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My Boss: Part 2 (F/M)

Pedigree5

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Joined
Aug 12, 2007
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Please see Part 1 here: https://www.ticklingforum.com/threads/my-boss-part-1-f-m.446864/#post-5864086

My Boss: Part 2

It was Thursday at dusk. My head was spinning, my heart was pounding, my brow was sweaty and adrenaline was coursing through my body as I drove slowly to Steph's house. A week prior, she'd manipulated and forced me into being mercilessly tickled for her own kinky desire and tonight was shaping up to be much, much worse.

The intervening week had been interesting. First of all - my wife was very unhappy with the fact that I'd been working late again ... this time with no idea when I'd be getting home. I had to promise to let her go on a girls’ weekend on at some future point while I watched the kids to make up for it. I secretly suspected that her trips with her college friends were an excuse to dress slutty and hit on younger men, but I was in no position to judge given recent events.

Worse yet, Steph took every opportunity in the office to remind me of what I'd been through ... and what was to come. The day after she tickle-fucked me on the conference table, I found a note on my office keyboard reading simply "See you next week, tickle bitch! 🙂 ". Over the course of this week, she stepped up her harassment. On Monday she called me into her office, closed the door, and squeezed my balls saying "these are mine on Thursday." In our ten-person team meeting on Tuesday she used the term "ticklish situation" three times, smiling at me each time. And yesterday - before I left for the day - she came into my office and (almost as an afterthought) told me not to wear underwear today. She was getting more brazen as the days ticked by.

Steph lived in a new, medium-sized, single-family home in a trendy mixed-use neighborhood not far from our office. It was an expensive part of town. I pulled my midsize SUV into her driveway and parked, taking time to catch my breath. I wanted more than anything to turn around, drive home and forget the whole thing. But she did (figuratively and, sometimes, literally) have me by the balls. I took a few calming breaths and checked the texts on my phone. Then I opened up the Microsoft Teams app that we use for office communication, spent a couple of seconds poking around, sighed and put my phone away. Slowly I got out of the car and noticed an empty cardboard box at the foot of the walkway to the front door. I walked up, pressed the ring doorbell and waited. She didn't take long...

"Hey there, Shawn," I heard through the ring camera. A cheerful and recognizable voice. "Right on time ... good start! But like we talked about, you need to listen to what I tell you and be a good boy. Would you like to come in?"

"No," I thought.

"Yes ma'am! Please let me come in," I said.

"Well, since I am your boss and this is my house, I'm going to need to set some ground rules before I allow you to enter. The main rule being that you are not allowed to wear clothes in my home. I already know you aren't wearing underwear, but you will need to take it all off."

I gulped.

"So, I need you to take off your clothes and put them in the cardboard box at the end of the walkway and carry it to the front door. I'm in a good mood, so I will allow you to strip in your car. However, you must walk from the top of the driveway to my door naked and ring the bell again. If I'm satisfied, I'll let you in and your discipline session will commence."

This was diabolical. The humiliation was starting already and I hadn't even entered her house. "Yes ma'am," I meekly replied and walked back to my car.

As I did, I scanned the street. The sun had just gone down, but the glow of dusk remained. Someone walking by on the sidewalk would definitely notice a nude 42-year-old man carrying a cardboard box. Someone driving by at 20-30 miles per hour probably would as well. Luckily the walkway was only fifteen feet and not fifty. I'd still be vulnerable though.

Wanting to get it over with, I picked up the box, got into the backseat and took it all off. I folded my clothes neatly in the box and put my wallet, keys and phone on top. I scanned through the rearview and side windows, didn't see anyone, and quickly stepped out of the car. Knowing that I'd be punished if I ran, I walked briskly to the front door and rang the doorbell. Ten seconds went by. Then twenty. I started sweating and spotted a car in the distance slowly driving up the street. After thirty seconds, just before I’d be in eyeshot of the driver, the door finally opened and I scampered inside.

"Come in, sweetie," said Steph with a smile, wearing a black silk robe that came down to mid-thigh level. It was open in the front so that I could see her amazing cleavage tucked into a silky black bra. She wore her hair up with black lipstick and - of course - had on her trademark black three-inch heels. One glance at her and blood involuntarily rushed to my midsection as I found myself begin to get aroused.

"Would you like a drink?" she asked.

Honestly craving something to calm my nerves I replied, "Yes, please, ma'am. Thank you very much. May I sit down?"

"What a polite little toy ... I mean boy!" said Steph with a chuckle. "Yes, you may. Do not cross or otherwise close your legs. I want you as exposed as possible at all times."

