Under My Boss's Authority: Office Romance Collection

by Jamie Knight

  “What do you say we get your pants off?”

  “Yes, Boss.”

  I undid her belt and opened her jeans like I was unwrapping a Christmas present and wanted to save the paper for next year. She lifted her ass to help as I eased her pants and then her panties down to her ankles and then down over her shoes.

  The sweet smell of her young, virgin pussy filled the recycled air. I just had to take a moment to admire its delicate beauty. Wetting two fingers, I reached down between her open legs and made first contact with her delicate lips, Ana jerking slightly and gasping as I did so.

  She was obviously really sensitive and would need a very light touch. Keeping that in mind, I started to run light circles around the outside of her pussy, slow and gentle at first, then a bit faster, gauging her responses all the away along, my young lover going from soft hums to moans and gasps.

  When I had gotten her sufficiently warmed up, I wetted my fingers more and then slid one inside her, getting about halfway in until her beautiful young pussy was just too tight to go any further. Staying where I was, I started to lightly move, lovingly caressing her sweet little clit while working her pussy, savoring each and every moan and gasp that came out of her.

  “Good girl,” I told her. “Let your boss warm you up for our trip and help you relax.”

  I could tell she was getting close to orgasm. Her whole body started to tremble, and her pussy got ever tighter around my finger, squeezing like a firm handshake. I slowed down my pace and stopped, letting her cum in her own time, the orgasm rising like a tide until she was absolutely vibrating with pure bliss, biting her bottom lip to keep from crying out.

  She came hard, her ass lifting from the seat with the intensity of it all. I coaxed her back down into the seat, able to feel the buzz still going through her, almost making it feel like she was softly vibrating. I held her and kissed her as she came down from her orgasmic high, Ana returning some kisses until we were making out, my hand still lightly covering her pussy.

  Kissing my way down her neck, I progressed my way down her body, taking off her shirt and bra as I went, spending some quality time with her beautiful tits. Then it was on down her tummy and over her pelvis until I was at her sweet pussy.

  “Yes,” I whispered. “This is what we’ve both wanted for so long, isn’t it?”

  She nodded.

  Starting off as light as could be, knowing she would still be sensitive, I licked her clean, holding her hand as I did. Intense new feelings ricocheted through her as I gave Ana her first oral sex experience.

  Ana shuddered and moaned under my tongue as I licked her ever closer to a massive orgasm. I took my time and did my best to try and make it special.

  She only had one chance at a first time, and I wanted to make sure it was as good as possible, despite the somewhat unorthodox circumstances.

  She put both hands on the back of my head, just in case I was thinking about ever stopping, which I wasn’t, and arched her back, pushing her hips forward, pressing her sweet pink pussy even harder against my lapping tongue. Impressively, she kept her moans to a minimum and even then, they were pretty quiet, especially for the intense pleasure she must have been feeling, getting eaten out for the first time.

  She peaked once again, driving her pussy into my face with all her might, doing her best not to scream, so they could hear her on the International Space Station. She dropped into the seat, limp as a rag doll, releasing my head.

  I licked her a few more times, just to clear her up and, when her pussy had settled down a bit, gently put her panties and pants back on.

  “There you go,” I said, doing up the buckle on her belt.

  To my surprise, but also delight, she embraced me, holding me tight, her face pressed against my chest. I stoked her back and her hair as she recovered from what we’d just experienced together.

  “Can I ask you something?” she asked, starting to rally.

  “Of course, anything.”

  “May I please suck you?”

  “Are you sure, honey?”

  “Yes.”

  “Okay but if it gets too much we stop.”

  “Deal.”

  Ana backed off a bit to let me undo my pants and take out my cock. Her eyes widened adorably when she saw it, the expression of surprise written on her face, even if she didn’t actually say anything out loud.

