We stopped around the corner from my house and kissed good-bye. My hand pressed against Mrs. Green's ( Joanne's ) tits and tweaked the nipples as I jumped out of the car. "Call me !" I ordered. "Oh I will, Lover !" and with a wink and that mischievous smile she drove away. I stood there wondering how I had been so lucky to nail such a gorgeous woman but , at the same time , was plotting my next move. I'd have to keep away from Bobby and my mother mustn't know but with some guile we could do it even if it meant sneaking around. That , in itself , was strangely arousing. The next day when the phone rang , I hurried to answer it , knowing it had to be her and I was right. "I don't understand the control you have over me. You're a handsome young stud and I'm an old broad but if you're interested I'm sitting in my car fingering myself thinking about you lover,"she offered breathlessly. "Can you get away ?" I had stayed home from school hoping she would call. "What are you wearing?" I asked. "Just a simple t-shirt and jeans ," she responded. Here was my chance to test Mrs. Green and fulfill a fantasy of mine.
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I had always wanted to have sex with a hooker but had never had the nerve to try to pick one up. I was just too shy and gutless. " Go home and change. Put on the shortest , tightest skirt you have along with a tank top but no bra and no panties. Wear your stiletto pumps but you must wear dark stockings and a garter belt . Do you have a garter belt ?"" What have you got in mind baby ? Sounds dirty ! I'm getting wetter just thinking about it. I haven't worn one of those in years but I can stop and pick up a couple of things at Lynda's Love and Lace erotic store on my way. Be around the corner in half an hour and I'll pick you up. ""No , meet me down at the corner of Jarvis and Dundas,"I countered. "Park your car and I'll pick you up. ""But Dennis that's Hooker's Alley !""Exactly , we're going to do a little role playing. Unless you're renegging on 'any time , any place, any how' . You're not are you , Mrs. . .
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ah. . . Joanne ?" I knew I had her. She figured out what I was after and decided to play along. When I got to Prostitute's Alley there were only a couple of girls working as it was early afternoon. This area would be crawling with hookers ,prospective johns , pimps and cops after dark tonight. Then I spotted her. She looked like a real hooker. She had obviously taken the role seriously. She had on black net stockings , a red micro-mini skirt that just barely covered her ass , a bare midruff , and a red tank top that hardly concealed her breasts. Instead of her high heels she was wearing these high heeled black leather boots that went all the way up to her mid-thigh. Wow ! They were better than her come-fuck-me pumps ! The makeup was plastered on and her pouting lips glistened with the bright red lipstick which matched her top and skirt. Shining with perfection was her long blonde hair. It was easy to distinguish her from the other girls as they all looked like teenagers.
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This was no kid. This was a REAL WOMAN and my cock started to swell just from looking at her. Even if I hadn't known her I would have had to stop my car and proposition her. As I pulled up , some guy was trying to get her to climb into his car but she kept shaking her head while nervously looking around for me. I heard the guy offer her 50 bucks . When she turned him down, he yelled at her that even though she looked good for her age she was just a little long in the tooth to attract the afternoon johns. After all he said the only ones interested in older whores were young guys looking to lose they're cherries and they only came around after dark. I rolled down my window and yelled at her, "Hey,babe, I want to party ! What will a hundred bucks get me ?"The first thing I got was a reproachful look and then a look of relief when she recognized me. She followed the look with the statement, "Sugar you just bought yourself a whole afternoon of party favours. " With a deliberate wiggle in her walk Mrs. Green shook her booty at the guy and climbed in. The dumbfounded look on the guy's face was priceless as we took off. Mrs. Green sounded like my mother as she started to berate me for making her stand on the street corner dressed like that. She said the other girls had threatened her for being on their turf and 2 other Johns had propositioned her.
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I apologized and promised to make it up to her. "Where are you taking me, Dennis ?" she asked. "You don't know me remember ! I'm just some young trick to you. ""Ok sugar. I get it. . . . . . . Well aren't you some sweet young meat, honey ? What have you got in mind ? Have you got some green for momma and what do you expect to get in return ?""I've got $100 and I need you to pop my cherry,"I answered. "The guys are constantly ragging on me about being a virgin and I'm fed up. " With that I started to maul her chest. "Hold on sugar or should I call you 'Cherry'? First we've gotta find a quiet spot to do it.
