My Boss in More Ways Than One

At the end of the staff meeting on Monday morning my boss, the principal Miss Robins, took me to one side and told that she had chosen me to accompany her to s special management workshop.

"It's only a day, but rather than drive back that night I thought we could drive up the afternoon before, stay in the hotel and drive back the morning after," she smiled at me, "does that sound good to you Pam?"

"Sure Amanda, that sounds like a great idea," I replied, smiling even though I dreaded the prospect of a day and two nights with her over some boring and stuffy workshop; after all, it wouldn't do my career any harm.

"Great, I've already rescheduled your classes," she beamed at me, "we leave Thursday afternoon and come back Saturday morning!" Great, I thought to myself, it was going to eat into my weekend too; good job John was away again.

The week flashed by and it was soon Thursday afternoon, the two of us heading out across state in Amanda's car. We chatted about all sorts of things on the long drive and it was fortunate that I actually really like my boss; Amanda is a few years younger than me at 35, quite attractive, with long blonde hair and a full and buxom figure. Although she can be quite severe and businesslike when she needs to be, I would consider her to be a warm, friendly and approachable boss.

By the time we got to the hotel it was quite late and I discovered that my boss had booked just one room for the two of us – we'd be sharing.

"Don't worry, it's got two beds!" Amanda chuckled when she saw my discomfort, "I'm just thinking of the school's budget."

Well, fair enough, I thought to myself, it's not so bad, and Amanda's not the worst person to be sharing a room with surely? We made our way up to the room and it was actually very nice, with two double beds, plenty of space and a very well-appointed en-suite – was this really the money-saving option?

"What I need is a drink!" Amanda said as she went to the mini bar, care to join me?" she produced a bottle of wine and poured it into two glasses, and we toasted each other as we sipped it.

We unpacked our overnight bags and I noticed that Amanda seemed to have brought a lot of stuff with her, but by the time I'd used the bathroom she'd put it all away. We agreed we were both hungry so we headed down to the hotel's restaurant, enjoying a rather fine meal and quite a lot of wine. We chatted away like we were old school chums and at several points I could have sworn my boss was flirting with me, but I put that down to the wine.

Giggling and joking, we made our way back to our room and both flopped back on our respective beds, tired but relaxed and satisfied. I kicked my shoes off but Amanda was going further – as I watched she stood up and slipped out of her blouse and skirt, revealing some very sexy looking lingerie.

"Mmm, that's better!" Amanda sighed happily as she stood there in front of me, showing her hot body off to me, "come on Pam, won't you join me?"

She smiled at me as she stood there, looking very sexy in her black underwear; a lace half-cup bra that lifted her breasts up and together and in no way hid her large nipples, a matching suspender belt with the black stockings they were clipped to, and the skimpiest, smallest excuse for a thong I'd ever seen, which left me in no doubt that my boss's pussy was shaven and hairless.

I wasn't sure what was going on here, but I decided to go along with it; under Amanda's gaze I slipped out of my blouse and skirt, revealing the pale cream lace bra I was wearing, the matching skimpy panties and the tan hold-up stockings to complete it. I looked up at my boss and I could see the hungry look in her eye – Christ, did she fancy me?

"Take them off Pam," she ordered me, "your panties, take them off."

"Excuse me?" I asked her, staring at her in disbelief as she stepped closer to me, "You want me to do what?"

"I want you to take your panties off and show me your pussy!" she said forcefully, "why do you think I invited you along to this thing?"

"To help my career, to learn from the management course!" I blurted out.

"Oh, you're here to help your career all right," she purred as she casually undid her bra and let her tits spill free, "I guarantee that you will still have a career if you do everything I tell you to do."

"I, I don't understand?" I asked her, watching in a mixture of shock, surprise and excitement as my boss proceeded to ease her thong down and off, standing before me with her legs spread in a dominant pose and showing me that she was indeed clean-shaven down there.

"Every now and then I choose one of the staff as my sexual plaything," Amanda told me as she reached out and stroked my face gently, "and I've had my eye on you for some time Pam. Do everything that I ask of you and your career is assured and will blossom."

"And if I don't do what you want?" I asked her, staring into her eyes as her hand slowly made its way down to my bra-covered breasts to caress them.

