Date: Fri, 19 May 2006 02:24:47 -0400
From: Blair Cutiepie <melancholy_exile@hotmail.com>
Subject: Fate Or Chance? (TG)

FATE OR CHANCE? (TG - m/tg, oral, anal, romance)
by Blair aka Suburban Cutiepie (melancholy_exile@hotmail.com)

Responses welcome.

Chapter 1

"Did you see that?! Holy hell!"
I screamed along with about 5000 other people as the band sang its last song
of the night. The bassist in the band had just played a kicking' solo behind
his back, wowing the crowd. My sentiments were echoed by everyone else in
the two feet that my voice carried before being drowned out by the band, and
undoubtedly thought up elsewhere in the crowd.
Looking up, all you could see was the cloud of smoke hanging in the small
concert hall, highlighted by the pinks and greens of the stage lights. The
air smelled of marijuana and cigarettes - the lead singer of the band had
lit a smoke halfway through the gig and, when he needed use of his hands for
the guitar, had placed it between two strings on the headstock. And I of
course followed suit, saying "screw you!" to the anti-public smoking laws
that the Nazis at Toronto's Queens Park had ordered in place.
The concert ended with a minute of the guitars revving up to a complicated
symphony, then drowned out in applause. I cheered and roared with my friends
and all the other entertained patrons.
My friend Matt looked up at me - I was only 5'8", but taller than most of my
friends. It gave me an advantage at the concert - my friends were all in
front of me, and since they were shorter I was guaranteed a good view of the
stage. He said something, but the echoing in my ears was still fading so I
tried to tell him to wait until we were outside.
As the concert was ending and people were waiting to see if there was going
to be a second encore, I looked to my left and made eyes with a cute
brunette who happened to look over at the same time. I gave her a shy grin
and she smiled back at me. We shouted a quick exchange, barely audible but I
had put more effort into hearing her than my friend. She had asked me if I
wanted to go to a bar after the concert, and I couldn't refuse.
I turned to tell my friend where I'd be headed, but my pack of friends had
already started migrating through the thick crowd and had lost me. It seemed
like my schedule was free, anyways. But turning back to the girl, I found
her missing too, swallowed up by the crowd that was shuffling towards the
door.
Down on my luck and hoping to catch the brunette or at least my friends out
front, I moved with the crowd until I was out in the fresh, cool air.
Standing shoulder-to-shoulder with so many people made for hot, sweaty, and
occasionally smelly people.
It was nice to be outside again. But unfortunately, my friends were nowhere
in sight and I had no luck finding the girl. I waited around on the street
corner for a while until it all seemed hopeless and began to start walking
to the subway to catch a ride back to Yorkdale and from there to my bed in
suburbia. I was rather depressed, kicking stones. Without friends and
without the girl. The girl part hurt more, I had to admit. I was a hopeless
romantic, and had been single for a few years now.
As I walked, I passed a fairly reflective storefront window and stopped,
turning to look at myself, asking silently if I was unattractive? I was
short, but not too short. And my face had a good sense of symmetry with a
strong jaw, fine eyebrows, kissable full lips and a full, thick set of
eyelashes. I even had a beauty mark in the exact place as Marilyn Monroe's.
I wasn't very muscular. Don't girls like muscular guys? I was so thin in the
arms, and curvy around the hips.
I walked on, trying not to be so self-conscious. "It'll happen," I told
myself. "All you have to do is wait."
The street was quiet - few cars drove by, and even fewer pedestrians walked
the streets. It was coming close to midnight, and most were either safe at
home in their beds or on their way to doing so. Which is what made my
encounter with Loren so strange.
She was sitting on a set of steps leading up to a residential building
drinking a beer. She seemed cute - her hair was dyed a deep, dark red that
complimented her fair skin wonderfully. It wavered from its place as she
turned to look at me, and smiled, raising her bottle to me in cheers. "Did
you just go see them?"
I stopped in my tracks and looked at her with an oblivious expression on my
face. "Pardon?"
She gestured to my t-shirt. "The band, did you see them tonight? I heard
they were playing at the Underground tonight."
"Oh! The band! Yeah, I'm just on my way home. It was a great show, totally
blew the crowd away."
She laughed some. "I saw them last time they came. They've got a real
ambient sound."
Ambient. Huh. "Want to go grab a beer?"
She quirked her eyebrows at me and shook her bottle in front of my eyes.
"Just how high did you get?" My eyes must have been really red. "I already
have one right here, cowboy."
I laughed nervously and stammered a response, fighting the urge to blush
like a tomato. "I mean like at an actual place. Isn't Finn McCool's just
around the corner? They'll be open for another three hours and I've been
stranded high and dry in the city by my friends."
She smiled at me from the steps. "Sound's like a plan."
Standing, I got my first good look at Loren. I placed her at my age, 20. She
wore a green top with a nonsensically cute phrase printed on the front and
back and form-fitting jeans. She wasn't a thin, frail looking thing. Her
jeans were filled out in the right places, ample but not excessive, her
stomach looking cushy but flat, breasts petite but a handful. What a sight.
And she seemed to have good taste - in style and in music. Her eyes spoke of
intelligence beyond what she would show. Her ears perked over her red hair,
which she had pulled back except for a few locks left hanging on either side
of her face, pierced with two simple amethyst studs.
We walked halfway, laughing all the way about music and old concert
experiences when she stopped dead in her tracks and turned on a dime to face
me. "Oh my god." She looked at me and started laughing. "What's your name?"
I blinked. We hadn't even introduced ourselves. Yet here she was, more than
willing to come to a bar with a perfect stranger. Was it bad judgment on her
part, or just plain chemistry?
And so I introduced myself to Loren. "Holy hell, I thought we'd already done
the introduction bit! I'm Blair."
"Hi Blair. I'm Loren. Are you a rapist?"
I blinked again. A rapist? "What? Hey, you're the one who came with me, I'm
not dragging you kicking and screaming."
She laughed. "Just making sure." She grinned and walked with me to the bar.
And that was how I met Loren.

