[continued from previous message]

of my “ panties she calls them “ into a bag to take with us. I was in
and out in few minutes holding a plastic shopping bag with 15 to 20
different styles of satin lingerie from thongs, g-strings, bikinis and
even a lipstick red thong satin leotard.

We arrived at her house just after midnight and she immediately made me
feel comfortable and welcome. She put on some music and poured us both a
large brandy and coke. We began just talking about anything again when
she asked if i was going to model my bag of satin lingerie for her . I
was very nervous and excited at the thought of modelling for her but
wasn't brave enough to start. Come on she said lets start with a proper
look at them you have on now. She reached out and opened the butten and
zip on my shorts letting them drop to my ankles then lifted my shirt up
and over my head. I then stepped out of my shorts .

I was now standing in my neighbours kitchen with only my white trainers
and a baby blue satin tanga briefs. Oooh she said circling me and
touching and fixing my underwear into her correct position. I was told
to walk in and out the kitchen for her a few times and all the time she
would grope and feel me. I would leave the kitchen and change into
different satin panties for her as we talked and drank brandy for the
next hour or two when she asked me to try on something else for her. I
was a little drunk by now and was enjoying modelling for her so agreed.
She disappeared upstairs and returned holding a pink satin french maid
costume which she held against me to check for size. Yes it will fit she
told me and to go change in to it. I was by now in a white satin thong
g-string and a little drunk so i went and put it on. I zipped up the
maid costume and adjusted it a little then walked back into the fully
lit kitchen. My neighbour looked at me with a wicked smile and was all
over me in seconds kissing and touching me. She kept putting her arms
round and lifting the satin dress to pull my thong up higher between my
ass cheeks as we kissed. Soon i was talking with my mature neighbour in
her kitchen dressed in a pink satin maid dress and drinking brandy while
she takes any moment to start feeling me up and talk dirty to me.

It was early morning by now and the sky was no longer black as daylight
broke. She came up close behind me squeezing my ass in the satin dress
and said iv got something else for you . Pour us a drink each and il be
right back. I poured the drinks and was putting the ice back into the
freezer when i felt her behind me, she squeezed my bum and then i felt something else sliding up the satin dress between my cheeks. I turned to
look and she was wearing a black rubber strapon. I stood straight and
said im not sure.

She told me that I would like it if i tried and that she would be gentle

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James
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Former Retired 2y
I like to crossdress in the privacy of my own home and it makes me feel
so aroused and horny.

One Saturday morning during Covid lockdown I decided to clean my
apartment wearing crotchless panties and fishnet holdups. I had just
slipped into a pair of black lacy crotchless panties and my cock was
starting to get aroused and stiff when the doorbell rang so slipping on
my dressing gown I answered the door to the Amazon Delivery man who had
placed a parcel on my doorstep and was social distancing. As I bent down
to pick up the parcel my dressing gown slipped open and the guy had a
good view of my semi stiff cock and balls.

Sorry I mumbled as I tried to cover myself, oh that's ok he replied it
looks amazing and sexy, not what I was expecting him to say so I said
would you like to come in?

Well he just walked in and as soon as I closed the door he started to
unzip his trousers and I opened my dressing gown.. by now my cock was
rock hard, but the best was yet come when he slid down his trousers and
boxers there was a huge cock getting very aroused. Well I reached over
and started to masturbate it and he did the same for me.. within minutes
we were rubbing our cocks together, so good I could feel my getting
ready to squirt my hot creamy cum, as I told him that he said yes he
also wanted to cum and at that moment we both squirted together… after cleaning my creamy cum off his huge cock with a few tissues and a quick
goodbye that was it he was gone to deliver his next parcel.

I have ordered several things from Amazon since but I never saw the guy
with the huge cock again.

10.6K views
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Kylie.j.96
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Been crossdressing most of my life1y
The most fun but also scariest at first was the first time i went out
dressed. It was haloween my freshman year of college. It’s the only time
I have actually had friends help with my costume and I killed it! Some
girls in my dorm “talked” me into doing a school girl costume.

I let them pick it out. Was the classic red plaid miniskirt, white
button up top, garter belt and fishnet stockings. With a white bra and
panties. Initially they were gonna have me to wear some regular undies
but I ended up wearing a thong…. Some prefunk drinks, jokes, and a dare
led to that.

