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6

Caught by Uncle in Aunts things

When I was a young boy, I started to find a fascination with feminine things.  Not sure how it started, but one day I found myself trying on some of my Moms things and enjoyed the feeling.  The issue I found early was that my Mom was very vanilla in her things, so I started to explore with an Aunts things, one I spent a lot of time with, as her son and I were very close.  She had very...Read On

30

Humiliated by my best friends

I had recently met a kinky lady online who agreed to be my mistress on a frequent basis. Tasks she set me included wearing panties to sleep in, leaving a butt plug in me, while we chatted and other kinky things. Last night, while we were chatting, I told her I was going to a friend's house with a few of the guys, to play cards and have a few drinks. Her dominant side took over and she told me...Read On

28

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

41

Mom made me a Fluffer

another story between Missy adventures. Enjoy and please rate and comment all stories. :)

For most of my life I never knew exactly what my mom had done for work, neither did I know who my dad was. As such I just continued with life and thought to myself that I would find out what she did in time. My curiosity first peaked when I was 16, I was looking for my moms purse so I could exchange some of the money I got mowing lawns for people around my neighborhood for different bills....Read On

42

Neighbor fun

Slutty fun with neighbors

It was a typical Friday night. I would hurry home from work to complete my ritual. Take all of the necessary steps for a lot of anal sex, shave all over and transition from a male to a female. I put on a typical “uniform” for the trip to his house. A lacy black top with a lacy black bra under (looked more like a teddy than a top), a short pleated black skirt, black stocking, garter, and...Read On

17

My Parents Friend

Get's Me Hot Every Time I think About It

The year was 1987 and I was home on leave from the military. One particular Saturday night my parents were haveing a get together with some friends so I decided to go out and try and find someone to have fun with. I couldn't decide what to wear until I just decided on what I thought would make me look sexy. I grab my things and head into the bathroom and put on my sexiest black...Read On

30

Chelsea's New Slut

Chelsea makes me her new slut and begins to train me.

            I was wondering why Chelsea wanted to go swimming with me that day.   She had never shown interest in hanging out with me before, but I figured why not go for a swim with friends.   I thought she was way out of my league; she was 5’ 9’’ with beautiful straight black hair and huge double d breasts.   I was just 5’3’’ and a science nerd.   I mean she said it was just between the two...Read On

18

Smooth Sensation

A t-girl get what she wants......

  God I was glad to be home, a two-hour train nightmare. Every stop from Liverpool Street London on the 6pm slow train to the dreary little Essex village that was the only place I could afford to rent a studio flat. My only consolation was the bag of goodies I brought in my lunchtime and the anticipation that tomorrow was Friday and my big night in with my mysterious blind date. I had...Read On

51

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

12

My First Cock

My cousin's Suprise for me

I am now Staying with my cousin after my previous story so I can dress up as much as I like.  my Birthday was coming up soon and my cousin said she would have a celebration all weekend for me as it was during the week she said this would be my entrance into womanhood.  It finally arrived this weekend I thought would be the best I just showered shaved what body hair I had off then left...Read On

37

TV Repair Man

DISCLAIMER: Story is merely fantasy and completely fictional. So please do not believe this happened to me or ask me questions about it, thinking it is true. I am writing from the first person perspective simply because it is a fantasy and it’s just more fun that way;) About a month ago my TV broke and it is kinda big and expensive, so I decided to have it fixed rather than buy a new one....Read On

16

Becky's Video

I watch a movie that surprises me in more ways than one.

I suppose I was the one that first mentioned porn to Nikki. We'd been chatting on a girls' night out and laughed abut how I'd never found any porn in the house. She giggled and said I was bound to find some sooner or later – all men had some, somewhere. A few days later, I'd completely forgotten our drunken conversation and so when Nikki showed up at mine after you'd gone out with...Read On

50

Been A Long Time

Once I got married I pretty much gave up my crossdressing lifestyle to lead a more "normal" life.You know,settle down,have a couple of kids. I was a happily married man with two kids,what could be missing? Well one day while at work,I was on the internet and stumbled onto a crossdressing website,and all kinds of memories came rushing back to me. The feeling of sexy panties,bras...Read On

13

My first Cross Dresser and me

My first cross dressing experience

I laid down beside her and gave her the soda. We sipped slowly and talked about what had just happened. I sat the sodas on the night stand and moved up closer to Toni (a name we will use for this article) crossing my leg over hers so that my clitty rested on her nylons. We kissed for several minutes as I played with her nipples thru the silky bra. Toni looked up with lust in her eyes and said...Read On

41

Susan is Complete

Love of pantyhose turns me into Susan

Like most of us, my cross dressing started with wearing pantyhose. This is a true story. My older sister (she was 14 and I was 9) would wear them to school (private school with uniforms) everyday. She started to notice that I would stare at her legs when she wore them. To this day I don't know why, but she would tease me trying hard for her not to be obvious about it, letting her skirt hike up...Read On