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Pull around that corner and park in that abandoned building's parking lot. "In my haste I cut the corner too fast and my tires squeeled in anger. I pulled into the parking lot , turned off the ignition and undid my zipper. I grabbed Mrs. Green and tried to force her head into my lap. "Blow me first !"I demanded. Not being in control bothered her and she fought me at first but my strength was too much for her. She pulled my cock out and as she stroked it to erection she played the part to perfection by telling me what a big cock I had for such a young man. It was so big that her poor little mouth wouldn't be able to handle it. She belied that statement by opening her lips and allowing me to push my 8 inches past her lips. At the same time she grasped my balls and applied a steady suction on my shaft. For the first time I wasn't interested in pleasuring her. I don't know whether it was because I had no respect for street hustlers but I felt the need to use her like a john might abuse a whore. I grabbed the sides of her head and started to force her head up and down. I don't know why but I seemed to be filled with rage.
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Unaccountably, I pictured her son , Bobby , walking in on us a couple of days previously just as I was finishing what you might say was my first cumming - of - age . I remembered his anger and this caused a rage in me because he refused to forgive me . He had been my best friend . Surely that should have accounted for something but he wanted nothing to do with me. My anger turned into a sexual rage that I started to take out on Mrs. Green. I wanted to hurt her as Bobby had hurt me. "Suck me you fucking cunt !" I screamed. Mrs. Green's eyes displayed fear when she heard this. I was out of control and I pressed her mouth onto my dick forcing her to take it all the way into her throat. I held her head so tightly as I forced it up and down on my rod that she started to beat me on the legs . I couldn't stop myself ! I needed to cum and I needed to cum in Bobby's mother's mouth. I could feel the cum building in my balls and suddenly I blew jet after jet of my hot cum into her throat. "EAT .
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. . . CUMMMM. . INGGGG!"The cascading sperm shot out of my cock-head and directly into her throat which forced her to gag. She fought like crazy to expel my cock from her mouth and finally I relented. Puddles of cum splashed around her cheeks and down her chin when I finally relented and eased up on my grip. I was spent but she was livid !"You fucking bastard,Dennis !"she sputtered. She spit some of the cum at me. " What was that all about ? You hurt me ? You scared me ?"I apologized profusely and truthfully told her that I had gotten caught up in the role playing.
I had found her outfit and the chance to treat her the way men treated whores too realistic. "Let me make it up to you," I pleaded. I tried to kiss her but she was still too angry. " Just then a police car pulled into the lot and pulled up along side of us with its window down.
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Looking at Mrs. Green's face which still had a mixture of tears and cum on it,the cop smirked and said, "You the new whore on the Alley I been hearing about ?"he queried. "You're one fine looking pro but you should have settled down and gotten off the track by now honey. Leave the hooking to the young girls. " My god he thought Mrs. Green was a real whore !Looking at my pimply face he continued, " Get your rocks off Boy ? Looks like you been fucking someone who could be your momma. She ain't your momma is she boy ?" Without waiting for an answer he ordered, "Get that car in gear and take her out of my precinct. We got enough whores . We don't need another even if she looks classier than the losers on the Alley although she don't look too classy right now with her face covered in god knows what. "I didn't need to be told twice. I started the engine and raced out of there. Mrs. Green continued to sob and I knew I couldn't take her home like this. If Bobby saw her like this I would definitely be a dead man. I decided to take her to nearby Kingston Road which has numerous motels with lots of privacy.
There I could clean her up and try to make it up to her. At the check-in the clerk peered at me through his dark glasses and looked out the window to see what he seemed to believe was a whore sitting in the passenger seat. He smirked and asked how old I was. After telling him that I was old enough, he sarcastically asked me if I was with any adult. He looked back out at Mrs. Green and licked his lips as he admired her prominent chest. He smirked again. "That your momma,son ?"he laughed . He thought his question was hilarious. I was getting really irritated. "No. It's my aunt !" I countered sarcastically. "What do you care ?Look just give me a room !""Do you want it by the hour or for the night?"Being naïve, I hadn't even realized that I was checking into one of those adult motels . "How much for 3 hours,"I asked. "Three hours !"he laughed.
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"Boy you are young, ain't you? Most guys want an hour and they're out of here in less than that. Tell you what. Let me have a go at her when you're done and you can have the room for free. That's one fine looking 'aunt' you've got there. I don't mind sloppy seconds. " With this he disgustingly stuck his tongue out and flicked it up and down. "Know what I mean ?"My disgust showed and without waiting for an answer he told me $30 but no registration. Obviously , this was going straight into his pocket. He tossed me the key. I turned and got out of there as fast as I could. When I got Mrs. Green into the room she seemed in a much better frame of mind. She was in control again. "Sit on the bed , Denny . I want to show you what you're going to miss if you ever treat me like that again.
