Gay First Dildo Stories

20,665 results
Orientation
Length
Source
Infinite Scroll

Surprise First Anal Experience

by BottomBoyUK on Jul 9, 2019
Gay Male

I was 21 and had just finished at university. I knew I was into cock and had sucked one before but had been too nervous to take one in the ass. To me it felt like crossing a threshold into being gay that I wasn't sure about. I had been chatting to a man called David online, who lived in my town for months by this point, and he made me feel comfortable enoug...

Am I Really Gay? Pt. 01

by Str8NotSoMuch on Jun 9, 2020
Gay Male

I stared at the little blue pill in my palm for several seconds, then I poured two more Viagras into my hand. "Fuck it, this stuff doesn't really work anyway," I thought, as I threw the handful of pills into the back of my throat and chased them with a glass of water. I thought erection pills were supposed to give you an instant hard-on. It turns out they...

Member of the Club: Teaching

by hasnoalias on Aug 18, 2017
Gay Male

A few weeks ago I had been requested to teach a class on sucking cock and ass rimming by James. I had scheduled everything with Dan, and now I was in the "party room" waiting for everyone to get here. I had asked James, Ken, and Alex to attend. They were happy to do so, once I told them what I had in mind. I had organized this class on the club's website, an...

Submissive's First

by SilverShade on Aug 18, 2017
Gay Male

If reading gay porn is illegal where you live or if you dislike it try clicking the X in the upper right corner! I own the copyright to all my works. Disrespect that and my lawyer will do very horrible things to you while I watch... * I had agreed earlier to this little roleplay, but now I had butterflies going beserk deep inside my body. I didn't really...

The Package Pt. 02

by A_Can_Of_Beans on Sep 14, 2020
Gay Male

A week had gone by since Max first discovered that wonderful package. Since then he had been a lot more curious about himself. First of all he learned of his new obsession with texture. The cool silk of his nightgown sent shivers down his spine. The feeling of smooth, freshly shaven skin was freeing. And best of all was the excitement of dressing feminine....

You'd Let Him Do Anything To You

by catch1986 on Sep 14, 2017
Gay Male

You see him standing in front of the bathroom mirror, in nothing but a red pair of boxers. Just imagine him masturbating in front of that mirror. His hands sliding down his skin. His fingers slipping into his underwear. The stirrings of a boner getting started. His hand moving around in the fabric. A wet spot appears in the front. Maybe one or two fing...

A Vacation in Mexico

by luvcurious on Aug 18, 2017
Gay Male

When I started chatting with and mailing letters and stories to him, it was just fun sexy electronic play. We talked about everything. Most of the time it was real hot and we’d both cum to the stories and chats. Then after about three months of this we began making suggestions to meet each other. I live and work in Long Beach. Jerry lives in Cleveland....

Trips We Take

by bi golly on Sep 14, 2017
Gay Male

Some times, we go places we didn't intend to go, but are happy to get there when we do. That is certainly true with the way my wife and I developed sexually. We married after she graduated from college. I was two years ahead of her. I graduated and moved about 30 minutes away to my first job. We saw each other each weekend and also during the week. Sex was a...

Seven Minutes in Devin

by NickyNoxville on May 11, 2020
Gay Male

All my stories take place in a parallel world, very similar to our own, where STI's do not exist, so my stories are filled with practices that are highly unsafe in this world. I'm not going to say don't try this at home, but take care of yourself. All my characters are of legal age, and you should be, too—do not read my stories if you are under the legal ag...

Teachers Pet

by Guy521 on Jun 5, 2019
Gay Male

It was a hot summer afternoon, when Nick arrived at Mr Jenkins house. He'd missed a lot of work over the past few weeks, but Mr Jenkins had offered to help him catch up. Checking his reflection in the door, one last time, Nick gave it a knock. A few moments later Mr Jenkins answered the door. He wore nothing but a pair of tight black shorts. Nick immediately...