screaming with ecstasy as Mike ploughed into me or bouncing on the end
of his pole like a demented nymphomaniac. Watching myself being fucked
was quite a turn on but I was embarrassed and a little tearful to hear
myself saying, to Helen as Mike fucked me, "I love cock. I love cum.
Whore me out I wanna fuck guys for you. Let them cumm all over me." I
also urged Mike to "fill my asshpussy with cum" exclaiming to nobody in
particular that I was "a cock hungry shlut." Noticing I was upset Helen
said, "don't worry sweetheart you were drunk. It was just fun."
I asked Helen what this all meant and was I gay. Helen told me to stop
worrying and enjoy new experiences, adding as she eased her hand up my
night dress to fondle my excited cockette that bisexual seemed more
likely. After the experience with Mike my feminisation accelerated and
the relationship with Helen became more intense with there no longer any
doubt that she was my mistress and I was her sub sissy. Two weeks later
on returning home on a Friday evening she told me to dress in the
clothes she had laid out on the bed for me and follow the makeup
instructions she had written down for me. I did both without question.
By the end of it I had made a very passable impression of being a young
hooker dressed in a tight red top, black leather mini skirt, fish net
hold up stockings and shiny black knee boots with 4" heels. Helen also
told me to lube my ass and insert my largest butt plug, which gave me a
pronounced wiggle when I walked. When I went down stairs I met Monty,
who was one of the guys that Helen I had met with to decide who would be
my lover. He was a large, slightly fat, middle-aged black guy. I
remembered I had thought he was quite amusing company when we had met
previously.
Turning to Helen when he saw me Monty said, "perfect, she looks amazing,
just like a trashy street whore. Very sexy."
I looked confused and noticing Helen said, "well Sasha you said you
wanted me to whore you out and you remember Monty wanted to fuck you
while you acted like a hooker, so here we are. I decided one lover was
not enough I think you should be broken in by several cocks so you
realise that you are just a pathetic little pansy. Not a proper man at
all. Just a soft effeminate receptacle for real men's cum. And Monty
here has a wonderful, large cock, just like you need. You want this
don't you baby?"
"Yes," I hoarsley and uncertainly whispered not wanting to disappoint or
upset Helen.
Helen told me I was a good girl and demanded that I take some snorts of
amyl nitrate and share a large joint with her. My head was soon buzzing
and I felt relaxed and excited at the same time. Helen pronounced me as
ready causing Monty to break out in a lascivious grin. "Okay then you
tart come over here and suck my dick," demanded Monty, standing in our
living room with his straight, veiny, large cock pointing straight out
from his trousers. As if in a dream I found myself kneeling in front of
him. Did I really want this, my mind seemed uncertain but my hand had
already grasped his erection and was guiding it to my parting lips. My
next thought was how nice his cock tasted as I ran my tongue around
Monty's glans and probed his pee hole and how nice it was to have a
really big cock to play with this time. Soon I was bobbing my head
enthusiastically as Monty's penis slid in and out of my mouth. As his
passion rose so he grabbed my head and began to face fuck me. I
struggled not to choke or retch as his cock entered my throat.
"Oh yeah baby you are a great cocksucker" Monty groaned as I felt him
tense a moment before his cock spasmed and spewed forth his hot seed
into my hungry mouth. I felt proud of myself that I had made this guy
cum in my mouth and I wanted to please him. I kept sucking and licking
as his penis shrank, drinking every drop of his slightly tangy cream. I
was amazed by how much I liked the taste but I did and I wondered how
different other guys would taste.
"Come here and kiss me sweetheart," Monty demanded after I had licked
him clean. Monty had me settle on his lap as he sat on the couch. We
necked enthusiastically and I felt him tug my panties to one side and
begin to move the butt plug inside me, making me whimper. Suddenly he
removed it with a plop and briefly I felt cold air enter my well
stretched rectum. A momentary feeling of emptiness was fleeting as
Monty inserted a thick finger into my well lubed ass, quickly following
it with two others. By now I was feeling really turned on and very happy
to play the role of the little slut which my appearance made me seem. I
snaked my delicate hand around his fat black cock and began to coax it
back to an erection. His cock was so thick and smooth and it fascinated
me. I felt a tingling inside and knew that Monty's fingers were not
enough for me.
