My Boss's Big Surprise

Again I looked up at her. This time rather than disappointment my boss wore a look of satisfaction. Wanting to keep her happy I looked back down at her twitching cock before considering my next action. It was at this moment I noticed the smell of her womanhood. It was musky and strong, but nothing like mine. Her cock, massive as it was, still held a very feminine scent. Captivated by that I smell I decided I wanted a taste as well. My tongue first hit the underside of her glans, giving me a taste of her precum. It tasted as good as it smelled, so I continued tongue-bathing her penis, licking every inch of what flesh protruded past my hands. I found myself suddenly addicted to my boss's cock, but I felt unsatisfied. Driven by my newfound lust for cock I gave the head a few wet kisses before engulfing it. At that point the noises Gloria made shifted from ahs and moans to grunts. With a bit of effort I could fit the top of her cock in my mouth, but I wanted more. No, I needed more, so I pulled my left hand away and began inhaling more of my boss's beautiful cock into my mouth.

At that point something snapped in Gloria. Her hands grabbed me by the hair and she started thrusting at me. Suddenly I was almost completely out of control. The only thing keeping her from ramming her tool down my throat and choking me out was my right hand and its stranglehold around the base of her cock. This was about to change, too. Gloria shifted a hand to the top of my head, still grasping my hair and forcing me onto her or herself into me. It was tough to tell which was actually happening. Then I felt her left hand grab me right by the wrist. I tried looking up, hoping I could reason with her as she drove into my mouth over and over. It was hard to see past her heaving breasts, but the woman who was my boss was gone. Her face was angry and the only communication she seemed capable of were grunts and groans of ecstasy. I was tired and out of breath so it didn't take too much for her to wrestle my hand away from the base of her enormous member. When it was finally free of my hand she drove herself forward, forcing her fully engorged womanhood down my throat. I fully expected her to start fucking my throat at this point, but that's not what happened.

Buried as she was in my gullet I felt her massive cock start to twitch and I realized then what was about to happen. A moment later she shuddered and began literally pouring her semen straight into my stomach. As out of it as I was I was briefly saddened that this meant I wouldn't be able to taste her cum. Next time, I thought. Yeah, I guess I was already resigned to servicing her again, should she want that. Gloria pulled her cock out of me in one swift motion and I realized she'd already finished filling my gut.

"You OK?"

I looked up and to my relief the sex demon of a few moments ago was gone and my boss was back. I nodded, as exhausted as I'd ever been from using my mouth.

"I must admit, Lang, you did indeed handle me like you said you would," Gloria praised. "Most of my prospective partners are far too intimidated to do anything but run."

"I think it was you that did all the handling, though."

She laughed.

"So I guess you're just fine with all of this," she motioned at her large cock, which appeared only slightly less rigid than it had been when it was jammed down my esophagus.

"It's definitely not what I anticipated, but yeah... it was an interesting experience."

"And you'd like to continue this experience?"

Looking up at her I nodded.

"I notice that you haven't had any, relief, yet," Gloria continued. "Would you like some?"

Again I nodded.

She knelt down before me and approached, initiating another series of kisses. These were much less urgent than they were before. I suppose that orgasm she poured down my throat mellowed her a bit. I reciprocated, enjoying this much gentler exchange. A moment later she broke away, then her hands were at my waist.

"Alright Lang, let's see what I've got to work with here," she deftly manipulated my belt as she spoke and in moments my cock was free. "Hmmmm... this'll do it," she rubbed me to full hardness as she continued her evaluation of my penis.

"It'll get the job done, Miss Libbey," I ensured her. "I'm told it's above average, but I don't think the scale really applies given what you're packing."

Gloria laughed then looked me in the eyes. "I suppose I am on the outer edge of the bell end curve, aren't I?" she exploded into laughter at her joke and I joined her. "But seriously, though," she left the thought hanging as she dove forward and inhaled my penis, leaving me dumbfounded as her nose quickly tapped my stomach.

"Holy f... UHHH!" I exclaimed, my words quickly turning to nonsense as I felt her throat muscles start to undulate. Given what she was doing to me I was somewhat out of it, but it felt like quite a long time before I felt her pull away, my cock sliding back out of her throat. I did not hear her gag or even gasp for breath. When my senses returned I looked down to see her looking up at me, a broad smile playing across her face.

