Bucket List Exhibitionism
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Bucket List free porn video
Bucket List
I'm 52 and I've been a closet crossdresser for over 30 years starting
with my mother's underwear and women's underwear I stole from local
washing lines. When I got married my crossdressing took something of a
back seat although I did try and get my wife interested by buying her
underwear I could also wear. We were much the same size back then. But
she did not want to know and whilst I wore the underwear I had bought
when she was out she threw it out quite quickly. Over the years I had
acquired quite a collection of women's underwear, nighties and other
female clothing. As far as I know my wife never knew of the collection.
My wife died six months ago and after all the formalities had been
completed I did two things. The first was to seek out a woman who would
convincingly feminize me. The second was to write a new will.
I expect most of you, good readers, will find the latter surprising? Let
me explain. Apart from the usual observation of being of sound mind and
how my estate was to be distributed I specifically said I wished to be
buried wearing my pink full length nylon nightdress. Full tarty makeup
and fingernails and toenails painted to match my red lips. I've no idea
if my wishes will be carried out or even if they are legal but think of
the look on the faces of my executors, my sisters-in-law whom I detested,
when they read the will Instructions. I left a note where the nightdress
could be found.
Seeking out the woman was far more problematical. All the Mistresses and
Dommes I contacted wanted to dictate their own terms rather than
accommodate my requirements. Eventually, however, I found Mary, who for a
high price, would dress me as I wanted and provide the other services I
required. As this was going to be a once in a lifetime experience the
cost was not relevant, not that I told Mary that. Certainly she wasn't
cheap.
Mary told me I would have to wait two months before visiting her in the
West End of London. In the meantime I was to email her three pictures of
online crossdressers showing the kind of clothing I wanted to be forced
to wear. I emailed the following pictures:
A transvestite wearing a pink bra and matching full cut nylon panties,
suspender belt and brown nylon stockings.
Another transvestite wearing a pale pink full length lace trimmed nylon
slip etc.
And Paula Satjn wearing a scarlet satin teddy trimmed with frilly black
lace, black stayup stockings, 4" red heels and a matching scruncthie
around her left wrist.
Time passed very slowly but eventually the agreed date arrived. I was
told to be outside Mary's very expensive looking house promptly at 10 in
the morning. It was a Sunday and I decided to travel by train and
underground and with limited cash. Payment was to be made by PayPal which
caused no problems as I only needed my online ID and password to make
payment. I rang the bell using the entry phone. "Hello. Who is it?"
"Nancy." That was the name Mary said I was to be called. I agreed
although I thought it somewhat old fashioned. "Come in," she said as the
buzzer to open the lock clicked. I went in and saw Mary for the first
time. I guessed she was in her late fifties. She had permed hair, modest
makeup and was wearing a frilly pink blouse through which could be seen
the outline of her well filled black bra. She was also wearing a wrap
over knee length skirt.
"Follow me." Mary led me upstairs to a front bedroom with net curtains,
the kind you could not see out of but not see in unless the lights were
on at night. "Strip and put on the items on the bed." With that Mary left
the room. Shaking, I removed all my clothes. I applied the breast forms
first. I eased a little of the adhesive from a tube and smeared it onto
the reverse of the forms including the slight indentation for my nipples
using the applicator supplied. The instructions on the box said allow ten
minutes for the adhesive to set so I lay on the bed on my back until the
beasts were firmly affixed. I did notice before fixing the breasts forms
were marked 44DD. Evidently Mary intended I was to be a buxom woman.
Once the breasts were affixed tightly I stepped into a bright red satin
teddy. It was trimmed with black lace and had no poppers or clips between
the legs. The teddy looked virtually identical to the one Paula Satijn
wore in the picture I sent to Mary. Next I drew a pair of black nylon
stayup stockings up my legs followed by a pair of red 4" heels. Unlike
Paula there was a black leather spiked collar which I secured round my
neck. But there was the red scrunchie which I put on to my left wrist.
Mary seemed to know I had finished putting on all the items on the bed
because she called me into the adjacent bedroom and had me me sit on a
stool in front of a dressing table and mirror. The image in the mirror
looked ridiculous; a man in women's underwear. Mary soon changed my
appearance applying black makeup to my eyebrows and eyes plus thick
bright red lipstick to my lips. Finally, the Paula Satijn image was
completed by Mary affixing a shoulder length black wig complete with a
fringe to my head. Apart from being a little fatter and older I could be
Paula's twin!
