Message-ID: <34836asstr$1011417006@assm.asstr-mirror.org> Return-Path: From: "John Ashcroft" Mime-Version: 1.0 X-Original-Message-ID: X-OriginalArrivalTime: 19 Jan 2002 00:25:00.0806 (UTC) FILETIME=[BB60D260:01C1A07F] X-ASSTR-Original-Date: Fri, 18 Jan 2002 19:25:00 -0500 Subject: {ASSM} The Baby-Sitter Escort Service, Ch.2 {jashcroft} Date: Sat, 19 Jan 2002 00:10:06 -0500 Path: assm.asstr-mirror.org!not-for-mail Approved: Newsgroups: alt.sex.stories.moderated,alt.sex.stories Followup-To: alt.sex.stories.d X-Archived-At: X-Moderator-Contact: ASSTR ASSM moderation X-Story-Submission: X-Moderator-ID: hecate, gill-bates This is mine. I wrote it; you can read it. (N.B.: "Read" is not synonymous with "steal," "repost," "archive," "rewrite," "redistribute," or "use on a pay site.") --- [Generic fan mail response for the 42 people who wrote after Ch.1] Thanks for writing. Fan mail is cool. Yes, there is more to this. Maybe a lot more. No, I haven't written it yet. Keep writing and I will. Story ideas rock. -John --- [Those of you who read Ch.1, liked it, and didn't write, go on to the next story--you don't get to read this chapter.] --- The Baby-Sitter Escort Service by John Ashcroft Ch.2 A room, harsh fluorescent lights in the ceiling. A table, three people seated around it. One of them's a girl. She looks like Britney Spears' little sister: low-cut jeans, belly shirt, frosted blonde hair. Two of them are cops; bad suits, bad haircuts, bad attitudes. One's tall, fortyish; the other's on the far side of fifty, marking time until his pension kicks in. Pensioner is talking. "Okay. So he was number one, um--" "Mr. Taylor," the girl says. "I don't know what his first name was." "Jack Taylor, right." "We got him already?" the tall one asks. "Yeah. Nabbed him this morning with the rest of them. Wilson said he cried like a baby when they told him what they were there for," Pensioner says. "You were with him again?" the tall one asks. "A bunch of times," the girl says. "He was probably my best customer." "But you never even knew his first name?" Pensioner asks. "He liked me to call him 'Mr. Taylor.' I guess I never asked." "So what was next?" "I went and bought my jacket. That was so fucking cool. The salesgirl was all ready to bitch at me again, when I--" "I mean, call-girl-wise. What happened next?" "Oh. Well, we hadn't exactly gotten into the whole escort service thing yet. See, first I called Tricia from the mall after I bought my jacket." --- "_Well_?" Tricia asked. "It wasn't too bad. For five hundred bucks, I mean." "I still can't believe you fucking did it. How long did it last?" "The sex only lasted like two minutes. He stuck it in, fucked me, and came. But we did some other stuff before that." "Like what?" she asked. "He went down on me. That was actually pretty good." "Eww. Did he get you off?" "Yeah, he did actually. That part I actually liked. He's a lot fucking better than the guys at school." "I guess he would be. Being married and all. _God_. Did you get your stupid jacket?" "Uh-huh. You got to see it. It's so fucking hot." "Do you have any money left?" "Yeah," I said, "like about ninety bucks. It was marked down. I'm going to keep shopping." "I'm doing it. I swear to God, I'm going to do it. There's like fifty different things I'd buy with that kind of money." "With who? Do we have anyone else scheduled this weekend?" "Hold on, let me check." I heard her moving around her room and shuffling some papers until she came up with our work list. "Oh, yeah, the Dillards want us tomorrow night. Mr. Dillard is a total perv." "You think he'd go for it?" "I know he will. I know it. He's always trying to look down my fucking shirts." I told her what I'd done with Mr. Taylor, about the Lycra tee and no bra. Tricia's tits were bigger than mine, so she might not have to try so hard, though. "That's a good idea. Do you think I should hold out for five hundred? What if he tries to bargain?" "Let's stick with it. The Dillards can fucking afford it." I'd baby-sat for them a couple of times and knew he drove this big Mercedes. "Okay. Then I'm doing it." --- That night, after I'd finished my homework, I started doing some research. My folks had a web filter on my computer, but Lauren was a computer geek, and she'd shown me how to get past it. At first, I tried running searches for "hookers," but that pulled up all sorts of porn sites. I started getting frustrated until I thought to search on "escorts." That got some results, and pretty soon I was cruising through a whole long