Cumming of Age

The images of the past month rushed through my head like an editing session. In truth, it wasn't like an editing session, the images really were from an editing session: I had spent the weekend looking through all of the tapes I had of her, and my cock was sore from jacking off. She had no idea what I was able to put together, but when she saw it, I had a feeling she would be overwhelmed – humiliation on steroids. At least I hoped that's what she would be feeling, 'cause otherwise she was going to go ape shit. It wasn't quite time to reveal that little gem, however. There were a few more paces to put her through, including breaking her of the impression that we were somehow a couple.

"And the dildo, Robbie. Let's make sure that's properly inserted today."

She blushed every time I used the word – she said she preferred 'toy' or 'vibrator,' but she responded so well to the humiliation...I made sure to embarrass her every time I could. She took out the thing – it was bigger than me – and slowly rubbed it along her slit, pushing the material to the side. In a moment she had it inserted as deeply as she dared – she still had the faintest hope she'd make it through this thing without losing her cherry – and looked at my cock, as she fumbled with the strap.

"Why don't you use the thong to keep it in today instead of the strap, yeah?"

She slipped the material over the back of the thing, holding it in. It stuck out like a stiff cock pushed down at an odd angle. I started the camera. This was one freaky looking thing: she could have been a hermaphrodite – those gorgeous breasts and this odd stiff cock pushing out her underwear.

"I've decided to reward you today: you can suck me before we get started. If all goes well, maybe you'll get a bonus at the end. What do you say?"

Her eyes lit up, whether from the thing in her cunt or the prospect of sucking me twice in one day, I didn't know and didn't want to find out. In a flash she was on her knees, the vibrator waving around wildly, her teeth and lips making short work of my clothes, until she had her prize deep in her mouth. She'd come a long way in the past month, having learned to gobble my shaft deep into her throat to massage me completely. It wasn't nearly the same as having it in her cunt – I knew that would be nothing short of heaven – but it was amazing nonetheless. The most amazing thing was how easily she had overcome her gag reflex. It's one thing to be a gifted runner or any other athlete for that matter. It's another thing entirely to control the semi-autonomous nervous system. Or, maybe that is part of the athlete's gift: to control the parts of your body you need to excel. Whatever it was, she had a gift and she was all too happy to share it with me.

I came to enjoy these sessions during this early period. Although she never lost her sense of adventure and was always willing to push herself, even at the end of summer when we both knew the thing was coming to a close, it was these early weeks I remember most fondly. Maybe it had to do with her emotional attachment – the very one I was concerned about no doubt made her all the more tantalizing. Whatever, she was a cunt and I was going to make her a star. For starters, she had learned to suck cock like nobody's business. I held her head in my hands and felt her open her throat to take me as deeply as she could manage, and then, amazingly, she would move off and onto me like I knew she would do when I had her on her back. Maybe it was because she hadn't fucked anyone yet that she was able to do the things with her throat that she did. Thankfully, even long after she'd lost her virginity she didn't lose that throat. Little did I realize then how soon she'd cross that point of no return.

I told her to turn on the vibrator and felt the thrumming of it all the way into her throat. She would moan, knowing I didn't want her to cum until I had climaxed – the mere prohibition intensified her struggle. She still didn't know if she had an orgasm, but each time she took me, I reminded her she couldn't go over the top before I did. It seemed to make whatever she was feeling more powerful.

I knew today was going to be a quickie, and I wanted to make sure she understood the arrangements for Thursday before I finished.

"Robbie...that feels so fucking good. You are the best cocksucker I've ever had, you know that, right?" It sounded crude to my ears, but I knew in her twisted way, she filled with pride hearing me say it. "I wanted to let you know that Greg will be coming over on Thursday to help out...Don't STOP!" I slapped her ear just a little, shocking her back into her rhythm and I knew she was freaking out. This was the way I really wanted her to feel: out of control facing me with my cock buried in her throat and unable to stop. If she wanted to stop she knew what she had to do, but I doubted she would start humming 'dadadada dumdum dum da da.' She hadn't yet, although this last little revelation was probably bigger than anything I'd put her through before.

