I knew every one of my friends was doing it and always telling me how wonderful it was and how much they loved it. Taking it up the butt, I mean.
Me, I was stuck with a dick of a boyfriend in Phil who got grossed out at the thought of sticking his precious pecker up my ass in case he got some poo on it. Lord knows, I tried with him. I wiggled my ass, I gyrated my butt, I even tried to make him miss his intended target, my pussy, when he was taking me doggy style, but I just couldn’t get his cock into my ass.
“Just fuck me in the pooper once,” I begged him, “if you don’t like it we won’t do it again, promise.”
“It aint going up your shit hole,” he answered.
“I’m eighteen years old and I’ve never been butt fucked,” I complained, “I feel like a freak.”
“Ass fucking is
freaky, that’s what queers do.”
“Screwing a girl’s ass doesn’t make you a queer, you nut!” I screamed.
“It isn’t natural.”
“Maybe not, but it’s supposed to be good. Ellie Davidson said ..”
“Ellie Davidson is a slut.”
“She’s my friend and she says being buggered is great, so why am I not getting any?”
“Because your boyfriend, who you love very much, is not going to do it, is why not. Accept it, I am not going to ass fuck you. Not today, not tomorrow, not ever.”
And he was right, I did love him, because apart from the ass thing we got on great, loved the same things, were a real couple. Which is maybe why the anal thing really bugged me.
“It’ll probably really hurt me and I’ll never want to do it again,” I insisted.
“Which is a good reason for not doing it. Ass holes weren’t built to take cocks.”
“Just once,” I pleaded.
In answer he pulled out his cock and waved it in my face. “Blow me!”
It was always his way of ending an argument. And it always worked.
“What’s up, honey?” my Mom, May, asked me at the breakfast table the following morning.
I continued shovelling my cereal into my face.
“Did Phil do something?”
“It’s what he won’t do,” I complained. There had always just been my Mom and me so we were pretty close.
“What’s that, Lisa, what won’t Phil do for my little girl?”
“He won’t fuck me in the ass, Mom.”
My Mom was cool. Since my dad had left us she’d had lots of boyfriends but she insisted on not getting too involved with any of them and settling down till I was twenty one. I knew it was a sacrifice and I appreciated it.
“You take it up the ass, Mom?”
“Yes, I do, as a matter of fact. Not too often, but it’s nice now and again.”
“That’s what everybody says, but Phil’s scared he’ll get shit on his cock so he won’t stick it up my pooper.”
“Phil is a young fool, he doesn’t know anything.”
“Ellie Davidson says it makes her come every time. That would be real nice.”
“Yes, well,” Mom said reaching out and stroking my hair, “getting a dick in your butt can be quite intense.”
“Doesn’t it hurt?”
“Uncomfortable at first, yes, especially if it was an inexperienced young pup like Phil trying to bugger you, which is why I don’t think you should have him as your first anal lover.”
“But he’s my boyfriend.”
“Yes, I know. But young boys aren’t very good at sodomy. They’re too impatient, too rough, they could hurt a girl and that might put her off something that is truly pleasant and enjoyable.”
“So, what are you saying?”
“I think that if you really want to be buggered you should find a more experienced lover who knows what he’s doing.”
“I couldn’t cheat on Phil,” I insisted.
Mom smiled. “Sure. But if you get real desperate to take it up your pretty little ass, you come and tell Mom and I’ll see what I can do for you.”
I wasn’t really listening. It was the same offer she’d made me when I’d told her I was going to lose my virginity to Phil a year ago. She’d suggested I find some older, more experienced, guy who’d teach me how to do it right. But the thought of doing it with some old guy really grossed me out so I’d passed on it and sure, Phil did make a mess of it the first few times we fucked, especially with coming real quick, but we’d got there in the end. Now, though he never made me come when he was fucking me, he did at least last a little longer and I was pretty sure that eventually he’d be able to make me come. In the meantime it was just me and the little vibrator that Mom had bought me for Christmas that gave me my special thrills. But I could see her logic, I was a year older and mature men didn’t seem so threatening any more. And they certainly would know how to treat a girl’s ass better than Phil.
I would have forgotten all about it, however, if Phil and I hadn’t had the Mother of All Fall Outs a couple of weeks later. I’d woken up over at Phil’s place with Phil spooned behind me. He had morning wood so I decided to enjoy it a little and started wiggling my ass against the head of his cock. It wasn’t really going anywhere, my pooper was too dry and tight, but he woke up and screamed at me, “Were you trying to get my cock up your ass, you dirty bitch?”
“Hey, I was only fooling around.”
“You’re obsessed, you dirty slut. That’s all you think about, getting your ass fucked, and I’m getting damned freaked out with it.”
“You’re over-reacting,” I said quietly, trying to placate him, but that just seemed to get him more worked up.
“Don’t play that innocent little shit with me, it don’t work anymore.”
Before I knew it we were cussing each other out and I was getting dressed and grabbing my stuff swearing I never wanted to see him again. And that was the end of Lisa and Phil.
“It’s just a spat, he’ll be back,” Mom said, but I wasn’t convinced. Despite that, Mom really did seem to know best because sure enough within a few days we started missing each other but, both being stubborn pigs, refused for another week to make that fateful phone call. Eventually it was Phil that relented and called, which was points to me!
