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23

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

23

Switching roles

She dresses up as a policewoman and plays the dominant part

In most play I tend towards the dominant side but I do like to switch from time to time. One of the most intense experiences of my life, not so very long ago, was an unexpected switch. Halloween night. I traveled by train to visit with my lover. She'd made all the arrangements for costumes for us to attend a party later that evening. I didn't know what she chosen or anything about the...Read On

14

Telling Mom I'm A Crossdresser Part 8.5: Cops and Prostitutes

What Missy needs to do instead of going to jail for prostitution. (continue of part 8)

When morning came, I told mom what had happened the previous night. She had a surprised look on her face and I could tell she was feeling uneasy at the thought of me getting arrested while dressed as Missy as well. We talked for a while and she was glad as well that the police officer was a Missy fan. “We can definitely let him have a free night in exchange for not getting a criminal...Read On

14

Felix becomes Felicity - Chapter 7

FELIX  becomes FELICITY Chapter 7 …We both fell asleep almost immediately. I got up whilst he was still asleep in the morning and put on his shirt loosely over my naked body. I woke him up with breakfast , we kissed and he left late morning.  I had been lucky to escape him not discovering my penis! I had to think hard about what to do about this. I would just have to have to tell him...Read On

14

Jessie's Fantasy: Chapter 6 Turning the Tables

Now that Jessie fooled his friends, who will turn the table on whom?

I was floored by what Tracy had said to me. “Because, the male Jesse is no more for the time being, it is womanly Jessie that needs to go.” It seemed that my love just told me that I had to meet up with my male friends tonight. My mind was going a mile a minute. I already fooled my friends once. But can I do it again? If I do, what is going to happen? What will I let happen? My stomach felt...Read On

14

Jessie's Fantasy: Chapter 3 The Night Club

Jessie's all set for her first night out. Will she catch a guy or be caught?

After an amazing afternoon with Tracy, Suzy, and Brooke regarding my transformation and amazing feminization via sexual acts that wore me out, it was time to meet my friends. Before we left, I called my friend John and told him that female Jesse would have to wait. I told him a little white lie that I had developed stomach flu and had been throwing up all afternoon. John told me that he...Read On

14

What Do You Do When....

The weekend arrives and mom and dad are going out and I assume they are going to one of their swinger parties and won't be home until early the next morning. So I do my normal thing when they are gone and play dress up and go out and hunt for dick. But this time I knew they would be gone and had already planned an evening of fun with a couple of guys I had met at the adult bookstore my...Read On

14

Ready to Perform, Part Two – All Crossed Up

I get more than I bargained on!

Much happened in the next twelve months following that first session with my ex and her new partner: Ann began divorce proceedings which I didn’t contest, I financed myself into another home, and Ann, David and I met for two more sessions of torrid sex. These sessions were pretty much replays of the first; I would first screw Ann thoroughly through at least two climaxes, and then she would...Read On

45

My First Time with a cross dresser

Introduction to crossdressers

Growing up, like many children I went through phases. I would climb trees and play football, then as I reached my mid-teens I continued these phases but also became a lot more sexually aware, thanks to the porn magazines and porn films usually belonging to my mates dads or older brothers. Now I am in my late teens and at college. One day my Dad made a pot of tea and breakfast.“Did you...Read On

36

Can't I Have Them Both?

Can I Make This Work?

Waking up to the sound of my alarm blaring, I roll over and slam on it. Of course it doesn't go off, just crashes to the floor. I know I shouldn't have stayed up so late last night playing video games, but what can I say? Too late now, I suppose. I reach down to pick up the clock, seeing the time blinking at me. Getting out of bed, I grab the shower before anyone else can. I know what...Read On

29

Telling Mom I’m A Crossdresser Part 4: Repeat Business and Roleplays

4th installment of Missy :) please rate and comment :)

When my mom and I had gotten home, I immediately ran into the house to take a shower and change as quick as I could. I re-shaved my entire body and removed my makeup so that I could start from scratch and apply it again. Once I was finished with my makeup, I see a new outfit laid out on my bed. This was a cute nurse outfit with a short tight skirt that barely covered my ass. It was also...Read On

