Note: This story was dynamically reformatted for online reading convenience.
 
 Author: Calypso
Title: The Transformation of Evelyn Thomas
Part: Chapter 6
Summary: The erotic journey of a young man through transgender
transformation to a new female self.
Keywords: MF, MMF, TG, cons, reluc, oral, anal, rom, 1st

   Send me your comments at calypso93<at>gmail<dot>com

   CHAPTER 6

   Day Twenty-Eight

   Rick's best man was his best friend and West Point roommate, Barry. 
Barry was a less hunky but more charming man than Rick, an odd set of
contrasts.  Where Rick was friendly and sexy in a masculine athletic sort
of way, Barry was an average sized man, about 5' 10" to my 5'8", in
non-athletic but still good physical shape who nevertheless dominated the
room when they were together.  Where Rick was a bit retiring, almost shy,
Barry was a flagrant extrovert and a charming and witty conversationalist
who could have the whole room laughing within minutes.  He had an amazingly
infectious smile and sparkling eyes and a boyish cowlick over all-American
good looks that made him look like a mischievous character in a 1950s
sitcom.  Appropriately, he was an Armored Cavalry officer, with the typical
Cavalryman's brashness and near-arrogant self-confidence.  I was charmed
and entranced by his bubbling exuberance.

   The only thing that kept me from melting into a warm, wet, giggling
puddle in Barry's lap was the arrival of the man who would "give" Karen
away, Major General Don Matson.  He was a tall, straight-backed, firmly
chiseled man with graying dark hair, the bluest eyes I had ever seen, and a
handsome, lined face that radiated authority and power.  Friendly in a
confident way, he was patrician without being condescending and powerful
without being overpowering.  He was incredibly sexy, so attractive I had to
force myself away, and so powerful that I was tongue tied whenever I was
around him.  I felt ridiculously weak and submissive and vulnerable and
feminine around him, like a naughty schoolgirl waiting to be caught doing
something she shouldn't.  I know it sounds a little like a bodice ripping
romance (and there was bodice ripping yet to come, to be honest, and I have
since come to appreciate the languorous sensuality of romance novels) but
that's how I felt about him, then and now.



   Well, I saw less and less of Karen and, to be honest, I was feeling a
little lonely and even a bit jealous...  of both of them.  I was jealous of
Karen, since I had had my big sister all to myself for the beginning of
transformation, and even of Rick, since Karen was getting her brains
screwed out on a nightly basis (I was adjacent to their room, remember)
while I was lying in bed jerking my little cock while reaming my ass with a
plastic dildo.  I was still coming about the same amount, but I noticed
that my erections were less intense.  The hormones were really working. 
But it still wasn't quite the satisfaction I wanted.  I wanted a man and I
wanted to be his woman.

   Day Twenty-Nine

   Things started looking up at the wedding rehearsal dinner.  The
rehearsal itself was casual, but I was still healing and I didn't want to
risk my scars so the jeans I had hoped to wear were still out.  It was a
cool (for California, anyway) spring day with some fog forecast for later
so I decided on a ribbed silk sweater dress in dark brown.  It had long
sleeves, a modest v-neck, and a shortish skirt that came to about two
inches above my knees.  I stayed with the comfortable beige knit cotton bra
and panties and added elastic-topped taupe thigh-highs and matching brown
knee-high leather boots with three inch heels.  Some simple gold stud
earrings and I was all set.  I brushed my hair into a casual part from the
left side and made myself up lightly and with restrained coloring.  I
looked good, if I do say so myself.  Barry, the best man, thought so too.
All through the rehearsal he was finding little ways to compliment me.

   "Wow, you look fantastic," he said when we first met.  "But then, you
always look fantastic!"

   "How would you know?" I said.  "We've only just met...  what's your
comparison sample?"

   "I can't imagine you not looking good."

   "What about me in sweats, with no makeup, messy hair, and just out of
bed?"

   "I think you would look especially good just out of bed." He winked
broadly at me!  What a flirt!

