Jens first babysitting job
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Jen's First Real Lover free porn video
This is an autobiographical story about my initiation into being a
"girl". I hung out with a group of guys when I was a teenager, mostly
to get high with. One of these guys had an older brother who had his
own group of guys... Real Badasses. Guys you wouldn't ever want to fuck
with. No one under 200lbs and really tough. Over the years I got in
pretty tight with this group. Hanging out, scoring weed and getting
high. One guy in particular became my dealer and "friend". I often went
to his apartment to score weed and hang out. It was a tiny room on this
ranch that had guys living in different places all over the property.
There were about 5 different guys living there at any one time. Joe's
apartment was a separate one bedroom shack, enough room for a bed, TV
dresser and one chair. I sometimes hung out there for hours watching
movies and getting loaded. Joe was as big as a house and really
straight, but because I was young, fare and well built, and he was
twice my size he would make comments and innuendos about my build, and
my ass (kind of in a jailhouse way). I never said anything till one day
he told me a story about one of his buddies picking up a transvestite
at a bar and getting a great blowjob. What he or anyone else didn't
know was that I had been a closet cross-dresser since I was a young kid
and would dress up in my mother's lingerie and masturbate my ass with
anything and everything that I could get in my hand that would fit
inside me. Candles were my favorite. Even now in my early 20's I often
dress in my girlfriends panties and fantasize about being a real girl,
pleasing men with my cunt, and mouth. I had often wondered about Joe's
cock because he was so big. His hands were huge, his chest was broad
and he could easily pick me up with out a thought and handle me.
Without realizing it I opened my mouth and asked Joe what he would have
done with the transvestite. To my surprise he said although he wasn't
gay he also wouldn't have passed up the opportunity for a good blow job
and to bust his nut in someone's ass if he had it in front of him. With
that statement in front of me I boldly stated, "what if it was me?"
Joe's look changed. We had been drinking and smoking and now he had a
funny grin on his face. So I shyly repeated my question and he told me
that if I was willing to be his whore and shave my whole body and go
all out to be a hot tranny that he might give me a try. I smiled at him
in my best girlish smile and whispered, "I would like nothing more than
to please you however you want. We set a date late the next Saturday
night. I had never been so nervous and excited. I had planned to come
over after he and the guys had been out drinking and partying. After
what seemed like forever of planning and shopping I got ready that
evening. I showered and shaved every last inch of my body. It felt
great. I have never felt more feminine and free in my life. I put on my
brand new garters and stockings, my silky panties, a padded bra and a
tight summer dress. I wore big platforms and a blond wig. It took me
forever to do my make up but when I was done I looked at myself in the
mirror and thought to myself that I was hot and definitely fuckable.
Before I left I greased my boy cunt and inserted my sized buttblug in
my ass to make sure I would be ready when the time came. It was getting
real late and I got into my car and headed over to his place. I liked
driving around wondering if the guys were looking at me as a freak or
because they wanted to fuck me. After all I did look like a hooker. And
I realized most were fuck looks. When I got to his place I was really
glad he lived close to the gates. I walked up to his door and gave it a
quick knock. Joe answered the door and after a second of astonishment
he asked me to come in. In my best feminine whisper I asked him if he
liked what he saw. He responded by asking me what my name was. Jennifer
I answered. Then Joe did something completely amazing. He said
"Jennifer would you like a drink". After a few drinks and some silly
small talk I asked him to lie down because I was really excited to get
to his cock. I pulled off his shirt and started playing with his
nipples, licking and lightly biting them, I could tell he was getting
excited, but what was to come I couldn't even imagine. He began to push
my head down to his cock and with my hand I began to rub it through his
jeans. It felt so solid and massive. I was hardly able to free it from
his zipper before he shoved my head down to meet it. I didn't have much
time to size it up but it was like a 16 oz beer can in front of my
face. I did what I could to get my mouth around it before Joe began to
work my head up and down. Before I knew it he was jamming my face down
on his massive pole and fucking my mouth. I couldn't breath but he
