Caught Crossdressing Stories

164,111 results
Orientation
Length
Source
Infinite Scroll

The New Coach

by DetailedRPer on Aug 30, 2017
Group Sex

Tyler was a senior player on his school's tennis team. He has been the leader and all-time best player even as a freshman. This year is different though, he is getting a new coach. He hasn't heard much of the coach just knows that the team is just going to be different. The first day of practice doesn't seem to have as much of effect on Tyler like it used t...

Doing Us Both

by receptive2 on Sep 13, 2017
Group Sex

One night while the wife and I were out partying at a club on the East side of the River we ended up sharing a table with a gentleman named Bill in his late thirty's or early forties. The place was packed and there was virtually nowhere to sit so since he seemed to be by himself we asked if we could join him and he graciously agreed. We found out through c...

A Bubble Bath Warm-up

by Brandy Chase on Sep 12, 2017
Loving Wives

Terri Phillips was going through her normal afternoon routine, preparing for her husband's arrival from work. He always liked her to be waiting for him when he came home. A little kiss to show affection and a martini waiting for him was his idea of wifely duty. She loved Paul so much; she had no problem with this old-fashion idea. So, in her best wifely mann...

What I Wouldn't Do - Where It Started

by Sully_M on Sep 14, 2017
Interracial Love

Summers in Minnesota were an interesting experience. For most of the year, you spent your life in some variation of sweatshirts, coats, gloves, hats and scarves. But then summer would come, and you couldn't believe that you were living in the Midwest. The heat was humid, but tolerable during the day. The nights, though. That's what made living there worth it...

I Want Your Love

by beautyzdizaster on Sep 13, 2017
Interracial Love

Okay so this is my first time ever posting a story here on literotica. I'm excitedly nervous about this. I don't have an editor yet so I'm sorry for all the errors, I tried to catch them all. I hope you all enjoy this first chapter. Hugz and kisses @--'---,---- beautyzdizaster ****Lalaine's POV**** Yes! My boss decided to let me go early and to enjoy the w...

Mona and Her Orgies

by freeman64 on Sep 15, 2017
Group Sex

Moaning Mona had an undying passion for Saturday night orgies. The epithet had its source in her habit of letting out throaty sexual moans, almost similar to the call of animals during mating season, when she approached men who were part of her orgy or would soon be recruited to take part in it. When Mona joined a computer programming firm as a receptionist...

Sue, Rita, and I

by Justtoold on Sep 1, 2017
Group Sex

This story is another one about me and my wife Sue. This one took place before we were married and yes it is an actual true story of our younger more adventurous days. This story is like all my others in that I don't write with too much descriptive sex in them. I like to think my writing style is more of describing the chase than the actual catch. That is ju...

The Hard Sell

by RobertDaniel on Sep 17, 2017
Loving Wives

I work at a retail hardware store just down the street from where I live with my husband. I've worked there for quite a few years so I was comfortable with the job and all that it entails. As of late my husband and I have been exploring our sexuality and sending each other dirty pictures and texts throughout the day. We aren't permitted to use our cell pho...

Shelly Caught on My Cam

by _brent_123 on Sep 15, 2017
Loving Wives

My wife has been a severe pain in the ass lately. Now I can't say it is ENTIRELY her fault that we have not been getting along, but to make a long story short we've been having difficulties for quite a while. Due to this, our sex life has been in a nutshell, pitiful. I have always been a very sexual person. My wife, Shelly, used to be as well, but over the...

The Lottery Changed Everything

by mikoli5763 on Sep 17, 2017
Loving Wives

My name is James Boozer and I met Katherine Williams when the RA's for our dorms decided to have a meet and greet for new residents. I was a junior who had transferred from the large state university eighty miles from my home town to the smaller state college twenty miles from my home to be closer to my mom who had been diagnosed with lung cancer. I had to l...