"I'll make every day for you so bad that you will quit your job," she smiled sweetly at me, "but that's not going to happen is it? You're a smart woman; you'll do whatever is necessary won't you? After all you love your job and want to keep it don't you?"

She gently pulled one of my bra cups down and rubbed her fingers across my nipple, making me shudder and moan with pleasure – my nipples are super-sensitive and I love having them played with. I looked down to see my nipple stiffening to her touch then looked back up into her eyes.

"Seems I don't have any choice do I?" I asked her as I carefully hooked my fingers into the waistband of my panties, easing them down a little bit.

"Go on, all the way," Amanda murmured, pulling her hand back from my breast as she watched me closely.

Acting like I didn't want to be doing it, I slowly eased my panties down, sliding them down my stockinged legs and stepping out of them, straightening up and surprised to see Amanda holding her hand out for them. I passed my panties to her and watched as she lifted the gusset to her nose, inhaling deeply.

"Mmm, yes, a fine perfume," she sighed happily, "the scent of your pussy is quite delicious!"

She stepped up to me and while one hand gently caressed one of my small breasts the other dropped to my groin, running down my hairless mound to rub lightly across my slit. I moaned with delight at that touch and she smiled at me, moving ever closer to my face. I closed my eyes in acceptance and felt her lips on mine, and as I gasped from her twisting my nipple her tongue entered my mouth.

I responded to her kiss – how could I not – and our tongues danced wetly together as her fingers slid into my wet folds and teased my opening, while her other hand twisted and tugged on my sensitive nipples, making me groan and sending shivers of pleasure through my body. My pussy was really getting wet now, especially as Amanda was exploring it with her fingers.

"I'm going to fuck you all night," Amanda growled when our mouths finally parted, her finger right up inside me, "we are going to eat each other's holes and share each other's fluids until we pass out from sexual exhaustion."

"Oh sweet Jesus!" I groaned as Amanda smiled lewdly at me, her finger wriggling deep inside my pussy.

"You're going to submit fully to me aren't you Pam?" she said in a sultry voice, "You want to keep your job don't you? Yes, I can see it in your eyes and feel it in your cunt; you're going to be a good little slut aren't you?"

"Yes Miss, I am," I whimpered as my boss twisted my nipples again, making me wriggle about, "I... I'll do whatever you want!"

"Great, I knew you'd be sensible," she grinned, "now, go and kneel next to your bed."

I knew this was the first test for me and I was determined not to disappoint my boss, so I made my way over to the side of the bed and dropped to my knees, looking over expectantly at Amanda.

"Good girl!" she beamed at me as she walked over to me, "now, eat my pussy!"

She stood over me and lifted her left foot up onto the bed, reaching down and pulling my face into her groin, pressing my mouth against her exposed slit. Her pussy smell was strong and pungent – it had been a long drive – but it just turned me on even more as I started to lick her sticky folds; her pussy was ripe and in need of my attention, and that aroused me.

"Yes, that's it Pam," she purred as she gazed down at me, stroking my hair as I licked, lapped and sucked on her tangy pussy lips, "you're getting into it aren't you?"

In all truthfulness I was; Amanda's pussy was slippery with her juices, which I liked the taste of, and I liked how her puffy labia felt in my mouth. I gazed up at her as I slid my lips up to her clit, giving her the puppy-dog eyes as I sucked on the hard little bud, making her gasp and smile at me.

"Oh sweetie, that feels so good!" she sighed happily as her hand gripped my hair and pulled me harder into her sex, "makes me want to ride your pretty face..."

She pulled away from my face, leaving me kneeling there licking her cum off my face as she went over to her bag and searched inside for something. I gasped when I saw what she had found, a pair of handcuffs, padded but still proper serious-looking handcuffs.

"Lay face down on your bed Pam," my boss ordered me and I meekly did as I was told. I got up and lay on my front, Amanda quickly joining me on the bed and pulling my arms behind me. She cuffed my wrists and then helped me roll onto my back, so that I was lying on my hands.

"Perfect!" she smiled at me as she climbed on top of me, straddling my head and taking hold of it with both hands, "now I can ride your face!"

I was helpless, bound and trapped under her as she pulled my face into her gash and started to grind it against me, rubbing her wet folds against my chin, mouth and nose. She really was literally fucking herself against my face and making a right mess as she did – which I started to enjoy. Her slick pussy lips spread wide open and smeared her tangy love juice all over my face, coating me with her creamy secretions.

