• long from Quora - best crossdressing experience (2/7)

    From a425couple@21:1/5 to All on Mon Aug 26 08:27:33 2024
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    of slick lubrication and as i spread my legs, the first cock slid into
    me. I felt wonderful as his hot cock fucked me until his cock filled my
    ass with his cum. The next guy had me on my knees, on the bed. He buried
    his cock in me and fucked me furiously until he came. I fucked and
    sucked until it was the biggest guys turn. By then, i was stretched out
    and very wet and i took his cock easily while the others watched and Lea videoed the action. I guess it got to be too much for Lea, because she
    locked down the camera and brought a guy to the bed. I watched her fuck
    the first guy, then the second, then all of them. My lover was still
    fucking me as i watched Lea enjoy the multiple partners.

    They finally finished and Lea and i thanked them for coming up. They
    said they would be happy to come up anytime we wanted to fuck. After
    they left, Lea sat down next to me, spreading her legs, asking me if I
    ever saw a pussy that wet. I told her I hadnt. She then asked if there
    was anything I'd like to do with it. I found myself licking my lips and
    telling her I would love to eat her out if she wanted. She said, “I
    want. My pussy is full of cum and I want you to eat me.” I spent an hour eating her pussy and having her fuck my ass with her large dildo.
    Afterward, she fucked my mouth with the big fake cock, asking me if i
    was now a real cocksucker, a if i really liked sucking big black cock. I
    told her i was a faggot cocksucker and loved big black cock. At that
    point, Lea turned off the camera. She said Ron would love it.

    I dont know what happened to that video or who watched it. I did find
    out that Ron was in a small group of Army guys that made and shared
    videos. Ron did bring a couple of officers up to meet me, telling them I
    was the sexy girl in the videos. Luckily, I got orders and moved on to
    another location.

    But I always think back about how Lea helped me to understand that I was
    really OK and it was OK to follow my dreams.

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    Profile photo for Jenni Gee
    Jenni Gee
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    Loves a cute pair of bootiesUpvoted by
    Wendy Hand
    , former Crossdresser at Cross-Dressing (1971-2020)4y
    Originally Answered: What is the best crossdressing experience you have
    ever had?
    I was in my early 20s and had met a married man who traveled to Chicago
    on business on a monthly basis. He was introduced to me by my boss at
    the time who told his friend Tony “I would help him with whatever he needed”. Fresh out of college, I wanted to make a good impression on my
    boss and a guy who was a big deal when he came to our hotel. Three or
    four months passed and there were a few meaningless things I had done
    for him but his glowing review to my boss was all I cared about.

    One afternoon I get a call from him that he needs a gift picked up from
    a store and delivered to his room. I get the details including that it
    was in the lingerie department ready for pick up after 4pm. There was a
    slight delay in getting the order ready but it gave me a few minutes to
    browse. These weren’t the bra and panties I had bought for myself. I
    peaked at a few of the price tags and couldn’t believe of expensive some
    of the items were. The woman brought me the package with the message
    that if something didn’t fit right to bring it back and she’d take care
    of it.

    I got to his hotel room, package in hand, a little after 6pm. He was on
    the phone but told me to come in. He opened the package and took out a
    very cute white lace bra and panties. I pretended not to look but
    couldn’t help think how I’d love to have them. He hung up his call and asked what I thought of his gift? I told him they were nice, very cute.
    He walked over and handed them to me.

    He explained there was one occasion before he thought I was wearing a
    bra. He confirmed it when he saw a bra strap marks one day when we were changing to play golf. In face, he said he was pretty sure I was wearing
    a bra at that moment and he was right. So there I was, holding very
    expensive lingerie in a hotel suite being outed as a crossdresser by a seemingly understanding guy who is a good friend to my boss. Needless to
    say I was speechless. I could feel my cheeks turning red.

