Alleys

This is a semi-true story names changed and places obscured. Please send feedback and constructive comments.

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My mother told me never to take a girl into an alley at night. She went on about how dangerous they were, with strangers lurking in dark doorways waiting to do horrible things to the people who wander in alleys. Alleys can be dark, imposing and dirty especially in the city. I spent my youth avoiding them, but being drawn to the unknown dangers of alleys. I am sure my mother would be shocked to know how her caring comments had grown into a fetish. Now I can scarcely pass an alley without thinking of sex.

Eve was my first. We lived in a suburban area with alleys between every street. She was my first girlfriend and we quickly advanced from kissing to making out. It was summer and the night was warm and muggy. We had found a quiet spot in the alley, and Eve had managed to get me out of my jeans. I was on my back with Eve between my legs and she was kissing me when my mother found us. She sent Eve home and then she dragged me into the house. She scolded me and that was when she told me about alleys. She also said good girls don't go into alleys with boys.

Eve went from girlfriend, to best friend and then to girl friend. If this story was a movie you would see the montage about now. Eve feeling me up. Her coaxing me into her clothes. Spending time together swimming, me in one of her suits. Watching boys at the junior high school hang out. We stopped the kissing and touching and began talking about boys. Eve started dating and we would talk long hours about what they had done and what she wanted. We were inseparable. She was always lending me clothes and giving me panties and lingerie.

Eve fixed me up with my first date with a boy. It was on a warm spring Friday night we were still in high school. Eve insisted I get dressed at her house. She looked amazing and ready to dance when I arrived. She dressed me in some of her pants and a blouse with lingerie under it all. She had me wear a pair of her shoes with some light makeup, and I looked like a waifish girl. Our dates were at the club when we arrived. Tom, my date, was a big boy fully four inches taller than I was.

Tom pulled me onto the dance floor. Soon I was dancing and having too much fun to worry about how I looked. Tom was a perfect date. He bought round after round of drinks, and after a while, we slipped into the alley to smoke a cigarette. It was a typical city alley with dumpsters and dark doorways and few lights. We walked down the alley to a doorway smoked and made out. It was dark and strongly erotic, Tom was so much bigger than I was, and my mothers words crept into my head. I thought about how I was not a good girl to be in this alley with Tom. I was not a good boy either and I was excited to realize it.

Tom was gentle, he slipped his arm around me pulling me close. He smelled my hair and his lips touched my neck. I could feel him getting aroused. His cock grew as his hands touched me. I could feel it pressing against my side. I opened his jeans and took his cock in my hand as we kissed. I felt his hand on my face as he explored my mouth with his. I stroked his cock with both hands as he kissed me. He orgasmed in my hands while his tongue played in my mouth. I can still feel his cock throbbing in my hand and the smell of cigarettes and the alley. He kissed me again and slipped away. I stood there shaking, the smell of he cum was strongly erotic and I was thinking how bad I was because good boys didn't do these things in alleys or anywhere. Eve found me walking back to the club door with his cum still on my hands. She cleaned me up and took me home. She had me describe every detail, and she noticed how wet my panties were when we were changing.

That was only the first of a string of encounters with boys and men in alleys. Usually ending with their cum on my hand or in my mouth. Eve followed my sex life closely and kept supplying me with lingerie, and helping me to be more feminine. Soon I was always wearing sexy panties, but as time went on I was drawn to camisoles and stockings as well. Halloween soon became my favorite holiday and Eve my costumer. She talked me into dressing as Lucille Ball in a Christian Dior dress, pearls and pumps. I was floored by the dress and Eve's belief I would look beautiful.

I came out to my mother after my father left her. She told me she had know for years. She supported my new lifestyle, and allowed me to dress full time. She soon began dropping little feminine gems like "always dress and act like a lady, enjoy being a girl, real men love girls." Of course she gave me dating advice like "Never let a man's hand wander under your hem in public." She is a true southern lady and wanted me to be the same. The best advice she gave me was "Dressing is an art it takes thought and time to be beautiful."

