Chicago Surprise Ch. 02


I woke up the next morning, and immediately thought, “please tell me that wasn’t a dream.”

I looked over, and saw the incredible curves of a sexy woman next to me, still in her light blue and white bra and matching garter belt, and dark opaque stockings. In my hand were the matching panties (seems I had been clutching them thru the night, after having spit them out after stuffing them in my own mouth during our encounter). The realization that the whole story that seemed too good to be true, that I just assumed must have been the best fucking wet-dream I’d ever had, was, actually, in fact, totally true, made my cock instantly hard. I wrapped my arm around the soft curvy lady in bed next to me, and made myself the big spoon, my hard cock pressing against her big soft ass, sliding between those incredible cheeks.

She looked over at me immediately. She wasn’t asleep! “I was wondering when you’d wake up, sleepyhead.”

“Hey there, gorgeous.” I kissed her neck, brushing her beautiful brown hair aside.

“Remember what you promised last night?”

“I thought I DREAMED last night, it was so good…but here you are.”

“You didn’t answer my question.”

I laughed. “Well, seems my dream was true. So yes, I remember.” I reached around her, pulling her toward me and making her roll over onto me. There’s nothing like a big woman on top of you, right?

She was straddling me, and instantly maneuvered to get my cock back into her, as I was already hard with morning wood after dreaming of this goddess all night. She slid back onto me, nice and slow and lovingly…that pussy as hot and warm and tight as I’d remembered…

“Mmmmmmm…that young cock is just as good in the morning as it is after a few drinks at night…”

“…and that lovely pussy remains the best goddamn feeling I’ve ever had…well, maybe your pretty mouth might beat it out, I don’t know, I might need to do another comparison, I WAS pretty drunk last night…” I winked at her, sliding my hands all over her curves, and bouncing those huge tits…

“Really? Drunk enough you didn’t realize you were fucking an old lady?”

I grabbed her hips, and thrust fully into her. She moaned. “No, just drunk enough that I need to fuck your pretty face again to get a comparison to this incredible pussy I just woke up to, sexy old lady.” I pulled her down to me, and kissed her, my tongue exploring her mouth again.

She kissed me back, hard, grinding onto me for a moment, before…

“Mmmmmm…shower time,” she said, rolling off of me.

What a tease.

“What the fuck!” I shouted.

She laughed, giggling as she walked to the bathroom, that incredible plump ass jiggling as she walked away. Looking over her shoulder, she said, “maybe you should come join me?” She winked back.

I ran up to chase her, but she locked the door—apparently just long enough to pee, start the water running, and get out of her lingerie and stockings before unlocking it, opening the door for me and kissing me hard, looking up at me with those big sexy brown eyes, then grabbing my hard cock and guiding me into the bathroom with her.

I was kissing her shoulders and back, reaching around her to play with those nice big exposed titties as she pulled me into the bathroom. almanbahis Lucky for me (both of us, really) she’d gotten a really nice suite, and her bathroom was huge, with a nice big tub that could probably fit four people comfortably. It was already half-full, and she turned on some jets so it started to bubble. She stepped in, and slid her nice big sexy body into the water, her huge tits bouncing along the top of the water.

“Come on in, young man, it’s nice and warm—and I want to suck that cock again, but not until you clean it a bit,” she winked.

I jumped right in, splashing her as I did. She laughed and giggled—how the hell was this woman in her 50s? She was acting like a horny, adventurous 18-year-old, but with the sexy mature curvy body of a woman who hows exactly how to please a man, which just instantly drove me even wilder. I grabbed the hotel soap, pulled it out of its paper, and immediately pulled it under the water, imitating a silly scene of “washing my dick” with it before throwing it back onto the side of the tub and lunging at her.

“Ok, it’s ready!” I said as I got on top of her in the tub, the warm water around us, kissing her pretty mouth again and feeling, once again, like, holy shit, how did I get so lucky, this woman is insanely fucking gorgeous.

