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This installment was 10 months in the making. Back in March of 2023, I was heading to the windy city for work. This was my first time, and per usual, I was checking out the local pages for the general vibe. Long story not as long, but certainly not short, I started talking to Anya and Alli. They were good friends. Both are active on reddit in their own respects. Anya posts her boobs and bourbon. While Alli posts with her tits and starbucks. I’m told they are a sort of “accountability buddies” for posting various NSFW photos of themselves on the internet.

That trip I met up with Anya and we had a great time. You will find her story in a previous post. In that writeup, I mentioned I was supposed to have a threesome with Anya and another woman later that week, but it fell through. Well Alli was that woman. Since my last time in town, we had talked a few times both bemoaning the situation in which we weren't able to dance the forbidden polka, and generally talking up what was going to happen when I was back in town.

As soon as I had the slightest idea that I was going to be back in Chicago, I messaged her. She still was interested in a threesome, but she told me, and I quote, “I want you all to myself first.” Apparently I had passed the Spice Girls test. See their smash hit “Wannabe” for any further detail. The plan was us first, then her and Anya the day after. Sounds like a fucking plan to me! rimshot

The night rolls around and, due to our schedules, we decided to meet up the night I flew in. We were going to start late and hope the neighbors wouldn’t mind. We were lightly sexing throughout the day and even a bit on my flight. Once I was in the uber and enroute to my hotel, I told her to start her journey. This gave me a little bit of time to get in my room, shower, and do everything I needed to get ready.

She was on her way. It was finally happening. I found out that night that when I met up with Anya, several months prior, it was actually Alli’s birthday. So this was her extremely late or very early birthday present depending how you view it.

Finding parking at around 11 pm was a bit of a challenge in the city, but she managed. I was sitting in the lobby of the hotel patiently waiting as the bulge in my pants kept reminding me of the night to come. The lobby was quite large, but from the couch I could see a blonde woman in a leather skirt and stockings confidently walking up to the revolving door.

Her smile said “hi.’” Her eyes said “hello.” But her outfit said “why the fuck aren’t we upstairs yet?”

Walking in we exchanged pleasantries and she even commented that she “felt like a lady of the night” coming to a semi-strangers hotel so late. I told her that she looked great. Earlier in the night she had posted to reddit what she would be wearing tonight with both “Daddy and Sirs approval.” I don’t know either of these men, but they do have very good taste!

Her ride in, plus finding parking, had her quickly going to the bathroom before we started in on each other. I sat down on the comfy chair overlooking the city smiling. Of course there isn’t a 100% chance knowing you are about to have a great fuck, but this is about as close as you can get without putting in the tip. We both had a eskimo sister that vouched for each other. Now that’s what I call "nettwerking".

Strutting out of the bathroom, she locks eyes with me and says, “I’ve been waiting A LONG time for this.” Sitting in my lap, I felt her lips for the first time on mine. My hands instinctively on her ass, letting her feel the strength of my fingers. Her lips were candy apple red. A classic, but wonderful, choice. No idea why this color is so attractive, but I’m here to tell you the who, what, where. Let's ignore the why for now.

I ended up picking her up and carried her over to the bed. She was delightfully surprised. Even commenting she didn’t know the last time someone had done that. I always warn women I can and will pick them up if they like it. Most of the time I get the “you are welcome to try.” I don’t try, I succeed.

She was laying on the edge of the bed, her hair splayed out behind her. Her legs are up and she looked as coy as one can with her tits spilling out of her top and her perfectly waxed pussy peeking out the bottom. Grabbing the office chair, I decided to do some work. I teased her a bit. Lightly touching the inside of her thighs. Getting closer and closer to her clit. I could physically see the anticipation of her wanting me to finally touch it. Slightly brushing her hood she started to let out an mmmmm, but I pulled back, stood up. Towering over her I kissed her once more and told her I was ready to make her cum for the first time. “Yes please” she purred back.

Sitting back down, I spread her labia and gave her very excited and sensitive clit a large lick straight on with a flat tongue. With the energy of a melting DQ ice cream cone in July I started in. I gauged her reaction, and everything was green for go. My tongue did a whole Simone Biles floor routine on her clit. We're talking before she got the yips in Tokyo. My fingers were inside her going for gold in the 200 meter g-spot stroke. She came fairly quickly, but no judgment here. I usually do as well the first time.

“I am already so glad I came”

She was talking about actually coming to the hotel that night, but I’ll take the double entendre compliment!

It was my turn to spend some time on my back. I laid flat on the bed, my cock at full attention and ready for her. The intensity in which she started blowing me was incredible. She had been waiting for this a long time, and wasn’t sparing a single moment to do her thing. If I had to venture a guess, this wasn’t her first time doing this... or second. She was very good. This was no Coors light blowjob, this was a craft blowjob.

I found myself way closer to the edge than I would have liked to have been in the moment; trying to think of anything I could do to stave off the inevitable. I settled on pulling my own hair, just a few strands. My yum has never been pain, so this was a strategy to try and hold on. It worked, kinda. I hadn’t cum, but it was hard; oh so hard.

Between moans I told her that I was going to cum soon if she keeps up with the ShopVac impression. She stopped abruptly, looked me in the eye.

“I need you to fuck me. Now!”

I’m way too out of shape to do a kip up, but like one of those “ a car is crushing an innocent bystander kind of situation” I found the strength and did one. While grabbing the condom, she had flipped back onto her back and scooched to the end of the bed. Using the head of my dick, I teased her clit a bit. She was not kidding when she said she needed me to fuck her. So she did like any person would do after asking politely to be railed and not immediately getting what they wanted. She wrapped her legs around me and Trapdoor Spidere'd me into her. It was totally unexpected, but unbelievably hot. Ladies, take note - it doesn't get much hotter than this.

