Never Saw His Face The Game Crossdresser Fantasy free porn video

This is a FigCaption - special HTML5 tag for Image (like short description, you can remove it)

never seen his face the game

here i was sitting parked in my car at my destination it had just gone
one am as i looked at my phone waiting for it to ring five minutes went
past then it rang i answered to a low quiet voice thats me entering the
high street go to location il be there in five minutes i hope your be
ready gave me a few extra orders
i opened my car door picked up my bag got out and closed the door and
got out thinking to myself how did i get here and was it really
happening remembering how it all starting from the begining

it was a sunday afternoon and i was looking threw the meets section as i
came across a headline that caught my eye open minded person wanted for
outdoor role play fun must like blindfolds i clicked the posting and
started reading - looking for that special individual must be open
minded not shy like outdoors avalible nights and also drive and most
importantly has no qarms about wearing a blindfold if interested send
message only if you agree to these terms intrigued i clicked the profile
the name on it was blankface which went well with his profile it was
rather blank no pictures and discribed his appearance 6 foot 4 well
built smartly dressed and his usual likes dislikes he had been a member
for five years i decided as i was curious i sent a sort message hello i
say your add in the meet section im interested to know more thanks x

a few days later i got message in my inbox with a email address attached
thank for replying to my ad please email me asap thank you i sent a
email with my profile name hi thanks for replying heres my email address
i would like to know more about your ad thanks x

within ten minutes i had a reply hello there i liked your profile i
enjoyed looking at your pictures even tho your face is hidden i
understand that we all have our security but very nice before we decide
on going any further you must agree to never want to see my face and if
we meet you must wear a blindfold simple yes or no will suffice if you
say yes you can change your mind anytime if you say no that will be the
end and you will never hear from me again also was attached was a
picture of a man in smartly dressed suit holding today's paper with my
name written on it his face blanked out

my first thought was this sounds dodgy but the curious part of my mind
wanted to know more well i could end it anytime i wanted so i replied
one word yes his reply was a simple thank you i will be in touch soon as
i am at work just now

two days later my inbox popped up as i had another message hello thank
you for agreeing to my requests are you very open minded and do you
enjoy sexually activities safe of course

yes i replied to both of them

that is very good it is nice to hear would you like to assist me in my
role play fantasy please bare in mind this will be outdoors and late at
night it will be a quiet park i know and may take a few hours and will
consist of many requirements before we meet

i thought to myself this is really interesting i cant wait to learn more
so i replied yes what's the requirements

well heres the main one when we meet you must be fully dressed before we
meet and when the meet ends you must wear what ever i want you to wear
also agree to role play and you must agree to be dominated and be my
sexual slave for one night protection will be used and most important
you will wear a blindfold the entire meet there will be exceptions where
you will need to take it off but you will never see my face it will
either be covered or hidden

ok if we meet i will have to find somewhere to change first as i cant
drive dressed i then asked can you send me pictures of you holding
todays paper in your boxers please and can you tell me more about this
game

his reply was a few pictures of him in his boxers a very muscled man
standing in black boxers holding todays paper also was attached was some
cock pictures with it resting on the paper it was very long and quiet
fat written was i know somewhere you can change dont worry about that
and will discuss more on the game when we meet

so i took a few moments thinking to myself this is horny and very erotic
i finally decided yes i will agree to your requirements' why not i
thought to myself you only live once

thank you for agreeing was the message back i will need a mobile number
and the name of the supermarket closed to you i will be in touch in a
few days also your shoe size

i replyed to his questions

a few days later my phone bleeped from an unknown number hello do you
know the recycling bins at the supermarket

yes i replied

i have left a gift for you behind the blue bin its in a grey bag this is
to prove im a not a timewaster please hurry as i dont someone else to
find it

so out i went to my supermarket i parked across from the bins and looked
around the car park was nearly empty i got out walked towards the
supermarket looked around and then walked back towards the bins i looked
behind the bin and a saw a grey bag i quickly grabbed it and walked back
to my car once inside i opened to find a shoebox and inside were a pair
of stunning ankle strap stilettos with a five inch heel a very expensive
brand just over a 100 pound this guy was really serious about this
inside was a note wear to get practice in them i then drove back home

the next day i recieved a text message i hope you like the shoes and i
hope its enough proof that im not wasting your time

yes there more than enough thank you x

thank you im glad you liked them may i ask one more reqirement of you

yes i replied you may

i would like you to sign a contract agreeing to my terms it saves
wasting my time and yours as we are going to alot of effort if you agree
when we meet i will take some pictures of you fully dressed with out
your face hidden if you break the contract i will upload them to the
supermarkets page where people will see you if you keep the contract i
will give you the memory card there on at the end of meet and you can
keep them
if you dont wish this to go any further that is fine we can just leave
it and go our seperate ways

well i thought i to myself if i agree to this theres no going back so
stuff it i replied yes il agree to a contract

thank you very much now i will leave another package for you at the bins
within the next few days once ive done that we will arrange to meet i
will write up the contract and you can sign it when we meet

the next few days went by then around 10 pm my phone bleeped package
waiting for you with instructions inside

i drove to the bins went round the back to see another grey bag i picked
it up inside the bag was another box containing a a remote vibrating
anal plug with no remote and very expensive thick blindfold one people
use for sleeping and a chastity cage there was also was a map and
instructions sheet be at this location on the 20th around 1 pm park your
car on the main street and wait for my call then walk to the location
instructions were as follows
i want you wear your school uniform outfit in your 5th picture blond
hair and with your lingerie from your last the red basgue with the black
stockings big lace tops and please wear diamond tights over them as i
like a schoolie to wear them aswell more layers more fun and the heels
also have the anal plug inserted inside you and the chasity device i
know these may be uncomfortable so please get some practice in wearing
them and i look forward to our meet
also please have full makeup on

