2 comments/ 26452 views/ 1 favorites Midwestern Mystery Woman By: djm298 "She's really nice. We met her this weekend at the picnic. Her brother is on the planning committee with Tim." I continued to read the e-mail message from my sister, noting the phone number and name, Kristen. Apparently, she had just moved back to Chicago from Baltimore, where she lived for a couple of years. Every once in a while, I would find one of these notes from my sister in my inbox. It was part of her continuing effort to fix me up, transform me from lonely, single, urban guy. At thirty-six, I suppose the sting of single life grew stronger, making that subtle transformation from freedom to desperation. I shouldn't complain, for I had my share of fun when I was younger, as well as a few opportunities to take a relationship further, as in commitment. But, that was then. Now, it is the occasional fix-up. That was all I got. I didn't blow off these arrangements; it's just that my attitude was clouded by experience. I would send my sister a thank you note and contact the woman in question. Then there would be a meeting and likely no physical connection and little in the way of rapport. It's not my sister's fault. She just doesn't know me. I could tell her my type, but that would involve a long, intimate and involved discussion. Something we didn't do and that wasn't in accordance with our relationship. The subject of what I find sexy. That alone could be nettlesome. Perhaps, I should just show my sister the stories I've written for Literotica. Oh yeah, that would work. Hah! I laughed to my self at the absurdity of the thought. In short, I am open minded, liberal and a curious person. When it comes to sex, you could say I was a bit kinky. Not that I'd had a lot of experiences, but all the women with whom I'd had satisfying relationships were somewhat the same. The women with whom my sister set me up with usually were boring, conservative, corporate drones. Kind of like my sister. We would meet for a coffee, a polite chat ensued, then we would make vague promises to send e-mail and that was that. Neither party enthralled. So, there I was at the coffee house, on a warm summer morning in Chicago, waiting for a vaguely defined person. Surely this was she. A woman who looked to be in her early thirties, just above the shoulder blonde hair and WASPY good looks (think soccer mom in the suburbs) approached me. "Andrew?" I smiled and stood up. "Yet, but please call me Andy. You must be Kristen." I extended my hand, noting her long, slender fingers. Sure enough, a pleasant conversation followed. I would like to say that it was markedly different from the dialogue of other blind dates, but it wasn't. She spoke of her childhood in Indiana and despite her being an accountant she told few tales from the controller's office. But, there was a notable exception. Actually, a few. First, her eyes lingered on mine just a little longer and she seemed in no hurry to go somewhere else. Also, she had very nice legs - long, well shaped, with slim ankles. This last part was noteworthy, for with the other women with whom I was fixed up, I never had the inkling of sexual thoughts. That alone can tell you something about the stilted, awkward nature of my recent experiences. Yet, while I admired her legs, that was as far as it went. She spoke of her undergrad years at the University of Indiana and not the barest hint of a wild streak crept out. She was nice and friendly, though. Not hardened and bitter as far as I could tell. We spent the day engaged in chitchat while we walked all over Lincoln Park and Lakeview. In the next few weeks, we would meet for lunch or a drink every few days. Our meetings remained pleasant, but always slightly awkward. Mostly, because she spoke so little of herself and of her recent past, while I babbled on about anything, volunteering information about myself since she asked so few questions of me. I inferred she was politically conservative, and all that implies, since her dad was in the military and she was raised in Indiana, a mostly Republican state. The less she spoke of herself, the more curious I became. It was striking how blatantly she avoided certain topics. For instance, I asked her why she had moved to Baltimore (never mind why she returned - that didn't seem likely to get a response). She said her mother had family in Maryland and "that was the past, now I'm here. Oh, look at how the weather has changed." Just like that. I almost chuckled, but noting her earnest demeanor, I didn't push it. Her attire didn't give me much in the way of clues, either. Usually Polo blouses with Bermuda shorts, basic, faded jeans and sensible shoes. Pretty much clothing she could still wear when she was fifty. I did fish around a bit during conversations. For instance, on the subject of Halloween, I asked her about costumes she had worn. She said she had once gone as a flapper to a party in Baltimore. I