Coach s Winter Retreat
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Lola's Retreat free porn video
Lola's Retreat
Some of this story is true and much is fantasy. I'm a heterosexual
crossdresser and have never had a gay experience. But, "maybe the lady
doth protest to much!" I'm dedicating this story to Regina who gave me
the idea.
A Cry For Help
A rather large elderly man nervously approached my table where I was
relaxing and enjoying a double Martini. "Miss Lola?" he asked. "Yes, I
am! Can I help you?" He seemed really awe struck at my appearance. My
black satin blouse was accented by a gold necklace with a pretty gold
cross. Black midi skirt, nylons, and knee high boots. Around my waist
was a gold chain link belt and ears adorned with multiple gold hoops.
He was shaking so bad I told him to sit down, relax and tell me what
was on his mind.
"Mistress, you have a great reputation with your training programs.
Could you take me on at your retreat?" "What kind of training are you
interested in? It is rather expensive!" He looked around nervously and
whispered, "I want to be a sissy cocksucker." We all come in different
packages so I wasn't really taken aback. Usually candidates for my
programs are brought in by their spouses who specify the type of
training desired. "I've only got this coming weekend free. My wife
thinks I'm off on a business trip and not due back until Monday.. I
have very little money but maybe we could work out something in trade?"
I was looking for a maid to do housework and assist with other
candidates. "Tell you what I can use some help at my retreat this
weekend. Are you staying at a hotel?" He indicated that he was so I
told him I would transport him out to my retreat and call the hotel to
send his belongings over to my place. I tossed off my drink and we left
the bar.
How I Got Started
I started wearing panties when I was nine years old. Dressing came
years later after I came home from Nam. My wife was not thrilled and we
fought over it constantly. When ever I had an opportunity I would get
all femmed up and enjoy the wonderful calm that would come over me. I
soon developed a fascination with oral sex and would spend hours
watching videos involving blowjobs. I found myself getting sexually
excited, my mouth would be would be working in time with the person
giving head and I would find saliva drooling out of the corner of my
mouth. I was wanting to be that person. I had never given anyone a
blowjob and didn't think I would ever find the opportunity. I sure as
hell wasn't going to find some stranger and I wasn't about to ask any
of my friends. An idea unfolded in my mind. Buy a package of jumbo
hotdogs. Cook 'em up. Take a stiff straw and hollow out the wiener.
Jerk off and inject the cum into the wiener. I'd call it a training aid
for cocksuckers.
I didn't know what the real thing felt like but the feeling of the
wiener sliding over my lips was really exciting and of course squeezing
it gave me a shot of cum. They were all day suckers. They were also
good to eat when you were finished. I really became hooked on them and
always had one to suck on while watching videos.
One day I was deeply engrossed in a video and deep throating a wiener
when it was jerked out of my hands. "What the fuck are you doing?
What's this stuff leaking out of this wiener? Cum!" She shrieked! "You
faggot mother fucking cocksucker. I've had enough of your shit. Get the
hell out of this house right now. I'm filing for divorce and am going
to take your for everything I can. I'm e-mailing your boss and everyone
I know to tell them you are a cocksucking sissy! Get out now! Come back
tomorrow to collect your things."
So I grabbed my purse, keys and drove to a nearby motel. I first
stopped at a liquor store and bought some booze. I got a few strange
looks but, no one questioned me. Probably figured I was a tranny
hooker.
The divorce was messy. She took everything except my car. Lost my job
but, I had a separate bank account no one knew about that could keep me
afloat till I got my feet back on the ground.
After a lot of thought I decided to continue my life as a tranny and
become Lola a dominatrix. I would use some old contacts and be a call
girl. Fortunately some of the stuff I saved from the divorce was a
great collection of latex wear, toys, and bondage equipment. All I had
to do was buy the appropriate clothing for my new profession. I started
taking hormones and got a boob job. Later on I thought I might
transition all the way.
Business was good. Word of mouth and business cards provided me with
more business then I could handle. It's amazing how many executives
and highly placed persons look for these services if they are discreet
and provide the desired fantasy.
During one of my sessions with a customer that I knew fairly well I was
relaxing from an excellent blowjob when she stood up sporting a large
bulge in the front of her dress. Lifting up her dress she pulled down
her panties, which were soaked, and produced a very angry looking cock.
Strings of precum were trailing down to the floor. This was to be the
day I became a cocksucker. I put my hands on her hips and pulled her
toward me. I was trembling all over as licked the precum off the head
and wrapped my lips around the shaft. Sucking came automatically. I
found I could deep throat her cock all the way down to the pubic hair
without gagging. My head was swimming as I frantically sucked and
bobbed up and down. It became almost hypnotic. All too soon she tensed
up and cum started spurting in my mouth. I clamped my lips tightly
around the base a sucked like mad. The spasms were like electric shocks
to my lips and I had a violent orgasm that filled my panties and
started running down my leg. I had finally acted out my fantasy and
felt good about my self. It was a great experience and I was looking
forward to more encounters.
