[continued from previous message]

amazing. We were married 9 years before I lost her.

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Keri
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Masters in Computer Science & Dance (activity), Carnegie Mellon University
·
9mo
My mom put me in ballet when I was 9 because she decided it would stop
me from being a bully and getting in trouble. Before my first class she
told me I would be the only boy and that there was a uniform for the
classes which I would have to wear. Then she handed me a pair of pink
panties because she said boxers wouldn’t work under the pink tights I
would be wearing. There was also a baby blue leotard. That’s how it all
began for me.
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John Smithe
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Ready to go both ways.
·
Apr 1
Mine was with my first mistress. I had decided one day to tell her I was
into wearing panties, and then brace myself for the fallout of that
reveal, I thought we would break up, but much to my surprise she was
really into it and encouraged me to take it as far as I wanted. She
picked out panties for me to wear, also put makeup on me, and had me
dress in some of her other clothing. It truly was the greatest of times
with her. After some of our sessions, I would be in tears of joy and thankfulness.
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Stephen Walton
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Cheese is my guilt pleasure1y
Related
What was your first encounter with a crossdresser? Was it a positive or negative experience?
Seeing a cock in nice knickers is one of my biggest turn ons. I wear
them myself and they are more comfortable than men's. My first sexual experience with another chap was a cross dresser. I had been curious
about oral for a long time. We started chatting through a crossdressing
website and we got on really well. He was, like myself married. The
chatting finally came round to meeting. I packed some clothes into a bag
and went to his house. The door was opened by a really nicely dressed cd
in a purple dress and stockings. He showed me a place to change and I
slipped into a skirt,top and knickers and holdups. I went to the bedroom
and sat by him. It felt really strange but exciting sitting next to
another crossdresser. We had a slow kiss and I remember Softly kissing
and stroking his stocking up his dress. My hand then found the lacy
knickers he was wearing. They were so soft and I was stroking his cock
feeling grow. I had been curious about giving oral for ages. I teased it
from the hiding place and was slowly wanking it. He asked if I was ready
to try sucking and OK. At this point I was hard myself with my heart
racing. I slipped my lips and mouth over and started to suck and work my
tongue around the head. My mouth was soon bobbing up and down and I was enjoying it. He warned me that he was about to cum. I thought better now
than later. I held the head in my mouth. I felt a drop of precum he
groaned and a pulsing spasm of warm cum filled my mouth and I just
started swallowing. It was electric! I sucked his cock a few times after
that, each time enjoying a mouthful of creamy sperm.

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Jane
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I’ve crossdressed for over ten years.!Upvoted by
Wendy Hand
, former Crossdresser at Cross-Dressing (1971-2020)1y
Related
Did crossdressing ever lead you to any gay acts or vice versa?
Gay acts….yesss but I’m straight and not attracted to men yet for me I still wouldn’t call it gay acts l call it straight acts..

I’ll explain….. Oh b4 I do here’s a pic to help with the explanation k…..!!


So I started putting pics online because looking at myself turned me I I couldn’t believe how feminine my body looked dressed up. Being straight
is why I feel that way lookin at myself which is still the reason I do
it now.. Having said that because of the photos I put online I got hit
on by men constantly like in DM’s it’s was like nothing I’d experienced b4 like I couldn’t keep up tbh thick and fast and I realised how much
that made me more “female” so when I’m dressed up I walk, and move like
a female and yes I always sit to pee and wipe of course lol. Now I’m completely do everything the way a female does including the way they
would masterbait which led me to thinking what a real cock would be like
plus being able to lie there an just cop it..🤔🤭 so eventually I found
out and it was great and from there I’ve progressed to getting paid for
it and like I said it’s straight sex to me still and I’m completely straight whilst doing all of it because when its happening I’m always
fully dressed up the whole 9 yards makeup expensive wig etc. and I look
female he looks male so it’s just a male and a female having sex and in
the exact same way Im treated like a female I act like and do the exact
role any actual girl does in straight sex acts.. For the guy he’s no different than any straight guy infact 90% of guys that I’ve fucked or
even spoken to say they are completely straight and most of them are
even married men…!! Which in my mind it straight acts..😘😘


