Prostitute Stories: Sherry and Kerry Part 1I’m usually vague about the cities I lived in when I recall these stories and I have my reasons for that. I believe this is the first story I’m telling in this location. This particular city is interesting in that it has two blades (or two tracks or whatever you want to call it). Two main streets that run parallel for about a mile or so where girls walk. One street is where mostly white girls walk and several blocks over there’s one where mostly black girls walk. Strange huh? It also serves as a metaphor for the city’s history itself. Now this isn’t enforced or anything, and this is unrelated to my previous story about race. What this comes down to strangely enough is d**gs. Believe it or not there are cultural preferences for d**gs. While I’m not as bold to say it’s a cultural preference between races I am comfortable saying it is one between communities. The track dominated by mostly white street walkers was also dominated by heroin dealers and the one dominated by mostly black street walkers was dominated by mostly crack dealers. I frequented both tracks regularly but tonight well . . .From her back I can see a mess of curly blonde hair jostling about I pull up beside her to get a better look. It’s a quick look but enough for me to know she is very much my type. She looks a little older than me at the time probably early 40’s, dirty blonde hair, and she was pretty, yet she still had this trashy quality to her look that I personally love. I asked her if she wanted a ride and she hopped right in. We introduced ourselves, “Hi I’m Sherry”. Usually at this stage I slowly and aimlessly drive the car around to give us some time to talk and negotiate a price. Strangely Sherry didn’t want to negotiate she just wanted me to drive down the block. “We can go to my place I’m sure whatever you give me will be fine. Do you mind driving me to the gas station first though?” I was a little surprised “Oh I’m sorry I thought you were out here working”. It turns out she was just walking, “No I don’t walk the streets like that. I mean don’t worry it’s fine I’d like to do the date with you but that’s not why I was out here. I just wanted to stretch my legs and get some snacks”. Wow that’s very surprising I love when I just happen to catch someone out of their normal routine like that.Sherry seemed warm but she was very quiet. She didn’t do small talk, she was perfectly content to sit in silence rather than fill the space with pointless chatter. She only talked when she actually had something to say and even then it was at a whisper. I liked this about her there was something comfortable about sitting with her in silence. We get to the gas station and I park and wait while she goes to get her snack. She gets out and walks to the window and I pull my phone out to check my non existent messages. While I’m waiting I can hear some murmuring going on outside. I look over and see a line of people waiting outside. If you live in a nice quiet neighborhood in the suburbs at night your local gas station probably operates the same way it does in the day. If you live in a seedy neighborhood in the city it’s a different story. Gas stations are up and running but are operating with the entry way locked down and communicating with the cashier behind bulletproof glass on the outside. Sherry is at the front of the line shouting something. I roll the window down.“No you stupid Mother Fucker I want a Reese’s peanut butter cup!” “Right there! No you passed it! Right next to your hand!”You could see people in the line getting agitated. “You fucking Idiot! Why don’t you speak english!?” She starts banging her fist on the glass. “I hope you do call the cops! What the fuck are you going to tell them? You don’t speak english asshole!”I feel sick to my stomach I’ve only known her for a few minutes but I would never have guessed this is the kind of person she was.She pushes her way past the people in the line and starts booking it towards my car, get’s in and starts crying.I tried to put my arm around her, “Don’t do that! I’m not some little fucking baby girl I’ll be fine just give me a second”. “I’m sorry, I’m really not like this. I don’t cry. I don’t like when I get this angry I feel out of control.”I drive around the corner to the next gas station hop out and buy some Reese’s cups. We crack some open and chow down. Were they delicious? Of course! They’re fucking peanut butter cups.We go to her place in the projects and her sister opens the door, Sherry introduces me, “Hey don’t worry he’s ok.” She lets us in. It’s a 2 bedroom apartment, very clean and nicely decorated. Her sister looked like she was settling in for the night, no makeup, and a big bathrobe on. Along with her sister are some