The Dogging Diaries
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The Dogging Diaries
Diary Entry: July, 2009
"Guys, guys, guys! Settle down. Now listen. This girl will open her
legs for the whole room, so you're all getting laid tonight. As long as
you're treating her well and keeping her as the center of attention,
she's all yours to do with as you please. Just make sure you don't treat
her too well."
The room laughed.
"You can fuck her, cum on her, cum in her, slap her, spank her, she's
fucking hot and she will go all night if you can."
I could hear Ryan getting the crowd of guys ready to do me as I listened
through the closed bathroom door. The room sounded full. I'd be filled
with hard, heaving cocks within ten minutes. I picked up the short straw
with my French cut nails and proceeded to finish the lines of cocaine
Ryan had chopped out for me earlier.
"Now I took all of your opinions into consideration when I dressed her
and I think you're going to like the way she looks."
I checked myself in the mirror and casually wiped away a flake of coke
from my nose. My auburn hair was teased to porn star extremes, while my
eyes were blackened with kohl liner and smoky, purple, grey and white
shadow. My lips were fat and plum. I was wearing 6" spiked heels,
clear, with ankle straps around red painted toes and black fence net
thigh highs. My silver miniskirt was only 4" long, exposing my black g-
string panties and my wide, fuckable hips. My matching silver micro
bikini top barely covered the erect nipples on my surgically enhanced DD
tits. My midriff was bare, tanned and toned, tapering to my 26" waist.
I was pure shemale sex.
"So let me bring her out boys."
The room cheered and Ryan opened the bathroom door, stepped inside and
said to me: There's 19 out there. Then he dumped another cluster of
cocaine onto the counter and began preparing two more lines.
I began doing the math in my head. Nineteen cocks at roughly 10 minutes
a cum - if each guy wanted to pop twice I was going to be fucked for the
next seven hours.
I picked up the straw again and put it to my nose, doing one line with my
left nostril and the other with my right. I sniffed hard to get it all
into my system and then looked at Ryan as a dog would her master.
"Don't worry hon, there's plenty more, he said. But you're going to have
to work for it. You ready?"
I retouched my makeup around my nose and then added more glitter to my
lips, hair and body. Then I nodded and he opened the door.
"Boys, I give you the dirtiest fucking slut you have ever laid eyes on -
Kristy! She's all yours!"
The room erupted in cheers as a hard rock song began to play on a
portable player. I checked my face again and stepped out into the room a
bitch in heat ...
End Diary Entry
Upon Meeting Me OR The Introduction, August 2011
I am a whore and my name is Kristy. What I am comes before my name
because what I am defines me and defines what you are about to read. I'm
holding in my hand a series of diaries that I've kept for the last
several years. I haven't read them in a while and as I flip through, I
see it captures my journey perfectly. From the physical extremes I have
pushed myself to so I could be beautiful, desired and admired, to the
sexual limits I broke through to participate in the bizarre and erotic
world of dogging - gang bangs and marathon fuck fests with anonymous
strangers. It's an orgy, but I'm the only girl, a shemale whore so cock
and cum crazy that I would do anything to get my fix.
I don't mind the term "shemale" - I've been called much worse. I am also
35 years old now, old enough to reflect on the life I have lived to this
point and the journey I have taken to arrive at this level of whoredom.
I am happy. I have no regrets. What you will soon read are extremely
real accounts of how I came to be what I am today. They are extremely
graphic in nature. Not all of it is pretty and not all of it is dirty.
However I will warn you, there is a lot of dirt here and this strain of
dirt does not wash clean.
I will skip the vast majority of my childhood; although I will point out
that my journey to Kristy is different from many of the other tgirls I
have encountered. I was not a slight boy, not shy nor sickly. I was
just a kid, into games and my imagination and doing well in school. I
was decent looking, a little husky as a little guy, but not fat. Just a
kid with some freckles, some Hot Wheels and a He-Man action figure. My
sister, five years older than I, made the move from tomboy to young adult
lady when she was 16 or 17. I was about 12. She had panties and
pantyhose. I tried them on because it seemed like they were calling to
me. My penis grew when I did. I tried her skirt on too. My penis
couldn't grow anymore because it was harder than it had ever been. I did
this three times in the course of three weeks. The fourth time I
dressed, my mother caught me. She wasn't happy or mad, she simply asked
why. All I could tell her was what I was feeling inside - "I wanted to
know what I would look like if I was a lady." That was good enough for
her. I was 12. No big deal.
