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Crossdressing

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49

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

25

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

15

Extended Vacation Chapter 3

Cassie continues her new life

Cassie has her first full day as a woman as she continues her seven weeks living as a woman 24/7. EXTENDED VACATION Chapter 3 I arrived at my new apartment around 5 PM, and it took me over three hours to unpack and get organized. It was very enjoyable to move in and have a fresh start. I loved looking at my closet and all of my drawers as everything was for Cassie. My bathroom...Read On

15

My First Time

Melissa was excited, it was her first time.

The sheer thrill of what I was about to do was bursting through my body. My nipples tingled at the thought and my heart was pounding in my chest. I pinched one of my nipples until it hurt, just to prove that I was not imagining it. I simply couldn’t wait to see Mark. Three hours to go before I would stand in front of him and let him touch me, caress me and fuck me if he wanted to. All I had...Read On

15

Further Exploration

Shauna and Jerry make a video.

After Jerry kissed me goodnight and returned to his own room, I had time to reflect. Sex with him was so different than it had been with Jack. Jack took his time, slowly and steadily pumping his hard shaft in my man-pussy and making me feel like his special girl. Jerry was passionate and urgent, riding me hard and making me feel special in a whole different, slutty, way. I was Jerry’s...Read On

15

Service Call

What a service call!

I spent the entire morning and afternoon to transform myself into a busty, curvy woman. I did my typical routine to feminize my face and make my body look womanly. I shaved very close, three times. I moisturized my face. I added concealer, and then three coats of foundation. As I waited for that to settle, I cinched my waist. I added my very real feeling and looking breast forms. I lined...Read On

64

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

62

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

46

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

40

Put it on!

A not-so-reluctant housemate dresses for his live-in landlord

I was living and working in London, my first job after college. No chance of having a place of my own with these crazy house prices and this being my first job at the age of 23, so I rented a room from a guy older than me, in his mid-30s. His name was Steve and he was a masculine type, split up from his wife but seeing a feisty Spanish woman called Manuela. There were big arguments now and...Read On

37

Feminized

My first time in panties

We had just finished making love, but Amy was still not satisfied. “I wasn’t done,” She complained. “You came too soon! Let’s go at it again.” “You know that I can’t get hard again this quickly. It will take me a couple of hours to recharge my batteries before I can fuck you again.” I replied. “That is completely unacceptable.” she pouted. “There must be something that we can do. I...Read On

37

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

30

Seducing Uncle Frank

A tale of a Crossdresser seducing his attractive Uncle.

This is a story that happened some time ago, when I seduced my Uncle Frank. Uncle Frank Uncle Frank was married to my mum's sister. He was about 10 years older than Aunt May, and it was both their second marriages. Uncle Frank had an Italian father, French mother, three older sisters, loads of nephews and nieces, and had property in Kensington, the Algarve, and Telluride. You could say he...Read On

30

All the Way (Part 1)

Kathy makes Richard pay the price

I'd only been married a little over a year when my wife came home early and found me jacking off using a pair of her panties and to be sure, this wasn't the first time. There I was lying in bed with her wispy little nylon panties wrapped around my dick and cumming like nobody's business. I was so wrapped up in my own pleasure that I hadn't even noticed her standing in the doorway watching me. ...Read On

24

CAUGHT WEARING MY UNDIES.

Found out and 'forced' to educate respected women in village - inc vicar's wife.

CAUGHT WEARING MY UNDIES. Having recently been left quite a large sum of money by my late aunt in her will, I decided to buy my own house, and start my own business as a handyman. Because I was bored with my present location in the north of England, I moved down to the midlands and bought a very nice isolated cottage about 20 miles south of Birmingham on the outskirts of a...Read On

23

First Time Bareback

The first time I let my boyfriend fuck me bareback

I have written an earlier story about the first time my boyfriend Mike and I fucked. After our first encounter, I couldn't get enough of Mike and his cock. We went from meeting every other week to him spending some weekends at my house with me dressed the entire time. As we got to know each other better, we started to discuss our sexual histories and some of our fantasies. I could tell Mike...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

Tammy, Lisa, and Karen part 3

Please read: Tammy, Lisa, and Karen part 1 and 2 first

I woke up the next morning with Lisa sucking on my little clitty, making it hard. I pulled her panties to the side and began to kiss her beautiful pussy and suck and lick on her clit. I began to plunge my tongue as deep as I could into her hot wet honey hole. Lisa was about to make me cum, then she stopped. She knew just where my breaking point was. She turned around and sat down on my...Read On

14

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

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

44

What a Girl Wants

'Katie' finally fulfills her fantasy of having sex with a man.

"Come on, Katie. Give in to your desires. You've gone this far. You're almost there. You're so close to your goals and dreams of being treated like a lady. Accept it. Embrace it. Give in and complete your journey. Tell me what you want." Todd and I had been friends for years and even co-workers at one point in our respective careers. It had been almost ten years since I'd seen him and it...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

29

Cruising The Drive In

It was a Friday night and all of my friends were at home with family. I was really bored and I asked my dad if I could take the van and go to the movies. He said it was ok and told me to be home by midnight. The van was a 1977 Chevy van, it was brown in color and had the moon windows cut into the side. It had the typical "Captain' s chairs" up front and in the back had what you'd expect from...Read On

28

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

22

Punished

A crossdresser finds himself punished.

I glanced around the second hand clothing shop to make sure that no one had seen me pick out the pink, pleated netball skirt from the rack. I hid it beneath a pair of long pants in my hand. I felt my heart start to beat furiously as I stood next to the change room and caught the attention of the shop assistant by waving the pair of pants I was carrying, and the hidden netball skirt in...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