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Crossdressing

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29

Dad Catches Me With His Friend

From an early age like most I started to get a desire to wear womens clothing. I would always take my mom's thing's and put them on and masturbate in them. The feeling was nothing like I have ever felt before. Around the age of 16 I had gotten a job and started buying my own things,lingerie and such with the money I earned from the job. Prior to that,around the age of 13 my mom had left...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

Becoming Anthea

Anthony is persuaded to cross-dress

My name is Anthony and I am twenty-two years old. I have extra-long dark hair and darker eyes. I tie my hair into a ponytail and have a close trimmed beard. I look handsome and enjoy keeping myself in shape. I am a lucky guy as I have a very sexy girlfriend who is two years older than me. Zoe and I met at a mutual friend’s party and hit it off right away. She has short blonde hair and...Read On

18

Telling Mom I'm A Crossdresser Part 8: Bus Driver's and Cops

Part 8 enjoy and please comment at the bottom ;)

My mom and I spent the next few days practicing and exercising with the stripper pole until we felt confident and extremely sexy while doing it, which I have to admit did not take long. One night I came home late from my part time job I had at a local restaurant and took the bus home. I didn't have a car because I hadn’t decided on what car I wanted to get yet and what I could afford. I...Read On

18

Telling Mom I'm A Crossdresser Part 11: Girl time

sorry it took so long and that its a bit longer then my last one but I hope you enjoy. com at bottom

Part 11 It had been a while since my last time as Missy. I had been doing some jobs for people, nothing special mostly working on decks and mowing lawns for neighbors to not only keep up appearances so as to not give to much suspicion of where my money was coming from. This continued for what seemed like 2 weeks before and started to wonder if my fun as Missy had ended. I walked in the door...Read On

18

My oddesy 2 - Liam

A friend cheers me up

It had been a few weeks since Glen's puzzling rejection and I was in a slump. I hated my body more than I had in years. Not even sneaking into my sister's old room and playing dress-up could cheer me. And my best friend noticed. Liam was in most of my classes at school and we knew each other since third grade. He had olive skin and a solid German build. Noticing my gloomy disposition he...Read On

18

Born to Be a Babe

Sexy girly boy ponders the allurement of lingerie.

I don't know why I started wanting to be a girl. But I do know when it started. I was sixteen when I first started looking at photos of sexy models wearing lingerie in Cosmo . These beautiful, statuesque women wearing the sexiest clothes I'd ever seen turned me on so much. In fact, I was more turned on by looking at these women in lingerie than I was looking at the naked women in...Read On

18

Telling Mom I'm A Crossdresser Part 14: Back to the spa and a familiar face.

Part 14, yes I feel it is long but please read the whole thing you will not be disappointed.

Part 14: Back to the spa I'm sorry this story is a fair bit longer then my usual ones however I didnt want to separate thes and have another story with almost no sex in the first one so soon. Having said that I hope you enjoy my story and please read the whole thing. I promise you will not be dissappointed. I woke up the next morning lying next to mom in her bed. I was wearing a pair...Read On

48

Picked up in the Toilets

How an encounter in a public toilet turns into a lot more.

Here I was just turned 16, I liked to dress in girl's clothes and was very curious about cock, no about sex. Oh, god yes! My hormones were driving me mad with the desire to not only dress up whenever I could but also to have sex. Anything I saw in newspapers or magazines about women, girls or with sexual meaning had my mind just a blur of indecent thoughts. This particular day I had...Read On

13

Andrew to Andrea - Chapter 2

Andrea's first small steps.

In all honesty, I should have been mortified by the events of the past few minutes, but I wasn’t…I was excited. I walked into our bathroom and set up the steamiest shower that I thought my skin could handle. I grabbed for my body wash, but realized the scent might be too masculine, so I set it back and grabbed my wife’s. It had a slight scent of vanilla and had a couple of butters and oils...Read On

13

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

13

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

13

A friend with something extra.Part 2

Ian and Grant test the waters.

