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Crossdressing

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19

Jack's Little Bitch

Learning to be a girlfriend

Steph had been gone for about one week out of her two week visit to her Mom. She'd asked me to pick up the mail and water the plants while she was away, because her boyfriend, Jack, was also going to be away for the month on a business trip abroad. “Jack wouldn’t remember to water the plants even if he was there,” said Steph, laughing. “At least I can trust you.” Steph was right...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

32

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

21

My First Time

A true Halloween cross-dressing story

I met Lydia while living in Florida. I had recently won a law suit and didn’t need to find employment for a while, so I spent the first three months partying. A good friend had sponsored my membership at a well known and popular yacht club. They had a public side and a members-only side; the members-only side had better bands and more folks. If you parked your yacht and paid the docking...Read On

21

Halloween

Boys will be boys

This story is not to be copied or moved to another web site Well here it is Halloween and I have an idea to dress up with my older bro and take the two younger bros out to trick or treat. When the big night came I got some of my sisters things to dress up in. I took all I needed to look just like her with the panties bra and skirt and blouse with a short jacket over it all. I must say...Read On

14

Sissy Slut Gets All His Holes Filled

Desperate sissy slut boy gets what he wants.

He was waiting for me as instructed, dressed in the bag of clothes I had left for him earlier in the week. I entered the motel room to find him sitting on the bed in the mini skirt, sheer blouse, lace topped thigh high stockings and stiletto heels from his goodie bag. With his legs crossed, he appeared to be quite demure but I knew the desperate, horny slut that was raging beneath the...Read On

10

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

16

She'll Never Know... (Part 1)

A young man discovers a taste for the finer things in his wife's lingerie drawer.

Once again they had argued before she went to work. The reason was also the usual one – sex. This particular morning Mark had woken unusually early, with his usual erection. Deciding to test Clare's mood, he had rolled over and nudged his naked penis against her, just after the alarm had gone. Letting his hand slide up her thigh, she had moaned gently and pushed back into him, letting his...Read On

32

Ray and the Halloween Party Part Two

Part two of my wild night at the Halloween party and with Ray...

   When Ray and I arrived at the front door at Sharon ’s house I noticed my lipstick on Ray’s lips from passing the tequila bottle and as I was wiping if off with my fingers the door sprung open. Sharon was dressed as a Playboy bunny and she looked surprised when she saw us. I thought it was because she recognized me but evidently not. “Well, well, Ray, you dirty dog....Read On

38

Debbie's Place

A crossdresser gets more than he bargained for

My girlfriend, Linda, was kicking me out of the apartment for the night because her sister, Sandra, was coming to stay. Linda didn’t want her parents to know that she and I were living in sin together. I found it all a bit far-fetched that a girl of 23 years old either couldn’t or wouldn’t tell her parents where to stick their beliefs. But, I knew well enough not to argue with Linda over...Read On

12

An Uneven Christmas

He is dressed up by a girl for his friend's entertainment.

By Christmas, Sarah and I had been ‘dating’ for a few weeks. If you could call it that. I had been spending a lot of my time with her, but I often felt more like a servant than her boyfriend. Most couples might curl up together to watch a film, I was more used to curling up at her feet. Worse, I was sure my friends realised there was something odd going on. Mark, who had the room next to...Read On

12

A Gift for Daddy

A CD Sub gives her owner a new toy...

"I brought you a present, Daddy," Stephanie said, giggling, as we stood on the porch in the run-down neighborhood in the industrial part of town. The man standing inside was in the shade inside of the house and I squinted to get a look at him. "Eyes down," Stephanie hissed, elbowing me. I did as she said and smiled inwardly. She was usually very submissive and proper when we were together and...Read On

19

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

6

My Night at the XXX Video Theatre - Part One

My adventure in a bad part of town at an XXX Video Theatre

It was almost 2 AM when I pulled into the Big Town XXX video theatre in the southeast part of where I live. It was a Saturday and the parking lot was full. I had never been to this particular theatre but it was in the adult theatre chain that I had been visiting for the past two years. Each theatre is different depending usually on the part of town where it is located. Southest part of my...Read On

27

The Meter Reader

Caught Wearing My Bikini

I'm basically a 'city boy' but one summer decided to rent an old two story farmhouse in the country. It had its good and bad points. The bad was that it was quite a way from town. I was working nights at a bakery and had to drive the twenty or so miles to work in the dark every night. The good part was that it was secluded. I could walk around the house in just my bra and panties, a short...Read On

45

Pamala's first adventure

This happened to me years ago when i was in the Army

I joined the army after I quit school in the 12 th grade. After joining the army it put a crimp in my dressing up as a girl. I did wear panties whenever I got the chance but I really wanted to dress up completely as a girl. I wanted to go out dressed and I have to admit I was attracted to several guys in my unit. My third year in the army I went to Viet Nam in December 1967. I was in the 101...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

32

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

21

Crossing A Different Line

A married family man's growing interst in female lingerie leads to his being taken as a woman.