  Cautiously, she put her hand around my thick, throbbing shaft and started to stroke. She was nervous at first but before too long she was pumping, using her other hand on my balls. It felt heavenly, her soft, warm hands on me like that. I thought I might cum right then and there, but she hadn’t sucked me yet.

  Putting a hand on the back of her head, I gently guided her down to my cock. Still pumping my shaft with her hand, Ana licked the head experimentally.

  She must have decided it was nice because she then dropped her whole mouth on it and started to suck like it was a jawbreaker. I stroked her back as she sucked me hard, impressed at how well she was doing, considering her lack of experience.

  As she sucked, Ana got braver and started easing down further, caressing her soft, wet lips along my shaft. Eventually, she was swallowing over a third of it, the head pressed up against the back of her throat, tapping against me as she bobbed her head as though to her favorite song.

  She was so good that it wasn’t long at all before I knew I was going to cum. I wasn’t sure about coming in her mouth, as I didn’t want to risk downing her, so I tried to ease her up. To my surprise, she let out a little whimper and just kept on sucking, working my cock in her warm little mouth, softly gagging on occasion when she got a bit too ambitious.

  I figured she would know about cum even if not by experience, though I still subtlety eased back a bit to make room in her mouth for the load that was about to flow out.

  I flooded her mouth with my thick, hot cum, sending it cascading down her virgin throat like a waterfall. Ana took it like a champ and swallowed down every last drop.

  On instinct, I pulled her to me and kissed her tenderly as she kept on gently stroking my cock. Finally, I put it away and snuggled with her for the rest of the trip, so glad to have her with me and excited for what was to come.

  Chapter Six - Ana

  I could still feel it when we landed. Tucker had warmed me up so well, I didn’t think it was ever going to go away. Not that I wanted it to, of course.

  It was the best thing I’d ever felt in my life and I wanted to hold onto it for as long as possible. I was still a virgin but had a taste of what sex could be like, and I wanted more, with Tucker. I wanted to try everything, even the things that kind of scared me.

  He was quiet on the drive in from the airport. Things had gone pretty well. We showed our doctor’s notes and the letter Tucker got from his contact in the government, and we were allowed through with a minimum of fuss. We just had to wear masks at all times when outside, which was easy enough.

  We already had to do that back home and I, for one, was used to it. I wasn’t sure how Tucker felt about the whole thing, mostly because the airfield was the first time I’d seen him outside. Though I had to admit, he looked pretty good in it. Like a sexy doctor from a hospital themed porn video.

  I could feel the tingle down below again, but I did my best to hold on until we got to the resort, hoping we could carry on with what we’d started on the plane. Truth be told, I wasn’t sure why we hadn’t kept going. It was a rare opportunity to lose one’s virginity and join the mile high club at the same time.

  Sadly, the moment had passed, though doing them in succession also seemed like a pretty good opportunity. Despite his silence, Tucker was in no way shy about contact. He was touching me in some way the entire time, except for when we went through security.

  His warm hands made me feel all heated and sexy even through my clothes. I’d never felt sexier than I did with him. He really didn’t seem able to resist me, which was nice.

  As he stayed
close to me, but far from the clerk, we checked in to the resort and were given information on everything the facility had to offer. It was a somewhat redacted list because of the new pandemic protocols but there was still a lot to enjoy. Not that I really planned to be leaving the room all that much.

  Slipping an arm around my waist, Tucker shepherded me to the elevator and then to the room, never once breaking contact. It was like he could sense how much I liked it.

  It was almost like a physical need. I’d never really noticed it before, but I’d also never really had that much physical attention before, and once I did it was difficult to imagine being without it.

  I’d hoped we would get to the room and then hop right into bed and get down to business, but Tucker had other ideas. First, he unpacked, putting everything just so in the closet and dresser. He really was exacting.

  I’d heard he never did anything by half but had never really noticed until now. He’d cut our session on the plane short but probably more out of fear of throwing it off balance from all the hard pounding. I imagined him doing just that and could feel my cheeks going red.

