An Unexpexted Tryst

by Janey

   

I had just finished putting gas in my car when I looked across the street and saw a used video game store, for some reason, maybe boredom I decided to go in a check to see if anything peeked my intrest. I walked in and was greeted by the 17 year old clerk. "Hello, Welcome to ********, can I help you" He said. "No, Im just going to look around for a few minutes Thanks".

There was only two other customers in the store one trying to haggle a higher price for the game he was trying to sell to the clerk and the other palying on one of the consoles up front. I continued browsing the different titles looking for anything interesting, but most games I had either played before or just didn't have a desire to play. Nothing. I was about to leave when a beautiful women walked in. She immediantly began looking through the games. Of course the clerk gave her the welcoming speech, his voice slightly craking as he did, they way he stared at her it was obvious that he wanted to help her with something other than games, but I couldn't blame him. She was absolutley gorgeous. She had dirty blonde hair that fell past her shoulders and stood at leat six foot tall. The little b;ack dress she wore did more than justice for her. I noticed I was staring at her so I diverted my attention before she noticed, I have no idea if she caught me or not. It's just I havent seen a women that cought my attention as she had in quite a while. It wasn't her body, dont get me wrong she was svelte, but still had nice curves that were perfectly perportioned. Her face was also very pretty but even moreso there was just something about her that made her irresistable to me. Maybe it was the way she walked, she strode with a certain confidence, but at the same time seemed very humble and down to earth. I was enamored with this beauty. Well I wasn't about to leave now.

I made my way onto the aisle behind her as I wanted to see what she looked like from the back. Yes I am an ass man, and I must say I was very pleased. Agian the black dress accentuated her nicley. I was trying to figure out a way to approach her, to star up a conversation. So hello i was just wondering who made that dress I'm looking at some different stock options and anything that can look that good on someone must be a great investment. As you can see lines arent really my fortay. I was looking down at some game I had picked up when I heard a voice saying "excuse me". I looked up and it was her.

"Yes, Ma'am" I said. She was smiling and i felt like a fourteen year old talking to the head cheer leader.

"I was looking for a christmas present, for my nephew. He told me he really wanted a game called zelda." she said.

"Well, I'll help you look for it." I half stammered back to her.

"Ohh, OK, so you're going to buy that copy" as she pointed at my hand.

I looked down to see I was holding a copy of Zelda in my hand. I smiled at her realizing that I must have just sounded like an ass a moment ago. Oh yeah I can help you look. "You know, I didn't realize what I was holding in my hand. My mind was somewhere else when I picked it up, Here you can have it, I wasnt planning on buying it."

Agian she smiled sweetly at me. "It was very nice of you to offer to help me look, bye the way I'm Allision, but you can call me Alley"

"I'm John, nice to meet you Alley, my friends call me idiot for short."

"Dont worry about it hun, Ive had those days to" She said. I was alittle impressed that she caught my lame ass attempt at a joke.

"Thanks" I really didn't know what else to say, but I didn't want the conversation to end

We walked toward the counter and Alley paid for the game.

I turned and left while alley finished the purchase. I was almost to my car when I heard heels falling quickly on the pavement behind me. "John, John"

I turned around knowing it was Alley. "Yeah, Whats up."

"I cant believe you were going to leave and not say anything. I thought we had a little spark".

"Really, I mean I did too. I just thought it was one sided. Anyway I was about to grab something to eat do you want to join me?"

"Yes I'd love that John. Where are we going?"

"I was just going to order pizza, but we could got to Marcianos."

"Mmm, That does sound good, but i dont really feel like having to be on my best behavior"

"Then what would you like my lady."

"How does pizza at my place sound?" Alleu asked.

"Sounds great. sure your roomates wont mind."

"No the place is all mine. My boyfriend lived with me at one point but we had some different tastes and now the place is all mine" it seemed she was being a little aloof in her statements but we had just met and I wasnt going to press. I mean she did just invite me back to her house.

"Alright I'll follow you then"

"Ok" she said with a little giggle. and turned go to her vehicle.

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I followed her for about ten minutes. Until we got to an upper middle class neighborhood and she pulled into one of the drives. I parked behind her and folowed her through the door.

"John would you like something to drink?" Alley asked as she walked towards the kitchen. I of course watched her saunter into the other room. My mind was reeling. This really incrediably beautiful woman just invited me into her home and was serving drinks. I don't want to get to far ahead of myself but at this point, I had to believe my chances were good.

"Yes Please, whatever you're having will be fine."

