The Matchmaker - 6. Chapter 6 - My Girlfriend

Sarah has a new boyfriend. The news came roaring across the school. And it's the small, insecure dude who looks like a six grader. All less than a week after she broke up with the school sports superstar.

I can't escape hearing rumours about us.

She only did it to make James Mitt mad!

She did it out of pity. He doesn't deserve it.

What is he hoping to do with his 5-cm dicklet?

I give them two weeks if he's lucky!

And so on, and so on.

Meanwhile, away from the commotion, Sarah and I are cherishing our blooming relationship. At first, it's kind of awkward but I get to hold her hands when I walk her home from school. We draw many eyes from people of all genders and ages. In the school and on the streets. I couldn’t care less. I'm proud and beaming. I’m dating one of the prettiest girls in town.

We go on our first date on Friday, only four days after Sarah agrees to give us a chance. I'm not wasting a single second. We talk a lot and I give her as much attention as I can. I have a good memory, so I bring up stuff she told me ages ago. She loves it when I listen to her. I don't talk much about myself. I try to focus on our common interests and my plans for the future.

Whenever we say goodbye, we go for a hug. I touch her waist and hips but don't want to rush capturing more bases yet. Sarah is not shallow and neither am I.

But I am horny. Horny as fuck.

I brought her home two times over the first two weeks. Just for a while, though but she met my parents and they took a liking to each other. When Sarah was helping my mom fix the tea for us in the kitchen, my dad placed his hand on my arm and looked at me with pride. We exchanged smiles and he gave me a soft pat on the back.

One evening, I'm watching TV with dad. My sister and mom are at my grandparents'. There is a commercial break and dad mutes the TV.

"You and Sarah," he says, "it's looking serious."

"Yeah," I say, "I told you I’ve had a huge crush on her. And she's smart and a great friend. We get along so well, dad."

"Good for you, sonny boy. You look great together."

"Thanks, dad."

"So, did you…” dad clears his throat, “you know?"

"No, not yet. I don't want to rush it. But I hope it happens soon. I almost cum in my pants whenever we hug."

Dad laughs.

"Then how long do you hope to last when you actually do it?"

My eyes open wide as I realise this.

"Do you think I will cum too fast?" I ask.

"Prematurely? Don't wanna lie to you, boy. It can happen. But she’s a smart girl. She won’t give you hard times even if it does."

"Thanks, dad. I'm not even sure she wants to do that in the first place."

"Oh, she does,” he says and makes a pause. “Listen Kevin, your mom and your sister will be away next weekend. It will be only the two of us. If you and Sarah go to the movies and can't think of a place to go next, I won't mind if you land here."

"Do you mean it?" I look at him in shock and feel my dick getting hard.

"Just don't tell your mother," he winks.

I jump on dad and hug him, accidentally poking him with my boner through my briefs.

"Hey sport, watch it. You'll poke my eye out."

"Sorry dad," I say and back off a little. I see there is a wet spot on my tented briefs and I shyly cover it with my hand.

"Don't sweat it, son. It only means everything is working fine down there."

"Yeah, I guess."

We go back to watching the movie and I discreetly touch myself through the fabric. It only makes things worse and before the movie ends, I excuse myself. Dad smiles and shakes his head as I run up the stairs and shut the door to my room.

***

I'm euphoric but not for long. Sarah gladly accepts when I suggest we could go see a movie next Saturday. But when I mention going back to my place and having some sweet time together, she politely rejects.

"Sorry Kevin, I know what you mean and I want to get close with you, too. I just don't feel ready yet."

"Uhm, sure, no problem. I don't wanna push you, babe. I love you," I say, trying to hide my disappointment.

"I love you too, Kev. It will be worth the wait, I promise," she says and kisses me on the lips. Some heads on the school corridor turn our way and I hear whispers. I don't care. I return the kiss and we make out softly for a while.

My heart agrees. No point in pushing it. It will be well worth it in the end, especially if I want us to last more than a few months.

But my dick on my shoulder begs to differ. If I wait for too long, she might lose interest. And I will have to live my life knowing I wasted my shot at having sex with this girl, worshipped more or less secretly by every other boy in school.

So in the end it's my dick and not my heart that dials Torry's number.

***

"Don't you think it's a lot to ask for?" Torry says.

"Get to the point, Torry, can you do it or not?" I insist.

"Oh, I can. But it's gonna cost you."

My heart sinks when he names the price. I was hoping it wouldn't be that.

"That's my final offer, Kev. Take it or leave it."

"I'll come by tomorrow and we'll talk," I say and hang up.

I'm not sure if I have any cards to play against Torry. I have less than a day to come up with something.

***

I don't come up with anything, though. The best I can do is to put faith in my charm and my powers of persuasion.

The worst part is that I know I will let Torry fuck me if he makes it a dealbreaker. I can only hope he doesn't.

