Stuart part 6
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Inside Out Part 1 Stuart Fitzgerald Need To Disappear free porn video
Inside Out - Part 1 -- Stuart Fitzgerald Needs to Disappear
By Suzanne Knight
Well I don't know how to explain the situation I am in, I guess I was in
the wrong place at the wrong time. But I might as well start at the
beginning. My name is Stuart Fitzgerald, I live in Boston am in my mid
forties, divorced, and I work as a management consultant. Since my
teenage years, I have been a cross dresser. My alter ego is named
Sheila, as Sheila I am pretty much a loner. I look decent, actually
pretty good from a distance but not all that passable up close. I love
the thrill of getting dressed and being seen by men but seldom ever talk
to them. After the divorce I went through a phase of hanging out with
other tgirls and satisfied some bi curious fantasies. Once after having
a bit too much to drink I even did it with a guy. I felt awful afterward
and grew more concerned about being found out at work, it had cost me my
marriage and I didn't want to lose my career as well. I still dressed
but I was very careful and never interacted with anyone else as Sheila.
I was coming home very late from a business trip, the new tunnel from
the airport was closed for repairs and the old one had a massive tie up.
During the height of the construction I knew a way to bypass the traffic
jam by navigating through some back streets by the oil and gas tanks in
East Boston. As I drove down a deserted road I realized they must have
once again changed the traffic pattern because it appeared the road was
coming to a dead end. There were two cars pulled over. As I got closer I
saw a group of Hispanic looking men and two other men, all of a sudden
the shots rang out and the two other men were on the ground bleeding. I
immediately did a U turn as got out of there as fast as I could, in my
rear view mirror I could see the Hispanic men holding guns and I thought
I heard shots ring out.
My heart was pounding in my chest, in a panic I called 911 and reported
what I saw, not thinking too clearly I hung up before giving them my
name, then of course it occurred to me they surely have caller ID. I was
torn, I wanted to do the right thing but I was afraid my secret would be
somehow discovered. Discovery in the past had cost me a lot, I had
slowly rebuilt a life and my greatest fear was going through it again. I
had recently had an old friend who knew nothing of my cross dressing
stay with me for a few days. As a precaution all of Sheila's stuff had
been moved to my personal storage compartment. I had quite a bit of
stuff in there since I have a hard time getting rid of things. Some time
ago I had set up a false identity to buy things on line. I used the name
Steve Callahan so I had the storage unit, a VISA card, a not too bad
phony Driver's license, and a mailbox at the UPS Store all in that name.
I parked back at the Airport thought about it for a while and finally
drove to the police station.
The Police had responded quickly, it turned out it was an undercover
drug operation and had two guys in custody but didn't find them at the
scene or find anything incriminating on them. Now there were at least
four that I saw. The officers were both dead, so they needed my
testimony at the Grand Jury to indict them. They kept me in a hotel in
Boston for about a week. During that time a DEA agent came up from
Washington to talk to me. His name was Sam Phillips, and he was about my
age. He told me the two guys that the Boston Police had arrested were
Colombians and linked to a Drug Cartel. He showed me some pictures of
other members of the gang and I picked out the other two. Their names
were Edgar Velasquez and Carlos Jimenez. Sam indicated that he thought I
was in great danger and that the Feds should take over my protection.
Then there was a big hassle between the Boston PD and the Feds and it
was decided that the Boston PD would continue my security and the US
Attorney would impanel a grand Jury and indict the other two.
I went back to the hotel with my two guards, Billy and Jack who seemed
well suited to watching the Celtics and eating pizza but I wondered how
effective they would be in a crisis.
The next morning they were to take me to the Federal Courthouse. I was
walking out to the car, stopped, bent down to tie my shoelace, just then
all Hell broke loose bullets flew everywhere, I hit the ground and
stayed as flat as I could, Billy fell dead on top of me. Jack was badly
wounded. I heard the car screech away, people were screaming, the
doorman was calling 911. I decided I just had to get out of there and
pushed Billy's lifeless body off of me and started running down the
block. I turned the corner slowed to a walk, saw a McDonalds and went in
to the restroom and locked the door and tried to compose myself. What
the Hell was going on. I just came within a loose shoelace of being
killed. Who could I trust? What should I do now? Two things were clear I
couldn't depend on the Boston Police and Stuart Fitzgerald needed to
disappear.
