My First Boss- Two Playmates

by George Punwell

  I cringed as the head of my cock slowly sank into her hot, wet, cunt. As she let her hips down, more and more of my cock disappeared into her, moans escaping from both our throats.

  “Oh god Eve, you feel so good.” I groaned with a sigh as she settled her hips, my cock completely buried in her boiling confines.

  She giggled quietly, “Mm so do you Tommy, you always…f-fiuuhhh!” she cried out as I put both hands on her ass and pushed myself up into her. From there, coherent words and sentences became very difficult to make. She pushed her hips back, cramming my dick as far as it could go inside of her, sitting still for a moment, reveling in the feeling of the throbbing bar of flesh and blood inside her.

  Her breasts were now just out of reach, a tantalizing prize if I could only bend my body in an impossible way. But I was far from lacking in something to play with. She had propped herself up on her elbows and was looking away from me with her lips parted in an inadvertently seductive look. Instead of holding her firm ass with both hands, I put one arm over the curve of her lower back and held her down like that while I pushed up into her. With my other hand I gently took her chin in my hand and turned her head so I could kiss her. She smiled and giggled into my mouth, swirling her hips in a ridiculously sensual movement.

  I pumped my hips against her a few more times, to her unintelligible encouragement. And after a few moments she wrapped her arms around my head and held it tightly to her sternum.

  “Tom! Aahh don’t…uhn…please…I’m!” she moaned loudly, her body stiffening as her cunt contracted around my cock. She squeezed my head hard against her and cried out as she had what must have been a powerful orgasm. I could feel her juices trickling down my shaft onto my crotch and legs. I grinned and pumped my dick into her harder and faster, prolonging her orgasm. The tone of the noises coming out of her changed in pitch, from low to high, until she was almost screaming. I was so into it I didn’t even notice that familiar welling up sensation and barely registered the immense release. Eve squeaked in the middle of a dying scream as she was suddenly and unexpectedly filled with a large amount on hot cum.

  I deflated under her as her head dropped down onto my chest with a thud, my cock still pumping inside of her gently twitching pussy. After a minute or two she patted my shoulder and picked her head up, a massive grin on her face.

  “How…jeez…how did you know how to do that? I didn’t tell you, did I?” she gasped. A wave of warm self-satisfaction washed over me, and I put on my best nonchalant look.

  “Oh, you know, it just sorta…came, to me.” I winked at her and she burst out laughing.

  After calming down she gave me a long hard kiss on the lips and rolled off of me. “You’re so cute.”

  “You know you guys keep saying that, and I’m starting to wonder whether it’s actually a good thing, or a bad thing.” I said suspiciously, turning my head to look at her as she lay next to me.

  “Haha, I…we, we’re just proud of what we turned you into. From tall, awkward, and suppressed to…to, my tall awkward stud.”

  “Hey!” I lightly backhanded her in the stomach and rolled on top of her, getting on my hands and knees. She bit her lips and gazed up at me with an excited look in her brilliant blue eyes.

  “I…am…not…awkward.” I stated softly, punctuating each word with a tender kiss on the lips.

  She giggled girlishly and pulled me down on top of her, “Yes you are.” I gaped at her in mock shock, “And I wouldn’t have you any other way.” My face burned which just made her laugh harder. “And you still can’t take a compliment from me without doing that.”

  “I can’t help it.” I said sheepishly.

  “Awww.” That did not help the color of my face one bit. I sat up and looked away, trying to will the red from my cheeks. I could tell she wanted to say it again but thankfully restrained herself. I composed myself after a few moments and looked back down at her. She was still lying back on the bed, her arms folded just under her breasts, looking back at me with a little smirk on her lips.

  “Oh! I have an idea.” I said, grinning down at her. She raised a delicate eyebrow in question and propped herself up on her elbows eagerly. I reached out my hand for her to take and pulled her up into a sitting position, leaning in close. “What do you say to giving the beast one last hurrah?” I whispered in a conspiratorial tone, my eyes alight.

  Now it was her turn to change colors, she blushed hard and averted her eyes. “O-okay.”