so this was how it all began i parked my car up waited for his call then
my phone went im in the high street walk to the location il be there in
five minutes i hope your be ready and remember the blindfold you must be
wearing it or im leaving and have your back to me when i drive up
so i got out my car locked the doors walked towards the location it was
a short walk to a darkly light private road i was wearing a jogsuit over
my uniform i stopped just under a lamp post that wasnt working and
looked around no one around so i dropped my jog bottoms to the floor and
put them and my shoes i was wearing in a bag i then slipped into the
five inch heels i had been practicing wearing as the cold air touched my
diamond tights covered legs and took my top off putting it in the bag
leaving me wearing my uniform and lingerie which was black cardigan a
white black blouse with tie black pleated mini skirt diamond tights red
basque with suspenders black stockings and five inch heels and my blond
long hair peice i had the chastity and butt plug in place

i put the blindfold over my eyes and waited for what felt like ten
minutes rather than five as i heard a car engine coming towards me i
felt the heat of headlights go across my legs as a car stopped behide me
and a door opened and voice spoke hello there dont you look lovely i see
your wearing what we agreed as i heard footsteps walking towards me as i
felt hands touch my sides and my heart beating like mad arent you cold
il take your bag for you as he snatched my bag from my hands dont turn
around just yet and keep the blindfold on as i heard a door opening as i
could hear his footsteps walking around

are you ok to sign this contract then

yes i replied

ok here it is as i felt a folder being put in my hand and a pen in the
other

how am i meant to read it i asked

ive thought of that he replied as i felt a light go across the back of
my head as he held it above me i was alot smaller than him even with
heels on

dont turn around pull your blindfold aside then read and sign but do not
turn around

i pulled the blindfold aside as my eyes adjusted to the light i quickly
read over the contract which was basically i agreed to his terms and
would obey his every command and be his personal sex slave for four
hours four hours what
i know he wanted sex but four hours dont know if i could handle that

he then spoke

well are you going to sign it then

i thought this is it as i quickly signed and spoke ok thats its signed

good your all mine now put on the blindfold

i put the blindfold back on as he took the folder from my hands

wait 2 secs he replied as i was standing i heard the door shut then his
footsteps behind me

stand still for a moment as i heard a camera sound and a flash as he
took my photograph turn around he spoke i turned and felt the flash on
my face thats the pictures taken have you got the plug in yes i replied
as i felt the plug vibrate inside me ohhh i moaned in pleasure making my
legs tremble i now know where the remote was

good thats good now wait there

i stood standing for a few seconds as both his hands touched both my
arms come this way my dear as he guided me towards the car opening the
door he guided me into the seat pulling the seat belt over me clicking
it in his car smelt of apple air fresher as i heard his door opening and
him sitting in the seat beside me

well my little schoolie you look lovely we are going to go a drive for
about 20 minutes then we will go out a walk and the game will begin

as we drove along the car went a few turns i couldnt see at all with the
blindfold on as we went along a bumpy road we didnt really speak on the
drive a few words

i asked why the blindfold

he replied i work in a high profile job i need to remain a secret

oh i replied

yes its hard meeting im very grateful that you agreed

have you had many offers one or two mostly timewasters

then the car stopped thats us here ok i replied

he then got out and walked round

opened my door as he reached in unclipped the belt then took my hand and
guided me out

standing outside i felt the wind blowing up my skirt and him going woo
nice one

he then spoke we are going to a long walk

a long walk im blindfolded

dont worry il guide you as he put one arm round me and the other arm
took my hand as we started walking i could smell grass and tree bark

we walked for ages for what felt like an hour over uneven ground stones
gravel and what felt like wood my feet were getting sore i hadnt really
walked much in heels this high before

we then stopped

right thats far enough i think now we shall discuss the game now

ok as i said as i sense him standing in front me

ok now i want to listen carefully this is the game

how would you like to win back the contract and the pictures without
having to do anything we agreed

my feet were really sore by now and was really cold i thought to myself
i really could do with this and go home so why i asked

its part of the game makes it more exciting dont you think if you agree
to play the game you can win and go home without giving anything up and
i lose or i win and your ass and mouth is mine for the next four hours

ok then what have i to do

simple im going to go and hide and then your going to take the blindfold
off make your way back to the car now when your making your way back to
the car im going to hunt you down
everytime i find you il buzz the butt plug you have to stop and put the
blindfold back on then il run up and rip parts of your clothing off and
i mean rip they will be no use to you once there off dont worry il
replace whatever your wearing but note whatever clothing you have left
on is what im leaving you wearing when i drop you off
then il go hide again and you can go back on your way back to the car i
cant get you straight away i have to wait and give a head start of about
five minutes and then this will go on until your down to your lingerie
and stockings and heels on then your get final change to get to the car
if you fail that i will handcuff you and use you for my own pleasure for
the next four hours

and this is one rule if you remove the heels at all this forfits the
game in my favour and your lose two bits of clothing at time your have
about six times in total so dont break the rule and i wodnt hide as if
i dont find you il have to leave you here

if you dont want to do this i can bend you over right now and ride your
little sweet ass for one hour straight or we can play the game you
decide

i asked but i dont know where i am

thats the point my dear we are in a park with a few paths not many any
route you can take will take you back to the car some longer some
shorter i will point you in the right direction and give you a torch
that is all

what do you say then you up for it

i took a few seconds thinking i can do this

yes i will play

ok as he took my shoulders and turned me around this is the direction
and heres the torch as he slipped it in to hands now count to aloud to
100 and then go on your way im going to go hide now ok as i started
counting out to 100

