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4
vote
tvk3983

Jaime's Way (part 3)

Jaime and Jeff step it up a notch

As Jeff closed the door he grabbed me by the hand and spun me around, pulling my nude body close to his, breathing in my perfume before locking his lips over mine. My fingers found the button on his jeans and opened them with urgency, more than a little pleased when his huge cock sprung out. “Damn, I want you so badly, Jaime,” Jeff moaned when he broke the kiss. “I'm yours to do with as...Read On

Added: 11 Nov 2015 | Category: Crossdressing | Avg Score: 5 | Words: 8,894 | Tags: cd  oral  anal     | 2 Comments

4
vote
tvk3983

Jaime's Way (Part 3)

Jaime gets uncaged and left alone for a week - she doesn't lack for company.

As Jeff closed the door he grabbed me by the hand and spun me around, pulling my nude body close to his, breathing in my perfume before locking his lips over mine. My fingers found the button on his jeans and opened them with urgency, more than a little pleased when his huge cock sprung out. “Damn, I want you so badly, Jaime,” Jeff moaned when he broke the kiss. “I'm yours to do with as...Read On

Added: 08 Nov 2015 | Category: Crossdressing | Avg Score: 4.5 | Words: 8,895 | Tags: cd  oral  anal    

6
vote
Maid2frill

Evie Gets Her Reward

The final part in the story of Mistress Sarah and Evie

I went downstairs to the kitchen, carrying the cold tea. As I walked into the kitchen, I could see up the drive through the window. There was a car parked at the top of the drive, a taxi. I ran back upstairs to Mistress Sarah. “Mistress, are you going out again?” I asked. “No dear,” she replied. “why do you ask?” “There is a taxi parked at the end of your drive. It looks like the same...Read On

Added: 07 Nov 2015 | Category: Crossdressing | Avg Score: 4.67 | Words: 4,655 | Tags: lingerie  crossdressing  mistress   | 2 Comments

11
vote
pentup47

The girl with green hair

An extra-special birthday surprise

"Is this cab taken?" Languorously, she lifted her green mascara-clad eyelids and gave a half-smile. "'Fraid so." I'd left the party in the local wine bar and decided to get home before I passed out. I was feeling pretty squiffy. Two taxis cruised by with their engaged signs on. It began to spit with rain. I looked through the back window of the parked cab. The interior light was on....Read On

Added: 07 Nov 2015 | Category: Crossdressing | Avg Score: 4.64 | Words: 840 | Tags: cross-dressing   | 11 Comments

12
vote
tvk3983

Jaime's Way (part 2)

Sherry has transformed Jaime into a sexy slut

I awoke to feel the dried cum on my face, ass and balls, and then remembering how I got that way made me smile. Crawling out of bed I made my way to the bathroom and took a hot shower and then easily shaved my already smooth legs. Out of the shower I brushed my hair and did what I could to make it appear more feminine. After I put on my make up I walked back to the bedroom and slipped into a...Read On

Added: 31 Oct 2015 | Category: Crossdressing | Avg Score: 4.75 | Words: 8,332 | Tags: crossdressing  anal. oral  strap on  cuckold     | 5 Comments

9
vote
COMP
Tier_innerhalb

Skye High

Best friends discover their mutual romantic interest in one another

It was more of a small gathering than a party. Eight friends hanging out in one house for the night, to enjoy a a late night hockey game. In the mean time, the living room stereo system played the local electronica radio station, while the small group enjoyed various activities. One, however, was not having a good time at all. Skye sat in the upstairs bedroom, her back to the door, her...Read On

Added: 30 Oct 2015 | Category: Crossdressing | Avg Score: 4.78 | Words: 1,223 | Tags: crossdressing  straight sex  romance   | 6 Comments

23
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tvk3983

Jaime's Way (Part 1)

Sherry make Jim become Jaime

I'd only been married a very short time when my wife came home and caught me masturbating while wearing a pair of panties and a bra. This in itself was bad enough but then she caught me again, and then again. The first time she caught me she was shocked and appalled but the twentieth time or so that she found me wearing panties and bra and with a dildo in my ass she really lowered the boom...Read On

Added: 26 Oct 2015 | Category: Crossdressing | Avg Score: 4.95 | Words: 9,151 | Tags: crossdressing  anal  glory hole  oral   | 9 Comments

4
vote
Maid2frill

Mistress Sarah plays mind games

The continuing story of Mistress Sarah and Evie

I woke up at 7am when my alarm went off, I was wrapped up in a pink quilt, Mistress Sarah had obviously thrown it over me as I slept. It was soft and comforting despite the fact that I had been sleeping on the floor in the hallway. I had been banished from the bedroom after I had cleaned her strap-on. I had stayed close to the door listening to the sexual tones of Mistress Sarah. I...Read On