I bought some clothes and a baseball cap and sunglasses at a nearby
Marshall's, changed, and took a taxi to my storage place. I got my fake
ID and credit card, and then I walked to a nearby shopping plaza and
bought a prepaid cell phone at Target. I called Enterprise and told them
to pick me up at the plaza because my car had just been towed. I rented
a Nissan Altima sedan and drove 50 miles west to Worcester and got a
cheap hotel room, the kind you just park in front of so nobody sees you
come and go. I lay down on the bed, so far so good, but I still needed a
plan and I needed one fast. It would not be long before my name and face
would be all over, with both the good guys and the bad guys looking for
me. I knew I had to avoid the bad guys but I wasn't too sure about the
good guys at this point. I dug Sam Phillips card out of my wallet I used
the prepaid cell I had to call him. Damn! his message said he was away
for a week, I transferred to his assistant and said I really need to
talk to him but she said it was impossible to reach him, she said she
was sure someone else could help, but I wasn't so sure of that and hung
up. How the Hell was I going to last a week! I didn't think the fake ID
and credit card could not be traced to me, so it was my appearance that
would give me away. The first part of the plan came to mind quickly, I
could drastically change my appearance and become Sheila. But I could
not pass well enough to function as Sheila for a week nor did I have any
ID or credit cards in that name. No I needed someone to play Steve to my
Sheila, but who?
Well first things first, I needed to get Sheila's stuff so it was back
to the storage unit. As I drove out of Worcester I passed a Veteran's
shelter, there were about a dozen middle aged guys standing outside
smoking. I thought to myself, there has got to be one in that crowd I
can recruit. I drove on to the storage place racking my brain thinking
of a way to do it and trying to get up enough courage to be Sheila on a
full time basis. Like most cross dressers I had an terrible fear of
being out in public and being read. I knew I would need to get past that
fear because in my current circumstance being read was a whole lot
better than being dead.
I got back to the motel and took a long hot shower, then I went about
shaving my entire body. In all my years of dressing I had never done
that. I had relied on long sleeve tops and shimmer tights to cover my
body hair. I loved the feel of my newly smooth skin.
Among the things I have going for me in passing are small hands and
feet, a cute well defined rear end, and relatively soft skin. On the
other hand I am not skinny, my shoulders are broad and I have a
prominent brow line with somewhat small eyes. One of my better talents
is the ability to raise my voice an octave or so. It sounds a bit
breathless, definitely husky like Kathleen Turner or Lauren Bacall but
it doesn't give me away immediately. To bolster my lagging confidence I
decided to go the whole nine yards, false eye lashes, glue on finger
nails, breast forms, faux vagina ( a Sheath Vee String from Castle
Supply), and of course Nina Ricci perfume.
I started by using transparent medical tape and stuck one end just above
my eyebrows and then pulled up and stick the other end at my hairline I
used a few pieces in a similar fashion. It has the effect of pulling my
brow line away from my eyes and making my eyes seem bigger and my face
more feminine. Then some liquid make up the kind that covers a lot of
flaws. Next came false eyelashes, eyeliner and shadow all to make my
eyes look bigger. Now I turned to the body. First I glued on my breast
forms, then I put on the faux vagina, then I took a deep breath and put
on the waist cincher. It gets my waist down to 30" so I wind up being
about 44" 30" 38" which isn't too bad for a 5'11" gal. I pulled on a
sheer black pair of pantyhose, they felt great on my smooth legs. Then
came a scoop neck red ribbed top that clung to my curves. I had to
fiddle with it until it showed a lot of cleavage. Next I wiggled into a
gray skirt which came to about 2" above the knee and stepped into a pair
of 3" black pumps. My crowning glory was,a shoulder length wavy blond
wig with bangs. I need the bangs to cover the tape on my forehead. I did
my lips in a dark red and glued on nails to match. A couple of gold hoop
earrings and a knock off Hermes scarf to hide my Adams Apple finished
the look.