100 as i pulled the blindfold down and my eyes adjusted to the moonlit
path it was a narrow pathway with trees all around very dark as i
switched the torch on i could see two paths in the distance i started
walking towards as the cold air breezed my legs i tried walking at
quicker pace but the ground was uneven and the plug was moving around in
my ass

after stumbling along the dark pathway for around ten minutes i felt
the plug start to vibrate ooh ooh i moaned

then his screamed voice blindfold on

i slowly pulled the blindfold over my eyes as i heard his footsteps run
towards me as he spun me round his heavy breath breathing on my face as
he grabbed my gardigan and ripped it open i felt the buttons fly off as
he pulled it down my sleeves and pulled it off flinging it to the ground
he then spun me back round right walk straight ahead count 20 steps then
take your blindfold off theres anything in front of you but take your
time

i walked counting my steps as i reached 20 i took my blindfold off and
turned around but it was too dark to see anything i started walking
again in the direction going along dark paths the torchs light wasnt
very bright but i could still see the path i walked along for another
five or so minutes then vibrate started again and oh oh

then blindfold on you know the routine

as i pulled the blindfold on he ran behind pulling at my skirt come on
come on he screamed as he pulled at the zip trying at get it to go down

il get it i said

its ok he grumbled as he ripped the zip open then pulling my skirt down
and lifting my feet one by one pulling the skirt away and throwing it
away

thats two done now count 20 steps and take your blindfold off

ok i replied as i felt the cold air on my bum cheeks now as my shirt
blew around in the wind pulling the shirt down to cover the top of my
tights i carried on down the path

shining the torch down the dark paths i came a cross a wooden bridge as
my heels clicked as i walked across the vibrate started

ok ok i shouted i know what to do know as he shouted ok back

i then heard him walking up to me as he undid my tie now thats one easy
now you know what to do now as he turned me in the direction in which to
walk i started to count

i was now only wearing my tights and shirt and undies underneath great i
thought to myself as the cold breeze went around me

after walking i tried to speed up my pace with bigger strides coming to
three split paths i had no idea which one to pick so i picked the middle
one just as i started walking down the path the plug vibrated again ok i
know i know i shouted

good stuff now il take those lovely but i wont rip them as i want to
keep

how will you get them off the i asked

good question as i felt my legs getting pulled away from me as he picked
and lay facedown on the cold grass and and kneed over me undoing my
ankle straps and taking my shoes then proceded to pull my tights off
struggling i went no no its cold i screamed

its ok il warm you up remember now two more attempts and then your ass
is mine he wisped in my ear as he put my heels back on me and pulled me
up from the ground

now you know what to do as he pointed me in the direction

last two times i had to pick up speed

as i started getting into a stride of walking faster my feet were
killing me so i stopped and sat on bench and i decided to relax for a
few seconds but it was a mistake as not long after sitting down the
vibrate began and i put the blind fold back on

having a rest a we oh dear oh dear as i was pulled up from the bench as
grabbed my shirt ripping it open and pulling it off

oh my don't you look wonderful all in your undies in the great outdoors

thanks i replied

now as this is your last try il give you a ten minute head start after
that if i catch your mine ok

ok i humbley replied

good stuff now as he turned me walk this way and keep going your on the
right path

this was it my last chance or i was getting used and abused for the rest
of the night so i put more effect into trying a light run with the heels
on as minutes passed as i speedly walked along the path i lost my
footing and feel straight on to the grass i was hurt it was long grass
but i picked myself and started again not long after the vibrations
began ohh ohh i moaned but this time it wasn't a quick vibrate this time
he kept it going as i dropped to my knees i heard him running behind

aww babe don't worry il be gentle plenty of fun your enjoy whats to come

ok ok il do anything i moaned back stop the vibrating as it was
vibrating my bum like mad

good stuff as he pulled my hands behind my back and the cold hard steel
of handcuffs were put on me

i then heard a zip get undown as i was kneeing i felt standing front of
me pulling my head up now suck nice as his hard penis touched my lips
and slowly entered my mouth and i started sucking away and he slowly
vibrating the plug in my ass

after a few minutes he started to facefuck me deep throating as i gagged
as his penis hit the back of my mouth holding my head going faster and
what felt like ages he pulled out and put a penis in my face

lick with your tongue up and down so i preceded to lick
thats it lick the balls lick all that juice up like that like that he
commanded
after what felt like an hour of sucking and licking he zipped his
trousers back up and pulled me to my feet frogmarching me down the path
where we going now i asked your find out

after a short walk felt the cold touch of steel we were at the car as i
was bent over the bonnet

stay there he said as i heard the door getting opened seconds later
closing then a packet getting opened and what sounded like a squirt and
a condom getting put on

now here we go as the voice sounded behind me as he pulled my knickers
to the side and the warmth of lube getting rubbed around my hole

now ready one two three as i felt him push the head of his penis into my
hole

ooh ooh i moaned be gentle

i will be don't worry a he slowly started thrusting in and out getting
deeper and deeper

too deep too deep i moaned as he kept trying to push it all the way in

its fine it fine il go slowly as he started a slow thrust

i put my hand over my hole to try and stop him going deeper

cant have that can we as he pulled my hands up undoing the cuffs then
holding my wrists he started thrusting faster and faster pulling me off
the bonnet standing me up as he thrusted in and out holding my wrists

no no no i screamed

you want me to stop

no no no keep going keep going i was enjoying it too much to stop for
him to stop

after what felt like hours he dragged me to the back of the seat of the
car throwing me in on my back and climbing on top of me and putting my
legs on his shoulders as he reinterred me thrusting in and out i had
multiple orgasms by now and as he was thrusting away i tryed to pull my
blindfold away but he said no as he grabbed my hands holding them at my
sides

