Crossdressing Stories

3

MicheleNylons

Whores and Pimps - Part III

Third installment; our reluctant transvestite heroine gets a gang bang

Whores and Pimps - Part III By Michele Nylons Michele pulled at her bonds, struggling and wriggling on the bed trying to break free for a few minutes until she realised that she was securely tied and had no way of escaping. Ellie sauntered over to the bed and looked down at Michele, "Well honey, looks like we have you just where we want you; I think we are going...Read On

5

vote

tinycush

The Opportunity

a journey from gentle travestism to anal slut

THE OPPORTUNITY PART ONE I suppose looking back, that my childhood was to blame, that is if there was any real blame to be attached. It could have just been my inherited genes so I can happily blame my mother and father for being the smallest in the class, but I somehow also got left out when the popularity genes were issued, I became a loner and spent far too much...Read On

13

vote

summer1979

Airing Out the Laundry

sex at the laundry mat

Rick was so excited to be moving to the big city. He was 22, from a small town, and got a good factory job in the city a few hours from his home town. Rick would be far enough away from his parents that Renae would be able to roam free. Rick found a little 2 bedroom apartment on the ground floor of a building in a gay community, though he did not tell his parents it was. Rick's parents...Read On

30

vote

summer1979

Summer sexing a friend

A tale of sex, not love.

The night was especially dark that night. The moon was hid by a blanket of clouds. It was only 6:30, but that time of year it always gets dark that early. I left the empty bar after a couple of drinks, but I didn't want to go home. I wore skin tight jeans, a cute little tee, some cute tennis shoes, and a sexy underwear set. I took a little detour and found that Rod was having a fire....Read On

Added: 21 May 2009 | Category: Crossdressing | Avg Score: 4.39 | Words: 1,167 | Tags: crossdressing anal oral rimming voyeur

8

vote

summer1979

Summer in the fields

A one nooner stand

Steve is an average 19 year old on the outside. He has a full time job, a live in girlfriend (Amanda), divorced parents, and 2 cats. On the inside he's about to erupt. Summer is the eruption. Summer is Steve's "alter ego" who comes around every now and then. Steve used to let Summer drive around on the many less traveled roads in the area. Summer has never been with a guy, and she only...Read On

36

vote

summer1979

A night at the resturant

I was looking sexy enough to eat at the resturant.

I met John online; he was the owner of a small town restaurant, who was also married. I agreed to meet him that night after he closed. When I pulled up to the restaurant the lot was dark. I hustled up to the door in my tight mini and stiletto heels, my heart was racing faster with each step. When I got to the door John was waiting and quickly let me in. We sat in the back and he offered...Read On

33

vote

LisaLeeCD

The very first time....with lots more to come...

My very first sex as a crossdresser.

I guess we all remember our “first time”, and in my case the first time I was with a man while dressed was a awesome experience that I still remember vividly, and it happened by accident. I started crossdressing when I was about 14 due to my fascination with sexy women. The first time I slipped into a bra and panties and put on mascara and lipstick I knew I was hooked. I felt...Read On

19

vote

MicheleNylons

Whores and Pimps - Part II

The party begins and Michele has fun with Jill however the evil TV Ellie has other plans

Whores and Pimps - Part II By Michele Nylons Michele sat silently in the car as she watched the taillights of the police car disappear in the distance; the bitter aftertaste of the policeman's sperm still in her mouth. She was confused; the fat cop with his stubby fat cock had forced her to fellate him; but she had become sexually aroused and hadn't even realised it. She...Read On

Added: 16 May 2009 | Category: Crossdressing | Avg Score: 4.42 | Words: 4,245 | Tags: crossdress transvestite reluctant

12

vote

MicheleNylons

Violation

Michele is a closet TV and awaits her lover so they can play out their fantasy

Violation By Michele Nylons I have been home from work for over an hour; I lift my head from the brief that I have been reading by the light of a desk-lamp. The room is full of shadows. I look at the antique clock on the mantle and see it is approaching eight o'clock and I look over at the window; it is dark out. I close the file on my desk and then close the curtains in the study. I...Read On

8

vote

MicheleNylons

Whores And Pimps - Part 1

Malcolm is a closet TV and gets to choose the theme for staff party; he chooses whores pimps

Whores and Pimps - Part I By Michele Nylons Malcolm was a middle manager with a small business in a large city. Malcolm led a pretty boring life; he was in his forties, single, devoted to his work, he liked to keep himself fit, all of his family lived interstate except for his older sister who lived nearby, and he led a quiet social life. Malcolm had a few girlfriends over the years...Read On

54

vote

redhotfun4u

Little Black Dress

The events were all the result of a lost bet.