"Oh yeah, that feels so good!" Amanda groaned happily as she thrust herself back and forth, "your pretty face feels so good, I'm going to cum all over it!"

I was a mess and I loved it, being used in this fashion, helpless to be nothing more than an object for my boss to use. My pussy was twitchy and wet but I couldn't get to it, my hands were at the wrong angle underneath me; all I could do was lay there and have my face used as a masturbation tool. I pursed my lips so that Amanda's labia spread over them and she was using my nose to rub her swollen clit against, holding my head firmly and humping it like a schoolgirl against her pillow.

"Ungh, Pam, yess, I'm going to cum!" she groaned loudly, her hips thrusting faster and her movements more urgent, "all over your pretty face!"

I was struggling to breathe properly and my arms were getting uncomfortable underneath me, but there was nothing I could do except lie there and be used. Amanda was grunting and moaning as she moved faster and faster, pulling my face ever tighter into her drooling open sex, rubbing it across my slippery chin and mouth, thrusting her clit against my nose and filling my nostrils with her cum.

"Fuck!" my boss cried out as she started to cum, her body shaking and her spread-open gash drooling and dribbling all over my slick face, "yesss!"

Her hands were tangled in my hair and her hips jerked spastically as Amanda climaxed, copious amounts of love cream pulsing from her cunt and covering my face, dribbling down my cheeks and neck. I could feel her contractions as her pussy discharged more and more juice over my face, until eventually she was spent, her hips slowing down and her hands releasing their grip of my head.

"Oh Pam, baby, thank you," Amanda sighed as she eased herself back and bent down, kissing me and licking up some of her own spend, "that was wonderful; you deserve a reward!"

For a few moments Amanda busied herself cleaning my face up a bit, kissing and licking me as she scooped up her cum and fed it to me, smiling as she stuck her slimy fingers in my mouth and watched me suck them clean. Then she climbed off me and went to her bag again, producing several more pairs of handcuffs.

I was rolled onto my side and she undid the cuffs that held my wrists together. The relief was sweet but I barely got a chance to massage my wrists as my boss got to move up the bed, lying back with my head and shoulders propped against the bed frame.

"What are you going to do?" I asked nervously as she cuffed my hands back together and pulled them above my head.

"Giving you your reward," she smiled at me as another pair of cuffs secured my hands above me, "I'm going to make you cum again and again."

With clear practise Amanda snapped cuffs around my ankles and clamped the other ends around the bed posts, leaving me secured to the frame with my legs pulled back and spread wide – I was completely exposed and utterly helpless, ready to be my boss's plaything again.

"Pam that is such a beautiful sight!" Amanda gushed as she stepped back and admired her handiwork, "I need to record this for my collection."

"No, wait, what are you doing?" I panicked as she retrieved a digital camera from her bag, "you can't do that!"

"Oh, but I can, and I will," she smiled at me as she lifted the camera to her face and started to snap away, "don't worry, these are just for me, I have a collection of all my pets!" There was nothing I could do to stop her photographing me like that, bent double, and tied up, my pussy and ass hole displayed for all to see.

"Now then, let's have a taste of your beautiful body," Amanda said, putting the camera down and joining me on the bed, kneeling before me and running her hands down my stockinged thighs, leaning in and inhaling deeply, enjoying the smell of my wet pussy. Then she stuck her tongue out and started licking me, lapping wetly all over my groin – inner thighs, pussy, taint, my tight little ass hole, everywhere.

I was quivering and moaning as Amanda focused on my pussy, pulling it wide open and feasting on the slick interior, licking and lapping and sucking on my flesh. She was driving me wild with her mouth and tongue and the look of utter delight on her face turned me on even more as I wriggled and writhed against my restraints.

All she used were her mouth and tongue, and boy did she know how to use them! With her fingers holding my pussy lips wide open she explored every inch of my juicy cunny, every little nook and cranny. She teased my clit out and made it stand to attention, sucking and nibbling on it, drawing such loud cries of pleasure from me and such huge amounts of cunt cream.

It was like this that Amanda drew my first orgasm from me, straining against the cuffs, panting, gasping and crying out as my body convulsed. I bucked and pushed against her mouth as my boss sucked on my clit, chewed on my pussy lips and drank the juices she was drawing from me as I came hard.

