Crossdressing Stories

9

hoterotica

Steve the Crossdressing Cat Lover

Cat lovers are a breed of their own and my boyfriend, Steve, is one of them.

My boyfriend, Steve, has a lot of cats. I can't tell you exactly how many because the little critters come and go out the pet door and scatter as their furry little paws please. Steve lives on a farm. Well, it's kind of a farm. I mean, he has a lot of land, but he doesn't exactly grow anything on it except cats from what I've seen. And he has a barn, too. You'd think with all that land...Read On

35

vote

hoterotica

My Boyfriend's Blue Silk Panties

a crossdressing shortie

My boyfriend, Allen, is a man's man. Let's get that straight from the start. He rides a Harley and he scoops me up in his big strong arms like I'm light as a feather (which I'm not...let's get that straight from the start, too). So it was a big stretch for me to ask my masculine lover to slip into a pair of silk panties just for me. It was a secret fantasy I'd harbored for years but had...Read On

63

vote

Lucy_CD

First time sex with a man!

How my first time anal started and happened.

So there is this guy who I've been talking with for awhile. I wasn't too interested because I was still on the edge about meeting up dressed with another person. At the time I was under the influence and I sent him this message. "I have recently been dressing up more as a woman as my family have been busy. I have been eating my cum all dressed up like a sissy! I have been eating my...Read On

24

vote

kylie_kained

The Wedding Present

Chardonnay wants to show her boyfriend and lover how committed she is to him.

Chardonnay had been Phil’s live in sissy lover and constant companion for just coming up to two years. She wanted to do something very special for him and had saved enough money at last. She phoned an exclusive hotel, giving great detail into what she required. She made a few more calls that afternoon while Phil was working. As she finished the last call, she gave a huge grin to herself in...Read On

47

vote

AbigailThornton

The Neighbour's Knickers - Part 1

A man who just can't resist the opportunity to get into his neighbour's knickers

It was a sultry summer night but it wasn’t the muggy air that was making me hot. It was my clothes. I’d felt the urge to dress up in a very sexy outfit. My preparations had started much earlier in the day, and they had been thorough: my whole body was clean and smooth, shaved so that there was not the slightest hint of hair anywhere other than on my head. My heart thumped wildly as I...Read On

18

vote

biguy2play

After the Show

An invitation to a drag show proved to be an invitation to more.

I‘d met David through my (now ex) wife. He lived in the Twin Cities with his partner Dennis. His being gay made it very easy for me to talk openly about being Samantha. He hosted a drag show on Saturday nights at a small gay bar so he’d invited me to come along, meet the ‘girls’ and see the show. I could stay the night so I could go dressed and have a fun ‘girl’s night out’ while he MC’d...Read On

28

vote

biguy2play

Keeping A Secret

The drive home from the Cities was always long. After work I had stopped at Kim’s to change and emerged as Samantha. I drove to the meeting and then went out for a drink (or maybe two) with some of the other ‘girls’. By the time I was half way home my eyes just wouldn't stay open any longer. I decided to pull over in a secluded wayside rest area. If I could just catch a little catnap I knew...Read On

13

vote

novaguy

Ready to Perform, Part Two – All Crossed Up

I get more than I bargained on!

Much happened in the next twelve months following that first session with my ex and her new partner: Ann began divorce proceedings which I didn’t contest, I financed myself into another home, and Ann, David and I met for two more sessions of torrid sex. These sessions were pretty much replays of the first; I would first screw Ann thoroughly through at least two climaxes, and then she would...Read On

67

vote

hummmph

A surprise ass-fucking in panties

A friend displays her kinkier side

A very curious thing happened to me the other day and I feel I need to share it with you... I have been 'mildly’ crossdressing for over a year now. I say 'mildly' because I am not into full feminization, I just love the feel and look of lace panties when they are hugging a good looking cock, not to mention the taboo. I have taken to wearing stockings too which feel amazing, it's like...Read On

40

vote

snowball

What a Girl Wants

'Katie' finally fulfills her fantasy of having sex with a man.

"Come on, Katie. Give in to your desires. You've gone this far. You're almost there. You're so close to your goals and dreams of being treated like a lady. Accept it. Embrace it. Give in and complete your journey. Tell me what you want." Todd and I had been friends for years and even co-workers at one point in our respective careers. It had been almost ten years since I'd seen him and it...Read On

10

vote

ThePhantom

My First Time - Part 3

The story continues...

