Josh’s Escort Chronicles, Ch. 01

I'm sitting in my hotel room, looking at the clock. Scarlett said she'd be here at 6:30, and with about five minutes to spare, my heart rate is picking up and I'm peeking through the curtains of my room every time I hear a car pull into the parking lot.

I'd text her about 15 minutes ago to let her know I was here and what room number I was in. She'd responded with a 'Ok, be there in a bit,' along with a kissing face emoji. I had nothing now to do, but wait.

Staring off into space, my phone buzzing startled the hell out of me. I picked it up, with a new message that just said 'pulling in', so I peeked through the window again. A small blue car was parking next to mine in front of my room, and a woman with jeans, a tank top and sunglasses got out with a small bag. She walked to my door, and I twisted the doorknob as she was about to knock. She walked in and I shut it behind her, turning toward her with a hopeful look on my face.

She took off her sunglasses and sat her bag on the dresser, turning to me with a big smile.

"Hey, Josh!" She walked up to me and wrapped her arms around me, hugging me tight. "How are you today?" I found my words again.

"I-I'm good, how are you?" I asked.

"I'm really great!" Scarlett said. She had a nice, bubbly personality, but I'm not sure if it was an act or not. I guess it didn't really matter.

"So, Josh," she said, sitting down on the bed and grabbing my hand, pulling me to a seat next to her. She put her hand on my thigh and looked at me. "You seem a little nervous. Am I right in guessing that this is your first time?"

She was right. If you hadn't guessed by now, Scarlett was an escort I hired to fuck me. Don't get the wrong idea about this. I'm not some incel that can't get laid, I actually do ok on my own. But, I'm single, I have plenty of money, and I saw something not long ago on escorts that intrigued me. I decided to scratch the itch, so I browsed online on an escort website and found one, then looked on reddit for etiquette tips, and contacted her. She did some sort of screening, I guess just to make sure I wasn't a criminal, and when she decided I checked out, we scheduled a time.

"It is my first time," I said, a little nervous, and blushing.

"No worries, I love newbies! Plus, you're cute! I can work with you." She leaned over and kissed my cheek.

She was an all-American bombshell. About 5'7", blond hair, blue eyes, great tits and an ass that filled her jeans out nicely.

"So, Josh, I want to lay out some ground rules. I'm super easy-going and fairly open minded, but I do have a few hard 'no's'. When we are having sex, we use a condom the entire time. I'll end this session immediately if you try to take it off or suggest that we do."

I nodded enthusiastically. "Absolutely, I'd expect nothing less."

Scarlett smiled. "Good! Now, I'll blow you with no condom. You can even cum in my mouth, just give me a heads up. And finally... nothing in my butt. I'm not an anal girl."

"Check, and check, Scarlett, thanks." I was strangely becoming more comfortable and looking forward to it what was coming.

Scarlett leaned in and kissed me on the lips. Surprised at first, I returned, getting more and more involved, finally ending up with our tongues in each other's mouths. She broke the kiss and smiled. "You're a great kisser! I'm not making that up, some guys I visit are really pretty sloppy. Now, I'm going to use your bathroom to get ready. Is there something in there for me?"

She was referring to the envelope I prepared for her that had $500 in it. I told her there was, and she smiled sweetly to me before skipping off to the bathroom and closing the door.

Less than two minutes later, it opened slowly. Scarlett stepped through it slowly, wearing a red lingerie set. The fabric was a fine mesh, so I could easily see her nipples and the hood of her clit peeking out from between her legs. She walked up to me sitting on the bed, and straddled me, laying me back. Then she leaned over and kissed me. As we were making out, she took both of my hands and put them on her breasts, allowing me access to explore her body, while she reached a hand down to my pants and expertly unfastened them, freeing my quickly hardening cock. Feeling its length, she smiled against my mouth and stroked my shaft slowly.

She stood back up and made a little show of taking off her lingerie. In no time at all, we were both completely naked, back on the bed and kissing. She pulled back and looked at me.