"OK, I ll be there in a minute." I heard glasses rattling and her talking to someone.

She came around the corner carring to glasses. "I ordered the pizza, It will be here in about thirty minutes." She looked absolutley ravishing, Shakespere could have written an endless prose about the way her hips swayed as she walked. I dont think I've ever been on the edge of such anticipation in my life. I was taken aback for a moment I knew she saw me staring at her.

"Ohh um that Sounds great, yeah yu know your house is really nice"

"Thanks" she said giggling. We sat on her couch and talked. we told each other about our jobs, intrest, and what we did for fun. all the basics. the pizza finally showed up. The evening really was going well. It was just a relaxing night in for the most part. I caught several hints of her upper thigh as she would adjust herself on the couch. She always moved so elegantly and carried herself with poise. Every moment I spent around her I became more enchanted by everything about her. Her body, her smile, her voice, and her personality.

After we ate Alley refreshed our drinks and sat back down. "So John"

"Yes, Alley"

"Well I've really had a great time tonight"

"Me too"

"I'm not really ready for the night to end"

Fireworks were going off in my mind yes yes yes yes yes yes yes yes...... whhhheeewwwww hooo!!! "Ok, I can stay for awhile."

"John that would be great" she lightly placed a hand on my thigh. I looked at her, I could see nothing else but the crystal blue of her eyes as I moved towards her lips. The kiss was light, but electric, there was a warmth between us and a shudder of ecstacy rocketed down my spine as our lips caressed.

We parted for a moment. I was amazed at what her lips could do to me. I have never had another person so completely enrapture me. Not with just a kiss. We kissed agian lightly our lips greeted each other for just a moment in time. She cooed when the kiss broke. and of course I thought that was the sexiest thing ever. "John, I want this. I want you."

"Alley this is amazing I've never wanted anything so badly in my life"

"but its not that simple, There something....."

"Its alright, you know you can tell me. Whatever it is."

"Well, its just, I came out of that relationship I was telling you about. It wasnt just diffrences in opinion." I placed my hand on her leg hoping to ease her and give Alley a sense that things were all right. She continued. "it was a diference in opinion but it was Umm with what we did in bed together. sexually" they way she looked at me I could see her eyes pleading with me to stay, that everything would be fine.

"Alley whatever it is I'm fine. You can tell me". She looked at me sweetly, but holding back still unsure if what she was to tell me would send me running out the door. "Alley really, I won't leave, I wont be angry"

"I don't know where to start."

"What is it? You don't like going down on guys? It's OK really"

"No, I like that. Its weird I feel like such a freak." There was a fall of silence over the room it became uncomfortable after a few moments. It was definatly on me to do something about it, as she was wrestlng with her demons at this point. I didn't know what to do so I kissed her. I kissed her full on the lips, my body pressed into hers, She was hesitant at first, but soon responded to me. We kissed for several minutes our bodies laced together, her back arched and her breast pressed to my chest the sensation was heavenly. I wanted her to know I was there for her, and I found her uttelry beautiful. She couldn't scare me off easily.

"Your not a freak, We cant help our desires. Its not as if we could just wish them away. I know that. Look We dont have to do this if its to hard for you there's always another night."

"No, John I want this, I have to find the courage to allow myself to be open with you. John I'll just show you. Will you come with me to my room?"

"Yes Alley", I stood up and helped her to her feet, holding her as we walked forward. I put my hand on the small of her back as we moved towards her bedroom" Alley smiled at me, weakly but I could see the courage in her as she turned and began shuffiling through her dresser. She took out several items of clothing and tossed them on the bed. I looked at the clothes, there was black stockings, lace panties, and corset. She continued until the bed held another matching set in white with a pink corset. I hadn't figured out what was going on but imagining her dressed up in the attire layed on the bad was definalty getting me excited. She turned and faced me with a renewed resolve.

"John I'm attracted to men, I love men."

"Well thats a relief" I said joking

"Im serious. but the thing is. When I have sex I'm only turned on when my lover is dressed like a woman." I turned around alittle taken aback for the second time tonight, but this time for far different reasons. Alley became histerical "John please don't go. I dont want you to leave please stay here. I had to explain things to you. I couldn't not tell you. I hope you understand. John! John!".

I turned back around to face her. "Alley I'm not leaving. It just hit me kind of hard at first. I don't think your disgusting at all. You're extremely beautiful, Im still here, I'm not leaving."

"Really You dont think Im a big freak"

"Of course I do. But you know we all have our things. Im glad you were honest with me."