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"My eyes adoringly took in all her features. Her long blonde hair cascaded over her shoulders as she shook her head seductively. Her compact breasts were barely being held in by the thin material of her red tank top. Her tummy just barely stuck out over the skin-tight micro-mini skirt. This was the only real sign , aside from a few wrinkles around her sparkling deep blue eyes , that she wasn't a teenager. As I said earlier the thigh-high boots rose seductively to her muscular thighs. She pirouetted slightly , threw her hair back and smirked, "Like the outfit?"My erection was very prominent by this time and she looked seductively down at it as it strained against the material of my pants. "Did I do that ? Take it out and play with it. "she ordered. I couldn't wait to let it out. I would have done it anyway but I know she needed to feel in control. As I released it, Mrs. Green started to move her hips seductively back and forth while massaging her breasts. The nipples were poking out. She bent over and shook them at me.
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Looking down her cleavage was always a turn on for me and she knew it. "Want to touch sonny boy ? Want to kiss these babies ?" With that she pulled the top right over her head and shook her blonde tresses from side to side again. This caused her boobs to shake as well and I started to lick my lips. I pleaded with her to come to me and let me suck on them but she kept her distance. Next she rotated slightly and showcased her firm ass. I remembered that first time I had explored them at the base of her steps and reached out to touch them. "Not yet lover!"she admonished. With that she bent over even farther and her tight skirt rose all the way up her ass until her black garter belt and thong panties were exposed. "Oh my god ! Mrs. Green you don't know how fucking excited you're making me. I've got to touch you ! I've got to taste you ! Please !""Not yet , Dennis , and remember I'm 'Joanne' when we're alone. And by the way, I can tell that you're excited !" And with that we both looked at my raging cock which was standing at full attention pointing out at her. We laughed in unison. She pulled out the chair , sat on it and turned slightly as she pulled each boot off . It seemed to take forever but when they were finally off she sat on the chair,turned seductively and started to unfasten each garter.
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Painstakingly , she slowly rolled them down her gorgeous , perfectly formed legs. I remember wondering if she had been a dancer in her younger days. She posed like this with her toes pointed and looked for my approval. She chuckled gently when I pleaded with her to finish her disrobing. As she turned from side to side she stroked herself through the thin see-through panties. Her free hand continued to caress her boobs. Suddenly she got a glazed look in her eyes and I realized that she was having an orgasm ! What a turn-on !She pulled the crotch away,spread her legs and raised her feet up off as she pulled her pussy lips apart. I was going crazy and my hand was really stroking my cock in earnest now. I was getting ready to cum when she noticed . "Save that for me !"she commanded and flew across the room . Pushing my hand away,she squeezed the base so hard that the pain kept me from cumming. She pulled me to my feet using my own cock. I was at her mercy now ! She could have done anything she wanted ! Fortunately , she wanted my cock in her mouth ! She knelt down on the floor and looked up at me. "Now, Dennis, fuck my mouth but remember what happened the last time. If you hurt me this time, I swear I'll bite it off !""OW !" I thought.
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I don't know how I could have stopped anyways but my rod once again proved that it had a mind of its own. It began its assault on her mouth. In and out . In and out ! "Mrs. Green , I mean , Joanne ! You have the most fabulous mouth ! I can't hold out much longer ! Your strip show and your sexy outfit have made my cum boil in my balls.
You've got to let me cum now !" She released me long enough to mouth the words "Okay,Denny boy ! Fuck my face ! Give me all you've got ! Drown me with your juice 'cause I'm GONNAAAAA. . . CUMMMMM. . . . . MYYYY. .
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. SELFFFFF !!!!" The warmth of her mouth and slurping tongue along with the squeezing of my scrotum brought me to the precipice. Without regard to her warning, I grabbed the back of her head and pulled it into my groin as my hips pushed my cock right to the back of her throat. She grunted but didn't try to fight it. This time she encouraged it by grabbing my ass cheeks and pulling them into her face herself. A couple of more violent thrusts and I knew I was about to release another fountain of cum ! "HEREEEEEEE. . . IT. . CUMMMMMS, BAAA. . BBBBBY ! seemed like I was shooting gallons of cum into her throat and she was vainly struggling to swallow it all but there's only so long that you can hold your breath so she gagged and pushed my cock away from the back of her throat. I continued to ooze my jism into her mouth but she didn't force me out of her mouth. As the spasms subsided, she started to lick and finally released the head.
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Once again the excess spilled over onto her cheeks and chin and drops even fell onto her tits. What a difference from our previous encounter in the parking lot. I guess it was a matter of her feeling that she was in control. Even though her face glistened from all the cum, she smiled and proceded to clean me up with her tongue. She had some on her hand and offered it to me but I declined . That's not something that I felt the need to experiment with. She crawled past me and pulled herself onto the bed. Kneeling on all fours,she spread her ass cheeks totally exposing her womanhood. "Your turn lover !" was all the prompting I needed. I realized while looking at magazines and watching videos that this was one of the biggest turn-ons for me. . I started at her knees and worked my way up the inside of her thighs until my tongue touched her anus. She grunted when I teasingly stuck my tongue in . "Oh my god ! That's incredible ! I'm gonna cum again !" and sure enough she spasmed and her legs started to squeeze together. Not giving her any rest, I continued my assault with my tongue.