list of web sites run by actual escorts. (Though, by that point, I was sort of an actual escort myself, I guess. But I had a long way to go.) Bit by bit, I realized we had a lot to learn. Mistake number one was not getting the money from Mr. Taylor first. That had been a risk. So that was out--from now on, no pay, no play. I'd have to warn Tricia about it, just in case. Mistake number two was probably being too direct with him. I probably should have been more subtle, in case he had freaked and turned me down. A while later, I found this online book written by a real New York call girl. I figured it would be a great source of ideas, and I wasn't wrong. But when I got to the part when she talked about how she got started, I almost had a heart attack. She'd started just like me! She'd turned her first trick at fourteen, not because anyone had pushed her into it but just because the idea turned her on. Whoa! Cool! Maybe this thing wasn't so weird after all. After about an hour, I logged off to think. Based on what I'd read in her book, we were at least pointed in the right direction. We already had a client list, guys who knew us already and who we knew well enough not to have to worry too much about. We just had to turn the baby-sitting jobs into sex jobs, and we'd be set. And that book had given me all kinds of ideas about what these dads would want out of us and want us to act. I pulled up our list of clients and began sifting through it. I discarded about half of them right away, either because the mom was single or because the dad was just too uptight. I thought one or two of them might be doable eventually, but I figured we'd start simple first. I knocked out a couple more simply because the dads were jerks or otherwise no one I wanted to sleep with. When I was done, I had a list of about ten possible names. Mr. Taylor I'd already gotten on board; Tricia would probably have no trouble with Mr. Dillard. The other eight had all sent me horndog vibes at one time or another. We probably couldn't get all of them, but it was enough to start with. I called Tricia and went over what I'd done. She was cool with all of it, even telling me she'd fuck a couple of the guys on our list even if they didn't pay her. But she was like that. She'd lost her virginity when she was twelve and she'd fucked, so she said, three guys so far. Then she brought up something I had completely forgotten about. "What about Lauren?" "Oh, shit. I forgot about her." "Have even told her what you did?" "Not yet." "You'd better. If we're going to do this." "Yeah," I said. "I'm not sure she's going to go for all this, being a virgin and all." "Yeah, but listen--I had this totally killer idea. Don't you think some guy would pay a whole lot of money to do it with her her first time?" It took me a second or two to absorb this proposal. "You mean, _sell_ her virginity?" "Yeah! Don't you think we could make a shitload of money from it?" I had to think about this. "I bet we could. But I don't know if she'd go for it at all." "So ask her." "_You_ ask her. It was your idea." "Okay. But after you talk to her." "Okay. Let me call her." --- I called Lauren. I had to work up to the subject, but when I started hinting around what we'd talked about that first night, she completely interrupted me. "You did it, didn't you?" I took a deep breath. "What if I did?" "Oh, my God. Oh, my fucking God. Who was it? Was it Mr. Taylor? When you sat for them the other night?" "Yeah," I said softly. I listened to her breathing hard into the phone. "You had sex with him?" "Yeah." "And he paid you?" "Yeah." "How much?" "Five hundred." Another pause. "No way." "He did. And I went and bought that jacket I've been jonesing for all this time." Lauren gulped. "The leather one?" "Uh-huh." "Oh, God. I can't believe that. That jacket is like so incredibly hot. How much was it?" "About four hundred." She sighed. "God." Another sigh. "You remember that ring at Tiffany's? The birthstone one?" "Yeah." I knew what was coming, and that was when I knew she'd do it. She'd been drooling over this platinum ring with a little row of rubies across it even longer than I'd been jonesing over that jacket. "My mom said there was no damn way she'd buy me something like that, that I had no business wanting jewelry like that at my age." "You could get it." "But . . . I've never done it at all. What could I do?" "You've given blow jobs." "Nobody's going to pay me five hundred for a blow job." Her voice began getting strained. "And I'm no good at those