Those feelings never really went away. Not that I thought about it much,
since I had moved on to other games, other toys or whatever. Maybe the
Atari and Missile Command or something. But I know they never completely
went away because when I was 15 my neighbor and I started buying Playboys
and Hustlers at a convenience store that was kind enough to sell them to
underage kids and when I looked at them I 1) became turned on and 2)
wanted to be the girl. I wanted to be wanted and I wanted to be fucked.
I needed to feel that desire.
I thought about transitioning or going on this journey throughout my late
teenage years and throughout college, although I never did anything about
it until I was 25 years old. When I said a few paragraphs back that I
have no regrets, I lied. I regret not accepting my feelings until I was
25. I think of the 7 to 10 years I could have had as Kristy that were
lost. Maybe I'm still making up for lost time.
It was late 2002. The internet had been born. There were others like me
who had the same feelings about women. They wanted to be one too. So I
did it all in one day. I became Kristy in one day. In one day I shaved
my body from head to toe, I trimmed and sculpted my eyebrows. I spent
about a grand on skirts and dresses and blouses and breast forms and
cinchers and shoes and jewelry and makeup. At 8 in the morning I had
crawled out of bed as Stephen and by 8 that night I was Kristy, wobbling
my way to a Boston T-friendly bar on 3" heels.
I began keeping a journal the very next day and did so loyally for the
next seven years. As I flip through, I see there's a lot of "fucks" and
"cocks" in these pages. I'll be getting to all of that shortly. First,
here's an excerpt from my very first entry:
Diary Entry: December 2002
As I said, the club is dark. The ladies room - I can't believe I am
writing that, I can't believe I was in there - is not exactly nice in the
least, but it's a ladies room and I am a lady and that is what we do ...
coming back, I could feel the eyes on me. I was fresh meat. I could
barely walk in my heels - my heels! - and tried to not topple over.
End Diary Entry
I was so na?ve back then. I was also hooked on Kristy. I went out to
the club for seven straight days. I met some people. I made some
friends. I wanted more. I never wanted to be a cross-dresser (not that
I have anything against it). I wanted to be a shemale or tgirl - for
life - very quickly.
But I was not-not-not into guys-guys-guys. I still found women so
incredibly attractive. I wanted to be like them and be desired by men,
but ... guys were, well guys and girls were soft and sexy.
Diary Entry: May 2003
I went to a party that a couple of tgirls were having in [name of town
deleted to protect the guilty]. At some point, the sex started. Not me,
obviously, but Tara, one of the hosts. She got absolutely railed by some
dude about two feet from where I was sitting. She seemed to be enjoying
it, although I think I'm all set with sex with guys. I'm just not
feeling it. That girl could party though, bless her. Still, not my
speed, I could definitely tell she was still a guy by the way she walked
and talked. Nothing against her, but either do it right or don't do it
at all. I suppose that's harsh. I still suck at a lot of this. Being a
woman is h-a-r-d.
End Diary Entry
I continued on my path searching for tgirl acceptance. I made some more
friends. I went to more parties. Boys hit on me. I resisted. I let a
few take some pictures of me. I worked on my voice, I worked on my walk,
I worked on my way. I could definitely flirt, especially if I was at the
bar and there were drinks to be purchased. I knew just when to smile, to
touch an arm, to rest my hand on a thigh. These boys wanted to take my
flower (I supposed), they wanted to put their cock in my mouth. I just
went home. I was still into girls.
And that was basically it. For a while anyway. I'd go out with my t-
friends, we'd have a blast and I'd go home. Some of them were getting
into sex with guys. I was still the demure type. But I began thinking
about having sex with men at some time in mid-2003. My friends were open
about it. They were doing it. It just started to feel and look right.
I had lost more weight and was down to 145 or so. At just under 5'10", I
was looking good (or so I thought at the time) and showing a little more
skin. And then, well ...
Author AK Remenko talks about "drift" in her Femme Your Hubby analysis.
Drift is the premise that a tgirl, in all her glamorous glory will, over
time, drift towards a sexual encounter with a man as a result of her
growing femininity. This is because as the feminine feelings increase,
the need for a penis as a means to completing the full feminine puzzle
increases as well. I believe drift exists. I drifted. I saw plenty of
others drift as well. We all did. I had lots of friends and every
single one of them drifted. Some went all the way, some just dabbled,
but all of them moved towards guy/tgirl sex over time. Was it the vodka
tonics?
Diary Entry: February 2004
I think it is just lovely that I do not remember his name. I am sitting
here and I cannot for the life of me think of his name. I can't believe
I am writing this, but he was hot. A guy was hot. And nice. And
French. And certainly many of the others wanted him and yet I, the
virgin, the virgin vixen, was who he chose.
