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Crossdressing

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19

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

4

Settling In

Escaping oppression closed one door. Now Dawn has to find the next one.

I didn’t know why James had asked to meet me at Penny’s. He’d said that it was important for me to show up on time because they needed to talk to me. When I arrived, Penny greeted me at the door, and told me to go get Dawn out of the bathroom. I emerged a few minutes later completely changed into Dawn Summer, and into a mini-surprise party. “Happy Birthday Dawn!” Penny and James sang together....Read On

13

Telling Mom I’m A Crossdresser Part 7.5: Amateur Pole Dancers

I thought I would try something a little different and involve more teasing to my story. enjoy :)

After our time at the spa, I spent a lot of time in my room trying out all the new sex toys we got from Richard and Monica. They were all exciting in their own ways and I came so much with each one. Some vibrated, some went deep and some felt good stretching my ass wide. The feeling of all the sensations I could get from my new plastic and electric friends were amazing and found myself...Read On

4

Karren Gets Fucked and Sucked

Sex is abundent in this story

Adventure in Nylon 3 Part 1 Karren gets Fucked and Sucked He was all dressed up in his finest outfit. Starting with the prettiest white lace panties he owned. A white lace teddy with attached garters, a built in under wire bra that was filled with breast shaped silicone pads to look and feel like the real thing. He covered these with a silky smooth full white nylon slip. His shaved legs...Read On

18

Park-n-Play

State parks are not just for nature lovers...

Being the social butterfly that I can be at times, I was checking a website that listed my area to see of there were any 'cruising' areas I could check out in hopes to share my fetish for crossdressing and pleasure. There were several areas, too many to choose from, so I opted for a forested state park. Since much of the funding for the parks in Ohio have been suspended or cut, the chances...Read On

13

Ready to Perform, Part Two – All Crossed Up

I get more than I bargained on!

Much happened in the next twelve months following that first session with my ex and her new partner: Ann began divorce proceedings which I didn’t contest, I financed myself into another home, and Ann, David and I met for two more sessions of torrid sex. These sessions were pretty much replays of the first; I would first screw Ann thoroughly through at least two climaxes, and then she would...Read On

14

And It Begins

I make my first real steps into the real world.

There seems to be a common belief, if you want to call it that, that there are basically three “levels” of Crossdressers or Crossdressing. The first of these is what is referred to as fetish dressing. These people have no intention of doing anything other than wearing items of feminine attire. They have no desire to even attempt to emulate the female persona. This is purely a very temporary...Read On

9

Sissy sperm bank

I started the morning my favorite way, really the only way I know how: with my bull's big cock between my lips. This was one of those nice slow blowjobs that he liked to start the day with. I made it especially wet for him today, slobbering all over his thick shaft while lovingly looking up at his eyes. I grasped the base with my dainty hands and licked the head like a lollipop while smiling...Read On

10

Confessions of a Sex Crazy Cross Dresser Part 4

Chapters 7 and 8 of Book #1

Hi Everyone, I hope you like these chapters, please let me know if you want the next two. Chapter 7: Triangle of Fun I slept great that night with a full stomach of drink, food and Peter’s cum. I woke up on Friday and thought this is going to be a hell of a weekend. I played around with my cameras and had finally figured out how to use the self timer on the 35mm and how to use all...Read On

6

Karren Gets Sucked and Fucked Part 2

It gets hotter for Karren, Nancy and Kevin

Karren followed Kevin to his home in her own car so if she had to leave she could do so at her leisure. Karren wondered what Kevin's wife looked like, would she like the idea of a man dressed like a woman making love to her? Would she like sharing Kevin's cock with another man dressed as a woman? She hoped everything would turn out for the best.  Her thoughts were arousing her cock; she...Read On

14

Extended Vacation Part 2

Cassie continues her new life

Chapter Two in my novel of Cassie living 24/7 as a woman...please read Chapter 1 and let me know if you want more. EXTENDED VACATION Chapter 2 After experiencing a great sexual adventure less than two hours after becoming Cassie full time, I was now in a even better mood as I got back on the freeway and headed north. Due to the low air pressure in my tire, I drove around 50 MPH for...Read On

7

Beach Day

Wearing my sexy panties to the beach gets the men turned on for me.

Wearing my sexy panties to the gay beach always gets the men turned on for me. Being the only girlyboy there, I get hit on by lots of big studs. The attention they give me is flattering and leads to lots of sexual pleasure. Being topless, I get to show off my nice titties and the sexy panties I'm wearing let the men know I want some dick like a woman gets. It was a beautiful day for the...Read On

9

A Master For Julie Jizzbucket

A story i have written in regards to my master and myself

I had spent the last couple months indulging in some mild cross dressing. After a few nights wearing clothes that made me feel so sexy and womanly. Until recently I had only worn panties, bras and a few sets of stockings and teddys that I had bought for an old girlfriend before she broke up with me to date a guy that had more money. I have also been going online to a site called Lush...Read On

20

The Cabin, Chapter II

I do my best to comfort the two frozen wanderers stumbling through the door.

