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Introduction:

Rachel and I establish some ground rules for our arrangement, but a revelation about her leads to an experience that changes everything.
Four days later, having forgiven (yet not forgotten) about Rachel’s discovery of my late wife, I decided I would keep the promise I had made to Rachel’s best friend, Rebecca, and schedule our next meeting.

-Hey

-Dont have this phone number, who is dis

-It’s your dear old uncle

Along with the text, I included a picture taken from our last session. I doubt Rachel had even noticed the cameras I had installed several years earlier at my late wife’s request. She used to love watching herself when I fucked her. This picture showed the young blonde with her hands bound behind her, her face against the ground. Not evident from the picture, but she had been busy licking my cum off the floor at the time.

-We need to talk

-Indeed, we do

-I’m coming over after school. U better b there

I had worked an early shift that day and was due to finish up in about an hour. I ought to be able to make it home before she arrived. If not, she could wait, I wasn’t sweating it. Sure enough, by the time I pulled into my driveway, Rachel was waiting for me, arms crossed over her chest, leaning against the tailgate of her beat-up truck.

“You’re late.” I unlocked the front door and she stomped passed me, going straight to the recliner in the corner of my living room.

“Perhaps we should get you a key, you’re getting pretty comfortable here.” She looked like she would’ve thrown something at me if anything had been close at hand.

“You’re late,” she repeated.

“Aye. Came straight from work.” My seat already occupied, I sat down on the couch facing her. “So, what did you want to talk about?”

“We need to discuss our…arrangement, I guess, if you want to call it that. How-how much has…Has…Look, how much more do I owe you still, and what do I have to do to finish paying it off? I can’t go through what I…what you did to me this weekend again.”

“Well, you came and gave me that magnificent show. I think my bed sheets are still drying from that.” She blushed, dropping her head to stare at the floor. “And you spent, what, about two hours? I think it was about two hours, yeah, let’s call it two hours in my little playroom. So, we started at $1250, I’d say you’re down to about…$1050.”

Her jaw dropped, tears welling in her beautiful eyes. “Two hund-hundred dollars? That’s it? I let you tape me masturbating, you made me pretend it was for your weird nephew. You put something in my ass. You-you-you beat me.” She stood up suddenly, whipping around and pulling down her shorts to reveal the crimson welts still striping her firm ass. “See? See what you did to me? It still hurts to sit down. And I did all of that for 200 bucks? No, we’re going to renegotiate.”

“Well, I thought for each fantasy of mine you indulge me in, I’d knock $100 off your debt. That seems fair to me.”

“Wait a minute, I also gave you a blowjob that first night. So it’s $300, right?”

To Rachel, I’m sure it seemed I was weighing over her suggestion. In truth, I hadn’t (couldn’t) forget that blowjob. “That’s a good point, but I’m afraid that it was you who offered. That wasn’t my fantasy, that was yours. We’ll just call that a good faith gesture on your part. Much appreciated actually, really made me feel like I could trust you to honor our agreement.”

“MY FANTASY? YOU THINK THAT, FOR ONE MINUTE, I’VE EVER FANTASIZED ABOUT YOU?”

“Well, you were quite wet last time. And the way you sucked me off on Saturday, it certainly seemed like you were enjoying it every bit as much as I did.” She strode over to the couch and slapped me with more power than I thought a girl her size could muster. “Now, look here. You don’t have any, understand me, ANY leverage here. You think that I only had the one copy of those videos? Thought you could pickpocket my phone and I’d lose my collateral. How fucking stupid are you? Of course, I made backups.”

“Wait, what? Why would I steal your phone?” I glared at her and, realizing the logic behind the accusation, she continued, “Well, okay, I guess I have a pretty good reason, but I didn’t do it. I figured a perv like you probably made copies as soon as you could.” Trying to compose herself, another realization flashed across her face. “And another thing, dear old uncle, our agreement doesn’t include my friends, my family, or my boyfriend, so stay the hell away from them.”

“Fair enough. But that means my wife stays out of it, as well.” She nodded her head in agreement. I took a few deep breaths, trying to clear my head. Perhaps realizing how heated things were getting, she did the same. “I think maybe setting some ground rules makes sense. Just so you know what you’re getting from this, I pay by encounter, not by hour. I won’t expect you to be 24/7 at my command, but I do expect you to make a reasonable attempt to be available when I ask.”

“I guess that makes sense.”

“Good. As for standards, any hair below your eyebrows is to be removed before visiting. Since you won’t always know when I’ll be calling, I suggest you just keep up-to-date with it. Bra and panties are to be removed before coming through my door and, except for those times when you are coming straight from work or school, I expect you to be wearing a skirt and low-cut blouse when you arrive. Now, are you on the pill?”

“The pill?”

“Yeah, I don’t like wearing condoms and I’m certainly not looking to father any kids with you.”

“Well, I think I should get to set a couple of rules, too. I know, I know, leverage, blah blah, but that’s only fair. I have limits, there are things I won’t do.”

