Crossdressing

Dividence

The Wedding Proposal, chapter VI

Reality catches up to me.

The dinner was wonderful. Tina was the sweetest sister-in-law I could ever wish for. We found that we had lots of things in common, and quickly bonded. She told me all sorts of stories about Tony, and I shared stories from my time as his friend. I had to concentrate to adapt the stories to the new ‘reality’, but as long as Tony played along it went great. He seemed a bit uncomfortable with...Read On

Added: 16 Mar 2016 | Category: Crossdressing | Avg Score: 5 | Words: 1,594 | Tags: party  dance  alcohol  fight  one night stand  anal  random encounter   | 2 Comments

Kasey

Late Night Bus

Ben makes and receives a deposit at the depot...

It's a beautiful, foggy English night. Panting, my lungs aching from the cold, I reach the bus stop at a dead run skidding to a halt on the loose crumbling tarmac. The salty taste of Steve's cum still fresh on my tongue and my anger unabashed. Catching a breath, I realise just how much I love nights like these. The ubiquitous street lights struggle to penetrate the gloom of their...Read On

Added: 14 Mar 2016 | Category: Crossdressing | Avg Score: 4.67 | Words: 4,985 | Tags: oral  anal  bisexual  crossdress  femdom   | 8 Comments

Dividence

The Wedding Proposal, chapter V

With my life back to normal, I cannot seem to relax, until a fateful call makes my life whole again.

I turned the key in my apartment door. As I heard the lock click, and the door swinging open, I suddenly felt a strong sense of abandonment. The sensation was so strong that I had to close my eyes and draw a deep, long breath. I was surprised, but instantly knew what it signified. Stepping through that door would be the final return to myself. To who I really was. The magic would be broken...Read On

Added: 08 Mar 2016 | Category: Crossdressing | Avg Score: 5 | Words: 1,968 | Tags: lingerie  crossdressing  friends   | 1 Comment

SashaCD_ThongPanties

My Foggy Late Night Story

On a foggy late night, Sasha gets fit, lucky, and... loved?

It was a cold, wet December night. Here I was in my room, feeling exhausted, and laying on my bed doing the whole Netflix and chill thing. I had just pulled a long afternoon and evening event with my college study group. We spent the day as total masochists painfully cramming whatever we could into our tired brains for our finals. It had worn me out so much that I didn’t want to do...Read On

Added: 03 Mar 2016 | Category: Crossdressing | Avg Score: 4.71 | Words: 6,808 | Tags: crossdressing  yoga pants  thong  anal  oral  reluctance  creampie   | 3 Comments

sissycderica

Erica Meets Sarah: Part 1

Slutty CD Erica meets Sarah to fulfill her ultimate fantasy for the first time.

I woke up alone on Saturday morning in my nylon blue g-string and nothing more. I wanted to feel it the instant I woke up, my sexually charged femininity, I wanted to feel it all day. Today I'm not a man, today I'm the girl every man wants. Today I'm a slut, your slut. I showered and shaved myself smooth. Ridding myself of body hair was always the first step. Nothing could make me feel...Read On

Added: 28 Feb 2016 | Category: Crossdressing | Avg Score: 4.92 | Words: 3,744 | Tags: crossdressing  sissy  first time  slut  anal  blowjob  toys   | 8 Comments

Dinata

Park-n-Play

State parks are not just for nature lovers...

Being the social butterfly that I can be at times, I was checking a website that listed my area to see of there were any 'cruising' areas I could check out in hopes to share my fetish for crossdressing and pleasure. There were several areas, too many to choose from, so I opted for a forested state park. Since much of the funding for the parks in Ohio have been suspended or cut, the chances...Read On

Added: 25 Feb 2016 | Category: Crossdressing | Avg Score: 4.68 | Words: 1,642 | Tags: bisexual  crossdressing  park  sex  cum  blowjob   | 10 Comments

Dividence

The Cabin, chapter III

As the storm clears, we decide to make the most of our time together.