She was laughing thru the kiss, but pushed me off, saying, “nuh-uh, dirty boy, we’re going to do it right.” She grabbed the soap in her hand, pushing me back to sitting in the tub, then brought her soap-filled hand down under the water to run the bar of soap up and down my still-hard cock, teasing my head and then down to my balls, before dropping the soap and just slowly stroking me. She was looking into my eyes the whole time, smiling that gorgeous smile I remembered from the very first time I saw her the night before at the hotel bar.

“How’d I get so lucky?” she said in a beautiful, loving voice, looking into my eyes.

My eyes went wide. “YOU, lucky? I’d say I’m the lucky one, gorgeous.”

“Oh c’mon, you fucked an old lady!” she laughed.

“No, correction: I got to fuck a gorgeous, beautiful, mature woman, who fucked me better than any woman I’ve ever had,” I smiled at her, and leaned in to kiss her, moaning as I got to touch those luscious lips again, her hand still slowly jerking me under the water. “And I really hope I get to fuck her again…”

“Oh you better,” she winked at me. “You promised.”

“Am I clean enough, now?”

She laughed, then looked into my eyes, her tone shifting from playful to lusty. “You could have fucked my face the moment I woke up and I wouldn’t have cared, that big young cock is so nice…”

“Well that goes equal for you—I could have woken up to that hot pussy sitting on my face, still wet from getting fucked so good last night, and I would have eaten you out like a fucking madman…”

She lunged in and kissed me hard, pulling me toward her soft body. I held myself up on the edge of the tub, my cock pressing against her belly until she reached down and started to stroke me again as she held my stiff dick against her soft skin. I love when a woman grabs me, and her grip was the perfect mix of insistent and tender…just fucking amazing.

I pulled myself up on the rim of the tub again, planking my body so my almanbahis giriş cock was right between those soft, massive tits, and started sliding back and forth. She kept her eyes on me as I titty-fucked her, her mouth agape and moaning a little, her tongue darting out to lick the head each time I’d thrust up. Her hand was at her pussy, and she was working her clit as I worked her tits.

“God those tits are so fucking marvelous…”

“You like them dirty boy?”

“Fuuuuuuck yes Valerie I love those nice big soft titties…feel so fucking soft…mmmmm…”

“When you promised to fuck me, I didn’t mean titty-fuck. But then again, that hard young cock does feel nice there…and it’s hot to watch you enjoy my breasts…plus I get to lick that fat dick a bit more…”

She reached up and grabbed my ass, pulling me away from her tits and guiding my cock to her mouth, then pushed me all the way down her throat. Fuck, this lady could deep-throat…and she kept looking up at me the whole time.

“Holy shit, baby…goddamn that mouth is fucking magic…”

She popped it out of her mouth, still squeezing my ass with one hand and working her clit with her other. “Time for your comparison?” she winked at me.

After putting it down her throat a few more times, she grabbed my hips and guided me back down into the tub with her, the jets still going, her voice still purring as she spread her thick thighs and invited me in. I didn’t waste any time plunging into her again, the second time that morning, and already having her last night, but still instantly going wild at the sensation of her wet warm tight little pussy.

“Mmmmmmmm…fuck, Ms. Valerie, that pussy is divine.”

“Mmm, so’s that hard cock, young man…but which is better? My mouth or my cunt?”

She started to work her muscles in her pussy, massaging my dick with her canal. “Fuuuuck…”

“Hm? Which, dirty boy?” Those sexy eyes looking at me, still hungry…

“I think Ms. Valerie is a goddess, and any way she allows me to touch her or fuck her is the best fucking feeling I could possibly have…” I said as I started to thrust into her, nice long strokes.

