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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.

8

Taking That First Step. A new chapter begins

Cassandra introduces a new pleasure.

The Summer was drawing to a close, and Lance would soon return to school for his senior year. As excited as he was about his final year, he was saddened that meant no more early morning rendezvous with the stunning Cassandra. It had been a great Summer. Thanks to her assistance Lance had taken his desire to crossdress to a whole new level and he became Lana. In order to complete his...Read On

1

Alexia's Tale Chapter 3 - Sensual Outgoings

Venturing out to embrace her fem side, Alexia discovers a glimpse of her desires...

Sunlight beamed through the curtains, warming up the room. Under the sheets, a mildly aroused Alexia laid half asleep, one finger halfway up her ass and her mouth gently sucking on her other hand’s fingers. Her cock was slightly bulging, as it tried to break free from its fabric cage, causing it to pull on the thong. Her hair was messy, but in a way that you’d love to see after a good...Read On

10

Busted by My Step-Sister's Boyfriend - Chapter 1

My Step-Sister's boyfriend catches me watching the two of them having sex

My step-sister Alicia is two years older than I am and built like a Greek Goddess with her braided blonde hair, slender body, long silky legs, tight round ass, and 36D breasts. Her boyfriend Bob is a college freshman soccer player who regularly spends the weekends at our house. My parents do a lot of weekend travel to relieve the stress of their jobs, so the house is virtually ours to...Read On

2

Alexia's Tale Chapter 2 - Online Exploration

Continue the tale of Alexia as s(he) goes down the path of being a gurl!

Looks like it's never gonna stop," Alexia muttered, the warm vapor from the cocoa rising past her face like a discounted sauna. Her voice pitched higher, much to her liking, she continued, "twenty-four years old, with a job as a writer. Yet I'm bored." The maroon cardigan wrapped her exposed shoulders, but did little to envelop her breasts upon which she rested her hands that held the...Read On

3

Rainy Day For Alex(ia)

Alex copes with a rainy day Sfw. Please comment, rate, and i'll develop her NSFW!!!

The smell of rain danced near his nose, as Alex sat by the window. It had been raining for two hours now, with no sign of stopping. The clouds were ever so gray and the wind gave the trees reason to dance. “I guess I know what will make this afternoon cozier,” he said, making for his wardrobe.  Passing his mirror, he caught sight of himself again, 5 foot 8, 62 kilos, with long brown...Read On

13

The man of My Dreams - Continued

I opened my door and there stood my beautiful black lover!

When the second day of my conference was over I returned to my room to change and become Melanie.  My hopes was that my beautiful, black god with his massive, uncut cock would be waiting once again at the bar.  For tonight I chose a sexy floral mini dress.  It was a white background with a floral print.  It had a tight strapless bodice and a full skirt.  My heels were 5 inches with a 1...Read On

15

I met the man of my dreams

I noticed him at the gym when his cock was peeking out from under his shorts

I work from home and only have to go into the office at the beginning of the week and at the end.  So with travel and time in the office and a few extra chores, I dress in guy mode about 10-12 hours a week.  The rest of the time I am Melanie!  In the morning I dress as if I am going into the office.  I often wear a skirt and pretty top or a dress.  I always wear hose, my wig, full makeup...Read On

20

My best friends dick

After giving my first blow job it was time to let my sissy ass be fucked

I was a closet crossdresser with a crush on my best friend and finally, after we had both graduated I worked up the courage to show him how I felt.  I invited him only and met him at the door dressed in my sexiest/sluttiest outfit.  I fell to know knees and gave him his first bj.  It was also the first j I had ever given.  It was wonderful for the both of us.  It was something I had wanted to...Read On

11

Wife Gets Even, Chapter 2

Amy wins a bet and turns the tables on her husband.

