Inside Out Part 3 The Return of Sheila
- 1 year ago
- 6
- 0
Inside Out Part 6 Sheila Settles Down free porn video
Inside Out Part 6 Sheila Settles Down
St Kitts is an island in the Caribbean part of the British commonwealth
mostly known for growing sugar. It is English speaking, there are no
income taxes, and you can buy citizenship for a $35,000 fee and either a
$250,000 investment or a $200,000 10 year loan to the government.
It was originally known as St Christopher's and eventually shortened to
the nickname for Christopher " Kit" It seemed appropriate to settle there
since St Christopher was the patron saint of travelers and I was
certainly on an interesting journey. Also St Christopher was removed from
the official list of Saints some years ago and I felt I was not in good
standing with the Church either.
I arrived and stayed at the Marriott while I looked for a place to live.
It didn't take long because it is a fairly small island. Finally I found
a house with a pool, on the side of a hill overlooking the ocean. It was
a short walk to a small beach and the views were spectacular. The main
house had two small bedrooms, a master suite, upstairs and a kitchen,
living room and lovely veranda on the first floor, that lead out to a
small pool. To the right of the pool was a little guest house that was
like a studio apartment. I got it for $350,000 and that in turn helped me
get my permanent citizenship and new passport.
The first day I am in my new place lounging my the pool in a two piece
swimsuit when I hear a man say "excuse me Ma-am "
I looked and there was a black man about 35 years old, probably 6"3" and
painfully thin. I said " Yes can I help you"
He replied "I am Jeremy I was the caretaker for this place for the former
owners."
I recalled that the real estate agent had mentioned him and replied "Of
course, I was told about you"
Jeremy said " I hope to work for you Ma'am, this place has been empty for
6 months, the real estate people had their own landscapers and I have a
wife and 7 children to feed"
I said " that is a large family Jerome but I don't know that I need a
caretaker"
Jeremy looked panicked and replied "Please Ma-am I'd do anything for you"
I smiled wickedly and undid the hook on my top and let it fall, his eyes
grew wide. I slinked over to him and rubbed his crotch.
I said " There might be more than shrubbery that needs to be cared for,
how would you feel about that? I could see how he had 7 children because
he got hard very quickly.
He replied "Oh Ma'am I don't know about that"
I frowned and said "But Jeremy you said you would do anything? I unzipped
his fly and grabbed hold of his cock. I thought "perfect it is long and
thin, just what I want."
He said "No Ma'am I could never cheat on my wife with another woman"
I smiled and said" Excellent!, that will not be an issue" I took my left
hand and pushed down my swimsuit bottom, he looked stunned. I turned
slowly to my left and bent down, while holding his cock in my right hand.
I guided his cock into my anus.
I said "Your Hired, you can start immediately."
Jeremy was an energetic worker who seemed to get some satisfaction from
his job. I felt his long skinny dick slip past my sphincter and tickle my
prostrate with each powerful thrust. It wasn't orgasmic but it was quite
pleasurable I am sure the pleasure was enhanced bu the fact that Jeremy
was my employee/servant and utterly dependent on me to support his
family. Power is my true aphrodisiac.
When he shot his load. I turned around and said " Very Good Jeremy, now
why don't you start your yard work, by the way you are the only one on
this island that knows my secret, if it should come out I would that it
was you"
Jeremy nodded and replied "Yes Ma'am I understand"
I said " Excellent, and call me Mistress"
He replied "Yeas Ma'-am er Mistress" and went about his work.
Most everything I needed could be found on St Kitts. One thing that
concerned me was medical care. I preferred to keep my true gender a
closely held piece of information but that might be difficult on such a
small island. Now the shopping and nightlife was much better on the
nearby island of St Martin so I made a occasional trips over there.
Fortunately, I found a French Doctor on St Martin, Segolene Decourcy. She
was an attractive woman about 40, short hair and glasses. When we first
met, she took my medical history, asked if I was seeing a Psychologist. I
said I had in the past but did not currently. She didn't seem to have a
problem with my withholding details of my medical history like the names
of my doctors.
She gave me a physical and he prescribed some hormones to counteract some
of the testosterone. and asked to see me again in a two months.
