Ronnie and I have been through a lot being best friends watching all kinds of porno, discovering paraphernalia, pulling our pricks alone or together nothing was taboo between us. We even explored our bisexual curiosities for a while never really making it beyond cock sucking which prompted us more to challenge each other in pursuit of our other sexual endeavors. Picking women at random of whom we could fuck before the other and this went on for some time until the challenges became too easy that we had to raise the bar?

One day after the gym we’d gone to my house for a little light weed smoking, post workout relaxation of porno watching and jerking off when Ronnie said, “we haven’t had a really good challenge in a while have we”? Ronnie was a short muscular guy with dark short hair and a truly thick hard dick, I his much taller blond counterpart sported more length on my cock than girth as we enjoyed stroking our dicks. While talking about something a little more challenging it just so happened my mother knocked on my door, we quickly pulled our pants up and turned off the porno.

My mother May was the typical divorced housewife who had put on a few pounds over the years nonetheless beautiful, voluptuous, sporting massive tits and an ample ass that caught Ronnie’s eyes whenever she walked into the room. My mother was no fool and could smell the weed (being a pot smoker herself), but being over 18 she didn’t really care of our recreations or Ronnie’s evident crush over her. By the look in his eye I could see that he’d like nothing better than to pull out his still hard dick and fuck my mother right there if she’d let him.

Mother asked, “you staying for dinner Ronnie, I’ll set another spot” he smiled and accepted the invitation jubilantly as she turned to walk away with his eyes affixed on her ass. As the door closed Ronnie said, “my God how could a man like your father let a woman like that go or not want to fuck a woman like your mother”? I replied, “as mothers go yeah she’s pretty hot for her age, but your mother’s just as hot” Ronnie’s mom was a tall, leggy blond bombshell around my mother’s age of whom was flirty around me and subsequently liked younger men.

Whether it was the weed or our hard cocks that made us think as we finished jerking off then cleaning up for dinner Ronnie proposed an unusual challenge. I could see his wheels turning I said, “let me guess, the first to fuck each other’s mother right?” Ronnie smiled saying, “I thought that at first, but then how simple would that be?” he paused, “how about a real challenge of seducing our own mothers”? I replied, “really?” Ronnie laid it out in such a way that made sense from the level of difficulty it would take to entice our own mothers and neither he or I were averse to try something that wild.

I agreed on the conditions, but that the terms of win would be higher than usual if we were to succeed “the winner fucks the loser’s ass” something Ronnie and I had never done. Ronnie approved of the debaucherous proposal in that he felt we’d both probably fail the test this time, so as we went downstairs and sat together with mom eating. I soaked in her beauty calculating my first steps based on (surprisingly) my now departed father’s drunken recollections in graphic detail of my mother’s preferences and prudishness.

Ronnie thanked my mother for dinner as I walked him to the door and we shook hands on the agreement for the last time, the caveat would be visual proof of a photo or video that we really fucked our mothers. As I returned to the table to help my mother clean up I pondered what if anything I could use to entice my own mother to see beyond the fact I was just her son and beyond that I’d have to see her differently as well. The first few days of testing the water were interesting, randomly leaving my door ajar more as I came home from the gym to shower and change when I knew my mother was upstairs.

Standing naked in my room I’d flex my muscles in the full length mirror while I could see my mother stroll by glancing inside which she (at first) would pass by quickly. A week had passed meeting Ronnie at the gym with any updates of anything that had transpired on either of our sides, though I was careful as to what steps I’d taking thus far giving him any ideas he could use too. By all accounts Ronnie and I weren’t any further than the other although it was time to ramp up my enticement which would come in the form of something a little more obvious to my mom.

As I came home from the gym I would always take my showers at a time I knew my mom was upstairs waiting till I heard her near the bathroom door in the hallway. Mother was in her nightgown with a load of towels for the bathroom closet when I walked into the hall with my towel wrapped around my neck and not my waist. A surprise to her standing there with my cock exposed that I played it off as if I didn’t care, fact is she saw me as I excused myself to my bedroom. Leaving the door open again looking in the mirror mother stopped by the door, this time she paused longer looking at me more interestingly.