was hoping she would elaborate. Did this include a long, cigarette holder? But, she changed the subject quickly, saying only she had forgotten other costumes and that the guy who invited her was a jerk. I did wonder about smoking. Seeing a woman with a long white cigarette is such a turn-on when it's held a certain way, a certain look is evoked. Red lipstick staining a white filter. You get the picture. It seemed miles away from her, though. I just knew if I asked her directly if she smoked I would probably get some evasive answer. She never smelled of smoke and neither did her car. Somehow the subject of cigarette smoking came up when we were in a smoky bar. She gave the curious, corporate answer that those who smoke surely know of the risks since warnings have been on labels for so long. We didn't go into it. Then, trying to do the impossible, I turned the conversation to sexy clothing. You may wonder why I fished around? Well, it was this sense that something was being hidden from me. Oh, something was, but I just had this impression and couldn't put my finger on where it led. We went to the movies and during the coming attractions we saw a preview of Halle Berry as Catwoman in her fetishistic suit. After the film, she asked me my favorite actresses. Among other names, I said Halle Berry was not my favorite, but that I certainly liked her outfit for Catwoman. She simply gave me a bemused look and talked about some other actress. It didn't matter, for I was still puzzling over what transpired during the film. After we were seated and the previews rolled, she kept looking at me. Staring at my profile. When I turned and asked her "what," she simply turned back to the screen. Later, when a lone, attractive woman entered the theater, she turned her head to look at her. She continued to cast looks at the woman every once in a while. Her behavior was right at that edge where she could either be attending to the woman out of boredom with the film or a more than casual interest. I looked over at the woman, noting her long, lean appeal, her blonde hair and striking features. The woman left the theater early and I soon forgot about it as Kristen's head didn't seem to turn at her leaving. The dinner following the film was a struggle for conversation. It wasn't that we had no rapport, but that what was not being said made the air between us pregnant with suspicion. So much so that it was hard to dredge up a topic. She tried. After favorite actresses, it was favorite actors. Then, what she should do with her free time before her new job started. Stuff like that. At the end of the evening, I leaned in for a kiss. Actually, I didn't lean in now that I think about it. She sort of paused as I was getting my seat belt off and then we kissed. It was our usual chaste meeting of lips. I tried for more, but she had pulled back and smiled, thanking me for the nice evening. Again, for some reason I didn't sense the slightest opportunity to go for more. She was so nice and polite, but reserved. I thought we might as well be shaking hands. I'm a curious guy, as I might have said. Also, when something doesn't seem right, my head won't let it go. My brain was trying to put together pieces. I hatched a plan. It was time to do some investigating. Without seeming obvious, or like a stalker, I'd find a way to be in her neighborhood. She knew I was a long distance runner, training for a marathon. If I happened to be going through her area it wouldn't be that odd should I be discovered. It was sort of on my way to Evanston, my turnaround point. I was moving along, crossing the streets on a quite and cool Sunday afternoon, heading through the business district around the corner from where she lived when I started to feel creepy. This really was kind of like stalking and I was disheartened. Sighing, I changed course to head home. I passed by a coffee house and glanced automatically in the windows. Among other folks inside, my eyes couldn't miss a striking blonde woman. It was her attire that made me stare a moment longer and almost collide with an old man. She had on tight jeans with the legs cuffed up towards the knee, in the style of the moment, to reveal the tight, black shafts of gleaming leather boots. The heels were very high it seemed and came down long and straight in a stiletto. My pulse raced and I smiled to myself. The whole impression lasted a few seconds, but it is glimpses like that which can set off a whole chain reaction of thoughts. After deftly dodging the old man, I righted my course and headed back towards the lakefront. My mind played over what I had seen. Then I stopped dead in my tracks. The woman. She was familiar. It couldn't be. Kristen? This woman's eyes were heavily made up, her hair was sort of different like her whole style. No, no, I'm just fantasizing for sure. How could it be? Kristen didn't dress like that or wear much in the way of makeup. I tried to convince