I met Kevin through Eve. He is a man. Strong, big, handsome, he made me weak in the knees when we met. It started as a blind date with Eve and her boyfriend. We girls arrived together wearing dresses and heels to a pub. Flashing curves and legs to a crowd of jeans and T-shirts we were noticed immediately. It stands out in my mind as a flagrant feminine display, and one that got the attention of every male in the room. Eve was a pro at that. Kevin and Mark stood and held our chairs. He played the gentleman to the hilt--standing when we went to the ladie's room and being very attentive--now I know he was coached before the event by Eve.

Kevin is the adventurous lover I had never known I wanted. He has sparked my imagination and we have followed many of these sparks to public liaisons, costumed scenes, and long sexy nights at home. I told Kevin about my thing for alleys and how they were strangely erotic and naughty to me. I shared my first time with a boy in an alley with him. He responded, as I had hoped, with an erection on a warm night with his cum on my hand.

That brings me up to last night. It was a cool fall evening and we were going to dinner in the city. I wore a dress I had bought from an online vintage clothing store, a short shirtwaist dress. It came way up above my knees and my slip showed lacy at the hem. I was wearing stockings that were held up by my corset garters and four inch heels, so I would be closer to Kevin's height. I wore just a hint of makeup, and my hair fell down my back in flaming curls. I carried a shoulder bag with all my necessary girl stuff as Kevin would say.

The restaurant is an upscale place in the middle of the block with a blues club next door on the other side of an alley. We parked a block away and as we walked to the restaurant, Muddy Waters' Short Dress Woman was rocking the club. We passed the alley, unconsciously I slowed and stared. One light could be seen far down casting a weak light on some trash cans and recessed doorways. The music was loud and I could feel it through my heels. Kevin pulled me close, and then he pushed me away playfully spinning me around, and he pulled me back to kiss me.

The meal was good, I am sure, but all I could think of was the alley. Kevin commented about my lack of attention. I kept thinking about the alley and the music. He was playing it cool but he knew where my mind was. His hand would slide over my thigh or touch my neck as we drank our wine. He was keeping me turned on with his touching. I knew I needed to send him a signal, but he almost dropped his fork when my stocking covered foot slid up his calf. Giving him a smoldering look as I sipped my wine he passed on the waiters offer of desert. He just smiled knowingly and asked for the check.

We walked out into the cooler air and the music washed over us. Kevin pulled me to him and we danced right to the club. He pulled me into the place as I tried to slip back outside. I was hit by the heat first. The club was dark and filled with swaying people. The band on the stage was paying a tribute to Muddy Waters, and the singer was holding an unlit-cigarette as he played his harmonica. The smoke machines gave the feel of a place from another time. The smell of hot dancing bodies and alcohol washed over me as Kevin pulled me to the bar. He ordered drinks and held me tightly at my waist. Swaying to the music I could feel him grinding on my hip. Soon we were on the dance floor moving to the music. I was getting hot and slightly drunk from the constant flow of Jack and Coke. I moved close to Kevin and ran my hand up his thigh. His cock was hard as my hand slid over it. His hand covered mine and he held it on his crotch. Pulling me to him he kissed me hard.

He took my arm and guided me toward the restrooms of the club. In the hallway there were three doors and one of them had a battered exit sign on it. His hands on my waist he guided me to the exit. With a shove the door opened into the alley, right under the one light. The cold air was a shock. He pulled me close, and kissed me. Holding me tightly his hands were hot on my back and neck. He held me closely, kissing me. I could feel his cock against my belly as his hands slipped to my butt. He was grinding to the music a slow driving blues tune. I was lost in the music and my desire. I wanted him badly. I could feel my desire burning in me.

He broke our kiss and took my hand. He led me to an inside corner, like a room would have. It was shadowed from the light but still light enough to be seen. He pushed me back into the corner, and standing over me we began kissing again. Now I could reach his belt. I unbuckled it. I managed to get his fly open as we kissed, and his hands wandered over my body. He pushed my breasts up and out of my corset, and he fingered my nipples through my dress and slip. I bit his lower lip sucking on it as he touched all the buttons that excited me. I felt the cold brick wall against my back, as he pushed closer to me. His hands moved to my butt rubbing up and down working my dress up, as I held his cock in my hands. Stroking his heavy cock and occasionally letting my nails move over the soft skin. I broke our kiss and told him "You know I want this cock inside me right now! Right here, I want you so badly. Right now."

