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Crossdressing

87

Vicky's First Time

My first time having sex as Vicky

I was very open about crossdressing when I met my wife when we were in our 20s. She has been very supportive and helpful. She helps me with my hair, makeup, and picking outfits. We started having sex with me dressed up as Vicky. This soon escalated to her taking me with a strap on. I loved the times she would fuck my ass with her cock. I had never considered myself gay or bisexual but the...Read On

20

My First Boyfriend Part Two

My boyfriend and I get closer

NOTE- this story will make more sense if you read part one,it can be accessed through my profile page. The week leading up to today had been one of the longest of my life. I was very excited that today had finally arrived. My boyfriend Steve’s parents left early that morning and would not be back for three days. My parents had agreed to let me stay over while they were gone. Steve and I...Read On

33

Wonderful crossdressing shopping experience

A wonderful Christmas eve to remember

Following is a true account of my recent experience of shopping for clothes (crossdresser, no sex). I just wanted to share a couple of very pleasant experiences I had shopping at the Natick Mall near Boston. It was the first time ever that I managed to shop with confidence and without any stress. I really want to give compliments to lovely women who made this possible (in case any one of...Read On

66

Crossdressing Fun From A Woman's Point of View

I have enjoyed reading the stories written by men to get a better understanding of what it is like to crossdress. As a woman, I find that I really enjoy and am very aroused with a feminized man. I guess I have always been a bit of a tomboy and enjoy doing athletic things, so being with a man that is the opposite seems natural to me. I used to play gender swap cross dress role play with my...Read On

19

Surprise

Aubrey greets his boyfriend home from work in a new way. Slight BDSM ahead.

Aubrey swallowed the lump in his throat as his wrists grew sore from his restraints-being handcuffed to the headboard of the bed, naturally he grew stiff. Speaking of stiff... he peered down, under the frilly black miniskirt of his maid outfit was a visible bump, straining against the panties that constricted it, said lingerie was clinging to his soft pale skin. He bit a plump bottom lip...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

59

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

24

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

44

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

45

Total Sub CD Slut

His total sub CD slut

I could not wait to get home from work on Friday. My routine was the same. It was total preperation for the weekend. I was a highly placed executive with the company I worked for at the time. Nobody knew that I lived as a total sissy slut cock worshipping whore on the weekends. I was seeing a guy who was very dominate. I met him online. The first night he took me home he dressed me...Read On

Mistress Hannah's Pathetic Husband Part 9

The final forbidden fantasy fulfilled

When we returned home, we had a big late lunch because Mistress informed me that we might want only a light dinner and then a late snack. I spent the afternoon preparing as best I could for an unknown special night. This meant hair removal, nails, wig, makeup, enemas, buttplug, lotions, powders, perfumes, the whole works. When I finished, she laid out the clothes and jewelry I would be...Read On

Mistress Hannah's Pathetic Husband Part 8

A return to the body art parlor

As we tried to sleep one Friday night after Mistress Hannah had used my ass with unusual vigor, she was tossing and turning and keeping me awake. I got the impression that she was struggling with some personal demon that was becoming an urgent threat. Something had changed around the time two months earlier when I had first achieved the goal of putting my puny pud up her ass. I don't think...Read On

Mistress Hannah's Pathetic Husband Part 7

Mistress makes good on her promise

It was 8 months since the first time Mistress Hannah had ordered me to put on her panties. In that time I had become both more of a man and more of a sissy. When we went to the theater club on Sunday nights, I had a variety of dresses, wigs and shoes to choose from. My aerobic workouts had boosted my stamina and I had gotten good control over my premature ejaculations. I still occasionally...Read On

Mistress Hannah's Pathetic Husband Part 6

Mistress Leelee uses me hard.

Having accepted the riding crop, Mistress Leelee seemed to understand that she was being given the opportunity to do something to me, but she was clearly lost. "He's yours now Leelee. It starts with the first order. If you're going to turn your cheating husband, a little experience with Michelle here will give you confidence. I suggest you order him to stand in front of you and work from...Read On

Mistress Hannah's Pathetic Husband Part 5

I serve lunch to sorority sisters

I was making progress as a slave but unkown to me, one of my stories helped Mistress Hannah see an opportunity for a particularly fun afternoon and a chance to help an old friend through a rough spot in her marriage. Several months of aerobic classes and feminization had increased my stamina and made me more comfortable when we spent our Sunday evenings out for dinner and as member/patrons at...Read On

Mistress Hannah's Pathetic Husband Part 4

Mistress takes the humiliation to a new level

The third and final day of my transformative weekend started poorly. I had aches and pains all over. My neck and back and thigh muscles were sore. I had a little irritation from body hair that was growing back. And of course, my asshole felt all stretched out and very tender. I wondered if it would ever feel tight again. I also wondered what the evening would hold. I couldn't imagine that...Read On

