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Crossdressing

3

Sissy Blane's Liquid Assets

A Sissy is forced to repay a debt to a sex club in trade

I became familiar with the Plumrose Dossier one cool February morning when it was read to me in the private rooms of Madame H at the Clinic. ***** I'd arrived that morning for my weekly 'therapy' and had only enough time to hang up my outer clothes in the Sissies' cloakroom and don my Eva Gabor wig before a facilitator poked her head in and told me I was wanted in Madame H’s office...Read On

7

The Only Cure Possible

Sometimes your body can win over your mind!

Mia was standing in front of the dresser, checking her reflection in the large mirror that gave me such a wonderful view of her beautiful face and upper body. I could see her glance to the side and knew she caught me staring at her ass and legs. Her smile was warm and genuine, and I knew she didn’t mind the lasciviousness in my countenance. If anything she considered it a complement, or...Read On

22

Initiating Stephanie

Stephanie's secret is discovered and exploited

** Discovery ** The first time I set eyes on her, she was wearing the sluttiest underwear one can imagine. Totally oblivious to my presence, she was admiring her scantily clad body in the full-length mirror on the wall. The lingerie was black, my favourite colour , sheer in texture and cut to a design that left little to the imagination. Black leather, ankle boots adorned her feet...Read On

6

That First Halloween. Part 2

Princess Jasmine and Zorro spend the night together.

They parted company long enough for Guy to reach his own car and pull up behind the SUV that was already on the street. As he followed it to the Carriage Hills condos, he was unsure how the evening would end. Carriage Hills was a gated community and the SUV stopped long enough for Zorro to address the guard on duty in the shack.They proceeded to an underground parking garage and parked...Read On

11

That First Halloween

Guy ventures out on Halloween dressed at Princess Jasmine.

Guy just sat there in his car wrestling with the decision to get out. Every time he reached for the door handle it caused his heart to beat harder in his chest so he stopped. He would occasionally check his make up in the mirror expecting that something changed since he last checked it.There was no change, he was still as stunning as ever. He finally worked up enough courage to exit his...Read On

2

A friend with something extra - The Conclusion

Lorna gets Grant ready for his lover.

It was on the following day that Lorna woke her step-brother up very early. "Come on and get up and get breakfast," she told him shaking him by the shoulder. "Huh? What?" he mumbled, still half asleep. "Come on. I need you to become sexy again," she insisted. He then stripped down to a pair of silk, hip hugger panties and donned a silk dressing robe that he found hanging on his doorknob....Read On

17

The Irresistible Dress

I just wanted some new jeans but I couldn’t resist the dress.

I entered the store as soon as it opened. I knew entering this early helped to ensure I would be the only customer so I could try on the boot cut jeans I wanted to buy. I said hello to the saleswoman and quickly wandered over to the jeans section but as I did I noticed a rack of new dresses. The one that stopped me dead in my tracks was a simple sleeveless sheath, but I loved the simple...Read On

3

My 2 AM Phone Call (Part Four)

I had no idea I was to be auctioned in that motel bar

They let me finish my cigarette and glass of wine which I appreciated very much. I sat very still on the bed smoking and sipping the wine while they watched me intently. A few minutes earlier when he locked the motel room door and I heard the lock click, I felt just a little fear, but that now gave way to excitement. The guys remaining in the room of this cheap, motel had seen me perform...Read On

7

Tina, Bob, Vicky and Amanda

An evening of surprises.

Recently, I paid a visit to a Trans/Crossdresser friendly bar in the city, accompanied by my wife Victoria. It was a night out to premiere my new wig and my new Marilyn Monroe style, short white dress. My online extravagance also stretched to a pair of white three inch heeled sandals. Vicky looked stunning as always in a short white denim mini ensemble, that showed off her midriff. Underneath...Read On

21

Becoming Anthea

Anthony is persuaded to cross-dress

My name is Anthony and I am twenty-two years old. I have extra-long dark hair and darker eyes. I tie my hair into a ponytail and have a close trimmed beard. I look handsome and enjoy keeping myself in shape. I am a lucky guy as I have a very sexy girlfriend who is two years older than me. Zoe and I met at a mutual friend’s party and hit it off right away. She has short blonde hair and...Read On

