Crossdressing

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 | 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: 4.9 | Tags: lingerie  strap on   | 2 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: 4.57 | Tags: crossdressing  bdsm  fetish  high heels  bisexual   | 9 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: 5 | Tags: crossdressing  dancing  teasing  hermaphrodite  oral  rim job  anal   | 10 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 | Tags: crossdressing  lingerie  high heels  ex girlfriend  bondage  fetish   | 11 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 | Tags: slave  crossdresser  tranny  bdsm  domination  anal  oral   | 3 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: 4.86 | Tags: wife  role playing  crossdressing   | 8 Comments

irishfella

The slight mix up

New place New underwear Old girlfriend

Let me introduce myself I'm Jake. I'm a 23 year-old man, who recently got a place of my own. I decided to do a little bit of shopping for new underwear because I left mine in my parents home and I only have the pair I'm wearing and also to get some food and drink, for the next week or so. I started with some specials which were right where I entered the store. Soon after that, I grabbed...Read On

Added: 20 Jun 2012 | Category: Crossdressing | Avg Score: 3.94 | Tags: crossdressing  strap-on  anal   | 2 Comments

Cherism

His Dirty Little Secret

His wife finds his stash of clothing, leading to some role reversal

Julia was doing some spring cleaning in the house. She had scrubbed everything, cleaned the oven, scrubbed the floors and was in the process of cleaning out the closets. Stuffed in the back of a closet was a bin. She didn’t know what was in it. The sight that greeted her caused a jumble of emotions in her. The bin was full of women’s clothing. It was all silky and sexy; Nightgowns,...Read On

Added: 19 Jun 2012 | Category: Crossdressing | Avg Score: 5 | Tags: crossdressing  fem dom  dildo  strap on  light bondage  lingerie  male submissive   | 17 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: 4.72 | 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: 4.91 | Tags: cross-dressing  first time out  teasing  3-way  oral sex  cum swapping   | 8 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: 4.65 | Tags: follow up  morning after  chatting     | 5 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: 4.69 | 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: 4.65 | Tags: crossdressing  milf  strapon   | 13 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: 4.83 | Tags: anal  chatline  surprise  orgasm  trans     | 7 Comments