Sissification 101 Stories

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Sissification 101: Ch. 06

by silkstockingslover on Sep 28, 2020
Interracial Love

Sissification 101 Ch 06 Summary: Eric gets fucked by BBC for the first time; Joan gets black pussy. Thanks to Eric who requested and helped plot this lengthy story. Recap so far: Sissification 101 tells the story of Eric, a mid-30s Asian, who has been hiding his sissy side curiosity for years until he is caught in pantyhose watching hypno-sissy porn by...

Sissification 101: Ch. 04

by silkstockingslover on Jul 14, 2020
Transgender & Crossdressers

Sissification 101 Ch 04 Summary: Eric sucks his first BBC in a threesome with Joan. Thanks to Eric who requested and helped plot this lengthy story. Recap so far: Sissification 101 tells the story of Eric, a mid-30s Asian, who has been hiding his sissy side curiosity for years until he is caught in pantyhose watching hypno-sissy porn by his...

Sissification 101: Ch. 05

by silkstockingslover on Aug 31, 2020
Interracial Love

Sissification 101 Ch 05 Summary: Erica practices taking BBC in both of her sissy holes. Thanks to Eric who requested and helped plot this lengthy story. Recap so far: Sissification 101 tells the story of Eric, a mid-30s Asian, who has been hiding his sissy side curiosity for years until he is caught by a very supportive girlfriend in pantyho...

Sissification 101: Ch. 03

by silkstockingslover on Jun 8, 2020
Transgender & Crossdressers

Sissification 101 Ch 03 Summary: Eric(a) gets pegged for the first time. Thanks to Eric who requested and helped plot this lengthy story. Recap so far: Sissification 101 tells the story of Eric, a mid-30s Asian, who has been hiding his sissy side curiosity for years until he is caught in pantyhose watching hypno-sissy porn by a very supporti...

Sissification 101: Ch. 02

by silkstockingslover on May 18, 2020
Toys & Masturbation

Summary: Both Eric(a) and Joan discover the joys of toys. Thanks to the real Eric who requested and helped plot this lengthy story. Thanks to Tex Beethoven and Robert for editing this story. Recap so far: Sissification 101 tells the story of Eric, a mid-30s Asian, who has been hiding his sissy side curiosity for years until he is caught in pantyhose wat...

My Initial Sissification

by ShemaleMaid on Sep 16, 2017
Transsexuals & Crossdressers

I love cum. Always did. Whether my own when I started experimenting, or that of friends later on. By now it's mainly the seed of older gentlemen who enjoy spending time with a sissy, and I love every minute! My clit simply drooling. By now it doesn't get hard anymore, and if there's a hint I slap it good. Stay small! I'm shaved, small, uncut, and the dream...

Sissification 101: Ch. 01

by silkstockingslover on May 4, 2020
Fetish

Summary: Straight guy is caught watching sissy porn and...Note 1: Thanks to Eric who requested and helped plot this lengthy story. Note 2: Thanks to Tex Beethoven and Robert for editing. Note 3: All characters are at least 18 years old. Sissification 101: Ch. 01 1. MY SISSY CURIOSITY I've always liked nylons. I grew up when they were still popular and...

Sissification Fad

by NaughtyEricka on Sep 30, 2019
Transsexual

Sissification hadn’t just become some sexual fad overnight it had actually become a practical way of life for numerous families across the country. The act of sissifying a male family member and using them as a family sex toy and also as an alternate source of income had started in China and Japan but had quickly spread to and across the US. Now 3 years late...

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Building a Better Girlfriend

by DocGrok on Apr 22, 2025

Have you found yourself lonely for too long? Awkward conversations that were supposed to be a meet-cute, dating apps empty or non-responsive, clubs or nightlife not really your jam? Wishing for someone that gets you on your level? If any of these apply to you, read on. In the pages beyond we join our protagonist in a reality close to our own, wherein strange...

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Sissy RoomMate

by OathkeeperPath on Apr 22, 2025

Story on hiatus until the current released rough drafts are fully finished chapters, I'm also going back to only releasing fully finished chapters, I know alot of you liked how much quicker it moved the story along, but it hurt the overall quality as I tended to take along time to come back and finish them if they were already released. You finally did it, Y...

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