Whilst admiring myself in the mirror Mary caught me by surprise. She
pulled my wrists behind my back and cuffed them together with pink
handcuffs. Then she pushed me onto the bed and similarly chained my
ankles together so that I could only hobble on my heels. "What the f...."
Mary put her hand over my mouth. "Shush. Because you look so good I've
decided to provide an additional experience which I know you will like
and at no additional cost to you. I'm going to display you in the Notting
Hill Carnival in about an hour's time."
"No you can't do that. I'll be humiliated and possibly be arrested for
indecency."
"What if you are? Think of the public humiliation of explaining in court
why you were dressed as a whore wearing women's sexy underwear. Just to
make sure you are decent though I'm going to cage your cock. We don't
want a big hard cock sticking out of your pretty sexy teddy do we. That
will be inviting trouble." Mary forced my flaccid cock into a pink
plastic cage the inside of which had sharp pins that were forced into my
cock every time I tried to get hard. They hurt and although I tried not
to get hard it was difficult as Mary showed me pictures of well known
female celebrities being raped. The pictures were photoshopped fakes of
course but they had the desired effect of making me hard only for my cock
to be painfully deflated by the pins.
A rubber cape was put around my shoulders so I looked like an oldish
women and not what I was; an old man feminized in women's underwear. A
chain was attached to the collar and I was led to the underground car
park and forced into the back of a van without windows. It took Mary
around fifteen minutes to reach the edge of the carnival site. I was
pulled out of the van to join six other sissies with their Masters and
Mistresses. Two wore well filled bras, panties, garters and stockings. I
guessed they were both in their late teens. An older one was wearing a
see through nylon nightie complete with matching panties. Like me the
other two s(hemales) had big fake titties. They were dressed as
schoolgirls with tiny pleated skirts that ensued their regulation school
knickers showed as did their well filled bras through their short
blouses. Again like me they all wore wigs, makeup and heels.
Mary and the other Mistresses coupled our collars together and then led
us out to join the long and very boisterous parade. The pavements were
crowded with people and the parade seemed to include virtually every kind
of perversion you could think of. Why some of the perverts, both male and
female, were not arrested escaped me.
As we slowly walked we were jeered, catcalled and subjected to obscene
comments like - I want to fuck you; what about giving me a blowjob, do
you have a cunt, are you a virgin, sissies, whores and fags. Our bums
were pinched, effeminate men kissed me and my caged cock exposed causing
me to fear I would be arrested for obscenity. But worst of all we were
spat upon usually by women who delighted in calling us perverts. One
woman even smeared a thick white fluid into my mouth with one of her
fingers telling me to enjoy her boyfriends cum. Apart from the
humiliation I felt utterly degraded. Our Mistresses and Masters paraded
us in women's underwear for nearly five hours.
Eventually the parade came to an end and I was driven back to Mary's
house exhausted. Mary told me to remove all my clothes, shower and the
put on the nightdress that was on the bed. The shower was good removing
all the saliva and goodness knows what other obnoxious fluids that had
been flung at me during the parade. I took care to avoid the wig getting
wet. I was not sure if the breast forms were OK in water but they seemed
to be. After drying myself in a thick towel I went back to the bedroom.
All my dirty underwear was gone. I slipped the nightdress over my head
and allowed it to fall to my ankles. It was made of soft baby blue nylon
and had a princess neckline and flutter sleeves. I seemed to recall my
gran wearing something similar.
I lay on the bed waiting for Mary to return which she did after about
fifteen minutes. With her were two men both aged around 30. "Meet Chris
and Jamie," said Mary. We all said Hi. "The boys are are to going to
fulfill your other desires." Mary motioned to Chris who immediately
removed all his clothes to reveal a very hard 6" cock. Chris had me lie
on the bed slightly propped up. He then sat on my chest and pulled my
head forward towards his cock. "Most women love to suck their husband's
cock. You're my wife and I want you to suck me." I've always fantasized
about sucking cock and now it's about to be a reality. I opened my mouth
and took Chris's cock into my mouth. I immediately tasted his pre cum and
didn't like the taste. I was now beginning to have second thoughts and
tried to get the cock out of my mouth but Chris wasn't having any of
this. He pulled hard on the back of my head causing his cock to enter my
throat. I immediately started to gag. "Breath through your nose slut." I
did just that and whilst my breathing became a little easier I was still
gagging.
