The Sitter
- 3 years ago
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Cat Sitter free porn video
The following story is the 100% true account of my first sexual
encounter.......
Growing up in South Florida in the 1980's was really an amazing
experience. Watching what was considered by many to be a sleepy
retirement town metamorphosis into a chic metropolitan international city
was quite a sight to behold. While there were many changes occurring in
the world around me there were equally as many changes occurring within
me.
I was fifteen years old in 1985 and attending an educational excellence
magnet school for gifted children. At the time I hated going to "Nerd
High" because I did not get to spend all day with my friend's from the
neighborhood. It also was hard because of the volume of homework I
usually was not walking out my door to hang out until about 5:00 PM or
so. In retrospect it was a good thing because that experience provided
me an edge that I utilized to my full advantage to get into a great
college and then springboard into a better law school.
My neighborhood consisted of a collection of townhomes derived from the
Latin word "new" and is usually associated with the birth of a star in
the heavens. The homes were of modest construction and the occupants
were equally modest. Mostly working class people, recent transplants
from colder climates and the retired. My family wound up moving in after
my parent's divorce and my mother's decision to attend law school at the
University of Miami.
My mother's decision to attend law school put an enormous amount of
pressure on me. Between the long hours of her studying and the complete
lack of money to pay for babysitters, I became the de facto parent to my
younger brother. That time without parental supervision also provided me
an opportunity to explore the contents of my mother's bedroom, more
specifically her lingerie drawer. My mother was an attractive woman but,
she was not sexual type woman either. She was very no-nonsense and her
taste in clothing reflected that part of her personality. It was in
those quiet times that I discovered that I enjoyed the feeling of silky
panties covering my youthful ass. That sensation would cause my penis to
swell with excitement and I would often take my afternoon "study breaks"
masturbating in a pair of panties.
Across the street from us lived my friend, Richard, who was also being
raised by a single mom. His mother, Patricia, was the polar opposite of
my mother. She worked as a secretary of some type after getting divorced
from Richard's father and moving him to Florida for a new opportunity at
life. Patricia was sexy as hell and always had a steady stream of
boyfriends. I remember how cool she seemed with her white Trans-Am
Firebird with the T-tops off. She was also incredibly sexy too. Long
brown hair and very big natural breast in a time that you could not run
out to purchase if you did not get them "from the factory".
During the summertime, my friend would go visit his father in god only
knows what state. One evening Patricia came to the house and asked my
mother if I would be able to take care of her pet cat while she went on
vacation with the cock de jour. She said that she would pay me for doing
it. I believe the sum for seven days of making sure that the cat was fed
and litter changed was the sum of fifty dollars and I eagerly accepted.
Little did she know I would have done it for free because I had much more
nefarious plans on gaining access to her bedroom. I had seen a pair of
her panties in their dirty clothes basket once and I was completely
amazed. Unlike the primary colors of my mother's collection which
included white, black and tan, Patricia's were hot pink. Even sexier was
that they were not briefs at all. These were string bikini and they
looked like they barely covered anything at all.
The first day of my duties arrived and I let myself into the townhouse.
I immediately did what I was there to do by giving the cat a few fresh
scoops of dry food and changing the water. Then, I walked around the
residence and ensured I was alone.
The master bedroom was located on the second floor and comprised nearly
half of the available floor space. The room still smelled like Patricia,
a mixture of perfume and smoke. I remember the wicker headboard on the
bed and the mirrored closet bi-fold doors, which was popular at the time.
I walked to the dresser and began to open all of the drawers. I was very
lucky for two reasons. First off, there were panties, bras and lingerie
of every imaginable color and texture. The bigger reason was apparently
she did not believe in neatly folding her intimate apparel. That meant I
did not have to memorize how things were folded or where there place in
the drawer was. I had full run of the contents of that drawer for the
next seven days and I intended to use it to my advantage.