"Did you enjoy that?" she giggled.

"Uh huh," was all I could manage.

That's when Gloria went back to task, again engulfing my entire member. She sent her throat muscles into overdrive once more, but only for a moment this time. When she stopped, she began lifting off of me only to impale her mouth yet again. She continued this action repeatedly. In an absolute blur of motion she fucked my cock with her face. I could do nothing but groan and revel in her expertise. Again I heard no signs of gagging as she abused her throat with my cock. Thankfully she pulled away after not too long because I was fast approaching release. This time when I looked down at her she caught my eye only briefly before giving a sweet kiss to the head of my cock.

"Oh my god, you're incredible," I gushed.

"I get that a lot," Gloria responded. "I figure if you're gonna do a job you do it right. That goes for blowjobs, too."

"Well, you're definitely doing it right," I agreed. One thing though..."

"Hmm?"

"I gotta see those tits of yours."

"That's extremely unprofessional of you, Lang," Gloria reprimanded as she shrugged off her suit jacked and began unbuttoning her blouse. Before tonight I had no idea she had such a good sense of humor. When finished she pulled her blouse from the waist of her skirt, leaving it hanging as her hands went to the clasp between her sizeable breasts. She looked up at me and smiled again as she opened that clasp and freed them. Given how well endowed she was downstairs, the way her tits practically defied gravity should not have surprised me. They were perfectly formed and capped with large pink nipples. They were puffy, but not grotesquely so like you might see in some freak out porn. I wanted to taste them.

"Those are incredible."

"Yeah, I know," was all she said. Then she laid back and beckoned me with a finger. I guess she knew what I wanted. I placed my hands on either side of her then went in for a kiss. She seemed surprised, probably because she thought I'd dive right for those tits, but I'm nothing if not thoughtful. We shared another pleasant kiss before I did indeed seek out her breasts. At first I just squeezed them, caressing them gently before I lowered my mouth to her left nipple. I'd never sucked on nipples like these before and I found the experience left me wanting more. I switched to her other nipple, hungrily sucking it into my mouth. With my right hand I began toying with the unattended nipple, pinching and flicking as I saw fit. As I did so Gloria emitted soft little noises of pleasure. I was glad she liked having her tits fondled and sucked. Breasts as perfect as these really should be enjoyed. Wondering how far I could push it I began to nibble gently on the nipple in my mouth.

"Oh my, Lang, you really are hungry."

She didn't seem at all upset so I put a little more force into what I was doing. If her moans were any indication Gloria was liking what I was doing and it wasn't till I was quite literally biting her nipple that she let out a sound of pain and pushed me away.

"Just a bit much there."

"Oops."

"It's alright, but I feel we could be more productive here."

Is she seriously evaluating our sex play professionally? Yeah, she was made for an executive position.

"What did you have in mind?" I asked, curious how she thought we were being inefficient.

"Seems to me we could accomplish twice as much here if you'd fuck my tits."

Her expression was neutral so I honestly wasn't sure if this was more of her sense of humor. Regardless, I definitely agreed. I stood, kicked off my shoes, and dropped my pants. Once naked, from the waist down, at least, I stood over Gloria and lowered myself. As I did she grabbed her tits at the sides and held them apart slightly. I dropped my cock between her perfect white mounds as I settled down. Wasting no time Gloria used her hands to move her breasts over my manhood. I let this go on for a moment, luxuriating in the feel of her supple flesh as it rubbed along me. I was beyond horny at this point though, so once that moment was over I grabbed her hands with my own and the two of us cooperated in working her tits over my cock, but at a much more insistent pace than she was doing it alone.

"See, I told you this would be more effective," Gloria said as the two of us continued stroking my cock with her tits.

"You're absolutely right, ma'am, this is definitely a more constructive use of our time." It seemed almost ludicrous to carry on a conversation about how to most efficiently engage in sex play, but in the moment I didn't care. I began thrusting my hips in time with the motion of Gloria's tits in our hands and I could feel my orgasm approaching. "I'm about to cum, Miss Libbey. Where do you want it?"

"Paint my nipples, Lang," Gloria almost shouted. "Cover them in your cum. That's an order."

