The Boss Squash (True Story)

[Jericho3]

The Boss Squash (True Story)

This is a true story about one of my better encounters in adulthood. It is broken up into 5 parts and is fairly one sided. It features pins, chokes, scissors and smothers. It is a bit more sexual than some of my other true accounts. Enjoy!

Part 1: The Impromptu Matchup

"Chloe" was my boss. She was a new hire for a brand new branch. Since I was a long time employee I was sent there on a temporary basis to help train the new staff. On my first day, I was pleasantly surprised to discover that she was quite a stunning lady. Standing at about 5' 8" she was about 2 inches taller than me and probably weighed at least 25 pounds more than me at around 150lbs. Not only was I incredibly attracted to her juicy figure, but because she was technically my boss, she seemed to project an air of authority and dominance which drove me even more wild. I remember meeting her for the first time and immediately thinking it was going to be a challenge to remain professional around her.

Chloe had a knack for saying things that would turn me on without her even realizing it (or maybe she did?) One day after a playful argument, she told me she was going to kick my ass. Because of my obsession with mixed wrestling, it's tough for me to hear a comment like that and not push the issue. Even though I knew any type of relationship could easily jeopardize my employment, I knew I had to at least test things out to see if maybe she was into similar things as me. As many of you know, these scenarios aren't exactly frequent.

"Kick my ass? You'd have to catch me first!" I responded, figuring this was giving her a chance to continue the line of thought without giving too much away about my fetish.

"Oh you think you're faster than me too?" She spat back with her hands on her hips. I couldn't help but notice the dominating stance she took while staring back at me. She was wearing tight gray dress pants and heels that made her a good 5 or 6 inches taller than me. Her medium length dark brown hair was down and the white blouse she wore was unbuttoned just a bit, but still enough to be considered professional.

"Well maybe not always, but you're wearing heels. Good luck catching me in those!" I joked back, wondering if the rest of branch was picking up the same vibe I was getting from her, or if maybe I was laying things on a little thick.

She simply sighed, shook her head and walked away. At first I was a bit embarrassed. I was worried that maybe I made it a bit obvious that I was attracted to her by referencing her attire. But my embarrassment turned to intrigue when I saw just how she walked away. It wasn't a normal walk, but more of a "I know you're staring at my ass so here you go" type of walk. I was practically drooling watching the way her ass cheeks rose and fell with each stride. I spent the rest of the day sweating out if I was making something out of nothing.

Nothing more of it came up that day, but we'd each make suggestive comments to each other from time to time. Fast forward about 3 months and I had moved on from her branch, but we remained in constant contact. Throughout our convos, I learned that she was fiercely competitive and I decided that she had no reason to keep speaking with me unless she was looking for something more.

One night I decided I couldn't keep going about things this way. I had to know for sure if she really was this dominant figure I had built up in my mind. After losing to her in a mobile game and taking some smack talk I took my shot.

"Yea, you're real tough when playing games but you never kicked my ass like you claimed you could!" I texted. I then waited anxiously for a response. I stared at my phone, hoping things would go my way. When she finally answered, I was thrown off by her response.

"How tall are you again?" She asked. Huh? I taunt her about a fight and she asks for my height?

"Idk about 5' 6" I guess... Why?" I answered.

"Yup, just what I thought. You're shorter than me." She replied. This comment really ripped the rug out from under me. As a shorter man, I'm constantly believing that I'm viewed differently than other men taller than me. As I struggled to figure out how to get the conversation back on track, my phone buzzed again.

"You wouldn't stand a chance" was all it said. Now THIS was something I could work with.

"Oh you think height is the only thing that matters? I'd love to show you otherwise!" I texted back.

"Try me" was her answer and it was on. I was officially determined to suffer under Chloe.

Despite all the talk, it would be another couple of months before we actually met up. We didn't live near each other and at this point worked for different places but we enjoyed each other's company so we decided to meet just to sort of catch up. After hanging out for a bit, smoking some pot and enjoying some wine I decided to take my chance. She was wearing dark jeans that hugged her hips and thighs tightly and a pink hoodie.

"You know... I think we would have a very competitive wrestling match." I suggested, sitting next to her on the couch.

"Again with the wrestling?" She asked with a chuckle before adding "Trust me, you don't want to go there. I grew up with 2 older brothers. I know how to fight."

"If you're that confident, then show me. I'd love to see if you're as good as you claim." I answered.

She looked back at me and twirled her wine glass a bit before bringing it to her lips and downing the last bit of it. She slammed it on the table and stared at me for a moment.

"You sure you want to do this?" She asked, rising to her feet. I had a girlfriend at the time and she was concerned about ruining that.

"Positive" I responded, standing up to meet her. As soon as I did she was grabbing a headlock. She yanked roughly and I held firm for a moment. The two of us struggled but ended up losing our balance and falling to the floor. She landed on top of me and went for a pin. I attempted to escape but was forced to the floor by her hopping a bit forward onto my chest. Her ass hit me hard and her aggression caught me off guard as I realized she was heavier than I had first thought.

