Gay Cross Dress Stories

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Can I Try? Pt. 02

by ShyTammy on Sep 14, 2017
Gay Male

That kiss was the highlight of my life to that point. Randy, my sexy blonde best and secret crush had kissed me after I had given him a blow job. My mind was reeling and my heart was beating so hard I thought my chest would explode. I was ready right there and then to give him anything and everything he wanted. A lifetime of shaming and indoctrination wasn'...

Corey and Noah Ch. 04

by shaneo94 on Sep 25, 2017
Gay Male

Noah's birthday weekend was one of the best, if not the greatest of my entire life. The rest of the sleepover passed without anything sexually notable, yet I was pleased to know that Noah wasn't at all uncomfortable with the prospect of getting undressed in front of me. When I wasn't sitting around eyeing Noah's beautiful body and begging my boner to go down...

The Pictures Ch. 05

by Mike Cindy on Aug 17, 2017
Gay Male

I woke the next morning and checked the house before leaving for work. I made sure everything was in its place. I hoped my wife would be home tonight and I didn’t want any problems. Jack called me about 10:30 and said, “you’ve got e mail”, and hung up. I opened the mail and saw 2 pictures of me dressed in female clothes; the poses Jack had put me in last n...

Bi-Brad Ch. 01

by Martins on Aug 18, 2017
Gay Male

My name is Brad. I know, the name sounds either gay or preppy. But, I'm single and have a busy work schedule. So I don't get to meet wild women, engage in sex orgies or the like. I just have time for occasional sex. Besides; I sort of like men. Oh, I like women too, but I'll be honest, I've fucked just one man steady since college. I think I'm just too lazy...

Running With Kings Ch. 01

by rjvansen on Aug 18, 2017
Gay Male

Scott Griffin pulled his blue Ford Mustang into a parking space just to the left of the loading dock of Stonewall Hall. At least six cars were battling for spaces closer than his to the door in the loading area, but he didn't care. He was only a little farther away but he could walk his bags in the little extra distance. He wouldn't have to deal with the pus...

Found Ch. 06

by cowboi on Sep 26, 2017
Gay Male

Walking up the stairs, Melania heard her brother Lucas walking around his room. She wondered about his and Calen's outing to the property earlier. The expression she saw on Luke's face when Calen walked in during the meeting was priceless. She knew she HAD to bug him about it. "Hey can I come in?" Melania asked as she softly knocked on Luke's slightly opene...

Superman's Dilemma

on Aug 31, 2017
Gay Male

He was getting close, and Lois showed no signs of stopping. She was riding his sodden shaft like she was riding a bucking bronco, except he lay utterly still. Her bouncing breasts drove him crazy. He wanted so much to explode right inside her, but he couldn't. "Stop, Lois." "Almost there. Just a little –" He lifted her off his penis with utmost care and s...

How Did I Get Here

by bart_allen on Oct 15, 2017
Gay Male

I found Wendy on OKCupid. She was just another face as I scrolled down, albeit a fairly attractive one. I clicked on her profile, glancing over it: she was older than me, which is not usually my type, and she was six years older than I at thirty two. She had a darker natural red hair in shoulder length cut, but a sort of light olive complexion, and pouty lip...

How Sweet It Is!

by walterio on Sep 16, 2017
Gay Male

PRELUDE Rick Jennings rolled over in bed on a Saturday morning and took a hold of his erect 7" cock. He stroked it for a few minutes and then decided to get up and take his morning piss. He rolled his 6'2" muscular body out of bed and walked naked into the bathroom. After relieving himself he left the bathroom after cleaning up a bit and made his way down t...

Turning the Teacher Ch. 02

by Dave933 on Aug 18, 2017
Gay Male

I woke up early, sunlight pushing through the feeble barrier provided by pale yellow curtains. I was lying on a double bed in a strange room, and for a moment I wondered where I was. Then it came back to me. I was at my teacher's house, Mr. Wild. I had found a sordid and sexy video he had starred in before he became a teacher, and used it to blackmail him...