u/prvyattrny

Emily’s favorite activity was going through my phone when I wasn’t looking. This was still in flip phone days—I had a RAZR—so there wasn’t much to go through but she couldn’t stop herself from reading every text and scrutinizing every call.

And there was always something. Not something I actually did that was wrong or inappropriate, but something she would maniacally fixate on. Some call or text that she deemed suspicious. A name she hadn’t seen before. Could it be a girl! Then it would begin:

“Who is Jesse!”

“Oh that’s a new guy at work.” Androgynous names were always an issue. I should have just named everyone the male version of their name.

Regardless, Emily was undeterred.

“Ok. Well, Who is ‘Mal’ and why did you talk to her for 30 minutes on March 18?!”

Emily’s least favorite activity was ever admitting doing anything wrong. When it came to apologies, Emily was a champion defensive boxer. Or any Olympic judoka. Every argument was misdirection. Every accusation could be turned into a counter accusation. It was exhausting as she was untethered to the truth…. There was always an overhand right you never saw coming.

And, in case it’s unclear, Emily was also stunningly beautiful. Elegant, poised, a true southern belle in how she held herself.

But, like with many people worshipped for their beauty, Emily was also a deeply insecure and jealous person. Especially when it came to any interaction that I may have had with women. When called out, she rationalized that she had been cheated on before. Supposedly.

I put up with it because (I) I was young and uncertain as to how deeply inappropriate this behavior was and (II) Emily was smoking hot (see discussion above and below).

Emily was tall, thin, pale with huge, brown, searching eyes. Her breasts were small handfuls but she had thick, pink nipples and an absolutely ridiculous ass. Watching her stuff it into a pair of skinny jeans was worth the price of admission.

The first few times these phone arguments happened, I humored her and answered her ridiculous questions. But I quickly learned this was a mistake. You don’t talk to the cops without your lawyer present. Honestly, don’t talk to the cops at all.

Because there was no explanation, no set of circumstances, that would satisfy. She was jealous, suspicious, distrusting and smart. She loved a good argument. Misconstruing my words, poking holes in my story, starting a fight.

Inevitably, it escalated. Rifling through my phone turned to deep dives in my social media, scrutinizing old photographs, cross-questioning timelines. It had no end. Hostilities could only escalate further.

One evening, I went to a concert alone. It was a band she didn’t know well and I loved them so she said she wasn’t interested. I left my phone in her apartment because I didn’t want to risk losing it. We had already had the argument numerous times and she said she was done with the behavior so I figured I was safe.

You shouldn’t trust an alcoholic alone in a liquor store.

When I came back a few hours later, elated and sweaty, she was sitting on the bed, knees pulled up to her chest. The energy in the room was frigid.

She was cold. Didn’t greet me. I immediately knew something was up.

“I went through your phone.” At least she got straight to the point.

I sighed and went silent. Thinking about what to say. We had done this before. I braced myself for the coming storm of accusations, tears and bullshit.

But then, suddenly, an idea formed. Something I hadn’t considered before. Something so obvious and simple, I was immediately kicking myself for not thinking of it months ago.

I didn’t actually need to respond. I didn’t actually need to argue. I didn’t need to defend myself. I could just leave.

So I sighed and started packing up my stuff. Emily watched me silently for a bit before realization dawned.

“Hello! We need to talk about this! What are you doing.”

“No. Actually we don’t need to talk about this. We don’t need to talk about anything. What you did was wrong and you know it. You had promised to stop. I’m going to go home.”

This did not sit right with Emily.

“You can’t leave!” Emily’s suspicion turned quickly to anger.

“I can. And I am.”

“We need to talk about this!”

“We definitely, definitely don’t. We’ve had numerous fights about this. You promised to stop. You did it again. I can’t trust you and I don’t want to try.” While I would normally be angry, I was now strangely calm. Like I had distanced myself from the situation enough to find it entertaining instead of wrought.

“Are you breaking up with me?!”

This I had to consider for a minute.