She smiled with such a sense of release and peace. Her wholke auroa took on a glow. I could have sworn she was an angel. But my angel had on a little black dress with legs I was dying to see wrapped around me. I wanted to make love at that very moment.

"So does this mean you'll try on the clothes for me John." She was excited and I wanted to see her happy. I loved it when she smiled.

"Sure Alley, I'll try anything for you."

"Great, Lets get you started"

"OK what first panties, corset, or stockings?"

"Well first lets take a shower, and get cleaned up a bit" Alley grabbed my hand a lead me to the shower. She started the water while I got undressed. "John thank you for doing this. I promise I'll make it worth your trouble." She knew how to get me excited and wasn't holding back. She handed me a razor, shaving cream, and a bottle of nair. "I want you to shave all over baby" She put the cream on my chest, arms, back, legsand hips front and back. After a few minutes I could feel the cream lightly burning. It was uncomfortable, but to see how worked up she was kept any complaints I had at bay. I stepped into the shower and washed the cream off, my hair along with it. I finished up with a close shave to my face. I got out and dryed off.

I walked into the bedroom to her standing there. She sat me down at a desk and straddled my lap. She began to put makeup on my face.she worked using several brushes. The pencil on my eyes were a little scary, but it was painless. As she went through the process she kept grinding her hips forward into me. It kept my attention while she finished. "Sweetie you look good" I wanted to see what Alley was talking about but she wouldn't let me see the mirror. "No wait, you cant see until we are all finished." She reached behind her and pulled out a blonde wig. "OK hun I wont to be suprised the wig is already styled. So all you have to do is put it on."

"That sounds easy enough"

"Baby put the clothes and wig on and then come get me. OK?"

Alley left the room. As I looked at the bed mentally preparing myself for this, I was already made up to look like a girl, but I had to put the clothes on to finish. I put on the corset first. It was a very beautiful corset and to see a girl wearing this would have given me shivers. The corset buckles in the back so I was only able to cinch my waist down a little. Next were the stockings, once they were pulled up my smooth thighs I attached the six garter straps. I could feel the tightness within the straps as I moved. The two straps running over my ass pulled at my cheeks whenever my legs moved. I was almost finsihed. I only panties left. I pulled them over my knees feeling the light fabric moving over my legs and up to my ass. I wiggled a little to get them to fit properly and lay on my hips. Well I thought I was finished until I noticed a pair of heels sitting beside the bed. I pushed my feet into the heels noticing how my hips went forward and ass tightened as I stood atop the four inch heels. I walked to the mirror to see what I looked like. I was stunned. I really did look like a girl maybe not the most beautiful girl in the world but non the less a girl. For the first time tonight I felt small and feminine.

"Alley I'm ready"

I could hear heels pattering down the hall quickly, right before the door swung open. She was wearing the black corset set that had been layed on the bed. She looked positively hot and my temprture rose. "Oh Honey you look so good. I've just got to have you." She walked to me and turned me around. She undid the corset buckles and told me to breath in deeply as she readjusted the straps to the tightest posittion. My waist had shrunk at lest three inches and my breathing became faster. I was feeling a little light headed. My mind was on my breathing. She grabbed my head and kissed me. I felt flushed still breathing in small tight inhalations. She kissed my neck. I whimpered at the feelings of pleasure. She had taken the lead role in our play and was not going to allow me to settle myself. She continued kissing my body and pushed me onto the bed. Alley lowered herself in front of me at the edge of the bed. She kissed up my thighs and let her hands brush agianst my encased cock. I could feel my panties being pulled down and then off. my cock jumped out of the constriction. She just laughed at the moment watching me breathing heavily layed on my back. "You know hun if it wasnt for this between your legs anybody seeing this would think you were just a girl letting your girlfriend have her way with you." She kissed the tip of my dick "Baby do you like being Alley's girl"

"Yes Alley Ohh God Yes. You make me feel so good"

"What am I going to call you? John wont work anymore." Her tounge licked from the bottom of my shaft to the head as if she were holding an Ice cream cone. She repeated the motion one more time. "I like Janey. Will you be Janey for me?"

"Yes Alley I'll be Janey for you. I'll be whatever you want me to be."

"Good girl. Janey, your mine now. Your my little slut" She was massaging my penis the whole time she spoke to me. I was turned on and being held there. "Can I have you anyway I want."

"Yes Ma'am" I'd love to say that just slipped out but given what was happening it felt right.

