It must be well after midnight, I thought, glancing around the dark room. I could hear car tires hissing on wet pavement outside the window. My trip down Amnesia Lane -- as one of my college buddies called memory daydreaming -- had lasted more than an hour, maybe longer.
I stretched my sore back and stood for a moment, working the kinks out. I desperately wanted a cigarette, even though I quit years ago, and I gave up drinking alcohol in 1994, so that was out of the question. I hated coffee and most places don't serve tea so I'm usually reduced to chewing on breath mints or sipping a soda. None of those were options right now, so I sat back down on the hard metal chair and resumed my vigil, if you could call it that.
Where was I?
"Paging Dr. Wheeler; paging Dr. Wheeler." Oh yeah, prep school. It all seemed so long ago and yet very present, very real, especially on this night.
Not long after the circle jerk at the willow tree on the shore of the lake at St. Philip’s, and for the rest of the fall term, Harry, Tyler, Colin and Wes became regular visitors to our rooms in the evening. We studied together and talked about our college prospects and what we wanted to do with the rest of our lives.
But there was always an undercurrent of sexual tension, as if Harry and the others wanted to repeat the circle jerk but were afraid to ask.
Another boy who began to drop by fairly often was Chad Wheeler, a neighboring roommate during our first year who had never really connected with us very often for the past three years but suddenly rediscovered us during winter term that final year.
Chad had evolved from an adolescent string bean into a tall, wiry, lithe runner who excelled at cross country and track. He'd set regional and prep school league records in most major events and was well-known as a good student and good friend. But we never seemed to cross paths until that term.
I remember helping him with math and chemistry assignments during that first year when he lived down the hall. He was a quick study and moved on from needing my help to helping others. Even in a small school like St. Philip's there were always subgroups of boys and I guess we never intersected with his group.
That doesn't mean I didn't notice him. My recollections came mostly from our almost daily contact in the large group bathrooms that first year. My memories focused mostly on his bright, chipper attitude and his very long, very thin cock which hung low over a nice pair of balls and a bright red bush of pubic hair.
I sometimes saw him in the showers after a track event during the past two years and I had more than a few good photos of him in my sports photography portfolio at the student paper office. Despite my monogamous love affair with Teddy, Chad intrigued me.
One Friday evening, after dinner and before Harry and the others arrived to go to the movie being shown in the Great Hall -- our only sanctioned weekend entertainment -- Chad tapped on the door. This was a newer Hollywood extravaganza with a cast of thousands that I was, for once, looking forward to seeing. Chad timidly knocked on our door and wondered if we could talk.
Teddy and I invited him in and offered a cup of coffee from our forbidden coffeemaker in the bathroom. He sat, all legs and arms and bouncing feet, looking as if he might spring jump to the ceiling at any moment.
Teddy and I looked at each other and Teddy said, “So, Chad, how's it hanging?”
"Low and to the left," was his too-quick reply, and he brushed his long fingers along his trousers and looked down, turning bright red. (I love strawberry blonds!)
Teddy let out a single "Hah!" before choking on his coffee and I laughed and said to Chad, "Pay no attention to the Neanderthal in the other chair," while handing Teddy a tissue to wipe the spilled coffee.
"So, umm, Chad, what brings you to these hallowed rooms," I asked, curious about his motives for reconnecting after three years. "Classes going all right?”
"Yeah, thanks, Mike for your help that first year. Hartner would have buried me in chemistry without you," he said. "I've been on Dean's List for the past three years and it looks like Harvard will make an early decision in my favor."
I was impressed. For a geeky sort of kid, Chad had done OK.
"But you seem to have something you want to say," Teddy egged on. "Anything special?"
Chad was silent, looked down at this sneakers, then at me, then Teddy, then back to his feet which were bouncing up and down rapidly.
"Um, well, do you guys swim in the lake a lot?" he offered. "I mean, I like to swim too and I thought I saw you and few other guys swimming the other night and wondered if you like, y'know, wanted to go the Y in town and, um, y'know, swim with me every week?"
Teddy and I glanced at each other: so someone else had seen us and the circle jerk!
"Sure, Chad, that would be fun if we can find the time," Teddy said. "How do you get there? I mean, we can't have cars and cabs would cost a fortune."
"Dr. Trumbull takes me every Wednesday and Saturday night," Chad said. "He was a champion swimmer at Yale and he thinks it's stupid that St. P's doesn't have a swimming program, and he knows I used to swim before I came here, so we sort of struck a deal and go swimming together every week."
Trumbull was a young, attractive, witty, fun master very unlike the old farts who usually taught English. I'd had him for a Renaissance survey last year and he made it sound so alive and real, not merely a bunch of dead poets moaning about loves lost. Plus he was hot.
