Blackmail Come True Chapter 4
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Blackmail Come True Chapter 1 free porn video
I walked out to my car, steeling myself for the 45 minute commute to
work, when I noticed a manilla envelope stuck under the windshield
wiper of my ten year old Honda Civic. The outside of the envelop simply
read, "From an admirer." I'd only moved to this neighborhood about a
month before, coming out of a horrendous divorce, and hadn't really
even considered dating yet, so while I was flattered to receive a note
from an admirer, I was also a little bit creeped out because it might
mean that someone was stalking me.
I slowly opened the envelope, starting to think that it was probably
just a prank by someone from work, or my friend Greg who had helped me
move and was the only friend who had been to my new place since the
divorce. I pulled out a folded piece of thick, watermarked, cream
paper--the kind you would use for a resume. As I opened it, I read in
the authoritative handwriting of an older man, "Please leave your
curtains open again tonight, but this time wear these instead of those
cumbersome tights you were wearing last night."
"Fuck, fuck, fuck," I muttered out loud as I pulled a pair of sheer
Wolford stockings and lace boyshorts.
One thing that no one in the world knew about me, at least not those
who knew Jack McGarrity, except for my wife, was that I loved
crossdressing. In fact, in the end, it was the reason she divorced me.
She came home one night from work after telling me she thought she'd be
working late and when she walked in she caught me sitting at my
computer wearing a tight, soft, wool mini dress I'd just ordered
online, with a pair of thick tights, 5" high heels, and my auburn wig.
I was chatting with men online, playing out the fantasies there that I
never thought I would have the chance to live out in real life. When
she walked in, I had a large black dildo halfway inside of me and was
on cam, telling some guy who called himself Jim how much I wanted to
feel his cock in my ass in my very best fem voice.
To say she was surprised would be an understatement. Anything I have to
say about her reaction would actually be an understatement. And while
she did actually make an attempt to process the situation and even
understand where I was coming from, ultimately it was too much for her
to handle, and she filed for divorce two weeks later.
Her family was rather wealthy, and she had never signed a pre-nup. So,
wanting just to end things as cleanly as possible, she actually left me
with a very generous settlement. For the first time, I was relieved
that we'd never been able to have kids. I was also relieved that at 32,
I might still have time to figure out what I wanted in life.
She asked me to leave the house when she handed me the divorce papers.
She'd cover a hotel room until I found a place to live. At first, I
felt fairly lost. I never imagined that this was a thing that could
happen. I'd fantasized about being able to leave her when I was dressed
sometimes, and in the throes of professing to some strange man how
amazing I thought his cock was, but that felt like make-believe, and
usually when I finally came, those feelings would gradually fade. And
honestly, Jocelyn and I had a pretty happy marriage. The same ups and
downs that everyone deals with, but divorce was not a prospect I'd ever
put any thought into.
So there I sat, with a few suitcases (one of which until recently had
almost always remained locked in the back of my closet) alone in a
hotel suite and newly single. The first night I found myself wondering
toward a pharmacy and buying a lady's razor, shaving cream, lotion,
deodorant, and perfume. I felt as if I was lost in some weird foggy
haze as I stepped to the counter and paid for the items. It was the
same fogginess that enveloped me as I stepped into the shower and
slowly lathered pretty much my entire body in pink ladies shaving
cream, and then proceeded to shave my entire body. This was something
I'd dreamed about doing before. I'd even once mentioned to Jocelyn
whether she thought it would be sexy if I shaved my body. Based on her
reaction it was a topic I decided never to broach again.
Looking in the mirror, I looked like a 12-year-old boy instead of a 32-
year-old man. I sucked my gut in though, and found myself tucking my
penis between my legs, arching my pack and doing my best to remember
the poses of girls I'd seen on pin-up calendars; it was definitely a
more feminine image then I'd been able to accomplish before, if I kept
my gaze below my neck. I needed to work on the extra pounds I'd packed
on though over seven years of marriage though.