"Yes ma'am," I groaned as I lifted to kneeling and aimed myself at her right breast. I only had time to give my cock three pumps before the orgasm took hold and I launched the first shot of cum at my boss's nipple.

"Excellent work, Lang."

She was really getting into the boss/employee power dynamic here. It was definitely doing it for me too. I grunted and launched another rope of jizz, this one at her left tit. My aim was true, painting the puffy pink nipple white. I was losing steam at this point, but I was able to glaze each nipple a second time before I ran out of semen.

"I'm impressed by your production, Lang."

Holy shit, she was still cracking jokes. This woman is amazing.

"Yes, ma'am. I aim to please." I can crack jokes, too.

Gloria laughed.

"You've really made a mess here, though. I'm going to need you to clean it up."

"OK, where do you keep your tissues?"

"I'm sorry, Lang, I thought you were dedicated." Her voice took on a harsher tone. Again I found myself unsure whether this was a joke.

"Miss Libbey?"

"I want you to clean me up with a more delicate instrument than tissues. Your mouth should be sufficient, and this time no biting."

Again Gloria had me in a bind. I definitely wanted this to continue. Whatever this was, but I never anticipated licking my own semen off of her nipples. On the other hand I did let her jam her own cock down my throat and unload in me, and in that moment I felt resentment that I wouldn't get to taste her cum. Is there really such a difference between mine and hers? I guess that settled it.

"I'd be glad to, Miss Libbey."

I again dove for her breasts, this time starting with her right nipple. I gave it a tentative lick, finding myself actually rather curious what it tasted like. I guess that thing about it being salty is true, since that's the first thing I noticed. I don't mind salt so I threw caution to the wind and latched onto her breast with my whole mouth. That's when I was hit with a stronger flavor. Oddly it was sweet. I expected sour or bitter since that what people tend to call it, but I guess not mine. I sucked her nipple clean then licked all around the area ensuring I got it all.

"That's some good work you're doing. The other one now, please."

I moved to her remaining breasts, taking its nipple into my mouth as soon as Gloria instructed me to do so. I was definitely getting into the subordination and if the stiffening cock that was beginning to poke me in the belly was any indication she was getting off on ordering me to do something so depraved. It didn't take me very long to finish cleaning her up and following a few more licks to pick up a stray drop here or there both breasts were free of semen.

"I suppose that'll do it," I said as I pushed myself off of my boss. As I stood her penis stood as well. I was again impressed by its sheer size. I didn't let that keep me from being polite, though, so I reached a hand down and helped Gloria to her feet. Once I did she came in for a kiss and shoved her tongue into my mouth. I felt it swirling around and suddenly realized she was probing my mouth for the taste of my cum. Was it greedy of me to have already swallowed it?

"Am I wrong or did you enjoy that as much as I did?" Gloria asked after breaking the kiss.

"I'd be lying if I said I didn't," I answered, "but I don't know if it's because of what I did or that you made me do it" I hoped this admission wouldn't put her off, but I had a strong suspicion I was right after all.

"See, I knew it," she said. "You do have a thing for me. If that's the case I've got more orders I could give." She grabbed her impressive member to emphasize her point.

"Well, Miss Libbey, you're the boss." I hoped these words wouldn't wind up hurting me, figuratively or literally.

"That I am," she smiled as she spoke. "Lang, your next assignment is to face my desk and bend over. I need to know, though, are you experienced in this position?"

"To be honest, not at all, Miss Libbey," I answered truthfully. "I hope I live up to your expectation, though." I was having far too much fun playing this little game with her, and I knew she was, too. I turned around just as instructed and leaned over her desk, resting myself on my forearms.

"We'll start slow then," she said in a surprisingly gentle voice. I heard a drawer open and saw her flicking open a bottle of lubricant as I looked over my shoulder. I briefly wondered why she kept that in her desk. "Can you spread your legs a little more for me?" As had been the trend tonight I did as Gloria said. A moment later I felt a cool sensation on my anus as she rubbed a lubed finger against it. It was yet another new sensation that I found myself liking. I heard the bottle sputter as Gloria squirted a generous amount of additional lube on her finger and my asshole. "We're going in, Lang," she announced just before working her index finger inside of me. I let out a slight gasp, but there was no pain. She continued inward till I felt her knuckles hit my taint. She stopped there momentarily, then placed her other hand on the small of my back. It felt oddly comforting. I wasn't able to consider that much further though as my boss began withdrawing her finger from my ass before pushing it back in. She began a slow rhythm in and out of my me as she gently caressed the small of my back with her free hand. The whole situation felt surprisingly comfortable. So much so that I found myself leaning forward on my arms, closing my eyes and releasing a deep sigh.