After completely stripping down to nothing, I began to plumage through
the panty drawer until I located what were on my mind....those pink
string panties. I stepped into them and slid the silky material up over
my ass and around my already hard cock. I felt electricity shooting off
of my body and waves of pleasure coming over me. In the bra drawer next
to the panty drawer, I located a pink lacy bra. Having plenty of
experience with them already I placed my arms through the straps and
fastened it. Inside another drawer I found black panty hose and put them
on. I looked at myself in the mirror as I walked to the bed and lay
down. On my back stroking my hard cock, I thought about what sort of
things Patricia was doing with the men in her life. After several
minutes of stroking my cock I exploded hot white cum and put the clothing
back where I found them.
Over the next few days, I began to check on the cat in both the morning
and in the evening. Of course, each time I went I would spend about an
hour dressing in her clothes and masturbating furiously.
On the third day, I walked into the house for the morning feeding and my
heart nearly dropped. Patricia's older brother, Bob, was sitting on the
couch watching television. Uncle Bob, as I knew him, was a nice enough
of a guy. He usually would crash at my friend's house whenever he and
his girlfriend were on the outs. It occurred often enough that he had a
twin size bed and some clothes in the spare bedroom. I think the only
way I could describe him kind of bland. The celebrity he most resembled
was either Stephen King or Reverend Jim Jones, only without the charisma.
I stammered to explain why I was in the house only to feed the cat and he
acknowledged that I was not a burglar since I had used a key.
Furthermore, Bob told me that he knew someone had to be feeding the cat
in his sister's absence. I went about my duties and quickly left.
I returned later in the day to feed the cat and to hopefully find the
residence empty. As soon as I entered the courtyard I knew that I was
out of luck because Bob's Honda Goldwing motorcycle was parked there.
Upon entering the townhouse I called out for Bob and he acknowledged my
presence. While getting the cat food from the pantry, Bob came
downstairs and sat down on the couch. Upon finishing the task at hand, I
started to leave when Bob called for me to come into the living room and
sit down. Sitting on the far end of the sectional couch and Bob drinking
a beer while watching television, we engaged in small talk. Without the
slightest warning of what was about to come, Bob asked me "Have you been
in my sister's room since she left??" My heart sunk and all of the blood
drained from my face. I was so stunned that I did not even have the
capability to deny it. My lack of response and the look on my face must
have been absolute indications of my guilty acts. Bob told me that he
had stopped by to use the bathroom the day after his sister had left and
noticed that the closet doors were closed. When he returned this morning
he noticed that the closet doors had been opened. Thinking fast I said
something about not being able to locate the cat and had gone into the
closet looking for her. Bob just smiled and asked me if I thought the
cat had been hiding in his sister's underwear drawer as well because that
appeared to have been disturbed as well. With the sound of my pounding
out of my chest Bob told me to relax. He told me to be honest with him
and everything would be alright and that he would never tell anyone my
secret. It was at that time that I had admitted that yes I had been
helping myself to his sister's wardrobe.
Bob asked me if I had ever seen a porno and I said only on Cinemax late
at night. Bob just laughed and told me that was not a real porno. He
stood up and pushed play on the VHS. Next thing I know I am watching my
very first, very bad 80's porn complete with bad acting and cheesy music.
But, I overcame all of those obstacles and still managed to get a raging
erection. On the other end of the couch I could see that Bob was equally
being affected by the images on the screen.
Bob stood up and went into the kitchen. Upon returning to the room, Bob
had another beer for himself and had poured me a glass of red wine. Bob
gave me the glass of wine and told me that I should go upstairs and do
what I had really come over to do.
I knew the path to the room and went up to do what I knew I wanted to do.
By this time I had conducted a full accounting of where everything was.
I put on a black lace body suit with a black lace garter belt with thigh
high stockings. I went to the closet and put on the only pair of heels I
really fit into. They were three inch heels with an elastic cloth
material over the foot. The final piece was the black polyester wrap
dress with the red and pink roses on it. I stood in front of the mirrors
and admired how I looked. I looked like a teenage boy wearing women's
clothes. It was so depressing that I almost took it all off and fled.
