Obnoxious I admit I can be an obnoxious 32 year old spoiled man. But not as obnoxious as I was at age 30 when my life changed doing a boxing match with an older woman. I grew up with money thanks to my awesome grandfather and parents who started a beer and soda distributing company that is now in 27 states. There is nothing I wanted growing up. Had a BWM as my first car at 17, the best clothes, schools and friends who were all like me, spoiled. I screwed more women than I could count and admittedly I was not the nicest guy at times towards women. At almost 6 feet and 180 pounds I had the looks and body matched with all the money to do what I want and when I want. OK, so you have the picture. Maybe I needed this event to happen when I was 15 and maybe I would have been a better person as a result, but it didn't and it's time to own it. To be all in and see through honest, it was strongly suggested by one specific woman to write everything down so let's proceed. I travel a lot for business, from state to state and because I am a proud member of the lucky sperm club I have little pressure on me at work. My last name carries a lot of weight let's say. When I travel I would do so first class, taking my employees and customers out first class all the way and everyone loves it. One of my favorite spots to travel is Florida since they have good weather for 6 months of the year, sweet looking babes all over, awesome strip clubs plus my company has two supped up condos there. Can I mention I get layed there more than any other state and even though I pay for some of that the others I just pick-up at clubs. Just being transparent here. My parents are always bothering me to get married like my 3 siblings but I am having too much fun. Over the years I have hired personal trainers in various states to keep up and improve my physique as much as possible since I am VERY into my looks. I have a few well placed tattoos, good amount of muscle and definition that I like to flaunt and added a boxing regime for the past three years. And I love it on all levels and have some talent to match. I am not the rough and tough type of guy in fact just the opposite, I would rather flex my muscles, throw around some money and screw as many chicks as possible than get into a fight. Disgusting behavior some say. I might agree, however, I never take advantage or at least not too bad, ha ha ha. No means no and all of that and afterall who cares if she says no, there are 10 more right behind her, plus with my looks, body and money, no is not a very common word for me to hear to be frank. Now the boxing- I have been in 11, let's call them amateur bouts and I won 8 of them with the other 3 I got tagged and lost. I have never been in a streetfight and have no plans on doing so. From my perspective only low lifes, the mentally weak, the poor and jerkoff's would ever be in a streetfight. The boxing and added muscle and even the tattoos have given me a lot of added macho type of confidence, not that I need a lot of confidence in my day to day activities since I was never lacking for that. Last summer (2017) I was in Florida and working out at this high level boxing club when I saw a fox, a piece of ass like I rarely see around much. I put a target on her and wanted to show her a good time. I have bagged plenty of A+ ass in my day and nailing this one was going to a good one. The first time I saw her she was banging away, like a pro I must add, at the heavybag with a good healthy number of people watching her, plus a trainer who looked like a beast himself. She was tall at least 5'8, she had amazing musculature with really developed arms, a back that looked like it could pull down a wall and abs that apparently she spent a great deal of time perfecting. Her brown hair was tied back in a ponytail, her orange sports bra was soaked showing off a nice natural pair of tits with judding nipples which were poking out since she knew all these people were staring at her, her punches were crisp and powerful looking and obviously she has been at this longer than I have, her legs looked developed and strong and she appeared very pretty although hard to tell for sure at that moment. This broad was put together solid and she knew it. My goal with this chick was to blow away with my charm, money and gift for gab. When she was done a lot of people clapped, she bowed and flexed and smiled one of those " I know I am awesome smiles" and walked past me and winked. I knew I had her! Or at least I thought I did. I only had three days left before I had to leave for my next city so I went back to the gym and she was never there but sure as heck I asked about her and it was easy to describe her. As nonchalantly as possible I hired a trainer for those days and asked about the foxy chick with the muscles I saw working out on the heavybag. The dude smiled ( I never get a female trainer since all I would do at the end of the session was take her back to my room and bang the shit out of her) and poured out everything he knew and it was like we were bonding over this woman. She was much older than I thought, in her 40's and while I banged my share of "milf's" this one was on a different level in all regards and I was fine with it. She was married, which never stopped me before and had kids, again no big deal to me as I just wanted to sleep with her. She was a competitive and accomplished boxer and when he told me this he looked deadly serious and he said " I am deadly serious brother, this babe can put you away". I laughed as I said to myself, oh ok, that is exactly what I want from her, I want to fuck this chick like her husband is not doing I am sure and if that's what you mean by putting me away then I am all for it. He tells me she is loaded, is a lawyer and she plays for real. I looked at him and said mockingly " my knees are shaking" and laughed. He shrugged and said "it's your funeral, man" In any event it was only on the third day she finally showed up and my time was limited as I had a business dinner so I went for it. She was walking through the weights area and was on her cell and was walking by me, looking seriously gorgeous if not strong and I said, that's not polite, you are talking so loud! She turned and looked at me, while still in conversation and told whomever she was speaking to to hold on. She stared at me like a teacher who was going to discipline a child, took two steps closer to me and I had a strange sensation. She wore a simple t-shirt tied underneath so showoff a very impressive set of abs and cocked her head and said, "excuse me?" I smiled to lighten the mood since she looked pissed off and I repeated myself and she looked at me inquisitively and said "and who are you?" I put out my hand and introduced myself and she stared at my hand and picked up her phone and placed it next to her ear and when she did that distinctive bulge of a bicep that got a lot of work and spoke into the phone and said " sorry, just another jerk begging for a beatdown" and she walked away. For one of the few times in my life I stood there speechless knowing I was not coming back here for at least 4 months. Over the next four month's I was back to my normal life, that's my normal spoiled having a ton of fun life. But one thing I did was do my research on this woman and I discovered she was seriously the real deal when it came to boxing. The summary is that she has been fighting for at least 20-years and seriously doing it full contact and competitive. Her other credentials that I learned about, including her education and family status were all correct. She even competed in amateur bodybuilding contests in her early life. So what did I do? Knowing in my head that I can whip her ass right now, being the spoiled jerk I was I have to say, so I went hardcore into the gym and hired a boxing trainer. It helped! Over the next few month's I added a LOT of skill, extra power, 5 pounds of muscle and a tremendous amount of added confidence. I also had 2 more scheduled fights and totally dominated these guys. Naturally, I screwed some new chicks with my hard body and I was damn well proud of it all. I looked forward to my upcoming Florida trip. However, and let me be clear, I had no desire to box her to prove that I am better than her, beating on an older woman who I outweigh by 50 plus pounds meant nothing to me. Getting her into my hotel bed was my goal and if that meant getting her into the ring for a round or two to punch her around some was fine. Nothing more. She has a website that is free and I spent a lot of time on that thing checking her out and reading what people wrote. I was surprised by the large volume of people writing to her each day and clearly she had both a loyal group of followers who loved her and many who hated her with a passion. After seeing all of her videos and pictures I was more psyched to have this trophy in my bed where I know, based on a lot of experience, I would own her. My plan was to spend a weekend with her in my hotel, treating her well, letting her know what a real stud can do and making her part of my travel plans each time I went to Florida until such time I got bored with her. I was both mentally and physically prepared. I was anxious driving to the gym in Florida and was able to find out from a "paid friend" that she was there working out so I shot over. I dressed the part wearing some tight and fashionable high end jeans and t-shirt to showoff the new muscles and it easy locating her. All I had to do was follow the crowd since there was always one nearby watching her workout. I stood there and watched with about 25 others as she sparred 9 rounds for 5 minutes each with 4 different sparring partners, 1 woman and the others guys. Everyone wore 12 oz gloves and headgear and she was impressive. I saw the speed I heard about on her website, I saw the power and what really stood out to me or the two things that did were; first her ability to take a punch as she was tagged a lot. Yeah I knew the headgear helped but there was no body protection and she got banged plenty in her abs. The next thing that stood out was her stamina. I know I could not do 9 rounds of 5 minutes each, no way. I am not sure I could do 9 rounds of 3 minutes since the longest I have gone was 3 rounds. And the definition in her muscles stood out like some of the fbb's I screwed with over the years. Well, maybe not true female bodybuilders but heavily muscled women nonetheless. When the sparring was over she was surrounded by people so I had no opportunity to make any kind of move so I decided to do some lifting and write this day off in terms of speaking to her. I was lifting without a trainer and after an hour I was bored and ready to leave, shower and meet some other hot chicks on South Street. As I was walking to my rental Escalade I had the luck of seeing her going to her car nearby. I called out her name and she looked up through her sunglasses and it was obvious she had no idea who I was. So I walked over to introduce myself and she became quite defensive. In her stance She was wearing some baggy sweats and a loose fitting top that was cutoff to show more of her cut bod and as I got closer she dropped her gym bag and faced me. Best way to describe her look at that moment was one of attack or at least ready to strike back at this attacker! I was anything but that person so I raised my hands and assured her I was just saying hello and stood still when I said this. Still, she looked ready to pounce. I did what I do best, I talked! I gave her my name again, told her I admired her sparring and LOVED her website and she lowered her hands. I was going to walk