My First Boss- Two Playmates

by George Punwell

  “We work at the same place and he drives me anyways mom.”

  “Just don’t break his arm sweetheart.” Mr. Landry chuckled as Brook yanked me through the door and across the lawn to my car. We stopped next to my car and she turned me, so my back was up against it.

  “Are my parents watching?” I scanned the windows but couldn’t see anybody and I assumed that they had moved back into the kitchen, further into the house.

  “No.” I said, looking back into her eyes. Even in the weak light from the streetlamps they sparkled with mischief.

  “In that case,” she leaned in to kiss me lightly on the lips, “you should get your keys.”

  It went over my head for a moment, “But they’re…” I trailed off, letting my finger point at her pocket.

  Her teeth flashed in the dark, “Yes. Come on and get ‘em, I want you to take me home with you.”

  I couldn’t help but laugh, “Fine, come here.” I put my arm around her and pulled her close to me. She was wearing those typical tight jeans and I had to flatten my hand against her hip, and I still had to force it into her pocket.

  She was giggling hysterically as she watched me try to get my keys out of her pants. I managed to get most of my hand into her pocket and I could barely feel the hard edge of a key with the tips of my fingers, but just couldn’t get any farther.

  “C’mon Tom, get in there, you can do it.” She breathed, kissing my face and moving her hips.

  “Ehr, you’re not…mmff, not helping Brook.” I grunted.

  “I know.” She managed to squeak in between fits of giggles and bouts of kissing my face. I almost managed to pin a key against the side of her pocket but it got away.

  “Alright that’s it!” I pulled my hand out and spun her around, pulling her back against me. I wrapped my other arm around her middle and shoved my hand back into her pocket. She loved this, and just to make it more difficult she started pushing her ass back against my crotch, rubbing against me. The close contact combined with what she was doing to me, was starting to affect me in a way I was hoping to avoid. However, due to this new position I was able to get my hand deeper into her pocket and managed to pull my keys out with little more effort.

  “HA!” I declared triumphantly, brandishing them in the air. Brook sagged back against me and made a loud disappointed noise. I chuckled, the thrill of victory making my blood pump faster, however minor it may be. I put both arms around her middle and gently squeezed her, leaning in and kissing her cheek.

  “Aw, smile. So, what do we do when we get to my house?” That cheered her up right quick.

  “You’ll see.” She said with a sly smile, getting into the passenger seat. I shook my head and got behind the wheel. We spent the short ride in comfortable silence. Walking inside was interesting but not too bad, my parents had the same concern as Brook’s. I gave them the same excuse she did and moved on, leading Brook upstairs to my room. There was an open room at the top of the landing that we used as something like a reading area, and my younger brother Dan was curled up in an overstuffed chair, tapping away on his PSP.

  “Hey dude. Kel in her room?” My brother and I had a good relationship, treating each other like best friends rather than siblings.

  “Yeah, but she’s being a bitch; I think you pissed her off again. Mentioned something about seeing you at the mall with some whore.” He said all this without looking up, his entire attention focused on the little screen. I looked at Brook with a shocked and appalled expression. She looked pissed for a second before she smiled broadly.

  “I hope those are her words.” She said smoothly. Dan actually jumped at the sound of her voice, looking up so fast I was surprised he didn’t break his neck.

  He looked from Brook to me, then back to Brook before responding, “Y-yeah, that’s um, that’s what she said…whoa.” Brook was struggling to hold back an even bigger smile as she watched my brother turn red at her attention.

  “Do all men in this family react like that in the presence of attractive women?” She giggled girlishly, making my brother turn a darker shade of red. I could feel my own cheeks burning at this. She looked between the two of us and broke into higher pitched giggles.

  “Alright that’s it! That’s it, let’s go!” I said, smacking at her supple rear to get her moving.

  “Hey!” she squealed, taking off down the hall towards my room, trying to escape my reach. Of course, never having been in my house before she didn’t know where to go. All the doors were closed so there was no indication of which was mine. She stopped at the end and looked at all three doors, doing a little dance of frustration as I sauntered down the hall, cornering her. I looked at my hand, moving my fingers around.

