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Crossdressing

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32

Mike's new girlfriend - part 2

The following Monday couldn’t come round soon enough. It had been a long, difficult and very confusing seven days at home, with my wife, Amy. I had been so distant and argumentative with her and I could see how upset she was. However all I could think about was Mike and how much I wanted to be back in his arms and have him make love to me again. Again, the morning started in the usual way....Read On

20

Jack's Dirty Secret

Jack walked into his bedroom, seeing his wife laying on the bed with a dildo in hand.

Jack and Mary had been married for ten years or so. Mary never thought that Jack would keep such a large secret from her. She sat at the house all day and did laundry, Jack's and hers. She never usually did his since he's picky, but she was bored and it needed to be done. As she was putting away some of Jack's clothing in his dresser, she saw something. It was a shiny pair of silk gray...Read On

20

Busted by My Step-Sister's Boyfriend - Chapter 1

My Step-Sister's boyfriend catches me watching the two of them having sex

My step-sister Alicia is two years older than I am and built like a Greek Goddess with her braided blonde hair, slender body, long silky legs, tight round ass, and 36D breasts. Her boyfriend Bob is a college freshman soccer player who regularly spends the weekends at our house. My parents do a lot of weekend travel to relieve the stress of their jobs, so the house is virtually ours to...Read On

30

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

16

Mom's Old Boyfriend: Part Two

Courtney becomes an escort like her mother, after fucking Ron good like she did.

Having adopted my mother's appeal for wearing sexy clothing and turning on men, I had just sucked her rich former boyfriend's cock while she flew to Las Vegas for a long weekend with her new rich boyfriend. Mom had a love for the jet-set lifestyle and I was sure she was enjoying staying in an exclusive hotel and fucking her new boyfriend's brains out when he wasn't at the table gambling....Read On

16

The Sexy Girl-Next-Door: Part One

Wearing too many sexy clothes gets Courtney a big cock inside her.

As a sweet sixteen-year-old boy, I started my life of having transvestite proclivities. Being sexy for men and making their cocks hard for me became my favorite thing to do for pleasure. I already had a boyfriend, the blonde college boy lifeguard at my community swimming pool. He had seen me wearing some sexy little hot pants and come on to me, one day. The fact that he was handsome and all...Read On

23

Where do I begin? Chapter 1

Young man lets his inner woman out during an encounter with an older man.

Where do I begin? I’m normally not very open about my private life, seeing as I grew up under the pretense that secrets are meant to be secrets. However it seems I have come to a point where I am comfortable with who I am and where I have been. Comfortable enough to bare to you all my deepest secrets. Deep breath in, slowly let it out. My name is Alicia, well that's my new name, my old...Read On

30

Summer sexing a friend

A tale of sex, not love.

The night was especially dark that night. The moon was hid by a blanket of clouds. It was only 6:30, but that time of year it always gets dark that early. I left the empty bar after a couple of drinks, but I didn't want to go home. I wore skin tight jeans, a cute little tee, some cute tennis shoes, and a sexy underwear set. I took a little detour and found that Rod was having a fire....Read On

6

Friday Night Maid - 1

On Friday nights she goes out with friends, He becomes the Maid for the night

Friday Night Maid - By: Diane Leonard I am a Friday night maid. After a week of hard work, I relax by dressing up in a sexy maids outfit and serving, pleasing and pleasuring my wife. While she is out dancing with her friends, I am dressed up as a Friday uniform waiting for my wife to return home. She doesn't like my fetish, but this agreement, once a week seems to work for us. But ...Read On

23

Initiating Stephanie

Stephanie's secret is discovered and exploited

** Discovery ** The first time I set eyes on her, she was wearing the sluttiest underwear one can imagine. Totally oblivious to my presence, she was admiring her scantily clad body in the full-length mirror on the wall. The lingerie was black, my favourite colour , sheer in texture and cut to a design that left little to the imagination. Black leather, ankle boots adorned her feet...Read On

14

Pure Innocence

Well, maybe not...

It was an unseasonably warm Saturday and I decided to go out for a walk and clear my head. Instead of my normal guy garb, I decided to go out dressed as Aimee. But I was looking for a different look—totally cute and innocent which was not like me at all. I put on a little blue cotton dress, a pair of sandals, and donned a blond wig. The wig was long enough that I could put pigtails on...Read On

17

My First Time

Fist time oral

This a fantasy of mine and my first story that I am submiting. For a long time I had thought about oral sex with another man. I was married a few times and it never really satisfied me completely, I loved sex with them but I longed for sex with a man. I had wondered what it would be like to find a man looking like a woman, I talked to female friend and she helped me to dress up like a sexy...Read On

22

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

15

Felix becomes Felicity - Chapter 2

Life gets more girly for Felix!

