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My first time crossdressing with a man
It was Christmas night 2016 and I had gone out to the bar with a few friends. Came home a little tipsy and very horny! I rushed to my room, took off all my clothes and put on a very sexy, slutty outfit (black lace thong with matching bra, a blue sweater, black mini-skirt, and black knee high boots) ... Read full Story
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Crossdressing with my moms friend
Mom opened my bedroom door. she stood there in the doorway and stared at me obviously repulsed. after 10 or so seconds she closed the door and walked away. i was mortified. i was kneeling on my bed, with her clothing catalogue open at the lingerie section laying on the bed before me, hard cock in h... Read full Story
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Asian Crossdresser - How My Crossdressing Journey Began
My name is Patrick (Pat) Young and I was in Hong Kong. It all started when I was 5 years old. I was an innocent and naive boy, who had no idea the difference between boys and girls. I thought the differences were that girls had long hair and they wore skirts. When girls grew up, women were sh... Read full Story
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Sara by Sara
1000 – Sissy Story 29 – Sara by Sara Filed Under: Sara, Sissy Story by Anna Malice — 3 CommentsFebruary 26, 2012 4.00 avg. rating (81% score) - 3 votes Post number #1.000 I never thought to reach this moment.. in truth i always thought to cancel this blog.. a lot of time before of this.... Read full Story
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Step-Mom China (Part One)
I was at Jon’s house that night thinking he would be home instead he was at some “party” I was not invited to and I found his “step-mom” home alone. I always found it odd he referred to China, as his step-mom since he was an orphan with no Dad to speak of she seemed only a few years older than he di... Read full Story
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The Greatest Lie Part 16
As soon as we were safely back in our hooch, I retrieved the iBook from its hiding place under the floor and opened up Spartan's main Excel spreadsheet. I re-sorted the list against the data from the last three weeks of our frustrating field work, by district, language group, age, and every other ca... Read full Story
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Working hard
My name is Micheal my birth. But I am known as Michelle As a child I had began cross dressing at around ten years age. I had actually been allowed to pick out and wear anything from my mother's closets and drawers. I was a very feminine boy and was often mistaken for being a little girl.My mother un... Read full Story
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The Greatest Lie Part 10
Don’t you hate commercial air travel? No matter how many drugs I take, when they wear off, I’m disoriented, my legs are twitchy, and there are still three hours (or whatever) to go. Not enough time to take the last of the Sonata I had borrowed from Mom’s medicine cabinet before tou... Read full Story
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Bar trap Part 2
I was supposed to put on heavy makeup. Starting with the foundation, I applied a generous layer of a brand especially designed for the use on stage, that did a very good job covering up any dark shadows. After I was satisfied with the effect, I used a brush to put on powder and make it all smoot... Read full Story
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My Clipped Cock
Technically, right now I am an "It." A few weeks ago I was a "He." In another few weeks I will be a "She." The adventure is a celebration for me. I am doing everything right, and sensually documenting and sharing the adventure with my very-supportive and very-erotic fri... Read full Story
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The Greatest Lie Part 12
My Own Worst Enemy Let’s face facts. The so-called the "War On Drugs," "Just Say No," and all the other anti-drug campaigns are complete failures because they ignore reality: getting high is fun. College students drink and take drugs to break a boring routine; the poo... Read full Story
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Fender Bender
It was the first week of June and school was out for the summer, I was 18 and had just finished my Senior year. One night while we were eating dinner, My Mom and Step dad informed me that they were going away for a week. When they got married they did not go on a honeymoon so they wanted to take one... Read full Story
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Fender Bender Chapter 2
The bright sun shining through the window woke me up, for a moment I was confused and disoriented. Then it all came back to me. I had sex with Mark and Susan James last night and I was still wearing a pink baby doll nighty and matching panties she had given me to put on before we went to bed. I w... Read full Story
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Fender Bender Chapter 3
Susan called me early Monday Morning and asked if I wanted to come over and lay out by the pool with her, she told me that Mark had a business meeting and would be gone most of the day so it would be just us girls. I remembered what happened on Saturday when we were laying by the pool and of course ... Read full Story