My release from the throat fuck was slow in coming as Chris deliberately
held back his climax so as to prolong my experience. When Chris finally
came I wasn't given any choice about swallowing. His cum slid straight
down my throat into my stomach. Straight after Chris had pulled out of my
throat I wretched. I felt sick but nothing came up. Chris left me on the
bed and after around 15 minutes my stomach settled. I remained on the bed
for another hour still wondering if I was doing the right thing. I still
wanted to experience what a woman experiences from a man so I stayed on
the bed waiting.
I had to wait until Jamie came into the bedroom, again naked. If anything
I would guess his cock was at least 2" longer than Chris' cock; it was
certainly much thicker. Without saying anything Jamie climbed on top of
me lying prone preventing me from moving. He immediately starting kissing
my neck passionately before moving on to my earlobes which he sucked and
bit causing me some pain. Then he kissed me on the lips and his tongue
went down my throat. Although I gagged it was nowhere as severe as when
Chris' Cock was in my throat.
At this stage Jamie decided foreplay was over and he pulled himself up on
me a little. As he did he also pulled my nightdress up parting my legs
and placing them over his shoulders. Then I felt the head of his cock at
the entrance to my bum. My mind was in turmoil. Did I want to be fucked
like a woman. Jamie did not give me any choice. He pushed into me tearing
my sphincter as he did. The pain was excruciating and I tried not to
scream but scream I did. Jamie again kissed me as he forced his cock
further into me. If this was the sort of pain a women suffers when she is
penetrated for the first time I began to regret I ever wanted to have sex
like a woman does. It couldn't be called a violation since I had agreed
to being sodomized; for fuck's sake I was even paying for it to happen.
By now Jamie was fucking me like I was a bitch on heat. I sensed him
cumming on several occasions but each time he stopped leaving his cock in
me as far as it would go. Then he would start fucking me again until some
fifteen minutes later he finally shot his thick hot load as far as he
could inside my rectum and into my bowels. When he pulled out of me the
pain hit me. I was in agony writhing all over the bed. Both blood and cum
seeped out of my ass and on to my nightdress.
"Here. Insert this," said Mary who had entered the room. She handed me a
tampon and I did as she suggested. I inserted the plastic applicator into
my bum, withdrew it leaving the rather large sized tampon in me. The
string dangled from my bum. Seeing my surprise Mary said, "How did you
think you remove it." Although I found it kinky to have a feminine
hygiene product inside me I found it did ease the pain a little but the
pain still persisted and I found sitting very uncomfortable. "Here take
these" Mary said handing me two pills and a glass of water. I quickly
swallowed them, wondering why the were slightly different shapes and
colors.
"Well that's all your desires fulfilled. I hope we lived up to your
expectations. Now I only need payment." But I didn't hear the bit about
payment. I had passed out. I later found out one of the pills was to put
me to sleep. The other was the first of many hormones pills I would be
forced to take.
I don't know how long I was out but it must have been many hours. I
gained consciousness to find myself laying on a surgical bed in what
seemed to be a hospital theater. I was no longer wearing the long nightie
it having been replaced with a fuchsia satin baby doll that had a fringe
around the hem and frilly shoulder straps. But what terrified me was my
wrists were bound behind my head and my torso was bound with leather
straps. My legs had been parted and my ankles were tightly strapped in
slings attached to stirrups, the kind used in the examination of a
woman's pussy. The baby doll was short and ensured my genitalia was fully
exposed. I had also been shaved. It could be this could be Mary's further
idea of humiliation but my predicament suggested she had other, more
sadistic, ideas. I was by now shouting, screaming and squirming in an
effort to get free. But there was no one in the room and nobody heard me.
My mind was all over the place. She can't keep me tied up this way; it's
illegal and I will go to the police when I'm free and Mary will get a
long prison sentence where the prison dykes will see to her pussy. I
guess being left for hours fearing what was going to happen to me was
Mary playing with my mind. Well if she was she was making a very good job
of it.
Eventually a woman, whom I guessed was in her mid fifties, entered the
surgical room accompanied by a much younger woman. They were both wearing
surgical scrubs with the older woman seemingly in charge. I screamed at
them. Let me go. I'll have the police onto you. You'll spend years in
prison." It didn't do me any good. The two ladies just smiled
sadistically and said nothing. "Where's Mary. I want Mary." Knowing it
likely I was going to be castrated I shouted, "I didn't agree to being
turned into being a woman. That wasn't part of our agreement ."