When I awoke the next morning sun was shining in through the windows, bathing my golden hair in its rays. I got up quickly, but careful not to wake my lovers. The nice weather made me think that we would soon have to leave the cabin and my taste of life as a girl would be over. Regretting this, I was determined to make the best of my morning with them. I went to the bathroom and once...Read On

Added: 21 Feb 2016 | Category: Crossdressing | Avg Score: 5 | Words: 1,641 | Tags: anal  crossdressing  threesome  cumshot  kissing  cd  m2f   | 5 Comments

jerrixdresser

My 2 AM Phone Call

Sissy cross-dresser is told to report to a motel at 2 AM

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 that barely came below my nipples, five inch platform heels, lots of junk jewelry and a bushy Vegas platinum blonde wig. He said to come to the Diamond Motel on the Gulf Freeway and then he hung...Read On

Added: 18 Feb 2016 | Category: Crossdressing | Avg Score: 4.5 | Words: 912 | Tags: sissy  cross-dresser  motel whore  thug  gang bang     | 2 Comments

Dividence

The Cabin, Chapter II

I do my best to comfort the two frozen wanderers stumbling through the door.

I do not know how long I sat there gazing into the flames and sipping wine in complete peace. The wind outside was far away in my mind, but suddenly a huge bang broke the silence. The door flew open and slammed into the wall. Rain swept through the small cabin and sprayed me with icy cold droplets. I nearly fainted from shock, and the noise from my pounding heart overshadowed the howling of...Read On

Added: 14 Feb 2016 | Category: Crossdressing | Avg Score: 4.94 | Words: 2,969 | Tags: crossdressing  threesome  m2f  transsexual  blowjob  anal   | 13 Comments

tvk3983

Dana Finds A Lover

Dana meets a man and becomes his

I've been dressing since I was ten, always being careful to never be seen by anyone. The whole time I grew up I'd never had any girlie clothes of my own but I'd always worn my sister's things, even used her makeup. I always made certain that she never ran out of makeup too quickly. When I knew I had the house to myself, I would dress up and pretend I was a girl. These sessions ended in a...Read On

Added: 04 Feb 2016 | Category: Crossdressing | Avg Score: 5 | Words: 3,292 | Tags: anal  oral  crossdressing     | 10 Comments

Dividence

The Cabin, chapter I

I accidentally stumble a "rich" crossdresser's secret cabin, thrilled by my find.

The latest months had been quite rough on me and I’d been looking forward to this trip for a long time. My girlfriend had left me, muttering something about me not being manly enough for her. In reply, I had buried myself in work and self-pity. When I finally came to my senses, I knew I had to take a break. My backpack was burdened by everything I would need, which wasn’t much. I...Read On

Added: 29 Jan 2016 | Category: Crossdressing | Avg Score: 4.71 | Words: 2,269 | Tags: storm  crossdressing  transgender  lingerie  panties  stockings  garter   | 10 Comments

tvk3983

Terry Gets It In The End

Terry's girlfriend finds him in panties and leads him down the path.

The converted attic was my room and it gave me loads of privacy. So as I grew up I could wear the clothes I liked, as long as I stayed in my room. By the time I was a senior in high school, I kept my toe nails painted all the time and I wore panties every day. At night I wore frilly little night gowns and more likely than not I would masturbate, always fantasizing that I was the girl and...Read On

Added: 27 Jan 2016 | Category: Crossdressing | Avg Score: 4.91 | Words: 8,310 | Tags: taboo  cd  tv  oral  anal  straight     | 9 Comments

ThePhantom

How Andrew became Andrea - The Conclusion.