  “You know, I haven’t used this yet. It’s actually starting to ache.” I said, giving her an evil smile. Her eyes went wide, and she made a decision on which door to choose. Unfortunately, it was the wrong one. She turned and pushed into Kelly’s room. I quickly followed after her; I probably shouldn’t have taken my little act that far, now my sister would never leave us alone.

  “What the fuck!” I heard Kelly yell. As I came into the room behind Brook, I could just see Kelly in her bed, pulling her sheets higher up her body. To my surprise and horror, there was way too much skin displayed and as she brought her hand up to give me the finger, I could see it was slick with something. My mind immediately envisioned the worst scenario.

  “Are you gonna just stand there or are you getting the fuck out?” she growled. I grabbed Brook’s hand and tugged her back, she seemed rooted to where she stood, a shocked expression on her face. I gave her a little push out the door and turned back to my sister.

  “Tsk, tsk, Kelly what have you been up to?”

  “None of your fucking business!”

  “Well in that case I won’t give you your present early then.”

  That changed her expression completely, “Present?”

  “Yes. Something you might actually enjoy,” I couldn’t hold back a chuckle, “and it looks like you might have wanted it before we busted in on you.”

  She frowned, anger flaring up again, “Just give it to me, and I’ll leave you two alone tonight.”

  “Deal.” I chirped happily, digging into my pocket and pulling out the beast enclosed in my hand. Without looking at what might blind me, I lifted up the sheets and tossed it towards her feet.

  “You dick!” I heard as I ran from her room. Back in the hall, I closed my sister’s door and found my own open. Entering, I closed the door and found Brook sitting on my bed with her legs dangling over the edge, looking around my room.

  “So, what did you see?”

  “You know what I saw.” She said quietly. I walked between her legs and took her hands, playing with her delicate fingers as I looked down at her. Her cheeks were red, but I chalked that up to seeing what she did. Without warning she threw off my hands and looped her arms around my neck, pulling me down on top of her.

  “Can we…can we…” she trailed off, turning dark red, her mouth working to get out what she was trying to say.

  “Can we what?” I asked, lightly pushing my hips against her. She sighed and pushed her hips back in response.

  “Can we…Christ, can we…do it now? Please?” she asked in a tiny voice.

  I smiled and kissed her, “Baby you know I’d love to but, I think we need to wait until later ok?”

  “Why?” she whined, putting her hands on my shoulders and shaking me.

  “Because,” I lowered my voice and shifted my eyes sneakily, “we don’t want my family disturbing us, do we?”

  “No, uh…but why?” she just didn’t want to accept it.

  “Were you that turned on by what you saw?” I teased.

  “No!”

  I pulled myself off of her and sat down next to her, taking her hand in both of mine. She was pouting and avoiding looking me in the eye.

  “What’s the matter huh? You can wait a few hours, can’t you?”

  “I can’t To
m, I want to now.” She actually sounded like she was going to cry.

  “Aw, come here sweetheart.” I cooed, pulling her into my lap. She put her head on my shoulder and her arms around me. I had one arm around her middle, and the hand from my other was on her knee.

  “What would you rather have, a short, probably interrupted bout now, or a long hot and heavy session later tonight?” I asked reasonably, letting my hand wander up and down her thigh.

  “I…I, uh…oh god.” She whispered in my ear as my fingers began playing over the junction of her jeans. She buried her face in my neck and made little whimpering noises when I unsnapped the clasp of her jeans and slipped my hand into her pants. Her panties were totally soaked, and her slit was so wet that my hand stayed dry for less than a second.

  “What about…waiting?”

  “Well who says I can’t just use my little digits to…take care of your problem?”

  “Ohh…ohhk.” She breathed as I slowly pushed my middle finger into her tight cunt. She made a high-pitched little noise as I pushed my long finger in as far as I could.

  With a tiny strained giggle, she said, “Nhh-not little.”

