I went down to the hotel bar to relax. It was early (barely 5 PM), but I didn't have anything else to do, and I figured I might find somebody interesting to talk to. As I walked in, I noticed a woman sitting at the bar alone. She was neatly dressed in a tight blue blouse, a black skirt that came about half way down her thighs, and black heels. From the back, I could tell that she was curvy, with thick thighs and an ass that was stretching her skirt wonderfully. I sat down a couple seats down, said hello, and ordered a double bourbon. As I sipped, I noticed the ring on her left hand, and I couldn't help noticing her cleavage. Her blouse was so low cut that I was surprised she wasn't showing her nipples, and so tight that her breasts were practically jumping out onto the bar.
Her glass was full of a brown liquid - probably an amaretto sour or something similarly sweet, I figured. I asked what she was drinking, and pleasantly shocked when she said "Same as you, honey. Bourbon on the rocks."
"Wow, I'm impressed," I said. "Most women can't handle a drink that strong. May I buy you another?"
She looked down into her drink, talking to it as much as to me. "I'm not most women. And yes, I'd love another!" She turned to me and smiled. "but only on one condition. You'll let me buy the next round for both of us."
An idea flashed into my mind, and I figured I had nothing to lose. I ordered another round for each of us, then said to her, "Let's play a little drinking game, shall we?" She gave me a smile and a curious, look, so I continued. "When we're done drinking, we'll go someplace private. Every round I buy you, you have to take off one piece of clothing. Every round you buy me, you can buy it back, or make me undress too. Sound fair?"
She turned to face me and leaned over a little, putting her amble cleavage to good effect. "So, basically, it's like strip drinking, right? The goal is to get d***k and naked, or at least very d***k?"
I smiled. "Pretty much. Both sound good to me tonight, especially with you. So, what do you say?"
She grabbed a napkin, and took a pen from her purse. "So, right now, I owe you one article of clothing, and I'll even the score with the next round. Do we decide now how or score is settled, or wait until the end of the game?"
"Ladies choice, but I'd just as soon wait and see. Why spoil the surprise?" Besides, I figured, if she's d***k enough she might make a different choice later on. So, we kept score on the napkin as we sat and talked. I pointed to her ring. "Are you here alone?" I asked?
"Business trip," she said. "Another boring fucking business trip. Meetings, conferences, meetings, blah blah blah. And If I have to sit through another goddamn Powerpoint presentation, I think I'll kill myself. But, fuck that shit. I'm here and having fun! And you? I'm not the only one with a ring on, I see."
"Work, like you. I travel a lot. Different hotel every night. My wife loves the money, and just between you and me, I think she's glad to be rid of me. But, like you said, fuck that shit! I'm having a great time with a gorgeous lady!" I ordered another round, and made a mental calculation that I ought to have more than covered every article of clothing she had on, unless she was wearing a bunch of extras I couldn't see. I glanced at the clock. "Do you realize it's almost 10:00? It feels like we just got here. I guess time really does fly when you're having fun."
She picked up the napkin and looked at our score. "One more, and we're even, baby!" She ordered another round. "What do you say we head upstairs and settle up?" After finishing our drinks, we headed up to her room. She sat down on the bed, I on the chair facing her, and she slipped her heels off, showing off her curvy legs and black stockings. As she raised her leg, I thought I caught a glimpse of a stocking top. "So, I figure that's two, right?" She kicked her shoes toward me playfully" One, two. So the question is, do I put them back on, or make you take something off?" She turned and put her stocking-covered feet in my lap, rubbing my crotch through my jeans. "Take something off! In fact.. " she glanced over the tally sheet, and at me, "you're going to have to take a LOT of somethings off! So come on, mister, strip! I paid for your nudity, and I want it!"
"I like your style of foreplay," I said, as I removed shoes, socks, and began unbuttoning my shirt. "But what about you? If you're using all your credit to get me naked, that means you're going to have to get naked as well. I'm not going alone here."
