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The Lesson free porn video
"The Lesson"
I stood in the living room of Jane's apartment and watched the black and
white picture on the television as her and Martha looked on. It showed
Jane down in the apartment laundry room putting a load of clothes in the
washer and another in the dryer. Then she fast forwarded the tape until
I came into the laundry room, then let it play once again. It showed me
going through the dryer she was using and going through her things. It
show me "borrowing" two pairs of panties, a camisole and a nightgown! I
was caught putting Jane's lingerie into a brown paper bag then leaving
the laundry room. I was now at the mercy of both women who know knew
nearly everything.
"I think he's either a panty sniffer or a little sissy cross dresser.
What do you think?" Marsha said.
"I think Tim here must like wearing the clothes because he took my
camisole and nightie too, see there?" Jane said as she rewound then
replayed the tape and we watched as I put the panties, the camisole and
the nightgown in the bag then left with them. They then started
wondering how much I had taken over the last year and a half I had been
living in the apartment complex! It wasn't long until Jane and Marsha
were over at my apartment down the hall and looking through the box of
ladies clothing I had stashed at the back of the closet!
I gathered all the things that had belonged to both ladies and offered
to give everything back. They didn't want the things back, so I offered
to pay to get everything I had taken replaced. They seemed to think that
over and after I gave Marsha a hundred dollars and Jane another two
hundred I figured we were even. I then mentioned the tape they had and
asked if I could have it to erase and then toss. But Jane decided to
hang onto it for a bit longer. It didn't take long to realize that she
wanted some leverage against me!
"So, by the look of your clothing collection Tim. It looks like you've
been wearing ladies clothing for quite some time," Jane said as she
looked through the skirts, blouses and dresses.
Meanwhile Marsha was looking over my little makeup case. The room got
silent, I could feel my face begin to redden.
"Why don't you get all dolled up for us sweetie? We'll wait in the
living room for you. And when you're ready you can give Marsha and me a
little fashion show!"
I told her I wasn't in the mood but that didn't matter. Jane mentioned
she still had that tape showing me at the very least stealing! I didn't
want that getting out so I decided to go along with them.
It took me nearly an hour to get made up and dressed. Then I entered the
living room where Jane and Marsha had been waiting. They switched the
television off and turned to me. Marsha stifled a giggle while Jane
looked on amused at my appearance. I wore five inch heels and had a
little trouble walking in them and my clothes were hopelessly out of
date. My accessories didn't fit my outfit, my shoes didn't match and my
black slip showed glaringly through the sheer white polyester blouse I
was wearing. They looked me over a bit more and noticed my amateurish
makeup job which appeared to them a bit much and overdone. But it was
the best I could do.
"Hummm," Jane said as she got up and looked me over. "With a little work
you wouldn't look all that bad!" she said. "Yes, it might be fun."
She continued as Martha looked on with growing interest. "He's small for
a man and with a little work he could wear anything I have in my closet!
Would you like that Tim? Since you love playing 'dress up' why don't you
come over to my place and I can show you a few tricks-of-the-trade. Me
and Martha could have you looking like a doll in no time!" she said.
"I...I don't think that would be such a good idea," I said as I
nervously stammered an answer. I apologized about taking their things
and figured since I paid them for everything the matter was closed.
"I wasn't making you an offer silly, I was telling you what you were
going to do!" Jane said with a now serious tone. "You like playing dress
up sissy boy? Well that's what we're going to do all weekend!"
Martha then added, "Since he likes girls clothes let's just see how much
little Tim here can take!"
They both giggled as I ushered them towards the door but before I could
get them out of the apartment they grabbed me and pulled me across the
hall stumbling on my high heels to Jane's apartment!
It didn't take long until they had me in a bubble bath. They noticed the
lack of hair on my body.
"He shaves everything and there's not a hair on his legs either!"
Martha exclaimed.
They Naired me hairless and smooth just the same and after my bath and a
shower to rinse off I found myself sitting at the vanity in Jane's
bedroom wearing a pair of her lace trimmed nylon panties! While Martha
fitted a brassiere on me Jane went to work giving me a complete pedicure
and finished with a gloss red polish on each of my toenails!
