Michelles Continuing Affair Ch 2
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Michelle's Story free porn video
Warning: The following story deals with the subject of
transgendered people. It includes graphic sexual
descriptions and is intended for amusement only. No
endorsement or denigration of any of the activities or
actions contained herein is expressed or implied.
If you are bothered by graphic sexual description and/or
issues related to transgederism DO NOT READ THIS STORY.
The author retains all rights to this story.
Michelle's Story
By Bootlover
It all started, as it so often does, with that odd
combination of boredom and curiosity. Home alone, the wife
and kids away, some sexual energy built up from watching
the young secretary at work, or an R rated movie on TV or
just reading Playboy and the need for gratification builds.
He started just by trying on a pair of his wife's sexy
panties. Little did he know but Michelle was born.
Over time wearing women's lingerie, stockings, heels,
boots, gloves, dresses became the source of the thrill.
Those rare stolen moments when the secret collection could
be opened and tried on. Worn for an audience of one,
mirrors adjusted so that side and back views could be
achieved, so that the curves of calves, thighs and buns
from 5" heels and sheer nylons could be appreciated. Daring
purchases of must have items from stores, long hours of
internet shopping for more special items, shipped to a Post
Office box for just that purpose. In time the items took on
more of a fetish bent, more leather, significantly more
trashy or slutty and some toys. When fully dressed, with
wig and make up he became Michelle, felt as Michelle would
feel. The next step was to fantasize about experiencing
life as Michelle. Alas, fantasy was all it could be.
He had begun to wear women's panties under his clothes to
work on most days. Some days he did not because his wife
was still around when he dressed, because he knew would be
in a situation where he might be discovered, such as
playing golf at the club. As often as he could, however,
underneath his pants were silky soft panties. He tended
toward the sheer, slick nylon/acetate panties that were
available most anywhere and not too expensive. Lace
panties, though sexier sometimes chafed and did not send
the same waves of pleasure from the head of his cock as the
material caressed the smooth, sensitive skin. He could feel
the soft caress as he walked and a hard on, with the head
pushing tightly against the nylon the feeling was pure
pleasure. How often he found himself in his office looking
through the Victoria's Secret or Frederick's of Hollywood
or Northbound Leather website, longing for an item to be
the newest addition to his collection, absentmindedly
caressing his cock through his pants.
And so it came to pass that in a pair of tiger striped gold
panties he found himself working late one night.
Now this was not an uncommon occurrence. When you own a
business you need to do what needs to be done, and very
often that means staying late, when others won't, to finish
paperwork, loading boxes, finishing a process, whatever.
While he never wore more than panties at work, being able
to move freely in them around the office and manufacturing
area added to his enjoyment. He contemplated bringing a
pair of heels to wear someday so that he could hear that
wonderful "click" as the spike struck the concrete of the
workshop with each stride. But, he felt that was too risky.
If he were discovered it could ruin everything. So he
continued his extreme discretion.
This particular night the private bathroom attached to his
office was being repaired and so he went to use the
employee bathroom down the hall. Martha had forgotten to
turn off her computer, how many times did he have to tell
them to shut them off at night? Save energy, save the
screens he repeated as he powered the PC down. As the
screen flashed it's final good-bye and he switched off the
power he had a sense of the darkness increasing by more
than just the glow from the screen, as if an overhead light
somewhere had gone out too. He almost sashayed down the
hall, feeling the seat of his pants brush against the nylon
covering his cheeks and the sensation felt at once cool and
arousing. He pushed open the door and moved to the urinal.
Now as opposed to wearing boxers or briefs, where he had
the option of using the flap, to pee when wearing the snug
nylon panties he had to unbuckle his belt, open his fly and
drop the band of panties. And then, as his secret was
exposed, the door of the bathroom opened and in walked
Tony, the tall, strong and handsome foreman on the line!
There wasn't anyway for him to stop in midstream and cover
up so he tried to finish up as fast as possible as Tony
moved to the urinal next to him. He could not tell how much
of the panties were exposed and he dared not look down to
try and determine whether they could be seen. Out of the
corner of his eye he could see Tony's gaze wandering toward
him. He fear rising he wished he could finish but the
tension only slowed the process. When the last drops came
out he deftly tucked himself back in and began to hitch up
his pants.