Before I left she asked Ms Collins Do you have intercourse with males? I
answered 'Yes I do" She continued "and females?"
I replied "No not since I started living as a female full time"
The second time I saw her she asked about any changes in my physical or
emotional condition..
I replied "my hair is thicker, skin a little softer"
She asked "Any sexual side effects?"
I replied "Perhaps I am deriving a bit more pleasure from my male
partners"
She looked pensive and asked "Do you mean you are more attracted to their
penis?"
I smiled and said "Well Yes I guess you could put it that way"
She continued "Any issues with erections/"
I said "No none whatsoever"
She then insisted on giving me another physical. She told me to put on
the johnny and excused herself for a couple of minutes. She came back in
and told me to lie on my back. She opened the johnny and reached down to
my crotch and felt my balls. She seemed to be playing with them as
opposed to examining them. Then she leaned over and kissed me on the
mouth and grabbed my cock and jerked it twice. As I had said there were
no problems with erection. She unbuttoned her white lab coat and revealed
a very perky set of tits on a very shapely body.
She climbed on the exam table slipped a condom on my dick and topped me.
It was wild and passionate. She fondled my tits and I fondled hers, we
exchanged passionate kisses an tongue thrusts. I was astonished at how
passive I was. It was as though I had reverted to Stuart. When confronted
with an aggressive woman, Sheila's personality faded into the background
and Stuart's passivity came to the forefront.
I shot my load into the condom and we collapsed into each others embrace.
Finally she got off the table, buttoned her coat and checked her
appearance in the mirror and said "You can get dressed now"
I must have looked surprised and she added drolly 'I needed to make sure
the hormones hadn't compromised your male sexual function"
I laughed and said "Well Doctor there must be other ways to do that, but
probably not nearly as enjoyable"
She smiled and relaxed a bit and said" I am a lesbian, but I do
occasionally like the feel of a cock inside me".
I smiled and replied "That's completely understandable, but may I ask you
an question?'
She replied "Of course"
I said "Don't you also miss the taste?" The color seemed to fade from
her face, she made no reply but looked down at my crotch to see the start
of an erection.
As she dropped to her knees in front of me I heard her say" Oui"
She took me in her mouth and with what seemed like constant suction
seemed to draw my cock further and further down he throat. Then she slid
her lips over and over it. She was in no hurry and was extremely skilled.
Eventually she slid a condom on it and went to work vigorously sucking
and eventually sucked every bit of cum out of me.
Without another word she went on to her next patient. She had the nerve
to bill me for the appointment but there was a handwritten note with the
bill asking if we could get together outside the office. I must say,
after a steady diet of kinky sex with straight, gay and bi males I really
enjoyed sex with Segolene.
I made regular trips over to St Martin and she made infrequent house
calls in St Kitts.
At one point Segolene introduced me to a Plastic Surgeon, Thierry Greze.
Now when my initial work was done in the Witness Protection Program there
was still a question of going back to my male identity, so the facial
feminizing only went so far. There was no going back now. So I decided to
have Thierry do more work around my eyes, nose, and lips. The changes he
did were subtle in one sense, but made a huge difference in the overall
look. I still wasn't what anyone would call pretty but I had a decidedly
more feminine countenance and a definite sexier look.
Although the sex was great, Segolene was bossy and bitchy and a weekend
was more than enough time to spend with her at any one time. Now if I am
to be totally truthful, yes she was a bitch, but I really didn't like not
being in control no matter how good the sex was. I didn't like Stuart's
personality taking over anymore
Now Segolene had a vested interest in keeping my dick working, so the
hormones she prescribed kept my skin soft, hair silky and occasionally
made my nipples sensitive but in no way kept me from being functional.
I loved my place and pool but it was a short walk to a little beach where
I would snorkel most every day. I was intrigued with all the brightly
colored tropical fish, it was like swimming in aquarium. The other thing
it did was keep me in excellent physical shape.
