My New Girlfriend
Chapter Two

      The next morning I was awakened with a blowjob, just like I’d asked. After Courtney swallowed, she strutted into the kitchen and made me a full breakfast, still in the buff. On a whim, I had her sit on the table with the plate between her widespread legs and feed it to me. Then it was time for me to get ready for work.
      She thanked me for a wonderful morning before I left.
      So now that I’d committed to this, it was time to figure out how to proceed. I was normally a relationshippy kind of guy; I got involved with a woman not just looking for a good time (though that helped), but to seek out someone I could see myself growing old with, someone who might make a good mother if we ever decided to go that direction. I’d been with several women in committed relationship, divorced once and almost married another time. 
      Courtney was obviously not such a woman, and the first thing I had to do was abandon any romanticized notions of converting her into one. Hell, I didn’t even know if I wanted to. Having someone I could trust and confide in, someone who challenged and supported me… that was great, really. It was.
      Having a woman whose face lit up when you snapped your fingers and pointed to your cock… well that was new territory, and I aimed to explore it. It was for her sake as much as for mine, honestly; the last thing I wanted to do to this adoring, insatiable, generous woman was to turn her away by not giving her what she wanted in return.
      Namely, my approval, and the means of acquiring it.
      I texted her on my lunch break to tell her I was taking her out that night, to wear something nice. As so often happened, I underestimated the results of my simple request. When I picked her up, I was still wearing my suit from work; she met me outside her apartment building in a dress I’d have parked there all day just to see her walk by in. It was Asian-inspired, tight across the bodice, clinging to the front of her while revealing most of her back between the laces holding it on. The dress itself was a dark green silk, with a slit along one leg to the knee and on the other to the hip.
      I almost choked on my breath mint; she apologized for having startled me.
      We went to a nice restaurant, not the top of the line, but as nice as you could hope for without a reservation. She asked me to order for her; I did my best. There was even a subtle change in comportment of the wait staff around us. A little more formal, a little swifter to serve us, a little more respectful in their address.
      “So, how’s come you took me to such a nice place?” Courtney asked as we started in on the bread. (She said she could only do half a piece, because of the carbs.)
      “Well, I wanted to go somewhere we could talk a little for a change.”
      “Drew, you know you can talk to me any time you want.”
      “Yes, but if we stayed at home, we’d just wind up having sex all night.”
      Her eyes sparkled. “Check please?” she called out, though quietly enough not to actually be heard by the staff.
      I laughed. “See? So tell me about yourself. I only got the basics, way back on our first date. You ask me questions all the time, and hardly ever talk about yourself.”
      “I just think you’re a lot more interesting is all. Speaking of, how was your day?”
      I waved the question away. “See, that’s what I’m talking about. I show interest in you, and you immediately try to make it about me. Not tonight. Tonight, if you want in my pants, you’re going to have to talk about yourself.”
      “You sure drive a hard bargain, darling.” Beneath the table, concealed from lookers-on by the table cloth, her stocking foot worked its way between my thighs, rubbing at my groin. “I tell you what. You ask me a question, then I get to ask you a question. I’ll be totally honest if you agree to the same.”
      I cleared my throat and tried to concentrate through her distraction. For a moment I almost told her to stop, but so help me it just felt too darned good. Besides, the little thrill of it, knowing I could have her pleasure me here, in this fine establishment, surrounded by all these fancily dressed people… 
      Focus. “Agreed.”
      “Yay!” Courtney clapped her hands. “All right, you can start.”
      “What do you actually do for a living? I know you’ve said you modeled, used to do the… err, art studio work.” I fumbled my way around bringing up what had initially been a sore subject, that she’d modeled nude for a local art school. Funny, now that I’d loaned her out to my friends as a stripper and blowjob queen, it seemed pretty trivial.
      “I don’t actually work any more.” 
      “What? But how do you pay your bills and all that?” I had to fight to form some of my words as she tried to distract me with her footjob.
