Gay Crossdressing Sissy Stories

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That's My Good Boy

by Submissivegoodboy on Sep 21, 2020
Gay Male

Bethany and I arrived at the hotel early that morning. We spend the day talking, snuggling, kissing, giggling and getting ready. Around midday I go into the bathroom and shave my body, we want me to feel extra sexy and feminine for my first time with another man. Mmmm as I come out naked and smooth Bethany giggles and jumps up and runs over to me. After sl...

Research Pt. 02

by eviltwin52 on Aug 18, 2017
Gay Male

Please read Research part one first. ***** "So in summation I submit that although a certain portion of the male population engages in homosexual acts, they aren't homosexual at all. No, they are under-endowed males who wish they could have heterosexual relationships but whom women shun. Through aggressive parenting, peer pressure, and social activities th...

Converted to Gay

by bart_allen on Sep 14, 2017
Gay Male

This story is partly inspired by messages from fans, with slight adjustments. Thank you for reading. ***** I wanted to share with you one of my current projects. A twenty five year old male by the name of Eric. Nothing too special in the looks department, but not too shabby either. He was neither heavy or slim, perhaps a slight softness to him. His eyes we...

At the Movies

by Michele G on Sep 14, 2017
Gay Male

Everyone knows Bobby and I are friends, but the don't know how close of friends were are. He's known about my crossdressing for sometime because we have been lovers for that long. One weekend my folks were away Bobby called me and asked if I'd like to get dressed up and go to the movies. At first I balked at the idea of going out in public dressed up, even...

House Rules Ch. 07

by EROTICbearscribe on Aug 7, 2019
Gay Male

WALKING THE WALK "We're going to have a visitor today," Daddy announced during breakfast one morning. He was wearing a suit because he had a business meeting. He looked very sharp. My daddy was so handsome. I was such a lucky sissy. When I asked him who was coming, he told me it was Miss Marguerite. "Miss Marguerite from The Beauty Mark?" I asked. L...

How I Became a Sissy Slut

by DixeenormousToo on Sep 15, 2017
Gay Male

I wish I knew I had these sissy urges when I was younger. Who knows, instead of getting married, having kids, and living the "American Dream," I might have discovered hormones, worked my body into shape, and become a tranny porn star. After all, how often does the American Dream really work out anyway? I'm unhappily divorced, my oldest is on his 6th year of...

My Inner Slut Ch. 03

by SlutAlexR on Oct 15, 2018
Gay Male

Well, no doubt about it: I was a slut. I had sucked my first cock; I had been fucked hard in the pussy; I wore girlie clothes for my Man; and here I was, his load drying on my face, ready to leave the house. Todd had laid out a few things he wanted me to wear during the day. Skinny jeans, a tight white t-shirt. Nothing too drastic there. But I had to wear b...

My Gay Crossdressing Vacation Ch. 02

by Flame666 on Apr 21, 2020
Gay Male

We pulled into the parking lot, Paul kissed me again and told me that they would pick me up at 9:30 the next night for our date and tour of the gay bars. I got out of the car and started to walk into the resort but noticed that the bar was closed and I was hungry. There is a Circle K about 2 blocks way and I decided to walk over and get some cokes and some e...

Sissy Dream Come True

by Sjen451 on Oct 6, 2020
Gay Male

It was Friday and I had one job left before I could start my weekend. I didn't have much planned other than watching some of my favorite sissy porn and playing with a few of my larger dildos. Not too exciting, but it's how I spend most of my weekends when I don't have other plans. Today I wore my red lace panties under a pair of black break-away running pa...

The New Order Pt. 04

by Iamkrazy4 on Apr 21, 2020
Gay Male

Part 4: On The Road to Love There I was, on my back, a dick in my butt, mouth, and both hands as I laid on table they had brought into the locker room. Around 3/4ths of the football team, and the coach stood around cheering as they celebrated their upset victory over our rivals. My throat and ass were sore as this onslaught had been going on for over an h...