Crossdressing

sarahricegirl

576 Shadow Oak Drive - Part 2

Sarah and Molly arrive at the party and Sarah has another first experience.

As Molly drove down the highway, I sat in the passenger seat. Although I had always had a feminine side, I was experiencing all kinds of new emotions and feelings that I hadn't felt before when dressed. I don't know exactly what brought it out. Maybe it was the love and support of Molly. Maybe it was seeing myself truly dolled-up for the first time, seeing my own cleavage, having my manhood...Read On

Added: 19 Jun 2016 | Category: Crossdressing | Avg Score: 4.93 | Words: 5,435 | Tags: crossdressing  femdom  first time  oral  anal  party  sex party   | 4 Comments

Nadia5831

Finally Pregnant

My wife finally inpregnates me

It was a lazy Sunday morning. My wife and I were sleeping in a little. As I went to bed last night, like I do most nights, I put on my sexiest female lingerie. I chose a tight little corset number that has garters attached. It was bright red so I also chose red panties and black stockings. I tightened up the waist to give me a more curvy figure. To fill out the bra cups, I chose some 3XL...Read On

Added: 17 Jun 2016 | Category: Crossdressing | Avg Score: 4.38 | Words: 1,397 | Tags: role play  gender reversal   | 5 Comments

sarahricegirl

576 Shadow Oak Drive - Part 1

Sam meets Molly

I met Molly on a seemingly random day. How could I ever have known she would change me forever? It was late April and I was working behind the cash register of a local department store. I was eighteen, just out of high school, and didn't have any sort of plan for my future. I figured that I would take a least a year off before applying to any universities. I liked working at the...Read On

Added: 14 Jun 2016 | Category: Crossdressing | Avg Score: 4.68 | Words: 2,703 | Tags: crossdressing  femdom  lingerie  sex  first time   | 10 Comments

crevels

Being Christy - Part 2

Caught by the neighbour!

To be honest, I was panicking. From the outside I looked like an average teenager. Skinny black jeans. Indie band tee, maybe a size too small on my Bowie-thin frame. Cherry red Converse high tops. Straight dark hair cut into a fashionable (if you were an NME reading indie-kid) boy bob. But underneath I was sporting skimpy black panties and stockings and suspenders, all ‘borrowed’ from...Read On

Added: 28 May 2016 | Category: Crossdressing | Avg Score: 4.95 | Words: 3,932 | Tags: crossdressing  oral   | 7 Comments

ctvictoryrider

First Time Bareback

The first time I let my boyfriend fuck me bareback

I have written an earlier story about the first time my boyfriend Mike and I fucked. After our first encounter, I couldn't get enough of Mike and his cock. We went from meeting every other week to him spending some weekends at my house with me dressed the entire time. As we got to know each other better, we started to discuss our sexual histories and some of our fantasies. I could tell Mike...Read On

Added: 27 May 2016 | Category: Crossdressing | Avg Score: 4.86 | Words: 1,874 | Tags: boyfriend   | 12 Comments

ThePhantom

A friend with something extra. Part 4

Grant dresses Ian for the first time.

Ian woke up around 9:00 AM and headed to the bathroom where he found his clothes hanging on the doorknob. After dressing he headed to the kitchen where he found Grant drinking coffee. He looked like he normally did, there was no trace of the sexy stunning female that Ian had sex with last night. Where's the girl?" Ian asked pouring a cup. "She's gone for now, but she'll be back,"...Read On

Added: 25 May 2016 | Category: Crossdressing | Avg Score: 4.57 | Words: 1,113 | Tags: memories  desire  mastrubation   | 3 Comments

ThePhantom

A Friend With Something Extra.Part 3

Grant collapsed on carpeted floor of the living room. The ropes of semen his friend shot on his chest were beginning to crawl down to his bra. The ones on his bra were slowly moving down toward his belly. His tiny silky bikini panties were filled with his own cum as the sight of his friend's cock shooting on him had gotten him off. He looked up at Ian who was still sitting on the couch with...Read On

Added: 21 May 2016 | Category: Crossdressing | Avg Score: 4.88 | Words: 1,212 | Tags: bedroom  nightgown  anal     | 7 Comments

ThePhantom

A friend with something extra.Part 2

Ian and Grant test the waters.

Ian headed to the bathroom to clean up. As he did he allowed his mind to recall the most recent events of the evening. He arrived at his best friends house for one of their pizza and movie nights and discovers a sexy girl in his buddy's bedroom. He soon discovered that the sexy girl was, in reality, his friend Grant. He didn't look or talk like the Grant he knew, he talked and looked like...Read On

Added: 18 May 2016 | Category: Crossdressing | Avg Score: 4.77 | Words: 880 | Tags: night gown  nylons  heels  experimination.   | 4 Comments

ThePhantom

A friend with something extra.

Ian makes a discovery about his boyhood friend.

So here Ian was standing in the doorway to his buddy's room and staring at this drop dead hottie clad in silk, lace and heels that he found inside. It was just a typical Friday and he'd dropped over his friend's house for a pizza and movie night. It was a rotating event for them on Fridays. They didn't have their own cars as of yet and had no desire to walk to the mall and hang out....Read On

Added: 15 May 2016 | Category: Crossdressing | Avg Score: 4.8 | Words: 1,238 | Tags: cross dress  bedroom  humping  first time   | 9 Comments

Dividence

The Wedding Proposal, chapter VIII

An apology is needed, but how will we end up? Lonely? Pals? Friends? Friends with benefits? Lovers?