Amy said, “So I think you are going to need to take next week off from work. I guess you could go to work with your new look if you want to but I am doubting you will want to subject yourself to the ridicule and questions about your look. You should get some sleep so you are ready to go in the morning. Have coffee made by seven and make sure you shave your face and body again.” I simply...Read On

27

Sucking My Best Friend's Cock

He never expected that I was sissy and never dreamed he would be one of my lovers

This happened when I was beginning to dress up as Mel frequently.  Saturdays were the best days for me, except that my friend Pete would always stop by in the middle of the afternoon, so I always needed to be changed back into my boy clothes before he showed up.  One Saturday morning I decided that it was time for Pete to meet Mel. I took a warm bath, removed my unwanted hair and applied...Read On

1

Ladies Night at the Leather Bar Part 3

The plot thickens, as does the crowd and the cum.

The aftermath of Round One found Carter and me cuddled together on one of the couches in the huge fuck room at the Roughrider Bar. We were soon joined by a cum covered Chloe, who sat, leaving me in the middle. I laughed and sang to her: "Rebel rebel, what's on your dress? Rebel rebel, your face is a mess. Rebel rebel, how could they know? Chloe joined me for the hook line, "Hot tramp... I...Read On

6

Ladies Night at the Leather Bar Part 2

A lot of dressing, a tossed salad, and then: the meat.

Now that you've met Chloe in Part One: Today I want to remind myself of how much I owe her for luring me into the circumstances wherein I met a beautiful man, a man who would change not only my life, but my basic conception of myself. I found him in the most unexpected of places. A place where Chloe brought me. SUMMER 2011. THE SAN FERNANDO VALLEY. I had just gotten home from work, put...Read On

18

crossdresser confession part 1

I really loved my wife; she was the most beautiful creature I have ever known. Tall, brunette and the longest legs you have ever seen. Myrtle's beautiful face is framed by her gorgeous brown hair. She was about 5'8" and had a great ass. Her curves were soft and very feminine, not a big chest but nice and perky tits I loved to play with. She would drive me crazy when she donned a pair...Read On

8

Ladies Night at the Leather Bar Part 1

Lingerie Love in the Land of Leather

Chloe McGill never led me astray. I was a fulltime, tax paying citizen of Astrayville long before I met her - I just wasn't that good at it. Then Chloe came along, and that girl has ended up getting me into some of the most outrageous adventures. I adore her. It must be made clear how much more she is than just a cohort in gangbangs and sexual trysts of all sorts and sizes.  She is the...Read On

23

becoming a cock worshipper

I first realized I was bi the summer after high school. Up until then I had only been really interested in girls. Like any high school guy I watched a lot of porn and soon realized that I really liked really nasty deep throat blow job scenes.  I especially enjoyed watching a girl choke and gag and cover a hard cock in her spit. I also realized that my favorite scenes always involved a...Read On

3

The Best of Both Worlds 2

"Oh, God, Daniel!" Arya cried out in ecstasy, as her body came to orgasm. Sitting on top of Daniel, she let her body bounce on him, as he shot a load of cum into her with every upward thrust. She screamed excitedly with each push that Daniel gave until he was finally finished, and Arya rolled off and lay beside him. The sex had been both exhilarating and disappointing. As always, it...Read On

1

Sissy Blane in the Hart of the Valley

Having had the first date with Plumrose, Blane visits a t-girl club with Cindy

When I got home from the Hollywood Hills I barely had the strength to remove my makeup. I was so exhausted I just wanted to flop on the bed and pass out, but I persevered and undressed properly, removed all makeup and even put my wig back on its wig head. But when I was finally between the covers my brain refused to cooperate, rethinking the night's events, imagining how they may have looked...Read On

8

Taking That First Step. Part 5.

Lana began to protest at being pulled toward the bed; she felt she had been punished enough. Her ass was on fire due to the spanking she had just received. Her protests were ignored. Lana was pushed face down on the bed and she felt Cassandra sit on her back before she could attempt to rise. She felt Cassandra attach something to her wrists. Lana opened her eyes and saw restraints....Read On

5

Special Soiree

The two sissies meet for their special party

“Amanda” was fully dressed when “she” opened the door. She almost shyly greeted her close friend “Suzette.” “Hi Suzette. It’s been a while,” Amanda said. Suzette had an unhappy expression on her face. “I know, too long.” Then she looked around clearly nervous. Amanda knew that sensation, and opened the door wider. “Please, come in.” “Thank you, Amanda,” Suzette said her confidence...Read On

17

Wife Gets Even - Chapter 1

A husband takes advantage of his wife over a bet but the wife gets a chance to turn the tables.

