First time raw, planned or unplanned?

[subiboy]

My first was unplanned, it was also my first anal. It was completely spontaneous for both of us, but it was enjoyable.

[PozTalkAuthor]

Planned and consenting, he was a trusted person. We started dating and used condoms at first both me on top role, and him. 

Then we decided to give it up and feel "more natural" we said! 

[cboycam]

First time was unplanned, but I still would not have used a rubber if it was planned.

[Close2MyBro]

Unplanned. Was a high school friend I had just started sucking off a week before at a sleepover . Was sleeping over again and was sucking him off and he told me to lay down on my stomach. I turned around and laid down face down and he started rubbing his dickhead against my hole and trying to push it it. I had already been playing with my ass on my own for a while by then so I told him to get some lube and he came back with some lotion. He lotioned up his dick, squirt some lotion on my hole and then worked his way in. The lotion stung but I enjoyed feeling his dick in my ass. Once he was in he didn't waste any time and went to work pounding my ass till he shot. I felt his dick throbbing like crazy and his cum spurting into my ass. When he was done, he left his dick in my ass for a bit until he caught his breath and then pulled out and cleaned his dick off with his boxers. I put my underwear back on and we went to sleep. That was one of the best summers of my life.

[Guest]

Unplanned in the moment

More fun that way...the adrenaline rush increases with excitement....pretty sure those involved subconsciously know what they are getting into ...

[ktopper]

The first time I got fucked raw was the first time I had gay sex. I have told about this encounter elsewhere on this forum. This was back in the 1970s before anyone had even heard about AIDS. Condoms were not a thing back then even with the ladies, which I had fucked a lot of before I got around to sex with guys. This entire hook-up was unplanned, I was in a city far from home and went into a gay bar without realizing what it was. A guy hit on me and I went for it thinking it would be a one time thing. It wasn't. After a couple of years bottoming I met a complete total bottom and topped for the first time, raw of course. That hot and sexy little bitch made me a commited top. We got together every chance we had for over a year. I would have crawled across several naked and horny centerfold models to fuck his sexy ass, LOL! On one occasion the two of us ended up in bed with a girl and I fucked him with her watching. After I came he proceeded to give her a good fucking with me watching, my cum oozing from his ass as they fucked. I, being the gentleman that I am, proceeded to clean up her wet pussy with my tongue when they were finished. It was a nice night, the girl wanted a repeat but it never happened.