I have long hair allready so they put my hair into pigtails and did my
makeup. They made me shave my legs. Was the first time I ever did that.
I was super nervous but excited. They had no idea I liked to crossdress
in secret. It was my first time ever doing it around someone or in
public. They definitely threw me in head first.

When we all were ready we walked to the house party. I was the only guy
dressed as a girl but everyone was really chill. People thought it was hilarious and awesome. Got lots of compliments. I was actually almost
passable and looked super cute! It was so awesome to be in a short skirt outside and moving around!

I got pretty drunk and had a great time! Only awkward part was falling
down on my way home. Totally flashed my ass to everyone. Waking up the
next morning with the skirt and top on the floor of my dorm, still in a
bra and undies was great. My roomate was passed out in his bed and
totally thought it was hilarious when he woke up.

It built a lot of confidence. It made me keep doing it every haloween. I
habent missed one yet!

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Fun Open-Minded and Nonjudgementail
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D Johnson
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4y
Originally Answered: What has been your best cross-dressing experience?
I met a woman in a chat room. We were both married and started to chat
quite often. As time progressed we decided to meet for a weekend. I flew
to her and we had a wonderful time. We were both in almost sexless
marriages and the excitement of a rendezvous was powerfull. We were both
in our 50's at the time. We enjoyed fantastic sex the entire weekend and decided to continue in our secret relationship. At first I did not tell
her that I enjoyed crossdressing but as we chatted each night on the
internet she realized my long held secret.snd said that the next time we
met she would help me to explore my femininity. It was incredible. She
was very accepting and enjoyed transforming me

I would keep my male persona the first day and night and then I would
become “Dawn” the next day and night. She convinced me to go out with
her in public fully dressed. We went clubbing and dancing (as
girlfriends) I was in heaven when we went to lunch in a very fancy
restaurant. She ordered so I didn't have to use my male voice. I even
got the courage to use the ladies room at her urging. All went well. Unfortunately. Her husband became ill and she cannot get away for our
wonderful times together. We still chat and send text messages almost
daily. She is an incredible lover both as male and female as well as girlfriends. We have matching nighties and have fun posing for each
other. Hopefully wr can explire more in the future.

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Blackie Shepard
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bi sexual, gay, 2y
dressed up, full makeup, knee high stiletto boots, diamond stud earrings
and walked in the ‘red light area’ got talking with some of the street girls, one of whom invited me to be part of a three some, but her client preferred another GG


8.6K views
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Heather
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full time crossdresser
·
1y
Being able to go out in public as just an ordinary woman with no
problems. Just wonderful.
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Dan
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May 19
Wearing the 40DD under a loose-fitting shirt and going grocery shopping.

It is so exciting knowing that I might get recognized or “caught” … (though not “hard”, I will often “ooze” a bit thru my shorts during the outing).

And, the reality is, I am not hurting anyone nor cheating on my wife!

I masturbate when I get home “safely” … (then put the groceries away!) Profile photo for Bobbi Cd
Bobbi Cd
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Unbelievable feeling of them on my legs and body Feb 26
I was at motel next to adult book store and I had pantyhose on my hole
body and hoddi and my 6 inch open toe heels under my arms and I walked
over to the book store and I got poppers and a booth for a hr and then I
got my shoes on and I was playing with my body and I was doing poppers
and I opened the door and walked out and I was at the end of hallway and
then I got on my knees doggy style with my legs spread wide open and
then I was sniffing poppers and I was so high and I went back to the
Booth and left the door open halfway and I got a freaky and a black guy
looking at me and I got up and spread my legs wide open and then I was
playing with my pussy doing poppers and then I said u want me baby and
then I was being a little sissy and he locked the door and he puts his
big cock in my pussy and it was a big cock and he fucked me nice and
hard and he said I love u baby and he said I would like to sit down and
u get on the top and ki

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Tallsis4
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May 14
When a straight guy pick me up at the club , took me to his apartment,
we kissed , I give him bj and he didnt know I was transgender until he
took my panties and wanted to do it! He wasn’t even very drunk! We both
found this very funny!! We didn’t do it that night , but he called me
and we dated for a 4 months with sex!!😊
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Khloe West
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Boss at CEO of My Own Life6y
Originally Answered: What has been your best cross-dressing experience?
Wow!