"I don't have any nail polish remover at my place!" I exclaimed as Jane
finished up.
"This is just to keep you in line Tim dear, we're just getting started.
So relax! We'll have a little fun for a while and if you are a good boy
and play along Martha and I will give you the only copy of that tape and
we'll forget the whole thing ever happened. Are you going to play along
now or are you going to be difficult?" she said as she looked up at me.
I told her I would do what she said and play along.
In another hour and a half I was fully made up, my hair was styled in a
feminine style and I was totally dressed and mincing around the bedroom
in one of Jane's dresses while Martha selected another outfit from the
closet. They were making me try on outfit after outfit complete with an
array of lingerie and different looks with makeup.
By the time I had tried on a few more outfits I was getting tired and
wanted to leave. Jane then rummaged through her closet and found one
more dress. This was a gray maid's work uniform complete with cap and
starched white apron and came with a pair of three inch heeled white
leather pumps. I watched as she unzipped it and took it off the hangar
and remembered the outfit from when she had been a motel maid a year
earlier! Martha unzipped the dress I had on as Jane handed me the gray
dress.
"Put this on, the shoes too!" she said.
I did as I was asked. As Martha zipped me into the dress and tied the
apron around my waist and bobby pinned the little cap to my hair. Jane
found a large feather duster and handed it to me.
"Since he like playing dress up and looking like a woman he might as
well do a little women's work, don't you think Martha?" Jane said with a
smile.
"Yes, that's a great idea! And after he finishes your apartment he can
start on mine!" Martha said with a smile!
The ladies watched television while I whistled through the living room
dusting and straightening like their personal maid.
"Don't worry Tim sweetie, you'll be a pro in high heels and a dress in
no time!" Jane said with a giggle and a pleased smile knowing she
wouldn't have to dust!
An hour later I was doing the same thing over at Martha's apartment! It
was fortunate we lived on the same floor and that nobody else had seen
me as they marched me from my place to Jane's and then over to Martha's
apartment. Another hour and a half later I was back at Jane's changing
back into the blouse and skirt I had on when they brought me over! They
then told me I could return to my apartment. Jane mentioned that I was
to come over every night for lessons in hair and makeup and to practice
walking in high heels! I didn't refuse but became a bit worried at how
long this would go on! I returned to my apartment with nobody else
seeing me and after changing back into my regular clothes I collapsed in
the living room chair exhausted.
Over the next few weeks I spent a lot of time at Jane's place and while
there she always had me dressed and made up and always had me in very
high heels. And to my misfortune the maid service I originally provided
continued on as well but was usually reserved for the weekends. Then
another day was over. Once back in my street clothes I left Jane's place
to return to mine.
"You're getting pretty good Tim! Don't you think so Martha?" she said
with a smile as Martha looked on.
"Yes, he's getting to be quite the 'little lady'! Maybe we should get
him all dolled up some Saturday morning and take the little sissy boy
shopping! After all the work we've done I'll bet he could pass for a
woman in a crowd easily!" she said with deepening thought.
But luckily Jane stepped in. "I don't think that's necessary, but you
know, Halloween is only two months away! We should have a little party
over here. That's it! We'll get Tim here all dolled up in a pretty
outfit and say it's his Halloween costume!"
They both smiled in agreement at that idea but I didn't and began to
complain. Enough was enough I thought. Then Jane said, "Don't worry Tim.
Nobody is going to find out. You just play along and after the party you
can have that tape. After all, I think we've both gotten enough maid
service out of you to make up for everything, don't you think?"
I agreed then returned to my apartment. I then looked at the calendar
and counted the days with dread until Jane's Halloween party! And it
wasn't long until the day arrived and I was back at Jane's apartment!