friends, a girl and a guy, maybe a couple. I couldn’t help but notice the girl had a smoking body she was thick as hell with an hourglass figure. I tried not to stare too long but I felt like she caught me looking. In the corner is an adorable little blonde boy on a toy horsey he looked to be around 3 years old this was the sister’s son. “Sherry where the hell were you?” She gave her a big hug, Sherry pulled out some snacks from her pockets including the Reese’s cups. “Sorry I just needed to take a walk.” She introduced me to everyone else then grabbed my hand and led me towards her bed room. “If you need anything we’ll be in here” She closes the door, turns on the TV and tells me to make myself at home. I have to say this is one of the nicest places I’ve been to. You know, for a prostitute. Then again she did say she wasn’t a streetwalker looks like she’s telling the truth. “Are you in a rush? I just wanted to go freshen up”. It is always a great sign when your date asks if you’re in a rush. The worst thing is a fucking clock watcher. I sat back, kicked my shoes off, and put on some Law and Order waiting for her to get out of the shower. She enters the room with a little lara escort white towel wrapped around her, and a mini towel sculpture on her head. “Why do you still have your clothes on? I thought you’d be waiting for me naked”. I start stripping down “Oh god I love this show I think Benson is so pretty. You know she doesn’t look like a supermodel or anything but she is really pretty like in her own way”. Astute observation, I agree. She dropped her towel and . . . look I already told you that Sherry was pretty but seeing her naked in front of me it became very clear she was a god damn knockout I mean completely out of my league. Now I personally have a thing for thick girls that’s my preference big boobs, wide hips, fat ass the bigger the better. Sometimes you meet women that transcend your preferences. Sherry had a perfect body in the classic sense she was hot by just about any guy’s standard. She had small but toned shoulders and arms, small perky breasts, a flat toned stomach, great abs, a thin waist tapering into nice shapely hips and a perfect cute little ass. She had toned but thin thighs with that space between the legs that drives guys nuts. Jesus that girl had great legs.We got on the bed and the second I sat on it I realized “Oh this is an airbed” and as if reading my mind she says “Sorry about the bed I’m waiting until the end of the week before I get my real bed” She reached up and started rubbing my shoulders and I reached across to rub her back. She leaned in and gave me a soft kiss and we started making out. You know from the second we entered this apartment none of this felt like a date. This all felt very natural nothing felt sordid about this. She leans back and I’m rubbing my hands all over her tight body. She’s clearly enjoying this I can hear her breathing heavy and making light moans. Every time my hand goes anywhere near her pelvis she quivers and arches her back and I take that opportunity to suck on her small perky tits. Her nipples get hard and stand at attention. Jesus her nipples are fucking thick and long I sucked on one while she pinched the other one biting her lips. I reached down feeling for her crotch and once my hand landed she breathed in hard, grabbed my arm and stopped me.I asked her what was wrong, “Nothing I just know once you do that I won’t be able to control myself. Why don’t you turn over and lay on your back?” I did what she asked, she made her way between my legs and started sucking my dick. I looked down at her face as she took these long hard pulls, watching her cheeks cave in. I could tell that she was enjoying this all of it even the blowjob. I reached up to move her hair out of the way and with both hands she grabbed me by the wrist and pinned my arms to the bed. Her lips vacuum sealed around my shaft and her head bobbed up and down. She would suck and then stop to look at my hard wet dick, running her tongue up and down from the tip to the balls. Then when she thought I had enough teasing she’d dive back in mouth first, swirling her head up and down, back and fourth in a circular motion. I was leaning back having an out of body experience when she paused and looked at me “Are you ready? . . . or do you want me to keep going?” I looked towards her and before I could even open my mouth to reply she was right back on the dick sucking me brainless. I thought I knew exactly what I like in a blowjob fast, aggressive head, all the way down the throat and lots of spit. This girl was showing me why you should always try something new. Her style was very different it was slow, precise, she focused on sucking the head so hard it felt amazing I’ve