Thanks for the A2A and I’ve no idea where to start or stop. Never
thought that I’d type these words, but there have almost been too many awesome experiences to recollect! I could likely write a quite unlikely
novel length tome about it all, and all in the past 6–7 years!

After surveying myself and my wife? A few high points that had great
pics. I was going to choose my top 3, but asked her and she had some
great input as well, so visuals shall be the bar to clear. BRB while I
review lists vs. pics…and apologies if this gets long.

Top of the pops and where this all began in earnest? My “drag makeover”
at the hands of legendary drag queen Courtney Act. There was an odd
array of events that led to this, but this was rather the “kick off”.
You can use this link, or if you hit YT and query “straight husband goes drag”, I’m about the only thing that pops up.

One of my first choices? About falling out of my chair at being asked to
model for a Trans* fundraiser book project that I was going to volunteer “boots on the ground” support to.


Getting stage direction while in face, but not dress, in my first film
op…and the residual glitter that was with us for ages after the film
ending in a very Busby Berkley manner with LOTS of falling glitter.



My first request to do print/web advert photo shoot for a local resale
joint that leans vintage?


A MOST unexpected “kitchen makeover” at the talented hands of Stephen Dimmick, who has done Vogue cover work. I was out to make notes on a
home repair job and things ran off the rails. I loved this! What he did
with my eyes? Amazing!


And you thought I was kidding when I said I could blather on all night…

In closing? (I know, most thought I likely never would at this point).
One of my fave moments was pushing beyond the visual in to the social at
a play called “Casa Valentina” by Fierstein and based loosely on the
book “Casa Susanna” and that escape in the day of the early 60’s. We saw it with pals while I was in colorful drab, and liked it so much that we
decided to see it again, but this time I dressed for the event! It was a
play about transvestites, so why not fly the flag?



And yes, it did cause a few raised eyebrows in the “Men’s Room” during intermission.

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Answer requested by
Gisbelle Belle
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Ezra Jones
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Auto Mechanic at Self-Employment5y
Originally Answered: What has been your best cross-dressing experience?
I can say that the best for me was the time I got pulled over by the
cops wearing a pink bustier with garters and stocking I was driving to
get a new dress to get with my outfit and I was stopped by the police
for having a out light when he came to the window u was wearing a pencil
skirt and a satin top with my pink stocking and hi heels. I was asked to
step out of the car and I was happy to do so.when I got out I was asked
why I was dressed like that and I told I had a date I was going to and
my girlfriend likes me to show up wearing something sexy I was thrilled
when he patted me down. I was wearing a bustier with underwire cups and
push up in a size 38c he asked me of my chest was all mine and I told
him that it was I had a lot of people drive by which was a thrill to
have people looked at me while I was all dressed up. I even paraded
around a little bit to she off for his dash camera and for the other
people who were going by I was nervous about it but I was also very
turned on when he e searching me

19.8K views
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Amber Fountaine
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A well experienced old Queen with a young heart.7y
Originally Answered: What has been your best cross-dressing experience?
Quite a few years ago there was a bar at a local Holiday Inn that got a
lot of business travelers. The bartender and waitress were both friends
of mine and knew both my male and female personas. Occasionally my
girlfriend and I would let some guy pick us up and we had it worked out
where the guy never knew I wasn’t really a woman.

On one occasion we’d had a fairly good time with a guy, nothing at all spectacular, and the next night I stopped in on the way back from night
school in male clothing. The place was almost dead so I was able to tell
my friends about the night before and the girls were getting a big kick
out of it since the guy came to town often and was always bragging about
his sexual abilities.

No sooner were we done laughing about that then the guy comes in, having
stayed over another night and before he had his first drink in his hand
he starts bragging about how he’d serviced the two women he’d picked up
the night before and done such a masterful job that they’d both left bowlegged.

As you can imagine, it was all the two women and myself could do to keep
from cracking up and when he went on and on, one of the women asked him
which of the two did he think was the hottest and he told them the
blond. Then she pointed to me, sitting right next to him, and said,
“That’s her right next to you.”

He looked at me; I smiled at him and said something in my femme voice
that I couldn’t have known if I wasn’t one of the women from the night before. He slammed down his empty glass and that was the last time we
ever saw him.