myself of this, but found myself turning around. I strode quickly back towards the coffee house and from an angle, so as not to be seen, I glanced inside. There was no sign of the woman. I looked up and down the street, expecting to see her walking along the sidewalk. I shook my head and laughed. Surely, my lack of feminine companionship was making my mind play tricks on me. Fantasy life was intruding. Yet, when we met the next day I found myself more closely scrutinizing Kristen. Did I see any makeup? Here hair, was it different? No, it was just she. As we walked along the street after getting some gelato, we passed a shoe store that was featuring very stylish boots in anticipation of the Fall season. I cast a quick glance, but noticed she didn't turn her head. However, as we passed the store I saw her turnaround and look at the store and quickly turn back. I smiled at her, but she was looking straight ahead. At the end of the evening, we kissed. This time, rather than just let the simple closed mouth peck suffice, I forced her lips apart slightly with my tongue and tasted her mouth. She quickly pulled back and said she had a cold coming on and didn't want to pass it on. I would have laughed at this evasion if again she hadn't seemed so serious. As I walked back home, after she left in her car, I puzzled over the taste in my mouth. Coffee, the flavor of her gelato, but something unmistakable. Smoky. Smoke! Kristen's mouth tasted as if she had a cigarette. I walked back to my apartment in a daze of sorts. Does Kristen smoke? All in all a small matter, but it hinted at things hidden. It made me reconsider things that had happened during our dates. Channel surfing back at my apartment, I grew restless. I must have checked the fridge twenty times, not even knowing what I was looking for. Looking for a reason to go out, I decided to head over to a bar I sometimes went to in Wrigleyville. It wasn't that late. As I was walked on, I notices a car stop at the intersection up ahead. It looked like Kristen's Honda. The car moved on. I started to jog and headed down Halstead, through an area known for it's gay bars and clubs, following the car at a distance. The car pulled to the side and parked at a meter. A woman exited the car. What I saw next still burns in my mind. Kristen, exited the car, paused and rummaged through her bag. Not looking like the woman I knew, but like the woman I saw in the coffee house the other day. Her hair was slicked back. Lips were dark, maybe blood red and her eyes heavily made up, smoky. Gone were the Polo tops and Bermuda shorts. A black sleeveless blouse, practically see through and unbuttoned to her cleavage. Her lovely hips revealed by a tight black leather pencil skirt, to just above her knee, and with a long slit up the thigh. No stockings, for her pale skin contrasted with the black leather. Her long legs were covered in the shafts of her tight black leather boots. These were just the boots I'd glimpsed on her the other day. The toes wore pointy and wicked looking. I could feel my head grow light and this otherworldly feeling creep up on me. She extracted a long cigarette from her bag and with a practiced movement. A long drag followed as the tips of the cig glowed red. She walked, no strutted, across the street with an exaggerated sway of the hips as she exhaled a long stream of smoke. She entered a club across the street, nodding to the guy at the door. I approached the entrance and after showing my ID, I entered. My pulse was racing. The club was small and crowded, mostly guys, but a surprising number of women. I tried to see Kristen through the dark and smoke. The music was loud and disorienting. I looked towards the back where I saw Kristen embracing a woman. She looked oddly familiar. The woman was dressed quite provocatively, as well, in a black, low cut top and black leather pants. The women's arm was draped rather low against Kristen's back. I saw their heads come together. They were kissing slowly and deeply. Good god. They broke the kiss. As the woman was turning her head, she looked right at me over Kristen's shoulder. She had an inquisitive look on her face. I froze. She leaned into Kristen's ear and whispered something. Kristen began to turn in my direction. As soon as I saw her move, I ducked and walked quickly between dancing bodies for the door. My pulse was racing as I dashed out of the club. I looked back towards the door and turned a corner to go down an alley. My thoughts raced as I walked home. I kept pausing as I walked, shaking my head. My arousal was obvious, but so was my confusion. I slipped my hand in my pocket in an attempt to camouflage my prominent erection. The images of Kristen, the new Kristen, the one I just saw played over and over again in my brain. And that kiss. It was more than the erotic taboo of it. It was passionate and emotional. A lover's kiss. To see that person and try to reconcile her with the