Anthea s baby 1
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The Gawker free porn video
The Gawker
My name is Sharon, well actually it is Fred but for one weekend each
month it is Sharon.
I have stopped wondering why I like to crossdress I just do. I am a
heterosexual male who enjoys his feminine side but is not into sex with
men or other tgurls. While my enfemme weekend activities can vary the one
constant is a once a month Saturday night get together with three
friends
for a gurls night out at a bar in Cambridge. The bar is not quite
mainstream and not quite "alternative lifestyle." Someplace in between -
an eclectic mix of all ages and kinds. As such, it is in a sort of
sketchy part of town. Not particularly dangerous, but not entirely
"vanilla safe" either. While it was not unusual to see gurls around, they
had to be careful and alert. No telling what kind of weird pervert or
intolerant jerks would present themselves, particularly at the end of an
evening.
As for my friends, Allison and Sheila they are into each other. Suze is
strictly into men. Nevertheless, we enjoy getting together once a month
to check each other out, encourage ourselves and socialize. For a couple
of hours, we can just be ourselves with ourselves.
I was running a bit late so when I arrived there was no on street
parking, so against my better judgement, I parked behind one of the
businesses across the street from the bar. I walked quickly in between
the buildings and went in to meet the gurls.
We were having a few drinks. We take this opportunity to really put our
best feet forward as gurls. Not that we compete mind you, but we do
attempt to outdo one another. It's all friendly though. We have fun with
it. Tonight we were all dressed to kill. Full and detailed make up, sexy
shoes, blouses and extra-large breast forms to accentuate cleavage. I had
on a very tight fitting, low cut red dress which came up to about mid-
thigh.
The dress came with a little matching bolero jacket. To complement my
dress, I was wearing knee high black high heeled boots, underneath I was
wearing black thigh high stockings, a waist cincher with garters, and of
course my very realistic life-like 40 D breast forms. A gaffe concealed
my private parts. While the jacket served its intended purpose of
concealing my slightly over sized shoulders, there is nothing like a low-
cut dress and big tits to focus the stares on to my assets! I had on my
straight shoulder length blonde wig, and red lipstick and nail polish
that matched my dress.
Suze and I are smokers so every once in a while we excuse ourselves and
go out onto the sidewalk and light up. As we were puffing and talking I
noticed a guy standing in a storefront across the street. He was nice
looking and normally dressed. Not unusual except for standing alone at
night across from a bar known for its wide and varied clientele,
including a gathering place for local gurls.
He was watching us intently but made no move toward us nor did he say
anything. We didn't think much about it and went back in. However, I
hoped that he would disappear before I had to make my way back to my car
behind the building. About an hour later, we went out to catch another
smoke and there he was again. Just standing there. Looking at us. I
figured it out. He was "in" to gurls not so unlike quite a few men......but
secretly. I surmised he would venture to the door of the bar and not go
in. Never quite able to "consummate" his desires. Suze, who is a somewhat
more aggressive personality than me finally shouted, "Hey ass hole,
don't
be such a chicken shit! Be MAN enough to come over here and leer where
you can get a GOOD look. Don't gawk from across the street like we are
some sort of freak show."
At about 1:00am we decided to call it a night. We all walked out
together. I didn't see the "gawker" as we had taken to calling him. Suze
asked where I was parked and I told her across the street. She offered to
walk with me but I said I would be fine.
I quickly crossed the street and walked through the alley to my car. I
unlocked the door and as I got in out of the corner of my eye I noticed
some movement by the back of the building. I jumped into my car closed
and locked the doors. My heart was pounding. I peered into the night
trying to see if there was in deed someone there. A car drove by on the
street behind us and for a moment the back wall was illuminated. There he
was, I could see him clearly, it was the gawker. Strangely, knowing it
was him made me calm down slightly. I was still a little shaky so I lit a
cigarette and took a deep drag. As I exhaled, I glanced in his direction
to make sure he was still just standing there. He was still in the same
place but he definitely wasn't "just standing" there. His right hand was
at his crotch and he seemed to be rubbing it.
Now I suppose like a lot of tgirls, I like to be noticed and checked out
by guys but I have no interest in having sex with them. Now there was a
guy who was using me as jerk off material. I don't know why it was so
shocking I had jerked off countless times while looking in a mirror. But
suddenly a wave of slutty femininity washed over me. I was intrigued by
this man who found me so sexy and attractive that he could not resist
self-pleasuring. This feeling gave me enough self-confidence to open my
car door, swing my legs out and stand up. With my new found attitude, I
did a series of deep inhales and sexy exhales, a few pouty looks and a
couple of licks of my lips, while I stared at him. I was urging him on!