We left the club around midnight. He was staying at the Radisson across
the street. I know for a fact I walked better than I ever had getting
over there. That black skirt just seems to keep everything on display
and top of mind. Into his room. He kissed me. I kissed him back. Open
mouth too. He felt my breasts through my blouse.
"They're not real," I said.
"I don't care," he replied.
He took my blouse off. I reached for his belt buckle. He slid my skirt
down. Then my hose. I was standing in front of him in my panties and
bra and cincher. I could feel him looking at me. He sat me down on the
bed. His open pants were at eye level. I reached in and touched the
first cock in my life that was not my own. It was warm and the skin was
soft, but underneath it was hard. And it was larger than mine.
I took it in my mouth and explored it with my tongue. I had seen enough
porno blow jobs to know what I should do. I was ready. His dick was
firm in my mouth. I loved the feeling.
Eventually he pulled out of my mouth and kissed me. Then he eased me
onto the bed and slid my panties down. My tgirl clit was exposed. I
loved it. Then he rolled me over. I offered my virginity to him. He
didn't know, but I did. I wanted him. He wanted me. He found me
desirable and wanted to fuck me just like those girls in the magazines
years ago. And I wanted him to fuck me. I wanted to give in. To open
myself. I felt some lube on my "pussy" and wonder still if he was
planning this hook up all along. What guy travels with lube? Someone
who plans on fucking some shemale ass is who. He greased me and I assume
himself. Then he pushed into me. I bore down and begged him to go slow.
He did. I wish I had more to drink, which is amazing because I know I
was hammered. Anything to take the edge off his 7" prick that felt like
it was splitting me in two.
When Stacy Hamilton loses her virginity to Ron Johnson, Audio Consultant,
in Fast Times at Ridgemont High, she confesses to her friend Linda the
next day that it "hurt so bad." Amen Stacy. It fucking killed. But he
came inside me. I felt like such a slut. Still do. I will get better
at this.
End Diary Entry
Looking at this diary, all I can do is laugh at myself. It's so
innocent, almost clinical. The funny thing is, I actually went about 4
months before having another encounter after that one. I find that
amazing because as I re-read my recaps through that time I was clearly
hooked on "the cock" at this point. All it took was one time. It's like
crack or something.
The Pharmacy OR These Are Tit Pills, August 2011
Hormones, the great dividing line for all tgirls. You either take them
or you don't. I started taking them when I was 26. I had-had-had to
have them. I wasn't interested in anything but looking and feeling as
feminine as I could. They took some time to do their thing, their damn
sweet time, and it didn't come without some trepidation. I was worried
about frying out my clit. I was worried about not being able to lose any
more weight. I was worried about mood swings. I was worried about my
health. I was worried - for a split second - about sprouting enormous
boobs and developing dangerous curves and then waking one day to realize
I didn't want any of what had happened to my body - that I wanted to be
Stephen again. For a split second. That fear went away fast and never
returned. I was in. All my chips to the center.
Diary Entry: October 2004
When? When? When are you little fuckers going to show yourself? When
will you sprout underneath my nipples? I have no soreness. My skin is
not softer. When?
End Diary Entry
Mind you, the whole time this was going on I was working at a pretty
decent job. I was still doing the Stephen thing at this time. I was
living alone in a little apartment north of the city. I'd race home from
work and Kristy would emerge within seconds. I was wearing panties to
work, so all it took was my cincher, my bra, forms and some face work.
Oh, and shoes. I fucking love high heel shoes. I'd parade around that
apartment all night, so vain, so silly, moving from mirror to mirror in
the best seductive manner I could. Want some fries with that shake?
Diary Entry: January 2005
I must recap the year that was. In short, I have taken the plunge. Sex
with three different boys and one girl last year as Kristy. Hormones
that don't seem to work (sadly). Friends! I have trans friends! People
seem to think I'm fun or funny or nice or whatever. So cool. I think
I'm nice too. Boys seem to find me attractive. I'm definitely a flirt.
Good-good-good dieting. I'm 142 as I start this new year. Getting
better! What will the year bring? I'd like to meet a girlfriend I
suppose. Someone who accepts me for who I am. The straight clubs will
hopefully help with that.
End Diary Entry
So fucking stupid Kristy. Meet a girlfriend? Are you fucking kidding
me?