never had a girl give me a bj like that. I was finally ready and actually had to stop her from sucking. She hopped over me on all fours perched like a cat she put her hands between her legs reaching for my dick and slowly guided it inside of her.She sat all the way on it and to this day the thing that’s so remarkable to me was how well we fit together. I’m not talking personality wise like we had a bunch of shit in common I mean literally, physically, my penis fit the mold of her vagina. I know I’m not crazy because she said the same damn thing. I mean she really fit like a glove I could literally feel her snugly all around my shaft, to the tip of my head. When either one of us would move she would take a short breath and I would immediately feel her tighten all around me. She starts slowly rocking and gyrating her hips gripping me tight with each thrust. We both moved slowly feeling each other out and almost afraid to move too much. I was fighting to keep it together I felt like I might explode at any second and she was wincing and pulling back with every little movement. After a few minutes we got comfortable and she began rocking harder, faster and moaning louder. She arched her back, her perky nipples look amazing I want to reach out and grab them but before I get a chance she leans over me. She grabs my chest and starts fucking me hard. She whispers “Oh fuck” and starts quivering, her nails digging in me. She clenches her hand into a fist and starts hitting and slapping my chest repeatedly, moaning, trying to catch her breath. “What the fuck was that?” I said in shock. She’s breathing heavy, “OH my god I’m sorry are you ok? I couldn’t help it.” I picked her up and laid her on her back. She wrapped her arms around my neck and her legs around my waist. She pulled her head back as I pushed inside her. I sucked on her neck and she starts moaning. I pull myself up to look at that gorgeous body and she puts both arms back running them through her hair god dammit she’s sexy. I start fucking her like I really wanted to without holding back not caring about where we are and who’s outside and she didn’t try to stop me. She puts both her arms out and grabs the edges of the sheets her head still leaned back. Then she starts wiggling her hips and out of nowhere she quickly grabs her escort lara pillow puts it over her face and starts a muffled moan into the pillow “Oh god, oh my god, oh god”. I tried to lift it off of her and she held it down all I could see was her chin and her mouth as she was biting the bottom of the pillow, grunting. There were two things unique to Sherry that would drive me wild whenever we were together this was one of them.It was as if she was doing her very best to just keep it together like she was on the edge of completely losing control. When I see her like this the only thing I want to do is bring her over the edge. I fuck her hard and fast testing the limits of that air bed. I rip the pillow from her face and throw it across the room. She lets out a yelp and wraps her arms around my neck again pulling me down to her chest. Under her breath she starts whispering in my ear. “Cum in me. Please. Cum now” She repeats this over and over again. I let loose.Of course I was wearing a condom but I can feel it I shot a huge load, my cock pulsing inside of her. “Oh my god I can feel you pulsing inside of me”. I’ve heard a lot of women tell me this. I started lifting myself off of her again she pulled me down “Hold on, stay still, don’t pull out”. This was the second thing Sherry did that would drive me wild. I laid still on top of her, her arms still wrapped around my neck and her legs interlocked with mine. She’s stroking the back of my neck, then running her fingers through my hair. She lies still moaning quietly in my ear and then she starts slowly moving her hips and she gets louder, her body starts shaking and ,“Oooooooo Shit!”, she came just like that. I had a huge smile on my face that was amazing she grabbed my face and started kissing me. Then a knock on the door. “Hey guys, could you wrap it up? It’s getting late”. It was her sister kicking me out. I pulled off of her and she grabbed me again, “Wait! Don’t move! Just one more time I promise”. She pinned me down shaking in the bed over and over, cumming over and over and finally she stops. “She’s panting heavily “Fuck ok I’m done now”. She waits a moment to catch her breath and then runs out to get me a towel and some wipes to clean up. Before she makes it back into the room I can hear her whispering with her sister they’re arguing. I couldn’t make it all out but one part I could hear clearly is her sister saying. “Who the fuck is this guy? Why is he still here?” When I heard that I checked the time. She was right I had been