"I'd like to go down and introduce myself to my new friend," she said.

"I think he'd love that," I replied, and Scarlett worked her way down my body. She took a look at my cock for a moment before licking its length, and then engulfing it with her mouth. Her moans got me even harder, and her skill was top-notch. I felt a little buildup, so after a few minutes I pulled her back up to me and kissed her some more.

She leaned to the bedside table and took a condom out of its package, and expertly placed it on the tip of my cock, rolling it down. She climbed back across me, lined up my cock to her pussy, and guided me in, gliding down my length until her ass was sitting on my thighs. She was in charge now, ricking her hips and moaning softly, bringing my hands up to squeeze her gorgeous tits as they bounced in front of me. She bit her bottom lip and leaned her head back with her eyes closed. She was either really enjoying it, or was a great actress. Either way, it was totally hot.

I sat up and she got off to switch positions, asking me what I wanted. I told her to lay on her back and I entered her missionary, with her legs perched on my shoulders. I quickened the pace of my thrust, looking down to watch my cock moving in and out of her folds. Foolishly, I was surprised that Scarlett's pussy was tight and felt amazing even despite the condom. I assumed that with the amount of men she probably slept with, her pussy wouldn't still look and feel like a virgins. I was wrong!

"Finish me in doggy style, baby!" She cried. I removed my cock from her and before I knew it, she was on her hands and knees in front of me, reaching back and guiding my cock back into her from behind. As soon as I was inside her, she lowered her chest to the bed and arched her back, and I pounded her pussy. I felt her tighten up and moan really loud, maybe she came, but I wasn't too sure. It worked, though, because the sensation was enough for me to instantly build up and fill the condom tip full of my cum.

I pulled out of her and laid down on the bed, my cock still standing hard. She turned over and took the condom off my cock, careful not to spill any of the cum I inserted into it. She held it up after tying it in a knot.

"Damn, Josh! That's a ton of cum, I'd definitely get knocked up from that!" She said excitedly. "I think I want the next load going down my throat, what do you think?"

I nodded at her in agreement, still catching my breath. She threw the condom in a trash can and rejoined me in bed, cuddling up against me.

"That was fun, baby," She said, caressing my cock and pushing her breasts against me.

"I thought so too," I said, relaxing more against her. She leaned down and kissed me, smiling.

"So tell me, Josh. It's your first time, thanks for letting me pop your cherry, by the way! What made you want to call an escort?" She asked.

I thought about the question, and figured I might as well answer it honestly.

"Well," I said, "I read this article online that talked about modern sex workers and honestly I was intrigued about it. So I wanted to find out what it was all about, and usually when I have an itch I just scratch it!"

Scarlett laughed, "Well, I'm glad you got me to help you scratch! So is it everything you ever dreamed of?"

"Yeah, I think it is," I answered.

"Good!" Scarlett said. "So, Josh, the not-a-hooker-virgin anymore... I love to hear about fantasies. Tell me what your ultimate fantasy is."

"Ehh..." I said, looking at her, unsure. She probably wanted nothing to do with my particular fantasy. It was something that I'd tried with girlfriends and even hook-ups, but no one I'd met seemed to be into it. Scarlett noticed my hesitation.

"Come onnnn," she pleaded, "You can tell me and I won't freak out. Unless your fantasy is to fuck an escort and then kill her, then, yeah I might freak out a little," she said with a laugh.

I laughed as well, then quickly said, "No, I promise it's nothing like that."

Scarlett didn't say anything, just looked at me with a smile playing at her lips.

"I, uh... geez this is so embarrassing. Ok, fuck it. I want a girl to... take a piss on my cock and balls." I felt my face redden. I launched into an explanation, as if I was trying to apologize for my raunchy desire.

"I mean, it's not like a dom/sub type of thing, I'm actually not into that at all. It's more like... a trust thing? I don't know, like being intimate with someone enough for them to want to do that with me. It's weird, forget I said anything," I said, with a nervous chuckle.

