Crossdressing Stories

31

sarahricegirl

Becoming Sarah

A man embraces his femininity and gets changed forever.

I was driving home from a work trip. That is how it started. There was roughly 85 miles to home. I had been driving for about an hour when my mind began wandering the way it always does when I'm not preoccupied. It always goes to the same place. For the better part of five years, I have been cross-dressing in secret whenever I have the house to myself. Sometimes I do it because it...Read On

21

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allfours

Becoming Chloe - Part 5

Friday night - part one

I got home, tired and cold from work, only to find Vickie already there. That in itself was unusual, because she normally didn't get home until after me. Before I'd even taken my coat off, she greeted me with a really passionate kiss, then turned me round and pushed me back through the front door. "Where are we going?" I asked, but she just gave me a big, mischievous grin. "Out." We got...Read On

12

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ThePhantom

Weekend Discovery 3

Simone was left alone in a room that held the most extensive collection of lingerie that she had ever seen outside of a retail store. She was amazed that she was as turned on as she was and not shocked at the current events. She had gone to her boss's house to confess just how much she wanted him and to see if the feeling was mutual. She was momentarily heartbroken when a stunning...Read On

25

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tvk3983

Michelle Gives It Up

Michelle provides him with everything she has to ffer

When my best friend, Jimmy, left my house late that afternoon he was a very well satisfied guy, sexually. For the two years prior we'd had quite a few mutual masturbation sessions. This had progressed from jacking off while talking about various girls we knew in school to jacking off each other. Of course, at that time neither of us had actually done anything with a girl, but that never slowed...Read On

12

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tvk3983

Karen Goes Out

Karen gets the nerve to go out and discovers who she is.

I was so nervous I was almost sick. For years I'd dreamed of going to a bar that catered to the LGBT community but I'd always come up with an excuse not to, no matter how flimsy it might be. Yes, I'd gone out in public several times, shopping mainly, but also banking, getting gas, and even meeting with other girls like myself. So far, the only sex I'd indulged in while dressed had...Read On

11

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ThePhantom

Weekend Discovery 2

Simone's eyes grew wide when she realized that the stunning blond she was sitting next to was, in reality, her boss and the object of her most intimate desires. Now she had seen transvestites and drag queens before, but none of them looked this good. She was sitting just mere inches away from his face and still couldn't see any trace of Andrew Lippincott. Without warning Andrea leaned...Read On

21

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allfours

Becoming Chloe - Part 4

Vickie reveals her past...

On Sunday, I was awake first. Eager not to disturb Vickie, I snuck to the bathroom to empty my rather full bladder. The chemise felt so natural that it was almost instinctively that I sat down to pee instead of my usual standing up. After I'd wiped myself dry (another first!), I crept downstairs and made us both coffee. The curtains were all closed, so I felt comfortable wearing lingerie...Read On

9

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ThePhantom

Weekend Discovery 1

Friday had finally arrived. Andrew Lippincott glanced at the Rolex on his wrist and then began to pack his attaché case. It was only 4:00 pm but he was the office manager and one of the perks that came with this title was the ability to leave early. Winter had the city in its grasp and a travelers advisory had been posted.That meant there would be no unannounced guests to prevent him...Read On

29

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allfours

Becoming Chloe - Part 3

Chloe gets her name - and much more...

When we arrived home, I was desperate to change, but Vickie said no, much to my frustration. The rest of the afternoon went like any other Saturday, and after dinner, we sat and watched tv for a while. Around nine o'clock, Vickie got up and suggested that we have an early night. By now my frustration had almost abated, so I followed her upstairs and we both got ready for bed. I was delighted...Read On

27

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allfours

Becoming Chloe - Part 2

Their first shopping trip, and a changing room revelation...

As I lay there, my heart racing, I wondered what my wife would say. After all, she'd just caught me cross-dressing for the first time. So far, it had turned her on and we'd had the most fantastic sex since we first got married, a few years ago. Now that we were both spent, I started to get nervous about what she would think of me. Vickie rolled off me and then snuggled up as I put my arm...Read On

40

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oceanrunner

My Wife's Thong

Mike wears his wife's panties to win a bet

“I don’t see what the big deal is. You look so sexy in them!” “You do know what a thong is and how it works, right? It might as well be called ‘automatic wedgie underwear.’ I don’t really like walking around all day with a string up my butt just so you can get worked up by what kind of underwear I’m wearing when you’re not even around for it!” She wasn’t angry, but she did sound a...Read On

37

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allfours

Becoming Chloe

Caught in my wife's lingerie...

