[continued from previous message]

I think I passed out before my head hit the pillow. I woke up to him
telling me breakfast was ready downstairs. I knew I was in for a long
day as soon as I sat up. My butt was throbbing and on fire. Just wearing panties made it hurt to walk. He made me sit down at the table with him.

After breakfast he called me up to his room where he was getting ready
for work. He asked me if I had any questions about anything we talked
about last night. “No, Sir.” Then he told me to pull down my panties and bend over the bed. I didn’t even ask, I just did it. Quickly.

Which was apparently the right answer. He said he would have repeated my
entire spanking from last night for the slightest hesitation, but since
I obeyed immediately I was only getting 20 with the belt.

I heard him unzip his pants and call me over. I got back on my knees in
front of him once more with my panties pulled down around them. I wanted
this to be the best ever. Something he would be thinking about all day.
I licked the tip, then took it slowly to the back of my throat. I licked
down the shaft and slowly made my way to his balls. I licked them while
I stroked him, then slowly made my way back to the tip. I could feel him
about to cum and took him deep in my throat. “Thank you, daddy,” after I finished swallowing him. “Can I have it again soon?”

“Yes, princess. You’ll be back tonight.”

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Scott
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Retired truck driver
·
9mo
When I got dress in my mini dress black pants hose heels and went to my
local park and walk around had men looking andyelling at me then I sat
down on a bench and a older guy set down next to me pulled his cock out
and ask me to suck it so I did and when he got hard he said I want to
fuck you so I hope on his lap and he put it inside me and made me his
batch for the night it was great I had to orgasms and he had one huge
one inside me
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Steffi
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All my life 1y
I’m thinking the night I went to a well known dance club with three
women friends of mine, they all knew about my crossdressing and seemed
to like it. Well we were all very dolled up, all of us wore cute dresses
and sexy heels and I as always was very nervous, huge difference going
to a regular dance club as to a gay club. But once I get to are table
and get my first cocktail down I’m usually ok, so on this night for some reason I was getting all the invites to dance and the other girls who
love to dance were getting pissed and asking what the heck 😆 they were
all blondes and I a brunette so I said I guess blondes don’t have all
the fun. But we all really had a blast just dancing and chatting with
guys that would come sit with us.

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Fun Open-Minded and Nonjudgementail
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Lacey Femme
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20 years dressing up1y
There were two experiences I remember when the crossdressing itself was
very memorable, independent of where I was or what I was doing. They
both occurred when I was beginning to get comfortable with going out
dressed, but wasn’t quite there yet. The first event was going out to a
bar for a drink wearing an LBD, just sitting and talking with several
people. The second time was a visit to an adult theater when I had
dressed pretty provocatively, and parked 2–3 blocks from the theater and walked the rest of the way after dark. In both cases, it was just so
rewarding and liberating to finally be myself in front of other people
without worrying about it, and realize that the sky wouldn’t fall.

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Fun Open-Minded and Nonjudgementail
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Denise Parker
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Wearing skirts as often as possible
·
2y
The answers here are awesome stories, for me, it was buying my first
breast forms. My dressing experience had been awesome, but as soon as I
added breasts, that look and felt like breasts, I was over the top! My “girls” D cup have taken me to a new high. You gotta try ‘em!
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Evelyn
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50 plus years of wearing womens undies and clothes.2y
I have had lots of good experiences related to the “hobby”. The most memorable was getting a bra fitting and learning a lot about lingerie
while there.

I went to a small lingerie store in an shopping center, more than a few
years ago, and wanted to buy forms. The lady asked me my bra size and I
was stumped, other than what I had bought. She said the only way to know
what I needed was a fitting so off we went to a dressing room. after
trying some bras and forms, ended up with a beautiful lacy 38C and a set
of weighted foam forms. Tried on panties over boy undies and body
shapers, bought one also and several pairs of panties. A great hour or
so and two bags of quality lingerie and a lifetime of knowledge.

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Kinison Maxel
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Driver at Self-Employment (2014–present)
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3y
Originally Answered: What has been your best cross-dressing experience?

Mine was doing the census! And she said that she had to ask if i
identified as male or female! That was great!… (more)
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Yudro Borges
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Wearing dresses and other casual cross dressing since 1980
·
7y
Originally Answered: What has been your best cross-dressing experience? Shopping for a leather bustier at a store in San Francisco. The
saleswoman was SO nice, helped me pick something out, helped lace me up
once it was on, suggested other things I would like - made the whole
experience SO MUCH FUN!