Despite how much I enjoyed the feeling, I didn't want her to think I was weak, so I intended to escape. But when I tried to roll free, she sat harder onto my chest and folded her arms. Her weight and leverage gave me no chance to break free and she clearly realized it.

"You go picking a fight and can't even escape one simple pin? I don't even know why I wasted my time." She casually remarked as I planted my feet, trying to squirm my way free. For once in my life I didn't know how to respond. I had chatted Chloe up so much about wrestling and she was holding me down easily without even having to weaken me first. She rode my attempts across the living room floor as I continued to try to slide free but there was no escaping her pin.

"Still think I can't kick your ass?" She taunted as she uncrossed her arms and placed her hands on the tops of her thighs. Her attitude of complete disgust at how easily she controlled me was humiliating, but also a huge turn on.

"I'm just... gathering... my strength..." I answered between labored breaths. She laughed in amusement.

"Please. My ass is crushing you right now. You're lucky you have a girlfriend." She remarked and gave me a light slap before rising off of me.

I quickly got to my feet and rushed her. She snatched my head into a front chancery and widened her stance, blocking my attempt at a takedown.

"You should probably just go before you get hurt." She commented nonchalantly, cinching in her hold. I didn't respond and continued battling, determined to make things at least somewhat challenging for her. I gathered my strength and managed to lift her legs up. As I did she quickly fell backwards still clutching my head. For a brief moment I thought I had control but I was snapped back into reality by her legs locking behind me and unleashing a powerful squeeze on my abdomen. She simultaneously wrenched on my neck causing a great deal of pain, so I had no choice but to tap out. She quickly released the hold as I rolled to my back breathing heavily.

"I think I proved my point. You should leave. We wouldn't want your girlfriend to find out about this." She spat with a bit of attitude, standing over me in a dominating stance. Defeated and emasculated, I muttered in agreement, grabbed my things and headed out.

After this encounter, I craved another chance with Chloe. Only a few times had I ever faced a woman that could overpower me from the very start of the match and I needed to experience it again. I broke up with my girlfriend shortly after this match because Chloe seemed so bothered by it. I wanted to eliminate any potential hurdles at getting a rematch and lucky for me, a couple weeks later and I had another chance to face off with her.

Edit by admin: This story has been voted the story of the month in [Only Registered Users Can See LinksClick Here To Register]. Congratulations, @[Only Registered Users Can See LinksClick Here To Register]!

[warthog]

Great start, love the pacing and the characters, and also their proportions
Good stories are few and far between here, looking forward to the next chapter.

[mixfightor]

Yeah, man, women in authority are damned hot. Not to mention that Chloe just sounds damned hot anyway. Thanks for sharing this with us. I can't wait to read more.

[musclead]

I love it, a great first part!

Here are my suggestions for whats next: describe Chloe physique in more detail. Also, it would be nice to propose strength tests like Arm Wrestling and finger lock during your next encounter.

Thanks

[Jericho3]

Thanks guys... the chapters are already written but I suppose I could go back to try to desribe her physique a bit more. As for the tests of strength, we pretty much just stuck to wrestling. But the next encounter will really illustrate her strength over me.

What were you and Chloe's ages at this time?

[Jericho3]

Originally Posted by bigbadbootyboy [Only Registered Users Can See LinksClick Here To Register]

What were you and Chloe's ages at this time?

We were both 25

[notsostrong]

Very well written..I can't wait for the next encounter

[kendawg]

This is an AWSOME story. You are so lucky to have lived it can't wait for part two

[Jericho3]

Part 2: The Rematch

In the time between matches, we had texted a lot. Chloe informed me that generally in her relationships, she was more submissive, but a part of her enjoyed controlling me on that day. I told her about some of my previous matches and how I had lost. She seemed obsessed with our height discrepancy, and often cited that as the reason I had no chance against her. So I told her about my encounters with a shorter girl Amanda and her headscissors and how height didn't matter in that encounter (from my previous story "dancer strength")

Chloe's response was "that sounds pretty extreme but you probably deserved it" She also indicated that if I was losing to smaller females that only proved her point even more, which was that if I couldn't handle a shorter girl, I definitely wouldn't be able to handle her.

I then told her about a face sit and she responded with "If I did that, it would probably kill you lol" before following up with a photo of her round ass in pink laced panties with the caption "but at least you'd die happy" These exchanges only served to motivate me to get under Chloe again.

When the day finally came, I went to her place and was pleased to see she had already pushed the furniture in her living room against the walls to give us more space. It seemed like she really was intending to give it her all this time.

She looked almost like an entirely different person. Her dark brown hair was pulled up in a pony tail and she was wearing black yoga pants with a white tank top and white ankle socks. Her attire and preparation showed me that this was something she actually wanted to do and not just something I was talking her into like our last encounter.

