Crossdressing Stories

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cdbottom2

Telling Mom I'm A Crossdresser Part 3: Missy's Weekend

Part 3 of my Missy series :) enjoy and please rate and comment.

One day while watching T.V, my mother had come in and told me Missy’s services had been requested for the entire weekend and we needed to go shopping. I smiled as we got into the car and went to the store to buy lots more sexy clothing for me to play in. After we had bought all the clothes and makeup needed for the weekend, my mother and I went home so that she could give me the details of...Read On

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cdbottom2

Telling Mom I'm A Crossdresser Part 2: The Adult Store

Missy goes out and meets her first gloryhole. Please comment and rate all of my stories. :)

I awoke the next morning a little groggy as I slowly recalled the events that had taken place last night. I rubbed my body up and down feeling how the latex had now become a little sticky and how my ass and cock were still sore from the pounding I had taken. I read the note again left by my mother and decided to make breakfast as I was for when she arrived. It was just past 9am when I heard...Read On

61

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cdbottom2

Telling Mom I'm A Crossdresser

A story of me being open with my mom as a crossdressing slut andher becoming my pimp. Plz comment :)

When I was younger, my dad had passed away leaving only my mom and I. She is 45 years old with long brown hair, bright green eyes and stood about 5'10" in height. She is also a fairly busty woman with a 30DD chest with about 35" hips and in pretty good shape for a woman her age. I had been crossdressing for a few years and my mother had caught me a few times wearing her clothes. The first...Read On

39

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Jess_cd

A new friend

As I had a nice, big empty house I did what any good 17 year old would do. That first weekend I had a massive house party! I took a night off from dressing up and invited everyone I knew and when it came to the big night there were plenty of people, including a few I didn't know. I chatted to people and made new friends, sharing drinks and having fun. There was one girl there in particular...Read On

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cindytranee

My First Boyfriend Part Five

I step out on my boyfriend and end up getting gangbanged

Things had pretty much gotten back to normal after our wildweekend a week or so before. My boyfriend Steve and I had our unofficial “honeymoon” where I had dressed in a wedding dress and we made love. I had been out dressed as a girl for the first time and had gone to a party where I sucked off a bunch of guys for money. Steve and I had taken two of those guys home with us and they all banged...Read On

33

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libertina

My Girly Fantasy

A night with my friend changes everything between us

I wake up and smile, remembering where I am and who I'm with. I'm warm and comfortable, wrapped in your arms as you sleep. I think back to last night, finally showing you my girly side. We've been best friends for ages but I always had a crush on you. Finally, drunk on wine, I decided to do something about it. I came into the living room we share and straddled you; taking off my robe to...Read On

19

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cindytranee

My First Boyfriend Part Four

I suck off a bunch of guys at a party and take two home to have a foursome

The drive home from the party was quiet because I had sucked off ten guys at the party and my mouth was sore and we were pretty drunk too. Two of his friends were following us home I assumed to have sex and party. I lay on the seat with my head in Steve's lap and rested while we listened to the radio. I asked Steve how were going to keep those two from finding out I wasn’t a real girl and...Read On

21

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cindytranee

My First Boyfriend Part Three

My boyfriend pimps me out to his friends

Steve and I had spent our first night together as a realcouple and in a real bed and it was wonderful. I had intended to wake him up with a blow job but he was already gone when I woke up so I had the whole day to wait for him to return from work. I spent the day just like a housewife would. I wore a house coat and some fuzzy slippers and after cleaning up the place sat down and watched...Read On

43

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SluttyTammyCD

Gang banged at a private club

This is what happened when a friend took me to a private members only gay, bi, and transgender party

After yet another hot weekend at my friend Heberto’s house, I was packing up and getting ready to go home when he told me he had something “special" in mind for us next weekend. I begged him to tell me what he had in mind but he refused. So I left. My curiosity was peaked. The week dragged on thinking about all of the possibilities. The anticipation was killing me. Finally Friday...Read On

32

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iltns2569

Friend Becomes My First Part 1

The true story of one my best friends becoming my first

*This is a true story of my first time having sex dressed a girl* It finally happened, and it was a dream come true. I started dressing as a girl when I was 17. For me, it started with a thong I stole from my mom's drawer which eventually went on to lingerie, to normal clothes, and all the way to dressing fully. Im now 24, and all I wanted to do was to show myself to a man and be the little...Read On

88

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hotvicky

Vicky's First Time

My first time having sex as Vicky

I was very open about crossdressing when I met my wife when we were in our 20s. She has been very supportive and helpful. She helps me with my hair, makeup, and picking outfits. We started having sex with me dressed up as Vicky. This soon escalated to her taking me with a strap on. I loved the times she would fuck my ass with her cock. I had never considered myself gay or bisexual but the...Read On

20

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cindytranee

My First Boyfriend Part Two

My boyfriend and I get closer

NOTE- this story will make more sense if you read part one,it can be accessed through my profile page. The week leading up to today had been one of the longest of my life. I was very excited that today had finally arrived. My boyfriend Steve’s parents left early that morning and would not be back for three days. My parents had agreed to let me stay over while they were gone. Steve and I...Read On

