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Crossdressing

30

Night Trawling: The Crossdresser

Sometimes the streets offer the most delicious surprises.

The streets of Pomona live two lives. Like maternal twins, they coexist in parallel, appearing as virtually identical to those merely passing through its old and storied neighborhoods.  During the day, with the sun high overhead, myriads of people — whether they’re commuters traveling like drones or soccer moms distracted by their busy lives — they choke the streets in a constant pulse of...Read On

5

Being Christy - Part 3

Christy finds release after moving to university

My experiences with Jenny and James had been amazing, but summer drew to an end and it was time for me to take up my place at university. I didn’t need much and only took a couple of bags with me, but the move did mean saying goodbye to my sister’s wardrobe. My parents gave me a lift to my student digs and after some typically over the top parental farewells, I was left alone three hundred...Read On

10

Stranger Fuck

A crossdresser is pegged in a sex club.

  I noticed the time strike 10pm on my watch as I got out of the cab outside the Red Circle. Hopefully tonight I was going to get lucky. After paying the cabbie and stepping out of the cab, I fixed my tight pink and black striped dress as I stood outside the club. The Red Circle was the most notorious Sex Clubs in the city where couples and singles went to hook up. Tonight was their...Read On

24

She Made My Dream Cum True

A girlfriend helps me bring out my inner slut

I had been seeing Ellie for a few months before I told her about my little secret.  We enjoyed straight sex, but something was always missing for me.  After I told her about Vanessa, and my desires to dress up and be treated like a woman, I was really scared she was going to cut and run, but she actually was interested in knowing more.  I confessed some of my innermost desires to her.  I...Read On

5

Taking That First Step. A New Chapter Begins. Part 2

Cassandra's new idea

September had arrived and Lance returned to high school for his final year. He still found himself attracted to and flirting with all the girls and not the guys. He surmised that it was only when he was dressed as Lana did his choices change. He couldn't see Cassandra during the week as he worked out after school and then went to his part-time job. He got home in time to join his family...Read On

10

Soldier Standing to Attention

A soldier and the slutty nurse

I had been flirting with a soldier that I had met online for a while. He was a lot younger than the guys I normally go for, but surprisingly open minded for his age. He was also really hot and had a nice body, so I agreed to meet. We toyed with the idea of some roleplay during our online chats. My favorite was the wounded soldier and the slutty nurse; it made me very hot. I got myself a...Read On

26

My First Time With Two Guys

I got more than I bargained for when I met a guy for sex

I had made a date with a guy I had been exchanging emails with on and off for three months. He seemed nice enough and was pleading with me to meet with him. He convinced me to meet him at a nearby hotel and left the key at reception. Then, he was going to wait at the bar whilst I got ready and I would text him. Then, he would come up to the room and let himself in. I arrived at the room,...Read On

13

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

2

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

15

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

4

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

17

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

21

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

30

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

13

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

32

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

3

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

7

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

20

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

26

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

4

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

2

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

9

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

18

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

8

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