Crossdressing

allfours

Becoming Chloe - Part 15

An agreement is reached...

Tina's car pulled into the drive around ten the next morning. Once the front door was closed behind her, she greeted Vickie with a passionate kiss, and then did the same to me. It felt good to be in her arms again, and I knew it would be hard not to give in to her, but we needed to sort things out. The fear of losing Vickie to her had not gone away, so I needed to make sure we kept our feet...Read On

Added: 15 Feb 2016 | Category: Crossdressing | Avg Score: 5 | Words: 3,371 | Tags: crossdressing  anal  oral  toys  threesome  fff  bisexual   | 4 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: 5 | Words: 2,969 | Tags: crossdressing  threesome  m2f  transsexual  blowjob  anal   | 15 Comments

DarkSide

My First Time

Melissa was excited, it was her first time.

The sheer thrill of what I was about to do was bursting through my body. My nipples tingled at the thought and my heart was pounding in my chest. I pinched one of my nipples until it hurt, just to prove that I was not imagining it. I simply couldn’t wait to see Mark. Three hours to go before I would stand in front of him and let him touch me, caress me and fuck me if he wanted to. All I had...Read On

Added: 14 Feb 2016 | Category: Crossdressing | Avg Score: 4.87 | Words: 3,661 | Tags: crossdressing  mutual masturbation  oral  anal   | 17 Comments

allfours

Becoming Chloe - Part 14

The aftermath. Chloe and Vickie have a heart-to-heart.

"Shit!" I was immediately awoken by Tina's curse. I opened my eyes to see her gorgeous, naked ass fly through the door to the bathroom, so I turned to my naked wife next to me, still half asleep. "Good morning," I murmured. "What was that all about?" "She's late for work. She should be at the shop for nine and it's gone half eight." "Oh," I said as I moved to snuggle next to her. ...Read On

Added: 09 Feb 2016 | Category: Crossdressing | Avg Score: 4.92 | Words: 2,801 | Tags: crossdressing  feminisation  transition   | 6 Comments

allfours

Becoming Chloe - Part 13

Ménage a trois...

Vickie sat down on the sofa and, spreading her legs wide, directed me to her snatch. I willingly let myself be guided to her most intimate parts and breathed in her womanly aroma. I wanted to savour her, so I took my time. I kissed her inner thighs, so different from Vickie's, and brushed my nose against the thatch of hair between her legs. I flattened the mass of curls, revealing her...Read On

Added: 06 Feb 2016 | Category: Crossdressing | Avg Score: 5 | Words: 2,457 | Tags: crossdressing  bisexual  lesbian  toys  dominance  oral  anal   | 6 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

allfours

Becoming Chloe - Part 12

A meal with a difference...

I walked through the door, and almost immediately all my resolve disappeared at the sight that met my eyes: my wife was sitting on the sofa with her legs spread wide with Tina between them, eating her out like no tomorrow! Vickie's knickers were wrapped around one ankle, and she held up her legs high to give her lover better access to her quim. It glistened in the late afternoon light with...Read On

Added: 03 Feb 2016 | Category: Crossdressing | Avg Score: 4.93 | Words: 1,606 | Tags: crossdressing  bisexual  anal  toys  dominance     | 5 Comments

allfours

Becoming Chloe - Part 11

Vickie meets Tina, and and Chloe has a surprise for dinner...

Vickie was naked, apart from her white jacket, stockings and suspender belt. Unlike the woman who left several hours ago, her hair was now loose and dishevelled, falling softly to her shoulders. Her make up was no longer pristine: her mascara had run a little and her lipstick was definitely in need of refreshing. Her lips seemed a little swollen, and her jacket was parted just enough for me...Read On

Added: 01 Feb 2016 | Category: Crossdressing | Avg Score: 4.77 | Words: 2,560 | Tags: crossdressing  feminization  toys  anal  lesbian     | 5 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

allfours

Becoming Chloe - Part 10

Chloe gets fucked by Vickie's new cock, and then Vickie arranges a meet with Tina

As I started to strip off, Vickie insisted that I leave my bra, suspender belt, stockings and heels on. She lay on top of me on the bed, kissing me and fondling my smooth body, which was something I adored. I felt her hand snake between my legs and gently caress my balls. "Mmm, my baby feels full," she whispered in my ear before she started sucking on my lobes. Then she got up and went to...Read On

Added: 29 Jan 2016 | Category: Crossdressing | Avg Score: 4.83 | Words: 2,937 | Tags: crossdressing  anal  pegging  strap-on  bisexual   | 6 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

allfours

Becoming Chloe - Part 9

Vickie has an 'episode' while out shopping for a bigger cock...

