I am James, living in Toronto, Canada's very affluent Rosedale area. My best friends and I live beside and across the street from each other. Brayden is beside me, Scotty is across the street, and Sam is beside him, diagonally across from me. We did everything together for 13 years, from kindergarten to the four of us just graduating from Catholic High School.
It was fantastic as I was closer to them than I was with my older brother and sister. The four of us lost our virginity to the same Catholic School Slut Girl over the last 12-18 months, but each of us admitted together that there was just so much baggage and bullshit, not just with her but with all the girls; we just wanted to fuck, get fucked, sucked and cum like volcanic eruptions down throats and up orifices. Sorry, but it is just how we boys are made. As I said, the four of us were inseparable and always together, doing everything together; usually, from Friday nights to Monday morning, we were together non-stop for at least 60 hours.
Just a few weeks ago, we even jerked off in front of each other for the first time; a day before, the four of us were off to a Boy-Bonding Caribbean trip to the British Virgin Islands for two glorious weeks to party with each other, and who knows what else may happen.
Teen boy circle jerks are a right of passage and cumming of age, a natural event that should be embraced and celebrated. It was a hot summer Saturday night in June of 2024. Scotty’s parents had gone to a wedding in Montreal, having already said goodbye… had fun, etc, as all our parents had.
We had the entire place to ourselves, as he had no siblings. Of course, teen boys sniff out the booze like a dog finding an invader dog's shit. None of us were driving, and the airport limousine was supposed to collect us early in the morning.
After several shots (3) of rum down each of our throats, we ended up in the basement on the leather sectional, two on each side and the TV angled across. Because it was so hot out, even with the AC in their basement, it was still about 77F. Scotty put on some hot 18+ teen girl porn, and in a few minutes, you could see the tented cocks all around the room. We were nervous and anxious as this was our first time flying for any of us, so we needed the stress release.
Scotty was very hot and cute reminded me of the Twink porn star Scotty Clarke, but with lovely flame-red hair and excellent white skin and great freckles on his face. Brayden, who lives beside me, is a total Blonde Greek God with long blonde hair past his shoulders, the spitting image of Valentin Bonnett from East-boys. Sam is pretty much the clone of porn star Kyle Ross, and me, James…. well, I think I look exactly like Darius Straube from Doggy Boys. Yes, the four of us are cute teen boys in great shape, close to 6 FT tall and under 165 Lbs.
We were all accepted and enrolled in the same downtown Toronto University, with our Programs starting in September. I was enrolled in general sciences and headed toward my career goal of becoming a botanist. I loved plants and everything about them around the world and studied the agri-botany of each world area on my own time. I lived a vegetarian-pescatarian-vegan mix diet, so I ate some animal products and fish but no land animal meats.
I am a very macho guy with a great body and, like all 4 of us, loved sports, such as hockey, football, and basketball. We often got stiff and dripped pre-cum rubbing up against each other and the hot boys on the ice, field and court; it was easy to see our tented cocks and wet spots. The shower time afterwards was the best. All nearly fully erect around! Incredible boy, fun seeing the swollen cocks of your buddies!
Scotty was enrolled in the culinary program. He was very masculine, as all of us were, but he loved to cook, so we often created dishes with my Botany love and his culinary skills and desires. It was great fun.
Sam was in pre-med. He loved the human body. Often, when we would horse around and play wrestle, he would identify what organ, vein, artery, muscle, nerve, etc., he was punching or squeezing. He knew the human body inside out and had big 18 x 36-inch laminated posters of every body system and parts plastered all over his bedroom. He dreamt of being a thoracic and vascular surgeon like his dad and grandpa.
Brayden was in Construction Sciences. His family owned one of the largest home-building companies in the GTA for decades and generations. He had been doing apprentice training in framing, electrical, plumbing and HVAC. All he talked about was building shit…any shit. He could not stop using his hands if his life depended on it.
Back to our rec room pre-flight night. Scotty said in a nervous voice with our board shorts all tented and wet spots forming, “I dare any one of you fuckers to whip out your dick and jerk off till you blow cum on your face.” Sam bugged his eyes out at him like they had some secret.
