Yale…

If only she knew what it had cost me to leave her there, and not follow through. I wanted her, badly. I was so hard it was to the point of pain, and when I arrived home and shucked out of my jeans, there was a spot of pre-cum the size of a damn half-dollar coin on my boxers. The difference between Ally and me, however, was that I was under no imposition to be hands-off.

Finally stripped nude, my clothing in the hamper by the bathroom door, I flopped onto my back on one side of my bed. I reached up and clicked on the bedside lamp, reaching for the thick, tri-folded sheets of homemade paper resting below, in the pool of golden light.

I unfurled them and smiled at the first line…

Dear sex diary…

Okay, I’m sorry, I just had to get that out there. I’ve never penned anything like this before and I’m not sure what to do or really even what to say. It’s embarrassing almost – but not at the same time. I don’t think they have a name for what I’m feeling right now. I guess if I had to come close it would be ‘anxiety’ or ‘apprehension’ but those don’t quite cover it either, do they?

I pictured her pausing here, and I wrapped my hand around my shaft. I’d been hard for a while, and the head of my cock was super sensitive, and I wasn’t quite ready to get off so quickly. I wasn’t to the best part of her letter yet.

I’m stalling, aren’t I? Okay. You asked me to tell you what and how I felt while we played. I guess the first and most important thing is that I felt safe. That’s not a luxury I get afforded very often here. Like now, I hear yelling above me. It's two men so I should probably go into the bathroom. If a bullet is going to come through the ceiling, it’s most likely going to happen in the living room.

I’m not writing any of that for sympathy; I’m just trying to explain myself, I guess. It’s not just being in your apartment that I’m talking about when I say I feel safe. It’s guys and men in general. You think you’re safe with them but are you really? How do you really know? My grandmother raised me to be super cautious, to always spend the time figuring out what they want and their ulterior motive… that they always have one.

With you, I don’t have to do that. Do I think you have them?

I pictured her biting that lush bottom lip of hers and closed my eyes as I swept my palm up my shaft and over my head, slicking through the pre-cum and back down. Electricity flowing down from it and sweeping through my body in that pleasing first rush. I opened my eyes and picked up where I left off, that first rush echoed by her next words…

Yes. But I have them too, and for now, I think they align and it’s something… magical.

Standing there, in your kitchen, nude… I wanted you to see me. I wanted you to want me and it felt powerful and so good that you did, but I have a confession to make. It felt even better that I could just switch off for a time and not have to make any decisions. That was the best part. I like it when you get bossy. It’s like a relief like a weight lifted off my shoulders. I feel like this whole adulting thing is hard and even though I’m making it? I feel like I am on the edge of failure daily and you give me that back. That sense of purpose, like I am good at something like I do something right and I love that.

It’s the thing I cherish the most out of our encounters, the pleasure I get from pleasing you is almost like a drug… and I know that should scare me, but it doesn’t. It feels too right.

I’m sorry, I’m babbling and probably procrastinating again because honestly who writes a detailed report of their sexual encounter with their boss for review? But I’m liking this, too… It’s dirty in all the right ways. Hot and erotic and I’d be lying to you if I said I wasn’t turned on.

Fuck, yes. I moved my hand up and concentrated more on the head, swirling fingers and palm around it, the energy from her words galvanizing me, turning things up a notch, I was close. Really damn close, so I rushed to read the best part…

I can’t stop thinking about you. Your hands on my body, your mouth on my body, the feel of you inside me… I want it again. I want more of it, and I know that’s probably not the best thing but it’s true. I want more of you –

“Oh, god yes!” The pressure built, and I sucked in a breath as the first weak spurt painted the backs of my knuckles, the second and third pulse of my orgasm bringing more cum hot and sticky against my hand but immediately cooling against my skin. My balls tightening, my asshole pulsing along with it as I shuddered and lay still completely spent and satisfied.

Still, I wouldn’t waste a single one of her precious words… even if I knew them all by heart by now.

– and I’ll take what you’re willing for as long as you’re willing to give it. I can’t explain it, but what we do feels right. It feels good in a way that I’ve never experienced before, and I enjoy that exploration of that part of myself. I would be lying if I said that I wasn't scared of what you’re going to think of all of this. Of what this means, or if this will drive you away, but you asked for the truth and so here it is.

