Long Road to Ruin Ch 01
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Jaymie's Road To Ruin Part 5 free porn video
Jamie's Road to Ruin Part 5
At this point my life I was pretty much torn between my desires, almost
compulsion, to cross dress and have sex with men and clinging to whatever
semblance of what was left of my former normal life. I am a bit of a
hypochondriac, and was worried about disease. I had already learned my
lesson regarding that the hard way. In any event I was hanging out at my
apartment with my roommates and one of them came in with the campus
newspaper and was laughing about an ad in the personal section. The ad
said "free lodging and a Mustang convertible to use during the week in
exchange for pleasurable weekends." It went on to say that the person
that placed the ad lived in New York City but traveled to my town
frequently for business. While my roommates were making fun of this, it
sounded like a pretty interesting idea for me.
In any event I called the number that was in the ad and spoke to a
pleasant sounding man. He said his name was Malcolm and he was a doctor,
and that he managed emergency rooms and hospitals and as part of his
business, he came to my town pretty much every weekend. We arranged a
time for him to "interview" me and I thought about how I would prepare.
I did not ask him over the phone if he was looking for a masculine
boyfriend but figured there would be plenty of those but I might stand
out if I should come fully dressed.
In any event, I want the whole 9 yards. I put on panties, thigh highs,
stiletto heels, very short miniskirt, and my biggest breast forms, very
tight top and with the full make up including eyeshadow, false eyelashes
and deep red lipstick. To top it off, I put on a beautiful blond wig. I
really looked pretty hot. The big question of course was whether or not
the good doctor wanted a submissive girl or a masculine boy.
I snuck out of my apartment and drove over to the meeting place. I rang
the doorbell and my heart was pounding. The man that opened the door
looked to be in his early 40s, he was tall maybe 6'3" and had very
chiseled good looks. He was clearly surprised to see me dressed up as I
was, but after the first look of surprise, he got a really big smile on
his face and invited me in.
He asked me if I wanted anything to drink and I told him that a glass of
wine would be very nice. He brought me glass of Cabernet and we chatted
for a few minutes about his business and his marital status, which was
single and how his interviewing process was going. He said he talked to
three other men but certainly nobody like me, and the way he said it he
seemed very impressed with me. I finished my wine and he asked me if I
wanted another glass and I said not at the moment. He took my glass back
to the kitchen and came back out to his living room. He sat down in a
chair and told me to sit wherever I like. I thought about it for a few
seconds and then decided to play this up for all I was worth. Instead of
sitting in a chair I walked over to where he was a knelt down at his
feet. If he was looking for a submissive slut, I was the girl for him.
If he wasn't, it would not have worked out anyway.
So I asked him, "Sir what do you expect from a person you wish to share
house with?" Unfortunately, he answered with a question. "What are you
willing to give up?" I told him everything. He stood up from a chair
and I reached up and unzipped his pants. I pulled his rather large cock
out, and kissed it with my red lipsticked lips. He got hard immediately
and I toyed with his penis for a long time. I sucked on his balls and he
seemed to enjoy that as well. I then started sucking his cock in
earnest, and it did not take very long until I realized he was about to
come. I kept going and felt his cum hit the back of my throat. I just
swallowed all of it and kept sucking until he pushed my head away.
He seemed very pleased. He pulled me up to a standing position and kissed
me very hard. He then took my hand and lead me into the bedroom. He had
me remove my panties and skirt and lie facedown on the bed. I felt him
lube my ass up and then moments later I felt him enter me. This second
time around it took quite a bit longer and since I was facedown, I
couldn't use any of my usual tricks to get him to come quicker. But I
was pretty happy and I was pretty turned on by how things were going.
It may have been a casting couch kind of interview, but I got the job.
We made arrangements for me to move in and in a week I had my very own
sugar daddy. I was to keep the house clean while he was gone and when he
showed up on Friday afternoons I was to greet him at the door on my
knees. I was falling in love but it did seem pretty clear to me that, to
him, it was just an arrangement.
One night, after we had been doing this for about a month, we were
talking for a bit. Malcolm asked me how much I wanted to be a woman. I
told him as much as possible. He asked if I would be interested in
taking hormones and perhaps getting breast implants. I told him I was
very much interested, especially in getting breast implants. All through
this I dreamed about having large breasts. He said that since he was a
doctor, prescribing the hormones would be easy and he would do it right
away. He said he just wanted to read up to see what the doses would be
correct. He told me that he had a friend that was a plastic surgeon that
we might talk to about getting implants.
Needless to say, I started on the hormone regimen right away. I felt
kind of odd physically at first and I didn't see much difference other
than my nipple seem to be very sensitive. However, after about three
months I could detect changes in my physique. All this time my
benefactor was buying me new dresses and shoes to wear. He also bought a
variety of restraints and toys for me to use. He bought a stainless
steel collar for me that looked kind of like jewelry, but it was pretty
obvious that it was a slave collar. When he was home, I would frequently
have to wear handcuffs and a ball gag in my mouth. I would make him
dinner and kneel at his feet waiting for him to finish. Clearly he
wanted me to be a serving wench.
After a while, he took more and more control. He liked to control my
bathroom habits too. He would lock my penis in a chastity cage and also
make me wear a butt plug that was locked in place. In theory, I was only
supposed to go to the bathroom when he said it was allowable. Of course,
the bathroom control was only when he was around, however the chastity
cage was locked in place constantly. There were times when I couldn't
control myself and ended up soiling myself. When that happened he would
make me sit on my own filth and suck his cock first before I could go to
the bathroom and clean up.