cant have that you naughty girl as he pulled out and sat down with my
legs lying across him pulling me over onto top of with my back to him he
pushed back inside me

now ride girl ride me

i started bouncing up and down on his penis as best i could was hard
with heels on going up down but i did my best

after a while of doing this he pushed me off and sat me beside him now
we shall finish i felt my head getting pulled downwards and i felt the
warmth of his penis entering my mouth again after sucking for about 20
minutes i felt his breathing getting heavy as he shot his load into my
mouth

swallow swallow it all he ordered me to do after a few minutes of him
blowing his load he pushed my head up and i lay down in the seat

is that me done i asked yes it is just lie down on the back seat now im
going to handcuff you just now don't worry its just a precaution i don't
want you to take your blindfold as he locked them and i heard the door
opening and closing then another and the engine started as we drove back
i suddenly remember im wearing nothing basque and stockings and i don't
know where i am after a while the car stopped and the doors opened and i
felt legs getting pulled out of the car

we are here as he pulled me out the car as i stood aside the car i felt
a bag getting dropped at my feet right heres the keys to the cuffs i
wodnt drop them and heres the memory card with the pictures as he put
one in each of my hands

great thanks i cant see
your be fine just stay very still once ive drove away unlock yourself

thank you for playing my game it was truly enjoyable as he kissed me on
the cheek ive left something in your bag for the clothes you lost thank
you and good night i might be in touch i might not as i heard footsteps
walking away and a door closing then a car driving away
i fumbled with the keys unlocking myself i was back at the lampost
standing in my lingerie i grabbed the bag and ran to my car as it was
nearly daylight as the heels clicked on the concrete i didn't even know
who he was but he gave me a night to remember and i was wondering if i
would see him again or not see him

0
0

04.11.2021
9
0

Same as Never Saw His Face The Game crossdresser fantasy Videos

crossdresser fantasy

hi - my name is franny and i am a pantyhose addict - been that way since puberty wearing my mothers clothes - but lately, i have really indulged myself with buying spree at macys - loading up on hosiery . shapewear . dresses and heels - can never seem to satsify my fantasy of transformation to a woman - what would really put me over would be to entertain horny men and it might go something like the following wishful thoughti like meeting others on line who have the same passion i do for...

A Crossdresser Gets Caught

Johnny was gentle and had slightly feminine mannerisms for a guy. He had had quite a few escapades with women, a couple of failed marriages and a dozen or so relationships but all had fizzled out. He had never thought about the fact that maybe he was gay or bisexual and although he was not homophobic he thought the idea was not for him. He found women attractive and loved them wearing sexy lingerie and became almost obsessed with lingerie and all its variations, sometimes even more than the...

Crossdressing

Jaq Invites Crossdresser Over

Anyone who follows our adventures will know what type of lifestyle we lead.A short while ago Jaq got chatting to a crossdresser online. It turned out that he only lived a short drive from where we live. Kieran was twenty-two, his pictures looked amazing. Jaq asked me if she could invite Kieran to visit, an offer that I could not refuse.All was set for the Friday evening. To say we were excited would be an understatement. Jaq and I showered and dressed. Jaq looked amazing as always in a very...

Crossdressing

Milwaukee Cuckoldrsquos Wife and the Crossdresser

Judy used several sites over the years to find her friends with benefits. She never tells me until afterwards what she has done. It’s rare she tells me anything in advance. One day she advised me the k**s were at my parents and she was entertaining that night and I would have to stay in the family room. My curiosity was getting the better of me.She went and took a shower and asked me to come in and shave her pussy. She had me paint her fingernails and toenails. Once she was ready she put on her...

A Crossdressers Night in the Park

Last night I was on line in a crossdresser chat room where I was talking with Master Brian about me being a pain loving, submissive, bisexual crossdresser who was looking a master to use and abuse me. As we talked Master Brian asked me if I was dressed as a woman while I was on line with him. I told him that I was and then he asked me what I was wearing. I told him that I was all dressed up wearing a black silk mini skirtwith a black stretchy lace blouse. Master Brian then asked me what I had...

The Crossdresser Body Swap Part 1

The Crossdresser Body Swap Chapter 1 Ashleigh finished polishing her toenails with a final dab of red nail paint. She rolled onto her belly whilst letting her feet dangle off the bed to dry. She noticed the time on her phone and let out a sigh of annoyance, her neighbours would be coming around for another dinner night soon. Ashleigh always thought they were a weird bunch, always practicing meditation in their garden, plus their house was littered with all this voodoo and spiritual...

Crossdresser Got Caught By The Neighbor

Hello readers, my name is Rajesh, a 24-year-old guy who likes to dress like a girl. I am in Australia now. This story will tell you how a crossdresser got caught by a neighbor and had to do whatever the neighbor ordered. His name is Roy (name changed), he is 6’1 height with a well-built body, and he is in his late 50’s. I recently had to move to another unit as my old unit’s lease got finished. On a Friday morning, I was leaving for my office. I saw an old man (who lives in the next door unit)...

Gay Male

Crossdresser for mature couple

I am a bi crossdresser....love some pussy or cock. I registered on an fabswingers looking for a meeting with similar people.I was actively looking for an older couple to have some fun with. To cut a long story short, I finally got talking to a guy called Bill. He and his wife could entertain a gurl like me for a fun filled evening, if I was game. We both had a list of dos and donts for the night and we went over a few ground rules etc.I was to be their maid and waitress for the evening. They...

