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First, please bear with me - I've never written an autobiographical story quite like this before, so I'm a little uncertain and feedback / criticism is welcome! Fair warning that my post ended up WAY longer than I expected - I probably went overboard explaining the circumstances where I met Abby, etc. It was just so much fun to relive this weekend! Also, names changed, blah blah, you know the drill.
(Feel free to jump to "" if you aren't swept away with my poetic descriptions of the hotel check-in process)
I work in sales for a manufacturing supply company based in Southern California, so part of my job involves travel around the US to visit with partners, attend trade shows, etc. The events I'll write about here took place earlier this year - recently enough that they're still pretty fresh in my mind, but long enough ago that it's starting to feel a bit like a crazy dream.
Anyway.
I had been sent to attend a sort of small trade event / sales conference in Chicago. It was exactly what you're probably picturing: tons of balding middle-aged men in corporate-branded polo shirts standing around in a rented hotel ballroom, all trying desperately to sell each other stuff. These sorts of events can be quite lucrative, but are just about the most boring thing you can imagine. The event was broken up over a four-day weekend, and since I was going to be on stage presenting to the attendess about halfway through the conference, I'd flown out to O'hare a day ahead of the start-date, just so I'd have some time to prepare, review my materials, and maybe relax a little.
My company had booked me at the same bland name-brand hotel that was hosting the conference, so at least I wouldn't have to deal with rental cars and trying to navigate an unfamiliar city. Due to a delayed flight, I didn't actually arrive at the hotel till quite late in the evening, so when I wheeled my little suitcase toward the check-in desk, there was only one person ahead of me. I stood there, a little zoned out after a long day spent mashed into a too-small airplace seat, and it took me a moment to realize that, A) the person ahead of me had walked away several moments before, and B) in my zoned-out state, I'd been staring dead-eyed at the girl working the check-in desk. I sort of snapped-to, shuffled up to the desk, and started to pull out my ID to check in. As I was doing all this, the check-in girl gave me a knowing smile and said sympathetically, "long day, huh?"
I confirmed that I was jet-lagged, tired and hungry, and I apologized for being the creepy staring guy. She gave me that same sympathetic smile again and dismissed my apology as unnecessary. It was then that I noticed just how pretty she was - she stood a few inches shorter than my 5'11" height, and her jet-black hair and deeply tanned skin gave her an exotic look - not quite hispanic, not quite middle-eastern, but perhaps some intriguing combo of those ethnicities plus something else I couldn't pin down. She was wearing the standard-issue drab hotel staff shirt, but even with that boring shapeless cover it was obvious that she had a nice figure - slim, but with a noticable chest. The nametag pinned to her shirt read Abby. I thanked Abby for her kindness and told her my name - Jake - which I immediately realized was a little silly, since she'd just finished reading my info from my ID while getting me checked in. We both chuckled a little at the redundancy.
I finished the check-in process, grabbed the magnetic keycard, and turned to head for the elevators. As I started to walk away, I realized how hungry I was, so I awkwardly stopped in my tracks and returned to her counter. Abby looked up from her computer screen and asked if I needed anything. I mentioned that I was ravenous and asked if I could still get some food from the little bar and grill at the other end of the lobby. Abby sadly confirmed that the kitchen had just closed down for the night just before I arrived, and she commiserated by mentioning that she too had missed dinner. She pointed out that there would be a small selection of (junky, wildly overpriced) snackfoods in my room, and that room service would resume at 5:30am. Oh well. I thanked her and headed up to my room.
After getting my baggage unpacked, I was tempted to just hit the sack, but instead opted to take a shower. I let the hot water work the tension of the long travel day out of me, and once I felt like I could breathe again, I stepped out from the shower. Just then, I heard a faint knocking sound at my door. I quickly grabbed a towel, wrapped it around myself, and cautiously opened the door a crack. I was quite surprised to find Abby standing just outside my door, holding one of those metal-covered room service trays.
"Oh, I'm so sorry for intruding, Jake! I felt bad after telling you that the kitchen had closed just before you arrived, so I checked in with the kitchen staff and they mentioned that a guest had called in a room-service order right before they shut down but then cancelled it after it was already prepared. If you don't mind a salmon burger and side-salad, you are welcome to have it, complements of the hotel-"
I was honestly floored by her kindness, and it took me a moment to collect myself.
"Th-thank you, Abby - this is such a pleasant surprise!"
I reached to take the tray from her hands, but since I was still quite wet from the shower, my fingers slipped and I nearly dropped the whole thing. Abby took a firmer hold on the tray and offered to bring it into my room for me. I smiled and gestured, inviting her in. With precise movements, she set the tray down on the bedside table and laid out the napkin and silverware. As she walked back toward the door, she gave me that beautiful smile again and said, "I'm off for the evening, so if you need anything, please just ring my colleague at the front desk and I'm sure they can take care of you. I hope you enjoy your stay!"