In a flash, Brayden stood up and threw his shoes off and a muscle shirt and pulled down his board shorts as his considerable cut cock sprang out about 9” with a lot of stringy pre-cum.
I said, “Holy Fuck, Brayden! That is a huge fucking hard cock. It looks bigger than what we see in the gym showers, buddy. I can’t let a buddy beat alone, so boys, I am going all in, too!” I pulled off all my clothes, same as Brayden, and my hard 8” cut cock popped out with even more cum strings than Brayden. Sam did the same giggling. His cut cock is about the same size as mine. Scotty, laughing and clapping, stood up and stripped as we clapped. He has lovely flame red pubic hair and a nice cut 7” very thick cock, and the biggest balls any of us have ever seen on a boy, the biggest of all of us, that is for sure.
Within less than a minute, with the four of us naked and pumping, stroking like mad, the moaning and groaning started. What we all noticed, giggling and laughing, was that none of us were watching the teen girls getting fucked in the video but were glued to each other's jerking cock. Each of us moved our eyes from one cock to the other to the other. Brayden was such a sight with his blonde hair and dark pubes. He started to writhe and thrust; his butt and his hips tightened, so we all knew he was about to cum. I got so excited seeing his gorgeous substantial whole hard erect cock for the first time; knowing he was about to blow hot creamy boy-cum put me over the edge as I ended up ejaculating first with five massive torrent volleys of one of the biggest cums squirted all over my upper chest, face and mouth.
That was it for Brayden, gawking at my blowing cock. He came with the same number of rope strings hitting his face, mouth and throat. Scotty and Sam were watching him as well. Brayden took his cum covered thumb and fingers and licked them off, dropping his semen into his mouth. Seeing this, I went nuts and scooped up my semen and dripped it into my mouth. That put both Scotty and Sam over the edge as each leaned forward and pointed their open mouths so wide as their hot creamy boy cum went straight down their throat with even more torrents than we had done.
None of us had cum out as gay or bi to each other; we just sat there staring and panting at each other cum covered naked and still slowly softening cocks. We wanted to explore our sexuality with each other.
Brayden said, “Scotty, this was your idea, so do you have a towel or something to wipe up what we did not swallow?” Scotty grabbed his White Calvin Klein Jocks and threw it at Brayden. He giggled and wiped the bit of cum residue and then threw it to me to clean up the same. Then I passed the sticky cum-webbed soggy undies to Sam, where he wiped the bits that he left, and then he threw them to Scotty. Scotty grabs it after wiping his cock and balls and inhales it intensely, rubbing the cum covered undies on his mouth and lips. We all giggled.
Brayden said, “That is so fucking Gay Scotty. Can we go for a swim, dudes?”
Scotty said, “Yes, the last one in has to eat all our assholes on the trip.” We all pretended to bolt for the basement walkout stairs, but I wanted to be last…I was dying to eat all three of my besties' boy-cunts.
Our affluent neighbourhood meant huge lots separated by many mansion-like gated homes. Yes, our parents were all well-to-do snobs who inherited scads of money from legacy family members. We could easily and freely converse in the pool at night; no other neighbours would hear. They laughed and started calling me the Boy-cunt eater.
After about 20 minutes, we got out, towelled ourselves, and sat on the patio. We knew it best not to drink anymore, as we wanted to be well and awake to get through security and on to our flight at 5 AM. The real party would happen once we were at our B&B in the BVI on or about noon local BVI time.
On the Patio, Sam said, “Guys, this first-time circle-jerk was a lot of fun; I was so relieved to see that we all like to eat our own Cum and semen. I thought I was a bit of a weirdo sick perv for years since I've been jerking off since I was 12 and slurping it up each night.
I answered, “Well, if we ever wanted anyone to eat and swallow our boy-cum then I always wanted to know how it tasted and felt. I find it lovely and exciting.”
Brayden replied, “That was my thoughts exactly. I have been eating and doing things at about the same time. I agree. If you can't stomach it yourself, why would anyone else?”
Scotty laughed to the point of tears: “You guys are so Gay! I am glad we got through this, and we will continue having more fun on the trip. But seriously, it is 9 PM, and the Limo picks us up at 2 AM for the 25-minute drive to the airport, so seriously, dudes, I know we are pre-checked in online and boarding passes, but we best get in and sleep some.” We all nodded, agreed, and did just that. We put on our tight Jockie-undies, grabbed different parts of the sectional sofa and two recliner rocker chairs, and tried to sleep.
