Crossdressing

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: 4.95 | Words: 2,969 | Tags: crossdressing  threesome  m2f  transsexual  blowjob  anal   | 15 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: 4.92 | 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   | 7 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

Dividence

The Wedding Proposal, chapter II

Part 2 of 4: A nervous fake bride attends her friend's fake wedding.

The large gown rustled, and the heels clicked loudly as I descended the stairs in my home and walked towards the front door. I would be picked up by my friend’s sister before going to the church. I had never met her before, but he’d assured me that she knew nothing of my secret. It would be nice to have someone to confide in, but I knew being treated as a girl by everyone would probably...Read On

Added: 09 Dec 2015 | Category: Crossdressing | Avg Score: 4.78 | Words: 1,541 | Tags: bride  wedding  crossdressing  lingerie  gown  dress  friends   | 5 Comments

Dividence

The Wedding Proposal, chapter I

Part 1 of 4: Real friendship is measured by how far you are prepared to go.

I slowly let the sheer, white stockings slide up along my closely shaven legs. They were smooth as silk, and no hint of coarseness caught the fabric as I stepped into them. The broad bands of elaborate lace hugged my thighs and made me feel great. Four straps, each decorated with a small silk ribbon, held the stockings attached to the garter belt I wore around my waist. The coarse lace felt...Read On

Added: 29 Nov 2015 | Category: Crossdressing | Avg Score: 4.57 | Words: 1,050 | Tags: crossdressing  wedding  proposal  lingerie  underwear  lace  stockings   | 9 Comments

tvk3983

The Adventures of Patty

Patrick becomes Patty and doesn't look back

“You're wearing my things again!” Brenda screamed when she came home early from community college and found me prancing around the house in one of her short skirts. “Take them off, you little pervert!” It wouldn't be nearly as bad if I were her little sister and trying on her clothes but I was her brother. But it wasn't as bad as it could be. I mean, if she knew what Tommy and I had been...Read On

Added: 29 Nov 2015 | Category: Crossdressing | Avg Score: 4.82 | Words: 8,605 | Tags: cd  tv  oral anal  threesome  first oral  first anal   | 12 Comments

Jakladd

Wifey's Panties

What a hottie little sissy bitch I have become.

Our phone sex is always so hot; you egg me on in so many ways. My wife has no idea how much I wear her panties not to mention her lingerie, stockings and dresses. We talk about what I'd wear when we get together as I suck your cock. You always have me send you pictures of me dressed in panties, stockings and high heels, telling me how perfectly stunning my penis looks in silky panties and...Read On

Added: 27 Nov 2015 | Category: Crossdressing | Avg Score: 4.25 | Words: 1,594 | Tags: crossdressing  sniffing  panties  cocksucking  cum   | 5 Comments

tvk3983

Sharon Goes The Distance

David becomes Sharon at his wife's request

When I woke up Saturday morning, I knew it would be a very eventful day. My wife, Donna, had been making plans for quite some time, which included me dressing up as Sharon, my female alter ego. Three years ago, I had confessed to Donna my desire to wear feminine attire from time to time and she had embraced it more than I could ever imagine. In fact, she took pictures of me all dressed up or...Read On

Added: 27 Nov 2015 | Category: Crossdressing | Avg Score: 4.8 | Words: 5,572 | Tags: cd  oral  anal  first time   | 7 Comments

Tara85

The Engineering Costume Party: Part 2

A college freshman gets more than he bargained for.

After realizing I might be the only guy dressed as a skank for the Skanks and Robots Party I timidly waited in the dorm room and “pre-gamed” with Anthony and Jillian for the upcoming festivities. I drank vodka and cranberry with Jillian while Anthony had beer. I hoped some “liquid courage” would help me to feel more comfortable going to the party dressed in such a slutty outfit. Now, I...Read On

Added: 19 Nov 2015 | Category: Crossdressing | Avg Score: 4.73 | Words: 1,931 | Tags: college  blowjob  crossdressing   | 7 Comments

tvk3983

Deann Finds Out

Deann finally works up nerve to go out in public

Jimmy sat up in bed and felt the dry cum on his belly from last night's masturbation. A quick look at the clock told him his parent's had already left for work and their weekend trip so he knew he had nothing to worry about. The plans he had for the day could begin right now. Stepping out of bed, he padded to the bathroom and began the process. A long shower began the day. He made sure...Read On

Added: 12 Nov 2015 | Category: Crossdressing | Avg Score: 4.81 | Words: 4,698 | Tags: first time oral  first time anal  first time out   | 6 Comments