I was beginning to get used to this now. My heart had stopped racing when I ventured out the door. I did not examine every approaching face for signs of suspicion, or spend all my concentration on every little detail a women would do unconsciously. I walked onto the bus as a free and independent woman. Never questioning my right to be there. A text message arrived as I watched rows and...Read On

Added: 13 May 2016 | Category: Crossdressing | Avg Score: 5 | Words: 2,176 | Tags: crossdressing  transvestite  ts  public  love  friends  romance   | 2 Comments

ctvictoryrider

First Love

Crossdressers first love

This is the story of the first time my first boyfriend and I fucked. Before I get started I should give you some background information about myself. I had always considered myself straight and had been happily married for fifteen years before my wife and I drifted apart and divorced. While we were married I had wondered what wearing some of her heels would be like. Unfortunately my feet were...Read On

Added: 11 May 2016 | Category: Crossdressing | Avg Score: 4.94 | Words: 2,552 | Tags: crossdressing  anal   | 7 Comments

crevels

Being Christy - Part 1

Part truth, part fantasy. My story begins

The summer before I went to university was hot. Really hot. It barely rained for weeks and when it did, it came down in torrential downpours. The air would get heavy during the course of the hot humid mornings and by lunchtime the clouds would darken and you could feel that it was going to be getting very wet, very soon. The day I first met Jenny and James I’d been into town in the morning,...Read On

Added: 09 May 2016 | Category: Crossdressing | Avg Score: 4.67 | Words: 1,729 | Tags: cross-dressing  awakening  solo-masturbation   | 5 Comments

jerrixdresser

My 2 AM Phone Call (Part Two)

I became a perfect motel whore that night.

My day started around 2:00 a.m. with a phone call from a Black man I knew from an intense relationship that started in a video store theater several years before. After using me as he pleased for several months, he suddenly dropped me and just vanished until this morning when he called and gave me very specific instructions where to come, what to wear and when to arrive. That is why I...Read On

Added: 28 Apr 2016 | Category: Crossdressing | Avg Score: 5 | Words: 1,916 | Tags: motel sex  anal  forced sex  group sex   | 1 Comment

rushman1uk

Office - Caught 2

I couldn't focus, my head was racing with all kind of thoughts. I had no idea what this would result in. My manager and teammate noticed something was wrong. I just told them I was coming down with something and felt ill. As there was only about an hour before closing time, my boss told be to finish early and get myself home, dosed up and to recuperate over the weekend. I didn't need to...Read On

Added: 07 Apr 2016 | Category: Crossdressing | Avg Score: 4.83 | Words: 1,142 | Tags: office  colleague  tights  crossdressing   | 13 Comments

Dividence

The Wedding Proposal, chapter VII

No sex. No eroticism. Just a good, old intermission.

I did not speak with Tony after that. Tina sent me a few messages, though I do not remember giving her my number. She was still in town and kept nagging me about meeting her again. I tried to refuse, although I lacked any convincing arguments. Even though I was a bit down about my row with Tony, I tried to go on as usual. The following Monday, after a night of constantly interrupted sleep,...Read On

Added: 06 Apr 2016 | Category: Crossdressing | Avg Score: 4.67 | Words: 1,056 | Tags: crossdressing  friends  emotion  

rushman1uk

Office - Caught

Guy gets caught by work colleague wearing tights

My name is Peter. I'm twenty three and I'm a member of the small internal IT team at a large corporation. It's a typical office setup and our small team of three were kept busy with the day to day tasks; failures, PCs and printers and general support. I'm generally pretty quiet and unassuming and, whilst polite and good at small talk, I'm pretty shy, so just keep my head down and do my job....Read On

Added: 05 Apr 2016 | Category: Crossdressing | Avg Score: 4.71 | Words: 1,098 | Tags: office  colleague  tights  crossdressing   | 8 Comments

ThePhantom

The Magician's Assistant Or How It began. The Conclusion.

The Halloween show they performed seemed to open the floodgates of bookings.The demand for his shows grew and soon they were working almost every weekend instead of every other one. Carl was forced to find a new headquarters for his magic workshop as his equipment began to overcrowd his garage. With Ken's business contacts he located a vacant factory that was only a few years old for a...Read On

Added: 27 Mar 2016 | Category: Crossdressing | Avg Score: 4.67 | Words: 1,380 | Tags: experimenting  revealing  confession  top hat  cape  wand   | 4 Comments

ThePhantom

The Magician's Assistant or How it began. Part 2

Ken's life changed dramatically since under going the transformation at Mistress Elaine's. His time at the gym was spent doing high reps with low weights, concentrating on his legs and rear. He added a lot of cardio and crunches and this gave him lean muscle mass rather than bulk. As a result his whole body took on a toned and sculpted look. He worked on his makeup almost every night and...Read On

Added: 20 Mar 2016 | Category: Crossdressing | Avg Score: 5 | Words: 1,397 | Tags: dress  attraction  kissing  blowjob  anal   | 7 Comments

ThePhantom

The Magician's Assistant or How it began - Part 1

Ken had led a pretty normal life until the year his longtime friend needed an assistant for his growing magic act. Magic had always been a hobby with his buddy Carl and he spent many a day watching him perform a new trick in his garage seeing if he could detect the secret. Their being forced to take woodworking classes in high school really paid off when Carl expanded into the realm of...Read On

Added: 16 Mar 2016 | Category: Crossdressing | Avg Score: 4.8 | Words: 1,394 | Tags: magic  equipment  assistant  dressed   | 8 Comments

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: 4.93 | Words: 3,744 | Tags: crossdressing  sissy  first time  slut  anal  blowjob  toys   | 9 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