Looking For Trouble In The Big City

I was travelling on business in New York, and decided to go looking for some trouble. To be honest, I am a pretty square guy, and my idea of trouble would be considered tame at best. I have been married to a wonderful woman for 20 years, and have no desire to hurt her or damage our relationship, and so I really like to go out and people watch. An extreme night might include some flirting, but nothing more. Then I'll go back to my hotel room, masturbate, and turn in.

I found a bar within a few blocks of the hotel and decided to walk over and get a drink. The place was called "Adventures" and walking in, I was a little disappointed to find an upscale bar, with a very business-type crowd, not very adventuresome. In my past travels, I had found that the nicer the bar, the less enticing was the people watching. True to form, the clientele were dressed in business attire, suits and dresses, very conservative. Disappointed but thirsty, I decided to stay and grabbed a spot at the bar.

I ordered a Manhattan from the beautiful bartender Kylie. A brunette with a nice rack and tight ass in yoga pants, I did my best to chat her up, but she wanted nothing to do with me. She set down my drink and walked away.

I took a sip and surveyed the crowd. Several tables full of suits having conversations I'm sure about sales quotas and annual plans. Boring. I continued searching the crowd hoping for something to fantasize about later, and while there were some attractive women, none struck me as naughty or sexy. There really wasn't much to work with for a fantasy.

I sat there nursing my drink and slowly the bar started to empty out. I was left with a few tables of what I figured were desperate men, but soon they, too, gave up and left as well. I ordered another drink as I was in no hurry. My presentation wasn't until the afternoon, and I was hoping to find some inspiration.

I looked the place over one last time and just as I was about to give up, she caught my eye. In the corner sitting all alone was a gorgeous tanned blond in a tight pink top, a knee length black cheerleader skirt, fishnet stockings and stiletto heels.

I was seated across from her, but a bit off to the side, maybe she wouldn't notice me. I glanced at her face quickly to see if she saw me watching, and then pretended to watch the TV near her. I focused on her stockings and skirt hoping I might spy her panties, creating my fantasy for later.

My good fortune, when she reached down and adjusted the strap on her shoe, her breasts fought against her shirt and I had great view of her cleavage. Her breasts were beautiful, natural and, while not huge, they looked great in that tight shirt. She moved her hands and I was drawn to them moving slowly and sensually up the stockings on her leg. Mesmerized, I stared intently as her hands moved slowly up her leg, the calf, the knee and then to the hem of her skirt.

"Please," I thought, mentally begging for a glimpse under her skirt. She stopped and massaged her thigh,and then slowly the fabric rose up her leg. I felt my cock harden and sat frozen, staring. as she moved her skirt further up her thigh. Suddenly, my prayers were answered as her skirt flipped up, exposing her pink panties with a red accent - maybe a bow? - on top. Slowly, she moved her hand toward the panties,

"Look away," I thought, but I couldn't, even if I really had wanted to. Her hand hovered over her pussy, her palm rubbing against the shiny pink panty. My cock twitched in response,

"Does she know I'm watching? Is she giving me a show or just rubbing one out in public?" After what seemed like an eternity, she stopped rubbing and pulled her panties to the side, I sat there breathless. "Please," I thought. "Please, show me your pussy."

She hooked her fingers into the side of her panties and pulled them aside. "YES!...WTF?" That was no red bow;, I looked even more intently...,

Was I seeing what I thought? Yes there, poking out of her panties was a large red dildo. She took it in her hand and stroked it. It looked lifelike (except for the color) and must've been seven inches long. She rubbed it slowly and deliberately.

I felt my cock spasm in my pants and I squirmed in my seat. She stroked the dildo up and down, up and down, up and down. My eyes followed her every stroke, and then her hand made it's way up her belly, between her breasts, and she put her middle finger on her lips and sucked it in. She pulled it out and held it right in front of her face- flipping me off.

"Fuck, busted," I thought. I looked up, our eyes met, and I was caught. She smiled a wicked smile and beckoned me to her, I blushed and turned away. I sat at the bar afraid to move, and set my credit card down hoping the bartender would process the bill so I could leave. After what seemed an eternity , the bartender came over and, instead of taking my card, brought me a drink. It was pink in color in a martini glass with a maraschino cherry.

"I didn't order this," I said hoping to just pay and leave.

"No, she did, It's a pink lady," the bartender replied with a smile.

"She?" My heart jumped as I turned slowly to look back in her direction. To my surprise, the table was empty. I breathed a huge sigh of relief, figuring she had gone and I was safe. My relief was interrupted by a demure cough behind me. I froze, and then slowly turned around to find her standing before me.

