I fell for Heather at The Perk Place on one of their Open Mic Nite. I was just sitting in the back watching all the people go up on stage and read their poetry and sing there songs. Heather was a waitress there but she always got off on open mic night because she would perform. I had seen her perform many times but this time it was different.

Heather was a little 5 foot nothing girl. She had curves and this beautiful head of curly brown hair. She had broad shoulders and muscular arms. Flat as a board, nothing really there on her chest but she made up for it in many ways. Her hips where full and so were her ass. Her legs I could assume were masculine but I never had really seen them before this night. As my assumuitions were proven to be correct, tonight she was wearing this black velvet skirt that hung to right below her knees. She sat on the barstool in front of the microphone with her guitar in hand and began to sing.

Before long, the entire coffee shop was singing along to it. I knew the song but didn’t know from where or even why I knew it. It didn’t really seem to matter for I was more in entranced by Heather. Watching her play. Watching her lips move as the words escaped her mouth. I had never seen her before like this. It was almost as if I was the only one in the room with her. She was singing only to me. I looked around me and noticed that no one was paying any attention to me. No one could see or hear my thoughts.

Her song ended and everyone applauded. She began another song. One that she had written and I caught her glance. She was looking directly into my eyes. Her stare was mystifying. I was lost in her eyes. I didn’t notice that the song had ended and Heather didn’t seem to notice it either. The entire coffee shop was quite as she stayed on the stage just staring into my eyes. Finally it looked as if something had awakened her for her dream and she said her thank you’s and left the stage. I watched her leave trying hard not to jump up and run after her.

I had talked to her numerous times. Never about much really. I was very attracted to her but I thought everyone here was and didn’t really think that I had a shot with her. Something inside of me was telling me that I was wrong. Why would she have stared at me like that if there was anyone else in her life?

I decide to get up and get another cup of coffee. I thought that maybe she would be at the counter getting one for her and there I could ask her to join me and tell her how beautiful she looked. To my surprise, or maybe fear, she was standing there talking to one of her coworkers. They paused so I could get my order in and as the girl went to get me a new cup of coffee I looked at Heather. She looked even more stunning than she did on the stage. Her brown eyes seemed warm and inviting and I felt that this was my only shot.

“Heather?” I asked hoping that I didn’t sound like a 5 year old. “Would you like to join me over some coffee to talk? I really enjoyed your set and I just…”

“I would love to Shelly.”

Oh my, it was really happening. I showed her the way to my table and we sat in silence for a couple of minutes. Then we began telling the story of how we both came to the city. Heather had lived here in Chicago all her life. She was planning on going out east to New York to try to become a song writer like Ani Difranco or Amiee Mann but she had found it just easier to deal with the people here and this was her home and she wasn’t sure if she would ever leave. Then I shared my story of a small town girl who moved to the big city to find herself and I found myself gay. She laughed. Well, we both did but I found it more amusing hearing her gentle laugh.

The conversation soon turned to the lack of love or love partners in our life and I got this feeling that I should ask her to go to my loft for the night.

“Um…would you like to come to my place to have a couple of drinks and maybe watch a movie or something?”

“Sure Shelly…I. well…I don’t have any spare clothes or anything.”

“That’s fine; you could borrow some of mine if you want.” Could I sound more dispret? I really liked her and didn’t really care if anything happened I just didn’t want this night to end where we both just went home and that was it. I had enough friends and I was more and more attracted to Heather with every passing minute.


After a 30 minute drive into downtown Chicago and finding out more and more stuff about Heather, we arrived at my apartment complex. It wasn’t much really just an old warehouse with about 20 loft apartments in it. We entered my loft and Heathers mouth dropped to the floor.

“I didn’t know you were an artist!”

“Yup. I don’t like to brag about it or anything because I don’t really think I am that good.”

I watched Heather make her way around my loft looking at all the canvases and paintings of women that I was still working on. She would stop at each one and ask me a couple of questions and move on to another. I approached her from behind and put my hands on her shoulders.

“Would you like a drink?”

“No thanks.”

I didn’t know what to do now. I have this woman, who, yes I really like and really want to, um, you know. I also have no clue how to let her know that I want to. Or even if she wants to.

I slowly moved my hands from her shoulders down her arms. My hands found their way to her hips and I pulled her back to me. Or was it she moved back to me and I just thought that I moved her. Heather tilted her head to the side exposing her neck and I began to kiss it. Soft and slowly. Making my way down. Her breathing got heavier as I grab her hand and pulled her to my bed.

