Coming Out: An after-school job leads to a sexual awakening

I wake up in my bed Monday morning with a hard-on … Hello, I’m 17. Of course I have a hard-on despite cumming three times last night. Before getting ready for school, I lie there and jerk off to thoughts of both Grant and Shawn. I shoot imagining them taking turns fucking me. 

I smear my load into the t-shirt I wore in bed and head to the shower. I need to deal with Shawn about the dating situation. I determine that I’ll do that today, confident since everything went well with Grant. 

I know Shawn’s class schedule and head to the hallway by his first class at Cleveland High. Shawn is his normal bouncy self when I spot him. I suggest lunch at Darlene’s, the hamburger joint across the street from school. He agrees. 

We meet at the front door of the school. It’s a warm late November day, what we would call at the time an Indian summer. It’s 1984. We still talk that way. 

Our school is grumbling about the decorations going up around town for the football championship, unhappy that it involves our crosstown rivals. Cleveland High has no town spirit for the Roosevelt Bison’s undefeated performance. Our quarterback is working the halls urging jocks to go to the game and root for Smithfield. 

Shawn and I order our lunches and take a table. The smell of hamburger frying in grease hovers through the air. They have these big, juicy burgers that any 21st-century cardiologist would abhor. 

As we eat, I tell Shawn that I need to talk about something. I stick to the script I used with Grant. I remind him how both of us are freshly out with ourselves and dating in general. I tell him about Grant and that he and I had a couple experiences before my first date with Shawn and that I just wanted to be honest. 

Shawn’s reaction is the opposite of Grant’s. Shawn is so livid that I must concentrate to understand what he is saying because he is talking fast and with a stronger than normal accent. 

“What the hell, Matt?” Shawn exclaims. “Isn’t he one of the jocks that abused you in the Taco Casa bathroom because Chris said you were his bitch? He mocked me that night, too, if you remember! And the next time you’re with him is because he demands you pay off some sex debt? And then he gets you to be his after-game sex toy in the locker room?”

He continues: “You and I went on real dates! What has he done but use you? Great, I’m so happy that this asshole has realized he is gay. Fuck that! And Thanksgiving? So I say no to dinner so you invite him instead? And how did that go for you? You get your ass kicked by his best friend? That’s a great relationship for you.”

Shawn is building toward a conclusion. 

“You’re right. My program ends in mid-January, and I go back to Sydney. But guess what? You can fuck off right now!” He stands up and dumps his Coke on me and storms out. All the other tables of students are staring aghast at the scene.

I manage to hold it together in front of everyone, but I’m upset and feel overwhelmed and alone. Maybe more alone than than I was before this all started since I have no one to talk to that fully understands what I’m going through. The one sympathetic person is Sebastian, but he’s straight. As much as he can try, he can’t comprehend what it’s like to come out and get flooded with everything all at once. I head to the little-used bathroom by the gym, sit in a stall and cry before my next class. 

Sebastian is in that class and sees how red my eyes are. He stops me after the period is over, but I say I don’t want to talk. He takes my arm firmly and tells me that it will be alright. He reminds me we are working together that night and says he hopes I will be able to tell him what’s wrong then. 

It’s 9 p.m., and my shift at Taco Casa is ending. Sebastian is standing at the door to the manager’s office as I punch out. He asks if I want to talk. I sigh and head into the office, the same office where just some two months ago I sucked a dick for the first time and began my adventure into this new reality. 

After listening to my story, Sebastian says that at least I didn’t lose both Grant and Shawn and that honesty was the best option regardless of the outcome. He says I need to understand that there are differences in Grant and Shawn’s personalities and life stories that caused them to react differently. He adds that Shawn may have been caught off guard and I shouldn’t give up on him. 

He switches topics. 

He says his parents are flying to the state capital on Wednesday afternoon and spending the night. The governor is having a dinner for top members of the state bar association, and his dad was invited. Jamie is coming over for the night. He says he is hopeful this leads to their first time having sex. 

He flashes me his flirtatious grin. “As for you… I can’t forget my new best friend. Jamie and I talked about how tough it is for you to find anywhere even to make out. We want you to bring someone over for the night if you want. It can be Shawn or Grant.”