11

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

57

My First Boyfriend - Part One

I learn to cross dress and get a boyfriend

Since my family had moved to our new house, Steve and I had become best friends. He lived next door and had moved in about a month before we did. With both of us being the new kids on the block we bonded quickly. He was two years older than me at eighteen and I had just turned sixteen a few months back. He was also taller and had more muscles than I did. He had tan skin and black hair where I...Read On

31

Sissy at the Bookstore

Or how I humiliated myself in drag

I had gone to adult bookstores for many years and had done it in drag many times but never dressed as a sissy and never during the day. On this day I was so involved in humiliating myself that I decided that I need to take that extra step and I did. I had checked into an adult motel the night before and booked for two days so I had a lot of time on my hands. The night before I had pranced...Read On

15

In Wonderland, Pt.1

Costume mandatory...

When I was in high school I was always very camp, which was probably why almost all of my friends were girls. This was definitely why I first ended up crossdressing. I was sixteen and round one of my 'girlfriends' house for a few drinks on Halloween before we went to a house party nearby. I never much cared for Halloween, so just came as myself. When I came in they all sighed since I wasn't in...Read On

42

Mike's new girlfriend

It started as a typical Monday really; I waved my wife off to work and then went upstairs for a long bubble bath and shave, as I stood drying myself and rubbing baby lotion into my body my cock started to grow as I got excited about the morning ahead. I quickly put on sweat pants and then raced to the outbuilding at the back of the garden to fulfil my cross-dressing desires. I opened...Read On

56

Do you want to wear my skirt?

Katie caught me looking at her skirt and made me wear it.

As I sat in the meeting I couldn't take my eyes off her. She was young and so cute and she was wearing a short pleated wool skirt. The skirt was a pink and light blue plaid color. She would cross her legs and pull the skirt down being sure not to show too much. When we went on a break many of us went outside. It was a nice comfortable fall day. I watched as she came out and stood by herself....Read On

11

The Young Crossdresser Part 2

So after my little adventure at mom and dad's bookstore,the next couple of years were uneventful. I did have sex a couple of times with Phylis,the older lady that was part of mom and dad's swinger group. I knew that I was wanting something more,something was still missing and I kept thinking back to how the guy's cock felt as it spewed cum into my panty covered ass. Now I was 15 and...Read On

42

Telling Mom I'm A Crossdresser Part 2: The Adult Store

Missy goes out and meets her first gloryhole. Please comment and rate all of my stories. :)

I awoke the next morning a little groggy as I slowly recalled the events that had taken place last night. I rubbed my body up and down feeling how the latex had now become a little sticky and how my ass and cock were still sore from the pounding I had taken. I read the note again left by my mother and decided to make breakfast as I was for when she arrived.   It was just past 9am when I heard...Read On

34

Caught

Based on true events....

A couple of years ago I had a girlfriend named Sara, we met at work and were starting to have a great relationship. In the bed things started to get interesting and we got more and more kinkier ever time. We would tie each other up and and play with each other. Then we started using chains and gags and having a great time. Now, she has always had bisexual tendencies but at the time I...Read On

52

Becoming Ginna

First time sucking cock, first time fucked, first time girl !

We were just over 16 years old when I and my childhood best friend Tim, discovered masturbation. And once we did, we couldn't have enough of it. More often than not we would be at secluded places jerking off over porn magazines. From then onwards I realised I was getting more excited watching Tim masturbating rather than the porn, and soon I started wondering rather intensively how would his...Read On

18

Caribean Vacation part 2

Lost luggage leads to wearing girlfriend's panties as a swim suit and more

We strolled down the hall to the elevator. I did not notice what floor we went to, as I was so pre-occupied examining my sexy self in the reflective surface of the elevator. We got off the elevator and walked down the hall to a door marked 469. “This isn’t the dining room,” I objected. “No, this isn’t,” she replied as she knocked on the door. “Who’s room is this.” I asked. Before...Read On

25

Prom Date- Part 1

Jody is forced to dress as a girl for prom.

Jody was pretty much a typical 18 year old boy. He liked sports, hanging out with his friends, and playing video games. However, Jody had one deep, dark secret. He was addicted to wearing his sister's clothes. Every time the house was empty and he had the chance, he would sneak into her room and try on something pretty. Jody was always mortified of getting caught so he was very careful....Read On

13

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

11

Crossdresser and I at Costco

I went to Costco over the weekend with my friends girlfriend. She went off shopping, and I went off to get a few things. I walked down some random isle, and saw a girl leaning down. I snuck a peek at her butt and saw a little bit of a thong showing over the top of her shorts. She was wearing a blue hoody. I looked up and saw that she had really short brown hair. I tried to see her face, when...Read On

21

A Fantasy to Remember

Halloween was rapidly approaching and my girlfriend of 2 years was planning something big. She had been a stripper for 10 years and was as kinky as they come. She and I had done a lot, so only a few of her fantasies were left unfulfilled. She had already had women and men, group sex, bondage, been a submissive and a dominate. We had a no holes barred policy. I could have any hole I...Read On