lola goes black
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Lola's Beginning free porn video
Lola's Beginning
It was a wonderful day for me. Mom and I were in the kitchen preparing
dinner. I was all femmed up with my hair in a pony tail, jeans and a pink
pull over. This had been a daily routine for us after I came home from
school. Suddenly I heard my Dad's voice shout, "Jesus H. Christ! My son
is a fucking faggot! Get your pansy ass up stairs you little cocksucker
and get in some proper clothes! Good lord woman! What is wrong with you?"
This tirade led to a breakup and my father filed for divorce, He was a
Marine and had been deployed for many years. His time at home had been
minimal and he wasn't there when I had been having my gender problems.
Mom had been great and understanding, she got me into a school that was
accepting of TG challenged children.
I had found out at an early age that I was flexible enough to suck my own
dick. In the beginning I was just sucking a little stiff weenie that
really felt good. It was sort of like nursing on a pacifier. From the
time I started to get boners I was able to suck my self off. Usually 2 or
3 times a day. It was wonderful to wake up in the morning and take my
cock in my mouth and drain it. Like most teens I had a boner every five
minutes and if I couldn't get away to beat off I would find a place where
I could blow my self. I started to develop a taste for it and wondered
what it would be like to suck some else off.
One morning I was happily sucking away just short of cumming when a hand
on my butt forced my cock down my throat up to my pubic hair. "Honey I'm
really impressed that you can blow your self. I didn't think it was
possible. I'll hold you until you finish." I had a spectacular orgasm
that went on and on. My Mom was cool about it and would watch every so
often. I got so used to her presence that would blow my self when ever I
felt the need most anywhere in the house.
On my way leaving the house to go to school one morning I heard some
strange sounds coming from My Mom's room. She should have been gone to
work. I knocked on the door and called her name but there was no answer.
Opening the door I saw a rubber cocoon humping up and down on the bed and
moaning. I stood over the bed staring at my Mom entirely encased in
rubber and apparently in distress, I quickly unzipped the hood and
removed the penis gag from her mouth. "Quick, honey find the remote and
turn it off", she gasped as another orgasm tore through her. I searched
the bed and found the remote which I turned off. She was into solo
bondage and had got into a predicament where she was trapped with a run
away vibrator. I helped her out of her cocoon and agreed to check on her
every morning. We both had our kinks. Much later I developed a love for
latex, toys and femdom.
Once Mom had enrolled me in the TG friendly school I went fem full time
and adopted a fem name, Lola. It was great getting all femmed up in the
morning to go to school. Mom helped with the makeup until I was good
enough to do it on my own. She checked me over every morning before
leaving for school. All male clothing had long been trashed. I became
fully accepted at school as Lola and was treated as a young lady.
I was 15 when I developed a close relationship with a boy at school. We
started dating before he knew I was a boy. When we were on a date he
discovered my secret while we were necking. Instead of being shocked he
unzipped his fly, and guided my lips to his throbbing cock. It was my
first experience and instead of being what I had dreamed of I was face
fucked. I gagged on his cock as he rammed it down my throat and came. He
outed me to the guys at the school and frequently they would catch me in
a secluded area and line up for blow jobs.
By the time I graduated I was known as the school cum slut.
One of my female teachers picked up on what was going on and introduced
me to eating pussy. She would keep me after class and position me under
her desk and guide me on how to please a woman. I became very confused
about sex. Intercourse was still a mystery but I didn't feel any need
when I could blow myself.
At around twelve years old I discovered my Mom's lingerie in the clothes
hamper that was in our bathroom and was fascinated with the silkiness. In
a very short time I donned her panties, and slips. I would put on a
couple pairs of panties, add the slip and roll up in a sheet tightly
binding my arms and legs. I also had a pair of panties over my head with
the crotch over my nose. Her aroma was heaven to me and I would skip
school so I could bundle myself up in her clothes. One afternoon I heard
the front door close and my mom's high heels approaching and my bedroom
door opening.. "So you like to sniff my cunt girl! Get out of there and
come into my bedroom." I crawled out of my comfy cocoon wondering what
she had in mind. She was sitting on the bed when I came into her room.
