Sissy Brother Stories

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Orientation
Length
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Infinite Scroll

Siss the Bride Ch. 02

by theonewhowas on Sep 19, 2017
Transsexuals & Crossdressers

Anyone who tells you that married life is hard must be part of a straight couple that survives on vanilla sex once every two months or so. I love being married, I get to live out all my wildest fantasies and adventures with the man I love; just over a year ago I married my brother (I could explain why right now but that's a whole other story), but because I...

Stan to Stella Pt. 01

by Maximus_eros on Sep 16, 2017
Transsexuals & Crossdressers

Disclaimer: All persons depicted are 18 or over. The names have been changed to protect identities as this did occur in reality to some degree. ***** Like any story, everything has a beginning and thus we have the day that Stan began his journey of self-discovery at the manly hands of Jason. He like so many was subjected to years of ridicule and shame. Th...

Close Shave

by Tomsparty on Sep 13, 2017
Transsexuals & Crossdressers

My sister, Sharon caught me naked, shaving my legs in the family bathroom. 'I thought you where in Court all afternoon.' I cried dropping the razor in surprise. My sister dressed in her smart black skirt, white blouse and black fitted jacket raised an arched eyebrow patronisingly. 'Obviously so, brother dear but my case finished early. I wasn't required f...

Being Jenny's Summer Boyfriend Ch. 03

by Lucas96 on Jan 21, 2020
Fetish

Disclaimer: this story involves cuckolding, humiliation, cross-dressing, and gay incest. *** I have to admit, it was difficult to contain my excitement as Jenny invited my dad and brother over to show them what a little sissy slut I'd become. To prepare, Jenny let me try on the outfit she'd had on when we'd come over to Andrew's house: a pink, tight-fitt...

Riley's Bar Ch. 07

by Just Plain Bob on Sep 15, 2017
Loving Wives

When I got back to my apartment there was a message on my answering machine to call my brother. I called him and he told me that what we had talked about at the courthouse was doable and I told him to go ahead and do it. Then I went to bed and slept like a log. Friday was a busy day at work and even though I had my hands full trying to finish the job I was...

Mistress Chantel, Tranny Dominatrix Ch. 15

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Fifteen: We Meet Each Other's Parents and There Is A Wedding Ready to Go. [Sunday late morning]. "How many sissy maids have agreed to come clean for us Hun?" Kerri asks. "Three little sweetie maids Babe." I smile and reply. "They will be by on Wednesday before our Friday wedding. They are all so excited to play sissy house maids for us while t...

Explore the Inner Woman In You

by Tomsparty on Sep 14, 2017
Transsexuals & Crossdressers

I fancied the arse off a girl at school called Sharon. The problem was most of my year did. She was beautiful with long blonde hair, willowy legs, a butt to die for and stunning pert tits. She was way out of my league but quite amazingly we did get on and began to make slow but steady headway. My dizzy ambition was to ask her to the end of year college dance...

My Husband. My Love. My Sissy. Ch. 01

by RandomAuthor on Sep 25, 2017
Fetish

Please don't misunderstand what I'm saying here. I'm not trying to be demeaning, cruel or diminish my husband in any way. I'm actually extremely proud of his honesty and his courage, and I'm convinced that the fact he's a Sissy is one of the reasons I fell in love with him. It's also one of the reasons our marriage is so strong, wonderful and rewarding. Tony...

A Sissy Saga Ch. 02

by Snurge on Sep 15, 2017
Novels and Novellas

When Jennifer went out onto the terrace William was nervous but relieved to be with someone his own age and gender, even if that person had been sissified just like himself. The two eighteen-year-olds regarded each other and their feminine attire silently for a moment before Archie at last broke the tongue-tied awkwardness. "Better make a start," he said,...

Mama Mia Pt. 02

by grizzley123 on Jul 27, 2020
Fetish

This story contains many themes including cuckolding, gay sex, bsdm, incest and submission. If these are not your things, please skip. This is the second installment and it obviously helps to read the first part. The starting point here: I have just finished sucking off my temporary neighbor's cock. I have been set-up by my wife and her lover to be a submis...