I sat her down on my bed and took off my shirt. My nipples were poking through my lace bra and I knew that Heather was enjoying the site of them. I unzipped my pants and let them fall to the floor before I stepped out of them. Now I was standing before her in just my bra and panties which of course matched. I strattled Heather on the bed and pulled her shirt over her head. To my surprise she wasn’t wearing a bra. I kissed her neck, making a trail of kisses down to right nipple. My tongue danced around it before I kissed the top of it. Hearing her moan I began to play with it more and more.

I laid Heather back on the bed. With my left hand I reached up her skirt to find that she also wasn’t wearing any panties. If she was they would surely be soaked to the bone. My fingers danced around her wetness as I kissed her nipples. I felt her hands reach up to undo my bra and as I felt it fall onto my shoulders, I began to bite her nipples softly.

Heather pushed me off of her and took my bra completely off. She then began to kiss my neck and roam my body with her fingers as if I was a foreign map. I ran my fingers through her hair as she ran her fingers down my thigh. She moved lower down my body so I could not touch her and took off my soaked panties.

Starting at my feet, Heather ran her nails up my leg to the inside of my thigh. When they reached my wetness, they danced a dance that I was not aware of. I began to move my hips slightly. Her nails then traveled out of my wetness and up my stomach. I could feel just how wet her fingers were as they left a trail on my stomach and I could still feel it as she traced my nipples.

She moved up to my lips. Leaned down and we engaged in one of the softest kisses I have ever had. Tongues were gently darting around each others mouths. Hands were moving all over our bodies. Holding each other, I thrusted my knee between her legs. I could feel her wetness on my knee. She began to ride me. I could feel her moan. My hands traced her sides, slowly dragging my nails up making her shudder. I kissed her neck as she bit my shoulder. I knew she was close.

“Oh my god I’m cumming!”

I started to move faster and harder. Pushing Heather down on my knee, not wanting it to end. I could feel her cumming on my knee. I felt her wetness drip down the side of my leg onto the bed. Her breathing was rapid and her movements were slowing down. She then collapsed on the bed next to me. Her hand still on my stomach. Her fingers making circles on my stomach, making sure that I was still aroused.

Heathers’ fingers traveled down my thighs into my, almost flooding, hole. She place one finger in me and played with my clit with the other. While doing this she sucked on my right nipple. Her movements were smooth and soothing. I started to move my hips to the rhythm of her fingering me and as I did so she placed another finger in me. Moving it faster and harder. Sucking on my nipple harder. Everything seemed to get “supped up”.

I arched my back as she moved down to my pussy. Keeping her fingers inside of me, she started to lick my clit. Playing with it using the tip of her tongue. Moving her tongue slowly from side to side. Her fingers were moving in and out, gentling brushing my g-spot every time they entered my body.

Her movements quickened. She began to suck on my clit and finger me. Licking me on the down stroke and biting my on the up stroke. I didn’t know if I could take much more of this. She pulled her fingers out and began to lick me all over. I could feel her tongue in my hole. Pushing her tongue deeper inside of me. Then moving up to lick my clit, gently biting it. Moving on to lick my lips, and then back to my hole.

I had my hands on her head, in her hair. I was pushing her closer and closer to me. My legs on her shoulders so she could lick every inch of me. I arched my back and began to moan. Her movements slowed down and when I was flat on the bed again, she would quicken them. Her tongue moving faster and faster, darting around my entire pussy. My hands left her hair and grabbed the sheets. Arching my back again, Heather didn’t slow down. Her tongue was on my clit, another finger was in my hole. They moved as if they were one. I couldn’t take it.

“Don’t stop Heather. Please don’t stop.”

With that said Heather snuck another finger in me and began to move faster and faster. She licked me harder, grabbing my clit in-between her teeth as she massaged my g-spot. Hitting that spot harder and harder, my entire being spasm and I came. Thinking that maybe she would slow down, I moaned and she moved faster. Her fingers never leaving my g-spot. Her tongue never left my pussy. She began to taste my cum, licking it all up. She pulled her fingers out of me and I came again. This time, her tongue was in my hole, catching all of my juices that were escaping my body.

She then stopped. Moved next to me on the bed and lit a cigarette. She handed it to me and lit another for herself. I was surprised that I could even smoke after the work out that we just had but it was the sweetest cig I have had. After a drag or two, Heather leaned over to me and kissed me. I could taste myself on her. Her tongue pushing what was left of my juices in her onto my tongue.

She stopped and smiled at me. After finishing her cigarette she got on her clothes and left. I guess she took a cab back home, I’m not sure about that still. I passed out before I heard the down shut. I still go to the coffee shop and we still share a glance that only us know what it means.

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