A fairly sharp slap on my ass forced my eyes open. I threw my head around to see what Gloria's problem was. She caught my eyes with her own.

"You're going to want to be awake for this part, I'm adding number two," she announced. I simply nodded. Her hand left my back and I heard the bottle sputter again as she added more lube. "Here we go," she called just before her second hand returned to my back. A moment later she withdrew her finger till just the tip remained, then I felt a second finger join the first. She again pushed in. I let out a sharp hiss. She was definitely opening me up farther. After a little while her knuckles again came to rest against my skin. "Is this alright?" she asked. I faced her and saw that she was genuinely concerned that I was OK with what was going on. I nodded. "OK, I'm going to continue then." True to her words she began to fuck my ass with her fingers. After taking a few deep breaths I relaxed and suddenly it became much easier. "That's it," she said, "you're loosening up good. Are you ready for number three?"

"Yes ma'am"

"Good, good." She didn't warn me this time, she simply added her ring finger to the other two already in my ass. Again I felt stretched, but surprisingly the third finger was easier for me to take than the second. "I see a lot of potential for you in this position, Lang."

"I'm proud to have lived up to your standard, Miss Libbey," I replied, playing the game we were both enjoying so much. "I think I'm ready for the next stage of your assignment."

"You're showing great promise," Gloria replied. "If you think you're ready then I'm inclined to agree." With that she pulled her fingers out of my asshole. "I must warn you though, the next part of your assignment involves a steep learning curve." She punctuated her statement by dropping her large penis onto me. It came to rest in the crevice of my ass. "I have great confidence in you though, Lang. If you can fully accept my... instruction... shall we say, I'm sure the both of us will reap immensurable benefits." She was really stretching the metaphor here, but I was far too invested in the game to care in the slightest.

"I'll do my best, Miss Libbey. Give me your instruction, I'm ready." I felt her apply a fresh helping of lube to my anus, so I again craned my neck because I wanted to see what was about to happen as best as I could. What I saw was Gloria applying lube to the last seven or eight inches of her huge cock, using long slow strokes. I couldn't deny the way it glistened was beautiful. And that massive hunk of meat was about to go inside of me. She caught me looking and smiled.

"I have quite an attractive lesson plan, don't I?" she asked with a grin.

"I'm looking forward to experiencing it, ma'am," I replied. At this point she'd finished lubing herself up.

"And I'm eager to give it to you, Lang." I watched enthralled as she brought her left hand down and gripped my hip with it as best as she could. With her right hand she grabbed her womanhood about halfway up so there were maybe four or five inches exposed. She guided the head forward and soon I felt it pressing against my backdoor. "The first part of the lesson is the hardest to take, but I have confidence in you." With that Gloria leaned into me and I felt a great deal of pressure build up on my anus. Pressure turned to pain and I was sure I was going to fail, but to my surprise my asshole slowly began to open, accepting the head of my boss's penis.

"Oh fuck, that's a lot," I moaned. It hurt, but I was determined. Gloria stopped where she was though, as soon as I yelled out.

"Is it too much? I can stop," she offered.

At this point most of the head of her freakishly large penis was inside of my ass. I'm no quitter though. I looked over my shoulder and nodded to her. "It hurts, ma'am, but I can take it. please continue."

"You're a good employee, Lang. Taking one for the team is an important task." She leaned into me again as she finished her little speech and the effort forced the rest of the head of her cock into my ass. I grunted as it did, and with it a fresh blast of pain rocked my poor anus.

"Ugh... oh fuck, Miss Libbey, this really is a lot," I gasped, "Can you give me a little breather here before you continue?" My anus burned, but being stretched as I was added an unfamiliar sensation of pleasure to the pain. I absolutely wanted more of her inside me, just not quite yet.