Chapter 2

Loren and I had begun seeing each other regularly. I would catch a bus or
the train down to Toronto and see her about three times a week. And at least
once during that week, we would go to Finn McCool's and sit in the same
booth we sat at the first night. I discovered we not only shared taste in
music, but in a great many other things. We accepted the things we didn't
share with one another, and in that we managed to make it work despite the
traveling involved in the relationship.
Things were progressing between her and I. I was beginning to invite her to
dinner at home or out with my group of friends. She seemed to enjoy the time
we were spending together, and so we continued on a steady course as our
relationship grew. It was clearly romantic in nature, and yet we had only
kissed twice in the two months I had met her on the front step of what I
later found out was her home.
She worked as a waitress part time, and at a call center for the rest of the
time. She made enough, she said, to get by. Her parents had kicked her out
when she turned 16 for what she called "irreconcilable differences". I told
her she sounded like a lawyer (she didn't find it funny). She was originally
from Manitoba, but had moved to the city when her parents had put her out on
the street. With just a bit of money from an inheritance, she finished high
school and paid her way to Toronto.
"And to where I am today, working in a Denny's, selling an All-American
Breakfast in Canada and getting jack-all for tips."
She didn't like thinking about her past. Mentioning her parents got her very
upset.
The one-bedroom basement apartment of hers was small enough to be a cage,
but she had done well in decorating it with furniture themed in a mahogany
stain. I was spending more and more time there, and while it normally would
have felt cramped, the two of us were always close anyways.
It was a strange friendship, one always kept just shy of anything more. I
was kept dreaming, as was she (I hoped) though I could not understand this
seclusion from more intimate romance. We had shared a great deal of time
together. I took her out as often as I could. I even surprised her on her
birthday by taking her to Montreal and then Quebec City, declaring the
entire weekend her birthday. Yet still we bordered between friendship and
romance. I had asked her many times if she was seeing someone else, but each
time she got more angry at me for even suggesting she was being untruthful
about that and more importantly each time she told me, flat out, "No."
The relationship was pleasing though - just spending time with her was. And
we knew of each other's feelings but simply chose not to pursue them any
further. Yet I longed for the day that she would just let me wrap my arms
around her and not see an awkward look on her face.
I was brought back to that night when I had first met her. When I stared at
myself in the reflection of the storefront window. Was I right for thinking
I had a face that would sink a thousand ships? Or was it really just fate
simply taking its time to come around to my neck of the woods?
The summer was finally ending, the days slowly getting shorter and cooler.
When I wasn't working, I was spending time with her. And so it was only
natural that when University began in September, I decided to move to the
city. However, with the price of places downtown I knew I could not find a
place alone without living in a cramped, barely-livable apartment like
Loren. We had grown closer by now, and were regularly kissing. It was still
quite clear that she was setting the pace, and it seemed our relationship
was more in the romantic side of things than the friendship. Yet still, we
kissed only between long interludes and never for too long a time. This
relationship took a lot of diligence. So I approached her on the subject one
night while we were in the kitchen at her place, making some chicken
Alfredo.
"So... classes start soon."
She rolled her eyes some. "Every September."
She didn't like me talking about University much, either. She must have had
some shattered dreams, I thought. "The commute is going to be awful, getting
into the city every day. It'll be at least a two hour round trip."
She retrieved two plates from her cupboard and set them down as if to say
`enough with the pussyfooting' and gave me a stern look between wisps of red
hair. She was wearing it down to her shoulders now, and I couldn't decide if
I liked her better with it pulled back or down. She looked great all the
time - even when looking at me as rigidly as she was now.
I finally decided to just be out with it. "Want to find a place together?"
She laughed and the stern look washed right away, and soon she was blushing.
"Of course."
And so we moved in together. We found a nice little apartment that had a
rent that we both could split and still live comfortably. Loren got a
promotion at the call center and quit her job waiting tables. I worked
weekends at the dockyards and from Monday through Thursday I worked as a
clerk for some high profile business in the city.
Moving in together had some definite perks. For one thing, our relationship
finally solidified. We became a couple. I guess being together with someone
long enough, a bond just inevitably forms. I finally could run my hand
through her hair, or kiss her forehead and nose and ears and lips. And she
grew a habit of nibbling on my earlobe when I had my head turned, then
nuzzling my neck. We still strayed quite shy of the sexual bits and pieces -
I mostly out of respect, being the second to make a move normally - but we
had effectively transcended into couplehood.
Still, we kept two separate rooms. Never did we sleep in the same bed
together, and for some reason she kept a lock on her door while mine
remained completely open. I again thought back to the first night we were
together, when she asked if I was a rapist.
Great, first I thought I was ugly, and now I think I look like a rapist, I
thought to myself. I dismissed the lock as a need for privacy and carried on
with my life and our relationship.