I put on my black leather hip length jacket grabbed my purse put on a
pair of large sunglasses and took a look in the mirror. This was as good
as I ever looked, took a deep breath and walked out to my car and hoped
it was good enough. I drove to the shelter and circled the block a few
times waiting to see if the men would come out for another smoke break.
All this time I was time practicing my lines in my best femme voice..
Around 5PM they came out. I parked about 50 yards away and watched them.
It was a rough looking crowd but there looked to be a couple that were
about my size and fit my general description. Finally one of them who
had not seemed to mix with the crowd wandered away from the group. A
loner was precisely what I needed. He was probably in his mid fifties, a
bit older than what I was looking for, but otherwise was a good fit. I
was in no position to be picky.
It was now or never, I unbuttoned my jacket, hiked up my skirt and with
my heart pounding started the car drove right up to where he was,
opened the passenger side window and said, "Excuse me sir, do you know
where Oak st. is?"
He stuck his head in the window and what he saw was cleavage, thigh,
blond hair and red lips. He replied, "Sorry Miss, I don't."
I handed him a slip of paper and said, "These are the directions, maybe
if you look at them it would help."
On the paper was written:
Help Wanted: Travel Companion 1 week, $1000 cash
Nothing illegal, Nothing immoral involved
If you are interested I'll be parked around the corner at 7 pm
He looked surprised, I gave him a smile and said, "Hope to see you
then," and drove off down the street. Once out of sight I pulled over
and caught my breath. So far so good, the next two hours dragged. I
watched the, 6 O Clock news and as I thought, my picture and story were
all over the place. One piece of good news, the feds had arrested Edgar
Velasquez. I circled the block a little after 7 PM and there he was
standing on the sidewalk, I pulled over and put the window down and
said, "Get in," he complied. As soon as the door closed I hit the gas,
he said, "Wait, what's going on?"
I replied, "Don?t worry, we are going someplace to talk." I drove back
to the motel and parked in front of my room. I got out of the car, and
looked at him and said, "It's OK, I don't bite," and went to the motel,
he got out of the car and followed.
I needed to see if I could get through even a short interaction with a
person who didn't know about me, if I didn't get through the next 15
minutes I'd never make it for a week. I took off my jacket and
sunglasses and said, "I'm Sheila."
He nodded and said, "I'm Mike."
I lit a cigarette and fixed a drink, both of which I needed badly. I
offered him a drink but he refused I sat down on the edge of the bed and
crossed my legs showing a lot of thigh and said, "This is a little road
trip as far as DC, but we will take our time getting there. Your job is
to pretend to be my husband Steve Callahan, I have a credit card and
Driver's license in that name for you to use. You will drive the car,
open doors for me, light my cigarette, and otherwise treat me as a lady.
At the end of the week you will get $1000 and a bus ticket back to
Worcester." I thought my voice might have slipped out of character once
or twice but he gave no reaction.
He looked pensive and finally said, "Using somebodys credit card and ID
is illegal."
I replied, "I have permission to use the credit card, the bills would be
paid so there will be no fraud, and the ID is only to make it easier to
use the card." I noticed he was not making eye contact with me he kept
looking at my chest and legs.
He replied, "OK what do you mean by pretend to be your husband?"
I said, "Don't worry Mike, you are really not my type, we sleep in
separate beds."
He looked at me quizzically and said, "This room only has one bed."
I replied, "That's why we are going to get you a room of your own, now
practice this signature a few times."
He did and then went down to the office and got a room. We went to
Marshall's and bought him some decent clothes for the trip. It was all
going pretty well in terms of passing, or maybe Mike was just dense. The
sales clerk at Marshall's was completely oblivious, so she didn't count.