In my personal journey from straight, married heterosexual to bi male, I discovered, along the way, that I was aroused by women’s lingerie. It started with trying on a pair of my wife’s nylon panties. The feel of the silky material, and the sight of how it fit, quickly brought on an erection. I used another silky pair in my hand to jack myself off, being careful not to get any cum on the...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

An Introduction to Crossdressing

Up until this point in time my crossdressing has consisted of wearing stockings or pantyhose and enjoying some anal penetration with one of my toys. I have recently had strong desires to move further but really didn’t know anyone that could help me. I was chatting recently with one of my friends on Lush about our mutual desires and needs. I had said that I really would like to do the whole...Read On

15

The Feminisation of Michael. - Chapter 4

The Feminisation of Michael. Chapter 4 Sue had replenished my wardrobe again with new work clothes and had taken the secretary theme to heart! The skirt suits had been replaced with pencil skirts and pencil dresses. The blouses had been supplemented further with lace and ruffle fronted blouses. There were also several ribbed tight fitting cardigans in black, red and various...Read On

19

my discovery

my story of becoming a crossdresser

Here are some stories about my sex life and exploration of who I am. Before I started cross-dressing, I fell in love with high heels, mainly cumming in high heels. When I was younger, my parents used to have a large walk-in wardrobe and when they would go out at night I'd search for my dads porno mags. One night when I was reading some mags and my parents were out, I got a bit too excited...Read On

15

A Little Walk

A late night walk turns into a dream come true

I love autumn nights, the air is cool and the weather is still nice enough to allow for some late night strolls to the park and through near deserted streets.   Another bonus is that the nights are longer which means that I could escape the seclusion of my home earlier to enjoy the freedom of the outside while dressed as I so enjoy doing. For this particular outing I had decided to go with...Read On

15

the summer I became Suzie

this is my fantasy

I was 18 years old and taking estrogen for about two years. As my ass and tittles started to grow my desire to dress up became all consuming. I wore sexy panties to school everyday and the excitement about getting caught, grew as well. I was very tiny for my age and picked on by the jocks at school regularly. I'm 5foot 5inches tall, with long brunette hair and blue eyes. I had no body hair and...Read On

23

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

24

All by mistake

A chance encounter

It all began by mistake. I had spent the morning at home, relaxing in one of my favourite outfits. I was starting to think that work beckoned, and had begun the transition back to drab. I took off my wig and make up, but decided to keep my panties, tights and bra on, as my clothes would hide what I was wearing. My attention was caught by a news item, and I sat watching the television for...Read On

27

Meeting my Ex-Girlfriend's New Boyfriend

being seduced at the bar

Not long after I got out of the service, I met Trish at a house party. She was a hot little brunette with a great body and we hit it off right away. After a few months of dating we ended up moving in together and she was a great lover...with one little quirk. She always wanted me to wear a pair of her panties while we were having sex. I readily obliged because she was so good on her back and...Read On

18

The Slut Within part 2

part 2 of the slut within and if you like it PLZ comment :) enjoy!!!

As I continued on my knees, I felt my little thong riding up my tight little butt. My skirt got in the way of spreading my legs and my tube top and my skin was all sticky with cum. Thankfully, I wouldn’t be wearing any of this much longer. Their watching eyes so aroused my slutty nature. I took off my tube top and skirt leaving my fishnets and six inch heels. I also wore a black thong and...Read On

37

Becoming Chloe

Caught in my wife's lingerie...

It was a mistake. I realise that now. I just don't know what came over me. One minute I was tidying the bedroom and the next minute I'm lying on the bed in my wife's basque and stockings, and using her panties to have the most fantastic wank I've ever had. I realise now that it probably wasn't a good idea to go through her underwear drawer while she was at her Mother's, but the lure of...Read On