either. I couldn't even get Kevin or Jason off. I don't know shit." I'd agreed with Tricia to let her propose the idea about the virginity sale, but I could see Lauren was ready for it. "But with some guys, these old guys," I said, "that's good." "What do you mean?" "Tricia and I were talking . . . we bet some of them would pay a whole shitload of money to do it with you, the first time." She gulped. "Because I'm a virgin." "Yeah." She panted into the phone. "How much?" "I don't know. But probably a hell of a lot more than five hundred." "A thousand?" "Maybe more. A lot more." "God. I don't know. That's pretty fucking sleazy, when you think about it." "It's just an idea." "But you guys are going to keep doing this?" "I think so. I bet we could make all kinds of money doing it. Tricia is going to try Mr. Dillard this weekend. And I know Mr. Taylor is going to want me again." "But what if someone found out?" I ran through all the stuff I'd found out that night in all my research, about how we would run it. She calmed down a little but still wasn't sure she wanted to sell her cherry, even for a few thousand bucks. "So start with blow jobs. Maybe ask for three hundred instead of five hundred." "But what if I'm no good at it?" "I think these dads would understand. It's not like they could expect a whole lot out of us. Tricia thinks it's all about the age thing, you know, perving on us being fourteen. I don't think they care whether we know anything. Mr. Taylor sure didn't. I just lay there and let him do what he wanted." "You think so?" "I know it. In fact," I said, "you should tell them you've never done anything at all. That you want them to teach you." "Eww." "I bet they'd get off it." "But what about the money?" "Do it just like I did. Tell them you want to buy that ring, or something else. They'll get the point." --- So, like six o'clock on Friday afternoon, Tricia called me to work out what she was going to do. We ran over the basics again, then she wanted to know what I thought she should wear. "So you think he likes your tits?" I asked. "Are you kidding? You'd think my eyes were on my chest the way he looks at me sometimes." I'd been thinking about this, and I'd come up with a plan. The Dillards had two kids, a boy and a girl both in grade school, but more importantly for us, they also had a spa in their backyard. One night I'd baby-sat for them, they'd let me go into the spa with their kids, and unless it was super-cold tonight, I figured Tricia could talk them into it too. So I pitched the idea to her. "You want Mr. Dillard to see me in a bikini," she said. "Don't you think that would get him all worked up?" "No shit, it would." "Call them right now, as soon as we get done, and ask. Then show up with your suit under your clothes, and make sure you strip down where he can see you." "Okay." "Listen--this is the best part. When they get back, make sure you've changed out of it and that he sees your wet bikini so he'll start thinking about how you're not wearing any underwear. In fact, don't bring a beach bag or anything like that. Don't even bring your purse. Make it obvious as hell you didn't bring a bra or any dry panties." She laughed. "Oh, God. He's going to rape me." "Can't rape the willing. Or the paid, at least. Maybe even wear just a T-shirt or something that will let him see your tits bouncing around. Don't let his wife see you like that, but see what you can work out." "Okay. That should work." "And get the money first. No matter what he wants to do, get the money first." "Got it." "Call me the instant you're home and let me know what happened." --- I figured I'd just sit around the house and wait for Tricia to call after she'd fucked Mr. Dillard. My folks didn't really let me date yet, or even go out much at night, so it wasn't like I had anything else to do. But like half an hour after I talked to Tricia, I heard the phone ring, and then Mom stuck her head through my door. "Honey, it's Mrs. Wellington. I think they need a baby-sitter tonight." That got my attention in a big hurry. Mr. Wellington looked just like Mel Gibson, and he was definitely on my list of potentials. He was one of the dads Tricia said she'd fuck for free, not that I was about to let her do it. I took the phone. "Hi, Mrs. Wellington." "Kaitlyn, hi. This is Rachel Wellington. I know this is late minute, but are any of you free to sit for us tonight?" "Sure. I'm free. What's up?" "We've got a minor family emergency. We need to go over to my parents' house, and it would help