Hotel Escapades - Chicago: Pt. 01

What is it about hotels that bring such naughty, such daring thoughts to us? Is it the anonymity? Boredom? Or perhaps in some of us, we have an inner desire to do those things we deep down want to explore but won't, or too afraid to do at home. This is the first of a series stories about such hotel escapades.

About me--I'm late 30s male in the midst of a successful business career. A one time athlete, the remnants of a sculpted body are still there, but far from the stage in my early 20s. At home, I live a normal life...married with no kids, and a normal, but maybe boring sex life. The days of rampant sex with the wife have faded, or maybe just in a rut, with the last few years with our lives consumed with our careers. My job requires me to travel from time to time, a burden or maybe just the perk I need to explore my deep inner sexual desires.

Chicago...

I was booked at a nice downtown hotel for a few nights. My days were booked solid with meetings and had several dinner meetings planned as usual. I flew in late to O'hare on Tuesday evening, and made my way to the rental car center to pick up a rather boring car which luckily was at least equipped with bluetooth. After connecting my phone, I pulled up a nice audio story from Literotica of a woman recording a long, drawn-out masturbation session for the 30 minute drive downtown. I really enjoy the stories on the site and love the sound of a woman un-restrictively pleasuring herself. The soft moans and deep inner grunts make my cock grow every time, and this time is no exception. As I reach downtown, my hard cock is straining against my suit pants. I turn off the audio to let myself come down a bit before embarrassing myself in the hotel lobby.

After a quick check in at the desk, I take the elevator up to my room on the 8th floor. I walk slowly down the hall, hoping to hear the sweet sounds of someone or some couple enjoying themselves, but no such luck this time. Exhausted from the long work day and travel, I swipe the key card to Room 804 and enter. I drop my bag and briefcase on the floor and walk towards the window and open the curtains to explore the view...hoping to see maybe another window nearby with a chance to peak my voyeuristic tendency. Unfortunately, no good options but the views across the river downtown aren't too bad. After a moment of mindless thinking, I hear the door to the adjacent room slam shut. Hmm, I think, I would have thought these rooms would be a bit quieter for as nice of a hotel this was. Nevertheless, I strip out of my clothes in hop the shower to rinse off the day and try to relax before bed.

While in the shower, the warm water is quite soothing and the water pressure was very intense. Enjoying the moment, my mind drifts back to the audio story that cut off too soon. The deep moans flood my thoughts causing my cock to twitch to life. My hand slides down my torso finding my member to give a few slow strokes. Unfortunately my phone was on the bedside table so I decide to cut my shower short and continue a much needed self-pleasure session on the bed listening to the rest of the audio story.

While drying off, I think about the neighboring room again and wonder who it might be, and what they might be up to. Were they naughty like me when in hotels? Instinctively, I place my ear against the wall next to my bed. I've been in enough hotels to know that headboards are placed back to back for some reason. To my delight, I am in luck in that the walls are indeed thin and poorly insulated, again surprising for the quality of this hotel. From the other side, I hear the sounds of a woman talking on the phone. I listen for awhile and try to imagine her and what she might look like. An innocuous conversation at best, with the woman seemingly talking to her family.

"How was dinner? Were the kids good? I'll miss you and see you at the end of the week. Goodnight honey, I love you."

With that the conversation ended. From there I hear the sounds of luggage unpacking followed by the sound of the shower turning on. Nothing too exciting sadly.

Leaving my new neighbor to her own, I'm anxious to get back to the story. Reaching into my small carry-on luggage, I pull out a bottle of lube for my self pleasure session and grab my cell phone to get back to where I left off. The story lacks a plot really and is a 45 minute session of a young woman desperately pleasuring herself. No words, no story-line, no build up...just the sounds of soft moans, and deeper moans, and heavy breathing. Occasionally, the sweet wet sounds of her fingers vigorously pleasuring her pussy as her sweet nectar accumulates. The audio ebbs and flows as she builds to climax time and time and again. Building with primal verbiage of:

"YES! OH YES! I'M CUMMING! I'M CUMMING!" She follows with groans of orgasms. Although I have listened to this audio many many times, I'm not sure just how many times she orgasms but I can only imagine the pleasure she must feel.

Laying on the bed I turn the audio up a little to bring clarity to the sound. Her distinct soft moans bring my semi-hard cock back to life. I drip a generous amount of lube over the head of my hardening cock and bask in the feeling as it drips down my shaft, running down my balls finding the channels to each side. The coolness of the liquid finds my ass hole which makes me twitch--lets just say I'm not afraid of a little anal play from time to time. My left hand reaches for my balls to massage their tenderness. My right hand grips my head and slowly slides down my shaft releasing a long audible exhale. My hands start to work in tandem as my mind is lost in the audio, imagining the young woman on her bed, legs spread wide, sweat covering her body and the scent of her womanhood filling the room. Her fingers curling in and out of her dripping wet opening, pressuring her special inner spot. My own orgasm building as her next one arrives...

