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16

Phoenix Park Night

My first time getting a blowjob from another man while wearing lingerie

I am a 32 year old married guy who happens to like wearing ladies' lingerie. My fondness for wearing lingerie goes back to my late teen years when I would wear my mother's clothes and underwear. I went on to wear my sister's undies and this continued into adult life where I have worn the undies of many ladies (without them knowing it). Until the time of this story, I never ventured...Read On

16

Andrew to Andrea - Part 3

..the next step...

 BRRRRIIIIIIINNNGGGGGGGGGG!!!!!! The alarm clock that my wife and I mockingly referred to as “Baby Ben” sounded off and pulled me from what I first thought was a great dream. As my senses slowly came online, I could feel my hand laid over my naked wife’s breasts and that I wasn’t in my usual gym shorts and t-shirt. I was surrounded in silk, and it was not unpleasant, but it was a floor...Read On

16

Club Night

Wearing my sexy minidress out to the club, I give the boys lots of thrills.

I hadn't been at the club very long when he came over to me: a very handsome man, tall with dark hair and blue eyes. "You have a perfect ass," he said. I was wearing a sexy, little minidress which barely covered my ass and I knew it would turn men on, but I didn't know it was going to happen this quickly. I smiled up at the tall stranger. "I'm flattered," I said. "I'd like to pull up...Read On

12

Tennis

A panty sniffer is tamed

Sandra and I had been going out together for about six months. She was the perfect looking girl for me, with her beautiful freckled face, slim turned-up nose, pouty red lips, light green eyes, long blonde hair that she usually kept in a ponytail or braids, a great body topped with perky B-cup tits, and a cute firm ass that just screamed to be pumped. She was only 23, but Sandra already knew...Read On

12

My First Thong

How the thong panty changed my sex life so young

When I was a little boy in grade school, I developed a curiosity so strong that it could not dare be mentioned to my parents...well, except for my father, since he was quite a perv despite being married to my mother who was more conservative than he was. Typical behaviors in a hispanic couple's life, really. No, it was not about my sexuality, but it involved underwear. Specifically, a...Read On

12

Adventures in a Woman’s Body – Chapter 4: Public Humiliation

Used as a playtoy at the mall

I stepped out of the shower and began to dry myself with a towel. On this bright Monday morning, all I could think about was what happened on Friday night. After being gangbanged and cumed on thoroughly, Daddy drove me home that night. On our way there, he explained to me the situation that I am in. Daddy took out his phone and showed me pictures he had taken of me being a dirty little whore....Read On

12

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

12

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

12

Late Night Bus

Ben makes and receives a deposit at the depot...

It's a beautiful, foggy English night. Panting, my lungs aching from the cold, I reach the bus stop at a dead run skidding to a halt on the loose crumbling tarmac. The salty taste of Steve's cum still fresh on my tongue and my anger unabashed. Catching a breath, I realise just how much I love nights like these. The ubiquitous street lights struggle to penetrate the gloom of their...Read On

36

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

33

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

33

A Whole New Me - Part 1

Borrowed panties and a day with my friend reveal a whole new side to me!

“Honey! Are you around?” I shouted from my room, rummaging through my drawers and naked from the shower. “What’s up, sweetie?” My girlfriend, Lisa, popped her head around the bedroom door. Her eyes taking in my body and a cheeky smile forming on her pretty face “Oh, looking good.” I wasn’t the most muscular guy but I wasn’t fat at all and Lisa always claimed she liked my body not being...Read On

33

The very first time....with lots more to come...

My very first sex as a crossdresser.

I guess we all remember our “first time”, and in my case the first time I was with a man while dressed was a awesome experience that I still remember vividly, and it happened by accident.   I started crossdressing when I was about 14 due to my fascination with sexy women. The first time I slipped into a bra and panties and put on mascara and lipstick I knew I was hooked. I felt...Read On

29

A Tale of Two Clitties

A notice posted on a bulletin board in an adult bookstore leads to a white hot sexual encounter

A Tale of Two Clitties One day I was checking out the bulletin board in a local adult bookstore. My eyes danced across the listings. Dungeon masters, couples looking for a third, but then I stopped, there it was, "Lonely virgin crossdresser seeks same". My heart jumped in my chest, and my cock twitched in anticipation. I tore off a tab with her number and promised my feminine side I'd call. ...Read On

29

The Slut Within

This is my first story. If you like it please comment and I will write chapter two :)

I was 22 years old at the time, and I had been crossdressing for a few years. For some reason I could never control my desire to put on women's clothes and prance around my apartment looking all sexy and slutty. Normally I can never decide what specifically to wear as I like to change it up all the time, from wearing latex lingerie to sexy roleplay outfits and beyond. I am 5'9 with a...Read On

