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Crossdressing

Our crossdressing (cross-dressing) stories feature tales of either gender (usually male) dressing up in the clothes of the opposite sex, for reasons of sexual gratification. Crossdressers are akin to the transvestic fetishism, which is a sexual fetish for the clothing of the opposite gender. The crossdresser can be of any sexual orientation.

20

House Sitting for the Holidays

A favor for a friend turns into a sissy adventure.

My friend Teresa was planning her summer holidays but was beginning to stress about leaving her home unattended for such a long time. She lived with her husband in a large house in the middle of nowhere and the two of them were planning a cruise, which meant the house would be left empty for the next eight weeks. She invited me over for lunch and after the meal, we sat down in the front...Read On

5

Stage Ten Of My Journey To Becoming Joann

Nearing the end of the journey to becoming a full time cross-dresser...

I was excited about the next soccer practice. There were no guys at the last practice due to Gurls Night. I was hoping Donny would be there this week. I stopped working at 4:00 so I would have enough to time to get ready.   I went into the bathroom and filled my douche bag with a little over two quarts of warm water and special soap. I took off my shorts and panties before pushing the...Read On

5

My Adventure into Crossdressing Part 2

The deeper Ron gets involved, the better he likes it

I left the car at the end of the driveway, letting Carol get out of the garage without all the fancy maneuvering. The front door was open, and when I walked by the rec room door, I saw my wife on her knees in front of the couch. Her head was bobbing rhythmically, and the look on Andy's face told me he was enjoying her mouth immensely. I was jealous either because I wanted to do that to him or...Read On

8

My Neighbor's Wife Pt. 2

I've never been so humiliated, but was loving every minute.

Suddenly, I was awake. Or was I just dreaming? It was hard to tell. Then I tried to move but couldn't. I could feel that what I was wearing when I last conscious, had been removed. I was naked, except...  The last thing I remember was being face down and Carol on top of me steadily fucking my ass, somewhere in all that pleasure and pain, I must have either past out or have withdrawn inward....Read On

5

Stage nine of my journey to becoming Joann

Moving into the last stages of becoming a complete cross-dresser

It was almost midnight when I got home from my foursome. When I walked into the house Mandy was sitting on the couch watching the television wearing a shear teddy with nothing underneath. She looked at me and said, “Where have you been all night young lady?”   I answered, “Out with the boys, Sis.”   “I hope you don’t mean what that sounds like.”   I responded, “If it sounds like I had...Read On

16
gerry15
online

Practice Pays Off

First time out in public dressed as a woman.

It was a beautiful Saturday late afternoon. I was done with all the things I had to do around the house. My wife was gone for the weekend and I was feeling a bit bored. I thought I would take a shower, shave and pull out the makeup and see if I could do myself any justice in looking passable. Many attempts before had failed, but I was getting a little better each time. I got out of the...Read On

10

My First Time Out On The Town All Dolled Up

I learn about a sex club in Los Angeles and attend, with delightful results.

It was Christmas time but still warm in Los Angeles.  I was living in West LA and heard about a club called Club Sex Addict in the valley, a haven for crossdressers.  I had a fairly extensive warddrobe that I bought in a Culver City lingerie shop.  I just bit the bullet and went there and told the girl who worked there that I was a CD and she would help my pick out sexy slutty stuff to wear....Read On

9

Jack Has A Secret.

Jill's fuck friend has a little secret.

“When is he due back?” “Who?” Audrey gave Jill a look. “Oh, you mean Jack? Not sure actually.” “I call that bullshit. You know exactly when he will be back.” Jill smiled dreamily . “Yeah, tomorrow at 8.15pm.” “And by 9.30pm you will have his cock deep inside you?” “Hopefully.” “How long has he been gone?” “Three months almost, hiking in South America with his other macho friends.”...Read On

8

Getting More Than I Went For

I went to the mall to get one thing and came away with a lot more than I could have ever imagined.