tremendously if you could watch Hunter for a few hours." "Sure. No problem." "Thank you so much. I'll send Neil over to pick you up." --- He showed up about five minutes later, which meant I had no time to put together a good call-girl outfit. Mr. Wellington seemed a little distracted as we drove away, so I figured I was going to have to work at this a little more than I had with Mr. Taylor. "What happened tonight with Mrs. Wellington's folks?" He shook his head. "Nothing. Nothing I want to go into, I mean." "Oh. Sorry." He glanced at me quickly, a look of guilt shooting across his face. "I didn't mean it like that. Rachel's parents are just . . . difficult." "Oh." "She lets them manipulate her far more than she should. This happens about once a week, and ninety percent of the time, it turns out to be nothing." "Huh." "You'll understand when you get older. You don't just marry someone, you marry their entire family." I nodded, then stretched in my seat, pushing my tits out against my blouse. As I expected, he glanced over at me. I pretended not to notice. But that was as far as I got. He pulled up to their house, came in just long enough to get Mrs. Wellington and hand their son off to me, then they were gone. --- Hunter was four years old and a real brat, so I was completely occupied with keeping him under control until he finally ran out of gas and passed out around nine o'clock. Once I'd put him to bed, I called Tricia. "How's it going?" "Great so far. You should have seen the look on his face when he saw me in my bikini. I practically had to mop up the drool after they left." "Mrs. Dillard didn't notice?" "Not really. She was more worried about my being careful with their kids in the spa." "Okay, so stick with the plan." I told her what I'd been up to, and she let out a cry of disgust and envy. "God! I hate you! _Of course_ you get to do it with Mr. Wellington first." "I don't know what will happen, actually. He wasn't as friendly as he usually is." "Well . . ." She sighed. ". . . fuck. We've got to get him some time. Might as well be you. Figures." "Just worry about Mr. Dillard. If we get him into this, I bet he'd want to do it with all of us, like all the time. That could be big bucks." "Yeah. Okay. Let me know what happens." "You too." --- Frankly, I wasn't too optimistic about Mr. Wellington. I didn't think he'd be much in the mood to perv on me with all this stuff with his in-laws going on. It got later and later, and at eleven, I called Mom to let her know I was still there and they hadn't gotten home. She told me not to worry about it, since it wasn't a school night and she trusted the Wellingtons. At eleven-fifteen, the phone rang. "Hello?" "Kaitlyn, it's Neil Wellington. We're going to be here a while longer, but I should be back before midnight." "Is everything okay?" He groaned. "Everything's fine. But Rachel is going to spend the night here. I should be home within another hour. If you get tired, feel free to lie down and rest." Oh, boy. Talk about playing right into my hands. "Okay." He asked about Hunter, and I told him, as I always did--I learned early on in the baby-sitting business that parents don't like people telling them their kids are brats, even when they know they are--that he was just fine and no problem at all. When I hung up, I thought for a minute about what to do. The Wellingtons' house was laid out kind of weird, with the master bedroom downstairs and the other bedrooms upstairs. So having him find me "asleep" on his bed would be easy enough. The question was whether that would be enough to do the trick. Or turn it. Anyway. I thought about just getting naked and under the covers, but that was probably way too much. Even stripping down to my underwear would be tough to explain. Unless-- That was when I had the perfect idea. Baby-sitting, especially baby-sitting little kids, could be really hard on your wardrobe. I'd lost count of the number of times I'd had kids barf on me or throw food at me or make some other kind of mess on me, and more than once I'd had to strip down and run a quick load of wash before their folks got home. So all I had had to do was pretend Hunter had dumped his dinner all over me, and you know, I _tried_ so hard to get my clothes clean before you got home, Mr. Wellington, but I just fell asleep waiting on the dryer. I ran straight to their washing machine and stripped off my top and jeans, then, just for good measure, threw in my bra too. The wash cycle was done pretty quickly, so it was only eleven-thirty