I stepped out into the room wearing only a robe and went to the locked
suitcase. Just at the thought of it, my cock had started to harden. It
wasn't very big even when fully hard, maybe five inches. It was always
something I'd felt very self conscious about with Jocelyn. I pulled out
a pair of opaque, black tights. I'd always bought opaque to hide my leg
hair. The more I'd dressed the more obsessed I'd become with projecting
an image or an illusion of femininity. I'd wear long sleeve turtleneck
dresses with fingerless opera gloves, just to make sure not a single
speck of body hair could be seen.
I sat down on the side of the bed and rolled up the tights to pull them
on. The moment I pulled them over my calf, my cock went rock hard. I
thought for a moment that I would cum right then and there. In that
moment, I wished that I'd been shaving my legs my entire life.
That night, I spent hours online, seducing men in chat rooms, having
phone sex, showing off on video. I didn't go to sleep until 3am and
only got 4 hours of sleep before having to get ready for work the next
day. In the light of day, I cleaned the lipstick from my lips, and
wondered what anyone might think if they noticed how entirely hairless
my body had become. While I usually rolled my sleeves at work, I
decided to keep them buttoned that day.
The next month continued this way, except for the fact that I started
to work out obsessively. With nothing else left to occupy my time after
work, it just seemed like the logical move. I found myself staying away
from any sort of muscle-building activities and preferring activities
that toned my body. Pretty soon I had a flat, but not all that
articulated stomach. The same could be said for my arms and legs.
Right before moving into a new place, though, I'd become extremely
paranoid. My family was coming to visit, I'd need help moving. I threw
out everything that had been in the locked suitcase. I stopped shaving
my legs. I started thinking about what I really wanted with my life
after Jocelyn. Didn't I want to have children eventually, start a
family? Would I ever really find a woman who would really be okay with
this side of me?
I'd found myself missing it though a few weeks after moving. Late one
night, drunk on bourbon, I'd ordered $300 worth of new clothes. The
packages had arrived the day before and I'd spent the evening playing
dress up in the living room. Apparently, I'd done so with the blinds
and curtains wide open, and now I was left to wonder, as I drove to
work with the handwritten note on the passenger seat, who my admirer
was and what exactly they wanted.
By the time I got to work, I'd rationalized the whole situation. I'd
ignore it. If the person who had written the note continued to harass
me, I'd claim ignorance. "It was my brother, visiting from out of town,
and alone for the night, who indulged in a habit he hid from his own
family." I'd been successfully hiding this from almost everyone my
whole life, I wouldn't let this ruin anything. Then I started to
wonder, "Wolford nylons? This is a guy with good taste and money. I was
only renting. What if this was my chance to live out my fantasy with
someone who might understand me? If it didn't work out, I could just
move some place else.
I had a busy day ahead, filled with meetings and client phone calls, by
lunchtime I'd pretty much forgotten about the whole thing. When I came
back from a meeting, there was a large package on my desk. It has a
"Same-Day Shipping" label on the top. I put it down next to my chair
and checked my email. There was one that made my heart jump. The
subject line read, "Read Before Opening Package" it was from
[email protected]. My address was 1444.
I closed the door to my small office, thankfully windowless and locked
it. I opened the email. Embedded at the top were pictures of me, taken
through the living room window. While they were slightly grainy, it was
clearly me, sipping a glass of white wine while wearing a clingy, black
minidress, with long sleeves, and a cowl neck. I had on patterned
tights and 5" ankle booty heels. There were more pictures. He captured
all four of the new outfits I'd tried on.
Below the photos the email read, "I especially like the first outfit.
Please wear that one again tonight, and, additionally, what is in the
package. Based on the opaque tights and the long sleeves, I assumed you
could use some of the other supplies I have included. I?ll expect that
you use them daily and trust me when I say that I will know if you do
not. I?ll expect that at 7:45 pm this evening you are standing in the
easternmost window of your living room, waving your hand. If you fail
to comply with any of my requests, the photos I have attached and any
additional photos will be sent to the email addresses listed below.? I
scrolled down and saw about 25 email address including my parents, my
grandparents, my brother and sister, and all of my closest friends, as
well as a few of my co-workers and my boss.