Chapter 3

"Oh come on Loren, it will be fun."
She looked at me questioningly. "Cuba? At your grandparent's expense? I
can't, Blair. It's just too much money."
I laughed. "Oh, come on! You know you'll enjoy yourself! Lazing in the sun
on the beach all day... an all-inclusive swim-up bar..."
Her eyes lit up. "A swim-up bar??"
I shrugged my shoulders playfully, a smile from ear-to-ear across my face.
"Glad to see something caught your attention. Come on. They offered the
invite to you specifically."
She seemed like she was dealing with a massive internal struggle. "I...
can't. Blair, I can't. I'm sorry."
I sighed. "Why? A free vacation, all expenses paid, and you're turning it
down. You know I won't want to go if you're not going to come with me. And
my family really loves you. They think you've got spunk." That made her
giggle some. "Please?"
It was now her turn to sigh. "Blair, can we sit down?"
I was worried. Very. That is the number one sign of a breakup. A girl wants
to talk about why she can't do something with you, and then tells you to sit
down before she breaks the news.
"Why? What's this about?" She was biting her lip, looking at me
questioningly. "Loren? What's this about."
She grabbed my sleeve. "Just come here." I went with her and walked to the
living room where we sat on our couch. She was holding my hands now,
squeezing them every now and then, running her thumbs against the contours
of my knuckles.
"How long have we been together?"
I tried counting in my head. "Five months?"
She smiled warmly as I said the number, and then leaned in and kissed me
with her cupid's bow lips. As the kiss ended, she rested her forehead gently
on mine, and I could feel her eyelashes tickle me as she opened and closed
her eyes. And then she pushed me back onto the couch and leaned in, pursuing
the kiss even more. I held her, my arms wrapped around her slim waist,
feeling her weight and warmth against me. The kiss was fevered now. I
tickled her arms with my fingertips some and felt her shiver in mid-kiss.
She broke off with straggled breath, perched over me on my lap, her legs on
either side of mine.
Oh, what a sight. She had her palms resting beside my shoulders, arms
straight, gazing down at me. The light let in from the balcony shone around
her head and for a moment it seemed like she was a glowing effigy to beauty.
Her pert breasts determined the fall of her shirt, slightly riding up the
front to reveal her navel, an inny. I leaned in and blew a large raspberry,
and she giggled with a delicacy I adored.
She slid down my body and I held her for a long while, just looking up at
her, our noses nuzzling on occasion. We laid there for hours after those
frenzied kisses. And while I was transfixed by the tenderness, the love I
felt, I knew she was deep in thought. She had brought me to the living room
to tell me something, not to lay with me. Unless of course what she wanted
to say was that she loved me, but I already knew that.
I ran my fingertips along her spine, very gently, feeling the soft bumps. My
nails lightly raked along her back through the fabric of her shirt as they
drifted back up to redo its course along her spine.
"Blair..."
I opened my eyes and saw hers, half-opened, looking sad. And it was then
that she took my hand again, stood up, and brought me to her room. She
unlocked it and then did something I did not expect - she gave me the key. I
pocketed it and walked hand in hand into her room. It was decorated with a
sense of conservative style and a little teenage charm. A few posters were
pinned to the wall, but there was also a few paintings and some elegant
photographs she had taken. Her large bed was unmade but looked warm and
inviting. She led me to it, pushing me to lay down on it. I sprawled out and
propped my head up, watching her at the end of the bed.
She reached down to the bottom of her shirt and lifted over her shoulders,
and at once I was bestowed with a sight of this beautiful, fair-skinned
body. She looked at me with love in her eyes, this half-naked goddess before
me, my beautiful Loren. Her red hair had become tasseled as she took off her
shirt, so she shook it free, her pert breasts bouncing somewhat with the
motion. I was transfixed as I sat there watching her, and then she began to
remove her jean skirt. It fell in a pool around her ankles, and I could see
her standing before me now, in nothing but a pair of lace panties, and I
drank in the image as if I were a man exiting the Sahara. I said one word.
"Beautiful."
She crawled onto the bed and over me, her soft body like that of a nocturnal
prowler stalking prey. I felt her breasts press against my chest, and she
dipped in to kiss before breaking off to take off my shirt. The buttons came
undone quickly, and she kissed along my revealed chest. Her tongue traced
little circles, enticing me, making me shiver.
And then she stood. She looked worrisome and I could see the internal
conflict behind her eyes. I wanted to reach up and stroke her face gently,
tell her it's all right, and that we did not need to continue if she didn't
feel comfortable with it.
Then she slid her black lace panties slowly downward, letting them fall to
her ankles. In the dim light I could see her. She was trimmed, her soft
patch of what I saw to be blonde hair in a broad rectangle. She reached
behind her and seemed to struggle with something as she had pulled down her
panties. I watched her curiously as she stood before me.
My heart leapt into my throat. I couldn't believe what I was seeing.
Loren, my sweet Loren. Why did you lie?
I saw clearly, despite the dim light, a phallus swing between her legs, half
flaccid, about five inches in length.
"I'm sorry."
I said nothing. I stared. I looked up at her to see we both looked crushed.
Why did you lie? I loved you.
I love you.
Internally I felt conflicted, but my last thought rang so true in my ear. I
loved her. And yes, she was a she, regardless of her actual gender. She was
Loren. She was a woman. I could never see her as anything but. Looking at
her face, stricken with tears at my distraught look, I could see no sign of
the male within. Her face was not blocky but finely made, elegant, with
cheekbones like Rita Hayworth and lips like Judy Garland, the fairest of
bodies that was petite yet rounded in the right places. She was no man. And
yet, between her legs, I saw what I saw. A penis, plain and simple.
I stood, feeling weighed down by the thoughts racing through my head. What
do you say to the woman you moved in with, you took home to your family,
after they have just revealed such a devastating secret?
I will admit I have no reservations when it comes to sexuality, and in my
past I had sexual relations with several of my male friends. In the culture
of this day and age, it seems everyone as bisexual except the select few and
I accepted that term as the definition of my sexuality. However,
transsexuals were taboo to me. They were the cross-dressers with obviously
male faces and bodies in go go dresses and red wigs on Church Street. Yet
this woman, Loren, changed my perspective. She was not one of those. She was
beautiful. She was feminine. I knew that she was a man, but to me, looking
at her now, I did not see man or woman. I saw Loren. My sweet, sweet Loren.
She kept standing there, waiting for me to say something. Waiting for me to
make it better or worse. "Loren..." her name was choked out.
She bit her lower lip and looked down, her hands folding together above the
topic of discussion, fidgeting with nerves.
I took her in my arms and held her as she cried. I felt her body against
mine as I had so many other times before. And was it different this time?
No. It wasn't. It was the same as the night before. The same as the first
time we met.
I took a hand and lifted her chin, and she looked up at me with her mascara
running and a quivering lip, and I kissed her. I kissed her hard and
lovingly, and I kissed her like it was my first and my last time doing so
all at once. The embrace heated as I held her as did the kiss, where now our
tongues had slipped from their velveteen mouths to meet.
She moaned and mewed with contentment as we kissed and I knew I had made
things better. And in myself, I knew I made the right decision.

