Shemale Stories: A MILF Fucked

My ass had rarely been penetrated and my chute was pretty small. So my eyes went big as I joked, hoping it really was a joke, "Even my ass?"

"Definitely your ass," she nodded, not joking.

I prevaricated, as I continued fucking her dick between my tits, "I'm not sure that thing could ever possibly fit in my ass."

"Your daughter can take it," she revealed out of the blue, suddenly dropping a virtual grenade into the room! This wild surreal night had suddenly gotten very real.

"M-m-my daughter?" I stammered. As far as I knew my daughter was still a virgin.

"Oh yeah, she is one horny little slut," Chelsea said, as she stood up and got a bit aggressive. She turned me around slightly and pulled down my pants. "Shit, were you coming here already expecting to get fucked? No bra, no panties."

I admitted, lifting my feet up so she could finish removing my pants, "No, I was coming to feed a kitty, but after I got home I was going to read some erotica and get myself off with one of my toys."

"Big Black?" she asked, as she moved back up and put her cock between my tits.

"How do you know about Big Black?" I asked, in awe as I looked up at her. Big Black was the ten inch suction wall-cock I used when I wanted to fuck myself really hard.

"I made Simone ride it while I face fucked her one day while you were at work," she revealed.

"Oh God," I moaned, as she resumed fucking my tits... which had always turned me on.

"Simone and I went through all your toys and learned you like big things in your cunt. You have a pretty impressive selection, may I add. She knew what you really needed was a good hard fuck from a great big dick and she also knew that I had a big dick. Simone tells me all the time how much she loves my great hard fuckings, and I've had a crush on you for fucking ever. So here we are." My head was reeling as her big dick continued fucking my big tits.

"This is too much," was all I could get out.

"The truth about your straight A sweet daughter pounding a wall with her cunt, or the fact that my big hard dick will soon be pounding that wet cunt of yours?' she questioned.

"Both," I admitted, the conflicting emotions of being a mother and doing the right thing on the one hand and being a woman with needs and wanting to fuck that big thing right now on the other warring inside me.

"Just give in to your lust, my pet," she ordered, as she pulled me up, spun me around and moved her cock between my legs... teasing my wet pussy lips.

Although I wanted to do exactly that, I asked, so much information having been coming at me so fast I couldn't possibly process it all, "Are you two dating?"

"No, we're just fuck buddies," Chelsea answered. "She loves my big dick and I love her submissive, obey-every-command willingness."

Chelsea's cock was moving back and forth, not inside me, but teasing my fevered box intensely. I moaned, "Like mother, like daughter."

Although I hadn't guessed it was there, my daughter's submissiveness didn't surprise me at all. She was caring and compassionate and always trying to please others... it wasn't much of a surprise that those traits would accompany her into the bedroom.

My head was still spinning with lust for the big cock between my legs and with the revelation that not only was my sweet fresh-faced daughter no longer a virgin, but she also enjoyed taking a fucking huge she-cock up her butt.

"You didn't think your daughter was a virgin, did you?" Chelsea asked, as she pumped her dick faster across my slit, making my head light and my body burn.

"I had hoped so," I answered, still trying to come with grips with Chelsea's shocking announcement. My own little girl ass-fucking?

"If it makes you feel better, I'm the only one she's ever fucked," Chelsea offered. "But for me she sneaks over here regularly for a load of cum or a nice hard fucking."

"I can't believe it," I said, even though I couldn't help but believe it. I knew Chelsea wasn't lying.

"It was her idea to seduce you, too," Chelsea compounded the shock, and my eyes went big as everything suddenly made sense... twisted, kinky sense.

"No!" I gasped, somehow finding this newest revelation even more shocking than the fact that my daughter was an ass slut for our she-male next door neighbour... as I finally connected the dots to the earlier conversation about her using my toys on my daughter.

"Yes," Chelsea confirmed, before asking me the question I had been dying to hear. "Ready to go for a ride?"

"I've never wanted to take a ride more in my life," I answered, lust completely taking over as the time had finally come to squeeze that massive cock into my burning inferno.

She pulled away from between my legs and sat back on her bed.

"Well come ride me," she said, her cock standing at full salute for me.

"Yes, Miss, right away!" I nodded, quickly straddling her and lowering my cunt down onto her massive cock. As I descended, the visible portion of her cock was already shining. I wasn't coming, but I was so burning with lust that my fluids were flowing down her cock, coating it completely. "Oooooooooh," I moaned loudly as her cock spread my pussy lips apart and disappeared inside me... plunging to depths no flesh and blood cock had ever before navigated.

