First Time Sissy Sex Stories

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Casey's Submissive Journey Pt. 01

by corduroysissy on Dec 14, 2017
BDSM

Karen walked into the bedroom and Casey thought he would have a heart attack. He was reading a book in the corner chair and looked up at his lovely wife. She was wearing a pair of dark red, mid-wale corduroy jeans. Casey had a corduroy fetish, corduroy turned him on a lot. He'd purchased many pairs of corduroys for her over the years and she knew the red o...

Mistress Viagra Pt. 01

by Njstraponlover on Sep 13, 2017
Fetish

This story is 100% pure fantasy. None of it ever happened. If you are offended by stories of a mature nature containing references to bondage and humiliation, please do not read. This is fiction!! ***** I had been chatting with a new online mistress for a number of months and during that time she had me buying all kinds of sexy woman's cloths, new sex toy...

Sissy for a Day

by silkstockingslover on Oct 16, 2018
Fetish

Summary: With his wife's help and support, a man becomes a sissy for black cock. Note 1: This is a Halloween 2018 Contest Story. Be warned: this story involves sissy sex, obsession over black cock and a bukkake. If this isn't your thing, please don't read any further. Note 2: This is dedicated to the real Paul who requested this story. Note 3: Thanks to:...

Sissy

by TxRad on Sep 14, 2017
Mature

I came in from work about noon on Friday. I had been gone for a little over two weeks. Pulling in the driveway, I noticed that my daughter's car was gone but her best friend's car was parked in front of the boat on the far side of the carport. You talk about a pair to draw to; those two were it. My daughter is tall, dark, and slender, Sissy is even taller, b...

The Perfect Handjob

by Ricky_writes on Sep 13, 2017
Loving Wives

I've been married for 20 years. It didn't take my wife Tammy and I too long to figure out that I had a much stronger sex-drive than she did. Frankly I have thoughts of sex about 5 times an hour and my wife has the same thoughts about once every 5 days. I'm sure it is a rare occurrence when two married people have the exact same desired level for sex. The way...

Fantasy Weekend

by DWornock on Sep 24, 2019
BDSM

MF, MM, MMF, FMF, Fetishes: sexual role-playing, cross-dressing, domination and submission, and pain. The youngest person in this story is a 19 year old receptionist. 4Play has given me permission to make modifications and additions to his story "Date Night." I changed the title to "Fantasy Weekend." I also added the first paragraph to chapter 1, deleted...

Behavior Modification Institute Ch. 05

by NancyPan on Sep 12, 2017
Fetish

"I am so proud of you, Tom," Ms Jensen said warmly, approaching me and taking my hands in hers, "It will help you so much to accept this about yourself, Tom. We will help you turn the fantasy of being a sissy into the reality of sissy life. Ms. Panington will be pleased with this progress, and I am quite sure that Kelli will be pleased as well. Let's get you...

Robin and Jimmy Olsen - Sissies Ch. 01

by tawnysuede on Sep 15, 2017
Celebrities & Fan Fiction

Note that this story stands separate from other stories I have posted. * "If you hunky men will excuse us for the moment, we girls have to go... powder our noses!" Robin said as she scootched around on the cushions of the private booth. Jamie rose and joined her. Their dates watched the two girls' rounded asses sway back and forth as the two sissies walked...

Getting Nailed

by jbirdman on Sep 25, 2017
Fetish

This story is not intended for children and if you are not old enough to read sexually explicit material, go away. This story features some elements of female domination (femdom), cross-dressing (CD), mild bondage, Trangender (TG) and a few other fantasies of mine. I hope you find it entertaining, but if you might be offended, stop reading and do something e...

I Put on A Cock

by ndeavour on Jan 6, 2020
Erotic Couplings

Hi, my name's Liz. I'm not about to tell you how old I am -- but I have a 25 year old son, so that should give you a sense. I've only just stopped coloring my hair and begun letting a whole lot of silver to emerge. I no longer have the slim figure I did before having my son; I gained nicely in the boob department, but picked up some extra padding all over. I...