Before I could even compose a reply, she strode confidently out from my room and the door swung closed behind her. I stood there dripping on the carpet for a moment before I realized that the fates had just presented me with an opportunity. I bolted to the door, wrenched it open, and poked my head out just as Abby disappeared around the far corner of the hallway.
I shuffle-ran down the hallway after her, barefoot, wet, wrapped in a towel that I now realized was way too small. I called her name in the loudest whisper I could, and on my second try, she heard me. Startled, she turned around and looked at me with a mix of surprise and puzzlement and maybe a little fear. "Uhh- Jake? Is there something else I can help you with?"
"Well, it was so kind of you to bring that tray of food up to my room, and you mentioned that you also missed dinner, and I think you said that your shift is over, so- would you like to have dinner with me? I suddenly have a feast to share-"
The question hung in the air for a moment as I stood there, wearing only a towel in the hallway before this gorgeous girl. Finally, she smiled a little and replied, "well, I don't generally accept midnight dinner invitations from soaking-wet guests, but I suppose once wouldn't hurt-"
We went back to my room, and suffice to say, we really hit it off. I ate the sandwich while she ate the salad, and we talked about various small-talk topics for a while. Where are you from, how do you like working in the hotel, etc. etc. I learned that her ancestry included Indian, Brazilian and German (among others), which must have contributed to her lovely features. Somehow, despite me being overtired and still wearing nothing but that towel, she seemed to find me charming and witty - her laugh was loud and full-throated, in sharp contrast to her delicate features. I was surprised to realize that a couple hours had passed, and we were still deep in conversation. I joked that it was a shame that the bar was closed, and she gave me a devilish smile and pulled some of the mini bottles from the hidden bar under the TV. I joked that this had suddenly turned from a free dinner to a pretty expensive date, and she gave that loud laugh again and promised to abuse her powers and remove the booze charges from my bill.
sexy stuff starts below
We shared a few drinks and kept talking, and (as you might expect given the now-obviously-mutual attraction and the addition of alcohol), the conversation rapidly turned to relationships (both of us had recently had a semi-serious relationship sort of fade away to nothing) and then to more sexual topics. She confided that her last serious boyfriend had been mostly a decent enough guy, but pretty immature and self-centered. Worse (from a relationship standpoint) he'd identified as bisexual when they got together, but as their relationship wore on, his attraction to guys became more powerful than his attraction to girls, and they'd both ultimately been very unsatisfied. She seemed lost in thought (and maybe a little drunk by now, or at least quite tipsy), and finally muttered, "-we had sex sometimes, but he never really- you know- fucked me. Like, really fucked me."
Even in my exhausted and tipsy state, I knew that this was a real moment. I thought of half a dozen suave, sensitive things to say in response, but when I finally opened my mouth to speak, I was surprised to hear myself say, "he sounds like- like a real fuckin dumbass. Seriously. I mean, look at you-"
Abby stated at me for a moment, and then she lost it and completely dissolved into giggles. "Right? He was such- a fuckin- dumbass!" Giggling uncontrollably and totally unable to catch her breath, she slumped over toward me and I caught her awkwardly from the side, her gleaming black hair pressed against my left side. She sat upright again after a moment, but now my left arm was around her midsection.
Abby turned to say something else, thought the better of it, and just pushed her face directly onto mine. Given the awkward angle it took us a moment to adjust, but quickly we went from awkward fumbling to full-on passionate kissing. She kissed me softly at first, but within moments she was pulling my body toward hers and kissing me roughly. Her hands began to run lightly up my already-bare back and sides, which felt intense and erotic and ticklish all at the same time.
We continued to kiss for a while, and as her hands began to roam, so did mine. I slid my hands under her shirt and found the skin of her back, warm and taut under her work-shirt. As I slid my hands up toward the back of her bra strap, she broke the kiss and pulled away, standing quickly. I instantly worried that she was about to leave, but to my delight she smiled that wide smile and lifted her arms over her head. Standing before her, I quickly pulled her shirt off and threw it to the side, revealing her lithe tan midsection and bra-enclosed breasts (which I later learned were a C-cup, if that helps with the mental picture). She wasn't overly muscular, but she was obviously quite fit - like a distance runner.
Abby quickly bent and removed her black pants, and then pushed her body against mine. By now the towel was barely hanging on, and as she ground her body against mine the towel slipped fully away and fell to the floor, revealing my giant throbbing 14" cock. Okay, not really - I'm rocking a pretty average 7ish-inch dick, though I will state for the record that I was so fucking turned on by this point in the evening that itfelt like I was the living reincarnation of John Holmes.
Abby felt the sudden pressure of my cock against her stomach when the towel fell away, and without breaking our kiss, I felt her long fingers wrap tightly around my dick as she stroked slowly and firmly. I fumbled with the clasp on her bra until it finally popped loose, and with a shimmy of her shoulders it was off and immediately forgotten. Her breasts were amazing - high on her chest, small enough to be insanely perky, and big enough to feel weighty in my hands. Both were capped by dark pink nipples, and I couldn't resist bending a bit to lick and suck them each in turn. They were already slightly stiff, and quickly became rock-hard under my tongue - that transition is a sensation I'll never forget.