And then, in 2005, I went the wrong way. Looking back now, I definitely
went the wrong way. Let me explain. I had been at this tgirl thing for
a couple of years. I could walk and talk and live. I had had sex and
knew my way around a cock and balls and a man's psyche quite well. I
could pass in most situations. I went to straight places far more than
ever. I shopped. I was basically living full time at this point, albeit
that existence required me to be a very femmy boy at my job. But it had
become obvious to everyone by now. My shape was changing, my face was
changing, everything was changing. I was becoming the new me. I had
ventured outside of the nest, so to speak.
And then I got the crazy idea that hey, I look like a girl and I think
like a girl and I identify as a girl - I should really and truly exist
that way, the way girls really do. Sounds good, right? Wrong. Well not
wrong, but not good for my sex life. I went chick all right, in all my
yoga pants and sweatshirts and jeans and flip-flop glory. I was the girl
at the mall who totally blended because I was dressed down and
comfortable. There were no statements to be made. I wore pants a lot.
I covered up. I thought I was doing myself a favor and honoring my
fellow genuine sisters. Sure I still rocked a pair of heels and a dress
from time to time, but I was reveling in just being a girl. I partied a
little bit, but I took false pride in talking about how I had chilled
out. I could not have been more wrong.
There is a simple law of physics. For every action, there is an equal
reaction. In certain cases, like mine, the reaction is sudden, jarring,
and almost violent in some ways. My reaction in 2006 was exactly that
and it opened the door to a world I couldn't have comprehended just a few
short months before and would change me forever.
Innocent Beginnings OR That Just Made My Honeypot Buzz, August 2011
It started simply enough. I had a date with a guy named Harry [not his
real name]. When I say "date," it should not legitimize it. Harry was a
friend of a friend, married, and our dates, when we had them, consisted
of him coming to my apartment with a bottle of wine. We'd chit chat
about the news of the day, about my transition or something else mundane.
When the wine was finished, we'd fool around a little bit and then he
would fuck me. This had happened a few times before. Harry was a good
lover with a sizable dick and, outside of the fact that he would push
into me too hard at first, it was always a decent time and I was glad to
be getting a semi-regular fucking from a nice guy. Mind you, this was
the beginning, when my cunt wasn't as easily accepting of a good sized
cock the way it is now. Hundreds of dicks change a girl.
Well, given Harry's married status, it was consistently up in the air as
to whether or not he was going to be able to make it. At that point, I
was just beginning to snap out of my dressed down lesbian phase and
really enjoying being a girly-girl and being comfortable in my skin. For
fun, I put an ad on Craigslist to find a rain check date in case Harry
cancelled. I'll let the diary tell the rest ...
Diary Entry: February 2006
My date with Harry wasn't going to come off. Enter Kevin. A lovely name
for a lovely man. With a lovely cock. I met him at my door in a short
black dress and black thigh highs, the dress short enough that the thigh
high tops were visible when I sat and crossed my legs. Black bra/black
g-string/black 4" pumps. My auburn hair was down. My eyes were dark and
smoky with a little bit of glitter on my eyes and brows. Pretty/slutty.
I cannot fucking believe I used to wear jeans and flats. What the fuck
was I thinking?
Kevin was pretty hooked from the get go. We made small talk for a while.
I think he was nervous, tgirl and all. He claimed he had been with a
shemale before, but I'm not buying that. Eventually the wine was gone
and he asked if he could kiss me. I said yes and he gave me a long drawn
out French kiss as I let my body melt into him. We broke the kiss and I
felt him with my hand through his jeans. Divine. I opened his belt and
buttons and he began to feel my breasts as we kissed. I reached into his
undershorts and felt his erection. I knew I had to have it. I pushed
his pants down and dropped to my knees, his cock flaring in front of my
face. Then I parted my lips and took him inside of my mouth, gently
lapping at him with my tongue. Heaven. I let my hands wander up the
front of his thighs and find his balls. They were heavy with cum and I
was delighted by the thought. I moved him back to the couch as he
fumbled to remove his clothes - oh the power a sexual woman has on men.
He sat on the couch and I resumed my blowjob, licking his balls gently
and stroking his shaft with my hand, my long red talons wrapped around
his stiff member. Then I looked up at him with hungry eyes.
"Do you want to fuck me?"