"Greg and you will be moving some of the boxes out of the basement for me. Depending on how far he gets on Thursday he may be coming back again." The double meaning swirled in my head even as I said it and I couldn't hold back any longer. I felt my balls curl up and hurl their load up and out of me deep into her throat. She groaned as she felt me spasming and I watched her move her hands onto the vibrator, using my pubic bone to rest her forehead as she came.

"Sir," she started quietly after recovering a few minutes later. "Sir, I...I understand you think I'll be unable to move the boxes myself and that's why you've asked Greg, but...but..." She was blushing so deeply her skin was deep red all the way to the tops of her breasts.

"You can say it, Robbie. I won't be angry." I had gotten dressed and was preparing to head into the basement. She was still on her knees, the vibrator still sticking out of her.

"Will you be expecting me to...to do this..." she waved her hands around her and left the question unfinished.

I loved this part. This is the part that made me jack off at night: her shame and shyness about what she was. She still didn't get it; she was still in denial. "I'm not sure I understood, Robbie. Could you be more specific?"

Her lips got thin from annoyance and shame, but she knew what she had to do to stop it, and she still didn't pull the switch. "Sir, will you be expecting me to work naked and to suck your beautiful cock when Greg is here?"

"Bravo, Robbie. You are truly a slut, aren't you?" I waited until she agreed. "Yes, I don't see why having Greg here should make any difference. Is there a problem?"

She knew she could always stop it, and I could imagine a series of statements by me, followed by 'turtle' from her, and that could very well be what would happen. At that moment I couldn't have predicted. I just loved her struggle and the tingles I knew that struggle sent up and down her spine. Her crush would see her demeaned and humiliated; she knew I was planning even more for her and that was the part she was really struggling with: being forced to suck him off before they had even gone on a date. Ho ho! The look on her face as she thought through the possibilities was precious.

She shook her head and stood up, waiting for her next assignment.

"Today, Robbie, so that we can make the most of Thursday, I need you to start inventorying the boxes in the basement. You can use a clipboard or your laptop, whichever you think you can get done fastest." I continued to explain what I needed done as we walked downstairs, pointing out the various supplies she might need, what I wanted her to catalog and how I wanted the boxes marked.

It wasn't a trivial task: I had several dozen boxes containing material stretching back over 20 years. Professional material I might want to keep, tax records, client records, awards, personal papers, my marriage, the kids' art projects – all of the detritus accumulated over a lifetime. I couldn't face the cataloging – it would have taken me a week to go through one box – and I wasn't sure I could face the decisions once I had a catalog in front of me. I did know that I had to go through the stuff, the sooner the better – it was weighing me down – and I knew I couldn't do it in the dark basement – I needed it in the light where I could breathe and cry and get over it without feeling like the house would cave in on me.

But none of those feelings would hamper Robbie or slow her down. It was all just papers and stuff and she would diligently do what I asked her to do, dildo up her cunt or not. Just knowing a naked woman with a dildo shoved in her was going through my things made it easier for me. It made it almost desirable – a sweet torture that I tried to ignore as I got down to my own work.

Shortly after she started, I heard her grunting, trying to shove one of the heavier boxes out of the way, but aside from that, she did her work quietly, letting me forget about the whole affair and focus on my own obligations. About an hour into the afternoon I thought I heard her gasp and I looked up from a tricky piece of editing.

"Is everything okay in there?" I shouted from my chair.

"Yes, Sir. I'm sorry. Everything's fine."

"Keep it down, please. I need to concentrate."

"Yes Sir."

And I continued to ignore whatever she was doing until several minutes later I thought I heard her crying.

"Robbie! What's going on out there?" I got up and strode quickly across the carpet. Looking into the outer room where the boxes were stacked, I saw her sitting in front of an open carton, her eyes streaming tears. She looked up at me and tried to apologize, but her voice caught on the tears and sobs. "What are you doing?"

"I'm...hugup...sorry, Sir. I'm so sorry. It must have been awful." She hugged herself, pushing her breasts against her arms, the vibrator peeking out from her thong. She looked pathetic and miserable and I couldn't imagine what she had found. I walked over to her, annoyed at her behavior and saw the box she was working on: photographs, stacks and albums and sleeves of photographs. Our wedding out-takes, Mary pregnant with Bruce. Brucey and Anney, the trip to Acapulco, and on and on and on. Anger boiled up even as my stomach cramped. This was why I needed her to do this. I would never have been able to even open the box, let alone try and list its contents. The anger threatened to turn into a blind white rage, but I nipped it as best I could. It wasn't her fault – she was doing what I had asked. I turned away and breathed as deeply and slowly as I could.