at their place for nearly 3 hours.Sherry came back in with the towels and I cleaned up and we talked some more. I asked if everything was ok, “Yea me and her are always fighting. I love her to death but we argue a lot”. We start talking a little bit about her c***dhood and she had it rough growing up. I got dressed and was ready to go at that point I didn’t want to overstay my welcome any more than I already did. The problem now was Sherry it turns out she’s actually quite the talker. This wasn’t like earlier now that we got to know each other she was opening up to me and like I mentioned earlier she doesn’t talk about trivial things. We were deep into conversation about some serious stuff and I would be a complete asshole If I was just like “Ok hey sorry about your shitty life, and disaster of a c***dhood, but thanks for being a great fuck I’m taking off”. So I sat and talked with her. It was almost one hour later when her sister came and knocked on the door again to kick me out. At this point she hated my guts but there was nothing I could do about that. Sherry walked me to the door, everyone was gone, she gave me a long goodbye kiss. “Listen I had a great time with you. I don’t get a chance to talk to anyone like that. I want you to stop by and see me again.” I told her ok I would definitely stop by again.Sherry became my new regular I really liked this girl I would see her at least once a week sometimes more. While her sister was always kind of cold but she got used to me being around. I would often play legos with her k** if I was waiting for Sherry. Sometimes I would watch him while she ran to the store. Their friends also got to know me. That cute girl with the thick body turned out to be the sister’s best friend and unlike her sister we got along really well. Hell even the boyfriend and I got along. This was definitely a problem because I clearly had a thing for her that I wasn’t hiding so well.There were a few times where we were left alone and got to talk. She knew about Sherry and my arrangement. One time she cornered me and started asking questions. “So do you like, do this with other women or just Sherry? How much do you pay her? Do you make her do weird stuff?” She could see how easily I became embarrassed around those questions. For the most part I thought she was just trying to get a rise out of me. However towards the end of one of our conversations she casually drops “I never showed you my place before? I’m right upstairs, my boyfriend doesn’t live with me he’s a few towns over.” I’m thinking to myself yes I’ve met your boyfriend a million times, I know. Jesus Christ this girl wants to get me into some serious trouble. “If you get a chance you should stop by and say hi sometime.” I told her maybe but I never did visit her I didn’t want to ruin things.As time went on she got bolder. She once flashed me her g string pulling up the back of her skirt, then pretending she didn’t know I was there. She also once handed me her phone to look at a photo of her and her man at the beach. She encouraged me to keep scrolling through and sure enough there were pictures of her naked showing off her ass, her tits, and spreading her legs. She gave me this devilish smile. “Give me your number and I’ll send them to you.” Dammit. I know it’s only a matter of time before I fuck this chick’s brains out and then everything’s going to go to shit. Also let me be clear I’m not some Don lara escort bayan Juan women just throw themselves after at the sight of me. This girl just wants the same arrangement Sherry and I have. She’s not after me she’s after money and I know this but I can’t lie all the flirting and attention still feels good.Other than the friend, things with Sherry and I were amazing that is until the day I invited her to stay over at my place. I’d been trying to get her to stay over for weeks and she finally agreed. I drive down in the morning to pick her up early, she was already up cleaning the apartment. “Just give me a second I’m just going to finish up here then get dressed and we could get going” I sat and waited her sister popped out for a second I tried to talk to her but she was acting weird. Sherry was finally taking a shower but she seemed to be taking forever. I sat and watched TV. When she finally got out the shower I’d been at her place for almost two hours! “Hey come here and keep me company while I get changed.” I walked in and she kissed me then asked me what’s wrong, “What’s taking you so long? I’ve been here 2 hours and you’re not even dressed yet”. She starts digging through her clothes “Ok I’m sorry I’ll hurry up we’ll be out of here soon.” She grabs some clothes and runs to the bathroom. I sit and wait in her room, and wait, and wait. I knock on the bathroom door “I’ll