My lust is quickly interrupted by a sound from the other room, the sound of someone getting into bed I figure, causing the head board to knock against the wall. My pleasure session stops and I pause the audio. Adjusting to the new quiet reality my mind is still dreary from the prior pleasure. A thought comes to mind wondering if the woman heard me...or heard the audio. More interesting is the opportunity to have another listen to see if any sounds of pleasure may radiate from my new neighbor. I wipe my sticky hands on the towel laying beside me and lean against the wall, pressing my ear to listen. All is quiet unfortunately aside from random snippets of sounds, which I guess are from scrolling instagram stories or something. Ten minutes or so pass, and I'm disappointed that nothing more interesting has happened and an idea comes to light. I wonder if she, like me, loves to hear the sound of someone getting off. With that, I reach for my phone and restart the audio story from the beginning, turning up the volume loud enough that I'm sure anyone passing down the hallway could hear.

The sweet unmistakable sounds of my audio story woman come back to life. Beginning again with lighter soft moans, slowly building to louder and deeper sounds. A few minutes later, still listening against the wall, I hear the bed creek and the sound of feet hitting the floor and suddenly and light knock on the wall. This was not the expected keep-it-down type of knock, but the sound of someone leaning against the wall to listen...a sound I'm all too familiar with. I smirk to myself as I know I've caught her. I reach for my phone to adjust the sound up one more notch, the moaning and groaning building.

The story continues for a few minutes more before I hear shuffling from the wall and a slight sound of heavy breathing. Another shuffle and the breathing subsides but I hear a few footsteps and the sound of a luggage zipper. I'm left wondering if I've lost my prey. Moments later I hear footsteps and a the sound of a body sliding down the wallpapered wall. A few short seconds later the unmistakable sound of buzzing arrives to my ear and my senses are on overload. The familiar sounds of a young woman ravishing herself blaring through my phone speaker and the sounds building through the wall of a mystery woman pleasuring herself with a vibrator. My cock is throbbing at the aural sensation and precum builds on the tip. My hand slides over the head, using the precum to reinvigorate the drying lube. Building my stroke with more and more pressure. The audio story woman is building to an orgasm with the demonic sounds of "YES! YES!"

I hear the neighboring woman begin to moan as well and then I'm taken as she begins to speak:

"That's it. That's it. Cum you little slut. I'm going to cum with you...".

The sounds over take me and my shaft releases its built up warm load of cum, spurting on the floor and wall. The warm tacky liquid coats my hand as the audio woman reaches climax herself.

A few short seconds later the neighboring woman screams herself with a deep "Yessss. I'm cumming!!"

The sensation must have taken control of her as a very loud thump comes from the wall. I imagine its the sound of the back of her head hitting the wall in her release.

I quickly stop the audio, bringing an eerie quick silence to my room. Through the wall I hear the woman shuffle quickly followed by footsteps.

"Busted!" I say to my self quietly and chuckle.

The bedside clock now reads 12:30am and exhaustion takes over. I wipe up my mess and clean myself off with the towel on the bed and fall to sleep pleased.

The next morning, my alarm clock comes early. I follow my normal routine and head down to the lobby bar to grab a coffee and croissant before heading off to my scheduled day. Half way through my coffee, a smartly dressed woman takes the seat beside me. She looks to be in her early 40s, maybe, with an very attractive fit-mom build. I can't help but notice her black stocking-covered legs as her skirt rises up her thigh from sitting at the bar stool. The bartender approaches and asks:

"May I get you something ma'am?"

She responds, "Yes please, a skim latte please...with an extra shot."

He responds, "Yes ma'am, busy day today? That's a lot of caffeine!"

The lady smiles "Yes, it was quite a late night for me."

"Yes of course," the bartender retorts. "May I have a room number to charge?"

The woman answers "Sure thing...Room 806."

I nearly choke on my coffee at her response, knowing she is the mysterious neighbor.

She looks at me puzzled..."Everything ok?"

I smile back at her "Yes, it was just hotter than I expected...the coffee...it was hotter than I expected."

I start up a meaningless conversation while I take in her appearance. Short blondish hair starting to turn, blue eyes, with a nice but not oversized pair of breasts strained beneath a white blouse under her suit jacket.

"Have you stayed here before? Its a great hotel but I'm surprised how much you can hear in your room" I say to her.

She looks startled and responds "Oh, I must've not noticed. I'll take that into account tonight".

I smirk at her, "You're stuck here for another night?"

"Yep, leave on Friday morning." as she grabs her coffee and stands. "I've got to get going, nice talking with you."

I wave as she gets up. "Likewise, I hope to hear you soon!"

She stops and looks back quizzingly. I take it that she didn't hear me or didn't hear correctly so I repeat differently this time, "I said I hope to talk to you again soon...I'm here until Friday as well."

She smiled and waved back and rushed out the front revolving door, her ass looking amazing in her tight suit skirt. I chuckle to myself as I finish my coffee, imagining Miss 806 with her trusty travel vibrator pressed against her pussy, listening to the naughty 'slut' in room 804.

To be continued...