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Crossdressing

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27

Changing Room

I had finally worked up the courage to explain to my wife that I liked to wear panties. I dressed off and on in her clothes for years, and she didn't suspect a thing. Before that, when I was single, I had taken to snatching the odd pair of panties out of the dryer in whatever apartment building I was living at the time. When I was a little boy I had always wanted to be pretty like a girl,...Read On

21

Learning to be submissive - part 1

A gift comes at a cost

Before the days of internet chat rooms and social media I was very lonely as a young cross dresser. I can't speak for everyone of course but I would use telephone messaging services to talk to like minded people. I had received my first mobile phone for a recent birthday and I would often call up to chat to people. Sometimes things would turn into phone sex and on the rare occasion I would...Read On

19

Miss Teresa's Beauty School

Princess has been caught stealing at work and has to pay the price!

I wrote this story as a narrative and I made it into a 45 minute audio story. The Interview: Come in, I've been expecting you. I had a long talk with your boss the other day and it seems that you have a little fetish for women's underwear, isn't that right? In fact-you've been caught stealing things from the other girls lockers. Mostly their panties and pantyhose. Is it just too hard to...Read On

19

Adventure in St. Louis

Cassie's adventures on a night in St. Louis

A NIGHT IN ST. LOUIS Work can really suck. At this moment I am sitting on an airplane wrapping up a three day business trip. Thank goodness I know how to make work fun. If someone gives you lemons, I say make lemon meringue pie, because lemonade is not good enough. What I am getting at is you have to make the most fun in your life, because life is too short. If you have a passion, make...Read On

19

A weekend with Nancy part 3

Get used to it, you're going to be my bitch alot from now on.

Upon arriving back at the car Nancy said that we had to hurry to our next destination because it would be closing soon and then she instructed me to drive while Alice and herself got in the backseat. "Honey, do you know that porn shop up the road a couple of miles?" said Nancy. I nodded that yes I did and I was instructed to drive there quickly. At the porn shop, Nancy suggested that I...Read On

19

My First Boyfriend Part Four

I suck off a bunch of guys at a party and take two home to have a foursome

The drive home from the party was quiet because I had sucked off ten guys at the party and my mouth was sore and we were pretty drunk too. Two of his friends were following us home I assumed to have sex and party. I lay on the seat with my head in Steve's lap and rested while we listened to the radio. I asked Steve how were going to keep those two from finding out I wasn’t a real girl and...Read On

19

My New Neighbor

Slender cross dresser can't resist well-hung guys.

I'm a slender, thirty-two year old, bi white male. I've been cross dressing since my teens and love the look and feel of wearing women's clothes. I'm not into all the heavy stuff like wigs, breast forms, padding etc. I mostly wear lace panties, bras, lingerie, garter belts, sheer nylons and heels. I was blessed with long legs, a slim waist, nice round hips and a very shapely little ass. As...Read On

65

My Strapon Fantasy

A girl helps her boyfriend live out his fantasy

I woke up in the middle of the day and smiled; my girlfriend had gone to work a few hours earlier and promised me a really good time when she got back. I ran upstairs to shower and make sure I was hairless before getting ready for her. I wandered into her room to dress for her arrival. I found a purple sheer thong and matching bra in her underwear draw that would be perfect. I really wanted...Read On

38

The Awakening of Susi

Susi discovers the joys of anonymous cock sucking at a glory hole (true story)

Ever since I can remember I have loved being feminized and being made to wear very slutty clothing. This is a true story of my first experience at a glory hole and a coming of age for my sissy self. I had many female friends who loved to dress me up in their sexy clothes and strut me around in front of their boyfriends. They thought it was cute to see me in full makeup and a wig wearing a...Read On

32

Andrew to Andrea - Part 4

...the next few steps...

Chapter 4 It seemed like the time would never arrive. I watched the clock limp around the dial for the last hour between 5 and 6, but finally the time came…the time to go home. I still felt the pressure, not unpleasantly, of the plug installed by my wife yesterday, and still had the memories of the sensations that I felt each time she activated it…again, not unpleasant. Finally, I had the...Read On

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

31

A Fantasy

This is something that I’ve always dreamed would happen…

I have been dressing in women’sclothes since I was little. My grandmother used to dress me up in her old dresses and pretend I was her granddaughter. As I grew older it started becoming more of a sexual fascination and turn on for me. I have been more a closet cross dresser getting clothes here and there and then dressing up and having incredible masturbation sessions looking at tranny...Read On

26

The Party

After two visits to Bill's I had been invited to a party.

