Introduction:
I had just taken a new job at a mid-sized company, and my initial reaction was that the team I was working with were a fun bunch of people who were very diligent about doing their jobs, but also treated each other in a friendly way. There were six people in our team headed up by Maxine, a tall (5’10”) attractive blonde who was probably in her late 20s, at first I wasn’t sure how things would work out given she was more than 10 years younger than me, but it became obvious that she was both very smart and treated everyone on the team as peers, in fact there were times where I wondered if she was too accommodating given she was the boss. Overall, my new work environment was the best I had ever worked in and I would go home at night thinking what a great decision it had been to move to the company.
About a month into my new job we were working on a large presentation which Maxine was going to deliver to a new client on the following Monday. I was working hard on the Thursday afternoon to wrap it up so that we could have a final group discussion on the Friday when Maxine walked by my desk and asked how close I was to being complete, because she had an offsite meeting with a different client at 5pm. I told her that it was going to be at several more hours, but I should be done by 7pm.
“Good work” she replied, “Unfortunately my home printer is screwed, so can I get you to bring me a copy at my apartment?”
“Sure, no problem” I said “I’ll drop it by at 7:30, unless it takes longer to finish, then I’ll text you to let you know”
With that she gave me her address and left the office for her other meeting.
I made good time on the rest of the project and was soon in a cab heading to her place. As we drove I was thinking to myself how committed she was – we had a full day to work up additional changes to the presentation, but she still wanted to give it a preliminary review tonight. “I guess that’s how she managed to get to be a boss at such a young age” I thought to myself.
The streets were surprisingly busy, but since I finished my work faster than anticipated I was right on time as I rang her buzzer.
“Hello” the voice at the other end crackled
“Hi Maxine, it’s Mike, I have your copy of the presentation” I replied
“OK, come on in” followed by the door buzzing unlocked
I proudly walked up the steps thinking to myself what a great job I had done not only on the presentation, but also on going out of my way to deliver it. This will help strengthen her impression of me. I knocked on the door, and after a couple of moments it was opened and I saw a stern looking Maxine, dressed as she had been at work all day, looking back at me.
“Here is the…” I said half stepping into her doorway, before being cut off
“This is very disappointing” she said tersely, snatching the envelope out of my hand
I was completely stunned and stammered some jibberish as I tried to understand what I had done wrong.
“Come in here and we’ll have to sort this out” she blurted at me, maintaining the unfriendly expression that I hadn’t seen on her face since I took the job.
“I’m sorry, I don’t understand what I’ve done wrong” I said sheepishly stepping into her apartment and hearing the door click shut behind me.
“You said you’d be here at 7:30, or you’d text to advise me otherwise” was the snapped response, “what time is it now?”
I fumbled to check the time and replied “7:32”.
“Exactly. Now I realize that you’re new on the team, but I don’t tolerate team members failing to deliver on their promises. Come into this other room and we’ll have to figure out what your punishment will be”.
I followed her into the other room too stunned to have an immediate reaction, but feeling my anger building after I had stayed late and gone out of my way to deliver the presentation. Before I could say anything she turned and disappeared out of the room throwing a comment “Wait here, I will be back in a couple of minutes to deal with this matter”.
The silence of the room left me to think more about a response to Maxine’s excessive reaction, and I started to formulate what I was going to say to challenge her over what was basically a negligible time difference. The wait was at most a couple of minutes, but by the time I heard the door start to open I was ready to verbally assault her over her unreasonableness.
First I heard the click of high heels on the floor, followed by the sight of her wearing a tight black short skirted PVC outfit combined with exceedingly high heeled boots, a paddle dangling from her hand. The contours of her body were perfectly silhouetted by the outfit, and while she was not a large breasted woman, her outfit had pressed her breasts upwards so that she had a tantalizing glimpse of cleavage on display.
She slowly, walked across the room to me in steps which left the click of her heels echoing in my brain. She stopped inches in front of my face, and by virtue of her high heels she was staring down at me, leaving me intimidated by the combination of her attire, her height superiority and the completely different persona from anything I had encountered from her in the previous month.
All of the thoughts I had about what to say were lost, I was confused, silent and powerless to react. She looked down upon me for several seconds seeming to relish the control she had of the situation, and then spoke in a soft measured tone.
“I know that you are new with the company, but we still all need to know the rules. I have to give you 6 stokes of the paddle so that you understand for the future.”
Mentally disoriented, I found myself incapable of doing anything other than turning and bending over to receive my punishment.
“No, no, no” she tsked “your trousers have done nothing wrong – you are the one who needs disciplining. Take off all your clothes immediately.” She said in a still soft tone, but with an obvious stress on “immediately”
Completely lost in the situation, I unconsciously started to disrobe down to my boxer shorts at which time I looked to see her eyes in a silent but determined stare drilling through mine, no reaction was required for me to know that she was waiting for my absolute compliance. I dropped my boxers to the floor and then bent over to receive my paddling to supplement the humiliation of my complete submission to my boss.
