Role Swap Stories

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Infinite Scroll

And Now I am Marcella?

by HerSubBoy94 on Jun 19, 2018
Transsexuals & Crossdressers

I'm so glad you're back! I have some news about my role with Miss Marsha. I am so tangled up with her now. She keeps pushing me to be like a woman. She inspects me every day after I've done my personal preparations for the day. I have to shave my whole body, every day! That takes a while because if I miss an area, she makes me go back and do it all over ag...

Boobs are My Passion Ch. 02

by SDRogers on Aug 7, 2018
Erotic Couplings

It has become time to bring you the further iteration of my Big Boob adventures of my early twenties.. Just to recap on the story so far..."Occasionally we would suck the same breast together and I have to admit that I never done anything sexier in my life". And that's the catalyst for the following... Let's take off from there... Relaxed on the couch and...

Room 143

by Rusty6891 on Sep 13, 2017
BDSM

***This is my first submission, this work is completely fiction... Please give me feedback.** It was the first time he and Stacey had agreed to do anything like this, he wasn't too sure how he felt about it, knowing that two hours from now he would be tied to his own bed at the mercy of his girlfriend. He was just finishing up in work and was about to mak...

New School Nurse

by idope247 on Nov 1, 2017
Erotic Couplings

Following a number of incidents of sexual harassment at Biddlecomb High, the principal Lorne Smith decided that he would file a request for someone to conduct sex education classes. The young lady hired by the authorities to do the job exuded sexuality herself. She was slender, petite, had flaming red hair and hypnotic green eyes. When she called into his o...

Miss Clemar's Dilemma Ch. 02

by thewilds on Dec 2, 2017
Loving Wives

Author's note. This is a continuing story and although you might enjoy this chapter on its own merits, you would be advised to read the first chapter first. (It is a short chapter!). ***** For several weeks prior to the incident, Miss Clemar's mind had been going through an inner battle - a battle that a winner was slowly emerging from, and as the stronge...

Caught In Lingerie Ch. 02

by hicutlover on Mar 5, 2018
Transsexuals & Crossdressers

As I awoke, I found myself on my side, with Tim's arm wrapped around me. He too was sleeping. I looked at the clock and figured I was out for 30 minutes or so. My bed sheet was covering the two of us and all I had on was my bra and thigh highs. Tim was still naked. My sissy clitty was hard; my horniness woke me up and I wanted more cock in my boypussy, right...

A Teenager's Monologue

by Jester72783 on Sep 12, 2017
Non-Erotic

Every guy at some point in his life is confronted with the worst of a teenager's problems: sex. Specifically, the opposite one. Men have for years attempted to analyze women. See what makes them tick. What gets them ticked. Philosophers for centuries tried to get inside a woman's mind, only to find themselves maddened at the prospect. All that philosophy and...

Bi-Sexual Cuckold

by Anal Slave on Sep 13, 2017
Fetish

Bi-Sexual Cuckold Pt 1 My wife likes to role-play her favorite game is for me to be a nasty boy and she is the teacher. It usually starts out like this, she will go out on the town and come home about 1 A.M. I know she is out fucking and sucking other men but it turns me on to know that she will be home nice and horny and will share her sexual adventures wi...

Need To Be Bad 11

by need_to_be_bad on Sep 17, 2017
Exhibitionist & Voyeur

need to be bad adventure - 11 My adventures in being bad began slow with my sharing some of the exciting things that a past boyfriend made me do. After that relationship ended I was left with a hunger for being bad. My adventures resumed at Literotica with my taking the risk of posting a thread entitled “A Strange Request” in April 2004 in the Literotica...

Mrs. Constance W...'s Letters 12

by bbtp41 on Sep 12, 2017
Letters & Transcripts

Hazel Park E..., Virginia Tuesday March 10th, 1863 Mrs. Annabelle K... 82 Piedmont Avenue, NE A..., Georgia My Dear Sister, I fear that this war is far from the end and it will be the ruin of our fair land and of us all. We will all be reduced to utter destitution on the bayonets of northern industry. General Sheridan's cavalry swept through E... four da...