A few weeks later, Chloe was a regular weekend resident in our house. Once I was home on Friday evening, I would shower and shave, and then spend the rest of the weekend as Chloe. This included going out shopping and even the occasional meal out. I'd worked hard on my appearance, and especially on my voice, and now I felt confident that I could pass even close scrutiny by anyone. Of course,...Read On

Added: 25 Jan 2016 | Category: Crossdressing | Avg Score: 4.94 | Words: 2,236 | Tags: crossdressing  bisexual  lesbian  reluctance  toys  cheating  feminisation   | 8 Comments

allfours

Becoming Chloe - Part 8

Chloe goes out on the journey to womanhood

Framed in the doorway was my beautiful wife, wearing four inch heels with fishnet stockings that were attached to a shiny PVC corset. But the thing that really grabbed my attention was the sexy way in which she was firmly stroking the cock jutting between her legs. The look on her face was incredible, and I knew what was going to happen next. Vickie walked over to me, swaying her hips,...Read On

Added: 24 Jan 2016 | Category: Crossdressing | Avg Score: 5 | Words: 2,728 | Tags: crossdressing  oral  anal  toys  rimming  transformation   | 5 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: 5 | Words: 3,223 | Tags: crossdressing  anal  blowjob  m2f  friends  college  dorm   | 14 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  

allfours

Becoming Chloe - Part 7

Vickie and Chloe go for a ride...

I awoke to find the bed next to me empty. Disorientated, I turned over and dozed until I'm awakened by the smell of coffee and Vickie walking through the door with breakfast. All she's wearing is her thin bathrobe, through which her full breasts and nipples are clearly visible. Her hair is dishevelled and she has the most wonderful smile on her face. She looks adorable. "I thought you...Read On

Added: 16 Jan 2016 | Category: Crossdressing | Avg Score: 5 | Words: 2,992 | Tags: crossdressing  oral  anal  toys  public  feminisation     | 10 Comments

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

allfours

Becoming Chloe - Part 6

Friday night - part two: A dream comes true.

My hands trembled as I slipped on my new stockings, and it took me all my concentration to attach them to the suspenders that hung from my waspie. Of course, all this was made the more difficult because of the stunning new 38B's I'd just acquired, and I had to stop myself from keeping my hands off them, plus, they were slightly in the way as I bent down to attach the stockings. Calm down,...Read On

Added: 13 Jan 2016 | Category: Crossdressing | Avg Score: 4.95 | Words: 2,744 | Tags: crossdressing  anal  toys  feminisation  pegging  orgasm  fulfilment   | 5 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   | 15 Comments

allfours

Becoming Chloe - Part 5

Friday night - part one

I got home, tired and cold from work, only to find Vickie already there. That in itself was unusual, because she normally didn't get home until after me. Before I'd even taken my coat off, she greeted me with a really passionate kiss, then turned me round and pushed me back through the front door. "Where are we going?" I asked, but she just gave me a big, mischievous grin. "Out." We got...Read On

Added: 06 Jan 2016 | Category: Crossdressing | Avg Score: 5 | Words: 2,541 | Tags: crossdressing  bicuriosity  shopping  lingerie  toys  strap-on  embarrassment   | 6 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   | 5 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

allfours

Becoming Chloe - Part 4

Vickie reveals her past...

On Sunday, I was awake first. Eager not to disturb Vickie, I snuck to the bathroom to empty my rather full bladder. The chemise felt so natural that it was almost instinctively that I sat down to pee instead of my usual standing up. After I'd wiped myself dry (another first!), I crept downstairs and made us both coffee. The curtains were all closed, so I felt comfortable wearing lingerie...Read On

Added: 30 Dec 2015 | Category: Crossdressing | Avg Score: 5 | Words: 1,901 | Tags: crossdressing  straight  bisexual  ff  feminization  teasing   | 6 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