As Lydia had promised, on the first day of her vacation I got my first lessons in high heels. It took most of the day before I was able to walk across the room and not fall on my face, and these were only a moderate heel. I took her to dinner to celebrate and, at her request, I wore the satin thong under my jeans. Lydia could not resist reaching out and squeezing the bulge in my jeans,...Read On

21

vote

torpedoman

July 4th Celebration

My wife Ann sets up a mini vacation over the 4th of July.

On July first I returned home from our health club. Ann was packing my suitcase for a mini vacation at a bayside resort. My suitcase was filled with all my girlie things: lubes, vibes, wrist and ankle restraints and the paddle she used on me when I was bad. She also said Ben, his brother Josh, and two others were joining us. Before continuing, I should mention how I became the man I am...Read On

7

vote

iluv2tosssalad

The Business Trip - Part 1

A man has a wild experience on an unexpected business trip.

I work for a small web design company in northern Connecticut. We acquired a rather large account with a lawn care company in Virginia, and my boss asked me to go with him to present the design we had created, since I was the only other male at the company. My boss told me he didn’t want any of the women to think he was hitting on them. Never having been asked to go on a business trip for...Read On

8

vote

vanessagrrl

Just the Two of Us, or Four

Vanessa and Greg fail at trying to spend a night alone

As time went on, the line was beginning to blur between me being Greg's girlfriend and Amber's pet. Greg decided that we needed a night alone. That didn't work out exactly as planned. He booked us into a lovely, fancy hotel in the heart of the city. Next up was going to be a nice dinner at a gourmet restaurant, and then we'd see where the night went from there. I wanted to impress, so I took...Read On

24

vote

libertina

Caught!

Crossdresser is caught by his flatmate and fuckec

I stood in front of my full length mirror wearing my new black heels. Not just the heels of course! I had a sexy, short black dress to go with them. Underneath, I had some incredible purple and black underwear; all silk and lace. I twisted on my heels and pulled my dress up a little, wiggling my thong covered ass at the mirror pretending somebody could see... ...And that’s when he knocked!...Read On

24

vote

xavier5269

Caught By My Girlfriend

Hitting puberty late in high school had its disadvantages. A slender, almost feminine body and a small dick was not something a lot of women tended to go for, however, I was lucky enough to find Adrian. We hit it off right away, shared many things in common and we couldn’t get enough of each other. She was gorgeous, standing at six feet, she was just as tall as me. Her beautiful crystal blue...Read On

21

vote

libertina

An Uneven Romance - Part Two

He's taken further into her strange, kinky world

“Hey, Sam.” I jumped and spun around, startled. One of my housemates, Mark, had walked into the kitchen where I was preparing breakfast for Sarah, the incredible girl I’d brought home the night before. Sarah was a pretty special girl; after a night spent with my head between her legs she had eventually let me cum this morning. She’d somehow coaxed me into wearing her wet panties from...Read On

35

vote

libertina

An Uneven Romance

He picks up the girl of his dreams only to find himself being used

I couldn’t believe I’d gotten her home with me. We’d met in a bar when I was drinking with my friends, I spotted her early in the night but didn’t have the courage to talk to her. She looked perfect. She was slim, with long red hair that came down to a tight, round ass. When she turned around, I saw she had a truly beautiful face but there was a sexy, dangerous look in her eyes that scared...Read On

25

vote

cindycdvb

Anonymous Encounter

An Anonymous Encounter of a Crossdresser with someone from Adult Friend Finder!

Well it was a boring day. It was fairly hot outside,somewhere around 93 degrees. The sun was shining, there were very few puffy clouds in the sky, and I was home alone. As usually happens when I am bored and home alone, I was horny as hell. I wanted to jerk myself off, but I wanted to do it to something different than the normal porn that I usually watch. I figured since no one would be back...Read On

10

vote

stockingssussies

film fun

I get fucked while her husband films it

I met Lucy on the net, she was a married BBW with massive breasts (46g) and ass to match and loved to dress how I like my ladies to. That means mini skirt, high heels, stockings and suspenders and a low cut top. We had met a couple of times before I got to meet her husband Ray. Lucy and Ray had arranged to come to my house one Saturday night for some food , drink and fun, but I had no...Read On

52

vote

snowball

From Shock to Awe...some

The day my sex life was unexpectedly changed forever by a loving wife

To this day, I don't know what caused my wife to come home early from work that morning, and although at the time I was sick to my stomach with dread and fear when she walked in on me, I'm now glad that it happened. For the first time in over ten years of marriage, we can now finally talk about what sexual desires we have. But I'm getting ahead of myself. Let me back up a bit. I met my...Read On

16

vote

TinaTim

First Night Nerves - Part 2

Tina agrees to meet Barry without 'the girls'

