Loopholes
88. Loopholes
🤍🖤💜 Jacob 💜🖤🤍
I would have fallen asleep if Natalie would let me.
“Does blow job count as sex?” She asks.
She has been trying to find loopholes in Ira’s order for the last hour. I am tired and trying to sleep.
“uhmm I think the word is - Oral Sex!” I grumble, laying on my stomach while Natalie lies on my back.
“Damn!” she says, and I cannot help but chuckle.
“Can we please sleep now?” I ask her, yawning.
“Such a boring boyfriend you are!” she says.
“Yeah??” I mumble.
“I wish I could have found someone better…”
I turn to throw her off my back, then press her under me. She looks amused.
I pin her wrists above her head and say, “I guess I should fuck your pretty mouth just to make a better use of it. It talks too much…”
Looks like my hesitation is gone.
“Why don’t you shut me up now…” she whispers.
It’s hard.
Being around her is hard.
She doesn’t miss a single chance to tease me. I literally have blue balls right now. She stroked and left me in the middle so many times.
She unhooks her wrists from me and rolls my boxers down with her delicate fingers. My dick gets harder again under the constant torture she has been giving me.
“If you tease and leave me now, I will literally shag your mouth!”
I warn her. She grins and ushers me towards her mouth then licks my balls. Sensation is so unique I pull away and chuckle in embarrassment.
“I think I need to wear a condom. I don’t wanna spill on her bed.”
“But I… I want you to come in my mouth…” she says with hesitation. "You think you could do that?”
I go painfully hard within seconds just thinking about it. I stuff my dick inside her mouth without answering her. Her mouth feels wet and warm. There is an edge to do her like this. As if it’s more intimate than fucking her cunt. She opens her mouth wide while covering her teeth. I pump into her, trying not to go too deep or choke her. My dick sliding in and out, with her plum lips wrapped around tight. It feels too much to handle but I keep going. She gags a few times and I try to pull away. She holds my hips in place, encouraging me to keep going. I feel a strange thrill and pump in her mouth faster.
Suddenly I realize face is smeared with tears, and she is breathless.
Way too much.
I pull out and ask her, “Are you ok?”
“Yeah… Why… did you stop?” She says, trying to catch her breath.
She is breathing too hard. “Why didn’t you tap me to stop?” I ask.
“I… I didn’t want you to stop.” She says, still trying to take longer breaths.
uhmmm… Is this normal? I don’t have any experience, but I don’t think so. I look at her, speechless.
She realizes my turmoil and blushes.
“God.. This is embarrassing…” she says, covering her face.
I frown and pull her hands away. “Hey.. Talk to me…”
She sits up, not meeting my eyes and says, “I…. I like that.. this breathless thing… and choking too…”
Okay…
“You mean, like a literal choke or the act,” I ask genuinely curious.
“Like the literal thing…” she meets my eyes in hesitation then looks away.
“Hey.“ I lift her chin with my finger. “I just panicked, thinking I went too far..”
She shakes her head. “No.. I was fine.. I guess I should have told you before…”
She looks at my soft cock and sighs. I cannot help but smile. This make-out session is lost cause, so I ask her, “What do you like about it?”
“There is this strange thrill… The sudden burst of air after being held for too long…. all senses heighten.”
Wow, I thought sex already does that!
She adds after a pause. "Although I haven’t tried choking before. I always liked the idea.“
“We could try it another time.. I want to make sure everything is safe.”
In my one-day-old sex life, that’s an enormous responsibility on my shoulders. I won’t go blind into it.
She blushes, but I feel honored. I cannot help but feel warm thinking she trusts me to try something like that.
…
We take a break. She assures she will tap if it gets too intense for her. Then I finally fuck her mouth just the way she wants. Hard and fast.
My arms are shaking with intensity while I am trying not to smother her face with my weight. I am amazed how she is even managing. When I finally release, I spill a huge load inside her mouth. She swallows and licks my dick intently. When I am about to return the favor, a voice comes from another room.
“Girls, are you awake?”
Oops, It’s Ira’s mom. I hope we were quiet enough!
“I just woke up, Ms. Winona,“ Natalie replies.
“Hun, can you open the door? I need to grab some stuff from the closet. “
I pick up my clothes and tiptoe into the bathroom. Praying she doesn’t check the bathroom.
Natalie opens the door, and she says, “Thank goodness you are awake… Ira doesn’t wake up until it’s 5 minutes to school time… God knows how this girl will manage college.”
Ira’s voice comes from behind. “Seriously mom.. Look at me, I am awake!“
She is probably in room now.
“ohhh you guys didn’t sleep in the same room?” she asks
“ No, Natalie’s kicks in her sleep.. “
Smack!
Ira giggles.
“Why are you taking that out?”
I am not sure what they are talking about.
“Oh.. your brother needs it…”
“Liam… Mom, use his name,“ Ira says.
She chuckles. “He is coming here in sometime. I am going for a bath. Can you hand this to him? “
“ohh… but I am going out now… to drop Natalie. otherwise she will be late for her school,” Ira says. Her voice seems frantic.
“But you ain’t even ready yet.”
“I am going to get ready now. Why don’t you hand it to him yourself?” Ira says and barges into the bathroom.
“ohh ok..” Her mom says and I hear her leaving the room.
I stare at Ira awkwardly. Thank goodness I wore my clothes. She would kill me if she figured what I was doing with Natalie barely five minutes ago.
“I thought Natalie would go with me. Why did you say you will drop her?“ I whisper at her.
“Don’t ask!” she whisper-shouts at me.
Natalie comes inside and says, “Your mom is in for a shower. Time to go out!”
Once the girls change their clothes, we three slip out of the house. As we walk out of the building, Natalie says, “oh Fuck I forgot my phone!”
Ira rolls her eyes and gives her keys. “Go get it. clumsy girl!”
We stand next to each other and she asks me, “You guys talked? “
“yes..” I am wondering if I need to talk more… We apologized though.
“Use better words, Jacob… Things cut way deeper than you can imagine.”
I nod. I am embarrassed by my choice of words too.
“Ira!” a deep voice calls out and Ira goes stiff.
“Oh.. Hey.. Liam. You are early..”
I turn to see a big, bulky guy walking towards us.
Huh!
Looks like Ira does have a big, bulky brother. I am so glad he wasn’t around last night.
“Yeah… Were you planning to avoid me?” He asks.
“Nooo…” Ira scowls.
He throws a glance at me. As if trying to weigh me in.
“Did he stay for the night?“ He asks with a strange edge in his voice.
Now it's my turn to get stiff.
“Yeah.. Don’t tell mom…” Ira says.
I am not sure if I am imagining it or if this dude wants to strangulate me.
Soon Natalie comes out and exclaims, “Liam!!! How are you?”
They talk, and then Natalie introduces me. “Did you meet Jacob? My boyfriend.” She grabs my arm, leaning onto me. I grab her by the waist.
“Oh… “ He says.
Did he think I was Ira’s boyfriend?
Protective much?
We make small talk and when we head out, he asks Ira, “Why are you going with them? Do they need a ride?”
“No, I have my car…“ I say and regret it immediately.
Ira glares at me and says,” I am going to see them off. I will be back in five"
… .
“What was that all about?” I ask Natalie as we head towards home.
“Liam is her ex-boyfriend and soon to be Step Brother…”
“Oh,” That’s all I can say.
That’s messy!
….
We have no choice but to go home to get ready. We leave for school at the usual time, in hopes to attend the whole school day.
The day goes smoothly and pleasant until we get called into the principal’s office.