Brayden and I were on the sectional. Our heads were close in the centre V-shape, each with our pillow. In about 15 minutes, the 3 of them around me were asleep. The low night light that was on cast just the perfect illumination onto Brayden’s Gorgeous face and lips. I knew I was in love with him. None of us had cum out to each other, fully gay or bi, but seeing as that Circle jerk and cum eating was pretty revealing, I was sure we were all wanting to explore our sexuality with each other on this trip.
At about midnight, I woke up having had a bit of a nightmare with the first flight flutters and nerves. I felt dread. I kept gazing at Brayden’s face and lips. God, his eyes and brows, nose and hair, and lips…fuck I wanted him so bad. Tears started to drip from my face with all the anxiety of everything.
Unexpectedly, he jolted a bit and opened his eyes; seeing me weeping right back at him, he became so concerned.
He whispered so gently, “James, what is wrong? Why are you crying?”
I answered, “Brayden, I am so scared and anxious—I just dread this trip. And... and I…I….Love you….you…. guys.”
Brayden whispered, “I love you too, James; don’t be so nervous. I am anxious also. It is expected to be nervous the first time flying a big trip. The boys, away from parents and alone, about to…to…party and…and….” I noticed he lifted his head and brought his lips closer to my face. The sexual tension as I saw his tented underwear and cum staining again was so exciting. I lifted my face and lips a bit as well. He came even closer, peering into my eyes; I closed mine and opened more as I felt his lovely, wet tongue enter my mouth and his lips close around mine. I ejaculated immediately in my underwear from the joyful eroticism. We quietly sucked face for about one minute until I heard Scotty say,
“What are you two horn-toads up to!” We pulled apart quickly in fear and trepidation. Scotty got up from the rocker recliner, and Sam woke and sat up.
Scotty asked earnestly, “Were you two boys kissing?” We both sat up on the sectional. I started to drip tears again.
Sam stood up, followed by Scotty. They reached for each other's hands, and Scotty said, “We need to clear the air before we leave, boys. We have been the Four Musketeers and lifelong best friends and neighbours forever, and we have never had any secrets from each other.
We should have told you before now, so please forgive us, but last week, on Wednesday night after our final exam, Sam and I …Sam and I …we….we……we had sex with each other. We think we are in love with each other.” Tears dripped from them both as they wept, sniffling and holding each other.
Brayden looked me straight in the eye and said, “James, I have been in Love with you since Grade 2. Will you please be my Boyfriend?”
I answered, “Oh Fuck, Brayden! I have wanted you since then also. Fuck I am so in Love with you!” the four of us jumped up and hugged and kissed each other passionately, sharing each other's lover’s lips and tongues.
I stated, “OK, Guys. I am so glad we all just came out and loved each other as always. But we have two hours before the limo picks us up, so let's cuddle our lovers and continue this four-boy bonding in the BVI Tomorrow night, agreed?” We all agreed. Sam and Scotty cuddled on one side of the sectional, and Brayden and I on the other. Brayden had his tented cock in his undies pressed to my ass cheeks for the next few hours. Sam had his cock pressed to Scotty's ass undies as well, and we held each other tightly, kissing.
This was going to be the most prolonged foreplay and edging in history! If not booked for this trip in hours, we would surely be in the middle of the hottest four boy-fuck fest since I do not know when, but it was all I could do not to pull down my Calvins and have Brayden slide right in my real boy-cunt and fill my virgin hole with real boy-cock.
I had never felt such peace and release cumming out and confirming my lover all in a matter of a few minutes was fantastic. I was also acutely aware of my desire to have sex with Sam and Scotty and all four of us to do anything; it was apparent that we would be in a full-blow boy orgy shortly in the next 24 hours; everything boys can do to each other all together at once flashed through my mind as my penis ran pre-cum like a hot geyser spring stream.