FELIX  becomes FELICITY Chapter 2 My Mum and Sister went downstairs and I had a moment to myself looking in the mirror.  I didn’t recognise me in the reflection I saw a teenage girl, a very attractive teenage girl! I joined my Mum and sister downstairs. I was becoming better on the heels “Mum I have to reiterate that this all ends in 6 weeks time right?”, “Of course sweet that’s...Read On

19

Number Off A Bathroom Wall

Back in highschool I got a job working at the local mall at the Sears store. I was a stockboy and all around general gopher. I would always wear sexy outfits under my work clothes. On my second day I was asked to clean the bathrooms and I did. I started in the womens room,kind of hoping I would stumble onto a pair of panties or something,but no luck. I then work my way over to the...Read On

15

my first date with Ben

I had been chatting with Ben online for a while and we had talked on the phone several times before I decided to meet with him. I had met him through Craigslist so he knew what I was all about from my ad. We arranged to meet at restaurant for an early dinner so there would be plenty of people around. That Saturday, I spent my time getting ready. I showered and shaved smooth and used a...Read On

19

Just For The Taste Of It

Vanessa is trained to love the taste of cum

Many years ago, before I was the experienced sissy girl I am now, I was living with a man named Jake. Jake took me under his wing. He wanted to help me become as girly as I could be. One of the things that he wanted to get me used to was the taste of cum. I had tasted it before, but only my own and his. Jake wanted to make sure that I was a cum expert. He said to me, “A true sissy...Read On

22

My First Date

I had met Pete over an on-line dating site, and we had chatted for several weeks and developed a rapport when we decided to have our first real date. We agreed to meet at a local shopping mall parking lot and would do some shopping together. I spent the morning shaving my body smooth and getting ready. I went with a natural look for my make-up, and peachy pink lipstick. I slipped into a...Read On

18

My wife finally indulges in my fantasy

This story is a work of fiction I wrote for my wife.

I come home from work to find you dressed in your sexy jeans, a tighttee shirt, and a pair of heels. I can tell you are horny by the way you tell me to get into the shower and that my clothes are laid out for me after I finish cleaning up. My cock throbs as I shower and lather my body up with some scented soap. I know you want me squeaky clean so I insert a soapy finger into my ass,...Read On

16

How It Started

I looked and saw her panties in the hamper.

At twenty five and being a blonde haired blue eyed light skinned guy, I had little hair except on my head. So, it didn't take long to achieve the smooth feminine look that I wanted. Of course, I left some "down below" because I looked young and if I shaved it all off I feared looking underage. My blonde hair was long, during the week I wore it in a guy style. On the weekends it was different,...Read On

12

Discovery

Kyle is discovered indulging in his secret passion.

Discovery, one of the greatest fears he has. All others take a backseat to his fear of being discovered indulging in his passion. You see Kyle is a cross dresser. Like so may others he doesn't know where this desire to dress up came from, but soon it was too strong to ignore. He started out with pilfering a few items from his sister's room and wearing them behind closed doors when the house...Read On

9

My Story

 This is my story in a short form of how I became me a 22 year old black gay crossdresser. I've always had gay tendasies from as long as I can remember but at age 17 I met a guy who house I use to walk by after school and we would chat, after a while I told him about me and he said he always thought I would make a cute girl, now he was white and a bit older than me at 30.  After a couple...Read On

33

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

13

the day i became Suzie chapter 4

this is my fantasy

I went back the next day dressed sexier than ever, but Jack and Harry did not show up. I waited for hours. Then cried all the way home. I cried myself to sleep three nights in a row. Now I knew how a women feel after being fucked then forgotten. But then on the fourth day Harry called. I instantly went into my sweetest voice and asked, "Where have you been?" "Guy stuff Suzie.You...Read On

31

An Unforgetable Experience

Caught By The Best

I will never forget the day Carrie enter my secret world. It was the summer I was 17, I had been dressing my sisters clothes since I was about 8yo. In more recent years I had started buying a few of my own clothes and lingerie nylons and make-up. It was a Saturday and I was home alone and decided it would be a good day to dress and be girlie, excited about my day I waxed my legs and bikini...Read On

25

The Compromise: Part 1

A suggestion from a counselor sets in motion a fantasy compromise that changes my life forever.

My wife, Ally, and I have been married for eight years. What once could be considered a torrid love affair had subsequently lost its sexual passion. We don’t have any children, both being career focused, but our sex life had become quite stagnant from the steady grind of life and over-familiarity we had with one another’s sexual tastes. That is, until one crazy night changed everything. ...Read On

12

My First Encounter

This is about my first sexual encounter with a man

I had been cross dressing for years but only in private. I had also had a thing for bondage for a long time. A couple of years ago, I met two other cross dressers who were into bondage. We had been getting together every couple of months and playing bondage games with each other. We would take turns tying each other up and taking photos and videos. But, it was always clear that the other two...Read On

4

Night at the Video Store, part 3

bimbo crossdresser cruises video store in Black part of town

There I was a sissy bimbo dressed like a slut in a short black micro mini skirt, spike heels, lots of junk jewelry, huge platinum blonde wig, shoulder strap white fur purse and, of course, perfect make up. I had never been to this video theatre before and was nervous at first, but I waited for my eyes to adjust to the darkness and then moved into the theatre area. Screen five was recommended...Read On

8

Adventures in a Woman’s Body – Chapter 5: Secretarial Duties

Serving some very important people as the secretary

John waited for me to finish eating my cum burger, and then he told me to get up because we were leaving. I stood back up onto my six inch stilettos and walked with his arm around me, which firmly grabbed my ass. We exited the food court and made our way to his office building. The mall had a vast underground network so we were able to walk to his workplace without going outdoors. Along the...Read On

18

Office - Caught 2

I couldn't focus, my head was racing with all kind of thoughts. I had no idea what this would result in. My manager and teammate noticed something was wrong. I just told them I was coming down with something and felt ill. As there was only about an hour before closing time, my boss told be to finish early and get myself home, dosed up and to recuperate over the weekend. I didn't need to...Read On