It was a mistake. I realise that now. I just don't know what came over me. One minute I was tidying the bedroom and the next minute I'm lying on the bed in my wife's basque and stockings, and using her panties to have the most fantastic wank I've ever had. I realise now that it probably wasn't a good idea to go through her underwear drawer while she was at her Mother's, but the lure of...Read On

6

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Dividence

The Wedding Proposal, chapter IV

Part 4 of 4: The young newlyweds spend their honeymoon on the yacht.

The first week at sea was wonderful. We set off to the Mediterranean, and the sea was calm and pleasant. A refreshing breeze made slight ripples on the quicksilver surface. I guess we would curse the heavens if we had to rely on sailing wind, but in the motorized yacht, it felt like a blessing. There were no other people around, and I could fully succumb to my feminine side. I spent long...Read On

6

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Dividence

The Wedding Proposal, chapter III

Part 3 of 4: After the wedding comes further complications. But not necessarily for the worse.

I woke up and saw the bright, yellow orb of sun shining in through the broad windows. It was warm, and the thin linen was wrapped around my sweaty body. I was glad I remembered to remove the tight corset before going to sleep, and I was now wearing only the thigh-high stockings and garters. A pair of white panties lay on the floor where they had been hastily thrown. My fake breasts were...Read On

9

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Dividence

The Wedding Proposal, chapter II

Part 2 of 4: A nervous fake bride attends her friend's fake wedding.

The large gown rustled, and the heels clicked loudly as I descended the stairs in my home and walked towards the front door. I would be picked up by my friend’s sister before going to the church. I had never met her before, but he’d assured me that she knew nothing of my secret. It would be nice to have someone to confide in, but I knew being treated as a girl by everyone would probably...Read On

13

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thatfemininUrge

My First Glory Hole

Sucking off strangers.

I have thought about it for sometime about going to a glory hole while dressed en-femme. Naturally, the problem was where to find one or what adult book store would have one. I knew that I would have to drive some miles to find one. So after doing some research online, I was able to find one that was about a forty-five minute drive from my house. After rationalizing and convincing myself that...Read On

14

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Dividence

The Wedding Proposal, chapter I

Part 1 of 4: Real friendship is measured by how far you are prepared to go.

I slowly let the sheer, white stockings slide up along my closely shaven legs. They were smooth as silk, and no hint of coarseness caught the fabric as I stepped into them. The broad bands of elaborate lace hugged my thighs and made me feel great. Four straps, each decorated with a small silk ribbon, held the stockings attached to the garter belt I wore around my waist. The coarse lace felt...Read On

16

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tvk3983

The Adventures of Patty

Patrick becomes Patty and doesn't look back

“You're wearing my things again!” Brenda screamed when she came home early from community college and found me prancing around the house in one of her short skirts. “Take them off, you little pervert!” It wouldn't be nearly as bad if I were her little sister and trying on her clothes but I was her brother. But it wasn't as bad as it could be. I mean, if she knew what Tommy and I had been...Read On

4

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COMP

Jakladd

Wifey's Panties

What a hottie little sissy bitch I have become.

Our phone sex is always so hot; you egg me on in so many ways. My wife has no idea how much I wear her panties not to mention her lingerie, stockings and dresses. We talk about what I'd wear when we get together as I suck your cock. You always have me send you pictures of me dressed in panties, stockings and high heels, telling me how perfectly stunning my penis looks in silky panties and...Read On

9

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tvk3983

Sharon Goes The Distance

David becomes Sharon at his wife's request

When I woke up Saturday morning, I knew it would be a very eventful day. My wife, Donna, had been making plans for quite some time, which included me dressing up as Sharon, my female alter ego. Three years ago, I had confessed to Donna my desire to wear feminine attire from time to time and she had embraced it more than I could ever imagine. In fact, she took pictures of me all dressed up or...Read On

11

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Tara85

The Engineering Costume Party: Part 2

A college freshman gets more than he bargained for.

After realizing I might be the only guy dressed as a skank for the Skanks and Robots Party I timidly waited in the dorm room and “pre-gamed” with Anthony and Jillian for the upcoming festivities. I drank vodka and cranberry with Jillian while Anthony had beer. I hoped some “liquid courage” would help me to feel more comfortable going to the party dressed in such a slutty outfit. Now, I...Read On

16

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tvk3983

Deann Finds Out

Deann finally works up nerve to go out in public

Jimmy sat up in bed and felt the dry cum on his belly from last night's masturbation. A quick look at the clock told him his parent's had already left for work and their weekend trip so he knew he had nothing to worry about. The plans he had for the day could begin right now. Stepping out of bed, he padded to the bathroom and began the process. A long shower began the day. He made sure...Read On

4

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tvk3983

Jaime's Way (part 3)

Jaime and Jeff step it up a notch

As Jeff closed the door he grabbed me by the hand and spun me around, pulling my nude body close to his, breathing in my perfume before locking his lips over mine. My fingers found the button on his jeans and opened them with urgency, more than a little pleased when his huge cock sprung out. “Damn, I want you so badly, Jaime,” Jeff moaned when he broke the kiss. “I'm yours to do with as...Read On

4

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tvk3983

Jaime's Way (Part 3)

Jaime gets uncaged and left alone for a week - she doesn't lack for company.