For some reason the stairs seemed like they went on forever as I
descended the stair case. I got to the living room and Bob had stood up
and smiled as he looked at me. Bob told me that I looked very sexy and
had me turn around for him. I was complimented on my ass and he told me
that I had real knock out legs. Bob told me to come sit next to him on
the couch. I told Bob that I had had sex with one girl and that I did
not think I was gay. But, I did have to admit that while wearing women's
clothes I did picture myself as the girl and did think about men as my
sexual partners during those events. We sat on the couch for several
minutes watching the porno that was still being displayed on the
television and I continued to drink my wine. Bob stared straight ahead
and said, "I am going to do something I want you to promise that you
won't get freaked out."
The only thing I could respond to that was, "No more freaked out than
sitting here in women's clothes." With that Bob pulled down the front of
his shorts and pulled out his dick. I wish I could write some big lie
about how it looked like a baby's arm holding an apple, but, it was not
much bigger than mine. It was just sort of like Bob......average. But I
could not take my eyes off of the hard dick that he exposed to me. I had
never seen another hard dick in real life besides my own and to be honest
I was scared shitless. Bob asked me if I would be willing to jerk him
off while he watched the porno. My hands were shaking like leaf as I
reached over. I knew that what I was doing would technically make me
"queer" or "gay". As my hand touched Bob's hard dick he let out a
shutter and moaned as I began to run my fingers along the underside of
the shaft. I knew that I liked the way that felt when I masturbated so I
figured he would as well.
After several minutes of using my hand on Bob's hard cock, I felt his
hand on my shoulder and eventually on the back of my head. Then, I felt
him begin to apply a little amount of pressure to the back of my head. I
had tired the same tactic on a girlfriend so I know exactly what I was
wanted to do. At first I tensed up and hoped he would get the idea that
giving him head was not what I wanted to do. But he was persistent and
began to beg me, "Please put it in your mouth....please!"
I told Bob that I did not want to and that I was afraid. He told me the
first of many lies men would tell me about sex. "I promise I won't cum
in your mouth."
I leaned over and began to hover my mouth over his still rock hard cock.
I was hesitating because I was still frightened out of my mind. Then, in
one motion Bob pushed my head down and raised his hips up. With that
singular action his cock entered my mouth. Upon feeling the warmth of my
mouth Bob let out a big moan. And with that one action I had officially
crossed the line and I was now a fully fledged faggot. As his hard dick
slid in and out of my mouth, my own cock became rock hard. The feeling
of my lips sliding along the length of his cock was amazing and I reached
down to free my own cock from the satin that held it back. I could not
believe that there I was dressed fully as a woman sucking the cock of a
forty year old guy. It just seemed so dirty and yet so much fun.
I was getting so much into my own thoughts and feelings that I did not
even notice that Bob's cock was swelling up even more and his balls had
constricted. It was not until he began to shoot hot sticky wet cum into
my unsuspecting mouth. And like any normal kind of guy, Bob held my head
and mouth in place as he drained the contents of his balls into my mouth.
As my mouth was flooded with the salty tasting warm sperm from Bob's
obviously neglected dick I could not help but think that it was not so
bad and I did not know why girls acted like it was so gross. Truthfully,
I sort of liked the taste of it. More importantly I enjoyed using my
mouth for Bob's pleasure.
Bob and I sat there on the couch for the next hour and talked as if
nothing had just happened. After I changed into my regular clothes and
started to leave Bob told me, "I really liked that. If you are not
opposed I think I would like to do that again."
I returned home that night with a little souvenir, a pair of red satin
panties that I wore to bed after making myself cum in them.
The following morning I went across the street to check on the cat.
Bob's motorcycle was out front and I found him eating breakfast. While
taking care of my duties and trying to stay cool, Bob told me that I did
not need to feel embarrassed about what had transpired between us. Then,
Bob asked me to go put something else on for him. I ran up the stairs
and practically ripped my own clothes off. This time I picked out a
floral patterned pair of flutter panties with a matching bra. While I
was trying to decide what else to put on Bob walked into the room and sat
on the wicker chair with the high back.