"May I join you?" she asked.

"Su-sure," I stammered, heart racing. The bartender brought her a drink, she took a gulp and smiled.

"I'm Jessie, What's your name?" she said, smiling.

"I'm Alex, look, I'm sorry..." I started to say, nervously.

"Really, you're sorry, That's not what it looked like to me."

I blushed. "I was just, well..."

"Ogling me? Getting turned on?" she asked, eyebrow raised.

"Yes, um no...I" I said before she cut me off.

"Did you like what you saw?"

I froze and was speechless. Jessie put her hand on my thigh.

"I think you did," she answered for me. "But there's only one way to tell."

Jessie moved her hand up my thigh to my now throbbing cock. "Yup, there's the answer... You liked it, alot!" Jessie smiled, squeezed my cock, and stood up. She leaned in close and whispered in my ear. "I know you think I'm pretty, and I think you want my cock." She released my crotch and sat back as if examining me. "I suppose your wife is waiting for you"

"My wife? Oh, no, I'm from out of town, business," I stammered.

She shook her head. "So cliche, horny businessman on the road looking for trouble. BUT, I think I can work with this."

She stood up reached under her skirt, pulled her panties off and put them in my hands.

"So sweetheart, If you want me, you're gonna have to work for it. Are you in for a little adventure?"

I sat unable to speak, and managed to nod yes.

"Good," she continued. "Take these, go into the men's room, and put them on. Then bring me your undies." She squeezed my cock and stroked it gently. I sat there in a daze, she grabbed my shirt, stood me up, and slapped my ass. "Go on, Alex, get your panties on and bring me my boxers"

I walked to the men's room, my cock aching and straining against my pants. "What am I doing?" I thought. "I'm not going to put on these panties."

I stared into the mirror, looking at myself standing there with her panties in my hand, my cock almost tearing through my pants. "I can't do this, I'll just call it off," I thought, but I stepped into a stall, took off my pants, then my boxers, and pulled on the pink panties.

They felt so soft, and the silky material massaged my dick with every move. I looked down to see my cock barely restrained by the skimpy panties, a drop of pre-cum bleeding through the fabric. My mind raced, the room spinning I was so drunk with lust. My cock felt like it was about to explode as the smooth panties rubbed me the right way. I pulled up my pants, put my boxers in my pocket, and walked back to Jessie. As I walked back to the bar top, Jessie turned toward me and spread her legs. I could see her pussy and the huge red cock hanging from it. I didn't know what she had in mind, but I NEEDED to find out.

"Hi honey," Jessie cooed as I walked up. "let me see them." I handed her my boxer briefs. "Thanks, honey." She smiled, took my boxers, and grabbed my cock. "But I want to see your panties. Show me.

I unbuttoned my pants and flashed the pink panties.

"Oooh, pretty!" Jessie squealed "I bet they feel great on your cock, and that thong is riding up your ass, isn't it? Teasing your tight little butt hole."

I stood there frozen, wanting to admit that the panties felt great on my cock and that I liked the thong strap rubbing against my ass hole. Jessie took the boxers, lifted up her skirt, stepped into them and leaned into whisper "Now I'm the man and you're my whore."

I stood there, lost, waiting for instruction, my cock hoping for release.

"Sit down, baby, let's take our time and finish our drinks." She patted the bar stool next

to her and I sat. She lifted up her skirt and showed me my boxers. They were too big, but her cock pressed out, straining against them. Reaching down, she started to stroke her cock through the material. "Oh, that makes me so wet, thinking about my cock and wearing your boxers. I bet you feel good, too. Tell me, sweetie, tell me how it feels."

I sat silent, and started to blush.

"Oh, sweetie," she cooed, "don't be embarrassed. Tell me, how do my little pink panties feel?

"Good. They feel good," I said in a near whisper.

"Mmm, I bet." She rubbed my thigh, the sexiness of her tone almost pushing me over the edge. "The silkiness rubbing your hard cock, the thong tickling your sweet ass." She leaned in and bit my earlobe "Do you know what I want to do to you?"

I nodded.

"Tell me sweetie, what is Jessie going to do with her slut?"

"Fuck him." I looked down.

She placed her hand on my chin, lifting my gaze to hers. "Fuck who?"

"Fuck me." The words echoed through my head.

"Fuck you where, honey?" she asked, staring into my eyes. I hesitated and she moved her hand to my cock, stroked it once, and asked again. "Fuck you where?"