      “Bup bup bup, you asked, I answered. My turn. Why did you lie to me about your age?” 
      I averted my eyes before her knowing smirk. “How did you find out?”
      “That’s another question, darling.”
      “Fair enough. Well, it was our first date, and I guess when you told me yours, I was worried you’d think I was too old. I didn’t want to blow it before we had a chance to see if we had chemistry.” When she’d told me she was only twenty-three, I’d panicked a little. Twenty-nine seemed like a much more palatable reply than the truth of thirty-four.
      “Fair enough. And to give you a free answer, I was looking through your old social media pictures and one of your friends tagged you in a high school dance photo from when I was still in third grade.”
      I laughed sheepishly. “Yeah, didn’t cover my tracks too well on that one, I guess. OK, my turn again – back to my first question. What do you mean, you don’t work? How do you cover your bills?”
      “I was working part-time as a model and part-time as a waitress right up until we started dating. I had a few thousand saved up, and that’s paying for things now.”
      “In this city, a few thousand will dry up in a matter of months! What happens then?”
      “Sorry Drew, but it’s my turn.”
      “But…!” She applied a wonderful little nudge along my cock, and I let her off with the evasion again. “All right, all right. Go.”
      “Are you going to loan me out to more people like you did with your friends last night?”
      “Huh. You know, I guess I hadn’t really planned it out. Last night just kind of… happened. I hope I didn’t upset you – you always seem to like being shown off, and I guess I… I’m sorry.”
      She shook her head. “I wasn’t accusing, lover. I enjoyed it, just like I always enjoy when you give me a chance to be useful to you. I just wondered if you were going to keep doing it.”
      “I… I guess I don’t know for now. I don’t have plans to. That’s the best I can say for now.”
      She smiled, then stood and moved her chair right alongside mine. Before I could even register disappointment at the absence of her stocking-clad foot, there was her hand in my lap, replacing it. I blushed – this was far less subtle, though those not looking closely might think her hand was in her lap and not mine.
      “All right. Well don’t avoid doing it on my account. If I can help you or please you in any way, let me.” She smiled at me, then when I didn’t say anything, she gave my cock a soft pat. “Your turn, by the way.”
      Oh. Right. “OK, Courtney. Explain what’s going on – why you quit your jobs, what you plan on doing. No more being coy, no more bullshit. Tell me.”
      Her hand stopped, and her face drained of color. “You’re worried I’m using you. That I’m trying to score a sugar daddy.”
      “Well, the thought had crossed my mind.”
      “How long have you thought this?”
      “Since you told me you quit working as soon as we began dating. So like, two minutes. Am I wrong?”
      “Oh god yes!” she cried out. This time, nearby heads turned. She hadn’t meant it to sound like she was climaxing, but it could be mistaken for it. Courtney didn’t seem to register the attention, the wives snapping fingers to regain their husbands’ attention. “I’m so sorry – that’s not it at all, I swear! I quit so that I could always be available to you, Drew. I didn’t want you to want me on some night and have to give me up so I could wait tables or stand around naked for a bunch of art students. If you wanted me, I wanted to be available to you, 24/7/365.”
      Before I could even formulate a response, our food arrived. Courtney discretely withdrew her hand and expressed her delight with the look of her meal. I thanked the waiter, and then an awkward silence grew after he withdrew.
      “Mmm, this is really good. Excellent choice as always, Drew,” Courtney commented as she dug in.
      I silently watched her eat for a minute, then picked up my own utensils. “You don’t need both hands to eat that, do you?”
      A grin stole over her face as she slipped her hand back to my crotch and resumed her surreptitious handjob. “I suppose I don’t.”
      We wolfed down our meals. It wasn’t ten minutes later that I fucked her in the back of my car. I wasn’t surprised to learn she wasn’t wearing panties under that dress of hers.
      “Thank you for the fancy night out,” she said as I pulled up in front of her building.