away at that point not meaning to upset or scare her and it was who said, what was your name again? I told her and from a distance I held out my hand to shake hers. I heard her accent and thought it was cute and within a few minutes we were standing a few feet from another talking. Nothing special just my way of inching in there to eventually make my move and get her back to my hotel and into the bed. After about 10 minutes we both went our separate ways. Unfortunately for me, I had to go to Georgia for business the next day and cut my Florida trip at that moment. I could not get her out of my mind. She captivated me with her smile, her body and her attitude. Not to mention her website is so revealing in showing many personal items, such as, all the details of her fighting life, her family and when I read all the notes that people write to her, both pro and con, well I knew I had to bed this chick, just had to. If that involved strapping on a pair of boxing gloves to show her what I can do, than I was all in. Two months after our last visit I was back in South Florida and ready to pick this lady up, as they say. I arrived at the gym with a fresh haircut, totally in the best shape of my life and ready for this major conquest. I started walking around the place looking for her and it did not take long to see her and a bunch of others coming in from a training run. They were all drenched in sweat and speaking among each other and I waited for a chance to get her alone. One thing I found interesting was that she ran this 6 mile "training run" with 4 oz weighted gloves on each hand, which is quite the feat! When the opportunity arose I walked right over to her. Between thinking about her so often and for so long and going through her website so often I felt I knew her! Boldly but slightly nervous I walked over to her and re-introduced myself by sticking out my hand. She was pleasant but had no idea who I was and that was OK since I have a great rap with women. I told her how impressed I was with her fighting skills and that I saw all of her videos on her website and asked her if I could spar with her today. She looked me up and down and asked me several questions regarding my boxing history and details. I was perfectly honest with her and she smirked once I was finished. I asked her what was so funny and she just said, "are you sure you want to go full contact sparring with me?" and added " I may make that pretty face of yours a little swollen". I was taken aback by her bluntness and I said "well, if I can beat you will you have dinner with me?" She laughed out loud and said, " oh I see, so you, like all the other guys, want to have a date with me?" We both laughed and she said, "OK young man, give me an hour to shower, eat something and change and I will meet you in ring #3 and speak to Anna who will give you everything you need and something to sign" and with that she walked away. When I made my way to Anna, who I was told was a well known female bodybuilder and my opponents strength coach and who was VERY nice and had a very beautiful face too, she gave me all the gear plus a waiver to sign and I was ready. One hour on the dot and she entered the ring where me and Anna R. were standing. Anna told me there would be 3 rounds of 5 minutes each and that Anna would be both the ref, timekeeper and my corner person. She asked me 3 more times if I wanted to go through with this. I told her yes but was getting an uneasy feeling about this. Especially as I looked across the ring and saw her shadow boxing and warming up. What I saw was a SUPREMELY fit and incredibly fast punching an experienced opponent. My mind went through all of the videos and stories I read about her on her website. One time even I wrote something on her website and her husband Charles wrote me back a personal note. The bell rang for round 1- She bolted out of the corner so fast I thought she was running towards me as I walked towards the middle of the ring. I stuck out my glove in a gesture of "hello and let's have a good fight" and she smacked it away and landed 2 left hooks to my face and a right cross to my chin. Fast, powerful and shocking to my system blows. It was like wow, OK lady let's do this. I circled to my right like I was taught but believe me it was not like I had to look for her as she followed me like a tiger after it's prey. I threw some stupid and awkward jabs that sailed over her head and when I did she threw AND landed a number of blows to my belly. I felt all of them and was in a little state of panic. I began to back peddle but she was on me when my back hit the ringpost and I tried to tie her up and do something but this lady was really strong and her arms were pumping like pistons blasting away at my belly and I felt my legs going goofy like I was losing it. Then she blasted me with the fastest 3 punch combination I ever experienced, left-right-left hooks to my face and I felt like I was in a dream, a bad dream and next thing I knew I was on my ass looking up at the ref as she pushed this woman into a neutral corner. I got my legs back pretty fast but realized I was bleeding from my nose which was unacceptable and I was pissed off. When I got up at 7 Anna asked me if I was OK, truth was I was still a little dizzy but I told her I was fine and then she told me there is still 4 minutes left in the round!! Anna held my gloves and with a very sincere, almost motherly nurturing way asked me if I wanted to go through with this. I looked her dead in her eyes and said yes and she smiled and said OK handsome man, go to it. I wanted to beat the shit out of her as she was smiling with her hands resting on the top ropes stretching out that incredible body I wanted to bring back to my hotel asap. As I walked towards her she waved me over with her glove and started talking to