Long Road to Ruin Ch 01
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Jaymie's Road To Ruin Part 2 free porn video
PART 2 - Jaymie's Road to Ruin
First Inter-Racial Experience
Dear readers,
Thank you for your kind comments. This is part two of my story. Since
this is a true story it may not be as adventurous for some as they would
like, however, my development began at a slow pace and during the
process I was full of self-doubt.
Since the time of my first experience, I spent a bit of time troubled by
what happened. On the one hand, it turned me on like I had never
expected. On the other hand, I was experiencing a lot of conflict with
my sexuality. I will say in those days, that I would have more than a
bit of anxiety thinking that I was gay. I was more than a bit ignorant
of the transgender scene, which was non-existent in my home town as far
as I knew, and the internet was not as sophisticated as it is now. It
may sound odd, or contradictory, but I guess I convinced myself that if
I was a woman, it would not be so wrong, but I was a man. In any event,
I was pretty sure that I had taken my walk on the wild side and spent
some time overcompensating for it. A nice fantasy to use, but not
something I would repeat. I would walk down the street desperately
trying to make sure that I was attracted to every woman that went by.
Unfortunately, my period of real chastity didn't last all that long.
After a few weeks of trying to be very macho, I reverted back to being
more feminine, at least in private. In short order, I became addicted
to my closet dressing and wore panties underneath my regular clothes
almost every day. I also painted my toenails and went about my business
with my covered up toes screaming alternative lifestyle. In addition
to the feminine clothes that I had purchased, I went to the local
"marital aids" shop and purchased a number of toys. I bought a butt
plug and a couple of dildos. My fantasy life for masturbating mainly
consisted of me dressing up fully, putting on makeup and getting one of
my dildos and putting it in my mouth and pretending that I was sucking
cock, while at the same time, stretching my ass with a fairly good sixed
butt plug. I really liked wearing bright red lipstick for some reason.
I would also practice sucking cock on the dildo and got my jaw muscles
in better shape than they were before.
I fantasized about men cumming in my mouth. I liked to watch bukakke
videos. I would tell myself that I would swallow my own cum to practice
doing it for the next man I might pleasure. Of course, as soon as I had
an orgasm, I would be disgusted with myself and take off my clothes,
wipe the cum off my hand and not swallow anything. Fantasy and reality
do not always mix. I did have a few times where I would lay on my back
and bring my legs over my head so that my cock was in front of my face.
If I really forced it, I could just get the head of my cock in my mouth.
I started getting some neck pain from that and stopped that practice
pretty quick.
In any event, as was my practice, I had driven to school for class and
was driving home to the West side of town. From the outside, I looked
like a typical college student with boots, bluejeans and a flannel
shirt. However underneath I had painted my toenails red, had red thigh
highs on and red panties on underneath everything. I picked up a hitch-
hiker who was going about half way down Main Street. He said his name
was Frank. Frank was a tall very built, black man in his early 20's.
We started talking about music and found we had a lot in common. We
both liked the same kind of music and he said that he invited me back to
his place. He seemed like a nice guy and I had nothing to do, so I
agreed to take him home.
It was snowy out, so I took my boots off when we got to his place. We
spent what seemed like a few hours talking and we were drinking a fair
amount and I was pretty buzzed. He was playing a bunch of records by
artists that I was not familiar with and I think he enjoyed turning me
on to new music. At some point, his phone rang and he picked it up.
The conversation sounded like he was talking to a friend. All of a
sudden, he had a odd, kind of puzzled look on his face and it looked
like he was staring at my feet. I looked down and to my dismay, saw
that there was a hole at my big toe in my right sock. My bright red
toenail and the red stockings were poking out, and apparently, giving
away my secret. I could tell from the conversation that his friend
wanted to come over right away, but Frank was telling him to come by in
a few hours. I could make out what sounded like the question being
asked on the other side of the line: "What, do you have a girl over?"
and definitely heard Frank say "you might say something like that."
Frank hung up and gave me a funny look. I kind of raised my arms and
shrugged. Frank said "is there something you want to tell me?" He took
a step towards me, but still was about 3 feet away from the couch I was
sitting on. I wasn't sure what to say, and maybe Frank wasn't either,
but I said "I have a bit of a secret - here let me show you. " I stood
up and pulled off my jeans, which exposed my thigh highs, panties and
toenails. He kind of stared at me for short while, and I wasn't sure
how he would react, but in a few seconds, it was clear what he was going
to do. He simply unbuckled his belt and zipped his fly down and let
his pants drop to his ankles and then looked at me with an Ok, what are
you going to do now look? I could have said something, or jumped up and
left, but instead, l found myself looking at the most perfect cock I had
ever seen in my life. I was immobilized for a few seconds. Flaccid, his
dick was bigger than mine when it was fully erect. In any event, I
found myself kneeling in front of him with my mouth open. I put my lips
on the head of his cock and started sucking, feeling him getting bigger
and bigger. Frank's cock was a "shower" because while it did get bigger
when he was erect, it didn't increase in size proportionately the way
mine does. That was a good thing, otherwise, I could not have taken it
in my mouth. In any event, Frank had to be a good 8 or 9 inches when
hard. I licked his shaft and sucked on his balls for a while and then
got to work on the head of his shaft. I had one hand on his balls and
another on his shaft and was sucking on the head of his cock for all I
was worth. I could feel him start to shake and in a few seconds after
that, felt his cum hitting my mouth. I swallowed and swallowed until he
was done and then sat back up on the couch. The whole event couldn't
have taken more than 5 minutes. I wasn't sure what was going to happen
next. Frank told me that I was the first man he had been with and I
told him he was the second. He said that his friends were coming over
soon and I should leave, but he said I should call him later in the
week. He gave me his phone number and I left his apartment with the
taste of cum in my mouth and thought to myself that I was pretty sure I
was about to begin another bout of anxiety and self doubt. And indeed I
did. While I went home and masturbated to the memory of what I had just
done, I am sad to say that I never called Frank and never got together
with him again. Looking back on it I got the sense that might've been
the most normal relationship I might've had in all this. But at the
same time, what was a pleasant afternoon ended with a blow and go (and
with no though of my pleasure at the time). In any event, this second
step pretty much made it impossible to pretend that my feminization was
something I could stop at any time. Also, it worried me that my
immediate reaction to seeing another man's cock was to drop to my knees
and start sucking. And why was I only concerned about pleasing him and
not myself at the time? As future episodes will reveal, that reaction
would dictate the path my life was about to take.
Libbie
- 01.11.2022
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