"Who else goes?" Teddy asked.
"Just me and Trumbull," Chad said. "It's sort of our secret `cause Trumbull thinks the headmaster wouldn't approve or something," he paused, turned a light red, awkwardly adding, "you know, because of Trustees' ironclad opposition to building a pool."
"Sweet," Teddy said. "Do we have to join the Y to go?"
"Not sure," Chad answered. "Trumbull takes me as a guest so I never considered it. Plus it has a steam room and sauna and Trumbull and I like to talk while we soak up the heat after swimming."
This was getting interesting, I thought, and Teddy obviously agreed. Back then, YMCAs were for men only and swimming was naked and the steam room, sauna and showers were obviously naked, so Trumbull must be getting an eyeful -- or the other way around and Chad was enjoying the view every Wednesday and Saturday.
"Sometimes we go out to eat afterwards and sometimes we go back to his rooms and listen to music or something..." Chad trailed off.
This was definitely getting interesting.
"More coffee?" Teddy asked. "And maybe a little something to spice it up?" he said, wriggling his eyebrows and pointing toward the closet. Teddy had liberated more than one bottle of brandy from his father's cache during the past two years and we sometimes celebrated with a little nightcap, especially after some thunderous sex on weekends.
"Um, sure," Chad said, looking a little too eager. "It might relax me. Kinda wound up right now," he said, his legs bouncing up and down.
"Right," Teddy said, pouring a good shot of brandy into the warm coffee. "We have plenty, so don't be shy."
Teddy topped off our cups, too, and sat down, waiting for Chad to continue.
Just then, Harry knocked once and barged in, followed by Tyler and Wes.
"Hey, going to the ..." he looked around at Chad "movie?" Then looked from Teddy to me, then to Chad and back to Teddy. "Sorry, didn't know you were entertaining," Harry said, looking at Chad as if he were an intruder. "Hey Chad, how's it hanging?"
Chad blushed and said a squeaky "Hi, didn't mean to intrude," and got up to leave.
"Chad, don't go yet," Teddy said. "Harry, gentlemen, Chad has come to us with a serious concern and we would like to continue our conversation. Shall we say you return tomorrow night? Enjoy the movie."
Realizing they had been politely dismissed, Harry and the boys backed out and quietly closed the door.
"So, where were we, Chad," Teddy asked, as if the interruption hadn't happened.
Chad responded by chugging half of his brandied coffee and was quiet for a few moments.
We talked for a while about classes, other classmates, what we'd done over the summer -- Chad had gone trout fishing in Montana with his father and brothers -- and I told him the basics about my father's death.
The conversation wound down and I was about to suggest we try to get together some time, when Chad chugged the remains of his coffee and handed his cup to Teddy.
"Could I have another?" he asked. "Light on the coffee and heavy on spice?"
Teddy smiled and gave us all another round of his father's superb stolen brandy.
Chad took a gulp, cleared his throat and took the conversation in a whole different direction.
"So, I guess I saw you guys down at the lake last week and wondered if I could, um, like, maybe join you some time," he whispered, "um, y'know to, uh, go swimming, or, um maybe study together, or umm, whatever." His cover was blown. He'd seen us jerking off and wanted in on the fun. Plus it sounded like he was having some of his own fun with Trumbull on the side.
"Sure," Teddy beamed. "We'd be honored to have you join us for some whatever'. Mikie and I specialize in a lot of whatever,' don't we," he said, nodding and looking at me. I could tell he was half hard; I could see his cock poking straight up under his khakis. He adjusted his rod, Chad following his every move, and stood up.
"How about doing some intense `whatever' right now?"
Teddy openly rubbed his crotch and Chad went beet red. I went instantly full-on hard realizing what was about to happen.
Teddy stood up and placed a large chair in front of the door -- we didn't have locks -- and walked back shedding clothes.
"Mike and I find it easier to study without clothes," Teddy explained. "So you can get comfortable if you want," he added, taking off his pants and underwear, his hard, fat cock bouncing.
I thought Chad would choke. His eyes bugged out and his breath was ragged and short.
I stood and removed my clothes, folding them and placing them on my desk. I turned and Chad said "Shit" as he gazed at my rod.
"C'mon, Chad, you know you want to," Teddy said and walked over to Chad's chair and rubbed his neck. "Let's get you comfortable."
This was the moment: either he would bolt and run -- and the game would be up -- or he would get naked and join us.
This would be the first time we had played with another boy, aside from the spontaneous circle jerk at the lake, and it was new territory for all of us. I wasn't sure I wanted to share Teddy but I definitely wanted to see more of Chad.
