“Let’s get this dress off you and you on your knees.”

~

When I come to New York, my goal is to see shows, and for the first time ever I had a ticket to go see Shakespeare in the Park. This year’s production is Twelfth Night, and with a stacked cast including Lupita Nyong’o, Sandra Oh, Peter Dinklage, and Jesse Tyler Ferguson, I knew I was in for a wonderful evening.

But I can also be greedy, or optimistic depending on your perspective. Therefore I found myself on Tinder, shortly before getting ready for the show, swiping left and right, hoping for the best.

Enter HC.

HC is a walking green flag. 

In his profile, he mentioned being ethically non monogamous and open to brief dalliances with visitors to the city. He was handsome, with kind eyes, curly salt and pepper hair, and a small septum piercing. Basically my catnip.

After matching, our text exchanges included my plans for the evening. HC too loved theatre, was encouraging of my plans, and offered himself as a nightcap for my evening. He had plans to be in the area near my hotel with an already set engagement with a friend with benefits. We estimated a time for our meeting, and I went about my evening with even more to look forward to.

The show was indeed hilarious; I highly recommend seeing it, if you can get a ticket.

And so it was that, around 11pm, I found myself at a small high top table in the hotel restaurant, nervous excited for what the rest of the evening bode.

“Striped dress, poofy pony tail, small table by a column,” I texted.

“White shirt, jeans, grey chucks,” he replied.

I’d asked for his drink order prior to his arrival as the bar was about to have last call; a glass of Prosecco sat on the table waiting.

“Hey.”

“Hi. Are you a hugger?”

“Of course.”

I knew within sixty seconds I wanted to fuck this man. The same kind eyes from his profile stared at me as we spoke, but this time a wink and a grin accompanied them.

I talked about the show; he talked about his evening. As the conversation meandered on, the more I realized we were well matched. The banter flowed; we talked about our respective jobs, where we were born and grew up, a tangent about D&D and Dropout TV, and eventually we came around to the topic of kink.

“I actually have my toy bag with me. I just came from a play date. No pressure, though. This is a good time to ask: what do you want tonight?”

I wanted this man to fuck me silly.

We made our way to the elevator. As we waited, a group of late teen or probably early twenty something’s also stood by, the girls adorned in head scarves. I found myself nudged up against him and his hand found its way to my ass. We stepped onto the elevator and stood against the left wall as the younger ones joked and crowded towards the right. Again his hand surreptitiously settled onto my rear end and our interaction all the more lewd and fun for it. As the group exited onto their floor, he whispered into my ear, “Hand on the neck?”

As the elevator door closed, my answer: “Yes. Press, but don’t squeeze.”

“Like this?”

His hand found my neck and his mouth found my lips. The juxtaposition of his soft lips and scratchy facial hair was intoxicating; the tone for our time together was set. 

As we stepped off the elevator, I looked back at him and remarked, “Oh, you’re gonna be fun.”

After we entered my room, I asked if there was any music he hated. “Some country music. But I know where you’re from. I trust your musical taste.”

He took a moment to freshen up in the bathroom. After I started my Graduation Party playlist, I hurriedly unbuckled my sandals and tossed them aside just as he reemerged from the restroom.

“Okay, let’s get this dress off you and you on your knees.”

He knelt down and grabbed the hem of my dress, lifting it up over my head and deposited the fabric onto the bed. I descended to my knees, my focus now on his crotch. I unbuckled his belt, unbuttoned his jeans, and helped ease the stiff fabric down. He took off his shirt as my hands rested on the elastic of his boxer briefs. In that quick moment, I remember thinking, hoping, praying he wasn’t small but knowing even if he was this could still be quite enjoyable.

He was not small.

I pulled off his briefs, took his dick into my mouth, my hands resting behind his thighs. My tongue swirled his tip, then my lips sunk down his shaft. I traced the veins, lapped and then sucked his balls into my mouth. 

“Good girl.”

He sat on the bed, myself still on the floor, and laid back to fully enjoy himself.

“I appreciate how you are not using your hands.”

Instead, as I continued to enjoy his length with my lips, I reached back to unhook my bra. He, being happy to assist, reached down and flung off the fabric, access now granted to my nipples. He rubbed and then lightly pinched as I continued with his blow job.

“That’s it. You, up on the bed. I want to taste you.”

I stood, slipped off my own underwear, and climbed up towards the headboard.

He turned and in passing remarked, “Kushiel’s Dart?”

“Yeah, I’m rereading it for the second time.”

“Great fantasy book.”

Like I said, we were well matched.

I reclined against my pillows and let my knees fall away.

“Wow, you are already so wet.”

His finger briefly circled my clit before dipping into my wetness and then bringing it to his lips. 