"Oh Daddy put that big boy in me," I begged.
"Sure thing sugar plum," Monty replied.
Monty lifted me up slightly and I felt him position his bulbous cockhead
against my rosebud. The pressure built and it hurt a little at first
but all those hours of dildo play and butt plug insertion ensured that
my ring could expand to take him in. I squealed a little as he entered
me and the feeling of fullness was incredible. As his cock hit the
target of my prostate I felt simultaneously both discomfort and intense
stimulation. The pain receded quickly so that I was soon bouncing
enthusiastically and comfortably in his lap, as his shaft slid in and
out of my eager love tunnel. I knew instantly that I loved the feeling
of a big cock filling me. It was mentally so emasculating and
feminising which I craved but as I moved in time to his surges it was
also intensely physically pleasurable. The strength of these feelings
grew as I tried to keep pace with Monty's increasingly urgent thrusts.
His hands began to knead and claw at me as his excitement mounted. The
physical stimulation was overwhelming, my body trembled, I tossed my
hair as I shook my head moaning with lust, craving his cock.
Aww fuck, fuck yes. Oooh yes yes, YES, FUuuuuuuuck," I cried out as my
insides felt like they were melting and my anal orgasm threatened to
blow my head off. I cried out with the unspeakable glory of it, as wave
after wave of divine electricity coursed through my body and my still
flaccid cockette leaked a little watery jizz without even being touched.
Helen watching us with a vibrator deep in her pussy noticed my little
orgasm and smiled at me.
As I calmed a little Monty lifted me off his lap and turned me over so
that I was leaning forward onto the sofa. Having spread my legs he then
buried his cock once more into what now felt like my gaping bum hole.
"Take this you cunt, whore," he snarled as with animal passion he
brutally ploughed into me. I loved every minute of being his little sex
doll as he pounded me ever faster until he reached his climax. "That's
it milk it" Monty demanded as I clenched and rippled my anal muscles
around his erupting manhood, in wonder at the complex of emotions and
physical yearnings that washed over me as he filled me with his baby-
making cream.
Sated he whacked my ass as I slumped forward and sprawled in exhausted
bliss across the sofa, "your a good fuck slut," he said. "For a
beginner she is a terrific cockwhore," Monty said to Helen as he left
having shagged me half senseless and quickly pulled his clothes back
together. I may have been good but I was clearly just a quick fuck as
far as Monty was concerned but far from feeling disappointed I was
excited to be treated as disposable sex trash. After he had gone Helen
embraced me and kissed me deeply. Pushing two fingers into my sloppy
hole she laughed "my little sissy likes to be fucked by men so much it
makes her cum. You like being a girly boy cockwhore don't you."
Ashamed I meekly replied "yes but Helen it is you I adore." "I know
sweetie, I know," she said soothing my confusion with erotic stroking of
my ass.
The next day being a weekend Helen had me dress as a very sexy secretary
to meet another guy that lunchtime, Robert. He had an office fantasy
and wanted Helen to take me to his office for an afternoon session. We
had talked long into the previous night about how I felt looking and
acting like a slutty girl for men. I confessed to being turned on by
it, but also confused and humiliated by it. This humiliation stemming
as much from my desire to act like a slut as to have sex with another
man. She admitted that for her the thrill was wrapped up in three
things, seeing her boyfriend have gay sex, seeing me humiliated and
emasculated and knowing she had the power to change me from a normal guy
into an effeminate fairy faggot. She wanted to extend my humiliation so
the next day I was to be dropped off at Robert's office and to get to it
I would have to walk through an open plan office just as his Saturday
morning employees were going home.
Helen prepared me by tightly lacing me into a corset, which pulled in my
waist, defined my hips and with the added assistance of silicon breast
inserts gave me a decent cleavage and the appearance of quivering breast
flesh through my naughtily partially unbuttoned white silk blouse. My
outfit was completed by a grey waistcote, very tight black pencil skirt
to 4" above my knee and 5" high stiletto heeled black suede court shoes.