    He asked me if his assumption was correct? I sheepishly told him he was.
    He told me not to worry and not to be embarrassed. He said to go try
    them on come out and show him how it looked. He poured himself a drink
    and pointed to the bathroom to go change. Part of me was scared shitless
    while the other part, sinfully aroused. I stripped down, taking off the
    cheap bra I was wearing, and slid on the panties first then put on the
    bra. Both fit perfect. I reached for the door handle and thought I’m
    either getting a raise or getting fired for this. I walked out into the
    suite and walked toward Tony. He looked up from his file and gave a nod
    of approval and motioned for me to come closer. Standing next to him,
    his hand rubbed the lace material over my ass and then gave it a light slap.

    He told me I looked great and that we would build on this. He asked me
    how far I was willing to take this. I wasn’t sure what “this” was but I told him I was willing to try anything (thinking to myself, I’m so fired
    or ready for a promotion). He had a dinner meeting at 7pm. He said I
    could go and that the bra and panties were mine to keep. I needed to be
    back at his room at 3pm sharp tomorrow.

    I had been crossdressing for a few years and had some fun experiences.
    College was a little on again off again but now graduated, in my own
    apartment, with a job, I was starting to buy some things, experiment w
    make up, and had been with a few guys as well. Tony was a completely
    different league though. Successful. Good looking. He was what I wanted
    to be. Right now, my goal was to please him.

    I showed up the next day and let myself into his room. There was a black
    dress, lingerie, shoes, and a few other items laid out on the bed. I was looking for a note or some kind of direction from Tony. There was
    nothing. A few minutes later there was a knock on the door. It was a
    woman from the spa. She recognized me and identified me as Tony’s
    “special fiend.” She told me my secret was safe with her, Tony had taken care of her.

    She had what look like a tackle box that ended up being her traveling
    make up kit. WTF had I got myself into? I flashed back to being made up
    as a teenager but here I was a 20 something professional, playing “girlfriend” to some rich businessman. Confused, scared and highly intoxicated at the prospect of what was going to happen, I was ready to
    get started.

    Debbie had specific instructions from Tony for me to follow, making sure
    I was shaved and as perfect for him as possible. Then it was into
    Debbie’s makeshift makeup chair. She had produced two separate wigs as
    well. She said it was time to work her magic. I’ve never done my make up
    like she did. We tried both wigs, settling for a shorter sandy blond. By
    the time she had walked me through dressing, put on a cute pair of
    heeled booties, I was amazed at the transition.

    She said she was certain Tony would like it. She put a few items in a
    small purse for me in case I needed to freshen up as the evening
    progressed. I asked if she knew where I was heading but she produced a
    bottle of Champaign and told me Tony would be there shortly. She poured
    a glass for me, told me to act natural and have fun. And off she went.

    I was a few sips in when Tony arrived. His silent head nodding followed
    by a “you look amazing” was all I needed to hear. I walked over and gave him a kiss on the cheek and thanked him. I told him I’ve never felt so amazing and it was because of him. He held my hand and pulled me back
    toward him, paused and then kissed me on my lips. He started to pull
    away but I wanted more. I kissed him again but this time neither of us
    stopped.

    Tony stopped us after a minute. We had plans. He had to change and I
    fixed my lipstick. About 10 minutes later we were heading out the door
    and then it hit me. I was walking through the hotel I worked at, in a
    public area for everyone to see. We made are way down the elevator, the
    lobby and to the waiting car and I realized that all anyone saw was a
    rich dude and his girlfriend. My heart stopped racing once the limo
    started to pull away. Tony said I looked amazing.

    We ended up at an art show. Neither of us really wanted to be there but
    it was a friend of Tony’s so he was obligated. No one looked twice at me
    in a suspicious way at all. My confidence grew by the minute, sipping
    Champaign and walking with him. We ended up having a great time. We
    stayed for a few hours and then headed back. The car ride back resulted
    in giving my first limo blowjob, getting a chance to taste all of him. I
    was in love.

    We got back to the hotel and were enjoying each other in the room. Tony
    was a great kisser and had an amazing cock. It wasn’t long before he was stripped naked and me down to my bra and panties, in bed. After a good
    amount of touching, kissing and cock worship, i felt his cock rubbing
    against my ass. Then his finger slid in with a little lube.