It was easily one of the best summers of his teenage years. Now along with being allowed to indulge himself in his secret desire, he had sex with the stunning Lacy on a regular basis. She had become a friend, lover, employer and tutor. When school resumed in the fall he was forced to limit his visits as there was homework and studies that needed his attention. However when his parents went...Read On

Added: 26 Jan 2016 | Category: Crossdressing | Avg Score: 5 | Words: 1,333 | Tags: halloween  makeup  heels  decisons  future   | 9 Comments

ThePhantom

How Andrew became Andrea Part 3

Andrew leaned back on the couch feeling the warm cum had just let loose in his panties beginning to cool and a stain become visible on his slip. "Looks like you will have to clean up and change," Lacy said with a smile. "Looks like," Andy responded. "Shall I pick out something or would you like to?" "I would like you to." Andy headed to the bathroom where he removed his cum...Read On

Added: 23 Jan 2016 | Category: Crossdressing | Avg Score: 4.89 | Words: 687 | Tags: lingerie  heels  halloween  makeup   | 9 Comments

ThePhantom

How Andrew became Andrea Part 2

"Did you cum?" Lacy asked.   "Yeah," he answered trying not to look at her.   "No need to feel embarrassed. Its all right."   "I think I better go," he said and stood to leave.   "Can you come over tomorrow?"   "Yes, if you want me to."   "Yes, I want you to. I will have a proposition for you," she said as she escorted him to the door.   "A proposition? What kind?"   ...Read On

Added: 22 Jan 2016 | Category: Crossdressing | Avg Score: 4.94 | Words: 1,310 | Tags: milf  silk  learning  slip  panties   | 11 Comments

Dividence

My Best Friend

My friend's reaction to me dressing as a girl caught me by delightful surprise.

I always wanted to be a girl. Every time I saw those pretty girls prancing around the college campus I’d become green with envy. Their feathery skirts caressing glossy thighs. Long, silken hair cascading across bare shoulders. High heels clicking on the pavement as they paraded their fit asses in front of all the guys. They were allowed to be sexy, and no one would stop them. And the warm...Read On

Added: 21 Jan 2016 | Category: Crossdressing | Avg Score: 4.96 | Words: 3,223 | Tags: crossdressing  anal  blowjob  m2f  friends  college  dorm   | 13 Comments

ThePhantom

How Andrew became Andrea Part 1

How it began.

Andrew Lippincot's childhood had been quite normal, as were his teenage years. At sixteen he hung with his friends, played baseball, rode their dirt bikes and talked about girls. One of his friends always managed to produce a Playboy magazine from their Dad's collection. He and his buds would peruse these forbidden pages with wide eyes and trembling fingers as their pricks hardened. While...Read On

Added: 21 Jan 2016 | Category: Crossdressing | Avg Score: 4.61 | Words: 1,260 | Tags: beginning  secret  lingerie   | 10 Comments

CDDeeDee

Lovers in the Afternoon

Once upon a time, on a quiet afternoon.....

Through the scrim curtains, the soft afternoon sun lights the room with a pastel glow. I sit at the chair in front of the dressing table, quietly smiling to myself. I finish putting on my make-up; a light touch of lip gloss. I look at myself in the mirror. Quite good I think. I am getting better all the time. I can feel the tension and excitement in my body. My perfume fills my head. My...Read On

Added: 20 Jan 2016 | Category: Crossdressing | Avg Score: 5 | Words: 2,410 | Tags: afternoon  affair  

Micha8d

Mischa's First Time With a Man

First anal experience dressed up 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 to be the live-in 'girlfriend' of an older daddy-type of man, who would let me please him all the time. The thought of being a man's personal companion and sex toy is extremely gratifying. There's...Read On

Added: 15 Jan 2016 | Category: Crossdressing | Avg Score: 4.64 | Words: 1,506 | Tags: crossdresser  first  anal   | 7 Comments

sarahricegirl

Becoming Sarah

A man embraces his femininity and gets changed forever.

I was driving home from a work trip. That is how it started. There was roughly 85 miles to home. I had been driving for about an hour when my mind began wandering the way it always does when I'm not preoccupied. It always goes to the same place. For the better part of five years, I have been cross-dressing in secret whenever I have the house to myself. Sometimes I do it because it...Read On

Added: 12 Jan 2016 | Category: Crossdressing | Avg Score: 4.97 | Words: 4,345 | Tags: crossdressing  first blowjob  first anal   | 16 Comments

