Crossdressing

cdbottom2

Telling Mom I'm A Crossdresser part 13.5: Missy Brings Home A Stud

the continuation to Missy going out and finding a man.

I told Thomas all the details of why I was out this night and he loved the idea. He took one of his Viagra and he led me out of the bar. I felt a little embarrassed at all the cum leaking down but some of the cross dressers were just smiling at me like they were saying “you go gurl!” which made me a little proud. Thomas followed me in his car until we got to my place and I took him by the...Read On

Added: 14 Jul 2012 | Category: Crossdressing | Avg Score: 4.09 | Words: 2,630 | Tags: crossdressing  bisexual  cream pie  anal  bedroom hopping   | 1 Comment

cdbottom2

Telling Mom I'm A Crossdresser part 13: Missy's Turn

here is part 13 part 13.5 will be up ASAP Plz enjoy and comment and rate at the bottom :)

Sorry not much sex in this one but its a lead up to 13.5 and I hope you enjoy both of them. :) Once mom and I had gotten our car back, we took it out for a spin and I have to say it worked and looked like new. It had everything from a new paint job to new parts in the engine. Now in all honesty, I did have to go back a few times and give Ray a few blowjobs to help pay for them but it...Read On

Added: 13 Jul 2012 | Category: Crossdressing | Avg Score: 4.25 | Words: 2,421 | Tags: crossdressing  oral sex  bar  blow up doll  milf. lesbian practice   | 2 Comments

MistressCheyenne

CD Domina training two slaves

CD Mistress commands two slaves for a hot 3-way.

Just five days had passed since my last session with my slave Candy and already I was yearning for his sexy body again. I was in need of another meeting and had something special planned for it. I called Candy's phone and just like previously he answered before it could ring twice and greeted me anxiously. "Hello Mistress Cheyenne," Candy said as he answered his phone. "Hello slave Candy,"...Read On

Added: 12 Jul 2012 | Category: Crossdressing | Avg Score: 4.83 | Words: 2,719 | Tags: crossdresser  mistress  bdsm  anal  threesome  oral  rimming   | 3 Comments

cdbottom2

Telling Mom I'm A Crossdresser Part 12: Tow Truck Driver's Big Score

Missy gets her car towed and makes a deal with the tow truck driver

Sorry it has been so long since my last story. I have been busy with alot of things and I thank you for your patience. Lately, I’ve been working part time at a restaurant to make a little extra cash on the side along with my nights as Missy. I was saving up for a cruise I wanted to go on that I heard was for like minded people such as Missy. When people ask me about what I want to do...Read On

Added: 10 Jul 2012 | Category: Crossdressing | Avg Score: 5 | Words: 2,473 | Tags: anal  crossdressing  tow truck driver     | 3 Comments

subguy

Fun on Business Trip (part 1)

This is a account of real-life events. -------------------- After the first couple of outings at the mall, I lost some of the nervousness around shopping fem clothes and started actually enjoying it. So much so, that over next two-three weeks, I visited many more stores and ended up buying nearly a dozen skirts, bra and sexy panties. I had begun to get a hang of interacting with the...Read On

Added: 09 Jul 2012 | Category: Crossdressing | Avg Score: 4.75 | Words: 2,420 | Tags: nosex   | 10 Comments

skipspence

A trip from his Hotel Room - Part One

Paul likes dressing up on his business trips, but this time it goes a little further.

As Paul did when he made every business trip to the big city, once he had checked in to his hotel room, he quietly made his way to the streets where there was a profileration of sex shops. He wanted to find the sexiest, sluttiest clothes that he could change back into when he returned to the hotel, and maybe a toy or two to enhance the stimulation. First up was some lingerie – definitely...Read On

Added: 04 Jul 2012 | Category: Crossdressing | Avg Score: 4.63 | Words: 680 | Tags: crossdressing  gay     | 13 Comments

MistressCheyenne

CD Mistress Cheyenne can't fight the craving for Candy

CD Mistress Cheyenne's kinky side comes out in the second meeting with new slave Candy.