He stood up trying to shield the huge bulge in his pants. He was sweaty and shaking but he unbuttoned his shirt and pulled it from his waist then undid his belt and dropped his trousers.
God, he was huge! His bright red cock head stood above his briefs by several inches and a smear of pre-cum shined on his quivering, hairless pale belly.
Teddy bent down and pulled Chad's underpants and socks off, then stepped back to admire the view: a wonderfully slender, lanky, quivering specimen of beautiful manhood with a huge hard dick.
"Damn!" was all Teddy mustered as his hand encircled Chad's huge pole. "I thought you were big, Mikie." There was enormous truth in what he said. My cock had grown -- a lot -- since freshman year. I was longer but not as thick as Teddy. But Chad's pole made both of ours together seem puny.
"Where have you been hiding this for the past three years?" Teddy asked. He waved me closer and I reached out and cupped Chad's significant balls and tweaked his left nipple.
"Fuck," Chad said, his knees shaking so hard we feared he would collapse.
"Perhaps we should take this to a more private area," Teddy said, leading Chad into our room. I followed, feasting on Chad's scrumptious bubble butt and strong runner's legs. This definitely was going to be interesting!
Teddy pulled Chad into our bedroom and backed onto his bed, moving his hand from Chad's arm to his amazing cock; he simply slid it into is mouth and began sucking. I had the backside view and I saw Chad's buns tighten as he let out a loud hiss.
`Awwww, fuck, Teach!" Chad said. His legs were shaking so fast that I stepped behind him, wrapping my arms under his and held him up -- my dripping hard cock planted squarely in his hot ass cheeks. I almost shot a load right then. None of us were going to last long at this rate.
Teddy was jerking his boner as he sucked Chad and I began sliding my prick between Chad's cheeks. Chad was arching his back and standing on his toes and my cock slid under his balls. That was all I needed. I throttled out five ropes of cum under Chad's sack, some of it landing on Teddy's lips and chin as he valiantly tried to deep throat Chad's monster. I felt Chad tighten up, his buns clamped onto my still-pulsing dick and he unloaded.
Teddy gagged and pulled off; his face was immediately covered in ropes of Chad's cum. Then Teddy pumped one more stroke and spewed cum all over Chad's legs, the second shot flying under Chad's balls to hit my slippery cock.
We were a mess. Completely drained, Teddy pulled us all onto his bed, bodies writhing in cum-soaked slipperiness, and we piled together -- a huge, panting, grunting, exhausted, cum-covered mess.
It was the hottest sex Teddy and I had had in a long time -- and we had some really hot sex. But this was different. This was with another boy, and it was both exhilarating and disconcerting.
We slowly untangled and Chad sat up looking a little nervous.
"Umm, wow, I never expected that," he chirped. "That was intense." He reached down between his legs and smeared our commingled cum through his pubic hair then brought his hand to his nose and took a deep breath. The combined scent was intoxicating for all of us, but it was a sticky, gooey mess.
I extricated myself from the tangle of sweaty limbs and walked to the bathroom, my still-half-hard cock swaying from side to side. My balls actually ached and I wondered if I had broken something. I grabbed two wash cloths, soaked them in hot water from the tap, and returned with a hand towel to find Chad and Teddy crushing their crotches together and kissing. I stopped dead in my tracks and watched, fascinated and instantly jealous.
I knew I had a choice: I could protest or I could join them. I chose the latter, going down on my knees and gently mopping the cum from their legs and crotches. They pulled apart to allow me access and I gently cleansed their balls and cocks and ass cracks and legs, then dried them and kissed their various parts. I was hard again performing these ablutions and their cocks sprang to life as well. Ah, youth!
I took Teddy into my mouth first, sucking him to complete hardness then licked my way across his crotch to Chad's. I licked Chad's balls and held each one in my mouth, then licked all the way to the tip and put his head in my mouth and licked the underside with my tongue.
I was rewarded with a big gob of almost-fresh cum and even fresher pre-cum. He rolled away from Teddy and I tried to take his whole cock into my mouth. He was huge. I could only get about halfway down before gagging, so I concentrated on the upper half, paying special attention to the underside of his tender cock head. His legs began shaking as Teddy rolled toward him and licked his right nipple. Chad groaned and he hunched up unto my mouth.
I was lost in a pure-sex haze, stroking my own cock which had shot a huge load only minutes before. But I was ready again -- and I wanted more this time.
Reaching under Teddy's bed, I found the jar of Vaseline we used and I quickly dipped my fingers in, rubbing it into my ass crack, trying to push some inside with my fingers.
Chad was hunching up into my mouth and I knew he wouldn't last long.