wouldn't let go and my only choice was to open my throat and let him
rape my face like the hooker I felt like. I gagged a couple of times
and Joe let up his grip enough to let me catch my breath, but as soon
as I was ready he would go back for more. This must have lasted about a
half hour. My jaw was getting sore but I was actually enjoying being
manhandled the way I was and wanted to please him even more. Before my
eyes this nice guy had turned into an animal and was throwing me around
the room like a blowup doll. So much for my sexy lingerie, Joe lifted
up my dress grabbed the side of my panties and ripped them right off
almost ripping me in two in the process. He lifted me up and positioned
me with my ass in the air on the edge of the bed. His hands were so big
they made me feel small and petite. He saw I had the buttplug in my ass
and made the comment that it would take more than that toothpick to be
ready for him he pulled it out slowly and threw it away. Leaving my ass
spread and my cunt gaping waiting for him to be inside of me. He
grabbed my wig and pulled it off and threw it aside. Then he grabbed my
real hair and shoved my face into the bed and hiked up my ass even
further. I felt him spit into my already spread hole a few times and
working his finger in and out making sure he had enough lube to get
inside of me. As he positioned himself above me I felt like a tiny girl
under him. He was so large my knees were spread as far as I could to
let him in up to my rear. He said something into my ear about it going
to hurt, but what he didn't know was that I had been preparing for this
moment since the first time I found how much I liked having something
in my ass. He positioned the head of his massive cock at my hole and
began moving the tip in and out just slightly. I could feel my hole
open to let him in and release when he pulled away. Then he said he was
ready to really test ride me and I felt him lean forward on me and
press his cock into my ass inch by inch deep into my cunt. He felt even
bigger than in my mouth. I felt as if I would split at any moment.
Before to long he was deep inside me. I could feel his balls begin to
press into mine. Joe had a firm grip of my hair and was able to move me
back on his cock with just a strong pull. I yelled out in pain and
pleasure into the bed with my face pressed against it to muffle my
cries. I knew Joe had been able to get his whole cock inside me when I
suddenly felt his enormous weight begin to come down on top of me. My
knees buckled and he came down upon me pressing me into the bed and
completely smothering me with his mass. I was able to work my head to
the side and take a deep breath and while still trying to maintain my
girlish persona tell him to give it to me like the fucking slut I was.
This was about all the encouragement Joe needed and he began to move
his cock back and forth inside my boy cunt. He let go of my hair and
released me from under him and lifted himself up. He grabbed on to my
waist by my garters and began to work me back and forth on his gigantic
pole. I started getting his rhythm and picked up the pace. By then my
ass was able to accommodate his size and girth and I began to ride back
and forth on his cock smoothly, each time letting him pull almost
completely out of me and then letting him shove the length of his cock
completely into me. Each time I would let out a cry as he filled me up
with his gigantic cock. I could feel his balls slapping the soft skin
between my cunt and balls. My own cock swung wildly beneath me as our
pace got faster and heavier. We worked ourselves into a frenzy. Joe
moaning loudly with each thrust and me breathing heavier and crying
encouragement for him to fuck me harder. I began to feel exactly what a
girl must feel when she cums. I never have felt an orgasm so hard and
internal as what I felt while Joe was pounding my ass. It came from
deep within me. I started to scream and moan loudly so Joe pressed me
again into the bed. From my ass and cock driven by something even
deeper in my soul I began to cum harder and more powerful than I ever
thought possible. My cock erupted beneath me with cum all over me and
my ass gripped harder and tighter than ever around Joes cock. He must
have felt my explosion and reacted with one of his own. With everything
that happened so fast I never put a condom on Joe's cock so when he
erupted with his own orgasm he came deep inside me with his cock
pressed up to the hilt. He trembled and shuddered for what seemed like
minutes and I could feel his cock twitch and pulsate deep inside my
body. I could feel the rush of come shoot out warm and thick inside me
and coat my entire canal with his cum. It was such a tight fit in my
asshole that it began to ooze out the sides of me around Joe's thick
cock. It begin dripping from my ass cheeks and running down my legs.