"Don't worry about that! I've always had a fantasy of being a stripper. But I want you naked for me first. Just to prove that I don't mean to hurt you, "she dropped to her knees in front of me, and began unbuttoning my jeans as she spoke, "I'll give you a little present." She opened my fly, pulled my cock out, and swallowed it, balls deep, then pulled away slowly, sucking the tip so hard I thought she'd pull my eyes down through my crotch. "There, how's that? You believe I'm playing fair now?" I stood up and stripped in front of her, taking care to pull a couple condoms out of my wallet as I pulled my jeans off.
When I was naked, she sat me on the edge of the bed, then stood over me. "I don't really know what I'm doing, so bear with me, baby." As she spoke, she straddled my legs, rubbing her skirt against my prominent erection. Slowly, she lifted the hem of her skirt, exposing the lace tops of her stockings, and then the faintest hint of black fabric covering her crotch. She pulled away, and leaned in close, letting me look down the top of her blouse. As I had suspected, she wasn't wearing a bra, and as she pulled the neckline down I saw her dark aureoles surrounding her large, firm nipples. "You like them, baby? They're all natural, I promise." She lifted her blouse and stood over me topless, her large breasts sagging just enough to tell me they were real. "Go on, suck them! I love having my nipples sucked."
She leaned in again, and I tenderly caressed her breasts, pulling my mouth up to first one nipple and then the other. Her skin tasted sweet and felt soft and supple, and her gentle moans as my tongue played around her nipples drove me mad. Then, slowly, she pulled away and turned around. She backed up to me and rubbed her ass against my naked lap, then pulled her skirt up again. This time, instead of teasing me with a hint of a peek, she pulled her skirt up around her waist, exposing two soft round ass cheeks with just a black g-string hidden between them. She rubbed her ass against my cock slowly, and then leaned forward, letting me see the little patch of fabric covering her pussy. She reached down between her legs and massaged my balls, then my shaft, and then barely pulled her g-string aside. Her outer labia were fat and juicy, and sopping wet as she rubbed them against my shaft. She pulled away slightly, then took both hands and pulled her g0string down over her ass until her pussy was only loosely covered.
She got up, ass exposed, g-string still on, and got one of the condoms. Holding the tip between her lips, she knelt in front of me, pressed the head of my cock into the condom, and unrolled it over me. Then she pushed me back onto the bed and crawled up me, rubbing my erection between her generous tits before straddling my lap. "Don't say a word, baby. You don't love me, I don't love you. We're going to spend the night together and fuck like mad, and tomorrow morning we'll go our separate ways and never see each other again." As she said that, she pulled her g-string aside and nestled herself onto my cock, the head of my cock buried between her fat cunt lips. By the time she'd said we'd never see each other again, I was balls deep inside her.
It had been so long since I'd been laid that I lasted only a few minutes. The sight of her thick naked body riding me, and especially her in her stockings, was more than I could handle, and I came hard. "Good!" she said seductively. "Now that that's out of the way, let's really have some fun. She got up and then turned around on the bed, with her freshly fucked pussy inches from my face. "I hope you like 69?" As an answer, I rolled over to face her and buried my face in her mound. Her neatly trimmed landing strip tickled my chin as I lapped at her slit. She pulled the condom off and began gently licking the cum from my half-erection, avoiding the head until I was hard enough to take it again.
It was a recipe that worked, and she knew it. We spent the next several hours trying every position we could think of, and every time I would cum she would feed me her now gaping and sopping wet cunt, while lovingly resurrecting my cock. Eventually, we both drifted off to sl**p, my cock nestled between her soft ass cheeks. A couple times in what remained of the night I woke up hard as a rock, slipped a condom on, and fucked her silently, then went back to sl**p. In the morning, we showered together and went down to breakfast. We made small talk over coffee, and something occurred to me. "You know, I never asked your name." I held out my hand in a mock introduction. "I'm.."
She stopped me with a dainty finger over her pursed lips. "Don't. Let's keep it the way it is, just two strangers in the night." She got up and kissed my cheek softly. "Thanks for making a fantasy come true, baby. I'll never forget last night."