Hi - I'm Shawn. I'm in my early 40s, happily married with two kids. I'm in good shape for my age and professionally successful as an account executive at a mid-size manufacturing supply firm. Up until very recently I was living a somewhat boring, if traditionally successful, American suburban life. This story is about me ... and my boss.
Stephanie (who goes by Steph) is the youngest Vice President in our company at 24, and she leads our team. I'm quite confident that, if she weren't interested in business, she'd be making significant money as an Instagram model. She is a smokeshow. Wavy, mid-length brown hair, smooth tan skin, large brown eyes with a hint of an exotic look and a gorgeous face made for an ad in an upscale magazine. Although I've never seen her in a bikini, everyone can tell that her body is on another level. She stands at around 5'7" with perky natural C-cup breasts, a tight toned tummy, an incredibly plump and firm ass and long smooth legs. I have to admit that her physical appearance alone is intimidating, but she's also quite smart and didn't just get to her position in the company based on her looks (although I'm sure that didn't hurt).
The way Steph dresses can be distracting. It’s about as sexy as it could get, whilst remaining within standard professional boundaries. She has 3-inch high heels of all colors, which she frequently matches to her outfit. Most days she wears a tight skirt that ends just above the knees. Sometimes she’ll spice things up with silk stockings of various colors. Occasionally on a "casual" day she'll wear tight jeans that accentuate her shapely rear. On top - it’s a mix of tight blouses or button down shirts that do not hide her large boobs. In the summer, she'll sometimes go with a sundress - even her shoulders are somehow hot! The guys in the office try not to stare and, mostly, succeed. But occasionally some hapless intern or newbie gets caught with his mouth agape. I have also heard that she works out at the on-site gym early on Tuesday and Thursday mornings, resulting in the gym being quite crowded on those days from the men (and a few women) trying to get a look at her in yoga pants and tight belly shirt. She typically wears her hair up - which I like - but mixes it up from time to time with rarely a hair out of place.
The other distracting (and weird) thing about Steph is that I’d started to get the feeling she was flirting or, more likely, teasing me. Not to sound arrogant, but I'm the best looking man on our team of 10, even though I'm almost 20 years Steph's senior. I'm a pretty good performer ... third on the team in sales ... which I'm sure she has some respect for.
Now, Steph's never said anything flat out inappropriate, but it was impossible not to notice the odd behavior. Like when she came to my office and put her notebook down on the table behind me. She accidentally knocked it on the floor and bent way over right in front of me to pick it up, her skirt riding up her thigh more than usual and her great butt stretching the fabric of her skirt. Or when I went to her office for a 1-on-1 meeting and she pulled her chair directly in front of me, crossed her long legs with her skirt (again) riding up and repeatedly rubbed her tan toned thigh right in front of me. Then just last week she leaned over in front of me to point to some numbers in a sales report with the top two buttons of her shirt undone, which made for some fantastic cleavage!
The last straw came as Steph left the office on Friday. After catching me out of the corner of her eye, she sauntered over and said that she had a "really fun weekend" in store in a sultry voice. I asked what she meant and she smiled, giggled and stretched her arms in the air. Her shirt came up to just below her belly button and a silky blue thong strap was poking out of her tight skirt around six inches from my hand. I left the office almost immediately after she did ... unable to concentrate. Later that night - I had relatively (for us) wild sex with my wife (who hasn't worn a thong since our second kid was born) while closing my eyes and picturing Steph stripping out of her skirt at the end of the day.
Things changed permanently this week. On Wednesday morning, Steph came into my office and leaned on my desk. My eyes trained straight ahead I said - in a friendly way, "What's up boss?" Steph replied, "I need to see you after work on Thursday. Let's make it 7 PM. We need to talk about your performance." I was baffled ... "My performance ... what do you mean?" Her response was a flat, "See you then..."
My wife would be annoyed at the prospect of my working late on short notice, but that was the least of my worries. I reviewed my sales data and pipeline again to make sure that I wasn't slacking. Nope, nothing has changed in terms of productivity. My wife didn't work and I needed my job, so you can imagine how on edge I was! I could barely sleep Wednesday night and, on Thursday, the hours of the day ticked by as slowly as possible.
When 7 PM finally rolled around, the office was deserted except for Steph and me. I knew the night janitor showed up around 7:30. I began to wonder if she wanted to be alone. I showed up at the door of her office and she cheerfully said, "Let's head over to the conference room." Since there was nobody around to judge, I could stare at her luscious butt as we walked to the conference room. I could tell through her tight dark green skirt what a work of art it was. Round, firm and - I was sure - smooth and blemishless like the rest of her body. She wore green thigh-high stockings, yellow heels and a tight yellow skirt. Typical Steph outfit.
She sat down at the conference table and, when I began to sit, asked me to remain standing.
"Shawn - we need to talk..." she began.
"Ok," I replied in as calm a tone as possible.
"You've been with the company for over ten years. And, yet, your career has stalled. I've been here two years and I'm already your boss! Your productivity numbers, while solid, should be much better for someone as talented as you are. I think one of two things is going on, and we're going to take care of both tonight. Either you aren't as dedicated as you should be ... or something is distracting you."