My hope that this would be over quickly was mistaken as she walked a very slow, methodical circle around me as though I was her prey. Again each heel strike on the floor seemed to send electric shocks through my brain interrupting my racing thoughts over how I got into this predicament, what I was going to do to get out of it, and an additional mass of jumbled incoherent synapse firing. After what seemed an eternity she stopped on my left side, then I felt her gently make a cross on my left buttock with a finger nail, followed by her softly uttering “one”, then the paddle connected with my left buttock creating a solid smacking sound and a warmth which seemed to spread towards my head after a couple of seconds, refocussing my attention on my plight.
As the radiating warmth died down, I quickly realized that the paddle stroke had actually been far more gentle than I had feared. My mind raced trying to analyze this fact and what message it delivered. In my mental distraction I blocked out the continued footsteps as she circled to my right side, crossed my right buttock, notified “two” then brought the paddle down onto my right buttock with similar strength to the first stroke.
More circling, finger-nail crosses, a “three” and a “four” and the warmth in my buttocks was supplemented by a further pair of blows which seemed slightly more gentle than the first pair. Just as my mind was beginning to gain comfort and balance with the rhythm of the situation, Maxine then destroyed the cadence with a longer delay, no walking and dead silence. After what seemed endless, but was probably only 15 seconds, she issued a “five” and as I started to contemplate the fact she had marked no target buttock, the paddle connected across both cheeks, slightly more gently than the second pair of strokes. This blow scarcely registered to me and it immediately solidified my opinion that she had realized that she had accomplished her goal and she was simply going through the motions before allowing me to leave in humiliation.
Knowing I was all but finished, one gentle paddle stroke to be delivered, I started thinking about collecting my clothes, dressing and fleeing as quickly as my legs would take me. I would regain my composure at home {“six” echoed somewhere beyond my attention} and figure out what to do about this whole situation and…..
“WHACK” the paddle connected one final time with a decidedly ungentle blow that immediately and for the seemingly umpteenth time since I entered Maxine’s apartment told me I was out of my depth in whatever was occurring. Only later that night, in retrospect, did I conclude that the blow probably wasn’t much harder than the first pair, but it might as well have been delivered by a fully running swing of the paddle based on my inappropriately established expectation. I sucked in deeply, letting out a slight gasp and was distracted from my thought process around escaping Maxine’s lair.
I stood up, feeling like a somewhat punch-drunk fighter trying to get his bearings, and staggered towards my pile of discarded clothes. I knelt down on one knee to gather them, only for Maxine to kneel behind me looping one arm around my body, under one arm, and up across my neck and pulling my body tight to hers, her cool PVC outfit pressing against my back as she moved her mouth to my ear and whispered “you’re not done yet” as her other hand reached around me, cupped my testicles in her hands briefly, then slid along the length of my throbbing penis.
That was the first time I realized how aroused the paddling had made me. The collective impact of the constraint of her arm across my chest and neck, her hand around my cock, the sensation of cool PVC insistently pressing against my back contrasting with her hot breath caressing the side of my face started to snap me out of my stunned stupor.
Her hand lingered on my rod, sliding once ever so delicately from base to head and back down, her tongue flicking delicately at my earlobe. While I now realized that she had vastly expanded her concern from her initial “punishment” I had no idea whether I had any part in the decision of how this was to progress, and whether I would simply be meat put through the tenderizer for her satisfaction. The one thing I was sure of was that I now was comfortable with whatever way she wished for this to evolve – she had me completely under her control, though for the first time that night I had escaped my total sense of confusion at the proceedings.
In a soft almost sweet voice she murmured “I’m sorry for having to punish you, but it’s my responsibility as a boss to ensure that the team understands how the rules work”, before adding with a slightly more devilish tone “besides, it seems like you enjoyed your punishment” coupling the second statement with a steady squeeze of my throbbing member.
I barely whispered a “Yes Ma’am” as I closed my eyes and inhaled a deep breath of her erotic scent.
She rose up, never removing either her arm or her hands from where they were placed, somewhat dragging me to a standing position, my eyes still closed as I luxuriated in the awareness of the situation.
She released her physical grip on me then led me by the hand to a bed and had me lie on my back. She quickly straddled my chest and pinned my wrists to the bed each side of my head, then leant forward pushing her constrained cleavage into my face, permitting me to greedily bury my face in the valley of her breasts. She had allowed me my first dose of control for only a couple of seconds when she shifted to my left, reached for something unseen and in no time at all had my left wrist bound in a leather cuff which was strapped to the bed. Moments later she had rocked back to my right and repeated the task with my other wrist, leaving me to ponder how fleeting my episode of control had been. She returned to her perch on my chest, sliding down to bring her face in line with mine, her blue eyes glimmering as she stared into my eyes.
