Long Road to Ruin Ch 01
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Jaymie's Road To Ruin Part 4 free porn video
PART 4 - MY MOM'S DATE
This chapter is a bit creepy, but it is part of my story. I had a very
weird relationship with my mother. She was an alcoholic and very
flighty. In many ways, I feel that she unmanned me growing up. In any
event, I had not seen her for a while, and she called me up and told me
that she wanted to come by and take me to the movies. When she got to
my apartment she then said that she had been dating some guy for a while
and wanted him to come along as well and asked if I would mind. I said
no, I wouldn't mind (like I had a choice).
On the way over to the fellow's place, (his name was Bob) mom was
complaining that she wondered if the guy was gay. She said usually when
she went out with a man, he would be all over her but this guy had never
made a move on her or had even tried to kiss her. (Mom had a habit of
sharing her sex life with me-never mind that I had told her that such
talk makes me very uncomfortable). She said Bob was a photographer and
indeed when we go to his house he did have a very elaborate photo studio
in one of his rooms with a backdrop and lights.
We made some small talk and then went to the movies. Mom and Bob talked
through the entire film, with people in the seats around us telling them
to be quiet. Mom always did things that embarrassed me and never seemed
to care. After the movie, we went back to Bob's house to have some
drinks. Bob made us all martinis and the conversation livened up quite
a bit. It was the first time I had ever had a martini (or three) and I
was pretty buzzed.
We spent a little time talking and Bob seem to be a bit taken with me,
or so I thought. He spent most of the time talking to me and ignoring
my mother. He asked a lot of questions about my long hair and asked if
men confused me for a girl. My mom did not like that line of
questioning and it made me a little uncomfortable too, since she was
there. I am not sure how I would have felt about it if she wasn't with
me.
At one point, as Bob was showing us around the house, we were standing
in Bob's living room. My mom asked to use the bathroom, which was down
a long hall. As she was walking down the hall, Bob stood to my side and
sort of caressed my ass with the palm of his hand and told me that I was
welcome to come by anytime. Oddly, I did not pull away at this touch.
I started getting hard and took my hand to adjust my cock to be more
comfortable in my jeans. Bob noticed immediately and ran his hand up
underneath my ass and cupped my balls. I heard the toilet flush and
found a couch to sit on so that mom would not come out of the bathroom
and see me with a hard-on. Bob was grinning like the cat that ate the
canary and I knew I was in trouble, again.
When it was time to leave, Bob told me in front of my mother that I was
welcome to come by anytime. He said if I want to use his place to study
I could do that. When mom went to use the bathroom again before we
left, the conversation changed a bit. Bob said that he would be
interested in photographing me with some other young men he knew. He
mentioned the word "masculine" when describing them. The whole time he
was talking, he caressed my ass. I felt like he knew my secret. I was
a bit nervous since I expected my mother to come out of the bathroom at
every second. What a weird situation to be in. He slipped a business
card into my hand and said, "Call me." Moments later, mom got out of
the bathroom and off we went
I have to confess that I was pretty curious about all this, although at
the same time, to be hanging out at this guys house would be bad news if
it got back to my mother. Also, Bob was considerably older than I was,
by at least 25 years. Despite any misgivings, I waited a couple of days
and gave him a call. He seemed very happy to hear from me and asked me
to come over that afternoon. As usual, I had my red panties and
stockings on underneath my clothes. I went to his house and he greeted
me very warmly with a big smile and invited me in. We talked for what
seemed a long time and after a number of drinks and after swearing him
to secrecy I told him my life story. He acted like he was very
interested in hearing my story and kept urging me to continue telling it
to him, though I was not sure at the time what his goal was.
At some point he put his hand on my thigh and I was pretty sure where
his hand was going to go next. Next thing, I knew he had his hand on my
cock and he was kneeling in front of me. He unzipped my pants, pushed
my panties aside and pulled my cock out and started sucking my cock. I
came in seconds. Moments later, I stood up and took my outer clothes
off. Exposing my panties and stockings. I undid his belt, unbuttoned
his pants, unzipped his fly and attacked his cock for all I was worth.
He too came in just a very short while and I swallowed his cum. This
act was getting easier and easier for me.
Since I had already told him my story about how I like to dress in girls
clothing and he seemed kind of turned on by it, I didn't feel too much
anxiety at the time. He asked me if I wanted to come over another time
and have him take pictures of me dressed but that made me very nervous
because I didn't want pictures like that of me circulating. After all,
it was possible that my mother would come by and see them and that would
really be a problem for me.
Bob asked me if I would come by on the weekend. He told me that he had a
couple of other young "masculine" male friends that were coming over and
he would like us all to get together. I told him I would come by. He
asked if I would come by and get dressed and I said that I would think
about it. He said that I could come by dressed normally and get dressed
as a girl at his place. He also said that if I was a girl, that I might
have a very nice time with his two other young friends.