Before we knew it, our phones went off. We had 20 minutes to put on our shorts, shirts, and shoes and grab our phones, wallets, and passports with backup hard copies of our trip tickets, boarding passes, and one carry-on bag. The limo was a minivan with a very flaming driver that looked like Neil Patrick Harris. It was fun because, during the ride, Brayden and I held hands and kissed lightly, as Sam and Scotty did as well in the very back seat. The driver smiled and beamed from ear to ear.
We got to the airport, and after he helped unload our carry On’s, he slapped us each on the ass, wishing us a super fun boy bonding trip! We each laughed and gave him $20. We got through security and to our gate area. It seemed like no time at all, and we were finally boarding.
Luckily, we realized that the four of us were in a middle row near the back of the plane, near the washroom. It was an Airbus A350 on a British Airways flight. We boarded and got to our seats with no problem.
While facing the plane's back, Sam was on the far left, with Scotty next inward to the right. If you were facing the back perspective, then myself with Brayden beside me so that he was on the far right. The double seats across the aisles on both sides were empty. The plane was about 65% full, so it was not packed like sardines; that was nice.
We four started to sweat and shake as we got to the runway. We grabbed each other's hands and held on for dear life, whispering how we loved them. A girl group two seats ahead was doing the same, so they turned around and smiled and then kissed each other in a very hot lesbian display. They looked back, and the four of us put on a show for them, sucking faces between us all.
Finally, we were in the air, and the gear was up. I have always heard this was the first part of the most dangerous flight times. In another 10 minutes, we were at max cruise altitude as the captain released the seatbelt sign announcing calls for a smooth, low, turbulent flight—thank God, we were almost there.
We kept our seat belts on and chatted about our sightseeing daytime plans and tours. It was apparent we all decided we needed to go back to the B&B stay earlier than we planned as we were dying for that major four-boy-on-boy orgy.
We started to notice an older gay girl group ahead of us, maybe in their late 20s. One at a time, they kept getting up to go to the washroom many times, one by one, smiling and staring at our crotches and shorts. As the fourth one got up for the third time, I decided it was showtime.
I reached out and grabbed Brayden's cock to my left and Scotty’s to my right.
They both whispered and giggled, saying, “What the Fuck are you doing! James, are you Fucking crazy!”
I answered in a whisper, “Let’s put on a show for the dykes.” They giggled but started to get so hard. Sam reached in and started to play with Scotty’s cock, and Brayden reached into mine. The four of us went quiet and just watched each other's crotch as our cocks became titanium hard.
In a few minutes, we saw the flight staff start to come down with the first refreshment offering; time was limited. The dykes kept getting up one at a time, watching us rub each other's tented, dripping shorts. They smiled ever bigger and slowed their pass. The four approached with two on either side of the aisle as soon as the last one returned to their seats. The four smiled happily and nodded, making a visual block to anyone else coming down the aisle.
The one hot dyke with blond hair said, “Come on, boys, let's see them. With that request. We released our seat belts, pulled down our shorts and lifted our shirts and kept pumping each other's big hard cocks and rubbing our pubic hair mounds and balls. They pretended to make innocent chatter with us about the BVI’s. As they kept edging us on, it only took a few more dozen seconds, and the four of us almost came simultaneously with cum flying up, hitting our faces, mouths, hair and the back of the plane wall. It was so exciting to masturbate with each other as a boy group in front of girls as we surrendered our feral animal-like bonds.
The brunette went to the washroom and returned with paper towels to clean us up. They wrote their cell numbers on the nappies and asked, “Bi-orgy, call these numbers. We smiled and put our cocks away and said we would let them know as we cleaned our cum from each other but left it dripping on the back of the plane wall. They returned to their seat, raving about our hot penises and looks as it sounded.
After that relaxation and stress release, we chatted about our stay at a place called Gray Lily Escape in Parham town. It is a few hundred meters from the beach and bay marina and very close to Terrance B. Lettsome airport. Brayden loved to watch the planes land and take off, so it was perfect and looked like an awesome view—not too close and not too far. Our room was a studio with one queen bed, but they allowed another queen cot to be brought in.
About five hours later, we were landing. Again, we squeezed each other's hands so tight I thought our fingernails would explode. After much thudding and panted breath, we slowed and were off the runway. After a few minutes at the gate, we stopped. Thank God, Alive!