    I remember the head of his cock slowly moving inside me and the feeling
    of him slowly filling me up. And then, when I felt his hips again my
    ass, he stopped. I could feel him swelling inside me. All of him. Slowly
    he began to slide himself in and out of me. We were in perfect rhythm
    and about ten minutes of his cock fucking me, I felt him cum in me, shot
    after shot filling me up. The most amazing feeling knowing he was truly
    inside me in every way possible.

    We had sex twice more that night and it was the start of an incredible
    two year relationship. Those were two of the best years of my life
    getting to be Tony’s girl, Jenni. Our story only started with that
    night. But all great things did come to an end. Tony sold his business
    at one point, retired and we broke things off. Some heartbreak. No
    regrets. An amazing time that easily was my most memorable time Getting
    to be Jenni.

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    Profile photo for Marian Andersen
    Marian Andersen
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    Mature crossdresser who loves dressing whenever possible.Upvoted by
    Wendy Hand
    , former Crossdresser at Cross-Dressing (1971-2020)3y
    Originally Answered: What is the best crossdressing experience you have
    ever had?
    Believe it or not, It was being caught by a policeman and being taken to
    the Police Command Post trailer in handcuffs! He stopped me while I was
    out one winter evening enjoying a nice drive while dressed quite
    lavishishly: thigh high heeled boots, pencil skirt, long black sweater,
    winter coat, handbag, fully made up and wearing jewelry and a shoulder
    length wig. I was feeling adventurous and quite feminine. I went to
    various malls and walked thru their parking lot to the doors of several
    stores where people were entering and exiting. I usually go out at night
    but not to such crowded places. But I had on a heavy coat and boots so I blended in well. It was thrilling to be walking among the various crowds
    of people as a woman shopper. After a few hours, I decide to take the
    long way home, but I dropped something at my feet and reached down to
    get it (I did not want it to lodge under my brake or gas pedal).

    Suddenly, blue and red lights are flashing behind me. By reaching down,
    I inadvertently was swerving outside my lane. I stopped but could not
    find my registration and tried telling the policeman my enfemme name. He
    made me, but was not sure if I was transgender and legally had changed
    my name to Marian A. After several calls to HQ with no acknowledgement
    of a Marian A., he asked me to come clean. I told him my real name and
    hoped that would satisfy his persistence. But although I passed the
    breath analyzer test, he thought I may have been on drugs due to my
    swerving on the road, so my car was impounded and I was handcuffed and
    put in his patrol car to go take a drug test.

    Surprisingly, at the Police Command Post, I was treated very courteously
    as a female by both the female and male staff members, even the
    policeman had loosened up and continued to call me Marian even though he
    knew my male name. They told that since I was presenting as a female
    they would treat me as such. They said not to feel ashamed or
    uncomfortable about dressing and presenting as a female. They said crossdressing was quite common and very prevalent in today’s society and
    that I was well dressed and acting civilly. Even when other “guests”
    came in escorted by policemen, I was constantly referred to as “Marian”
    in their presence.

    Although I was there for several hours, we had a delightful conversation
    about my clothes and my crossdressing. They treated me as a woman the
    whole time and let me go to the unisex toilet. Of course the toilet seat
    was up! But not for long as it then crashed down very loudly as I was
    preparing myself to sit on it. All I could think of was that I had now convinced them that I was not merely a crossdresser but actually a
    transgender female!

    When the EMT took my blood he was very gentle and courteous. I was told
    that no record of my arrest would be kept if the drug test was negative
    (it was). Eventually, they called a cab for me and the policeman took my
    hand as I walked down the steep steps in my heeled boots. He then walked
    me across the parking lot to the waiting cab, opened the door for me and
    said goodnight MARIAN as he closed the door. I rode the several miles to
    within a block of my home. It was about 3am and I did not want the cab
    to stop for a while under a streetlight by my house; have the door slam
    shut with a female exiting to my house where no female lived! I felt
    more confident to walk the block to my home and then suddenly turn
    quickly up my walk to the door as quickly and quietly as possible.

