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TinaTim
vanessagrrl
jennaryder13

Crossdressing

Our crossdressing (cross-dressing) stories feature tales of either gender (usually male) dressing up in the clothes of the opposite sex, for reasons of sexual gratification. Crossdressers are akin to the transvestic fetishism, which is a sexual fetish for the clothing of the opposite gender. The crossdresser can be of any sexual orientation.

7
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TinaTim

First Night Nerves - Part 2

Tina agrees to meet Barry without 'the girls'

I sat by myself on the bus, my briefcase on my knees, counting the stops and wishing it would go faster. Since Barry’s text message last night and his surreptitious call to my mobile that morning, I had been so excited, planning what I would wear to please him most. Debbie hadn’t heard the beep on my phone so didn’t know that I would be meeting him without her that afternoon. So far I had...Read On

Added: 17 Jun 2013 | Category: Crossdressing | Avg Score: 4.86 | Tags: crossdressing  cd  seduction  lovers  anal  

5
vote
vanessagrrl

Starting to Have Fun as a Slave Girl

Vanessa is won at an auction to do one man's bidding for the night

Greg and I had resumed our relationship as normal after my experience at Mistress Amber's. I was enjoying being his girlfriend. He treated me so nicely, and we enjoyed our time together. It was the most intense sex life I had ever had with anyone. For the most part he enjoyed being the dominant one, and he was happy to make me his little fucktoy after a nice night out. But it was that line...Read On

Added: 15 Jun 2013 | Category: Crossdressing | Avg Score: 4.6 | Tags: bdsm  crossdressing  oral  large insertion   | 2 Comments

17
vote
jennaryder13

My New Sissy Life

A sissy lives out her ultimate dream.

I was so stunned I was unable to speak. I only thought things like this existed in my fantasies and could never actually exist in the real world. It had been three weeks since I found an ad posted online seeking two submissive males for "training." I read the description which said, "Attention sissy boys! Have you ever wished that you were a trained sissy slut? Of course we both know the...Read On

Added: 12 Jun 2013 | Category: Crossdressing | Avg Score: 4.35 | Tags: sissy  feminization  sissification  oral sex   | 7 Comments

25
vote
TinaTim

First Night Nerves

Nervous Tim becomes Tina and loses her virginity

My name is Timothy. I live in a large city in the English Midlands with my girlfriend Debbie. We are both 22 years old and have lived very happily together for over three years. We both work in a call centre for a large financial organisation. I am not tall – 5' 4" on a good day – and have always been very slim. I am blonde with blue eyes and very fair skin. Debbie is two inches shorter than...Read On

Added: 09 Jun 2013 | Category: Crossdressing | Avg Score: 4.83 | Tags: cd  crossdressing  virgin  anal  seduction  first time   | 7 Comments

13
vote
vanessagrrl

Transitioning and Bound

Vanessa and her man find a mutual pleasure - her with other men

It had been a while since I started the hormones, and I couldn't have been happier. I was looking and feeling more womanly than I ever thought possible. It brought me a new confidence when I was in public, and made me feel so much sexier, and girly when I was in the bedroom. My breasts weren't that big, but they were growing over time. I had a nice handful, and Greg said he loved to suck on...Read On

Added: 20 May 2013 | Category: Crossdressing | Avg Score: 4.62 | Tags: crossdressing  bondage  oral  anal  hormones  gang bang   | 5 Comments

9
vote
1936Storyguy

First Meeting with a CD

A cross dresser experiences his dreams with a man

It was strange, he contacted me first and his profile stated he was looking for a domme or trans to submit to. I guess the hidden desire to please a man won out. We communicated through mail and messenger for months. We even met for coffee and some groping, where I tested his desire for nipple play, some severe pinching and even squeezed his sac to express the control I wanted and what he...Read On

Added: 18 May 2013 | Category: Crossdressing | Avg Score: 4.44 | Tags: cross dressing  sm  anal  first time   | 5 Comments

28
vote
CAPITALLETTERJ

Dirty Little Me

Caught, with panties on and my pants down...

