Crossdressing

borrowothers

A Night of Firsts pt 2

Pam meets some new friends

I opened the door to the club and walked inside. From the outside, the older brick building looked sort of run down, but once inside I found myself in a club with large bar on one side, polished brass railings, mirrors, subdued lighting, tasteful seats at the bar, hardwood floors, tables, a few booths further away and at the very end of the club a large stage with karaoke being sung. This was...Read On

Added: 06 Dec 2016 | Category: Crossdressing | Avg Score: 4.83 | Words: 1,326 | Tags: crossdressing  seduction   | 4 Comments

CourtneyFux

Girlyboy Gone Wild - Part Three

Playing dress up for men at my panty party is lots of fun.

With my little sexy blue plaid school girl skirt pulled up, I leaned over the desk for teacher Dan to spank me. Dan reached down and pulled down the back of my little white cotton panties revealing my very sexy ass. I saw how big his eyes got when he saw two of the sweetest cheeks he ever saw. He looked up at me. "You have a nice butt on you, Courtney." I smiled. "I hope I get to sit on...Read On

Added: 29 Sep 2012 | Category: Crossdressing | Avg Score: 4.67 | Words: 1,617 | Tags: crossdressing  oral sex  voyeur   | 4 Comments

starbelliedboy

Webmeets Diary Ch. 04

Celebrating the end of university as a slutty schoolgirl.

Note to the reader: In this diary I will tell the true stories of my sexual encounters that have come about thanks to the internet. Some more precise details such as names and places will be left out to protect mine and others privacy, and also because they don't matter, but otherwise I will try to be as accurate and truthful as possible. As I neared the end of my university course I had...Read On

Added: 08 Feb 2010 | Category: Crossdressing | Avg Score: 4.86 | Words: 3,281 | Tags: crossdress  gay  69  blowjob  anal  schoolgirl   | 3 Comments

MelanieCD

The man of My Dreams - Continued

I opened my door and there stood my beautiful black lover!

When the second day of my conference was over I returned to my room to change and become Melanie.  My hopes was that my beautiful, black god with his massive, uncut cock would be waiting once again at the bar.  For tonight I chose a sexy floral mini dress.  It was a white background with a floral print.  It had a tight strapless bodice and a full skirt.  My heels were 5 inches with a 1...Read On

Added: 20 May 2017 | Category: Crossdressing | Avg Score: 5 | Words: 1,836 | Tags: anal  corssdresser  inter-racial  bbc   | 12 Comments

ThePhantom

The Magician's Assistant Or How It began. The Conclusion.

The Halloween show they performed seemed to open the floodgates of bookings.The demand for his shows grew and soon they were working almost every weekend instead of every other one. Carl was forced to find a new headquarters for his magic workshop as his equipment began to overcrowd his garage. With Ken's business contacts he located a vacant factory that was only a few years old for a...Read On

Added: 27 Mar 2016 | Category: Crossdressing | Avg Score: 4.67 | Words: 1,380 | Tags: experimenting  revealing  confession  top hat  cape  wand   | 4 Comments

CallmeJulie

Call Me Julie part 3

The night gets more interesting

I stretched and reached out like a cat waking from a nap. Scott was resting on his side with his elbow down and his head resting on his hand looking down at me. "Enjoy your nap?" he asked as he stroked my shoulder. "How long was I out, how long have you been watching me?" I replied. "Not too long on either of your questions," he replied. I glanced at the clock and it read 8:00,...Read On

Added: 04 Apr 2014 | Category: Crossdressing | Avg Score: 5 | Words: 1,102 | Tags: military  crossdressing   | 7 Comments

jshub

Happy to be Used (Pt. 5)

I finish my day of private booth service.

I was walking gingerly in my heels and panties from the assault my ass had just received. While it likely looked like I was just trying to be more effeminate, my ass hurt so bad it was the only way I could walk. When I reached the front of the store I saw Sir talking to an older man who was behind the counter with him. The man appeared to be in his early sixties.  I looked at him and Sir...Read On

Added: 11 Aug 2017 | Category: Crossdressing | Avg Score: 4.75 | Words: 4,893 | Tags: butt plug  glory hole  anal  oral   | 1 Comment

Sexybottom4u

My First Experience With A Man

My first experience with a man and he made me crossdress

It happen when I was 18 years old. I was working for a clothing company at the time and it was a slow Tuesday morning. As I was folding clothes, a tall (I’m 5’5 he was 6’2) light skinned black man approached me. He introduced himself as Sam. He looked like he was well into his forties but was really fit. He inquire about several clothing articles in our store and slowly the conversation...Read On

Added: 26 Mar 2018 | Category: Crossdressing | Avg Score: 4.86 | Words: 1,900 | Tags: crossdress  gay  anal  first time  sex slave   | 4 Comments

carichristi

Towards an Advanced Degree - Part One

Cari seduces a handsome but dominant man.