25.5K views
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Anonymous
Updated 5y
Originally Answered: What has been your best cross-dressing experience?
I put out an ad for men who wanted a CD, talked to several online for a
week or two and choose a couple that I liked and seemed compatible. Made
a date for drinks. Went in skinny jeans and silk top with A cup unpadded
bra so I was androgenous but not too obvious. We talked and it got more
and more into what we liked sexually. He finally invited me home. I had
a micro skirt and thi highs with make up bag in my car. Changed and made
up at his place right after walking in the door. Super slut outfit
basically. Got a bit tipsy and did a line as he got down to boxers. Then
I stroked him awhile. He just lay back looked me over and moaned a bit.
Thought I might rip my panties. Teased him orally awhile then he turned
me over pushed my undies aside and lubed me. I made sure he had a condom
on before he took my virginity. Saw him about every week till he
transferred out of town.

17.6K views
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Anonymous
3y
Originally Answered: What has been your best cross-dressing experience?
My best experience was becoming a full-time sextoy slave slut for a
daddy. I have a daddy who has been constantly offering me to move in
with him and be his sissy slave. Back when I still had a job, I kept
rejecting his offer. Then, covid-19 pandemic came and I was laid off in
the beginning of the year. That’s when I eventually accepted his offer.

He laid out the rules that if I accepted the offer, there is no going
back, I will be a full-time sissy slave sextoy for him, I have to do
everything he asks for, no exception with complete submission. I was
hesitant at first but finally decided to accept. First thing he had me
do was to throw out all male clothes I had since I don’t need to be a
male any longer.

Next was to increase my slave clothings. He dropped me off at a mall and instructed me to shop as much clothes and lingerie as I could. He
restricted my clothing to only revealing, transparent, sexy, or minimal coverage type clothing. I had to come out looking like a slut when he
picked me up.

I had to update my ID with new address and photo of my slutty self. At
this point I already accepted my old life was over and there is no going
back.

The last 8 months have been the best time of my life living as
submissive slut. As a sextoy, I have been put to regular use either by a fucking machine or by him. He also regularly shares me with strangers.
My only concern now is if he decides to kick me out if he finds a new
slut. I asked him and didn’t get a firm answer. I begged him not to ever
kick me out since I can’t do anything without him, nowhere to live, no
decent clothing, etc.

10.4K views
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April Marie
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Been in transition for 4yrs now1y
All of it is amazing, but my best experience was the first time I went
outside dressed female. My wife and 3 daughters went out on the 4th of
July to lite some fireworks …I was so excited amped up being outwhe out
of the blue two cops drove up on us as we were lightning fireworks they approached us my heart beating so fast aasked for i.d they ran us and
searched the car top to bottom just harassing us but they had nothing so
they started questioning me about why I was dressed female I just said I
am a girl so I'm dressed as such..they finally left and we proceeded to
lite our fireworks..But omg what a rush for my first time out.

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Answer requested by
Fun Open-Minded and Nonjudgementail
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Phil Gray
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4y
Originally Answered: What has been your best cross-dressing experience?
The most amazing experience ive ever had,was the first time i dressed
for someone else

This was a girl i had reconnected with after several years

After communicating on socail media for some time,she out of the blue,
asked if i would share something that ive never told anyone.i asked what
she meant, she said “you know,sexual fantasies"

I thought on this for a week or so and decided i could trust her enough
to let her into my private thoughts and doings

I d been dressing for a long time previous to this,and knew what style
suited me,sizes,shoes, makeup,etc,so i messaged her that i love sexy
lingerie, stockings, heels,etc

She messaged back,

On the women youve been with,or yourself?

Well that was an opportunity i wasn't going to let go by and answered
“both but me especially “

I nervously awaited her reply which was

“id love to see that ,got any photos"

I replied, i would rather show her in person

We arranged a date where i would travel to hers and live out that fantasy

The time came,i had already shaved ,i made my self up,dressed myself in
her bedroom, while she waited in the lounge

I was ready to open up this whole new world although very nervous.