As Jeff closed the door he grabbed me by the hand and spun me around, pulling my nude body close to his, breathing in my perfume before locking his lips over mine. My fingers found the button on his jeans and opened them with urgency, more than a little pleased when his huge cock sprung out. “Damn, I want you so badly, Jaime,” Jeff moaned when he broke the kiss. “I'm yours to do with as...Read On

Added: 08 Nov 2015 | Category: Crossdressing | Avg Score: 4.5 | Words: 8,895 | Tags: cd oral anal

6

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Maid2frill

Evie Gets Her Reward

The final part in the story of Mistress Sarah and Evie

I went downstairs to the kitchen, carrying the cold tea. As I walked into the kitchen, I could see up the drive through the window. There was a car parked at the top of the drive, a taxi. I ran back upstairs to Mistress Sarah. “Mistress, are you going out again?” I asked. “No dear,” she replied. “why do you ask?” “There is a taxi parked at the end of your drive. It looks like the same...Read On

11

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pentup47

The girl with green hair

An extra-special birthday surprise

"Is this cab taken?" Languorously, she lifted her green mascara-clad eyelids and gave a half-smile. "'Fraid so." I'd left the party in the local wine bar and decided to get home before I passed out. I was feeling pretty squiffy. Two taxis cruised by with their engaged signs on. It began to spit with rain. I looked through the back window of the parked cab. The interior light was on....Read On

12

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tvk3983

Jaime's Way (part 2)

Sherry has transformed Jaime into a sexy slut

I awoke to feel the dried cum on my face, ass and balls, and then remembering how I got that way made me smile. Crawling out of bed I made my way to the bathroom and took a hot shower and then easily shaved my already smooth legs. Out of the shower I brushed my hair and did what I could to make it appear more feminine. After I put on my make up I walked back to the bedroom and slipped into a...Read On

9

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COMP

Tier_innerhalb

Skye High

Best friends discover their mutual romantic interest in one another

It was more of a small gathering than a party. Eight friends hanging out in one house for the night, to enjoy a a late night hockey game. In the mean time, the living room stereo system played the local electronica radio station, while the small group enjoyed various activities. One, however, was not having a good time at all. Skye sat in the upstairs bedroom, her back to the door, her...Read On

24

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tvk3983

Jaime's Way (Part 1)

Sherry make Jim become Jaime

I'd only been married a very short time when my wife came home and caught me masturbating while wearing a pair of panties and a bra. This in itself was bad enough but then she caught me again, and then again. The first time she caught me she was shocked and appalled but the twentieth time or so that she found me wearing panties and bra and with a dildo in my ass she really lowered the boom...Read On

26

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Melanieatplay

High Fashion Queen

A transformation changes the lives of two college friends.

I felt like such a loser. It was Friday night and instead of going out and hitting the clubs to dance, drink, and have fun, I was in my dorm room with my best friend. We had known each other since the 6th grade and today was his birthday. No one should be left alone on their birthday right? To be honest, I didn’t really feel like going out anyway. My boyfriend, who I had been seeing for...Read On

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Popular Tags

Crossdressing

Becoming Sarah

Becoming Chloe - Part 5

Weekend Discovery 3

Michelle Gives It Up

Karen Goes Out

Weekend Discovery 2

Becoming Chloe - Part 4

Weekend Discovery 1

Becoming Chloe - Part 3

Becoming Chloe - Part 2

My Wife's Thong

Becoming Chloe

The Wedding Proposal, chapter IV

The Wedding Proposal, chapter III

The Wedding Proposal, chapter II

My First Glory Hole

The Wedding Proposal, chapter I

The Adventures of Patty

Wifey's Panties

Sharon Goes The Distance

The Engineering Costume Party: Part 2

Deann Finds Out

Jaime's Way (part 3)

Jaime's Way (Part 3)

Evie Gets Her Reward

The girl with green hair

Jaime's Way (part 2)

Skye High

Jaime's Way (Part 1)

High Fashion Queen