As the corset had garters I wore stockings attached to them. They were
a nearly nude colour but with a very prominent black seam, which made
them very tarty looking, an impression enhanced by the clear outline of
the garter tabs through my tight skirt. Robert wanted me to have long
hair so Helen had bought a strawberry blonde wig very similar in colour
to my own hair but this had light blonde highlights in it. Unlike my
natural hair it had a light wave and cascaded to the middle of my back.
I knew I looked attractive and passable at least at night but at 6'2" in
my heels I was bound to attract attention and in the glare of office
lights most would suspect my true gender if not know. As Robert ran an
events company it was likely that I would be considered to be a drag
queen looking for a booking so Robert would not arouse suspicion amongst
his staff, but I would be gauped at as a freak. Scared and embarrassed
I entered the reception area of Robert's company. I tottered over to
the reception desk, "Can I help you err miss?" asked the receptionist,
an attractive brunette in her late 30s. "Sasha Dickard to see Robert
Hawley," I lisped. She grined, "of course" and escorted me through an
open plan office to a rear private office. A few people were still
preparing to leave as I passed and I received some knowing looks and
even the odd lustful stare. My heart beat with excitement at the same
time as I blushed with embaressment and a little shame. I was so
effeminate and submissive now, how could I ever claim to be a man.
"Through here Miss Dickard," the receptionist said ushering me into a
private office. She closed the door behind me and I stood in a large
room on a plush maroon carpet, with a big desk at the far end and a sofa
and comfortable chairs between me and the desk to one side of the
office. A video camera was on a stand in one corner angled to cover the
centre of the office. It guessed it was to film the proceedings and I
flushed a little at the thought of having my homosexual encounter
recorded by strangers. A thick set, powerful looking man in an open
necked and expensive shirt and suit trousers, stood up from behind the
desk, "ah you must be Sasha," he said coming towards me and extending
his hand, "yes sir, pleased to meet you," I replied taking his hand. He
didn't shake my hand but pulled me towards him, "no need to be so
formal, Mr Hawley will be fine," he said as he kissed my cheek lightly.
"Now then Sasha," Robert began indicating that I should sit on the
couch, "you know I am looking for a personal assistant, a very personal
assistant, yes?" I nodded and smiled. "She needs to be a very special
girl. Pretty, attractively dressed, willing to undertake any reasonable
tasks, obedient, a little subservient even. Above all she must want to
please me. Is this you Sasha?
"Yes I think so Robert."
"Well you look good I must say. Take off your waistcote and unbutton
another one on your blouse. Mmmm that's better, very nice."
Robert slipped one arm around my back and pushed the other into my
blouse to massage my breast through the bra cup. "Very pretty corset by
the way and I like that you have at least the illusion of breasts. Very
good."
Passively I sat there whilst he explored me. When he finished with my
breasts he began to ran his hand between my thighs, so I parted my legs
a little for him as he stroked the fine denier stockings, flirtingly
fingering my stocking tops. "Oh yes very nice," he breathed heavily." I
thanked him submissively. Suddenly Robert was all business and pulled
away he moved me to the desk and got me to follow him. Putting me in
front of a laptop he told me to take a letter. I was not a good typist
at the best of times and with my long nails I was hopeless. The printed
letter was full of mistakes, some bits of text were jumbeled and there
were misspellings and typos galore. Robert examined my effort, "this is
terrible Sasha, absolute rubbish. This does not please me at all. You
will have to try very hard to make up for this." I suppressed a giggle
at Robert's unconvincing role playing but was surprised when he picked
up the phone and asked someone called Janice to join us. "Janice can
type the letter while you take another form of dicktation." Robert sat
in an armchair and gestured for me to kneel in front of him. As I knelt
he undid his fly and produced a thick 6" circumcised cock. I bent
forward and gently caressing his balls with one hand used the other to
guide the shaft into my yearning mouth. Sucking and licking his dick I
was disturbed by a cough as Janice, the receptionist I had met earlier,
entered the room and smirked at me. I blushed from my neck to my
forehead as my face burnt with shame. "Keep going you little whore and
don't mind me. Please the boss because I suspect that is all you are
good for," Janice said sneering at my typing attempt. Later I was told
that Janice was not a receptionist but Robert's sister and business
partner.