He says we all could hang out. Then, he says he and Jamie would take his bedroom and I could have the guest bedroom. I told him that Grant is on a sex-free regimen for the week because of the upcoming game. Sebastian laughs. “All the more reason to make peace with Shawn,” he says. 

I try to catch Shawn a couple times Tuesday at school. He sees me coming each time and heads a different direction. We were scheduled to work together that night at Taco Casa, but he calls in sick. 

I have all but given up as I head to school Wednesday morning. Shawn is waiting at my locker. 

“I’m sorry, Matt,” he says. “I overreacted. It’s true that I’m not here that much longer. It’s not fair to lock you down. I’ve had so much fun with you and coming out together. I don’t want that to end and particularly not end like this. I still don’t understand why you would want to have anything to do with that jock. Tell him to come to Australia and try rugby. Then, we’ll see how butch he is.”

I’m quivering. “I didn’t mean to hurt you, Shawn. I’ve been feeling awful. I’m sorry, too.”

“Good, you deserve to feel awful,” Shawn says. “Now, how do you plan to make it up to me?”

I tell him about Sebastian and Jamie’s offer. “That sounds great!” he says.

The four of us meet for lunch in the cafeteria and finalize plans. Since it is still unusually warm, Sebastian says he’ll stop at the grocery store and get ingredients to grill hamburgers on the barbecue. When I get home, I tell mom that Sebastian, Shawn and I are working on a class project and that Sebastian suggested we spend the night. She says OK. 

I stop at the mall on my way to pick up Shawn. 

I run into Camelot Records and ask the manager if there are any recent releases of groups or singers from Australia. He flips through some inventory papers and tells me that the closest he can find is a group called Eurogliders. They released an album in May entitled “This Island.” I ask if they have it. Five minutes later, he returns with a tape. “We have one,” he says. “Do you want it?”

I pull up at Shawn’s. He dashes out carrying a gym bag with a change of clothes. He’s in jeans and an ABBA t-shirt with a light windbreaker over it. 

I give him a quick kiss. “I got you something,” I add.

I hand him the tape. “It’s an album from a group called Eurogliders. I asked the manager at Camelot if there were any recent releases from any Australian groups and he found this.”

“Oh my God!” Shawn screams. “I’ve wanted this so bad. I meant to buy it before I left home. I never thought of asking here. That’s so sweet. I promise I won’t make any comments tonight about that Neanderthal you like.” 

I give him a dirty look. He sticks out his tongue and pokes me in the ribs. “I get to make fun of him all I want,” Shawn says. 

Sebastian greets us at the door, giving us both a hug and telling us that he’s glad that we figured things out. Jamie is standing in the kitchen and asks us if we’d like a beer or Coke. Both she and Sebastian are in shorts and t-shirts. 

Shawn knows Sebastian from school and work, but hadn't ever met Jamie. 

We sit out on the back porch drinking beer as Sebastian grills hamburgers. We eat and chat for a while. Jamie suggests we go inside and proposes we play truth or dare. 

She sets the rules. You can’t do two of the same things in a row. Nothing is off limits. An empty beer bottle spin determines who you are asking truth or dare to. Most of the game is stupid questions and dares.

Shawn ends up once with a truth or dare to Sebastian. Sebastian chooses truth, and Shawn asks who has given him the best blowjob ever. “Of all the girls I’ve been with, Jamie gives the best blowjobs,” he replies. I’m not sure if anyone else caught the nuance in his answer but me. 

Sebastian gets Shawn back. One of his spins lands on Shawn, and Shawn chooses dare. Sebastian tells him that he has to make out with Jamie for five minutes. Shawn is squirming uncomfortably as he and Jamie kiss. 

Jamie once spins and get Sebastian and he chooses truth. 

She asks him to tell us about his first time. He says it was his 14th birthday, and he was hanging out that weekend afternoon with a group of friends. He was embarrassed when asked if he had ever kissed anyone and he said no. A 16-year-old girl in the group suggested they make out in a closet, and his friends taunted him into doing it. After a minute of kissing, she began fondling him and then dropped to her knees, pulled his dick out and sucked him off. He loudly shot his load. He said he turned red when they exited the closet because everyone cheered. 