"Nice panties, boss." Tony said with a sneer. Mortified he
tried to make light of it.
"I knew this wasn't a good idea," he said. "My wife got
behind on laundry and I was without any underwear this
morning. She said to just wear a pair of hers, who would
know?" He felt rather proud of this little story, concocted
on the spot.
Tony replied, "Well you made a lovely selection. Maybe I
should call your wife and tell her she needs to do a better
job at home."
Now he shouldn't have, but upon hearing the statement about
calling his wife he panicked. "No, not that" he blurted
out, the red rising in his face.
Tony looked confused. The smirk he was wearing as he made
the statement turned to a questioning look, then it
abruptly changed to understanding. "Calling the wife would
be a bad idea, eh?" Tony said in a cold, surly voice.
"Yes, yes a bad idea" he replied.
"Well now, seems I'm in a position here." Tony continued.
"I know a little secret about you that it appears you don't
want your wife, and I assume others, to know."
His shoulders fell as he realized his secret was out. "What
do you want?" he asked, "A raise? More vacation?"
"Oh no, nothing to do with work. But there is a price to
your secret."
Two nights later he was working late again, or rather
trying to work late. Sitting in his office he went over the
conversation with Tony that occurred after his discovery in
the Men's room. Tony wanted his "Pound of flesh" alright,
but Tony actually wanted it in flesh! More precisely, Tony
wanted it in Michelle's flesh.
As they talked he told Tony everything about his dressing
and Michelle. Surprisingly, Tony wasn't disgusted, in fact
he was turned on, as clearly evidenced by the bulge growing
in his pants. In fact Tony's proposal for his silence was
related solely to Michelle. He got up from his desk and
walked to his bathroom. He had never brought any of
Michelle's things to work but at Tony's insistence he had
selected items from his collection, brought them to work in
the trunk of his car and carried them into the office in a
gym bag early this morning before most of his employees had
arrived.
The bag was in his hand, having been removed from the
locked bottom desk drawer, as he walked to the bathroom.
Inside he removed his male clothes, stripping down to his
black Victoria's Secret French cut bikini panties. Then he
began to withdraw items from the bag and put them on. First
was the black satin corset, snugged tight around his body
and then laced up as tight as he could manage by himself.
He added the breast forms, which filled out the top nicely.
Then he pulled a black stocking with back seam onto his leg
attaching it to the garters on the corset. He repeated the
procedure on his other leg. He turned to the mirror and set
to applying the makeup, then the long black wig with the
rings of curls.
Every time the transformation was made Michelle couldn't
believe how good she looked. With glossy lips, eye shadow
and gentle shading of blush she looked most attractive. As
she stepped into the 5" spike heel patent leather pumps her
legs and ass took on feminine form and curves. With corset
and boobs she looked tall, leggy with a shapely ass and
hourglass figure. She slipped on her maid's outfit, with
all of the white underskirts fluffing up the dress. The
skirts barely reached the tops of her stockings and she
felt almost fully exposed.
Her heart was racing as she moved toward the door. She felt
nervous, of course, but, strangely, she felt excited and
aroused. She could feel her clit growing inside her sheer
panties. It made her think of the discussion two nights ago
with Tony on the other side of the door. The strongest part
of the memory was how she kept noticing the bulge in his
pants, why was that? Michelle pulled on the long silk black
gloves that reached past her elbows, took a deep breath and
reached for the handle.
As she stepped through the door and into the office there
was a flash, and then another. "Just a little insurance,
baby." Tony said coolly. He stood and surveyed Michelle,
his eyes travelling up and down her body. A smile crossed
his face "Very nice, baby. You're even hotter than I
thought. Give me a little show."
Michelle walked around the office, feeling the corset move
with the sway of her hips caused by the 5" heels. Several
more flashes went off as she performed her fashion walk.
She felt her clit straining against the smooth nylon of the
panties. Her hands were shaking from nerves and her pulse
was throbbing.
"Come here." Tony commanded.
Michelle walked toward him, trying to look at his face but
her eyes straying to his crotch and the noticeable swelling
there. As she reached Tony, who was sitting perched on the
edge of the desk she felt his hand reach out. He touched
her waist, then glided over the ruffles to her nyloned
thigh and moved slowly up under the ruffles until it cupped
her cheek. His large firm hand kneaded her ass as he pulled
her closer to him. Now between his thighs she felt a heat
burning in her.