There was a post script as well: ?I know that you have the package I
left on your car in your bookbag at work. Put on both items and text a
picture to the following number no later than 1:30pm.?
It was 1:24. My hands were shaking, I felt sick to my stomach, but at
the same time I had the biggest, hardest erection I think I?d ever had.
I started to open the box, but then remembered the time, his final
request, and the not so veiled threat in the email. I double checked to
make sure that my door was locked and quickly stripped off my pants,
boxers and socks. I immediately wished my legs were shaved, but was
pretty certain they would need to be tonight anyway. I slipped on the
panties, loving the way the lace felt, and then rolled up each leg of
the nylons, before I had even finished pulling them up all of the way,
I felt my erect cock spasm and suddenly found myself cumming all over
the floor. I cleaned up my mess quickly, pulled up the tights and
pulled out my phone.
I sat down in my office chair and leaned back, crossing my legs at the
ankle. I lifted my phone up, looking for an angle that would make my
legs look best and then snapped a photo, and quickly sent it to the
number listed in the email. A reply came back after just a few seconds,
?I almost thought you wouldn?t make it. Keep them on for the rest of
the day, my dear. Do not reply, unless I ask you to do so.?
I?d daydreamed about wearing pantyhose and panties to work before, but
not like this. What was I getting myself into? Could he be bluffing?
Was this just a prank from one of my ex's friends? Had she told
someone? Was this her, trying to punish me? Ultimately, I realized it
didn?t matter and that my only choice was probably just to play along.
I pulled my pants back on, put my socks on so that no one would see the
nylons in case my pant leg started to come up. And then put my shoes on
and sat back down. God I loved how my nylon clad legs felt against the
inside of my pants, and the way the panties hugged my shapely ass. I
could already feel myself becoming erect again. Shit! The box, I
thought.
Someone knocked on my door, it was Veronica reminded me we had a
meeting in 10 minutes. ?I?ll be on time. Don?t worry,? I yelled through
the locked door.? I took out a letter opener and used it to cut the
tape holding the box shut. There was a handwritten note on top of
everything, ?Can?t wait to see you tonight.? I tucked the note into my
bookbag and continued to unpack the box. There was a can of extra
strength hair removal cream, a brand I?d never even heard of. A post it
note on the can read, ?Until we get you signed up for electrolysis.? I
shuddered, but kept unpacking things. There was a box of fake nails,
extra long, red nail polish, concealer, foundation, lipstick, false
eyelashes, mascara, perfume, lotions, and a large make-up palette, all
from top of the line cosmetics brands. I pulled out a heavy box from
inside and opened it up to find myself staring at two very large and
very realistic looking silicone breasts. Inside the box was also a
large bottle of theater adhesive.Next I pulled out a sleeveless black
minidress that had see-though nylon paneling on top, with nylon cut-
outs that ran around the mid thigh. Below that was a high-quality,
laced corset, a pair of gaffe panties with built in hip pads, and a
pair of suede, leopard print, platform stiletto heels. There was also a
bottle of throat spray, that said something along the lines of
professional use only in French (I had to use Google translate) and
something else about constricting and warnings about possible damage to
your larynx.There was also a very long, human hair, dark brown wig with
just the right amount of wave in it. I was actually pretty sure I?d
bookmarked this wig on my browser, but at almost $1,400, there was no
way I ever really planned on buying it. I then pulled out a red,
leather Coach purse, hearing something rattle inside as I put it down.
I opened it up and found four bottles of pills inside. I read the
labels: Estradiol, Finasteride, Spironolactone, Progestin. Late at
night and drunk, after the divorce had been finalized, I had toyed with
the idea of started on some hormones, transitioning to becoming a
woman. I?d gotten far enough into the research process to know what
these pills were for. Inside the purse there was also an envelope.
There was a knock on my door, Veronica yelling, ?Jack, come on, let?s
do this.?