"In my ass," I moaned

"And is that what you want? To be my ass slut?"

"Yes, yes please." This time I was almost shouting.

"Oh Alex, that makes me so happy, and sooo wet." Jessie finished her drink, stood up, and took my hand. "I think I've kept you waiting long enough." She led me by the hand to the ladies room. I paused at the door, and she gently pulled me inside. I started to enter a stall, but she had other ideas. Jessie led me to the middle of the room and knelt down in front of me. She unbuckled my belt, unbuttoned my pants, and then unzipped my fly. Holding my pants up, she looked up into my eyes.

"This is so hot, time to see my panties, slut." With that, she dropped my pants at my ankles and stared at me. "So pretty, look at your cock in my little panties. Oh, is that pre-cum?" she said pointing to the stain on the front. "Now turn around, I wanna see that ass."

I turned slowly and felt her hands grab my ass cheeks, massaging them, then her finger traced down my crack from the top of my back to my hole. "What a nice ass you have, sweetie, and there's that virgin butt hole. Oh, I bet it's so tight...MMM."

Jessie spun me around, pulled my cock from the panties, and started to suck me. My legs buckled, she helped steady me and took my cock all the way down her throat. Holding my cock at the base with one hand, she moved her other hand around to my ass. Without a doubt, the best blowjob I had ever had. My cock was throbbing, my mind lost in shock, was this really happening?

Her tongue and mouth felt great, hot and wet, and then suddenly I felt something warm and wet on my ass. Instinctively, I jumped. Jessie took her mouth off my cock.

"It's okay, honey, it's just lube. Trust me." She returned to sucking my cock and I could feel her index finger rubbing the lube around my ass hole. It felt great, but I felt conflicted. "Does liking her playing with my ass make me..." She slipped her finger in and all my thoughts faded away as I moaned in pleasure.

"That's it, Alex, just let it happen. It feels so good getting finger fucked, doesn't it?" Jessie stroked my cock faster and faster as she spoke. "Now, I want you to cum in my mouth."

She didn't have to ask twice as the fingering and dirty talk were just to much. I shot what felt like the biggest load of my life, trembling and swearing loudly.

Jessie took it all, then stood up, grabbed my head and kissed me deeply, forcing my own cum in my mouth. I gagged and some spilled from my lips. She grabbed my cock and put her finger on my lips to calm me. I swallowed a mouthful of cum, and she moved her finger from my lips to caress my cheek.

"That's it, Good sluts swallow." She licked my lips and chin, grabbing the cum that dribbled out. She took it in her mouth and swallowed hard.

I was spent, and as Ii wondered what would come next, Jessie put her hands on my shoulders and pushed me to my knees. "Now it's my turn. I hope you're hungry." She undid her skirt, It fell to the floor and she stepped out of it. Wow! Standing in front of me, I was awestruck by her tanned, perfect body, wearing only fishnet stockings, a garter belt, and her high heels. My jaw dropped. I have to admit, she was even hotter than I expected, and my cock stiffened again. She turned around and bent over, exposing her pussy and ass. Leaning over the sink, pushing her ass toward me, I knew what to do. I grabbed her hips and pushed my face into her pussy. This was amazing, she tasted so sweet like honey, and her cunt was so smooth and wet. I had fantasized about eating a woman from behind. My wife liked to have her pussy licked, but only in the missionary position. This sweet, sexy, amazing babe, seemed to have no inhibitions. I licked her pussy slowly bottom to top, from her clit to her opening.

"MMM, baby, that's good, just take it nice and slow. You are such a good whore."

I did this again and again, and then I went too far, my tongue grazing her sweet ass hole.

"Oh, did you just lick my ass. MMM, you're such a dirty whore. "

My fingers rubbed across her clit as my tongue focused on her ass hole, licking and darting. She moaned loudly, so I pushed my tongue into her ass and started fucking her as deeply as I could. She pushed back against my face, and I pushed my tongue in swirling it around. She trembled, so I repeated this move over and over, and as I felt her draw near, I slipped my thumb in her pussy and finger fucked her. My fingers rubbed her clit, my thumb fucked her pussy, and my tongue fucked her ass. Moaning and shaking was my reward from her and I increased the pace, rubbing and fucking her holes. She came furiously, her juices spilling all over my chin. After what seemed like an hour, she stopped bucking, shaking, and moaning and rested leaning against the sink breathing deep. I turned her around and kissed her deeply, sharing her pussy juices and the taste of her ass with her. She kissed me back, like she was starving for it. Then she pulled back stared into my eyes and said: "Wow, you sure know how to eat a woman. And thanks for sharing."

