First Time Sissy Gets Fucked Stories

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Infinite Scroll

Happy Marriage Ch. 02

by yesplease8 on Sep 25, 2017
Loving Wives

Well, our marriage just keeps getting better. My wife and I love that I'm submissive and that I was bi-curious. I say I was bi-curious, because my wife set me up to realize I am truly bisexual. After begging her to use me like a sissy slut with a strap on, she not only treated me like a slut with her strap on, she happily watched me with another man. She se...

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...

Sissy Cuckold & The Old Bull Ch. 01

by DirtyDaddyHunter on Sep 19, 2017
Loving Wives

He waited on the bed as instructed. He had dressed exactly as he was asked: A pair of lavender lace trimmed panties stretched tightly over the young man's small cock; a matching bra covered his hard brown nipples too. He also had on a garter belt and some high heels. Too top in off he had on some coral lipstick and he had painted his nails perfectly. There...

HypnoSissy: Educated to be Pegged

by silkstockingslover on Aug 13, 2019
Fetish

Summary: Cock sucker's training is advanced to hypno videos on anal sex. WARNING PLEASE READ: -This is a hypnosis story with potentially influential subliminal messages within it. -The story also contains hypnosis video scenes. -So if you begin behaving differently after reading this story and all your friends start pointing fingers, don't come crying to...

My Mistress Ch. 03

by Kandy5647 on Sep 12, 2017
BDSM

Hello Peoples of Literotica! It's Drew Nelson again! And I'm back in full force! This time I'm here to not only tell you about my stunningly gorgeous Mistress Tameka. But! I'm here to tell you about my new Master Quentin Devonté Sterling as well. My God what a man he is! Wait! What am I saying?! He's a pure bred God! He's this 6'6, 210lbs, dark brown eyed,...

Dominican Slut: Orgy Finale

by silkstockingslover on Sep 18, 2017
Group Sex

Summary: Slut and black husband submit to white men and women. Note: This is dedicated to the real Johnathan and Elizabeth who inspired the story. The entire back story is based on real events...the plotlines are real fantasies of the lovely couple. Note 2: This is part eight of a multi-chaptered story: In part one, Dominican Slut: Ass Slut, Elizabeth,...

Not The Team Mom

by redpilldad on Oct 10, 2018
Loving Wives

This is a tale of seduction, rough but consensual sex, and a cheating wife. Comments are welcome, anonymous trolls will be deleted. * Spending yet another weekend at the ballfield, Eric Joseph was killing time waiting for his daughter's next softball game. Ashley's Lady Hawks team had won her first game and had a one game break before the next one started....

Nancy and Her Boss Ch. 03

by MidniteSpanker on Sep 19, 2017
BDSM

Part 3 – The Weekend. The initial stories in this series Nancy Remembers Chap. 1 Nancy Remembers Chap. 2 Nancy Remembers Chap. 3 Other stories continuing in this series Nancy and her Boss Part 1 Nancy and her Boss Part 2 Nancy and her Boss Part 3 - The Weekend Nancy and her Boss Part 4 - More Weekend Then the following are separate but related stories...

Mike's Fantasy Wife 01

by avalon_sunset on Sep 12, 2017
Exhibitionist & Voyeur

Introduction. Mike and I have been sharing emails since he placed a few images of his wife Linda on an 'amateur wife' website. I commented on his wife's good looks and admired her breasts. He quickly told me that he loves to imagine Linda being fucked in public by a mature guy with a long cock; someone who knew how to make her squeal, to give her intense pl...

He Wanted To Fuck My Wife

by rangeeladesi on Sep 16, 2017
Group Sex

I was pleasantly surprised when my wife Vineeta told me that she and two of her female friends had organised an out-of-town trip for the three couples. In our family, such responsibilities generally rested on me. Her friends were Neha and Sunita. I had met them a few times as they were office colleagues of Vineeta. Neha is a beautiful woman of 25 years with...