I felt my dress pulled up to my hips and the cold air hit my exposed skin like a slap from his rough hand. His hand covered my left cheek, but my right was pressed against the brick wall cold and hard against my bare skin. His fingers found the string of my thong and they moved over my ass. I felt a finger rubbing my eager hole. Pressed as I was against the wall I couldn't move for him. I did relax and try to push myself onto his finger. His other hand was pinching my nipple hard. His cock was rock hard in one hand and his balls were heavy in the other. His mouth was on my neck just above my collarbone and his chin felt rough on my chest.

I felt his hands moving me, turning me away. I was facing the corner, and he was behind me rubbing the head of his cock over my butt. His cock found my hole and his hands moved to my hips. I let out a sigh and pushed myself back onto his big cock. I felt him push past my sphincter. I had enough lube in me for him to have his way, but the first few inches felt as if I had no lubrication at all. He pulled back and I pushed myself onto him again. I had to feel him deep inside me. He pushed as I did and he slipped all the way in. His hips resting against my ass. The music had stopped and I moaned loudly as his cock filled me. The exit door crashed open and a couple stumbled out into the alley.

Kevin groaned his cock was pulsing inside me but he did not move. The couple lit a cigarette and were smoking and laughing. Kevin pushed my hips gently then pulled them back. He was grinding his cock inside me and trying to keep our movements down. I began moving myself without his pushing and pulling. I managed to get a long stroke of his cock and let out a moan of satisfaction. I looked over at the couple and saw them looking at us. He was standing behind her with his arms wrapped around her holding her closely. I kept moving under Kevin. Slowly working his cock inside me.

The woman said a little too loudly, "That is fucking hot!" and she groaned softly. The light was behind them so I could only see them swaying silhouetted in the light.

Kevin needed no further encouragement and began to fuck me. I put my hands up on the wall pushing myself back as he fucked me. The couple were talking softly and still swaying to the music. I could feel an orgasm building as Kevin was grinding into me holding my breasts and kissing my neck. I told Kevin I was close and he grabbed my hips and fucked me harder. My orgasm came over me. I felt wetness flow into my panties. My legs were shaking and my heels were tapping wildly on the alley pavement. Kevin held me up impaled on his cock.

The woman moaned and her lover said, "She is amazing look at her take that cock."

She answered him but I wasn't listening. I was coming down from my orgasm, and Kevin was starting to grind again. Kevin said softly, "He is fingering her, she is gonna cum watching us. You naughty girl."

I groaned loudly and pushed my body back onto his cock. I was fucking him back knowing that couple was watching us. Kevin held my hips and fucked me hard. I could tell he was getting close. He was using long deep strokes and moaning. Quickly he was jackhammering me and I was moaning my body orgasming over and over. He took one last half stroke and drove his cock deep into me groaning loudly. I felt his cock swell and his hot cum splash over my insides. It made me cum so hard Kevin was holding me up. My legs had given out. He pushed me up against the wall holding me up with his body.

The woman groaned loudly the man holding her with his hand inside her panties. I recovered enough to stand on my own. Kevin's cock was still inside me and I flexed my muscles around his cock. He groaned loudly and said, "You want more do you?"

The woman laughed saying "She is a fucking slut! Did you hear she wants more?" They were moving back to the door. "Oh yeah look who's talking." They disappeared into the club. Kevin was spent. His cock popped out of me and he slid my thong back into place. I could feel the wetness of his cum around my well fucked hole. I could also feel the wetness of my own cum soaking through my panties and onto my stockings.

Kevin took my arm and I tottered down the alley to the street. There were fifteen or so people in front of the club. We walked arm in arm through the crowd. Every step I took I could feel cum between my thighs. I knew I had that look of being well fucked and I was strutting down the street on my man's arm.

We made it home but it was a long drive. Kevin offered to stop and get a room or use a rest room to clean up but I wouldn't hear it. I was loving this feeling of being well fucked all the way home.