We giggled and grabbed our single carry-ons and passed the dyke girls who were disorganized. Each of us made sure to brush past their asses with our still half-hard cocks puffed out. We got out of the airport lickety-split and grabbed a local multi-destination taxi. We got to our lovely Studio check-in and did a quick cum clean in the bathroom. Seeing the two beds in the studio made each of us drip again.
Sam said, “Come on, guys, focus! We already came twice in 18 hours, so we have 14 nights here to suck and fuck the shit out of each other, but let’s stick with our daytime plan, please!”
We all agreed. We dropped our bags and locked the door. As advised by Global Affairs Canada, we zipped our wallets, cellphones, and keys in our board shorts, along with our passports. We then headed down to the Marina for Island tours and lunch supper.
Walking up and down the marina, we saw many chartered medium-sized fishing crafts offering extended tours of the islands, fresh fishing, cooked meals, and all the booze we could stomach. Prices varied in USD from $100 to $350 for a 5–6-hour island tour by sea with meal and drink.
We settled on a nice-looking middle-aged black gentleman named Leroy for USD 250. His boat was probably about 65 feet, but he had two great king-size Wicker-bamboo-ratan type partially covered loungers that looked comfy and some incredible island rock music playing. The rest of the boat looked older and slightly out of shape, but nice fishing gear and safety were prioritized.
He would not even take our cash until we all had our life jackets tight on and inspected by him. Today, yellow flags warned of large, sudden rogue waves and rough seas. The jackets looked okay but well-worn, and there were no other safety signals.
Massive plastic pools about 5x5x5 filled with ice and covered with a large stainless-steel lid with rubber straps and wooden handles. Much of the boat was what one would expect with many fishing supplies, spears, machetes, axes, with metal this and, wood that, rubber thing there and plastic that over there…. A shit-tone of metal and plastic buckets, tools, ropes, hoses and locked wooden chests of who knew what. Empty glass-capped booze bottles and many cases of water, beer, wine, liquor, bolted gas BBQ, and tanks.
We sat on the loungers and headed out of the bay. After 45 minutes, we could barely see the shores of the islands. God, there were so many islands of various sizes, and it was a vast open sea area. Leroy had the boat on a medium-speed autopilot. We realized he had stripped down to his speedo only and was proudly displaying a considerable package, even making Brayden look like a juvie- school boy-cock.
He came around and started pouring island drinks randomly to us. It was then that we became aware that the thermos he had been drinking out of was total liquor. He was so drunk a few times that we got up and grabbed him from swaying and nearly falling overboard.
He giggled and asked, “If you Laddies want to strip down and sunbathe in the raw of your boy skin, I am cool with that as long as I can strip too.” He giggled and swayed some more taking off his speedo, displaying the most enormous black cock we have ever seen. Fuck me, it must have been 12” long and 7.5” around at its base, and he was not even fully hard as his uncut glans were covered.
The boys and I looked at each other and replied with a smile, “Maybe later, Leroy, we are getting hungry for lunch.” We kept our shirts on and had our second beer after his few island drinks of something. Finally, an hour later, we started to get pulls on our fishing lines. It was some good-sized Yellowfin Tuna and Groupers. Then, a few minutes later, a Mahi-Mahi, Brayden had caught. It is a big fucking fish, the size of a small shark, and so ugly and scary!
We had been out now four hours, and Leroy was still drinking away, signing the song “Show Me the Way to Go Home!” Hammered. He started the BBQ and opened his stainless-steel mini fridges for veggies and sauces to make fried veggies, fish lunch, and supper. He barely could stand, but he came around and managed to help him. Every time he swayed, he made sure to grab our crotch and cocks and slap our ass-cheeks, almost pulling down our shorts. We all stood far back when he started to hack up the fish. I thought us fags were going to puke and pass out right there…not pretty. Finally, he accepted some water. The boat never stopped as he kept it going on autopilot, so we had no idea where the fuck we were, and many times saw no land at all as far as we could see all around.
It was not only I who started to get that doom feeling. Finally, an hour later, supper was cooked, and the rest of the fish bits were in the large ice-covered bins. We each had some water and another beer. The first meal was delicious, and Leroy realized he was still the only one naked, so he hitched up his speedo at least.