Added: 13 Oct 2015 | Category: Crossdressing | Avg Score: 4.5 | Words: 3,351 | Tags: crossdressing  lingerie  mistress   | 1 Comment

4
vote
Maid2frill

Mistress Sarah fucks Evie Chapter 4

The continuing story of Mistress Sarah and Evie

I knelt by the door, anxious for the arrival of my Mistress. I could feel my arse pulsing around the butt plug in anticipation of what was to come. As I knelt and waited I could smell the pretty floral scent of the perfume that I had sprayed on my neck earlier. I felt soft and girly from all the day's events. I was in a prime mode to be fucked like a sissy. Even though I was not touching my...Read On

Added: 09 Oct 2015 | Category: Crossdressing | Avg Score: 4.75 | Words: 3,237 | Tags: crossdressing  lingerie  mistress   | 1 Comment

4
vote
Maid2frill

Mistress Sarah Gives Evie an Assignment

The Continuing story of Evie and Mistress Sarah, Ch. 3

Mistress Sarah led me back into her bedroom and sat naked in a chair in front of a large dressing table. She ordered me to fetch my maid's dress. It was time for me to learn how to properly dress her for a night out and she wanted me in full sissy attire for the event. Mistress Sarah watched me step into my sissy dress. She told me to turn around slowly for her as she pulled down on the...Read On

Added: 28 Sep 2015 | Category: Crossdressing | Avg Score: 4.75 | Words: 5,068 | Tags: crossdressing  lingerie  mistress   | 2 Comments

16
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tvk3983

I AM A Slut (part 1)

Becky has a lovely evening - in bed.

My roommate and I live in a nice house in a very nice neighborhood. We're roommates because of convenience and not because we're lovers. Well, not steady lovers anyway. Sandy is drop dead gorgeous and a very free spirit, meaning that when at home she is usually running around naked or nearly so. I'm a cocksucking, take it in the ass crossdresser with very little interest in women. I guess...Read On

Added: 18 Sep 2015 | Category: Crossdressing | Avg Score: 4.56 | Words: 3,241 | Tags: cd  oral  anal   | 7 Comments

6
vote
Maid2frill

Mistress Sarah makes Evie a Sissy 2

The continuing story of Evie and Mistress Sarah

"Look at you Evie. You're so slutty in your teddy and stockings,” said Mistress Sarah. Then she looked down at my hard cock and said, "....and your clitty is so big. Excited are, you?" Mistress Sarah reached out and firmly squeezed my cock a few times. It was a welcome sensation that reverberated though my entire body. Before I could respond, she ordered, "Turn around slut. Let me see...Read On

Added: 16 Sep 2015 | Category: Crossdressing | Avg Score: 5 | Words: 5,127 | Tags: crossdressing  sissy  mistress     | 3 Comments

7
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Maid2frill

Meeting Mistress Sarah

This story, although fiction, is dedicated to Mistress Sarah, a real person who I lost.

My heart pounded fiercely as I stood at the door to Mistress's house. I did not expect to be so nervous at meeting her again. After all I had known her for quite a while now. Mistress Sarah had been gracious enough to allow me back into her world. I was fortunate to fall under the control of such a dominant woman. She had moulded me into an obedient and submissive slave through the use...Read On

Added: 15 Sep 2015 | Category: Crossdressing | Avg Score: 4.86 | Words: 4,829 | Tags: crossdressing  spanking  mistress     | 4 Comments

6
vote
SxyJackyLeggs

Dreams come true. Part 1

A dream trip thanks to my Queen.

Here I am, tied up and being fucked by the biggest and first cock I've ever had. "How did I get here?" I think to myself and begin to think back on how this came to be. *** Today is Thursday and I see a huge box at my front door. Knowing that I'm not expecting anything my curiosity has the best of me. I take it in and open it to find two more boxes and an envelope. I start with the...Read On

Added: 11 Sep 2015 | Category: Crossdressing | Avg Score: 4.67 | Words: 880 | Tags: first time  exhibitionism  bdsm   | 3 Comments

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stockingluvr

An Introduction To Crossdressing, The Finale

As Jackie, Chandra and I finished up our food, we chatted about the evening yet to come.

Reliving our evening’s events had Jackie and Chandra pretty worked up. “You girls seem to be getting a little excited," I stated. "Are you ready for some more fun?” Simultaneously they both grunted, “Yes we are!” I leaned across the table to find them both holding the others cock and slowly working each other into a frenzy. “You should probably save some of that for back at the...Read On

Added: 24 Aug 2015 | Category: Crossdressing | Words: 3,457 | Tags: crossdressing  anal  gay  straight  oral  bisexual  backseatsex   | 1 Comment

21
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tnbiguy4men

Crossing A Different Line

A married family man's growing interst in female lingerie leads to his being taken as a woman.