?Five minutes, sorry. I got stuck on a client call,? I yelled back. I
heard her walk away, the sound of her heels clicking on the floor
outside my office. I imagined the knee-length pencil skirt she was
wearing, the silk blouse, how I?d always been so envious of her. I
picked up the envelope and opened it.
?Right now you?re probably wondering, why do I care if he tells
everyone in my life about my secret. If I do what he?s asking there is
no way they won?t eventually find out. Log into your bank account and
look at the last deposit. If you continue following my instructions.
That same amount will be deposited in your bank account at the end of
every month. If you don?t, I will empty your bank account and max out
every line of credit you have.?
I opened the banking app on my phone. A deposit had been made at 1:30
for $10,000. Holy shit.
Veronica yelled through the door again. I threw everything back in the
box quickly, put my coat and bag on top of it, shoved it under my desk
and walked out to join her in the meeting.
It took every bit of effort to keep focused the rest of the day, and
even with that I found myself daydreaming and wondering what would
happen tonight--wondering what would happen in a month, two months, a
year. I thought about transition videos I?d watched online. Men who?d
looked much worse than I currently did, who after 18 months of hormones
were suddenly buxom, bombshells. Was that what I really wanted? Did I
have any choice now? Fuck, fuck, fuck.
I walked through my front door, half expecting to be surprised by
another package. Or maybe the mystery neighbor who I had never seen
standing there, or maybe my mom holding a print out of the picture he?d
sent me, demanding to know what all of this was about. Instead, I came
home to an empty house. It was 6:30. I had an hour and 15 minutes
before I needed to be standing in the front window. I had a lot to do
before then. I was too excited to even think about eating. I opened a
bottle of white wine and poured myself a glass. I pulled everything out
of the box and set it on my bed, then stepped into the bathroom.
After washing, I took the mysterious bottle of hair removal cream and
read the directions. I stepped out of the water and applied it all over
my body. It said to leave it on for eight minutes if I wanted it to
remove hair beneath the surface of the skin. After three minutes it
started to tingle. After five minutes it started to burn. At six
minutes, the burning was more than a little uncomfortable, and at seven
minutes I thought my skin was on fire. Right as the timer on my watch
hit eight minutes, I stepped back under the shower and vigorously
scrubbed with my loofa. I was amazed at how immediate the relief was,
but even more shocked at how smooth my skin felt. I stepped out of the
shower, still amazed at how different everything felt as I dried
myself. I proceeded to cover my entire body in the apricots and cream
body lotion. Then I pulled out my razor and shaved my face, which
didn?t have much of a beard to begin with, as closely as possible,
wondering how much longer I?d even have to do this.
I sat down on the edge of my bed and pulled on the gaff panties and was
amazed at how smooth it made my crotch look. Then I pulled on the
Wolford tights. This time, I really couldn?t help it, before they were
all the way on, I just started to uncontrollable stroke my cock, which
had broken free from the gaffe. I leaned back on the bed as I was about
to cum and sprayed it all over my own stomach. I wiped it up with my
hand and licked it from my fingers. I cleaned myself up and resituated
the panties and pulled up the tights the rest of the way.
Then I pulled on the corset, pulling it as tightly as I could, glad
that I hadn?t eaten anything. When I thought I couldn?t pull it any
tighter, I let out a deep breath and pulled even harder then laced it
up. Looking in the mirror, between the corset and the hip padding built
into the panties, I could not believe how much more feminine my body
looked than ever before. I looked at my watch. Shit. 7:05. I had to
hurry.
I went to the bathroom and unpacked the make-quickly. I put on some
lady?s deodorant and sprayed myself with perfume. I applied concealer,
then foundation, making sure to powder between coats. Then I carefully
applied the false lashes, before finishing the rest of my makeup, going
for a dark smoky eye, and lots of definition. I got to the lipstick,
kissing the mirror in front of me, and then adding a coat of gloss.