15

Falling for Zak

A young man let's himself go to another man's desires

I hadn’t noticed the time, and I’d missed the last train home. The student party was fun, but I was in a bit of a panic not knowing what to do. People were leaving, and the crowd was thinning out. If it had gone on for several more hours, I would have stayed there and taken the first train in the morning, but that didn’t look likely. The hostess was already clearing up. I figured she’d...Read On

14

Exploration (Discovery II)

Shauna's second lover.

After my neighbor, Jack, caught me dressed and made me his girl, my mind was awash with conflicting thoughts and emotions. I had been dressing as an added thrill to masturbating for years, and had fantasized about being with a man, but always considered it just fantasy. I never thought of actually doing it, but now, it had gone from fantasy to reality in just a few hours. Not only had I...Read On

2

Toby: The Little Rascal

A follow up to "Toby's Story"

Annabelle's last minute phone call altered our plans for the evening. "You'd better come as yourself because Toby's fucking hanging about!" She sounded a tad perturbed. Maybe the fact that her son was encroaching on her 'me time,' explained her tone. Never mind the fact that I had already started my transformation. My two-week beard growth had gone, and I was in my wife's bra,...Read On

12

My Good Friend Pete (Part 2)

In order to enjoy this story, I advise the reader to read "My Good Friend Pete."

From where I stood, I could hear the crunching of gravel under Pete's feet, as he made his way to the front door. I took half a dozen deep breaths, waiting for the doorbell to ring. I didn't have to wait long. "For fuck sake, pull yourself together man." I actually caught myself smiling in the wall mirror. "...or is it woman!" One of the most difficult things to achieve...Read On

14

The Incredible Mrs. Mac

My Mrs. Robinson

During my adolescence there were a few of my mom's friends that featured regularly in my lone periods of self gratification. None more so than Mrs. Mac. She was bottle blonde, attractive, with great legs, and magnificent breasts. She was the mother of three kids, two teenage girls, 15 and 13, and a boy of 7. Her husband Danny was one of my dad's work colleagues, and together they had earned...Read On

16

Seducer or Seducee?

Male attends a costume party as Tessa and is seduced by a beautiful woman.

Every year a city about an hour away from where I live hosts a big charity costume party that coincides with Mardi Gras. I had decided to attend the event as my female persona, Tessa. Since I don’t get many chances to go out in public I decided I was gong to go all out for this event. For the last two months I had been on a strict diet, more like starvation but I knew the results were going...Read On

6

My Mother's Boyfriend, My Slut! (part 2)

Now that he was my slut, I couldn't seem to get enough of him.

The day had been wonderful, seeing my slut skewered on my strap on. His nipples peeking through his netted shirt as he begged to come with me buried deep inside of him. After he came all over his chest and face, I had exited the room, needing my own release. I headed for the shower, happy to leave him to clean up his mess. With the taste of him still on my lips, I turned on the water....Read On

6

Three nights in London, night 3, Irene rocks!

Cute Dutch Tgirl goes for it

I woke up looking into the smiling face of a pretty redhead. Sunlight was streaming through the curtains of her bedroom. "Good morning, Irene," she said, and she kissed me on my nose. I smiled back and slowly remembered my adventures of yesterday. When I moved my legs it dawned on me that I was still fully dressed. I even had my high heeled boots on. My skimpy black dress was pulled up...Read On

8

Toby's Story

Now this doesn't happen every day!