Janice sat down and typed the letter as Robert dictated with complete
indifference to me sucking his cock.. Finished she brought the printout
to Robert who told her it was perfect and that perhaps she could give
the sissy lessons. As a reward she was invited to play with me. As I
continued to work Robert's cock with my mouth, Janice came up behind me
and pushed my skirt up around my hips. Reaching forward between my legs
she massaged my groin with the palm of her hand. Pulling my panties to
one side she fingered some lube into my anus and then removing a pritt
stick from a desk draw she thrust it into me. As I grew hotter and
bobbed my head up Robert's cock ever more enthusiastically she finally
crawled between my legs and sucked on my little erection. She was very
good and I erupted my seed into her mouth shortly before Robert flooded
mine with his.
When recovered Robert told me to kneel between Janice's legs and tongue
her clit and pussy while he watched. Janice positioned herself against
the desk her skirt hitched up and her panties around one ankle. I knelt
before her parting her sopping pussy lips and tentatively touched her
clitoris with the tip of my tongue. She tasted as she smelt, clean and
nicely tangy. I flicked, sucked and nibbled as guided by a gasping
Janice whilst Robert watched cajoling his prick back to an erection with
his own hands. My jaw was aching by the time Janice clamped my head
between her thighs and began to moan loudly, shaking as an orgasm ripped
through her body and her juices flowed over and into my mouth. She
continued climaxing for at least another three minutes. Finally,
pushing me away so I could at last breathe freely she announced that I
was a great pussy licker and suggested that I come with her to freshen
up my make up.
Taking my hand Janice took me to the ladies. Holding my face in her
hands she kissed my messy mouth deeply. "I needed that," she said
before telling me she would repair my make up for me. After a few
minutes she said, "there all done, now knowing my brother he will be sat
there with a raging hardon with which having come once he will now fuck
you senseless for at least the next hour. So good luck girl. Make sure
he has fun." Janice took me back to the office. "Pretty as a picture
and all yours," she announced as she half pushed me into the room like a
piece of meat into the lion's cage.
"Strip for me baby," Robert demanded. "Take your skirt and blouse off
slow and sexy. Then your panties but leave your corset, stockings and
heels on."
"Yes Mr Hawley," I replied in my best munroesque ultra girly voice.
I seductively minced and wiggled as I slowly removed my skirt and then
my blouse. I eased my panties down my legs with my back to Robert as I
looked at him coquetishly over my shoulder. "My that is a fine ass,"
Robert said standing behind me and cupping my bum cheeks. I giggled
receptively. His hands were all over me as I thrust my bum at him and
rubbed it suggestively against his groin. His jacket, tie, trousers and
shoes were soon discarded. I could feel him iron hard against my ass
crack as I ground my pert bum against his crotch. Reaching back I
tugged his boxers downward and immediately his hardness began to press
against my rosebud. This man was so hot for me that his lust infected
me increasing my desire for him to invade and possess me. "Please Mr
Hawley fuck me," I panted.
"Is that what you want you stupid cunt. Is that all you are good for to
have me fuck your ass."
"Yes Mr Hawley," I replied. "That is all I am good for to be fucked and
filled with cum. I am just a stupid bimbo cunt in need of a good
fuucking."
"Oh baby you are so right."
Bending me over the table his cock head pressed against my pre-lubed
anal opening and it gave way with little resistance to his invading
penis. Inexorably he pressed forward until I could feel his balls
resting on my ass cheeks. It got easier with every new cock I took and
this my third felt better than the other two as Robert quickly built up
a gentle rhythm. As he slid back and for up my well lubed rectum he
reached around clawing at my stockinged thighs and fondling my clit
stick making it hard. He nibbled my neck and licked my ear as he
started to pound me harder. "Aww yeah slut take it all," Robert
exhorted me as his balls slapped against my ass. My head shook in
passion and my knees felt week as tingles of excitement built in my
stomach. "Yes Mr Hawley fuck me hard, mmm harder, fill me with your
baby juice," I squealed and gasped. He rammed me ever harder until I
had to steady myself against the desk with my arms. "yes Im gonna fill
your sissy ass," he shouted moments before he ejaculated copiously
inside me. I spasmed with orgasmic pleasure as he filled me. I moaned
with lust and need.