"Ok you little cunt, here's what a real one looks like." With that she
spread her legs showing me a shaved beaver. "On your knees between my
legs and take a sniff!" I dropped to my knees between her legs and
inhaled her muskiness. My tongue came out and flicked her cunt before she
jumped up. "No, honey you can't eat your Mom, but now you know what
you've been sniffing." The experience left me looking forward to more.
The erotic odor never left me. God help me I love to eat pussy!
Once I was out of school I realized I needed a daddy for my sissy self.
As a trannie I was very good looking and had no trouble attracting guys.
My goal was to find one that had money and could foot the bill for a sex
change. This was a revelation that came to me in my late teens. I wanted
a sex change and needed to find the means to pull it off.
"Well honey I guess you have some experience giving blow jobs," mom said.
"Let me give you some advice on how to become a kept sissy! When you are
on your knees make little mewling noises when pulling out his dick like
you can't wait to get started. Once it is free go down on it like you are
starved and take it all the way up to his pubic hair, Suck real hard and
pull back so it pops out of you mouth with a loud sucking sound. Make
lots of gobbling and sucking sounds while looking into to his eyes. Once
he starts cumming make little happy sounds as you suck it out. It is very
important to swallow. Don't stop sucking until he pushes you off.
Anytime you get a chance go down on him. Nurse the flaccid ones while he
is relaxing. He will treasure your oral services."
Mom's advice worked! Eventually I found a rich guy that really loved my
oral services. He had enough money that it wasn't necessary for me to go
through years of therapy. Money talks! A trip to Thailand and shortly
there after I was the girl I always wanted to be. 44Ds, slim build and a
cunt opens a lot of doors. Of course it helped that my "daddy" had passed
away and I inherited his millions.
The doctor did a great job on constructing my cunt. It was everything a
girl could hope for. I was able to have extraordinary orgasms. What was
really neat was when wearing a skirt with pockets I could play with it in
public. I cut an opening in the pockets so I could finger my self when
ever the urge came over me. Doing this most of the time allowed for mini
orgasms that would cause me to gasp. People around me would show concern
and often ask if I was okay. Once I had a strong one at a restaurant
where I almost fell out of my chair. The reaction of those at other
tables reminded me of the movie "When Harry Met Sally." I even took to
wearing a vib during the day. I kept the setting on low. By time I got
home my clit would be twitching something fierce and juices would be
running down my thighs. I would head for the couch and click the vib on
high. The ensuing orgasms would be screamers and many times I would pass
out. The vib would wake me up shortly there after for many more until I
turned it off or the battery ran out.
The novelty of sucking dick had passed with my daddy and I wanted some
pussy to eat. I decided a sex slave was what I wanted and placed an ad on
Craig's List.
Now that I had the money and mansion to boot, I decided to turn the
basement into a playroom with all the bondage equipment I could and all
the toys and latex wear both for my self and "guests."
Once all of the bondage equipment arrived I hired a contractor to
renovate my basement into a dungeon and playroom. There would be a sound
proofed isolation chamber, latex covered tables to strap down visitors,
exercise cycles, chains and hoists, fucking machines, and couches for
oral services.
Several days after I had my playroom all set up for business I felt the
urge to try on some of the latex ware I had ordered. After I had powdered
up my bod I donned a pair of briefs, bra, catsuit, a mask with eye, nose
and mouth open. Thigh hi boots topped off the outfit. The aroma of latex
was overpowering and my hand was already rubbing my cunt which was
dripping wet. The feel and smell of the latex is so erotic that my head
was swimming. My nipples were as hard as nails as I squeezed them. It's
hard to explain the feeling of latex sliding over your skin almost as if
it is caressing you and the orgasm that followed my expert teasing was
extraordinary. I was hooked and stayed dressed the rest of the day,
frequently my hands would wander to my crotch and tease out another
orgasm.
