Scott's Boxing Adventure (Chapter 1)

In my sophomore year of college started taking boxing lessons down at the Y to get in shape, and after a few I got a surprising email from my mom's friend Carol inviting me to have a match with her. We're friends on Facebook and I guess she'd seen the pictures I posted of myself in my boxing gear and liked what she saw.

I had to think about it before replying. I'm 20 years old and six feet tall, and Carol is 43 and 5'5", and I was afraid of hurting her. After chewing it over for a few days, though. I accepted; I figured she must have been doing this for a while and wanted to see if I could pick up some tips, plus I figured she'd be a good first opponent to build my confidence up. (Did I think my chances of winning were higher against a guy my age or a 43 year old mother of 2? Not a hard decision.)

I said yes and Carol took care of the rest. She set the match up for a Friday night, so we'd have the weekend to recover. Carol's husband knew, but nobody else - not my mom, not Carol's kids, and definitely not my girlfriend. The cover story was that I'd be doing a report for my college economics course on the food truck Carol owned with her husband all weekend.
I showed up at the small cabin Carol's family owns late on Friday night. She invited me inside and I saw that she'd cleared almost the entire floor and put up a small portable ring with thick blue mats and red ropes. There were also two cheap digital video cameras on tripods - I made a note to ask for a copy of the fight afterwards to review my performance.

I'd packed my outfit in a gym bag and set about changing. By the time I was in my trunks, boots, and gloves, Carol was wearing a white silk robe. No sooner had I turned to look at her than she dropped it to reveal that she was going topless. My eyes almost popped out of my head as I took in her bare 38DD breasts. I'd never seen any this big up close - my girlfriend's got a 32B which are very nice, but they were totally dwarfed by Carol's jugs.

"Like what you see?" she laughed. I swallowed hard and nodded. Carol's gaze was going up and down my body - one of her eyebrows arched slightly at the growing bulge in my trunks - and I did the same to her, trying to assess how she'd do in the match and not just ogle her tits.

Frankly, she looked pretty formidable. She's pretty strongly built with a thick neck, broad shoulders, and big hips; she stands 5'5" and I'd guess weighs in at 160 pounds or so. She's in pretty good shape for a lady her age, but I zeroed in on what I hoped were weaknesses: her strong arms had started going a little flabby, and her huge tits and soft belly looked like obvious targets. While checking out her body, I noticed her outfit - a short set of green silk boxing shorts trimmed with white, along with matching green gloves and boots with white laces. I was hoping Carol was feeling at least a little nervous, but she looked calm and collected, her big green eyes placid. Her short chestnut hair was in a little ponytail in the back, the front left loose to hang down and frame her large, round face.
We finished sizing each other up; Carol smiled at me and asked if I was ready. I nodded and we came to the center of the ring.

We touched gloves and backed up about five feet each. Carol nodded at me and I guess the match had started. We approached and I waited for Carol to make the first move. She obliged, coming at me in a flurry of quick jabs. She was much faster than I had anticipated and caught me by surprise, pulling my hands up and then snaking in a low punch that hit just above the waistband of my trunks. I grunted and dropped my guard, leaving her free to come in with a quick left-right-left jab combo that stunned me. She landed a heavy right hook to the jaw and just like that I was down on my chest. Carol started counting and only got to 2 before I was on my feet. She asked if I wanted to continue and I bit down a sarcastic reply that yes, I could still fight after a whole 45 seconds of boxing. I nodded at her and we came at each other.

This time I decided to go after her first. I started probing her defenses with jabs. I could already tell I was a little bit faster than Carol and had longer reach, but her years of instincts and experience overmatched my physical advantage as she weathered my assault, blocking, ducking, weaving, or swatting away all of my punches. I was backing her up and I hoped that she'd hit the ropes and have nowhere to go, but I left her an opening before she ran out of room as she surprised me with a short left straight punch into almost the same spot just over my waistband. I couldn't stop myself from coughing out some spit and covering my stomach, and Carol hit me with a devastating uppercut under my chin. I was knocked down and took a minute to admire the heavy wood beams in the ceiling as Carol started counting.