Rushing around all day, it seemed like this was starting become a ritual for my Fridays but this particular Friday I would never forget!  Waking up late as usual I flew out the the door as fast as I could, not giving any thought to what I had done the night before. As usual my boss wasn't too pleased but I never really minded his attitude because everything he lacked in personality he made...Read On

Added: 15 May 2013 | Category: Crossdressing | Avg Score: 4.73 | Tags: gym  locker room  older  panties   | 6 Comments

17
vote
vanessagrrl

A New Level

Things escalate for Vanessa and her man

Greg and I had been seeing each other for a little while at this point, and things were going great. We had gone on a few dates and I loved how he always treated me like a lady. He made me feel so sweet, sexy, and vulnerable. Tonight was four months since our first night together and I wanted to surprise him with something a little special. I bought a long coat, and I thought it would be fun...Read On

Added: 13 May 2013 | Category: Crossdressing | Avg Score: 4.41 | Tags: crossdressing  buttplug  anal  oral  hormones   | 4 Comments

18
vote
cuckoldmalesub

Caught, Used and Loving it Part 2

My descent continues

It had been two weeks since I had been caught and used by the mystery woman and her boyfriend. They had left as quietly as they came, and I was left kneeling on the floor dressed in all my best female clothing, cum dripping off my face, and my own cock dribbling cum on the floor. Since then, I had had only two emails. One was sent immediately after they had left and contained ten pictures...Read On

Added: 10 May 2013 | Category: Crossdressing | Avg Score: 4.94 | Tags: femdom  crossdressing  forced  oral  whore   | 8 Comments

15
vote
ThePhantom

My First Time - Part 2, or The Beginning

Once was not enough

It was about two weeks after Halloween that the dreams began. I began to dream about being transformed again. I was able to recall the feel of the silky garment against my skin, the sensation of the nylons brushing against each other as I walked. I recalled all the women at the party who danced with me and rubbed my silk covered ass. "You feel like a real girl," more than one said, and I...Read On

Added: 08 May 2013 | Category: Crossdressing | Avg Score: 4.47 | Tags: nightgown  nylons  thong  heels   | 7 Comments

16
vote
vanessagrrl

A Great Date

A first date that I hoped might lead to a first steady boyfriend

I was so excited to sign online and see a message from my sexy college boy. We hadn't spoken in a while and I guessed that we would never get the chance to finally meet. Many a night had I masturbated thinking about his lovely cock, though I had only pictures to please me. It turned out that he had been thinking about me too. "I can't get you out of my mind," he said. "I need to meet you....Read On

Added: 05 May 2013 | Category: Crossdressing | Avg Score: 4.75 | Tags: crossdressing  anal  oral   | 8 Comments

20
vote
ThePhantom

My First Time

A true Halloween cross-dressing story

I met Lydia while living in Florida. I had recently won a law suit and didn’t need to find employment for a while, so I spent the first three months partying. A good friend had sponsored my membership at a well known and popular yacht club. They had a public side and a members-only side; the members-only side had better bands and more folks. If you parked your yacht and paid the docking...Read On

Added: 30 Apr 2013 | Category: Crossdressing | Avg Score: 4.61 | Tags: halloween  nylons  garter  miniskirt   | 5 Comments

14
vote
CourtneyFux

Hitch-hiking Baby Doll: Part Two

Being a sexy girlyboy for a trucker stud leads to lots of sexy pleasures.

I woke my trucker stud up in the middle of the night by sucking on his cock and making it hard for him. When I had him good and hard, I climbed back up between his legs and let him put it in me again. His cock was nice and big and my ass was good and tight. It felt good to feel like a girl receiving anal from her big Daddy. While we lay on our sides in his bunk and fucked, my trucker...Read On

Added: 16 Apr 2013 | Category: Crossdressing | Avg Score: 4.86 | Tags: crossdressing  oral  anal  bisexual  spanking   | 7 Comments

15
vote
CourtneyFux

Hitch-hiking Baby Doll: Part One

Hitching a ride with a trucker leads to loads of fun for this sexy little tranny boy.

I hadn't been in his cab for more than a half hour when the driver who picked me up, brought up the subject of sex to me. "Last week, I had a guy and girl riding with me and they both liked giving me blow jobs. And, you know, if I closed my eyes, I couldn't tell the difference of which one was sucking me off. They were both excellent at sucking cock." "That sounds like you had a fun ride,"...Read On

Added: 14 Apr 2013 | Category: Crossdressing | Avg Score: 4.67 | Tags: crossdressing  oral sex   | 6 Comments

16
vote
CourtneyFux

A Picnic in the Park

Wearing my sexy thong bikini to the park leads to hot action with a big stud.

It was a beautiful spring day, the kind of day a girl starts to think about wearing her new bikini to show off her hot body for lots of men. I was feeling frisky and thought meeting some new men would be fun. There was a county park near my town where lots of men go to meet up for some good blowjobs and hot encounters. I planned to go there today. My new bikini still had the tags on it and...Read On

Added: 10 Apr 2013 | Category: Crossdressing | Avg Score: 4.56 | Tags: crossdressing  oral sex  anal  exhibitionism  bisexual  voyeur  spanking   | 5 Comments

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