I began to take off my clothes as I continued to suck him, careful to
readjust my breast forms out of his line of sight. I had the lube tucked
away but at the ready and I offered my ass to him as I slid my panties
down my nylon encased legs and stepped out of them. Then I turned my ass
to him and bent slightly, allowing him to see his prize before he fucked
it. Kevin was nice enough to rim me before applying grease to my eager
ass-pussy. Then he gently pushed me to the floor - head down, ass up and
entered me. My whole body felt electric. I just felt so good to be
fucked again, to feel sexy and wanted again, to feel glamorous again. I
needed it. I needed the ritual of getting ready to get fucked. To
slowly select an outfit, to make sure my lingerie is just right. The
ritual of sexiness. It's back within me.
Kevin began to thrust deeply inside of me as I moved my hips back to meet
him. So perfect and perfectly sized, it didn't take him long to
establish a hard, deep rhythm inside me. I could feel his heavy balls
slapping me as I threw my head back and took the fucking like a good girl
should. He moaned and grabbed for my hips and I knew he was close so I
reached my hand between my legs and pressed his ball sac gently. That
was all it took. He cried out as I felt several heavy streams of cum
fill me. I had satisfied him and he pressed against me and eventually
lay on top of me for a few moments to catch his breath. As we lay there,
I felt his shrinking cock slip out of me. Then he stood and dressed as I
kneeled on the floor with my bottom between my feet, my semi-hard clit
exposed for him to see as a drop of his cum dripped out of my cunt. Then
he was gone.
After kissing Kevin goodbye my thoughts turned to cleaning myself up.
That's when the phone rang. Harry. He didn't have to cancel completely
as it turned out. He was running late and a little frantic, but he had a
little time:
"Kristy, honey, I have the wine and I'd love to see you. I don't want to
sound like a jerk, but I only have about 20 minutes if you know what I
mean."
I knew what he meant - Kristy, will you skip the small talk and open your
legs for me?
Of course I will honey. Let me put my panties back on and touch up my
makeup so I can skip the part about just being fucked. And your thick
dick should have no problem slipping inside of me. I'll just say it was
my vibrator. I didn't say that, of course, but I thought it.
Harry was at my place 10 minutes later. We popped the wine, had a few
sips and then he was all over me. We kissed, he took my hands in his and
placed them on his dick through his pants. I stripped off my dress, my
bra and my panties and dropped to my knees to receive his cock in the
exact same spot I had sucked Kevin from 40 minutes earlier. I blew Harry
for a couple of minutes, lovingly worshipping his sensitive glans before
I laid him down naked on the floor and lubed my pussy for show, his erect
pole standing at attention. Then I straddled him, placed his cockhead on
my open, cum filled hole and slid down on it. The whole thought of
having two cocks in one night is mind-blowing to me and it turned me on
with a force I've never felt before. In control and on top, I lightly
slapped at his balls as I worked up and down on his stiff dick, making
sure to take all of it to the hilt as I did so. Harry was clearly ready
to go when he got there because a few minutes later he yelled out and I
sat down hard on his shaft and felt his hot spunk filling me and mixing
with Kevin's as the orgasm rocked through him. Feeling his cock pulsing
like that was wonderful.
Then I was off of him and he dressed, leaving me naked, save for my thigh
highs and two dicks worth of cum dribbling from my gaping pussy. He took
another sip of wine, kissed me and was out the door.
End of Diary Entry
Looking back, that was the switch, the lever that did it, the blooming of
something inside me. Something had changed. Some reckless embracing of
my sexuality that I didn't (and still don't) fully comprehend. As I re-
read the entry, I laugh at my innocence. Later on I probably would have
taken a few extra minutes to let some of the cum drizzle into Harry's
mouth as my own diabolical way of making him pay for being late. I
certainly wouldn't hold it against him for getting right to the point and
saying, my cock-your ass, right now. That's a good man who says that.
But I learned a lot on that night. I learned that my ass could take a
two cock pounding. I was always a little worried things would be unclean
down there. As it became more of a regular thing I learned different
ways to ensure cleanliness, but back then this gave me the confidence to
not worry so much. I was barely eating anything anyway. I learned my
ass could take 10-12 thick streams of cum without boiling over - who
knew? And I learned that embracing my sexuality and dressing sexy and
not being afraid to do what feels good is OK - that I didn't have to be a
prude to be a woman. I had fought so hard against the stereotype that
transsexuals are just horny he-shes, that I never considered the fact
that I was a horny fucking chick who craved cock. This was who I was.
It's who I am. I had spent the past year fighting all of that. With
every action, there is a reaction and for me, it was the end of
considering girls to be an option. From that night on, I needed a hard
cock like the air that I breathe and my reaction to all of this was to
care less, wear less, suck more and fuck more.
End Part 1
There is more. Please review and comment. Thanks!
Yvette
- 23.11.2021
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