“No. Not yet anyway. But I don’t want to be here now.”

I turned to go. Emily lunged to stop me, catching up to me and throwing her arms around my neck.

I turned around and she was crying already. Emily was always quick to tears. Normally, I found them moving. Now I just found them irritating and performative.

“Wait.” Emily’s voice had softened.

“What? And stop crying, Jesus.”

“I can’t help crying! I’m sad! We should at least kiss before you go.”

The trap was set. Emily was no good at apologizing with words… but she didn’t at all mind apologizing with sex. She would later admit that she loved make-up sex. The raw emotion of it. The anger and sadness. Trying to fuck away your problems.

I, however, didn’t like make up sex. It was more violent, angry, dominant. Emily would rile me up and then have me take out my anger on her body. I would be holding her down, bottoming out inside her, my teeth sunk into her shoulder and she’d be panting, crying and begging for more.

“I really like how you bit my back….” She would shyly reveal as we lay there in the post-fucking glow. Her little pussy leaking my cum on to the sheets.

I was younger back then. Not yet used to my dominate side. After we were done, I’d be afraid I had hurt her… but in the moment I couldn’t help myself. Reason went out the window and I fucked her in an animalistic rage while I made her tell me she was a slut for my cock.

But I was done. I didn’t want to fight any more. The sex was great but the drama wasn’t worth it.

After you learn to recognize a trap you can avoid it.

“No, Emily. We shouldn’t.”

She was facing me now. Eyes wide, her arms around my neck. Pressing herself against me. Tears running down her cheeks, smearing her makeup. Her voice soft and kittenish. Like a little girl who did something bad.

“Don’t you want to kiss me?”

“It doesn’t matter. I’m leaving.”

“Is there someone else?” Emily had a knack for sucking you back into the conversation.

“No.” She was pressing her tits against my chest. One hand drifting down my neck, over my stomach and hooking around the waistband of my jeans.

“And don’t you think I’m pretty.” Her hand was on my cock now. Rubbing me through the denim. Cupping my bulge.

“It… It doesn’t matter.” My voice caught in my throat. She was good.

It’s one thing to know you can walk away. It’s another thing to actually do it.

“And don’t you want me to suck your cock, baby?” She was reeling me in aggressively now.

“Emily….” She was undoing my belt, pulling down my zipper. Slipping a hand inside.

“Look it’s already hard for me. Are you sure you don’t want me to suck this cock?”

“Em.”

“I just want to taste your cum one last time. You can leave after.” Fuck this girl was good.

Of course I should have pushed her off. Of course I should have left. Of course I didn’t. Turning down a blowjob is a move I had not yet mastered.

Instead I just watched helplessly as she kneeled down, pulled down my underwear and kissed the head of my cock with her perfect pink lips. Instead I just stroked her hair as her little tongue darted out and tasted my precum, licking all over the head of my cock.

“Mmmmm, I knew you wanted to stay.”

Something about her pleased little smirk as she started to take my cock into her mouth really pissed me off. Fuck this girl. This was bullshit. She had fucked up enormously and was trying to get away with it all over again.

Fury rose inside me. Fury at her manipulation. Fury at my weakness. Fury that I had fallen for her stupid little trap again.

I was going to make her pay.

“That’s not sucking cock, Emily,” I said, wrapping my fingers in her hair, “this is.” I grabbed her head tightly and pulled her face down on my crotch, driving my cock into her mouth, over her tongue and toward the back of her throat. I felt it stop there as I bottomed out in her throat, unable to go further. My cockhead pushing up against her tonsils, cutting off her air.

Emily choked and gagged, trying to retch my cock out of her throat. Great globs of spit came out of her mouth. She tapped my leg in a panic.

I pulled out for a second.

“Jesus, baby, you’re so rough. You know I can’t….”

My cock cut off her words, lodging once more in her throat as I felt her gag and convulse.

I did know Emily had a small mouth. I did know she couldn’t deepthroat. I didn’t care.

Emily looked up at me, her face a mess of tears and spit, and tapped my thigh again. I let her breathe.