I did go to his house that Saturday afternoon and spent a fair amount of
time in his bathroom getting ready. As I have told you, I had really
long hair in those days. I had a bra and breast forms, panties, thigh
highs, short miniskirt, spike heels and a nice blouse that I put on. I
spent a lot of time on my makeup. I put on false eyelashes and
foundation and eyeliner and bright red lipstick. When I came out of the
bathroom, I felt I look pretty hot. Bob's two friends came over and
they looked like they were about 18 or 19 years old thin and built.
They had apparently been over to Bob's before and were quite familiar
with the place. In any event, they quickly took off their clothes and
were standing naked in front of me. Bob took charge and told me that
these two boys were my dates for the day and that I should take care of
them.
Somehow I felt like I had no will of my own and I took a few steps
towards these two guys I had never seen before in my life. Next thing I
knew I was on my knees sucking the cock of the first of the two to get a
hard on. There was a mattress on the floor and he pulled me onto it. So
he was lying on his back and I was sucking his cock. The other boy got
behind me and pulled my panties down and I could feel his cock probing
my ass. Next thing I knew I had one cock in my mouth and one in my ass
and both boys were pumping me for all they were worth. Neither of the
two was very well endowed so I had an easy time on both fronts.
Apparently, while all this was going on Bob had a video camera going.
So I was being recorded for posterity without my knowing. The two boys
took turns with me and I was their receptacle for what seemed like a
couple of hours. When they were done, we all got dressed and the two
boys left and I got ready to say goodbye to Bob. He told me about the
video and I got pretty upset since I told him I didn't want him to take
pictures. He showed me the video and said that he was only going to use
it to jerk off, but then he said that he wanted me to come to his
"parties" again. He told me that if I didn't cooperate that he would
show the video to my mother.
I didn't know if you would or not but I felt like he was blackmailing me
into being a sex slave for his videos. Also, I wanted to know what he
was doing with the videos. I was worried that he might be putting them
on the Internet. However he had me in the worst possible position and I
felt like I was stuck doing whatever he wanted. Bob told me to show up
the next Saturday and to come fully dressed.
I did show up the next week and when I got there, five naked college
boys were standing around in Bob's house. I went into the bathroom to
put on my make up and when I got out Bob said to all of us, "Well, you
know what to do." One of the older boys walked up to me and kissed me.
I kind of liked that as it made me feel little less used than what had
happened the week before. But that was short lived.
Next thing I knew I was on my knees with cocks surrounding me. I went
from cock to cock keep it all five hard for a while. I then started to
concentrate on the boy with the biggest cock, sucking and squeezing his
balls. Pretty soon I could feel him tense up. He puled pulled his cock
out of my mouth and squirted his cum on my face and in my hair. With
his cum dripping down my face and onto my blouse, I then turned to the
next hard cock I could see and concentrated on it. In about two
minutes, this boy blasted my face with his cum as well. A that instant
a third guy who had been jerking off said "look at me" and sprayed me
down with his cum.
The fourth boy told me to lie down on the mattress and spread my legs
and pulled off my panties. He lubed me up and entered my ass and I
wrapped my legs around him. As soon as he came in my ass, the fifth
boy took his place and pumped me for all he was worth. Bob seem very
happy with all this and I noticed that he had a camera in his hands.
After all the sex was done, the boys got dressed and left. I was pretty
spent and in the need of a little time to recover. However while I was
lying on the mattress, Bob came over and unzipped his pants and motioned
me over to his cock. I had cum dripping off my face and my hair and all
my clothes and also dripping out of my ass. My jaw was tired but I
opened my mouth and started sucking on the head of his cock. I guess
the show had really turned him on because it only took him about half a
minute to ejaculate. When it was done I got up and went to the bathroom
and cleaned up a bit. As I was leaving he told me to be sure to come by
the next weekend for "more fun." I left his house wondering what I had
gotten myself into.
Unfortunately a few days after all this, I started to get a sore throat.
I had trouble swallowing and there were white spots on my throat. When
I went to the doctor I was diagnosed with oral gonorrhea. I was pretty
freaked out. I called Bob yelling. I told him I didn't care what he did
but I wasn't coming back. Oddly enough he did not give me a hard time.
I never did see any pictures of me having sex on the internet, but I am
not sure that I would know where too look. One comforting thought that
I had was that if the boys gave me VD, I probably transmitted it to Bob
at the end of the day. I took my tetracycline and put away my clothes
for a while. I later was told that my HIV test was negative, so I had a
bit of relief, but this was a real wake up call about safe sex and what
I was doing. But the memory of the group sex really turned me on and I
think that I was hooked on the adrenaline rush of it all. Talk about
conflicted. But no death wish here, so I vowed to be more careful in
the future.
Sherry
- 08.02.2023
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