So what would you have done if you were me?

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??

Interesting question.

I am a bisexual woman. If I were a man, I would have opted for oral sex. You could make another date and butt fuck another time after being cleaned out or having condoms.

I agree with switchablesusie.

Yep, BJs for each of you. By breaking the ice of having sex, it sets up another chance to fuck later. Afterwards you could express your interest in fucking and be very upfront about the practicality of having an empty and clean rectum. You made the right call at the time because you want your first anal sex outing to be as clean as possible, which makes it very enjoyable and makes you want more in the future.

An informative thread so far! I've just finished telling a correspondent about a couple of close-up glimpses of other boys that I had in my teenage years, when I experienced very definite gay feelings - but neither of those glimpses led to any hands-on stuff, etc., more's the pity!

- Ken

I think you made the right decision. I would not have worried about him being not super clean, though. I rather think that unprotected sex is in general not a good idea. Plus, I assume that you did not bring any proper lubricant, which I believe is very important for a pleasant and enjoyable experience.

I agree entirely with enema jock. Apart from it being potentially a mucky and off putting experience for both of you because of no chance to clean up beforehand; without condoms and a lubricant, it would be a painful experience for both of you too. Far better to have perhaps played with and jerked off each other, or as switchable Suzy recommends, a blow job. If both of you enjoyed the time spent together, then it would bode well for a future weekend or time away with just each other for company!

Handjobs are quick and easy - and once you cum, the sexual tension is released...

It looks like there is a lot of agreement here. I have a young friend who thinks he is gay work for me on occasion. He knows underwear is a turn on for me and often opens his pants to show me what he is wearing. He has given every sign that he is interested in something and from time to time wants to jack off but so far nothing more. Our friendship has lasted for many years now. Sometimes if friendship is the ultimate goal it is best to let it go where it goes.

You both must have thought possibly, intended, to see if you would be comfortable with a physical experience. The excitement you both had making that progress to undressing and exploring each other, you both will look back on with fond memories, no matter how long you are together. Lots of touching, stroking I think would have been very erotic for you both.

I think the move, to anal, would have proved to be a step too far and too soon. I hope you both enjoyed mutual mastubation. This is an excellent introduction, and I am sure over the remaining evenings of you trip you both would both have looked forward to this activity and enjoyed. Taking it forward to giving each other a blow job. Possibly moving to 69 position, However why rush to advance to other activities, mastubation is wonderful in its own right.

The move to anal can be taken when you both are ready, when you both have the desire to do so and you both are able to prepare with hygiene, lubricants and condoms.

I think you would then find the excitement similar to the very first moment you had on your first camping trip.

I would have stuck to handjobs and maybe oral. It is likely this will develop into something long term, and there is time for anal later when proper hygiene is easier