    I had made it! I then sat down and reminisced about how elegantly I was
    treated by the police staff. I realized that after spending nearly three
    hours as a female conversing with other people and being accepted as
    such made me comfortable talking with a female voice and brandishing
    female mannerisms: crossing my legs, gesturing with my hands, taking off
    my coat to show off my figure, and walking the length of the trailer
    every so often (with a wiggle) to stretch my legs. Again the women were
    nice and smiled which further encouraged me. Now, it was time to go to
    bed, and after I undressed and put on my nightgown and matching panties,
    I laid in bed thinking: Yes, it was the best experience I ever had crossdressed!!

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    Profile photo for Assala Shamsi
    Assala Shamsi
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    Adult Model at Faphouse (2020–present)
    ·
    Mar 15
    I really love Crossdressing. From the childhood I wish that I'll be like
    my mother as a house wife. And when my elder sister married my instincts
    got increase she looked so beautiful in bride dress. till the I decided
    to wear my elder sister dresses. And talk with the guys online to
    encourage me.





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    Profile photo for Samantha Hopkins
    Samantha Hopkins
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    Bi-sexual CrossdresserFeb 1
    My boyfriend and I went away for a long weekend skiing in Vermont.
    Skiing has alwys been one of my favorite things to do in girl mode.
    Women's ski outfits are uber sexy and feminine. Because of hats and
    scarves is really easy to pass and no one questions. My first excursions
    as a girl were to go skiing.

    So we are having a great time and are walking through the parking lo to
    our condo we rented. And this lady calls my boyfriends name and we both
    freeze its his grandmother. I don know how he is going to react, no one
    knows about us. My BF introduces me as his girlfriend and in the dimming
    light I feel confident

    Then his sister shows up and we do the introductions again.

    Now in the bright lights of the lobby, We scurry to get Mikes sister and
    his grandmother onto the elevator. Everything is going good.

    Then we hear mikes sister very loudly say “I knew it !!!” “I Knew it all along”

    Then she starts wagging her finger at me and saying “You, you !!” “Its You !” “I Know who you are”

    Then she says I am not going to tell a soul. I have known about you
    since high school but I just couldn't prove it. You guys outlasted my
    first marriage,

    So the next day we all skied together. and we had a great day. It was
    amazing.

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    Profile photo for Meran Berwyck
    Meran Berwyck
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    CrossdresserJul 28
    Originally Answered: What is the most special moment on your
    cross-dressing journey?
    I was dressed up and visited an adult novelty shop as one of my male
    friends was working there. He knew I was a crossdresser so it was no
    surprise to him. He asked me to watch the shop while he went to get
    himself some cigarettes! I said okay. While he was out, two young women
    came in to shop. They chose a few items and came up to check out. I
    asked them in the most feminine voice I had if they found everything
    they wanted. They said yes. When I told them their purchase total, my
    voice changed and they suddenly realized I was not a real woman. But
    they were very impressed and began looking me over and complimenting my
    choice of clothes, especially my gold knee-high boots. The asked where I
    bought them, I told them FOH by mail order. The kept checking me out
    until I had bagged up their stuff and they walked out, They were really
    nice and sweet to me. I was on cloud nine. I had initially fooled them.

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    Profile photo for TRANSEmilyxo2022
    TRANSEmilyxo2022
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    Fucked and creamed by 11 guys Upvoted by
    Wendy Hand
    , former Crossdresser at Cross-Dressing (1971-2020)2y
    Originally Answered: What was your best experience in cross-dressing
    publicly?
    Having my first anal with a stranger at a public look out i was on my
    knees and hands with my ass up in the air when i felt a cock slide
    inside of me for the first time ever i cant describe how dam good it
    felt too it was so amazing when he began to fuck me so dam hard his
    balls slapping against of me every thrust all i could say to the guy is
    “cum inside of me i want your cum deep inside me i want you to fill me
    up now “ He fucked me harder and harder he was treating me like a true
    slut He started groaning while he grabbed me by my waist with both hands
    i felt his cock swell and twitch inside of my ass as he was pushed all
    the way in me he gave me a couple more thrusts before moaning so loud
    and then said “here it is slut im cumming oh fuck yeah baby your a good slut”I felt a warm gush and could feel his cum filling my ass up until
    his balls were empty then he pulled out of me a big stream of warm thick
    cum followed ooozing out of me