The more we interacted the more I thought he was seeing that something
wasn't quite right with me. I knew it couldn't go on much longer but I
was having a good time, it was taking my mind off my problems and if the
truth be told, I loved being Sheila and interacting with a man. I told
him to shower and shave and put on one of his new outfits and come back
to my room for some pizza. I ordered from Domino's and then got out of
all my clothes but left the breast forms and fake vagina in place and
slipped into black satin robe. As the kid from Domino's left he kept
giving me the eye. Did he think I was sexy? Or maybe it was the big tip
I gave him.
Mike came back and he had cleaned up pretty well. We ate some pizza and
he talked a bit. It turned out he was Viet Nam Vet, drug addict,
alcoholic, but claimed to be clean and sober now. The more we talked
without my cleavage and thigh showing the more doubt I saw in his face.
Finally after we finished eating he said, "I don't know what it is, but
there is something not quite right about you."
I gave him a smile took a slow seductive drag on my cigarette stood up,
exhaled in his direction, sucked in my gut, undid the belt of my robe
and let it fall open, exposing my breasts and vagina. His eyes got wide.
I said, "You see anything wrong here?"
He shook his head and I said, "Now go back to your room and come back
here at 9 AM sharp."
He ran out of the door, I let out my breath and laughed hysterically. I
was sure I couldn't keep the pretense up tomorrow but at least that last
sight should keep him tossing and turning all night. Well I had
interacted with Mike for about 3 hours, and he hadn't blurted out
"You're a Man!" Indeed, it seemed to take him quite a while to even get
suspicious. So all told it was going OK, but it was very stressful.
I took off the breast forms, got out of the vagina, removed my makeup
and wig and tried to sleep. Sleep was hard and I was awake by 6AM. Just
as well I needed a lot of prep time to be Sheila all day. I got up and
showered and shaved, decided to go with the breast forms because they
made me feel feminine and that would help keep me in character. I
figured I needed the waist cincher but decided to fore go the
uncomfortable faux vagina in favor of a gaffe. Now there weren't a lot
of casual clothes in Sheila's wardrobe but I decided on a black zippered
cardigan, a short denim skirt, and mid calf boots with a 2" heel. I used
the false eyelashes but went much easier on the eye makeup figuring I
would be wearing sunglasses much of the time, and when I didn't I would
probably wear my reading glasses. The nails were still on so I used the
same matching shade of lipstick as yesterday. Spritzed a little perfume,
put on large silver hoop earrings and slid a phony diamond solitaire
ring and a rhinestone encrusted band on the ring finger of my left hand.
Laughing to myself, I said in my male voice, "I now pronounce you both
man and wife," and replied in my femme voice, "Oh this is the happiest
day of my life."
It was still only 8AM so I made some coffee and watched the morning
news. I was still a big story but at least I wasn't the lead story. For
practice I repeated aloud in my femme voice everything the newscasters
said. Around 9AM there was a knock at the door, it was Mike. I let him
in said, Good Morning he nodded in reply. I handed him the car keys,
pointed to me luggage and said, "Please put these in the car."
Mike silently complied, I called the front desk to say I was leaving and
the key was in the room, grabbed my purse and leather jacket and went to
the car. Mike was standing next to the passenger door and opened it for
me, I slipped in and got comfortable, he got in the driver's side and
off we went.
It was a chilly late March morning the sky was overcast and gray. For
the first hour I tried a little small talk but didn't get much out of my
taciturn companion. After passing through Hartford, we were driving
south on I 91in the middle travel lane. There had been a large truck
next to us for a while and the noise was irritating. I glanced over and
saw the truck driver leering down at me, my denim skirt had ridden
pretty high up on my thigh. For some reason instead of covering up, I
found myself slipping the shoulder harness of my seat belt under my
breasts and unzipping my sweater to show some cleavage, I stroked my
thighs a couple of times, looked over at the trucker and licked my lips.
He blasted his air horn in appreciation which brought me back to my
senses.