Chapter 4

And so our bodies feel against the bed once more, and this time I was atop
her. With my hands running through her hair I finally broke the kiss,
gasping for air. My face had some of her running mascara on it and she
reached up with a thumb to brush it away with her thin, delicate hands.
"I love you." She giggled. "You're Loren, no matter what. My sweet Loren."
We resumed kissing, our bodies entwined. We rolled about, and again she laid
on top of me. I felt her rigid penis against my clothed legs. I didn't mind
it. In fact, I enjoyed that feeling just as the warm pelvis of any girl I
had ever laid with. I ran my hands along her back, feeling the contours of
her shoulder, the dip in the small of her back, the rise of her bottom and
finally the smoothness of the back of her thighs. Her entire body was an
unmarred milky cream colour, complimented by a small collection of dark
freckles on her right shoulder. I kissed that spot profusely as she nibbled
along my neck, kissing up to my earlobe to take it in and give it a soft
nibble to send a quick jolt through me.
Sliding down my body, she removed my jeans with ease, then took her time,
teasing me, as she removed my jockeys. She had never seen me in my entirety,
and I saw the anticipation in her eyes as her prize was at long last
revealed. My rather erect manhood stood at attention before her, popping out
as soon as the elastic band of my shorts had passed the point of no return
along my shaft. While just shy of seven inches, it was thick and uncut,
engorged with blood and emanating heat. She too was wordless, though her
expression told me she was pleased and that the sight had heated the fire
between her legs. She reached out and tried to wrap her fingers around it,
and stroked my endowment slowly for the first time, placing kisses along my
thigh. I sighed in delight as the kisses were laid closer and closer to the
root of my shaft, where she began letting her devilish tongue snake out and
give a taste to my flesh.
She crawled up the bed and over me, straddling my waist. And shyly though
with confidence, she showed off her cock to see. It was beautiful, the head
seeming polished and reflecting some of the dim light in her room. She held
it, and I watched her stroke it before instinctively putting my own hand on
it and gently doing the same. I held it and ran a fingertip along the v of
her head, down its length along the blood-laden vein. I was amazed at the
beauty of this exotic creature before me. This attribute of hers, it did not
mar her but enhance her.
She slowly moved her hips in concert with my hand, and brought herself
closer to me with each thrust. Eventually I could feel the heat of her on my
face, and leaned forward, a strong arm pulling her close and firm while my
other hand held the base of her hardened phallus, I leaned forward and
opened my mouth and accepted it between my lips. I heard her gasp, surprised
by my willingness to do this deed she did not request, and she helped by
slowly thrusting in synch with my mouth. My hands slid up and grasped each
cheek of her soft, round and supple backside as I had done so many times
before through her jeans, as my tongue slithered around her rigid shaft
between my lips, my mouth salivating.
She began to lean back, placing her weight on her curled up legs and one arm
planted by my feet. Her back arched, I looked up to see her flat stomach;
her perky breasts with the protruding, hardened nipples and her mouth locked
in a sanguine shape, dark red hair hanging freely in a raw and sexual
manner. My nose buried in the soft patch of blonde hair, I realized how much
I enjoyed pleasuring her and watching her react to those delicious feelings.
This carried on for a good long time until she removed herself from my
mouth. One look up at that beautiful face and I knew that she was beginning
to get incredibly close. She slowly stroked her cock in front of my face,
her eyes shut, back arching like a cat stretching. Her hips were gyrating
against my chest as I watched a steady leak of watery liquid begin to seep
from her and down her shaft, over her knuckles and onto my chest. She moaned
and quivered in delight, pulling herself slightly faster. She came a viscous
creamy white, coating her cock in it with each stroke, her lip bitten in
ecstasy.
I was wowed by my first experience with her. Yet I knew it was not done yet,
for she looked down at me, tiredly, but in an absolute devilishly manner.
"You've done that before, haven't you?" I blushed viciously. Of course I had
never told her about my same-sex exploits.
She slid down against my body and nuzzled close to me, and I could feel her
slowly softening organ laying against my chest, slightly sticky. I ran my
hands through her hair as her hands made her way downwards, along my body
until they stopped between my legs, an achingly longing cock jumping at her
touch. She handled it gently but with control and knowledge, and I shuddered
with delight. As she continued to slide along my body, it became clear that
she intended to return the favour.
Now laying between my open legs, she held my manhood with pride and began to
give it soft, gentle kisses all across and throughout. This of course was
quite stimulating, and the effect was doubled when her hands went to
delicately massage the aching, filled globes that hung beneath my shaft.
Her lips ran upwards, brushing just firmly enough against me that as she