Then, my favorite part: the wig. As I pulled it on and flipped it back
and looked back in the mirror, I was amazed. I?d dreamed of looking
this good, but had never come even close. I was almost as frightened as
I was excited. I could already tell I was going to take this much
farther than I?d ever thought and probably much farther than I was
really prepared to. I looked down at the throat spray, wondering if it
could actually do anything. It was a trope I?d read in stories on
websites on places like fictionmania, but from everything I?d
researched, it didn?t seem like such a thing had ever or could ever
really exist. Still I sprayed it apprehensively, wondering as I did if
the effect, if it worked, would wear off by the morning when I had to
go back to work, and immediately thought about taking a sick day
regardless. Right away, I felt something tighten in the back of my
throat. When I tried to speak, nothing came out. Then I felt it relax
slightly and when I spoke again, I found my voice easily an octave and
a half higher. In fact, when I tried to speak in my normal male voice
or anything deeper. I found myself unable to do so. 7:35. Shit.
I quickly put on a bra and slipped in the breast forms, liberally
applying the adhesive and repositioning them. The weight of them, the
way they pulled on my skin, besides the fact that I could feel the
breasts themselves, they still felt real on my chest, just numb. I
pulled on the black dress and stepped into the platform heels. 7:42. I
looked in the mirror and was, again, absolutely shocked by the feminine
form staring back at me. As I started to walk out of the room, I heard
my phone beep, a text. I picked it up quickly. ?You forgot the pills
and your nails.? I looked around. What the fuck? Then another beep.
?Take them now and do your nails. I know you?re ready. Don?t worry
about the 7:45 deadline.?
I walked back into my bedroom, taking in the click of my heels on the
hardwood, the feel of my nylon-clad legs rubbing against each other as
the tight dress made me walk in mincing steps and sway my hips. I
picked up the purse and dumped out the pills. I took them out, two from
each bottle and set them down on the counter top in the bathroom and
poured a glass of water. ?Oh what the hell,? I heard myself say in a
voice that sounded surprisingly like my sisters. I tossed the pills in
my mouth and took a large drink of water. Staring at the red outline of
my lips on the glass as I set it down.
I touched up my lipstick and then set down to apply and paint my nails.
I crossed my legs as I sat on the closed toilet in the bathroom. Never
in my life has I felt more feminine. Never in my life had I felt more
like this is who I was supposed to be. Never in my life had I felt more
complete. Holy shit. I was really going to go through with this all,
wasn?t I?
I opened the curtain and started out into the darkness toward the
neighbor?s house. I knew that someone was watching from one of those
window. Did he like what he saw? I thought. Was he standing there
jerking off while he watched me primp and pose? I started to make
kissing faces toward the house. I twirled. I arched my back and stuck
out my ass and my breasts. I didn?t even care who else could see me. At
this point, the way I looked, no one else in the neighborhood would
even believe it was me. They?d all assume I?d gotten lucky with some
unbelievably sexy girl. Let them think that, I thought.
My phone rang. The number was blocked. I answered. ?Very, very, very
nice. My dear,? the deep, masculine voice said on the other end.
?You?ve made me very pleased tonight.?
?Thank you,? I said, still amazing at the tone of my voice.
?Ah, I see the spray has worked. Still, I don?t remember asking you to
respond. That is okay for now, you are still learning my dear. Now, I
need you to respond. Please say, ?Yes, daddy. Thank you so much for the
nice things.?
?Yes, daddy. Thank you so much for the nice things.? I felt my
breathing increase. My heart was pounding in my chest.
?Now, and I know this will make you nervous, but please remember what I
am capable of, in five minutes you will walk out to the corner down the
block. You will stand at the corner, with your purse on your left
shoulder. And you will wait. When a black BMW pulls up and rolls down
its window you will say the following: ?Do you think you could give me
a ride? Pretty please?? You?ll bat your eyelashes and then when he
opens the door you will get in and cross your legs. From that moment
on, you will do exactly what he says.?
?---?
?Now, dear. Say, ?Yes, daddy. I promise to be a good girl.?
?Yes, daddy. I promise to be a good girl.?
To be continued...
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