I mulled it over, deciding that, as long as her requests were reasonable, I would respect them. I didn’t waste my time patting myself on the back over this, I had already forced her to do several things that, whether she enjoyed them or not, she never would’ve done with me. “Okay, what did you have in mind?”

“We can’t have sex.” This time it was my turn for surprise. I felt like a cartoon, sure that my jaw had literally fallen from my face and struck the floor.

“Uhhhh, yeah, I don’t think that’s going to work. You won’t be getting a hundred bucks trying to suck off your debt. Unless…”

“Unless what?” The hope on her face was evident. Evident, and badly misplaced.

“I have a few friends over for poker once a month. You come, strip for us, serve us drinks, suck off a few of them, I’m sure they would help contribute to your debt.”

“No. Absolutely not. My debt is to you, my arrangement is with you, I am not a whore to be passed around to your friends. I will, you know, do stuff to you, but not for anyone else.”

“Fair enough, it was only a thought. How about this for limits, if you would do something with your boyfriend, then I have the right to expect it from you as well.”

She suddenly seemed very interested in the hem of her shirt, anxiously twisting and pulling at it. Several times it seemed like she was on the verge of speaking, only to shake away whatever words threatened to spill forth from her lips and resume fiddling with her clothes. I wasn’t sure what had gotten her so worked up; I knew it had to be more than breaking our previous rule and invoking her boyfriend. A thought buzzed through my brain as I watched her. I swatted it away, but the more I stared, the more insistent the thought became.

“Rachel?” She looked up at me, her shirt still balled up in her fist. I noticed there were tears in her eyes. “Are you a virgin?” Fresh tears spring from her eyes, leaking down her cheeks. Never before had I seen her as something so vulnerable, and a part of me wanted to draw her into a big hug and assure her that this would all be okay. She nodded slowly. I was completely stunned. Feeling suddenly heavier than I had been only two seconds ago, I collapsed back into the couch. Rachel had sat back down in the armchair, curling up into as tight a ball as she could, her knees to her chest, her arms wrapped around them.

“I’m on the pill, but I’ve never had, you know, never made love before. I wanted to save that for Ryan. I can do other things for you, though.”

I could say that I wanted to respect her wishes. I could tell you that, having finally recognized her vulnerability, I was going to call the whole deal off. I had already paid for the repairs to my truck. I had earmarked some of that for a vacation later in the year, but I still had quite a bit in savings and would be able to make up the money I had spent within a few months if I made a few adjustments to my budget. The problem is, if I told you any of that, I’d be lying. At that moment, all of my thinking, all of my decision making, everything was being controlled by a different part of my body, this one a couple feet below my neck. “Rachel, I’ll take $500 off your debt right now if you have sex with me. I’ll be gentle, foreplay, make sure that you cum, too. What do you say?”

It’s what I had been thinking, but I was still surprised to hear it issuing forth from my lips so coldly and confidently. More surprising was her response. Rachel didn’t immediately say no. She seemed to be seriously considering my offer, and I was ready to do and say anything to be the one to claim her virginity. “Ryan would never have to know.”

“I would know.” She looked genuinely upset to have to decline my offer. No doubt her regrets were over the idea of ending our arrangement faster and had nothing to do with turning me down for sex, but it was a surprise, nonetheless. She chewed on her lip, clearly still deliberating something. I sat patiently, waiting for her to tell me. “What if…what if you fucked my ass instead? I’ve never done that with Ryan, so you’d still get to take my anal virginity.”

“You would rather have a cock in your ass first than in your pussy?” She hesitated, then nodded, hanging her head as if ashamed after doing so. “I’m not giving you $500 for that, you know?”

“How much then?” I could tell that the idea of bartering over the value of her body hurt her deeply. She clearly considered herself above such the type of people who sold themselves like that, and I relished watching her agonize over her decision.

“Hmmm.” A deep breath in, then, “$150.”

I expected more pushback, a little negotiation, an outright refusal to allow me her virgin asshole. What I got were sniffling tears and a deeper sob as she nodded her head in agreement. “Is that *sniffle* really all?”

“You were willing to offer up that sweet ass of yours pretty quickly. Clearly, you don’t consider your two virginities as equals, why should I?” She didn’t respond, but she didn’t argue, either, and that seemed to be the most important takeaway. “Well, Rachel,” I said, standing up, “I believe you remember where the bedroom is.” I gestured for her to go ahead of me, smacking her firmly on the ass as she passed me. She shot me a wounded look over her shoulder but continued towards the bedroom. Upon following her through the doorway, I found her sitting on the bed, anxiously playing with the hem of her shirt again. I was starting to think I was breaking the poor girl. “Rachel?” I asked politely, almost gently. “You’re going to need to undress for this.”

She seemed unable to speak but began undressing anyways. Her breath was coming in hitching gasps, and far too rapidly. “Rachel, breathe.” She flashed me a small, grateful smile and tried to calm herself as she removed her shorts and panties, now sitting naked on my bed.