Sated Robert quickly dismissed me and I hurriedly redressed. On wobbly
legs, encased in laddered stockings and with a sore ass, I minced
towards Janice. "My you look like you had fun and were a great fuck.
Sounded like it too." Blushing I thanked Janice who ordered me a taxi
to take me back home. Before it arrived she handed my a DVD telling me
it was something to remember my visit by. That evening Helen and I
watched it and the sight of me having my submissive, girly butt pounded
by Robert turned her on hugely so that soon enough my legs were drapped
over her shoulders as she ravaged my ass pussy once more with her
largest strap on.
The male visits to and from Robert, Monty and Mike plus a few other guys
went on for about seven months before Helen got bored with them,
probably because she realised I was enjoying them too much and certainly
was no longer humiliated by them or any of the scenarios she or the guys
dreamed up. The rapid immersion in sex with men that Helen forced on me
but which I rapidly grew to crave, left me increasingly frustrated when
she turned off the tap. She allowed me tasters of what I was missing as
on three occasions in the next five months she made me suck off guys at
tranny friendly clubs, and the clear frustration it caused me added to
the pleasure of inflicting humiliation on me. Each time I was made to
act slutty and suck cocks in back alleys or toilets which made me feel
cheap and desperate. Helen even called me a spunk addict. Without
relief my need grew until my sexuality appeared to be a confusion of
conflicting desires.
Because Helen and I experimented with my cross dressing together whilst
I was confused about my emotional and sexual feelings and desires I did
not feel guilt. What we were doing was consensual and generally
bringing mutual pleasure so there was nothing to feel guilty about.
Helen increased my confusion to an extent by emphasising my role less as
a make believe girl and more as a sissy and highly effeminate male. She
did not want me to hide behind the safety of being a passable woman when
fully dressed. I worked for a community arts project in the back office
so not only was I with a very liberal, broadminded group of people, I
was also not dealing directly with the public so no one made any adverse
comments about my increasingly feminine appearance and mannerisms at
work. We were a small team of nine of which just two others were men
and one of those, Colin, was openly gay, though at 6'1" and well built
he was nothing like the little fairy I was increasingly coming to
resemble. Helen got me to wear increasingly tight trousers through
which the line of obvious panties would show. I was encouraged to wear
more feminine style shirts and sometimes to let the lace of a camisole
show through them. Helen often made me wear a butt plug to work which
forced me to roll and sway my hips. On my well moisturised and
increasingly smooth face I was encouraged to use a little powder and to
apply lip gloss, both of which hardly drew attention away from, double
pierced ears, my ultra long eyelashes, my well defined eyebrows which
seemed to become thinner and more feminine with every visit to Amanda's
and my girl's hair do. Eventually the fear, embarrassment and concern
about what I was doing subsided, though the humiliation of being such a
sissy remained but it did so as an almost exquisite thrill.
Helen usually got me to travel home from work on the bus to increase my
humiliation but sometimes she would pick me up. On one such occasion
she asked my boss Michelle if I was ready and used Sasha as my name.
Michelle was confused but when told that her employee Josh was known by
his girlfriend as Sasha she readily agreed that it seemed a more
appropriate name for a girly boy. From then on I was known as Sasha to
everyone irrespective of whether or not I was dressed as a girl. In
work my slow transformation into a transgendered pansy helped the other
employees to gradually change in the way they acted with me. Almost
imperceptibly the women increasingly treated me as one of them. The
more they accepted me the more I was comfortable with them and the more
I acted like them. Both of the guys also began to treat me differently,
including opening doors for me and helping me to lift heavier objects.