I watched as Bob took off his boxer shorts to expose his hard on and
motioned for me to come over to him. I walked across the room to him and
sank to my knees. Bob stood up and told me to open my mouth for him.
Like any good girl I did as I was told. For the second time in less than
twenty four hours, I took a man's cock into my mouth. The feeling of
being on my knees while my mouth was being used to give him pleasure was
beyond words. At one point Bob began to hold my head and rock back and
forth with his hips. Remembering everything for our previous encounter I
paid particular attention to his cock size and his balls. Right when I
felt his balls get tense I made sure my mouth was on his dick sucking
away. I was rewarded with a mouthful of cum that I quickly swallowed.
Over the next few days this became the routine..... I go to feed the cat
and wind up getting fed dick by what a man I was quickly beginning to
develop feelings for.
Friday night came and my little brother was spending the night at a
friend's house and my mother was going out for the night. I knew that I
would have a lot of time to play house with Bob. I went over and found a
note from him. "Be back at 7. Be ready." I had over an hour to kill so
I decided to make the best of it.
I took a shower and used a razor to get rid of all the hair on my legs,
chest and underarms. I knew that it was a little ballsy but, I also
figured nobody would notice. I walked into Patricia's room and found the
perfect outfit. I put on a pair of purple satin string bikini panties
with a purple satin bra that snapped in the front. I filled the bra with
a few pairs of pantyhose to give me the illusion of breast. Next I slid
on a pair of fishnet stockings and slid on those strappy sandals. In the
closet I discovered a leather skirt that I could just barely fit into and
a white silk top. Once again I stood in front of the mirror and realized
I looked like a teenage boy wearing a skirt. This time I decided to do
something about it. I sat down at the vanity and looked at the makeup.
I had a rough idea of what to do from all the times I watched my mom
getting ready. I applied some foundation, blush, eye shadow, eyebrow
pencil and some scarlet red lipstick. When I was done I had to say I
felt pretty good about myself. I even applied a little of the perfume
from the counter to my neck.
After spending about ten minutes admiring myself, I heard the door open
and I called out for Bob. "Down here," he replied and I told him that I
would be right down. I felt like a girl going to meet her prom date.
When Bob saw me all he could say was "WOW!!!"
After a couple of minutes of admiring me Bob told me to hold on as he
raced up the stairs. I could hear him moving some items and when he
returned he was holding a blonde wig. He sort of grinned and told me
that his sister had gone to a Halloween party as Loni Anderson and that
the wig had been stored in his closet. I tried it on and it felt very
weird having something touching my neck as I moved and talked. We sat
and talked for a while when he asked me if I felt a little crazy. When I
asked him what he had in mind he said, "Just trust me".
Bob led me outside for my first exposure to outside air while dressed.
The feeling of standing in the courtyard of the townhouse felt electric.
Bob handed me a motorcycle helmet and it took me a few moments to process
what he wanted to do. "No way," I told him.
Bob assured me that nobody would be the wiser because I looked so fucking
hot and I would have the helmet on. To this day I don't know why I
trusted him but, I did. I hopped on the back of his Goldwing and wrapped
my arms around him. We cruised off along the roads of South Florida
until we finally got on A1A, the road that runs along the ocean. I felt
so sexy and as alive as the motorcycle hummed along and I had my arms
wrapped around Bob's chest. At a redlight I even caught some guy
checking out my legs and my short skirt. It was pretty funny when his
wife caught him as well and began to hit him. We finally arrived at a
small bar on Hollywood Beach called "The Dock". Bob told me to act like
an adult woman and act like I belonged there and nobody would challenge
me. Much to my amazement we walked in to the dark bar hand in hand. Bob
escorted me over to a booth with a view of the intercostal and fetched us
both drinks. We sat in the booth and had a few drinks and talked about
life. He told me that he was getting his own place because he was sick
of his girlfriend's mood swings. Bob grinned and said that he really did
not mind since he had already found a "new girlfriend". Bob took my hand
and led it under the table. I could feel his rock hard cock straining
against his jeans. I had already learned in a few days that he really
really liked me doing certain things to his dick. After running things
fingers lightly along his cock he just shivered and said it was time to
go.