He locked his stare on me while he openly and vigorously worked his cock.
I kept my teasing up, this time raising my foot on the door jamb and
hiking up my short skirt to just under my right buttock. Looking over my
shoulder at him while licking my red glossy lips, I noticed the telltale
lurch and heard a heavy sigh. I threw down my cigarette, crushed it out
with the sole of my shoe and got back into my car, started the engine and
drove off without looking back. It was a short drive back to the motel
where I had been staying but I was hard as a rock when I got there. I
went into the room lit a cigarette and did the same exhales and
expressions as I pleasured myself. Somehow knowing I had made a man cum
made the pleasure more intense.
The next day I had to be back in boy mode but over the next two weeks I
thought about the incident over and over. I wondered about my true sexual
orientation, but I could only imagine that night as a woman, not as a
man. I am not sure there is a label for this "orientation." Because
without the makeup, lip stick, stockings, garters and other
stereotypically sexy feminine accessories, I just felt like an ordinary
guy. But every time I thought about the encounter as my "en femme" self I
got hard as a rock.
Finally the next weekend for dressing and going out came. I spent the
entire afternoon getting dressed, carefully attending to every detail. I
took a long bath and shaved my whole body. I attached my life-like breast
forms with medical adhesive. I put on a black waist cincher with garters
holding up black thigh highs and black lacy panties. Over this I put on
a satiny white blouse and a short black skirt and wide patent leather
belt. I pulled on knee high black patent leather boots with 3" heels. I
wore large l gold hoop earrings. I decided on my shoulder length, wavy,
blonde wig.
I finished off with very long eyelashes, dark red lipstick and nails to
match. Over it all I put on a tan microfiber trenchcoat.
There were a couple of spots to park on the street but I decided to park
back where I had the last time. I guess I secretly hoped for another late
night encounter. But it made no sense that he would be hanging around
again, and I certainly didn't know how I would react if he was, but
nevertheless, it seemed to give me a tingle of excitement as well as
heighten my expectations for the evening.
As usual the gurls and I met and had a good time. The first time Suze and
I went out for a smoke I looked around but didn't see the gawker. The
storefront was an attorney's office on one side and a nail salon on the
other. I felt disappointed but not surprised.
At the end of the evening we said good night and I walked quickly back to
my car but I lit a cigarette and lingered for a moment, and in a way
more
than a tiny bit disappointed. As I exhaled I heard a man's voice
"You look beautiful tonight!"
I tensed up and turned around. He was there! I jumped.
He said, "Please don't be afraid."
I took a drag and exhaled it slowly as I tried to regain my composure.
Finally nervously I said, "What err, what do you want?"
As the words came out I thought, now that's a dumb question!
He smiled and said, "I don't exactly know, I just like to look at you, to
watch you smoke."
I looked him up and down, and then said, "You know I'm a Tranny."
He nodded in the affirmative.
At this point my fear had subsided and I was feeling slightly more in
control of the situation. What's more I seemed to be enjoying the
attention he was giving me. No "seemed to be enjoying the attention"
doesn't come close to describing what was going through my head. I was
reveling in this moment and it seemed like somebody else started
controlling my body.
I licked my lips and twirled my hair with my finger. I took another drag
and exhaled and said, "So what do you feel when you watch me?"
He replied, "I get very excited! I watch tranny porn on my computer and
it gets me hard but it is just so much more of a rush with you."
I smiled and said, "So you jerk off watching tranny's smoke?"
He nodded.
I continued, "And is that what you have in mind right now?"
Sheepishly he replied, "Yes I would like that very much."
I took one last puff and threw down the butt and crushed it with my shoe.
I slipped off my trench coat, took another cigarette out and lit it, blew
the smoke right into his face and said, "OK, let's see you perform."
He unzipped his fly and an erect penis popped out.
I smiled approvingly and took another long drag and exhaled a plume of
smoke and gave him a sexy pout.
He started vigorously working his pre greased cock as I continued to
smoke, lick my lips and twirl my hair.
I was mesmerized; I was watching another guy jerk off as he looked at me.
I felt so empowered!
I just kept staring as he stroked the bulbous head of his stiff cock. But
soon looking didn't seem to be enough. I had an incredible urge to touch
it.
I reached down and touched the head of his cock with my finger; a shiver
ran through my body.
In a husky sexy voice I said, "I think we will both enjoy it more if I do
it."
And I took hold of his penis. I felt a rush like never before; I looked
down and saw my feminine looking hand with the long dark nails wrapped
around a seven inch cut cock.