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    Profile photo for Jamie Richards
    Jamie Richards
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    Crossdressed since age 10Upvoted by
    Wendy Hand
    , former Crossdresser at Cross-Dressing (1971-2020)Updated 5y
    Originally Answered: What's the greatest time you had while crossdressed?
    I went to a gay club on Halloween with a young lady who was close to 30
    years my junior and who liked crossdressers. I was 53 at the time and
    she told me she was 18, but she later confessed that she had a 10 year
    old daughter. She came over to my house and helped me to get dressed up
    as a woman. This was one of the first times I went out in public dressed
    and we must have looked good as we approached the club on foot as
    someone asked if they could take a picture of us. Once inside, I was
    playing pool with her and it was such a rush to bend over the table with
    my short dress hiking up behind me and my cleavage showing for the folks
    in front of me. Later on, I sat the bar by myself while she was playing
    pool with someone else and I felt so comfortable and, apparently, no one figured out that I was a man. A friend of my brother-in-law came up and
    sat next to me, but never figured out that it was me, even though we
    knew each other pretty well. I didn’t introduce myself because I didn’t want my brother-in-law to know that I cross-dressed.

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    Profile photo for Joanna
    Joanna
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    a trans girl for 4 yearsUpvoted by
    Wendy Hand
    , former Crossdresser at Cross-Dressing (1971-2020)1y
    I still remember it is a crossdressing party.When I was 18 years old, I attended a crossdressing party. I knew this party from the local trans
    forums. Actually, I was afraid to meet some familiar people. But as this
    party was 50 km away from my block, I came to see some new friends.In
    the party, I found many hot guys. I admited that I liked to date with
    hot guys. On the party, I got many phone number. I wore as a bunny. I
    thought this could be a nice sytle for me. Many people came to chat with
    me. But I could also feel most people came here for casual dates. If you
    want to find serious relationship, it is very hard. In order to be back
    home, I didn’t drink too much but I found so many people drunk a lot.
    Now, I am trans woman and I know guys on some trans dating sites. But
    there are also many crossdressing men who are looking for dating.


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    Profile photo for Starla
    Starla
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    Former Hostes at Gay Bar (2012–2014)
    ·
    Apr 6
    I went to a gay bar, and was hit on several times. The owner didn't have
    any help so I offered to help. I helped him close he payed me and
    offered me a job. I was only able to work for one week.


    … (more)
    Profile photo for George Fraser
    George Fraser
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    Studied Mathematics at Arapahoe High School10mo
    Originally Answered: What has been your proudest crossdressing
    experiences ever?
    when I had the courage to buy my first pieces of lingerie at Dillard's
    and Macys. I was so nervous, and I know the sales lady noticed. She
    asked me if she could assist me, and I said yes but I do not know my
    size. I was looking at the rack of baby doll nighties and the long
    gowns. She said how tall are you? I said 5′10″ she said OKAY. now the
    long gowns that will fit you, so they do not drag the floor are here.
    And the baby dolls are next to them. Do you have a bra size? I said no,
    need help with that too. She took me into the changing room and tape
    measured me for size. She said if you were to wear forms, I think a 36C
    will work just great for both your gowns. She took me to the bras and
    panty section and told me it is always wise to purchase your bras and
    panty that match. And get your bras underwired to assist in holding
    breast forms in place.

    I spent over an hour at the store and purchased 186.00 worth of very
    pretty and sexy lingerie. At the checkout I heard the sales lady tell
    the clerk. I will check him out. She asked if I found what I was looking
    for? and i said yes and thanked her so much for all her help. She gave
    me her card that had her store hours that were on the back. She said
    call this number I work 3 days a week and If I’m here I will assist you.
    Her name was Karen, and she just made my first encounter so memorable.