29

How my Best friend gave me what I always wanted

My Best friend discovers my naughty little secret

The day started from me being all alone in the house for a full day. My parents and sister were out and wouldn't be home until the next day. I decided that I would give my best friend a call and get her to come over to see me, we hadn't seen each other in quite some time. She was just as eager to see me as I was her and we were both very excited as we really enjoy each other's company. Now...Read On

25

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

19

The Worm Turns-Part 1

My submissive girlfriend turns into my dominant wife

I must have read about a million of these stories and I have to confess that mine isn’t so unique--maybe only in the details, but not so much in how things started or how things ended. You can probably write the first lines yourself: “Things started out so innocently. We had a typical relationship that somewhere, some way, took a dramatic turn that I never saw coming. At first, I was all for...Read On

19

Bo Peep and the neighbor

crossdresser role play

It had been a hot summer and I had no luck finding a job. My parents did not seem to understand that there just weren't that many companies hiring that year due to the economy so they had really been pressuring me to find a job. They all wanted someone with experience but having just graduated high school I had none. I was nearly at my wits end so when I was asked to house sit for my uncle...Read On

19

Christmas Shopping

My favorite thing about the holidays is that I can freely shop for lingerie without feeling nervous. Plenty of guys buy sexy underwear for their wives and girlfriends so there is always a feeling of freedom at this time of year to shop and take my time. I could really spend hours in Victoria’s Secret looking at all of the pretty, lacey thongs, boy shorts, bras, and garters. On this trip I...Read On

19

My Lesbian Lover

My first adventure out as a woman ended in the arms of a woman!

My wife was trying to come to grips with the realization that I cross dressed, with marginal success. Part of her plan was for me to meet in the Twin Cities with other CDs so I could have a ‘safe’ place to dress up, away from our small town. To be safe, I was to drive up, change clothes there, meet with my friends and then change again for the drive home. A good plan … a safe plan … but not...Read On

19

Afternoon Delight

Hot afternoon session with two gorgeous ladies

I was stuck in the office on a pleasant sunny day in late summer, daydreaming about the afternoon of delight that lay ahead of me; I was meeting up with my lover, Kate, later that day. Kate is a girl I have been friends with now for a number of years, we met through some mutual friends and hit it off straight away. We are both in relationships of one kind or another but we are good together...Read On

19

Mom's Old Boyfriend: Part One

Courtney seduces her mom's old boyfriend and sleeps with him, all weekend..

It happened quite by chance and we managed to keep it a secret, ever since. I was home alone on a Friday evening wearing my mom's favorite black lace lingerie and her old boyfriend, Ron, came by to see her. He still had a key from when he was seeing my mom and he walked in without knocking on the door, startling me. And he caught me playing with myself through the sexy little black lace...Read On

19

A Great Date

A first date that I hoped might lead to a first steady boyfriend

I was so excited to sign online and see a message from my sexy college boy. We hadn't spoken in a while and I guessed that we would never get the chance to finally meet. Many a night had I masturbated thinking about his lovely cock, though I had only pictures to please me. It turned out that he had been thinking about me too. "I can't get you out of my mind," he said. "I need to meet you....Read On

65

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

28

Emmy's Games (Part 1)

Emmy takes control. Continuing on from the original encounter 'A Surprise Ass-Fucking in Panties'

“Put my panties on,” says the text message from Emmy. It is 9:30am and I have just woken up. I look across to the bedside table and see Emmy’s panties sitting there all dried out from last night's shenanigans. I lean over and pick them up, and can’t resist the urge to hold them to my face momentarily and savour their aroma. I do as the text message asked and put on Emmy's cotton panties....Read On

15

Becoming Mary - Part II

A girl discovers her dominance while a guy discovers his submissiveness

When Lucy had told me about Amanda liking men wearing panties I thought she was talking about a fetish thing. I didn’t realize there was more to it than that. About a week later I had just arrived home from work when I met Amanda in our apartment hallway. She had been to see Lucy and was on her way out. “Hi Amanda,” I said as she stepped into to the elevator, “How are you?” “I’m fine,”...Read On

15

My feminine Urge Satisfied

My feminine urge took me to a new level at transforming myself into a sexy woman.

I had a three day weekend for me to dress en-femme, and so I took advantage of it. I was not looking to do anything other than dressing, behaving, and acting as a woman. I was content to just relax and be feminine at home without any expectations. I don’t know why I felt as such, except that I needed just to enjoy being feminine and doing so alone. With that in mind, when I got home...Read On

15

Park-n-Play

State parks are not just for nature lovers...

Being the social butterfly that I can be at times, I was checking a website that listed my area to see of there were any 'cruising' areas I could check out in hopes to share my fetish for crossdressing and pleasure. There were several areas, too many to choose from, so I opted for a forested state park. Since much of the funding for the parks in Ohio have been suspended or cut, the chances...Read On

15

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