  I smiled and turned her head again so I could kiss her, “You don’t have to if you don’t want to.”

  She kissed me back harder and grinned, “No, I want to. Lemme go get it.” She hopped off the bed and scampered into the bathroom. She reappeared a moment later, throwing the little white vibrator at me. I snatched it out of the air without even realizing it, my old baseball reflexes kicking in. But it was merely a distraction, because the next thing I knew she tossed her naked body at me, driving me back onto the bed.

  “Mmm, so what are you gonna do with me Tommy?” She purred, clambering atop my waist once more. I looked at the small device in my hands and turned it on, smiling as it buzzed to life between my fingers. For a moment my mind filled with where it had been, my heart rate picking up a notch.

  “Well, I was wondering what this might do to you.” I palmed the buzzing machine and held it to the center of her right breast.

  “O-ohh.” She looked down at my hand, concealing the vibrator between my hand and the supple flesh of her breast. “Ohh that feels good.”

  “Not weird?” I asked curiously.

  “We-whell, kinda. But it still feels good.” She looked me in the eye and smiled, amused by my curiosity. I switched to her other breast, this time running it directly around her nipple. She squeaked and giggled when I did that, pushing my hand in adjustment.

  “Better?”

  “Mmhmm.” She closed her eyes with a little sigh. I kept that up for a couple minutes before taking it away from her skin. I had to hold back a chuckle as her hand jerked, inadvertently trying to stop my hand’s retreat.

  “Aww, now who’s cute?” I teased. She blushed again and then gasped as she felt the vibrator’s touch on the sensitive area just above her clit. I slowly touched the tip to her skin and moved it in long slow circles around the little nub.

  “No explanation needed here I see.” I quipped happily. She looked down at me with eyes that could barely focus; before she squeezed them shut again as I drew the tip slowly over her clit. She was straddling my waist on her knees and they began squeezing me spasmodically, the rest of her body tensing along with them.

  After a few long minutes she scrunched up her face and gritted her teeth, a strained noise filtering through her clenched jaw. A little more moisture seeped onto my skin from her glistening slit.

  “Do all girls react like this to one of these things?” I asked, turning it off and lightly running my fingertips over her outer area. They came away wet and I rubbed my fingers together.

  She sat there for a moment, looking up at the ceiling and panting, before responding, “I don’t know, probably.” She let herself fall to the side and lay on her back with a sigh.

  “Tired?”

  “God yes! I’m not a teenager anymore.”

  “Eve, I swear to god if you keep calling yourself old…”

  She picked her head up and smirked at me, “You’ll what?” I grinned evilly and raised my hand, spreading my fingers wide apart.

  “Oh, I see. Well maybe I want to save that for another time.” She giggled before yawning unexpectedly.

  “Aww, want to close your eyes for a bit?” She nodded and yawned again as I leaned over and kissed her tenderly on the lips. I rolled off the bed and shut off the lights before stepping out into the main room, closing the door behind me. The TV was on and I could see the back of Brook’s head over the back of the couch. I tiptoed into the room and quietly pulled on my clothes.

  “Took your sweet time Tommy.” Her voice made me look back up a
t the couch. She was resting her chin on her folded arms and looking at me over the back of the couch.

  Smiling I said, “So what would you know about how long this stuff takes?” She blushed and gave me a dirty look. I came around the side of the couch and sat down next to her.

  “So.” I started, kissing her cheek, “You mentioned telling me about wanting something if I survived? Well, I survived.”

  She giggled sadistically and tented her fingers, eyeing me with her beautiful grey eyes, “Keep your pants on Thomas, you’ll find out what I want eventually.”

  “Evil! Evil girl you are!” I gasped in mock horror.

  She lifted her chin and smirked, “Maybe, but at least I know what I want, and I know

  you’re gonna give it to me.”

  “Oh, you think so?” I replied, jabbing her in the ribs with a finger. Though, one thing she said nagged at my mind. I know she wasn’t being serious, and she was talking about something completely unrelated, but did I…did I actually know what I wanted? In any case, that was a question to be answered another time.