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Brian and Bree, and Mitch Chapter 1
"Hey, so I'm going to be at Sarah's all night," Mitch said as he was walking out of the door, "Brian, it's Friday night. Get out and do something this time." "Man, I had class all day, it's been a long week. I think I'm just going to call it an early night," Brian re... Read full Story
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Daddy’s Little Girl
Tony was a beautiful baby boy. Perfectly healthy and well formed. The mother, Susan remarked to her husband James that Tony got a little stiffy everytime she nursed him and wondered if that was normal. They all slept together and that night as soon as Tony started to nurse he sprang a boner. Susa... Read full Story
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Becoming a Cock Worshipper
I first realized I was bi the summer after high school. Up until then I had only been really interested in girls. Like any high school guy I watched a lot of porn and soon realized that I really liked really nasty deep throat blow job scenes. I especially enjoyed watching a girl choke and gag and... Read full Story
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Army Slut
My name is Ray,16, I've always been into crossdressing as long as I can remember. Since I was about 11 or 12 if I could guess. (Started with sister's clothing) I am about 5'8, Skinny, Asian. I must say I look very cute dressed up. I would always call my self Megan When Dressed. (Little background ... Read full Story
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A Murder Misstery Finis
For those who came in late, Matt McCoy -- now Madeline Moreau -- is on the run for a crime he did not commit, and a murder which she did....as the saga concludes, Maddy vows to end her life on the lam. "Jacques, when I saw Dr. Villiers, the name I gave him was Madison Monroe. Do you think w... Read full Story
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Dressing at work
Having been crossdressing for sometime now I love the feeling of having fem things on when ever possible. I have started wearing things like garter belts, nylons and bras under my regular clothing. About a year ago I began to take some supplements to help grow breast and they are now a nice 36b and ... Read full Story
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Your Waitresses
You begin your evening by taking a long luxurious bubble bath followed by taking the time to apply your makeup at a beautiful white makeup table and mirror from the 1920's. You then slide a sheer pair of black stockings up each leg and attach them to your black and red lace garter belt. You then run... Read full Story
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A Strange Romance
Although I was over qualified after I graduated and accepted a one as an Internet operations officer for one of the high street retailers. I was offered better jobs but I took the one with the retailers because it paid reasonably well and more importantly meant that I would have to relocate down to ... Read full Story
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And Life Goes On
I am sitting in the living room waiting for my date to show up. A date arranged by my wife Gwen. I am dressed in a slinky red dress, underneath my torso is encased in a white corset which reduces my waist to a mere 25 inches. On my legs are a pair of black nylons attached to the straps hanging down ... Read full Story
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Eric...a Part 2
I was well into my first semester of college. The University I chose was close enough to drive to, but my parents thought it would be a good idea to for me to live on campus. I didn't mind, and actually wanted some freedom. I lived in a single dorm unit and was not having a difficult time of transit... Read full Story
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Lady in the House
How had it come to this? I was dressed as a woman and standing in the far corner of a darkened cell on E Block of Chelmsford Correction Facility for Men, and waiting for the most dangerous inmate in the jail. How had a mild mannered, and diminutive but highly successful accountant in his 30s ended u... Read full Story
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Blame Abba
Transgender-themed stories which I hope will be of interest to those who like women, or would like to be a woman. Which includes me! *** Part 1 - Well, I knew I was bound to be caught one day .... *** Thinking back - wow! So much, in such a short time, or at least it seems like that. Whe... Read full Story
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Blame Abba Chapter 2
Part 4 Out alone I wanted something which would let me wear my black 4 inch leather stilettos with ankle straps, really sexy shoes, my very first pair of TV heels. I opened the wardrobe to get them out, then started choosing; black seamed stockings; a black thong; my waist cincher bustier; my sho... Read full Story
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Body Types
My name is Carl and I love to cross dress. My alter ego, Carissa, is an out going and friendly person who first appeared in public recently. The occasion was a corporate Christmas party. I had been by that time dressing privately in front of my computer and participating in a video chat for several ... Read full Story
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Dressing for Pleasure