There it was - the sultry voice when she said "distracting you". As she said it, she took her hair tie out and shook her head slowly as her wavy hair fell to her shoulders. I felt myself began to harden beneath my slacks, but I knew she wouldn't be able to tell. But nothing could prepare me for what came next.
"I need you to prove your dedication to this company. Start by taking off your shirt."
I was flabbergasted but tried to laugh it off. "Haha, very funny. Look the kids have been a lot of work late-"
Steph cut me off. "I'm not kidding," she said. I want to see your shirt off. Undershirt too.
"You can't do that!" I responded, "That's not professional and you know it."
"Who cares?" she replied, leaning back with a smug look on her beautiful face. "I'm your boss. There's nobody else here who can see what's going on. If you try to tell this story to HR, there's no way they'll believe you. It's much more likely that someone like you would be harassing someone like me. I see the way you look at me ... as I said ... distracted! So do what I tell you or you're fired."
I couldn't believe what I was hearing. Did I have a choice? Was I really going to do this? I needed the job so, almost against my better judgment, I began quietly to unbutton my shirt. Nobody would mistake me for a body-bulider but, like I said, I was in pretty good shape for a man my age. I folded my shirt neatly on the table in front of me, not wanting it to be disheveled when my wife got home.
"Very nice," Steph purred. "Now the pants."
"What?!" I almost shouted. The look in her eye made it clear that Steph wasn't kidding. I needed my job. She was right, absolutely nobody else in the company would believe this story if I told them. And ... did a part of me secretly enjoy what was happening? My dick started to get noticeably hard and she'd definitely be able to see my erection through my boxers at this point. But what choice did I have?
Slowly I took off my shoes and pants, folding them on the table in front of me. "Steph, this is humiliating. I'm dedicated to you and the company. I'm one of the best performers on the team, there is no reason to get rid of me."
"Yes, Shawn. You're one of the best. I want you to be the best," Steph said as she stood up. "And I'm going to motivate you ... and hopefully get rid of these pesky distractions." As she said "distractions" she grabbed her boobs through her shirt and patted her ass. Was this really happening?!
It seemed impossible, but in the back of my head I knew what was coming.
"Now the boxers," Steph demanded.
"Please - I'm married. This is embarrassing enough. I really don't wa-"
She cut me off. "Listen, I'm the boss. Take em off. And for that back talk, you're going to get a spanking!"
Was she for real? A spanking? In the office? From my sexy 24-year-old boss? I couldn't imagine anything more humiliating or arousing. Little did I know what was coming.
As with Steph’s other commands, I complied. I removed the last shred of modesty I had and stood in front of this bronze goddess naked. I was fully erect, by now, which did not go unnoticed. "Looks like you're enjoying this motivational session! Now, come over here, put your hands on the table and bend over."
Unbelievable, I was really going to get spanked. I slowly walked around the conference table to where she was standing, as she eyed my nude body up and down. I turned around and put my hands flat on the table in front of me. I barely had time to brace myself when the first slap came, hard against my left butt cheek. "Ow!"
Just like that - Steph was actually spanking me. "Ow! Ouch! That hurts ... come on stop!" I cried out. After thirty seconds, I had gotten ten stinging slaps on each side and my ass was as red as a tomato.
"Ok, Ok ... you've proved your point," I whined as I stood up. "Ouch!" Steph slapped me again and ordered "Hands on the table, Shawn! Eyes straight ahead."
I didn't dare disobey. After thirty more seconds of silent anticipation I heard, "Now turn around."
I stood up and slowly turned around, buns on fire, dick pointing straight up. She had taken her shirt and skirt off and was even hotter than in my imagination. Tan everywhere, with a bright yellow bra two sizes too small barely containing her tits. A tight, flat tummy with not an ounce of fat and a cute belly button ring. She was facing me, but I could see her butt from the side. It looked unreal in her yellow g-string. Color coordinated, the outfit was complimented with her yellow thigh-high stockings and 3-inch heels.
I couldn't move. I couldn't speak. I just stared dumbly at this powerful, confident, hot-as-fuck young lady who seemed intent on turning me into her personal pet. And it was about to get worse.
"Now that you've made up for your back talk, we're going to get down to business. I'm going to make you prove you are dedicated to this company and to me. Now lie down on the table."
I wanted to object. I wanted to stand up for myself. I wanted to regain some dignity. Instead, I found myself saying softly, "Yes ma'am." I lied down on the cold long table with my hands at my sides.
"Shawn, I have a question," Steph said seductively. "Are you ticklish?"
At hearing the t-word, I sat straight up. I was, indeed, very ticklish. Although nobody had tickled me since grad school, when a girlfriend of mine almost accidentally discovered it was a major weakness. We were horsing around one night and she gave my sides a quick goosing. I immediately recoiled and started chuckling. She pressed her luck and discovered - much to her delight - that although I was naturally bigger and stronger than she was, I was ticklish enough to even things out when we were wrestling. She even tickled me once or twice during sex. Unfortunately, she wasn't at all ticklish, so I couldn't fight back. But I did learn something about myself ... that I couldn't stand tickling.
"Lie down!" Steph ordered.