"Unbutton my shirt." he ordered.
With trembling fingers she began to undo the buttons on his
shirt, exposing his hairless and muscular chest. As her
hands brushed back the shirt she touched his chest and she
felt strange. This was so new. Tony released her ass and
pushed back a step and stood.
"Now my pants."
Nervously Michelle dropped to her knees and began to
unbutton and unzip his pants. As Tony stepped out of his
pants his body was exposed except for the tight red bikini
underwear. Smooth, muscular and olive skinned he was a
prime example of male power and looks.
"I've never had a virgin," Tony said in a low, throaty
voice. "I want to take this slow, but I think I need you to
take the edge off."
Michelle looked up at him, knowing what he wanted. With
tantalizing slowness that teased her as much as Tony she
slid her hands up his thighs and for the first time in her
life caressed a cock. Slowly and gently she ran her gloved
fingers over the outline of his shaft and head through the
thin cotton. Tony's low breathing indicated his positive
reaction. Abruptly Tony grabbed her hands and pinned them
behind her. Quickly he bound them with a short length of
rope. Then stepping behind her he bound her ankles too. Her
clit was threatening to rip through her panties and it was
leaking. Kneeling there, wrists and ankles bound behind her
she felt a rush of excitement.
Moving back in front of her Tony hooked his thumbs into his
underwear and slowly peeled it down. Michelle could not
help but gasp as a big, thick 8" cock engorged to it's full
size in front of her. He placed the head on her lower lip
and she parted her glossy lips and took in the fat head.
The texture of the skin felt wonderful to her tongue and
the roof of her mouth, her jaw was stretched wide open from
the size, but she didn't mind.
Tony took several pictures of her with his cock in her
mouth, including one of her looking right up at him. Tony
took her head in both his hands and began to piston his
cock into her mouth. Amazingly she felt his cock swell even
more, then pulse and explode a huge glob of cum. Michelle
swallowed as fast as she could but each pulse brought a new
load. Furiously she gulped down the hot cum. As Tony
relaxed and she finished the last drop it was harder to
tell who was happier.
When Tony recovered he moved Michelle to the centre of the
room and laid her on her side. Wrists and ankles bound
Michelle was helpless. Her ruffles rode up and exposed her
panties. Tony produced a ball gag and strapped it into her
mouth. A few more flashes and then he knelt beside her.
Reaching between her thighs he pulled down her panties,
exposing her hard clit. With one swift hard yank he ripped
the panties off her.
A few more flashes and Tony returned to her. He teased her
hard clit with slow strokes, increasing her desire and
frustration. She whimpered behind the gag in her desire for
release. Tony picked her up, and moved her to the coffee
table. He retied her legs to the legs of the table. Her ass
was now exposed and up in the air. Her clit was trapped
between the top of table and her dress. Tony kneaded her
ass and massaged her balls. She moaned through the gag. She
knew what was next.
She felt a lubed finger explore her pussy, opening her up.
Tied and helpless to react other than how her body's
animalistic urges made her respond. She felt her pussy try
to pull his finger into her. Tony's hands grasped her hips
firmly. The head of his cock moved between her cheeks,
searching for her pussy as if it had a mind of it's own. As
it reached her lubed hole it nestled into the opening,
primed for entering her.
With firm, steady pressure Tony's dick worked it's way in,
the head stretching her cunt until it popped in completely.
Then, with agonizing slowness, inch-by-inch the shaft kept
sliding in. She knew when he was in her to the hilt. He
held it there letting her get accustomed to him. Michelle
had never felt so full, so feminine before. Tony began to
thrust into her and she matched his rhythm as best she
could. She ground her ass into his crotch each time he
buried his meat in her.
She mumbled "no" against the gag on each withdrawing stroke
as he came so close to completely removing his cock. His
pace increased until he was ramming his cock into her. She
felt his groin slapping against her ass and his hands
gripped hips harder. Again, she felt the telltale swelling
of the head as he buried it deep inside her and for the
second time Tony erupted into her. Michelle, overcome with
emotion, arousal and excitement passed out.
When she awoke she was unbound and alone. Next to her on
the floor was the camera Tony had been using with a note.
It read:
"To my new lover. I hope these pictures will help you to
release your tension."
Maddy
- 29.12.2022
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