“Where do you want me?” I positioned her on her hands and knees, with her ass sticking out over the side of the bed. Admiring the view in front of me, I gave her a few light slaps. Not enough to hurt her, I just wanted to watch her ass cheeks jiggle. Pulling her cheeks apart, I bent over and breathed in deeply from the cleft of her ass. She smelled musky, but clean, and I darted my tongue around her hole. She jerked forward at first, surprised by the feel of my tongue, before leaning back into me and moaning. Pressing forward with my tongue, I managed to slip the tip of it through her tight opening. “Ohhhhhhhh, that feels soooooo gooooddd.” Even relaxed under my careful ministrations her ass was still exceptionally tight. My jaw was soon aching as I continued fucking her with my tongue but listening to her moan and feeling her body trembling were enough to keep me going.

Trailing kisses between her pussy and ass, I noticed that she had grabbed one of my pillows and was buried face down in it. With one hand she was squeezing her breasts, her nipples taut. With her other hand, she was busy rubbing at her clit. My tongue joined her hand, lapping at her pussy with long strokes as she focused on her clit. I slid my hand across her slick center and, lubed with her own juices, slowly stuck my finger through her puckered rosebud. She let go of her breast, her fingers stopping abruptly. I had only gotten to the first knuckle and began pulling my finger back out when she reached back, grabbing my wrist and pulling it towards her, burying my finger fully in her ass. At that, she came. Loud, long, and hard. Rachel thrashed around wildly, her fingernails digging in and leaving deep marks around my wrist, her ass clamping down hard enough on my finger I feared she might break it.

Rachel collapsed on the bed, breathing heavily and mumbling incoherently. I withdrew my finger, holding it to my mouth and savoring the musky, coppery flavor. I traced more kisses across the angrier looking welts on her ass, evidence of our time in my playroom. “Rachel?” Her breathing was returning to normal, and she looked back at me, my hands and lips still on her perfect ass cheeks. “Did you just cum with my finger in your ass?”

She smiled. Beautifully. Sincerely. A smile I’m sure she had never intended to favor me with, but there it was. “Mmhmmm, I did.” Her voice almost dreamy, ethereal, like she was talking to me from another plane. “But I need more than a finger. I want your hard cock inside of me. Please, I feel so empty right now.”

Smiling wistfully at her, I told her, “Rachel, as much as I love hearing that, I wasn’t recording this. You don’t need to act today.”

Scooting to the edge of the bed, she laughed as she sat down in the large wet spot she had created moments before. It was a whimsical laugh, fully unbefitting a woman about to lose her anal virginity for $150 to a man she found morally repulsive. Wrapping her legs around mine, she pulled me closer to her, pressing her breasts against my stomach and laying her head on my chest as she hugged me closer. “Go get your camera set up and then get your cock out. I’m not acting right now. Let’s not ruin this with talking.” I turned to stare at her, suddenly unsure of myself. “Go,” she giggled, tossing a pillow at me.

I was barely able to get the door closed behind me before I felt my legs giving out. Using the wall, I was able to hold myself up, stumbling towards the kitchen. I poured myself a large glass of ice-cold water from the fridge and drank it on shaky legs. “What the hell was that?” Her orgasm had been genuine, I still had the fingernail marks to prove it, but was she really turned on by this? Even if she did enjoy her first foray into ass play, shouldn’t she be running off to try it with Ryan, not begging me for more.

“Are you coming back?” Her voice drifted through the house, sounding soft, plaintive. I grabbed my camera and tripod and went back to the bedroom to find her still at the edge of the bed, legs spread wide before me. “Oh, I though maybe for a minute you were having second thoughts?” I stared at her. Suddenly, she had become very hard to read. “You weren’t, were you? Having second thoughts? You still want to fuck my tight, teen ass, don’t you?” All the moisture seemed to evaporate from my mouth, and all the air disappeared from my lungs, so that all I was able to do was force an awkward nod. She smiled expectantly, and I suddenly became aware of the camera still in my hand. Setting it up seemed much harder than previously. Not because I was worried about camera angles, but because my mind was still whirring. “Let me help you with that”

“I think I’ve mostly got it.” She knelt at my feet, unbuckling my pants and smiling up at me.

“Not the camera, silly,” she giggled, finally extricating my cock, “this.” She grabbed the camera, turning it on its tripod so that it now faced her. Flipping it on, I could’ve sworn she winked into the lens before quickly takin the length of me in her mouth. She didn’t gag or choke, holding me in her mouth for several seconds before slowly pulling back, her eyes locked on mine the entire time. When only the tip remained in her mouth still, she dove back forward, inhaling my cock again. The passion and hunger with which she was now sucking me had this easily surpass the admittedly very skilled blowjobs she had already provided me with. In no time at all, she had covered me in a shiny sheen of saliva. When it was enough to start dripping down my balls, she withdrew and took each one lovingly in her mouth. Perhaps, I thought, this was her intention all along. Get me so turned on, so worked up, that she could easily finish me off with her mouth, sparing her ass for at least another day. Even with that in mind, I wasn’t about to, or even able to, ask her to stop. I was fully in her power, under her spell, and if she hadn’t stopped when she did, I would’ve soon been shooting my cum into her waiting mouth.