As I slowly lowered myself back to the table, I started blabbering. "Yes ... yes I'm really ticklish. Please ma'am. Don't tickle me! I'll do whatever you want. You can spank me. I'll clean your shoes. I'll improve my productivity. I'll wash your car. I'm really can't stand being tickled.." For some reason, the more I talked about my ticklishness, the hornier I got. Even though I couldn't stand it.
"I have a confession of my own," Steph replied. "You hate tickling. I love it. I had two older sisters when I was a little girl who tickled me relentlessly. The experience honestly made me who I am today. Ever since my 18th birthday, I've resolved to be the one in charge, the one doing the tickling. It's one of the many things that intimidates boyfriends." Then, with a nod and a wink towards me, she added, "And others..."
"In fact, I used restraints with my last boyfriend," she continued as I got increasingly nervous. "I told him that I wanted to experiment with bondage and let him have a safeword, which I promptly ignored when he tried to use it. I kept him tied up for two hours. I tickled him for thirty minutes and then went to take a shower and watch some TV. I loved listening to him beg to be let out. After ninety minutes in bondage, I went back and tickled him for thirty more minutes. He actually ended up peeing himself!. It was hilarious. He was super mad when I finally let him out, but I didn't care. I dumped his ass ... can't respect a man who wets himself. Getting a new boyfriend isn't a problem for me, obviously!" she said with a careless giggle.
This was a whole new side to my boss. I kept my mouth shut and resolved to do whatever I needed to get through this situation and then regroup. Thank god the janitor was showing up in 20 minutes. 20 minutes could be a looong time, though.
"So," continued Steph. "Spread you legs. Spread your toes. Put your arms in the air and keep them there!"
I did as I was told and closed my eyes, bracing for the worst. It was bad. She started with the bottom of my feet and scribbled her nails up and down. She started with my right foot and then my left foot and then both at the same time. She tickled my toes, my heels, in between my toes (my worst spots). Hell, even the tops of my feet were somehow super ticklish.
"Ohhhhhhmygod ... that tickles so much! Hehehahahahaa!"
"Pleaase Steph ... a break! I need a break! hahahahohoho ... no not there, not again!"
As she started, I pulled my feet back multiple times, getting reproached by Steph repeatedly.
"Now now now ... keep your toes spread for momma. That's a good boy!" she cooed and laughed, intent on humiliating me.
"Shawn the big strong man - you aren't so tough hehe!"
"Keep your leg straight! I'm not going to tell you again. If you can't do it, I'll have to get some rope and do it for you! Hell maybe I'll leave you here for the janitor to find!"
I begged, I pleaded, I bellowed and laughed until I cried. After she was done with my feet she methodically moved up my body. Playing itsy-bitsy spider with her fingers and she got closer to my balls and cock as I involuntarily rubbed my sore butt up and down on the cold conference room table. I was so erect that it hurt. The perverted situation was really turning me on.
She took her time spidering my balls and tickling up and down my shaft with her finger tips. "Who's got a ticklish dick?? You do! I could play with this thing all night!" she taunted.
Opening my eyes I looked down through my tears. As torturous as the ticklish sensations were, my mind was still clear enough to register how hot this woman was. Her boobs were squished together in front of me as her eyes remained on my quivering shaft. Her tanned and round ass was up in the air, perfectly framed by the yellow g-string as she kneeled on either side of my legs. Was this a nightmare? Or a fantasy? Or both?
After ten minutes on my lower body, Steph sat up and straddled my midsection. She seductively took off her bra to reveal a perfect, perky, large set of tits with dark pointy nipples.
"Ooooh," she teased me. "I bet you want to touch these don't you. Sorry Shawn, but that's not allowed ... you're my employee after all ..." she said in a soft, almost breathless way. I could tell by her tone that she was getting turned on. It was a little less teasing and a little more seductive. "Maybe one day I'll let you touch my body ... but for now I want to you be still. Keep those arms up, champ, this is going to tickle sooo much!"
With that, Steph leaned in and put her tongue in my belly button and started swirling it around. She was careful to bring her boobs achingly close to my rock hard dick, coated in a layer of precum, but she did not let them touch me. As she did this, she started to lightly scribble her nails up my body towards my forearms.
With this lighter, teasing tickling, I didn't laugh quite as hard. But it still really tickled! "Hehehe ... oh man .... hehehehe you're good at that ma'am" I managed to say. I hoped that appealing to her ego would end my ordeal and maybe even get me a reward. Thoroughly dominated at this point, by the younger woman, I just wanted to be a good boy.
I'd soon get my chance. Abruptly, Steph stopped teasing. Sat up (with her butt on my lower abdomen) and started cruelly raking her fingernails up and down my upper arms and in my arm pits.
"Yeeeaaah!" I screamed. "Nononono! Please that's soooooo baahahahahahaaaad!"
Steph smiled maniacally as she rubbed herself on my torso, scribbling her nails up down and around.
I tried to be good, but I couldn't help bringing my arms down. "I'm sohorohohorry ... it just tickles so much!" I lamely exclaimed.
"Bad boy!" she yelled. With her left hand still trapped under my arm, wiggling around to great effect, she took her right hand, rolled me over with her legs and smacked my still sore left buttcheek three times. "Keep your arms up!"
