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Crossdressing

18

Jenny and Mike: Date Night

A loving husband and wife begin a long weekend of crossdressing and pegging.

It’s Friday night, but for me and my wife it’s Date Night. Most couples have date nights on Saturday, but we have it on Friday nights to get an early start on the weekends. Michelle and I have been married for a little over two years now and we live a very happy life. I was not always so happy because I am a crossdresser and have been dressing up ever since I was 16. I met Michelle when we...Read On

9

slut on the town

I got put in a full nelson the other night by a naked black guy. It happened in a video preview booth at Corey's Adult Video store in Oakland. I had been hanging out in the arcade, wearing just a black two-piece string bikini, and a pair of fire engine red high heels. I had been there for about a half hour, but I hadn't seen anyone. But it was early, only 3.30 p.m. Then I heard the buzzer go...Read On

4

One On the Way. Part 1

A new plan was required if he wanted to see Vicki.

Darren had met Vicki through Charlene, one of the girls from his school. He had just attended a Saturday movie matinée and was waiting for the bus to take him home when they walked up. Apparently, they were there too. From the moment they were introduced and locked eyes on each other, there was an instant attraction. He mentioned that he was surprised that he had never seen her in the...Read On

24

The Compromise: Part 1

A suggestion from a counselor sets in motion a fantasy compromise that changes my life forever.

My wife, Ally, and I have been married for eight years. What once could be considered a torrid love affair had subsequently lost its sexual passion. We don’t have any children, both being career focused, but our sex life had become quite stagnant from the steady grind of life and over-familiarity we had with one another’s sexual tastes. That is, until one crazy night changed everything. ...Read On

8

Discovery Part 2

It had been an amazing year for Kyle. At eighteen he attended his first get together for those that cross dressed and their supporters. It the first time since the urge to dress up came upon him he finally felt safe and accepted. Over the following months, he perfected his skills at makeup along with dressing, walking and talking like a female. Soon he was one hundred percent passable in...Read On

31

Confessions of a Ladyboy - Part 1

He helps me resolve my boy/girl confused sexuality dilemma

I was eighteen and new in the boy's hostel. No one had wanted me at home. I had never known my father. I saw my mother go out with a different man almost every night ever since I was old enough to remember such things. She taught me some valuable lessons - how to be attractive, how to carry myself, how to be seductive, how to do my makeup. She always said, "You are such a cute boy, you...Read On

17

In and Out of the Closet

A Young Man Gets Caught Inside His Employer's Walk-in Closet.

I had just turned eighteen when I started gardening for a young couple in their early thirties. The Shelby’s were quite well off, living a large four-bedroom house with both a swimming pool and a tennis court. Both were good-looking too. I had observed them playing tennis just the day before. She was a little blonde bombshell with light blue eyes and a terrific body, ample boobs, and...Read On

8

An Unforgettable Halloween

Tessa gets tricked at a Halloween ball but it turns out to be an unforgettable treat.

This past Halloween I took advantage of a chance to attend a charity Halloween ball. I had to travel for business to a city in upstate New York for a few days, and my first day there I saw an advertisement for an annual Halloween costume ball taking place in the mansion of local philanthropist. The annual party raises a significant amount of money for a designated charitable foundation. This...Read On

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

18

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

13

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