My wife and I get together with our neighbors to play cards to play cards about once a month. We generally have a good time but there are no stakes involved. For a poker player like me who is accustomed to gambling for large amounts of money playing just for fun is a little, well… boring. One night about a month ago, I tried to make the game a little interesting by including some drinking....Read On

7

Taking That First Step. Part 4

Lance gets fully dressed.

It had been a long week for Lance. He didn't think the weekend would ever arrive. It was his summer job and kept his mind occupied during the seemingly endless days. He worked for a small company in their shipping department. The job was not very glamorous, but it paid well and kept him clean.  Even as we worked his mind thought about what Saturday would bring when he visited Cassandra's house....Read On

10

Taking That First Step. Part 3

Lance's transformation continues

Lance had arrived at the specialty shop as himself, a young man wearing women's lingerie under his jeans. He was met by the stunning Cassandra, the shop owner and his confidant. She treated him to a wig, lipstick, eye shadow and then directed to one of the changing rooms. Waiting inside was one of the sexiest lingerie combinations that he had ever seen.  Upon exiting Cassandra reappeared...Read On

7

Two Cross-dressing COCK SUCKERS

It was a somewhat long and wide almost horseshoe shaped semicircle line that contained seventeen different men either bare ass naked or with full-frontal open-fly cock exposure that special Friday night last Dec. 24th. Yes, it was the finals of our Private Gay Club's BEST 2004 COCKSUCKER OF THE YEAR CONTEST. Just like each of the eleven preliminary monthly contests held before it, the rules...Read On

14

Taking That First Step. Part 2

Lance returns to the specialty shop

Lance's family was surprised to hear him up and moving at 6:00 AM. Saturday was his day to sleep in now that school was out for the summer and he didn't work on the weekends. They didn't question it and soon fell back to sleep as Lance headed to the master bathroom. He showered and then toweled off before heading back to his room. Once in his room with the door locked behind...Read On

15

Further Exploration

Shauna and Jerry make a video.

After Jerry kissed me goodnight and returned to his own room, I had time to reflect. Sex with him was so different than it had been with Jack. Jack took his time, slowly and steadily pumping his hard shaft in my man-pussy and making me feel like his special girl. Jerry was passionate and urgent, riding me hard and making me feel special in a whole different, slutty, way. I was Jerry’s...Read On

6

Jenny & Mike: Romantic Picnic

A nice romantic picnic that culminates into public pegging.

It was close to 10 a.m. and I was still in bed with Michelle sleeping peacefully next to me. Last night had taken quite a bit out of me. Having been used and fucked by two cocks was a huge turn-on. ‘Mike’ and ‘Carlos’ had given me quite a workout! I received the fucking of a lifetime. Sex with Michelle had always been great, but having a third person added a totally different edge. The...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

10
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Sharing Jessica With Nick

We introduced Nick to Jerry's secret, leading to one hot evening in preparation for his initiation.

Jennifer and I sat at my kitchen table on Saturday afternoon sipping beers following our fuck fest with Holly and Nick the night before. Jennifer didn’t have to worry about picking up her kids until Sunday late afternoon and Jerry wouldn’t be home until later Sunday night. We had both woken up late that morning and just now sat down to chat about what happened the night before. Jennifer...Read On

Saturday With Al

One of those rare days with a new lover that doesn't disappoint.

After a great night of sleep, I awoke Saturday morning thinking of spending the day making love to Al. After coffee, I drew a nice hot bath and proceeded to spend the next thirty minutes getting clean and smooth. After drying off I applied liberal amounts of a lavender-scented lotion to keep me soft and smelling nice. I also made sure that my feet were quite soft as well, since that seemed...Read On

15

Never go into an alley

Pulled into the alley behind a dumpster

It had been months since I had the opportunity to dress En-Femme. With so much time having passed and not being able to indulge my feminine needs, I was about to explode. The tunnel was long and dark to fulfill that need, but I knew that at the end of it would be a light. Not realizing just how long that tunnel was, I had purchased a new blonde wig, a new pair of tight, low hip riding...Read On