“Fuck, baby, is this what you want? To fuck my mouth all…”

I wasn’t really interested in what she wanted to say. My cock hit the back of her throat again as I started to face fuck her in earnest. I could feel her esophagus twitching. Pulling all the way back and then thrusting all the way in, mashing the ridged head of my cock against her tight, impassive throat.

The sounds of a violent blowjob filled the studio. Gluck Gluck Gluck. Punctuated by Emily’s involuntary gags and chokes.

I pulled my cock out of her mouth and let her go. Emily fell to the floor. I stood over her while she caught her breath. Panting and wheezing. Her thick saliva made long strings as it dripped off my cock and on to the floor.

“Oh god baby, you’re doing it so rough, I don’t know if I can take it.”

“It might surprise you to know that I don’t care.”

I grabbed her by the hair, lifted her up, picked her up by her crotch and body slammed her on the bed. She was unbuttoning her jeans and I was ripping them off of her legs. I climbed on the bed in front of her, shoved her legs apart and pushed her panties to the side.

Her pussy was absolutely glistening. Her panties were soaked. She was red with desire.

I was inside of her in one thrust. My hips met her, my balls rested on her ass.

“Oh fuck baby, it’s so thick. Slow down!”

I ignored her.

I enjoyed the feeling of her pussy for a few seconds. The hot, wet envelope around my cock. The familiar feeling. And then I started to brutally fuck this girl.

I wrapped a hand around her neck, pushed her thighs to her chest, bit down on her tit right through her shirt and power-fucked her with violence and intention.

“Oh fuck, oh fuck, oh fuck, oh fuck… can I touch myself?”

Emily wanted permission to play with her clit.

“No. You dumb slut, you can’t.”

“Oh pleaaaaaaase! Please baby. Please.” The room was filled with her cries, my grunts and the sound of my balls crashing against her ass.

But this wasn’t about her pleasure. It wasn’t even about my pleasure. It was punishment, pure and simple. Punishment for snooping. Punishment for trying to seduce me. Punishment for her inability to apologize for the simplest things.

I stopped fucking her and slowly pulled out my cock.

“What, what the fuck, why are you stopping?! I’m so close.”

“Shut up.” I watched my cock as I pulled out of her. It was coated in her thick juices. That would have to be enough lube.

I took the base of my cock in my hand, squeezed and slowly lowered the head until it was lined up with her ass.

“Wait. No. Are you serious. We’ve never….”

It’s true. We hadn’t done that yet. But I had tried fingers and she had liked it. This was happening. Now.

“Wait, wait, slow, wait, wait, mmmmffmmffmf.” I clamped a hand over Emily’s mouth. I felt her tongue dart out and lick my palm. I switch to two fingers in her mouth while I continued to press into her ass. She sucked my fingers hungrily.

I was increasing the pressure. Backing off and then pushing forward. I felt her start to give. And then, just like that, the head of my cock popped in.

Emily screamed. “Oh god, oh god, of god…. It’s in my ass! Wait. Go slow. Please!”

I gave her a break. I stayed there for a few moments, just enjoying the new sensation. The tight ring of muscle of her ass squeezing the head of cock.

“Oh god, ok. Keeping going.”

And so I did. Slowly, inch by inch, as I felt her relax. Right there and then I took Emily’s anal virginity as the length of my cock slid into her ass.

Pushing forward until I was buried, down to the balls. I felt the tight ring of muscle gripping the base of my cock as she struggled against the thickness. Maybe she’d finally learn to apologize.

“Now you can touch yourself.”

Emily’s fingers flew to her clit. She was rubbing it like a bitch in heat. Desperate, wanton, vulnerable. My cock in her ass and her fingers erratically rubbing her clit.

“Fuck. Fuck. Don’t move. I want to cum.”

“Did I say you can cum?”

“No.”

“So beg. Beg for it like a good girl.”

“Please, please, please can I cum.”

“Where’s my cock?”

“What?”

“Tell me where my cock is.”