Putting her hands on my shoulders, she pushed me to my knees. I stiffened up as I came face to dildo with her massive red cock. Jessie moved a hand from my shoulder to my cheek, and then to my lips, gently pulling them apart.

"Sweetie, does my big red cock scare you?" She pushed two fingers in my mouth and slowly thrust them in and out. "You don't want to suck my cock? C'mon, you had to know this was coming, I need you to suck my cock before I fuck your tight little ass."

Hearing her say she was going to fuck my ass made my cock rock hard again. Jessie leaned forward, her cock at my lips and withdrew her fingers, inserting her cock in their place. I gagged and struggled mentally with sucking her dick. I put my hands on her hips to push her away, but then she started talking dirty again and I was too turned on to resist.

"Oh, your mouth feels so good on my cock, honey. It makes my cunt so wet, watching it slide in and out of you. I can feel my juices dripping down my legs."

Her sweet seductive voice, and the thought of making her cum, filled me with a strange desire to suck her cock. I took it all the way in my mouth and down my throat. Each time her hips met my face I could smell her sweet pussy. It was intoxicating and exhilarating.

"You're the best whore ever." she said as she thrust her cock all the way down my throat again and again.

Just then, I heard the bathroom door shut, and stopped in absolute panic. My hard on vanished, and I tried to cover it with my hands.

I must have been quite a sight kneeling there, pants at my ankles, wearing skimpy pink panties and sucking a big realistic cock.

I froze, thinking about what would happen if pictures of this went viral. "What would my wife do? Would I lose my job? And what would the guys at the gym think?"

Jessie must have sensed my fear and pulled her cock from my mouth. "It's okay, sweetie, it's just Kylie and?"

"Kylie?" I thought and turned quickly to see the gorgeous bartender and a beautiful Asian woman. My cock pulsed as I looked at the beautiful intruders.

"Oh, hey, Jessie. This is Mia" Kylie said casually, as if we were meeting at the bar top, and not in the ladies room. It was as if what was happening was completely normal.

"Well, ladies," Jessie said enthusiastically, "'you're just in time, and you're in for a real treat. Alex here is the best slut ever."

I felt myself blush, a little embarrassed, but my cock was raging hard again.

Jessie stroked my cheek. "My sweet little whore really knows how to eat pussy and ass. He's got a real gift. So who's first?"

Mia and Kylie looked at each other and then Mia spoke: "I think it's my turn first." Kylie nodded and Mia stripped off her clothes.

Now, I have always fantasized about being with an Asian woman, and seeing Mia's awesome body almost made me cum on the spot. I stood there thinking about fucking her beautiful pear shaped ass. I was lost in the fantasy as she stripped naked and stood in front of me.

Jessie's voice brought me back to reality. "Alex, honey, I want you get on your hands and knees."

I looked at her confused.

"Sweetie," she said gently, "I want to fuck your tight little ass while you eat Mia." And she guided me into the doggie position.

Mia lay down on her back, but Jessie spoke up. "No, Mia, trust me. You want to be doggie style in front of his talented tongue."

As Mia got into position in front of me, I began slowly licking her pussy from her clit up to her sweet hole. Just as I had with Jessie, I did this over and over and then let my tongue graze her ass hole as if by accident. Mia shuddered and I heard Jessie say: "Isn't that awesome? And that's just the beginning."

I licked Mia's asshole, preparing it to be tongue fucked, and just as I pushed my tongue to her ass, I felt a warm fluid dripping down my crack into my ass.

"Oh God, she's going to fuck me in the ass," I thought, and felt myself tremble. An hour ago I might have been freaked out, even afraid of what was coming next, but now I was so horny. I trembled with anticipation, more than anything I wanted Jessie to fuck me in the ass with her cock. She was right, I was her ass whore.

I felt Jessie's finger tracing my eager hole, and as she penetrated me with her finger, I froze like a statue, my tongue still buried in Mia's ass. I let out a low guttural moan, and Mia wriggled in ecstasy as the vibrations rolled from my throat, through my tongue, and into her ass.

Jessie thrust her finger in and out of my wanton ass, and I rocked back and forth in rhythm. She added a second and pushed deeper and faster. My tongue fucked Mia's ass with each thrust. For a moment, we all rocked back and forth together, Jessie's thrust controlling our bodies and Mia and I eagerly pushing back against each thrust.