She loved that. “Mmmmmm…” her eyes rolling back into her head. “That’s the right answer, that’s a good boy…now fuck Ms. Valerie good…”

I kept at it, missionary-style, just enjoying the feel of her sexy plump curves in my hands, the water swirling around us, the feel of that tight pussy as I worked in and out of her—and of course, going wild for the look of this gorgeous woman looking at me as I enjoyed her incredibly sexy body. We fucked like that, staring at each other between kisses all over both of our faces and mouths and necks and chests, for probably a good 20 minutes—I held off on my orgasm as long as I could, just not wanting this incredible pleasure to end…

That is, until she reached down, and started to rub her clit again. “Mmmmm…my hot young stud, I want to cum with you inside me…and I want you to fill me up…will you do that for me?”

“Anything for you, Ms. Valerie…”

I kept up the speed, increasing it only slightly as she started to work her clit—after fucking for so long, it didn’t take her long to start to get short of breath. She was about to cum, and almanbahis yeni giriş watching that pretty face start to feel the orgasm building up in her was just insanely fucking hot. “Mmm, Ms. Valerie, cum for me…you look so sexy, you look like you’re really enjoying this young cock, are you, Ms. Valerie? You like how I’m fucking you?”

“Ohhhhhhhh my god yes Monty holy shit…god yes, fuck me, baby, fuck me, don’t stop, just like that, don’t stop, keep going, yes yes yes yes yes…”

Her fingers now whirling around her little clit, staring at me, practically screaming as she came around my cock as I kept up the speed of fucking her…but watching her cum like that was too goddamn hot, I needed to cum, too. I didn’t change speed, but rather enjoyed those nice long strokes as my balls tightened and I started to make a lot of noise myself…”

“Fuuuuck you are so sexy, Ms. Valerie, you look even more gorgeous while you cum from taking my cock…fuuuuuuck…you’re sure you want me to cum in you?”

“YES, fuck yes, Monty, I demand it, give Ms. Valerie all that young hot spunk, fill up my pussy with it I want it I fucking need it you dirty boy fuck me fuck me cum in me fuck me fuck fuck me give me all your hot young cummmmmmmmm…”

She was still coming down off her orgasm as I started to spurt in her, and the feeling made her start cumming again, both of us screaming in ecstasy…I think I heard the door getting knocked on while we did, presumably by hotel staff getting noise complaints, but neither of us bothered to acknowledge it, we were just so engrossed in each other…

I kissed her hard as we both came down, my body on top of hers in the water…we kind of snuggled there, enjoying the jets on our beleaguered bodies.

“Holy shit…my old hips haven’t had this kind of action in a long time…I’m going to need a vacation from this vacation…”

I laughed at her, and kissed her hard, but lovingly. “You could always come to New York” I winked at her.

She laughed back, that sexy, school-girlish giggle of hers. “Then I’d need a vacation from that vacation!”

“Sure…we’ll meet up back here in Chicago again!”

We both laughed, and held each other. Then a terrible idea popped into my head.

“Ooooohhhh fuck. What time is it?”

“I’m not sure…I was too distracted by a young man with a hard cock to pay attention to the time…”

I jumped up out of the bath, spilling water everywhere, and checked the bed-side clock—9:35. My first meeting was at 10.


I grabbed my clothes, quickly throwing on my pants (no underwear) and just my under-shirt. As I was running for the door, my lover was standing by the bathroom door, smirking.

“Fuck & run, huh?”

“Only because I’m supposed to be 14 blocks from here in 25 minutes, and I’m still un-showered!” I grabbed her around the waist, and pulled that gorgeous plump body to me, my hand sliding down to get a full handful of that incredible ass as I kissed her. “When do you leave?”

“I’m supposed to be heading home Friday…but maybe I could extend until Sunday…” she smiled.

This was only Monday—but I knew I needed this goddess all week, as much as possible. “Do it,” I said. “I’ll be sure you’re taken care of,” then kissed her again.

I ran back to the desk in the room, and scribbled my cell # on the hotel stationary. “Text me, lover.” I kissed her quickly, spanked her ass (and admired it jiggling for just a moment) before running out the door.

Bir yanıt yazın

E-posta adresiniz yayınlanmayacak. Gerekli alanlar * ile işaretlenmişlerdir