A Miss Understanding

It was Friday night and I had no plans. I'd broken up with my girl friend a few weeks earlier, and had been wanting to play the field. I decided to go and get a couple drinks at my favorite dive bar downtown. It was a local pick up joint, and it was where I had met my former flame. I wasn't really looking for love, more like a good buzz and a quick fuck.

I had been nursing a bourbon and soda for a couple of hours waiting for an opportunity to present itself (or herself), but it was getting late and I was starting to think that internet porn was my only option. I finished my drink and was waiting for the bartender to cash me out when she walked in and sat down next to me.

She was gorgeous, a petite babe with huge tits, a small waist and an ample ass. It was like someone had drawn the perfect female form. Her face was naturally beautiful, and although she used a little makeup to accentuate her features, she really didn't need makeup. She had amazing green eyes that lit up the room like emeralds on fire. I bet she looked as beautiful waking up as she did after dolling herself up. She was a dream come true, but there was one thing that was a bit of a red flag. Her clothing, if I had to describe it, I would say it was masculine. It was a business suit, but it was a man's. Yeah, she dressed like a dude, and she had one of those pixie cuts that could be feminine or masculine. Her auburn hair was the perfect shade to offset her, light skin and green eyes, But it was short like a guys.

As beautiful as she was, I figured she wasn't interested in what I had to offer, and set down my card to pay. She looked me up and down like she was measuring me and smiled.

"Giving up there champ?" Her voice was sweet like honey, and a little raspy or sultry, whatever it was sexy. She spoke with a calm and confidence that told me she knew how hot she was.

"What? I, um, well I guess you could say that." I was caught completely off guard and didn't know what to say or do.

"Are you sure that's what you want to do? Why don't you let me buy the next round?" She slid my card back towards me. "Nice to meet you, I'm Karyn."

"Well, if you're buying, I'll drink. I'm Alex." I picked up my card and put it in my pocket.

"Good boy Alex. I could use the company." She motioned for the bartender and he brought us another round. "What are we drinking?"

"Manhattans." I picked up the glass and took a swig. "God, I love bourbon."

"Oh yeah, tell me more. What else do you love?" Her words were soft and genuine, and i felt at ease like I had known her for years.

We spoke for what seemed like hours and hours. We opened up to each other. I told her about my recent breakup, and we played a crude version of truth or dare. It was really more like truth or drink, and I was unaware of the real game that was being played. A few Manhattans later, the game was getting pretty risky.

"Okay stud, Truth or drink?" She smiled and ran her finger along the rim of her glass and then sucked it seductively while staring in my eyes.

"Truth?" I said nervously.

"What is the kinkiest thing you have ever done?" She took a gulp of her drink, and slid her hand into her pants.

I was awestruck watching her, she was beautiful, sexy and sensual. She had a grace and strength that was unlike any other woman I had ever met. She moved her hand up and down in her pants, like she was masturbating, but not like a woman. She was moving her hand up and down like she was jerking off her cock.

I must've had a pained look on my face as I struggled to make sense of her movements because she stopped and looked me in the eyes. "Is this to much for you stud?"

"No, well, I um, I. Well, it's just that. Are you packing?' I fumbled and stammered to answer confidently, but I couldn't. I was rattled by her motions and the thought that, well that she had a dick.

"Am I packing?" She asked me like she was confused, but something told me she understood the question. "Am I packing? Hmm. You wanna a shot?"

Her question hit me as both a question and a statement. I sat confused temporarily trying to determine a witty response.

"Is this too much for you stud?" She asked again knowing she was pushing me past my comfort zone, and she knew she was completely in control.

I took a swig of my drink trying to but some time, and gain my composure. "Too much for me? What do you mean by that?"

"Well" she swallowed that last of her drink in one gulp, "I know that some men find dominant women, well difficult." She smiled and grabbed her crotch again.

"I don't have a problem with strong willed women." I smiled and spoke confidently.

"Alex, honey." She leaned in her boobs fighting against her shirt to break free, and her emerald eyes sparkling at me. "I didn't say strong willed, I said DOMINANT!" She grabbed my balls and gave them a squeeze. I almost jumped out of my chair. It hurt, but felt good in a different way. My cock jumped and started to stiffen.

