Please Let Me Try

I look over the brim of my laptop. He is still staring. I sigh in frustration and continue typing my report. I get my next paragraph written, and look up again. Still, he continues to stare, sipping his coffee. What is this guy's problem?

I shake my head and continue typing. A few more sentences later, I look up again. He is gone. I want to feel relieved, but a small part of me is disappointed. I haven't been gawked at in quite some time. I at least wanted to know why he was staring at me like that. Did I have something on my face? I rub my hands across my cheeks. Nothing.

"Hi, there beautiful." I almost fall out of my seat as he touches my shoulder. I twist my head to look at him and he holds his confident smile. "Sorry to have frightened you, I couldn't help it. I had to come over."

I catch my breath and muster up some courage to respond. "What do you want?"

"Well isn't it obvious?" His smile grows darker.

"No."

He cackles low in his throat. Now that he is closer I can see he is very young, much younger than me. Probably 19 or 20. He has dark wavy hair, grown out a bit too long. He is slender, sporty. His dark blue eyes are almost haunting.

"What is your name, gorgeous?" His eyes drift to my cleavage, and I wrap my coat tighter around me. He cackles again. "Aw, why don't you want me to see?"

"You're creeping me out. Please just tell me what you want."

"Well let me just come out with it then. I have seen you around for quite a while. You come in here and type on your little laptop. You look so concentrated, so focused. You are very beautiful."

What the hell is this kid trying to say? I'm a bit shocked. I know I must have about 10 years on him. "This is the only place I can come to have complete quiet. My house is pretty chaotic."

"Kids?"

"Yes. I have three. "

"Mmm, that's that validation I needed."

"I'm sorry... what?"

"So you are what I thought you were. A MILF."

I put my face in my hands and start laughing. "Oh my gosh... can't say I've heard that one before."

"It means mom I'd like to fu--"

"No, no I know what it stands for! I just have never been considered one before." I stop laughing and immediately realize what is happening here. This guy actually wants to fuck me?

I look up at him. His eyes are hooded and he smiles even darker now. What is his game?

"I'm sorry, but how old are you? You seem young."

"19."

Holy shit, he is way too young. "Um, well I think that's a bit of a stretch for me, hun. I'm in my mid 30s."

"Mmm, just my type." Is he kidding?! I take a deep breath, and regain control. I am older than this kid, I need to assert my status here. I can't let him get to me like this.

I crack a half smile and darken my eyes, "Move along, hun. You couldn't handle me."

His eyes widen. He wasn't expecting me to respond in such a fashion. Good, I have asserted my position. Maybe he will leave me alone.

Suddenly, he bends down, our eyes level. "Oh, please... please let me try."

His voice is a deep whisper, almost a plea. I purse my lips and look up, considering my options. "First tell me why I should."

A look of hope washes over his face. "Because I have wanted you for so long. The scenario plays over and over in my head. It's driving me insane. Please, please let me try. "

I look at him with a blank stare now, studying his sincerity. I almost feel bad for him. No one has ever obsessed over me before. It's... a turn on.

Maybe I should give this a try... what have I got to lose? He is very handsome, but I have never been with someone so young.

"Our age difference concerns me."

"No, no. I prefer it this way. I always have."

"So you have been with someone much older before?"

"No, but I've always dreamed of it. Please, be my first. Let me show you what I dream about at night; what I think about when I stare at you. I want to see what your body does when it's under my touch. I want to hear the sounds. I need to have you. Please, I'm going crazy."

"You are asking for a pity fuck. You realize that, right?"

He looks down in shame, "Yes."

...Dammit he has made me feel bad for him. I take a deep breath and take him by the hand. He exhales and closes his eyes at my touch. His mouth falls open as he looks up at me. "I still don't get it, but show me what you can do."

He seems to grow superhuman strength. He packs up my laptop for me, grasps me by the wrist, and pulls me towards the door. Adrenaline shoots through my body. Holy shit, what have I agreed to? When we step outside he releases me and hands me my laptop. "Where is your car?"

"Right over there."

"Okay, go put your laptop in there and then come back...please, come back."

I nod at him, put my laptop in my car, lock it, and walk back over to this curious 19-year-old. He takes my hand and leads me over to a tiny alley just around the corner. "I pass this place every time I walk home, and I always dream of the same possibility."

"I am not going in an alley to do this."

"No, no. I wouldn't do that, but I would do this." He then pulls me around the corner of the building, pins me roughly against the brick wall, and presses his lips to mine. He kisses me so passionately, moaning soulfully into my mouth. I invite his tongue to caress mine and I wrap my arms around him. His body tenses and he runs his hands down my shaking body. He then cups my face, and stares into my eyes. "You taste better than I ever could have imagined." He kisses me harder now, rough, demanding. His fingers run through my hair. I can feel my breasts swell and become heavy with arousal. My pussy starts to heat up and I can feel myself getting wet.

I place my hand on the front of his pants, his bulge filling my palm. He gasps at my touch, moaning deep into my mouth. "See? See how much I want you?"

His hands roam down my body, pausing at my breasts, squeezing and kneading them. My hard nipples strain against my bra. He kisses down my neck, nipping a bit. He savors me. I grab one of his hands and place it between my legs. He looks up into my eyes, his gaze burning with arousal. "Oh my god, you are so wet. I can feel it."

I sensually nod. I move his hand up and down the front of my pants, "Like this."

I move his hand faster, watching his cock grow harder in his jeans. My breath starts to quicken and I suddenly force his hand into my waistband. My lack of underwear makes him moan. "Fuck... so, so wet."

"Uh huh."

He kisses me again, this time more passionately. He forces two fingers inside me and crooks them upward. I clench around him and he moans into my mouth. He is putting off so much heat. He starts unbuckling his belt and let's his hard cock peer through his boxers. He starts to jerk himself as he rubs me. I look down and watch him pleasure himself. Wow, that is incredibly hot.

He smiles when he notices I'm watching, "You like that?"

"Yes.. oh god yes."

He jerks harder for me and my heart starts to race. My pussy is starting to pulsate. "I want to see you cum. Can you make me cum with you?"

We stare into each other's eyes hard as he works us both. We are both so close.

"Oh fuck.. ah, ready? Ready to cum with me?"

Before I can answer I clench around him hard as I release, squeezing my eyes shut, trying not to scream in pleasure. It is complete sensory overload; complete bliss. I bite my lip hard, almost to the point of blood.

He then lets out a deep, guttural moan and I see the cum shoot out of him, all over his hand. One, two, three times he shoots, creating an impressive puddle in his palm. As I come down from my orgasm, I bring his hand up to my mouth and suck the cum out of it slowly, savoring the warmth. He gasps and watches me with fascination. "Oh, that is so fucking hot." He is breathless when he speaks.

I give him a devious smile and release his hand, licking my lips. "Do you think you could make me cum harder than that in the future?"

He smiles and runs his fingers down my flustered cheek. "Oh, please let me try."