Almost two long weeks had passed since my first meeting with my new slave Candy. Our first encounter was special and my sexy new sub had not left my mind since he walked out of my door. His juicy ass and hard thick cock have filled my thoughts each day since. I had found myself wildly attracted to Candy and lusting for him constantly. After deciding that ten days was long enough to make him...Read On

Added: 04 Jul 2012 | Category: Crossdressing | Avg Score: 4.88 | Words: 3,103 | Tags: bdsm  mistress  domme  slave  anal  oral  crossdresser   | 4 Comments

CindyUSA

Cindy's makeover

This is a account of my makeover and my three days in London, not a lot of explicted sex in the stor

I would like to share my latest cross-dressing experience. Like many cross-dressers, I dress up part-time. I am married and my wife does not know of my fetish of warning woman clothing. My dressing need stems from my enjoyment to the attention I received from admires. I am new at this cross-dressing having only started dressing five years ago. Many cross-dressers started their fetish when...Read On

Added: 03 Jul 2012 | Category: Crossdressing | Avg Score: 4.75 | Words: 3,129 | Tags: makeover  glamour shoot  sweet wednesday     | 6 Comments

jimymac

Date with my wife - her story

Today started like any other day, except for one thing. My husband informed me as he brought me morning coffee, "Sweetheart, tonight when you come home, go straight upstairs, cleanup and put on the outfit I have laid out on the bed." He said this with a grin on his face. You know that grin like the one you see on a child's face as you enter the candy store. "But what if I need something?"...Read On

Added: 03 Jul 2012 | Category: Crossdressing | Avg Score: 4.79 | Words: 1,768 | Tags: lingerie  strap on   | 10 Comments

kinkychrissy

Caught

Based on true events....

A couple of years ago I had a girlfriend named Sara, we met at work and were starting to have a great relationship. In the bed things started to get interesting and we got more and more kinkier ever time. We would tie each other up and and play with each other. Then we started using chains and gags and having a great time. Now, she has always had bisexual tendencies but at the time I...Read On

Added: 02 Jul 2012 | Category: Crossdressing | Avg Score: 4.56 | Words: 912 | Tags: crossdressing  bdsm  fetish  high heels  bisexual   | 13 Comments

DeedraCd

The Change Up - Part 3

Deedra continues to have fun on her first date, and gets what she been hoping for!

Sammy looks at us and says, "You know that Elsie gets pissed when you tie up the ladies room like that. Then Trish came back and saw that you were all gone and wanted to know why you didn't invite her along?" Emily says, "You know Trish is working, and it's too early for Elsie to be at the club." The band started to play swing music. I remember the song, Jumping Jack. I danced to it...Read On

Added: 02 Jul 2012 | Category: Crossdressing | Avg Score: 4.96 | Words: 4,417 | Tags: crossdressing  dancing  teasing  hermaphrodite  oral  rim job  anal   | 13 Comments

kinkychrissy

A Fantasy

This is something that I’ve always dreamed would happen…

I have been dressing in women’sclothes since I was little. My grandmother used to dress me up in her old dresses and pretend I was her granddaughter. As I grew older it started becoming more of a sexual fascination and turn on for me. I have been more a closet cross dresser getting clothes here and there and then dressing up and having incredible masturbation sessions looking at tranny...Read On

Added: 29 Jun 2012 | Category: Crossdressing | Avg Score: 4.83 | Words: 1,301 | Tags: crossdressing  lingerie  high heels  ex girlfriend  bondage  fetish   | 8 Comments

MistressCheyenne

Crossdressing Domina gets a new slave

A new slave drives a crossdressing Mistress wild.

I have been a crossdressing Mistress for several years now. I have a petite body and always looked good in a dress. I take on many slaves but my favorites are other men who look great in dress. This is a story about my favorite slave I have ever trained. I had been anticipating the arrival of my new toy all week, and he was moments away. My new slave, eager to be trained under my heels....Read On

Added: 29 Jun 2012 | Category: Crossdressing | Avg Score: 4.7 | Words: 4,091 | Tags: slave  crossdresser  tranny  bdsm  domination  anal  oral   | 4 Comments

jimymac

Date with my wife

It started with my love of sexy lingerie. I planned a date with my wife. She was to come home from work and go up stairs to clean up. Once all cleaned up she was to put on the outfit I laid out. She had lots of questions that I wasn't answering. She wasn't to come into the rest of the house until she was dressed. Well my day started by going to the store shopping for dinner and an outfit....Read On

Added: 24 Jun 2012 | Category: Crossdressing | Avg Score: 4.88 | Words: 1,165 | Tags: wife  role playing  crossdressing   | 7 Comments

cdbottom2

Telling Mom I'm A Crossdresser Part 11: Girl time

sorry it took so long and that its a bit longer then my last one but I hope you enjoy. com at bottom

