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Story tag results for crossdresser

Found 43 result(s)

OMG Last Night

- I suppose I'd better start at the beginning. Well, my femme name is Carly Hughes.I'm a 47-year-old male who has probably been cross-dressing since he was seven. I started dressing in my mum's and sis...

By: carlyhughes2018 | Category: Crossdressing | Score: 4.8| Added: 13 Aug 2018

Dressing up.

- It was the summer of my sixteenth birthday. It was when I first thought of girls’ clothing as the clothes I would like to wear. My name is Matt and I live with my three sisters and mother. I am the...

By: SeanR83 | Category: Crossdressing | Score: 4.8| Added: 20 Jun 2018

Part 1: Abandoned Parking Lot

- It begins... Well, I found out that Anne fucked that professor again. She came to my dorm, drunk at 3 am, fighting with me, calling me a little bitch and pussy, and she began slapping my face. I won...

By: sissyscarlet2 | Category: Crossdressing | Score: 3.9| Added: 09 May 2018

The Foreigner

- I had been chatting online with him for a while now, and he was keen to meet me. He identified as straight and was married, which is normally a deal breaker for me, but he was persistent. After a lot...

By: NaughtyAmy | Category: Crossdressing | Score: 4.9| Added: 05 Feb 2018

My first time in a bar

- For a while now I had been chatting with a sweet guy named Allen, who was bisexual and was eager to meet a crossdresser. He was very muscular and handsome, a hard body but with friendly eyes. He seem...

By: NaughtyAmy | Category: Crossdressing | Score: 4.9| Added: 22 Sep 2017

Unexpected Turn of Events

- I sat in my favourite bar sipping at my glass of Chardonnay; I had been coming to ‘The R Lounge’ for a couple of years. I watched the guy talking to his friends across the room. They were all dressed...

By: jessicaCD08 | Category: Crossdressing | Score: 4.9| Added: 21 Aug 2017

Hostess With The Mostest - Chapter One

- “Fuck! Fuck! Fuck!” Christopher Nyland threw the letter on the desk. “It’s just not fair!” he lamented. The piece of paper he has tossed on the desk was a letter of rejection from Goldwing Airways ...

By: MicheleNylons | Category: Trans | Score: 4.9| Added: 05 Aug 2017

Exploring Even Further

- For the rest of the week I was a total wreck, dreading, craving, anticipating, and fearing, the arrival of Jerry’s wife and Rocketman69, whose real name I'd discovered was Jim. Just thinking about al...

By: BadDog9 | Category: Crossdressing | Score: 4.9| Added: 23 Jul 2017

Stranger Fuck

-   I noticed the time strike 10pm on my watch as I got out of the cab outside the Red Circle. Hopefully tonight I was going to get lucky. After paying the cabbie and stepping out of the cab, I fixed ...

By: fernandezh1983 | Category: Crossdressing | Score: 4.8| Added: 16 Jun 2017

My First Time With Two Guys

- I had made a date with a guy I had been exchanging emails with on and off for three months. He seemed nice enough and was pleading with me to meet with him. He convinced me to meet him at a nearby ho...

By: NaughtyAmy | Category: Crossdressing | Score: 4.6| Added: 27 May 2017

Alexia's Tale Chapter 3 - Sensual Outgoings

- Sunlight beamed through the curtains, warming up the room. Under the sheets, a mildly aroused Alexia laid half asleep, one finger halfway up her ass and her mouth gently sucking on her other hand’s f...

By: CynthiaSissy | Category: Crossdressing | Score: 5| Added: 22 May 2017

Alexia's Tale Chapter 2 - Online Exploration

- Looks like it's never gonna stop," Alexia muttered, the warm vapor from the cocoa rising past her face like a discounted sauna. Her voice pitched higher, much to her liking, she continued, "twenty-fo...

By: CynthiaSissy | Category: Crossdressing | Score: 5| Added: 21 May 2017

Rainy Day For Alex(ia)

- The smell of rain danced near his nose, as Alex sat by the window. It had been raining for two hours now, with no sign of stopping. The clouds were ever so gray and the wind gave the trees reason to ...

By: CynthiaSissy | Category: Crossdressing | Score: 5| Added: 20 May 2017

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 like...

