Gay Shaving Sissy Stories

1,448 results
Orientation
Length
Source
Infinite Scroll

You are a Sissy Pt. 05: Master

by Roland15Rollin on Dec 24, 2019
Gay Male

Hello, sissy. Welcome back, princess. Welcome back to our journey through your sissy mind. You will always come back because I am what you want. I am what you need. You need my soothing voice. You need to hear my voice telling you what a fucking faggot you are. You need my voice telling you what a faggot you have always been. That makes you so happy. You...

Exploring my Sexuality Ch. 02

by alexis19901 on Jun 2, 2020
Gay Male

Just a quick recap from the first chapter. I'd made my first trip to a sauna, lost my virginity, got spit-roasted and then another guy came in my ass all before I left. The last guy left me his number and I just couldn't resist. This story will contain some crossdressing. I'd gone back to my normal life for a number of weeks since my trip to the sauna. Havi...

My Time in the Monastery

by brownmonkk on Aug 18, 2017
Gay Male

Brother / Sister/Slave, ("TML") November 1970 "Good loving & Good Scourging" The story of a MASTER and his slave! WOW, "it" finally happened!!! I had had my first sex, and it was with a fellow brother monk in the monastery. It was great. I always imagined having my "first time" with a sexy gal, but nonetheless my first sex was great! I often fantasize and...

Uncle Saul

by Kent100 on Jan 13, 2018
Gay Male

I would like to do two more installments to this if there is any interest... one about Danny... one more about Uncle Saul's business... all comments are welcome and will not be deleted... When I was a young kid, both of my parents were tragically killed overseas. They were on vacation in Israel and were collateral casualties in a café bombing. They were ne...

PIXIE Sissy Stripper Ch. 02

by EROTICbearscribe on Dec 24, 2019
Gay Male

Sunlight played peekaboo through the blinds and woke Benji from the best sleep he'd ever known. He opened his eyes and breathed deeply. His eyes adjusted to the bright light and he looked around the strange bedroom he found himself in. He noticed a fuzzy pink sweater draped over the back of a chair in the corner of the room. There was also a pair of yello...

Brother/Sister/Slave

by brownmonkk on Aug 18, 2017
Gay Male

Brother / "Sister" " TML", November. 1970 A Monk's monk or two virgins in the monastery; "Good loving & Good Scourging "Sissy" does her magic. WOW, "it" finally happened!!! I had had my first sex, and it was with a fellow brother monk in the monastery. It was great. I was a 20-year-old virgin and had fantasized about lots of women. I distinctly remember...

You are a Sissy Pt. 08: Future

by Roland15Rollin on Dec 30, 2019
Gay Male

Hello, sissy. Well, we have come to the end of our journey together, princess. We have explored every corner of your gay sissy mind and now we have come to the end. And what a journey that was. We learned so much, sissy. We learned about who and what you are. We learned about what you want. We learned about what you need. And we finally got rid of all of...

House Rules Ch. 05

by EROTICbearscribe on Jul 31, 2019
Gay Male

Chapter Nine BEYOND THE PINK DOOR For the next hour I explored the sissy wonderland which Daddy had created just for me. It was a bedroom fit for a sissy princess. I guess that was me now, Kitten, Daddy's sissy princess. There was a closet of pretty clothes and shoes. The large dressers were full of so many girly things my head was spinning. There was a...

House Rules Ch. 08

by EROTICbearscribe on Aug 12, 2019
Gay Male

READERS: The story of Kitten is beginning to cross boundaries into other genres. Just as Kitten has changed and evolved, so is his story changing and evolving. ***** Chapter 14 SEDUCED AND SISSIFIED "What's this, let's see. Oh I feel sexy
. What's come over me? Oh, here it comes again. Oh I feel released. Bad times deceased
My confidence has increased. R...

PIXIE Sissy Stripper Ch. 03

by EROTICbearscribe on Jan 6, 2020
Gay Male

Darryl Powers was on his way to one of the two popular nightclubs he owned. His new sissyboi, Benji, was beside him. The boi looked pensive and vulnerable, especially sitting next to Darryl. At 6'5 and a muscled but well-sculpted 230 pounds Darryl dwarfed the, for lack of a better word, 'petite' college boy sitting next to him. Anyone seeing the two pass b...