The next day I returned to the playroom for more rubber fun. Remembering
how my Mom was into solo bondage I decided to try it out. First I lubed
myself up to allow easier access to my selections. First was the hood
with eye, nose and mouth openings. This was a back zip with a hole in top
to pull my hair through. It covered the neck and flared out over the
shoulders. I slipped it on enjoying the smell of latex. Next came the
above the elbow gloves and then I donned the cat suit. As I slid into it
my nipples stood up and I shivered a little. The crotch had a service
port that would allow strapping on the double dildo chastity belt. I
greased up my butt and cunt and inserted the 4 inch butt plug first
followed by the 6 incher. Pulling it up tightly I locked it in place.
Thigh high boots with 5 inch heels followed.
Next came a penis gag which I locked into place.
Picking up a latex bondage sack and ankle cuffs I entered my padded room.
Sitting on a padded bench I locked on the ankle cuffs and placed all of
the keys on a nearby shelf. I slid my feet into the sack and swung my
legs up on the bench sliding the sack up to my waist. Straps were then
buckled below and above my knees. Laying back I zipped the sack up from
the inside to my neck and placed the cord for the zipper were I would be
able to reach it along with the remote for the vibs in the dildos. I slid
one arm into the inner sleeve and placed the remote in that hand. With a
bit of struggling I was able to slip the other arm into remaining sleeve.
The excitement of the adventure already had me on the verge of an orgasm.
I snuggled down as far as I could luxuriating in the smell and caresses
of the latex. I clicked on the vibs which were set on random. Besides
vibrating these rotated and elongated. So you would really get a good
screwing. As soon as they came on I started having orgasms that would
peak and start up again. Since it was random at times I would peak and it
would stop leaving me frantically humping trying to get off. I'm not sure
how long I was encased but when I finally wanted out I discovered that I
had dropped the remote and couldn't shut it off. I was humping
frantically and trying to get my arms out of the inner sheaths but I had
slid down so far that I couldn't get them out. I was in a panic. Was I
going to be fucked to death? I was giggling hysterically and felt I would
go insane from the unending orgasms. Finally the batteries ran out
allowing me to fall into an exhausted sleep.
"So, are you able to free yourself?" the voice of my house keeper Ingrid
jarred me out of my exhausted sleep. Seeing that I was helpless she
extracted me from my rubber cocoon and helped me up to my room so I could
get cleaned up. She had been my Daddy's housekeeper and was used to kinky
behavior. In fact, Ingrid was from Germany and had been a dominatrix.
Later when I came down stairs wearing a new black catsuit, blue latex
dress, hood, and 5 inch heels an applicant for the slave position was
waiting in the living room. He was very young and slender, wearing a cute
leather skirt, purple satin blouse, and 5 inch black stilettos.
"So you are here in response to my ad for a sex slave?"
"Yes ma'am!"
"I had a female in mind not a fucking sissy!
This position requires utter surrender and full obedience to everything
demanded. Are you up to that?"
"Yes ma'am!"
"What's you name cunt and address me as mistress!"
"Jo-Ann, mistress."
"Are you gay Jo-Ann? Do you suck dick?"
"No, mistress."
" If I accept you as my sex slave, I will train you as a oral services
slave and my personal attendant. Room and board are provided but you
would be mine to do with as I please. This is an unpaid position. Any
questions?"
"No, mistress."
"In that event you are hired. Report to my housekeeper tomorrow morning
to begin training. You may go."
The next morning I decided to check on Jo-Ann and entered her room
without knocking. Jo-Ann was sitting on the edge of the bed, bent over
and bobbing up and down. Bemused I stood there watching. Sucking sounds
increased and I saw all of her muscles tense and body shudder as she
orgasmed over and over. When I thought it appropriate I cleared my throat
to signal my presence and was rewarded with a finger held up indicating I
should wait a minute. After much gobbling, sucking and heavy breathing
she lifted her head allowing a 9 or 10 inch cock flop out of her mouth.
Wiping the cum off of her lips and licking it off she looked at me with a
lifted eyebrow. "Jo-Ann I expect you to be up before me, dressed
appropriately and kneeling beside my bed every morning for servicing me.