It was only early afternoon and the party didn't start till seven but
Jane wanted to get everything right. After another bath I was plucked,
powdered and painted once again and my hair was styled in period
fashion. Jane had picked out my outfit and told me I was going as a
1950's housewife complete with pearls and heels! I groaned at the idea
but didn't have much choice. I was going to be dressed from head to toe
and from the skin out for the party which seemed to excite Jane to no
end. After putting on the white satin panties complete with lace and
little satin bows she fitted me into a brassiere and added a pair of
silicone breast forms. A matching garterbelt came next complete with old
fashioned seamed hose. To get the right shape she then laced me into a
tight white satin corset and finished my foundation with a well padded
girdle which she made sure I was completely tucked into so not a trace
of a male bulge would show.
After putting on the white, lace trimmed nylon full slip she put me in a
frothy white petticoat. She had me put on the shiny rayon house dress
and had me step into the black patent leather stiletto shoes with five
inch heels! As she fluffed the dress out it was amazing how the nylon
chiffon petticoat held the skirt out! She finished by putting a pair of
pearl earrings into my now pierced ears then clasped a simple pearl
necklace around my neck. After checking my makeup, fluffing my dress and
adding another splash of perfume she felt I was ready for the party!
Martha and Jane had told me to just "go with it" and enjoy the party.
After all, I was just wearing a costume. A costume though that was a
little too feminine a little too real! I worried about that as the
guests started arriving but after a few stares and double takes things
quieted down and the party got underway. There were pirates, gangsters,
dance hall girls and the whole array of costumed guests at the party. I
was lucky I didn't know anyone there! Martha pointed out a couple of the
other guys that came dressed as women but it was a campy, phony style.
You could instantly tell they were guys. But with me the eyebrows would
go up when Jane would introduce me as her next door neighbor Tim! But
once again and after giving me a good look over, the moment quickly
passed and the party continued.
The drinks flowed and everyone got into the mood. There was food and
music and dancing too! I helped out doing my maid thing by bringing out
more refreshments like Jane had instructed me to do but everyone only
giggled at my being 'in character!' It wasn't long though until I was
noticed by someone else! It was a middle aged man in a suit and tie.
He'd come as a business man or something complete with briefcase. I
could see him from across the room as he chatted with the other guests
but noticed he would often watch me and look me over as I moved about
the room! I finally decided to take a drink and a seat at the couch.
Through force of habit after all of Jane's training I sat on the couch
and crossed my legs and smoothed my dress out. I couldn't get over the
swish my shiny nylon stockings made or the rustle of the chiffon
petticoats under that shiny, floral patterned rayon dress! A few people
looked my way but were soon back to dancing, chatting and working over
the punch bowl and refreshments. I set my drink down and gathered my
purse. I opened it and found my cigarettes then took one out. I put the
cigarette in my mouth then not being able to find a lighter I set it in
the ashtray. I immediately noticed the red lipstick print on the filter
as I put the cigarette down and then realized that I was now totally
feminized and dressed as a woman. I thought I looked alright but
remembered how Jane had went to the extra trouble to make me as
attractive as she could. When I saw outstretched arm holding the lit
lighter it didn't take long to realize that Jane had done her job more
than well! I took the cigarette from the ashtray and lit it from the
lighter the man in the suit held in front of me.
"That's a pretty wild look you have going there! I'm Jacob, Jacob
Watson," he said as he offered a handshake.
I accepted with my feminized hand with the long glamor length nails done
in a bright red. My thin gold bracelets tinkled as I shook his hand.
"I'm one of Jane's co-workers down at the office," he said. "Quite a
party isn't it?" he said as he moved in. "You mind?" he said as he sat
down beside me on the couch.
"I'm a neighbor of Jane's here in the apartment. The outfit was her
idea. I guess she went a little overboard," I said trying to deflect the
man's growing interest but it didn't work. I noticed him looking me
over, smelling my perfume.
"Yes," he said. "I really like that 50's look. That's when women looked
like women! Very feminine, very exciting!" he said. "And I love those
seamed stockings! I didn't think they made those anymore!" he said with
excitement.
I finished my cigarette then looked to the clock and saw that it was
getting late. I then noticed that Jane was saying goodbye to several
people and that they were leaving to check out a few other parties or to
just go home. But a few people hung around. Jacob continued with me.