I closed my eyes and did as I was told. How much longer could this go on? All in all, it was about ten more minutes of torso tickling, during which I occasionally couldn't help bringing my arms down, to get spanked as punishment each time.
Steph was getting more and more turned on by her dominance and my submission. At last, she couldn't take it any more. She leaned in and whispered in my ear, "Time for a reward," as she slipped her soaking wet g-string off (keeping her stockings and heels on). Could that mean what I thought it meant??
She lifted herself up and hovered over my shaft. With that, my hands instinctively gripped her hips. Her skin felt as good as it looked - soft, smooth and, now, slick with sweat.
"Now ... she said ... you need to be a really good boy. Show me how disciplined you can be. No cumming for five minutes! I'm going to ride you and get off as many times as I want. You have to hold it! If you can last five minutes, you'll have proven to me your dedication. If, however, you don't last ... you are going to come to my house next Thursday. And I'm going to tie you up and tickle torture you for as long as I want. One hour, two hours, hell maybe I'll even keep you all night. You'll have to make up some BS to tell your wife. So - if you know what's good for you - don't cum!"
As hot as I was, the way Steph said "torture" made my blood run cold. It's as if what she had done to me so far was just a walk in the park.
She slowly lowered herself onto me. Her slick, smooth (waxed) and wet pussy was as good as anything I could remember. My hands instinctively moved from her hips to the outsides of her thighs as she began to move back and forth. I almost lost it within ten seconds! I somehow remembered her threat and decided that I needed intense focus to last five minutes. I closed my eyes to avoid looking at her incredible body and took my hands off of her ... as hard as that choice was given how good she felt.
"Oooh," Steph moaned as she picked up some steam. "Smart ... you don't want to cum too quickly. Good boy!"
The demeaning taunts were impossible to ignore. I was struggling to hold it.
"Are you gonna lose it?" she whispered.
I knew there was only one thing that would distract me ... "tickle me," I said softly.
"What was that baby! I can't hear you!"
"Tickle me ... tickle me! Oh my god ma'am please tickle me!" I shouted. All of my sense of dignity was now gone.
"Smart boy," Steph replied and started wigging her fingertips up and down my sides and riding my dick rhythmically as I bucked and bellowed with laughter.
As it turns out - her tickling was just agonizing and distracting enough to keep me on the edge, close to cumming but not quite there. As long as I kept my eyes closed and my hands off her body, I should be able to make it.
Steph was having the time of her life. I could tell by how her body clenched up that she enjoyed two orgasms in rapid succession. Running her hands all over my body, exerting dominance, listening to my anguished laughter and pounding my rock hard cock was as good as it got for her. It's good to be the boss!
I had lost track of time when suddenly I realized the tickling had died down and she was, instead, rubbing my chest and building to another orgasm. Oh no ... this would be trouble. Then she whispered in my ear "Only 30 seconds left, Shawn. Then you're free."
She ground her hips three or four more times but I bit my lips and kept concentrating. I knew I could hold out. I was going to make it!
Then, she did something entirely unexpected. She grabbed my hands with hers. The she pushed them against her perfect, shapely ass, and squeezed. In my 40-odd-years on this earth, I'm not sure I ever felt so good. It felt better than it looked. Firm, tight, round, with soft slick skin. As close as I was ... two handfuls was all it took. My groin lifted clear off the table as I came as hard as I ever had. This prompted Steph to enjoy her third orgasm of our session. After I pumped out a few loads, she climbed off and sat back, breathing heavily.
"Well, will you look at that," Steph said after a minute of heavy breathing. She stood up and reached for her panties. "Four minutes and 55 seconds. Oh well! Guess I'll have to teach you a lesson next Thursday. You better start thinking of an excuse for your wife."
Through my tears and exhaustion I managed to moan, "That was a dirty trick ... it wasn't fair ... I took all the tickling, there was no way I could hold out after grabbing that ass."
Steph pulled on her thong. "Hey, it's not my fault I take care of my body. Look, if you last a few hours next week and don't pee yourself like my ex did, maybe I'll even let you give it a few smacks!" she said with a wink. To accentuate the point she smacked her own plump butt. It seductively vibrated for a second or two but didn't move given how rock hard it was. Incredible.
She put her bra on, picked up her shirt and skirt and strode out of the conference room without another word.
Wait a minute? Wasn't the janitor out there? I didn't have time to worry about that. My goal was to get dressed as quickly as possible and get to my car. Driving home, I'd clear my mind and come up with a strategy. What do I tell my wife? What do I do about my job? I can't possibly let this maniac tie me up and torture me, right? Then again ... is this something I secretly want? I hadn't been this confused in years.
As I staggered out of the conference room, I did indeed see the janitor emptying the trash can at a nearby cube. How long has he been there? Did he see anything or hear anything? He didn't give me a funny look, so I'm guessed I was ok ... Then I heard the ding of the elevator bell and looked up. Steph, now fully clothed, was waiting to head down to her car. She was about ten feet away from our janitor, who was now gazing aimlessly in her direction. She dropped her notepad and bent way over, with her butt in the air. Then, almost as if it were a practiced skill, she hiked he dress up to show the poor janitor the bottom of her butt cheek. In a split second, the straightened up, smoothed her skirt out, and without acknowledging either of us entered the elevator to head down to her car.