   I loved it.  I kept loving it right through the rehearsal dinner.  Barry
made sure he sat next to me, and I noticed he scooted his chair closer than
was absolutely necessary.  I didn't mind...  in fact, I encouraged it by
crossing my legs to show him some thigh on his side.  I made sure my skirt
rode up just enough to give a hint of the lace top of my thigh high
stocking.  I've learned that the old "oops, look at my thigh" trick is a
cliché that works over and over again...  and I never get tired of the
naughty thrill it gives me to "accidentally" give someone a look.

   I love Irish Coffee.  It makes you feel relaxed and happy and giggly and
euphoric...  but without the drowsiness of non-caffeinated alcoholic
drinks. So I had one as I flirted with Barry.  And then another.  And
another.  Now, I'm not that big...  so three drinks is about my limit for
my body mass.  I was feeling wildly happy and attractive and sexy and I
really, really, really wanted to be fucked by Barry.  God, he was
attractive!  I was thinking of a wild variety of completely impractical
ways I could let him in my pants (where he clearly wanted to be) without
having to confront the issue of my having a cock.  Simple honesty occurred
to me, but it was just too risky...  what if he reacted badly?  He could
ruin everything, Karen's wedding included.  But I wasn't drunk enough to
think my fantasies of cock-concealed ass-fucking would work...  so it
looked like a blow job followed by jerking myself off in private was going
to have to suffice.  Damnit!  Unless...  how drunk could I get him and
still have him perform?  An idea began to take shape.  First, I would have
to stop getting drunk myself, but keep him drinking.

   So I surreptitiously scooted my chair a little closer to his, and leaned
on him so that he could put his arm around me, which I noticed he wasted no
time doing.  I played sexy-but hard to get for the next few minutes... 
fending off his attempts to get a feel of my thigh, and being noncommittal
to his wild flattery.  As I expected, the conflicting signal of my
closeness and my defensive body language inspired him to order more drinks.
Hoping to get me drunk and have your way with me, hmm?  I thought.  Well,
maybe it's going to be the other way around...  I let him order me another
Irish coffee and then did a quick switch with the one I had already drunk
while he was distracted by the waiter.  Pretending to drink, I watched him
knock back what was probably his fourth scotch and soda.  Another couple of
these, I thought.  He was already getting silly and more than a little
flushed, so I decided to add to his disorientation.

   "Do you think you can just hop in my pants, mister!" I exclaimed in
false tones and a bit of feigned slurring of my speech in response to a
completely innocuous statement about how he liked my hair style.  I pushed
him back a bit.  He was startled and I could see the worry in his slightly
befuddled eyes.  How had he made me mad?  He didn't know, but he laid on
the apologetic tones and soothing so thick that I almost burst out
laughing. I gradually allowed myself to be placated by another round of
drinks.  Bingo!  I thought.

   With yet another full-empty switcheroo by me, he downed his fifth drink
and became almost tearfully maudlin and "sorry." I was "so beautiful" and
he "only wanted to get to know me better" and couldn't we "just spend more
time together because who knew when we would meet again" and "of course he
respected my wishes and wouldn't think of pressuring me" and so on.  It was
working!  One more drink ought to do it, I thought.  I made a big show of
"finishing" my actually empty drink.  He quickly ordered another round.  He
knocked his back as if seeking liquid courage, while I pretended to sip. 
He looked like a kicked puppy, so I acted placated and let him snuggle
closer, with one arm around me and his hand on my knee.  He cheered up, but
from his slurred speech I could tell he was completely hammered.  Now for
the next step in losing my virginity, I thought.

   "Oh," I said, stretching and yawning.  "I am sooo sleepy..." I feigned
losing my balance and "caught" on to him, my arms around his neck, as if to
regain my balance.  "Oh!" I exclaimed.  "I guess I shouldn't have had all
those drinks!  I hope I can get back to my room like this!" I giggled and
snuggled my forehead under his chin.  My lips "accidentally" brushed across
the exposed skin of his upper chest where his golf shirt was open.  I
breathed, my warm breath stirring the hairs on his chest, and I felt him
shiver with desire.