Understood?"
"Yes Mistress!"
"How often do you blow your self, if I may ask?"
"Two or three times a day Mistress."
"From now on you will only be allowed when I say or else a chastity
device will be applied. Now that you've got me all wet you can do me. So
saying I sat on the edge of the bed and indicated that she should kneel
between my thighs and get busy."
She wasn't very skilled but, I was able to get a couple of orgasms.
"Slave your pussy eating sucks and needs training. A lot of hours on your
knees between my thighs with my training panties are in order. Right now
report to my housekeeper for your daily duties. She will help you select
your proper attire."
I still needed to find a female slave for my oral cravings.
By the end of the week I had 10 applicants for the position. As each
applicant was called in I had them strip. They had to have freshly shave
cunts and I didn't want to see the inter lips protruding. Just a fat,
smooth cunt with a split. Odor was another requirement. I wanted clean,
sweet smelling pussy. Eventually I had the applicants narrowed down to 3.
I had a room set up with a couch of oral pleasure, which was a latex
covered back rest with latex covered leg rests that could spread their
thighs. Between that was a latex padded step to kneel on giving me free
access to the yummies. My next requirement was that they be able to have
multiple orgasms and be able to last for many hours. A typical muffdiving
session for me was about 2 hours. After a happy afternoon of eating all
the pussy one could dream of I settled on a cute little redhead with a
latex fetish named Summer. This girl was a screamer and she had a
snapping pussy to boot. I must have indulged my self for over 2 hours. By
then she was spasming like she had epilepsy. Even after I had finished
sucking the last of her vaginal juices out and sat up she continued on.
Maybe it was because I had inserted a vibrator towards the end of the
session and it was still humming away.
The next morning I awoke to find Jo-Ann kneeling beside my bed. She was
totally encased in blue latex with her pony tail pulled up thru the top
of her hood.
Having seen her equipment I felt the urge to try it out. "Jo-Ann I'm
gonna blow you and I like it rough. A good face fucking would start my
day off right."
I dropped down on my knees and unzipped her catsuit and out popped a nine
inch cock already oozing precum. The 2 inch in diameter cock stretched my
mouth to its limits. I sucked on it happily for a few minutes until her
hips started to thrust. As asked for she grabbed me by the back of the
head and rammed it down my throat. It was so big I couldn't breath. Cum
started spurting down my throat. I was unable to suck as my jaws were
jammed wide open with 9 inches of dick was being rammed down my throat. I
didn't know anyone could cum so much or for so long. I struggled to
breath but she hung on and kept pumping. I guess I passed out. When I
woke up Ingrid was wiping the cum off my face and Jo-Ann looked scared. I
smiled and tried to tell her it was ok and it was what I had wanted but
there was so much cum on my vocal cords all I could do was gurgle.
I had Jo-Ann report to office later that day for her training session. I
was sitting at my desk preparing to work on a project of mine. I was
thinking of opening up a training center for sissies.
"Ok Jo-Ann it's training time to improve you cunt lapping skills. A few
hours in this trainer will help. Place your hands behind your back so I
can put on these cuffs then kneel down under my desk while I slip this
over your head." I slipped a hood over her head and buckled it around her
neck. The crotch of a pair of latex panties was attached to the hood. I
stepped into the panties and sat down pulling her face into my cunt. The
hood had eye holes so I could look into her eyes every so often. I backed
her up under the desk so I could reach the keyboard of my computer and
snugged her up so she could get busy. "Time to eat honey!" I didn't get a
lot of work done but Jo-Ann was enthusiastic. After about 2 hours of
floating on a cloud of orgasmic pleasure I freed her. "A few more
sessions and you will graduate."
Now that I had the 2 slaves for my pleasure I told Ingrid of my idea of a
sissy training school and asked for her help. With her background as a
dominatrix I felt I could learn a lot from her. She agreed and we started
making our plans for Lola's Retreat.
Wynona
- 24.11.2020
- 13
- 0