"Oh baby." She cooed, her word were soft and sweet like honey dripping on my ears and slowly flowing over my entire being. "Do you like it when I squeeze your balls? Do you like the pain?"

I felt the blood rushing to my face and realized I was blushing. "I, well I um." I struggled to find words to express my feelings. "Look, I know this is just a game to you and well, well you have no interest in me."

My words hit her hard and caught her off guard. "No interest? Why would you say that?" She looked confused.

"Well" I paused "Look at you, your dress and well, whatever that is in your pants. It screams lesbian, and don't get me wrong I'm not judging, but well."

Karyn laughed hard, and took a swig of her drink. "Oh sweetie, you've got me all wrong." She grabbed at the appendage in her pants. "I don't want to fuck women, I want to fuck a man." Her words were both sweet and powerful and once again my cock throbbed.

"Well, that's cool cuz I want to fuck a woman." I smiled and stared into those emerald eyes. I was feeling pretty good, I had her right where I wanted her.

She Laughed loudly, and leaned into me so she could whisper in my ear. "No stud, I don't want to get fucked by a man, I want to fuck a man. Have you heard of role reversal? I am the fucker, and he is the fuckee."

I don't know if it was the liquor, or I just wasn't able to comprehend what she was saying, but I was completely lost. She must have sensed this, because she leaned in, kissed my cheek and took my hand. She guided me to her crotch and pressed my hand against her strap on cock. It was... HUGE. I jerked my hand back so hard I almost fell out of my chair.

"Easy big boy." Her words were both soothing and commanding. "Take a breath baby, just relax. I want to fuck you, I want to fuck you in the ass." She smiled and winked at me "but don't worry I won't hurt you."

I sat there on my bar stool, trying to understand what the fuck was happening. On the one hand there was this beautiful, crazy chick with a plastic dick looking to fuck a man something I wanted nothing to do with. On the other hand my cock was throbbing and oozing pre-cum at the very thought of how sexy this woman was. My cock pressed hard against my pants exposing my true feeling and leaving little to the imagination.

"Well stud, it looks like you're more than just a little interested in getting fucked." Her words echoed through my head and then the feeling rippled through the rest of my body electricity bursting through every cell. She grabbed my erect cock and held it in her hand. "Well stud, do you want to be my little slut? She whispered, but I felt as if she were shouting. My face flushed red and i could feel the sweat beading up on my forehead. I looked around the room to see if anyone else heard what she had been saying. "Relax honey, it's just you and me here, they're all in their own little worlds." It was as if she knew what I was thinking.

"Don't worry about me babe, I'm Fine." I spoke with a confidence that I didn't have, but unless she really could read minds, there was no way she would know. I finished my drink, and looked her in the eye. "Look this has been fun, and I appreciate the drinks, but I'm not your man."

She faked a smile, but I could see her disappointment. "Okay, I understand, but before you go, I would like to make one more...offer." She motioned for another round, and the bartender brought another couple Manhattans. "Look, I really like you and I think you like me."

"Yes, I do like you Karyn." I paused.

"Well then" She interrupted "Here's an offer you can't refuse, or at least you shouldn't" She ran her hand over her breast, down her stomach and into her pants. I couldn't see her fingers , but it was obvious she was rubbing her pussy. She closed her eyes, took a deep breath and then brought her fingers to my nose. The smell was intoxicating like a mix of Riesling and honey. I opened my mouth, and she pulled her fingers away and sucked them dry while staring into my eyes. "Mmmm." She moaned loud enough that the she got the bartender's attention. She giggled, and waited for the bartender to return to work. "I'll let you have me, any way you want." She paused, glancing at my cock and measuring my reaction. "That's right stud, I'll be you're slut. You can FUCK me any and every way you want." She emphasized the work fuck in such a way that it sounded both naughty and dirty. "If." She placed her hand on my thigh and slowly moved it up to my crotch. She gently patted my cock. "If, you're willing to be my little slut. You see what's good for the goose." She squeezed my balls and smiled.

My cock jumped and pre-cum oozed out, I pictured my cock buried all the way to the hilt in her ass as she climaxed in a screaming orgasm. FUCK! I really wanted to taste her cunt too. But, was I ready to be her little bitch?