The ladies left me ranting and raging as the younger one took a syringe
and filled it with a pale pink fluid. Then she flicked the end of the
syringe before pumping the contents into the right hand side of my
scrotum. I felt the initial prick and the fluid entering my scrotum and
then nothing. The procedure was repeated with the left side of my
scrotum. Then the ladies left the room.
They came back after fifteen minutes still saying nothing despite my
anguished protestations. Each of the ladies pulled a stirrup up towards
my nightie covered chest at the same time pulling them apart so that my
my genitalia was fully exposed. Then a trolley on which there was many
surgical instruments was wheeled along side. I tried again to get free
but to no avail. The two ladies propped me up. I'm sure they did that to
ensure I had a good view of what they were going to do to me. Then the
younger woman, who looked as if she might be a nurse, took hold of my
scrotum and parted my testicles in the sac. The other woman had picked up
a scalpel and slowly sliced open my right sac revealing one of my balls.
Easing it out of the sac she snipped the cords with a pair of surgical
scissors and the testicle dropped into a metal tray. As it did I fainted
but the nurse soon revived me with smelling salts so as to ensure I
witnessed the second testicle join its twin. The older women then used
the scissors to remove all the Scrotum leaving me smooth under my cock.
After the wounds had been dressed a syringe full of a pink liquid was
injected into my ass and I quickly passed out.
I don't know how long I had been with the fairies but when I came to I
was still wearing the baby doll nightdress. As I gained my senses I
remembered what they did to me. Yet I felt no pain. Then I saw them. I
had breasts, huge breasts trying to escape the nylon of the nightdress.
No longer did have breast forms glued to my chest. I had been given
implants. Judging from the pain I was experiencing my face and vocal
cords had been changed although I found I couldn't speak. I stayed in the
medical room fir the best part of two weeks and although I was allowed up
after a few days I was kept in my nightdress, by then a more modest full
length nylon one.
I was returned to Mary's house very late at night still wearing only my
nightdress. "I expect you want to know why you've been operated on and
why I've had you castrated and large breasts implanted into your chest. I
have an associate who supplies ladies like you are now to rich Arabs and
others who can pay for, erm, sexual favors. Until now all his ladies have
been in their late teens or early twenties. But recently a more niche but
profitable market has emerged. Frank has been asked to supply ladies of a
more mature age. But he didn't have anyone. When you arranged to use my
services both Frank and I thought you might be suitable especially when
you said you wanted sex as a woman. I made you wait two months so as to
check you out and to see if you were able to afford your operations. We
established you could. We have raised just over ?500,000 from selling
your apartment, closing your bank accounts and liquidating your
investments. More than enough to pay the medical expenses and leave me
with a nice tidy profit. I hasten to add you didn't make a PayPal payment
because I didn't want your disappearance to be traced to me. And
disappear you have. There was a very brief reference to you missing in
the local newspaper but nothing since. It's as if you don't exist. Which
is as it should be.
"After you've fully recovered Frank will have you collected and establish
you in a nice apartment with two young 'ladies.' You will have a full
wardrobe of your own clothes appropriate to your age. You will go to see
your 'clients' as a well dressed businesswoman; black business suit,
crisp pink or white blouse, stockings, low heels and appropriate
underwear. As a mature woman your hair will be shortish and permed with
simple makeup again appropriate to you age. You will carry a handbag and
a briefcase the latter to carry whatever items of clothing your client
wishes you to wear. I'm told a schoolgirl uniform, French maid dress and
whore's clothes are very much in demand. You will do any and everything a
client wants including sucking, swallowing and taking cock in you pussy,
all without protection. After all you can't get pregnant can you.
"You life won't be too onerous. Usually only one hotel visit a month
although there maybe more than one client to serve on each visit. Given
the number of five star hotels in London it is unlikely you will visit
the same hotel more than once per year so should not be recognized by
hotel staff.
"To put it crudely you will be a high class prostitute making a lot of
money for your pimp, Frank."
I've been working as a high class whore for nearly five years now. It's
not a bad life most of the time and some clients treat me with great
kindness giving me presents such as perfume, lingerie and nighties.
Others like to inflict pain and have me do humiliating and degrading sex
acts. C'est La Vie!
Ofelia
- 14.10.2021
- 18
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