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Chris
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X-dresser since young. Finally happy as my true fem self
·
Aug 18
Originally Answered: What is the most special moment on your
cross-dressing journey?
When I finally accepted that this is a part of me no matter what. No
more trying to keep it a secret from my wife. No more telling myself
that this is all wrong. No more self loathing as to why I liked women’s clothes. No more lying to myself that I should be something or someone
else. Once I realised all of this, life became that much more enjoyable
and happy for me.
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Keri
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IT Programmer
·
Jul 28
Originally Answered: What is the most special moment on your
cross-dressing journey?
When I was 14 I auditioned for the corp in a professional production of
The Nutcracker. The director knew I was a boy but that I danced as a
girl. She picked me and 15 other girls to be in the corp. I was so
excited and the performances were great. The corp wore white tutus for
the first act and pink for the second act. I have danced in many
performances since then but that was the first one and it was truly special. Profile photo for Laura L
Laura L
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Just a person exploring life and all its options.
·
Mar 20
Originally Answered: What is your favorite experience you had while crossdressing?
My favorite experience was when I was completely made up from head to
toe and feeling/looking so sexy. That night I went to a club with my ex
and friends, I was so nervous but they all told me how great I looked
and they were there for me. When we got there, and after a few drinks to
loosen up, I became the center of attention, an object desired by her,
our friends, and some “strangers” that later became friends of sort.
That was a feeling I never experienced before and I was immediately
addicted.
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Barry Jones
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Lives in London (2001–present)
·
Jun 6
Having sex with another guy.
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Joanne Watters
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Former Dancer (1991–1992)Upvoted by
Gregory Emmerling
, Love crossdressing and have been for over 40 yearsFeb 28
Related
When was the first time you cross-dressed and looked for a man?
This was not the first time I crossed dressed but it was the first time
I went after a man. It was Halloween & I got dressed up as a girl, my
mother helped me, doing my hair, nails & makeup. About two weeks ago,
while I was hitch hiking home, I was picked up by a guy who told me he
was bi sexual, I then told him about how I loved dressing up as a girl,
he told me that he hung out at a local mall. I & my friends also hung
out at that mall & I made it a point to find him & say hi on two
different occasions. When my mom finished with my hair, I got a purse &
a coat & went out, telling my mother I had a party to go to. I headed
straight to the mall to find my bi sexual friend, I wanted him to make
me a complete woman tonight. When I found him & told him what I wanted,
he didn’t believe me, he said I had to prove to him that I really wanted
to be a girl, I told him I would do anything because I wanted to live
full time as a girl. He took my hand into his & walked me to the salon
that was in the mall, he said he was buying me some acrylic nails, I
leaned over & kissed him before entering the salon. From there he took
me to the piercing pagoda where I had both of my ears double pierced. He
then took me to his place & made love to me.


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Dennisa Waggoner
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Former Firefighter/Tenical Rescue
·
Jun 14
Going to a big city late at night, finding a stranger , any male or
group of men that let me fill there sexual pleasure is the best. Never
knowing there names and probably never seeing that cock again, always a
new stranger.
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Jola Lavelle
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crossdresser sexUpvoted by
Wendy Hand
, former Crossdresser at Cross-Dressing (1971-2020) and
Gregory Emmerling
, Love crossdressing and have been for over 40 yearsUpdated 9mo
Related
Did crossdressing ever lead you to any gay acts or vice versa?
For years I thought I was only interested in dressing up. Then I started posting pics online and hanging out in chat rooms with other CDs. I
would get lots of sexy comments from guys and they would flirt a lot and
pay me so much attention. Over time I became comfortable with flirting
with men online - I liked the way it made me feel. I began to wonder
what meeting a man while dressed up would be like - just to talk - no
sex. One evening, my wife was away and I was fully dolled up - make-up,
wig, lashes, nails, lingerie, stockings, dress and of course heels.

I was chatting online to various random guys and I just thought it might
be fun to drive to someone’s house dressed as a girl. It didnt take long
to find a willing host. I arrived and confidently walked in (as best I
could in my 5 inch heels). Because i was dressed up as Jola, I was
acting ultra femme - so I gave him a peck on the cheek. Immediately he
put his hands around my waist and kissed me on the lips… his tongue
entered my mouth and I didn’t stop him.