when I moved my clothes to the dryer. Then I went to their bedroom, lay down under a blanket, and pretended to fall asleep. But that blanket, you know, it just wouldn't stay put over my tits. Such a bummer. Just before midnight, I heard the garage door going up, and a minute later, Mr. Wellington coming into the house. "Kaitlyn?" I stayed still, keeping my eyes closed. He called for me again. Then I heard his footsteps outside the bedroom. "Kait--" When I heard him choking on my name, I knew he'd seen me lying there with my tits on display. He didn't say anything else. Nothing happened for about a minute, and though I kept my eyes shut, I was pretty sure he was checking me out. I heard a soft footstep. Then another, moving closer to the bed. I could hear his breathing now, and he seemed to be getting choked up. He cleared his throat softly, and I took that opportunity to roll completely on my back, like I'd heard him but was still asleep. So now he had a totally clear view of my boobs. He took another step toward the bed, and he had to be right above me by now. For a couple of minutes, nothing seemed to be happening, until I realized his breathing had gotten heavier. No, that wasn't right. Something else was going on. It wasn't his breathing I could hear. It was something like it, some kind of rubbing or scratching noise. My curiosity finally got the better of me, and I very carefully opened my left eye just a crack. And I saw what Mr. Wellington was doing. He was standing right over me, staring down at me, with one hand inside his slacks. I couldn't see everything, but I could see enough: He was fucking jerking off over me! That was enough to disrupt my sleeping act, and I opened my eyes all the way in shock. Mr. Wellington let out a yelp and jumped away from the bed, jerking his hand out of his pants. I reached for the blanket out of instinct, but I wasn't quite shocked enough to blow my script. "Mr. Wellington--I'm sorry--I was washing my clothes--Hunter made a big mess, and I fell asleep." He stood at the end of the bed, face all red and flushed, trying to catch his breath. "Uh--uh--that's okay, Kaitlyn. I just--I just got home." I let the blanket fall down a little. "What were you doing?" "Uh. Uh." I let the blanket fall down some more, exposing my left nipple again, as if I was too surprised to notice. His eyes went right to it, of course. But he couldn't say anything else. So I looked down at my tits too. "Do I turn you on that much? I didn't think I really had anything." Which I didn't exactly, I'd just moved up to B-cups about two months before, but I was beginning to realize this innocent-teen act was what was going to work with these guys. He gulped. "You're beautiful, Kaitlyn." I batted my eyelashes at him. "I am?" "Yes." That seemed like my cue, so I pushed the blanket aside. "Do you want me?" His eyes bulged. "Kaitlyn, I--" "I want you." Another anguished gulp. "I couldn't. You're too . . ." "Young? I'm not a virgin. I've done it before. But only with guys my age. Not with a guy who knew what he was doing." This was straight out of that book I'd read, by the way. I would never have had the guts to say something like that otherwise. I would never have believed anyone would buy it, but Mr. Wellington obviously did. _God_. Guys are such idiots. Their brains are all in their dicks, I swear. He took an awkward step back toward the bed, so I lay back again. He began taking off his clothes, and though I knew I'd meant to get the money first, I could tell that wouldn't go over too well now. So I'd just have to chance it. When he was naked, he lay down beside me and began kissing me. Like I had with Mr. Taylor, I just let him do what he wanted, and like Mr. Taylor had, pretty soon he was sucking on my tits and heading for my puss. He dragged my panties down and spent about a minute just staring at my puss and touching me with his fingers. Then he bent forward and kissed me there. When I felt his tongue come out and start licking me, I moaned and arched my back. "Oh, Mr. Wellington." I was curious to see if he was better or worse at it than Mr. Taylor had been, and I got my answer pretty quickly. Obviously I had a lot to learn here--he was a _lot_ better. His tongue just fluttered and flicked all over me, teasing my clit until I grabbed at his head to pull him closer. He got me off in just a few minutes, a big tidal wave that made my legs shake. And to think I'd thought some of the guys in my class knew what they were doing. Fuck that. He ate me