   "Fair maiden," he said mock seriously, slurring his speech a bit, "your
knight shin...  in sh...  shining sharm...  armor will escort you shafely
to your castle!"

   "Oh, thanks!" I breathed softly, raising my head and brushing his ear
with my lips.  "You are so good to me!" And I let him stand, a bit
uneasily, and help me up.  Actually, I think I was helping him stand, to be
honest.  We headed for the door, my head on his shoulder, my arm around his
waist and his arm around my shoulders.  On the way out we ran into Karen
and her soon-to-be husband saying their goodbyes to some of the others. 
Karen looked at me worriedly as if to say, are you OK?  I smiled a sober
grin at her and winked...  our unspoken sisterly communications kicked in.
She didn't look concerned, but she did look a bit puzzled, as if wondering
if I knew what I was getting myself into.

   The trip back to my room at the hotel was an adventure in itself.  We
took a cab, and I spent most of the trip trying to fend off Barry's more
extravagant advances without appearing too hard to get.  The cab driver
watched in his rearview mirror with obvious amusement as I repeatedly
removed Barry's hand from its course up my thigh and under my skirt, while
he nuzzled my neck and kissed my earlobe and slurred what he thought were
sophisticated come-on lines in my ear.  We got to the hotel none to soon,
as he was getting really insistent.

   Barry paid the cab driver, wildly over tipping him (he probably couldn't
compute the cost in his head, he was so drunk) and I "let" him lead me
through the lobby to the elevators.  Luckily the was an older couple in the
elevator so he couldn't actually try to fuck me on the ride up, but he did
manage to grab my ass a few times as I giggled encouragingly and drew
disapproving stares from the other couple.  At my floor we staggered down
the hall.  The drinks were really taking effect now and I figured he
wouldn't even be able to walk soon.  He leaned on me and the door frame as
I unlocked the door and pulled him inside.

   As the door closed I backed him, unsteady on his feet, up against the
wall and grabbed his head and kissed him, hard and hungrily.  He stiffened
at first, startled by my sudden aggressiveness, but quickly responded in
kind.  As I kissed his mouth, chin, cheeks and chin as if I was trying to
devour him, his hands wandered from my shoulder blades down the small of my
back to grasp my ass.  I gasped slightly and pulled back.

   "Hey, careful, I just had some surgery back there!"

   "Oh, I'm sorry!" He sounded and looked genuinely contrite, so I went
back to exploring his face with my mouth.  He tried to keep up and kept his
hands carefully above my hips, with greater gentleness this time.  I sucked
at his lips and nibbled gently on them as I kissed his mouth in a circular
pattern...  across the bottom lip, up and back across again.  His mouth was
warm and strong and active and made me feel hot and dirty, like I wanted to
feel.  I could feel his cock straining through his pants, long and hard and
pressing against me.  He was rubbing his crotch on me, probably
unconsciously, and I could tell he wanted me, bad.  Well, that was great,
because I was having the exact same reaction....  Just not the one he
thought I was having.  My little cock was hardening too, but couldn't come
to full erection as I had it tucked back in my panties.  It throbbed
painfully swollen between my thighs, it's head tantalizingly near my anus.
That's where I wanted him: up my ass.  It was time for the next phase of my
slightly devious and very naughty plan.

   I kissed my way up to his ear and breathed in it, "time for the next
course, baby..." as I did I backed off and grabbed his waistband at the
belt buckle.  I backed slowly to the bed, towing him obediently along,
unsteady now as the drinks took their full effect.  As my calves touched
the edge of the bed I put my arms around him, as much to keep him from
falling as anything else, and kissed him gently as I rotated us both on our
feet so that his back was to the bed.  Gently I ended the kiss and lowered
him to the bed.  He was sitting on the edge of the bed, near the head so
that he could lean back against the pillows and head board at an angle,
with his feet hanging off the bed.  I bent forward and kissed him again,
gentle nibbling kisses, as I reached down and undid his pants and belt.