What had I gotten myself into?
To be continued...
Stephanie (who goes by Steph) is the youngest Vice President in our company at 24, and she leads our team. I'm quite confident that, if she weren't interested in business, she'd be making significant money as an Instagram model. She is a smokeshow. Wavy, mid-length brown hair, smooth tan skin, large brown eyes with a hint of an exotic look and a gorgeous face made for an ad in an upscale magazine. Although I've never seen her in a bikini, everyone can tell that her body is on another level. She stands at around 5'7" with perky natural C-cup breasts, a tight toned tummy, an incredibly plump and firm ass and long smooth legs. I have to admit that her physical appearance alone is intimidating, but she's also quite smart and didn't just get to her position in the company based on her looks (although I'm sure that didn't hurt).
The way Steph dresses can be distracting. It’s about as sexy as it could get, whilst remaining within standard professional boundaries. She has 3-inch high heels of all colors, which she frequently matches to her outfit. Most days she wears a tight skirt that ends just above the knees. Sometimes she’ll spice things up with silk stockings of various colors. Occasionally on a "casual" day she'll wear tight jeans that accentuate her shapely rear. On top - it’s a mix of tight blouses or button down shirts that do not hide her large boobs. In the summer, she'll sometimes go with a sundress - even her shoulders are somehow hot! The guys in the office try not to stare and, mostly, succeed. But occasionally some hapless intern or newbie gets caught with his mouth agape. I have also heard that she works out at the on-site gym early on Tuesday and Thursday mornings, resulting in the gym being quite crowded on those days from the men (and a few women) trying to get a look at her in yoga pants and tight belly shirt. She typically wears her hair up - which I like - but mixes it up from time to time with rarely a hair out of place.
The other distracting (and weird) thing about Steph is that I’d started to get the feeling she was flirting or, more likely, teasing me. Not to sound arrogant, but I'm the best looking man on our team of 10, even though I'm almost 20 years Steph's senior. I'm a pretty good performer ... third on the team in sales ... which I'm sure she has some respect for.
Now, Steph's never said anything flat out inappropriate, but it was impossible not to notice the odd behavior. Like when she came to my office and put her notebook down on the table behind me. She accidentally knocked it on the floor and bent way over right in front of me to pick it up, her skirt riding up her thigh more than usual and her great butt stretching the fabric of her skirt. Or when I went to her office for a 1-on-1 meeting and she pulled her chair directly in front of me, crossed her long legs with her skirt (again) riding up and repeatedly rubbed her tan toned thigh right in front of me. Then just last week she leaned over in front of me to point to some numbers in a sales report with the top two buttons of her shirt undone, which made for some fantastic cleavage!
The last straw came as Steph left the office on Friday. After catching me out of the corner of her eye, she sauntered over and said that she had a "really fun weekend" in store in a sultry voice. I asked what she meant and she smiled, giggled and stretched her arms in the air. Her shirt came up to just below her belly button and a silky blue thong strap was poking out of her tight skirt around six inches from my hand. I left the office almost immediately after she did ... unable to concentrate. Later that night - I had relatively (for us) wild sex with my wife (who hasn't worn a thong since our second kid was born) while closing my eyes and picturing Steph stripping out of her skirt at the end of the day.
Things changed permanently this week. On Wednesday morning, Steph came into my office and leaned on my desk. My eyes trained straight ahead I said - in a friendly way, "What's up boss?" Steph replied, "I need to see you after work on Thursday. Let's make it 7 PM. We need to talk about your performance." I was baffled ... "My performance ... what do you mean?" Her response was a flat, "See you then..."
My wife would be annoyed at the prospect of my working late on short notice, but that was the least of my worries. I reviewed my sales data and pipeline again to make sure that I wasn't slacking. Nope, nothing has changed in terms of productivity. My wife didn't work and I needed my job, so you can imagine how on edge I was! I could barely sleep Wednesday night and, on Thursday, the hours of the day ticked by as slowly as possible.
When 7 PM finally rolled around, the office was deserted except for Steph and me. I knew the night janitor showed up around 7:30. I began to wonder if she wanted to be alone. I showed up at the door of her office and she cheerfully said, "Let's head over to the conference room." Since there was nobody around to judge, I could stare at her luscious butt as we walked to the conference room. I could tell through her tight dark green skirt what a work of art it was. Round, firm and - I was sure - smooth and blemishless like the rest of her body. She wore green thigh-high stockings, yellow heels and a tight yellow skirt. Typical Steph outfit.
She sat down at the conference table and, when I began to sit, asked me to remain standing.
"Shawn - we need to talk..." she began.
"Ok," I replied in as calm a tone as possible.
"You've been with the company for over ten years. And, yet, your career has stalled. I've been here two years and I'm already your boss! Your productivity numbers, while solid, should be much better for someone as talented as you are. I think one of two things is going on, and we're going to take care of both tonight. Either you aren't as dedicated as you should be ... or something is distracting you."
There it was - the sultry voice when she said "distracting you". As she said it, she took her hair tie out and shook her head slowly as her wavy hair fell to her shoulders. I felt myself began to harden beneath my slacks, but I knew she wouldn't be able to tell. But nothing could prepare me for what came next.
