Pegging Sissy Stories

7,509 results
Orientation
Length
Source
Infinite Scroll

Coming Home, Coming Out Pt. 10

by EiryCGar on Jul 6, 2020
BDSM

Author's note: This chapter marks the end of this series, which seems to have run its course. I am grateful to my readers who have commented on my story. As ever, I should remind them that this is a work of total fiction. All characters are at least 18 years of age, and everyone who participates in any of the sexual practices described does so consensually....

Coffee

by Wes7 on Sep 12, 2017
Fetish

My sweetie is an Internet wiz. She finds the best shopping coupons and bargains, books and movies we'll both enjoy and once in awhile, something a little different. For instance. This is about "pegging." How many of you know what that is? I'm an experienced man and I thought I knew everything there was to know about sex. I was so wrong. We're a normal coup...

Journal Beginning

by Tripx713 on Jan 22, 2020
Reviews & Essays

My previous blogging on unnamed sites has been of several types of posts. As this title suggests, I've created journal entries which have been quite popular. I've also written many fictional stories across a range of erotic genres: sci-fi, coercion, polyamorous relationships, cheating, human furniture, gender modification (by magical, chemical or alien means...

The Making of a Mistress Pt. 03

by EiryCGar on Jul 6, 2020
BDSM

Author's note: This fictional series about a character first introduced in my "Coming Home; Coming Out" serial continues with Marie, now engaged, is going to meet Charles's parents. She also takes Charles to meet her mentor, Dr Sara Walters and her sissy cuckold, Paula. As in all of my work, every character is over 18 years of age, and all sexual practices a...

On Her Terms Ch. 03: The Descent

by econut on Sep 18, 2017
Fetish

To say Dale was confused by his new lifestyle arrangement would be an understatement. Over the past few weeks, his entire life had been turned upside down in a series of events that had escalated faster than he could even adjust to. And that was exactly the way Sam wanted it. Sam was Dale's ex-girlfriend's lesbian lover. And now Dale's Mistress. Or should i...

Jason's Secrets Exposed Ch. 09

by jlenil on Sep 14, 2017
BDSM

I suggest that the reader check out the first parts of this story before reading. Comments are appreciated. ***** The following morning, I awoke at 6 AM with a raging clitoral erection, having been dreaming about pegging Jason with other people watching. I summoned Jason from his spot at the bedside and told him to lick me. He did so, much to my satisfacti...

Reason? Nah.

by curdles on Nov 8, 2020
Bisexual

"Oh, fuck!" she gasped as soon as my cock had slid out of her throat. She had held it there for almost a full minute, massaging my balls with her tongue all the while. We hadn't seen each other for almost a week, so our appetites rivaled those of Erysichthon of Thessaly. "I'm almost there," I said, stroking my shaft. "Open up,"...

Open in Reader

The Live-in Maid Ch. 02

by Quietoldie on Jan 31, 2018
Transsexuals & Crossdressers

I think that everyone has deja vu every once in a while. Well when Barbara Kane walked through the front door of the shoe shop I had this strange feeling that I'd met her somewhere before. She has a commanding presence. Quite apart from her beauty there is something else about her. She's tall, but it's not just that, there's an air of confidence about her to...

Interracial Pegging Chronicles

by Samuelx on Mar 6, 2018
Interracial Love

Donna Baker, better known by her porn moniker Silver Thorne, carefully looked at the young African American man who sat less than a meter from her. Conducting interviews with new talent in her small, Spartan office was one of Donna Baker's many duties as the CEO of a major adult film company. Sure, the human resources department could have taken care of that...

A Pound of Flesh Ch. 05-06

by SEVERUSMAX on Sep 14, 2017
Group Sex

Chapter 5 When I awoke the next morning, it was to the sound of rather wild, raunchy sex, of course, but it wasn't what I thought. Nicky and Chelsea were getting it on, but she was hitting him from behind with a strap-on dildo. My fiancee was pegging my boyfriend, while his fiancee watched and pleasured herself in response. He didn't seem to mind it, either...