"Try. And. Hold. It. To. Gether. Robbie." In spite of my efforts to keep my voice level she could tell I was angry and she burst into tears, apologizing – afraid as much for how I would punish her as for the true sadness she felt. "Please. Robbie. This isn't helping. I. Need. You. To. Stop. Now!" I walked away and shut the door between us, leaving her to work through her feelings. I couldn't face this. Not now. Not a week from now. That box, and several others would wait, perhaps forever. I could hear her sobbing, trying to get herself under control, but I ignored it as best I could, redoubling my efforts to get the job done. This was one case of a crying woman not turning me on. I pushed down my own miserable little voice inside and focused on the video frames in front of me.

4 o'clock rolled around as it had to do and I heard her knocking softly on the door.

"I'm all finished for the day, sir, unless there's anything else you need."

I looked up to see her open the door and peek in, her eyes red and puffy, her makeup a mess. Why did kids feel the need to wear makeup? "Come in, Robbie. Come over here." I patted my lap. I watched as she made her way over, the vibrator still inside her, bless her heart, wagging like a grotesque tail in front instead of behind. She sat on my lap and put her arms around me, burying her face in my neck. My heart lurched a little – this was true affection, her need to nurture me or feel nurtured by me, I didn't know which was springing out of her. Something passed between us and I felt several conflicting emotions: of course, first and foremost, my cock twitched. I couldn't help feeling turned on when a woman truly offered her love to me. It had been years since I felt it and Robbie was practically oozing it from every cell in her body. Secondly I was afraid – I couldn't afford to feel anything like I felt at that moment towards her: she was my pet, my experiment, my pupil, my little slut. I didn't want to feel tenderness or, lord forbid, love. And third, I felt anger: anger at the world for taking everything away from me that had meant anything; anger at having to take care of this 18 year old twit because she couldn't get her act together; anger at having to feel anything after I had worked so hard to stop feeling at all.

She sensed something – I'm sure she couldn't begin to tease out whatever it was – and pulled away to look at me.

"I'm sorry, Sir," she said, and then she did something I never expected, but more incredibly didn't stop. She leaned over and kissed me. Passionately, with her lips wide open and her tongue pushing into my mouth. She pressed hard against me, giving herself to me and sucking the air out of my mouth. She pushed her hands against my head and held me tightly, all the while kissing me hard. She shifted for a moment and continued, keeping me off balance. She practically raped my mouth, forcing me to take her in. I knew I could have stopped her but I didn't want to, her lips felt so good against mine. She smelled so good.

Still holding me, she maneuvered her leg between us and turned to face me in the chair. We wobbled, off balance, but she held me tight and pressed the vibrator against my crotch, pushing it into her. I could tell we were in a dangerous position – if she moved a little too far back she might pull us over; if she pressed to hard into me, she might lose her virginity. The unbalance added to my disorientation. It, along with her lips and then her breasts pushing against me stiffened my cock. I knew if we kept at it I would be uncomfortable. I pulled back to get some air.

"Robbie!" I hissed softly. "If you keep this up, I'm going to fuck you right here."

She looked at me and melted, moving her hands down to my belt and working my pants off my rising cock. "Please, sir." Two simple words, and the way she said them: a servant, a personal assistant hoping to fulfill her boss' needs. Two words couldn't have been more complex in their meaning. The way she said it, she might as well have said: "I need you to. I've been wanting to feel your cock inside me for a week now. Would you Sir? Please. I'm ready and if you want to fuck me, I want to give myself to you." I didn't stop her, but watched a small part of me detached, taping us, wishing I had a camera going, but most of me completely lost.

In a moment she had my cock free and had reached down to remove the vibrator. It all happened so fast; I found myself swept up in a tidal wave of emotion – the past 18 months came sweeping in like a tsunami.