be out in one second.” More waiting. She finally comes out of the bathroom . . . completely naked.” It’s now been three hours and I’m fucking furious. “What the hell is going on with you?”Sherry looks at me with tears in her eyes “I don’t know what you want from me! Stop putting all this pressure on me! I can’t be this woman you want me to be!” What the fuck is going on? She starts crying uncontrollably and runs back to the bathroom. I step outside to get some air when I return Sherry is still naked running around the living room cleaning like a crazy woman. “I’ve just got to get this place clean before we leave! It’s filthy!” I walk in the room she looks up at me and pulls me by the arm. “Get in here!” She slams the door shut then puts her ear to the door. “Sherry what are you doing?” “Shut Up! I can hear them out there.” There was nobody out there. “The cops they’re still out there everyone stay away from the door!” Holy shit she has fully lost her mind. I’ve never seen her like this ever. I knock on her sister’s door she opens it and I can see she’s pissed. “Hey something’s wrong with Sherry she’s acting crazy. Do you know what’s wrong?” She walks out into the living room and stares at her for a while, then she looks at me and says “I can’t deal with this shit, don’t bother me again.” She pushes me out the way and slams her door. Now it all hits me, everything makes sense, and I feel like an idiot.Sherry’s not sick, her sister’s not acting weird, they’re both just high as hell, they’re both fucking d**g addicts. I don’t understand they seemed so normal I felt so stupid and if you’ve been reading my other stories then you should feel stupid too. Why? Because these girls are all addicts! They always are! How the hell did I miss the signs? The biggest one being addicts have zero sense of time. No fucking wonder I would be at their place for hours at a time without her noticing. No wonder she couldn’t do something as simple as get dressed in under a half hour without having a nervous breakdown. Sherry wasted most of my day I was pissed off and left. I didn’t see her for a few months after that. I just didn’t have the strength or desire to deal with what she was going through.On a day where I really missed her I finally decided to drop by for a visit. I knock on the door and some guy I’ve never seen before answers. I ask if Sherry’s there “Who? Oh wait yea she don’t live here any more but talk to the girl upstairs she knows her.” Oh no. I’ve done my best to avoid going to “the girl upstairs” because I know for a fact that if the two of us are left alone I will fuck that chick’s brains out. Plus she seems like the type to get off on the drama that would create. I have no choice though, and who knows maybe it’s for the best if Sherry’s actually gone now there’s no reason to avoid her thick friend.I head to the apartment upstairs knock on the door and she cracks the door open and . . . oh it’s Sherry’s sister. “Hey so looks like you finally found us. What took you so long?” I ask her if Sherry’s around. “Sherry’s locked up, she got busted right after you left. I had to move up here with my friend”. Damn that sucks, I felt bad, plus I really wanted to see her. We continued catching up outside her door but we never really got along so with Sherry gone I just wanted to wrap things up and get out of there. As I was getting ready to leave she drops this on me. “Look I know you and Sherry had a thing and you wanted to see her, but since she’s going to be gone for a while. . . you could . . . I mean if you want to . . . Look my friend’s not here, I’ve got the place to myself tonight”.Holy shit! I can not believe what she’s asking me. Hell she couldn’t even get the words out of her mouth and I was so dumbfounded I couldn’t answer her I pause in complete disbelief.She took that as a bad sign “You know what forget it! I knew this was a bad idea.” She started shutting the door. I stopped it with my hand “Wait! It’s ok. I want to. Can I come in?” She looked at me relieved, she backed away and opened the door all the way her expression changed to something more like embarrassment. She was wearing her usual uniform, a bathrobe and some house slippers, and . . . HOLY, FUCKING, SHIT! I may have been shocked by her question before but I damn near fainted when she opened the door. She is very, very, very pregnant. Her face turned bright red. She asked me sheepishly “Do you still want to come in?” I answer her in shock “Yes. . . yes Kerry I do”.So here I am once again walking into Sherry’s sister’s place for the first time. Once again I notice how immaculate Sherry’s sister’s place is, and once again I’m being led by the hand straight to the bedroom except this time it’s with Sherry’s sister, Kerry.To be continued.