Recently I have started looking online for woman’s clothes that I could wear incognito. I am on the larger size so I was searching plus size stores when I found something on one of the websites. It was a black lace bandeau which seems to be a bra-like garment that you can wear without straps. It seemed very sexy and I thought, perfect, no straps and it should be tight enough that no one...Read On

7

Stage eight of my journey to becoming Joann

Big steps as a cross dresser

After returning home from dropping Mom and Dave off at the airport, I immediately jumped in the bathtub and took a long bubble bath. While I was in the bathtub, I shaved the stubble that was starting to form from days of neglect. When I finished my bath, I rubbed most of my body with a good lotion to restore its smoothness, followed by a badly needed pair of sexy red lace bikini panties with...Read On

19

My Adventure Into Crossdressing

Ron finds out he likes more than just crossdressing

I finished my shower and toweled myself. I didn't put anything on because my wife was on a business trip, so nobody was home. On my way to my chest of drawers, I walked by her dresser. I stopped and opened her underwear drawer. There before me was a selection of sexy panties. A lot of them bikini, some opaque, some see-through, some thongs and the best of all, a pair of red crotchless...Read On

12

Turning into a Middle Age Slut - Part 1

Once I go fem, there is no turning back.

I have had the crossdressing bug for many years and have collected some items to fully dress with, such as a wig, makeup, fake boobs and all that makes me look as fem looking as possible. Being in my mid fifties however, there was really no way that I was going to be truly passable or that hot, so I thought  Over the years, I collected my lingerie, heels, wigs and experimented with makeup. ...Read On

18

Getting A Grip On The Situation. The Conclusion.

"You OK, son?" Dad asked Van as he saw him shift constantly in his kitchen chair. "Yeah, Pops, I'm fine, just a little sore. Went to the BMX park and for a couple of hours and then a group of us raced through the woods," Van responded. "You need to slow down. That's too much abuse on your body for one day, " his parent responded knowingly. 'If you only knew,' Van said to himself before...Read On

11

Getting A Grip On The Situation. Part 3.

Ken was sent home in plenty of time so Vanessa could become Van again. Van thought about the morning events as he stepped in the shower to remove his makeup and continued thinking when he returned to his room and carefully hid Vanessa's clothing and makeup. This long and laborious process was necessary as discovery by his parents would be disastrous for him. Still wrapped in a towel he...Read On

13

Getting A Grip On The Situation. Part 2

Ken felt himself being shaken and heard a voice urging him to wake up. When he opened his eyes he didn't know where he was for a second until he turned his head and saw Vanessa next to him. "Hey babe, you've got to get up and moving. It's getting late and my parents will be home," she said softly. Ken was out of bed like a shot and quickly redressed. He must have been so deeply asleep that...Read On

18

Getting A Grip On The Situation.

As our story opens we find sixteen-year-old Ken almost naked and laying at Vanessa's side enjoying the slow descent from his orgasmic high. The wonderful feeling is made even better by the fact that Vanessa's body is pressed against him and one of her satiny smooth legs is on top of his leg. He smiles to himself as he glances over at her and recalls her asking him not to tell anyone. It...Read On

6

Hard #2

An unsual situation.

Well, that didn't work out well.  I mean, we're fine at work, but once again, you're all proven right.  I accept what's been said and that I deserve anything else you have to say about me.  Well, maybe not anything, Azalea.  Remember to keep some thoughts to yourself, my love. In unrelated news, I've been wearing pants the last few days.  It's weird, but ultimately okay.  I get that...Read On

5

Stage six of my journey to becoming Joann

A defining year in becoming a complete cross-dresser.

As I awoke on Christmas morning I found three presents on the end of my bed. There were handwritten tags on each with the message: open in private. There was no doubt in my mind as I opened them that they were from Sis. The first was a body shirt that pulled down and snapped in the crotch. It was white with a v-neck trimmed with lace around the neck and sleeves. The second was a set of...Read On

23

My Own Story

A story about how I started crossdressing with a bit of a fantasy encounter

I have been into pantyhose for as long as I remember. I am not sure why I love them so much, but I can't seem to get enough, especially how beautiful women's legs look when they are wearing them. When I was sixteen I remember playing around my mothers nylon covered legs when she came home from work. She would always wear very sheer hose and had wonderful legs. During the summers when she...Read On

11

Stage five of my journey to becoming Joann

Enjoying myself feeling like a women

As I opened my eyes it was quite light. I sensed it was late morning. Bob was still spooning me, but his dick was soft and must have pulled out of my ass sometime through the night. I quietly rolled out of the bed and walked to the bathroom. Before sitting to pee, I reached around and pulled another condom from my ass. I guess when he lets his dick soften inside me it shrinks from the...Read On