woman I was dating seemed impossible. I remembered I had a date with Kristen tomorrow. Was it going to happen? I wasn't sure what to say to her or how should I act. Right now, it seemed the best course of action was to do nothing. Let her say something. At one point in the night it hit me. The woman with Kristen. I recognized her. She was the one at the movie theater. Kristen had been turning to look at her. Why had she been there? This led me to wonder what she had said to Kristen when she looked at me. Did she recognize me or merely say, "A guy is staring at us." Again, it was dark and it would have been difficult to give a detailed description of me, but I did recognize her so it was entirely possible she knew who I was. The next morning, I compulsively checked my voice mail to see if I missed a call. The anticipation was too much. I picked up the phone to confirm our date for an early dinner. I listened to Kristen's voice greeting and marveled at how chipper and innocent it sounded. Just like I'd known it. I left a message, being careful to keep my voice neutral, leaving out any clue that it was me her friend saw at the club last night. My hands were sweaty as I waited in the bar of the restaurant. I was wondering how she would appear. That question was quickly answered when she appeared at the entrance, looking just like, well, Kristen in a conservatively cut, long sleeve pastel colored blouse and khakis with flat soled sandals. She didn't quite meet my eyes during the meal and seemed a bit subdued. Her voice was little scratchy, as well. I tried to make small talk, which was pretty much the only talk we ever made. During dinner, I searched her eyes and face for the way I saw her last night, making adjustments here and there to see how it could be possible - that two so very different people were one and the same. After dinner while we were sipping our drinks a woman at a table next to us lit a long cigarette. My automatic reaction was to look at her, noticing the graceful way she exhaled. I turned my attention back to Kristen, it was merely a second glance the other way, but she looked at me with wide eyes. No words neededto be exchanged. Kristen's face flushed red. She looked down and whispered something. "What?" I said. "You know." My heart skipped. I gripped my napkin tightly. "Kristen, what are you talking about?" "Oh god, Andy you know." Her voice quivered. She looked up her eyes were glassy. She got up from the table and grabbed her purse. "Kristen. Kristen, wait!" I quickly threw some cash down and ran out the door, feeling the stares of the other restaurant patrons on me. She was running down the street. I sprinted after her. When I caught up with her she was shakily putting the key in her car door. I came around to her side and put my hands on her shoulders. Her whole body was shaking. "Kristen, don't, don't run." "Andy, please, just leave me alone." "No, it's okay." I leaned into her hair and gently held her shoulders. She turned to me. "Please. No one knows. No one knows! Do you understand? No one knows. That's not me." She was sobbing now. "Kristen it's okay. It is you and you were beautiful. Beautiful." I looked at her eyes and pressed my nose to hers. We were kissing. It just happened. I can't even remember whose lips moved first. This was not the mere peck of lips like before. Our tongues were swirling on one another's mouths. My hand caressed the back of her head as she grasped bunches of my shirt in her fists. We broke the kiss. "Let's get in the car and talk," I said. She nodded. We got in the car and drove to Lincoln Park. She sniffed and blew her nose then took a deep breath. "What do you want to know?" "Whatever you want to tell me." She took a deep breath. "I can't talk about this while I'm driving, wait until we get to the park." We drove in silence. She turned to look at me. I smiled, trying to make her comfortable. At the park, we walked along the quiet foot path. The evening was warm and still light with a weak breeze coming off the lake. "I was engaged." "When?" "In Baltimore. We me through work." "Was it a mutual decision to end the engagement?" She took in a deep breath and exhaled slowly. She stopped walking and sat on a bench. "Do you really want to hear this? Do you Andy?" "Yes," I said. I tried to sound resolute, though I had no idea where she was going. "I was taking a French class at night. Just something I'd wanted to do and maybe meet other people. That's where I met Kim." "Kim?" She looked at me. "Yes, Kim. The woman you saw me with. You probably saw her at the movie theater, too. She was curious about you and spied on our date." She paused. "God, that was so stupid." I nodded and attempted a laugh. "Kim and I became friends, but quickly something more. I'd been attracted to women in the past, but never acted on it. Quite frankly, I thought it was something I would outgrow. I was in one relationship after another with guys