  Deciding to take the initiative, I left my bags where they were and stripped naked on the spot, so my naked and ready form was the first thing he saw when his mind returned to reality, from whichever level of monastic focus he’d been on while sorting his luggage.

  “Wow.”

  I realized it was the first time he’d seen me all at once, the plane being more of a slow strip.

  “I want it,” I said, then realized I should probably be more specific. “I want you to take my virginity, I mean. I want you to pop my cherry, Tucker.”

  “Get on the bed,” he said, keeping his voice steady, while his hard-on raged in his pants.

  I could hardly wait to get it back into my mouth, and then some other places. Even my ass, though I wasn’t sure he would want to do that for the first time. I might need a bit more experience first, which was fine. I was willing to wait.

  Following his instructions, I sat on the edge of the bed and opened my legs in a way that I hoped was sexy. Even if it wasn’t, he sure liked my pussy, his gaze glued to it as he took off his own clothes, letting me see his beautiful cock gain.

  It really was gorgeous and had felt wonderful in my mouth once I’d gotten used to it. I’d barely been able to get it in there and could only imagine it would fill up my pussy.

  Tucker kissed me softly, like he had on the plane. As we made out, I breached the small gap of space between us and wrapped my hand around his cock, feeling it pulse warmly in my light grasp.

  Putting his hands on my shoulder, Tucker started to gently rock his hips, working his cock in my hand, so it was like I was jerking him off. Getting an idea, I put his cock in my mouth and had him face fuck me as I gently sucked on his beautiful cook.

  The thick shaft rocked with a regular beat between my lips, going in until the head touched the back of my throat. It wasn’t uncomfortable at all, and he never tried to go any further.

  I was familiar with deep throating, at least in theory, but thought I should get a bit more practice before I tried it. There was probably some kind of breathing exercise I could do to make it easier.

  For the moment I contented myself with sucking his big, hard cock again, savoring every last second of it. His hips gently rocked as I relaxed, able to just enjoy the warm comforting sensation of his magnificent manhood in my mouth.

  He came hard, filling my mouth with his sweet cm. I’d learned from the last time and did even better in swallowing it all down, smiling around his cock as I did so. Filled with warmth and happiness and not just from his cum going down my throat like a waterfall.

  I sucked him clean and then got him hard again before laying back into a more comfortable position, so he could fuck me for my very first time.

  To my surprise, but not really my display, instead of putting his cock right in me, he instead got on his knees and licked me until I was convulsing with a massive orgasm. His talented tongue buried in my delicate folds, bringing me to the gates of ecstasy.

  I came with a howl and a scream, letting out all the feelings and intensity that I wanted to back on the plane but that I had held in for fear of spooking the pilot.

  We were alone in the room though, on the entire floor as a matter of fact, and I could be as loud as I wanted. Which was good because with the way I wailed, I would have been scared someone might have called the police thinking I was being murdered.

  When I was warmed up and ready, Tucker stooped between my spread legs and got into position. Resting my legs on his elbows, so I was more comfortable, he stroked the warm head of his cock against my pussy.

  I immediately moaned, deep and long from the contact. It felt so good I could hardly believe it. I was a little scared, mostly because of the pain I’d heard so much about and wasn’t looking forward to experiencing, but with him there, ready to push inside me, neither seemed very likely.

  Taking his time, Tucker eased in, inch by inch, making me feel all of it and stopping regularly to give me time to adjust.

  “Good girl,” he said. “Let your boss all the way in. I need to go inside your pussy and make you feel good, okay?”

  “Yes, Sir,” I told him.

  It didn’t hurt, at least not at that point. There was a lot of pressure and I felt really full, but it was fantastic.

  He touched the tip of his cock to my cherry and I jumped a bit. He backed off, massaging my back, trying to calm me down.

  When I had returned to a more restful state, he tried again, pushing in and through, popping my tight little cherry.

  “That’s it,” he said. “Fuck yeah. That feels good.”