“Oh god. It’s all the way in my ass.”

“And do you like it?”

“Ughhhhh.”

“Tell me. Do you like my cock in your ass.”

“Fuck, yes. Yes I do.”

“Good girl. I’m so glad you can admit that you little whore. And is it the first?”

“Yes. Oh god. It’s the first cock in my ass.”

“And you like it?”

“Yes, I love the feeling of your cock in my ass.”

“Good. See that wasn’t so hard. Now you can cum.”

“Oh thank you, thank you, thank you, baby.”

It didn’t take Emily long. I stayed still while she played with herself and then l felt her tense and twitch. Her whole body convulsing. Every muscle firing. Her tight ass squeezing my cock. Her nipples hardening. Back arching as Emily came while impaled on my thick, hard cock.

It was amazing to watch. Her pussy empty. Ass full. Mouth open in a silent scream as she grimaced, twisted and came.

When her breathing finally slowed, I put a hand on her jaw and tilted her face toward mine. I looked deep into her brown eyes. She was calm now. Awash in the bliss of her own orgasm.

“That was so good, baby. I came so hard. Thank you, thank you.”

“I’m glad you liked it.”

“Oh please, let’s do it again.” I moved my hips a bit. My cock was still hilted in her ass. She groaned at the stimulation. “Oh god it’s thick, baby.”

“There’s something we need to talk about first, Emily,” I said as I slowly started to move my hips back and forth, dragging my cock out a bit and hilting it again.

“Oh fuck, what, what is it, baby?”

“Now that you’ve learned to admit you love a cock in your ass, maybe you can learn to apologize. With words this time, not just fucking.”

Back in 1999 Baz Luhrmann released a spoken word song called “everybody’s free (to wear sunscreen).” It was very popular for a short period of time. It was full of hopeful, pithy advice, including, of course, wearing sunscreen.

I think the sunscreen thing has caught on. Not much else.

Outside of what you already know, I don’t think I have anything hopeful to offer so I’ll just be as realistic as possible:

You’ve been captured by the horny tentacle monster that is Life and it’s going to fuck you, no holes barred, until you either submit or bite its cock off with your teeth…. And even then, at best, you get a moments reprieve while it grows a new one that’s slightly thicker than before.

While every generation has had to grapple with its own “tentacle monster,” the current one is a whole new generation of terrible. Present tentacles include: stagnant wage growth, inflation, AI, psychological damage through social media, War, autocracy, widespread and uncheck corruption… and so on. I’m sure you can think of some that are unique to you.

Now you know what Life has to offer, here’s what I can offer: a pleasurable way to ease in to the non-stop fucking that you’ll inevitably experience. What better way to steal yourself against life than by building up some anti-fragility.

If you learn to grit your teeth and take it you’ll be all the better for it.

So that’s me. A Millennial who thinks he has some of the answers. A white collar professional who likes to teach and give advice.

Tell me about you.

You know what I’m talking about.

The first time I saw it in porn—the humiliating position of hanging her head over the edge of the bed and using her mouth like a pussy—I knew I had to try it.

The only challenge is bringing it up with your girlfriend.

Luckily, the girl I was dating at the time was a submissive little slut who loved to please so it wasn’t that difficult to find inroads. Her mouth was a little small so her blowjobs were never particularly deep. She was self conscious about this. So I played on her insecurity. Suggesting that if I fucked her face upside down, it might be able to be more comfortable… for her.

She was sucking my cock one evening when I kept switching positions. I had her kneeling in front of me while I sat on the bed. I had her on her hands and knees while I fucked her face standing up. I had her put her head on my stomach while I gently thrust my hips in her mouth. But no matter what, I couldn’t get more than half my cock inside. I couldn’t find satisfaction.

“I have an idea,” I said. I motioned for her to lie down and I moved her down so her head was hanging over the edge of the bed.

“Are you sure about this?” She asked. I didn’t answer. I just stood looming over her with my cock bobbing in front of her face.