It occurred to me, barely, that this still mostly-virginal teen might’ve been reading me, bringing me right to the edge before crawling back on the bed on all fours, ass and pussy on full display for the camera. She wiggled her ass enticingly for me before sitting up on her knees, turning towards me with a contemplative look on her face. “No, I think you’d rather see my face when you take it from me, wouldn’t you? Want to watch the look in my eyes as I take my first cock up my virgin ass, don’t you?” She turned around again, bending forward so her elbows rested on the bed, beckoning me to her with one curled finger. One finger and the type of lascivious grin a woman her age shouldn’t have the experience for.

I crawled behind her on the bed and she rocked her hips back against me, my cock slapping wetly against her ass cheek. “Rachel?”

“Yes, baby?”

“You know this is going to hurt, right?” She didn’t respond, not verbally. Instead, she reached back between her legs, grabbing my cock and guiding it towards her ass. I grabbed her hips and slowly pressed forward. I could tell she was trying to relax, but she was still too tight to allow even the tip in. Pulling on her hips and thrusting forward, I could feel the muscles in her ass slipping, allowing my cockhead to gain entrance. Rachel hitched in a wheezing breath and with a little more force I was able to slip the head of my cock inside of her.

“Ohhhhhhhhh, ughhhhh.” The noise she made sounded like that of someone who has just finished a heavy meal but I knew this represented a different kind of fullness than she was used to. I paused as she took several deep breaths, trying to adjust to this new intrusion of her body. When her breathing had returned to close to normal, I began pressing forward again. I had maybe driven another inch into her when she released a short, pained shriek.

“Rachel, is that too-“

“Don’t stop.” Her voice was forceful, dripping with need, and I obliged reluctantly. I no longer needed to pull on her hips as she seemed to be trying to rock herself backwards farther onto me. I continued my thrust into her tightest hole, driving another pained squeal from her. With every inch, her moan seemed to go up an octave, but she also seemed to be redoubling her efforts to take all of me. I paused again, still only halfway inside of her. “Why are you fucking stopping?” Now she sounded almost angry at my continued delays. Angry, and desperate. With one savage thrust, pulling her hips violently towards me, I managed to bury the rest of my cock inside of her.

For a moment, nothing much happened. Rachel seemed to be having trouble exhaling, instead drawing in hitching gasps until I thought her lungs might burst. Her hands were balled up into fists, pulling at the comforter. Her head arched backwards, her body shaking, her asshole gripping me hard enough that I couldn’t withdraw from her. When it seemed like she was in danger of passing out, she exploded in a cacophony of sound and fury. Once again, she squirted all over the bed, screaming like a wild animal while bucking back and forth against me, my balls swinging forward and slapping wetly against her pussy each time she drove herself backwards onto my cock.

I tried to hold on, my grip tenuous on her hips. I still wasn’t entirely sure if she was in the midst of a powerful orgasm or a seizure, and the braying sounds issuing from her mouth were terrifying me that it was the latter. I thought that I had possibly torn something, that she was in enormous pain, but still she continued to thrash about, slamming her ass down onto my cock with reckless abandon. When she finally slowed, she lay her face down on the bed, her body heaving as though she were crying. I tried to pull out of her, but she turned to me, shaking her head and whispering, “Please. Don’t stop.” There were indeed tears in her eyes, but an exhausted smile on her face as well.

I started out slow, easing my cock out of her before slowly thrusting back in. It wasn’t for her benefit so much as mine. She was still incredibly tight, to the point of almost being painful. After a few drives, in which I was only able to extricate half of my length from her, she began to come back down from what seemed to be an earth-shaking orgasm. Her tight, anal ring loosened, and I was able to continue fucking her at a quicker pace. Completely exhausted, Rachel was unable to take as active a role in our tryst as she had previously, but she was still whimpering with pleasure. Eventually, she reached back between her legs with one hand and began rubbing her clit while I fucked her.

As my pace quickened, so did her enjoyment, and she was soon spurring me on. “Harder, baby, harder.” I didn’t need much encouragement, with my hands on her ass cheeks, I was able to pull them apart with my thumb, watching with incredible arousal as her asshole swallowed me up. A little pink sheath remained on my cock as I pulled out of her before I quickly drove it back in. “Ohhhhhhhhhh, yesssssss.” Despite her erotic moaning and the enticing scene before me, I felt far from cumming. I thought, fleetingly and guiltily, about her boyfriend Ryan. Would he, now that I had awakened his tight, teen girlfriend to the pleasures of anal sex, soon be plundering her asshole? Somewhat arrogantly, I thought that he would’ve surely blown his load inside of her by now, comforting my (apparently) desperate ego that, if only temporarily, I was the better lover. Then, with a concerted effort, I pushed the thought away, concentrating instead on the blonde beauty currently impaled on my cock.