   Barry was dizzy with alcohol and hormones and didn't know whether to lie
back and enjoy it or to try and help.  He fuddled helplessly with his
pants, but knew enough to raise his ass cheeks up as I pulled his trousers,
belt, and underwear down to his ankles, sinking to my knees between his
legs as I did so.  He mumbled drunken endearments as I undid and pulled off
his shoes and socks, throwing them over my shoulder to land somewhere in
the darkness.  Then I pulled his pants and underwear off, his pants inside
out in my haste, and did the same with them.  His cock, 8" long, hard, and
erect, bobbed in front of me at neck height.  I looked up at him.  He was
looking at me with an expression of awe and desire as I leaned forward and,
never taking my eyes off his, took his cock gently in my mouth.

   I closed my eyes and savored the taste of his leaking precum as I leaned
forward, taking his full length slowly into my mouth and down my throat. 
The angle was a bit sharp; I gagged slightly as the head of his cock rubbed
across the top of my throat, so I backed off a bit and concentrated on the
shaft and head with my lips, tongue, and teeth.  He exhaled a long ragged
breath as I ran my bottom teeth and tongue up the underside of his shaft,
rasping it along the part that I know (my secret, naughty knowledge of my
own cock) is the most sensitive.

   I settled into a fore-and-back rocking rhythm, sliding my mouth up and
down along the length of him, listening to his breath become faster, more
ragged, and shallow.  He took my head in his hands, gently, and I let him
take control of the pace, knowing he was getting closer to orgasm.  He
started moving his hips, thrusting his cock into my mouth, fucking my face,
and I relaxed and let him use me.  It didn't take long.  He thrust forward,
hard, almost gagging me and his cock began to pulse as long warm jets of
come began to splash the roof of my mouth.  I concentrated on sucking him,
swallowing the loads as he added more, tasting the warm saltiness of it. 
Barry tasted a little different from Pete; where Pete had been almost
neutral tasting and sort of blandly pasty, Barry's come had a decidedly
salty tang, almost like diluted seawater.  It wasn't bad, just different,
and I savored the erotic thrill of kneeling between another man's legs,
swallowing his semen, and knowing the power that I had over him even as I
submitted to his desire.  Barry finished coming with a shudder and a long
exhaling sigh, and fell back against the headboard and pillows to pant
slowly.  I let his cock pull out of my mouth as he did so.  Now for the
next bit of my nefarious plan.  He wasn't even going to know what had hit
him, but he was about to score a buttfuck on top of his blowjob.  But I had
to time it just right.  I was really turned on, my little cock throbbing
painfully between my legs as I anticipated having my ass taken for the
first time and I didn't want him going soft on me before I had his shaft up
my ass.  But I also didn't want him too alert...  I had a secret to
conceal, after all.

   I stood up from my kneeling position and leaned forward to kiss Barry
lightly on the cheek.  "Hey, baby, you OK?" Barry mumbled inarticulately,
his eyes closed and his breathing becoming deeper and slower as his
biorhythm bottomed-out from his orgasm and the effects of the alcohol. 
"I'll be right back, baby, don't go anywhere," I whispered in his ear.

   Quickly I moved across the dark room to the dresser, snatched up some
satin panties and a nightgown, and went in the bathroom where I turned on
the light.  I had the deep sea-green full-length nightgown, trimmed in
black lace, with a moderate, gently supporting bodice and with a thigh-high
side slit up the right side of the skirt.  The panties were red. 
Mismatched, but so what?  Maybe it was ironic...  green & red; stop & go?
Whatever...  I was in a hurry; Barry's erection clock was ticking.  I
pulled off my boots and dress and dropped them and my underwear in a pile
on the floor and pulled the nightgown quickly over my head.  My cock sprang
out, hard and erect in front of me.