      
      
      
      Over the next few days, I finally got my answers out of her. I let her make a game of it like before; most of her questions were about my fantasies and kinks, a list she had a knack for expanding. For my part, I began to finally see what should have been obvious from the get-go. Something wasn’t right in her head. 
      I asked her about some of her past boyfriends, how they’d felt about her submissive streak, why things had ended.
      “Oh, it wasn’t like that with them. Not at all. With those guys, I expected to be wined and dined, taken to nice places, bought expensive presents, taken to nice places. Can you believe that before our first date, I hadn’t sucked a cock since high school? I never used to like it much. Now, it’s the first thing I think about when I get thirsty.”
      I asked about how she planned to keep a roof over her head once her money ran out.
      “Well, part of me hoped that by then you’d take me in so I could be there for you whenever you wanted me for something. Still, I know some guys value their privacy. I figured if you didn’t want me, I have friends I could mooch off of for a while, or I could always find some lonely guy who’d let me stay with him rent-free just so he could leer at me. Creepy, and maybe a little dangerous, but between that and selfishly giving my time to someone other than you…” 
      On the subject of whether she ever found our situation uncomfortable or embarrassing:
      “Once, I might’ve felt that way. Maybe? I mean, I hear the whispers, people thinking I’m your paid escort, saying I’m nothing but a brainless bit of arm candy. But then I think, I’m your arm candy. I’d pay you to go out with me. I’m proud to be seen with you, and I get excited every time I make you look better, or help your situation out – whether that’s letting your boss stare at my tits or blowing your friends, I don’t care.”
      I even tried to see how far was too far, what my limits were.
      “None. Absolutely none.”
      I pressed. “None” extended to stealing for me, lying under oath, killing my enemies, prostituting herself, breaking off ties with every other person in her life and being my live-in sex slave.
      Yeah, something was definitely wrong. Still, as Courtney gleefully knelt at my feet and titty-fucked me, murmuring all the while how lucky she felt and how she couldn’t wait to feel me cum on her and how she finally understood why God had given her these big fuckable boobs… so help me, I didn’t really want to right it.
      
      
      
      There’s nothing like being told there are no boundaries to make you want to seek them out. For the next week, that was exactly what I did.
      First, I took her to the tattoo parlor. She was elated by the idea – “ohmygosh, you can permanently mark me as yours!” – and if anything seemed a bit disappointed when I discarded some of her less subtle ideas. “Property of Drew” on her lower back (or across her breasts, or stomach, above her pussy, in a ring around her neck like a collar); a likeness of her tits above her ass so I could see them when I was fucking her from behind; the shaft of my cock on her cheek so it looked perpetually like she was sucking my dick.
      Mostly she was having fun getting a rise of me, I think, but there was too much a spark of sincerity about it to playfully feign interest. In the end, she settled for a cheesy image of a small heart pierced by an arrow with my name on it on her bicep, and – after she pestered me to pick something more risqué just for us – the words “any time Drew” on her pubic mound, which she had kept bare.
      The tattoo artist almost waived the charge, but I’m not one to shun patronizing good art.
      Next, I asked if I record us in the bedroom. I don’t know why I even thought she might refuse – probably because any other woman I’d been with would’ve slapped me in the face and dumped me on the spot – but instead she squealed in glee. She immediately began brainstorming camera angles, positions, scripts… like we were making a porno.
      “You mean you’re not going to show anyone?” she whined when I told her to ease up.
      “Babe, who would I even show it to?”
      “Anyone you wanted! What, don’t give me that look. You like showing me off, and you know I like being shown off.”
      “All right then – go nuts with it. I don’t know that anyone else will ever see it, but it’ll be nice to have the option I guess.” I patted her on the head, and she dove back into her work.
      In the end, it was relatively light in narrative and dialogue (unless you count her pleading and shrieking blissful expletives), but it turned out pretty well. The premise was that I was her boss and I caught her stealing from the company, so she had to pleasure me or lose her job. 