Earlier in the week they arranged that this Friday his wife will pick Angela and Sonia up from school, then drive straight to his parents' place, north, up the coast. Up to the big old house they have retired to, nestled near the shores of the lake, not far from the beach. When they arrive it sh... Read full Story
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I am Baaack! Part 12
Dainie and Joan stood on the Adams Street sidewalk that ran in front of the Sears Tower, watching as the limo that had brought Dainie sped away with Rose inside it. Joan thought Dainie appeared very nervous to see her mommy driving away, but Rose had told Dainie that she, Dr. Joan, was in charge and... Read full Story
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The real me
Well let me began Iam not in the closet, I grew up in small town my mom raised me cuz my dad was not around. This town was dead and in my school days there was only myself and friend of mine that were the only k**s in town. It was summer and my friend had left to go spend the summer with his grandmo... Read full Story
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Flashes of Eternity
We were placed inside a sizeable auditorium. I felt like a giant screen was placed in front of me, and - for all intents and purposes - that was the case. Dim lights made it difficult to ascertain how many people were around me. Truth is indeed stranger than fiction. The phrase used by many, but... Read full Story
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Gangbang
I was just out to show off, and have a good time wearing a short skirt and high heels at the local TV club. Tonight, though, I went a little farther than usual. I had bought some new things, and I was dying to show them off. I wore my latex rubber corset: pitch black, very tight, and very heav... Read full Story
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Fortunate accident part 2
A couple of days passed since I accidentally sent the embarrassing email. I hoped she had just ignored my email or not read it all together. She emailed me a few days later to invite me to a meet up. I was relived and happy she wanted to talk to me so I responded immediately. We met up at a coffee s... Read full Story
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Blushing Bride Chapter 5
Chapter Five: The Wedding Night I guess it's natural to be full of nerves and second thoughts on your wedding day but I'm not sure how many grooms have the sort of thoughts that I was having on the morning of my wedding. It wasn't that I wasn't very much in love with Gina, my beautiful fiancee, m... Read full Story
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Robbed And
I was in the ensuite off the bathroom applying the last of my make-up to complete my transformation from Martin to ‘Michele’ when I heard the disturbance. My wife Kerry was waiting for me in the bedroom nursing a gin and tonic. We had just returned from a boring party and I had convinced... Read full Story
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Cross romance
I wake up in the middle of the night. I have psyched myself into such a state that I just can't go back to sleep. Thinking back over the years, everything started with a size 32A bra. It happened on one morning when I just turned 13. In my locked bedroom, I clipped on a flimsy unpadded white cott... Read full Story
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Life Lesson #2: Freaky People Attract Other Freaky People :)
So for the most part, having sex while crossdressing is a bit of a fetish and once people know you are into it they are now free to share their own fetishes with you. That’s were my next life lesson comes in and I have a couple of stories about people doing some surprising shit near me or to me. ... Read full Story
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Embrace
I enter the room in my satin chemise, relishing the feel of the gown sliding across my body as I make my way towards the bed. With every step, the gown flutters, caressing my body, making me feel...sensual. I no longer lumber when I walk, like I do when I'm dressed in my male clothes. Instead, the f... Read full Story
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The change
Hello my name was Joe until I got caught in my girl friends cloths one day. Then my life changed ,some say for the better others say its for the worse. Here is how it all began. MY girg friend was out of town for a few days and I was house sitting for her . She had a cat I had to take care of. I ... Read full Story
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Nylon and lace
Well, I know it will be difficult to take this story seriously or as true happenings, it will seem far fetched and made up. I know, I know. It is however the story of my sexual awakening. The story of how I grew up to be what I am. I do not pretend to find psychological explanations or even less bio... Read full Story
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Yes Sir
I've been meaning to write this story for some time. It could have easily happened had I taken the initiative but instead, I chickened out. It remains a favorite fantasy of 'what if' though. I hope you enjoy. Saturday evening and I'm sitting in the living room of my small mobile home. Nothing to ... Read full Story
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Kylie and Chrissy