I started stroking. I pulled the skin taught around the base and slowly
stroked the head and shaft - accentuating the erotic friction. He started
moaning, and I found it was far more pleasurable than masturbating
myself. Faster and faster I stroked he rocked back and forth and suddenly
he came, in a throbbing pulsating squirt, It was warm and sticky and it
went all over my hand. I felt triumphant. I took some tissues out of my
pocketbook and wiped the cum off my hand. I was feeling sexy, empowered,
not to mention hard as a rock.
I took one last drag and exhaled, and said, "Do you need a tissue?"
He nodded.
I turned to get one out of my pocketbook and as I did he got a side view.
I handed him the tissue.
He said, "Thanks, err would you like some help with that stiff one under
your skirt?"
Somewhat flustered I replied, "No, No I can take care of it."
He smiled and said, "But it would be more fun for both of us if I did
it."
I replied, "Really I think I should be going."
I turned to get in my car and he reached out and took my hand.
I stopped and turned to face him.
He said, "Please don't go!"
With that he dropped to his knees and put his hand under my skirt and
pulled down my panties.
I gasped, I didn't know what to do, I didn't think I wanted this but I
did nothing to make him stop.
He kissed the tip of my cock and my whole body tingled, he slowly took
the length of my shaft into his mouth, his lips moving slowly up and down
my erect cock. His hands caressed my butt cheeks, and then his right
index finger started to probe my anus.
I moaned with delight. I found myself running my hands through his hair,
my red fingernails lightly scratching his scalp, pulling his head onto my
cock. His other hand was now fondling my balls while his other hand now
pierced my anus with another finger, widening the opening and also making
it easier to massage my prostate, in a milking fashion. I felt like
there
was a river from my insides into his mouth. Pre cum was literally flowing
onto his tongue every time he withdrew my cock from his mouth to kiss
and
lick the head. Like strands of honey, my precum was running from his
bottom lip to the ground. There was no way he could keep up with the
flow, particularly with his fingers coaxing ever more from deep within
me.
I have to admit he was particularly good! The reverence he showed for my
now steel hard cock made me think that he was not "blowing" or simply
sucking me, he was savoring me, intently enjoying the smell, taste, feel
and reaction of my cock in his mouth, on his lips and in his hand. I had
never experienced head so intently given before.
Now with two of his fingers fingers pushing deep inside of me while his
his tongue danced over my overly engorged dick his attention and pace
became much more vigorous. Pistoning his fingers in and out and over my
prostate with his lips clamped over the head of my cock while his hand
stroked it up and down waves of pleasure ran though my body. I could feel
that I was about to cum and instinctively tried to pull away but he held
me firmly in his mouth with his hands as well as lips. Now he
transitioned from simply oral caresses and fondling to vigorous in his
sucking and pumping. Suddenly, I let out a guttural grunt so as not to
scream, my hips jerked forward, my cock spasmed and I started to shoot my
load in his mouth. Again and again, I lurched, his fingers in my ass
milking my prostate while his mouth continued to pump my now sensitized
cock head. He was going to drain me! He continued to milk me until he
felt my muscles relax exhausted from the most intense orgasm I had ever
experienced. He continued to lick and clean my cock and balls of any
"spillage" and finished with a series of sweet soft kisses over my balls
and up my shaft with countless little licks and kisses around the now
softened head.
I leaned against my car with a million thoughts and feelings running
through my head and completely unable to process any of it.
He swallowed most of my cum and wiped the rest off of his face using the
tissues I had given him earlier.
Having no clue how to exit this scene gracefully I simply jumped in my
car and started the engine. He turned to look at me and said, ""Third
Saturday of the month, I'll look for you next time!"
I drove back to the motel and proceeded to pleasure myself so hard and
often that I thought it might fall off.
Getting back to drab life was difficult. I became obsessed with cocks. I
checked them out on internet porn sites. I bought myself a dildo and got
dressed late at night and practiced sucking it and putting it up my ass.
I especially enjoyed sitting on it while I masturbated. I even got a
remote controlled butt plug vibrator which I used at the office. If the
boss only knew what was holding my attention during those staff meetings!
The next few weeks I tried internet dating sites looking for someone, but
I was turned off by the small talk, chit chat part of it. Some of the
guys were pathetic losers and other were macho acting ones that wanted to
be sucked up to as well as sucked off. Neither did much for me.