"Oh yes, take it all, my sexy MILF pet," Chelsea purred, as she put her hands on my waist and I touched down.

"Mission completed," I bragged, sitting proudly on her lap, her huge cock completely buried inside me.

"Don't get too cocky, you have many missions ahead of you, my pet," Chelsea promised, as I began riding her.

"I'm not cocky, you're cocky, you gorgeous she-male," I joked.

"I love fuck missions," I sighed contentedly, as I slowly rode her cock.

"And I love these tits," Chelsea declared, so I leaned forward and smothered her face with them.

"These old things?" I joked.

"These are perfection," Chelsea groaned as she kissed them all over, bit gently on my nipples, worshipped them, clearly in as much awe of my tits as I was of her cock.

"As is this dick," I complimented, beginning to ride faster, as her tongue gently explored the deep valley between my tits.

And for a few minutes we just fucked.

My moans increased.

Her moans increased.

I began to ride faster.

She began to suck on my nipples more roughly.

Then in one surprising move, she lifted me up with amazing strength, turned me around, lowered me back onto the bed on my back, kneeled very close to me while raising my butt to rest on the tops of her thighs, all this while staying buried deep inside me, and announced, "My pet, it's time to make you scream like that slut on the television."

"Oh yes Miss, make me your porn slut," I moaned, as she began slamming into me hard and deep, at an angle that somehow managed to rub against my clit, creating brand new waves of pleasure.

"You want my dick, my sexy MILF slut?" she demanded, pulling completely out of me and pausing just inches away from my pussy.

Desperate to come, desperate to have that cock back inside me, I answered, "Yes, yes, I want that big fucking pecker slamming into my wet, sloppy CUNT!"

In one stroke she slammed completely back into me and ordered, "I want you to come for me, Jill. I want you to come all over my massive hard dick."

"Yes, Miss," I moaned. "I'm so close. Please call me names, tell me what I am."

She laughed, but in a playful way, "Shit, it really is 'like mother, like daughter'."

"Simone likes being called names?" I asked, surprised, since I had only ever heard her swear once. That had been when her computer had crashed the night before an essay was due.

"Oh yeah, she only comes when she's being treated like a nasty cum slut," Chelsea revealed as she slammed into me.

"Ohhhhh," I moaned, as my orgasm was hovering near eruption but refusing to break free.

"Come now, you dirty MILF slut, you submissive cock sucking, cum swallowing whore," Chelsea listed, each nasty phrase sending tremors through me.

"Oh yes, fuck, yes," I babbled, my orgasm so fucking close, so on the brink.

"Come for me, you Mommy slut, be my three hole cum bucket just like your daughter," she demanded.

I have no idea why that was the sentence that broke the dam, but instantly my orgasm gushed out of me as I screamed at the top of my lungs, 'Yessssssssss!"

"Damn! You're even a gusher like your daughter," she revealed, as she kept pounding me throughout my orgasm.

"Oh God, I haven't come so hard... ever," I gasped.

She pulled out and said, "Now it's time to make this a trifecta."

"I'm serious, I really don't think I can take all of that in my ass," I repeated, even though the idea of a nice hard ass fuck was somehow appealing.

"If your daughter can take it, you can too," Chelsea said, as she went to a dresser and pulled out some lube.

I watched, terrified, but knowing that no matter how afraid I was, I was going to do whatever she told me to. She would never need to force me to do anything; all she had to do was ask, and I would obey. That's who I am.

"Get on all fours on the floor," she ordered.

"Yes, Miss," I obeyed, my body weak and still trembling after the earth shattering orgasm.

"Good pet," she purred, as she dropped to her knees behind me, poured lube down the crack of my ass, and slid a finger inside.

"Please gape my ass first, Miss," I requested, knowing that would make taking her mammoth horse cock a little easier to take.

She slid a second finger in and wiggled them both.

"Mmmmmmm, it's been a long time since I've had anything up my ass," I moaned. Giving up my ass had always been my ultimate act of submission. After that, there were never any barriers remaining.

"Well, I love to fuck tight assholes," Chelsea said, slapping my ass playfully.

"You're in luck, Miss. I have a really tight ass, and I'm anally retentive," I joked, as I felt her cock begin to poke at my back door.

"Ready?"

"My ass and everything else is yours to use as you please, Miss," I answered; brave words, but I was bracing myself for the pain that was bound to come any second now.