"Mmm I'm glad to hear that because there is alot of new experinces I want to share with you" She licked me agian and kissed my dick. I felt so amazing having her go down on me. She wasn't holding back I felt one of balls slip into her warm mouth and gently suck. 'Oh God Alley" agian she pulled my ball into her mouth it was the most heavenly experince I've ever had. I could feel her repostion herself at my side. Her mouth taking my cock into its warmth and bobbing up and down. I was moaning at the intenste pleasure of it all. She moved her mouth all the way down my dick taking in ever inch and sucking as she moved back to the head. Her tounge swirled arounf the head at the top of the stroke and back down. My breathing increased once agian. Alley could tell I was close to cumming and stopped using her mouth as she lent back moving her hand across the veiny flesh. "Not yet sweetie, we still have a long night ahead of us."

We both moved up the bed so our bodies weren't hanging off. I was laying down when she straddled me. Alley lent over me so that her breast were in my mouth. She grabbed each one of my arms and moved them to the headboad where she clsaped them using furry handcuffs. she leaned back and looked down at me. "Try to get out sweetie, I want you to know how helpless you are." I struggled agianst my bonds, but to no avial.

"Alley, there's no way out."

"Thats right Janey. Your stuck i think it makes this all more erotic dont you?"

"I guess, but I really dont need any extra excitment."

"Ow, thats so sweet of you, do you remember when you told me i could have you anyway I wanted"

"Of course Alley it was just a few minutes ago."

"Good then, I want you to be my girl. And what does a girl give to her lover."

"Her body"

"Yes, you are a quick one aren't you dear. But what part of her body?"

"All of it Ma'am"

"Yes but I want you to be specfic. Now what makes a girl special that she can give to her lover."

"Her pussy"

"Yes her pussy dear, and I want your pussy Janey. Can i have your pussy"

"Alley if I had a one I'd give it to you but I can't give you what I dont have."

"So thats a yes then baby"

"Of course, Gorgeous" Alley then produced a butt plug that she lathered with KY. I dont want to hurt my little girl. She moved so that she could reach beween my legs turning around on top of me. Using a finger she teased me a little putting pressure on my hole. I felt her work a finger inside of me. She hadnt moved the finger very far indside but the feeling was very weird and diffrent. She pulled her finger out and pressed the plug agianst my ass. It went in just a little at first then sunk all the way inside of me. Alley turned to face me agian. "Thats not so bad is it. my little girl. I'm glad you decided to give all yourself to me." Agian I was feeling small and very feminine. "Do you like how it feels?"

I didn't know how to answer, it hurt at first but now it was just there and it did make me feel like her girl even more and I liked being her girl i felt like it made us closer. "Alley, I like it because it's for you". She smiled agian, God I am truly falling in live with that smile.

"Janey, you'd make a wonderful girlfriend. I know I'm being selfish but, I want more of you. Is that alright?"

"Yes Alley you can have whatever you want."

"Janey, you've made me very happy tonight. I want you to know that, because if you do this for me you are going to make me the happiest woman in the world. If you don't then out relationship will have to be over and I'll cry myself to sleeo tonight thinking about it."

"Alley whatever it is I wouldnt have you cry for anything, nothing could be worth seeing you sad over."

"Thank You honey, remember that for the next few minutes OK"

"OK"

"Janey close your eyes." I closed my eyes and felt Alley moving up my body unitl her knees were resting beside my head. She cupped her hands under my neck and pulled my head forward. "Janey this is it OK, open your mouth and remember what I said please" I opended my lips not knowing what to expect, I felt something very warm slide agianst my tounge. Alley continued holding my head "Janey lick it." I licked with my tounge hearing her coo as I did so. "Lick it for me one more time sweetie" agian I licked. "OK, Open your eyes now." My eyes opened and saw the unimaginable. Tthis beautiful woman had a seven inch cock standing at attention in front of her. She was looking down at me. Her eyes were pleading with me hoping everything was alright. Before that moment, I could have beleived it was all lust. I layed there knowing that her feelings mattered more to me than what was happening. With that knowledge I kissed her cock and put my lips around the head. Sucking her into me. "Baby, Thank You!" Alley said. I kissed her a few times unitl the sweet moment between us gave way to her more primal needs. She rose to her knees putting more of herself into me. Alley liked the control, it was aphrodisiac to her. She started to rock her hips into me, feeding me more of her. "Damn thats good babe. I love fucking your mouth. Stick out your tounge and lick the head." She continued moving into me. Forcing more of her cock down my throat. Her dick was very hard. "Do you want me to cum in your mouth Janey. You'll really be my whore then. I want you to have a part of me living inside you." Her talk was actually getting to me I liked being her toy to use. I sucked her harder and faster moving as quickly as I could" Ohh God Janey. Ummmmmmmm Thats good. damn baby" Her weight lifted off me and her out of my mouth. She moved back and grabbed my dick and guided it into to her ass. She was riding my cock and staring striaght into my eyes as she fucked me. She buried my rod deep inside her and rocked her hips forward my dick moved agianst her insides.