I asked her to turn her back to the direction i would be coming from and
walked out of the bedroom and toward her

I know she could hear my heels on the timber floor,as i walked up to
her,put my arms over her shoulders and hugged her from behind and
whispered in her ear,

you can turn around anytime u like

Her eyes grew biggerand bigger as she looked me over taking it all in
then told me to do a twirl

She took a huge breath in and said"oh my god you are such a sexy little
bitch arent you,,wow,i love it,you certainly do have an idea of style
and class"

She then kissed me deeply on the lips then apologized for messing up my
lippy, but couldnt help herself

Needless to say we've had many gurl nights in,gurl days shopping

9.5K views
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The CCL Electrician
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Electrician (1995–present)
·
1y
When a man invited me into a booth at a local ABS. He pulled me to him
and gave me a long passionate kiss while his hands massaged and rubbed
my ass. Then he pushed me to my knees so he could feed me his cock.
After dumping his load in my mouth he pulled me up. Then dropped to his
knees, lifted my skirt and pulled my panties down. Then proceeded to eat
and finger my ass. Once he recovered he stood up and proceeded to fuck
me. We spent more than an hour In that booth. Making out and me sucking
and getting fucked. Ended up the start of an enjoyable friendship in
which we would meet for a repeat.
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Anonymous
5y
Originally Answered: What has been your best cross-dressing experience?
I'm a man with large breasts which amply fill a C cup. I've been wearing
a bra every day for many years with my wife's knowledge. In fact she
helped me with sizing and fitting when I first started but not I'm doing
it on my own. She's been sexually adventurous and likes to take the lead
and dominate me. She started the domination by using her fingers to
penetrated me, then a small dildo and finally a strapon. With the
fingers and dildo, I liked the feeling but with the strapon, it opened
up a whole new world. The first time she used it, she gave me a
memorable anal orgasm.

The cross dressing was her idea of making me submit. I was laid off from
work a few years ago and she told me I needed to take over the housework
and to do it dressed as a woman. Then she made it my job to fix her
dinner every night. One night she got frisky and showed up in the
kitchen with her strapon and had me bend over and take right there.

My best cross dressing experiences have been the times when she has also
cross dressed as a man and dominated me sexually.

17.8K views
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Kaleigh Andrews
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Experience in Cross-Dressing & Wearing What Is Comfortable, School of Life
·
4y
Originally Answered: What has been your best cross-dressing experience?
My ex was out supposedly working late (later I find out she’s been
partying and cheating) I got all dolled up and went to a bar and ended
up chatting the night away, while sitting at the bar, with an amazing
genetic girl who was in a messed up relationship. She was awesome and
the chat great. Have since wished I would’ve gotten her number and kept
in touch. She instantly was cool with me dressed as a girl and suggested
tips for my makeup and stuff. I was on cloud nine as we left the bar and
went our separate ways to our cars!
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Jo Dunne
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Under these clothes I am completely naked
·
1y
I have driven across the country dressed and that feels great. I once
went to meet a friend I had met on line, she knew I was dressed and
insisted I come across without changing. That was an incredible evening,
it happened a couple of times again and I keep in touch with her.
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Kalissa Foraday
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6y
Originally Answered: What has been your best cross-dressing experience?
Before my wife passed away her fantasy was to have a bi exp but cause
she was sick we never went out so i did the best i could for her and
surprised her and one night i fully dressed for her !

I wrote her a letter telling her i had a surprise for her and to be open
minded and enjoy ! I told her to come to the bathroom !

I had a bubble bath drawn candles and all and i was standing there all
dressed up and said hi im your maid slave for the night come and let me
bathe you !

She was like dazed untill i slowly bathed her and ran my nails all over
her ! Next i shavec her legs and pussy teasing her as i did till she was excited as hell and said lets go to bed !

She laid back and i handed her a letter saying i was her bitch for the
night hers to do or have do as she pleassd and told her to name me and
if she wanted to use it there was a strapon unddr the bed to use as her
cock if she wished !

As she read the letter i teased her with my nails and whispered feed me
my precum ! Quickly she had a huge gob in her hand and i was lapping if up !

Long story short we both loved it and i loved her using the strapon !