Colin especially began to spend more time with me and to ask openly
about my transgendered nature.
Helen and I were together for 18 months but soon after I had my first
gay experiences under my own initiative we mutually agreed to split.
She remains a friend and there was no animosity when we broke up we just
realised that I had moved on to another level. This move came about
following the Christmas party season. It was then I met Ryan at Helen's
works Christmas bash. I went in full fem glory, having pleaded with
Helen to let me do so rather than appear as a faggot at a fetish club.
I wore an off the shoulder red figure hugging mini dress, with a pvc
black corset laced tightly over the top of it. My hair had been dyed a
bright bottle blonde for the occasion. I attended the party as Helen's
partner and although it was fancy dress there was no doubt amongst all
the people there that I was not just dressed like a girl for the party
but that I was a fully fledged sissy. It was Helen's company so nobody
was going to criticise her and everyone was very accepting, especially a
6ft 3inch hunk called Ryan. He was a 30 year old client of Helen's
firm, well known to her and openly bisexual. He asked Helen if I would
dance with him and she agreed. I enjoyed dancing with him and after a
while Helen's staff stopped stealing furtive glances at us. I was
treated as one of the girls and was even asked to accompany two of her
secretaries to the toilet where one of them, Krista, told me that I was
very lucky because Ryan was cute and she did not think Helen would mind
if I had some fun with him. The other girl, Amy, told me that Helen
always liked to get drunk at the Christmas party and usually coped off
with somebody who was not her partner. Sure enough a little later on
the dance floor I noticed her passionately entwined around some young
stud, so when Ryan dragged me out on the dance floor again I resolved to
go with the flow.
We danced to a europop number and then some urban beats both of which
gave me plenty of opportunity to rub myself up against Ryan to squirm
against him and to thrust my ass against his groin. Then we were into a
slow number and Ryan held me tight to him and his big hands kneaded my
ass as our groins grinded together. There was no mistaking he wanted me
badly as I could clearly feel his huge hard-on against me. I continued
to overtly try to stimulate him, acutely aware of the stares and grins
of Helen's work colleagues and other party guest's watching my antics.
Somewhere as I did this I realised I had changed as I was not humiliated
but delighted by the attention. Cupping my arse Ryan steered me towards
the bar, as we were about to reach a bar stool Helen stooped us and
dropping her car keys into my handbag said, "Sash why don't you take
Ryan out to our car and give him what he so obviously wants." I smiled
my response and taking Ryan's hand I led him outside to the car park.
Leaning against the car we began to neck enthusiastically. His hands
were all over me and when my highly manicured slim fingers began to
fondle his flagpole through his chinos I was surprised by how much I
wanted to hold and stroke his cock. There was no doubt that I was not
being instructed and forced now (no matter how willingly I had allowed
myself to be coerced previously), now I was enthusiastically responding
to an invitation. Being with a man was no longer a humiliating
enforcement of my sissy soul, it was simply sex, a sating of animal
lust. I wanted to be lusted after by men and some men, like Ryan I
lusted after. There was no longer any doubt I was attracted to men.
I had a deep yearning for Ryan, almost a hunger. I wanted desperately
for him to take me across the hood of the car and fuck me wildly, but as
soon as I opened his flies and felt his heavy veiny and potentially
spectacular penis, he became concerned about possible passers by. He
clearly wanted me but he was not prepared to make love to me in the open
air potentially in public. He urged me to get in the car and once we
were both in the back he pushed my head towards his groin in the
unmistakable male demand that I suck his dick. I wanted more than that
and I knew it would not go anywhere near to meeting the growing need
within me, but I was trained to be a compliant cocksucking sissy and I
responded in the only way I knew how, by parting my lips and enveloping
his member in my mouth. After a mere five minutes of my expert
ministrations on a nervous Ryan he spewed his gooey seed into my mouth.
I swallowed and with his needs met he escorted me back to the party,
where a beaming Helen asked if I had enjoyed Ryan as much as she was
enjoying her young stud.
By Christmas 2009 Helen had turned me into the swishiest, most
effeminate pansy outside of a gay burlesque show. Anyo