Ripping Up The Card III (R-18)

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~~~(POV: Ulysses Kennedy)~~~

~~~(Date: May 12th, 2026)~~~

~~~(Location: Holiday Inn, Holden, Oregon)~~~

~~~(Time: 8:41 AM)~~~

My tip is being sucked into Hannah, and she winces with a few cuss words mixed in. There was a brief moment of resistance, but that resistance is gone now. I raise my head and look down. She's only got a couple of inches in, and there is blood already coming out.

It scares me. I have no shame in admitting that. I care and love Hannah, and I don't want to be the source of any pain for her. Seeing that I'm making her bleed... It's fucking with me...

But I push it to the back of my mind and watch her.

"Ha... Ha... Ha..."

She's taking deep breaths far apart from each other.

She hasn't moved up or down from the squatting cowgirl she's in. She's got 12 more inches to get through, but I don't think she can get all of me. Not on the first try.

"Do you need to get off?"

My hands are under her thighs so I can lift her off if she needs it.

Hannah decides to be stubborn and shakes her head no, and lowers her hips even more. Taking in three more inches. Making 5 inches total so far.

"Fuck! Fuck! Fuck!"

She's going through so much pain right now, and I feel even more terrible since I'm feeling nothing but pleasure. I can feel my tip pressing on something. Like a little entrance deeper inside. Which means I'm already...

"You're already kissing my womb?! How much more is there left to go?!"

Her eyes are tightly closed since she's trying to deal with the pain. This means she can't see how deep inside her I really am. Out of a total of 14 inches, only 5 are in her.

That's a total of 9 inches left, and that's not happening our first time. Not even close. The pussy is an amazing thing that can adjust to different sizes, but not like that so fast. Not on a girl's first time either.

She's waiting for an answer...

"You've got about 5 inches in you... There are 9 left to go..."

Her eyes shoot open in shock and look to where we're connected, and she sees.

"Let's just stay like this for a while. Let you adjust to what's already in you... Relax, and I'll hold you in place. It'll be easy for me."

It really will be. Hannah is a petite blond bombshell and someone that doesn't weigh over 95 pounds. Being a gymnast, she's got an incredible body and a low body fat percentile, just like me. Her's is even lower than mine. I'm 3.5 percent body fat, and she's 3 percent.

"Yeah, that sounds good to me..."

How fast she is to agree does make me smile. I feel her put her weight down, and I hold her from under her thighs so she can adjust. Holding 95 pounds like this is nothing for me.

The pleasure at the first five inches of my cock is hard to explain. I've never had such a tight experience in my past life, and the way it's warm, wet, and snug just makes it better as every second passes.

"If your parents could see us right now... They'd probably kill me and lock you away in the basement and throw away the key..."

As I make a joke to ease the tension and pain she's in. I can see it on her face that she's slowly getting more adjusted.

She smiles down at me at my lame attempt to ease her. I never said it was a good attempt.

"Yeah, but it's not like they can do anything now. I'm an adult, and there isn't anything that can get in the way of our relationship anymore.

After a minute or two of silence, she leans forward and rests her head on my chest as I keep her waist elevated 9 inches above me, so I don't spear into her.

"You can start lowering me now..."

I'm apprehensive, but I do as she asks, and I very slowly lower her. I spend 30 seconds lowering her an inch.

"I'm not going to break..."

Her voice is breathless and light... She's feeling pleasure now... I lower her to 7 inches, and I'm halfway in with 7 inches. And 7 more left, but I'm already kissing her cervix with my tip again, which means she needs time to adjust.

But I decide to do something stupid.

I lift her all the way up to only 1 inch in and lower her back down with some speed and light force to 7 inches in.

"Fuuaahh!~..."

That's a sound that I've never heard from her before... I look at her, and her eyes are closed with her mouth open... Some strings of saliva are connecting parts over her mouth, and some of the saliva connects to my chest...

"That felt so fucking good... Don't stop..."

Holy Shit!!

Does that turn me on... Unlike anything I've ever felt before... And my throbbing monster in her tells that to her tight virgin pussy...