Crossdressing Dare Stories

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Infinite Scroll

New Slave on the Block (Part 1)

by DragonsKitten on Sep 17, 2017
BDSM

What once was good was bad. What once was bad was worse. Kirk found it was a terribly different world, cruel and horrible, even, now that the new Manager had arrived. He hadn't met her yet, but the entire office seemed to have slipped out of his control and into hers. Sitting in his chair in the President's Office, it was all Kirk could do to keep from shou...

Two and Then Him

by irishabastard on Aug 31, 2017
Group Sex

He watched her climb from the pool, and the moonlight and underwater lights made her skin glow as the water dripped from her. He was mesmerized watching her, he was often mesmerized watching her. She was tall for a woman with long toned legs and her stomach was flat and firm with muscle below full, natural breasts that were almost impossible on her small fra...

Ken's Fantasy

by carolinky on Sep 17, 2017
Loving Wives

Ken settled down in front of his computer and clicked on the power switch. He took a deep breath as the machine slowly began churning through its start up routines. He carefully leaned forward and felt for the microphone hidden near the speakers and clicked it on. Stan wouldn't have to know about the recording. Ken had been thinking about sharing the speci...

The Loan Officer

by latinafmm2 on Sep 1, 2017
Group Sex

It's early afternoon, I and a female friend of mine have been discussing our financial difficulties as of late, in our new little restaurant. It's a new place on 57th, you can go and sit at the bar or order all kinds of good, and homemade food. The problem is, it seems that somehow we're $4,000 short, and there's no way that we can make up that kind of money...

Slutty Service Call

by biwifeplaying on Sep 15, 2017
Group Sex

Gorgeous weather again today, but my A.C. broke. I realized last night when I got home and the inside temperature was a stifling 79 degrees. It was a hot night but luckily, I got a service appointment today, during a time when I could be home to oversee the repairs. Two guys arrived as soon as I got back from the gym and grocery shopping. I'm not wearing an...

Still In A Fog Over Last Night

by firejunkie on Sep 1, 2017
Group Sex

I was still in a fog over what I witnessed last night. The image of my wife totally and completely taken in lust will forever be playing in my mind. The image of Kris pounding her fingers in and out of my wife and her reaching, pulling, trying to get into Kris's shorts will keep me hard for a very long time. In fact, I was hard as I stood at the sink cleanin...

Our Little Experiment

by Moosifer on Sep 14, 2017
Humor & Satire

"Are you sure you want to do this?" "Yes! Of course! It will be fun!" Terran had tried to reassure Lenn a countless number of times that he wanted to try it with him, but Lenn could not shake that feeling that It was wrong and twisted. That was perhaps why Terran had chosen to be the victim in the scenario. Moments ago they had gone over the safety procedu...

Dress Club

by BOSTONFICTIONWRITER on Sep 1, 2017
Humor & Satire

I was on the west coast visiting some of my friends and I went to a dress club. I still laugh at the connotation of it, dress club instead of strip club. I was confused. I didn't know what to make of it. Am I supposed to dress up formally? Am I supposed to wear a dress? What? I had no idea what to expect and what I was in for until I walked through the door...

Rear in the Air

by LadyCanine on Sep 11, 2017
Anal

So there I was with my rear up in the air, being fucked up my ass by a young lover. How did I get myself into this delightful position, you may ask? With a lot of lube, and a little manipulation. It had started with fantasies of relaxing so much in the moment that I would be able to take a nice, hard cock up my ass, where no man had gone before. Recently I...

The Three Graces Ch. 02

by Nicola_Italia1 on Sep 14, 2017
Group Sex

He slept fitfully and when he awoke he remembered the night's events and grimaced. The three little putas! They had kidnapped him from his home in exchange for the freedom of the youngest one -Maria. She was so determined to stay away from his father that she had kidnapped him in order to ransom him and ultimately embarrass him into stopping his pursuit of h...