  “I know so, baby.” She purred, pushing me over and positioning herself on top of me. She kissed me passionately, barely able to restrain the huge smile pulling at her lips.

  She pulled away for a second, allowing me to suck in a much-needed lungful of air; “This is your idea of eventually?”

  “Mmm, no, this isn’t what I meant.” She sat up and waved her hand in the air thoughtfully, “Merely a…side dish.”

  “Oh, now you’re comparing me to food?”

  “Maybe.” She squeaked in an incredibly girly tone.

  “Adorable.” I smiled, sitting back up and kissing her again. “Whatcha watching?” There were just commercials on right now.

  “Scrubs.” She looked at me sidelong, another smirk on her lips.

  I grinned broadly, putting my arm around her and pulling her close, “I knew I loved you for a reason.” She turned bright red and her lips parted in something akin to surprise. I didn’t realize why. After a second or two, I could have sworn tears began to well up in her eyes.

  “Are you all right?” Concern prevalent in my voice.

  She sniffed, wiping her eyes on the back of her hand. “Yeah, yeah, I’m fine.” She sighed contentedly and wiggled as close to me as possible. I smiled to myself, totally pleased with this situation. We stayed like that for a long time it seemed, until I heard Eve’s bedroom door open and close.

  “Make me jealous why don’t you?” Eve said, sounding like she was yawning again.

  “Says the one who fucked him.” Brook snickered. Eve sagged into her chair and shrugged. She had put on a light blue halter top and a pair of small shorts.

  “Your idea.”

  “Ladies, be nice.” I said, before anything else could happen. I winced as Brook pinched my thigh, hard.

  “Ow, what?” I asked. She gave me a hard look but said nothing.

  “She wants to leave, I think.” Eve said, smiling tightly.

  “Do you?” I asked, looking down at her. Brook nodded almost imperceptibly. I sighed, “I guess so.” I stood up, Brook doing the same. “So, I’ll see you bright and early tomorrow morning boss lady?” I knew that would get a real smile out of Eve.

  She chuckled and gave me what I wanted, a heartfelt smile. “Right you are boy toy, right you are.” She stood up as well, giving me a tight hug and a kiss. I grinned and followed Brook to the door. She seemed to be in a rush to leave. She hurried out into the hall while I threw a pained smile back at Eve as I closed the door. I was confused to see a knowing smirk on her face.

  I caught up to Brook at the stairs and took her elbow, turning her so I could see her face.

  “Are you gonna tell me what’s wrong?”

  I was actually startled to get a full-fledged, toothy white smile right in the face. She laughed and took my arm, pulling me close. “All part of my little scheme Tomsky.”

  “Couldn’t you have been…I dunno, more polite about it?” I asked weakly. I really didn’t want to throw off her mood, but I wanted to make sure there wasn’t any bad blood between the two.

  She giggled, walking me arm in arm to my car. “I told her about wanting to do this, don’t worry about it.”

  “You did?”

  “Mhm.” We got into my car and I turned to look at her.

  “So, you just want to go home?”

  “For now.” She cooed. As I drove her home, I couldn’t help but notice the furtive glances she cast my way. When I pulled up in front of her house, I put it in park but kept the engine running, expecting her to just get out, (yeah, I hadn’t gotten the whole romantic kiss goodnight thing down yet).

  Instead, she grinned and reached over, turning off the car and taking the key. I made a halfhearted grab for it, which she easily avoided, tucking it into her jeans pocket. Even if I wanted to, I couldn’t have gotten it out of there.

  “So, I’m going in with you then?” I’d been into her house, oh maybe two times, and seen her family all of never.

  “Yes…you are.” She said smugly, she loved when I didn’t have a choice in things like this. We got out of the car and made our way to the front door. I hesitated as she held the door open for me.

  “Aww come on big boy, you’re not scared, are you?”

  “N-no.” Fuck! Her grin threatened to split her face in twain. She took my hand and pulled me inside. I could hear her family throughout the house. Her parents in the kitchen and her brother blasting music upstairs. Still leading me by the hand, we passed the kitchen not stopping, and heading for the stairs.