“I told you I get what I want.”

I lasted as long as I could, but the writing was on the wall and the cum was vacating my balls.

Chatting in between rounds, she starts explaining how I was the first new person she'd met in about a year, and I did not disappoint. Always happy to hear!

Often, she plays with her Dom, and their encounters can get intense and quite kinky. I like to ask people's fav euphemisms for sex and apparently she and her Daddy love to "play pickleball." No wonder the boomers are so into it all of a sudden. I certainly enjoyed our match so far. But like any good game, there were more sets to play.

She asked about my favorite position.

"Don't worry. You'll see soon enough"

I was still soft, but that didn't stop her from taking things into her own hands (and mouth). Soon enough, her playtoy was much less pliable.

What she did next was a first for me. She got between my legs and wrapped her arms around them and "locked" herself in. I was transformed into a roller coaster at cedar point. Her head bobbing and pausing at the perfect time to slowly work up my shaft while maintaining intimate eye contact. Her amount of spit was perfect. I've never cum the second round via head and if I would have let her do her thing, she would have turned me into a damn dirty liar.

I reached my hand into her hair and took a firm, but gentle, grip.

"You are going to ride me now" I commanded. Her eyes wide and her mouth agape; my cock still between her sexy candy apple red lips.

With her pussy soaked again, she stood above me and we locked eyes as she squatted down and slid me inside her. Both of us let out a low moan of pleasure as she leaned back to fully feel my member inside of her.

If a woman has the hip flexibility, I am always a fan of letting them take me for a ride. I let them set the pace while I sit back and enjoy the tits in my face and my hands on their ass.

She understood the assignment and did with me as she wished. I'm guessing she was in this position for at least 10 minutes, changing pace and angle as she pleased. Her body said "I want more," but her face said "Holy fuck, hip cramp."

I grabbed both wrists and told her to lean back. She didn't fully understand, but I lowered her onto her back. My still stiff cock springing out of her.

Flipping over myself, I entered her again and commented on her longevity is a position that many had tapped out way sooner.

"Alot of pigeon pose I guess..." she mustered to say between her gasps.

I slowed down and whispered in her ear.

"You ready to see, no, be in my favorite position?"

"Mhm"

I grabbed a pillow and had her arch her back. I placed the pillow under the small of her back and moved the entrance to her vulva about 3-4 inches higher.

Sliding back into her, she immediately noted the difference.

"There's one more thing that's missing." I said. Making quick thrusts in, but taking my time when pulling out; I felt and watched her lips grip me. Without another word, I grabbed one of her legs and threw it above my head. I skipped a few gears and went straight into pounding her. The immediate exponential increase in volume, and the nails in my back, told me all I needed to know.

We hadn't had a complaint from a neighbor yet, but if they were going to file one, it was going to be then. Her volume only drove me to pound her harder and harder, I felt the head of my cock hitting her cervix. This position is perfect for me, it allows me to go as deep as possible.

My body was willing, but my lungs were dying. I hadn't [right?] cum again yet, but I needed a break from this all-out cervix assault. Trying to time it with her body, I slowed down and told her I needed water and a break. I assured her there was still a set or two in this pickleball game.

You know who has the best stories? Another self proclaimed slut. She had a few spicy ones you wouldn't find with someone that doesn't self identify.

I was told that this far exceeded her "sexpectations" and she might start looking for other partners through Reddit. Getting a slut to live up to their full p"hoe"tential is always nice to see. Most people are truly too goddamn uptight and just need a good fucking. That isn't the case with her in the slightest, but I think you get my point.

"Get fucked!"

And I mean that in the best way possible. But I digress...

After a few, she decided it was time for her portion of "Show & Yell".

"Let me show you MY favorite position!" She said as she flipped onto her knees and stuck her ass in the air, readying herself for doggy.

I play my part and penetrated her again, for the 4000th time that night. She begged for it hard. I'll have what she's having. so I was quick to reach full throttle.

There were still a few tricks up my sleeve. Her arms were planted firmly in front of her as an anchor because she was getting plowed harder than the I-90 in February. I reached for her arms and it truly didn't compute for her.

"What are you doing?" She asked quizzically and rather breathlessly.

"Trust me"

I grabbed her wrists and rotated them so they were at her sides. Like in the supine position earlier, I leaned back and pulled her onto my cock. To the surprise of no one, she responded with cock and awe. She told me later that "that wrist thing" was new to her and she'd definitely need to remember it for future exercise.

While this position is intense for all involved, I cannot maintain a super hard rhythm for a long time. We had been fucking on and off for several hours now, and I was starting to get tired. Just because I was getting gassed, didn't mean I was ready to stop getting some ass.

She had brought toys, but we hadn't put them to use yet. I grabbed her vibe and told her to get on her back, pillow under the hips of course.

I penetrated her and then took the vibe and held it on her clit. With minimal movement from me, I could feel all sorts of micro movements and twitching while completely balls deep inside her pushing on her cervix.

The movements started like someone dozing while driving. A slow roll down with a sudden twitch to recorrect. Each time this happened I'd flex my cock as hard as I could so she could feel the pulse from both inside her pussy and on her clit.

The movements then shifted to a steady squeeze and a quiver reminiscent of an expensive Brookstone massage chair. While on the cusp of her next orgasm, I kissed her deeply, thrusted slowly, and told her I wanted to see her cum. And cum she did. And then again.

DJ Khaled should have been there yelling, "Another one! Another one! Another one!"

I followed the leader and came again as well. By this time, we were nearing 3 am and we were both completely wiped.

The following day we were supposed to have a threesome with Anya, but alas, we were all fucked by the winter storm instead.

So another rain check was written. Soon to be cashed on my next trip to what is quickly becoming the horniest city I travel to.