Here I was nervous as anything at the railway station, I had just phoned Bill to tell him that I was on my way as promised. The journey itself was uneventful and I arrived in the next town on time. I walked out of the station my nerves getting worse and scanned around the people all milling around. I couldn’t see Bill and started to worry, my eyes were drawn over to a woman walking towards...Read On

25

Dave and I

Dave called and asked me to go out with him on Friday

This is a work of fiction. Any resemblance to any person living, or dead is purely coincidental. Later that day we sat at the table talking about the events of the past evening. The phone rang. It was Dave on the phone. He wanted me to go out with him on Friday and he wanted me to dress sexy..  I had been with Dave only one time; it was at my anniversary party. My wife arranged everything....Read On

25

Becoming Mary - Part I

A girl discovers her dominance while a guy discovers his submissiveness

Lucy and I had been living together for a couple of months when it all started. She was in her early twenties, and I was a couple of years younger. Up until I moved in with her, I’d lived my parents. My stay-at-home mother had taken care of all the household chores while my father went out to work. It was the typical old-fashioned family structure. From day one, living with Lucy was proving...Read On

25

Taking That First Step

A story from the seventies

Lance was seated on a bench on the tree-lined sidewalk waiting for the store to open. Despite the warm morning air he began to sweat and his heart pounded in his chest, this was a bold step for him. Now, this particular store was located in an older but still very popular outdoor shopping center despite the malls springing up everywhere. It was commonly referred to as a specialty shop,...Read On

20

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

20

A New Friend at the Adult Toy Store

I am usually not this forward, but he was so handsome.

I decided to go to my favorite Adult Toy Store.  Now, this is not one of those dark, dingy places that make you feel uncomfortable.  It is well lit and attractive.  The people who work there are very nice, polite, helpful and make you feel right at home.  So I can go and feel at ease while I browse.  This store carries lingerie, clothing for clubs or stripping, stripper shoes, toys, and...Read On

18

The Feminization of Michael - 2

The Feminization of Michael. Chapter 2 I continued with the “weekend” clothes for another few weeks and consistently had people commenting, laughing and making things difficult when I was out shopping. I continued at work in the more feminine suits and blouses too.  The rumours increased and somehow word had got around that at the weekend I wore dresses and full make up! This couldn’t...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

12

The Feminisation of Michael - Chapter 3

The Feminisation of Michael. Chapter 3 I endured the rest of the afternoon with continued suppressed sniggers and laughter. I was glad when 5.00pm came and I buttoned up my jacket and put my handbag over my shoulder and left with a big sigh of relief. Sue was waiting outside in the car. “Hi Michaela,” she greeted me. “How did it go honey?” she beamed. “Fucking awful!” I blurted out....Read On

12

The Sexy Girl-Next-Door: Part Two

Courtney has a neighborly affair.

Once a girl gets a big hard cock in her, there is no stopping her from wanting another one in her. At least, that's how it was for me after my first fuck with my neighbor, Ben. He had just fucked me with his twelve inch cock, with a big head on it and I loved it so much I couldn't wait to do it again. Our friendship was growing like our dicks were. And I was now having an affair with my...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

12

Stranger Fuck

A crossdresser is pegged in a sex club.

  I noticed the time strike 10pm on my watch as I got out of the cab outside the Red Circle. Hopefully tonight I was going to get lucky. After paying the cabbie and stepping out of the cab, I fixed my tight pink and black striped dress as I stood outside the club. The Red Circle was the most notorious Sex Clubs in the city where couples and singles went to hook up. Tonight was their...Read On

67

A surprise ass-fucking in panties

A friend displays her kinkier side

A very curious thing happened to me the other day and I feel I need to share it with you... I have been 'mildly’ crossdressing for over a year now. I say 'mildly' because I am not into full feminization, I just love the feel and look of lace panties when they are hugging a good looking cock, not to mention the taboo. I have taken to wearing stockings too which feel amazing, it's like...Read On

49

The Adult Theatre

A true story with the name and location changed for a good lush friend.

I got to the hotel early so that I could get myself fully prepared to meet a guy I had been chatting with via a chat room. I decided to wear my favorite pink check mini skirt with my sexiest pink undies to match. I added a white silk blouse and a white garter belt with some white stockings. I took time applying my make up, making sure I had dark sultry eyes and perfect red lips, I wanted to...Read On

48

Dressed Up and Used

Young Crossdresser gets Fucked again

     This is a continuation of my first story "MY First Time in a Dress".  I love reading your comments, enjoy!      I avoided Dan for the next few days by playing sick.  I was not ready to go over to his house again yet.  My ass was so sore the next day I had to have some relief.  I was still having a hard time comprehending what really happened.      I finally went to his house...Read On

43

Gang banged at a private club

This is what happened when a friend took me to a private members only gay, bi, and transgender party

After yet another hot weekend at my friend Heberto’s house, I was packing up and getting ready to go home when he told me he had something “special" in mind for us next weekend. I begged him to tell me what he had in mind but he refused. So I left. My curiosity was peaked. The week dragged on thinking about all of the possibilities. The anticipation was killing me. Finally Friday...Read On

35

A great experience as a crossdresser

Glorious glory hole session

I was born and grew up for the first 27 years in England. Ever since I was 16 years old I have always had an infatuation with sexy ladies lingerie. I used to dress up in my mothers and older sisters lingerie and get very turned on and wank myself off while dressed up. I am now 53 years old and still tremendously enjoy the thrills of dressing up and wearing sexy lingerie. One of my...Read On

35

Surprise Delight

It was a beautiful day outside and it had been a long hard week at work. I decided to pamper myself by taking a nice long bath and just soak my sore muscles. After my bath and weekly grooming I decide it was time to slip into something a bit more slutty to wear around the house (I don't go out dressed up, not quite passable for that step). I walked into my room and looked in my closet, where...Read On