After what seemed like hours Joe pulled his cock out of my beaten cunt.
And sat back down on the bed next to me. I looked up at him with a
feeling of lust and amazement and he must have noticed and said, "don't
just sit there, be the good little slut you are and clean my cock up,
you little whore. " I realized what he meant and I slid down to my
knees next to him and brought my face down next to his semi hard cock,
still oozing with cum and wet from my ass. Hesitantly I began to lick
the head of his cock pulling the bead of cum off the tip and savoring
it on my tongue. It was thick and a little salty, but still sweet. I
brought it into my mouth and swirled it around to really enjoy it. I
then got back to business and licked all around his cock with my tongue
removing all of the taste from my ass from his cock and bringing it
into my mouth. I had never licked another mans ass but I had tasted my
own fingers after masturbating myself. I actually enjoyed it, but I
acted hesitant so Joe would feel more dominate about making me do it.
It worked because his cock came back to attention and I began my most
skillful blowjob I could do. I grabbed his balls with my free hand and
massaged them while stroking and sucking his cock with my hand and
mouth. I let Joe take control and start fucking my face again and I
opened my throat and let him fill me to the limit. I gagged once again
but this time Joe didn't let me go and I continued to gag as he fucked
my mouth. This seemed to turn him on even more. If I tried to pull away
he slapped me on the cheek and told me I had to finish the job if I
would ever want to come back and get some more. So I didn't pull away
anymore and let him gag my throat as much as he wanted. I began to get
used to it and controlled it enough to make sure he would be turned on
by it and I would not puke. From my ass I could feel his cum start to
drip out of my ass cunt and it turned me on even more. Knowing that I
made him cum using my ass like a girl and now using my mouth to get him
off, I felt complete. I didn't know how much more he could take before
he would come, but he just kept going. The rougher he was with me the
more I could tell he enjoyed it and was getting closer to his limit. I
let him smack my face a few more times and I knew this was getting him
to climax, and without thinking I took my finger and put it up next to
his asshole. He didn't jump away, he just kept fucking my face. So I
started to push my index finger into his rear very slowly and I could
tell by his reaction this would be what would send him over the edge. I
pushed a little harder and my finger began to slip inside of his hot
hole. I had never touched another mans ass so I got more excited and
began to move it back and forth. Joe continued to pull my face down on
his cock and also started moving back and forth on my finger. This was
too much for me and I started to cum all over the floor and moaning
around his cock. Joe came down once more on my finger and tightened up
his rear and pressed down hard, he also pulled my face down and buried
his cock into my throat and let go with his cum. His ass pulsated
around my finger as his cock pulsated inside my mouth. I felt what was
left of his cum spray the back of my throat and start to fill my mouth.
I reached up and grabbed his cock and worked it back and forth until
every last drop of his hot cum was in my mouth and I worked it around
with my tongue to enjoy every last drop. I opened my mouth so that Joe
could see my mouthful of cum and then swallowed it in front of him so
he could see that I was willing to take him completely inside of me. I
let Joe fall back onto the bed and comfortably close his eyes. He began
to fall asleep and so I did what a good little whore does. I got
dressed and cleaned up my cum from the bed and floor. I fixed my wig
and put my lipstick back on in the mirror. I had no panties cause Joe
had ripped them in half so I was free under my dress. I felt even more
like a girl. By then Joe was sleeping so I gave him a kiss on his cheek
with enough lipstick so he would remember the next morning and I let
myself out. Driving home I felt a sense of accomplishment and sexier
than ever. I had reached a stage in my life when I felt happy that I
could please a man as "Jennifer". I was confident that I could be as
sexy as any other woman and that a man could want to fuck me. I got
back to my apartment and showered and put on my best sexy slip to sleep
in. I even put my wig back on so I could go to sleep as Jennifer. It
had been a few days since I had heard from Joe and I was beginning to
get a little worried. But then on my answering machine there was a
message for Jennifer asking what she was doing next weekend.
Cheryl
- 27.07.2022
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