33

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subguy

Wonderful crossdressing shopping experience

A wonderful Christmas eve to remember

Following is a true account of my recent experience of shopping for clothes (crossdresser, no sex). I just wanted to share a couple of very pleasant experiences I had shopping at the Natick Mall near Boston. It was the first time ever that I managed to shop with confidence and without any stress. I really want to give compliments to lovely women who made this possible (in case any one of...Read On

65

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Nicole94127

Crossdressing Fun From A Woman's Point of View

I have enjoyed reading the stories written by men to get a better understanding of what it is like to crossdress. As a woman, I find that I really enjoy and am very aroused with a feminized man. I guess I have always been a bit of a tomboy and enjoy doing athletic things, so being with a man that is the opposite seems natural to me. I used to play gender swap cross dress role play with my...Read On

19

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LilPandaKisses

Surprise

Aubrey greets his boyfriend home from work in a new way. Slight BDSM ahead.

Aubrey swallowed the lump in his throat as his wrists grew sore from his restraints-being handcuffed to the headboard of the bed, naturally he grew stiff. Speaking of stiff... he peered down, under the frilly black miniskirt of his maid outfit was a visible bump, straining against the panties that constricted it, said lingerie was clinging to his soft pale skin. He bit a plump bottom lip...Read On

24

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PaulineWendy

All by mistake

A chance encounter

It all began by mistake. I had spent the morning at home, relaxing in one of my favourite outfits. I was starting to think that work beckoned, and had begun the transition back to drab. I took off my wig and make up, but decided to keep my panties, tights and bra on, as my clothes would hide what I was wearing. My attention was caught by a news item, and I sat watching the television for...Read On

62

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cindytranee

My First Boyfriend - Part One

I learn to cross dress and get a boyfriend

Since my family had moved to our new house, Steve and I had become best friends. He lived next door and had moved in about a month before we did. With both of us being the new kids on the block we bonded quickly. He was two years older than me at eighteen and I had just turned sixteen a few months back. He was also taller and had more muscles than I did. He had tan skin and black hair where I...Read On

24

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jennaryder13

Prom Date- Part 1

Jody is forced to dress as a girl for prom.

Jody was pretty much a typical 18 year old boy. He liked sports, hanging out with his friends, and playing video games. However, Jody had one deep, dark secret. He was addicted to wearing his sister's clothes. Every time the house was empty and he had the chance, he would sneak into her room and try on something pretty. Jody was always mortified of getting caught so he was very careful....Read On

48

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SluttyTammyCD

Neighbor fun

Slutty fun with neighbors

It was a typical Friday night. I would hurry home from work to complete my ritual. Take all of the necessary steps for a lot of anal sex, shave all over and transition from a male to a female. I put on a typical “uniform” for the trip to his house. A lacy black top with a lacy black bra under (looked more like a teddy than a top), a short pleated black skirt, black stocking, garter, and...Read On

47

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SluttyTammyCD

Total Sub CD Slut

His total sub CD slut

I could not wait to get home from work on Friday. My routine was the same. It was total preperation for the weekend. I was a highly placed executive with the company I worked for at the time. Nobody knew that I lived as a total sissy slut cock worshipping whore on the weekends. I was seeing a guy who was very dominate. I met him online. The first night he took me home he dressed me...Read On

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1ball

Mistress Hannah's Pathetic Husband Part 9

The final forbidden fantasy fulfilled

When we returned home, we had a big late lunch because Mistress informed me that we might want only a light dinner and then a late snack. I spent the afternoon preparing as best I could for an unknown special night. This meant hair removal, nails, wig, makeup, enemas, buttplug, lotions, powders, perfumes, the whole works. When I finished, she laid out the clothes and jewelry I would be...Read On

Added: 02 Nov 2011 | Category: Crossdressing | Words: 4,600 | Tags: interracial cuckold creampie anal redemption | 8 Comments

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1ball

Mistress Hannah's Pathetic Husband Part 8

A return to the body art parlor

As we tried to sleep one Friday night after Mistress Hannah had used my ass with unusual vigor, she was tossing and turning and keeping me awake. I got the impression that she was struggling with some personal demon that was becoming an urgent threat. Something had changed around the time two months earlier when I had first achieved the goal of putting my puny pud up her ass. I don't think...Read On

Added: 01 Nov 2011 | Category: Crossdressing | Words: 3,127 | Tags: humiliation panties tattoos strapon | 2 Comments

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1ball

Mistress Hannah's Pathetic Husband Part 7

Mistress makes good on her promise

It was 8 months since the first time Mistress Hannah had ordered me to put on her panties. In that time I had become both more of a man and more of a sissy. When we went to the theater club on Sunday nights, I had a variety of dresses, wigs and shoes to choose from. My aerobic workouts had boosted my stamina and I had gotten good control over my premature ejaculations. I still occasionally...Read On

Added: 31 Oct 2011 | Category: Crossdressing | Words: 2,202 | Tags: buttplug anal panties humiliation | 1 Comment

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1ball

Mistress Hannah's Pathetic Husband Part 6

Mistress Leelee uses me hard.

