Chicago Surprise

Just my luck, I got sent to Illinois.

Not that I have anything against Illinois, really—it's just that the rest of my company got sent to New Mexico. From New York. In January.

This was my "reward" for actually being on the ball, doing what I'm supposed to, making myself into the "up-and-comer" in the business—I got sent as the only representative from the company to the more "important" conference. But of course the more important conference had to be in Chicago in the middle of the fucking winter.

Let this be a lesson to you: don't work hard. You'll just end up with the same pay for more work, delivering bullshit powerpoints in Chicago while your co-workers are living out their "Breaking Bad" fan-fiction dreams exploring the desert and chillin' with ladies in bikinis (or hunks in trunks, whatever your preference, no judgements).

Where would you rather be?

However, all that said: this trip worked out in my favor. Hence why I'm writing this story.

To (only slightly) make up for the fact that I was getting lake-effect snow while everyone else was getting pool-side cocktails, the company put me up at the best hotel they could score: I was on the Mile, great view of the lake, they were covering all the cabs or Ubers I could need or want, dinners on the company card, they got me Blackhawks tickets AND Bulls tickets, the works. 9 days in Chicago, I'd be frost-bitten and miserable, but at least I'd be well-fed & entertained.

Turns out, I didn't need any of that. I had all the entertainment I needed right at the hotel.

To preface: I enjoy beer. In both ways you're thinking: I both love to try new stuff, act like a beer snob and talk about the nose and the palate and all that b.s., and I also love to just DRINK. So my first night in town, I found the closest beer bar, made friends with the bartender to talk shit for a couple hours, and over that time went through 4 new brews I hadn't sampled before. 2 of those were really strong, so I was pretty-well ripped by the time I left.

But once I got to the hotel, it was only 9:15. I could catch the end of the Rangers game on tv if they'd show it, so I figured I see what was up at the hotel bar. It being a Tuesday night, there weren't too many people there, just a drunken guy in a suit hitting on a pair of bored-looking 20-somethings, and an older lady at the end of the bar, chatting amicably with the bartender, a busty 30-something with a lot of tattoos and too little clothing.

Having an affinity for busty, I figured I should sit close to the mature woman. I was thinking I'd try to chat up the bartender and enjoy the view, but when I got closer to her end of the bar, I realized, "you ass, you made the right decision and you didn't even realize it..."

Because forget about the bartender: the older woman who was chatting with her was incredible. Probably mid-50s, with a gorgeous face, wavy brown hair, brown eyes you could get lost in, wearing a sort-of-conservative-but-goddamn-you-can't-hide-curves-like-that kind of cream blouse and blue skirt combo...and insanely sexy tits. Nice and full and curvy the way I LOVE a lady to be...

My buzz was still on, but seeing this lovely lady made me focus. I had a mission, and I didn't want to fuck it up!

I sat down a stool away from her—the busty bartender immediately thrust her chest at me, winked and asked what I was having. Taking off my coat to put on the back of the chair, I said, "whatever's warmest." I winked back. "Just kidding, gimme the your favorite stout on draft."

Seeing that my neighbor's drink was almost empty, I added, "...and another one for the lady."

She seemed surprised, which surprised me in the moment—a lady that gorgeous should be used to getting sent drinks. But she responded, "not every night a handsome young man buys me a drink. Thank you." And she smiled.

And oh damn, was that mission ever on now. What a smile. My cock instantly stirred, she had the most naturally pretty "come-hither" smile I'd ever seen, without even meaning to. I'm getting hard again just thinking about it.

"I don't believe that for a second, pretty lady," I said back. "And who you callin' young?" I flirted back at her.

"My kids might have went to college with you, young man, you better watch out," she said, but in a playful way.

"I'm watching," I replied. "And I like what I see."

The bartender came back and was putting our drinks out at this point, overhearing the last couple lines of our exchange. She got this stupid grin on her face, winked at me again, and made for the other end of the bar, giggling as she left. My companion blushed, and she saw me notice.

"What was that about?"

"Oh, nothing." She was lying, so I gave her a side-eye. "Ok fine, we were having a little girly discussion before you arrived, and it seems she thinks I may have solved my little...well, what I was complaining to her about."

"Which is?"

"Oh, you're going to have to chat me up a lot more before I tell you." She winked.