I do not know how long I sat there gazing into the flames and sipping wine in complete peace. The wind outside was far away in my mind, but suddenly a huge bang broke the silence. The door flew open and slammed into the wall. Rain swept through the small cabin and sprayed me with icy cold droplets. I nearly fainted from shock, and the noise from my pounding heart overshadowed the howling of...Read On

22

Jessie's Fantasy: Chapter 2 The Transformation

Now that Jesse and Tracy had fun, what else is in store for Jesse?

Here I am in the bathroom buck-naked and hairless. An amazing thing happened in the tub of my best friend's bathroom. My secret love and best friend Tracy, just had an amazing love making session. We were starting to get hot for each other after I dried off when the door bell rang, and her beautiful naked self ran out of the bathroom to answer the door. I started reflecting on what just...Read On

6

Girlyboy Gone Wild - Part Two

The panty party weekend brings new boyfriends into Courtney's life.

It was very flattering when Bill told me I have a hotter body than his ex-wife. Since it was his first time with a girlyboy, I knew he was being honest. A more experienced gentleman might have said it just to be nice. But Bill really meant it. In fact, he said his cock was already hard for me just from seeing my nice ass poking out of my turquoise thong. Bill was my 7:30 date, then I had Dan...Read On

16

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

8

A Date For The Weekend Chapter 1

A perfect date for the weekend leads to more.

I've been crossdressing and living as a woman full time for years. I put a lot of time and work into transforming myself into an attractive woman that can accompany a man anywhere in public and never raise an eyebrow. I've long since moved on from having casual cheap hookups to expecting more elaborate playtimes, and generally only date men if we can plan a weekend or more together. I mean, if...Read On

14

Felix becomes Felicity - Chapter 7

FELIX  becomes FELICITY Chapter 7 …We both fell asleep almost immediately. I got up whilst he was still asleep in the morning and put on his shirt loosely over my naked body. I woke him up with breakfast , we kissed and he left late morning.  I had been lucky to escape him not discovering my penis! I had to think hard about what to do about this. I would just have to have to tell him...Read On

The Night Of A Thousand Dreams

I hope you enjoy

There was a few odd looking drugs laying on the side from a party. Being bored I decided to see what they were all about, I had dabbled before but had no idea what they all were. I had seen someone use a bottle with an inhaler on it, one good slug later I felt good. I looked through my wardrobe and decided that all guys seem to go for the more cute look in a girl. As I was feeling daring...Read On

22

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

9

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

3

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

11

Vanessa Spends a Night Semi-alone

One night I was laying around bored, so I decided to get all sexied up for no one but me. I got out one of my favorite outfits, which you can see in my picture. I was so excited as I undressed, and laid everything out that I was about to slip on. First I put on my sexy Victoria's Secret thong. It was white with black lace, and it felt so hot as it slid on. Then, I put on the matching bra. It...Read On

11

Telling Mom I'm A Cross Dresser part 18: Missy's Halloween Party

Part 18 is about halloween. Hope you all enjoy despite i was a little rushed for this one.

I had enjoyed my week of sex with Thomas and Lemar but in the end it left me sore and used but not like I was complaining. It was now getting close to Halloween and mom and I were making plans to go to a Halloween party a few city blocks away from us. Yeah, sounds kind of boring I know but it was no ordinary party with costumes and drinking alone. It was an orgy for bisexual people. It...Read On

18

After the Show

An invitation to a drag show proved to be an invitation to more.

I‘d met David through my (now ex) wife. He lived in the Twin Cities with his partner Dennis. His being gay made it very easy for me to talk openly about being Samantha. He hosted a drag show on Saturday nights at a small gay bar so he’d invited me to come along, meet the ‘girls’ and see the show. I could stay the night so I could go dressed and have a fun ‘girl’s night out’ while he MC’d...Read On

22

My First Taste of Cock

Tammy blows and swallows her first cock.

After fantasizing for so long about what it would feel like to dress as a slut and suck a cock, I decided it was time I tried the real thing. I posted an ad on Craigslist with a couple of pictures of me dressed, asking for someone to let me dress for them and swallow their load. I got a lot of responses and most of them just sounded creepy except for Matt. Matt was 36 (I was 25) and a hot...Read On

29

Confessions of a Ladyboy - Part 1

He helps me resolve my boy/girl confused sexuality dilemma

I was eighteen and new in the boy's hostel. No one had wanted me at home. I had never known my father. I saw my mother go out with a different man almost every night ever since I was old enough to remember such things. She taught me some valuable lessons - how to be attractive, how to carry myself, how to be seductive, how to do my makeup. She always said, "You are such a cute boy, you...Read On

10

slut on the town

I got put in a full nelson the other night by a naked black guy. It happened in a video preview booth at Corey's Adult Video store in Oakland. I had been hanging out in the arcade, wearing just a black two-piece string bikini, and a pair of fire engine red high heels. I had been there for about a half hour, but I hadn't seen anyone. But it was early, only 3.30 p.m. Then I heard the buzzer go...Read On

25

Taking That First Step

A story from the seventies

Lance was seated on a bench on the tree-lined sidewalk waiting for the store to open. Despite the warm morning air he began to sweat and his heart pounded in his chest, this was a bold step for him. Now, this particular store was located in an older but still very popular outdoor shopping center despite the malls springing up everywhere. It was commonly referred to as a specialty shop,...Read On