Gay Caught Cross Dressing Stories

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Infinite Scroll

Jamie - The Journey Begins Ch. 17 - Let the Rollercoaster Begin

by Hutchison12 on Oct 29, 2018
Gay Male

Ben steered us over to Mozart's Coffee. It looked rustic-ish from out front, nice although. I climbed out of the truck distracted, looking up to see Ben right next to me, blocking my pathway. He leaned in and kissed me gently, then rested his forehead against mine. "I could just stay here all day" Ben whispered. I smiled back at him, "Yeah, but I can smel...

Night Games Pt. 01

by EROTICbearscribe on Jul 17, 2019
Gay Male

It had been a grey, dreary Saturday. Snow had been falling almost as fast as the temperatures. The entire city was shut down. It was quiet except for the occasional scraping of a snowplow's blade along the street. It was the first Saturday I had off in a long while. In fact I had the entire weekend off and had no idea what I was going to do with myself. W...

Box Shaped Heart Ch. 07

by laurasfox on Nov 26, 2018
Gay Male

Chapter Seven - Stiff, Stiff, Stiffer Carter took the glass of wine from the table with a methodical gesture, brought it to his lips and took a long sip of ... nothing. "Do you want more wine?" Aron asked him. "Just give me the bottle," he mumbled. He needed more than that, but he had to make do with whatever he had at his disposal. So he just drank...

Grandpa's Summer Visit

by timmywells on Apr 3, 2019
Gay Male

I knew that my grandfather was going to visit us, so I wasn't shocked when I saw him that Thursday afternoon in the guest room. It was the way I saw him that set me back a bit. I walked down the hall that afternoon, and when I passed the bathroom I could tell that someone had gotten out of the shower recently. That someone was my grandfather, and while it w...

My Life is You Ch. 14

by mypussyandyours on Apr 3, 2019
Gay Male

HI ALL. THANK YOU FOR BEING PATIENT! I HOPE YOU ENJOY THIS CHAPTER. LET ME KNOW, BOTH THROUGH VOTES AND COMMENTS. I ENJOY BOTH. NOW, ON WITH DILLON AND SETH'S STORY. At the sound of the front door opening, Dillon carefully put his glass down onto the table beside the couch. He nervously wiped his suddenly sweaty palms on the material covering his thighs as...

Lesson Unlearned

by KeithD on Feb 3, 2020
Gay Male

"You really wanted it this morning, didn't you?" Leonard said. He laughed as he rose off Dan on the bed. "And, woowie, look at that hole." He grabbed a hand mirror off the dresser and held it between Dan's bent and spread legs, his buttocks elevated on a bolster, so the younger guy by a good twenty-five years could see the effects of how Leonard had worked h...

The Unexpected Meeting

by CoburnAisling on Feb 4, 2020
Gay Male

Adam leaned back in his chair, the leather creaking as his weight shifted. Motes danced in the light streaming through the floor-to-ceiling window behind him; the same light shone through his dark blonde hair, leaving him just slightly warmer than was really comfortable, but not warm enough to overcome the sucking lethargy that kept him from getting up to di...

A Favour Ch. 04

by BluePill on Feb 4, 2020
Gay Male

It was not long before Josh had essentially moved in to David's house. It didn't happen all at once. Progressively, he moved from leaving a toothbrush in his bathroom, to having a clean shirt and underwear for sleepover 'emergencies'. Before long, David cleared out a drawer for him in the dresser and before he knew it, he was calling to see if he should pick...

Coming Out on the Swim Team Pt. 07

by walterio on Jun 17, 2019
Gay Male

ESTABLISHING A ROUTINE The first week for the freshmen was always a challenge. They had to balance class time, training, homework and sex. They were for the most part too tired the first week for nightly sex. In fact, they waited until Saturday to have sex in their dorm rooms. On Sunday they were in the training room for massage foreplay and group sex. Coa...

Kidnapped Ch. 01

by AgirlcalledBob on Jun 19, 2019
Gay Male

Chapter One Ollie Slater slams his long body between Mikey and I on the ratty sofa with an 'oomph' of exhaled air. "I'm screwed!" His face is twisted in dismay as he plucks the joint from Mikey's elegant fingers before sucking in a heavy drag. The motion highlights the strong bones of his face, his deep-set brown eyes narrowing as the smoke rises. I'm a...