Otherwise, went to a drag club, and the performers were so cool - I was
in a dress and one of them pulled me out of the line to get in: “You
don’t have to stand there, there’s a drag line, baby!”, got me a seat a the front of the club. Realized that in a drag club, most of the guys in
drag were straight, and most of the guys in guy clothes were gay - gay
culture tended … (more)
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Kim
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Frequent restaurants wearing clothes from the womens dept.
·
6y
Originally Answered: What has been your best cross-dressing experience?
Today I stopped at a local bar in a hip part of town as a bald headed 60
year old man wearing missies Bermuda shorts, sling sandal with tan and
gold and and a floral sleeveless top that had a low v neck and a
friendly wait person told me I looked fabulous. She’s told me before
that she liked a shirt I was wearing but now I looked fabulous!
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Paula Hayes
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Gender female , eat drink everything girlie
·
10mo
Sorry but your question comes over as if it’s game they play ,from my
view it’s like everything in life ,you learn too get better at it ,&
once you know your destiny?ie the path ahead ,f/time , stay secret, but remember,someone’s Body ,looks , age weight, are different, but everyone
who progresses do so from their heart and mind x
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Nikky Fiuri
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Lives in Chicago Heights, IL (1973–present)
·
4y
Originally Answered: What has been your best cross-dressing experience?
I've had some great gangbangs and twice I went onstage with a
well-endowed gurlfriend and held on to to the stripper pole while she
impaled me really good.

I was at a sex party one night


and managed to take a HUGE guy half way up in me while a few people
watched. By “huge”, I mean his dick was as big as a bodybuilder's arm!
It took me 45 minutes to get half of him in me and he was shocked and
thankful and so was I.

What happened during the next two hours with three other people is a
whole 'nother story………

Mmmmmmm!… (more)
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Monika Sveet
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Part time crossdresser for 20 years and I am straight.
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Updated 9mo
I have a few very pleasant experiences as a crossdresser… For me when I
am dressed a woman, I like to be treated as a woman but at the same time
I do not like men… so, the options are either women or other CDs/TGs
like me. And all my best experiences as a crossdresser involve a female
partner who liked me dressed as a girl and make love like lesbians…

My best experience is written in detail at my space here. Visit this
story and tell me if you like it.

Quora
https://qr.ae/pKhlvN
Hugs.

Mona.
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Stephen Carr
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Owner Op4y
Originally Answered: What has been your best cross-dressing experience?
My favorite time was in Brownsville Texas at a hotel. I was fully
dressed and hogtied on the floor. My wife went to our rig to get some
things when housekeeping knocked on the door. Unable to objected through
my gag she walked in. I was laying beside the bed out of sight. She walk
to the bathroom and saw me. She asked if I need help and shook my head
no. She saw my keys on the floor but the dresser and I guess realized
what was going on. She asked if I wanted her to clean the room and I
nodded yes. So she cleaned it swept the floor. Got to me and grabbed my
ankles and pulled me to the side and finished sweeping. Than left asking
if I was sure I was ok.

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Howard Heckmer
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6y
Originally Answered: What has been your best cross-dressing experience?
Today, I am dressed in a black skirt,white blouse,my red wig,complete
make up,black nylons and low cut boots with 2 in heel.Walked into a
local lingerie shop and was treated like a true lady.I was in 7th heaven… Profile photo for Paula
Paula
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Lives in Nebraska (1999–present)
·
2y
The first time I let a man see me in bra and panties. I will never
forget it. He was gentle and supportive and when he caressed my panties
covered butt I came hard
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Anonymous
4y
Originally Answered: What has been your best cross-dressing experience?
It has to be wearing a huge black victorian petticoat of the 1860s with
blue trim just below the knee area that I bought for my girlfriend and I
did tell her my fetish for them before I got her it,loved it on her but
when she worked late i tried it on and loved the soft feeling of it on
me and rubbing my hands over the trim detail of it,masturbated like mad
to it n shot my load all over myself,love my girlfriend so much but the
huge victorian petticoats and skirts make my heart pound like mad too
for some reason.
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Soph Scots
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Lives in Glasgow, UK (1966–present)
·
1y
When along with 2 other girls I took part in a transgender fashion show
for charity,we practised beautiful for weeks and we loaned outfits from
dept store personal shopper.The finale was Bridal,and I was dressed in
the most gorgeous wedding gown,complete with tiara and walked down the
catwalk with my “groom" I felt so wonderful and beautiful just like a blushing bride.I even shed a tear or two knowing how fabulous I felt but
also Sadly I knew I had to take the dress off but it still remains one
of the best experiences of my whole life,trans related or not
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Davina Smith
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Cross-Dressing since puberty3y
Originally Answered: What has been your best cross-dressing experience?
Since I have been crossdressing for so long, there are many but many
times the experience is generally similar. First, it is important to
consider that I almost always present myself as a male wearing what may
be considered feminine clothing.

