The Sissy Bet (gay sissification rimjob)

The Sissy Bet (gay sissification rimjob)

by Sapphire Rush

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Chris and Nicky are two ultra-competitive jocks.  Chris is a thin, toned endurance runner; Nicky is a tall, beefy crew star, more at home rowing a boat than anything else.  They have a bet with each other; one thing leads to another; and the loser of their triathlon challenge will have to dress up in women's clothes.  Chris's confidence soon evaporates when Nicky beats him handily.  What costume will Nicky force him to wear?  And how will Nicky react to seeing his friend dressed up like a sissy?

This 5,600 word gay sissy erotica story is suitable for adults only and contains feminization, extremely dirty talk, a hint of tease and denial, cross dressing, a good hard fuck, and challenged expectations.


The truth was, I was enjoying being asked to dance.  I was enjoying being desired, and having other people desire me.  It was just as intoxicating as the alcohol, and although I knew they were doing everything with a nod and a wink, it felt great to just suspend my disbelief for a moment and think that they wanted me.

I was just about to haul myself off the couch and go off to see if people were far enough gone that I could get someone to jokingly grab my ass, when Nicky suddenly appeared on the couch next to me.  I had absolutely no idea where he'd come from.  One moment I was alone, the next he was there, sitting back and disposing of an empty beer can.

"Hell of a party," I said.  He looked at me, and he almost looked a little bit sad.

"It sure is," he said, somewhat distant.  "It sure is."

"You okay there?" I said.

He waved his hand.  "Thanks", he said.

"What for?"

"For not backing out.  For being a man.  Or a girl.  Or a sissy.  Whatever."

I jumped slightly as he said the word sissy.  "Oh, no problem", I said.  "We had a bet."

"I knew I was going to win", he said.

"So did I."

His lips formed a thin smile.  "How are you finding it?"  He gestured to my clothes.

"It doesn't completely suck", I said.  "Apart from, you know, the complete and total humiliation of it all."

"Heh.  Small things."  There was an awkward silence.  I realized my heart rate was shooting upwards, and from a look at him, I was pretty sure that his was doing just the same thing.

"You like what you see?" I said, deliberately casual; and it was like someone had flipped a light switch in his eyes.  They caught fire and gleamed like rare diamonds.

"Yes", he said simply, and there was silence again.  I knew I had to say something to him.  If I left it too long, he'd apologize, get up, leave, and we'd have to get on with our lives, knowing what we knew and not being able to do anything about it.

Product Details

ISBN-13: 9781498977944
Publisher: Sapphire Rush
Publication date: 05/14/2014
Series: Red Hot Rimming
Sold by: Draft2Digital
Format: NOOK Book
Sales rank: 982,122
File size: 141 KB

About the Author

Sapphire Rush is a two-handed author of one-handed stories who lives and daydreams with a slightly tubby cat in London, England.  Why not send an email to

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