To keep occupied at night I often frequented the Royal Beach Casino at
the Marriott
There I met a tall Puerto Rican Black Jack dealer named Javier. He is
about 6' tall, maybe 30 years old. He speaks with a slight accent, sounds
like Antonio Banderas but doesn't look nearly as good. He is not a
particularly good dealer, takes some risks he shouldn't which of course
makes him interesting to me. I always play at his table and occasionally
we converse briefly between games. He is intelligent and articulate and
has a decent sense of humor.
One night when I went dressed in a spaghetti strapped green dress that
showed a great deal of tit. Actually it barely covered my nipples. I was
hoping to distract him and win big. He didn't seem overly distracted and
played his usual game
He said "You are a very good player"
I reply "Thank you but I prefer to play games in which I have the
advantage"
He says "Well you won't find games like that here"
I smiled seductively and said "Oh I know where to play, the problem is
finding another player"
Just then another dealer came to the table and Javier said "Sorry I am
finishing my shift".
I played a hand or two with the new dealer and then cashed out. As I
walked out to my car, a yellow Saab Convertible, I wondered about Javier.
He didn't over react to all the tit I was showing but then again seemed
interested in me at some level. I hate a mystery so I drove around back
to where the employees que up to take a bus back to Basseterre. He was
standing there talking to some other men and saw me park a little
distance away.
He walked over and said " Were you lucky tonight?"
I said " Not yet, need a ride?" He got in.
I asked" where to?"
He replied " Wherever you want, you're behind the wheel"
I laughed and said " Good answer"
We drove along the coast, he was staring at my thighs as I stepped on the
accelerator, clutch and brake. I sensuously stroked the knob of the
gearshift as we drove.
We stopped at a small bar frequented mostly by locals and sat down a
table on the terrace. It was a bit seedy and the service was lousy but
the view was fabulous. It was a marvelous tropical night with a cool
breeze blowing off the Caribbean. I noticed that my nipples which were
barely covered by my dress were firm and hard and quite obvious.
I ordered a Corona and he did the same. I took out a cigarette and he
immediately pulled out a lighter and lit it for me. I took a long drag
and exhaled it.
I asked "So Javier what brings to to St Kitts?"
Now probably the part of feminine behavior that I have mastered the least
is conversational chatter. I usually try for the quiet smoldering sexy
approach. Not that I pull that off all that well but I just can't be
chatty Cathy.
Fortunately, it was not a problem with Javier, the man loved to talk. I
got his entire life story.
We were only a little past childhood when the beers arrived. I put the
slice of lime in the mouth of the bottle and sucked a little lime juice
out then pushed it down with my tongue and sipped the beer.
He claimed to be a writer who moved here from San Juan because the cost
of living was less. But he found he had to work two jobs, cook by day,
dealer by night to make ends meet and had little time to write.
I took a long drag and exhaled slowly, and said "perhaps I can help you
make ends meet"
He looked puzzled, as if he didn't know if I were serious or not or
whether it was a sexual overture.
I continued "I need a housekeeper for my place. I would pay you the going
rate and let you live in a small cottage on the property. But that
there would be more than cooking and cleaning required. "
He asked "Do you mean personal services?"
I took another drag, batted my eyelashes and said as I exhaled
"Indeed and some very special and versatile services."
He asks" Versatile?"
I replied "Services to both male and female if you are so inclined?"
He replied" and if I was so inclined what would be the next step?"
I said" well an interview to assess your skills and see how you measure
up to the competition"
He said "And when could we do that?'
I smiled seductively and said " I'm free at the moment is there some
woman or man expecting you?'
He shook his head and said "No, Now will be fine, but while you are a
most attractive woman, would the male I am to service also be there
tonight?"
I licked my lips, smiled and said "Yes in a manner of speaking he will be
there"
Javier looked puzzled but said nothing.
I settled the check and drove to the house .As we entered I showed him
the little cottage.
We walked into the main house and I said
"Now for your interview. Take off all your clothes!" He complied in
silence
I walked over to him and fondled his balls and gave his cock a few jerks
to get it hard, then I compared compare him to my dildo. It was not
quite as long or as thick.