One day he told me to get in the car and said that we're going to go meet
his friend the plastic surgeon. When we got there, it was clearly not
the surgeon's regular office hours. Malcolm told me to wait in the
waiting room and he went to talk to his friend. In a few minutes, he
came out and motioned for me to come in. I said hello to the other
doctor and then Malcolm told me to take off my clothes. I was little
surprised with this but at this point I was pretty used to doing what I
was told and it was a doctor's office after all. I got a pretty thorough
examination and there was a lot of discussion about what medical
procedures could be done. I didn't really participate very much in the
discussion. The one thing I did say was when there was some talk about
size of implants and I said I wanted very big ones. However as soon as I
said that, it was made clear to me that I was to speak only when spoken
to. Malcomb and his friend discussed breast implants, butt implants,
laser hair removal, liposuction, and lip injections.
To my great surprise, at one point Malcolm told me it was time to take
care of his friend. I started to ask what he meant, but in a few seconds
it became pretty clear as his friend opened his zipper and pulled his
cock out. Malcomb told me to start sucking. I was just stunned by this
because up till now, it had appeared as if Malcolm only wanted me all to
himself. He got a little cross at my delay, and said just do it. So,
dutiful slut that I am, I took care of the new doctor.
After we left the doctors office, Malcolm explained to me that the
various surgeries that he was talking about performing were very
expensive. Instead of Malcolm paying the surgeon, the surgeon was going
to take it out in trade with me. Malcolm would have me for the weekends,
and the surgeon would have me the rest of the week. This made me more
than a little nervous, as I was not crazy about being whored out for
medical procedures, but at the same time I had bought into my
transformation at this point. In any event, I could see that Malcolm was
conflicted by this and I leaned over and sucked his cock on the way home
to console him.
The first operation I got were the breast implants. They were not quite
as big as I would've liked but I was told anything bigger would've looked
like cantaloupes glued to my chest since I didn't have much breast tissue
to begin with. Still, I ended up with a nice large C cup. I spent quite
a bit of time with laser hair removal. Then came the lip injections
which I thought really altered my features quite a bit. The two doctors
kept remarking about my cock sucker lips, but it was the one thing they
did to me I thought made me look a little odd and that looked like I had
had plastic surgery. At some point, I realized I could never go home to
my parents again..
The one real mistake I made one was when I signed a release form for an
orchiectomy. I was signing release forms right and left and at one point
we were talking about shaving my Adam's apple and that's what I thought
it was for. Imagine my surprise when I woke up with no testicles. I was
somewhat upset but at the same time realize that this whole process has
been going on without a whole lot of input from me and that I was going
along with everything so why not this too? Malcolm said that they did it
so the hormones would work better. That did indeed seem to be the case.
I never got the butt implants, however they did do liposuction on my
stomach and injected the fat into my butt, which rounded it out nicely.
I got to a point where, if I went out, I couldn't walk down the street
without men whistling or making comments. Except for my limp penis and
the fact I had no vagina I was pretty much a girl at this point.
My life was divided between the two doctors, although they each treated
me quite a bit differently. Malcolm was becoming a little meaner and a
little rougher. I suspected that he was taking out his anger at having
to share me with the other doctor on me. He started taking to slapping
my face during sex which I didn't like all. I was completely on board
with getting spanked but slapping in the face was bad.
The other doctor like to have parties. He would invite friends over and
have me serve them. At first I was mostly window dressing. The one night
when I asked one of his guests what he wanted, he responded with beer and
a blowjob. I gave him a beer and walked away and the doctor accosted me
and said why aren't you giving him the blowjob he asked for? I started
to protest but he said just go and do it. Next thing I know, I'm giving
blowjobs to everybody in the room and then a short time after that I'm
face down on the bed pulling a train.
The doctor said I was to not to tell Malcomb any of this. And this
started a period of my life where for a few months, at least once a week,
my doctor friend would have a party with anywhere from 5 to 10 people
where I was expected to service anyone that wanted it.
Unfortunately between the hormones and the castration, my own sex drive
had very much diminished to nothing. Where in the early stages of this
transformation, this sort of thing would have turned me on like nobody's
business, it just didn't do anything for me at all. I could not get an
erection anymore and no amount of tugging would give me an orgasm. I had
had some girlfriends in the past that told me they were frigid and I
guess I could sense what they must have been going through.
It had now been almost two years. I could sense that things were going
wrong in many ways. Malcomb was getting meaner and more distant and the
good doctor was getting more and more perverted. Maybe I just needed a
rest, I don't know. I had no money, and had dropped out of school. I
hadn't seen my parents in all this time and figured they would probably
have a heart attack if they saw me. I needed a plan.
Malcomb was only coming to town two weekends a month at this point. So I
had a couple of weekends to myself. I started placing ads in the local
classifieds whoring myself out. I found that the going rate was $200 per
hour. I advertised a girlfriend experience, though business was not too
brisk. It seems that most men looking for a walk on the wild side want
the transsexual to top them, or at least be "fully functional." That
wasn't me. But for those generous men that wanted a submissive
girlfriend that would do almost anything, I fit the bill nicely and I
found I could make anywhere from $600 to $1200 on a weekend. At one
point, I found a fellow that wanted me to spend the night and was willing
to pay nicely for that. I managed to squirrel away some get out of town
money pretty quickly.
I bided my time. I figured the best time to leave was on one of those
weekends when Malcolm was not in town. I figured I could get a head
start and get out of town before anyone noticed. I am not sure why I was
acting like I was in prison. I pretty much had free reign when either of
the doctors were working. But I just didn't know how they would take it
and didn't want the confrontation. I had long ago found the key to the
chastity cage and at that point it was more self imposed than anything.
In any event, the surgeon dropped me off at the house and I wrote a note
to Malcolm saying thanks and that I was heading to Florida (I was really
going to California) and goodbye. I paid cash for a bus ticket to Los
Angeles and got on the bus. And off I went on my next adventure.
Angelica
- 17.12.2020
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