and so I was always preoccupied. Figured the girl thing was over and so turned off that part of myself. Hoped it would wither away, at least." Midwestern Mystery Woman She rubbed her eyes and temples. "I was wrong." She laughed. "Kim and I carried on in secret. It was amazing. She put me in touch with myself. Opened me to new experiences. She encouraged me to dress differently, act differently, to express myself. All of it in secret, away from my usual friends. Away from my fiancé, but he found out. It was inevitable and I guess a part of myself was glad. The lies wore me down. He didn't tell anyone, he was so proud and feared humiliation. But, we had so many mutual friends, but they were his friends first. I felt myself shunned. He told them I fooled around on him with some guy. Oh, god, it was awful." I reached out and rubbed her back. She looked at me. "Andy, do you really want to hear this?" "Kristen, yes." "Kim worked for an ad agency and they have offices in Chicago. She transferred. I then quit my job and came here. I told her it couldn't last. That I wanted other things in life. That we would be in Chicago as friends, only. I couldn't let it go, though. She knew it, too." "I'm confused then. Why did you continue to see me? I mean, Kim is your girlfriend." "I like you Andy. I wanted to be with you and I'm not that way. I'm not gay!" "But Kristen..." "Please let me just continue. Kim makes me feel incredible, amazing, so in touch with myself. It's just that I don't think I'm ready for a relationship with her. She's my friend first, my lover second. It was a friend who wanted to move to Chicago. Don't you see?" "Kristen, I don't know. I'm so confused." She sighed and looked down at the ground. "So am I. I'm so tired, maybe we should just call it a night." I nodded. I kissed her quickly in the car at my apartment building and I could feel her eyes on me as I walked inside. The phone woke me up. It was still dark. I looked at my clock. 3:00 a.m. "Hello?" "Andy, it's Kristen. Is it too late to come up?" "Kristen? Um, no, no wait, I'll buzz you in." I stumbled out of bed, noting my messy apartment. It's too late to clean. I made an attempt to mold my hair into some semblance of it's normal self. As I opened the door, I realized I hadn't put anything on and was wearing only a loose pair of boxer shorts. Seeing Kim in the crack of the yellow light of the hallway woke me up rather quickly. She was wearing tight jeans tucked into knee high, black leather stiletto boots. Her face was made up as I'd seen it that night at the club. She wore a black leather blouse with the buttons undone to her cleavage. "Oh god Kristen." She stepped in. I could smell a mixture of perfume, cigarette smoke and leather that made my cock stir in my shorts. Kristen reached up to the back of my neck and pulled my head to hers as she thrust her tongue in my mouth. I could taste her crimson lipstick as she searched my lips, gums, and tongue. We broke the kiss. "You didn't give me a real kiss when you said goodnight." She leaned in again and kissed, pushing me against the wall. Her hand slipped under the band of my boxer shorts and took hold I've my hardening cock. She cupped my balls and moved up the base of the shaft of my penis slowly, her fingers discovering the length and shape of me. I moaned into her mouth. Her voice was breathy with a faint smell of alcohol and cigarettes. "Mmm, Andy, I like that, don't you?" I moaned again, gasping an answer. "Yessss" She was whispering in my ear. "Andy, you like the way I look, don't you?" "Yes Kristen." "You like my boots, don't you?" "Oh god yes, Kristen....yesss" "You like my leather, ohhh..yes?" I kissed her deeply and ground my thigh against her crotch, feeling on my bare leg the heat and moisture through her denim "God, yes, Kristen. Yes. Oh...." I came hard on her hand, inside my shorts. She massaged the cum into my balls and cock and stomach. She pulled her hand up slowly and brought it to her red lips. Looking me in the eye, she slowly licked the cum off her fingers. She stepped back, the stiletto heels of her boots clicking on my hardwood floors. "Tomorrow at five, at my apartment." She blew me a kiss and exited. I leaned back against the wall, sighed, and shook my head. Looking up at the ceiling I said, "what the fuck?" It was a long while before I fell asleep. My hand was a bit unsteady when I pressed the buzzer on Kristen's door the next afternoon. She stood aside to let me into the apartment. Light was streaming through the windows and cast a pleasant glow to the walls. I could see candles lit on the tables and bookshelves. I looked at Kristen. Her eyelids were heavy with dark eye shadow, her lips full and glossy. Her hair teased out a bit and little wilder than before. She turned before me. "Do you like what you see?" "I do, but does anyone else see this, besides strangers and Kim." "No." Her leather skirt looked so soft and supple as it