I still pondered my sexual identity. I didn't think I wanted sex with a
man; somehow I wanted the cock but nothing else. But Sharon wanted to be
consumed. My gawker was perfect, we had exchanged only a few words, I
knew nothing about him other that I made him him hard, and he did the
same for me, but in an enthusiastic, caring way. Never before had
someone, woman or man ever got me off the way he did. Not that I felt an
emotional tie, but the feeling of "committed pleasure" was undeniably
exhilarating.
I didn't think I could ever muster the courage to go to an adult book
store but I toyed with the idea of pleasuring a cock sticking through a
glory hole. I found the scenario very arousing my encounter with the
gawker wasn't quite as anonymous as that, but more importantly it was
close and now seemed available. If I wanted to be fucked this was how I
wanted it to be, pure unadulterated sex for sex sake.
Finally the day came for my night out with the gurls. I checked into the
motel and took a long relaxing shower, and shaved my body all over. I put
on my breast forms with medical adhesive. If I were to see him again I
wanted to look as realistic and sexy as I could. Because this might be my
night to be fully taken and to experience as much sex as could be had.
Next I did my make-up; I used a moderate amount of eyeliner and applied
my false eyelashes. I had chosen a dark red color for my lips and nails.
I was going for a tarty look rather than my more commonly used classy
look. I used a lip liner to enhance the outline of my lips and achieved a
very full look. I wore a sleek, straight shoulder length Blonde wig with
bangs. I put on a black waist cincher with garters, very sheer thigh
high
black stockings. I wore a black and white dotted, low cut dress that came
to just above my knees, with a short white jacket with three quarter
sleeves that came down just below my bust line. I put on a pearl choker,
and drop pearl earrings, a large cubic zirconia diamond solitaire, and
slipped my feet into 3" pointed toe black pumps. The room had a full
length mirror and I had to pause and think to myself, "Damn, I look HOT.
Someone needs to fuck me tonight."
I parked in my usual place and when in to meet the gurls. They all
commented on my "new" look and asked if there was something special going
on. I demurred and said I just wanted to try something different - which
was more true than any of them could have imagined.
This night the place was full of men dressed as men.
Now Suze is the T equivalent of a babe magnet. Admirers or chasers flock
to her like moths to the light. She is comfortable with the repartee, and
thoroughly enjoys the scene. As would she cast them away and focused on
the lucky guy for the evening, the losers started paying attention to me.
One guy told me how pretty I was while his hand slipped under my skirt.
I
quickly removed it and told him to get lost. A few tried to impress me,
but they were just full of themselves. The best offer I got was from a
short stumpy guy who just walked up to me and asked if I would go into
the bathroom and suck his cock. I declined somewhat reluctantly.
Suze and the guy of the night took off and the other gurls decided to
call it a night.
I walked back to my car and paused and lit a cigarette, as I exhaled I
heard footsteps, as I turned I saw him.
He was wearing a trench coat, but as my eyes moved down I noticed his
legs were bare. Christ, what a pervert! He walked right up to me and
without saying a word he opened his coat.
I looked down and saw it. He was already hard as a rock. It was now or
never and never was not an option!
I took one last drag and exhaled, threw the butt away and I was quickly
on my knees. I was too timid to go right after the cock so I started by
pressing my lips lightly against his balls kissing them softly first then
licking them as he groaned with pleasure. Feeling empowered, I
tentatively reached out for his throbbing cock. I encircled my right hand
around the shaft just under the head and pulled my hand toward the base
while I continued to lick his balls. His excitement contributed copious
amounts of slippery precum to my hand job efforts making it easier to
stroke him from the purplish head to its hairy thatch of a base.
Replacing my tongue and lips with my left hand, I continued to fondle his
balls while I stared at that beautiful mushroom head, precum now flowing
out of the center. I reached my tongue out and flicked the tip and the
clear honey like substance flowing from it. There was sweetness about it
that I found pleasant. So I glided the head and shaft onto my waiting
tongue, my upper lip applying pressure to the top of the head as it
passed through my red lips and into my moist mouth. I gave it a couple of
quick pumps and while that excited me the prospect of what I was staring
at had me even more excited. My tongue darted out and licked the head of
his cock, it twitched in response. I sucked his balls and then kissed
his
cock. Then I opened my mouth and slowly took his entire length in. At
first I gagged. But I quickly got the hang of it and was able to take his
entire shaft into my mouth pressing my nose firmly into his pubic hair
at
the base. I took to lingering with him in my throat working the back of
my mouth to rub against the head of his cock. Over and over, and very
slowly I slid my mouth back and forth over the entire length of his cock.