I took a look around at the tasteful, minimalist decor and sat my naked ass down on the cream leather couch, carefully placing the cardboard box with my clothes and personal items on the floor next to me.

Steph came back from the kitchen and handed me a glass of top-shelf bourbon on the rocks. Strangely, she also had a chilled bottle of vodka in her other hand which she placed on the coffee table in front of us. I knew better than to ask any questions about it.

She crossed her golden legs and turned towards me. "I'm looking forward to this. I've never minded mixing business with pleasure and I know that you'll thank me for this lesson. I really think that, with a little more discipline and concentration, you can be the top performer on the team! While you are here, you are to obey my commands to the letter. You are NOT allowed to put your hands on me unless I specifically tell you to. You are not allowed to cum unless I allow you to. You are not allowed to go to the bathroom at any point. Do you understand?"

Regretting the bourbon, which I had already gulped down three quarters of, I responded as desired, "Yes ma'am. I'm very grateful for the lesson and for your leadership."

"Of course!" she said. "It's my job as a leader to properly inspire and motivate my team. And, this is a fun way to waste a Thursday night ... usually a pretty boring night of the week. Tomorrow, I have a Tinder date with a dumb jock from the university across town. He's pretty hot, so I think I'll probably bring him back here. Unlike you, he's not my pet. So, after I'm done torturing you, tonight ... it will be nothing but pleasure for him tomorrow! I'll give him the best blowjob of his life and fuck his brains out in multiple positions. I may even let him spank me the way that I spanked you last week. If he sleeps over, I’ll wake him up early Saturday and tell him to stick it between my perfect tits. Then I can get on with my day and go to the gym for a few hours and watch all the guys drool over my yoga pants while I maintain my amazing body. If the college boy is enough of a stud, I might even text him for round two Saturday. No man has every failed to drop what he was doing for me. I’ll never let him tickle me though ... I do the tickling," she said with a smile and a nod in my direction.

As my face got red with jealously, my curiosity was piqued. I knew questions were a risk, but I asked one anyway: “So what do you have against being tickled? Seeing that you like doing it so much…”

Steph’s response was surprisingly honest. Was she letting her guard down a bit?

“Like I told you last week, my two big sisters always tickled me growing up. I’m really ticklish and hated it! The worst moment came when I was 18 and home from college for Thanksgiving. It was a warm day in south Florida, where I’m from, and the three of us were at the backyard pool in our bikinis. My sisters are also hot, as you’ve seen from the pictures on my desk, so there were usually boys over. Well - on that Wednesday my sisters thought it would be funny to show the two guys they were with how ticklish I was. I was swimming and they actually pulled me out of the pool, dripping wet, and all started tickling at once. One held my arms and one held my feet and the other two tickled up and down each side. They took turns and made me beg for them to stop … but the guys wouldn’t agree until I took my top off. One of my sisters grabbed the top and threw it over the fence into the neighbor’s yard! Then my sisters held me down and let the guys tickle my boobs while I only had my string bikini bottoms on. It was really embarrassing. It lasted three or four minutes before, thankfully, my parents got home. I have no idea how far they would’ve gone! I still had to jump the fence in nothing but my bottoms and grab my top before they came into the backyard. From that point on - I resolved to position myself to be as dominant as possible personally and professionally … in all situations. And NEVER to be tickled again!”

As Steph was telling this story, I maintained eye contact and kept my hands at my side, as instructed. It took much willpower not to touch my throbbing dick as she recounted her sordid origin story, but this night was about my discipline and not my pleasure.

“Anyway,” she said as she regained her composure and dominant attitude. “You had something to drink, now it’s my turn. I’m the mood for a body shot … you know what to do.”

“Body shot” was a phrase that I hadn’t heard in years. It reminded me that Steph was only 24. Knowing what was expected of me, I laid down flat on the couch with my hands at my sides as she opened the chilled vodka bottle. Before she had her drink, she slowly undid the front of her robe and let it fall to the floor around her high-heeled feet. There was the hourglass body that I’d spent the last week obsessively picturing. She reached around and popped her bra off - revealing her tanned, round and perky tits - and ran her hand over her toned tummy which was accentuated with a cute diamond stud in her belly button. Of course, I also looked down at her long, silky, tan legs and could see the sides of that fantastic peach-like ass that she loved to show off.

Now wearing only a skimpy black g-string and heels, she slowly poured the ice cold vodka into my belly button and onto my tummy. I breathed in sharply and my stomach flexed and wiggled as a result of the cold and goosebumps immediately formed on my body. Steph knelt down and started lapping up the vodka with her warm tongue, being careful not to let her boobs touch my body or make any contact with my cock, which was sticking straight up by this point. She swirled her tongue around in my belly button, which tickled maddeningly and began to lightly scratch and trace her nails up my sides and skittered them over my chest as I began to softly laugh and vibrate.

