Seriously, what would you have done? … Stewart and I had become close friends to the point I felt we had a crush on each other. He agreed to a 3 day walking trip, camping along the way. We spent the first evening in the tent in just our underwear and becoming comfortable as such.
I said I quite liked the plain burgundy colored briefs he was wearing and asked where he got them. He didn’t know, so I pulled the back down supposedly to look for a label. I said it didn’t say much and pulled the front down to see if there was more info somewhere inside his briefs. Having got this far without a negative reaction, I held the front of his pants open longer than was necessary, making it clear I was ogling at his penis, and asking what it was like to have a foreskin.
He seemed very nervous and coy but also very accommodating and in the moment. I reached inside to play with his penis, slipping my other hand inside the back of his underpants to roam across his buttocks and bum crack. His cock was stiffening up and there was an unspoken air of submission on his part. My own cock bulge had clearly stiffened up too, which he released from my briefs by pulling back the elastic.
Emboldened, I let the tip of my index finger rest on his anus for a moment before wetting it with my mouth and then slowly easing it all the way into his asshole. He was clearly nervous and trembling but in a sense of anticipation, so I continued.
I had fantasized about easing my cock up his asshole and right now seemed to be an unmissable chance. However, although his rectum seemed empty enough, my finger showed that it was far from clean and we had no chance of showering or cleaning up. I wondered why I hadn’t taken condoms in case of getting lucky, but I really hadn’t thought I’d have achieved anything more than perving on him in his undies and perhaps seeing the odd flash of cock when changing or showering at a public baths. If he really was going to let me fuck him now, my cock was going to get really messy and I assume would risk a nasty UTI.
So … what would you have done??