passed my mushroom shaped head that I let out a very audible gasp, feeling
her tongue replace her lips finally at the crest. She took the first
half-inch within her mouth and suckled on it gently like a babe on her
mother's breast. Her tongue swirled across the head, and slowly she began to
press downward, adding a slight piston movement to her already decadent act.
"Oh my god Loren..." My moans were animalistic and wrapped in pleasure. My
hips were bucking now, and looking down I saw her looking back at me, her
large almond-shaped eyes wide-open and gazing into mine, her lips even while
wrapped around me were bent into a smile. I hadn't seen her look at me like
that before - and I was sure it was not our sudden rush to sexual intimacy
that was playing her emotions so. She no longer had any fears. She felt free
of the bondage of her past.
She had taken me entirely into her mouth, and with each press downward I
felt her tongue roll along the underside of my shaft, feeling the warm drip
of her saliva almost feel cold against my heated self. I took in the
feelings all at once - her lips tight around me, tongue caressing, her hair
tickling my thighs each time she lowered her head, and now a slight,
rhythmic tickle between my anus and my testes. I felt a cool breeze over my
naked body come in from an open window, chilling me and causing my hairs to
stand on end. And then very slowly she began to circle my rosebud with her
finger while she made quiet mewling and suckling noises.
The unexpected surprise had raise my hips high, my legs partially spreading
in an unconscious effort to help her in her efforts. I felt myself harden at
the excitement, and in turn knew I was getting close. So did she - my
breathing had picked up, and my withering on the bed had increased.
I popped out of her mouth with the sound of suction being lost and she
nuzzled against my manhood, slick with her saliva, before raising up before
me and once again moving to straddle me. Yet she paused halfway and reached
down, adjusting the direction my stiffened cock pointed. My hands reached
out on either side of her hips, holding onto her globes, gently kneading
them, pulling them slightly apart as she lowered herself onto me.
I felt the resistance at first. She tightened instinctively, not allowing me
entrance, but slowly she eased herself onto me and I felt her slowly open.
Quickly she withdrew and repeated, always taking her time, moving slow to
adjust to my size. After several agonizing tries of her testing the waters,
at long last I felt her sphincter tighten around the base of my head.
Her gasp was drawn out, a hiss of pleasure, feeling my fit with little
discomfort. Propped up by the strength of my arms around her waist, she
lowered herself slowly, my foreskin being pulled taut and then loose within
her, with each tightening moment sending volts through my shaft as the skin
of the head tightened in my cock's strain. I watched her, each thrust
downwards bringing her half an inch lower than the previous, always having
my head re-enter her as she dipped downwards until at long last she sat
flush against me. Her jaw was loose in pleasure, eyes somewhat glazed over
as she looked down at me. Her hips rolled along mine, gyrating as I
stimulated her from within. And between her legs I watched as her beautiful
penis became erect once more, stiffening ever so slightly at first, growing
in breadth and length, until it stood strained, pointed upwards, in her
moment of heat.
My hips were meeting hers in thrusts now, and I kept one hand on her round,
plush backside while another stroked her member. My thumb polished her head
with gentle friction, and I saw the squirming of her pleasure each time I
hit what I found to be a particularly sensitive spot on her.
Our pace was increasing, frenzied, and our bodies were wet with sweat. The
sound of flesh upon flesh filled the room as did her moans of absolute
sexual fulfillment. My thrusts were growing harder and deeper as she pressed
on, and I felt my hand around her slick with her precum. My hand, slick with
her juices, shuffled along her faster and my hips followed suit.
For the second time in one evening, I witnessed Loren ejaculate. She came
before me, and her hand took the place of my own and she pulled herself to
pleasure. I watched her cum dribble down, falling amidst my navel and the
trimmed hair above my manhood.
It was an incredibly attractive thing, to watch my beautiful Loren achieve
that state of sexual pleasure. Her eyes slightly squinted and she seemed to
always bite her full, red lower lip in the most attractive manner. Her
abdominals flexed and shuddered, the cheeks of her ass clenching, as did her
insides like a glove pulled tight around the skin. I delved deeper into her
and felt my own release into the depths of Loren's body.
"Oh... Christ... Loren..." I was not one for words at that point.
And then we both collapsed, she atop of me, myself still inside of her, my
own body limp against her soft bed sheets. Her hair was damp with sweat and
locks grouped together, falling on either side of her face and in strands
along her forehead.
We laid there kissing and cuddling for quite some time, not a word said,
just relishing in the fading moments of our first time together and the love
that surrounded us.
I fell asleep, her in my arms already dreaming of what I hoped was me.