In my personal journey from straight, married heterosexual to bi male, I discovered, along the way, that I was aroused by women’s lingerie. It started with trying on a pair of my wife’s nylon panties. The feel of the silky material, and the sight of how it fit, quickly brought on an erection. I used another silky pair in my hand to jack myself off, being careful not to get any cum on the...Read On

Added: 19 Aug 2015 | Category: Crossdressing | Avg Score: 4.89 | Words: 1,910 | Tags: gay  crossdressing  oral  anal   | 9 Comments

18
vote
tvk3983

Pam's First Time

Jerry is a friend from way back and meets Pam while looking for his friend, Kevin

Just a few days of spring break left and I was planning on making the most of it. Well, the most for me anyway. I'm a crossdresser and I have been for a long time. All through high school I'd secretly dressed, slowly building a wardrobe of pretty panties, a few skirts and blouses, bras, my silicon boobies, and most importantly, my shoes. The most important thing I had going for me, at...Read On

Added: 14 Aug 2015 | Category: Crossdressing | Avg Score: 4.61 | Words: 3,481 | Tags: cd  first time  oral  anal     | 9 Comments

6
vote
tvk3983

Carolyn Makes Her Way (part 3)

Business is booming and so is his hand on her ass!

Once I dragged my tenderized ass out of bed, tender because Mike had used a cane on me last night, I dressed in pantyhose, a navy blue, loose skirt, a cream colored satin blouse, black pumps with four inch heels, and a bra. After applying my makeup I took a look at myself in the mirror, making sure I looked good enough to conduct an interview at the leather goods store we were opening in just...Read On

Added: 13 Aug 2015 | Category: Crossdressing | Avg Score: 5 | Words: 7,084 | Tags: cd  oral  anal  bdsm  water sport     | 2 Comments

22
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CourtneyFux

My New Boyfriend

Workout buddy sweeps Courtney off her feet

I recently moved to a new town and joined a gym. It's not one of those fancy gyms with weight machines, a latte bar, and women in spandex running around trying to be noticed by men. It's a sweaty men's gym with barbells and dumbbells that require men to double up and spot for each other. The first day I was there, Jack "Kell" Kellson, a solid built six-foot-three-inch muscle boy my age,...Read On

Added: 09 Aug 2015 | Category: Crossdressing | Avg Score: 4.6 | Words: 1,292 | Tags: crossdessing  bisexual  exhibitionism  anal   | 8 Comments

19
vote
qt_sis

The start of my life as a submissive crossdresser

First forays into crossdressing and giving handjobs

I am a bisexual cross-dresser/sissy and have been enjoying my life as such for many years. It all began for me when a friend asked me to look at some of his 'girlie' magazines. We went up to his bedroom and looking through the magazine got Chris really excited and he got his cock out and started to masturbate. I couldn't take my eyes off his cock and I slowly reached out and touched it and...Read On

Added: 09 Aug 2015 | Category: Crossdressing | Avg Score: 4.58 | Words: 624 | Tags: crossdressing  handjob  masturbation  teens  caught   | 18 Comments

9
vote
Spooge

Not Crossing The Line

Crossdressing brings me closer to a woman than I expected

When I was a kid I had a book called, ‘What Do People Do All Day?’ It made a start at teaching me about the variety of jobs that exist in the world. As an adult I feel it would be equally beneficial if there was a book as simple as that one which answered the question, ‘Why do people do the things they do?’ Part of the trouble is that I often do not even understand my own...Read On

Added: 06 Aug 2015 | Category: Crossdressing | Avg Score: 4.89 | Words: 5,588 | Tags: crossdressing  photography  straight  fantasy  anal  sneaky  lust   | 4 Comments

6
vote
tvk3983

Carolyn Makes Her Way (part 2)

Mike paddles Carol - Hard!

After I left the office of my former employer I went immediately to see an attorney. There were two things I had to do: one see about suing the hell out of my former employer and two: I needed to get my name changed legally to Carolyn instead of Carl. I chose this attorney because I already knew him, very well in fact, right down to the birthmark above his nice cock. He wasn't surprised to...Read On

Added: 05 Aug 2015 | Category: Crossdressing | Avg Score: 4.83 | Words: 7,595 | Tags: cd  bondage  spanking  oral  anal  pee  

7
vote
JessieCD

Jessie Caught in the Act

After Jessie and Sue's office interlude, the boss catches them in the act.