Teenage crossdresser

Here are the usual disclaimers this story is for adults only if you are viewing this andare not 18 years of age or older please close this page immediatly.There is no cross dressing in the story but this is how I began my transformation fromregular boy into cock suckking teenage crossdresser.We were having a really hot heat wave. i meat with my older brother (wear red shorts, and a black T-shirt) wanted me to get out of the house and off the computer so she suggested a movie. I felt wierd going...

crossdressers 1st time

hi, im new to this. this happened about 3 years ago now.I had started off the night being at my ex gfs house looking at her sexy underwear thinking how it would feel etc. so, having just started a new job I felt it was time to relax a little while she was out working (from 10pm til 6am). from this simple thought I became massively aroused and started trying on her underwear, make up, and even a wig that was in the apartment. soon enough, I was looking like a slutty crossdresser.I thought enough...

mature crossdresser 18 year old PART 1

Myself being a fulltime crossdresser and wear mini skirt and dresses all the time an high heels. A few weeks ago some new people move in across the street from me to be extact it was a woman and her 18 yr son.I talked to her few times and she was very nice and in our talks asked her if it bother her that i was a cd/tv she said nope. Well after couple weeks we became good friends and found out her son was shy and kind of a nerd. One day she came over to me and was little upset over something she...

Amazing Night With A Sexy Crossdresser

Any ways, it had been awhile, and I wasn’t in any sort of relationship at the time, and the thought of being with a tranny again had started to be on my mind. Luckily, this was before Craigslist dropped its casual encounters section, so it was relatively easy to look for hook ups, and being there was a TS/Crossdresser section, I could easily contact one. I remember looking through postings, hoping to find one that was attractive enough, because as I’m sure you know, many cross dressers and...

Crossdresser Turns Gay To Seduce His Tailor

Hi all! I am a family man with a loving wife, but she doesn’t know about my crossdressing. It just so happened that she had gone to her mother’s place during her pregnancy, and I got ample time for my crossdressing. I did all of my shopping on Myntra and bought myself some nice soft satin sarees, dresses, gowns, tops, high-heel shoes, a makeup kit, perfumes, and loads of bras. I was waiting for the delivery like a curious kid waits for their birthday gifts. Finally, the day arrived and the...

Gay Male

more crossdresser fantasy

franny again and i am still a pantyhose addict with a lot of wishful thinking - the following is fact with fiction but could be realityso i just can't stop wearing hose all the time and dressing really turns me on and i think i might have sparked some interest with my tentative on line friend - he contacted me immediately and expressed a desire to explore some of his latent feelings -so he said he was going to arrange cover story of guitar shopping to excuse himself for another alternate...

my life as a sissy crossdresser

it should be noted that i did not ask for this disposition to crossdress, rather it was presented to me quite by accident. circa 1958...grade school PTA fashion show. PTA fathers were asked to put on a fashion show dressed as their better halves. my dad was right in the mix. I remember he wore some mid calf, grey business suit w/jacket, tan stockings and black heels. i remember this because he practiced dressing days before the show. he wore some makeup and a wig. not very passable, but not...

Room 209 First Sex as a Crossdresser

crossdresser – trans – interracial – lgbt – first time – virgin – black cock – crossdressing – natural tits – braI've been crossdressing for much of my life, as far back as I can remember. I would even go to sleep as a k** and pray that I would wake up in a girl's body. In the last few years, now that I live by myself, I spent about $1,000 on a whole wardrobe of women's clothes for myself - bras, thongs, dresses, tops, stockings, lingerie, make-up, perfume, etc... I have also been overweight...

Cd crossdresser sissy caught by mom and dad

Backstory - I just turned 19, in college and still live in my hometown with my parents. I've been crossdressing on and off for the last probably 10-12 years. Till I was about 15 it was just whatever my sister or mom had that I could get my hands on while they were gone. Then when I was 15, I would order some online, or sneak out and go to a store right before they'd close. I've only told two girls, one who didn't believe me and the other who was supportive but didn't really care. For the last...

Night Trawling The Crossdresser

The streets of Pomona live two lives. Like maternal twins, they coexist in parallel, appearing as virtually identical to those merely passing through its old and storied neighborhoods. During the day, with the sun high overhead, myriads of people — whether they’re commuters traveling like drones or soccer moms distracted by their busy lives — they choke the streets in a constant pulse of life. Each person is absorbed by their own petty concerns, each oblivious to what is happening on the...

Crossdressing

Danni The Crossdresser First Time Sissy

by - sissy debbie This is a true story about what happened to me after graduating high school and how I became a sissy for woman who was nearly twice as old as me. --------------------- The summer after my senior year of high school a neighbor asked me to look after her house and her cat for a week while she took a trip with some friends. Her name was Heidi and she was an attractive woman about 38 years old. She just wanted me to stop in and check on everything a few times. I...

My first time with another crossdresser

In this story, I'll go in depth on how I became the "girl" that i am today. It all started when i was about 5 years old. I obviously wasnt sexualy active way back then, but thats the age i remember i fell in love with pantyhose. One night after my parents came back from a wedding, i was home with my brother and sister. They came home, changed and what not and went to bed. well my mother who changed in the bathroom left everything that she wore in there. i happened to pick up her pair of sheer...

My first Crossdresser Part One

When she walked in to the restaurant I knew I was in trouble. It was the end of three long days at the convention and I was tired. I had come down to the NASCAR Cafe for a sandwich, mainly because it was the only bar in the Sahara that didn't have video poker...I lose a lot of money playing video poker. Well there I am with my beer and sandwich, and I glance toward the entrance just as she's strutting toward a table.Convincing she was not, a crossdresser without question. But pretty, really...

