Gay Boarding School Stories

7,643 results
Orientation
Length
Source
Infinite Scroll

Just One of Those Things Ch. 02

by cforester44 on Sep 14, 2017
Gay Male

Jack It was early Friday evening and I was going out to a little blues club near campus. I usually avoid crowds but I had it on good authority that Julian Monaco would be there. I gave myself a final once over in the mirror and headed out the door to my fifth story walk up. I was on the last flight of stairs when my cell phone rang. I didn't recognize the n...

Home Alone

by Soshameless11 on Dec 24, 2019
Gay Male

"We're boarding now. Call you when we land." With that text from my wife Cindy, my 10 days of bachelorhood officially began. She was off for a girls' trip to the UK, touring castles, drinking tea, wearing fancy hats. All the stuff one does once the kids are out of the house and there's more disposable income about. I'd feigned all the "babe, I'll miss you...

Blow, Blow, Thou Winter Wind

by EMauriceGlass on Nov 26, 2019
Gay Male

As Rob slogged through an icy squall in the dark on the way back to his dorm from the college library, where he'd been finishing his term paper on The Muffled Queer Voices of Colonial America, he took the opportunity to utter some choice words under his breath as well. "It's fucking cold!" A popular turn of phrase, notably among his teammates in JV football,...

Unexpected Ch. 17

by BNDMTL on Sep 25, 2017
Gay Male

I roll over to my side and look at the clock, and it's eight thirty. Shit! I slept in again. I roll to my back, and something is there this time. I move to my side and roll again, and it's Benny blocking my way. Alex is on the other side of him staring at me. I smile and reach over and cup the side of his face wiping his cheek with my thumb. I quietly whisp...

Gullible Guy in Testosterone Trick

by BeamMeUp on Aug 18, 2017
Gay Male

Being the fairly remote tiny country town's schoolboy cycling champion was not enough. I had to get to the big smoke to improve my speed if I was ever to really excel in my chosen sport. I needed some really stiff competition if I wanted to stand out in my last season as a junior. My 18th birthday and senior ranks coming up I was told that if I could find...

DJ Pt. 16

by o2byoung on Feb 13, 2018
Gay Male

Coming it Part 16 DJ and Jamie visit Disney World DJ models his sexy swim trunks Girls are chasing after DJ and Jamie DJ assumes his new position Joe's and Doug's wedding plans are completed DJ Part 16 Thursday night Jamie, DJ and I all got off work at 9:00 PM, and drove back to our house for the night. DJ had told Jamie that Joe was cooking and would...

North Star Ch. 03

by rem1324 on Apr 24, 2018
Gay Male

All characters are 18 years or older. I appreciate your feedback in the comments. Thank you for reading my story. ***** The realization upon awakening that I was not alone in bed brought with it the weight of more than the left leg, arm, and head laying on top of me. This other weight was a force beyond the basic gravity of his mass. It was the paral...

A New Direction

by dennycboy on Sep 14, 2017
Gay Male

He was fit and tight. Infantry, I thought. It was 1955. Miz Connie's was a boarding house. Detroit. Autoworkers, most of us. He came in a cab. From the railway station. "Just this suitcase. Gotta room?" She put him in a room off the foyer. Private. Most of us stay in the what we call the barracks bunks twelve men loud and public. He paid his money. P...

Mikey and the Chickadee Ch. 09

by kidboise on Feb 6, 2018
Gay Male

I settled back into wakeful existence with the fluttering undulation of a dead leaf, or of a sheet of paper, sidestepping erratically in its journey to the floor. Not one to suffer confusion upon waking, I resumed acknowledgment of my location without pause. Mikey lay still in dormancy next to me, chest exposed, swathed stomach-down by the comforter. With hi...

Husband Anon Chance

by Open4Husband on Mar 9, 2020
Gay Male

There I was with a cock in my mouth for the first time ever. I was in a stall at Denver International while my wife was likely at our gate waiting for me so we could board the plane. None of that mattered much to me at that moment. I was given this chance. I was given a chance to live out a fantasy. I was given a chance to earn the approval of the owner of t...