I quickened my pace, using her hips to pull her back onto me. Her ass cheeks made a loud clapping sound as they struck against my stomach which served only to make me fuck her even harder. Unable to articulate her pleasure, she punctuated each thrust with a satisfied grunt. “Unh, unh, unh, unh.” We were soon both covered in a sheen of sweat, but I had no intention of slowing down. My grip slipping, I turned to slapping her ass every few strokes instead. Soon, I had added several bright red handprints to the welts I had given her on our previous encounter. Admiring my handiwork, I continued spanking her in earnest, her cheeks soon glowing a bright red.

Unlike our experience in my basement sex-dungeon, this time the impacts drove her to new heights of arousal. Her fingers sped up over her clit, rubbing furiously as she resumed rocking her hips back to meet my frenzied thrusts. “Yeah, baby, smack that ass. I want you to smack my ass while you fuck it. Do you like that? You like fucking my tight, teenage ass, you dirty old pervert? Wanna make me your little anal whore? So fucking dirty, taking advantage of me like this, but you love it, don’t you? Don’t you? Are you going to cum? Going to cum for me, baby? Bury that huge fucking cock of yours in my little asshole and shoot your fucking load deep inside of me?”

I felt my orgasm welling up. Our bodies seemed a blur, each crashing into the other with incredible force, the impact seeming to echo throughout the room, ringing in my ears. I reached out and grabbed a handful of her blonde locks, yanking her head back up to face the camera. “Go ahead, slut. Tell the camera what a little anal whore you are. Little fucking butt slut. Won’t give up that pussy yet, but you’ll gladly let a guy twice your age pound your virgin asshole?”

“I DO. I FUCKING LOVE YOUR HUGE COCK IN MY ASS.”

“I’m going to cum so deep inside of you, Rachel. You’re going to cum with me, too.” I realized it wasn’t only sweat covering me, but her own juices were dripping down my legs, coating my balls as they slapped against her pussy with each violent thrust. “Not yet. When I say, cum with me. Can you do that, Rachel?” She nodded as much as she could, my hand still gripping her hair, arching her neck backwards in a manner that would surely have been painful had she not been so distracted. “Do it then, whore. Cum with me. NOW.”

Despite giving the command, I had narrowly misjudged the timing of my own orgasm. Rachel came first, and while it was nowhere near as intense as her previous orgasm, her satisfied moaning and trembling body assured me it was still powerful. A half a second after hers, I came, flooding her bowels with my warm seed. “Oh, woooow.” Then, staring into the camera, “I can feel your huge load inside me, you didn’t tell me it’d be so much. It’s sooo warm inside me.” I pulled out of her and she slid off the bed, somehow managing to be both awkward and incredibly sexy at the same time. With one arm draped over the bed, she put her head in the crook of her elbow and looked up at me. Without looking, she reached out and pulled the tripod to the side, so that it caught her in near profile. “Well?”

“Well what?”

“Come here, silly. I know you boys like it when a girl licks you clean after you fuck their asshole, don’t you?”

Shocked might’ve been a bit of an understatement. This whole afternoon had introduced me to a wild, and not quite believable, side of Rachel. That this woman had, not an hour earlier, confessed to being a virgin and was now asking to take my cock, pulled straight from her ass, into her mouth. Sure, I had been with women who allowed it before, but never with one who so actively sought it out. Not to mention, those were women who I was actively involved with at the time, who had a reason to try and please me beyond owing me a debt. Not being able to express or comprehend any of this, I stupidly spat out, “Are you serious?”

She giggled, and at that moment I realized I had lost all control in our relationship, or arrangement, or felony. Whatever label you gave it, Rachel had me in the palm of her hand. She might give me everything I want or ask for, but she had seized the power from me and I suspected that she knew it. “Come here and find out.” I slid to the edge of the bed, sitting down next to her outstretched arm. She placed her hands on my hips, pulling me into the camera’s view. Careful to keep herself in profile to the camera, she knelt, taking one of my balls into her mouth. Gently sucking, she lathered it with saliva before releasing it and turning her attention to the other one. Lifting my slowly deflating cock with one hand, she ran her tongue along the bottom, from base to tip, staring up at me around my penis as she did. She didn’t wince or make faces at the taste, seeming instead to enjoy it as she licked me clean.

Despite the loving attention, I was still too shocked to properly enjoy it. Fleetingly, I hoped that the camera wasn’t catching my face, as I was sure it was locked in something akin to dumbfounded surprise. She smiled again, not lewd or sexual as she released my penis. She had somehow gone back to vulnerable, like a small child looking to a parent for approval. She switched the camera off and crawled up onto the bed past me, flopping her head down on a pillow. She looked so inviting, splayed out comfortably on the blanket, perfect breasts rising and falling with each breath, her body glistening with the exertion of our torrid sex. I looked at her longingly but knew to go to her risked…well, whatever the hell was going on right now.

Maybe she read the look on my face, but it was easy to believe at that moment that she was inside my read, privy to my every thought. “It’s okay,” she whispered, and I came to her. She wrapped her arms around me, cradling my head to her chest, stroking my hair as I listened to her heart beating. With everything we had done (everything I had done to her), it seemed odd to me that this moment, far surpassing every other, was the most anxious. I was loathe to relax against her, worried that this was an intimacy far too close for her comfort, that any moment she would regain her senses amidst her post-orgasmic bliss and storm out. She didn’t. Instead, she sat, holding me, willing me to share in her sense of comfort. Eventually, I was able to.