* * *

Loren later told me her full story. She was raised in Kenora to wealthy
parents, her father the son of a wealthy oiler in Alberta. She had known how
she felt since she was young. Her body was a naturally feminine shape and
likeness, and her voice had always been pitched higher than others, more
feminine. Of course, she struggled with her sexuality before becoming
assured of herself when she turned seventeen years old. When she told her
parents how she felt and what she wanted in life, they had disowned her
immediately.
However, her grandfather had passed on some years earlier and she had her
portion of the inheritance as legally entitled to her, no longer in her
parent's trust.
She used that to get to Toronto, where she underwent a series of surgeries.
She did not need to get much done; she went on estrogen and her voice soon
found itself in the very natural, feminine tone it was when I first met her.
Soon her breasts formed, which she later replaced with implants.
"Very expensive implants." She noted.
She had her Adam's Apple shaved down some and had slight plastic surgery on
her chin to round it out more and two ribs removed.
"And that brings me to who I am today. Nearly broke. But I have you."

Chapter 5

The trip to Cuba was Loren's first time on a plane. We were flying with some
economy class airline but she remained impressed nonetheless and I was happy
to see her so enthralled with the sight of us flying high above South
Carolina, viewing the eastern coast of the United States from above. She
didn't even complain about the food - although I did, and by the end of the
flight she didn't want to hear about it.
To pass the time, her and I wrote little haikus making fun of the airline
industry and the people on the airplane in general.
"Tax-free alcohol / The pilot too drunk to fly / Fly Irish Airways!" I
laughed hard enough at that one that the stewardess told me to keep it down,
all the while with Loren elbowing me playfully in the side.
The plane touched down in a very basic airport, and we had to walk onto the
runway from a ladder as they had no real terminal. We passed a rather
militant-looking security check before entering the airport and soon enough
we were on a bus to the resort, my family along with.
Loren had worried a lot about wearing a swimsuit in public. It wasn't the
fact that anything showed because to be honest you would likely be oblivious
to the fact that she had more than met the eye between her legs, but more
that she would not be able to deal with public embarrassment in front of my
family had some accident occurred where she was revealed to one of them,
especially with limited places to run off and hide on the island resort,
surrounded by forests and poverty-stricken areas. But we had managed to get
her another one of her garments, called gaffs, in a swimsuit model before
traveling. It secured her invisibly, allowing her to wear a swimsuit she
wanted without worrying about the bulges she feared would show.
The bus ride to the resort was depressing - not just because outside we saw
the poor, hungry souls who chased after the tourist buses, the prostitutes
who rode their bikes alongside to show off their goods to the tourists with
hard currency, but also because my grandfather had decided to sit in front
of us, and had his back turned to tell us about how his father had helped
put down a rebellion here with the great Winston Churchill himself. It was a
good story, though there was not much to it, and that was readily apparent
five minutes into his reciting the events his father had told him.
The resort, however, was beautiful. White arches greeted the buses, and
within we saw that the lobby was an open-air environment, with large steps
leading upwards to where the registrar sat behind his desk.
We all moved together to the front desk, waiting in line, taking in the
vegetation and what little of the coast we could see behind the beautiful
buildings housing the rooms. And soon enough, we had our resort's wristbands
and were free to wander as we pleased.
The room we shared had one large king-size bed, with soft silk and Egyptian
cotton sheets that were a delight to lay in, and for the first thirty
minutes Loren and I spooned on the bed, enjoying the cool air of our rooms
and the warmth of each other.
We spent the first day wandering the resort, seeing all it had to offer. A
gymnasium, several activity centers, two pools as well as a white sand
beach, and both sailboats and scuba equipment for rent. The pools, however,
were full of fat and drunk German fellows playing water polo, and the
gymnasium was full of fat and drunk German women jazzercising, so we chose
that the beach would be the best place to spend our time.
Loren had gone swimsuit shopping a few weeks before we left, and she refused
to show me what she had bought, wanting to keep it a surprise. So she
hurried into the bathroom of our little hotel room with her beach bag and I
waited outside the door, wondering just what she would wear.
It took some time for her to come out, but when she did I was quite
surprised. She had chosen a wonderful red two-piece, her bottoms were broad,
almost like shorts, but crimson in colour and with very sexy circles cut out
along the outer legs, the short's material held in golden hoops. Her top had
two smaller hoops at the front in the milky valley between her breasts that
served as a clasp. And as she was in there, she had let her dark red hair
down to spill over her shoulders.
She spun around in a circle, showing the swimsuit off to me. It fit her form
so perfectly, complimenting her hair, eyes, and the fairness of her skin. I
played dumbfounded, then walked into the bathroom, shut the door for just a
moment before exiting with a grin.
"Did it work? Am I transformed into an Adonis? Or does it only work on
turning young ladies into an irresistible Aphrodite?"
She smacked my shoulder with a giggle. "How did you manage to nab me with
lines like that?"
We walked through the hotel rooms along the large open-air walkways that
lead from the rooms to the main complex, which backed off onto the beach.
Our stroll was silent but peaceful and comfortable, our hands entwined as we
enjoyed the hot sun and soon the sand between our toes as we searched for
some place to settle in amongst the hundreds of other people laying out on
towels trying to brown out in the sun.
Our day was spent on the beach, and my eyes continuously wandered over to
Loren to admire her lithe young body that I had never seen so revealed in