Scotty stood up from our lounger and said, “I have to take a piss or maybe a shit even.” We giggled, and he walked back to near Leroy and started to get down through the half door, expecting a small Sleep/Galley spot, living quarters, washroom, etc. We suddenly heard Leroy get upset and angry when Scotty was mainly down below deck.
He yelled, “Boy! What the fuck are you going down there for. That is my place, you little fucker.”
Scotty said, “I must go to the washroom, Leroy.”
Leroy answered, pissed off, “You whip your little white cock out and take a piss off the edge in the ocean, you dumb fuck!” He giggled and swayed.
Scotty said, “But Leroy, I have to take a crap, I think…sorry!”
Leroy laughed even harder, “Then you hang your White boy sweet ass over the edge and get your hot little Laddies to hold onto your little cock and balls and hope that the big shark doesn’t cum pull you in for supper! Now get the fuck up here!” He giggled and laughed some more. Scotty came back looking very upset and worried.
The rest of us noticed that the first small piece of land had appeared during all this. It looked like an E-shaped Island with a sizeable mountain, hill-like peaks, lagoons, etc. It was gorgeous, a few Kilometers long from our view.
I asked Scotty, who looked utterly white as a ghost, “Are you OK? Can you wait a few more hours before we are back?”
He answered, whispering to us quickly in a very urgent tone and speed, “I don’t have much choice, but the fucking below deck is like a small fucking liquor store. Empty and full booze bottles everywhere. Don’t light a match near him or the below, or we will be on the fucking moon!” We all roared.
Scotty stood back up, looking to the other side of the boat behind our partially covered lounger canopy—away from the Island a few hundred meters from us to the back side opposite our view of the island.
Scotty, concerned and pointing, said, “Oh Fuck Guys, look, what in the fuck is that!?!”
The three of us stood up and looked to that side. A few Kilometers away, we saw a white band that looked like a bank of thick, heavy fog, yet it was a hot, clear, sunny, near-cloudless day.
I said, “Fuck guys, what is that?” It came closer and closer. Leroy kept drinking and singing again. The anomaly sped up and got more significant, like maybe 25-40 FT high. When it was a few dozen meters away, Sam yelled,
“Oh, My Fucking God! It is a Rogue wave!” We ran and yelled to Leroy as he grabbed a Machete, threatening our death if we all did not strip down and take off all our clothes. We backed up and pointed at the wave. He dropped the machete and grabbed the boat wheel. It was too late. The wave was on us. I went to grab Brayden, and Scotty went to catch Sam.
Before we had each other, we were in the water, tossed far from the boat, with all its contents and parts spilling all over us as it exploded from the wave pressure and force. I was sure this was the end! It felt and reminded me of rolling down a ski hill through the water, but hitting this something and then another thing, I felt pain, impact bruises, and cuts. I tried to swim for the surface, and the wave kept rolling me over and over and over….I could not see anything but water and bubbles and screams of my best friends. Coughing and choking, we all were like rag dolls.
What felt like many minutes later, I heard screaming as I realized I was face down in some sand with debris all around me, tangles up in some rope and fishing lines. I raised my head and saw Sam on top of Brayden doing CPR compressions and Scotty delivering the air breath after 30 presses.
I screamed, “God, Brayden, No! No! Please, God, No!” I untangled myself and tried to run and felt a terrible stinging pain in my legs. I realized I was cut near my lower left calf, bleeding from my chest, and nasty scrapes and lacerations on my forearms. As I got closer, I saw that Scotty and Sam had similar types of lacerations and contusions randomly about us.
Once I was finally upon them, I screamed, “Please, Sam, Save him! Save Him!” Sam had tears dripping, as did Scotty, with both his hands together like a prayer bashed down on Brayden's chest one more time, dam near cracking his sternum in half!”
Brayden suddenly sat up, coughing and hacking, throwing up brown water, muddy sand, and seaweed! I ran to him, balling my head off, holding him so tight, sitting up as he continued to cough and hack.
“I love you, Brayden! You're OK. You’re OK! We’re all alive! I Love you so much!” I sobbed. We did not know where Leroy was and did not fucking care!
