11: Jessica in the Bedroom

As I kissed Jack I looked into his eyes. Did he trust me enough I asked myself? Would he go along with this?

I pulled his shirt free from his pants and tugged it up over his head. I ran my heads lightly over his mostly hairless chest, hearing him gasp slightly as my hand trailed down to his stomach. He was cute. Fit. But not rugged or muscular at all. Still, he was very cute.

My hands slipped lower and stared to unbuckle his belt, my lips finding his again, kissing him harder. A soft moan from him -- I could feel his excitement.

I opened his buckle and sank down to my knees in front of him. I tugged his pants and underwear down, smiling up at him as his small penis bobbed free, most of the way hard already. I heard him groan "Oh Jessica....." as I lightly stroked it with my fingernails.

I look up at him and demanded softly "Hands at your sides, and don't move."

A momentary look of confusion crossed his face, but he obeyed, moving his arms to his sides. I took the tip of his penis between my lips and quickly sank down on it, taking it all in without a problem.

I played with it with my tongue, rolling it around in my mouth, feeling it harden more. I looked up at Jack, watching the look of amazement on his face, watching him staring down at me, obediently keeping his hands at his sides.

I finally started bobbing up and down and his penis once he was fully hard. He groaned and moved his hands to my head. I slapped them away and stopped, his small penis still in my mouth.

"Keep them at your sides." I commanded, speaking around his penis. His eyes widened, but he obeyed, moving this hands back to his sides.

I sucked on him, swirling my tongue around the small head of his penis, eliciting a deep groan from him. I sucked harder, bobbing up and down on his little dick.

His breathing grew labored and he suddenly bucked, cumming in my mouth. I stifled a giggle at how little there was, easily keeping it all in my mouth and then swallowing it, looking up at him as I swallowed, letting his little limp dick slip out of my mouth.

Jack looked down at me as I swallowed, a look of surprise mixed with joy on his face. I giggled, smiling back at him as his limp little dick slipped out of my mouth. I asked coyly "enjoy that?" And then chuckled a bit as he nodded his head yes.

I played with his little penis with my fingers, looking up at him. "Ever gone down on a woman Jack?"

He shook his head nervously "Um, n-no."

I smiled a bit, still rolling his little dick between my fingers. "Well I want you to listen. You're a nice guy, and you're cute. But your dick is tiny. If we're going to date, you're going to do as I say and learn to please me other ways. Understand?"

I watched as Jack's eyes opened wide in shock, his eyes started to water a bit and he started to tremble. He stammered 'w-what? I -- I'm not that small."

I smirked a bit "Oh sweetie, you are." I wrapped my hand around his now partially hard penis and squeezed "My hand completely covers your little penis."

I added quickly "But it's ok -- there are other ways to please a woman, you just need to learn." I slowly stroked his penis "You can obey my rules and learn, or you can leave. What do you want to do?"

I watched as Jack blushed crimson and stammered "W-what d-do I have to do?"

I smirked a bit and stood in front of him, releasing his dick. "Good boy. Lie on the bed, hands at your sides."

I watched as Jack hesitantly climbed on the bed and laid down as instructed.

"No touching me unless I give you permission. Understand."

Jack nodded hesitantly.

I smirked a bit again as I pulled my dress over my head, revealing my black lacy thong and bra. I unclipped the bra and tossed it on my desk chair and then pulled the thong down, tossing it on the chair as well. "Like what you see little guy?" I asked playfully.

Jack nodded, swallowing hard, his little dick as hard as it could get.

I climbed on the bed next to him on my knees, towering over him. Straddling him, I trapped his arms with my legs. His eyes widened. "You're going to do only what I tell you to do, right?" He nodded yes.

I smirked and moved up, positioning my pussy above his face. "You've never tasted a woman before?"

I bit my lip, suddenly nervous. Was I really going to do this? It's one thing to see it on-line. It's entirely different to do it for real. Was I really could to make Jack my obey me?

Jack stammered "I, uh, n-no...."

I lowered my pussy to his lips demanding clearly "Lick me Jack, lick my pussy."

I looked down at him and placed my hands on the wall, one on either side of the window, and leaned forward. I watched as he tentatively licked my pussy.

I rocked my hips, grinding down against his tongue. I demanded "Harder Jack, lick me harder."

His tongue pushed more against me, still uncertainly, almost randomly moving against my pussy. I groaned in frustration "Lick along my lips, part me with your tongue."

He obeyed, his tongue opening me, running along my lips as I rocked against him, pressing down a bit more.

"Now move your tongue back and forth. "Mmm, yes, just like that Jack....more....right there....." I moaned as he found my clitoris.

"Keep doing that....."

I pushed down harder, grinding against his face, staring down at him, moaning loudly as his tongue ground against my clitoris. "Oh Jack -- more....."

Jack struggled to breath under me as I pushed down against his face, grinding my wet pussy against his mouth, his tongue. Still his hands stayed obediently at his side, even as I rocked hard on his face, moaning loudly, almost smothering him.

I suddenly came hard, my body shaking, involuntarily pushing down hard, pinning his head against the pillow. I cried out loudly and then groaned, collapsing forward against the wall, panting a bit.

Jack squirmed, freeing his nose and gulping for air, his eyes wide. He stared up at me in amazement. 'Y-you just had an orgasm?"

I giggled, climbing off of him and snuggling up against him. "A very good orgasm silly -- and you gave it to me." I smiled and took his hand, guiding it to my breast "You can touch me now."

I smiled at Jack, watching him as he gently caressed my breast, his chest still heaving as he caught his breath. He asked "I'm really that small? I really can't please you?"

I smiled softly at him "You just pleased me -- you just need to learn how. But yes, your little penis won't do it for me...."

He almost looked like he might cry as I finished saying that. I added quickly "But don't worry -- if you'll obey my rules, we can still both have a lot of fun together. Deal?"

He nodded slightly, though his cheeks were crimson.

I giggled and added playfully "Ok then, now, would you like to fuck me?" As I rolled onto my back and spread my legs.

Jack's eyes got wide in surprise and he quickly climbed on top of me. I pushed him off "Condom little guy -- you need to use a condom."

Jack blushed again and quickly found one in the pocket of his pants. I giggled, watching as he eagerly opened it and rolled it over his small, hard dick. He climbed back on top of me and pushed into me.

I looked up into his eyes as he thrust into me, barely able to feel him inside me. I smiled politely as he began thrusting, grunting a bit each time he thrust into me. He groaned "You feel so good...." I responded by stroking his back. "Cum for me Jack, come inside me...." I encouraged.

Jack thrust awkwardly into me, grunting. I smiled up at him and wrapped my arms around him, whispering into his ear "Cum inside me little guy, let me feel that tiny penis cum in me." Jack groaned, looking down at my in surprise.

I stared up at him, demanding more loudly "Cum Jack, cum inside me with your tiny little dick."

Jack suddenly spasmed, cumming, grunting loudly. He collapsed on top of me, sweaty, panting.

I rolled him over and laid on top of him. I kissed his lips playfully. "Enjoy that little guy?" He nodded as I giggled "Twice in one day. That's not too bad." He smiled a bit.

I looked down at him with a more serious look "Keep obeying my rules, and we can keep doing this. But I'm in the boss in the bedroom. You tiny little dick can't please me, but you'll learn how to obey and please me other ways. Understand?"

Jack nodded, blushing.

I smiled and rolled off of him. "Great, we should get dressed. It's 10pm already."