After several years I was able to move into a mansion in the country
that was willed to me by a satisfied customer. The interior was
remodeled to fit the needs of my trade by a contractor whose wife I had
trained to his specifications. Latex, leather, toys, bondage equipment
all were provided by manufacturers. Even new innovations were sent to
me for testing. All at no charge!
Because of the size of the mansion I needed some hired help to run the
place and to assist in training. One day the doorbell rang and I opened
the door to find a person standing there wearing a ski mask. At first I
thought it was a hold up but the figure held out an note instead of a
gun. The note said "I need help. I've escaped from some slavers. My
face is disfigured and I am unable to speak. I'm willing to work for
room and board. Please help!" I motioned him/her to come in. "Come into
the living room and have a seat." We sat down and I asked if he/she
would take off the mask. When the mask came off I was shocked to see
that where a mouth and nose should be, there was a cunt! I handed
him/her a pen and paper and asked for the story. It seems Gwen, that
was his name, had been taken by slavers at an early age. They had
surgically altered his face, removing teeth and altering his jaw. They
had then brainwashed him into a cocksucker. He said he craved it like a
drug addict and hoped that maybe I could find a use for his talent at
the resort. We struck a bargain and I gained a live in assistant.
Regina Starts Her Training
Gwen opened the door for us when we arrived. "Gwen this is Regina. She
will be staying here for the weekend undergoing training and assisting
as a maid. She will work for you. Please take her to the servant's
quarters and get her prepared. Be sure to show her around and explain
her duties after she is properly attired. Once you are finished bring
her to me so I can explain our training program."
Regina was startled by Gwen's appearance. She was encased from head to
toe in black, shiny latex. Only the eyes were visible "Regina this is
sissy Gwen. She is unable to speak but she'll get the point across.
Please follow her. I'll see you later."
Several hours later Gwen appeared with Regina. She was dressed as a
French Maid, full makeup and long wig. Underneath was a full black
latex catsuit and she was shod in 3 inch, black knee high boots. As she
tottered in I got a shy smile from lips adorned in bright red.
"Regina please remain standing with your hands clasped in front of you.
When you can address me it will be mistress or ma'am. Since you told me
you have never sucked cock and wish to become a sissy cocksucker, from
this point on will be humiliated, teased and called all of the pet
names applied to your chosen endeavor. You will now be fitted with a
penis gag to suck on. Headphones will supply lessons on how to suck
dick. You will listen to these 24 hours a day except when meeting with
me. I also have an extensive library of videos of men and women
engaging in oral sex which in your off duty hours you will watch. Any
questions? No? Gwen stuff that gag in her mouth and get this wannabe
cocksucker out of my sight."
I had got the training cds from a well known sissification site.
Employed properly along with other forms of reinforcement they were
very effective. Total enclosure in conjunction with the cds was one of
the keys. At night Regina would be totally encased in latex, placed in
a bondage sack and immobilized. A latex hood with built in earphones,
penis gag and only nose holes to breath through topped it off. After
she finished her duties I sent her off with Gwen to be tucked in.
The next morning I showered and shaved the body. Today I would wear my
latex Dom outfit. Latex briefs, latex bra, latex elbow length gloves,
full catsuit with back zip. Latex hood that only showed the eyes and
mouth. Drop dead red lipstick made a statement. Ponytail was pulled
through the top. I was so horny that the smell of the latex and the way
it caressed my body as I moved that I had a surprise orgasm. After I
cleaned up I headed down stairs for breakfast. Regina was there to
serve wearing a pink ruffled blouse, a pink mini skirt that showed her
white ruffled panties, a pair of 3 inch heels. The makeup was done so
she looked like a common slut. No wig today for her semi-bald head.
"Well how did you sleep slut? You really look like a big fuckin fairy.
The only way you will be able to suck dick is through a glory hole.
Hurry up and serve me, cunt!"
