Gay Petticoat Punishment Stories

1,321 results
Orientation
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Infinite Scroll

Simon And Sam's Second Weekend Pt. 01

by thameswatcher on Oct 6, 2020
Gay Male

A week had passed and the two mothers where again working combined shifts at the hospital, because of covid they were sleeping in a converted dormitory so Sam knew he had a whole week end with Simon alone. His mother was only too grateful that Sam volunteered to look after the boy, and also she'd noticed some changes in him lately, he was showering more and...

My Little Rose Ch. 02

by UndertakerKiryu on Aug 18, 2017
Gay Male

Authors note: sorry for the wait. The last version was rejected for smut. And the one afterwards. ***** I lay in bed naked and panting, feeling the traces of orgasm pulse through my veins, better than what usually pulsed through there. I turned over and saw the sleeping face of my boyfriend of six months, Garland. His naturally feminine features were beaut...

That Was Quick!

by zaphod40 on Aug 18, 2017
Gay Male

I never saw his prick and I only held it in my hand for about 45 seconds, but I heard the sharp intake of breath and felt the upward rush of spunk as he spurted and I was never quite the same again! It happened like this. I was nineteen and had been taking a year out between school and University. So had my friend Ollie, who was slightly older than me and...

Hoffner and his Elf

by BigWig69 on Aug 18, 2017
Gay Male

I was lying in bed next to Hoffner. He had just finished making sweet love to me and I was lying on his silver haired chest, slowly and softly, licking his soft pink nipples. Our legs were entwined, his large, powerful hand, caressing and squeezing my balls. We had been seeing a lot more of each other, meeting in hotels or at his place when his wife was out...

While the Wife's Upstairs

by timmywells on Sep 14, 2017
Gay Male

I remember how hot it was that day in August as I delivered the paper on my route in the unforgiving heat of the afternoon. It wasn't a very lucrative route delivering the Knickerbocker News, a paper than was published in the afternoon in Albany, not nearly as profitable as doing the Times Union in the mornings, but it was better than nothing and at least I...

Little Sex Toy Ch. 07

by keptsissy on Sep 26, 2017
Gay Male

The cum all over my face mixes with the tear smeared eye makeup. It's running down my cheeks. It's in my hair, on my neck, I'm covered with cum. The first man that came in my face came huge. He choked me too, deep throat fucked me and made me cry. I've been crying and tearing up ever since. That was three hours ago. He had very large spurts that soaked me,...

Julius and Tom

by Turbidus on Nov 27, 2017
Gay Male

Reader alert: this is not an erotic story I am conflicted about publishing this story. I do not mean, in any way, to trivialize the horrors a man like Julius would have dealt with. The idea came to me when I was half asleep, on a plane coming home from a meeting. I tried several times to tell it from Tom's point of view but I couldn't make it work. I am a...

Kevin Pettifer - The Warden

by JASONSHOMOEROTICA on Apr 17, 2018
Gay Male

This is the third and last of a group of three related stories: Petty Officer Pettifer Pettifer the Gay Disciplinarian Pettifer – The Warden ***** CHAPTER 1 Kevin Pettifer: Warrant Officer Kevin Pettifer, to give him his full title, stood, cane still in his hand, and looked with a sense of great personal satisfaction at the richly welted, muscular arse...

His Merciless Pastor

by Guy521 on Dec 24, 2019
Gay Male

Adam looked at the floor as Pastor Julian took a seat at the desk. No doubt his father had told the Pastor about what he had done. 'Look up at me son,' said Pastor Julian sternly. Adam looked up into Pastor Julian's eyes wishing the ground would swallow him up. He could see the disgust in the Pastor's eyes. Feel the judgement for the things he had done....

Daniel Meets his Master

by dhope75 on Aug 18, 2017
Gay Male

It was a cold, crisp November afternoon. Daniel had for a long time fantasised about sex with guys - ever since he was a teenager, in fact. Now, at 26 years of age, he was finally going to get the opportunity to. For three weeks he had been chatting - flirting - with a man he had come across on a gay website, an older man who had sent him a message liking...