Gay First Dildo Stories

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A Closet Faggot's First Time

by Closetfaggotnyc on Sep 14, 2017
Gay Male

I'm not a writer. This is my first story. It is totally true. Forgive my poor writing style. ***** My name is David and I'm a closet faggot. I'm 32 years old, work a boring office job and live alone. In high school and college I had a few girlfriends. They would blow me on occasion and let me fuck them, but even then I knew I wasn't enough of a man to sat...

My First Time with the Neighbor

by lotoplaz on May 12, 2020
Gay Male

I don't know where to start. I always struggle with starting new projects, for school or more private, but I really, really need to get this story out of my system. I can't tell my friends and especially can't tell my dad. For obvious reasons. Well, okay. I saw people here usually introducing themselves at the start? My name's Malcolm. I'm average I guess?...

Becoming an Anal Sex Whore

by Patrick2380 on Sep 14, 2017
Gay Male

"So, what made you decide to post your ad online tonight?" he asked as I we walked down the hall of my apartment building. "I don't know," I replied. "I guess I am just really horny and wanted to try something new." I knew, though, why I decided to post the ad that read "28 year old male looking to have sex with a man for the first time. Please, be open to...

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...

The Car Ch. 2

by rjohnson on Sep 14, 2017
Gay Male

The next morning, my ass was still sore from the night before so I sat in a hot tub for about an hour. After getting out, I started thinking about the wife again and had an instant hard on. I remembered the feeling of the father's fat cock and the son's thin, long one plowing into me and my cock got even harder. I decided right then that I had to go back and...

Learning to Surrender Pt. 01

by miked1983 on Oct 15, 2017
Gay Male

When Rick was in college, he came across an erotic stories website. He loved the stories of women who surrendered to dominant men and learned to satisfy every need of their lovers. Then one day, he noticed a category of stories for gay men and the first story he read of a man essentially becoming a woman in another man's bed was seared into his mind. He sign...

It Started So Innocently Ch. 02

by bogey4u on Jan 14, 2018
Gay Male

A few weeks ago I started a sexual relationship with a new male co-worker. Like me, Brad was not gay, we were just new friends, that really enjoyed hanging out together. Things got pretty hot between us after a silly dare. Eventually we lost control of ourselves and had the hottest, most intense, sex of our lives together. This is part two of that wild story...

A Dream That Might Come True

by NerdySex on Feb 25, 2019
Gay Male

"Oh, that feels so good. I just love what you are doing," I exclaimed as my co-worker fucked me in the ass. "So tight. God, it feels good." This was the third secret time I had been with Jim, a friend that worked at the same place as me. I was laying on my stomach and Jim was slowly thrusting his big cock into me. Each time it gets better. I remember well...

Master Comes on Sunday

by Cap_N_PieSissy on Dec 9, 2019
Gay Male

My Master is much younger than I am, and it would be entirely accurate to describe him as a twink. Small, lithe without an ounce of body fat in him apart from a certain softness of his facial features, and packaged in soft, smooth hairless skin. He fully enjoys all the greatest blessings of youth, but there is a devil in him. He found me on the internet. I...

A Soldier's Journey Ch. 01

by FenFenScreeScree on Apr 13, 2020
Gay Male

(This story is based on true events. Details have been changed to protect the identity of the characters) Sometimes, I worry if I've gotten too far in over my head... My journey through chastity play is not an easy one, and it's a path that many of my sexual peers would never have had the fortitude to walk down. Allow me to preface this story with what y...