"So sweetie, I can see you're thinking about what you would do to me." She licked her fingers again to remind me of the sweet aroma of her cunt. "I would love to know what you're really thinking. Is it fucking my face? Are you dreaming of stuffing my pussy? Or do you want to shoot a huge load in my tight little ass?" She closed her eyes and tossed her head back mimicking rapture. "I'm thinking about sitting on that face. Rubbing my sopping cunt all over your mouth, your tongue darting over my clit and then plunging into my hole. Maybe I make my slut eat my ass. Mmmm, Fuck I think you'd like that, I know I would." Her voice was part whisper and part moan. It was seducing, controlling and I was under her power. After a few moments that seemed to last forever she spoke again. "Well stud, what do you say? I'll give you mine, If...You give me yours."

"Yes, I'll give you what ever you want." I spoke with out thinking. The words came from deep inside me, a new place. An unknown side, fueled by lust that wanted to fuck and be fucked. I was desperate for her, the scent of her cunt filled my nostrils and rocked my brain. My cock throbbed and leaked. I was so horny, I would've done anything. Anything.

Karyn took my hand and held up her credit card. She paid the bill and led me out to a taxi. I sat there my head swimming from the combination of alcohol and lust. Karyn reached over and grabbed my cock and then took my hand and led me to her cock. She locked eyes with me and slowly started stroking my cock and guiding me to stroke hers in time. It felt so good to finally get some attention but it was just enough pressure to tease me not relieve me. "Not yet sweetie, there's so much I want to do with you."

Karyn kept the teasing up for the whole trip to her hotel, and then paid the driver and led me to her room. It was an executive suite with a king sized bed. She sat me down on the bed, and stepped back out of reach.

She took off her it coat and let it drop to the floor. Then she loosened her tie, lifted it over her head, and slowly unbuttoned her shirt. She turned her back to me and dropped it to the floor. Her red bra contrasted against her creamy pale skin. She then unbuttoned her pants and bent over almost touching the floor. The cheeks of her ass pressed against her slacks taunting me, as if begging for me to grab them. I sat there in awe staring at her, undressing her in my mind as she slow stripped. Then she dropped the pants and I saw what i can only describe as the perfect ass. She had a red thong that matched her bra. It rode up in between her perfect ass cheeks and disappeared between them. a small patch of cloth hugging her pussy lips. She reached behind and undid her bra, dropped it to the ground and then slowly turned to reveal her big beautiful breast. Her nipples were large, and pierced with rings could easily be chained. She cupped her breasts and then moved her hands down her body to her panties. Slipping her thumbs into the waistband, she slowly dropped them to the floor. Her pussy was magnificent. Shaved except for an auburn landing strip, her labia glistened in the soft light. She walked slowly to me, put her hand in my chest and pushed me back on the bed until I was lying on my back. She then climbed up until her cunt was right above my face. She stopped for a moment. "I'm all yours stud." Then she lowered herself onto my face. Rubbing her cunt up and down on my tongue from he clit to her soaked opening. She rode me like a mechanical bull her juices soaking my face. I grabbed her hips and moved her ass to my mouth, flicking my tongue on her tight little rosebud. She moaned and ground her ass into me and I took the hint licking and thrusting my tongue around and into her beautiful ass. The more I tongue fucked her, the louder she moaned and the more she ground into me until she began to tremble and moan.

She came screaming, and collapsed falling forward her sopping cunt just in front of my mouth. I realized it was her turn to be the slut and I lifted her from my chest and moved around behind her. I rubbed my rock hard cock up and down her slit and then thrust forcefully into her. I stuffed my cock all the way inside her and she moaned in pleasure. I slowly withdrew and then plunged back in. Even though she was soaking wet, her cunt was gripping me tightly. I began to fuck her slow and deep. She moaned loudly with each thrust and fucked back against me more and more furiously with each thrust. I sped up and thrust in deeper and harder. Karyn's breathing began to quicken and her moans grew louder and louder. I took my thumb and massaged her asshole, I spit on it and slipped it inside her. She grunted loudly, whimpered and then began fucking back against me again. I timed the thrusting of my cock and thumb to simultaneously fuck her cunt and ass ad she loved it.

"That's it baby fuck me like a cheap slut! Finger fuck my dirty ass!" Her words were mixed with moans and gasps. I increased the speed and intensity of my thrusts as I fucked her holes. I wished I had another cock to stick in her mouth, but as much as I wanted to make her swallow my load, I really wanted to fill that tight ass. I longed to see my seed drip out of her forbidden hole and cover her cunt. She began to tremble, shake and then spasm as she reached another climax. I pulled my cock from her cunt and pushed it into her tight little ass.