By: Tanyacduk | Category: Crossdressing | Score: 4.9| Added: 27 Mar 2017

Sissy sperm bank

- I started the morning my favorite way, really the only way I know how: with my bull's big cock between my lips. This was one of those nice slow blowjobs that he liked to start the day with. I made it...

By: Tanyacduk | Category: Crossdressing | Score: 4.5| Added: 30 Jan 2017

First time for 'Everything'

- My story is like so many I have read before and which I only fantasized about, till now. This story is all true. I thought about embellishing it to make it sexier but thought I’d let you know what ha...

By: CD_Danni | Category: Crossdressing | Score: 4.6| Added: 09 Jan 2017

Discovering a New Hotness

- Martin traveled a lot on his job. As a young, single guy he could finish up his installations and support work then head out to see what the local sights had to offer. He especially liked the south Fl...

By: AndyBrds | Category: Trans | Score: 5| Added: 20 Nov 2016

Curious No More

- I began dressing in my sister's clothes. I would get so hard and excited when I felt the soft panties against my cock and the bra wrapped tightly around me. But my dress up time was always short. Now ...

By: MelanieCD | Category: Crossdressing | Score: 4.8| Added: 16 Nov 2016

Confessions of a Ladyboy - Part 1

- I was eighteen and new in the boy's hostel. No one had wanted me at home. I had never known my father. I saw my mother go out with a different man almost every night ever since I was old enough to rem...

By: anagurl | Category: Crossdressing | Score: 4.9| Added: 04 Nov 2016

The Only Cure Possible

- Mia was standing in front of the dresser, checking her reflection in the large mirror that gave me such a wonderful view of her beautiful face and upper body. I could see her glance to the side and kn...

By: Strange4Utah | Category: Crossdressing | Score: 4.6| Added: 16 Oct 2016

Getting Used to Dildos

- Lucy had always wondered about having anal sex. Did anyone really enjoy it? When she first started thinking about it, the internet wasn’t like it is now. Apart from asking others who had had anal sex ...

By: LucyLou62 | Category: Toys | Score: 4.7| Added: 29 Jul 2016

A Real Big Surprise

- Jonathan had been seeing Katie for about two months. She was loverly, calm, beautiful looking with a voluptuous body. She had large breasts that were perfectly formed, a small waist, large pear shaped...

By: LucyLou62 | Category: First Time | Score: 4.7| Added: 13 May 2016

My 2 AM Phone Call

- It was about 2 AM when the phone rang. The voice on the other end simply said to get dressed. He told me exactly what to wear. Exactly. He wanted me in a black micro mini skirt, little black mesh top ...

By: jerrixdresser | Category: Crossdressing | Score: 4.5| Added: 18 Feb 2016

Mischa's First Time With a Man

- I have been cross dressing for a very long time, but it wasn't until recently that I decided to go full time girl. I have very feminine features and learned to embrace them over time. I always wanted ...

By: Micha8d | Category: Crossdressing | Score: 4.6| Added: 15 Jan 2016

Meghan's diary - Part 3

- A month has passed since that crazy experience with Jamie. Nothing ofthose sorts has happened since then but Jamie used every opportunity to remind me of it. I swear she was flirting with me and teasi...

By: xXMister_TXx | Category: Trans | Score: 4.8| Added: 21 Mar 2014

Meghan's diary:part 2

- The next morning I got up and got ready just like every other day. It was a beautiful Saturday morning, the sun shining in my face giving a nice and warm feeling on my soft skin. I really enjoy my sof...

By: xXMister_TXx | Category: Trans | Score: 4.8| Added: 31 Jan 2014

Meghan's Diary: Part 1

- This is the beginning of the start of my new life. Up to this point I'd been known as Michael but that would soon change. For months now I have been paying close attention to the girls but not like yo...

By: xXMister_TXx | Category: Trans | Score: 4.6| Added: 27 Jan 2014

The Awakening of Susi

- Ever since I can remember I have loved being feminized and being made to wear very slutty clothing. This is a true story of my first experience at a glory hole and a coming of age for my sissy self. I...

By: susi_swallows | Category: Crossdressing | Score: 4.8| Added: 05 Dec 2012

Motel Fun for College Crossdresser

- Before I start the story I want to describe the setting so you get a better idea: it's a highway side motel, very rundown and not very cleanly, not a dump either but not the best place to have a fami...

