Crossdressing

thatfemininUrge

My First BJ dressed En-Femme

I needed to confess this. It is not a story, but a reality.

I only cross-dress when the urge to be feminine comes over me. I mostly have dressed privately, but that has changed. The last four years I have ventured out in public. I was curious if I could pass as a female. Little did I know then, when I first went out in public what it would lead too? It is why I am going to tell my story here. I needed to confess and to tell someone even if it is to...Read On

Added: 27 Nov 2014 | Category: Crossdressing | Avg Score: 4.95 | Words: 5,635 | Tags:  blow job  crossdressing  sexual   | 18 Comments

AceInTheHole

Dressing up

For some reason, guys like me in a dress

This is a series of stories rather than one story. It talks of my experiences as a crossdresser. My first experience as a crossdresser came as a teenager when I tried out some of the clothes belonging to a woman who was staying at our home. She was a gorgeous French woman with very pretty clothes and I did enjoy trying them on, but primarily as it got me closer to this woman who...Read On

Added: 04 Sep 2012 | Category: Crossdressing | Avg Score: 4.22 | Words: 2,541 | Tags: crossdressing  bisexual  gay male  anal  mature  younger  first time   | 3 Comments

pleatedskirt

Punished

A crossdresser finds himself punished.

I glanced around the second hand clothing shop to make sure that no one had seen me pick out the pink, pleated netball skirt from the rack. I hid it beneath a pair of long pants in my hand. I felt my heart start to beat furiously as I stood next to the change room and caught the attention of the shop assistant by waving the pair of pants I was carrying, and the hidden netball skirt in...Read On

Added: 13 Dec 2014 | Category: Crossdressing | Avg Score: 4.85 | Words: 3,297 | Tags: crossdressing  bondage   | 12 Comments

BadDog9

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

Added: 23 Jul 2016 | Category: Crossdressing | Avg Score: 4.98 | Words: 3,339 | Tags: cross dressing  oral  anal  first time  older  neighbor  caught   | 25 Comments

pantyslut

My Parents Friend

Get's Me Hot Every Time I think About It

The year was 1987 and I was home on leave from the military. One particular Saturday night my parents were haveing a get together with some friends so I decided to go out and try and find someone to have fun with. I couldn't decide what to wear until I just decided on what I thought would make me look sexy. I grab my things and head into the bathroom and put on my sexiest black...Read On

Added: 23 May 2008 | Category: Crossdressing | Avg Score: 4.89 | Words: 1,947 | Tags: croosdressing  anal   | 7 Comments

ChelseyR

In Wonderland, Pt.1

Costume mandatory...

When I was in high school I was always very camp, which was probably why almost all of my friends were girls. This was definitely why I first ended up crossdressing. I was sixteen and round one of my 'girlfriends' house for a few drinks on Halloween before we went to a house party nearby. I never much cared for Halloween, so just came as myself. When I came in they all sighed since I wasn't in...Read On

Added: 07 Nov 2010 | Category: Crossdressing | Avg Score: 4.8 | Words: 1,079 | Tags: alice  crossdress  party  halloween  teen   | 7 Comments

Amatramp

Caribean Vacation part 2

Lost luggage leads to wearing girlfriend's panties as a swim suit and more

We strolled down the hall to the elevator. I did not notice what floor we went to, as I was so pre-occupied examining my sexy self in the reflective surface of the elevator. We got off the elevator and walked down the hall to a door marked 469. “This isn’t the dining room,” I objected. “No, this isn’t,” she replied as she knocked on the door. “Who’s room is this.” I asked. Before...Read On

Added: 02 Nov 2010 | Category: Crossdressing | Avg Score: 4.89 | Words: 2,296 | Tags: panties  crossdressing  anal sex  humiliation     | 4 Comments

LingerieBoy

Been A Long Time

Once I got married I pretty much gave up my crossdressing lifestyle to lead a more "normal" life.You know,settle down,have a couple of kids. I was a happily married man with two kids,what could be missing? Well one day while at work,I was on the internet and stumbled onto a crossdressing website,and all kinds of memories came rushing back to me. The feeling of sexy panties,bras...Read On

Added: 06 Nov 2008 | Category: Crossdressing | Avg Score: 4.88 | Words: 1,350 | Tags: crossdressing  glory holes  cum  swallow   | 9 Comments

TaraNicole

Smooth Sensation

A t-girl get what she wants......

