Swinger Sissy Story Stories

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Black Sissy For White Goddess

by Samuelx on Sep 16, 2017
Interracial Love

Finally, I feel like I am where I belong. Picture this, if you will. A big and tall, muscular Black man clad in a pink tutu and frilly White panties, my face fully made up and my lips properly rouged. I am kneeling before a six-foot-tall, slender red-haired White chick and sucking her strap-on dildo. My Mistress Amelia Heinrich smiles at me as I suck her dil...

Sissy Amy Loves Mummy Belinda Ch. 01

by Sissy Adele Howells on Sep 17, 2017
Fetish

My world had turned upside down, when realising that my favourite fantasy was about to come true. The story that I am about to narrate, is about my obsession of being a kinky, sissy, little girl. Everything seems so real and I could not stop myself from falling deeper into this kinky world of fantasy. For the benefit of the reader I am forty eight years of a...

The Settlement Pt. 02

by cathynylons on Sep 14, 2017
Transsexuals & Crossdressers

I went to my room and sat down at the vanity to remove my make-up, remove my clothes, and hang them up in the closet. Saw a glimpse of myself standing in front of a full length mirror wearing bra, panties, garterbelt, stockings, and heels and began to realize my predicament. When I got to bed I spent the night lying awake, tossing and turning. It was dawn be...

Teen Goes To Swinger Party Ch. 02

by Southernstud97 on Sep 1, 2017
Group Sex

I head back to the main room and decide to look around for a while. After looking around for a couple minutes, I turn to see two white BBW's approaching. They are about 5"8 and 5"5, with big tits and fat asses. The redhead introduces herself as Ashley and the brunette introduces herself as Carly. We start talking, they tell me how they always love breaking i...

A One Night Stand for Tranny G

by Creamyirish on Sep 16, 2017
Transsexuals & Crossdressers

The time had arrived for me to travel to see Tranny G, yet something felt different. I mentioned that HE is a soldier and really, I was never angry about the rape. It was such an experience, that I wander back to and repeat in my mind again and again, wet with the memories of the fear, the fight, the ultimate pleasure. I might as well tell you that I see mys...

Jacki's Journey into Sissyhood Pt. 02

by jacki697 on Sep 18, 2017
Transsexuals & Crossdressers

This is a continuation of: Jacki's Journey Into Sissyhood. Thank you for reading a continuation of that series. ***** I awoke as sunlight began to creep into my bedroom. I might have thought last night was a dream if it wasn't for the large hairy arm draped across my shoulders and the large cock poking at my backside. I tried to slowly slide out from unde...

A Conversation with a Lady

by OpenMouth on Oct 15, 2017
Transsexuals & Crossdressers

This story was inspired by Gemsissy and her wonderful shopping trips... ***** A select lingerie shop in a small northern English market town. The shop front reads 'Cherie.' I walk in and I'm surrounded by wonderful things by Lejaby, Aubade, Lise Charmel. A stylish woman is behind the counter; she's mid-40s, slim, blonde, tall. She has tanned skin, expe...

Mr. BBC is Totally Bisexual

by Samuelx on Mar 7, 2018
Transsexuals & Crossdressers

The Glebe area of Ottawa, Ontario, is usually a quiet and upscale neighborhood, but tonight at the Hiller townhouse, things were getting loud and steamy. Mark Dixon had Donna Hiller on all fours, face down and ass up, in the Hiller living room. The big and tall, burly young black man pulled on the curvy redhead's long hair and smacked her big white ass while...

Black Sissy for White Couple

by Samuelx on Sep 12, 2017
Fetish

Watching Robert Wiles sucking my husband Daryl's cock totally turned me on. I donned my strap-on dildo and began fucking the tall, muscular Black stud with it. Robert groaned as I penetrated his ass with my eight-inch strap-on dildo but didn't stop sucking Daryl's dick. Robert Wiles is a bisexual Black stud from Jamaica who goes crazy for White cock, and Whi...

The Evolution of Tranny G

by Creamyirish on Sep 13, 2017
Transsexuals & Crossdressers

My beloved Tranny G was so devastated by the one night stand and had lost her confidence. First she was made fun of while shopping, ending the evening with the "perfect" man, having her first true intimate experience with a man, only to find that his promise to call her was false. I did not see her on my last trip, as she was devastated and in her own lovi...