Crossdressing

fernandezh1983

Jenny & Mike: Romantic Picnic

A nice romantic picnic that culminates into public pegging.

It was close to 10 a.m. and I was still in bed with Michelle sleeping peacefully next to me. Last night had taken quite a bit out of me. Having been used and fucked by two cocks was a huge turn-on. ‘Mike’ and ‘Carlos’ had given me quite a workout! I received the fucking of a lifetime. Sex with Michelle had always been great, but having a third person added a totally different edge. The...Read On

Added: 23 Feb 2017 | Category: Crossdressing | Avg Score: 5 | Words: 4,860 | Tags: crossdressing  strapon  strapon anal  gender play  gender reversal  public sex  pegging   | 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: 4.38 | Words: 2,110 | Tags: | 1 Comment

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

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

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

allfours

Carl, Carla and Hannah - Part 11

Carla becomes more feminine, and then Carl has to make a decision...

"So," Hannah said as we reached the outskirts of the city, "How did you enjoy your first time dogging?" "Is that what it was?" I asked incredulously. "Well, sort of, yes. What did you think it was?" she laughed. "And the bloke who was watching thought you were a girl as well!" "I know," I said, proudly. "Hey, does that mean that the bet's already won, a week early?" I asked...Read On

Added: 07 Feb 2014 | Category: Crossdressing | Avg Score: 4.75 | Words: 3,361 | Tags: crossdressing  feminization  toys  strap-on  cum-swapping  

borrowothers

A Night of Firsts pt 3

Pam has a first

We all took a sip of our drink. Catherine, Anna and myself, presided over by Lauren. I felt like a new gurl at this party. I bit my lower lip, I wriggled in my seat for my dress giving an accidental glimpse of way too much upper pantyhosed thigh. I blushed so deeply. Lauren must have sensed it as she leaned in closer and told me that I was a flirty gurl and those legs of mine might get me...Read On

Added: 17 Dec 2016 | Category: Crossdressing | Avg Score: 4.8 | Words: 1,465 | Tags: crossdressing  seduction   | 6 Comments

ThePhantom

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

Added: 06 Oct 2016 | Category: Crossdressing | Avg Score: 4.67 | Words: 1,400 | Tags: princess  zorro  role play     | 6 Comments

allfours

Carl, Carla and Hannah - Part 25

The Honeymoon Party - the final chapter.

A knock at the door broke our reverie. Hannah turned to me quite pointedly and said that I should answer it. I looked at her questioningly, but she just gave me her mischievious grin. "Call it my wedding present to you, Carla," she said, enigmatically. "Now, go see who's there." Bewildered, I walked to the door of the suite, loving the sound of my wedding train rustling behind me. As far as...Read On

Added: 15 Mar 2014 | Category: Crossdressing | Avg Score: 5 | Words: 2,826 | Tags: crossdressing  oral  anal  transformation  bisexual  group   | 3 Comments

nymanirene

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

Added: 22 Jul 2016 | Category: Crossdressing | Avg Score: 4.88 | Words: 2,922 | Tags: crossdressing  makeover  transformation  lesbian  cute  blowjob   | 3 Comments

allfours

Becoming Chloe - Part 11

Vickie meets Tina, and and Chloe has a surprise for dinner...

Vickie was naked, apart from her white jacket, stockings and suspender belt. Unlike the woman who left several hours ago, her hair was now loose and dishevelled, falling softly to her shoulders. Her make up was no longer pristine: her mascara had run a little and her lipstick was definitely in need of refreshing. Her lips seemed a little swollen, and her jacket was parted just enough for me...Read On

Added: 01 Feb 2016 | Category: Crossdressing | Avg Score: 4.77 | Words: 2,560 | Tags: crossdressing  feminization  toys  anal  lesbian     | 5 Comments

havingsomefun

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

Added: 12 Aug 2016 | Category: Crossdressing | Avg Score: 4.8 | Words: 1,274 | Tags: crossdressing  caught  outed   | 2 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

ThePhantom

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

Added: 03 Oct 2016 | Category: Crossdressing | Avg Score: 5 | Words: 1,616 | Tags: dressing  secret instructions.   | 1 Comment

ThePhantom

Taking That First Step. Part 2

Lance returns to the specialty shop

Lance's family was surprised to hear him up and moving at 6:00 AM. Saturday was his day to sleep in now that school was out for the summer and he didn't work on the weekends. They didn't question it and soon fell back to sleep as Lance headed to the master bathroom. He showered and then toweled off before heading back to his room. Once in his room with the door locked behind...Read On

Added: 07 Mar 2017 | Category: Crossdressing | Avg Score: 5 | Words: 1,575 | Tags: lingerie  dressing  role play   | 8 Comments

ThePhantom

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

Added: 14 Nov 2016 | Category: Crossdressing | Avg Score: 5 | Words: 2,622 | Tags: kissing  touching  busted  grounded  first time dressing   | 4 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

allfours

Carl, Carla and Hannah - Part 17

Luke takes Carla to the cinema

As the week progressed, I looked forward to my date with Luke. I even found myself thinking about him when I was at work, and more than once found that I started to speak in my female voice before I'd realised it in the office. As Claire was 'unavailable' for a few days, Hannah went out of her way to make her life difficult at work. One lunch-time she went into her office, locked her door...Read On

Added: 21 Feb 2014 | Category: Crossdressing | Avg Score: 4.89 | Words: 2,436 | Tags: crossdressing  feminization  oral  swallowing  transformation  pegging   | 3 Comments

ThePhantom

Taking That First Step. Part 3

Lance's transformation continues

Lance had arrived at the specialty shop as himself, a young man wearing women's lingerie under his jeans. He was met by the stunning Cassandra, the shop owner and his confidant. She treated him to a wig, lipstick, eye shadow and then directed to one of the changing rooms. Waiting inside was one of the sexiest lingerie combinations that he had ever seen.  Upon exiting Cassandra reappeared...Read On

Added: 11 Mar 2017 | Category: Crossdressing | Avg Score: 5 | Words: 1,445 | Tags: lingerie  dressing  role play  first time  anal   | 7 Comments

AmandaCarrington

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

Added: 04 Sep 2016 | Category: Crossdressing | Avg Score: 5 | Words: 2,200 | Tags: crossdresser  masturbation     | 1 Comment

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

trinitytowers

A Nanny Femtastic - 7

A NANNY FEMTASTIC! Chapter 7 After that first dinner Bradley and Felicity retired to their bedroom. And even though they were in a separate wing of the sprawling villa I could hear them making love! I thought of what Felicity felt as a transsexual woman having had a vagina created out of what was her penis. To feel Bradley rigid penis inside her. I wondered how nice it would be to put on...Read On

Added: 07 Feb 2010 | Category: Crossdressing | Avg Score: 4.69 | Words: 936 | Tags: | 2 Comments

CourtneyFux

Girlyboy Gone Wild - Part Seven

Fifi, the sexy French maid, gets to do 69 with her handsome boss.

After getting Rich big and hard with my sexy outfit, I was now ready to put on a show for him Whenever men see me in my panties, they want me like a girl. It follows that whoever wears sexy little panties also likes big hard cocks to suck on and play with. My sexy French maid outfit was especially good at making me feel like a slut for a man. Since so many men had fantasized about being with...Read On

Added: 20 Oct 2012 | Category: Crossdressing | Avg Score: 4.33 | Words: 1,901 | Tags: crossdressing  oral sex  voyeur   | 3 Comments