I wish the best for us, whatever that may be,

Ally

I set the three pages aside, safe from the mess and just lay still staring at the ceiling for long minutes. Every time I read her words, I pictured her. Nude and perfect, riding me. Bright green eyes heavy-lidded with passion, lips gently parted, begging me, her hair wild around her face in a golden halo.

We were on the same page and I liked that, but everyone had their limits. I needed to find hers and push them, mostly because that was the kind of bastard that I was. I pushed up and, containing my mess with my hands, padded into the bathroom and started the shower. I stood under the spray and let out a gusty sigh, another scene playing out behind my closed eyelids. This one of her green eyes clouded with hurt as she asked me if I even liked her…

Yes, too much. The traitorous voice in my mind whispered.

I thrust my face into the spray and held my breath until colored spots went off in the dark of my vision. I came up for air and sucked in a deep and deeper breath and resisted the urge to punch something. I lost and took some skin from my knuckles against the shower wall.

Ally was sweet. She was a pure and innocent girl despite coming from the Point Side. She may have been street savvy enough, sure, but sexually her inexperience was clear. Clear and tempting. Completely alluring and a fucking siren’s call.

I knew, even young, I was different. That what I liked wasn’t normal. Let’s fucking face it; when you’re a rich kid going to a fucking prep school, there were all sorts of illicit and deviant wonders to behold. My introduction into the lifestyle I had become accustomed to, sexually speaking, had come by way of Veronica Pratchett.

She’d introduced me slowly, at first by begging me to hold her down while we made out. Pretty soon she was topping from the bottom – which I hadn’t known it at the time, but that evolved pretty quickly. I’d gotten a taste for the control and I’d liked it.

Right up until my mother walked in on me with another girl, Marion Becknell, tied to my headboard with a pair of my neck ties as I’d shoved myself in her with such a punishing force she’d cried. She’d cried… but she’d fully admitted that she loved it. It worked for her. Gave her some kind of catharsis… but my mother? Controlling, conniving cunt that she was, she’d gone ballistic. Sent me off to an all-male boarding school in Connecticut and hadn’t looked back.

Never hesitated to remind me or demand if I were still engaged in my ‘disgusting deviant behavior’ anytime we encountered one another, even to this day. I’d been fifteen when she’d caught me with Marion and I’d been eighteen when I’d graduated with full honors but still, nothing was good enough for her. Nothing would make up for me being a grade-A pervert in her eyes. So, it had become a battle of wills. I’d gone to Columbia instead of Yale; I’d become a city-paid prosecuting attorney rather than a high-priced defense lawyer, or, what she’d really wanted me to do, which was to go into finances like my father. My father, who had secretly practically begged me to do anything but go into finance.

And now the cardinal sin, you’re letting yourself fall in love with a girl from the fucking projects. Mother is going to have a conniption if she finds out.

I pushed back from my shower wall and swallowed hard, images and vignettes of Ally Blaylock flickering past my mind’s eye. Walking away from my building with her blind friend, looking back and up at me… Green eyes filled with tears on my countertop… Perfect body on display on my coffee table as I entered her… Nude and wonderful in my shower, eyes wide with shock and fear... A shy smile playing across her lips at the 10-13 as Golden had talked with her...

She was beautiful. The perfect amalgamation of sweet, shy, and, behind closed doors, bold, adventurous, and yet still submissive. I’d been resisting, I still needed to resist but those worried and sad green eyes, so full of hurt filtered back into my vision as she’d asked me tremulously, intrepidly… Do you even like me?

Communication, negotiation, consent. These were some of the top tenets to make playtime between adults, both sexual and otherwise, safe and fulfilling, and I had been neglectful of the first. I had demanded clear communication from her and yet had been giving her non-committal vagaries in return.

I shut off the shower and dried off, wrapping the towel loosely around my hips. I marched purposefully to my home office and pulled the cord on the banker’s lamp on my desk, flooding its top with illumination. I dropped into the seat and opened a drawer, extracting the fountain pen my father had given me upon my graduation. I pulled a blank note card from another drawer and sat staring at its crisp white interior for an age…

Shit. I wasn’t good at this part. It was damn near social suicide to confide the truth about yourself to anyone in white-collar high society. I took a deep breath and put pen to paper.