Road to Ruin
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Jaymie's Road To Ruin free porn video
Jamie's Road to Ruin Part 1
I am about to tell a story that is true. It was my first experience but
it shaped my life forever, not necessarily for the better. As a child,
I used to fantasize about being a woman, but never acted on it.
Anything "gay" freaked me out. In any event, I was very closeted and
repressed. And very awkward around women I was attracted to, but seemed
to be able to make a lot of female "friends."
Years ago when I was in my twenties, a female friend of mine, Karen,
tripped and fell and cut her chin open. One of her girlfriends, Kathy,
loaned me her car to give Karen a ride to the hospital. After taking my
friend Karen to the hospital and getting her stitched up I drove her
home and then drove the car to a bar that had bands that play jazz where
Kathy was, so I can return the car. I had expected Kathy to have the
courtesy to drive me home but she didn't want to do that so I was kind
of stuck.
I decided to hitchhike home. After a brief period of time, a fairly
conservative looking guy picked me up and asked me where I was going. I
gave him directions and off we started. I suppose I should describe
myself. In those days I have very long hair which reached down to the
middle of my back. I was tall and very slender. Jerks used to shout at
me from their car windows "are you a boy or a girl?' In any event, my
rescuer was a fairly large and burly looking guy, but seemed friendly
and we had a pleasant time talking. In those days, I lived in a college
town and hitchhiking was a viable means of transportation and a good way
to meet interesting people. He asked me if I needed to get home right
away and I told him not necessarily. We stopped at another bar he was
familiar with and listened to a live band this guy knew about. It was a
country and western band, which wasn't really my thing, but they sounded
pretty good. It didn't seem like a shitkicker bar so after my initial
anxiety, I was reasonably comfortable. I remember my benefactor kept
saying of the guitar player "he plays a mean guitar doesn't he?" He
said that many times and I think he was pretty drunk by then. We got
back into his car and he then asked if I wanted to stop at his house for
more drinks (he said it was close by and that he would drive me home
after that). I was pretty blasted at that point, having been drinking
all night. I said ok, and we talked some more, then, after a few minutes
as we were driving, he asked me if I had ever sucked a cock. Out of the
blue, as we had not talked about anything sexual all night. I was very
nervous, and felt butterflies in my stomach like never before, but at
the same time, I became pretty excited (and as I said, I was really
drunk).
It had been something but I had fantasized about for a long time but
never had acted on. I have always had fantasies of being a woman, or at
least playing that role with a man. When I looked at porn, it was
always straight porn, but I loved watching cocks and cumshots more than
anything. In any event, I said no I had never sucked a cock. He looked
disappointed, but then I told him that I had fantasized about it for
some time. I then asked him why he asked me that question. He reached
over and took my hand and put it on his crotch. I could feel him getting
hard and I remember thinking that he was pretty big too. I was filled
with anxiety but I got hard too. I was way too anxious to say anything.
With his hand over mine and, therefore, making me do it, I fondled his
cock on the way to his house, but only through his pants.
When we got to his house and went inside, he told me to strip. His
attitude changed quite a bit all of a sudden. He wasn't exactly mean
but suddenly he seemed very demanding. He told me he was divorced, but
had some of his wife's stuff still. I had long hair back in those days.
He left for a minute, came back with a skirt and some lipstick. He
again told me to strip and I was worried for a while that something
really bad was going to happen to me. However, I have always been a
little submissive and I felt like I should obey. I said "Yes Sir" and I
peeled off my clothes and was standing there in front of him naked with
my dick as hard as it has ever been in my life. He told me to put on
the skirt and then he applied the lipstick to me. My heart was
pounding.
At that point he kissed me and stuck his tongue in my mouth. He put his
hands on my shoulders and pushed me down to my knees and told me to suck
his cock. I unzipped his pants, he was partially hard and in order to
please him I licked the shaft of his cock and his balls and then
proceeded to start to suck his cock while my hand cradled his balls.
While I was doing that, he started calling me names, telling me that I
was a whore and a cocksucker. I pulled back a bit, startled that he
was treating me like this, but at the same time was incredibly turned
on. He told me to keep sucking and pushed my head on his shaft. I
started gagging a bit and that seemed to turn him on more. He really
was pretty big and my jaw was getting very tired and I wasn't sure how
much longer I could keep it up, but when I squeezed his balls a bit, he
came in my mouth and all over my face. I was freaked out and spit out
the cum, which dribbled down my chin, but he wouldn't let me get up for
a while and there I was, on my knees with cum dripping down my chin and
lipstick smeared on my face.
He did not do anything to get me off and I asked if he minded if I
jerked off. He told me I could if I ate my own cum, but then didn't
make me do it when I came. I never came so hard in my life and it only
took a few seconds as I was so turned on.
He told me to clean myself off in the bathroom. I went and wiped
everything off of me and came back to the living room topless and still
wearing the skirt. He pulled out the lipstick again and painted my lips
for the second time. He started kissing me again, really hard and then
made me lie down on the floor. He got some Vaseline (which is not a
very good lubricant as I was about to find our the hard way) and smeared
a handful on my ass. He then mounted me missionary style and I wrapped
my legs around him as he entered me. You read all of these stories that
say that anal sex hurts at first and then the fuckee loosens up and it
feels ever so good? I am sorry to say that it hurt a lot at first and
just got worse. I had a drunken guy fucking the hell out of me and he
would not stop until he came. I think that it took a very long time
both because he was drunk and it was his second shot of the evening. I
wasn't sure what to do, and I was in pain, so I reached around and put
my finger in his ass and at the same time, started sucking on his
nipples. That seemed to do the trick as he started grunting and I could
feel him shaking all over as he bred me.
After that, we both kind of passed out. I woke up a few hours later. He
was still lights out. I had sobered up a bit and the reality of what I
was doing hit me and I was in a panic. I tip toed to the bathroom,
wiped off the rest of the lipstick, put on my clothes and left. As I
sobered up, I was pretty freaked out. It had been my first experience
with a man and as a kid growing up, the worst insult anybody could throw
at you was fag. And here I was, completely emasculated, but really
turned on by it. I was not sure of what that meant, or the consequences
of my actions.
I had blood in the toilet the next day when I went to the bathroom, but
I was scared to go to the hospital. It took about four days for my butt
to stop hurting. I masturbated a couple of times every night reliving
the memory of that evening. I did not know my new friend's phone number
and wasn't sure if I wanted to, or should, ever try to contact him
again. I was not sure what my reception would be. At the same time, I
was fascinated with the role I had played.
I went back and forth about the experience, but what it did for me was
to start me on the road to my slow transformation. I shaved all my body
hair off, including my armpits and legs. I mail ordered some panties
and got some nail polish from the store and started wearing panties
under my regular clothing and also started painting my toenails. It
turned me on to think about having that secret as I went about my
regular business. I also bought a bra and some breast forms and would
put them on when I was alone. But I was scared to venture out with
those on.
Little did I know what was in store for me the next time I took a walk
on the wild side. To be continued.
Becky
- 13.03.2021
- 14
- 0
