Crossdressing Dare Stories

42,978 results
Orientation
Length
Source
Infinite Scroll

Ride On Shooting Star Ch. 02

by papershotglass on Sep 1, 2017
Group Sex

Still cooling from our first hard fucking, Salue was ready to go again when she asked for my "services" again. Unfortunately, I couldn't do it just yet and could barely move, I was so content. Salue, it seemed, had hungrier appetites than I did, or at least could revive quicker than I could. "Get up," she demanded. Those beautiful breasts bounced when she p...

An Office Fling

by PoeDali on Aug 31, 2017
Group Sex

You are sitting at your desk. It's Friday, about 4:15. Just killing time, waiting for the weekend to start. You are finishing up the last of your paper work, when Jen comes over. You are pretty much the last two in the office, besides a few people toward the back. She leans on the corner of your desk, and you start chit-chatting about plans for the weekend...

How to Make Turkey Soup...Naked?

by SusanJillParker on Sep 1, 2017
How To

Please give me the support of your vote. * Just turkey. This how to story is just about turkey and how to make turkey soup...Naked? Be honest. Being that this is Literotica, you wouldn't read my How To story if the word naked wasn't in the title, now would you? Am I right? So, staying true to the title, How to Make Turkey Soup...Naked, whoever makes this...

How to Have Great Sex on the Beach

by robert1000 on Sep 1, 2017
How To

This guide is not for committed exhibitionists, nor is it for the faint hearted. It's not a guide for nudists, as nudists don't usually associate nudity with sex. I'm writing it because being naked and fucking on a remote, secluded or even sparsely populated beach is the one of life's great erotic experiences. The combination of the exhilarating freedom of...

Bisexual Haitian Marriage

by Samuelx on Sep 1, 2017
Group Sex

Life is hell and then you die. That's my outlook on things most of the time, and it's got to change. My name is Timothy Joseph. Friends call me T.J. I'm a big and tall, dark-skinned and rugged young Black man of Haitian descent living in the city of Brockton, Massachusetts. Every day, I'm basically trying to make it in this life. I work as a security guard a...

A Purging

by rhody on Sep 12, 2017
BDSM

I had one hell of a week at work. I thought for sure that I was going to be fired on several occasions, but I managed to survive and on my last day of my week, I was blessed with a fairly easy evening. But before that easy night, Trainer had called to let me know that he was coming over and take me out to lunch. There was a sense of urgency that I never he...

Jake and Noel Ch. 05: Game Changer

by baldeagle509 on Sep 13, 2017
BDSM

Noel stared at Gabby. She wasn't sure if she should be embarrassed or not. On one hand she was sitting astride Jake who was naked and was supposed to be licking her exposed asshole. On the other hand she had spoken with Gabby less than an hour ago about some of her deepest sexual fantasies. The past two days had seen a whirlwind of amazing sexual adventures....

Group Fun

by jp67blue on Sep 13, 2017
Group Sex

We've been together for quite a while now & are both very happy & secure with each other & our relationship; we share our fantasies regularly & try to make them a reality for each other & so far there's only one outstanding one; and it's one we've both shared for quite a while; it's just been a matter of timing to get this one to come true........ We've bot...

Lanceolina and Guinevar

by dantemendoza on Sep 1, 2017
Humor & Satire

6th Century A.D. Legend tells of the great Queen Arthuria who pulled, tugged, and yanked the great wizard Merlin's long sword out of his rocks proclaiming her as the first female monarch of England. Uniting all the neighboring borders into one huge kingdom, which she aptly named Cameltoe, Arthuria created the historical Knights of the Oblong Table. She ori...

While Guests Were Talking

by vie_secrete on Sep 13, 2017
Group Sex

Jean-Yves could not stand receptions. He did not derive any pleasure from the small talk and the shallowness of exchanges, and he was put off by the artificial politeness that accompanied welcomes and introductions, the unspoken lines of taboos when it came to topics of politics, religion, and anything else covered under the umbrella of political correctness...