public. Yet she was comfortable as any, her milky thighs and toned calves
showing for all the world to see. I liked seeing her so confidant, and loved
it even more when our eyes met and I saw the warmth of her love gaze back at
me.
The water was very warm, and Loren had never swam in the ocean before so we
took the time to take a leisurely swim along the beach to the far end of the
bay and back. Every now and then, a jet ski or speed boat would roar past
the bay and send waves rippling towards us and we'd both go under together,
her trying to use me to keep her afloat, me sinking underneath.
After a day of tanning, swimming, and snorkeling over coral reefs, we
decided to go and grab some dinner, the airplane lunch long since absorbed
by my body through all of the activity. The dinner bar held several entrees,
much of which was seafood.
We enjoyed a quiet, relaxing meal afterwards as we listened to the soothing
sounds of a Cuban guitarist playing for the guests somewhere in the room.
After dinner, we joined the family for drinks at the bar. Loren faced many
questions, but my brother took me aside privately and complimented on her
figure, calling her a catch, and after I had echoed this to Loren, she began
to become even more at ease. I of course indulged in the drink, feeling my
sunburn on the fair skin of a man who had lived many Canadian winters and
trying to dull the ache. I played some pool with my brother and cousins for
some time before retiring for the evening, Loren waving to the family with
me as we walked to our room.
As soon as I entered, I walked to the bed and flopped down on it, then
suddenly wished I hadn't. My body tensed up and I gritted my teeth. "Ow."
Loren laughed at me and came to sit next to me, peeling off my shirt to look
at my burned, red skin. "Honey, I told you that sunscreen wasn't
waterproof."
I shrugged, wincing at how it accentuated the pain in my shoulders and neck.
"I wanted to be right."
She sat up, telling me she had just what I needed, and came back with a
lotion. I had stripped to my boxers and was laying on my stomach as I had
earlier when I fell asleep on the beach in the open sun. She put some of the
lotion on her palms and proceeded to rub it into my arms and, for a moment
as I lifted my chin my face, then moving up my shoulders, cooing soft
nothings to me. The lotion felt ice cold against my skin but it was a great
feeling and I sunk into the bed even more. Her hands roamed my back, running
all over my flesh with the softness of her fingertips. Her hands rolled
downwards, feeling the dip in the small of my back as she massaged the
lotion into my skin.
She seemed to hesitate as she hit my swimming trunks, and then pulled them
off too and cast them to the pile on the floor of other dirty clothes. She
giggled slightly and gave me a soft spanking on my bare bottom. "You've got
a terrible tan line, love."
She put more lotion on her hands and got off the bed, moving to my feet, and
rubbed slowly up my legs. It felt delightful, especially on the back of my
knees where it was stinging the worst. Her hands moved upwards onto cool
skin, and I knew she was doing more than just my burned area. Her hands went
along my bottom, cupping the shape of them and rubbing the lotion into the
soft skin. Her fingertips ran between my cheeks playfully, and she came back
on the bed and laid herself next to me, her hands still playing with my
tush.
Her almond eyes gazed mischievously into mine, and she leaned down for a
brief but passionate kiss. "You make one sexy lobster." She laughed, and I
joined in, then pulled her close, our noses touching." You'd love the
hideous lobster boy? Mmm, you must be heaven sent." And we kissed again.
She slipped off the bed and I rolled, somewhat painfully, onto my side to
watch her undress. She unclasped her top and slid it off her shoulders to
reveal the perfect handfuls of her breasts, and then she removed her
bottoms, untucking herself and stepping out of the bathing suit gaff.
"So beautiful." It was barely a whisper.
She got back on the bed and spooned with me, her breath, flush skin and
breasts against me, and I slowly felt herself harden along my lower back.
This felt good - it was hot and felt good against the only cool skin I had
after that sunburn.
Gradually she began to grind herself against me, lowering so that she
nestled herself between my cheeks without entering, the occasional bite on
the nape of my neck. I laid there, astounded, my own cock at full length and
width as the blood pounded to my loins. I wrapped my hand around my tool and
began to stroke it, needing no lube as I was uncut. I moaned along with her
now, and she reached around me to fondle my testicles while I bucked both
against her and my hand. Her nipples were diamonds against my back.
Then she began rubbing the head against my rosebud. I had never been
penetrated before, despite my past experience going down on guys, and I
began to protest but she swiftly cooed my complaints away and I felt her
gradually, in several deliberate attempts to loosen me up and have me get
used to it, fill me from behind.
It was, at first, painful. Just a little. She had gone slow enough that it
did not sting too much, although there was a distinct burning around my ring
at first. But after the head had passed, I felt much better. And in time,
the pain, it either dissipated in time or was overwhelmed by pleasure.
I felt her testes, close to her body, press softly against my cheeks each
time my hips met hers. I, pounding myself so hard in my hand, was also
grinding backwards and onto her. She was moaning and occasionally letting
out a yelp of pleasure that somehow satisfied me so much, to hear her
enjoying me that much, to know I was bringing her pleasure at any rate.
"Oh Blair, I love you, I love you Blair..." she whispered in my ear harshly
and suddenly bucked hard, deeply pressing into me and I felt pressure within
me. She was holding her breath, and suddenly let it out in a burst of
pleasurable sounds as I felt her spray her love inside me. She bucked
several times more, each like the first, each just putting me that much more
over the top. I came with her second-last thrust, my cum coming out in
ropes, pooling onto the sheets.
We laid like that for hours, sleeping until dawn, her still inside of me.
Shortly after we awoke we took a shower together, washing each other clean
of sweat and love, sharing kisses as we washed each other's hair.
Afterwards, we went and grabbed a quick breakfast before watching the sun
come up over the Cuban shore.