hugged her curves, stopping just before her knees. Her boots looked slightly different. They were tight, of stretch leather, and went to just over her knee. The heels seemed higher with an incredibly thin heel and pointy toe. She wore a see through, gauzy black top with lace embroidery. Her nipples were hard and prominent against the fabric. "Kristen, you are so lovely. I can't ..." She put her finger to my lips. "Shh. Enough of that. Let me just show you me." I sat in a chair and watched as she reached to her table for a pack of long, slim cigarettes. She pulled one out of the pack. I noted how she had changed her nails. They were long and red now. I reached across and picked up her lighter and lit her cigarette. She blew a long stream of smoke just over my head. "And this, when did it start. Along with everything else, with Kim?" She looked down at the cigarette between her long red nailed fingers, regarding it curiously. She laughed. "No, this was something I've done for a while. I've been a remarkably successful closet smoker. Not even my fiancé knew, or at least said anything. If anyone ever commented on smoke, I'd say it was on my clothes because I was with someone who was smoking, or in a smoky bar." I nodded and smiled. She held the cigarette by her head. "But is suits me, no?" "Yes," I said. "Certainly in your present attire." We both laughed. "So, what did you want to happen here Kristen?" "Andy, come here." She moved the table with her boot and indicated a place between her legs. I knelt between her boots and leaned forward, breathing in the scent of her leather skirt and running my hands along the soft leather covering her thighs. Kristen looked directly in my eyes and leaned back. I moved my lips over the leather and licked up to her crotch, pressing my lips down. I could feel her pubic bone beneath the leather and feel the heat radiating from her. She sighed softly and moved her hand to my head and running her long nailed fingers through my hair. "Andy," she said. Her voice soft. "Yes?" "Andy, rub yourself on my boots. Please." I reached down and unbuttoned my pants and quickly pulled my erection out. The cool, soft leather felt fantastic against my warm smooth cock. I moved back and forth as she pressed her boots against me. My lips continued to lick against the leather of her skirt, feeling her sex below. I was so lost in my pleasure that I didn't hear the heels on the floor. Looking up, I saw a black leather gloved hand cupping Kristen's chin and lifting her lips to hers. Kim. Her blonde hair was in a ponytail. She wore only long leather gloves that reached up to her shoulders and a pair of black leather boots to her thighs. She smiled at me after pulling her now messily lipsticked lips from Kristen. "Andy, kiss Kim." I leaned in and kissed Kim's warm lips. Our mouths opened and our tongues caressed one another. Kim's breasts were rubbing against Kristen's leather skirt as we continued to kiss. My precum was leaking from my cock onto the shafts of Kristen's boots. Kristen moaned. "I love you. I love you. I love you." Kristen stood up and I did the same. I took Kristen in my arms and kissed her again. "Undo my skirt." I reached around her and let the skirt slide to the floor. She wore nothing underneath. Kristen knelt facing away from me on the floor. I slid easily inside her. She was quite wet. I could smell her the minute she took off her skirt. Her nether lips swollen and pink. I watched Kim move to the couch and spread her legs. Her black leather gloved hands moved through Kristen's blond hair. When I saw Kristen's lips move to lick the boots of her lover I had to restrain myself from coming right then. I moved my cock in and out of the folds of Kristen's pussy, feeling her gasp against the leather of Kim's boot with each thrust. I could see Kim's boots glisten now with the saliva of Kristen's mouth. We looked at each other. I wish I could tell you that she was a stranger to me; that I felt lost in the situation and what I was doing. No. It wasn't like that. I looked at Kim and wanted her, loved her, felt tender towards her and her eyes revealed the same. Kristen was almost a conduit for the emotion that ran through each of us. When Kristen's lips met her glistening sex, I watched Kim arch her back and thrust out her body. She pressed her lover's head to her sex. I felt the cum surge within me and I was helpless to stop its flow into my Kristen's warmth and wetness. Her vagina contracted around my shaft. A muffled cry that matched Kim's. It was too much and I felt as if I would pass out. Later, as we lay in each other's arms in the glow of the candle and twilight lit room, I smiled to myself. Was it delight? Partly, of course, but more it was how I understood what little I knew of people and that included myself. I had no idea of what the future would hold, but I felt sound in the moment and peace in the midst of this chaos. Tomorrow never knows.