I lifted her up and placed my prick at the entrance of her slit. She was wet; no doubt she had come several times in the past hour with the vibe going the whole time and the taste of my cum on her tongue. "I'm going to fuck the living daylights out of you, Robbie! You have exactly 3 seconds to tell me to stop." I growled into her ear and slowly impaled her on my thickening cock.

"Please. Sir! Fuck me. Please fuck me! Yes! Yes! Agghhhhh...owwww....oohhh!"

And I was in. I could feel a little resistance and then a small 'plop,' and then I was buried deep inside her. She was so warm and tight. I just held her against my legs, feeling the warmth of her groin and the pulsing of her heartbeat on my dick. She moaned into my ear, begging me to fuck her to shoot my cum up inside her, but I just held her there. I felt a deep tenderness for her, at the same time I wanted nothing but to ravage the hell out of her, to take out my anger and rage on her innocent body.

She could feel the struggle going on in me. My hands pushing against her, holding her, even as my prick swelled inside her. I started sucking on her neck: focusing my anger on her skin, pulling a hickey from her. I knew it was stupid – what would she say to her parents, but I didn't care.

"Owwww, Sir. Yes, shit that hurts. Yes, suck me, Sir. Shit. Shit. Shit!" She vibrated from the pain, but hugged me tighter, pushing herself onto me and letting me take my anger out on her. She pushed her pubic bone against me and started a slow movement, trying to rub her clit against my shaft.

I couldn't shift my position; instead I just kept sucking her neck and collarbone trying to pull her skin into me. She rubbed harder, rotating her pelvis slightly under and up, under and up, until I was as deep inside her as she could get me. And then she stiffened and I felt her liquid gush as she came.

"Oh god ohgod ohod OHGOD, Sir! Please, ohgodohgod...oh shit shit shit.....fuck mefuck me fuckme yes yes yes." She screamed into my neck as the waves passed over her. I smiled even as I attacked her skin more fiercely, the realization that she had finally had an orgasm she could claim as "real" putting me over the edge.

"I'm cumming, Robbie. I'm going to shoot my cum inside you. Here it comes...." And I shoved my cock up inside her as hard as I could and hoped she could feel the pulsing of my sperm as it traveled up my shaft.

My mind was a swirl: rapturous, confused, angry and then sad. The sadness flowed in from my spine, my eyes, my brain. I could feel her kissing my neck, my cheeks and my lips and I couldn't turn away, but the tears filled my eyes and I let them flow down my cheeks. She stopped, for just a second, and then she kissed my tears, licking them and sipping them off my face. I saw she was crying too, but about what I couldn't begin to guess.

We sat like that for what seemed like hours, but was probably only a couple of minutes. And then I got scared.

"Robbie! Please tell me you're on birth control!"

She smiled wickedly and assured me she had been taking the pill for six months at her mother's urging "but don't tell my dad."

Women. Even as her mother was grounding her for having sex, she was taking precautions. Not stupid that family. I sighed – from satisfaction and relief of all kinds.

I almost apologized but caught myself. Even now, after we had breached some barrier (besides the obvious one) I wouldn't allow our roles to change. She was still my sub; my cum slut, my whore. All we had done was move the thing onto a new level. I tried to breathe and get used to the new status.

"Robbie. You've got to get home. It's getting late."

She smiled at me and kissed my nose. "Thank you Sir. Thank you so much for this. Now I know what people are so worked up about!" She slowly eased off of me, wincing at the stinging around her fresh wound. I looked down and saw a string of blood and cum oozing from her. "Oooh. I'm sorry. I'll get that cleaned up right away Sir." She quickly hopped off me, putting her hand on her cunt and ran to the bathroom to get a towel. I didn't move, letting the mess stay on my legs rather than dribble onto the chair.

I watched as she collected her things upstairs and pondered the situation. Thursday was going to be interesting. As if reading my mind, she looked up at me and blanched a little.

"Thursday, Robbie. Think very carefully about how you want to work Thursday. Greg already knows what you are doing here. I think he would enjoy having you very, very much." She looked sad and confused for a moment, looking down as if to recall what had gone on minutes before. "Oh, don't worry about that," I stroked her lightly. "I'm not the jealous type. I much prefer to share my enjoyment and share in others' enjoyment, and I know Greg will very much enjoy being here. You'll make sure of that, right?"