So going out in public like that takes some getting used to. Not easy at
first. I believe dressing the way I do shares a similar trait as the
many who dress completely but are still new to it. It is a fear that you
will stand out so much that people will make a scene and draw even more attention to you. So it is kind of a self fulfilling prophesy. You act
scared and it shows making you stand out.

It is very difficult to overcome without a lot of persistence. But
eventually things take a very interesting turn. You inevitably run into
people that you have to interact with. Even if it is only answering a
general question. But sooner or later, you have to face people if you
choose to go out dressed somewhat differently than most people expect.

What I found by accident is that after a while, you end up talking to
someone someone and “forgetting” how you are dressed. It happens when
you enter an unrelated conversation and talk for a couple minutes and
after you have what turns out to be a normal conversation, you suddenly remember how you are dressed and realize it hasn't made a bit of
difference in the outcome of that conversation.

So my best experiences are when I have been shopping or just out and
about and have had a normal encounter with someone only to realize after
the fact that you are dressed in such a way that you expected a horrible encounter and instead, you were treated just like anyone else because
your conversation was lacking any fear or self doubt and everything
feels completely normal.

I just love that feeling when I forget till after the encounter that
people can interact just as though nothing were amiss and you figure out
that dressing oddly doesn't really have as much to do with meeting other
people as does your attitude and body language. So many times, I have completely forgotten how I was dressed when I got caught up in an
interesting conversation. Then you think about how your were treated so normally that it makes you feel so much more at eased dressed like that.

It is a true indicator that most of the anguish and fright is just
generated in your own mind. And when you can relieve yourself of that self-incrimination, you can dress however you like and learn that how
you act has so much more to do with the way people treat you. I
personally like grocery shopping dressed in all feminine attire
including small breasts and by the time you get to the cashier, you are
acting just like you would any time.

It is quite a rush to be walking out of the store and suddenly realize
that “wow” look at how I am dressed and nobody made so much as a
comment. I am certain many people talked about it behind my back but
that didn't bother me. The thrill that you can dress however you like
and still be treated normally makes it so much more fun and easy to do
again.

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Patrick McNeill
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Retired Police Chief Inspector (1992–present)5y
Originally Answered: What has been your best cross-dressing experience?


It was on a cruise many years ago and I was with a group of lads. It was
fancy dress night and we decided to do a mock hospital operation. I was assigned the role of matron and given a pillow to wear under my apron to
make me look ‘female’, while I held the drip bottle as a string of
sausages was produced from the ‘patient’.

All very grotesque to my eyes after 40 years.

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Wendy Hand
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Former Crossdresser at Cross-Dressing (1971–2020)4y
Originally Answered: What has been your best cross-dressing experience?
I tried wearing my mom's panties when I was about 12. It made me feel a
funky kind of way. I never did it again.

1st ..10 years later... I met my first fiance. We we're very sexually
open and tried many things. One day she asked me to dress as a girl in
her clothes which I did and we had amazing sex.. we did it that way a
few times and then she started using and dildo on me..the relationship
ended because of other reasons.

2nd I was at a an adult party with a mix of men and other gurls like
me…it turned into and big pile of excited human flesh..everyone had a
great time.

rest of my history….Then forward another bunch of years.. my ex-wife and
I were on the outs and not having sex.. I got the urge to dress in her
lingerie and started using AOL groups.. then I had my first experience
with a man while wearing panties.. this went on ...I dressed more and
more for and with men.

I got married again I quit wearing for a few years and my wife still
doesn't know.. but I have restarted dressing full out and sharing time
with men.. I love my wife and sex with her too and tried many times to
bring this up as a let's have fun with our sex life but.. she always
says she won't like it.. I would love to get her involved with me
dressed and doing another guy. But for now it is only once in awhile
thing, it's not something I crave everyday.. but once in a while... And
then I get my fix.. and I'm done for a few months.

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Kari Crago
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Lives in Marion, IN (2012–present)
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2y
It was in 1997, I had just been out all-night partying at a local Gay
Bar dressed and I had to stop for gas and I wanted a coffee, when I
walked in the station a young lady looked up from a book and Said hello
and welcome and I waved to her, I got my coffee and she asked as I
approached the counter what the perfume I was wearing, I told her it was Beautiful by Este Lauder, she got a shocked look on her face (my voice
is a dead give away) and says OMG I thought you were really a Woman you
look so pretty and feminine, my heart sang! I thanked her as I paid.

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