"You gonna last longer than 5 minutes this time J?" She asked with a smile, standing in her signature dominant stance, hands on her hips and looking down at me.

"Just to be sure, want to go best of 5? I'm still getting used to your style" I suggested, hoping to get as much time with her as possible.

"Sure. However you need to rationalize it." She answered back grinning, and stepped closer to me. I believe she was trying to intimidate me. I couldn't help but laugh in her face.

"You're funny. Do you really think I'm scared of you?" I asked, refusing to back down.

"You probably should be. I'm bigger AND stronger than you. And I've had a hellish day. So make the first move tough guy and see what happens." She answered back, her smirk turning more into a sneer. I hadn't expected her to be so forthcoming but her attitude was partially why I was there in the first place so I contemplated my attack.

Thoughts of being caught in her front chancery rushed into my brain, so I knew better than to try a double leg takedown. Instead I went for a quick go behind and wrapped my arms around her waist. Her hands quickly grabbed at my wrists trying to break my grip but I just pulled her tighter. I gritted my teeth and lifted with all my might in an attempt to take her down. I managed to pull her off the floor a bit but she landed right back on her feet.

"Jeez at least buy me a drink first J!" Chloe joked as our bodies squeezed tightly against one another. I didn't respond and lifted her up off the ground again but still couldn't bring her down.

"You're persistent I'll give you that but you're not big enough. This is why we could never date." She said. This comment enraged me. We had been texting rather suggestively for months, she had even sent me pics and yet now suddenly she was acting as if there was no attraction here. I was determined to show her. So I gathered my strength again and yanked her off the ground. This time I fell sideways bringing us both to the ground rather hard. I rolled her to her stomach and released the waist lock, opting to snatch her wrists and hold them behind her back.

"Oooo stronger than I thought... what are you gonna do to me?" She asked, suddenly grinding her ass backwards into my crotch.

Surprised at her apparent change in attitude, I held her wrists together with one hand and grabbed her ponytail with the other, wrenching her head backwards.

"Whatever I want." I replied, giving her hair a rough yank.

"Mmmm maybe after the match you can have me, but not now." She answered back, biting her lip seductively.

I didn't know if this was a challenge or an agreement but by this point she had my attention. Still clutching her hair, I released her wrists and began grinding myself against her ass. She used the opportunity to rub backwards against me for a moment so I got to my knees as she pushed up onto all fours. She slammed back into me a few more times before rolling to her butt to face me. She then reached around my neck, pulled me down towards her and quickly rolled forcing me onto my back, with her sitting astride my hips.

"I said AFTER we wrestle." She cooed and then hopped forward onto my chest. I quickly realized I was about to be trapped and tried to scramble free but before I could she was grabbing my wrists and tucking her shins under my shoulders. She inched her crotch up to my chin and tightened her thighs against my cheeks as she relaxed her weight on top of me.

"Uh oh, there I go crushing you again. Good luck moving this!" She exclaimed, slapping her rotund ass. Despite my excitement of being pinned beneath my hot former boss, I still had this conflict with my manhood. I didn't want her to think I was weak but I also knew she was right. I wasn't going to be able to budge her but that wouldn't stop me from trying. I planted my feet and bridged as long as I could. I wiggled back and forth but she held strong as I collapsed back to the floor. I summoned my strength and attempted another bridge but this time she reacted by widening her stance and pressing her crotch forward under my chin. I quickly collapsed as she continued to stretch my head back. The pressure kept growing and I debated tapping out but soon she backed off, closing her thighs on either side of my face.

"You're not going anywhere unless I let you." She proclaimed as her stance widened again stretching my head back with her crotch. I gritted my teeth at the pressure as she again took me to my breaking point before relaxing. She then repeated the move several times, methodically breaking me down but always letting up before causing a tap out.

"So what do you say. One nothing me? Or should I hurt you?" She asked deviously. I looked back up at her and knew my answer.

"I haven't quit yet. Why start now?" I replied.

She smiled back down at me and thrusted her hips forward.

"You're going to regret that." She said and rolled to her side. She quickly locked her ankles behind my head, cinching in a perfect headscissor. I groaned for a bit before tapping out on her thigh. To my surprise, she didn't release the hold, instead she grabbed both of my wrists and unleashed another squeeze while driving her crotch further under my chin.

"You really are an idiot. You tell me a story about how some girl beat you just like this before and expect me NOT to try it on you?" She taunted. I could do nothing but moan back at her as her meaty thighs pressed tighter under my jaw. She held her position a few more seconds before relaxing her grip a bit.

"I want to hear you say it. Tell me you quit and I'll let you go." She demanded. I took in a couple deep breaths and looked up at her.

"I... quit..." I muttered and suddenly she ratcheted up the pressure again. I groaned out loudly as she punished me for a few more seconds before finally releasing the hold.

"Smart move." She remarked casually as she rolled to her feet before adding "So one nothing me. Ready for round 2?"