  “Brook? Sweetie, is that you?” Her mother called, poking her head around the kitchen entrance frame.

  “Yeah mom! Hi mom! This is Tom! Bye mom!” Brook responded at light speed, not stopping for a second as she dragged me upstairs. I only got in a partial wave before we were out of sight. Up in the hall we didn’t slow down either, her brother’s music was much louder up here, maybe why she didn’t like hanging around at home a lot. We busted through her door and she nearly threw me across her room and onto her bed.

  I lay on her bed panting, confused, and more than a little startled as she carefully closed the door and leaned back against it, composing herself. She ran her fingers through her hair, pulling it back behind her head, a band thing magically appearing in her hand as she deftly did it up into a ponytail. Brook took a deep breath and closed her eyes. She had cut her dark brown hair recently, shortening it by a few good inches.

  “Sorry about that Tom. I…I um, got a little carried away.”

  “No problem. So, uh what are we doing here again?”

  She looked at me sitting on her bed and bit her lip hard, bending her knees and squeezing her legs together. I couldn’t understand what was wrong with her, what was going on with her today.

  “This isn’t fair.” She growled to herself, bringing her eyes back to me, “I uh, I’ll be right back.” With that she opened the door, scooting out and down the hall. I heard another door open and close; I assumed it was the bathroom door. Nothing had changed in her room since that last time I was here. Big walk in closet filled with trendy clothes and the like, desk with computer, big bed, and bookshelves loaded with romance novels, a big mirror on her bureau that had all her make-up and other beauty products on it, posters on the walls featuring her favorite movies and half naked, Abercrombie-esque guys.

  I got up off her bed and walked over to her closet, a maroon and silver something had caught my attention. Walking into it I plucked her old cheerleader’s uniform from between some other random outfits. Not for the first time I realized just what a lucky son of a bitch I was, how many guys had fantasies about getting the cheerleader, and I got the captain! I put it back and walked back into her room proper.

  “Who are you?” I would be lying if I said her little brother didn’t scare the shit out of me. He was a full-blown Goth, a dying breed to be sure, but still. Pale skin, eye liner, all black clothing, chains, black hair, the works. He w
as a freshman at my old high school, or more accurately he would be when school started up again.

  “I’m Tom. You’re Ben, right?” I asked, standing up straight, I towered over the kid.

  “Oh yeah, she talks about you a lot.” He rasped. His voice was similar to somebody who’s been smoking for years. And I guessed ‘she’, was Brook.

  “Only good things I hope.” I joked. He just rolled his eyes and grunted, turning and walking back to his room.

  “Creepy little bastard.” I muttered under my breath.

  “What were you doing in my room freak?” I heard from the hallway. There wasn’t any answer, so I assumed he just ignored Brook. She walked back in and nearly ran into me as she wasn’t paying close attention, looking very distracted.

  “And where did you go?” I asked curiously. To my surprise she turned bright red and scurried into her closet.

  I leaned against the frame as she pulled out a backpack and started stuffing another set of clothes into it. “Oh, what did you do then? You don’t blush like that for any old thing.”

  “None of your business Thomas.” She replied uncomfortably. It was then that it finally sank in that she was packing clothes.

  “What are you doing?” She slid past me and pulled out some undergarments from her bureau.

  “Did you think this was the last stop?” she asked, a sneaky little smile making me nervous.

  “Where then?”

  She was grinning now, “Why, your house of course.”

  “M-my house?” I stammered.

  “Yes, it’s what I want.”

  Inside I was thrilled, but I forced that expression from my face, “We have work in the morning remember?”

  “Don’t worry, I won’t keep you up too late.” She purred, shouldering her backpack and taking my hand again. She led me back down the hall and downstairs.

  Both her parents were near the bottom of the stairs as she pulled me towards the door.

  “Staying at Tom’s.” Brook stated in a voice that one would be hard pressed to challenge. That didn’t stop Mrs. Landry from trying though.

  “You have work in the morning.”