I french kissed him for a full minute - his hands were caressing my body through my skirt. His hands on my ass felt so good. He suggested going
upstairs and for a second I thought maybe I shouldn't as I knew where
this was going, but I felt so girly I just wanted to please him. He had
a mirror in his room in which I watched myself as a girl as he touched
and caressed me. It was so sexy. I am not in any way attracted to guys
in my normal life. But when Im dressed as Jola I seem to take on the personality and desires of a girl.

update:

A lot of readers have been asking me whether it went further. I can say
that on that day I ended up in his bed giving him a hand job, and
allowed him to finger me. In the subsequent months I completed my
journey as a sissy having oral and anal sex with different men.

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Samantha
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Just here.
·
Mar 19
My best experience what a nice and simple one. A friend of mine, a
woman, told me that she would love to take photos of me posing on an
outfit. It was my first time being infront of someone like that and I
was nervous. As we were going however all she kept giving me was
complements. I didn't mean for it to happen but I did begin to get an
erection and didn't even notice until she pointed it out, I was
embarrassed but that made me realize how amazing it made me feel to be
told I look sexy and desirable!
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Cdmelanie
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Upvoted by
Gregory Emmerling
, Love crossdressing and have been for over 40 yearsJun 29
Related
Has anyone introduced you to crossdressing? How was the experience? Did
you enjoy or hate it?
I wasnt introduced into crossdressing but when my ex wife told me she
was divorcing me because I was a failure as a man and then suggested I
become a woman because I never was a real man nor would I ever be one.
to further humilate and emasculate me she also said she was leaving all
her lingerie behind because it would fit me better and I could see for
myself she was right that I'd be a better looking woman.

I admit hearing what she said about me after 22 years of marriage was a
hard pill to swallow. then one day while putting away my laundry I
looked at the lingerie and thought what have I got to lose. what if my
ex is right, so I tried on a teddy with matching thigh high hose and
panties. I must say I was quite shocked when I looked in the mirror and realized my ex was absolutely correct. I stayed in that outfit the rest
of the day as I went about doing chores around the house and even slept
in that outfit.

I got up the next morning feeling refreshed and excited, I decided I
wanted to explore this new life as a woman. I showered and put on a
clean pair of panties from another lingerie outfit and went on a
shopping spree. I bought several.outfits, panties, bras, and thigh high hose,make up, jewelry, shoes, wigs, lady razors,feminine body washes and lotions and perfume. I rushed home and began my journey into becoming
the best woman I could be.

the transformation was a complete success and I said a final good bye to
my beta male life and everyday I thank my ex wife for opening up my eyes
and heart to be the person I am now.



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MariaKim
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Mar 10

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Laura L
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Just a person exploring life and all its options.Upvoted by
Gregory Emmerling
, Love crossdressing and have been for over 40 years9mo
Related
Have crossdressers ever been gangbanged while cross-dressed?
Yes. My ex wife and I hosted a Halloween party and she demanded to pick
out my costume. She decided I should be a French Maid, and wanted to see
how feminine she could make me look. So, all of my body got waxed (ouch)
or shaved. Then makeup, blonde wig, nails, stockings, and very tall high
heels (that she made me practice walking in.) As I looked in the mirror
I couldn’t believe how sexy I looked! We proceeded to do some shots as
she teased me, making me hard and then letting me cool off. When the
guests started arriving there were quite a few men I had never seen
before, but we both loved ménage a trio’s before and she wanted to try
more than 2. So I write it off as that. As the night went on the guys
started taking pictures with me, groping and in various positions. I was
drunk, my wife was egging me on, and I loved the attention. The next
thing I know is there are 2 guys with their hard cocks out and my wife
is begging me to suck them. So, I did as she took photos. It wasn’t the
first time but these were large hard docks and I was extremely horrny. I
really got into it gagging myself on their cocks until the one said he
was going to cum. My wife told me to be a good host and swallow it all,
that was all it took and he unloaded in my mouth. I then started going
to town on the other guy and didn’t notice additional men coming into
the room. Suddenly I was surrounded by guys striking their hit cocks and
“ waiting for their turn.” I remember sucking off 4 cocks and swallowing all of their cum. Then things got fuzzy, but my wife was still running
the show and telling guys what to do to me as she took photos. The last
thing I remember was my mini skirt being lifted up and a hard dick
pressing against my ass, while another guy was holding my head so I
could suck him. When I woke up I was covered in cum, my stocking, wig,
face, and it was leaking it out of my ass. I felt like I had to use the restroom, but was very sore as I went to the bathroom. It was nothing
but loads of cum, and the mixture of pain, foggy memories, and cum
covering me made my cock get hard. I started jacking off and my wife
came in… she said “that’s a good lil bitch stoke that cock for me” and started showing me photos of what a whore I was!! I started cumming
looking at how I was used as a whore and the amount of men surrounding
me, she dropped to her knees and sucked my cock, but only so she could
kiss me and shove her cum covered tongue in my mouth. She stepped back
and said now you know how you taste as well as all her friends, and
explained she had set it all up to watch me come out and become the
sissy whore she wanted me to be.