Ian headed to the bathroom to clean up. As he did he allowed his mind to recall the most recent events of the evening. He arrived at his best friends house for one of their pizza and movie nights and discovers a sexy girl in his buddy's bedroom. He soon discovered that the sexy girl was, in reality, his friend Grant. He didn't look or talk like the Grant he knew, he talked and looked like...Read On

39

She wears the pants, over her cock

I stepped off the plane after three days travelling and was looking forward to going home after a long few weeks of travelling for work. My work regularly has me travelling and I don’t seem to get home as much as I would like anymore.   But it does make it even more enjoyable when I do get home.   Leaving the gate, I walked down the corridor, past the last security checkpoint, and toward...Read On

23

Halloween Fun

First time Out

My friend talked me into dressing up as a female this Halloween. It wasn't much of talking into; I was a closet cross dresser for sometime. The only person who ever knew was an old girlfriend, Mel, a few years back. It was a good thing she was bisexual because she was really into me wearing her clothes. She even mentioned that I looked better in her clothes than she did. So, I started wearing...Read On

23

Oh, Daddy

Making of a cum slut

It all started with an online ad. I had always known I was different. I tried to pretend I liked girls, but I really wanted to be one. Let me describe myself. My name is Tony. I am 17. I'm 5' 10", 125 pounds. I have long blonde hair that girls are always jealous of, but it's always my blue eyes that draw everyone's attention. I was pretty shy and mostly kept to myself. I had a few friends,...Read On

17

Surprise at Girls Night Out

Cassie's Encounters in New Jersey

Surprise on Girls Night Out in New Jersey I explained in an earlier story that my life took a strange turn when I turned forty. I had not been cross dressing for many years, but I had the urge again to bring out my alter ego and the urge was stronger than ever. I really prepared for Cassie, short for Cassandra (I also go by Sandy) by taking a year to buy all the things I needed and get...Read On

17

In Wonderland, Pt. 2

To recap, our protagonist didn't want to dress up for a halloween party, so his girlfriends decided it was time he joined in the fun. They styled his hair, did his makeup and put him into an 'Alice' dress. However, the disguise worked a little too well, as Chris Smith has taken 'Tilly' back to his house after a passionate kiss on the street corner... Chris put his key in the door...Read On

17

Laying the Groundwork

Extending the boundaries with my fiancee

My fiancée and I always have been a bit more adventurous than the average couple when it comes to sex. While we both enjoy the sensual feeling of pure, romantic love-making, we also tend to get a bit rough and voracious when the moment calls. In the past, we had experimented with some anal play, with me initiating most of the contact on her. Fortunately for me, her hands also had wandered a...Read On

17

One of my first times

My first time with a guy

They say you never forget your first time. For me that's kind of true but in my attempts to seduce over the years I've claimed to have so many first times and I definitely don't remember all of them. Being bisexual and, of course, with my dual gender identities I have probably had more first times than most though. I was still cross-dressing in secret in my late teens and I'd never had...Read On

17

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

17

Date with my wife - her story

Today started like any other day, except for one thing. My husband informed me as he brought me morning coffee, "Sweetheart, tonight when you come home, go straight upstairs, cleanup and put on the outfit I have laid out on the bed." He said this with a grin on his face. You know that grin like the one you see on a child's face as you enter the candy store. "But what if I need something?"...Read On

17

Made Maryanne

John is unaware of the female power to crush his manhood

It was 3 am. I was busy whacking myself off in the bathroom when Beatrice caught me. She and I had only been together for a few weeks when I started taking a special interest in her underwear. I loved the smell of her wet pussy, combined with the cozy softness of the cotton panty gusset pressed against my nose. Wearing one pair, feeling the delicate material clinging tightly to my ass, I held...Read On

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

Wedding Night For Ken And Barbie: Part One

Catching the garter at my cousin's wedding gets me a honeymoon fuck like the bride.

When I went to my cousin's wedding in Monterey, California stag, at the reception dinner she had me seated next to the only other male stag invitee, the photographer. He was my age and tall and we hit it off, immediately. Ken was a sports car enthusiast and he told me about the thrilling rides he took along the Pacific Coast Highway. He talked about the beautiful views at scenic lookout...Read On

16

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

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

16

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

16

Hitch-hiking Baby Doll: Part Two

Being a sexy girlyboy for a trucker stud leads to lots of sexy pleasures.

I woke my trucker stud up in the middle of the night by sucking on his cock and making it hard for him. When I had him good and hard, I climbed back up between his legs and let him put it in me again. His cock was nice and big and my ass was good and tight. It felt good to feel like a girl receiving anal from her big Daddy. While we lay on our sides in his bunk and fucked, my trucker...Read On