And so I did. We talked for about 2 hours, Valerie and I (she finally told me her name, after I got her to stop laughing about my name being Monty), about where she was from (Illinois, but in the city visiting one of her kids), what we both did for a living, a little about sports ('cause I was, in fact, keeping an eye on the Rangers game), and just general Chicago stuff, where to go, what to see, best pizza and hot dog and beer bar and whatnot, a nice conversation to have with a stranger at a hotel bar. Of course, after about 10 minutes I'd made my way to the stool directly next to hers, and after about an hour or so she was finding excuses to touch my arm and shoulder.

I only got thru one more beer after the first I'd ordered, and she got through another daiquiri, so while we were both lightly buzzed, neither of us was wasted. I'm usually kinda shy about these things, but this woman was way too hot to not try, so I brought it back to the earlier conversation.

"So, I think I've chatted you up a good amount...what was it that you were complaining to our busty bartender friend about?"

She blushed again, but kept my gaze, and said lightly, "Well. I was complaining that I haven't enjoyed the company of a man in a long time."

"Well good thing I arrived, huh? You've had my company for...oh wow, what has it been, over two hours now?"

"Does it have to end, though?" she asked, that really hungry look in her eye.

"Not at all, I'm really hoping it doesn't end for a good long while," I responded. "However, how about you let me show you back to your room."

I had to remind myself to pay the tab before leaving, I was in such a rush (I made the company cover my drinks, and hers, who was going to know?), but then I gathered up my coat, put my arm out to lead her out, and we walked—briskly—out the bar to the elevator bank in the lobby. I noticed her give a wave to the bartender on the way out, and she was giggling like a schoolgirl as she did.

Once in the elevator, after she'd pressed the button for her floor and the doors closed on us, I couldn't resist. One arm went to her full hips, pulling her toward me, and the other to her pretty brown hair to pull her head to mine, and I kissed her, gently but insistently. She melted.

"Oh my goodness, I've wanted that for hours now," she said.

"A lot more where that came from," I said.

She then kissed me, hard, her tongue thrusting in between my lips, lingering on my lips as the doors opened. "Good."

I put my arm around her, and followed her lead to her room. I was slowly sneaking my hand down her curves to get more of her nice, juicy ass, but her hand went right for one of my cheeks, squeezing.

"Mmm...nice and firm."

"I do a lot of squats," I laughed, then grabbed a nice big handful of that plump ass of hers.

"I don't," she giggled (my god, what a cute little laugh she had). "You don't mind?"

"I do not mind in the least...as a matter of fact, I'd say this ass is just about perfect." I gave it a nice little spank, as she put her keycard to the door, grabbed my hand, and pulled me inside.

I let the door shut behind me, then lunged for her again, I just couldn't help myself, I needed those lips on mine again. She kissed me again, hard, her tongue in my mouth again, both of our hands now all over the other's back and hips and ass as I slowly guided her toward her Queen bed. Her knees hit the side of the bed, and she fell back, laughing as she was taken by surprise. I laughed, too, and admired her sexy body lying there on her bed. She noticed me staring, and got a look like she was concerned for a moment.

"Something wrong, Monty?"

"Not at all," I said, just staring at her, drinking her in with my eyes. "You're just fucking gorgeous, and I'm admiring the view."

She blushed again, and did that giggle once more. Goddamn, I wish I could put that giggle into words, it was cute and sweet and sexy as fuck, and it drove me wild. "You don't mind if I get a little more comfortable, do you?" I asked as I started to unbutton my shirt.

She pulled herself to a sitting position, and started to untuck my shirt, undoing the buttons from the bottom. "Not at all. Here, let me help."

She pulled up my black undershirt and was kissing my stomach as she exposed it, until we had the buttons of my shirt off. As I was pulling my tee off, I could feel her at my belt buckle, undoing it, then going for the clasp of my suit pants, unzipping them, then letting them hit the floor. She was staring up at me as I was standing there in just my black boxer-briefs, one hand grabbing my ass, the other slowly running up and down the length of my already stiff cock thru the fabric. Goddamn, those eyes...

"Your turn," I said, taking her by the arms and pulling her up, switching places with her to sit on the bed.

"Help me with this, then," she said, turning coquettishly to show me the clasp of her skirt over her delightfully full ass. I grabbed her hips, kissed her ass thru her skirt, then undid the clasp. She stepped forward, and shimmied the blue skirt down to the ground.