After that night we would make it a all weekend thing sometimes

15.2K views
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Nick
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lingerie enthusiast also part time crossdresser
·
1y
It happened just a little over a month and a half ago. The day after
Halloween. My roommates were gone on a weeklong vacation. I took the opportunity to get my makeup done professionally. I had the best
experience! Her studio was in her house and did a FANTASTIC job. We
quickly became friends and to this day she will answer questions that I
have and was not bothered by doing makeup for a guy.
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Rexann Love
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Part time sissy slut and full time cock lover 2y
The best dick I have had iin me was a very well hung black mans cock he
was all of 11″ and thcker than a cock can and I want him to fuck me I
never had black black dick in my ass But at 25 yrs old I got it He had
to pussy very hard to ge in me yes it hurt some bu tthe fucking he gave
me was so well worth it I became a real woman then and many time after
with him Black me love to fuck white sissy ass like mine I knew I wanted
a black cock to take me and take me he did My hole wa sore for a week
and a week later I went right back and let him fuck me again I think
most white sissy;s want a black man to fuck us Just like white women who
once the black man takes there pussy there hook on it I got hook on it
But yet I still let white men fuck me to even some hot lation men fuck
me A coc is a cock and when I am whicof th is so much he time I want a
cock makin love in my ass I never can refuse a man that want to fuck me
I soread my legs open for and mans cock

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Geneviève...
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1y
Hello all you beautiful people… 💕

Im a Trans Woman have been out since July 2020… my best experience as an
open TW is receiving a birthday card from my Aunt with the correct name… “Ms. Geneviéve Sapha”… that put a huge smile on my face… Aunt ‘E' has
known my preferred name for a while… however, she texted me a few weeks
prior to my BD and asked me what my title is… geeze, never once
considered a title… I told her I'd like ‘Ms.’ 💕
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Andri
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1y
Impossible to narrow that down to literally thousands of instances..
Every situation although similar is completely different because every
human being, every age of either gender has their own unique personality
and reaction to my crossdressing in different environments. The
reactions from very young people under specific ages split between 4 age
groups within a 15 year spread is undeniably the best as far as confused reactions go..Its an exhibitionist trait to show oneself in infinite
ways, which by the very truest definition of exhibitionism is to shock
and confuse and its highly arrousing to watch and wonder what they're thinking..Born with a very female looking body, dressed passably to many scenarios, distance from near to farther imagining from my behind
thinking I'm a girl. Short short cute girly shorts ,tight to snug, to
more relaxed fit that in all give a different perception..Cute girl fit
t shirt, blouse, jacket, sparkly thong sandals..Hair styled like a girl.
Often wearing oversize stick on nipples or realistic silicone breast
forms in different sizes..Small barely noticeable breast curves make
people look more intensely wondering if I'm transgender on hormones.
Many times it's just these big outstanding stick on nipples that Cleary
cling to specific shirts that will really confuse..My jacket perhaps
covering my penis or in state of partial to full erection also clinging
to the shear or semi seethrough material in which all details, the head, length, ribs, veins can be seen..Its a right opportunity to take my
jacket off or pullover to expose the fact that I'm not female and that
ever unique confusing moment when the onlooker even in direct momentary conversation just stares in confusion with it being very large..Is it
just confusion or is there subconscious arrousal by them evaluating.
Actually going back out of their way to make up an excuse to look more..Naturally by that time a large wet spot is a natural occurrence.
In this heightened mood, prec,m so abundant its almost like mini ejaculations..Many times so arrousing, c,mming without hand stimulation
right in face to face conversation..I've long since understood that just dressing a certain way by many females to garner their exhibitionist
turn ons is different in only one way, they just don't have a penis that
can show they're turned on..Its not necessarily having a perverse
attraction to someone specific, or that would be your secret anyway,
it's the exhibitionism to cause confusion that's exhilarating on its own standing..

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Scott Helling
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Former Former ABS Worker (2000–2003)Apr 2
My best crossdressing experience was when I was working as a cashier at
my local ABS. When we were at work we had a choice on whether we wanted
to dress up or not. I always decided to dress up. I was getting ready to
close up for the night. I had to go around the store and make sure
everyone was gone. I was making my rounds and in one of the theaters
there was a male and female couple still. They had some porn playing and
they were still getting it on so I stood there and watched has they were fucking each other. The female saw me watching with my cock out stroking
it. She smiled at me and kept getting fucked. About ten to fifteen
minutes later I was still there jerking off and she came up to me and
grabbed my hand away from my cock and she proceeded to give me a
blowjob. While I was getting one of the best blowjobs I ever had I was
getting fucked on the ass by the male. This lasted for another 10
minutes until I was filled in the ass by the male and I came down the
throat of the female. After we all got finished we cleaned up and went
our separate ways.

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Chris Lowe
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35 years of reading history and WW2 wargaming5y

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