I was back on my feet by six and nodded when Carol asked if I wanted to continue. We seemed to be trading the initiative and this time it was hers as she closed in on me. I tried to keep her at bay with my longer reach, but my technique let me down as she was able to duck under a left and come in peppering my body with jabs. I threw a right hook, hoping to go over her guard and hit her in the head, but Carol darted in before it could land with a hard right that landed in my stomach. Winded, I covered up and backed off. Carol came after me, but I managed to keep her at bay using my reach and backing up when she came too close. This worked great until my back hit the ropes.
"Nowhere to go," Carol laughed, closing in on me. I tried to leap off the ropes with a surprise punch, but she weaved a few inches to the right and I whiffed. She pushed me back into the ropes, and I wrapped my arms around her, hoping I could clinch her and escape. Instead she hit me hard in the stomach. I gagged and she knocked the wind out of me with a second punch in the same spot. Carol put her left glove under my chin and pressed up, pushing my head back so I couldn't see what was happening. I flailed at her with my arms but she laughed this off as she started laying punches into my stomach with her free hand. I took four before I started sagging against the top rope, and Carol released me after two more. I sank to my knees and Carol laid me out with a massive right handed punch that hit me in the jaw. My head ended up laying outside the ring as we were so close to the edge, and when Carol didn't start counting, I figured she was giving me a break. As it turns out, she was simply stripping me naked as I felt her tugging on my boxing shorts. She pulled them down and off my feet, and I didn't have the energy to cover up my half-erect dick. Carol got out of the ring and walked over to my head and I stared up at her. I remember her looking down at me, gloved hands on her hips, tits swinging free. She asked if I wanted to give up and I managed a no. She walked away and took a drink of water as I slowly struggled to my feet, using the ropes to pull myself up.

Carol kindly pointed out that there were no rounds, but that I looked like I needed a break, and we both leaned on the ropes in our corners for a little bit. Carol was eying my cock and not making any attempt to disguise it; feeling a little embarrassed, I stared at the mat. After about two minutes Carol asked if I was ready and I nodded.

I was feeling a little better as we came out for, I guess, Round 2. I made the mistake of trying to cover my cock and Carol punished me with a few quick jabs to the body, then when I couldn't back her off, a heavy left to my aching stomach. I managed to keep my guard up, but I was too slow to block her followup as she launched a flurry of jabs at my midsection. I could tell she was trying to get me to drop my hands, but my inexperience was showing as I didn't know what else to do. Out of ideas I lunged at her with a quick right, but she easily ducked and I over-extended myself. Carol lifted a huge uppercut into my stomach and I covered up, barely able to stop myself from bending over, but not able to defend myself as Carol came in and hit me with a left-right to the face. I blindly pushed her away and backed up, bringing my guard back up.
I must have been more winded than I realized as I wasn't holding my hands properly; they were covering my face, but not the rest of my head, and I paid for it as Carol came in with a big swinging right hand punch that hit me in the temple.

She really knew how to put her body into each swing, and this one knocked me down with authority. I smacked into the thin mat and decided to stay down until 7 or 8 to give myself a little time to recover. Again Carol didn't count, and before I knew what was happening she was straddling my face. I didn't even have enough experience to take a big breath before she started the facesit. I could feel the heat of her pussy through her boxing shorts as she rested it against my nose and mouth. I lay there for a few seconds before she started moving her hips, pressing her crotch into my face. I started stirring after a minute or two, reaching up and pushing on Carol's hips. She didn't try to hold on, instead getting to her feet and backing away so I could do the same.

The whole match I'd been avoiding her chest, figuring this was cheating, but after her stripping me and rubbing her pussy against my face, I guessed we were not operating under the Marquess of Queensbury rules. This time as we closed I threw some jabs that managed to draw her guard up to set up my attack. Carol counterpunched with a hard right to my stomach that almost bent me over, but I stayed focused and managed to get her hands out of position. I lunged in with a quick left straight punch that mushroomed her big right tit. Carol screamed and tried to clinch, but I threw a hard right into her soft tummy. She gasped and tried to cover up and retreat, but I followed her, finally on the offensive as I smelled blood. A fake jab at her chest brought her hands back up and left her open for a followup left hook into her stomach, and she winced long enough for me to throw a straight right that hit her in the jaw. She took a step back and I came in with a left uppercut directly under her chin.

I scored my first knockdown as Carol crashed into the blue mats heavily on her back. I figured no holds were barred at this point, so instead of counting I straddled her stomach. I'd been mesmerized by her breasts and I went after them, using my gloves to press her boobs together, and pushed my cock between them. Carol groaned as I started fucking her tits, but she didn't move until I'd been doing it for about fifteen seconds - then she reached up and pushed me away.