The following story is the first part of ‘Kylie and Chrissy’, a story documenting the blossoming sissy-hood of two teenage boys. It is partially autobiographical and partially fiction. PART 1 - THE INCIDENT ‘Stop… we really shouldn’t be doing this’ ‘It’s just a bit of fun. Now just hold sti... Read full Story
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The reason why I became a crossdresser
At first, I was just a straight and ordinary boy who was into sexy lingerie, stockings and heels. But one day, I suddenly thought that I wanted to try on my mom's panties, stockings, and high heels. So I did it. It was so excited and I started to get addicted to cross-dressing. Before dres... Read full Story
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Candy Pink
Life pretty much sucked. I was the son of Ralph and Cindy Cassella. They named me Ralph Junior and my dad was thrilled to have a son he could raise to live out his past glory. My dad wasn't a bad guy and never abused me but I knew he was disappointed. He worked as a contractor in the present but he ... Read full Story
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The Greatest Lie Part 3
My weekend escapade with my first real lover, Jake, convinced me that I was destined to live as a girl, despite having been born a boy. Unfortunately, it was my male persona to whom the University of Minnesota had extended admission and a scholarship, and I wasn’t quite sure how they would rea... Read full Story
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Bar trap
Steven was a dead-normal guy. At the age of 28, he felt very happy. Everything had developed in the last few years like he always wanted it to be. His job in a big insurance company was secure with an outlook of a promotion in the next year. His partner, Nancy, was a very ambitious lawyer. That ... Read full Story
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Damsel In Distress Chapter 2
2. The new Beginning. Duncan awoke early. His room smelt strongly of nail polish and he felt something silky on his chest. As requested he had bathed, shaved all over and covered himself in her moisturiser. He didn't go downstairs late last night for his customary milk drink but feeling naked min... Read full Story
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Yellow Polka Dot Bikini(s)
"She was afraid to come out of the locker. She was as nervous as she could be. She was afraid to come out of the locker. She was afraid that somebody would see. Two, three, four, tell the people what she wore. It was an itsy, bitsy, teenie, weenie, yellow polka-dot bikini that she wore for the ... Read full Story
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Happy Halloween
Hello my name is Mike! Let me tell you a little about myself for the story. I'm about 5 foot 5 and thin, about 135bls. I am half white and half hispanic, so i have a nice light brown complextion. I don't have much body hair and am very GAY! I have always know that I was gay, there was never... Read full Story
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A New Me...
Flash back 10 years when I had just turned 18 years old and had just been accepted into the University of Vermont. I was ecstatic because this was my reach school (I wasn't all that smart book wise) and it was the school that my sister Elizabeth (20, a junior) was already attending. My sister and... Read full Story
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Fantasies Fulfilled
I enjoy crossdressing and do so when ever I can. About the only time I dress as a man is to go to work. I have been doing this since I was eleven years old. I love to have sex with a man as if I was a woman and really think I should have been born a girl. I think like a girl and naturally act like a... Read full Story
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Finding out my next-door neighbor was a crossdressing beauty que
Finding out my next-door neighbor was a crossdressing beauty queen. I mean fetish is trans women, but I don’t mind blowing a load to a beautiful cross-dresser. I used to live in a small apartment complex in Queens New York. My neighbor was a guy name Luiz from Brazil. A very friendly and fl... Read full Story
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X-dresser Turns Housewife
A friend of mine that I have been seeing for a while shocked me one day. He called me up wanting to know if I was free throughout the day. I told him I could make time and he invited me over to his place. He told me to wear something a housewife would wear and bring an apron. I didn't know why, but ... Read full Story
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The Dinner Guest
After meeting John, and immediately becoming his lover on my first-ever dressed meeting with another person, our relationship became a deeply satisfying, regular thing. I guess I became his “girlfriend” although some might see it more as his “wife”. We met at least twice a we... Read full Story
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A Trip To The Mall
Oak Park Fashion Mall had lived up to its listing in the yellow pages as the "source for all your fashion needs". I had been there for 4 hours and spent a lot of money increasing Tammie,s wardrobe from the skin out. I had been in almost every store that featured ladies clothes (I don't rem... Read full Story
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