  I cried a little, and it did hurt, but not as much as I thought it might.

  The pain was sharp but short-lived, ebbing its way to the most delicious pleasure as he continued to pump deep inside me.

  I thought he might cum in me, despite the fact that we didn’t have a condom.

  But at the very last second, he pulled out and got his cock to my mouth before unleashing his sweet load down my throat.

  “Oh yeah,” he moaned. “That’s right.”

  “I feel so good, Boss,” I told him. “That’s what I wanted. Thank you.”

  “Thank you, Ana,” he said. “It was exactly what I wanted, too.”

  It was late when we’d arrived and the time change had done terrible things to both of us.

  So, by the time we were finished, we were both read to turn in.

  I wanted to go again but I figured we would have lots more time, later.

  Tucker got into the bed with me, and we spooned, his lovely cock pressed up against my ass, and his arms around me, hands on my breasts, as we drifted to sleep together.

  I loved everything about this moment and wanted to savor it into the next year and forever if I could.

  I only hoped it was what the future had in store for us.

  Chapter Seven - Tucker

  Oh, glory in the morning!

  I was usually happy to wake up, thrilled in fact. Ready to face the challenge of another day. That morning, the first in Australia and the second waking up next to Ana, after the plane, there was no sense of challenge at all. Just wonder and bliss.

  I had morning wood like I usually did. My big, hard cock was pressing up against her ass. I was just getting ready to pull away, assuming she’d want to sleep, when Ana started grinding her hips, rubbing her ass up against my cock. Making it clear what she wanted.

  “Good morning and happy almost new year,” I told her.

  “Same to you,” she said.

  “More?” I asked.

  “Please,” she begged, her eyes still closed.

  I shifted our position a bit, bending her knees, so I had a bit more room, and slid my cock up inside her tight pussy, sweet little Ana moaning as I did so.

  Waiting until she was relaxed and ready, I put a hand on her hip and started to m
ove. I pumped my thick, hard cock, in her delicate young pussy, her pink lips squeezing me as I went.

  Her hips beginning to move along with me, so we were moving with sweet synchronicity, Ana slid her pussy along the length of my cock, and I was pumping it into her pussy. It was music to hear her moan with wonderful pleasure.

  New Year’s Eve was tonight, and I was very much looking forward to a new start with her. Something I’d hoped for, but never truly dared hope would happen until it started to come true. Ana wanted me as much as I wanted her, and there was so much I could teach her.

  Ana came first, her pussy getting even tighter and wetter on my cock as she quivered in pure bliss. I cuddled and kissed her as I eased from inside her, shifting our position, so I could unload into her mouth, which I did in four smaller volleys, giving her time to swallow one before giving her another, Ana opening her mouth excitedly to receive each one.

  “Want to try something a bit different?” I asked.

  “Yes!” she enthused.

  Sitting her up and bringing her to the edge of the bed, I penetrated Ana’s pussy and lifted her up into my arms, so I was holding her. Ana instinctively wrapped her legs around my waist and her arms around my neck.

  For my part, I put both hands firmly under her ass, helping to keep her up. When she was comfortable with the situation, I lifted her slowly up and down, stroking her tight little pussy the length of my big hard cock and back again.

  She moaned and hummed as I gently took her for a ride, letting me know that she liked it. My cock was stroking right up against both her clit and her g-spot spot, so it wasn’t really a surprise. I could tell when she was about to cum and slowly stopped bouncing, just holding her as she quivered sweetly in my arms.

  Settling her back down on the edge of the bed, I eased gently from her pussy and moved my cock to her mouth, feeding her my load, which she accepted happily, grinning around my cock as swallowed and sucked. When she was finished, I carried her into the shower, and we got ready to enjoy the day.

  There wasn’t a lot open in town, so we decided it would probably just be easiest to go to the restaurant at the resort. Anyone sitting inside had to wear a mask, making eating exceedingly difficult.