I backed off as she got up with my head spinning. I guess I was kind of distracted by what had just happened as we came at each other and Carol easily slipped my guard, hitting me with a straight punch in the face that had me seeing stars. I clinched her, desperately trying to avoid going down, pressing my body into her sweaty chest, her hard nipples rubbing against my bare skin. After a minute she managed to push me away and I aimed some jabs at her tits, but I was losing speed and power; Carol pushed my assault aside and came in with a devastating hook to the jaw. I was turned 90 degrees away from her and she came in punching me in the right side. I threw my right arm out blindly and she swatted it away and nailed me with a kidney punch. I screamed and she threw a hard hook into my stomach. I went down to one knee, looking up just in time to see her right gloved fist coming at me in slow motion.

My world exploded in a garish blast of ugly light and I found myself on the mat, flat on my back, struggling to breathe through swelling lips. Carol probably could have counted me out five or six times over. Instead she waited as I groaned, rolled over, slowly got to all fours, crawled to the ropes, and used them to pull myself up. She asked if I wanted to keep going, and I stupidly nodded. She nicely waited for me to roll my head on my shoulders and get some semblance of a guard up before she came in for the kill.

Instead of attacking, Carol started herding me towards one of the corners. Even after I realized what she was doing, I didn't have enough skill or stamina to stop her; I managed a few jabs that slowed her down, but she stunned me with a gut punch and I felt her shoving me back against the ring post. A left-right combo into my stomach knocked the wind out of me and I collapsed against the post. I ended up sitting down, shoulders against the second turnbuckle. Carol put her tits in front of my face and started slapping me with them, left and then right. I was humiliated as her big sweaty breasts knocked my head side to side, but I was dazed and couldn't summon the willpower to fight her off. Going in for the kill, Carol pressed her boobs into my face, one after the other, and when she saw I wasn't fighting back she smiled at me, then slid down my body. She fit my cock between her melons and started titfucking me, using her gloves to push her breasts together around my dick. I just laid back against the post, looking down at Carol as she worked me over.

I'd always wanted to try this, but my girlfriend's 32Bs were too small to really make this work. Carol's tits, covered in a sheen of sweat, felt even more amazing than I'd imagined; the soft, warm pressure of her chest drained any remaining resistance from my shaking body. I closed my eyes, wanting to feel this as long as I could - the image of a sweaty Carol getting me off with her boobs wasn't helping, and I thought about puppies and baseball.
That helped, but only for a little bit; soon I was half-aware that I was making mewling noises, and I heard Carol purring: "Scott, you're trembling. I don't think you're going to last much longer. Are you?"

I didn't. I opened my eyes and Carol started going faster, panting at me as she slid her melons up and down my rod. Maybe ten seconds later she pushed me over the edge, laughing as cum spurted out of my cock, some of it shooting up and hitting her in the face, the rest landing on her tits, gloves, and my penis.

Then I slumped against the post, totally defeated. Carol pushed me down with her foot so I was resting on the bottom turnbuckle. I watched as she shimmied out of her boxing shorts and walked over to me. She straddled my face with her thick brown bush, lowering her pussy until it was just an inch away from my mouth. I took in her scent, then leaned forward a little and started licking her. I was used to having my hands free to part the legs and really get my tongue in there, but I did the best I could -  after a few licks up and down her slit, I pushed my tongue in. Carol moaned as I set about eating her pussy. After a few minutes she started taking charge, pressing her hips into me, pushing the back of my head into the turnbuckle. She started fucking my face and I just held on for dear life. She was close to her climax and after just a little bit she came, a guttering cry bouncing off the cabin walls - then, spent, she almost fell off me, stumbling away and sinking down to her knees.

She shucked her gloves, then came over to help me with mine (she made it look easy getting her own off - I made a note to try to learn how to do that). She grabbed a bottle of water outside the ring and we both sat against the ropes.

"Listen, Scott," she panted, "I like you, so I'm going to give you some tips." I nodded at her, too blown to verbalize a reply. "There's three ways to dominate your opponent - physically, emotionally, sexually. In boxing it's easiest to do it physically, but - " she squirted some water in her mouth - "that's usually what everyone expects and trains for. It's not as easy to dominate someone sexually with boxing gloves, but - " here she squirted some water on her heaving, cum-spattered breasts - "that just makes it sweeter when you do." She leaned in and kissed me on the cheek. "Just something to think about in your career."

My career? My head spun as Carol told me to open wide and shot some water into my mouth. Did I want to keep doing this?