Crossdressing

Jess_cd

Learning to be submissive - part 1

A gift comes at a cost

Before the days of internet chat rooms and social media I was very lonely as a young cross dresser. I can't speak for everyone of course but I would use telephone messaging services to talk to like minded people. I had received my first mobile phone for a recent birthday and I would often call up to chat to people. Sometimes things would turn into phone sex and on the rare occasion I would...Read On

Added: 02 Jun 2014 | Category: Crossdressing | Avg Score: 4.84 | Words: 2,200 | Tags: lingerie  oral  anal  cross dressing  stockings  submission   | 15 Comments

vanessagrrl

Memories

Reminiscing about time spent before dating

Just for fun, I though it might be nice to share some of the experiences I went through on my way to becoming the sexy slut I am. Before I had the confidence to fully dress and go out, and to go on the few dates I've been on, I was completely closeted. The only way I could express my girly side was through playing on the phone and all alone. I loved dressing up a few times a week. I...Read On

Added: 30 May 2014 | Category: Crossdressing | Avg Score: 4.8 | Words: 619 | Tags: crossdressing  toys  phone sex  ass play   | 7 Comments

Jess_cd

The Secretary - Part 1

I receive an interesting job offer

A lot of my stories are based upon the more formative years of my sexuality. Things are much less complicated these days. There's less sneaking around as I am not quite so in the closet any more, as well as the fact I live alone in my own apartment. I divide my time quite evenly between my identities although work is somewhere I still don't bring my cross dressing. Sometimes I feel like a...Read On

Added: 24 May 2014 | Category: Crossdressing | Avg Score: 4.92 | Words: 2,045 | Tags: lingerie  masturbation  domination   | 13 Comments

Jess_cd

Returning To Old Habits

After an extended break, I return to an old hobby.

Like many cross dressers, I found my habit has a certain ebb and flow. I would bury myself into my kinky hobby for several weeks, only to hide everything away again. I used to have purges too from time to time, where I'd convince myself it was wrong and throw my clothes away, swearing I'd never do it again. The last time I purged was in my mid twenties. I'd been with my then girlfriend for...Read On

Added: 22 May 2014 | Category: Crossdressing | Avg Score: 4.87 | Words: 1,399 | Tags: solo  cross dressing  lingerie  toys  masturbation   | 12 Comments

CallmeJulie

Call Me Julie part 5

Julie is not the only one with a secret.

Kelly is kissing me passionately, and I am kissing her back. Her hands are all over me as she feels me up. My tucked package is straining against the material of my panties as she grabs and gropes at my feminine attired body. Her hand snakes its way under my dress and into my panties, which she pulls down enough to release my cock, and tugs on it vigorously. She breaks the kiss and snakes down...Read On

Added: 19 May 2014 | Category: Crossdressing | Avg Score: 5 | Words: 646 | Tags: bi  oral  anal  dp   | 3 Comments

Jess_cd

My birthday treat

After months of helping me dress, my neighbour plans a special night.

My next door neighbour had begun helping me with my crossdressing by buying me my own clothes, and despite her initial stipulation that I continue to dress in secret, we had experienced a moment where that had all changed. Once that day had passed, Ellie and I became almost inseparable. If we weren't together, we were texting or talking on the phone. We would do everything an ordinary pair...Read On

Added: 18 May 2014 | Category: Crossdressing | Avg Score: 4.89 | Words: 1,822 | Tags: crossdressing  helping  oral  lingerie  strap on   | 15 Comments

Jess_cd

Making friends with my housemates

People always react in different ways when they find out about my cross dressing. Girls are usually more accepting than guys but everyone is different. I was twenty-two when I went to university and decided I would be completely open about it with everyone I met there. I found that most people were pretty cool with it, although some took some time to get used to it. I spent the first...Read On

Added: 14 May 2014 | Category: Crossdressing | Avg Score: 4.73 | Words: 2,157 | Tags: lingerie  straight sex  oral  toys  dressing   | 5 Comments

SkittleMonster

Jack's Dirty Secret

Jack walked into his bedroom, seeing his wife laying on the bed with a dildo in hand.