Epilogue

After being offered a promotion to stay on the summer I was waiting to go
back to school to get my Masters, I decided to take the job and forget
school for a while. Loren and I earned good money together and we managed to
get a better place together. We lived as an ordinary couple despite her
unique attribute, and I have been loving her every step of the way.
We got married in August on a hazy day, the air warm but with that hint of
cool breeze that told you Autumn would come early. Because gay marriage is
legal in Ontario, we explained to the Priest our situation and that we were
very much in love but did not want to hurt my family, since they did not
know Loren's biological gender. So he agreed to treat this wedding as no
different than any other couple, which was perfect. We had rented a place in
Belleville with an expansive field and garden. We were married surrounded by
friends and family, seated around the gazebo where the priest, Loren in her
beautiful white gown, and I stood.
Her and I still live together, and have recently adopted three beautiful
children from Russia. Our sex life remains great, although it's hard to
sneak in nooky when the kids are sleeping next door. We still go to Finn
McCool's once a week on whatever day we can get a babysitter.
She's decided not to get her endowment removed, which I approved of greatly.
She's special, and I love her for who she is and she knows that and knows
she doesn't need to change.
My family is still in the dark about her, and I intend for it to stay like
that. My life may be secretive, but it is worth all the cloak and dagger.
Loren matters the most to me, and what we have is precious. I hope it stays
this way forever.

Did you like it? Hate it? Want some links to my various other Nifty stories
in the Gay and TG section? Want to give me pointers, completely trash the
story, or just chat? Send me an email at melancholy_exile@hotmail.com - I
respond to every email and I appreciate all responses!