Sue and I were starting to catch our breath from our office session when suddenly someone started knocking on the door. “Jesse! You’re late to your meeting with me! What in the hell was all of that noise coming from your office? I sounded like someone was having sex in there!” Now I knew I was going to get it. That was my manager Steve. Steve burst through the door and his mouth...Read On

Added: 31 Jul 2015 | Category: Crossdressing | Avg Score: 5 | Words: 2,166 | Tags: crossdressing  caught  romance   | 3 Comments

13
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Bunny12

He's So Pretty In Pink

Poor sissy's desires go wanting.

He is sixteen years my junior, six feet tall, blond haired and blue eyed, with an insatiable desire to be my submissive sissy slut. I never could figure out what drives his desire for an older woman, such as myself, but he can never keep his eyes off my long legs or my round, voluptuous ass. He pestered me to no end to dress him as a proper sissy and take his hungry ass with my strap on and...Read On

Added: 29 Jul 2015 | Category: Crossdressing | Avg Score: 4.46 | Words: 983 | Tags: sissy  bows  sounding  milked   | 15 Comments

6
vote
Recommended Read
tvk3983

Carolyn Makes Her Way (Part 1)

Carolyn meets her co-worker and the sparks fly.

After tucking my penis and balls away, I started dressing with the basics: panties first, a sheer yellow thing, then my bra with the silicon helpers we girls so love and then a pair of black stay up stockings. Next, I stepped into a short green miniskirt which I loved primarily because of how it would reveal my bottom when I bent over and shot pool. After that came my blouse, a long sleeve...Read On

Added: 21 Jul 2015 | Category: Crossdressing | Avg Score: 4.83 | Words: 8,639 | Tags: crossdressing  oral  anal  spanking   | 4 Comments

15
vote
Bunny12

Sissy Slut Gets All His Holes Filled

Desperate sissy slut boy gets what he wants.

He was waiting for me as instructed, dressed in the bag of clothes I had left for him earlier in the week. I entered the motel room to find him sitting on the bed in the mini skirt, sheer blouse, lace topped thigh high stockings and stiletto heels from his goodie bag. With his legs crossed, he appeared to be quite demure but I knew the desperate, horny slut that was raging beneath the...Read On

Added: 19 Jul 2015 | Category: Crossdressing | Avg Score: 4.93 | Words: 1,020 | Tags: sissy  strap on  motel   | 18 Comments

16
vote
CourtneyFux

The Frederick's of Hollywood Lingerie Model

Courtney's first job in Hollywood is as a Frederick's lingerie model.

When I first arrived in Los Angeles, I was staying at a motel on Sunset Strip in Hollywood. I had plans on working as a tranny call boy there. In the "L.A. Express" magazine, I saw an ad for a club on Sunset, called the Leather and Lace Lounge, that was popular with trannies and the men who liked them. I decided to go there and learn more about the tranny scene in Hollywood. It was three in...Read On

Added: 17 Jul 2015 | Category: Crossdressing | Avg Score: 4.69 | Words: 1,716 | Tags: crossdressing  bisexual  exhibitionism  oral   | 7 Comments

7
vote
tvk3983

Carolyn Makes Her Way

After getting fired Carolyn moves in with Mike

After tucking my penis and balls away, I started dressing with the basics, panties first, a sheer yellow thing, and then my bra with the silicon helpers we girls so love, and then a pair of black stay up stockings. Next, I stepped into a short green miniskirt which I loved primarily because of house it would reveal my bottom when I bent over and shot pool. After that came my blouse, a long...Read On

Added: 15 Jul 2015 | Category: Crossdressing | Avg Score: 4.86 | Words: 8,631 | Tags: crossdressing  spanking  anal  oral     | 4 Comments

12
vote
ThePhantom

Discovery

Kyle is discovered indulging in his secret passion.

Discovery, one of the greatest fears he has. All others take a backseat to his fear of being discovered indulging in his passion. You see Kyle is a cross dresser. Like so may others he doesn't know where this desire to dress up came from, but soon it was too strong to ignore. He started out with pilfering a few items from his sister's room and wearing them behind closed doors when the house...Read On

Added: 08 Jul 2015 | Category: Crossdressing | Avg Score: 4.92 | Words: 2,010 | Tags: learning  secret  lingerie  anal     | 6 Comments

5
vote
JessieCD

Jessie's Office Interlude with Sue

As Jessie's first date with Sue ends, now it cums down to the office...

I could not believe what a great time I had on my first date with Sue. Her planning was impeccable. From getting caught at the department store, to my new set of lingerie and clothes, and then a feminization session at the salon. Only to wrap this up with a surprise sexual encounter with Sue, her male friend Quenten, and all whom I met at the various retailers. It was a first date that I...Read On

Added: 07 Jul 2015 | Category: Crossdressing | Avg Score: 4.6 | Words: 1,848 | Tags: oral  panties  creampie   | 3 Comments

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