Jack and Mary had been married for ten years or so. Mary never thought that Jack would keep such a large secret from her. She sat at the house all day and did laundry, Jack's and hers. She never usually did his since he's picky, but she was bored and it needed to be done. As she was putting away some of Jack's clothing in his dresser, she saw something. It was a shiny pair of silk gray...Read On

Added: 08 May 2014 | Category: Crossdressing | Avg Score: 4.78 | Words: 1,355 | Tags: wife  husband  anal  vaginal  sex  love  marriage   | 7 Comments

Jess_cd

One of my first times

My first time with a guy

They say you never forget your first time. For me that's kind of true but in my attempts to seduce over the years I've claimed to have so many first times and I definitely don't remember all of them. Being bisexual and, of course, with my dual gender identities I have probably had more first times than most though. I was still cross-dressing in secret in my late teens and I'd never had...Read On

Added: 04 May 2014 | Category: Crossdressing | Avg Score: 4.76 | Words: 1,146 | Tags: cross dressing  gay  anal   | 13 Comments

transgurl

My Oddesy 1 - Glen (here and gone)

A (mostly) true story of my first time dressing for another

"But mum. I'm too sick to go to school." I give my best fake cough. It was late senior year and I had been busting my balls for months. I just want a day at home alone. She finally replies after a minute of withering glares. "Fine. I'll call the school. But you're seeing a doctor Monday if this persists. I'll be back around five." "Sure. Whatever." I lay perfectly still until the sound of...Read On

Added: 01 May 2014 | Category: Crossdressing | Avg Score: 4.71 | Words: 1,412 | Tags: first time  oral  lingerie  crossdressing   | 16 Comments

Jess_cd

A surprise helping hand

Getting caught paid off, in more ways than one

When I initially started to cross dress I would borrow things from those around me. At first it was my sister, then when I visited my father I would wear my step mother's things and eventually my girlfriend's. Mostly without their knowledge, of course. I was always as careful as I could possibly be, replacing things just as they had been left and making sure I had plenty of time when I...Read On

Added: 25 Apr 2014 | Category: Crossdressing | Avg Score: 4.92 | Words: 3,185 | Tags: crossdressing  lingerie  full sex  neighbour   | 13 Comments

CallmeJulie

While the Cats are Away

Kelly's best friend catches him dressed up

Thursday night, mom is going to visit relatives out of town; dad is away on a business trip and not supposed to be back until Saturday. It took a lot of convincing that being sixteen is old enough to be able to stay home by myself and not have to go with mom to visit relatives. Dad was going to be home in two days and I would be going with him to the family ranch. Finally my mom relented and...Read On

Added: 21 Apr 2014 | Category: Crossdressing | Avg Score: 4.88 | Words: 1,850 | Tags: crossdressing  threesome   | 13 Comments

CallmeJulie

Call Me Julie Part 4

Julie is not the only one in for a surprise.

Scott coaxed me out of the car and we walked the ten feet to the front door, he was practically dragging me while reassuring me that everything would be alright. "Kelly is expecting us, don't you worry about a thing." "She is expecting me? Dressed up like this? Somehow I don't think you are telling me everything Scott, if this ends badly I will be kicking your sweet ass," I told him. ...Read On

Added: 09 Apr 2014 | Category: Crossdressing | Avg Score: 5 | Words: 779 | Tags: crossdressing  threesome   | 5 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

jerrixdresser

Night at the Video Store, Part 2

a sissy, very blonde, bimbo slut goes to a video store in a rough, black part of a big city.....

There were some strong, black street toughs in the SUV, but they got quiet when they saw me step off the curb into the parking lot. My nipples began to get hard under my little black micro mini dress and I could tell they were looking at them. I must admit, my platinum blonde wig, a huge Vegas style wig that went down my back to my butt, swung right and left as I moved my head back and...Read On

Added: 15 Mar 2014 | Category: Crossdressing | Avg Score: 3 | Words: 722 | Tags: crossdressing  sissy bimbo  sissy slut  video store  black guys   | 3 Comments

CallmeJulie

Call Me Julie part 2

some secrets are meant to be shared

After regaining some of my composure, I got to my feet and pulled Scott up to his. I kissed him and pushed him up against the wall locker and pulled his shirt up and over his head. I kissed my way down his body and stopped at his gym shorts. I hooked both fingers at the waist band and yanked them down. The most perfect cock I have have ever seen was straining against the pretty pair of panties. ...Read On

Added: 11 Mar 2014 | Category: Crossdressing | Avg Score: 5 | Words: 898 | Tags: military  crossdressing   | 11 Comments

Kasey

Aunty's New Girl

Falling into the strange world of Aunty Trixie...