By: jess_xo | Category: Crossdressing | Score: 4.6| Added: 04 Nov 2012

Karren Gets Sucked and Fucked Part 2

- Karren followed Kevin to his home in her own car so if she had to leave she could do so at her leisure. Karren wondered what Kevin's wife looked like, would she like the idea of a man dressed like a w...

By: Karrenfuchmee | Category: Crossdressing | Score: 4.9| Added: 13 Oct 2012

Six Months

- After all those years of longing to be free, stuck in relationships with women that frowned upon my cross dressing, I was still very much relishing my freedom. I was dressing every moment I could, the...

By: TaraNicole | Category: Crossdressing | Score: 4.9| Added: 03 Oct 2012

CD Domina training two slaves

- Just five days had passed since my last session with my slave Candy and already I was yearning for his sexy body again. I was in need of another meeting and had something special planned for it. I ca...

By: MistressCheyenne | Category: Crossdressing | Score: 4.8| Added: 12 Jul 2012

CD Mistress Cheyenne can't fight the craving for Candy

- Almost two long weeks had passed since my first meeting with my new slave Candy. Our first encounter was special and my sexy new sub had not left my mind since he walked out of my door. His juicy ass ...

By: MistressCheyenne | Category: Crossdressing | Score: 4.9| Added: 04 Jul 2012

Crossdressing Domina gets a new slave

- I have been a crossdressing Mistress for several years now. I have a petite body and always looked good in a dress. I take on many slaves but my favorites are other men who look great in dress. This i...

By: MistressCheyenne | Category: Crossdressing | Score: 4.8| Added: 29 Jun 2012

Shopping outing for lingerie

- Following is a true account of one of my experiences of shopping for lingerie. (nosex). This happened a couple of months ago, and as far as I remember, the conversation went like I have described belo...

By: subguy | Category: Crossdressing | Score: 4.8| Added: 21 Apr 2012

Friend Becomes My First Part 1

- *This is a true story of my first time having sex dressed a girl* It finally happened, and it was a dream come true. I started dressing as a girl when I was 17. For me, it started with a thong I stol...

By: iltns2569 | Category: Crossdressing | Score: 4.2| Added: 22 Jan 2012

Chrissy Gets Bolder Meeting Todd Again

- I really hadn't expected Todd to call me after that night. I know how guys are when the night is getting short and you need someone to satisfy your needs. I did think about him a few times and wanted...

By: Chrissy_CD_slut | Category: Crossdressing | Score: 5| Added: 21 Oct 2011

Put it on!

- I was living and working in London, my first job after college. No chance of having a place of my own with these crazy house prices and this being my first job at the age of 23, so I rented a room fro...

By: anotherfeeling | Category: Crossdressing | Score: 4.9| Added: 16 May 2011

Cindytranee meets the maintenance crew

- This is a true story that happened a few years ago when Iwas living in an apartment complex while looking for a house. I had taken a small one bedroom on the 2 nd floor. It was very nice and private a...

By: cindytranee | Category: Crossdressing | Score: 4.8| Added: 04 Apr 2011

Crossdresser's Spanking Scene

- My roommate and I were both bi and part-time cross-dressers. We were also familiar with consensual B & D and had already worked out several code words, then went a step further and wrote scenes for...

By: JesseS | Category: Crossdressing | Score: 5| Added: 25 Jan 2010

Lingerie and Domination

- I had answered an ad on telephone dating service. She described herself as a ‘bedroom dom’. I am not sure why I answered the ad and I did not really expect a reply. She phoned when I least expected....

By: pam1950 | Category: Crossdressing | Score: 4.1| Added: 20 Nov 2009

I was a wartime TV for the US Army

-   'I was a Wartime Transvestite for Uncle Sam!               TJ Ryder                                            Chapter 1           Reform School Romance!     I couldn't believe that all I got from...

By: tjr | Category: Crossdressing | Score: 5| Added: 18 Mar 2009

Smooth Sensation

-   God I was glad to be home, a two-hour train nightmare. Every stop from Liverpool Street London on the 6pm slow train to the dreary little Essex village that was the only place I could afford to ...

By: TaraNicole | Category: Crossdressing | Score: 4.7| Added: 16 Feb 2009