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    Profile photo for Joanne Watters
    Joanne Watters
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    Former Dancer (1991–1992)Feb 8
    Originally Answered: What is your favorite experience you had while crossdressing?
    While I was still married to my first wife, I was really getting into my dressing up, I started making noticeable changes to my appearance. I
    grew my fingernails out & kept them shaped & polished with a light pink
    polish, I had my ears double pierced, I had my eyebrows waxed pencil
    thin with a high, feminine arch in them & I had my hair cut & styled
    into a very girlie look. My wife threatened to tell everyone I knew
    about my dressing up as a girl if I didn’t stop dressing up. I told my
    wife to go ahead & tell everyone because I wanted to live as a girl full
    time. A few days later, my wife told me she was coming home with two of
    her girl friends Tuesday after work so I better not be dressed up, I
    told her that I didn’t care if her friends saw me dressed up, in fact I
    want them to see me as the girl I want to be, my wife got pissed off at
    me & said to go ahead & get dressed up like the sissy I am & she will
    just tell her friends that she married a sissy, faggot who wants to be a
    girl & be with men, I told her to tell her friends because I will be
    completely dressed as a girl when they get home. My wife normally gets
    home from work at 6:00 p.m. so on Tuesday at 5:00 p.m. I was sitting on
    the sofa, wearing white panties, matching bra, super shiny, suntan
    pantyhose over my completely shaved body with dark red nail polish on my fingers & toes, I had on a white, button up the back, silk, long sleeve
    blouse, tucked into a black, belted, mini skirt, I wore black, open
    toed, four inch heels with an ankle strap, my hair was nothing but a
    mass of curls, my makeup was done to perfection & my ultra thin & highly
    arched eyebrows gave my face a ,feminine look. The extra large silver
    hoop earrings that swung from my pierced ears when ever I moved my head,
    drew attention to my perfectly made up face. I sat on the sofa with my
    legs crossed like a woman as I got out my nail polish & gave my
    fingernails another coat of dark red polish. As I started on my other
    hand, I heard the front door open & people talking, I continued to
    polish my nails. My wife led her two friends into the living room, upon
    seeing me sitting on the sofa, polishing my nails, my wife stopped dead
    in her tracks just staring at me in disbelief. I finished my last nail &
    put the cap on the polish then looked up at my wife with a slight grin
    on my face. My wife came to her senses & told her friends, this is my
    sissy husband, as you can see he want’s to be a girl, the two girls
    laughed as I said hello in my best female voice. My wife told her
    friends that she didn’t know that I was going to be dressed as I was or
    she would have told them beforehand, her friends said that it was no big
    deal then the one girl said I was quite good looking, I looked at my
    wife & smiled at her. My wife then said, well, this sissy has had lots
    of practice dressing as a girl, she has been doing it all his life, one
    of the girl’s asked my wife if she knew that I liked dressing up like a
    girl before we got married & my wife told her that, she didn’t know that
    I wanted to become a woman & be with men, the other girl asked me if I
    really liked men, I looked at her & said, yes, I really love being with
    men, I don’t have a boyfriend right now but I would like to, the other
    girl said were going to have to find you a boy friend, that would be
    nice I said. Later that night, when my wife got back from dropping off
    her friends, she said, I don’t believe you let my friends see you
    dressed as a girl, I looked at my wife & told her that I have told you
    many times that I want to be a woman & that I really want to be with
    men, maybe now you will believe me.




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    Profile photo for Ami-Nimi Singh
    Ami-Nimi Singh
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    Msc in Master of Science in Chemistry, University of AllahabadJul 31
    As I reminisce about my past, I am transported back to a singular moment
    in beginning of 2019, when my life was a picturesque tapestry of joy and contentment in Prayagraj. During my college days, I shared a memorable experience with my then-girlfriend, when she stayed with me for a week.
    With my distant relatives away, we had the privacy to indulge in various activities (excluding intimacy). Our days were filled with laughter, adventures, and deep conversations, creating an unbreakable bond between us.