This is the continuation of Tickets Please! Shakily, I keyed in the URL from Trixie's card, my mind in turmoil, heart racing as her sweet gift seeped from my aching pussy and soaked into the lacy panties I was wearing. I was wedged behind one of the 'tables' thoughtfully supplied for the busy passenger. You know the ones, if you move a fraction either way you end up concussing your...Read On

Added: 10 Mar 2014 | Category: Crossdressing | Avg Score: 5 | Words: 2,981 | Tags: group  oral  bisexual  shemale  anal  crossdesssing  fisting   | 20 Comments

cheryl_lover

My first boy experience

First time cross dresser ends up with well hung guy..

It was my friend, Karly's birthday. Her choice for going out to celebrate was a drag night at a club. It wasn't so much fixed on drag as it was on gender parodies and cross-dressing for fun. I had been a closet cross-dresser for a long time, although I had told a couple of girls I knew. Everyone was going to cross-dress and have fun, but I was going to revel in it. I had never been with a...Read On

Added: 09 Mar 2014 | Category: Crossdressing | Avg Score: 4.59 | Words: 1,322 | Tags: bigcock  crossdressing  blow job   | 5 Comments

PlayfulAshley

Free Clothes

Not what I expected, but definitely what I wanted.

I guess it is something that goes through the mind of every new or closeted crossdresser. Shopping for new clothes as a guy is awkward because it is difficult to do without making it obvious it is for you. Yeah you can go online, but it’s tough if you’re not used to the sizing and the clothes never seem to look the same as the picture. Thus, when searching for playmates on Craigslist, if you...Read On

Added: 07 Mar 2014 | Category: Crossdressing | Avg Score: 5 | Words: 2,722 | Tags: crossdressing  sissy  slut   | 9 Comments

CourtneyFux

Mom's Old Boyfriend: Part Two

Courtney becomes an escort like her mother, after fucking Ron good like she did.

Having adopted my mother's appeal for wearing sexy clothing and turning on men, I had just sucked her rich former boyfriend's cock while she flew to Las Vegas for a long weekend with her new rich boyfriend. Mom had a love for the jet-set lifestyle and I was sure she was enjoying staying in an exclusive hotel and fucking her new boyfriend's brains out when he wasn't at the table gambling....Read On

Added: 06 Mar 2014 | Category: Crossdressing | Avg Score: 4.94 | Words: 6,785 | Tags: crossdressing  exhibitionism  oral  anal   | 10 Comments

sluttracy99

My Sexual Odyssey Part III: Becoming a Slut (Continued)

A continuation of the journey described in part 2

We got to Tom’s car, and he opened the door for me, then walked around and got in himself. The drive was short and uneventful, and we parked behind the club. There were some people arriving at the same time we were, and I noticed several who looked like they could be CD’s. We approached the club’s entrance, and I began to feel more relaxed. It is always uncertainty that is anxiety-producing,...Read On

Added: 05 Mar 2014 | Category: Crossdressing | Avg Score: 5 | Words: 4,521 | Tags: self  discovery  autobiography   | 21 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: 4.71 | Words: 5,251 | Tags: crossdressing  exhibitionism  oral  anal   | 7 Comments

pantiejordy14

My First Night Chapter 2

The second chapter to my night with Marie

Previously She also included in this bundle of sissy goodies, sheer black thigh high stocking and black three-inch wedges. My legs were so high and my body so curvaceous, my soft red lipstick tied in with the red baby doll. She had placed a blonde wavy wig which I tied into my hair with grips and styled with a middle part-in. Marie also supplied red nail varnish and some very...Read On

Added: 05 Mar 2014 | Category: Crossdressing | Avg Score: 4.3 | Words: 868 | Tags: crossdressing  gay  firsttime   | 5 Comments

sluttracy99

My Sexual Odyssey Part 2: Becoming a Slut

A continuation of the journey described in part 1

After having had a few experiences, I became slightly more comfortable with my sexuality. I decided to branch out a bit, and see what life had to offer. I wondered whether there were any bars or clubs that I could go to to meet people who were looking for someone like me, so I went online and discovered, that yes, there were quite a few such places. It is so wonderful having the internet...Read On

Added: 04 Mar 2014 | Category: Crossdressing | Avg Score: 4.95 | Words: 7,314 | Tags: self  discovery  autobiography   | 25 Comments

CallmeJulie

Call me Julie

Never assume you have complete privacy.

Coming back to garrison, after a yearlong deployment, is one of the best things ever. Imagine having to go a year without having your favorite lingerie to change into, and not being able to shave and pamper your body as you would like. As it so happens, we just got back the day before yesterday, and after all the clean-up and inspections, we are being given a four day weekend. My...Read On

Added: 02 Mar 2014 | Category: Crossdressing | Avg Score: 4.5 | Words: 660 | Tags: military  crossdressing   | 11 Comments