I smiled wickedly and said. "Not quite large enough, I'll need more
input"
With that I slipped a condom on his dick and got on my knees. I first
took his balls in my mouth and playfully pretended to bite them. Then I
slipped my lips over his cock and slid them down his shaft as far as I
could. Then I slowly worked my lips back to the tip of his cock. With the
tip of my tongue I licked all around the head of his dick like it was an
ice cream cone. I took him into my mouth and slowly sucked as I caressed
his tight ass with my hands. I let it out again and looked up at him and
said"
"OK Stud let's see what you can do"
I slid my lips over his cock and grabbed onto his ass cheeks and he
started to thrust repeatedly into my mouth. Before long he shot a wad of
spunk into the condom.
I went into the powder room to fix my lipstick. When I came out I said
"Javier you performed quite well"
He smiled and replied
"Thank you, and asked "when will I meet the male I need to service?"
I lit a cigarette inhaled deeply and exhaled, I smiled wickedly and said
"you already have."
He looked puzzled
I pushed the the spaghetti straps off my shoulders and wiggled out of my
dress.
I pushed my panties down and said
"Meet the male member of the household"
His eyes grow wide but then a smile runs across his face, he got down on
his knees and , kissed the inside of my thighs and stroked my cock. I put
a condom on as Javier took me in his mouth. His technique was excellent,
in some ways very feminine.
When he finished I took him by the hand and lead him into my bedroom, he
gasped a bit when he saw the frames the chains and handcuffs, but I
simply lead him to the bed and crawled up on it and assumed a doggy
position, looked back over my shoulder, handed him a condom and said
"Put this on and then put it in"
He was good at following orders and was enthusiastic but I must say he
wasn't as good as Jeremy in anal fucking.
Next I took his hand and lead him over to wooden frame and said
"Don't worry I won't hurt you unless you want me to"
He made no effort to avoid being shackled. I ran my hands all over his
naked body, he was hard as a rock, but that wasn't my focus. I slipped a
condom on my swollen dick and rammed it into his ass. There was no wince
or look of pain on his face. Clearly this was not the first cock up his
ass. I thrust powerfully into his anus time after time. He grabbed his
own dick and masturbated while I was punishing his anus. We both came at
the same time.
I unlocked the shackles and said
"You get the job, you can sleep in the cottage tonight"
With that I fell on my bed and went to sleep.
I awoke the next morning and walked out to the pool still in the nude and
slipped into the pool and was refreshed by the cool water. Javier came
out of the main house carrying a hot mug of coffee and a towel. As I
stepped out of the pool and handed me a towel. I dried off and let the
towel drop to the ground.
He said" Ma'am I made you coffee as he handed me the mug, but there is
little food in the kitchen"
I replied " Now you know why I need a housekeeper, and call me Mistress
if you please"
He replied "Yes Mistress, if you allow me the use of your car I will go
to the market and purchase some things. Is there anything in particular
you desire?'
I replied" the keys are on the desk in the living room, I would like some
melons if they look good"
Javier looked at my naked tits and replied
"I doubt there are better melons on the island than the ones you have
Mistress"
I laughed and he went on his way.
I relaxed under the umbrella with my coffee for a few minutes. Jeremy
the Gardener arrived and when he saw I was nude averted his eyes and went
to work trimming the shrubs.
Javier was bisexual, more gay than straight. He had many issues with
sexual identify. It was like having a pet chameleon He was quite
comfortable in the housekeeper role and being my submissive boy toy. At
other times he would become quite macho and seductive. It was a bit weird
but mostly fun. He would even do parts in elaborate role plays which
broke up the monotony.
He came in handy as a dinner date, clubbing companion. He was handsome
charming well spoken and utterly at my service.
So I had a place of my own in paradise, plenty of money, and three
lovers. A reluctant straight male who serviced me out of fear of losing
his income, a bossy lesbian female who wanted to control of our
relationship, and a sissy male who mostly performed a submissive role.
But It is a small island and I was bored with being on vacation all the
time, as strange as that may sound.
Now Javier was a great cook but not much of a writer. When the little
place on the beach where Javier and I had a drink was for sale. I
suggested I could buy it and open a club. Javier could be the executive
chef, and I would manage the business side. He loved the idea. So I
requested some money from Herr Hofer and bought it for a good price.