In the afternoon after all of her chores were done I took her into the
media room for more reinforcement by watching videos. I watched her
through out the viewing and noticed she was sucking the penis gag in
time with the performer in the video and when she shuddered. I stopped
the video screaming, "Did you just cum in your panties? Take them off
and let me see." She stood up and slipped them off displaying a large
cum stain and more dripping off her dick. "Ok bitch, you will suck that
cum out of your panties and clean off your sissy cock . Once you get
your panties back on I want you to follow me. Today your cherry lips
are going to wrap around their first cock." We went into another room
where Gwen was relaxing in a nice stuffed leather chair. "On your knees
in front of Gwen!" Regina knelt down between Gwen's knees as she
pulled out a cock of at least 8 inches. The head was purple and precum
was starting to ooze. Regina stared at it in fascination as it pulsed
in front of her lips. "Ok Regina open up and live that fantasy!" Gwen
was pretty gentle with Regina but didn't turn loose of her head until
she had sucked her dry. Regina sat back on her heels with a stunned
look on her face. "Well honey, you ain't a virgin any more. Tomorrow
you will become a real sissy cocksucker. Today only qualifies you as a
cocksucker. How do you feel?" "Mistress, I feel shaky, my lips are
tingling, I feel ashamed, elated, relieved, but it was pretty much as
had fantasized." said Regina in a silky voice. "Great! Come into the
sitting room and have a Martini to cut the cum in you mouth unless you
want to savor taste." We had our drinks then went down stairs to my
playroom to check on my other guests.
When we arrived down stairs I pointed out the rubberized mummies
standing up in alcoves. All had various hoses and tubes hooked up to
them "These folks are here in storage for their mistresses and masters
for up to a month. The hoses and tubes take care of all of their needs.
Gwen takes care of some as you will observe." Gwen proceeded to unzip
the service port on the first figure and began sucking him off. "This
is Gwen's reward for working here. All the cock she wants to suck!"
While Gwen was feeding we strolled around the playroom and I pointed
out my toys.
The rest of the day was mundane house keeping chores as well as
preparing for a get together of some of my TG friends. Regina didn't
know it yet but tomorrow was graduation day.
A Dream Realized
The whole day was spent preparing for the evening get together. Regina
went about her duties in her cute maid's outfit. At the end of the day
she went upstairs to change clothes.
Regina was again dressed as a sissy faggot. A pink pullover with SISSY
in sequins across the front, a white mini skirt, pink ruffled panties,
white knee high boots. No wig and make up like a hooker. The guests had
all arrived as I entered the room with Regina. "Folks this is Regina
and she wants to become a sissy cocksucker. Please feel free to use her
services!" I turned to Regina and said, "Please circulate among the
guests and provide service when requested." I could see she was scared
and embarrassed but she started out into the crowd.
"Come here honey," said on of the guests. Regina minced over
hesitantly, being unsure of what was to come. "On your knees faggot!
Open your mouth and close your eyes and your going to get a big
surprise." As Regina complied he unzipped his fly and waved a semi-hard
prick in her face. When she hesitated her jerked her forward and fed it
to her. Becoming impatient with her ministrations he proceeded to face
fuck her while holding the back of her head. Regina was gagging as he
rammed his cock down her throat. A crowd had gathered around them. The
guys stood around stroking their dicks awaiting their turns while the
women snickered and made deriding remarks on her technique.
"Suck it honey! Don't blow! Make sure to swallow baby! A lady doesn't
drool! Hurry up the other boys are getting restless! What a poor excuse
for a pansy! Best get some knee pads slut!"
One of the guys yelled, "Hurry up cunt I've got an M&M dick for you.
Melts in you mouth not in your hand!"
As Regina finished one another would take his place. Some took great
pleasure in giving her facials and just generally treating her with
disgust.
At the end of the evening I found Regina sitting in a corner, lip stick
smeared, cum all over her face but with a small satisfied smile on her
face. "Well Regina how was it? Was it all you thought it would be?"
Regina looked up and said, "I should have done this years ago. I always
knew deep down that I was a fag. I just couldn't bring myself to try
it. I was afraid of getting beat up and of being branded a cocksucking
faggot. I've dreamed of this day and night. I could imagine the silky
feel of a cock sliding across my lips, the salty taste, the head
poking the back of my throat and how the spasms felt as I wrapped my
lips around the shaft and sucked as the cum spurted down my throat and
filled my mouth. How it felt to suck it dry until it shrank up. It was
all I dreamed of. Thank you mistress!" I took a gold chain with the
words "Sissy Cocksucker" on it and hooked it around her neck. "Happy
graduation Regina. You are now a confirmed Sissy Cocksucker! You really
didn't need training, just an opportunity to live your fantasy and find
out if that was what you really wanted. We humiliated you intentionally
tonight as I said I would so you could have that experience. At least
you didn't get beat up which usually is the end result of a real
encounter of that kind or raped. Go into the bar and make your self
some drinks and relax while Gwen straightens the place up. Sleep well
tonight. I'll drive you to the airport in the morning. If things don't
work out for you feel free to come back and work for me.
Hortense
- 07.10.2022
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