"Here it comes," she announced, as I felt my asshole being spread open very wide.

Pain coursed through me as her entire cock somehow crammed itself deep inside my ass.

"So tight," she moaned.

"So big," I whimpered.

"But you like them big, don't you?"

"God, yes," I admitted, loving her huge cock and knowing that the moment she beckoned, I would be back on my knees, offering all three of my fuck holes.

As she began slowly fucking my ass, she continued, "And you will be an obedient MILF pet, right?"

"Yes, Miss," I nodded, as I gradually got accustomed myself to the anal intrusion.

"Good pet," she said, her hands on my hips.

After a couple minutes of slow ass fucking, the pain dissipated... mostly... and was replaced by a growing pleasure.

I begged, wanting her cock deeper, wanting her to ream my ass, "Fuck my asshole, Miss, fuck it like you own it."

"As you wish," she chuckled at my word choice, suddenly bucking her entire body into mine.

"Fuuuuuuck!" I screamed, a new pain quickly ushering a new pleasure.

"You like it rough, my little MILF slut?" she questioned.

"God, yes," I moaned. "I love being pounded by you and your huge dick."

She fucked me for a good ten minutes, both of us moaning in unison by the end, until she grunted and without warning my ass was filled with cum for the first time since my prom night.

"Oh yes, fill my asshole with your cum, baby," I moaned, tightening my ass cheeks to milk her cock the best I could.

"Oh yes Jill, you have the tightest asshole I've ever fucked," she said, as rope after rope of cum spewed deep into my rectum.

After she was spent, she pulled out of me and collapsed onto her bed.

Feeling naughty, and wanting to show her just how big a submissive slut I was, hopefully a dirtier slut whore than my daughter, I crawled onto the bed and grabbed her still hard cock, that had just been buried in my ass, and took it into my mouth... even as I felt cum oozing out of my asshole and trickling down my legs. I managed not to gag at the taste... I would need to start giving myself enemas before visiting Chelsea. But that would be later; now was for the humiliation that was washing over me and that I relished... even if it was self-inflicted humiliation.

She moaned, "Oh fuck, that is so intense," as she grabbed my head.

I had only sucked her for a minute before she weakly demanded, "Stop!"

I did as I was told, looking a question into her eyes, and she laughed, "Sorry, but I really have to pee."

"I've done that too," I smiled welcomingly, although both times I had done that were long ago when I had willingly been peed on by girls in college. That had been humiliating too, and had left me with a very warm feeling, inside and out.

"Good to know," she said, as she stood up. "A bigger slut than your daughter... who would have guessed?"

She headed out and after waiting a couple minutes for her to return, I got dressed.

When she returned, Chelsea asked, "Do you have your cell phone?"

"Yes," I answered cautiously, patting my pocket.

"Good, pull it out. Time for a selfie," she said, as she guided me to my knees, stood behind me and draped her cock over my forehead.

"What? Really?" I asked.

"Yeah, to send to Simone," she revealed.

"I can't do that," I protested.

"I just finished talking to her on the phone, and she's super excited to know you finally got laid."

"Oh my God," I said, shaking my head. "Everything has been turned upside down."

"Upside down, that is a great position," Chelsea joked, before instructing, "now take the picture."

I sighed, but obeyed, like a good submissive.

Chelsea then took my phone and assumedly sent the photo to my daughter.

"Please tell me you didn't send it to my daughter," I asked, even though I knew she had.

"I also sent it to me and to your ex-husband," she said,

"My ex???"

"Yeah, I got the number from Simone. Now he can see what you really need around to please you."

I laughed, "Well, you are twice his size."

"Now I don't recall telling you to get dressed," she said. "The night is still young."

I shook my head, "I forgot how much stamina young dicks have."

"Oh, I have at least two more loads," she promised.

"One for my cunt and one for my face?" I hoped, as I quickly stripped.

"Sounds pretty good to me," Chelsea laughed, as she brought me back to the bed. "Now let's see if you and your daughter taste the same."

I straddled her face and took her cock back in my hand and said "I hope my pussy is like wine and mellows well with age."

As she buried her face in my pussy and licked, she smacked her lips loudly and said, "Yep, 'like mother, like daughter'".

As I took Chelsea's cock back in my mouth I really had no idea what I would say to Simone when I saw her, or when she called me, but that was a conversation for another day.

The task at hand was clear... get this cock to shoot at least two more loads....

The End

Here are a few great shots that didn't quite find good places in the story:

Jasmine 2017