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Tony Coxx
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Crossdresser, Retired Barber, Beautician at Shop Owner (1968–present)Mar 26 Related
What are some cross-dressing confessions?
I could confess a few things but this is somethinhg I never told anybody.

When I was 18yo, I was in the mall on a Saturday afternoon while
crossdressed when I ran into my mother's ex-boyfriend. He knew I was Bi crossdresser from when he dated my mother. After talking for a few
minutes, he said his daughter, who was away at college, had cleaned out
her closet and left a couple bags of clothing for him to donate. He
asked me if I wanted to look at the clothes before he got rid of them,
and I could have anything I wanted. I said yes, because I knew she had
nice clothing and getting some free outfits sounded good. He smiled and
took my hand and we left the mall holding hands. He walked me to my car
and I followed him to his house.

We went to her bedroom and as I was looking at the clothes, he said I
could try on anything I wanted. He sat on the bed and watched me as I
tried on several dresses, skirts and tops. It felt strange continually stripping down to my panties, bra and stockings and dressing in front of
him but the clothes were nice and I wanted to take them. He said I
looked cute in my high heels, bra and panties which also made me a
little uncomfortable. I got done and I packed up everything I wanted
into a couple bags and before I put my dress back on, he walked over to
me, put his hands on my waist, and said if I wanted the clothes, I had
to have sex with him. I was nervous at first and just stood there for a
minute saying nothing and my mind was racing. He was a handsome guy in
his mid 40s and I always liked him but it seemed strange to have sex
with a guy my mother had sex with first. I really wanted the clothing so
I said okay but I made him promise me he would never tell my mother. He
said okay.

He dropped his pants, sat on the edge of the bed, told me to get on my
knees and suck his dick to begin with. I went down on him and sucked him
until he came in my mouth and I swallowed his load. I thought I was done
but he told me to lay back on the bed until he was hard again because he
wanted to fuck my ass. He laid next to me and we talked for a little
while, he kissed me and had his tongue in my mouth and I kept stroking
him so he would get hard again.

When he was good and hard again, he pulled off my panties, lifted my
legs and slid his dick in my ass. It felt so good and he smiled as he
began pumping my butt slowly. His hands were all over me as he picked up
the pace as he went deeper in my ass. By now he was feeling great and I
was really excited as he squeezed my ass and my nipples and kissed me.

He fucked me hard until he came in my butt. He stayed in me until he
went limp and then he kissed my butt cheeks when he pulled out. He laid
back down next to me, kissed me, and said he liked fucking me. I said he
had a nice dick that felt so good in my mouth and ass and I was glad I
let him do me and he was happy. We laid there for a while talking,
touching and making out. He made me feel very good and knew just what to
do to drive me crazy.

When I finally got up, I got cleaned up, got dressed, grabbed the bags
and got ready to leave. He said he wanted me to come back the following
week and do it all again but I said no. He then kissed me with tongue,
rubbed my dick and said if I came back, he would suck me off too so I
said maybe, I'll think about it. I thought about it all week and decided
to go back to his place the next Saturday. He was happy to see me and
gave me a nice gold necklace. He said he knew I'd be back and wanted to
give me something nice. He put it on me and we headed for the bedroom.

It was a total repeat of the first time but I got more into it the
second time around because I knew what he liked. He didn't suck me like
he said he would but that's okay, I still had fun with him. He was 27
years older than me, he had a few gray hairs but he had a great body and
he was great in bed.

He wanted to make it a regular thing but I said I had to think about it
because it still felt strange being with a guy who had sex with my
mother. He told me to come over in the morning and we could go out as a
couple and spend the day together like a date instead of just meeting up
for sex. I said I'd like that.