"Josh," Scarlett said in a gentle voice, "I totally understand. I hear way crazier things from other people all the time."

"You do?" I said. I was astonished.

"Oh yeah. I have a guy that pays me to come in and hit him in the ballsack with a flyswatter, believe me, a little golden shower is pretty tame," she said.

"Oh... yeah I definitely don't want to get hit with a flyswatter in the nuts, that doesn't sound fun at all," I said with a laugh.

"I KNOW, right?" Scarlett said with a grin. "But hey, he gets off on it. I've probably seen him a dozen times, and I've never actually had sex with him. Literally just hitting him in the balls."

"Totally wild..." I said.

"Yep. But hey, enough about him, let's get back to you," she said, standing up and holding her hands out to grab mine. I stood up, and she whispered in my ear, "It just so happens that I kinda need to tinkle..."

My cock flooded with blood, instantly standing hard. I was flabbergasted as she grabbed it, and then led me to the bathroom by the dick. She opened the shower curtain.

"Have a seat in the tub, Josh," she said with a big smile. I did as she said, and as soon as I was seated, she was straddled on top of me, kissing me deeply again and rubbing my cock up and down her pussy lips. After about a minute, she sat up straighter, looking down at me with a smile. Then she let out a satisfied sigh, and I felt a warmth on my cock. I looked down and saw Scarlett's nectar fall out of her and all over my cock, running the warm sensation over my balls and into the tub. Her stream probably lasted 30 seconds before it stopped. I was harder than I can ever remember being. She stood up for a moment, still straddling me, then smiled again.

"Wait, I have some more! Here," She said, squatting over my crotch and once again releasing a stream of piss on my cock. Then she leaned over me once again and kissed me.

"How was that," she said in my ear quietly.

"That was...so fucking hot."

A satisfied smile crossed her face. She helped me stand, and then turned around and turned on the faucet, heating up the water before turning the shower on.

"Wash me?" She asked, holding up a wash cloth. I did, slowly and lightly running my hands over her body, washing her breasts and her tight little pussy, then down her legs. She took the washcloth from me and did the same, cleaning me up, then rinsing both of us off and turning off the water. We dried off and walked back into the bedroom.

"Let's take care of this little issue you've got," She said, softly grabbing my cock and lowering to her knees. She inhaled it, showing her expert blowjob skills. I was so worked up that less than a minute later, I was ready to cum. I told her I was getting close, and she looked up at me and smiled, my cock still in between her lips.

I let loose with abandon, shooting my cum deep in her mouth. She took all of it, continuing to move my cock in and out, and swallowing the entire load I had to give her. She kept on lightly sucking on my head until I couldn't handle it anymore, the sensitivity taking over. My softened cock flopped down as it left her lips and she smiled up at me.

"So, Josh... did I earn a call back?" She asked, standing up.

"That was amazing!" I said, still in shock at what I'd just experienced. "Absolutely!"

"Perfect! I'll save your number, text me any time, babe," she said, walking back to the bathroom. She dug in her overnight bag, producing some mouthwash and taking a swig, gargling it and spitting it into the sink.

"Can't go out in the world with dick breath, that wouldn't be very ladylike of me," she said, winking at me in the mirror. She put her lingerie in the bag, and I watched as she dressed herself, putting on a regular pair of panties and a bra, then the clothes she had on. I got dressed myself, and we talked for a few more minutes.

"I had a great time, Scarlett. Thank you for seeing me!" I told her, giving her a hug and kiss as she stood at the door.

"So did I, Josh! Let me know when you want to see me next!"

I told her I definitely would, then as fast as she came in, she was gone. I heard her car engine start up and she pulled away, I was $500 and two loads lighter, and checked out of the room to head back home.

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This is the end of my first foray, but I think I'm going to make this a series of Josh's escort encounters. Stay Tuned!