Part 11 It had been a while since my last time as Missy. I had been doing some jobs for people, nothing special mostly working on decks and mowing lawns for neighbors to not only keep up appearances so as to not give to much suspicion of where my money was coming from. This continued for what seemed like 2 weeks before and started to wonder if my fun as Missy had ended. I walked in the door...Read On

Added: 12 Jun 2012 | Category: Crossdressing | Avg Score: 4.79 | Words: 4,640 | Tags: anal  group sex  lesbian  toys  bisexual  milf  oral sex   | 8 Comments

DeedraCd

The Change Up - Part 2

Deedra has her first date out and meets new friends

I watch Emily get into her car and drive away. My mind just can’t believe what just happen. The clock on the wall says 5:00 oh my. I only have four hours to get ready. I am opening the packages that Emily drop off for me, the dress looks utterly gorgeous, lace and beading should be outstanding on me. Next the shoe box, the phone rings, looking at the caller id it's from India . I snap back...Read On

Added: 10 Jun 2012 | Category: Crossdressing | Avg Score: 4.92 | Words: 3,702 | Tags: cross-dressing  first time out  teasing  3-way  oral sex  cum swapping   | 9 Comments

shazstoned

The Note

I awoke, sorry came to the following morning, still had on my tiny red skirt, blouse, nails and all my make up. I walked into the bathroom and looked in the mirror, OMG what a sight looked back. My make up was smeared over my face and a thick dried string of cum was visible on my cheek. I went back to the bedroom and grabbed my handbag, opened it and took out a cigarette, lit it and inhaled...Read On

Added: 04 Jun 2012 | Category: Crossdressing | Avg Score: 4.67 | Words: 704 | Tags: follow up  morning after  chatting     | 6 Comments

DreamingofStrapon

My Dream story Part 2

My mistress gives me everything I can handle.

"So you like this huh?" All I could do was stare.. "Y...yes Sarah" She walked over to me and slapped my ass hard. "Don't you dare call me that. From now on you will call me Mistress and you will be my little sissy slut. Got it?" "Yes Mistress. Sorry Mistress." I said. The feeling of my ass being slapped had instantly made me hers. I could feel my clitty strain against the...Read On

Added: 03 Jun 2012 | Category: Crossdressing | Avg Score: 4.74 | Words: 754 | Tags: crossdressing  anal  milf  strapon   | 11 Comments

DreamingofStrapon

My Dream story Part 1

My first story, be nice! Just a start to this story line.

My name is John, and this is my dream. I am 18 years old, I have dressed before but never seriously, and down the street from me lives a woman named Sarah. She is the mother of a very wealthy family and just radiates control and success. Ever since I had seen her, this story has played over and over again in my mind. So here it is. I woke up and the weather couldn't have been nicer. The sun...Read On

Added: 02 Jun 2012 | Category: Crossdressing | Avg Score: 4.67 | Words: 631 | Tags: crossdressing  milf  strapon   | 12 Comments

cdhaley

Surprise Delight

It was a beautiful day outside and it had been a long hard week at work. I decided to pamper myself by taking a nice long bath and just soak my sore muscles. After my bath and weekly grooming I decide it was time to slip into something a bit more slutty to wear around the house (I don't go out dressed up, not quite passable for that step). I walked into my room and looked in my closet, where...Read On

Added: 01 Jun 2012 | Category: Crossdressing | Avg Score: 4.82 | Words: 2,166 | Tags: anal  chatline  surprise  orgasm  trans     | 12 Comments

libertina

A Whole New Me - Part 2

Lisa finds out what I've been up to

I had just finished cleaning up in the bathroom. A spontaneous encounter with my best friend whilst wearing my girlfriend’s thong had left me a bit of a mess and as for the thong... well I guess I’d need to find something new. Fully cleaned up, I ran naked into our bedroom and started looking through Lisa’s drawers for a new pair of panties. I wasn’t sure how I’d explain my change to her...Read On

Added: 30 May 2012 | Category: Crossdressing | Avg Score: 4.95 | Words: 2,841 | Tags: strapon  anal  crossdressing  panties  bi  bisexual  role reversal   | 7 Comments

cdbottom2

A Master For Julie Jizzbucket

A story i have written in regards to my master and myself

I had spent the last couple months indulging in some mild cross dressing. After a few nights wearing clothes that made me feel so sexy and womanly. Until recently I had only worn panties, bras and a few sets of stockings and teddys that I had bought for an old girlfriend before she broke up with me to date a guy that had more money. I have also been going online to a site called Lush...Read On

Added: 30 May 2012 | Category: Crossdressing | Avg Score: 5 | Words: 3,490 | Tags: anal  exhibitionism  reluctance  toys  spanking  fetish  bdsm   | 2 Comments

libertina

A Whole New Me - Part 1

Borrowed panties and a day with my friend reveal a whole new side to me!