That's what we did, he treated me like a woman all day long, treated me
like a sex doll at night and it made me want to continue seeing him. I
kept seeing him for several months until his daughter came home from
college for the summer but he was really great while it lasted.

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Lisa Lust
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Former Crossdresser May 1
Some of my best experience have been going to a sex club and having sex
with multiple men and other cross-dressers throughout the nights. Those
places are fun because everyone is open, there are rooms with beds on it
with people fucking everybody watching you people getting in line ready
to fuck you or get sucked off, Sections where they would have multiple
glory holes so you would just stick your cock through the hole and you
would get sucked off. I would be in the booth just waiting for the cocks
to come through and to suck them off. In between fucking and sucking, I
would just visit the rooms and just watch the excitement of men fucking
these cross dressers , and then me getting turned on and joining the
fun, I really miss those days and were really fun when I used to attend
and participate hopefully one day I get to join those parties again.



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Larry A Nelson
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Former Freelance Adventurer and BloggerUpvoted by
Wendy Hand
, former Crossdresser at Cross-Dressing (1971-2020)4y
Originally Answered: What has been your best cross-dressing experience?
The first time that I went to a women’s clothing store and tried on a
dress. I was underdressed wearing panties, a bra, a camisole and a half
slip. I went to the store, a Dress Barn, shortly after they opened on a
quiet Tuesday morning thinking there would not be many other shoppers in
the store. I had already searched omline and had picked out a dress that
I was interested in. When I got to the store, I was greeted and asked if
I needed help finding anything. I told the sales associate what I was
looking for and she asked me what size. I told her that I was not sure
but from the size charts, either a 16 or an 18. She pulled down both
sizes and I asked shyly if I could try them on. She lit up with a big
smile and said “Of course!”. She ushered me to a changing room and put
my name on the door.After a few minutes she came back to check on me to
see if either dress fit and she wanted to know if I wanted to try on
anything else. Well, the size 16 fit best and it felt so good over my
female underwear. I was too nervous but happy to try on anything else.
So as I was checking out, I asked if they had many male shoppers and she
said yes, that I would be surprised how many they had. Too bad Dress
Barn is closing, it was a wonderful,day and I have every intention of
going back.

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Answered by
Lisa B.

Upvoted by
Gregory Emmerling
, Love crossdressing and have been for over 40 years
·
Oct 15, 2022
I was 19, first time really having sex with a man. First time dressed in
front of someone one on one. He was in his late 30’s. I only had him
inside me for about a minute and I had my first sissygasm.


… (more)
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Delia Smith
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Lives in Hertfordshire, U.K. (2017–present)
·
Jun 13
I was seeing a guy on a regular basis. I loved getting dressed up for
him and enjoyed how he would take control. He eventually talked me in to meeting up with him and a friend of his. I was incredibly nervous at
first but pleasing two guys at the same time was such a turn on. The
three of us met up many many times after that evening.
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Joanne Watters
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I wore waterproof mascara without knowing it & got caughtUpvoted by
Wendy Hand
, former Crossdresser at Cross-Dressing (1971-2020)2y
My best experience was after I told my boy friend that I would like to
be with two men at once. Two weeks later, he told me we were going to
get a motel room for the weekend & that I should get dressed extra sexy.

I wore a white, tight, low cut sweater, a black, belted mini skirt,
white, shiny pantyhose & black, open toed, four inch heels. I wore my
hair up in a bun & had long, white, dangle earrings hanging from my
ears. When we got into our room, we started making out, soon I was on my
hands & knees on the bed as my boyfriend entered me. He had just got
into me all of the way when the door was flung open & a guy walked in,
climbed onto the bed, pulled out his cock & stuck into my mouth. I was
in heaven, there is no better feeling then having two cocks in you at
once. When we were done with round one, my boyfriend told me he set this
all up. God I love him.



I love being a feminine sissy

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Ms. Tasha Stokes
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Jul 27
I met a army friend while stationed in Germany we were talking one day
when she asked me do have any heels clothes hair make up and all the
good stuff telling me she me she knows she goes into the closet comes
out hold a pair of brown 6–7 inch Wedge peep toe heels and says I saw
saw these on your computer a while ago I wanted to ask you this question
for a while “when are we going out” idk I'm having a hard time with
myself and my desires. She says you have all those cute ass shoe you
need to wear and do it right we can do it together. She picks the wedges
back up and say your highest heel would be a wedge lets t

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Paula Ray
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Truck Driver (1993–present)Apr 21
I would say the best experience was when I was married to my ex-wife.
She worked with a gay man who was a bit older than me. Since I was
disability from car accident and I was dressing as Paula full time and I
had already had all my body hair completely removed permanently and
facial hair also expect my eyebrows and eyelashes and long hair on my head.