I sat by myself on the bus, my briefcase on my knees, counting the stops and wishing it would go faster. Since Barry’s text message last night and his surreptitious call to my mobile that morning, I had been so excited, planning what I would wear to please him most. Debbie hadn’t heard the beep on my phone so didn’t know that I would be meeting him without her that afternoon. So far I had...Read On

7

vote

vanessagrrl

Starting to Have Fun as a Slave Girl

Vanessa is won at an auction to do one man's bidding for the night

Greg and I had resumed our relationship as normal after my experience at Mistress Amber's. I was enjoying being his girlfriend. He treated me so nicely, and we enjoyed our time together. It was the most intense sex life I had ever had with anyone. For the most part he enjoyed being the dominant one, and he was happy to make me his little fucktoy after a nice night out. But it was that line...Read On

36

vote

jennaryder13

My New Sissy Life

A sissy lives out her ultimate dream.

I was so stunned I was unable to speak. I only thought things like this existed in my fantasies and could never actually exist in the real world. It had been three weeks since I found an ad posted online seeking two submissive males for "training." I read the description which said, "Attention sissy boys! Have you ever wished that you were a trained sissy slut? Of course we both know the...Read On

33

vote

TinaTim

First Night Nerves

Nervous Tim becomes Tina and loses her virginity

My name is Timothy. I live in a large city in the English Midlands with my girlfriend Debbie. We are both 22 years old and have lived very happily together for over three years. We both work in a call centre for a large financial organisation. I am not tall – 5' 4" on a good day – and have always been very slim. I am blonde with blue eyes and very fair skin. Debbie is two inches shorter than...Read On

14

vote

vanessagrrl

Transitioning and Bound

Vanessa and her man find a mutual pleasure - her with other men

It had been a while since I started the hormones, and I couldn't have been happier. I was looking and feeling more womanly than I ever thought possible. It brought me a new confidence when I was in public, and made me feel so much sexier, and girly when I was in the bedroom. My breasts weren't that big, but they were growing over time. I had a nice handful, and Greg said he loved to suck on...Read On

17

vote

1936Storyguy

First Meeting with a CD

A cross dresser experiences his dreams with a man

It was strange, he contacted me first and his profile stated he was looking for a domme or trans to submit to. I guess the hidden desire to please a man won out. We communicated through mail and messenger for months. We even met for coffee and some groping, where I tested his desire for nipple play, some severe pinching and even squeezed his sac to express the control I wanted and what he...Read On

37

vote

CAPITALLETTERJ

Dirty Little Me

Caught, with panties on and my pants down...

Rushing around all day, it seemed like this was starting become a ritual for my Fridays but this particular Friday I would never forget! Waking up late as usual I flew out the the door as fast as I could, not giving any thought to what I had done the night before. As usual my boss wasn't too pleased but I never really minded his attitude because everything he lacked in personality he made...Read On

19

vote

vanessagrrl

A New Level

Things escalate for Vanessa and her man

Greg and I had been seeing each other for a little while at this point, and things were going great. We had gone on a few dates and I loved how he always treated me like a lady. He made me feel so sweet, sexy, and vulnerable. Tonight was four months since our first night together and I wanted to surprise him with something a little special. I bought a long coat, and I thought it would be fun...Read On

43

vote

cuckoldmalesub

Caught, Used and Loving it Part 2

My descent continues

It had been two weeks since I had been caught and used by the mystery woman and her boyfriend. They had left as quietly as they came, and I was left kneeling on the floor dressed in all my best female clothing, cum dripping off my face, and my own cock dribbling cum on the floor. Since then, I had had only two emails. One was sent immediately after they had left and contained ten pictures...Read On

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Popular Tags

Crossdressing

Steve the Crossdressing Cat Lover

My Boyfriend's Blue Silk Panties

First time sex with a man!

The Wedding Present

The Neighbour's Knickers - Part 1

After the Show

Keeping A Secret

Ready to Perform, Part Two – All Crossed Up

A surprise ass-fucking in panties

What a Girl Wants

My First Time - Part 3

July 4th Celebration

The Business Trip - Part 1

Just the Two of Us, or Four

Caught!

Caught By My Girlfriend

An Uneven Romance - Part Two

An Uneven Romance

Anonymous Encounter

film fun

From Shock to Awe...some

First Night Nerves - Part 2

Starting to Have Fun as a Slave Girl

My New Sissy Life

First Night Nerves

Transitioning and Bound

First Meeting with a CD

Dirty Little Me

A New Level

Caught, Used and Loving it Part 2