A quirk about me: I've got a thing for sexy under-things. And she could not have been more perfectly dressed for my tastes. Black opaque stockings, with lacy tops, held up by a garter belt (be still my heart) in baby-blue and white lace, with matching cheeky panties only half-covering her delicious booty. She stood there, looking over her shoulder as she realized my eyes had gone wide and my mouth was agape.

"Like what you see, young man?"

"Good lord yes, Ms. Valerie. You certainly know how to dress."

"Mmm...Ms. Valerie, huh? You hadn't called me that yet."

"Sorry, does it bother you?"

She considered for a moment. "No, I don't think so. If I'm going to enjoy a younger man, I may as well indulge in the fact that he's a younger man. Just so long as you don't mind indulging an older lady..."

I reached out, and spanked her ass lightly. She giggled. "With a body like that, I don't care how much older you are...goddamn..." I pulled her hips toward me, my hand running up her back over her silky cream blouse, lightly pushing her down so she was bending over with her ass at my face. I buried my face into her panties, kissing her pussy, already getting wet thru the fabric, I could tell, moaning as I did so. And she was starting to moan, too.

"Ohhhhh...yes, Monty, god it feels so good to be wanted..."

"Then you're going to feel like a fucking queen tonight, Ms. Valerie," I said, taking her hips to turn her around so she was standing in front of me. I started to undo the buttons of her blouse the way she had undone my shirt, kissing up her cute plump belly as I did. She helped me by taking the top buttons, and we soon had her blouse on the ground, exposing her massive tits in a lovely blue & white bra, matching her panties, of course.

"Holy shit..."

My hands went right for her tits, and I was kissing her stomach, squeezing those huge soft breasts and moaning like a teenager just getting his first touch of boob. She was getting into it by now, moaning, her hands on my shoulders and in my hair—I think she was loving my enthusiasm as much as the touches, because she said, "Such a good young man...been so long since I've been touched..."

"After I'm done with you tonight, it better not be too long before I touch you again...you're the most gorgeous woman I've ever gotten my hands on," I said, staring up into those beautiful pools of brown in her eyes.

She leaned over to kiss me, my hands still bouncing those incredible tits in her perfect, sexy blue and white bra, and we made out a little more before she dropped to her knees and forcefully, but careful not to hurt by boner, pulled my boxer-briefs down. My 8" cock sprang free, and she almost went cross-eyed looking at it, pointing right at her pretty lips.

She looked up at me, then instantly went for it—she took as much as she could, keeping her eyes fixed on me as she got about 3/4" of the way down. I could feel her throat, my heart was racing and my breath was short, and I was worried I'd cum right then and there. With only one thrust of her mouth, this was already the best fucking b.j. of my life. And Ms. Valerie only wanted more.

She wouldn't take her eyes off of me, which was hot as fuck. She played with her tits a little, and I also saw her hand go to her pussy, presumably rubbing her clit as she kept sucking me, but she was sucking my cock like it was the only thing in the world that mattered. One hand was constantly on the shaft, working it a little, then playing with my balls, then back to stroking a little, as she sucked me better than I've even see porn-starts do. Thinking back, I wish I had just pulled out my phone to record her right then and there, it was so fucking hot—but no matter, that image is in my brain forever.

I somehow held on thru this crazy-intense-and-amazing blowjob, from the sexiest, most gorgeous lady I'd ever had the pleasure of touching, on her knees, worshiping my cock for what felt like an hour (though it couldn't have been more than 10 minutes, I'm sure I would have nutted if it had been that long!), as she took her lips away long enough to say between kisses of my raging-hard, slobbery cock, "this old lady still have the goods, young man?"

"Your goods at the best I've ever had," I said breathlessly. "But I haven't sampled them all...I think you need to let me try more out."

"Oh? And what do you mean by that?"

I pulled her up, kissed her gorgeous lips and frenched her for about 30 seconds, loving that those sexy lips had just been wrapped so tightly around my dick, before I pushed her back onto the bed, then took her spot, now on my knees in front of her. I spread her thick thighs, holding her legs apart, and kissing them up and down, rubbing her stockings.

"FUCK, you know how to dress..."

"You like a lady in her pretty under-things, don't you, Monty?" she giggled. "You're quite worked up."

"YOU work me up...your sexy clothes are just an insanely hot bonus...let me show you how much you've worked me up..."