out for a good twenty minutes before letting me catch my breath. He lay beside me watching me and stroking his fingers over my chest. I hadn't given Mr. Taylor any head, but I felt like doing it now, so I sat up and went for his dick. When I put my mouth over him, he let out a little gasp and reached for my hair. But he stopped me after a moment or two. "Have you done this before?" "Yeah. But--" "Just with guys your age. Okay. Let me show you." And he proceeded to explain to me what I should be doing. Watch the teeth, I knew. But it had never occurred to me to really work my jaw or my tongue, and I had no idea different parts of a dick were more sensitive. Wow. Obviously I had more research to do here if was going to expect to make money from this. Mr. Wellington was satisfied with my technique after a few minutes, and he let me go up and down over him for a while, just moaning and groping at me. Just when I thought I would get out of this with just a blow job, he stopped me. "Let me get a condom." I lay back as he went into the bathroom. He came back rolling it onto his dick, and then he was climbing on top of me. He wasn't quite as big as Mr. Taylor, and he got into me easily. After that, it was just a few minutes of moaning and grunting before he started to shake and I felt him coming inside me. --- "I kind of need to be getting home." He nodded, still lying flat beside me. "Give me a minute." I got up and went for my clothes in the dryer. When I came back, he was pulling on his pants. We didn't say much until we were in his car and heading back to my house. "I'd like to see you again some time," he said. I began the pitch I'd worked up while he was fucking me. "Would I be, like, your mistress?" "I guess so." "So, like we sneak around, and you buy me all sorts of stuff, right? That's how it always works in the movies." "Uh." He gulped. I could see him thinking hard about this, about what I might do if he said no. "Is there something you want me to buy you?" "Yeah. There's this really cool leather jacket at BCBG I've been wanting to get, but my folks totally won't buy it for me. My Mom said was like ten times more expensive than anything I should be wearing." He nodded. "How much is it?" "Like five hundred bucks." Another nod. "All right. Hold on." He hit the brakes and turned at the next signal, away from the way back to my house. I wasn't sure what he was doing until he pulled up to a bank. He went up to the ATM and got some money. He handed it to me when he got back to the car. I counted it out--five hundred exactly. "Cool. Thanks a lot." "But Kaitlyn, you understand that absolutely nobody can know about this. That's very important." "Oh, yeah, don't worry. I won't tell anyone, I swear." --- "I got five hundred," I told Tricia, "what about you?" "Five hundred too," she said. "He went for it like that." "The bikini bit worked?" "Like a fucking charm. As soon as he saw my suit wadded up on the table, his eyes were on me like glue. And because I was still a little wet from the spa, you could see right through my T-shirt." "So how'd you do it?" "_God_. He's such a pervert. I can't believe how easy it was. He put his hand on my leg on the way home, and I just said. 'Mr. Dillard, you can have it if you want it, but it's not free.' He pulled right over and went to his bank." I laughed. "So did Mr. Wellington. What did you do?" "I fucked him in his car, right outside my house. It kind of sucked, though. I had to jerk off after I went inside. How was Mr. Wellington?" "Great. Even better than Mr. Taylor." "Bitch. Figures." "You'll get your turn," I said. "Meet me outside Neiman Marcus? I am totally buying that blouse I saw last week." "Yeah, cool. I'll be there in ten." --- [Chapter 3 coming soon but not as soon as this one--I had it 3/4's written when I posted ch.1. The next one will take a tad longer] _________________________________________________________________ Send and receive Hotmail on your mobile device: http://mobile.msn.com -- Pursuant to the Berne Convention, this work is copyright with all rights reserved by its author unless explicitly indicated. +---------------------------------------------------------------------------+ | alt.sex.stories.moderated ----- send stories to: | | FAQ: Moderator: | +---------------------------------------------------------------------------+ |Archive: Hosted by Alt.Sex.Stories Text Repository | |, an entity supported entirely by donations. | +---------------------------------------------------------------------------+