"Care to dance?" he said.
"No! No, sorry," I said. "I can only lead."
He laughed then said, "Well we could try." He then got up and hustled me
to the middle of the large living room!
A slow song was playing on the stereo as he moved in and held me like a
woman! I didn't want to dance but played along hoping he would soon get
his fill and let me go back to the couch. I teetered on the stiletto
heels and heard my skirt and petticoats rustle as he moved me around the
room.
"You dance like a woman very well!" he said. "Yes, just like a real
'little lady'!" he continued and as he pulled me close I was shocked to
feel that he had a growing hard on in his pants! Once the song ended I
quickly pulled away and returned to the couch. Jacob mentioned getting a
drink then left me alone. But within minutes he was back at the couch
where I was sitting!
There were fewer people at the party now and the night was winding down.
Finally the only people who were left were me, Jacob, Jane and a male
friend and Martha and a guy she knew! Jane came over and sat down as
Martha and her friend were getting more than friendly. It wasn't long
until they got up and left the living room and disappeared into one of
the bedrooms!
Jane brought me a drink I didn't really want and told me to drink up! I
took a few sips then being thirsty downed the fruity punch bowl drink. A
few moments later she brought me another then struck up a conversation
with me and Jacob! I hadn't noticed Martha and her friend coming back
from the bedroom area and soon both men were leaving and now it was just
the four of us as Martha sat down. I mentioned it was getting late and
started to leave but the ladies insisted I stick around a while longer.
Martha brought me yet another drink!
The small talk continued and soon the girls decided to get up and pick
up the apartment and clean things up while Jacob continued talking with
me. I wanted to leave but started feeling tired and could have fallen
asleep on the couch right there. Jacob continued chatting and I got a
shock to feel his hand on my knee fondling my legs! I pushed him away
telling him it was only a costume party. Then the ladies returned.
"You look tired Tim," Martha said with a giggle.
"Yeah, I'm getting... should be going home," I said as I tried to get up
from the couch.
Jane got up and went to lock the front door. She then turned the lights
down low and came back to the couch. Jacob was still there putting his
arm around me, trying to feel me up and reach under my skirt to feel my
legs!
"You're so pretty dear, just relax! You're just so tense!" he said as he
whispered in my ear and held me close! He then kissed me on the lips!
I gasped as he held me and could feel my lipstick smear slightly as he
kissed me deeply his tongue probing! I struggled weakly but finally
managed to push him away. I tried to get up but was too dizzy and weak
to walk! I knew I had a few drinks but not that many. Then Jane looked
at me with a smile.
"Did you like your drinks sweetie? They were drugged!"
I heard both ladies laugh at my plight.
"It won't hurt you but we needed to make you a little bit more relaxed,
more pliable," Jane said as both her and Martha then lifted me from the
couch. I thought we were going to the door and that they were going to
take me back to my apartment but they led me to Jane's bedroom instead!
I was already groggy as they laid me on the bed. I felt Martha and Jane
fluffing up my skirt! They pulled the girdle off me then as Martha
finished pulling down my panties and taking them off Jane returned with
a tube of something. She put some on her fingers then reached between my
legs. She inserted two fingers and spread the substance deep inside me
and another dollop at the opening! I struggled and tried to get up but
this only made Jane mad.
"You just relax and take your medicine sissy or maybe you'd like to do
this without lubrication!?"
She and Martha pulled me up on the bed and put a pillow under my head
then fluffed my skirt and petticoats back down. I then noticed Jacob
enter the room. He took off his suit coat and set it across a chair then
started taking off his shirt and tie as he looked at me on the bed.
He then came to the foot of the bed. I could see his pants were already
tenting and that he had a hard on! I looked to see Jane and Martha still
in the room and instead of helping me they were taking seats to watch!
"You look so pretty Tim, we thought that since you looked so much like a
lady tonight that you might want to feel like one too!" Jane said as
both women then giggled and sat back to watch.