I kissed down to her panties, her underwear was now clearly wet. I ran my tongue over the wet mound, and she moaned, hard. It was incredibly sexy to hear her getting pleasure from my tongue on her...

...and she only got louder, as I pulled her panties aside, and started to lick up the full length of her slit. Her lips were visibly pulsing, she was so ready and eager, her hole so juicy I was practically drinking her as I licked up and down. I finally slid a finger into her pussy, and she moaned really hard, deep from within, "gooooooodamnnnn Monty fuck yes that pussy needs you Ms. Valerie's pussy needs that hard young cock stop teasing me and fuck meeeeeeee..."

But I kept teasing. Sliding another finger into her tight wet pussy, slowly starting to finger her, as my tongue went to her clit, lightly and insistently and rhythmically licking her button while I started to pump faster with my two fingers, my other hand holding her stockinged leg in the air, sliding up and down. She was going crazy, still begging, "goddammit you bastard fuck me, I need you to pound me fuck yes" while I kept up the fingering and the licking, until I locked in a tempo where she switched to "holy fuck fuck fuck fuck don't stop fuck yes holy fuck Monty yes fuck yes you dirty boy fuck yes fuck fuck fuck I'm cuuuummmmmmmmmminnnnnnng!!!!!!!!"

That would have been the most heavenly sexual experience I'd ever had, hearing her scream as she came, her pussy throbbing around my fingers and her juices gushing on my face, into my mouth, while I moaned and just drank it all in. That is, if not for what came next.

Valerie was sort of coming down from her orgasm, so I got up and lay next to her to kiss her, she was lightly kissing me back, still sort of moaning and grinding her legs around a little. But then her hands started to get a little more insistent, holding me tighter, then she rolled on top of me, her big plump tits pressing into my chest, her mouth on mine as our tongues twirled together. She stopped kissing.

"Bad boy. I told you to fuck me."

"I'm sorry, Ms. Valerie...you seemed to be enjoying yourself," I said, as she kissed down my chest, then took my cock in her mouth again, taking it all the way down. I gasped as she deep-throated me.

"You're lucky you can eat pussy well, young man," she said as she climbed on top of me in the bed. "But I need to see how well you can fuck."

She put her pussy over my still-stiff cock, and I reached down and slid her pretty panties to the side. "Then try it out, old lady."

She giggled at that one—playing the age dynamic with her was really hot. But her giggling stopped once she sat on my cock. She had to stop only a 1/4 of the way down, her breathing hard, before she slid up again, letting the head pop out, before she sat on me again, this time taking almost all of it, moaning the whole way.

"Fuuuuuuuuck you dirty boy your cock is so big..." as she slid up on me again.

"You make it so big, you gorgeous, sexy woman. It's that big just for your sexy fucking incredible body and your tight little pussy..."

The dirty talk worked—she obviously was loving it. She took it all the way this time, her hands on my chest, looking at me hungrily as she slowly started to grind while my cock was fully inside her, still dressed in her sexy lingerie. I was about to say out loud, thank you for not trying to take off your bra and panties, it's always awkward trying to demand my lover keep them on, but thought better of it—after all, I was getting exactly what I wanted. This woman just kept getting better. And her pussy was fucking tight...I had never been with a woman over 40 before, much less mid-50s, but she felt better than any girl I'd ever had...

So I just kept up the dirty talk. "You certainly know how to fuck, sexy lady...use that cock, exactly how you want it..."

Staring at me, those incredible eyes locked on mine. "I'm going to, young man, that cock is all mine tonight..."

"And that pussy is all mine, sweet, sexy lady...you're going to let me do what I want, aren't you, dirty Ms. Valerie..."

"I demand you do whatever you want, dirty boy..."

I grabbed her hips, and pulled her up a little, so I could get a few strokes in. Fuck, it felt incredible. She yelped a little as I did...I was worried for a second it hurt her, but she immediately went to, "God yes, fuck that pussy, I fucking need a good dicking..."

I kissed her mouth, and encouraged her to bounce on my cock. Goddamn, it was incredible...I love big women, and she was perfect, bouncing good and hard on me as I kissed her then kissed down her neck to her incredible tits, finally pulling one over the top of her bra to suck her nipple, but leaving that beautiful bra on, my hands grasping full handfuls of her luscious plump ass still her her pretty panties as she moaned how much she loved my cock...