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I started to lick her clit and as I did my nose touched her anus. This shocked even me as I would have thought that this would be a sure turn-off but it had no such effect. My woodie started to grow again. Teasing the sensitive clit with my fingers I now started to push my tongue into her moist crack as far as it would go. This elicited another orgasm. That pushed her over the edge. "FUCK ME NOW , DENNY ! FUCK ME !"I moved up over her back and mounted her. I don't know why but I knew instinctively how to do it 'doggie style' as she called it. I guess it was just animal instinct. My cock spread her lips apart and plunged into the moist channel. It was glorious. Over and over I drove my cock in as deep as it could go. My balls were banging against her sex. Each of my thrusts was met with her own grinding backwards movements. We went at it like this for several minutes.
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We were both groaning in ecstacy as we built towards a mutual climax. She pushed back so violently as she had another orgasm that my cock fell out of her channel. In a panic , I drove my cock back into her hole however this time her hole was extremely tight not at all wet like before. "Oh my god !"she groaned in pain. "No, baby, not there! You're in my ass ! No one has ever fucked my ass before !"Even though she groaned each time I drove my cock home, she must have liked it because she didn't make much of an effort to stop me ! In fact , her words encouraged me. I was in 7th heaven ! She was so tight ! In and out I drove my steel-hard rod . Knowing that I was now performing anal sex for the first time , the increased eroticism spurred me on ! My older and more experienced lover was letting me do something to her that no other man had done ! Even though some people consider it dirty it was having an incredible effect on me . I felt huge ! I felt like my cock was the size of my arm ! The more I fucked her ass, the harder she pushed back. My cock was buried to the hilt ! This intense feeling couldn't last much longer but I knew I had to make her cum with me so I reached around her waist and started playing with her clit. At the same time my other hand was squeezing her breast ! She seemed to be in agony but ecstacy each time I drove my cock home ! She screamed at the top of her lungs, "FUCK MY ASS ! MOTHERFUCKER ! FUCK ASSSSSS!!!!!!!CUMMMM. . IN. . . MY.
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. . . ASSSS!!!!!!" I'm sure the creep at the check-in could hear her and shamefully, somehow it made me proud. Finally, I was there too ! "HERE IT CUMS MY WONDERFUL SLUT WHORE ! I'M GONNA CUM IN YOUR ASSSSS !!!!!" The release of my cum into her ass elicited a woeful groan from Mrs. Green as she humped her butt back onto my surging cock matching every push of mine with an equal push back. Finally we were satiated and I collapsed onto her back with my cock still in her rear. Her knees buckled and she fell onto her stomach. We lay like that for what seemed like an eternity but probably was only a few minutes. My cock deflated and fell out of her ass with a plop. I looked down and her hole stayed wide open for several seconds. It was full of my cum which oozed out and onto her ass cheeks as the sphincter closed back to its normal size. As I rolled over onto my back , Mrs. Green seemed to come alive again. I couldn't believe my eyes and ears when she said that she had to taste me and leaned over and touched my glans with the tip of her tongue ! She seemed pleasantly surprised when she wasn't repulsed by the taste of her own bung hole and started to lick up all the left over semen on my cock and in my pubic hair.
"Only a whore would do this for you baby ! I'm your whore !"I started to get hard again with her ministrations and words. "Ah young manhood. Up again so quickly ? Lay back lover. Let me eat everything you've got left !"I took a little longer this time but eventually she was successful. She got what she wanted when I came in her mouth again. There wasn't much left but she drank every drop. We showered together and I got her off again with my hands but my cock now was so sore that I couldn't enjoy her lips wrapped around it. We dressed and headed for home. I couldn't help but give the check-in guy the finger as we left the premises. When we got back to her car,she sucked my tongue,patted my joint and climbed out. Seeing her in her hooker outfit reminded me of what I still had to do. I called her back , gave her an envelope and told her not to open it until I had gone. As I drove away, I looked back,saw her tear open the envelope,look inside and start to laugh. What had made her laugh ?Author's Note : You the reader can decide what was in the envelope . Give me your feedback.
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Let me know what you think would be most appropriate . The 3 choices are : (a) Inside I had left two fifty dollar bills as payment to my whore for the 'afternoon favours' ; (b) an IOU stating that I owed her $100 for the afternoon or ; (c) $ 100 in monopoly money as payment for her afternoon. .