Jacob didn't waste any time. He climbed onto the bed and began fondling
me! He kissed me, squeezed my silicone breasts and fondled my nyloned
legs as he rubbed against me getting more excited by the minute! I tried
to scream out but couldn't! I tried moving but by now was too weak and
could only lay there wide eyed at what was happening.
"Feel like a lady yet Tim?" Martha said as both ladies watched and
waited.
"Well if he doesn't he soon will, won't you darling?" Jacob said with a
smile as he got between my legs and began unbuckling and unzipping his
pants. He then pulled them down to his knees to reveal a stiff hard on!
I tried to move, to struggle away but could only watch as he took out a
lubricated condom and rolled it down his throbbing erection. He then
swished up my dress and petticoats up over my waist then spread my
nyloned legs while the ladies squirmed in their chairs watching the
spectacle.
"Oooooh, we're going to have so much fun aren't we Timmy?" Martha said
as both ladies began to laugh at my predicament! He then took me behind
the knees and after spreading my legs even wider he lifted them over his
shoulders then took his member in his hand and started probing me! He
then found the opening and started pushing into me excitedly!
I gasped and grunted as I tried to struggle away but with the drug laced
drinks in my system it was no use. I could only lay there and wait for
what I knew would happen. With my lubrication and his lubricated condom
it didn't take long for him to start entering me! I felt the bulbous
head as he pressed against me, working to get inside! I then felt him
grind his hips and push harder until I felt myself being stretched! I
grunted again as I twitched on the bed blinking wide eyed while the
girls continued to giggle and squirm in their seats knowing exactly what
was happening! I tried to move but couldn't and felt the pressure build
and the stretching feeling continue.
"Ahhh yes, yes baby that's it!" he said as he hunched over me steering
into me. "I like it nice and tight, yesssss" he said with excitement as
he pushed harder.
I felt myself being stretched even further now! I grimaced and gave a
weak squeal as he pushed even more! Then, just when I thought I would
split in two I heard Jacob moan as the head entered me! The ladies
giggled as I issued another pained grunt then watched as he then hunched
over me and began stroking into me sinking deeper and deeper as he
worked me! He then held my nyloned and high heeled ankles in the air and
held my legs wide as he continued working me until he was all the way
in!
His dangling ball sack pressed tight against me now, my skirt and
petticoats up around my waist, my legs wide and in the air and my high
heels twitching at the experience. He gasped, "Ahhhhh, ohhhh, yessss,
nice, nice and tight!" He then started stroking in and out in little
thrusts until finally he was able to hump me completely in and out the
full length of his throbbing erection! The ladies watched excitedly.
They squirmed in their chairs and enjoyed with great satisfaction
watching the neighbor sissy boy and panty thief get what he deserved.
"Oh yes, you are one cute, little bitch!" he said as he worked me. Then
not being able to take anymore he gasped then thrust in as deep as he
could and held my legs high and wide, my high heels twitching in the
air! I felt him swell even larger as his ball sack pulled tight then
heard him gasp and shudder as I felt him twitch as he came inside of me!
I gasped with glazed eyes and felt my face redden with embarrassment
then heard the ladies laughing at seeing Jacob coming inside of me. And
when he pulled out he was still coming, spurting on my nyloned legs and
my dress and petticoats as he continued gasping and finished by jerking
himself dry!
He then got dressed and quietly left the bedroom. Jane and Martha came
over to the bed and smiled as they looked at me. I was on the verge of
passing out now.
"I wonder if he feels like a girl now?" Martha said.
"Well if he ever steals from the laundry room again he'll be getting the
same treatment all over again either way, right sissy boy!?" Jane said
with conviction.
I heard the swish of my clothes as they pulled my dress back down then
picked me up off the bed and quickly carried me back to my apartment! I
awoke on the floor in my livingroom early the next morning still in the
rayon dress and everything then as I got up I noticed the video tape of
me in the laundry room sitting on the coffee table! Amazingly Jane and
Martha had kept their bargain! I knew now that I wouldn't be sneaking
any more souvenirs from the laundry room ever again!
Libbie
- 24.12.2020
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