Having accepted the riding crop, Mistress Leelee seemed to understand that she was being given the opportunity to do something to me, but she was clearly lost. "He's yours now Leelee. It starts with the first order. If you're going to turn your cheating husband, a little experience with Michelle here will give you confidence. I suggest you order him to stand in front of you and work from...Read On

Added: 29 Oct 2011 | Category: Crossdressing | Words: 1,926 | Tags: humiliation strapon lesbian | 1 Comment

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1ball

Mistress Hannah's Pathetic Husband Part 5

I serve lunch to sorority sisters

I was making progress as a slave but unkown to me, one of my stories helped Mistress Hannah see an opportunity for a particularly fun afternoon and a chance to help an old friend through a rough spot in her marriage. Several months of aerobic classes and feminization had increased my stamina and made me more comfortable when we spent our Sunday evenings out for dinner and as member/patrons at...Read On

Added: 27 Oct 2011 | Category: Crossdressing | Words: 2,575 | Tags: humiliation strapon | 3 Comments

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1ball

Mistress Hannah's Pathetic Husband Part 4

Mistress takes the humiliation to a new level

The third and final day of my transformative weekend started poorly. I had aches and pains all over. My neck and back and thigh muscles were sore. I had a little irritation from body hair that was growing back. And of course, my asshole felt all stretched out and very tender. I wondered if it would ever feel tight again. I also wondered what the evening would hold. I couldn't imagine that...Read On

Added: 24 Oct 2011 | Category: Crossdressing | Words: 2,828 | Tags: humiliation feminization humor beads strapon | 2 Comments

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Chrissy_CD_slut

Chrissy Gets Bolder Meeting Todd Again

Chrissy gets a good hard fucking by her new friend

I really hadn't expected Todd to call me after that night. I know how guys are when the night is getting short and you need someone to satisfy your needs. I did think about him a few times and wanted to see him again. I had enjoyed my first experience with a man so much it seemed that's all I could think about was my next cock. When I went to class I would catch myself looking at guys as...Read On

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1ball

Mistress Hannah's Pathetic Husband Part 3

I learn how manly my mistress wife can be

The first week of having a useful cock went well. For the first time since we got married, we had sex every night. After strapping my extension on, I would lick Hannah's pussy enough to get her turned on and then she'd choose a position. If I got physically worn out, she would choose another position. Because I was having sex so often and doing some research on the Internet, I was able to...Read On

Added: 20 Oct 2011 | Category: Crossdressing | Words: 3,357 | Tags: humiliation feminization strapon anal | 3 Comments

45

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anotherfeeling

Summer dressing

Long hot summer for crossdressing student doing vacation job

It was the mid 1980s, I was 20 years old and it was the summer holidays. For the long break from college I'd managed to find a vacation job in Kent in the south of England. It wasn't brilliant but I was going to get some experience of working with computers, and earn a bit of money to keep me going during term time. The company was based in a small town where I had found a room in a house with...Read On

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1ball

Mistress Hannah's Pathetic Husband Part 2

The transformation begins

During my first week as her new slave, Hannah decided that I was too hairy for a little sissy boy, so I had to begin removing hair from the tip of my nose down. The mustache went first. It really was kind of pathetic anyways. I actually got compliments from some of the women at work about how handsome I looked without it. I had grown it because I had a "baby face" and I wanted to seem...Read On

Added: 18 Oct 2011 | Category: Crossdressing | Words: 2,965 | Tags: humiliation sissyboy panties | 5 Comments

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Crossdressing

Telling Mom I'm A Crossdresser Part 3: Missy's Weekend

Telling Mom I'm A Crossdresser Part 2: The Adult Store

Telling Mom I'm A Crossdresser

A new friend

My First Boyfriend Part Five

My Girly Fantasy

My First Boyfriend Part Four

My First Boyfriend Part Three

Gang banged at a private club

Friend Becomes My First Part 1

Vicky's First Time

My First Boyfriend Part Two

Wonderful crossdressing shopping experience

Crossdressing Fun From A Woman's Point of View

Surprise

All by mistake

My First Boyfriend - Part One

Prom Date- Part 1

Neighbor fun

Total Sub CD Slut

Mistress Hannah's Pathetic Husband Part 9

Mistress Hannah's Pathetic Husband Part 8

Mistress Hannah's Pathetic Husband Part 7

Mistress Hannah's Pathetic Husband Part 6

Mistress Hannah's Pathetic Husband Part 5

Mistress Hannah's Pathetic Husband Part 4

Chrissy Gets Bolder Meeting Todd Again

Mistress Hannah's Pathetic Husband Part 3

Summer dressing

Mistress Hannah's Pathetic Husband Part 2