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Cross Dressing Stories

Crossdressing, usually more common for men, is an interest that explores self-expression by wearing clothes from the opposite gender.

Often the clothes chosen will either belong to a spouse or a partner which unlocks a door for new erotic pleasures. Adapting the comfort of clothes that aren't normally worn can be an activity that takes place behind closed doors or be an exhilarating experience outside as well. Wearing a dress, high heeled shoes, feeling pleasure from wearing lace and satin, and choosing the name of the opposite gender, are all traits associated with cross dressing.

Have you become a crossdresser or are sexually attracted to crossdressing? Share your exciting discoveries by writing your own erotic encounter below.

So I ended up at one of these parties last night and boy was it a sight and a half! Being a non-binary fem Queen amongst all those yummy dicks got me wanting to devour them whole, but again as usual I was a shy, pretty princess with just the tingles between my legs but never finding the guts to go down on my knees and gobble a few. After all of the watching and wanting to join, I sat in my corner and just let my tingles t...

Phantom432

14 reasons why a woman would want to date and encourage x-dressing men

Stay youthful, positive, and less likely to fall into depression and anxiety.

It is important to note that not all x-dressing men will have these qualities and that there is no one-size-fits-all in relationships. However, these are some potential benefits to consider: 1. They are often more open-minded and accepting, which can lead to a deeper and more fulfilling relationship. 2. They tend to have a better understanding of women's clothing and fashion, which can be helpful for picking out outfits a...

Phantom432

10 reasons why X-Dressing is not for Sissies

My new appreciation for ladies and thier efforts to look good for men

As a straight guy, who likes to wear ladies' intimate clothing in private, as my fetish would be, I am learning a lot about women and starting to feel quite a lot of empathy for them and what they have to endure just to leave the house every day. In my opinion, one way to describe wearing women's clothing to someone who does not know it would be like putting peddles in your shoes and having to keep them there all day. Her...

Phantom432

Fake Cross-dressing garments?

Unravelling the mystry of straight men who X-Dress

In the vast realm of human expression, there exists a vibrant community that challenges societal norms and defies expectations—we, the straight men who cross-dress, in private. While we may seem as hard to spot as a chameleon in the rainforest, believe me, there are a lot of chameleons in a rainforest! Our experiences, though, have often been shrouded in mystery and overlooked by research, so maybe it’s time to shine a sp...

Jennyx

Meeting another cross dresser

Fucking me to a siisy gasm

I said a story for another day! Well hope you cum like i did wile righting this story for you. Remember i am afrikaans. Back to my cross dresing friend. We met on the most funny way, let me explain. One night in winter with my track suit on,late night rushing to the shop for sigarets wich i forgot in the day. Wearing my sexy little very short mine dress under my clothing. I went in and looked for a treat aswell bending do...

Jenny

Life changing day

How we got to knowing each other

First of all, i am Afrikaans speaking but writing my story in English. Cross dress surprise. I love to cross dress when i am in the mood, which is easy and often as i stay all alone in a 3-bedroom house all private on a farm. This is the story of a day i would not change for anything. I am all excited and pleased with myself waiting for a fellow cross dressing friend all dressed up and ready for a nice day. Waitng patentl...

Crossdresser pleases new Master

Learning what it takes to become the perfect sissy for her new Master

Having had my first real taste of my new Master and how exciting the experience had turned out to be, I could not wait till we met again. Luckily, I did not have to wait long before he was back in town. A couple of weeks after my first encounter, Master contacted me to let me know that he was arriving the next day and that I was to meet him at his hotel in the pub at 3pm sharp and was given instructions what to wear benea...

Anonymous

Meating Samantha

My one and only meeting with a very hot cd

It had been almost two years since my first experience with Dave. That was the first time a man had sucked my cock. It was the first time I had touched another cock and the first time I had sucked a cock. That day was the birth of a new me. I no longer was a homophobe. Although, I did not look at men the same way I looked at women. I did not lust after them. What I did lust for was for a cock in my mouth, loads of cocks....

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kinkyswingers

he and his friend

nice threesome

on a day i started to challange myself and go in public and cross dress i always done it in private i got dressedbin this short black mini skirt and top and tucked my penis away i the decided to walk to the car all the guys were looking at me and one whistle also the gave me more confidence as i arrived at a bar i went to sit and order a drink after 5min three guys walked in and sat accross me i did not give to mich atten...

kinkyswingers

So i had this fantasie for a long time dress like a woman and get used So one day i decided to go out buy make up sexy clothes and naels and a wig i rented a at a guest house I got at the guest house paid the owner he was a tall black guy well biuld and kinda had a gangsta look I got in to the room and i started my make up got dressed in a black mini skirt with leggings and a sexy top showing my clifitch(i also ordered fa...

Indelicate

Fluid sexuality and primal truth

Heart-shaped, petite, tiny almost. And so beautiful and fluid. Her buttocks arching up with need in a slow rhythmic intensity. The white fine boxers showing her swollen cocklet. She was plugged, knowing I was coming over. Softening and opening herself, something I very much appreciated. Swollen, I felt the thick trunk of my naked cock swelling, rising. I heard her gentle ache for the mounting, the hunger in her sweet sigh...

My first

Read in full, you will understand

She saw my deficits. My flawed masculinity. She knew the pivot triggers that unsettled my decorum and control. Through it all, somehow, I kept trying to maintain the semblance of normality, diplomacy and coolness. Even though inside, I struggled to own that I was different. Her body had youth and energy on its side. Lean, the tone of dark, rich coffee. Nipples, nubile and fierce. And she had cunt power, though never acted...

A Xdresser with a new Master

Being a cross dresser and serving a Master can sometimes be very rewarding and humiliating at the same time.

A Xdresser with a new Master Being a cross dresser and serving a Master can sometimes be very rewarding and humiliating at the same time. This is one of those occasions. I had recently met a new Master and was learning the ropes on how to serve and please. I received a message from my Master informing me that he was coming to town and that I was to meet him for breakfast in the restaurant at his hotel at 8am. I was instru...

My first time with a crossdresser was about 3 years ago. When I was younger I was addicted to so much porn I got to a point that I clicked on shemale porn just to see, not knowing I would get addicted to seeing b*+ches get fucked with their hard dicks in the air. So as I got older and after many years of watching trans porn I decided I need to experience this in real life so I went on line to search shemales in cape town,...

When your Girlfriend discovers she is dating a cross dresser.

Being caught - The 3some - The humilliation - The happy ending

Part 1 Meeting Sally Arriving back from overseas and having had the amazing experience with Lars and Anna with them helping me to truly accept my other being, Samantha, it was time to get back into life here in South Africa. The experience of embracing my feminine side and accepting my cross-dressing was unfortunately going to have to take a back seat as I moved back in with my parents upon my return. For the next 3 month...