As a slower moving truck prevented him for keeping pace with us, I
wondered to myself what just happened? A big part of my thrill of cross
dressing was getting men to look at me but I had never been so overtly
sexual. Deep in my thoughts I glanced over at Mike, apparently he too
had been stealing furtive glances because there was now a very obvious
bulge in his lap. I felt an incredible rush of power I had never felt
before, I wondered what his cock was like, how long? how thick?, cut or
uncut? I found myself fantasizing about sucking it. It was odd that my
focus was only his penis and not him. But there was not much to him and
I didn't find him all that attractive. I wish I could say I wanted no
part of him but that would not be exactly true. It was as though he was
a blank wall with a penis attached, almost like a human glory hole.
Just then we picked up a New York Radio station WINS, I think it was,
and I heard them talking about the manhunt for me. That snapped me out
of my erotic thoughts and brought me back to reality. I had had my fun
with Mike, it was time to fess up otherwise one or both of us might try
something that could end badly, I decided we would stop soon and I would
tell him then, it wouldn't do to blurt it out while he was driving on
the highway.
We drove through New Haven and stopped at a Cracker Barrel in Milford
CT, it also seemed to be the largest truck stop in America. He parked
the car and I said, "Wait a minute Mike, there is something you need to
know." He turned and looked at me I went on, "I haven't been entirely
truthful with you, I am a transvestite, a man dressed as a woman."
His eyes grew wide and he said, "What, but I saw."
I interrupted, "All part of the illusion, what you saw was not real"
He protested, "Well I'm not gay."
I replied, "And neither am I, that's why I said you weren't my type.
This trip is fulfilling a life long fantasy of mine and I really am
grateful to you for being a part of it."
Then he said angrily, "If you don't like men what was that all about
with the truck driver?"
I said, "It is not something I can easily explain."
He shook his head and said, "Well don't come near me!"
So much for my open sincere and vulnerable approach, that clearly didn't
get me anywhere.
We went in and had an early lunch. I must say I was about the best
looking real or pretend female in the place and certainly the only one
in a short skirt and boots. I felt like I was in a fish bowl so my every
move was calculated to appear feminine. As we ate I felt a lot of truck
drivers eyes on me, some I am sure, mentally undressing me. Good thing
they can't see what's under this skirt.
When we finished Mike bought a newspaper and said he was going to the
men's room. I took that to mean he might be a while so I went out on the
porch sat in a rocking chair crossed my legs and lit a cigarette. In no
time one of the truckers who had been eying me in the restaurant came
out, he sat down in the chair next to me and lit a cigarette. I looked
him over he was about 35 years old, dark hair and eyes and pretty buff
but only about 5'9." Then, just like the incident with the leering
trucker back on the highway, it seemed like someone else took over my
mind and body I twirled my hair with my right index finger, and licked
my lips, took a long drag and exhaled it through my nose. He looked me
over and said, "Out to lunch with your Dad?"
I was holding the cigarette in my left hand up by my ear, I turned it
and pointed to the rings and replied, "He is my husband and we are on a
little road trip."
The trucker replied, "Too bad, a hot babe like you and an old coot like
that."
I smiled seductively reached out and touched his arm and said, "You know
lately he has seemed to lose some stamina."
The trucker replied, "What a shame, just how far are you going?"
I took another drag and exhaled right into his face and said, "I usually
go all the way, but since my husband is just in the bathroom we probably
won't have time."
Just then Mike came out I got up and said, "Nice chatting with you," and
walked to the car with Mike.
He didn't hold the door but just got in the driver's side, just before I
got in I looked back at the trucker and blew him a kiss. As I settled in
Mike muttered, "Pervert," which shook me out of my delightful revelry.
I turned to him and said, "If and when I need moral advice from a
derelict drug addict I'll ask for it, you are being paid to do a job so
just shut up and do it!" I sounded tough but his rebuke had hit home
with me. I didn't understand what was going on, what was even worse I
realized that my tirade against him was delivered in my femme voice. It
had come out completely naturally, without my having to work at it.