Acting like I couldn’t see her I began stroking my cock to its fullest, pumping my prick for quite a long time before she’d eventually move away from the door. The next step was crucial in making her aware that it was all about her that these circumstantial sightings were occurring, so after another (so called) misstep into the hallway naked. I left the door of my bedroom open a little more as I placed the towel under me as I watched a porno to jerk off, the difference was this time I was sniffing a pair of her own worn cotton panties. From the reflection in the mirror I could see my mother standing there staring intensely at my cock, licking her pretty pink lips as I wrapped the panties around my cock spewing a load of cum all over them.

The culmination of these calculating steps would come to light as Ronnie had informed me he made a move on his mother when they were drunk together that landed like a lead balloon. When I got home that day it was rather odd, but mother was downstairs in the dining room sipping on a glass of wine in her long nightgown as she said to me, “won’t you join me”? It wasn’t any special occasion that I knew of that she’d be drinking so early as she poured an extra glass of wine for me, in the center of the table a glass ashtray with a doobie. Putting my gym bag aside I joined her at the table as she lit the joint that we shared while sipping our wine and as we got a little higher she would finally confront her curiosities.

“You’ve been acting rather strangely, is there anything you’d like to tell me?” she asked, I remained aloof as she produced the pair of her worn cotton panties saying, “borrowing my panties to pleasure yourself, you don’t find that odd seeing that I’m your mother”? I feigned an apology “sorry it’s been kind of a dry spell for me and I needed something to make it feel a little more real” though she didn’t mention her seeing me naked or looking in on me jerking off. We toked up some more on our third or fourth glass of wine when I said, “you’re presence, I mean you’re an attractive woman I see everyday and I didn’t think it would cause harm to use your scent to excite me”.

These words seemed flatter her as thoughts about what it meant for her own son to notice her as just another woman given that mother hadn’t dated or fucked anyone since dad. Well aware of what I was doing to hopefully stimulate a longing of her curiosities further I said, “I’ll be glad continue this mom, but first I’ve got to get a shower I’m still dirty from the gym” and excused myself. In the shower I’d take my phone to listen to music and this time it was to taunt Ronnie with the message, “stay tuned, I’m getting close”! He replied “no way!” though I wasn’t sure yet I shut off my phone’s alerts off knowing that Ronnie’s texts would be relentless.

With mother downstairs after the shower I wrapped the towel around my neck and walked out into the hall once again nude. Intending on slipping into only a pair of shorts before rejoining her I grabbed my phone and as I opened the door my mother was standing there, my cock immediately hardened. Her long blond hair pulled back she smiled up at me with her pretty face as she dropped to her knees grabbing my cock as her pink lips encircled my throbbing knob. I casually snapped a photo and sent it to Ronnie as I set my phone to a live video streaming for his eyes only as I pulled my mom up off her knees.“Not here in the hallway mom”, we walked to her room where unbeknownst to her I placed the camera by the bed, I knew Ronnie was watching catching only the last text he sent “no fucking way dude”!

I turned my attention to my mother as she unzipped her nightgown to reveal her fully naked chubby body to me as her tremendous tits bounced upon releasing them. Producing the still soiled panties from her pocket she handed them to me and moved quickly forward to her knees once again. Sucking my swollen dick into her warm wet mouth I inhaled her essence from the crotch of the stained panties while deep inside her mouth her tongue circled around my shaft as she swallowed me deeper. My father was right when telling me my mother “was one hell of a cock sucker”! She forced my long hard cock to the back of her throat without gagging, her tongue wagging across my balls all while looking up at me with her pretty eyes. Her chubby body leaning in as she grabbed my ass, wildly deep throating my dick that made me want her pussy that much more.

Tugging her up off onto her feet pushing her back across the bed as I knelt in between her hefty legs that I placed on my shoulders. I spread her knees open to reveal her bushy blond cunt, my face pressed tightly inside her pink lips while my tongue lapped at her dripping wet pussy. Mother’s scent drove me wild as she screamed for me to “eat her pussy” lathering into a creamy white sticky mess as she climaxed for the first time. Plunging my tongue into her pussy hole as deep as my face would allow she grabbed the back of my head gyrating her cunt, washing my face in her juices to another incredible screaming orgasm. My throbbing cock had swelled to the point of a slight pain in the head, the incestuous taboo wasn’t lost on us fueled by her insistence referring me now as “son”.