      It wasn’t Shakespeare. (OK, it wasn’t even Cinemax.) Still, Courtney’s enthusiasm and sexiness made it incredible. It was barely even my idea (beyond the suggestion of recording), and she still thanked me like it was the best present she’d ever been given, and she said she watched it all day while I was at work on a loop.
      We tried role play, something I’d always thought about but never actually felt comfortable trying. With Courtney though, it was an exercise in pushing my own imagination to its limits. I got incredibly graphic texts throughout the day at work, and at night we’d pick our favorite and act it out.
      I was her professor and she was a bratty co-ed who came into my office to demand an A or she’d complain that I sexually harassed her; I turned the tables on her by showing I’d recorded her blackmail attempt, and would have her expelled if she didn’t gratify my every desire. With downcast eyes, she sucked my cock and became outraged by the suggestion she should swallow, yet finally relented and gulped it down. Then I bent her over my desk and made her apologize as I spanked her big round ass, after which I left her in that position as I fucked her from behind.
      (When I surprised her at the end by snapping a few pictures with my phone and told her she’d have to come back every week for another session or I’d release them online, Courtney literally came just from the suggestion.)
      The next night she was a sex robot; I came home to find her actually waiting inside a massive cardboard box she’d somehow sealed herself in. She was naked save for silvery metal bracelets and matching anklets, and some bits of tinsel she used to bind her hair in pig tails. She stood stock still as I fondled her all over, even keeping her blank and unblinking expression as she kneeled in front of me and let me thwap her in the cheeks with my cock. The blowjob suffered from her repetitive delivery, but she more than made up for it with the unbelievable stamina she displayed later when I had her mount me. Her face never broke character for a moment, staring vacantly ahead as she bounced and rocked her hips.
      The night after that she was a harem slave desperate to please her sultan. The next she was a hooker, and I paid my girlfriend almost $200 to do a less enthusiastic job of the things she usually did for free – yet was somehow every bit as pleasing. Courtney said afterwards that had been the hardest one to maintain character, pretending she wouldn’t take it up the ass unless I gave her $80 up front. (Still, I made her keep the money, and she said when she spent it on a costume for another scenario next week, she’d gotten so wet she’d left a stain on her bus seat.)
      The next night we didn’t role play, because it was football night and the guys were coming over. She at first offered to give us our privacy, since she thought I might like some guy time. It was, after all, our team’s match against their biggest rival, and fan though I was, I was a realist, I’d put a heavy bet down against our boys. 
      Of course, both Rich and Stu had already texted me to explicitly invite her. Rich said she’d been cool the last time we’d watched the game together; Stu just said he liked having her around. Since the last time she’d seen the guys was when I’d had them over I’d also had her do strip teases for them and give Stu a blowjob, she asked how we were to proceed.
      “How do you mean, babe?”
      “Well, do you want me to be like I was that first night I met them – you know, like a normal girlfriend who digs football? Or do you want me to be like the second time, where I was your submissive little pleasure slut who obeyed any command she was given?”
      I thought about it. “You know, I think I have an idea.”
      
      
      
      “No way dude. You’re not backing out of the bet now, Drew. When – not if – the Patriots smoke these fools, I’m getting myself an Xbox,” Stu said emphatically.
      “Seriously – you deserve to lose just for suggesting the idea of betting against our team,” added Rich.
      “Hey now, I’m not talking about canceling the debt. I’m just talking about making it a little more interesting is all. Sweetening the deal. I propose that if the Patriots lose, you guys owe $250 apiece, like we agreed. Giants lose by  seven or less, break even. Giants lose by eight plus, and–”
      “Whoa there. That’s double what we agreed to, man. And you want us to spot you a seven point advantage? Are you insane?” 
