Silkstockingslover Stories

186 results
Orientation
Length
Source
Infinite Scroll

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...

Mistle-Blow: Three Nerds and a Beauty

by silkstockingslover on Sep 19, 2017
Group Sex

Note 1: This is a Christmas 2013 Contest story...so please vote and enjoy. Note 2: Thanks to goamz86 and MAB7991 for editing this story. Mistle-Blow: Three Nerds & a Beauty When we hired Amber we did so with rock hard cocks. The three of us, Ben, Eugene and I (Blair), were all nerds, who spent way more time working on computers than talking to people...

Black Cock: Addicted to Cum

by silkstockingslover on Sep 25, 2017
Interracial Love

Summary: Husband and wife are shared by female black teen and grandpa. Note 1: This story is dedicated to goamz86 and in making one of his fantasies as real as possible. Note 2: Thanks to Robert, goamz86, and Wayne for editing. Note 3: Although this story is mostly a GAY interracial story, it is really a much deeper story about one man's lengthy journe...

Man of the House

by silkstockingslover on Sep 25, 2017
Transsexuals & Crossdressers

Summary: Step-mom-to-be gets major surprise when home alone with step-daughter-to-be Note 1: This is an April Fool's 2017 Contest Story so please vote. Note 2: Thanks to Tex Beethoven, Robert, Dave, and Wayne for editing this story. Man of the House My fiancé announced, last minute, he was going to Boston for a week on business, and that he was terribly...

Cocksucker: Crossdressing

by silkstockingslover on Sep 25, 2017
Transsexuals & Crossdressers

Summary: Straight man is forced to cross dress and suck cock. You do not need to read the first parts to enjoy this story about a straight man crossdressing in San Francisco. In case you are curious about how he ended up in this situation here is a brief summary of the first two parts of the "Cocksucker" series: Chris, a married straight man, is stuck at t...

White Sluts’ Club: Feminist Virgin

by silkstockingslover on Mar 28, 2018
Fetish

White Sluts' Club: Feminist Virgin Summary: Feminist becomes the focus of a black cock bukkake. Note 1: This is an April Fools Day Contest story so please vote. Note 2: This is dedicated to the real Alicia who inspired the story. Note 3: Thanks to Tex Beethoven, Robert, and Wayne for editing. PS: This easily could have gone into the interracial, and pe...

Sister's Shemale Friend

by silkstockingslover on Sep 12, 2018
Illustrated

Sister's Shemale Friend Summary: Family seduced and dominated by an irresistible shemale. Note 1: This is a Summer 2018 Contest Story so please vote. Note 2: Thanks to DarkBreezly for creating the pictures in this story. Note 3: Thanks to Tex Beethoven, Robert and Wayne for editing this story. I came home from work a couple hours early, as our manager...

A Sister Surprise: Drunk Mommy

by silkstockingslover on Feb 11, 2019
Illustrated

Summary: Mom comes home and catches son and daughter and... Note 1: Thanks to Tex Beethoven, Wayne, and Robert for editing this story. Summary: This is the fourth chapter of the story of Joey (a virgin before he attended last Friday night's Halloween party with his sister) and Sarah (his older college sister who belongs to a sorority at her college over a...

Cocksucker: Drag Queen

by silkstockingslover on Sep 25, 2017
Transsexuals & Crossdressers

Summary: Straight man is turned into a twink and drag queen. You do not need to read the first parts to enjoy this story of a straight man who gets submerged into the drag queen world of San Francisco. (but obviously it helps). In case you are curious how this straight married man got into this predicament here is a brief summary of the first five chapters...

Exploring Sexuality: A Pegging

by silkstockingslover on Sep 25, 2017
Anal

Summary: Husband is pegged by sister-in-law with wife's permission Note 1: Thanks to Robert, goamz86 and Wayne for editing. Exploring Sexuality: A Pegging I was almost in the city when my cell rang. I glanced at it and saw it was my sister-in-law Sabrina. I sighed. I loved Sabrina, but since her divorce she had been as exciting as a Nicholas Sparks mov...