“Honey! Are you around?” I shouted from my room, rummaging through my drawers and naked from the shower. “What’s up, sweetie?” My girlfriend, Lisa, popped her head around the bedroom door. Her eyes taking in my body and a cheeky smile forming on her pretty face “Oh, looking good.” I wasn’t the most muscular guy but I wasn’t fat at all and Lisa always claimed she liked my body not being...Read On

Added: 26 May 2012 | Category: Crossdressing | Avg Score: 4.77 | Words: 1,995 | Tags: panties  bi  bisexual  first time  thong  crossdressing   | 9 Comments

DeedraCd

The Change Up

Sexy outfit gets Deedra some lucky action

Finally a break comes my way. The children are off to college, the wife has to go out of the country for two months on business. I can’t remember the last time we had sex. She used to dress in all types of lingerie for me. It helped me suppress some of my crossdressing desires. That stopped and my crossdressing started to grow again. What an opportunity for me, I can change up and dress...Read On

Added: 25 May 2012 | Category: Crossdressing | Avg Score: 4.93 | Words: 2,317 | Tags: crossdressing  oral  anal  play  hermaphrodite   | 27 Comments

cdbottom2

First Time, First Fuck, New Porn Star

A story I wrote while on a short break from my Missy series. Don't worry, I just need inspiration.

I am just a normal guy however I have what some would call an abnormal fetish. I am a 23 year old guy and I like to wear and dress up as womanly as possible. I am 5’9, a little chubby but can still pass as a woman, with brown hair, brown eyes and a 5 inch cock. One night I had gone out with one of my friends and had gone drinking to a few bars. As we went from place to place we started...Read On

Added: 10 May 2012 | Category: Crossdressing | Avg Score: 4.72 | Words: 3,049 | Tags: anal  reluctance  toys  first time  gay male  crossdressing   | 5 Comments

GemmaCD

Mike's new girlfriend - part 2

The following Monday couldn’t come round soon enough. It had been a long, difficult and very confusing seven days at home, with my wife, Amy. I had been so distant and argumentative with her and I could see how upset she was. However all I could think about was Mike and how much I wanted to be back in his arms and have him make love to me again. Again, the morning started in the usual way....Read On

Added: 09 May 2012 | Category: Crossdressing | Avg Score: 4.84 | Words: 1,765 | Tags: crossdressing  rimming  anal  sissy love     | 13 Comments

sally21

Car Park No 1

My crossdressing dream

The Car Park No 1 The car park has always been a great place for meeting a fellow for a good time. I had been there several times over the years and felt a great satisfaction in satisfying the needs of a horny participant. It has become more of a challenge since the police seem to patrol it more often than in past years. However, I had the opportunity to have a few hours to my self as my...Read On

Added: 04 May 2012 | Category: Crossdressing | Avg Score: 4.5 | Words: 666 | Tags: crossdressing  dream   | 3 Comments

subguy

Shopping outing for lingerie

Fun time buying lingerie

Following is a true account of one of my experiences of shopping for lingerie. (nosex). This happened a couple of months ago, and as far as I remember, the conversation went like I have described below. If you have not read my earlier story 'Wonderful crossdressing shopping experience', I'd suggest reading it first. ------------------------------------------------ Following my...Read On

Added: 21 Apr 2012 | Category: Crossdressing | Avg Score: 4.83 | Words: 2,399 | Tags: nosex  crossdresser     | 6 Comments

gloryhole31

Pumped While Wearing His Pumps

Hitching A Ride with the Lothario of Lingerie

What a place to be stuck! Under a sign that says Coors Road and practically dying of thirst. I was now two-thirds of the way across the United States but perhaps the most difficult portion of my cross-country hitchhiking adventure lay ahead. It is all deserts from there on the outskirts of Albuquerque to the Pacific coast, my ultimate destination. I had left from Maine four days earlier...Read On

Added: 19 Apr 2012 | Category: Crossdressing | Avg Score: 4.71 | Words: 5,376 | Tags: anal  bisexuality  fetishism  exhibitionism   | 1 Comment