We drove in silence through the rest of Connecticut when we got into NY
I had him stop at a shopping mall where I bought some more casual
clothes, jeans, lounge wear, two hooded sweatshirts as well a a navy
blue business suit and while blouse. Mike bought a couple of sports
magazines, and I bought a package of condoms, clearly weren't on the
same page.
We drove on stopped for the night at a Residence Inn in Fishkill NY.
The young man at the front desk, who looked to be a college student,
said they had no more smoking rooms available, but we checked in anyway
and a had no smoking suite room. I had the bedroom and Mike was to sleep
on the sofa bed, I had decided Mike would never see me except as Sheila,
lest he see my picture somewhere and put it all together. We got a quick
bite at a nearby Chile's and went back to the hotel to watch pay per
view movies. My mind wasn't on the screen. I kept thinking about what
had gone on today.
My therapist had told me once that my urge to cross dress was strongest
when I was under stress. Like when it was getting too hard to be Stuart,
I would take refuge for a short time and become Sheila as a way to cope
with stress. I thought maybe he was right if stress brings out Sheila,
the more stress, the more Sheila, and I had never been under this much
stress nor ever attempted to be Sheila this long. Certainly Sheila had
never interacted with men to this extent, and in one way, I was afraid I
was getting a little too comfortable in Sheila's heels. In another way
if I didn't get more comfortable being Sheila it could cost me my life.
I had no choice but I really didn't understand who or what I was when I
was being Sheila.
I went outside for a smoke, It was clear, chilly night I was sitting on
the hood of the car when Bobby the desk clerk came by, it was about 11PM
and he looked like he was leaving work. He stopped and said "Oh Mrs.
Callahan I am sorry we didn't have a smoking room for you but are you
having a pleasant stay otherwise?" Bobby was cute, no he was adorable,
about 6"2" very athletic build, curly brown hair and bright blue eyes.
Like the other men I had interacted with he was talking to my tits and
thighs, probably had me figured for a frustrated wife and in his view I
qualified as a MILF (Mother I'd Like to Fuck).
I got off the car his eyes followed me, batted my eyelashes took a long
drag and exhaled, and said, "The room is fine, my husband is watching
TV. I just came out for a smoke."
Bobby replied, "Do you just smoke cigarettes?"
I laughed and said, "Well, I don't smoke cigars, pipes or joints if
that's what you mean?"
He replied sheepishly, "No, I was thinking of Mr. Callahan as well."
I threw down my cigarette crushed it out with my boot, and said, "He
just smokes cigarettes too." I fingered my hair and licked my lips and
said," But I do occasionally smoke meat." I reached over and touched his
bulging crotch. I opened the door to the back seat, and unzipped his fly
and reached in to pull his cock out, I didn't think about anything but
his cock, I gently pushed him into the car and climbed in on top of him,
I slipped a condom on, I took his balls in my mouth and toyed with them.
He was moaning, I told him to be quiet, with my tongue I licked his
shaft from his balls to the tip of his cock three times. I opened wide
and wrapped my red lips around his cock, feeling it slide way deep into
my throat, I let it out excruciatingly slow, he was squirming and
groaning but I wasn't about to take my mouth off his cock to tell him to
stop, so I bit ever so gently down on it. He got my point. Then I
repeated that two more times, but as much as I was enjoying it I sensed
I better get to work so I picked up the pace, going faster and faster
and finally furiously devouring his cock, until a huge load of hot cum
shot into the condom.
I slipped the condom off and tucked his cock back into his pants got up
and said "Thanks Bobby! See you around" and I went back into the room,
Mike was standing by the window, he looked at me with disgust but said
nothing. I looked at Mike with disdain and said, "Jealous?"
He shook his head and said, "No you goddamn queer!"
I went into the bathroom, my head was spinning. What did I just do? Why
did I do It? It was a long mostly sleepless night. Thoughts kept going
through my mind. Am I a pervert? It is beginning to look that way. Is
Sheila a wanton slut? There doesn't seem to be much doubt about that.
Who am I? I kept trying to clear my head because I had something
important to do tomorrow.
Jayla
- 10.02.2023
- 24
- 0