Javier took charge of the renovations and hiring. We called it Tequila
Sunset and we had a limited menu of mostly local seafood, and featured
local musicians. Given the great location and the terrific sunsets it
caught on quickly, first with locals and then with tourists.
I thoroughly enjoyed managing the business side and it gave me somewhere
other than the Casinos to hang out at night. Not only was the club making
money but I was saving all those gambling losses. Despite that fact that
he was making a good deal of money at the club Javier remained living in
my guest cottage and visiting my bedroom. I did have to hire another
housekeeper though. Our relationship shifted to business partners as well
as friends with benefits.
One evening just as we were about to close, Javier got quite upset at
something I said. He virtually fumed.
"You still treat me like a slave"
I gave him a sultry look and replied
"But darling I thought you liked it that way"
He replied "Well yes, but not all the time"
I though "Oh dear my boytoy is trying to be assertive"
So I said' Well what is it you want?'
He said "I want to seduce you"
I laughed and replied "Javier that is hardly necessary"
Frustrated he said "I want to control"
I frowned and said "All the time?"
He shook his head and said "No No, just once in a while"
I said "OK we will try it"
He looked surprised and said " Really, when"
We were finished for the night, so I reached in the purse pulled out my
car keys and tossed them to him and said
"How about now"
I walked over to my car and waited by the passenger side door.
Javier locked up and seemed to fly to the car and opened the door for me.
We drove home at a frightening rate of speed and after when we got to
the patio, he said
"I'll fix us a drink, what would you like?"
I replied "Oh whatever you think best darling"
He fixed a couple of gin and tonics and we stood looking at the ocean.
said "It's a beautiful night"
He replied any night with you is beautiful"
I almost spit out my drink but maintained my composure
Then he slipped behind me and kissed the nape of my neck, his lips moved
down my shoulder and back up to my ear. He nibbled at my ear while his
hand wandered to my tits.
I could feel his stiff cock up against the cheek of my ass. He unzipped
my dress and it fell to the floor. I turned to face him and he kissed me
on the mouth as his hands caressed my tits. I reached down and fondled
his balls and slid my hand up and down his cock. I sat on a chaise and he
knelt down and started to kiss the inside of my thighs, his tongue licked
the perimeter of my ass pussy. I did some shallow breathing and moaned
appropriately.
With his head still between my legs he stood up to a point where his cock
was at the same height as my ass. He slipped on a condom and entered me.
His strokes were powerful and with each thrust his loins crashed into my
ass. He was different than I had ever seen him and clearly enjoying
himself immensely. I, on the other hand found it to be a novel
experience but there were no sparks flying.
He shot his load into the condom, whispered "that was the best" and
drifted off to sleep.
I managed to slip out of his embrace without waking him and went for a
moonlight swim in the pool .The cool water refreshed my nude body. As I
swam I thought" he will want to do this again"
. Now the one good thing about was seeing this side of him was that it
seemed make him more desirable as a sub. Our Domme Sub sex had become
very routine and he was a very compliant sub. It occur ed to me that
occasionally playing these roles might help.
I devised a simple scheme. I told him the next morning he was fantastic
and that we should do this more often. He was beaming. To make it more
unpredictable, if the gross receipts for the night at the club were an
odd number I would be the domme and he would be the sub. If on the other
hand the total was even he could be the one in control. He loved the
idea.
Since I counted the money, and he was a bit mathematically challenged, he
never got suspicious that the number was odd three out of every four
nights. I never minded because I was still in control and the role
reversal every fourth night made the sex on the other three so much
better.
Now I thought this is probably as good as it can get, there is really
nothing more I want but still there seemed to be something missing
.
Then I got an email from Herr Hofer that said there was a $9,999 transfer
from the same account that the $5 million had come from. In the remarks
section it had the following message " Nutley
dawnland4.54litersbyflwrightshowaday1400"
Nutley was the safe word that Rick and I had used. It was also the first
word in my message that I needed to see him. A flood of thoughts went
through my mind. I was finally safe and happy, did I want to reopen that
chapter of my life? was it safe? What did the message mean? Why did he
want to see me? Did I want to see him?
Aeryn
- 17.08.2021
- 3
- 0