    One day, we playfully engaged in a role-reversal experiment, where I
    donned her attire, and she wore mine. She skillfully applied makeup to transform me into a feminine version, while she embraced a masculine
    persona. We immersed ourselves in this swap, relishing the novelty of
    our reversed roles. We played games, cooked together, and even mimicked
    each other's mannerisms, creating a hilarious and unforgettable
    spectacle. The experience was nothing short of enchanting, and I cherish
    the memory of that day, frozen in time, a testament to the joy and
    creativity that our relationship embodied.


    While I've repeated this playfulness with my second partner, the
    memories of that first time remain special. Perhaps, I'll revisit this playfulness after marriage, who knows. I miss those carefree days of my
    life. We enjoyed in every possible way we can.

    thanks for reading.

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    Cammie Jones
    ·
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    Dress at least weekly, have taken en femme tripsUpvoted by
    Gweneira Scott
    , Masters History, Miskatonic University (1997)3y
    Originally Answered: What has been your proudest crossdressing
    experiences ever?
    What has been your proudest crossdressing experiences ever?

    I wanted to say the first time out in public but that is not it. Last
    year I spent 10 days en femme with a week of that in Hawaii. That meant
    I was dressed as I packed and made a couple trips for last minute
    necessities. The morning I drove to the airport had me on full blown
    nerves. I checked in and showed my ID to the gate agent. As my bag
    disappeared on the conveyor belt I knew there was absolutely no turning
    back. Next was the TSA encounter. The ID checker said thank you mam as
    he handed my male ID back. I spent the entire trip as Cammie and loved
    every minute as I sunned at the pool, played at the beach, attended a
    luau and ate at the restaurants.

    23.2K views
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    Profile photo for Michael
    Michael
    ·
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    Upvoted by
    Wendy Hand
    , former Crossdresser at Cross-Dressing (1971-2020)Jan 18
    Originally Answered: What has been your proudest crossdressing
    experiences ever?
    More Than One 2 B Honest



    53.3K views
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    Profile photo for Jaime
    Jaime
    ·
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    Being sexually used
    ·
    Mar 16
    The best experience I have had crossdressing was a night I was fully
    dressed in lingerie, a sexy dress, wig, makeup and thigh high boots, a
    guy took me to a club, we ran into a friend of his who liked what he
    saw. Long story short they took me back to his house and used me so
    good, I never felt so good, the desire these guys had for me was
    exciting and I was very eager to please, it was the only time I ever
    sucked a cock while getting fucked
    Profile photo for Stephanie Cain
    Stephanie Cain
    ·
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    AS in Medicine and Healthcare & School of Common Sense, Crafton Hills
    Community CollegeUpdated 4y
    Related
    What is the best memory that you have as a crossdresser?
    I met a magnificent girl in highschool. We had several wonderful
    adventures involving my cross-dressing. After dating for about 3 years,
    we married and left town for the first week of our two week honeymoon.
    She wore a beautiful white wedding dress because she was a virgin and I
    wore a black tuxedo when we took our vows in front of almost 100 guests.
    During the week we were gone, her best friend Kathy altered the dress so
    it would fit me.

    In a very private ceremony, in Kathy's and Richard's backyard, we
    exchanged vows for the second time. Seven people witnessed me in our
    white wedding dress because I too was still a virgin and she wore a suit
    and tie. Kathy was the “Best-man” and Richard, who is also a
    crossdresser, was the “Maiden-of-honor” for us.

    Richard presented me, the “Bride”, with some beautiful white lace
    lingerie to wear before the ceremony. As he helped me get dressed, he
    said that only your husband is allowed to undress you tonight. Kathy
    presented her, the “Groom", with a strap on (& lube) to consummate our wedding during the second week of our honeymoon.

    We snuck back to the hotels honeymoon suite that night. My husband in
    his suit and tie and I wearing our wedding dress. The second week was

    [continued in next message]

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