At age eighteen I had finally made it into one of the best universities in the country, yet my true life lessons and deepest learning would ironically take place for me during the weekends. I’ve had the complicated urge to dress up as a girl since my early teens. Eventually I consciously chose to act on my need to do so. Though I live a mostly normal existence and also do enjoy my male side,...Read On

Added: 23 Sep 2017 | Category: Crossdressing | Avg Score: 4.83 | Words: 7,188 | Tags: crossdressing  seduction  anal  oral  first time  bondage and discipline  submission   | 5 Comments

Pudmeister

Crossroads Ch.4

Another chapter in this fantasy tale of a young man's journey into becoming who he is.

  I am on an airplane flying to Vancouver. I have an appointment with a doctor to have sexual reassignment surgery. I am so excited I can't stand it. I know this is what I want. My recent encounter with a woman convinced me. I have no doubt about it now and won't look back. We land and as we deplane I notice, as always, the admiring looks I am getting from men, including the pilots. I...Read On

Added: 25 Oct 2009 | Category: Crossdressing | Avg Score: 5 | Words: 2,110 | Tags:

MistressCheyenne

CD Mistress Cheyenne can't fight the craving for Candy

CD Mistress Cheyenne's kinky side comes out in the second meeting with new slave Candy.

Almost two long weeks had passed since my first meeting with my new slave Candy. Our first encounter was special and my sexy new sub had not left my mind since he walked out of my door. His juicy ass and hard thick cock have filled my thoughts each day since. I had found myself wildly attracted to Candy and lusting for him constantly. After deciding that ten days was long enough to make him...Read On

Added: 04 Jul 2012 | Category: Crossdressing | Avg Score: 4.88 | Words: 3,103 | Tags: bdsm  mistress  domme  slave  anal  oral  crossdresser   | 4 Comments

cassandrababy

Confessions of a Sex Crazy Cross Dresser Part 6

Chapters 11 and 12 of Book #1

Here are the next two chapters of Sandy's adventures Chapter 11: Photo Shoot and the Elevator Ride I slept great on Monday night after my craziest night of cross dressing. My body felt great as I slept in late. However, I had to admit, I felt like my ass had been torn up from Stan’s incredible cock. I realized now that almost all men wanted to get their rocks off with strangers. Stan...Read On

Added: 03 Jun 2010 | Category: Crossdressing | Avg Score: 4.64 | Words: 6,889 | Tags: crossdressing  anal  oral   | 4 Comments

pantywriter

Special Soiree

The two sissies meet for their special party

“Amanda” was fully dressed when “she” opened the door. She almost shyly greeted her close friend “Suzette.” “Hi Suzette. It’s been a while,” Amanda said. Suzette had an unhappy expression on her face. “I know, too long.” Then she looked around clearly nervous. Amanda knew that sensation, and opened the door wider. “Please, come in.” “Thank you, Amanda,” Suzette said her confidence...Read On

Added: 23 Mar 2017 | Category: Crossdressing | Avg Score: 5 | Words: 3,176 | Tags: sissies  chastity  teasing  crossdressing  oral   | 2 Comments

trinitytowers

A Nanny Femtastic - 10

A NANNY FEMTASTIC! Chapter 10 I rose early the next day and put on my white lace bikini, and took a dip in the pool. I was sitting on a lounger drying myself when Felicity came out. “Good morning gorgeous!” she said kissing me on the cheek. Our breasts rubbed together. “You know we have that party with those guys today sweetie?” “Are you sure we should go Felicity?” I said...Read On

Added: 16 Feb 2010 | Category: Crossdressing | Avg Score: 4.83 | Words: 1,397 | Tags:

CynthiaSissy

Rainy Day For Alex(ia)

Alex copes with a rainy day Sfw. Please comment, rate, and i'll develop her NSFW!!!

The smell of rain danced near his nose, as Alex sat by the window. It had been raining for two hours now, with no sign of stopping. The clouds were ever so gray and the wind gave the trees reason to dance. “I guess I know what will make this afternoon cozier,” he said, making for his wardrobe.  Passing his mirror, he caught sight of himself again, 5 foot 8, 62 kilos, with long brown...Read On

Added: 20 May 2017 | Category: Crossdressing | Avg Score: 5 | Words: 667 | Tags: crossdresser  crossdressing  change  lingerie  rain  sfw  feminization   | 5 Comments

trinitytowers

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

Added: 18 Feb 2010 | Category: Crossdressing | Avg Score: 4.85 | Words: 1,638 | Tags: | 4 Comments

ThePhantom

Taking That First Step. A New Chapter Begins. Part 2

Cassandra's new idea

September had arrived and Lance returned to high school for his final year. He still found himself attracted to and flirting with all the girls and not the guys. He surmised that it was only when he was dressed as Lana did his choices change. He couldn't see Cassandra during the week as he worked out after school and then went to his part-time job. He got home in time to join his family...Read On