“Oh come on,” she teased. “That doesn’t really tickle, does it?”

“I’m sohahaharry,” I replied, “it really hahaha does hehehe!”

“Well, I don’t want you getting too worked up,” she responded. With that she took two ice cubes out of my drink and began to run them both up and down my torso, starting at my nipples and trailing them lazily down my sides as I squirmed as a result of the cruel ice torture.

Steph took two more shots in this manner, following them up with more ice each time. After her third shot, she rubbed the ice cubes on my balls and shaft before rubbing them on my thighs and calves. Torturous as this was, this was actually a benefit as it calmed my hard-on a little bit and brought me that much farther away from the limit that I was not allowed to cross.

After she had her fill, Steph sharply commanded. “Now stand up! Enough messing around! I’m going to sit here and you are to stand in front of me, facing the opposite way. Spread your legs and put your hands behind your head.”

I hopped up and did as I was told. I was now facing away from her with my legs spread apart and my hands locked behind my head. I felt unbelievably vulnerable, which started to turn me on again.

“Good,” she continued. “Now, due to your undisciplined wiggling as I was barely tickling you, you spilled a four drops of vodka on my couch. That means you get four spanks. Each time you make a noise … that’s one minute of tickling. Remember, this is just a warm up. After we’re done here, we’re going into my bedroom and I am going to tie you up and tickle you until you beg for mercy.”

My mind quickly assessed the situation. Surely, I could keep quiet for four spanks, but did Steph really want that? Might it be better to take my chances and make some sounds? She obviously had a desire to tickle me in this position. Getting four minutes out of the way now could save me thirty minutes of hell later. Maybe I could satiate some of her desire before the main event began? I cursed under my breath given the ridiculous choice at my disposal.

I winced as the first smack landed on my right cheek. “Ow!” I yelled. I could almost feel Steph smirking behind me. Smack, smack, smack! came three more slaps on my left cheek in rapid succession. “Ouch! Ow! Ow!” I yelled. She gave me one more very hard spank on my right for good measure.

She slowly walked around to look at me, making sure that I got a full view of her jutting rear end, framed by her thin black thong. She then said, with a smile, “Bad boy! That’s four minutes of head-to-toe tickling. Are you ready?” She chuckled as she asked. It kind of seemed like she in disbelief about what she was getting away with.

“Yes ma’am,” I nervously responded.

Steph began with my exposed armpits, using her sharp tails to tickle from my elbows down to my underarms and sides and then back up again.

“Aaargh! Hahaha! Hohoho ooooh no! Stop oh no! It tickles soooo bad!” I roared. I was both expressing a genuine feeling and letting Steph hear what she wanted.

After one horrible minute on my upper body, she moved down to my balls and cock. I stiffened once again as she teasingly tickled up and down my shaft with one hand and spidered by balls and taint with the other.

This resulted in a slightly higher-pitched, but no less frenzied laughter.

“Hehehe … oooh! Ooh my cock is ticklish!”

“Not there … hahahehe … not my balls, oh please!”

“Steph no! Steph I can’t take it! Naahahaha!”

After one minute of this, Steph shifted to my legs and my feet. She actually made me stand on my tiptoes and she tickled my heels … one of my worst spots. Not being allowed to bring my feet down was agonizing. But it demonstrated the kind of discipline that she wanted to see. I was cried and begged as she teased me. Worse yet, my bladder was starting to fill and I wasn’t even in the bedroom, yet. Tears ran down my cheeks and my entire body turned red as I cried and begged.

Steph was characteristically merciless.

“You are my pet, Shawn! You work for me and I can get rid of you whenever I want. If I want to tickle you, tie you up, spank you, rub ice on your body or keep you on the edge without letting you cum, that’s what I’ll do. And there’s nothing you can do about it! HR will never believe you. Nobody will believe you!”

And that was what I needed to hear. I quietly brought my heels down and walked away from Steph, who immediately stood up and roared, “Get back here, Shawn!”

Wiping the tears from my eyes and catching my breath, I responded, “I don’t think so.” A mix of anger and confusion came to her gorgeous face.

I calmly walked over to the cardboard box where my clothes were folded as Steph eyed me quizzically. I picked up my phone, opened the Teams app and held my phone up to her face.

It was recording. I had evidence of everything.

Steph’s eyes got wide. She gulped.

To be continued…
 
Great story! I like the twist at the end and can't wait for part 3 (and 4, 5, etc lol)!
 
Spectacular story 😩.

Love the concept of tickle revenge !
 
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