Again, ever so softly she spoke “It’s very important to me that the team performs at its best, but while discipline is an important part of that – as you now understand – so is having a good team rapport. Part of that is to make sure that we on the team have fun together…..you have been very understanding of the need for discipline, do you think that you can demonstrate to me that you are also good at having fun?”
Bound or not, submitted or not, I knew I had no place I wanted to be at this time other than where I was, and I replied less meekly than before “I am definitely interested in having fun, and I want to prove to you that you can count on me to be good as part of a team”.
She brought her mouth to my ear and said “Good, I like team players, and think of myself as a good team player too….but at this instant you need to understand that you’re on MY team” as she finished she brought her face back in front of mine and ever so gently nibbled on my lower lip, then replacing her teeth with her red painted lips and suckling on my lip until she snaked her tongue into my eager mouth.
Our tongues danced and wrestled in my mouth before I pushed past her lips to reciprocate and taste her inner cheeks. Eventually she pulled her mouth away and rotated her body, reaching for my right ankle, strapping that to the bed, followed by the left – now I was spread-eagled in my awareness of being on HER team.
As she was binding me into place I had raised my head up and was watching her shaved pussy as the bottom of her skirt rode up while she strapped down my ankles. Then, once I was fully secured in place, she started to back up towards my head, uttering only the single word “Lick”. Once her shaven lips were within reach of my tongue I quickly obeyed, starting with long greedy passes of my tongue up alternating sides of her pussy, then riding deeper in the ridge between them, investigating the inner warmth and revelling as my taste-buds cherished her musky flavour. She hesitated there for a while, then slowly and rhythmically began grinding back into my tongue, allowing enough time in her motion for me to carefully flick at her hard clit with my straining tongue, feeling a very slight shudder in her thighs as each such flick sent shots of pleasure coursing through her body.
“Good boy” she said, purring as I continued bathing her moistening crotch “you do seem like a good team player, and I definitely like having you on my team. I don’t want you to think that I’m not a contributor just because it’s my team though.” With that I felt her warm saliva on the end of my now raging hard-on, followed by pressure as she closed her mouth around my purple head and began to slide her mouth up and down steadily sliding a little deeper each time, her tongue twisting like a snake as she lowered her face.
I let out a gasp breaking my tongue’s contact with her raging warmth, the cooler air refreshing my mouth. As I started towards her pussy again she rapidly flicked her tongue around the underside of the head of my cock causing me to flinch and suck my teeth in arousal. With that she rotated her body off of mine stealing away my mouth watering delight, and slipped my desperate cock out of her mouth and muttered
“Clearly something’s distracting you from my pussy – I guess if you won’t put your tongue to use on me I at least should make sure you don’t distract me from what I’m doing” and with a wicked grin she reached under the bed and pulled out a ball-gag, slid it into my frantic mouth and deftly buckled it into place, halting my ability to both interfere with her dining, but also blocking my as yet unsatiated tongue from the meal of my choice.
She stood beside the bed, then raised one boot to the bed to remove it, seemingly ensuring that I had a perfect view of her crotch as she did so. I had seen her legs before in the office, but only covered in stockings, so seeing the silky bare immaculate skin provided another to the overflowing reasons to be stimulated. Her flexed calf muscles and slender but firm thighs quickly reminded me how I couldn’t currently enjoy the possibility of having my face grasped between those sensual thighs, her calves straining against my back to ensure my face was sufficiently buried in her womanhood.
She delighted in carefully repeating the process with the other boot, watching me work against my bonds to no avail.
“All in good time my little team player” she snickered wrestling herself free from her PVC outfit, finally showing her full nakedness seemingly eons after she had forced mine. Much like her legs, she had a taut stomach and her arms showed that she worked out enough to be fit and strong, but not so much as to be overly muscled, and her breasts while loosed from the support giving outfit still remained firm and delectable, though the warmth of her outfit and our shared activities left her nipples needing some attention to make them as pert as I bet they could be – the mere thought of that sent a pulse through my groin, now becoming impatient at being ignored. She stood briefly, allowing my eyes to feast on her naked form before reaching down under the bed again, and resuming her perch over my member without me seeing what she had reached for.
Again she lowered her bright red lips down my shaft and again it sent shudders through me, only now I could only grunt around the gag filling my mouth. She looked up at me, teasing my cockhead with her tongue and smiled as I twitched – I was left hoping she wouldn’t leave me hanging at this state for too long as my testicles felt like beachballs waiting to unload themselves of the excessive tension.