"Alley, You feel so good baby" Her hands were cupping her breast as she gyrated on top of me. Alley's head rolled back in ecstacy as her pace increased. She was fucking me hard and her dick bounced with each movement she made. I was thrusting upwards moving as much of myself into her as i could manage. She began dropping her full weight on to me. She moved up my shaft and then her ass fell on me. "Janey I want you to cum for me." "Does my ass feel good on your cock" She rose up almost all the way off and then each time she impaled herself fully. "Oh God Yes Alley"

"Are you going to cum for me baby"

"Yes Ma'am" I was whimpering at the exertions.she was so tight. I could feel her slididng down ever inch of me. I couldn't hold on much longer

"Then cum Janey, Cum in my ass"

"Ohh God" I exploded into an intense orgasm and shot a jet into Alley. She was moaning loudly as my cock spasmed inside her. She gave me a moment to catch my breath as my cock softened inside of her.

"Its my turn now sweets." She said as she rolled me over onto my stomach and began kissing the back of neck. She moved the plug around my ass putting pressure on the end. I began to squirm. My nipples had perked from the sensation happening to me. Alley enjoyed teasing me for a few moments, but alas she slowly pulled the plug from my ass. She moved behind me and layed her body across me. I could feel her breast on my back and breath on my neck and ear as she wispered "Janey Im going to make you a women." My throat went dry and my breath stopped. "Relax, and this will be easier for you sweety." Her hand was between our bodies holding her cock as she manuvered it towards my ass. Alley ran the head of her penis along the crack of my ass. She began rocking her hips putting pressure agianst my hole. I felt her rock harder and slip into me. I yelped in pain as she pushed in to me. She stopped moving for a moment as I layed face down on her bed. "Janey relax your ass and the pain will ease." I tried to take her advice and concentrated everything I had on letting the tension from my muscles go. She started to rock gently again. Each time she move she went deeper into my ass until she was buried up to the hilt indside of me. Alley layed on top of me fully buried with inside of me. The pain subsided eventually.

"Is my little whore ready to make me cum" i continued to lay under her not saying anything "Janey I asked you a question are you ready to make me cum you little slut."

"Yes Alley, I think so."

"Then tell me"

"Alley I want you to cum"

"I need more than that"

"Alley make me your girl" She pushed into me.

"More, do you want to make me happy"

"Yes ma'am I want to make you happy."

"Do you like having a hard cock in your little sissy ass Janey" she pulled out of me until only the head was left inside before stroking all the way down on me agian. "Tell me you love it"

"I love having your hard cock indside me" I could feel her pace quicken. She began thrusting into me.

"You're the best little whore I've ever had. Your ass is so tight." I began having flashbacks of her and I in the shower, going down on each other, and then her riding my cock. I wanted her to be happy and feel good as she made me feel. I pulsed my ass around her cock and pushed back at the oncoming thrust. "Damn thats it my slut, fuck me back." I did pushing my body back and my hips down to increase the friction as she fucked me. I started to feel a wave of peasure rush through me and into my extreminties. I pushed back hard as I could and felt her bury herslf in me agian. We were moving in unison, fucking with everything we had. I could feel her starting to tense. "Janey are you my slut"

"Yes Alley Im your slut, My ass is yours, I want you to fill me up with your cum" Alley slapped my ass hard. as our bodies worked together to feel everything we could. MY hips were moving up and down I wanted her to feel good. "Oh Janey," I squeezed my ass as tight as I could trying to milk her of her liquids" "Thats it girl ohh damn"

"Please Alley, cum for me, make me yours. I wont to be yours forever" Alley pushed into me agian with a loud moan. I could feel her spurting into me. As ropes of cum shot into me. I was still moving into her, feeling her spasms inside of me was glorious. I really did feel like her girl and was happy to have made her feel so wonderful.

Alley rolled off me and lay beside me on the bed. She told how wonderful tonight had been for her. "Janey, you were wonderful tonight." She unbuckled my handcuffs and we both just layed there spent from our exertions. we both fell into a blissfil sleep laying beside one another.

  

  

  

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