  I had been admiring myself in the full length mirror for the umpteenth time in the last hour, as girls like us do, when I heard a vehicle draw into the driveway. Under normal circumstances, this would not be cause for concern. But circumstances were far from normal. I was miles from my home, in my friend Annabelle's house, and fully dressed in her clothes, and caked in her cosmetics! ...Read On

2

My 2 AM Phone Call (Part Three)

I became a much better and more confident motel whore as the night wore on

Everyone seemed to be talking at the same time at my table, and I was surprised by that. I must have zoned out for a while because when I looked around, suddenly I was wide awake. I was now suspicious of what they gave me to drink earlier. As I look back, there was probably some sedative in it that caused me to doze off, but whatever they put in it, when I came around I was more alive and...Read On

5

A New Beginning (Part 3)

My first experience in public

It’s been a while since I’ve written. For background, I’ve got a wonderful relationship with my wife Joan and an ongoing affair with my step-daughter Ellen. It’s possible since Joan’s job keeps her out of town for extended periods of time. Both of the women in my life have the same sexual tastes and to say things get kinky is an understatement. Ellen was very much in dressing me up from...Read On

11

Fantasy Meets Reality at the Peep Show

A crossdresser's fantasy comes true

I pushed my way through the purple curtain to the cashier’s booth. He looked up from his newspaper and asked me how many tokens I wanted. I figured a stack of twenty would be enough to complete my mission. I’d been there several times before but this would be my first time taking things further. My heart was beating fast as I scooped up the tokens and made my way to the viewing room. As...Read On

12

Jessie's Fantasy Chapter 7: The Tables Got Turned

Now that Jessie decided to turn the tables, how will she handle all of her friends?

Here I was, getting my boy pussy plowed by my good friend Scott, when Mark decides that he needs to call Jesse, the male me. As he was starting to dial my phone number I realized that I never turned the ringer to vibrate after we left the night club. I was panic stricken as they all knew the distinct ringtone that I used. I couldn’t let my phone blow my cover. I had to think fast, but what to...Read On

5

Three nights in London, night 2, Irene is going out

Cute Tgirl goes out for the first time

"Irene,wake up sweetie." Slowly the mist from my dream started to lift. Irene, who's that? I slowly became aware that I was holding something soft and cuddly in my arms. A Teddy bear? I moved and felt something tugging at my chest. Breasts? I opened my eyes slowly and saw the broad smile of a pretty redhead just in front of my face. "Wake up, pretty girl." In a flash...Read On

13

My Road to cross dressing

My road towards dressing and feeling Ok about.

I was bought up in a time when taboos about something alternative like transgender people or cross dressing was still considered to be a no go area. Society made one feel that you were an out cast or mentally ill. Luckily times have changed and it has become much more acceptable, even though we still have a long way to go. I first started dressing when I was about eighteen. My sister had...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

57

Discovery

The neighbor makes a discovery

How did I end up in this position?  This was the thought running through my head as I lay face down across the bed. My mind flashed back to the moment it all began. It was a beautiful Sunday morning with a cool springtime breeze blowing through the open window. I was cleaning the house. I hated cleaning, mostly because it is never fully done. No matter how much cleaning you do, there will...Read On

8

Three nights in London / Night 1: Irene's transformation

Cute Tgirl goes on the adventure of her lifetime

I met Gabrielle at a music festival where I played with my band. After our gig, she complimented me on our show and we started to chat. She was over from the UK and was staying with friends in Amsterdam. I was impressed by this pretty redhead, dressed in a bit of a Lolita style with ultra black makeup, a cute red tartan skirt and huge boots over fishnet boots. We directly clicked and she...Read On

11

Made Maryanne - Part 2

John is made aware of his new role

When I woke up the following morning, I immediately became aware of the situation. It was difficult not to notice the pretty white cotton and lace nor the fact that I was wearing it. I quickly recalled the events of the previous night, feeling ashamed at having been caught masturbating. I knew that Beatrice somehow wanted to make a point by telling me to wear her nightdress, but I had no...Read On

10

Ready & Waiting (In my wife's lingerie)

My wife has me dress up in her lingerie while she goes off to get a massage.

“Billy, can I see you in the bedroom?” I walked down the hall and into the bedroom, surprised to see lingerie laid out on the bed. I asked, “What’s this?” “We’re going to play a little game today. I need to de-stress, and you’re going to help me.” “Help you how?” “Take off your clothes and go shower.” After my shower, I returned to the bedroom completely naked. And erect. I kissed Betty....Read On