“Open your mouth.” She complied. Her tongue sticking out a little. Eyes fixated on my stiff cock.

I lowered my hips until my balls were hanging over her face.

“Take my nuts in your mouth.” She hesitated so I solved her indecision for her by taking her face and mashing my balls against her lips. I then felt her little tongue flicking around my scrotum. She was doing great. Sucking one ball into her mouth. Then the other. My cock was rigid and straining.

I wanted the main event.

I pulled my testicles out of her mouth with a pop and lined up my cock.

“Wait.” She said. But she was confusing me for someone patient.

I took her head in both hands and began to slowly thrust my cock in her mouth. I was able to get half way immediately. But then I felt it. The familiar resistance of her throat. Why wasn’t this working?

I’m not one to be deterred by biological reality. I was going to fuck this girls throat no matter what. I moved her head around, trying to get the angle right.

“Relax, baby. Relax.”

“Mmmmhmhhmmhmh.” I have no idea what she said.

But then, something changed. I lined up just right, the angle was just so and then I felt it. My cock popped past her barrier and into her throat. Just a little further. Fuck, just another inch!

And then, success. My cock was lodged on her throat. Buried in her gullet. Distending her neck grotesquely. What a good girl.

She was struggling against it. Trying to wiggle out of it. I’ve never sucked a cock but I can imagine having a thick Bavarian sausage half way down your esophagus is an unusual feeling. I relented for a bit.

Cough. Cough. Cough. Gag. Choke. “Jesus Christ, baby.”

“You’re doing so well.” I grabbed her by the tits and thrust inside her again. I had the angle right now. I popped into her throat much easier the second time. She was getting used to it. I think.

I leaned forward, putting my weight down on her face. Thrusting my cock deeper inside. We had success now. Her lips were at the base of my cock. My balls, still wet with her spit, were on the bridge of her nose. I took two fingers and hooked them in her soaking pussy. No wriggling out of it now. I was going to be satisfied.

How depraved and humiliating for her. Having your mouth, never even meant for sex, abused so violently by a thick ridged cock. My testicles bouncing off of her face. Drool flowing uncontrollably. Her Gluck, Glucks muffled by my body bearing down on her. Pinned down at both ends. At one, being impaled face-first on a cock. At the other, two fingers in her pussy, holding her hips in place.

Fuck, I would never be able to give this up.

When you think about it after the fact, breaking a condom makes you feel like a real champ. You hammered this girl so hard you tore right through an unbreakable piece of latex. You fucked her so hard you beat science and technology.

When I was younger, I bought someone condoms as a birthday gag gift. I then watched in amazement as she tore one open and proceeded to stretch the bejeezus out of it with ferocity. She later said she wanted to see if it would hold. It did.

Based on that experiment, I assumed they were indestructible.

So imagine my surprise.

I had been pounding this girl every which way—mating press, doggy, every angle I could think of— and I finally came buried deep inside her with her nails raking down my back. Her body writhing beneath mine. Her skinny legs pushed to her chest. Her small breasts now pock-marked with bites.

We both lay there panting for a bit. Her shallow breaths making her small chest rise and fall against mine, as my cock continued to twitch in her pussy. Flexing occasionally as I softened slowly inside her.

I reached down and held the condom at the base, as I had been taught to, and slowly pulled out. But something felt different.

Instead of a tight condom with a “reservoir tip” of semen, I pulled out a tattered piece of rubber that looked like it had been through a war. It didn’t just have a hole. It looked like I had set off a cum grenade inside her. No one made it out alive.

I stared at it stupidly, slowly blinking.

“What’s wrong?” That’s when she raised herself on her elbows and looked down, too.

We both watched silently as an enormous glob of my cum slid out of her gapping pussy and on to the sheets.

“What… what… WHAT THE FUCK DID YOU DO!”

The rest of that night was spent looking desperately for Plan B.

It really put sex into perspective. One wrong move and that sticky load could be seeding her. And it also sent me down a rabbit-hole of creampie / breeding kinks. C’est la vie.