"I need you to prove your dedication to this company. Start by taking off your shirt."
I was flabbergasted but tried to laugh it off. "Haha, very funny. Look the kids have been a lot of work late-"
Steph cut me off. "I'm not kidding," she said. I want to see your shirt off. Undershirt too.
"You can't do that!" I responded, "That's not professional and you know it."
"Who cares?" she replied, leaning back with a smug look on her beautiful face. "I'm your boss. There's nobody else here who can see what's going on. If you try to tell this story to HR, there's no way they'll believe you. It's much more likely that someone like you would be harassing someone like me. I see the way you look at me ... as I said ... distracted! So do what I tell you or you're fired."
I couldn't believe what I was hearing. Did I have a choice? Was I really going to do this? I needed the job so, almost against my better judgment, I began quietly to unbutton my shirt. Nobody would mistake me for a body-bulider but, like I said, I was in pretty good shape for a man my age. I folded my shirt neatly on the table in front of me, not wanting it to be disheveled when my wife got home.
"Very nice," Steph purred. "Now the pants."
"What?!" I almost shouted. The look in her eye made it clear that Steph wasn't kidding. I needed my job. She was right, absolutely nobody else in the company would believe this story if I told them. And ... did a part of me secretly enjoy what was happening? My dick started to get noticeably hard and she'd definitely be able to see my erection through my boxers at this point. But what choice did I have?
Slowly I took off my shoes and pants, folding them on the table in front of me. "Steph, this is humiliating. I'm dedicated to you and the company. I'm one of the best performers on the team, there is no reason to get rid of me."
"Yes, Shawn. You're one of the best. I want you to be the best," Steph said as she stood up. "And I'm going to motivate you ... and hopefully get rid of these pesky distractions." As she said "distractions" she grabbed her boobs through her shirt and patted her ass. Was this really happening?!
It seemed impossible, but in the back of my head I knew what was coming.
"Now the boxers," Steph demanded.
"Please - I'm married. This is embarrassing enough. I really don't wa-"
She cut me off. "Listen, I'm the boss. Take em off. And for that back talk, you're going to get a spanking!"
Was she for real? A spanking? In the office? From my sexy 24-year-old boss? I couldn't imagine anything more humiliating or arousing. Little did I know what was coming.
As with Steph’s other commands, I complied. I removed the last shred of modesty I had and stood in front of this bronze goddess naked. I was fully erect, by now, which did not go unnoticed. "Looks like you're enjoying this motivational session! Now, come over here, put your hands on the table and bend over."
Unbelievable, I was really going to get spanked. I slowly walked around the conference table to where she was standing, as she eyed my nude body up and down. I turned around and put my hands flat on the table in front of me. I barely had time to brace myself when the first slap came, hard against my left butt cheek. "Ow!"
Just like that - Steph was actually spanking me. "Ow! Ouch! That hurts ... come on stop!" I cried out. After thirty seconds, I had gotten ten stinging slaps on each side and my ass was as red as a tomato.
"Ok, Ok ... you've proved your point," I whined as I stood up. "Ouch!" Steph slapped me again and ordered "Hands on the table, Shawn! Eyes straight ahead."
I didn't dare disobey. After thirty more seconds of silent anticipation I heard, "Now turn around."
I stood up and slowly turned around, buns on fire, dick pointing straight up. She had taken her shirt and skirt off and was even hotter than in my imagination. Tan everywhere, with a bright yellow bra two sizes too small barely containing her tits. A tight, flat tummy with not an ounce of fat and a cute belly button ring. She was facing me, but I could see her butt from the side. It looked unreal in her yellow g-string. Color coordinated, the outfit was complimented with her yellow thigh-high stockings and 3-inch heels.
I couldn't move. I couldn't speak. I just stared dumbly at this powerful, confident, hot-as-fuck young lady who seemed intent on turning me into her personal pet. And it was about to get worse.
"Now that you've made up for your back talk, we're going to get down to business. I'm going to make you prove you are dedicated to this company and to me. Now lie down on the table."
I wanted to object. I wanted to stand up for myself. I wanted to regain some dignity. Instead, I found myself saying softly, "Yes ma'am." I lied down on the cold long table with my hands at my sides.
"Shawn, I have a question," Steph said seductively. "Are you ticklish?"
At hearing the t-word, I sat straight up. I was, indeed, very ticklish. Although nobody had tickled me since grad school, when a girlfriend of mine almost accidentally discovered it was a major weakness. We were horsing around one night and she gave my sides a quick goosing. I immediately recoiled and started chuckling. She pressed her luck and discovered - much to her delight - that although I was naturally bigger and stronger than she was, I was ticklish enough to even things out when we were wrestling. She even tickled me once or twice during sex. Unfortunately, she wasn't at all ticklish, so I couldn't fight back. But I did learn something about myself ... that I couldn't stand tickling.
"Lie down!" Steph ordered.
As I slowly lowered myself back to the table, I started blabbering. "Yes ... yes I'm really ticklish. Please ma'am. Don't tickle me! I'll do whatever you want. You can spank me. I'll clean your shoes. I'll improve my productivity. I'll wash your car. I'm really can't stand being tickled.." For some reason, the more I talked about my ticklishness, the hornier I got. Even though I couldn't stand it.