At first he seemed tense but then he relaxed a bit. Then started to
squirm. At that point I picked up the pace, and my lips more tightly
hugging the shaft and sliding quickly up and down the its entire length.
All of a sudden he started to thrust with his hips, I gagged and spit out
the cock, but quickly devoured it again, he thrust once more and this
time I was ready and got in rhythm with his movements which were coming
faster and faster and his breathing was getting very shallow and rapid. I
inserted my finger into his ass and rubbed his prostate the way he did
me. I then felt a tightening particularly as I pressed against it with my
finger. Then there was a spasm, and my mouth was filled with warm salty
cum. I was euphoric! I instinctively swallowed. And swallowed. And
swallowed. I was surprised at the volume, some even came out my nostrils.
I coughed and spit some of it on the ground. It was my first taste of
cum. The taste was not all that pleasant, but the sensation of taking it
from a man was not only exciting but made me feel a sense of power that
imparted both sexual gratification as well as self-confidence. I knew
right then it would not be my last.
Without a word, I got up and went back to my car where I wiped the rest
of his cum off my face and fixed my makeup.
I took out another cigarette and lit it and drew the smoke deeply into my
lungs. I turned my head to the side and glanced over my shoulder at him
as I exhaled. He was staring at me. I bent forward at my waist using the
hood of my car for support, pulled up my dress, and pushed my panties
down. I spread my legs wide apart and pushed my cock back so he could see
it was hard. He didn't need to be coaxed he was on his knees behind me
and took my cock in his mouth as his hands caressed my butt. While
grasping and gently stroking my cock, his tongue turned its attention to
my anus. WOW! What a feeling. His tongue orbited by anal opening and sent
electricity through my body. Up and down my crack he moved his tongue
using the tip to burrow into me as far as he could. Darting in and out,
up and down he pleasured my ass before returning to lick, suck and
finally kiss my cock head before standing up.
So much for the preliminaries, I felt sexy, powerful, and wanted more.
The blow job had made him hard, and the rim job made me ready, so I sat
on the hood of my car and pushed myself back, opened my legs wide and
said
"Come and get it."
He stepped in between my legs.
As he moved in closer I kicked my legs up and put one on each of his
shoulders. He stood up straight tilting me back
He grabbed my hips and pulled me onto his very hard cock. The quality of
his preparatory work showed as his cock head slipped into my anus with
little trouble or pain. I let out a moan and locked my lips.
He paused for a moment and said, "Did I hurt you?"
Breathlessly I responded, "Shut up and Fuck me! Fuck me hard!"
He didn't hesitate any longer. He thrust deep and quickly inside me. This
time I felt pain and it was excruciating, I screamed!
He pushed all the harder. Back and forth through my sphincter. Now my
screams of pain alternated with moans of pleasure.
He just kept thrusting over and over and over again, deeper and deeper
and deeper into me. The pain had subsided and now waves of the most
intense pleasure I have ever felt were washing over my entire body.
Suddenly, I had a feeling I had never experienced before, I wanted him
inside me more and more. "Deeper, harder, faster," I cried, He obliged
and this time I screamed with pleasure as my anal cavity expelled a clear
slippery liquid all over his cock and the hood of the car. I was
reaching
wildly for something to grab on to and tore a wiper from the windshield.
My body was shivering. I was out of breath and dizzy. My legs felt they
could not support me. I learned later that I had what is known as an
"anal orgasm." It was so intense, I was a bit scared, but I knew I wanted
more of that.
Then his face got all contorted and red and he started breathing hard.
I was in ecstasy! I felt him pound in my ass and I was reveling in
watching him do it. Too soon he went into what looked like a fit, but it
turned out to be his climax as I felt his cock spasm inside me and then I
felt the warmth of his cum.
I didn't move for a while actually I am not sure my legs would have held
me up, my whole body seemed like jello. I was breathing heavily. He
backed away slowly and my legs fell abruptly to the ground, I almost
slipped off the hood of the car.
I managed to get over and open the driver's side door and sat down. I lit
a cigarette and deeply inhaled.
Ecstasy was a memory and the pain was back.
He was sitting on the pavement looking spent.
Finally he said, "That was-"
I cut him off saying, "Shut up! I didn't come here for conversation."
He nodded and then got to his feet.
I managed with some difficulty to cross my legs, took a deep drag and
long slow sexy exhale.
He looked at me and said, "Third Saturday of the month, I'll be here."
I looked him straight in the eye and said, "Screw that I'll be here next
Saturday night."
A faint smile ran across his face and he nodded and replied, "I'll be
here."
He turned and walked away.
Jerri
- 08.04.2021
- 15
- 0