  God I was glad to be home, a two-hour train nightmare. Every stop from Liverpool Street London on the 6pm slow train to the dreary little Essex village that was the only place I could afford to rent a studio flat. My only consolation was the bag of goodies I brought in my lunchtime and the anticipation that tomorrow was Friday and my big night in with my mysterious blind date. I had...Read On

Added: 16 Feb 2009 | Category: Crossdressing | Avg Score: 4.68 | Words: 2,088 | Tags: transvestite  gay  bi-sexual  crossdresser  anal  oral  stockings   | 14 Comments

Karin

Old Friend, New Relationship-Part 1

As it turns out, I confided my crossdressing desires in just the right person

Old Friend, New Relationship-Part 1 I met Karen in my divorce support group while I was dealing with my second divorce and she was trying to cope with her first. About the only thing that we had in common was that both our spouses had cheated with good friends of ours. She was a couple years older and very attractive. I remember that she always dressed so well for our group meetings. We...Read On

Added: 11 Jun 2011 | Category: Crossdressing | Avg Score: 4.88 | Words: 2,649 | Tags: crossdressing  feminization  blowjob  beauty salon  first time   | 10 Comments

Chrissy_CD_slut

My First Real Outfit

My First Real Outfit I started completely dressing in women’s clothes shortly after high school. I didn’t really own anything of my own but I would fully dress in my mothers clothes a few times when I knew she would be gone for a few hours.. Usually it was just pantyhose, bras, and panties that I would borrow from my mom . I had experimented with it a bit when younger, stealing my...Read On

Added: 12 Nov 2009 | Category: Crossdressing | Avg Score: 4.63 | Words: 2,252 | Tags: crossdressing  masturbation     | 10 Comments

subguy

Shopping outing for lingerie

Fun time buying lingerie

Following is a true account of one of my experiences of shopping for lingerie. (nosex). This happened a couple of months ago, and as far as I remember, the conversation went like I have described below. If you have not read my earlier story 'Wonderful crossdressing shopping experience', I'd suggest reading it first. ------------------------------------------------ Following my...Read On

Added: 21 Apr 2012 | Category: Crossdressing | Avg Score: 4.83 | Words: 2,399 | Tags: nosex  crossdresser     | 6 Comments

philippasubmaid

Caught and the Consequences Part 3

Husband caught dressing and the wife's retribution continues

Part 3   I signed the contract and handed it back to my wife, well my Mistress now I guess.   She took it from me and said ‘Good girl’ ‘As you will have seen you are now Philippa, now go and get all your male clothes.’   ‘Can I get dressed’ I said.   She slapped me hard across the cheek. ‘When you speak it will...Read On

Added: 20 Nov 2009 | Category: Crossdressing | Avg Score: 4.11 | Words: 2,081 | Tags: crossdressing female domination bondage   | 2 Comments

purekink

Becky's Video

I watch a movie that surprises me in more ways than one.

I suppose I was the one that first mentioned porn to Nikki. We'd been chatting on a girls' night out and laughed abut how I'd never found any porn in the house. She giggled and said I was bound to find some sooner or later – all men had some, somewhere. A few days later, I'd completely forgotten our drunken conversation and so when Nikki showed up at mine after you'd gone out with...Read On

Added: 12 Apr 2010 | Category: Crossdressing | Avg Score: 4.6 | Words: 2,459 | Tags: crossdressing  strapon  mf  ff  masturbation   | 4 Comments

Toby

My first Cross Dresser and me

My first cross dressing experience

I laid down beside her and gave her the soda. We sipped slowly and talked about what had just happened. I sat the sodas on the night stand and moved up closer to Toni (a name we will use for this article) crossing my leg over hers so that my clitty rested on her nylons. We kissed for several minutes as I played with her nipples thru the silky bra. Toni looked up with lust in her eyes and said...Read On

Added: 08 Jan 2007 | Category: Crossdressing | Avg Score: 4.53 | Words: 689 | Tags: cross dresser  crossdressing   | 3 Comments

CourtneyFux

Mom's Old Boyfriend: Part One

Courtney seduces her mom's old boyfriend and sleeps with him, all weekend..

It happened quite by chance and we managed to keep it a secret, ever since. I was home alone on a Friday evening wearing my mom's favorite black lace lingerie and her old boyfriend, Ron, came by to see her. He still had a key from when he was seeing my mom and he walked in without knocking on the door, startling me. And he caught me playing with myself through the sexy little black lace...Read On

Added: 05 Mar 2014 | Category: Crossdressing | Avg Score: 4.72 | Words: 5,251 | Tags: crossdressing  exhibitionism  oral  anal   | 7 Comments

trinitytowers

The Feminisation of Michael - Chapter 3

The Feminisation of Michael. Chapter 3 I endured the rest of the afternoon with continued suppressed sniggers and laughter. I was glad when 5.00pm came and I buttoned up my jacket and put my handbag over my shoulder and left with a big sigh of relief. Sue was waiting outside in the car. “Hi Michaela,” she greeted me. “How did it go honey?” she beamed. “Fucking awful!” I blurted out....Read On

Added: 17 Feb 2010 | Category: Crossdressing | Avg Score: 4.83 | Words: 2,202 | Tags: | 4 Comments

1ball

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

Added: 20 Oct 2011 | Category: Crossdressing | Words: 3,357 | Tags: humiliation  feminization  strapon anal   | 3 Comments

SosaGood

My Mother's Boyfriend, My Slut

He seemed like a slut to begin with, who knew he really was.