"Mmm, quite delicious!" my boss sighed happily as she sat up, wiping her lips clean as she watched me twitching in the aftershocks of my climax. She grabbed her camera and took a few more pictures of my red and drooling pussy before pulling a few more things from her bag – she had clearly prepared for this.

"Did I tell you how kinky I am?" she asked me as I watched her place those items out on the bed, "how I love playing with women's asses? I like opening them up and sticking things inside, things like this." She picked up and showed me a string of big anal beads, a long thick glass dildo that looked a bit like a corkscrew, a strap-on cock that was long and thick; I wasn't going to be able to sit down for a week!

But to start with she didn't need any toys; she had a tongue and her fingers, which she started to use on me. Her tongue was hard but velvet soft as she licked and lapped at my puckered ass hole, generating those amazing feelings you can only get from having a wet tongue in your bum. Her tongue was soon joined by her fingers, her saliva being added in copious amounts to lubricate the way, my drooling pussy juices being used as well.

"Yes, your ass needs something bigger," Amanda said as she straightened up and looked at her little collection of toys, "yes, they'll do nicely."

I watched, helplessly of course, as my boss picked the beads and a bottle of lube, and I watched her carefully and thoroughly coat each ball. They were about the size of a golf ball and there were five of them on the string, and I was wondering how my poor little ass was going to cope with them – I soon found out.

"Now then, let's get started shall we?" Amanda asked me rhetorically after she had greased my ass with the lube, two slick fingers opening me up "I think you're going to enjoy this Pam."

I tried not to tense as she pressed the first ball up against my ass hole, and I groaned as I felt my body resist, but Amanda was relentless and my anus stretched and the first ball popped into my backside. It had made my sphincter sting and I gave a sigh of relief when the pressure released, but I saw Amanda's evil grin – one down, four more to go!

One soon became two and I was starting to feel a bit full inside as the third quickly followed. Amanda wiped her hands clean and picked up her camera again, snapping me with two fifths of the beads hanging out of my ass.

"Please, no more," I whined as Amanda put down the camera and pressed the fourth ball to my ass, "I feel so full!"

"Nonsense my dear," she smiled at me as ball number four was pushed firmly into my butt, "eventually I will have trained your backside so that it can happily take my fist! No, don't worry, I won't be trying that tonight, but one day you will feel my fist in your behind."

I let out a deep and heartfelt groan as I thought about that, the notion that Amanda wanted to push her fist up inside my bottom. Dear God, was that even possible? Would my tender little bumhole open up enough to take her whole hand? Thinking about that had distracted me to a certain degree from what Amanda was actually doing to my bottom, and I heard her purr with contentment as the fifth and final ball was pushed into me.

"Well done Pam, you've taken them all!" she beamed at me, taking photos of the cord hanging out of my backside, "How does it feel in there – full?"

"Yeah, feels odd, like I really need to go," I muttered, feeling uncomfortable.

"Well, they do need to come out again," she smiled at me, taking hold of the loop on the end of the cord, "don't worry, I'll do it really slowly."

It dawned on me that I now had to feel those balls stretch my ass again as Amanda pulled them out, and I groaned as she did indeed pull the first one out slowly, clearly enjoying the view of my anus being dilated by it and the pain/pleasure I was experiencing.

"Mmm, you're starting to enjoy this aren't you Pam?" My boss smiled up at me as she eased the next one out, holding it just at the point of maximum dilation of my ass hole to take some snaps, "you're not fighting it, and your pussy is dripping wet!"

I didn't say anything, not wanting to give her the satisfaction, but she was right – what she was doing to my ass was generating conflicting feelings of pain and pleasure. It stung to have my anus stretched wide open like that, but at the same time I liked the feeling of everything moving through me, through my back passage and through my sphincter. Even the feeling of being stretched open was starting to feel good, even if it did hurt a bit, and not being able to touch myself, to rub my throbbing clit, was only making those feelings more intense.

"Yeah, you're digging this aren't you?" she leered at me, "go on and push the next one out."

With her gently pulling on the cord I urged the next one out, feeling my ass resist before slowly opening up, and I gasped at the ball popped out of me, making Amanda moan with delight. Twice more she made me do this, twice more my ass was dilated as I 'pooped' out another ball, and suddenly my backside felt empty and my ass felt loose.