A Crossdresser8217s Life

Hi! This is my first story on ISS so don’t be harsh on me. This isn’t a real story, but a fantasy which i am going to share with you,though the characters are real. I am a boy(21)(crossdresser) doing my engineering in Bangalore in a reputed college. I stay at one of my fathers friends house, his name is Rajesh. His first wife died due to cancer so he married again. His new wifes name is Rajni. Rajni, in her 30s, is a damn hot woman with a plus size figure. Now lets move on to story… Initially i...

Gay Male

Nenu Crossdresser Nunchi Gay

Hi, na peru ajay. nenu tenth class ki vachinappatiki naku crossdressing alavatu ayyindi. enduko emo telidu, kani adavalla laga chira, jackettu vesukovatam istham. mukhamga Bra and Panty. ma inti venaka oka portion lo vunde oka ammayyi thana battalu vutiki bayata aresedi. ala aresina vatilo thana Bra lu kuda vundevi. mamuluga avi sayantram avi tisesedi. kani oko sari marichipoyo emo battalu tisedi kadu. ala tiyanappudo leka oko sari Valla bathroom lone vadilesina battallono (valla bathroom...

Telling Mom Im A Crossdresser Part 2 The Adult Store

I awoke the next morning a little groggy as I slowly recalled the events that had taken place last night. I rubbed my body up and down feeling how the latex had now become a little sticky and how my ass and cock were still sore from the pounding I had taken. I read the note again left by my mother and decided to make breakfast as I was for when she arrived. It was just past 9am when I heard a fumbling at the door, my mother had walked in with her heels in her hands and her clothes hanging loose...

Crossdressing

Crossdresser wanting some dick on the road

I`ve been crossdressing since I was 20 years old.One of my favorite things to do is get all dressed up in womens clothes and drive around on the open road.Several years ago I was mad at my ex wife for doing some stupid shit with our checking account and we were split up for some well needed cooling off time.The more I got to thinking about her stupidity the more I got to smoking some pot and drinking a few mixed drinks to get the crap off my mind.I got pretty stoned and decided to get dolled...

crossdresser violation

My house is a small two-bedroom cottage with a study, lounge and combined kitchen-dining room. My bedroom has an ensuite. It is located in a quiet cul-de-sac in a quiet neighbourhood where everyone keeps to themselves. It is perfect for me. Perfect because I am single (due to a messy divorce where she got everything except the debts), perfect because I work odd hours, and prefect because I like my privacy; oh, and also perfect because I am a closet transvestite. Like most...

CD crossdresser daughterrsquos bitch

Note : This story is completely fictional!How did I end up like this? On my hands and knees dressed in just sexy stockings and suspenders and a lacy corset, my face in slutty make up, my lips wrapped around my daughter's boyfriend's cock while my daughter herself rammed an eight inch strapon up my arse. The worst of it was, humiliated though I felt, this was really turning me on. This is the story of how I became my daughter's bitch and how I came to love it.I suppose I shouldn't have let...

Crossdresser in Love

I woke up with my hands bound, my mouth gagged, and my ass plugged. The bed I was on was comfortable enough. This was just a reminder that these parts of my body were no longer mine to do with as I pleased. For tonight would be my wedding night. For months we had planned things out. Picking out a dress, a place for the ceremony, all the things that brides do with their future husbands. But for me, it also included a regimen of hormones to complete my becoming as feminine as can be for my man. I...

Crossdressing

Hitchhiking teen crossdresser

It was a 200 mile journey from the city to the outskirts of a small town by the countryside where I live, I have hitchhiked this road many a time but this day proves to be an exhilarating adventure into my first cross-dressing sexual encounter, I had my large backpack I carried with me with my belongings including in secret my lingerie, heels makeup etc. about 60 or so miles out a 4 wheel drive hauling a horse trailer pulled up alongside me, rolled down the passenger window a man who seemed to...

Crossdresser and I at Costco

I went to Costco over the weekend with my friends girlfriend. She went off shopping, and I went off to get a few things. I walked down some random isle, and saw a girl leaning down. I snuck a peek at her butt and saw a little bit of a thong showing over the top of her shorts. She was wearing a blue hoody. I looked up and saw that she had really short brown hair. I tried to see her face, when she stood up. A box fell from her hands and onto the floor. Being the nice guy that I am, I picked it up...

Crossdressing

Closet Crossdresser Fantasy

I find your ad on CL and we exchange a couple of e-mails. You tell me you have some of your wife's things to put on me, my stiff cock pulses harder. I show up and you invite me in. You're a larger gentleman that is in need of some attention. You offer me some wine and then show me to the bedroom.You open the drawer with her nighties and let me pick one. I find a stretchy red camisole with some matching red fingerless gloves. Then you pull open her panty drawer. I rummage around while...

Crossdresser and I at Costco

I went to Costco over the weekend with my friends girlfriend. She went off shopping, and I went off to get a few things. I walked down some random isle, and saw a girl leaning down. I snuck a peek at her butt and saw a little bit of a thong showing over the top of her shorts. She was wearing a blue hoody. I looked up and saw that she had really short brown hair. I tried to see her face, when she stood up. A box fell from her hands and onto the floor. Being the nice guy that I am, I picked it up...

Crossdresser to Trans Escort Part 3

This is a continuation of my Crossdresser to Trans Escort series.After my first fuck for money with the restaurant owner, things escalated. I arrived at work the next morning wearing a pair of black trousers, black blouse and flat ballet shoes. The owner called me into the back office before we opened up for the customers. He was sitting behind his desk wearing a tight black t-shirt which showed off his tanned skin and bulging muscles. 'I really enjoyed our transaction last night' he grinned,...