   I left the panties off for the moment and opened the drawer where my sex
toys were located.  I quickly pushed them to the back (I didn't want Barry
running across them if he got up to use the bathroom), pulled out the tube
of lubricant, and squeezed a gob onto my middle fingers.  I reached back,
under the nightgown, and smeared a bit around my anus.  I bent forward to
get a better angle and poked my middle finger up my ass, pushing the lube
ahead of it.  It felt good.  The lube had a warming effect that made my ass
feel warm and tingly.  I pulled my finger back out and smeared more lube on
my anus and repeated it.  It took a few tries, but I had a little of the
lube smeared up my asscrack and most of it pushed into my anus, which was
decidedly warmer-feeling and tingling with anticipation, the pleasure of
finger-fucking myself, and the effects of the lube.  I wiped my fingers
quickly and grabbed the tube and pulled on the panties (I left my cock hard
and erect in front this time), turned off the light, and stepped back into
the darkened room.

   It took a moment for my eyes to adjust to the dark.  Barry was on the
edge of sleep, sprawled back and nude from the waist down; his cock still
semi-hard and his feet still on the floor.  I leaned over him, my hair
brushing his face, and he murmured groggily at me.  "Sshhh, baby, let's get
you on the bed," I said softly, and reached down and lifted his legs up to
the bed.  He cooperated passively as I rotated him onto the bed...  I'm a
little stronger than the average girl (grin).  Then I climbed up and
straddled him, on my knees, careful to keep high so my cock wouldn't rub on
him and give me away.  I leaned forward onto my elbows and began to nuzzle
Barry's neck...  light teasing kisses and nibbles up his neck and his ear,
then down under his chin and up the other side.  Barry mumbled at me and
felt up my belly for my breasts.  "Sshh, baby, let me take care of
everything," I said softly as I gently took his hands and placed them back
on the pillows.  I continued my teasing for a bit and then freed one hand
to feel for his cock.  It was hard and erect again...  Great!  He was
ready! One thing I have learned to like about fucking military guys (and a
couple of cops and firefighters along the way) is that they are always in
great shape and can get hard in an instant and keep it that way.

   I leaned back on my heels and carefully shifted my knees and rotated
until I was straddling his thighs, facing away from him, and with my bottom
poised over his crotch.  I squirted a last gob of lubricant onto my fingers
and tossed the tube in the direction of the nightstand, then I reached back
with both hands and, as I pulled down my panties in back, I grasped his
cock, smearing the lube on the head and around the shaft just below the
head.  Barry thrust his cock at my hand, enjoying the sensation, as I
finished lubing him and guided the cock head to my anus as I leaned back
onto him.  I felt the head at my tight little virgin entrance and thought,
well, this is it!  I leaned back, slowly, savoring the tightness and the
thrill of the penetration, and lowered myself onto him, inch by tantalizing
inch.

   Being sodomized for the first time was simply heavenly.  I really can't
describe it any better.  I had no idea it could be like that.  He entered
me easily, the lubricant made him slide in with a quick smooth `pop'
sensation past the ring of my anus; his cock slowly and easily slid deep
within me in one long, slow thrust.  I felt full and submissive.  His cock
was long and hard and warm and deep in my guts and it felt as if he was so
deep inside me that he was in my stomach and pushing up into my throat.  I
had a sensation of butterflies deep in my bowels and was short of breath
and my heart was pounding with the thrill as I withdrew slowly and then
easily sat back onto him.  From his position behind me he drunkenly reached
out to hold my hips as I rode his cock, rocking as I fucked him.  I rocked
back and forth and he met the rhythm, meeting me with thrusts, and with my
ass cheeks making a soft slapping sound on his thighs.  We were soundless,
but I was panting and I could hear him breathing raggedly and shallowly
again.  This went on for what seemed like a very, very long time.

   After what seemed like a sensual age of incredible waves of warm
electric desire I rode him too high and he popped out with a soft slurping
sound.  I gasped with the sudden loss of him.  He paused for a moment and
then wordlessly pushed his cock up to my ass, softly pulling on my hips.  I
wasn't disappointed for long.  I squatted onto him, reaching around my
thighs to guide him back to my anal opening.  I felt his cock probing
between my ass cheeks and I pushed my ass down against him.  I was quickly
rewarded as his warm hard shaft with its smooth firm head pressed slid
insistently between my warmly lubricated ass cheeks.  He probed for a bit
for my anus as I guided him.  I wiggled my ass, pushing my tight ring,
still buzzing with what felt like electric thrills, back against his cock
head.  I was panting harder now, anxious to have him back inside me.  There
he was.  He entered me again.