I landed on Shawn once who chose truth. I ask him to describe his most embarrassing hard-on. He says that’s easy — when Chris told him to strip to his underwear and try on different restaurant uniforms as I watched. 

Shawn spun once and got Sebastian who chose dare. Sebastian was ordered to grind his crotch into my face. Yeah, I was totally hard after that one. I got Jamie and asked the biggest cock she ever had — the answer was Sebastian. Sebastian sighed and said, “I’m so over everyone talking about my penis size.” Shawn and I both threw pillows at him in response. 

Sebastian lands on me and I choose dare. I’m required to nuzzle my face between Jamie’s breasts. As I’m doing so, Shawn announces that he thinks I’m hard. Everyone laughs. 

Another spin had Jamie answering a truth from me. I had her describe her favorite sexual position, and she responds “cowgirl.” Sebastian mouths “thank you” to me. 

The most embarrassing moment is created by Jamie. 

She spins, the bottle points toward Shawn, and he chooses dare. She announces that she has never seen an uncut penis and wants to see Shawn’s dick. Shawn’s shyness comes out, and he says he doesn’t want to do it. 

We all harass him until he relents. 

He undoes his pants and pulls them and his underwear slightly down and lifts out his soft cock, the head hidden inside its hood. He’s blushing brightly, but Jamie is having none of that. She says she can’t see it well from where he’s standing and makes him move closer. Shawn is even more mortified when she takes hold, strokes it a couple times and exposes the head. 

“Interesting,” she announces. We all laugh. 

Sebastian says he has had enough of the game. He says he’d like to go to the hot tub with Jamie. He says Shawn and I can join or do our own thing. I want to get in the hot tub, but Shawn complains that he hasn’t brought a swimsuit. 

“I’m not going to wear anything,” Sebastian announces as he undresses in front of everyone.

Shawn’s mouth is wide open as he takes in the sight of Sebastian’s naked, fit, Greek body. Sebastian ignores him and pulls Jamie up off the couch. She strips. As she pulls her blonde hair back in a pony tail, she looks at Shawn and says, "Come on, Shawn. They're human bodies. They are nothing to be embarrassed about."

Jamie is the first nude woman I’ve ever seen so it’s a little disconcerting for me, too. She and Sebastian head to the hot tub. 

It takes some convincing, but Shawn finally agrees to go to the hot tub. We both undress, but he covers his crotch with a hand as we head outside to the deck. The two of them are already heavily involved with each other on the far side of the hot tub as Shawn and I get in. It’s a huge family-size hot tub so we are on separate ends. I begin making out with Shawn. 

Shawn and I are deep into kissing and caressing each other when I hear moaning from the other side of the hot tub. Sebastian is sitting on the deck with his hairy legs spread while Jamie is in the water giving him a blowjob. Sebastian sees me looking and motions his head toward Shawn. 

I tell Shawn that I want to suck him and to sit up on the deck. I place my hands on either side of his thighs and begin a very intense, sloppy blowjob. Yeah, I’m being competitive. Jamie isn’t going to best me in the hot tub blowjob department. I soon have Shawn moaning so loud that Jamie has lifted up her head from Sebastian’s dick to look at us. 

Shawn screams, “I’m cumming!” He takes hold of my head and bucks upward. A large load of milk fills my mouth as he cries out. The last time he came, he says, was with me that weekend.

“Umm, I think you need to give me some tips, Matt,” Jamie says. “Isn’t that ending the evening early for you?” 

I laugh. “We can talk later. Ohh. I'm also pretty sure Shawn will be cumming again tonight.” 

“At least one more time,” Shawn emphasizes as he smacks his softening dick into my face.  

Shawn and I say we’re going to move inside. We dry off and are headed into the house when I hear Jamie say to Sebastian before restarting his blowjob, “You were right. Matt does have a cute butt.”

Shawn and I go to the guest room and roll around in the bed exploring each other’s bodies. 

“Sebastian and Jamie are sweet, but their openness freaks me out,” Shawn says. I reply, “Sebastian is such a nice guy. I wouldn’t have made it the last couple months if it weren’t for him. But yeah, is there anyone else like them? It’s kind of refreshing, though, that they have no hangups or preconceptions.”

