It is late spring and the high school baseball season is winding down. I’m the manager of the Boston Tech team. That sounds important, but it isn’t. I carry the baseball bats used in games to the ball field, write up the official scorecard, guard players' valuables. Menial stuff.
At least I have free entry to the locker room and can see the players undress, shower and show off their semi-erect penises. I keep track of who is hung and who isn't, who is circumcised and who isn't. I guess I’m a dickologist. The circumcision rate is about 40 percent. This is the ‘60s. These guys were born when male babies weren’t routinely cut.
After practice one afternoon at Elmont Field in Dorchester, I am walking up Blue Hill Avenue to catch the bus home when I feel someone behind me put his hands over my eyes. "Guess who?" he enthuses.
It is William, the 19-year-old senior I know from several hot encounters in the basement men’s room at school. He graduated last year and I lost touch. I still jerk off to memories of things he let me do to him in that bathroom stall.
William looks as delectable as ever with his handsome face and long dark blond hair flopping over his forehead and ears. In the past year he has become slightly more muscular, but happy to say that he hasn't overdone it. He still has a toned athletic build.
He is wearing tan Levis and fills them gloriously, especially in the crotch and ass.
"So, what are you doing in my neighborhood?" he asks. "I thought you lived in Uphams Corner."
"I was doing my gig with the baseball team. We had practice here. I'm the manager," I say with some embarrassment. It is such a degrading job.
William doesn't say anything disparaging, for which I am grateful. He puts his arm around me and lets out a "fucking fantastic. Great to see you, Pete. It's been a while. My mom's at work till late tonight. Wanna go to my house and smoke cigarettes?”
He is such a lovably goofy athlete, who could resist?
We had smoked a cigarette in our first encounter in the bathroom stall at school, which led to my blowing him.
His offer excites me, and I have no illusions about what he really wants. Off we venture the few blocks to a three-decker house — Dorchester is full of these structures that contain three separate apartments — and up the stairs to the third floor.
William leads me into his bedroom and pulls a pack of Marlboros from a hiding place in his closet. He stretches his 6-foot body onto the bed and lights a cigarette. He takes a few drags and hands me the butt.
"I think it's cool that you smoke. I would never have guessed that.”
I know what he means. I am 5-7, skinny and wear glasses in class. I suppose teenage nerds aren’t supposed to smoke.
William uses one foot and then the other to push off his loafers and sits back with his head propped up on a pillow. I sit on the edge of the bed waiting to be told what to do. He tells me to take off my shoes.
We fill a little ashtray with ashes and he lights another cigarette.
He is wearing a white T-shirt and Levis that are tight, especially in the crotch area, which bulges with promise.
He tells me to relax — he has noticed my nervousness — as he pulls off his T-shirt, revealing a hairy chest and dark blond treasure trail that climbs up to his belly button from his Levis. With his T-shirt off, I can see the elastic band of his BVDs tightey-whiteys rising above his belt.
As we finish the second cigarette he orders me to move closer and straddle his body. He takes my hand and places it on his left nipple. "We didn't have time in the stall to do everything I like, Pete. We have time now. I want you to rub my nipple.”
His hand pushes mine onto his nip. "Squeeze it hard,” he commands. I love it when he orders me around.
I squeeze the nub and he lets out a moan. “That’s hot,” he says. "I rub them when I jerk off, but having you do it feels so much better. Now do my other nipple."
Through his jeans, I can see his dick swelling.
William orders me to unbuckle his belt.
My hands are shaking in anticipation of seeing his beautifully shaped circumcised penis again.
As I undo his belt and the buttons of his jeans, I can see the outline of his mushroom cap flaring out. He raises his pelvis to let me shimmy his Levis down. He is naked except for the working class briefs that hold his jewels.
"You really love my dick, don't you, Pete. I can see it in your eyes.”
I nod a yes.
"You jerk off every night to the fantasy of sucking it. Am I right?”
I nod again.
You love the taste of my cum, don’t you? I bet it tastes really good.”
William’s ego stroking is obnoxious, but I can live with it. He is a paragon of studliness
“I suppose you know why I invited you back here today?
"You want me to suck you off again,” I quickly respond.
“You’re half right," he says, provocatively.
He has thrown me a curveball. What does he mean by half right?
"For sure, I want to see if your cocksucking skills have improved. You mentioned that you practice with a cucumber. Are you still doing that?"
"Yes," I say sheepishly."
"Great. Now pull off my undies.”
William is so hard that his dick looks glued to his stomach -- 7 fat inches with a large cap topping a meaty set of hairy balls.
"Lick my dick."
Damn, I am grateful I ran into him.
I coat it with spit as my hands grab his hips. I had to pull his cock out from his stomach to get my lips around the crown. That’s how hard he is. His mushroom cap tastes as if he has just taken a piss and didn’t shake off the last drops.
William puts his hands behind the back of his head in a classic “Suck Me” pose. I luxuriate in his manliness. I press my nose into his sweaty pelt of dark blond pubic hair and breathe in. His male crotch scent makes me shake with lust.
As I purse my lips on his crown I resolve to give him the best blowjob he’s ever had.
"Your mouth feels a little dry today,” he says, which takes me by surprise. I think I am producing the same amount of saliva as always.
“He orders me to open my mouth, then spits into it. “That’s better,” he says. “Now wet my dick.”
I find this new wrinkle totally hot and hope he spits in my mouth again.
I use his saliva as ordered and make slurping sounds as I caress his dick with my lips and tongue.