She pulled back her head, then I saw what she had grabbed from the floor, as she slipped on a white latex glove, swiftly dripped some KY on two fingers, and moved them to my unprotected ass crack, and gently worked one, then the second finger up into my back passage. She delicately manipulated them around for a short time, then lowered her head back to my straining rod, using her other hand to hold it still from all the exhilaration driven throbbing. With expert skill she massaged my cockhead with her tongue and my prostate with her fingers. This time she didn’t hesitate with any stopping and starting, building to a frenzy of lips, tongue and fingers leaving me no ability to do anything other than rapidly rise to the most powerful climax I have ever experienced spurting endless streams of cum into her diligent mouth, my body shaking and bouncing around as much as my constraints allowed, all the time being ridden by Maxine’s mouth like a rodeo cowboy.
As I slowly calmed back down, not helped by with occasional impish brush of her tongue around my cock, or extra little tweak of my prostate, I was able to relax and let some of the strain out of my now aching arms. She stood, removed the glove, cleaned up my softening member then removed the ball-gag from my mouth, allowing me to work my jaw around to release some of the built up tension.
“That was wonderful” she said with a broad grin “you have been a very good boy on MY team, now let’s see what you’re like on your own terms.” With that she started to unstrap my ankles, followed by my wrists until I was finally as free as she was.
“I must admit that I’m not very patient though, so don’t expect any rest time just because of what you just did” she continued in a selfish purr.
I didn’t care in the slightest, I may have been shattered by the power of that orgasm, but I reached around her waist, gently rolled her over so she was on her back, allowing me to see her fully naked beauty again. I sat across her stomach using the strength of my legs to take some of the weight off of her, then palm to palm I laced my fingers with hers, then turned my hands up so that each of our palms was fully exposed. Slowly but methodically I put my mouth to the inside of her right wrist and began nibbling, licking and kissing up towards her body, occasionally stopping and simply swirling circles with my tongue on her soft inner arm skin. As I got to her bicep I stopped, raised her hands above her head, and lowered my face to hers, first kissing her lower lip, then shifting back to repeat our tongue dance from earlier, lingering as we smeared our faces together as if forcing our faces to merge. After a period of kissing I lowered her arms back to her sides and started working from her left wrist back up to her bicep. Once there I slowly shifted across to the centre of her chest, moistening in expanding circles across the edges of her breasts moving out until the circles resulted in my tongue running across each now hardening nipple in turn. After ensuring each nipple had hardened into bumpy lumps I took care to vary between each nipple keeping both rock hard as I tweaked and drooled over Maxine’s buds. As I was doing this she was gradually wrapping her legs around my thigh and grinding her now sopping pussy against my leg. Breaking free from her snarling legs I gradually kissed and licked my way down her flat stomach working towards her steaming crotch. No sooner was my face at her groin than she wrapped a leg around the back of my neck and slipped her hands into my hair, clutching at follicles and urgently wrenching my face into place to pleasure her. Finally getting my chance at control, I broke her hands free, swiftly rolled her onto her stomach, clasped her wrists behind her back and managed to manipulate my hands to have my left hand controlling both of her wrists.
As she let out a pleading moan the trouble maker in me wanted to slap the ball gag in her mouth, but I was too busy getting my value elsewhere to worry about that battle just yet. I adjusted my body to be able to reach under her waist, raising her up, and slid two pillows under her hips, still maintaining my control of her wrists. This task complete, I set back to work, methodically licking from her clit all the along her lips, and back up the crack of her ass, flicking at her puckered asshole on the way.
Minute after minute of this delighted my sense of taste and smell, and the quaking of Maxine’s thighs, and her increased moaning left me clear that she too was cherishing this oral barrage. Finally I kept my focus on her protruding clit, licking, sucking, nibbling, flicking until in a spasm of epic proportions she cried out in ecstasy as her whole body shuddered to a raging orgasm as her legs started to give way limiting my access to her clit – releasing her hands I quickly lifted up her hips and slipped my face underneath her wrapping my arms round her thighs to allow her no escape from my continued tonguing. The noise of her moaning and bucking as I tended her highly sensitive parts must have been heard around the neighbourhood, and only after a little more fun did I relinquish control and allow her to collapse onto the bed, her face partially covered by her rustled hair, and her ribcage heaving from exhaustion.
After a couple of minutes of deep breathing and recovery she admitted
“Wow, you are a good player! Those are the sort of skills I’ve been looking for on my team!”
We weren’t done yet, sharing lots more positions and entertainment as we went well into the night, finishing with me pounding Maxine doggy-style as the bed screamed as though it was being destroyed. Even at the end of such a long session I came hard making me feel like I was still in my twenties – Maxine’s sexiness definitely had brought out the best in me. By the time I left, I struggled to find the energy to get home. All the way there I kept thinking to myself that in the future at work I’d be quick to volunteer, but doubted I’d ever deliver anything to Maxine on time!

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