#EroticJournalChallenge First Time…

When was the first time you realized you were ______? OR When was the first time you realized you liked or enjoyed ______?

Richard: Jayden and I thought it would be fun to do the same kink for this one, and we decided to do anal/painal. Here’s my story:

I was in my early twenties and had done various types of anal play a few times with different partners. It was fun for a change now and then, but on the whole, I didn’t see much reason to do it over vaginal— which was cleaner, didn’t need as much lube, etc. I started chatting with a new girl online. She explained that she liked anal play when she masturbated but generally didn’t enjoy it as much with partners. We fooled around with it a little, and I would often make her do some kind of anal stimulation if she wanted to get off, finger her ass for a bit in the shower, that sort of thing.

We met up a few times and eventually wound up coming back to my place. 

“Hand me your bra,” I said as we walked to my car.

She glanced around. It was dark, without too many people in the bar’s parking lot. “Yes, Sir,” she said with a playful grin. She reached back, unhooked it, and handed it to me. I unlocked the car and tossed it into the back seat. 

“How far is it to your place?” she asked, sitting down and pulling on her seatbelt, squirming the whole time.

“Less than ten minutes,” I said, reaching across and sliding a hand under her top. I twisted her nipple lightly between my thumb and forefinger and pulled out of the parking lot. “Panties next.”

She gasped as I touched her but managed to moan out a “Yes, Master” and reach down to slide the panties under her skirt. She held them up, letting me see the wet spot soaked in the crotch, then tossed them to join the bra. 

“If you leave a stain on that seat, you can take my belt off next so I can whip you with it.”

We pulled into the parking lot of my complex. I parked and leaned over the center console to kiss her hungrily, my free hand running between her legs to feel how wet she was.

“We better get going before I need that belt,” I said. I stepped out of the car and led the way to the door as she stumbled behind me, soaked thighs pressed together.

I unlocked the door and half opened it, then turned to face her, blocking the way. “Strip down. All the way, there’s no reason a slut like you needs to be dressed in her Master’s home.”

Her lip quivered, and she looked around, but after a moment she whispered, “Yes, Master,” and pulled her shirt off, handing it to me. She looked up and down the hallway one more time before taking off her skirt. “Please…” she said, staring at me, not finishing the request.

I nodded and swung the door open, kicking her skirt inside as she ducked under my arm.

By the time the door was shut, I was already starting to take my shirt off and pointed towards the bedroom door. She started walking towards it, and I followed her. She paused in the doorway to look for a light switch, but I shoved her back, sending her stumbling onto the bed with a gasp. I flipped on the light myself and then climbed onto the bed, kneeling over her.

“Get my cock out. That’s the only thing you’re here for anyway.”

She nodded and attacked my pants, getting my belt open and nearly ripping the button off before they slid down my thighs. I kicked them off on the side of the bed.

“May I, Master?” she asked, looking up at me with a slight pout. I rolled my eyes.

“Go ahead, slut. I told you that’s why you’re here.”

She slid her tongue out of her lips and dragged it along the vein on the underside of my cock. I moaned softly, hands exploring her body as she worked, letting her go for a few minutes. Eventually, her lips popped over the head, and I tangled my fingers in her hair, gently fucking her face.

After a few moments, I pulled her off with a pop and shoved her down on the bed. I slapped her thighs open and crawled between them, leaning in to nibble them and lap at her cunt. I came away with my lips and cheeks covered in pussy juice. “I don’t think I’ve ever had such a wet slut before,” I said.

“Sorry, Sir. No one’s ever done this to me before.”

I climbed on top of her, lining my cock up and slipping in almost before I realized I was touching her pussy. She moaned out and rolled her hips, taking me all the way to the hilt on the first thrust.

“Tight fucking cunt,” I gasped, looking down at her laughing face.

“You should see how tight my ass is,” she said with a wink.


Tomorrow, we’ll post the conclusion to this little story from Richard!

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