"I have a confession of my own," Steph replied. "You hate tickling. I love it. I had two older sisters when I was a little girl who tickled me relentlessly. The experience honestly made me who I am today. Ever since my 18th birthday, I've resolved to be the one in charge, the one doing the tickling. It's one of the many things that intimidates boyfriends." Then, with a nod and a wink towards me, she added, "And others..."
"In fact, I used restraints with my last boyfriend," she continued as I got increasingly nervous. "I told him that I wanted to experiment with bondage and let him have a safeword, which I promptly ignored when he tried to use it. I kept him tied up for two hours. I tickled him for thirty minutes and then went to take a shower and watch some TV. I loved listening to him beg to be let out. After ninety minutes in bondage, I went back and tickled him for thirty more minutes. He actually ended up peeing himself!. It was hilarious. He was super mad when I finally let him out, but I didn't care. I dumped his ass ... can't respect a man who wets himself. Getting a new boyfriend isn't a problem for me, obviously!" she said with a careless giggle.
This was a whole new side to my boss. I kept my mouth shut and resolved to do whatever I needed to get through this situation and then regroup. Thank god the janitor was showing up in 20 minutes. 20 minutes could be a looong time, though.
"So," continued Steph. "Spread you legs. Spread your toes. Put your arms in the air and keep them there!"
I did as I was told and closed my eyes, bracing for the worst. It was bad. She started with the bottom of my feet and scribbled her nails up and down. She started with my right foot and then my left foot and then both at the same time. She tickled my toes, my heels, in between my toes (my worst spots). Hell, even the tops of my feet were somehow super ticklish.
"Ohhhhhhmygod ... that tickles so much! Hehehahahahaa!"
"Pleaase Steph ... a break! I need a break! hahahahohoho ... no not there, not again!"
As she started, I pulled my feet back multiple times, getting reproached by Steph repeatedly.
"Now now now ... keep your toes spread for momma. That's a good boy!" she cooed and laughed, intent on humiliating me.
"Shawn the big strong man - you aren't so tough hehe!"
"Keep your leg straight! I'm not going to tell you again. If you can't do it, I'll have to get some rope and do it for you! Hell maybe I'll leave you here for the janitor to find!"
I begged, I pleaded, I bellowed and laughed until I cried. After she was done with my feet she methodically moved up my body. Playing itsy-bitsy spider with her fingers and she got closer to my balls and cock as I involuntarily rubbed my sore butt up and down on the cold conference room table. I was so erect that it hurt. The perverted situation was really turning me on.
She took her time spidering my balls and tickling up and down my shaft with her finger tips. "Who's got a ticklish dick?? You do! I could play with this thing all night!" she taunted.
Opening my eyes I looked down through my tears. As torturous as the ticklish sensations were, my mind was still clear enough to register how hot this woman was. Her boobs were squished together in front of me as her eyes remained on my quivering shaft. Her tanned and round ass was up in the air, perfectly framed by the yellow g-string as she kneeled on either side of my legs. Was this a nightmare? Or a fantasy? Or both?
After ten minutes on my lower body, Steph sat up and straddled my midsection. She seductively took off her bra to reveal a perfect, perky, large set of tits with dark pointy nipples.
"Ooooh," she teased me. "I bet you want to touch these don't you. Sorry Shawn, but that's not allowed ... you're my employee after all ..." she said in a soft, almost breathless way. I could tell by her tone that she was getting turned on. It was a little less teasing and a little more seductive. "Maybe one day I'll let you touch my body ... but for now I want to you be still. Keep those arms up, champ, this is going to tickle sooo much!"
With that, Steph leaned in and put her tongue in my belly button and started swirling it around. She was careful to bring her boobs achingly close to my rock hard dick, coated in a layer of precum, but she did not let them touch me. As she did this, she started to lightly scribble her nails up my body towards my forearms.
With this lighter, teasing tickling, I didn't laugh quite as hard. But it still really tickled! "Hehehe ... oh man .... hehehehe you're good at that ma'am" I managed to say. I hoped that appealing to her ego would end my ordeal and maybe even get me a reward. Thoroughly dominated at this point, by the younger woman, I just wanted to be a good boy.
I'd soon get my chance. Abruptly, Steph stopped teasing. Sat up (with her butt on my lower abdomen) and started cruelly raking her fingernails up and down my upper arms and in my arm pits.
"Yeeeaaah!" I screamed. "Nononono! Please that's soooooo baahahahahahaaaad!"
Steph smiled maniacally as she rubbed herself on my torso, scribbling her nails up down and around.
I tried to be good, but I couldn't help bringing my arms down. "I'm sohorohohorry ... it just tickles so much!" I lamely exclaimed.
"Bad boy!" she yelled. With her left hand still trapped under my arm, wiggling around to great effect, she took her right hand, rolled me over with her legs and smacked my still sore left buttcheek three times. "Keep your arms up!"
I closed my eyes and did as I was told. How much longer could this go on? All in all, it was about ten more minutes of torso tickling, during which I occasionally couldn't help bringing my arms down, to get spanked as punishment each time.