Abby's stroking of my cock continued at an increasing pace, and she was moaning and rolling her head around while I bent before her, licking and sucking her tits. Finally, she pulled my face up from her chest, kissed me deeply on the mouth, and then gave me ahard shove. Momentarily disoriented, I toppled over backwards, thankfully landing on the bed (as she'd obviously intended). The sudden spike of adrenaline from the fall was dizzying, and only became more intense as she knelt between my legs on the bed and took the head of my cock in her red-lipped mouth, looking into my eyes the whole while. She raked her teeth softly down my shaft, sending shivers through my body. Inch by inch she took me into her mouth, and then the back of her mouth, and finally I could feel the tip of my cock pressing into her throat. Unlike the girls in porn films, Abby definitely had a strong gag reflex, but she didn't let it stop her from attacking my cock - bobbing, sucking, licking, stroking, nipping - until it was becoming too much and I worried that I was going to cum. I wrapped my fingers in her thick black hair and forcefully pulled her up my body until she was laying atop me, her body heat radiating into mine, her tits pressed tight against my chest. I reached down and began to tug at her panties, and with a wiggle she was free of them.
Abby lay on top of me and we kissed intensely for another long moment, before I held the back of her head tightly and rolled over, so that now I was pressing down onto her body. I kissed and licked my way down her body until at last I was pressing my tongue into her pussy. Her scent was strong but really good - totally unlike the other girls I've been with. Her pussy smelled of woman and sweat and sex, but also of something I can't place - maybe the spices in her food, or a bodywash, or something else, but I found it wild and exciting. I licked up and down the sides of her outer lips, enjoying the feeling of her long legs writhing around my head as she twisted beneath me. Finally she clearly reached the point where the teasing was too much, as I felt her strong fingers grab onto the back of my head and forcefully press my face right into her pussy. Following her lead, I gave her long slow laps up and down her slit, and each time the tip of my tongue reached her clit, her abs would clench and her hips would raise right off the bed like she'd been zapped by an electric shock. On the forth or fifth time this pattern repeated, her hips shot up even higher and suddenly my tongue was pressed against her asshole.
Abby froze for a long moment, my tongue pressed into her ass, and then with a shuttering moan she pulled the back of my head against her even harder. She spoke for the first time in what must've been a while since our first kiss, but now her voice had taken on a low, rough, ragged tone. "Oh god Jake, what- what are you doing?"
Unable to offer any witty replies while my tongue was pressed hard against her asshole, I did the only thing I could - I made the tip of my tongue as pointy as I could, and I wiggled it right into her asshole. "OH OH FUCKINGSHIT WHAT ARE YOU DOING OHGOD OHWHAT OHFUCK WHAT?!" Her body was tense and shivering and I could feel goosebumps on the flesh of her inner thighs as they rubbed against the sides of my face. I kept wiggling my tongue in her ass, and as gently as I could, I snaked my right hand around her leg and pressed my thumb very, very gently against her clit- and just like that, she came,hard. Thrashing, twisting, clutching at my hair, her legs squeezing my head like a clamp, and all the while I kept licking at her tight puckered asshole.
Finally, her body went limp and she gasped, "no more, please Jake, I need- I need a break." I slowly withdrew from between her legs and slid by body up so that we were laying side-by-side, her feverish and sweaty skin pressed against mine. I ran my fingers over the skin of her side and stroked her breasts for a while, and we lay there as she drifted in and out of a post-orgasm haze. She finally opened her eyes and looked intensely at me.
"So, uhh- I've had guys go down on me before, but- umm- you were, uhh, your tongue was-. um, that was-gooooood-"
I chuckled. "Yeah, I noticed that you seemed to like it when my tongue was in your ass-" I widened my eyes and gave her an expectant, wide-eyed stare, and was rewarded with a bashful look and a blush across her already-flushed cheeks. She got a really far-away look, obviously thinking about something. Finally Abby laughed and said, "I honestly never 'got' why so many porno videos are all about anal stuff, but now- wow. I guess I sorta get it now-"
Pulling her closer, I kissed her neck while my hand slid between her legs, pushing the wetness from her pussy down toward her ass, which I could feel was still slick with my saliva. Gently probing her ass with my finger while her eyes lost focus, I chuckled and said, "there are some other tricks I'd love to show you-"
Whew. Cheesy cliff-hanger place to stop, but this post is already way longer than I expected it to be. Once I started writing it all out, it was hard to not want to really dive into every detail - this was BY FAR the best hookup I've ever had.
Obviously more stuff happened that night, but I've already spent two hours more than I intended writing this all out. I hate when other stories end with "upvote if you want part 2!!" so I won't say that - I'll just say that I really enjoyed writing this out (even though it's probably WAY too long), and that there was some more fun stuff that happened between me and Abby over that weekend. Let me know if you'd like more!
writes_at_nite
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