21

Chrissy Gets Bolder Meeting Todd Again

Chrissy gets a good hard fucking by her new friend

I really hadn't expected Todd to call me after that night. I know how guys are when the night is getting short and you need someone to satisfy your needs. I did think about him a few times and wanted to see him again. I had enjoyed my first experience with a man so much it seemed that's all I could think about was my next cock. When I went to class I would catch myself looking at guys as...Read On

Mistress Hannah's Pathetic Husband Part 3

I learn how manly my mistress wife can be

The first week of having a useful cock went well. For the first time since we got married, we had sex every night. After strapping my extension on, I would lick Hannah's pussy enough to get her turned on and then she'd choose a position. If I got physically worn out, she would choose another position. Because I was having sex so often and doing some research on the Internet, I was able to...Read On

45

Summer dressing

Long hot summer for crossdressing student doing vacation job

It was the mid 1980s, I was 20 years old and it was the summer holidays. For the long break from college I'd managed to find a vacation job in Kent in the south of England. It wasn't brilliant but I was going to get some experience of working with computers, and earn a bit of money to keep me going during term time. The company was based in a small town where I had found a room in a house with...Read On

Mistress Hannah's Pathetic Husband Part 2

The transformation begins

During my first week as her new slave, Hannah decided that I was too hairy for a little sissy boy, so I had to begin removing hair from the tip of my nose down. The mustache went first. It really was kind of pathetic anyways. I actually got compliments from some of the women at work about how handsome I looked without it. I had grown it because I had a "baby face" and I wanted to seem...Read On

Mistress Hannah's Pathetic Husband

She found my porn stash and now I must pay

My life had become miserable. It had taken two years of marriage for it to happen, but it had become much worse in the past few months. The worst part about it was that it was clear that my sweet wife's life had also become miserable and that she thought it was my fault. And maybe it was, but I didn't know why. I suspected it was because I'm a miserable example of a man and she deserves...Read On

23

Accepting an invitation

On the third day of house sitting, I awoke to a nice surprise. After my neighbour, Daniel, had unexpectedly visited, I had decided to work on my make up and mannerisms. After a day of walking in heels, I had perfected my sexy walk as well as getting my make up just right. I was feeling in the mood to show off my new found skills so was excited to see a note waiting by the front door. It was...Read On

43

Caught by a neighbour

I've secretly been crossdressing from a young age. In my late teens, around 17, I became more adventurous. maybe because I was enjoying it more. At that age I was very slender, had long dark hair as well has having a naturally smooth and hairless body. My brother and sister were both at uni and my parents would work a lot of the time meaning I was left home alone quite a lot. I would "borrow"...Read On

18

My day as a slut

Pleasing my Mistress

Again this is a true story from a few years ago. I had met a lady online, from a town about 40 miles away, we chatted, cammed and exchanged phone numbers. We texted and talked and eventually met, not quite in the way we wanted, but that's another story. We had met a couple of times and the opportunity arose to get her alone for a day at her house, so we planned something a bit...Read On

15

Early one morning

A surprise while walking

I work 12 hour shifts, days or nights, so I'm up at all hours. One morning, I was up at 4am to start at 6.30, so I had a quick cuppa then took the dog down to the park. It being September, it was very dark and very quiet. As I walked round the path, letting the dog do her business, I noticed a woman sitting on a bench under a street light. As I approached her, she said good morning, I...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

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

7

A Fantasy Come True

My wife and I went on a four day vacation to Charleston to enjoy the sights and especially to enjoy the nights. Our first night there I was no sure how it would go. I was wandering if my wife could really get in the role of being a Dominatrix. Would she really enjoy having DD as her Slave? Could my wife become the Dominatrix that I want and need? All my questions were answered that night. ...Read On

16

Andrew to Andrea - Part 3

..the next step...

 BRRRRIIIIIIINNNGGGGGGGGGG!!!!!! The alarm clock that my wife and I mockingly referred to as “Baby Ben” sounded off and pulled me from what I first thought was a great dream. As my senses slowly came online, I could feel my hand laid over my naked wife’s breasts and that I wasn’t in my usual gym shorts and t-shirt. I was surrounded in silk, and it was not unpleasant, but it was a floor...Read On

13

Andrew to Andrea - Chapter 2

Andrea's first small steps.

In all honesty, I should have been mortified by the events of the past few minutes, but I wasn’t…I was excited. I walked into our bathroom and set up the steamiest shower that I thought my skin could handle. I grabbed for my body wash, but realized the scent might be too masculine, so I set it back and grabbed my wife’s. It had a slight scent of vanilla and had a couple of butters and oils...Read On