“Mmm…”

He bent over, his mouth finding my nipples, and nipped and sucked to the beginnings of my moans. His mouth trailed down towards my pussy. He licked and sucked my clit, starting slow and deliberate. My hands found his hair, lightly gripping his curls; my moans grew louder. I rolled my hips up, undulating in admiration of his work. I had not had such wantonly lavish cunnilingus in far too long. My first orgasm ran through me, my exhalations rather loud, and I realized I hadn’t mentioned that before to him.

He reached over, slipped on a condom, and then slid inside me. His dick was so thick, his thrusts exquisitely rough, and soon, two more orgasms shot through me.

He paused, still inside me, a smile on his face.

I took that moment to say, “Hey, I forgot to mention I’m very vocal.”

“That’s alright.”

“Good, okay. Just, you know, I like to warn people. Informed consent.”

“No, I appreciate feedback. But question for you: are you a person where there is the long build up to an orgasm or do you cum easily and just keep cuming.”

“The second one.”

“That’s what I thought. What’s your record?”

“Um, 13 I think.”

“And what are you at now?”

“Three.”

“Hmm, well we have a record to break.”

He was ambitious. Apparently, this was his specialty, fucking folks until they lost count as to how many times they came. I love rising to challenges.

“I’m going to count down from five.” His finger gently circled my clit, his dick still deep inside me, his thrusts measured, deliberate. “At one, I want you to cum.” That was orgasm number five, and the first time I’d participated in orgasm control in years.

“On your knees.”

He fucked me doggy style, wave after wave of orgasms rolling through me. I cried out as tears kissed my eyes, my hands fisting the sheets, and my hips bounced back to meet his unrelenting thrusts. 

“Sir, you feel so good.”

I doubt he understood my exhalations through my moans. No matter. His dick was fucking magic, eliciting orgasms like exhales.

“I want your mouth back on me.”

He ripped off the condom and I gladly descended back down to his crotch.

“You can use as much spit as you want. I’m not washing the sheets.”

I took his dick and smacked it across my face, both cheeks, then rubbed my whole face against it. Somewhere along the way, he’d put on a cock ring on the base of his shaft and another around his balls as well. I used them, flicking my tongue near and around them, then sucking both his balls into my mouth. I ran my lips up and down his shaft, then plunged his cock into my mouth, easing as much of it into my throat as I could.

“Fuck, I love having my cock worshipped.”

“You’re letting me play. I haven’t gotten to play with a cock in a long while.”

I sucked on the tip, swirled my tongue, then eased down, down. He grabbed my hair and pressed just a little more. I gagged but held myself there, massaging his head with my throat before coming up for air and then returning, bobbing my head up and down, up and down, his hand in my hair encouraging me further.

“Oh, you messed up your makeup for me.”

I smiled; it felt so good to be appreciated for my efforts.

“On your back.” 

I turned around on all fours. He smacked my ass.

“I said on your back. Dick drunk.”

“Yeah, I am.”

Again, his lips were on my nipples, mean and insistent in the best way possible. He bit, and I moaned, my hands in his hair pulling his face into my chest as I lifted my nipple towards his wanting mouth.

“Oh god, oh god. Yes. Yes. Fuck, a little lighter on the bite please.” He too took direction well.

New condom on, he asked “What number are we at?”

“Ten.”

He spat onto pussy, thumped his dick on my clit, and sunk into me again.

“Fuck, you feel so good,” he said.

“I want all of you,” I begged.

He thrust as far as he could go, the mixture of pleasure and pain intoxicating.

“You can slap me.”

Three quick strikes on my left cheek, two on my right, and even more forceful thrusts followed. 

Again on my knees, he fucked from behind, this time also spanking my ass.

“You can play with my asshole, but no anal until after the third fuck.”

“I’d never assume anal on the first fuck or a one night stand.”

He rubbed my ass, slid his finger along the crack, and circled my hole. One day, though, I hope to experience his dick in my ass.

Eventually he had to tap out. I was his third fuck that day. It was late, well after midnight, and he still had to get home. 

Final count: 17 orgasms.

“What is your aftercare,” he asked.

“Just chatting after.”

We lounged naked in the bed, him reclined towards the headboard, me towards the foot of the bed, facing each other, our bodies skin-to-skin against each other. We talked yet more, venturing into stories about past fucks: orgies, play parties, gang bangs, birthday gifts, and his estimation versus my precise data about all the people we’d fucked. 

“I could tell you are a squirter. I could feel every time you came.”

“Really? Fascinating.”

“I mean, it does fill the space well.”

We laughed.

It was after 1am when he put his clothes back on and departed with his consent to write about our time together and an open invitation to message him the next time I was back in the city.

That I will absolutely do.

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