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

Defo a BJ first and see his reaction.

If he is ready to have sexual experiences with you, he would certainly enjoy you stroking him. Especially his stomach and genitals. You could examine his penis and testicles extensively and then lie behind him and instead of penetrating him anally, rub your penis between his buttocks and hug him tenderly. Or you could dance naked with him in a tight embrace. He can then feel your manhood without penetration. And when you're back at home and condoms, lubricant and hygiene are available, you can get inside him. It would certainly be a wonderful experience for both of you.

I agree that anal sex was in advisable, but your friend clearly was interested in exploring sexual activities with you, and maybe later with others. Stopping then would have sent him the wrong signal. I would probably ask him if I could remove his under pants, and be guided by his answer. Yes= interested and go further. No= I've had enough for this time. From that point on continuing you could be stopped at some intimate point, or could ultimately have a male lover, or playmate. As with all new potential sexual lovers ,only permission, exploration, or another sign will say where you end up. With patience and care, your chances of success are high. Good luck!

There’s lots of room for options. Definitely give him a nobber. After cumming in your mouth, he will appreciate the action. Invite him over for a bag or two to raise the stakes. Then take the plunge!

@Sten please share what actually happened after that and on the next 2 days of your trip....

SO, just to be a little contrary, and to express some true feeling for me and maybe a fetish, and if I was him (the potential receiver), I would have hoped or tried to talk you into taking me then and there ... that first experience, the subtle way you got to there ... it would have been a heated passionate moment for me and probably something I desired for so long. I would say there is always a way to clean up after.

Anyway, I believe you did what was right for you two just expressing my hopes.

I would’ve given him a hiney cleavage pearl necklace and a handy reach-around.

So you folks have asked me what actually happened … that’s fair enough and thanks for your replies, which have now made me feel ok about saying more. When we’d made our first moves Stewart said nothing verbally but although nervous he was clearly excited and keen for me to continue my exploration of sexual excitement together. We were still young & naive but I knew how strongly attracted I was just to seeing him in his tight jeans. It may sound silly but also things like glimpsing the waistband of his briefs down the back of his jeans when he crouched down. Fantasising about having seen him in just his underwear. Patting each other on the bum and feeling the outline of his briefs through his jeans. The close contact of playful wrestling together.

So having received good signals (and felt strong sensations) by Stewart letting me peek at his cock and probe his anus, there was no leaving it there. But there was also timidity at going too far at once.

I chose to keep it as equatable as possible rather than just have me imposing myself on him. So I took off my briefs to lie naked beside him in our little tent and was pleased to see him take his off too. I hugged him and he followed my lead as we tentatively caressed each other’s backs and buttocks. We took a moment to eyeball each other’s cocks, both fully erect and dribbling precum. Then I brought my hand to his penis. He shuddered as I touched it and lay himself back in surrender to being pleasured. Not having a foreskin myself, I was fascinated by his foreskin which only half covered the head of his penis now that he was erect. I really didn’t have a plan but I was on autopilot. I don’t think Stewart would have cared where or how I touched him, he was in ecstasy whatever I seemed to do or not do, and so was I. I was actually touching my friend’s penis and not only didn’t he mind, he liked it! I saw how his foreskin could be pulled right back and felt how stiff his cockshaft had become. The head of his cock looked like it would burst, but then again so did mine, and it felt like it too. I definitely felt the urge to rub my cock against him which I later learned was part of the natural urge for me to fuck him.

However, still early days, I rather unskilfully rubbed his dick then watched in awe as he convulsed as his semen forcefully spurted out. In a chain reaction, and without either of us touching my own cock, I also had a spontaneous and massive orgasm. As I fell onto my back, my cum shot over my head, with subsequent spurts splattering onto my face, chin and chest.

We were silent for a moment then laughed and cuddled, rolling onto each other, wetting each other with our respective pools of cum.

We stayed naked, holding each other while laughing and chatting. We were excited to have broken the ice on our mutual sexual attraction. We were relieved and also excited as to where it would go. When the time came, we squeezed together into just one sleeping bag but it wasn’t long before we were feeling each other up again and ejaculating another load together. Stewart seemed to like it when I put a wetted finger up his ass, and it turned me on to do so too.

Day 2 we remained free of guilt or regrets and were able to feel carefree love & sexual excitement as we hiked to the next place. For hygiene we went to shower at a public swimming pool. The showers were communal so although we were fortunate there weren’t many others around, it did feel like we should find other cleansing arrangements because we couldn’t help getting full boners together in the showers and changing area.

So on the last night of the trip we used up our money on a room at a farmhouse where we shared a double bed and had an ensuite bath. Our hosts knew we were tired from a few days of hiking and let us use the room till well into the afternoon of the next day. While in the bath I was able to finger Stewart’s anus and feel him to be clean enough that I soaped him up a bit, soaped my cock and we finally got to have our first proper anal sex, which was a great success.

He was very tight but I’d had to go very slowly, as much for me as for him. Any faster and it would have felt like the head of my cock would rip apart, but as his anus slowly yielded and the soap help me to ease my way in till I was able to go from slow shallow strokes to full length strokes and at a fairly lively pace. The sensations were fantastic, as was the feeling of cumming so strongly and deeply inside the rectum of my close friend.

It worked out that by the time the water heater had got us another tankful of hot water for another bath, Stew and I were ready to fuck again, which we did five times before we had to leave.

We’d also tried it with Stewart trying to fuck me, but it just didn’t seem to be my thing and we both preferred for me to give Stewart oral instead. I did like him sucking each of my balls and giving me a good rimjob though before guiding my eager cock into his tight ass.

After a few more weeks into our young sex lives, I was able to perfect oral pleasuring of my pal, and I never tired of the taste of his copious loads of thick semen. Even so, it didn’t seem that anything could compare to my extreme pleasure in buttfucking Stewart’s cute, hairless ass!

So as teenage first sex goes, it couldn’t have gone better after such a tentative exploratory start.

Please feel free to message me directly for any follow up, as I don’t always feel confident putting it all in public. It was hard enough for me to reveal as much as I have in the above