  I curled it up and lightly ran my thumb over her clit, “Pfft, you’re just obscenely tight.” I chuckled. She turned an even darker shade of red and took one of her arms from around me, using her hand to push my hand harder against her soft skin. My finger went deeper, and the rest of my hand put more pressure on her clit.

  “Yehaaea Tom.” She gasped in a long low moan. She pushed her chest out against me, her big tits squashing against me. With my free arm I snaked my hand up under her shirt, closing over the voluptuous mound and gently squeezing.

  “Ahh!” she cried out loudly, before pushing her face back against my neck, her lips working like she was trying to bite me.

  “Shh baby, gotta keep it down ok.” I soothed, managing to get a few fingers under her bra to tease her nipple. I pushed harder against her pussy, managing to cram another finger into her hot tightness. That was too much for her, her breathing suddenly became very fast and very heavy. She couldn’t stop the loud moan that escaped her, thinking quickly, I kissed her full on the lips. She let it die to a faltering whimper in my mouth as her orgasm slowly subsided. She took her hand away from mine and used it to grip my shirt as her juices flooded over my fingers. She broke away gasping and slumped against me, both of her hands grabbing fistfuls of my shirt.

  “All better?” I asked, holding her after pulling my hand out of her pants and out from under her shirt. She didn’t answer for a long time, trying to compose herself.

  “More?” she asked innocently, looking up at me with her big grey eyes, trying to look as cute as possible.

  “Aw, no baby,” I said apologetically, reaching down and refastening the clasp of her jeans with a bit of effort. “I want to save a little of this for later.” I said, holding up my fingers, still slick with her cum.

  “But…but I have more! I’m not gonna run out.” She said urgently, like if she said it fast it would change my mind. I took a quick glance at the clock and turned back to her, squeezing her tight.

  “Dinner’s going to be ready in a few minutes.” Again, she looked like she was going to cry. I had to remind myself I was supposed to say no to her.

  “Come on,” I said, patting her back, “let’s go get washed up.” I wiggled my moist fingers as proof.

  “But,” her eyes lit up with an idea, “it’s what I want.”

  I laughed, getting up, forcing her to do the same, “Ah but you said within reason sneaky girl. Getting caught isn’t within reason.”

  She looked like she was going to protest again but I turned her and gave her a little push towards the door. She gave me a dirty look but didn’t complain any further as we washed up and headed back downstairs. Dinner was interesting, my parents grilled us about the normal things one gets asked when they bring home a girlfriend. It was particularly rough when Brook revealed she’d had her eye on me for most of high school.

  “I told you Thomas! I told you but you didn’t believe me!” My mother crowed triumphantly.

  “Mom, you’ve never even seen us together.” I countered as Brook struggled to keep from laughing.

  “Oh yes I have. Whenever we went to one of those meeting things that everyone had to go to, she tried to sit as close to you as possible. Hell, she talked to you all the time at those things!”

  “Mrs. Morrison, he never paid any attention to me, it was horrible.” Brook put in. I glared at the side of her head as she connected with my mom.

  “Aw I apologize for that sweetheart; he can be a little dense sometimes.”

  “Mom!”

  “Kidding Tommy.” She laughed, elbowing my father. Kelly rolled her eyes and focused back on her food; she hadn’t said more than two words since she sat down. Ben kept looking between Brook and I, an incredulous look in his eyes every now and again.

  As the conversation died down later on, I leaned over and whispered in Brook’s ear, “I’ll get you for that.”

  “I know you will.” She breathed, her hand slipping down to squeeze my thigh. From that point on, I could not wait until my family went to bed and left us alone. Alas, it just went on forever, Brook and I ended up watching a movie downstairs, waiting for them to hit the sack. My parents went first, with work in the morning and a sensible train of thought, it made sense.

  As night came on, the temperature dropped, and Brook and I found ourselves cuddled up under a big blanket. Ben was next and he stumbled off to bed after casting one last look at Brook. I couldn’t decide if he was just fascinated with her or if he had never seen a girl as gorgeous as she was, but found it funny, nonetheless.