 Divorce often times traumatizes the children, but in my case, it set me free from all their arguments. Dad signed the papers and walked out the door on my seventeenth birthday; it was the best present he could have ever given me. I was finally free, I could go to parties and hang with guys. Mom was the lenient one who was always gone on some major trip. I was cool with it until she brought...Read On

Added: 14 Feb 2015 | Category: Crossdressing | Avg Score: 4.73 | Words: 1,943 | Tags: toys  cross dressing  collar  leash  crop   | 15 Comments

pam1950

Lingerie and Domination

Lingerie Shopping and something more

I had answered an ad on telephone dating service. She described herself as a ‘bedroom dom’. I am not sure why I answered the ad and I did not really expect a reply. She phoned when I least expected. I did not think she would be interested but I had mentioned in my reply that I like to dress in lingerie — panties in particular. I met her for a drink. She was younger ( 38 ) than me and...Read On

Added: 20 Nov 2009 | Category: Crossdressing | Avg Score: 4.07 | Words: 1,030 | Tags: lingerie  domination  crossdresser   | 3 Comments

Dividence

My Best Friend

My friend's reaction to me dressing as a girl caught me by delightful surprise.

I always wanted to be a girl. Every time I saw those pretty girls prancing around the college campus I’d become green with envy. Their feathery skirts caressing glossy thighs. Long, silken hair cascading across bare shoulders. High heels clicking on the pavement as they paraded their fit asses in front of all the guys. They were allowed to be sexy, and no one would stop them. And the warm...Read On

Added: 21 Jan 2016 | Category: Crossdressing | Avg Score: 5 | Words: 3,223 | Tags: crossdressing  anal  blowjob  m2f  friends  college  dorm   | 14 Comments

HollyInPantyhose

Adventures in a Woman’s Body – Chapter 4: Public Humiliation

Used as a playtoy at the mall

I stepped out of the shower and began to dry myself with a towel. On this bright Monday morning, all I could think about was what happened on Friday night. After being gangbanged and cumed on thoroughly, Daddy drove me home that night. On our way there, he explained to me the situation that I am in. Daddy took out his phone and showed me pictures he had taken of me being a dirty little whore....Read On

Added: 27 Dec 2013 | Category: Crossdressing | Avg Score: 4.77 | Words: 2,189 | Tags: stockings  vibrator  high heels  slut  cum  swallowing  public   | 5 Comments

rushman1uk

The feeding of sissy

I hold a prominent position in a world wide business firm and make a six figure salary and had been divorced for several years. I met Wendy through a newspaper add in the singles columns, she was a knockout looking gal. We dated for some time and she moved in with me. One night when we were out having drinks she ask what my deepest secrets were. She would share hers with me in return if I...Read On

Added: 11 Mar 2012 | Category: Crossdressing | Avg Score: 3.6 | Words: 713 | Tags: crossdressing  wife lovers   | 7 Comments

hoterotica

My Boyfriend's Blue Silk Panties

a crossdressing shortie

My boyfriend, Allen, is a man's man. Let's get that straight from the start. He rides a Harley and he scoops me up in his big strong arms like I'm light as a feather (which I'm not...let's get that straight from the start, too). So it was a big stretch for me to ask my masculine lover to slip into a pair of silk panties just for me. It was a secret fantasy I'd harbored for years but had...Read On

Added: 07 Oct 2013 | Category: Crossdressing | Avg Score: 4.61 | Words: 563 | Tags: crossdressing   | 26 Comments

philippasubmaid

Caught and the Consequences Part 4

Husband caught dressing and the wife's retribution continues

Part 4   I served dinner at 7.00pm as requested and I was made to stand by the table so that I could serve wine as their glasses were emptied and attend to them as requested. I did find the whole experience satisfying in a kind of way as I knew I was pleasing my Mistress and hopefully Sir as well, although neither of them had any conversation for me.   ...Read On

Added: 23 Nov 2009 | Category: Crossdressing | Avg Score: 4.28 | Words: 1,058 | Tags: crossdressing  female domination  bondage  cuckold   | 6 Comments

LingerieBoy

The Young Crossdresser Part 2

So after my little adventure at mom and dad's bookstore,the next couple of years were uneventful. I did have sex a couple of times with Phylis,the older lady that was part of mom and dad's swinger group. I knew that I was wanting something more,something was still missing and I kept thinking back to how the guy's cock felt as it spewed cum into my panty covered ass. Now I was 15 and...Read On

Added: 10 Jul 2008 | Category: Crossdressing | Avg Score: 4.64 | Words: 1,709 | Tags:

HollyInPantyhose

Adventures in a Woman’s Body – Chapter 1: Plugging Up

Dressed up, plugged up, and ready for some cocks

After two years of hard work, I've finally come as close to being a woman as possible. The hormones and drugs that I've been taking for the past five years have made my body and voice quite feminine. With the help of toning exercises, I now have long slender legs, a soft and juicy ass, very feminine hips and a thin waist. My skin is very soft, smooth, and white thanks to the skin care...Read On

Added: 23 Oct 2013 | Category: Crossdressing | Avg Score: 4.65 | Words: 1,143 | Tags: crossdressing  pantyhose  stockings  garter belts  butt plug  high heels  stilettos   | 15 Comments