Steph was getting more and more turned on by her dominance and my submission. At last, she couldn't take it any more. She leaned in and whispered in my ear, "Time for a reward," as she slipped her soaking wet g-string off (keeping her stockings and heels on). Could that mean what I thought it meant??
She lifted herself up and hovered over my shaft. With that, my hands instinctively gripped her hips. Her skin felt as good as it looked - soft, smooth and, now, slick with sweat.
"Now ... she said ... you need to be a really good boy. Show me how disciplined you can be. No cumming for five minutes! I'm going to ride you and get off as many times as I want. You have to hold it! If you can last five minutes, you'll have proven to me your dedication. If, however, you don't last ... you are going to come to my house next Thursday. And I'm going to tie you up and tickle torture you for as long as I want. One hour, two hours, hell maybe I'll even keep you all night. You'll have to make up some BS to tell your wife. So - if you know what's good for you - don't cum!"
As hot as I was, the way Steph said "torture" made my blood run cold. It's as if what she had done to me so far was just a walk in the park.
She slowly lowered herself onto me. Her slick, smooth (waxed) and wet pussy was as good as anything I could remember. My hands instinctively moved from her hips to the outsides of her thighs as she began to move back and forth. I almost lost it within ten seconds! I somehow remembered her threat and decided that I needed intense focus to last five minutes. I closed my eyes to avoid looking at her incredible body and took my hands off of her ... as hard as that choice was given how good she felt.
"Oooh," Steph moaned as she picked up some steam. "Smart ... you don't want to cum too quickly. Good boy!"
The demeaning taunts were impossible to ignore. I was struggling to hold it.
"Are you gonna lose it?" she whispered.
I knew there was only one thing that would distract me ... "tickle me," I said softly.
"What was that baby! I can't hear you!"
"Tickle me ... tickle me! Oh my god ma'am please tickle me!" I shouted. All of my sense of dignity was now gone.
"Smart boy," Steph replied and started wigging her fingertips up and down my sides and riding my dick rhythmically as I bucked and bellowed with laughter.
As it turns out - her tickling was just agonizing and distracting enough to keep me on the edge, close to cumming but not quite there. As long as I kept my eyes closed and my hands off her body, I should be able to make it.
Steph was having the time of her life. I could tell by how her body clenched up that she enjoyed two orgasms in rapid succession. Running her hands all over my body, exerting dominance, listening to my anguished laughter and pounding my rock hard cock was as good as it got for her. It's good to be the boss!
I had lost track of time when suddenly I realized the tickling had died down and she was, instead, rubbing my chest and building to another orgasm. Oh no ... this would be trouble. Then she whispered in my ear "Only 30 seconds left, Shawn. Then you're free."
She ground her hips three or four more times but I bit my lips and kept concentrating. I knew I could hold out. I was going to make it!
Then, she did something entirely unexpected. She grabbed my hands with hers. The she pushed them against her perfect, shapely ass, and squeezed. In my 40-odd-years on this earth, I'm not sure I ever felt so good. It felt better than it looked. Firm, tight, round, with soft slick skin. As close as I was ... two handfuls was all it took. My groin lifted clear off the table as I came as hard as I ever had. This prompted Steph to enjoy her third orgasm of our session. After I pumped out a few loads, she climbed off and sat back, breathing heavily.
"Well, will you look at that," Steph said after a minute of heavy breathing. She stood up and reached for her panties. "Four minutes and 55 seconds. Oh well! Guess I'll have to teach you a lesson next Thursday. You better start thinking of an excuse for your wife."
Through my tears and exhaustion I managed to moan, "That was a dirty trick ... it wasn't fair ... I took all the tickling, there was no way I could hold out after grabbing that ass."
Steph pulled on her thong. "Hey, it's not my fault I take care of my body. Look, if you last a few hours next week and don't pee yourself like my ex did, maybe I'll even let you give it a few smacks!" she said with a wink. To accentuate the point she smacked her own plump butt. It seductively vibrated for a second or two but didn't move given how rock hard it was. Incredible.
She put her bra on, picked up her shirt and skirt and strode out of the conference room without another word.
Wait a minute? Wasn't the janitor out there? I didn't have time to worry about that. My goal was to get dressed as quickly as possible and get to my car. Driving home, I'd clear my mind and come up with a strategy. What do I tell my wife? What do I do about my job? I can't possibly let this maniac tie me up and torture me, right? Then again ... is this something I secretly want? I hadn't been this confused in years.
As I staggered out of the conference room, I did indeed see the janitor emptying the trash can at a nearby cube. How long has he been there? Did he see anything or hear anything? He didn't give me a funny look, so I'm guessed I was ok ... Then I heard the ding of the elevator bell and looked up. Steph, now fully clothed, was waiting to head down to her car. She was about ten feet away from our janitor, who was now gazing aimlessly in her direction. She dropped her notepad and bent way over, with her butt in the air. Then, almost as if it were a practiced skill, she hiked he dress up to show the poor janitor the bottom of her butt cheek. In a split second, the straightened up, smoothed her skirt out, and without acknowledging either of us entered the elevator to head down to her car.
What had I gotten myself into?
To be continued...