12

Girly Obsessions

Based on a real adventure with embellishments of wishes

All of my life from the time I was young to now at twenty-five, I have had an obsession with women. It is not that I like them (which I most certainly do) but more that I want to be like them, act like them, and most importantly dress like them. It started when I was very young and developed an interest in the legs and nylons of women which I found fascinating. The sheer and soft material...Read On

6

Frank

A crossdresser tries to please his lover

Frank didn’t vocalize his orgasms. So I never knew he’d cum until he stopped his motion and pulled out of me. Then I’d look over my shoulder with a smile and ask, “Did you cum?” And Frank, already backing off the bed, his big cock curving downward now, would reply, “Yeah.” Although normally quite chatty, in the immediate aftermath of sex Frank turned into a man of few words, a regular...Read On

7

A Sissy's First Dildo Experience

After ordering his/her very first dildo, this sissy had a very, very special experience.

Buying a dildo online was a bit nerve-wracking, honestly. Not for any huge reason or anything – I live alone, and the packaging is supposed to be discreet anyway, but there’s just something that made me nervous when I first put in the order. Sure enough, it wasn’t like it was a fat box labeled, “Tasty Black Dildos for Sissy Whores,” all around it; just a plain box, inside which was some...Read On

5

For Mistress Sarafina (Part One)

A submissive feminized sissy serves her Mistress

Alice was clad in a tight pair of black lace silken panties that felt so smooth upon her caged genitals. This pair of panties, more so than any other pair Alice owned sent aroused shivers up and down her whole body whenever she was made to wear them by her Mistress.   Mistress Sarafina had left Alice a detailed text message earlier in the day explaining what Mistress Sarafina expected...Read On

10

A boy's femininity awakened, Part two - early girlhood

A sissy boy's experiences, good and bad, as a girl

Sissy boy John was petticoated at Secondary School after falling foul of Jenny Tough, a school bully. During his week of penance, John found that he was more at ease and happier amongst girls than with boys. John decided, therefore, to explore his feminine side by trying to live as a girl. John’s Mum was shocked when he first arrived at home wearing a schoolgirl’s uniform but calmly listened...Read On

9

A boy's femininity awakened, Part one

A sissy boy is petticoat disciplined in school and discovers his feminine side.

In the North East of Scotland, large families were the norm even up into the 1950s.  So, when I attended the local Primary School, there were scores of children of my age there, all shapes, sizes, and temperaments. This meld of kids meant that I didn’t stand out from the crowd despite being a softy. My time at Primary School was therefore quite comfortable and peaceful, but this...Read On

2

Bobbie Breaks

Bobbie submits to Joe's discipline.

Our routine continued for the rest of the time Amy was away on business. I would ask for money, and Joe would usually unbuckle his pants without a word. I’d give him a blowjob, and he’d give me some cash. I enjoyed it because it was the only time I was allowed to take my bra off. I channeled my frustration at having my girls locked away into being the biggest thot I could. He didn’t want to...Read On

12

Under His Thumb

A submissive college student submits to his alpha male roommate.

I was sitting at my desk in a t-shirt and running shorts when my roommate Dave came in. He saw the towel I’d dropped on the floor, and immediately his nostrils flared. “How many times have I told you to hang up your towel?” he said as he bent over to pick it up. He hung it on a hook on my closet door. I looked back at him and rolled my eyes. “You’re so anal,” I said, turning back to...Read On

22

Stage Two Of My Journey To Becoming Joann

Falling further into the journey of cross-dressing

Life was becoming a little confusing. I was out of high school and attending the local community college part-time at night while I worked at the machine shop during the day. I played soccer on the college team in the inter-county conference. Mom helped me buy a nice used car. Still, I wore panties, a bra, and nightshirt to bed every night. Sis was working part-time at a hairdresser while...Read On

22

His First Time In A Dress

Andy visits a very kinky club

The next morning, Andrew woke up to find a text from Emily on his phone. “Come over at 11,” it read.  “Gr8 idea 4 2nite.” That sounded intriguing, he thought. He showered, made himself some breakfast, then ambled over to Cavendish Hall. When he got to Emily’s room, Calum was already there, sitting with his feet on the table and nursing a cup of coffee. “Hey, Andy,” he said with a wave....Read On