Some time later, it could’ve been minutes or hours or days for all I could tell, she broke the silence. “Can I ask you a question?”

“I think, after all this, you’ve earned that much.” I couldn’t see it, but I could feel the warmth of her grin against the back of my head.

“How do you do it?” I wasn’t sure exactly what she wanted to know but sensed that she was still looking for the right words. So I stayed silent. “You said that Am-you said that your wife, well, it’s obvious you really cared for her. Still care for her. I’m sorry. How did you…hurt her, I guess?”

“Well, it’s hard to explain, really. To be honest, I don’t really know why, but some people like to cause pain in others. I guess that part shouldn’t be too surprising nowadays, but there are also people who like to experience pain. When those people find each other, it becomes kind of a loving experience. I’m able to provide her with something that she craves and she allows me an outlet for my…less socially appropriate desires. And there are limits. We talk about what we can and cannot do ahead of time, so that everything is agreed upon and cons-“ I stopped myself short, leaving the word hanging in the air. Maybe she hadn’t noticed.

“Consensual?” She noticed.

I sighed. Not because I was caught, but because she was right. “Yeah. That. What we had was consensual. What this is…well, this is probably rape. Sexual assault at least.” I knew it. She knew it. Saying it out loud, though, really changed things for me. Guilt washed over me and I tried to disentangle myself from her arms, but she held tight.

“Yeah, it probably is…was, I guess. I’m still not happy about it, not really, not entirely, but I get it. And in some weird, fucked-up way that requires a whole lot more insight than I’m capable of, I’m…well, a little glad that it happened. Does that make sense?”

“Honestly? Not at all. I can’t figure out how you don’t hate me, cause I sure do sometimes.”

“I do. Hate you.” Suddenly, it felt like all the air had left the room. My world, such as it was, seemed to fold in on itself with those four words. I had allowed myself to hope that…what? That I could sexually assault a teen girl until she decided that she’d just stay and fill the gaping hole in my life? Of course, she hated me. She had every right to and it would’ve been far more unbelievable if she didn’t. “Or at least I did. Sometimes, still do, I really don’t know. I sound like a real idiot, don’t I?”

“Not at all.” I propped my head up on my hand, staring at her. She was lovely. Confused right now, and I could see how much her inner turmoil was hurting her, trying to decipher what was going on between us and why she was treating it the way she was, but oh was she beautiful. “As you have dutifully pointed out, I’m twice your age, and I still can’t really figure out what’s going on here.” She smiled guiltily at the twice your age comment. I smiled back, reassuring her that I took no offense from her comment. 37 was, after all, slightly more than twice her age. “I can’t even imagine how this must feel for you.”

She sat up next to me, bringing one leg up to rest her head on her knee, her arms wrapped around her. “Yeah.” It seemed that, once again, the aftereffects of her orgasm had worn off and the tension returned, but this time felt different. She wasn’t storming out of the house, she didn’t appear to be angry with me. She was simply left trying to figure out where we stood, what was happening between us or inside of her. She turned to face me, the anxiety evident on her face. “I’m going to come back. Not just…because I owe you, but…I don’t know, because I…what the hell, because I’m fucked up in the head and I’ve somehow come to enjoy whatever the fuck this is. So I’m going to come back, and we’re going to see how far down the rabbit hole I’ve fallen, but I do need some time, okay? Just some time to wrap my head around this.”

I nodded. “That sounds reasonable. How about, whenever you’re ready, just let me know. I’ll wait.” Her face lit up again, and I knew that I wasn’t lying. I also knew that what we had wasn’t love, although I suspected I was closer to that particular emotion than advisable, but even so, I would be patient and whatever else she needed if she’d favor me with one of those smiles again. She wrapped her arms around me, pulling me into a tight hug and kissing my cheek.

“Thank you. That means a lot.” She released me, and I noticed her eyes welling with tears as she gathered up her clothes. Glancing around the room in confusion, she seemed unsure of whether to just get dressed or to ask me to give her some privacy. I guess Emily Post hadn’t written a chapter on the proper etiquette after you’ve just found out you enjoy backdoor action while giving up your anal virginity to a man twice your age who wasn’t your boyfriend. We both laughed, an honest chuckle that broke into loud guffaws that left us both in tears. Composing myself, I gave her the room so that she could dress herself again.

*****

Rachel kissed me on the cheek before leaving the house. I watched her from the living room window, her perky ass sway exaggeratedly, as if she knew I was watching. That same ass that I had recently made mine. She faced my direction briefly getting into her car, and I instinctively ducked behind the curtain. What instincts I was following, or where they came from, I couldn’t say, but I supposed that if I’m going to give her time to figure shit out, that probably didn’t include me staring at her forlornly from my window. Her door slammed shut and I risked a quick glance at her. She wasn’t looking my way, simply sitting in her truck, hands on the wheel, engine off.