She was working a night shift alone with an called me to bring her
something I said that I was dressed as Paula she said that it was ok
only Dan was there. I said ok I was dressed very sexy in red mini dress
thigh high stockings and g-string and my high heels. Well I went and got
full set of square tip gel nails done and painted and toes painted and
eyebrows done thin and arched feminine earlier that day.

Well I went to her work well I got there I was talking to her when he
came up and asked who was the beautiful sexy lady she was talking to.
She said oh and told him who I was. He was very surprised about how open
about it she was. He said that she must have to beat guys away from me.
She surprised me when she said that I was very bisexual and liked men.
He said that doesn't bother you to her. She said no because she likes
being with other men too.

We all talked for a few minutes and she even told him that I was a total
bottom completely. When he said that it sounded like she was trying to
hook us up. She said that was between him and I. She left for a few
minutes and he and I talked he asked me if I wanted to go a drink when
he got off I said yes.

Well that turned out to be what become a wonderful romantic relationship

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Judy
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Jun 3
I have had many great experiences over time. I just had a really great
one. My young neighbor, she just turned 39. She’s been going through
some rough times. We would talk about them. I’m 20 years older than her. I’m a good listener. Her talking about them really helped. She trusted
me so much. She then told me some very deep secrets about herself. Once
she told me I knew she kind of wish she didn’t. I told her, her secrets
were safe with me. There are. A few days later she was still worried
what she told me. I told her I had secret that no one knows about me
(except my sister). I have always wanted to tell her this but was
afraid. She asks what it was. I really didn’t know if I would tell her.
She kind of gave me this look. I trusted you with my secrets, so you can
trust me with yours. I’ve known her for years and always wanted to tell
her. I been wearing women’s t-shirts and shorts for years around her.
Also, other women’s clothes. there are neutral looking. I’m always
wearing Bras and panties under them. I’ve always wondered why she never
felt the bra under my t-shirt when we have hugged over the years. I knew
then that I was going to tell her that I was a crossdresser. So I told
her that I like to wear women’s clothes and at time I would get all
dressed up. Makeup, wigs, dresses, the whole works. She kind of looked
at me. It was a really big secret that I told her. She still gave me
this look if it was true or not. Before she knew it I lifted the t-shirt
and showed her I was wearing a Bra. I never showed anybody before me
wearing a bra. She gave me this look that I wasn’t sure what was going
to happen nexted. She then. got this smile on her face. She said I knew
there was something different about you, you always been very nice, and
I felt safe around you. She then told me we both have secrets to keep.
We talked for a while, and she wanted to see me fully dressed up. we
decide that later tonight I would get all dressed up and she could see
me. She said what time would you like me to come over. I spoke and said
what I would really like to do is get dressed up and come over to her
house. She said sure. Later that night, I was so trilled I walked over
to her house. I was in full girlie mode. She answered the door and took
a look at me. She asks me in and said I look nice. I know I don’t pass
like when I was young. It didn’t matter to her or me. We talked and had
a great time. We talked about my crossdressing and what we normally talk
about. for me I was such a good time hanging out with someone while I
was all dressed up. The nice thing was it wasn’t sexual at all, just two people enjoying the company of each other. It was one the best
experience I have ever had. As far as I know we both have kept are
secrets. We are good friends, and we do stuff together. go dinner and to
the movies so I don't have to go by myself

777 views
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Profile photo for Jamie Jones
Jamie Jones
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Bricklaying Teacher start Monday (1993–present)
·
2y
My best crossdressing experience happens every time i cross my door step
fully crossdressed, This is every weekend away from work, I count the
days down till every Friday night, then I prepare what im going to wear
on the Saturday to go out and about shopping or to any other places i
need to go, I always come back feeling happier and feeling a lot more
freer in myself.
Profile photo for Julie
Julie
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Telephone Operator (2022–present)
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May 27
It was one of the simplest thing that can happen I was invited to lunch

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