Aunt Sissy Stories

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Orientation
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Such a Deal Ch. 02

by Angelscuck on Sep 13, 2017
Fetish

Her request made my cock hard. I couldn't have fantasized a better situation. I ordered the Lobster, she had the Prime Rib. I watched her skillfully dissect the meat and devour it like a female lioness eating a gazelle. She was magnificent! We made small talk throughout the meal, never alluding to the proposition we had just discussed. We were on an equa...

A Straight Man's Perspective

by nancyvasquez on Oct 15, 2017
Erotic Couplings

As you enter the adult arcade you will notice that it is quite dark, with just dim lighting. What lighting there is only serves to illuminate just how filthy the place is. The stink of piss and semen is pervasive. You have to walk carefully because the floor is slick with semen. Once you get past this assault on your senses, and your eyes begin to adjust to...

Sissy Blane's Liquid Assets

by EvelynT on Sep 14, 2017
Fetish

ONE The Plumrose Dossier I became familiar with the Plumrose Dossier one cool February morning when it was read to me in the private rooms of Madam Harding at the Clinic. I'd arrived that morning for my weekly 'therapy' and had only enough time to hang up my outer clothes in the Sissies' cloakroom and don my Eva Gabor wig before a facilitator poked her he...

Birthday Wishes Ch. 03

by b_wishing on Sep 16, 2017
Transsexuals & Crossdressers

Everyone here is of legal age and they are having lots of fun. PART III "I am so glad you enjoyed me licking you earlier and how you enjoyed licking my pussy too. But now it is time for me to lick me some sissy asspussy. I have waited to do this for quite sometime now Kelly" she says as her hands massage my little backside. Soft kisses occasionally or a li...

Birthday Wishes Ch. 02

by b_wishing on Sep 16, 2017
Transsexuals & Crossdressers

Everyone in this story is above the age of 18 and no one was harmed in the writing of this story. Look for me on Yahoo messenger as b_wishing for some kinky play like this story. Please like my story too. KISS KISS Before I knew it there were two of my fingers engulfed by her wet cunt. I felt my head being pulled to her neck and I kissed her there a cou...

Girdled Ch. 11

by goodsonformom on Apr 14, 2020
Transgender & Crossdressers

After many hugs and kisses, Daddy and I left Jane and Carly with a bag full of new clothes for me. I had a new bathing suit, and a lovely garter belt and stockings, which were among my favorite things. I was very excited to have a pair of fishnets. Daddy was very generous. I was exhausted after my earlier argument with Rene, and then all the very intense sex...

A sissy visits the Headmistress

by maturesubmale_for_F on May 12, 2020
Transgender & Crossdressers

1. Miss Stern delivers both punishment and pleasure I knocked timidly on the heavy door and heard Miss Stern's voice from within, commanding me to enter. I slowly opened the door and walked into the presence of my Headmistress. She was in her mid-fifties and sat behind her massive oaken desk as I came in, studying a heavy file. I stood still just inside the...

Gretel Steals Her Lover

by kingkeywriter on Aug 18, 2017
Fetish

Gretel squeezed into another white girdle, hooked on her black stockings, and slid white panties up to cover her nest. After strapping on her bra, she wiggled into a tight black satin dress. Even in the dim bedroom light, the material glimmered seductively. She stepped into black patent leather pumps, two-and-a-half inches high instead of the stilts she'd w...

Summer at Auntie's

by BimboBarbie on Dec 18, 2017
Transsexual

You stumble off the plane and into the airport with your legs feeling like jelly having been seated for a few hours, heading down to the conveyor belt to collect your suitcase. Watching as a few familiar people you recognize from the flight all come and go, collecting their bags happily and leaving while you remain growing increasingly worried. Eventually it...

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Aunt Jo

by stories55 on Sep 14, 2020
Transgender & Crossdressers

He was getting ready to go off to college when his mother said he would be boarding with his Aunt Jo and save the money on the dorms. She said she would feel more comfortable with him under aunt Jo's watchful eye. It created a bit of disquiet in him. While he liked to have his way with women; the way his Aunt Jo had looked at him made him feel differently. I...