22

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

22

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

13

Felix becomes Felicity - Chapter 6

FELIX  becomes FELICITY Chapter 6 ..I put the gingham dress on that fit well and completed the ensemble with the shoes and cardigan. I looked like a fully grown woman in a school girl outfit. My breasts seemed to project and fill the dress with the buttons on the front tight. The fabric belt pinched in my already slim waste and the skirt part of the dress flared slightly emphasizing my...Read On

13

Dressmaker's Dummy

Girls always knows best

I was happy now that Kasia and I had moved in together. Not only did it mean that we no longer had to take turns going to each other’s place, but it also meant that I had closer access to a supply of her soiled panties. Kasia was a cute Polish girl, 23 years old, with deep blue eyes, shoulder-length hair trimmed in a cute bob, and a body to die for. We had decided trying to live together to...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

13

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

13

A Nanny Femtastic! - Chapter 11

A NANNY FEMTASTIC! Chapter 11 We walked to the harbour and found the boat. There were too bulky security guards checking people as they entered. The boat was in fact a massive cruiser! We joined the queue, it was obviously not a little gathering. The other women were dressed in classy whites and float summer dresses, we looked like too cheap hookers! “Trinity this was a...Read On

13

A New Chapter

Sensual Bliss

A few things have changed. One, I have accepted my desire and need to fulfill that urge to become feminine and girly. Two, having accepted that, I also had to invest to make myself look, and become as girly as I could. That led me on a near year pursuit to create a better feminine appearance than just using two suntan body stocking to shape and hold my feminine curves. After months...Read On

13

Becoming Chloe - Part 19

Tina and Vickie have some news, and Chloe has an interesting evening...

You know, they say that the thing about working in a sweet shop is that you soon seem to lose your appetite for sweets. Well, working in a sex store is pretty similar experience. At first, I was amazed at the variety and array of different toys, magazines, DVD's, clothes and nick-nacks that were available. After a while, however, I began to be less and less amazed (and aroused!) by the things...Read On

13

Night on the Town

The girls and I go out to a lesbian bar.

Night on the Town Barbara Marsh “Well, come on, chicken!” I responded, “Cluck, cluck.” Okay, so I know it’s not original, but it was the best I could do. Despite my misgivings, I got out of the minivan, smoothed my skirt across my hips, and waited for Alexis. Her name’s really Alice, but she was Alexis for the night. The same way Jeanna was Gina and I was Betinna. I don’t...Read On

88

Caught, Used and Loving It!

I was caught dressing up as female and used like a toy

I knew I had time now; my wife had gone out with her friendsand wouldn’t be back until 10pm at the earliest. As it was only 6:30, I knew I could spend time getting ready before playing around on the computer and enjoying a nice relaxing but exciting orgasm. My cock was more than ready as I hadn’t had sex for over a week and no chance to masturbate either due to either the kids being around or...Read On

63

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

59

Telling Mom I'm A Crossdresser

A story of me being open with my mom as a crossdressing slut andher becoming my pimp. Plz comment :)

When I was younger, my dad had passed away leaving only my mom and I. She is 45 years old with long brown hair, bright green eyes and stood about 5'10" in height. She is also a fairly busty woman with a 30DD chest with about 35" hips and in pretty good shape for a woman her age. I had been crossdressing for a few years and my mother had caught me a few times wearing her clothes. The first...Read On

33

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

33

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

33

My second visit to Bill's

This is the second part of Picked up in the toilets.

Here I was waiting to meet Simon, I had turned up an hour early. God I was keen after the week before, I just wanted more of the same. My mind whirred over wondering how many cocks I would suck and whether Debbie would suck me again. Would she tie me up this time? I just couldn't wait. Eventually Simon pulled up at the arranged place just like he said he would. I got into the car and we set...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

27

Becoming Chloe - Part 2

Their first shopping trip, and a changing room revelation...

As I lay there, my heart racing, I wondered what my wife would say. After all, she'd just caught me cross-dressing for the first time. So far, it had turned her on and we'd had the most fantastic sex since we first got married, a few years ago. Now that we were both spent, I started to get nervous about what she would think of me. Vickie rolled off me and then snuggled up as I put my arm...Read On

21

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