Gay Dress Socks Stories

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Orientation
Length
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Infinite Scroll

My New Daddy Ch. 01

by sissytoy20 on Feb 13, 2018
Gay Male

I'm 21 years old and I attend college but I still live at home for financial reasons. I've always been fem and young-looking for my age. I like to cross dress, but I don't usually dress fem in public. I've just found that it can be difficult for some straight folks to take a young male who likes to be a sissy slut. So you can imagine my surprise when I was r...

Meeting Frank

by clandestan on Sep 19, 2017
Gay Male

Frank laughs loudly at something I say. It's deep, husky, and inexplicably sexy. My toes tingle inside my dress socks. Alexandra beams at us both - the heavily charged undercurrent between Frank and I seemingly lost on her -- obviously pleased that I'm getting along so well with her father. "This is wonderful" she smiles, her fingers lacing with mine under...

Higballing

by sr71plt on Aug 18, 2017
Gay Male

If the CEO of my company hadn't seen me recently in that gay bar over on 12th and Madison, I don't know how long it would have taken me to get invited to the executive floor. But Pete Peterson had seen me, and there I was, in his conference room, sitting in a second-row position in the weekly executive meeting. I'd been surprised, but pleasantly so, to see...

Coming Back for More

by curiousfortoolong on Oct 6, 2020
Gay Male

I call John and make another appointment. I let him know that this is for a massage only, we can talk business later. Tomorrow at 4pm is his first available. I think about that for a split second - hmmm. If he has many appointments like mine, I want to catch him in the morning, first thing. I tell him I cannot do that and would rather have an early morning a...

Imprisonment Ch. 03

by AgentK on Nov 8, 2017
Gay Male

Justin looked up with a sigh as the warden opened his door at the end of the workday Friday. He'd been dreading this day all week, and he was just now starting to be able to sit down comfortably after the abuse his backside had taken the previous Friday. He'd considered perhaps trying to stretch and loosen his opening so the next round of penetrations wouldn...

Afternoon Delight

by Gil_Raleigh on Aug 18, 2017
Gay Male

Special thanks to my editor Cam. No matter how well you write, having an editor is invaluable. Disclaimers 1. If you're not supposed to read this due to the laws where you live, hit back and move along. If you read further, that's on you. 2. lf m/m sex isn't your thing, hit back and move along. 3. There may or may not be incest themes in any of my storie...

Fuckboy Billy Ch. 04

by hylas_ on Sep 14, 2017
Gay Male

Note: This story contains BDSM themes. It was edited by Naughty_Penpal; thank you for your work! Comments are always appreciated! * Billy woke up alone the next morning. He slid over to the empty spot beside him and sniffed the duvet, catching a faint trace of his Master's scent. He spent some time idly rolling around, then eventually got up. Master Xen...

Guy's Night Out Ch. 02

by jrzdogg on Aug 18, 2017
Gay Male

I woke up the next morning a bit hung over. "Did that really happen?" I asked myself. I wandered into the bathroom, took a piss, and looked at myself in the mirror. I couldn't believe I just stood there and let that happen. I guess the hardest thing for me to understand was that I liked it...I mean I REALLY liked it! Does it make me gay? I poured myself some...

At The Clothes Store

by Tedwar on Aug 18, 2017
Gay Male

More out of lack of ambition and the need to get out of the office for a while, I walked into Jeremy's, the clothing store near my office to see what was around. As it is a designer outlet store, sometimes you find wonderful clothes and sometimes you don't find anything. I'd been sort of dumped earlier that day, by Instant Messenger, by a guy who is intelli...

Kinky Kris Ch. 02

by Tara_Neale on Sep 14, 2017
Gay Male

Kris rolled sleepily over in bed. His cock pressed tightly against the firm bottom of his latest lover. He half smiled as he remembered the sex they had had the previous evening...and middle of the night. He considered initiating another round this morning but a quick look at the time on his phone told him that he did not have the luxury of even a quickie......