ThePhantom

Weekend Discovery 3

Simone was left alone in a room that held the most extensive collection of lingerie that she had ever seen outside of a retail store. She was amazed that she was as turned on as she was and not shocked at the current events. She had gone to her boss's house to confess just how much she wanted him and to see if the feeling was mutual. She was momentarily heartbroken when a stunning...Read On

Added: 06 Jan 2016 | Category: Crossdressing | Avg Score: 4.91 | Words: 1,485 | Tags: lingerie  heels  drinks  confession  oral  anal   | 5 Comments

tvk3983

Michelle Gives It Up

Michelle provides him with everything she has to ffer

When my best friend, Jimmy, left my house late that afternoon he was a very well satisfied guy, sexually. For the two years prior we'd had quite a few mutual masturbation sessions. This had progressed from jacking off while talking about various girls we knew in school to jacking off each other. Of course, at that time neither of us had actually done anything with a girl, but that never slowed...Read On

Added: 05 Jan 2016 | Category: Crossdressing | Avg Score: 4.96 | Words: 1,791 | Tags: cd  tv  oral  anal  first time   | 9 Comments

tvk3983

Karen Goes Out

Karen gets the nerve to go out and discovers who she is.

I was so nervous I was almost sick. For years I'd dreamed of going to a bar that catered to the LGBT community but I'd always come up with an excuse not to, no matter how flimsy it might be. Yes, I'd gone out in public several times, shopping mainly, but also banking, getting gas, and even meeting with other girls like myself. So far, the only sex I'd indulged in while dressed had...Read On

Added: 01 Jan 2016 | Category: Crossdressing | Avg Score: 5 | Words: 3,499 | Tags: cd  tv  oral  anal   | 8 Comments

ThePhantom

Weekend Discovery 2

Simone's eyes grew wide when she realized that the stunning blond she was sitting next to was, in reality, her boss and the object of her most intimate desires. Now she had seen transvestites and drag queens before, but none of them looked this good. She was sitting just mere inches away from his face and still couldn't see any trace of Andrew Lippincott. Without warning Andrea leaned...Read On

Added: 01 Jan 2016 | Category: Crossdressing | Avg Score: 4.91 | Words: 728 | Tags: silk  satin  nylons  toys   | 4 Comments

ThePhantom

Weekend Discovery 1

Friday had finally arrived. Andrew Lippincott glanced at the Rolex on his wrist and then began to pack his attaché case. It was only 4:00 pm but he was the office manager and one of the perks that came with this title was the ability to leave early. Winter had the city in its grasp and a travelers advisory had been posted.That meant there would be no unannounced guests to prevent him...Read On

Added: 30 Dec 2015 | Category: Crossdressing | Avg Score: 4.78 | Words: 1,178 | Tags: panties  nylons  garterbelt  heels  makeup   | 5 Comments

Dividence

The Wedding Proposal, chapter IV

Part 4 of 4: The young newlyweds spend their honeymoon on the yacht.

The first week at sea was wonderful. We set off to the Mediterranean, and the sea was calm and pleasant. A refreshing breeze made slight ripples on the quicksilver surface. I guess we would curse the heavens if we had to rely on sailing wind, but in the motorized yacht, it felt like a blessing. There were no other people around, and I could fully succumb to my feminine side. I spent long...Read On

Added: 15 Dec 2015 | Category: Crossdressing | Avg Score: 4.4 | Words: 797 | Tags: crossdressing  lingerie  honeymoon  yacht  blowjob  wedding  bride   | 3 Comments

Dividence

The Wedding Proposal, chapter III

Part 3 of 4: After the wedding comes further complications. But not necessarily for the worse.

I woke up and saw the bright, yellow orb of sun shining in through the broad windows. It was warm, and the thin linen was wrapped around my sweaty body. I was glad I remembered to remove the tight corset before going to sleep, and I was now wearing only the thigh-high stockings and garters. A pair of white panties lay on the floor where they had been hastily thrown. My fake breasts were...Read On

Added: 10 Dec 2015 | Category: Crossdressing | Avg Score: 4.5 | Words: 1,372 | Tags: wedding  lingerie  m2f  crossdressing  bride  honeymoon  anal   | 2 Comments