Sissy Karen Stories Stories

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Panty Consequences No. 01

by PantiesAndPies on Sep 11, 2017
Fetish

This series of stories are all standalone so can be read in any order. They are about my favourite fantasy -- my first time wearing, or first time caught wearing panties. Obviously then they include lingerie wearing men and the consequences may include cuckolding, creampie eating or cock sucking men. If this may offend you I suggest you stop now ... otherwis...

A Picture Perfect Sissy

by meeah sue on Sep 16, 2017
Transsexuals & Crossdressers

"Holly, hold your breasts up. That's it honey. Squeeze the nipples between your fingers. Make them hard for me, sweetie." Jason lifted and pushed his soft breasts together, squeezed the small dark nipples, and hurriedly looked up to see if what he was doing was okay. He really wanted what he was doing to be okay. It was dreadfully important to be okay. Kare...

A Friend Catches Me Ch. 03

by PinkPanties4me on Dec 2, 2019
Transgender & Crossdressers

Sorry it took so long to continue my story...For those of you just finding this, please read my first two sections, A friend catches me 1 and 2. *** Karen looked at me and said," I have had an idea for a while, so now is as good a time as any!" She took out her cellphone and made a call. "Hello Roberto, no I don't need to make an appointment to get my hai...

Auntie Jean Drummond Lloyd Ch. 4

by Sissy Adele Howells on Aug 31, 2017
Fetish

The final humiliation by Auntie Jean Drummond Lloyd was reaching its very kinky conclusion. I was looking really cute in Karen Lloyd's pink pyjamas. I could smell Karen's perfume and bodily juices on them. Karen had even left her shit stains in the ass part. I was now paraded in Auntie Jean's bedroom. Kimberley Holmes, laughed at my blushing face. Her black,...

A Friend Catches Me Ch. 02

by PinkPanties4me on Sep 16, 2017
Transsexuals & Crossdressers

So, here I am kneeling on the floor in front of my friend. I'm dressed in my mint green panties and matching camisole. I just sucked his cock off and he had exploded all over my face. The cum hadn't even dried when Karen, my wife walks in on us. "What the hell is going on?" I look up at her, the cum still on my face. Dave says," Your husband has just confe...

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...

Casey's Submissive Journey Pt. 07

by corduroysissy on Mar 6, 2018
Transsexuals & Crossdressers

Note: This part of the story, and those to follow, occur after Karen had been accepted into the Lady's Club. ***** Karen spotted Betty Jean from across the room and she looked interesting. The ladies were all watching their husbands sucking and fucking each other in full drag, it was Fag Night at the Lady's Club and the sissies were giving them a really go...

Auntie Jean Drummond Lloyd

by Sissy Adele Howells on Aug 31, 2017
Fetish

I had been caught red handed. My kinky secret was now known by the stewardess of my local club. At 45 years of age, without a girlfriend, my world was about to change. Of course this was a fantasy dream, but everything was so real. Stewardess Jean Drummond Lloyd was 58 years of age. Sixteen stone of obesity, with short, blonde, curly hair. This was going gr...

Dress Up For The Girls Next Door Ch. 02

by JackorJill on Jul 15, 2020
Transgender & Crossdressers

“Hot enough for you?” I looked up from the garage to see Lisa hanging her head out the window. She had a sexy turquoise halter on. Her tits bounced back and forth as she spoke. “Now it’s real hot with you hanging out the window.” No bra, Lisa never wore a bra when it was this hot. “I have a few cold beers in the fridge,” she cooed. “Why don’t you take a b...

The Auction Pt. 01

by phoenixcinders on Jun 5, 2019
Transgender & Crossdressers

Sorry I haven't posted in a while. I fell into a slump, but I'm back with a brand new story. All characters involved in sex are 18 or older. This story contains feminization, slavery, anal sex, transgender, sissy, blow job, cum swallowing and vampires. You have been warned. If you don't like the tags, don't read it and move on. Other than that, feel free to...