"Hey Dex," I say when I enter the brothers' room. It's become my habit to ignore Torry.

"Hi Kev," Dexter turns away from his game and gives me a smile that makes me blush. His Fortnite character gets killed while he does that but it doesn't seem to bother him. Damn, he's really happy to see me. And fuck, somehow I'm happy to see him, too.

But then Torry brings me down to earth.

"Kev, before you say anything, it's not negotiable this time."

"It is," I hold my ground. "You can't fuck me. I want Dexter to do it."

"Not this time, Kev," Torry says. "I want something for myself. This is the last thing you'll ever have to do, I swear."

"Not worth it. Sarah and I are an item now. Sooner or later, she'll do it with me anyway. This is as much as I can pay to make it happen this weekend."

"You're afraid of having my big dick up your ass, aren't you?"

"I’m not afraid. I'm engrossed by it. You're ugly and gross, Torry. You were my friend but now you're filthy and despicable. I regret ever knowing you."

I regret my words instantly. I did mean every one of them but they're not likely to increase my chances.

But then Torry loses his ground. He seems hurt. I’m not used to hurting people, even those that I hate.

"Okay," he says, "but I want to watch," Torry says without looking up and my heart starts beating faster.

"Okay, you can," I say, surprised by this unlikely victory and more sorry for him than I’d like to be. Torry could just say ‘no way dude’ and I would do whatever he wanted.

We both look at Dexter who's been silently watching our exchange.

I come close to him and reach out to take his hand. But he doesn't make a move.

"Dex?" I say.

"No," the boy shakes his head.

"You don't want it?" I ask with surprise.

"No, Kevin. I won't have sex with you," he says, not looking at me.

"Why?" I can't believe I'm disappointed that some guy won't fuck me. I probably should’ve asked him first.

Dexter gathers enough courage to look me in the eyes. His voice is shaking.

"I like you, Kev. I have feelings for you. But I know why you're doing it. I don't judge you but I think about you a lot. It would break my heart to have sex with you just so you can have sex with your girlfriend."

I take a few deep breaths. Suddenly I feel no better than Torry. But I already made my decision.

"I'm sorry Dex. I didn't think about it this way. I didn't want you to feel bad."

"Hey, you have a girlfriend," Dexter smiles softly but still looks a bit hurt, "I would do the same for someone I like. Anyway, call me when you're done."

I watch Dexter leave his chair and then the room.

It makes me nervous. I've never been alone with Torry in his room.

"So?" Torry asks.

"Let's get done with it," I say, still aghast, and start undressing.

I'm ashamed of my nudity and my less-than-impressive dick but I want to be out of here asap. I toss away my underwear and sit naked on the bed.

Then I watch Torry undress. He's always been a little sluggish and he takes his time.

He takes off his t-shirt. His belly is a little distended and most of all, hairy, just as the rest of his body.

Then he takes down his shorts. His legs are a jungle of dark, thick hair that seems to never end. Somehow, this guy is only three months older than me.

And then he takes down his boxer shorts and I see his dick for the first time. I assumed it must be big but it is bigger. It's still softish but it hangs low beneath his scrotum. It's dark. It's hairy. It's fat. It's long.

And it's curved.

Yeah, it's fucking curved. I think that's what's most scary about it. Most dicks are curved a little, but Torry’s is hanging to the left at about 45 degrees. It's disturbing just to look at it.

I instinctively retreat on the bed when he gets closer.

Sex with Sarah will be nothing but epic, I tell myself.

"Relax, Kev," he says as I watch his dick getting hard. "I know you think I'm disgusting but I'm still your friend. I will try to make it a nice ride for you."

Fuck, that's nowhere close to what I would call my idea of a nice ride. Torry's dick is now fully hard. Intimidatingly hard. Threateningly hard. Disgustingly hard! And curved. Did I mention it was curved? It is! And it’s even more apparent now that he’s hard. How is he going to…

Torry catches me off guard when he climbs on the bed, takes my hips and repositions me. I can't move. If I'd have to compare this feeling, it's so far much like a dentist appointment. I lie there, open and vulnerable. I know it will hurt but I need it to happen. The drill is just outside of my field of view but I know it’s getting closer.

Torry takes my knees and pushes my legs back, revealing my virgin hole.

"Keep them like that," he says. Fuck. That's what a fucking dentist would say. I grab my ankles and wait for the pain and the humiliation to come.

I tilt my head up. It's scary and hypnotising to watch Torry's dick swing left and right as he takes his place between my legs. Is that what I'm ready to do to get laid? Fuck.

Out of nowhere, he's got a bottle of lube in his hand and proceeds to generously pour it straight on his dick like on a hot dog sausage. It's torture to watch.

Then he squirts some more and I feel his finger touch my butthole. The fluid is cold and greasy. He massages my anus for a little and I hate to admit it feels nice. At least until he pushes his finger into my hole. It hurts. And it's scary. It feels cold but it also feels like it's burning.