I pulled in the driveway, and saw that my wife was already home. My thought was that she’s home early. I unlocked the door and went in. A few feet inside the door was my work stool with a box on it with a note taped to the top. I opened it and started to read. Hun, I’ve decided that tonight is the night I want to collect on our bet. You are to follow...Read On

31

vote

LisaLeeCD

Truck Stop Tranny Sluts

Steamy Tranny encounter at a truck stop

My girlfriend and lover Candi and I were driving back to her place for some steamy tranny sex after a night of partying at a tranny/gay bar in town when we passed a truck stop on the highway. Buzzed and horny as we were, we laughed about stopping in the lot and doing so hookin’ as a means to get us some trucker cock. After a minute or two of silence, Candi said lets do it and before I...Read On

16

vote

LisaLeeCD

Lisa Lee Xdressing Adventures

I just love crossdressing sex!

I have been crossdressing since I was about 14 and by the time I was 18 or so I was meeting with guys I met online for sex and I loved it! I got married to a hot and sexy lady when I was 23 and I thought that might take care of my tranny urges but in reality it only made it worse. I now have to go long periods between playing dress up and it’s often all I can think of so when I...Read On

28

vote

SabrinaStarr

The Meeting

Some first meetings turn out better than others

I initially met Richard through a TG Community site and we seemed to hit it off from the very start. He was very open about his likes and dislikes, about him being a TG admirer, about having had a fair number of encounters and dates, but he never pressured to know anything about me. Drawn by his gentleness and gentleman ways though I found myself sharing my deepest dreams and...Read On

9

vote

simonelovesyou

Luck ran out

Everybody runs out of luck!! There i was again wearing my G/F's bridesmaid dress with the 4 inch wedges, bra, thongs and stockings this time. While wearing this wonderful outfit i yet again decided to tie myself up while everyone was out of the house. but this time i put myself into a tight hogtie using cable ties, with a realise mechanism of sizzors. So there i was enjoying the feel...Read On

95

vote

redhotfun4u

My night as my wife's sissy boy

My wife surprised me, and how! It Was a night I will never forget.

The last few weeks had been extremely busy and my wife and I had very little time to spend with one another. We needed some alone time so we made arrangements for the kids to spend the night at their grandparents house. My wife asked if I would mind dropping them off by myself as she had a few things she like to get ready while I was gone. As I pulled into the driveway I...Read On

11

vote

kirankaur88

indian crossdresser

hiiiiiiiiii every one here's kiran from india ,punjab first of all its not a fictitous story ,it is a real part of my life my actual name is rahul and me a guy now of 20 yrs old. so lets start frm my age of 12 yrs............................... me frm starting was very likely to kiddish me always remain at home .not to go any where else than in my street. in mid of june when...Read On

14

vote

tjr

I was a wartime TV for the US Army

Reform school teenager is offered a unique chance to serve the troops during WWII

'I was a Wartime Transvestite for Uncle Sam! TJ Ryder Chapter 1 Reform School Romance! I couldn't believe that all I got from my uncle Bill when he died after all he said to me about my being his favorite grand nephew was an old diary from World War II. I mean I thought we got along pretty darn good, and its not...Read On

Added: 18 Mar 2009 | Category: Crossdressing | Avg Score: 4.64 | Words: 2,457 | Tags: interracial tv crossdresser teen gay

21

vote

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

7

vote

phsusan

Susan is Complete

Love of pantyhose turns me into Susan

Like most of us, my cross dressing started with wearing pantyhose. This is a true story. My older sister (she was 14 and I was 9) would wear them to school (private school with uniforms) everyday. She started to notice that I would stare at her legs when she wore them. To this day I don't know why, but she would tease me trying hard for her not to be obvious about it, letting her skirt hike up...Read On

3

vote

barryboi

GAG-A-RIFIC BARRY part 2

Barry's revenge continues as girl power reigns supreme!!