Mother screamed, “fuck me son, stick that big dick in mommy’s pussy please” she begged as I pushed her further onto the bed looking over at my phone to find just the right angle. Across the bed although it wasn’t a close up it captured the action well as I slid between her thunderous thighs and plowed my cock into her fiery soaking wet snatch. Mother’s pussy was so tight having not fucked for so long as she wrapped her legs around my ass, the bed shaking as I fucked her hard as tears began streaming down her face while she met my thrusts. I couldn’t resist sucking her huge tits as my cock plowed deep inside her sloppy wet cunt, a slightly too hard nip at her nipple made her jump and scream, “I like the pain son, fuck me harder”!

I pulled out to flip her onto her knees plowing deep inside her as I held her hips and fucked her even harder to her intense new orgasm as she screamed into the pillow. Mother was in another world of her own when she looked back over her shoulder to say, “make it hurt son, I need it bad” which I took literally. At the risk of possibly overplaying my hand I pulled out of mother’s sweet wet cunt and pressed the tip of my hard cock against her anus, looking at the camera to wink foreshadowing Ronnie’s fate. I pushed hard as my cock stretched my mother’s tightly puckered ass wide open, slipping deeper into her asshole as she screamed “that’s it, fuck mommy’s ass”! I wasted no time slamming my balls against her ample ass fucking her virgin tight ass hard and deep while she screamed my name. Nothing had ever felt this wrong and just right at the same time as I told her, “just think about all the times you were on my ass about something, now this” mother giggled as she climaxed.

My cock pumped hot loads of cum inside her fat ass as mother fell forward crashing into the bed, her ass dripping I spread her cheeks lying down and licked her clean of every drop of my cum before we’d finished. Needless to say this became a regular thing between mother and I though Ronnie would be next as per our bet. True to his word the next day Ronnie was over and after we’d gotten hard jerking off I coaxed him to suck my dick, something he really liked. Mother must have heard us, coming to my door with a rather curious expression on her face and naked. Ronnie tried as he might to look her way as she said, “can I join you two”?

I grabbed Ronnie’s head and pushed my cock deep into his throat as mother made her way to the bed with her tits pressed against my face as I licked her hard pink nipples. I looked up at my mother and said, “I know Ronnie wants to fuck you” as he sucked my cock even harder to convey his hope I would allow it. “Ronnie would love to fuck you, but first he owes me a debt” though mother didn’t know what that was I told her to lay down and let Ronnie lick her hot pussy. Mother climbed on the bed spreading her sweet cunt open as I brought Ronnie to his feet as he knelt on the bed, his face between her legs and licked mother’s cunt feverishly.

Mother looking up as I slathered my swollen long cock in lube and knelt behind Ronnie’s upturned ass. The hard tip of my throbbing dick piercing his virgin tight asshole for the first time mother’s words amused me, “so did he win or lose?” I replied, “with you here mom, I’d say both”! I slipped my cock deeper inside his ass fucking him harder than I thought and why not his gift of my mother’s wet wild pussy would outweigh a bit of a sore asshole. Ronnie put up a bit of a struggle as my cock buried deep inside his ass, turning to protest, “not so fucking hard dude” that instead of letting up I pushed his face into my mother’s cunt and said, “shut up and eat my mom’s cunt you bitch”!

Ronnie did just that as I fucked him furiously to his moans tickling mother’s snatch when I decided to let him off leash, pulling my cock from his ass quickly. “Fuck her, I’ll be watching” sitting beside them I stroked my cock hard as Ronnie plowed his big fat dick in my chubby mom’s awaiting pussy. Wrapping her legs around him Ronnie wasn’t long for this pleasant surprise as he fucked her juicy cunt hard and fast, mother watching me jerk off made it even more exciting. A long groan and Ronnie had nutted inside my mother’s snatch just as was cumming too, he pulled aside panting. I said, “that’s no way to leave her” and with my sticky hand I plunged two fingers into my mom’s twat while I licked her clit to a climax.

It eventually came out as we laid together in bed what exactly the bet had been to my mother’s amusement as she kissed Ronnie telling him, “maybe I could convince your mother to fuck you though it may mean licking pussy myself, I’ll see what I can do”? From that day you couldn’t have wiped away Ronnie’s smile every time he came to dinner hoping to eat something else!?

 

Terrific story!

 

Very hot! Wish it was a bit longer but that got me all worked up. Thanks!