Added: 31 May 2017 | Category: Crossdressing | Avg Score: 4.6 | Words: 1,345 | Tags: crossing dressing  kissing  anal  desire     | 3 Comments

vanessagrrl

Just the Two of Us, or Four

Vanessa and Greg fail at trying to spend a night alone

As time went on, the line was beginning to blur between me being Greg's girlfriend and Amber's pet. Greg decided that we needed a night alone. That didn't work out exactly as planned. He booked us into a lovely, fancy hotel in the heart of the city. Next up was going to be a nice dinner at a gourmet restaurant, and then we'd see where the night went from there. I wanted to impress, so I took...Read On

Added: 26 Jul 2013 | Category: Crossdressing | Avg Score: 4.88 | Words: 2,197 | Tags: crossdressing  group sex  anal  oral   | 4 Comments

ThePhantom

Taking That First Step. Part 5.

Lana began to protest at being pulled toward the bed; she felt she had been punished enough. Her ass was on fire due to the spanking she had just received. Her protests were ignored. Lana was pushed face down on the bed and she felt Cassandra sit on her back before she could attempt to rise. She felt Cassandra attach something to her wrists. Lana opened her eyes and saw restraints....Read On

Added: 25 Mar 2017 | Category: Crossdressing | Avg Score: 5 | Words: 1,046 | Tags: bed  restraints  lube  strap on  anal   | 4 Comments

carichristi

A Condition of Endearment

A Transvestite Finds Harmony in a Big City

I am a young, petite, passable and enthusiastic transvestite. I’ve been crossdressing and working on improving my look and appearance ever since I was a sixteen year old boy. Now after two years of weekends dressed in public as Cari, I had developed quite an attractive look and appearance. It often seemed at times, that many a man would come my way. Because of my exotic and sexy...Read On

Added: 25 Dec 2017 | Category: Crossdressing | Avg Score: 5 | Words: 3,888 | Tags: crossdressing  seduction  anal  oral  boy to girl  submission     | 5 Comments

dawnforever

Growth and Admissions

In a place where everyone cares, is the perfect place for a new beginning.

My initial impression that this town resembled Mayberry turned out to be reality, and that the people here where genuinely nice. Everywhere I went people introduced themselves and seemed to want to be my friend. At first, I really wasn’t sure what to think, but after the initial shock wore off, I began to relax and accept that this might have been the best decision of my life. After a few...Read On

Added: 11 Aug 2010 | Category: Crossdressing | Avg Score: 3.5 | Words: 1,144 | Tags: dawns summer   | 2 Comments

CAPITALLETTERJ

Big Green

Loosely based on true events and it is my first story so please be easy. Being a Marine for most meant traveling, working out and above all alpha males only. For me all of this was of interest but I didn't work out and I was definitely not an "Alpha Male". Slim in stature I stood all of five foot, six inches weighing in at a whopping 145 pounds. I wasn't much to look at in a uniform but out...Read On

Added: 05 Dec 2012 | Category: Crossdressing | Avg Score: 4.25 | Words: 702 | Tags: mm  blowjob  bj  roommates  marines  uniform  crossdressing   | 6 Comments

Satinfreak

A Satin Dream Comes True

An encounter with a dominant transexual escort

I’d explored my fantasies with a transsexual escort several times and after my last encounter, which was the basic girlfriend experience, though she did wear a corset and stockings with satin panties as I asked. She was very open to fantasy play I have long had a scene I’d wanted to play out and she seemed to be the perfect gentle dominant. Now my thing is dress up. My iconic Mistress isn’t...Read On

Added: 09 Dec 2017 | Category: Crossdressing | Avg Score: 4.5 | Words: 1,818 | Tags: transgender  escort  satin  submission  fantasy  role play   | 1 Comment

Kara1970tv

A Meeting of TV Girlfriends - Part 1

The meeting of two TV friends and future lovers.

I spent my day getting ready - shaving all over, showering, and cleaning myself inside too.   I gave myself a close shave and then moisturised fully.   My outfit was set - black holdups, matching red & black satin bra & knickers (a thong, maybe), black PVC midi skirt (or optional mini-skirt), and a dark lacy blouse.   Black patent stiletto heels.   Jewellery included rings, bracelet, watch,...Read On

Added: 02 Nov 2017 | Category: Crossdressing | Avg Score: 4.38 | Words: 3,098 | Tags: crossdressing  bisexual  first time  oral sex   | 4 Comments

sluttracy99

My Sexual Odyssey Part VII: Turning Tricks

A continuation of the journey described in part 6

The next day I went to work as usual, but skipped my noon time ‘date’ with Brad. When I got home, I called Candy and confirmed the party invitation. Then I called Trixie and asked if she could use me at the club. “Of course! Are you kidding? Anytime!” “Well great, what time should I come by?” “How early can you make it? We open at nine, as you know, but although nothing much...Read On

Added: 05 Jan 2015 | Category: Crossdressing | Avg Score: 4.88 | Words: 2,933 | Tags: autobiography  prostitution   | 10 Comments