William coaches me to go deep -- 4 inches at
first, then, as he tells me to breathe through my nose, I get to 6.”
"You’re becoming a first class cocksucker under my teaching," he brags. “Because I’m a fantastic teacher." His ego makes everything about him.
He forcefully takes the back of my head. "Almost there,” he says. Let's get that last inch down your throat." My gag relax prevented that in our bathroom encounters.
When I feel his pubic hair scratching my face, I know that my practice has paid off.
“That's making me crazy, Pete.”
I pride myself that I can handle all 7 inches.
Suddenly, William puts a damper on my plans to eat his cum.
“Wait, Pete, I almost shot my load, but that's not why you’re here today. Remember, I said getting blown is only half the reason I invited you here.
"I thought you wanted to cum?" I say, disappointed.
"Oh, I'm going to cum, but not down your throat."
I wonder, does he want me to jerk him off? That would be a major letdown. He springs up from his supine position and wraps his arms around me. I find myself being muscled, face down, onto the bed. My face hits the pillow. He unbuttons my shirt and pulls it off, then my white T-shirt.
He orders me to lift my pelvis, unbuckles my belt and pulls off my green corduroy pants. He removes my socks.
I lie on his bed in only my white Hanes briefs. It doesn't take long to figure out what he’s planning. He rips a hole in the back and whacks my ass hard. He has morphed from sweet Willian into rough, take-charge William.
He tears at the cotton until all that is left is the elastic band around my waist. My ass is now fully exposed.
“Relax, Pete, I’m not going to hurt you.”
I have my doubts. I haven’t done this before. Of course, I’m anxious.
He opens the drawer of the nightstand and takes out a jar of Vaseline.
That increases my level of anxiety.
“Wait, William, please. I want to, but I don’t know if I can. Your dick is a monster."
“I know you’re a virgin, Pete. I always wanted to be your first. I checked out your cute little ass all through high school.”
I am completely taken by surprise. I never saw my butt as anything special or noticed William checking it out. I was too busy ogling him.
I am stunned by his compliments. He never gave me any before now.
“Pete, do you have any idea how sexy your ass looks in your corduroy pants? I’ve been wanting to take your cherry for a long time.”
I have to admit the prospect of letting this stud fuck me is tantalizing. And yet, "It's gonna hurt," I tell him.
"At first," he says. "Then it's going to feel so good you’ll thank me a million times over.”
He takes my silence as a sign to proceed.
“Pull yourself up on your knees and raise your butt as high as you can. Bite into the pillow,” he says. "It might help.” The “might” part does nothing to ease my fear.
William unscrews the lid on the jar of Vaseline. A cool moistness envelops my hole as he lathers me and pushes a finger an inch inside.
“I’m surprised how hairy you are back there. I wasn’t expecting that. I love a hairy ass,” he enthuses.
“William, you know I’m Italian,” I say.
"This is going to get you ready for my dick. I know I’m big, but it’s time we got your ass fucked.”
His use of “we” makes me feel more involved in this process, even though I'm not.
He adds a second finger. "We're doing really well," he says.
He pushes his fingers in and out. I haven’t yet decided if I like the feeling that brings. There is some pain, but not as much as I expected. There is also a feeling of fullness I’ve never felt before.
William adds more Vaseline and pushes his fingers deeper inside. To my surprise I already feel looser and the pain is just about gone. I’m surprised how easily his fingers penetrate me.
"I think we're about ready," he says. "Remember to take deep breaths and think of how much you love my dick. You absolutely can't get enough of my dick. Think of that, OK?"
The head of his Vaseline-slicked cock rubs up and down my crack. I feverishly think about how much I adore his dick and how much I want it up my ass. I hope that helps.
I feel his shroom poking at my hole and slowly enter. "Take deep breaths." He repeats.
"We are both going to enjoy this,” he says with his usual enthusiasm. And he’s using the we word again.
He enters an inch or so and it feels uncomfortable, as if there is some barrier stopping it.
"There is a muscle in there,” he says, “But if you relax your hole, it'll open. That will make this easier for both of us."
I concentrate on relaxing and he pushes more of his cock inside. That last insertion really hurts, but he's insistent that the pain will ease up. He pushes a little more and tells me to push out.
He tells me that 5 inches is now inside and Ifeel this sensation that is hard to describe.
“My cock is hitting your prostate gland,” he says. You’ll feel pleasure every time it does that.”
When he pushes the whole 7 inches inside and thrusts in and out, waves of electricity flare through my body down to my toes.
I have surrendered to his alpha power and can’t believe the pleasure I’m feeling.
“Do you want me to fuck you harder?” he asks somewhat rhetorically and grins at me, already knowing the answer.
“William, your dick feels amazing.”
His body sweat drips on my back. He nibbles on my ear and tells me how tight I am -- tighter than any girl he’s ever had.
He shifts into another gear, thrusting hard into me. I push my ass toward him, increasing the penetration. His pubes bang against my butt.
"This was well worth the wait,” he says. “I knew some day
I would nail you. I’m glad it’s today.”
My ass is on fire, but in a good way. William blows his hot breath on the back of my neck. He whispers that he is going to shoot his biggest load ever inside me.
With one final thrust, he shouts out a "fuck" and cums inside me. I feel his cock pulse and spasm about 10 times. I imagine that there is a pint of his cum inside me.
William hugs my back and says that he has never had such a powerful orgasm.
On my side of the pleasure highway, I realize that something has happened to my dick and the blanket is wet underneath me. I came off without being touched. How wonderful is that?
