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9

Becoming Chloe - Part 18

Chloe goes home and gets a seeing to...

I have no idea how I managed to drive home with my skirt soaking with cum and my cunt full of the plug that Tina had slid into me. The scent of sex filled the car, and the fear of having an accident or having to stop kept me on my toes enough to drive more carefully than I ever had. The spunk on my skirt started to dry as it stuck to my legs, making me a little uncomfortable as I weaved...Read On

15

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

13

Becoming Chloe - Part 17

Chloe starts work, and receives an unexpected bonus...

Two weeks after the agreement between Vickie, Tina and me, I was a different woman. I'd told my parents about my planned transition. As I thought, it wasn't easy, but I felt so much better once it was out of the way. Mum took it fairly well, but I'll never forget the hurt look on my father's face as I explained how I felt, and how I wanted to be a female. Despite that, he still gave me a hug...Read On

6

She Made Me Do It

My package arrived in the post – I just couldn’t wait to open it.

Something inside me just grabbed hold of my male shackles and snapped them in two; discarding them into the depths of depravity. I had been writing stories about crossdressing and transsexuals all week. I had been looking at girly pictures, not the feminine girl ones, the ones that had dicks. Some of them were absolutely gorgeous, far better looking than some women and I wanted to be one of...Read On

10

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

2

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

10

Becoming Chloe - Part 16

Chloe makes her feelings known to Tina

Tina stayed the night, but I couldn't sleep with three of us in the bed, so I got up around two in the morning and went to sleep in the spare room. I didn't mind leaving Vickie and Tina alone together. Besides, I knew I would have to get used to at least a couple of nights a week on my own anyway, and my mind was still in a whirl with everything that was going on. I tossed and turned as...Read On

12

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

23

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

15

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

11

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

11

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

22

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

14

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

11

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

17

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

18

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

24

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

8

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

15

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

6
Recommended Read

The Evolution Of Lee - Part One

A man continues on his journey towards a new life...

The cloudless blue sky above and the crystal clear tropical waters below embraced our plane as it began its descent. As I shifted in my leather seat, I felt my Lola Luna panties slide against my soft, smooth skin, reminding me how wonderful those fabrics felt. After some dark times, I was again excited with whom I was and even more excited with who I was hoping to become. *** As my...Read On

13

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

10

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

22

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?" "Tomorrow," she said...Read On

26

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

19

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

5

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

15

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

14

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

24

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