   I cried out, wordlessly, with ecstasy.  "Aaaahhhhuuuuhhh..." He was
further forward now and from this new angle he thrust backward, stretching
me.  The world seemed to spin as rolling waves seemed to burst from my
groin, warm burst of pleasure and sensation that made the entire world
shrink to the feelings that seemed to pour from his cock.  We were fucking
harder now, and faster, slapping against my ass.  I leaned forward,
intensifying the pressure in my guts, gripping the bed surface in my hands,
my toes curled, and bit down hard, my eyes closed, tears of intense
pleasure and rolling emotions leaking from them.  I was gasping now as he
fucked my ass.  I felt gloriously humiliated and yet enthralled with
visions of being raped in the most personal and intimate way, captive to a
powerful master and yet holding him in my own thrall of erotic and
dangerous enticement and desire.  He was pounding me, and I was pounding
him, harder and faster.  God, it was like being impaled on a jackhammer. 
The bed was bouncing, I was bouncing on it, the springs were squeaking and
the headboard thumping and I might have been moaning along with it all, but
I kind of lost track.  Looking back on it, I'm sure the noise was audible
three rooms away.  At the time, I just didn't care about anything except
what he was doing to my ass and how deeply he was doing it.

   Drops of my sweat ran down my face and body splashed and his hands
gripped my hips painfully, forcing me onto him.  I was moaning in panting
cries that finally rose as I began to come in long, shuddering waves.  I
hastily pulled my nightgown away as my come squirted out and up into the
dark.  As I came, my ass tried desperately to force his cock back out as my
anal sphincter spasmed...  but he held me down on his cock and continued to
buttfuck me, drawing my orgasm out endlessly.  It went on and on and on.  I
don't know for how long.  The room seemed to spin around me with the
seemingly endless waves of what had to have been the most incredible,
deepest, and enduring orgasm of my life.  I came and I came and I came,
with long shuddering waves.  Then, just as I was catching my breath, he
began to come.  It wasn't as long or as full as the jets of come he had
ejaculated into my mouth, but it was still deep and warm inside me and I
felt the spreading warmth as his come leaked around his cock and out of my
ass.

   Afterwards I sat there on him, panting, for a moment; feeling my
heartbeat slowly return to normal.  I felt a warm glow inside me, the warm
glow of his cum, of my shattering orgasm, of the deep and passionate
fucking I had just received.  God, I had no idea it could be like that.  I
quivered, motionless, for a while.  I felt Barry's cock softening inside me
as his hands fell away and, exhausted, he fell into a deep snoring sleep.

   When I felt like I could move again without falling over I gently
disengaged his shriveled member from my ass and carefully climbed off him.
I stood in the dark for a moment, feeling a little dizzy.  My own cock had
softened and shrunk back into my panties; I could feel a little of Barry's
come running down the back of my ass cheeks.  I pulled the covers up from
where we had apparently kicked them to the foot and off the bed in our
passion (I had missed that bit, somehow) and covered Barry's sleeping form,
gently.  I left my panties pulled down in back and waddled quickly into the
bathroom where I left the lights off and quickly wiped myself with a damp
washcloth.  Satisfied with my hasty clean-up I pulled my panties back up in
back, made sure my cock was tucked safely and unobtrusively between my
thighs, and went to bed.

   I climbed carefully and quietly into bed next to Barry.  For the rest of
the night I felt that warm, loose, wet, quivering sensation deep in my
bowels.  I luxuriated in the feel of the cool, crisp cotton sheets as I
stirred lazily, enjoying the afterglow.  I felt Barry's warm presence next
to me and the wetness of his semen in my ass, a tiny bit leaking out as I
fell into a deep, warm, satisfied sleep.