A motorcycle ride later we were back at the townhouse. I walked in
feeling like I was on top of the world. Bob approached me and began to
kiss me while running his hands all over my body. I could not believe
how it made me feel as he told me I was beautiful and sexy. Eventually,
we wound up in his bed room making out on his bed. As he lay on his
back, I took the initiative and undid his pants freeing his cock.
Without encouragement or invitation I took his cock into my mouth and
began to move up and down.
I really liked the sexual response I received when I ran my tongue along
the underside of his shaft. While sucking his dick I felt his hand reach
underneath my leather skirt and along my ass. Since beginning this
little tryst that was the first time he actually touched me in a sexual
way. The contact only encouraged me to suck faster. That all stopped as
I felt his finger go underneath the back of my panties and touch my
asshole. Bob realized that he must have done something too much and told
me he was sorry. I informed Bob that I had learned all about AIDS in
school so anal sex was out of the question. Bob sort of chuckled and
said, "You really are being like a woman now. Telling me what is and is
not available."
Bob assured me that he only wanted to touch me and that I could not get
infected by him touching me. It seemed reasonable enough and I went back
to sucking his cock. I felt his hand slide across my panty covered ass
and then back under the material. I felt his middle finger touch me
again and I could feel my sphincter respond to the stimulation. After a
little while it began to feel really really good with Bob playing with my
ass while I sucked his cock. Bob had his forearm across his face while I
gave him head and he exclaimed, "God I want to fuck you."
Hearing that did not make me stop it only encourage me more. Eventually
Bob stopped me and went into his dresser drawer. Bob returned to the bed
and removed my skirt and blouse. I knew what was going to happen and I
was too scared to protest or consent. I just let things happen
naturally. I was rolled onto my stomach and told to arch my butt into
the air. I knew the position but, I let Bob tell me anyways. My panties
were pulled down to expose the target of his desire. I felt something
cold and wet being applied to my butt.
The next thing I knew I could hear the condom wrapper being opened and I
felt Bob position himself behind me. I could feel the hardness of his
cock against my anxious asshole. I was so scared that he kept telling me
to relax. As much as he told me I just could not. Bob tried for several
minutes to get his cock in naturally to no avail. Finally, he grabbed
his hard cock and began to rub it along my awaiting hole. Upon finding
the opening, Bob began to slide his cock inside me. My body's immediate
reaction was to tense up and try to repel the invading sex organ. Bob
very sweetly told me that the worst was over and to relax. As I did
begin to relax he began to slide more of his cock inside me. At first I
felt like I had to use the bathroom. I just felt very "full".
Eventually Bob began to move his cock back and forth to a good slow
rhythm. Inside my head a voice was screaming at me, "YOU ARE BEING
FUCKED!!!" The only sounds I made were moans of pleasure. Bob did not
say a word at all. It seemed like he was concentrating with all of his
might. He did not fuck me hard but, very slow and soft. I felt like I
was being made love to. Eventually, I could feel the grip on my hips get
tighter and Bob began to grunt and make some very animalistic noises. I
felt him put his cock as far into me that it could fit and he went limp.
I lay next to Bob and put my head on his chest. After a little while I
asked Bob if I had to leave and he wondered what my mom would think. I
threw on my regular clothes, ran home and left a note saying that I was
spending the night at friend's house before running back across the
street.
I was so sad when Patricia returned from her vacation and I lost my
"special time" with Bob. About a month later Bob moved into an apartment
a short bike ride away. Over the next year the relationship between Bob
and I grew more and more. My mother liked me hanging around Bob because
she said I needed a "male role model". Little did she know that I had
been introduced to the Fredrick's of Hollywood catalog and had a wardrobe
of women's clothes at his place. During my senior year of high school
Bob got a real girlfriend and eventually I saw less and less of him. I
will forever hold him as the standard for all the men since then.
Charlize
- 13.11.2020
- 9
- 0