me. I never had that experience before. She called me pretty boy, she pointed out the bloody nose and told me that she is going to knock me out like the weak shit I am, she called me a stud and asked me if all the girls loved me. WHAT????? Screw you I thought and I told her, COME ON LET"S DO THIS!! I threw a straight right into her face except that by the time my punch was supposed to land she moved to her left and landed another right hook to my chin. I felt it, no mistake about it but not like the last combo. Before I turned around to attack her she smacked me in my ass and was taunting me with bullshit. Anna was nearby and for a brief moment I studied her body and saw her arms were bigger than mine and her pecs in the shirt she was wearing looked like boulders on her small chest. I walked towards her as she backpeddled but I could not hit her, her defense was so good or maybe my offense was so bad. Plus I am getting a little tired since I never went more than 3 minute rounds and have never been smacked around like this, by anyone so much this beautiful muscular lady with whom all I wanted to do was screw. Then she motioned me over with her glove and said, "OK pretty boy, you are one shitty fighter so it is time for a nap" I went after her now but it was useless. First a barrage of hooks and uppercuts to my belly had me leaning over her as she pretty much held me up and she whispers in my ear " ok pretty boy time for mommy to beat the shit out of you and knock you out! I was exhausted and those belly blows sucked all of the energy out of me. I actually left blood onher shoulder while I was leaning on her and realized I was bleeding fromboth my mouth and nose. She pushes me off and all I can remember is the next thing I remember was Anna sitting next to me brushing back my hair and asking me if I knew where I was. I really did not for a few moments until the pain began radiating through my body and I noticed her holding a towel with a lot of MY blood on it. I stupidly asked, where is she, is the fight over? She laughed and said "darling, you were unconscious for a good 30 seconds or more and I do not think you landed a punch, nor did I think you would and chuckled". She added, "trust me you got off easy". Anna then said the following to me in a very nice but direct way. She called me by my name and said, " listen this may sound weird to you but you really have no choice and BELIEVE me you are getting off easy, but you see that dog bowl over there in the other corner? I looked over and sure as shit there was a dogs bowl in the corner of the ring opposite me. I said "yes, I see it". Well, Anna said "you have to crawl over there and drink all the water while on all 4's". I looked at her like she was mad and said " what are you talking about, I am not going to do that, get lost, I am leaving now". Anna flexed one of her massive arms and smiled and said " young man, trust me when I tell you that this is NOTHING compared to what could be happening to you right now, you said you saw Karens website, right?" Please, she continued, "for your own good, go do it, it will take 1 minute and then you can go home" She continued, " now kiss my bicep and start crawling". I thought about what I saw on the website and thought about how easily I was just beaten and how serious Anna was so I did it!!!! I crawled over and across the ring, still wearing my 12 oz gloves and as I crawled there was blood dripping from my nose and mouth that was making feel like shit and made my way over to the dog bowl. I heard Anna say in a soft and nice way " go ahead drink the whole thing and just get it over with". I did and felt like an ass doing it but remembering the things I saw in that website I knew it was my best option. It took longer than I thought to drink the bowl dry since I had to lick it all up like a dog. Once I was done I looked up and saw I was being filmed and lost it. I stood up and freaked out since I did NOT want any of this on tape and on her website for the world to see. I said a lot of crazy and uncharasteric things when from behind me Anna got me in a choke hold and told me to calm down and that giving permission to film the fight was all on the paperwork I signed before the fight. Things were going from grey to black when I heard Anna say " OK lover, do you understand now or shall I put you to sleep?" I said OK OK, through my choking voice and when she released me I dropped to all 4's unable to standup and was close to being knocked out by this huge lady. Eventually I stood up and believe me it took time and when I did, Anna explained to me thatKaren could have seriously hurt me, like hospital hurt me, so why don't you drive your fancy car to the hotel and count yourself as lucky. I stood there feeling like crap and turned to enter the shower area but had no desire to shower there since my hotel was a million times nicer. By the time I was walking towards the parking lot it was Anna who was following me and she tapped me on my shoulder. She said " OK lover boy, I think I want to see what you got" and she walked towards me and kissed me and grabbed my crotch and said " let's go back to your hotel and I will suck you off and fuck you like never before and maybe I will not beat you to a pulp" and with that she threw a hook into my already sore body and I doubled over with my head landing and resting on her incredibly hard but small tits and I sucked her left nipple for a second as she held my head with her hand and moaned. So yes, I spent the night with her and she was quite loving and good in bed and I knew I was the best she ever had. We both watched the fight between me and Karen on Karens website as she narrated the entire thing and she loved it FAR more than me. However, that damn video now lives for the world to see and I cannot do a thing about it. Darryn