After leaving Barry out in front of my apartment complex for 5 minutes, Jenna and I went to check on him. Actually, we went to laugh at him. What we saw was Barry trying to hop (handcuffed and anklecuffed) towards some bushes for cover. If you remember, Barry was wearing only a pink thong panty. We watched through the glass in the apartment stairwell and laughed until we cried. Barry...Read On

Added: 25 Jan 2009 | Category: Crossdressing | Avg Score: 4 | Words: 1,481 | Tags: barry panties cock cum humiliation

44

vote

Angelia

The Party

It happened one halloween

I am a closet cd. It was Halloween. My wife called from work and said she wanted to go to a party at a friends house. It was a costume party. She said she had a costume and I was to wear one as well. What, I don’t have one. Yes you do, your going as a girl. But I’ve never done this. Well you’re going to tonight. No one will care because it’s a costume party so get dressed...Read On

14

vote

Rachelcd

My First Cock

My cousin's Suprise for me

I am now Staying with my cousin after my previous story so I can dress up as much as I like. my Birthday was coming up soon and my cousin said she would have a celebration all weekend for me as it was during the week she said this would be my entrance into womanhood. It finally arrived this weekend I thought would be the best I just showered shaved what body hair I had off then left...Read On

11

vote

missunderstood98

My First Trip Out of the Closet

Crossdressing fun way over the edge

I have wanted to write this story for many years but I hesitated to do so out of my fear of the unknown. Since moving to Florida , I have pretty much been on my own for the first time in a long time. Let’s just say that now that I am older, I’m bolder! I no longer care who knows my sexual interests. It’s funny, because everyone I currently see understands my desires...Read On

Added: 13 Jan 2009 | Category: Crossdressing | Avg Score: 4.55 | Words: 3,824 | Tags: walking on the wild side

15

vote

missunderstood98

The Rendevous

An experience on the WILD SIDE!!!

The Rendezvous He called Saturday night just after ten. His wife was being admitted and they may induce her labor. He told me how much he missed me and how needy he was for my warm, wet mouth. I told him to be patient. His responsibility was to take good care of business. He told me that his wife was fine and that he hoped to see me on Sunday. We hung up. I...Read On

3

vote

PolaLeonor

Doing the landlord {Do It In Mexico (2) }

Make believe husband (cont. )

...........I got home from my first day gone public fully dressed as a lady. It was late in the afternoon, I filled my bathtub with warm water , put in scented bathoil in it , laid in there for an hour and 20 min. Thinking of that day in town , when I was getting fucked by FRANKLIN . Just thinking of that whole scenerio made me horny . I started slightly fingering my...Read On

Added: 05 Jan 2009 | Category: Crossdressing | Avg Score: 4 | Words: 3,866 | Tags: landlord

6

vote

barryboi

GAG-A-RIFIC BARRY

Brittany and Jenna take revenge on Barry.

When I first met Barry, I immediately noticed that his smile was gorgeous. The second thing I noticed about him was how great his ass looked in tight jeans. He was flirtatious and playful. Barry and I had been dating just a month when we made a bet on a basketball game. I won the bet and jokingly said that I wanted Barry to wear a pair of my panties. Barry blushed but...Read On

Added: 02 Jan 2009 | Category: Crossdressing | Avg Score: 4.5 | Words: 1,403 | Tags: barry gag cock panty

23

vote

Teresab

Christmas At The Salon

Fun for everyone at Susans beauty school...

Back in October I introduced my friend Susan to boys that wanted to be girls for her beauty school.They would come in for help with their hair and makeup and her students could practice on them.Everyone had a ball and it worked out very well. Soon the girls realized that this was a dream come true for the boys and became more demanding of them.Keeping the place clean was just one of their...Read On

9

vote

PolaLeonor

Do it in Mexico

Make believe husband

I live by the border to Mexico. I am a very low key cross-dresser . I moved out of my parents house at the age of 20 . Since I was financially O.k.. , like had a great job and was very independent. I was able to buy myself everything I wanted for cross dressing. When I turned 23 years old ,I decided that I wanted to go to Mexico and rent a house or apartment out there as a retreat or...Read On

4

vote

Rachelcd

Family Support

from the title u may think more than what it actually is i only have one family person who knows my cousin who is a lesbian she phones me up anytime she is alone for me to come and dress in her things. Any way to my story my cousin had phoned me up one day and told me to come over it was only a five minute walk and i was so excited. when i arrived she told me to go up to her room and once...Read On

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Crossdressing

Whores and Pimps - Part III

The Opportunity

Airing Out the Laundry

Summer sexing a friend

Summer in the fields

A night at the resturant

The very first time....with lots more to come...

Whores and Pimps - Part II

Violation

Whores And Pimps - Part 1

Little Black Dress

Truck Stop Tranny Sluts

Lisa Lee Xdressing Adventures

The Meeting

Luck ran out

My night as my wife's sissy boy

indian crossdresser

I was a wartime TV for the US Army

Smooth Sensation

Susan is Complete

GAG-A-RIFIC BARRY part 2

The Party

My First Cock

My First Trip Out of the Closet

The Rendevous

Doing the landlord {Do It In Mexico (2) }

GAG-A-RIFIC BARRY

Christmas At The Salon

Do it in Mexico

Family Support