We’ve rolled to where Shawn is on top of me, and he pins my arms down to the bed. He leans in and begins kissing my mouth and then my ears and neck before returning to my mouth. 

I ask Shawn what he wants to do, and he says he wants me to top him. He tells me he’d love a back massage first, though. “I think you owe me some pampering,” Shawn says. I free one of my hands and mess up his long, shaggy brown hair. “I love pampering you,” I respond. 

He rolls over onto his stomach. I look down at his broad shoulders, his tight bubble butt and largely hairless legs. I straddle his butt and begin kneading his shoulder muscles in my hands. He lets out a long sigh and says how good that feels, 

I work my hands down his back to the top of his ass crack and then go back upwards with my tongue until I reach his neck. I’m lying on top of Shawn and grind my cock up and down the exterior of his butt cheeks. I nibble on his neck. 

Shawn pushes me off him and reminds me that he’s setting the rules. He announces he wants to sit on my face and that I’m going to eat his ass. I say, “Yes, sir.” 

We maneuver and he sits on top of me facing the headboard, his ass cheeks splayed open for my mouth, his nuts resting on my nose and his re-hardening cock planted between my eyes and onto my forehead. He pushes his ass downward. I’m inhaling the musk of his crotch as I begin lapping my tongue over and over his hole. My hands run up and down his calves and thighs, feeling the muscles and the light coating of teenage hair. Shawn is moaning and telling me how much he loves it. 

He eventually tells me to stop and says that he wants to ride me cowgirl style until we both shoot. I lie back on the bed. Shawn applies a lot of lube to my cock and his own hole before he straddles me.

He pushes himself downward, but only take my head into his body. He rides up and down on just my head. I reach in front of myself and fondle his dick and balls. His cockhead is almost entirely exposed and dripping precum. His big nuts are loose and low in their sac. 

He tells me to stop stroking his dick as he sinks halfway down my shaft and starts riding me from that position. We hold eye contact with each other — seeing each other’s desire — as he fucks himself on my dick. 

He stops and sinks down onto my entire shaft, my pubes pressed against his ass cheeks. He leans forward against the headboard and begins fucking himself on me hard and fast. As he whimpers and moans, he tells me to stroke him off.

Shawn feels my body tighten and begins slamming himself harder down onto my dick. I scream out and shoot my load up into his ass. I next feel Shawn’s sphincter squeeze my cock hard and he arches forward, unleashing rope after rope of cum across my face as he cries out and collapses onto me. 

As we lie there panting, applause breaks out from the doorway. Jamie is standing there clad in one of Sebastian’s t-shirts. “I’ve wondered what gay sex looked like. I see you took my suggestion of the cowgirl position. Sebastian didn’t last quite as long as you guys did. He’s peeing. We’re going to have a beer in the living room. Want to join us?” 

“We’ll be right out,” Shawn says. “I need to clean some cum from Matt’s face first.”

He takes care of the cum, and then we lie there for a minute cuddling. He looks at me. 

“I’ve been thinking all night long, Matt,” he says. 

I go with sarcastic. “Does your brain hurt?”

Shawn gently slaps my cheek. “Hey, my GPA is as good as yours! But seriously. This whole situation with you, me and the caveman…”

“You mean Grant,” I reply. 

"OK, yes, Grant,” Shawn says. “We have to be realistic. Saturday is Dec. 1, and I leave in mid-January. You need someone here … something like what Sebastian has with Jamie. Someone who is going to make you happy into the future. And I need to find the same back home.”

He breaks down. “I’m going to be more than 8,000 miles away. I’m going to college in Australia. You’re going to college here. Neither of our families are rich. When would be the next time we see each other after January? If we’re lucky, five or maybe 10 years from now. Maybe 30. Maybe never.”

He wipes his eyes. “Let’s be friends … maybe friends with some benefits until I go home. I’d like that. OK? Can I meet this jerk? I’d like to know who I’m leaving you with. He damn well better make you happy or somehow or another I’m flying back and kicking his ass.”

I silently nod and we hold each other for awhile before we get up, dress and join Sebastian and Jamie in the living room.