Suddenly, I realized I wanted her to leave. That was, of course, not entirely true. At that moment, I wanted more than anything for her to stay. Of course, that would be a terrible idea, and now that I was no longer doing my thinking downstairs, I could see that. Still, I could see the mental anguish playing out on her face, and I pitied her. I was having trouble with it myself. We were both standing on a precipice, one missed step away from plummeting into…what? I honestly wasn’t sure where this metaphor was going. Did the pit represent some kind of deeper relationship that we were in danger of falling into, or was our fragile arrangement the cliff? And whichever it was, did Rachel feel the same way about it?

Then I remembered, and it once again became urgent that she leave, that I may have already set our demise in motion. If I acted fast, I might have time to fix it and save whatever the hell was going on between us. If not, well, these last few moments staring at her as she sat in my driveway would likely be the last time I spent with her. It was a bittersweet epiphany to admit that, yes, I did indeed care for her, but that…Well, there was no time to worry about that now. I heard her engine turn over, then her truck backing down my driveway. She caught me staring, and I thought I saw a hint of a smile playing across her face before I lost her face behind her steering wheel.

I nearly sprinted to my truck as soon as she had driven out of sight. Ten minutes down the road I realized that I hadn’t locked my house behind me. I wasn’t even sure that I had shut the front door. Thankfully, there was little crime near my house because I didn’t have time to turn around now. The drive to my brother’s house seemed to be taking forever, despite making it in record time. I took the turn into his driveway too fast, nearly clipping his mailbox. My truck had barely come to a stop before I was out the door. Compose yourself, you can’t go in there acting like a madman looking like you sprinted the whole way here. Willing myself to be calm, I paced his porch, inhaling deeply of the spring air. I had nearly brought myself back under control when my sister-in-law, Julie, opened the front door. Her smile died on her lips as she caught look of my face. “Are you alright, you look like hell?”

“Yeah, Jules, I just had this kind of eerie…you know what, it doesn’t matter. Just coming by to see my favorite nephew.”

“That’s just cause I’m your only nephew,” came a cheerful voice from inside. Soon, RJ appeared at the door behind his mom. His arm was in a sling now, but his legs were both still casted, and he was using an electric wheelchair to get around the house.

“True,” I said, lowering my voice conspiratorially, “but I like you better than your sister, too.”

“Har har, you know I can hear you, right?” RJ’s sister, Claire shouted in mock offense.

“Come on in, come on in, we’re just about to serve dinner,” Julie beckoned, opening the screen door wider for me. “Claire, will you set another place at the table, please?”

“Oh, well, if you insist.” Julie followed me through the open door as Claire and RJ headed for the kitchen. “I’ll just go wash up, if you’re sure it’s alright?”

“Nonsense,” she laughed, swinging a dish towel at me as I trotted off down the hallway. I stopped one door short of the bathroom, making sure that all three had returned to the kitchen. I pushed the door open, sliding into RJ’s room. My hand still on the doorknob, I wasn’t sure if I should push the door closed behind me or leave it open enough that I could quickly sneak back out if I heard movement. Deciding on the latter, I quickly searched the room for RJ’s backpack. It wasn’t on his bed, by his dresser, in his closet, or anywhere on the floor that I could see, but he had a schoolbook open on his desk, so it had to be nearby. Finally, I spotted it, pushed up underneath his desk against the wall. I heard footsteps coming down the hall, but at that point it was in for a penny, in for a pound, so I grabbed it, placing it on his bed as I rooted through it. Fortunately, I found what I was looking for rather quickly: a small silver flash drive, still in the side pocket that I had snuck it into several days prior.

I threw the bag back under his desk, hearing several pens and pencils fall out of an open pocket and clatter against the wood floor. Placing the drive in my pocket, I pulled my wallet out, walking back into the hall and nearly colliding with my brother Matt. “I thought I heard voices, and then I realized, there’s only one person whose coming calling at this time on Italian night.” Noticing it was his son’s room I had just exited and not the bathroom, he gave me a quizzical look. I made a show of putting my wallet back in my pocket.

“I got him a little something, I was going to leave it as a surprise for him. Just a gift card, figured he could use it for a new game or something. Something to do while he’s stuck inside.”

“Thanks, man. That means a lot. To all of us. Now come on, spaghetti’s getting cold.”

***** Rachel *****

For several moments, I simply sat in my truck, still parked in his driveway with the engine off. Get yourself together, girl. You’re playing a dangerous game here. I know, I know, but I’ve never been with a guy like that. Idiot, you’ve never been with a guy at all. No, but still, there’s no way Ryan could ever fuck me like that. Ryan would give his left nut to have your ass, and you know it. Yeah, but it wouldn’t be like that: forceful, dominant…manly. Eventually, over the two disparate voices arguing in my head, I became aware that my ass was painfully sore. Not in an altogether unpleasant way, but the seats in my truck weren’t doing me any favors right now.