I pulled off his cock with loud pop; he groaned in disappointment. Before he knew what was happening, I was astride his hips and my ass was heading right for his cock. Chad looked confused, then shocked, then amazed and he grinned and closed his eyes when he realized what was about to happen.
Teddy knew exactly what to do. Sliding his hand between our merging crotches, he held Chad's dick upright with one hand and guided my ass cheek with the other, aiming for my hole. I made contact, but I wasn't quite ready to accommodate such a huge piece. His cock was too big.
Teddy whispered, "Wait," and he reached down and scooped up more Vaseline and began rubbing my hole and sliding his fingers in to stretch me. He knew this was going to be a challenge.
My ass lips were used to Teddy's ministrations, so I relaxed quickly. When he could slide three fingers inside, he said to us, "OK, but go real slow."
Returning to his position beside us, he put his face right up to our hips and guided Chad into my hole.
To say it was a challenge is an understatement. The head alone was bigger than Teddy's cock at the base and I really had to flex and push out to accept the head and the first inch. My rectum screamed in pain; it was almost like the first time with Teddy. I held Chad still by grabbing his hips and I said to Teddy, "Just keep it steady."
When the spasms eased, I sat straight up and, with Teddy holding Chad's prong, I slowly slid down; Teddy let go but I got stuck halfway. It was like having a baseball bat up my ass. Chad groaned and pushed up slightly and he hit that spot inside that always drove me crazy. My whole body was electrified by the sensation and my ass opened entirely and I sat down hard, feeling his balls on my ass and his pubes under mine.
We both moaned and held perfectly still, knowing that any movement would send us over the edge. I looked down at Chad's beatific face, his eyes half-rolled back, his face and upper torso covered in a sheen of tiny beads of sweat. His mouth was formed into a perfect "O" and a drizzle of saliva ran from the corners.
I glanced over at Teddy and he was transfixed, squinting at our joined hips, amazed that Chad's giant dick had gone all the way in.
He looked up at me, his eyes ablaze and his grin lit up the room. "Sweet!" he whispered. "God, Mikie, THAT is SO hot."
He scrambled onto his knees, jerking his own cock, and tried to suck my pulsing dick, but I batted him away and said, "No. Too close. Stand up."
On shaky legs, with the bed springs groaning under the changing weight of three bodies, he stood next to us. I grabbed his cock and sucked him all the way to the root, holding him there and licking the underside.
"Fuck," Teddy said, and he began a slow rocking motion back and forth.
Chad came out of his stupor and began thrusting up into me, filling me even more, then pulling back and leaving a vacuum before pushing in again. My cock was throbbing wildly and pre-cum was steaming down into my crotch.
We picked up speed and raced toward a massive three-way orgasm of thrashing bodies and huffing breath.
We collapsed, Chad's dick still buried deep in my ass. Even though he went quite soft after the second time, he was still huge and it started to hurt. I feared I'd never walk again.
I slowly pulled off. It felt like he was taking the inside lining of my guts, and when the head head popped out I yelped in pain. I felt so entirely empty.
A gush of cum and ass juices flowed from my battered hole and I leapt off the bed, grabbing the cold, cummy wash cloths, and ran to the bathroom trying to staunch the cum with every step. It was not a pleasant time on the pot and afterward I felt even more empty and spent.
Chad and Teddy were splayed on his bed, dazed and hardly moving. I grabbed the towel from the floor and wiped up some of the mess and crawled onto the bed with them. We fell asleep, totally exhausted from our dual orgasms.
Chad stirred first and tried to climb out of bed. "Gotta pee. Bad," he said, and walked quickly to the bathroom where we could hear a fountain hitting the water.
Teddy stirred and pulled a sheet over him and rolled toward the wall. I was pretty sure he was out for the night.
I sat up and rubbed my eyes, shook my head to clear my brain, then reached tentatively to my ass to see if my guts were hanging out.
Chad tiptoed back into the room and began gathering and putting on his scattered clothes, avoiding my gaze. Even soft, his cock and balls hung low on his legs and his perfect butt was still tantalizing. No, I thought, don't even go there tonight.
I stood up and helped him locate an errant sock and sheepishly handed it to him as he jumped on one foot to pull on the other. He looked at me quickly then away, blushing.
"Are you OK, Chad?" I asked.
He nodded and said, "Yeah. OK. Just a little confused and tired. Talk tomorrow?"
"Sure," I said. "Tomorrow."
I pulled the chair away from the door and and he stuck his head out, looked up and down the hall, and walked quickly away. I clicked the door shut and straightened up the room, making sure any evidence of brandy or sex was safely hidden. I turned out the light, took a piss, brushed my teeth, and crawled into bed with Teddy, spooning against his naked back, my spent cock crushed against his ass. I was instantly asleep.