  Kelly was the only one left, pissing me off to no end by sitting in the chair opposite us. She didn’t seem tired at all; her eyes were still bright and aware, glancing from the TV to us and back every so often. And at this rate I wasn’t going to make it, I was yawning so much my jaw ached. Brook too, was having a hard time, fidgeting around under the blanket.

  “When is she gonna leave?” she whispered in my ear.

  “Tired yet Kelly?” I called across the room.

  “Nope.” She replied smugly.

  “Fuck this.” Brook muttered under her breath. When I turned to look at her, my breath caught in my throat as Brook’s small hand grabbed my crotch.

  My eyes bugged out. “Shh baby, relax. Let me handle this.” She undid my shorts and slipped a hand inside, delicate fingers fondling my semi-hard cock.

  “What’s with you?” Kelly asked suspiciously, noticing the expression on my face.

  “N-nothing, cramp.” I grunted, as if in pain. Brook’s grin was probably the most savage one I’ve seen yet. Kelly kept staring at me, the embarrassment was competing with the sheer pleasure of what Brook’s hand was doing to me, to keep me semi-hard for far too long.

  Brook leaned up and kissed my neck, lightly nipping at the skin, “Don’t pay attention to her. Pay attention to me.” I sighed, closing my eyes and leaning against her. “Good boy.” Because of the blanket, my sister was oblivious to what was going on, but by my face she must have determined something was up.

  “Tired already Tom?” she asked sarcastically.

  “Mm, yeah.” I replied quietly. Brook had circled her thumb and forefinger around my shaft, slowly working them up and down. Now, normally when I…’took care of business’, I didn’t pay much attention to the head, don’t ask me why, it just felt strange. But, when I had someone else’s hands, amazingly soft hands by the way, touching the head of my cock it just felt awesome. I wanted to make some kind of noise, it just felt appropriate for the situation, some kind of recognition of the fine job she was doing. But I knew better, one moan, one hint of pleasure coming my way and Kelly would squash it.

  Brook began making longer stokes, capping it by lightly playing with the tip. I still had my eyes closed but I could still feel my sister’s eyes on me. But by now I could care less if I was laid out naked
and Brook was performing something more involved than a hand job. That particular realization caused a shiver of ecstatic delight to run through my veins and straight to my dick, which gave a satisfying jerk of movement in response.

  Brook giggled and gripped my shaft tightly in her fist, squeezing and pumping at the same time. This time I couldn’t contain a tiny squeak of emotion. That did it for me.

  “Kelly, I recall a certain deal between us,” I began, opening my eyes and glaring at my older sibling, she held her hands palms up in question, “you know, about you leaving us alone tonight.” Mind you, Brook didn’t stop what she was doing throughout this.

  “Why, are you doing something you shouldn’t?”

  I sighed, “Go play with your present. I went through all the trouble of getting it for you.”

  She narrowed her eyes and sneered at me, “Why don’t you go fuck yourself?”

  “Oh my god,” Brook sighed in frustration, releasing my throbbing cock and quickly stuffing it back into my shorts to my sheer disappointment, as you can imagine. “Kelly, can I talk to you for a sec?” Her voice had a dangerously subtle edge to it that made my sister take notice.

  However, she just raised an eyebrow as if to say, ‘go right ahead’. “Alone. Upstairs.” She got out from under the blanket without exposing my tented shorts and started for the stairs. Kelly shot me a questioning glance before getting up and following Brook. For a second, I considered going after them, but figured it was probably not in my best interests to do so.

  Unfortunately, after five, then ten minutes, I became rather concerned when no sign of either presented itself. So, I shut off the TV and went upstairs after them. Just as I reached the landing and turned towards my door to see if she was waiting for me there, Kelly’s door opened, and Brook stumbled out. One look at her appearance told me all I needed to know. She was panting, her hair was a mess, and as she came closer, I could smell my sister’s perfume stuff on her.

  “You…” she growled, pushing me backwards into my room and locking the door behind her, “you owe me so much; you might as well get on your knees right now.”