Caught in between the pleasure of her orgasm and the initial pain of anal penetration, Karyn cried out. "Fuck, oh FUCK! Is that your cock up my ass? Oh my GOD I'm cumming with your cock in my ass!" She looked back at me over her shoulder. "Fuck it, FUCK MY ASS! Fuck my dirty hole hard and fill me with your cum!"

I slammed my cock all the way in and started thrusting hard and deep. I grabbed her hips for added leverage and pounded her ass like it was a punishment. She grunted, whimpered and moaned and began screaming as she neared yet another orgasm. "Oh, oh yes. You're gonna make me cum again! Fuck my ass with your big fucking cock, stuff my dirty hole, fill me with your cum." She slammed back against me as I thrust into her and her sphincter gripped me tight as she came. I took one last thrust and felt my load explode from every inch of my body through my cock and into her tight fucking ass. It was amazing, the feeling was like I've never felt before and my orgasm was so powerful, I thought I might pass out. My cum shot out of me with a force that felt like it might tear my cock in half. The mix of pleasure and pain was intoxicating. I collapsed onto her back, my cock throbbing inside her and her ass milking every last drop of sperm from me. Every inch of my body my tingled and my brain was shot lost on trying to make sense of all of the sensations I was feeling.

After what seemed like hours, but was probably a matter of minutes, Karyn pulled away and my cock popped out o her ass. I stepped back and watched a big spurt of my cum pour out. It was a beautiful sight to see. She took her hand, cupped it and scooped up the cum. She looked it over and then licked it up. She placed her hands on my hands on my shoulder and pulled me to her. She pressed her lips against mine and forced her tongue and my cum into my mouth. This was by far the kinkiest and nastiest thing I had ever done. Swallowing my own cum from a woman's ass, and I loved it. My cock spasm-ed and began to stiffen. I was ready for another round. I ground my cock against her cunt.

Karyn pulled away, clearly she had other ideas. "Not so fast stud. It's your turn to play the slut." She whispered, but her words echoed in my head. She walked across the room to her dresser and opened the top drawer. She rifled through the contents and then turned around victoriously. Smiling she held up a soft pink, satiny thong. "This will make that sweet little ass of yours look so good." She held them out to me, and when I hesitated she grabbed my balls. Squeezing gently she spoke in a soft but commanding tone. "Listen to me , you're gonna do what I say like a good little whore, or I'm gonna call the cops and say you raped me. So sweetie, what's it gonna be? Do you want to be my little panty wearing ass whore or some prison bitch? Either way your ass is fucked...literally." She was right, I was fucked. Well, at least I was about to be.

I took the panties and stepped into them. It was immediately emasculating. I looked down at myself, the panties looked silly and out of place. My unshaven legs contrasted hard against the soft shiny pink fabric. I looked like a joke and my once proud member was shrinking from the experience. I wasn't ready for the humiliation I was having to face.

Karyn must have sensed my feelings, or maybe she had experienced this with "other" lovers in the past. She stepped up to me, kissed me and put her hands on my shoulders. Then she leaned in and started whispering in a sexy, sweet and low voice. As she did this she slid her hands down my back to my ass and cupped my cheeks. "Oh baby, you look so good in those panties. I hope they feel as good as they look." She nibbled my ear and licked my neck. "Does that satin feel good wrapped around that big cock of yours? It's so big, I bet they can hardly contain you. Are they rubbing up against you? Massaging your big cock with that silky cloth? Mmmm, I bet it feels good." Her words changed my focus from how I embarrassing the panties looked to the physical feelings of wearing them. She pulled my ass cheeks apart and nibbled my ear. "And I just love the way a thong feels on my asshole, rubbing it, teasing it when I move. Reminding me of the pleasure that's yet to come." She took a finger and traced in down my crack to my hole and gently massaged it. My cock sprung back to life almost fully erect from her word and massage of my asshole. Suddenly, like a switch was flipped, I was no longer wanting to resist her or to just get this over with. Something inside me embraced the thought of being her panty wearing ass whore, and I wanted to experience this. No, I NEEDED to experience this.