About a year ago I was on a trip with a friend and his girlfriend, a couple weeks after breaking up with a girl who I’d been with for 3 years. We’d booked a 2-bedroom apartment on AirBNB in Sydney, Australia for a long weekend, and my ex had been invited, but we broke up too close to find somebody else to take the flights or accommodation so she just paid me back for it and what had been planned as a cute double date weekend was now a third wheeling situation.

Jack and I had been mates since high school and his girlfriend Sarah (names changed) was good fun to be around so I didn’t anticipate the trip being awkward at all. The first afternoon we flew in we went out for a late lunch and after a short walk around the typical touristy sites, the bridge and the opera house, we headed back to the place we were staying. It was a warm evening and as we arrived in, Jack and I were both in a huge hurry to use the bathroom. Being comfortable with each other and both too desperate to wait, we shared the only bathroom, he sat down as I shamelessly pissed in the sink and washed it down while washing my hands. For most of the rest of the afternoon we all sat together on the couch watching Netflix before heading out again for dinner. At the restaurant, after a few drinks and our entrees, I headed to the bathroom again, and didn’t think much of Jack following me and standing next to me at the urinal. He shyly couldn’t pee and left straight away; when I got back he and Sarah were whispering to each other and watching me approach. Dinner went pretty normally after that and we headed back to go to bed and the moment we were inside, Sarah pulled me aside.

“Hey, so Jack is pretty shy about this” she said, “but he’s got a fantasy that I want to tell you about”. Jack blushed and sheepishly turned his head down. “Basically, he’s seen you naked a little and, well we know you’re bi, but Jack’s wondering about maybe exploring his attraction with you and I together?”

Jack is a very handsome guy, very solid athletic build, a little under 6’, could pull anybody he wanted and Sarah made it no secret how lucky she felt to have him. He’s sweet and kind, with a great career as a doctor ahead as he’s in his final year of medicine. I admire him a lot for his personality, so easy to get along with, very funny but a little introverted, which was especially obvious in this moment, as his gorgeous girlfriend of 7 years was asking his best mate of 10 if he’d get naked with them both. Sarah is absolutely stunning. She is also an athlete, narrowly missed out on the Tokyo Olympics before starting to take her engineering degree more seriously. I knew her both as Jack’s girlfriend but also from the classes we shared at uni. She’s 6’2” with long, muscular legs and washboard abs that her little brown dress was framing perfectly, bleached blonde hair, and she’d done modeling too, not hard to see why either, with an amazing pretty smile and piercing blue eyes.

I hadn’t had any action in about two weeks, which was a long time for me, and after Jack assured me that he was down I immediately said yes. We giddily rushed into their room, which had a big double bed, and I put my arms around both their waists. I’m 6’4” and quite skinny, easily the lightest and probably weakest person in the room. Sarah and Jack kissed, and then I kissed each of them a couple of times, while we felt each other up over our clothes. Sarah pulled Jack’s shirt off, then mine, and they both kissed either side of my neck, holding hands at the same time which seemed cute to me as I held them both close and reached down their muscular backs towards their toned butts. Sarah then pulled her tight little revealing dress off, and Jack and I played with and sucked on her perfect little perky breasts.

“Mate” said Jack “I hope it’s not been awkward but I’ve checked out your cock a couple of times today, could I please play with it?” he said, clearly still nervous. I nodded and he reached down into my trousers, still holding Sarah’s hand and kissing her. I reminded them both that I was having a great time but would not judge or object to stopping if anybody was at all uncomfortable. They assured me they were on the same page as Jack’s light squeezes made me harder and harder. I’m pretty hung, a touch under 8” and about 6” around, and it was quickly obvious that Jack had not been blessed by the size fairy quite as much, as I felt in his underwear something that may have been almost 5”, definitely pretty average size among the men I’d been with.

“My turn, boys” said Sarah, putting a hand in each of our underwear while Jack and I kissed and touched each other’s chests. He was so muscular, pecs bulging bigger than Sarah’s breasts which had been a running joke among our friends, and huge round shoulder muscles, with thick, popping veins visible. Sarah moaned as she stroked both of our now-rock-hard erections and pulled them out of our underwear. “Shit Jack no wonder you were checking this thing out, that’s massive!” Now it was my turn to be shy as Jack lent a hand, now both stroking me while Sarah fondled Jack’s now visible big round balls with her other hand. We then awkwardly contorted into a strange sort of triangular 69 wherein Sarah sucked Jack, be sucked me with a hand on my shaft and I buried my face between Sarah’s round, toned butt cheeks and ate her delicious, smoothly shaven holes.

Jack then said “hey can you put it in me?” and Sarah began rimming him to “warm him up for me” while I ducked into my room to look through my toiletries for the condoms I’d brought. I had actually planned to hook up with some randoms, and had been cruising Tinder, Feeld and Grindr for a week set to Sydney, and in preparation I’d brought a 20 pack of 4 seasons King sizes and a bottle of lube. When I got back in there, Sarah was stroking Jack with one hand, two or three fingers of the other hand buried in his tight, pristinely manscaped hole. They were both on all their elbows and knees, Jack moaning with pleasure. Sarah turned around and grabbed me, guiding me dick-first towards Jack’s ass. I had already rolled the rubber on and applied lube, and her tight grip and stroke felt amazing.

"Be gentle please" said Jack as I pressed my glans into him and felt him push back into me. I later learned that they'd experimented with pegging before and had loved using a strap on on each other. With relative ease I slid deeper into him and curled down over him to kiss his neck. "Shit bro you're a lot bigger than our toy" he said, looking over at Sarah who was playing with her clit and nipples and clearly enjoying the spectacle. We switched around and Jack rode me so well, he felt so amazing and warm inside, and Sarah came over to sit on my face and kiss and stroke Jack. Feeling Jack's big, swinging balls drag up and down me was a huge turn on and I was harder than I had been in a long time.

Sarah wanted a turn being fucked now, so Jack began slowly sliding in and out of her dripping wet, juicy pussy while I remained inside him. After a while, she said she wanted to feel me in her so I changed condoms, with both of them remarking they'd never seen a wrapper so big. I lay down and Sarah straddled me, her tiny pink nipples just in reach of my tongue if I craned my neck a little to suck on them. For a while I sucked Jack's cock as they kissed, until he reached around her and began lubing up her butt. It turned out they'd been planning all day and were used to anal, I just couldn't distinguish between their meals being those of health-conscious athletes or people planning anal sex.

Even with just a finger in her butt, Sarah's tight pussy suddenly felt crowded and tighter. She began quivering with pleasure, and as she bucked her muscular hips, she ground her way down until I felt the prod of her cervix. Jack then entered, and the feeling was obviously mutually incredible as we were all moaning like crazy, but only for about two more minutes as Sarah came, which set me off to blast one of my biggest loads ever. Sarah screamed out about how great my hot load and throbbing pulses felt, setting her off to cum again, and in turn Jack, who pulled out and held his cock to drench us both with a fast-shooting, thick and delicious load Sarah and I then licked off each other.

All sweaty, and a little bit out of breath, we decided it would be hot to cram ourselves into the far-too-small shower and, after being a mess of soapy elbows, knees and cocks, we dried off and all spooned in their bed, me the biggest spoon and Sarah the smallest. We fell asleep chatting about how fun and hot that had been, and after fucking a bunch more the next day, got ready to fly out. I hooked up with the pair of them once more before I met my current partner and stopped, but we remain really good friends, only brought closer together by some great non-judgmental sex.