The next few minutes are blurry. Torry slowly prepares me for his dick with his finger. When he pushes the second finger inside, I clench my teeth.

"How do you feel down there? He asks.

"Weird… just do it already."

"Dude, it would kill you if I didn't stretch you out a little first."

"Okay, but I feel stretched out enough now."

My childhood friend is stretching my asshole with his fingers. And soon, my childhood friend will bury his dick in my ass. In exchange for his magical powers. Fuck.

My contemplation is interrupted when Torry removes his fingers and repositions himself to aim his dick at my butt. He clumsily places a pillow underneath my butt and I'm almost ready to abort. But I can't.

Next thing I know, I feel his fat cock press against my sphincter. I close my eyes shut and I grit my teeth. I'm scared.

“Ouch!” I yell as my defences fall.

He pops it inside easier than I thought he would. It feels like reverse shitting. Unnatural, yet exciting. Painful but irresistible.

I feel helpless and vulnerable as he pushes his dick inside me little by little. Torry clearly has some experience. He's persistent but gentle enough to make it bearable for me. I collapse on the bed and can't move a single muscle. I've no power left to fight.

My eyes are wide open and I watch the ceiling, focusing on the feeling of Torry impaling me deeper and deeper.

It hurts. But before long, he's fully inside me.

"It's all the way in," Torry says. "Do you need a break?"

"No," I lie. But I want it to end soon more than I need a break. "Just fuck me already."

"I didn't think you would be so eager," he smiles and partially retracts his fat penis. Then he rams back and I squeal.

"You sure you don't need a break?"

"Stop asking, just do it," I manage.

"Good boy. Take it like a man."

I should've probably been more careful motivating him. He goes from slowly penetrating my hole to pounding me with long, slow thrusts. I start seeing stars. I can't move a finger. The only thing I can feel or think about is his dick impregnating my ass.

Minutes pass and just when I think he can't go any harder, he starts rabbit-fucking me like there's no tomorrow.

I moan with his every push. I can't help it. I know anyone who happens to be outside the door will hear it but I can't help it at all.

"Say you like it, bitch," I hear Torry's voice.

"I… I…"

"Say you like it!" He commands.

"Torry… Fuck..."

"Your wish is my command," he says and somehow he manages to fuck me even harder.

I start moaning uncontrollably. I know I’m too loud but I can’t help it. Then, I feel Torry’s hand on my mouth, gagging me. I feel even more helpless but at least I’m happy he’s muffled my moaning.

It lasts forever. Torry speeds up, then slows down. Then he calls me his cunt and speeds up again. I barely hold to reality. His dick up my asshole becomes the new normal. This is my life from now on. Nothing else matters. I only exist to provide a tight and warm tunnel for Torry’s dick to fuck.

When he cums, it catches me off guard. I feel numb and sore but when the warmth fills my insides, I know it can't be anything else. Torry grunts and gives me a few last pushes as deep as he can get. Then he collapses on me and I feel like a bear decided to take a nap on me. And his dick is still inside me.

A few moments pass.

“That's enough, Torry," I say, when I catch my breath, "get up," I pat him on his shoulder.

Reluctantly he removes his member and lies next to me.

I can't move. I'm fucking sore. Humiliated.

Then, a few minutes later I hear Torry snore. I sit up and risk taking a glance at his dick. It's red and glistering but otherwise clean. No brown traces. I feel some relief.

I silently stand up and just as I do that, the door open and Dexter peeks inside.

He looks at me and he seems disappointed. He backs up and closes the door.

I dress up carefully not to wake Torry and go home. I immediately feel the need to change my underwear and shower for two hours.

***

The next day, Sarah calls me. She asks if my invitation is still valid. She says that she wants me. And I say that I love her and I want to love her body. I masturbate five or six times until my dick is sore.

But it’s not the only part of my body that is sore. My ass hurts. I’m aware of the fact that I walk funny. I try to conceal it but my dad is too perceptive.

“You alright there, son? You’re looking sore today,” he says, catching me off guard.

It’s funny that you say it, dad. See, Torry fucked me senseless yesterday. It was my first time so I’ll need a day or two to shake it off.

“I took a huge crap this morning,” I say instead. Bravo, Kevin, a wonderful save.

“Everyone does sometimes,” dad laughs and pats me on the back. “At least it was something coming out and not in!” he says and bursts with laughter.

I freeze. If only he knew it was both in and out! When he notices I’m all red and distressed, he contains himself.

“Sorry boy,” he says wiping a tear, “forgive me this dad joke, it was terrible.”

“I’ll go to my room,” I say and turn my back.

For the rest of the day, I only leave the room to eat and go to the toilet. But that was the final sacrifice. Starting this weekend, I will only be doing that with Sarah. In a few years, I’ll go back to this weird gay moment in my life and laugh.