I started the engine, putting off any further mental gymnastics for the time being. As I backed down his driveway, I saw him watching me from his living room window. Desperate not to let him see me smile, I ducked my head down behind the steering wheel before turning my truck around and pulling out of his driveway. Once I knew he could no longer see me, I couldn’t hide my smile. It was guilty and wonderful, all at the same time, feeling like it might stretch right off my face and float away out my open window. What we had wasn’t love, even as an admittedly naïve teenager I knew that. But, it was exciting in a way I hadn’t felt fumbling around in the backseat of Ryan’s car, or sneaking blowjobs behind the bleachers, not even that time I had let him finger me underneath a blanket watching movies on the couch with my parents.

Maybe it’s time, girl, time to give it up. You know he’s been patient. Yeah, but is that fair now? Fair to who? Fair to HIM? I wouldn’t even be considering sex if he hadn’t opened my eyes to this. So you think he should get your other virginity then, too? No…I don’t know…maybe. Let’s be honest, Becky hated her first time. Said the guy fumbled around down there, couldn’t even get it inside her without her help, and then thirty seconds later it was over. One of these two guys could make my first time pretty memorable, and it ain’t Ryan. Girl, you are really playing with fire.

Lost in arguing with myself, I hadn’t realized I was already turning onto my street. Several houses down, I could see Ryan’s car parked in the driveway. He was outside, leaning against the driver’s side door, arms crossed over his chest, a cigarette hanging from his mouth. Damnit. I had told him my parents didn’t approve of smoking, had told them that he quit. What was he thinking? I pulled in next to him, already preparing to light him a new one for this, but as I opened the door, he beat me to the punch. “Hey, Rach, who the fuck is he?”

“Who is who?” I had a sinking feeling in the pit of my stomach. Had Ryan driven by and seen my truck in someone else’s driveway? It seemed unlikely; our school, his work, and his home were all in the opposite direction. Sure, it was a main road, but Ryan didn’t really have any reason to be out there, did he?

“Don’t play dumb with me, you little bitch.” Ryan had never spoken to me like that before and it took a moment for the shock to wear away and the anger to set it. There was no way for Ryan to know what I had done. Whatever he suspected was based on his own jealousy, and even if I was actually cheating on him (although not altogether willingly), it pissed me off that he would talk to me like that without any evidence. I could explain away my absence, have Becky vouch that I was with her the whole time. She’d do it, no questions asked. How dare he?

He pulled his phone from his pocket, and that pit in my stomach seemed to open wider, threatening to devour us all. So he had driven by. How could I have been so stupid? The guy had a garage, pull your damn truck in there, or ask him to park behind you. Shit. I maintained my composure, but only just. Maybe Ryan didn’t know who lived there. Who could I tell him I was visiting? I was still desperately searching for a lie that would save me from all of this when I heard a voice coming from his phone.

“You’re sooooo big.”

“Am I bigger than your boyfriend?”

I knew that voice. I knew what came next. Suddenly desperate, I clawed at the phone, trying to turn it off, shake it from his grip, stomp on it and smash it before he heard any more. “Oh, yes, you’re definitely bigger.”

“Ryan, you don’t understand. You have to let me explain.”

Then, that same voice, so obviously familiar but so hateful at the same time, “Oh yeah, Ryan’s little high school boy-cock is nothing compared to you. This thing is a hammer, he’s like a tiny little nail.” He closed the video, glaring at me one last time before hopping back into his car. I tried to follow him, tried to grab him and make him listen, but he was quickly firing up his engine and peeling out of my driveway. All I could do was watch as he sped away down the street.

Well shit. I told you so, girl.
6 comments

stormking11Report 

2019-11-18 07:08:08
If she really is a cheerleader, how come she is NEVER WEARING HER CHEERLEADER UNIFORM???? Why isn't she doing a striptease out of that uniform?

mainerReport 

2019-05-29 11:10:25
More chapters soon?

johnnyberottenReport 

2019-05-14 06:22:48
Okay.... didn't expect that one! Are you sure you don't write for Game of Thrones.... LOL
You took a really good premise, added in your excellent writing, and came up with an extraordinary story.....
Keep up the great work!

as always
johnny rotten

mainerReport 

2019-04-23 15:45:51
This is a great story line and excellently presented. Please keep up the good work.

Dudley DowrongReport 

2019-04-21 15:11:35
Excellent presentation. The twists & unexpected turns made the story captivating.
The wording indicated to me was that Amber was deceased; since Rachel found out about Amber, it surprises me she didn't find her death being the reason of her absence.
Even the relationship between Rachel & "our hero" isn't love but it seems to have gone beyond a "business contract". Rachel's POV closing out the story is an interesting twist. That twist simply keeps the reader wanting more.
I kinda thought "Becky" would have become more involved. Ryan shows himself to be an immature, jealous, selfish, teen, dickhead. If he really cared, he would want a reasonable explanation. At least, "Is that what U really think of me or was that stupid remark just for show? What kind of a hold does this jerk have over U?"
Look forward to more of Ur works. Thank again for sharing Ur talent.

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