      “Not a snowball’s chance in hell. We believe in our boys, but… but…”
      Everyone in the room suddenly forgot the argument as my girlfriend made her entrance. I thought back to when they’d first met a few weeks ago, hanging out at my house watching the Pats just like tonight. Then, she’d worn a jersey with enough holes in it to tantalize.
      Tonight, she wore a pair of booty shorts, her perfect round ass cheeks hanging out the bottom, that normally would be the subject of attention from every male behind her for a thousand yards.
      Except that was all she wore.
      Well, I should clarify, she was wearing body paint across her torso and her face, colored in the red, white and blue of the Pats, their logo painted carefully by yours truly across her breasts. It wasn’t masterful, but it didn’t need to be. She bent down and gave me a thorough greeting kiss, then plopped down sideways on my lap. 
      “Uh, hey Courtney,” said Rich. Stu just gaped in silence. I knew how it was. Even if you’d seen those boobs a hundred times, you couldn’t help but marvel.
      “Heya boys. Drew talk to you about the bet yet?” she asked.
      “I was in the middle of it, but I don’t think they were into it. Sorry, babe.”
      “Aww, OK. Well I guess I’ll see you some other time.” She pouted, then made to stand up.
      “Wait wait wait – where you going? C’mon, stick around,” Stu implored her.
      She paused as I spoke. “Well as I was saying, you spot me a seven-point advantage, and Courtney here hangs out for the rest of the game. They lost by eight plus, and I not only make good my debt, but Courtney joins us for every game for the rest of the season.”
      Now this was a thing worth considering. My girlfriend smiled brightly at them, thrusting her chest out to sweeten the deal. We let them ogle her for a good thirty seconds before I cleared my throat to wake them out of their stupor. 
      “Oh fuck it, let’s do it,” said Stu. Rich agreed only a moment later. Courtney squealed and did a few excited jumps to show her glee.
      “You won’t regret it, we promise,” she said, settling back into my lap, angling herself so her best side was on full display for them.
      “Indeed. You guys need anything – beer, snacks, shoulder rub, whatever – just tell her and she’ll make it happen. Right, babe?”
      “Mmm, right.”
      “Blowjob?” Stu asked almost immediately.
      “Keep it in your pants, buddy.”
      He settled for the shoulder rub, as did Rich during the second quarter. During halftime, Courtney coyly asked if it’d be all right if she got in a quick workout, as she hadn’t had time earlier what with getting the place ready for them. So instead of listening to a bunch of paunchy has-beens discuss the highlights, our halftime show was my buxom, topless girlfriend doing aerobics. It was a good thing we only had fifteen minutes to wait or I’m pretty sure Stu’s erection would have exploded out of his pants.
      During the third quarter, Courtney sprawled out on the rug and finished her workout with a thigh master. I had to wonder if I’d been wrong about her best side. By the fourth quarter, she was so genuinely sexually frustrated that she curled back up in my lap and ground her ass into my crotch, whispering in my ear all the things she couldn’t wait to do to me.
      She was such an amazing girlfriend, I’d been hardly paying attention to the game, and was surprised to find out we’d won the bet. The guys didn’t even grumble when they forked over the dough.
      “Best bet I ever lost,” said Rich.
      “Hey, don’t sweat it. And you know what, if it’s OK with you guys, maybe we’ll have Courtney join us for game night on the regular.”
      “More than fine by me,” said Stu. Rich voiced his agreement, but I couldn’t wait any more. A sharp tug, and the stitching in her shorts gave. I threw the flimsy fabric to the side and went to shove Courtney over the arm of the couch, only she was already diving there before I could touch her.
      I don’t know if or how long the guys watched me fuck her sopping wet pussy, and I didn’t care. Courtney had just made me five hundred bucks, put me on top of the social ladder, and was now doing what she did best – throwing every inch of her body and every piece of her soul into getting me off without a second thought to anything but pleasing and obeying.
      Was I falling in love with her? Or was this something else?