My Date with a Crossdresser

A couple of months ago, I was contacted by a crossdresser here at Xhamster. She has asked me not to reveal her identity.We arranged to meet one night at a motel near the Pittsburgh International Airport. I arrived at the agreed time, but when I knocked on her door she told me she wasn't ready yet and asked me to wait half an hour. I agreed.Half an hour later, I returned to her room, but she still wasn't ready. She was apologetic, and asked me if I would rather come back in another half hour, or...

olderman and mature crossdresser part 1

It was just a normal friday day so I went to the store to buy some food for the week.I wore a jean mini skirt and pink t-shirt and tan pantyhose with my 3"heels and make up and all. As I made my way down thru the ailse I notice a older tall gray haired slim man following me.Well I gave him a couple bending over shots and eye contact.I made my way to the check out an seen him in other line.I finshed checking out when I got outside to load my bags in my car he was parked next to me.He spoke to me...

Crossdresser ke saath maza

Hello frnds.How is everybody.I recently got another hot encounter in July 2008.It happend at my sis home.Both my sis and her husband work for an MNC.They had recently employed a new maid.They were supposed to go to Pune for some seminar from their company.Since this new maid is new in town and has nowhere to go so my sis said me to stay at her at home so that maid will not face any difficulty.i said ok.I understood the problem and said ok for the proposal.So i reached her home on the day on the...

Incest

CL Memories 1 Crossdresser True Story

I used to get a lot of fun out of CL. I'll post some short stories about some of my experiences there. I sure do miss it. This happened about 10 years ago. I was divorced and living alone, and playing whenever I got the hots and had a good opportunity.I checked CL one weekend night to see if there was any fun to be had, and found a post from a crossdresser visiting a nearby city and looking for company. She (I'll use that pronoun here) had a room in a local motel for the night. I responded to...

AutoRide Made Me A Crossdresser Whore 8211 Part 5

Except for some dirty and humiliating ones, most of Raghav’s dialogue will be in English in this part about the crossdresser whore. I thought that it is easier for me than translating each of the dialogues. The ride home was uneventful. I just sat dumbfounded in the back seat while Ragahv just fled the auto fast. In a short time, we reached my place. I picked my bags and climbed the stairs. Raghav followed me, carrying another small bag. Where did he get it from? I am sure he was spotting a...

Gay Male

Thangaiku Theriyaamal Amma Magalai Oothen

Indru tamil kama kathaiyil ilamaiyaana magalum pinbu vithavai ammavaiyum eppadi usar seithu matter poten endru ungaluku solugiren. Suvarasiyam athigam irukum kama kathaikul selalam vaarungal, en peyar karthik. En veethiiyil oru pen ilamaiyaaga sexiyaaga irupaal, avalai thinamum sight adithu kondu irupen. Thinamum aval kalluri sendru varum pozhuthu iru velaiyilum sight adika arambithu viduven. Aval peyar nandhini vayathu 21 irukum, avaluku veetil aan thunai kidaiyaathu. Veetil oru amma iru...

The Game First Time Sex Part 21 Tonyas Fantasy

The Game ... first time sex: Part 21 - Tonya's Fantasy Please read chapters 1 - 20 to get to get acquainted with my friends and me and to get immersed in the story. This is a long chapter, so if you aren't into details, jump to the last half of this story to pick up our usual action. The intro to chapter 18 has the most expanded synopsis to date. The following is a brief history of our group. It's been nearly two years since I met Donna on a Sunday afternoon when I was forced to tag along with...

First Time

Clothesline GameChapter 2

"Let's review," shouted the upperclassman with the bullhorn. "The Green Team has won one event and the Gold Team has won one. In higher education we call that a tie. So here's the deal, we will play one more game. Winners will be considered very, very cool... losers... oh my... losers will have to be initiated. I can't tell you too much about the initiation, but just think mud pit... over there... yes, that one. Keep mud pit in mind as you play. Also think indentured servitude. History...

A crossdressers first time fantasy

Im not an author in any way but I would like to tell you about my latest crossdressing adventures. I have been crossdressing for many years but maybe only twice in a year when the mood took my fancy and only ever indoors, the feel off nylon on my legs would get me very aroused and looking at my self in the mirror wearing high heels and a very short skirt had my cock pumping and I always had an intense orgasm, but over the last few years it has became more frequent and not confined to indoors...

Never saw his Face The Game

never seen his face the game here i was sitting parked in my car at my destination it had just gone one am as i looked at my phone waiting for it to ring five minutes went past then it rang i answered to a low quiet voice thats me entering the high street go to location il be there in five minutes i hope your be ready gave me a few extra orders i opened my car door picked up my bag got out and closed the door and got out thinking to myself how did i get here and was it...

A FATHERS FANTASY

I am a single father raising two daughters and a son. My oldest daughter, Becki is still living at home as she commutes to collage. She is very beautiful, 5'4", long dark red-brown hair, about 100 lbs. and she has big tits. I know I shouldn't notice that about my own daughter but it is hard not to notice. I try to be a cool dad, open minded as well as I try to give her as much privacy as possible. I wouldn't say she is slutty but she does seem to go through a good number of guys; but with her...

Thelma and her brother

Note : This story is completely fictional!In nineteen forty six Thelma Lou Anderson was married with three kids. Linda was the oldest. She was sixteen. Guy and George was ten and Guy seven. Thelma owned a beauty shop in Kansas City. She suspected her husband Lawerance was cheating on her again. She followed him one day when he thought she was at work and saw him go into a house. A woman opened the door and he went in. That was all the proof she needed. She went home and packed her suitcase and...

Incest

Telling Mom Im A Crossdresser Part 14 Back to the spa and a familiar face

Part 14: Back to the spaI'm sorry this story is a fair bit longer then my usual ones however I didnt want to separate thes and have another story with almost no sex in the first one so soon. Having said that I hope you enjoy my story and please read the whole thing. I promise you will not be dissappointed. I woke up the next morning lying next to mom in her bed. I was wearing a pair of white stockings and a corset and mom had her bra on. After Thomas had left Mom and I spent the night licking...

Crossdressing

First Time With Crossdressers

For once, I actually decided to look at some of the other categories on the streaming sites I'd visit. So many things came up under fetish. Some of it I don't get but to each their own. A BBW was mixed in with the fetish and as I had expected before hand, it wasn't my cup of tea. Several videos had girls dominating guys in leather or latex outfits. I liked how tight they were, showing off every curve of their body, leaving little to the imagination. Upon thought, I had never been...

The Passion of Mother Ethel

Mother Ethel always enjoyed the short walk to the train station. It was beautiful Autumnal morning and Mother Ethel took the opportunity to walk to the train station as she knew that she had a very busy day ahead. Those that saw Mother Ethel along the way bowed reverently,they knew that Mother Ethel was a Nun of the Monastery of Repentance and when a Nun or a Monk walked past it was polite to bow, for many knew what the Nun's and Monk's of the Monastery were capable of. As Mother Ethel strolled...

Chronicles With Sexy Crossdressers

My email id is Do not forget to let me know how this sex story was. Who knows, we might get even lucky if everything goes well ;) Clean shaved men inside female clothes (or people who are known by the name crossdressers) are my new found favorites. Believe me, I always make it a point to taste every bit of them with passion and fire. My hands and tongue never leave an inch of their body. Hairless, like women and the ‘EXTRA’ jackpot called ‘COCK’, is simply divine. This is a story of how a...

Gay Male

Hispanic Fantasy

Marty had always found Hispanic men irresistible. He was a small guy, five-foot-six-inches tall and very fair. To be exact, Marty was hairless and blond, the exact antithesis of the men that he had always desired. There was nothing he desired more than being the bitch of a rough Hispanic daddy. Ever since he had entered the gay scene, this was the dream he had always yearned for.It took him a full two years to build up the courage to test this fantasy, but one Saturday night he simply could no...

Gay Male

Hispanic Fantasy

Marty had always found Hispanic men irresistible. He was a small guy, five-foot-six-inches tall and very fair. To be exact, Marty was hairless and blond, the exact antithesis of the men that he had always desired. There was nothing he desired more than being the bitch of a rough Hispanic daddy. Ever since he had entered the gay scene, this was the dream he had always yearned for.It took him a full two years to build up the courage to test this fantasy, but one Saturday night he simply could no...

Gay Male

Dot Dorothea and Dick

Dot, Dorothea, and Dick Chapter One Dear sister: I found this letter among some others, scrolled up and tied with purple ribbon, in a chest belonging to our great grandfather. The name Charles has belonged to several in our family line, but I believe I know the one who received and saved this letter, and kept it preserved for so many years. I believe the letter speaks for itself, so I will now offer it up to you. Dearest Charles: I hope this missive finds you in such good...

Experiences Of A Crossdresser

This is an introduction to my crossdressing experiences – touching upon highlights along my journey. I will write more about these, and other encounters in detail, in time. These really are all true stories, no embellishments whatsoever.I had always been fascinated with women's clothing, specifically tights (pantyhose) and anything silky and sheer, like slips and sheer blouses. I would typically be drawn to anything black, but did have a fondness for nude tights and white slips, also. I usually...

Blackmailed Crossdresser part II

A few weeks after that first incident with Stefan where he had blackmailed me into having sex with him, I got a text message off him. I was a bit surprised, as we had managed to ignore each other in work. I was growing optimistic that this incident was behind me. Even though it was left me feeling violated and with lots of confused feelings about myself.I was shocked to open the message on my phone and seen two pictures of him fucking me in the hotel! I was on all fours on he bed, in bustier,...

Bisexual Crossdresser Fucked By Drunken Roommate

Hello, people. I am Sahil. I am currently living in Mumbai in a shared apartment with my roommate Raj. We both doing our engineering from different colleges in Mumbai. This story is based on my and my roommate’s real life experience. Which is how I am engaged in a sexual relationship with Raj. Let us start with the introduction. Introduction: Sahil The author of the story. I am 24 years old. Since I was at 14 I have a very strange fantasy of Crossdressing as a beautiful girl. Whenever I was...

First Time With A Hot Crossdresser

My email id is Please contact me for any queries, doubts or proposals. I usually work late nights, and leave home by 1 am. I take a rickshaw for home, which happens to cross this one spot where post-midnight you usually find young crossdressers here on business at the side of the road. They are dressed mostly in skimpy western outfits, some of them are really attractive. That’s saying a lot coming from me, for a 26-year-old straight guy. I’ve never been bi-curious either. It’s been months I’ve...

Gay Male

My Golden Summer with Blythe Ch 01

Our Last Day of School. I can’t believe it. This is my last day of school, I thought, not sure how I felt now that the long awaited day was here. Stepping out into the beautiful sunny afternoon, heading toward the group of waiting yellow school buses I breathed a sigh of relief. I was glad school was finished. Throughout High School like a ship at sea, I had plotted my course, studying hard. However, the Scholarship that many felt I had rightfully won had somehow ended up going to one of...

Antheas baby 1

“What’s wrong? What’s wrong?”Anthea looked up at her mum as she sat down at the dining table. “Nothing is wrong,” Anthea responded watching as her mum hurriedly dried her hands with a tea towel.“Is the baby okay? Are you okay? Is Jack okay?” she asked as her husband came into the room and pulled up a seat at the table.“We’re all fine Mum,” she responded exasperated with her mum’s anxiety. “I have something to tell you.”“Sit down Helen,” her dad snapped. “Give the lass a chance to speak.”Anthea...

Porn Trends