He apologised and admitted he’d flown off the handle, but I knew that I had the upper hand for the moment, so it was important to wring some concessions from him.
“Will you fuck me up the ass?” I demanded.
“Yeah,” he said finally, but not very convincingly, “but I’m gonna wear a condom.”
I hated the damn things and would rather have had it bareback, but anything was better than nothing.
“Okay,” I agreed.
I had him where I wanted him and it looked like I was finally going to get my pooper stretched but I still had to punish him. For one thing, I decided, he wasn’t getting my anal cherry. He’d had my pussy one and that was enough for one guy.
So I said to my Mom, “That thing you said, about an older guy teaching me about anal, who did you have in mind?”
She was making dinner and I think my question caught her by surprise. “Uh, I don’t know, honey. Is there any of my men friends you really like?”
I’ll say one thing, my Mom had good taste in men. All her boyfriends were hunks, well-built and attractive. What really got her going , though, was a man’s smile which I also realised was very pleasing. But to pick one from the half a dozen guys that were nailing her was a hard call.
Finally I said, “How about Ken?” because her shortest lover was a character and made me laugh.
Mom frowned. “Ken’s kinda big, honey, down below, if you know what I mean.”
“Little Ken?” I said, quite shocked.
“Never let a guy’s height fool you, sweetie. Ken’s hung like a horse.”
I tried to imagine Ken, who couldn’t be more than five six, with a horse cock but couldn’t raise such a weird picture.
“Ken’s fun, Mom, I like him better than your other guys. Plus he treats me like an adult.”
She grimaced. “On your own head be it. I’ll see what I can fix up.”
The following day I was screaming at her to cancel everything. “Daisy Travis told me that taking it up the ass stretches you and loosens your pooper muscles so much that when you get older you shit your panties.”
Mom made a face. “Do I shit my panties?”
I shook my head.
“Well I’ve been taking it up the ass from before you were born. Just don’t do it every day and give your butt hole time to recover and you’ll be fine.”
“Are you sure?”
Mom hugged me. “Listen, kid, I wiped your tush plenty of times, so I’m no stranger to shit. Don’t worry about it.”
Re-assured I waited for the weekend and losing my anal cherry. I was nervous as a kitten, of course. This would be my first time with any other guy but Phil, my first time with an older guy, my first time up the ass. And to top it all off, the guy was going to be one of my Mom’s boyfriends. That was a lot to firsts to take onboard.
When the time came, of course, Mom became a control freak and tried to run the show. She’d no sooner sat Ken down and given him a beer than she started handing out orders.
“There will be no kissing, no booby feeling, no pussy fucking. This is not for your pleasure, Ken, this is for Lisa.”
“Go to hell,” Ken said. He stood up to my Mom, which was another one of the reasons I liked him. “If hot-pants here wants her boobies felt then, hell, I’m gonna feel them.”
“Ken,” Mom said sternly, “You are my gentleman friend and I am not having you fondling my daughter’s titties.”
“Yeah, but you want me to fuck her pooper,” Ken protested.
“As I’ve explained, that is so that she will have her first experience of anal sex with a more mature and knowledgeable man, not so you can enjoy yourself.”
“Hell, if I’m not allowed to enjoy it, I’m not doing it.”
Mom smiled and played her ace. “Show him your butt, Lisa.”
I was sitting with a glass of wine but I’d dressed special. I was wearing a short, frilly skirt which really showed off my legs. I stood now, bent over and flipped the back of it up, knowing that my panties didn’t hide much.
“Jeeze,” Ken breathed, “No fair.”
“You’re not going to screw that?” Mom asked sardonically, adding to me, “Play with it, honey.”
I ran my hands over my ass cheeks, unsure of what she wanted me to do.
When Ken spoke there was a croak in his voice. “I think Lisa should decide what she’s going to allow me. If she doesn’t want me to kiss her and stuff, I won’t. But it’ll be a whole lot better if we didn’t do it like a medical demonstration.”
I think Mom and I could both see the strength of Ken’s argument especially me. The last thing I wanted was to be bent over, lubricated and have Ken stick his dick up my butt. There should be something special about the event more than the basics. But Mom didn’t give anything up without a fight. “She’s a kid, she doesn’t know nothing,” she said, which didn’t exactly endear her to me.
“Shit, this is crazy,” Ken barked, waving me over to him, “Come sit on my knee, honey, let’s get this party started.”
“Don’t you dare!” my Mom warned.
“Do you want me to fuck her ass or not.”
“Not if you’re going to be pawing her up first, you pervert!”
I’d straightened up and looked at the pair of them, bickering. I couldn’t help but laugh. The pair of them turned to glare at me.
“It’s my butt,” I said firmly, “and if I remove it the party’s over, so we’ll do it my way.”
They regarded me with a new respect which was kinda cool. “No, Mom, you go sit beside Ken and start making out with him.”
“What?” my Mom asked, puzzled. “This is meant to be for you, baby.”
“Yeah, yeah, but I want to watch you and Ken get it on. I want you to go all the way, with Ken fucking you to show me what you like. If I’m into it I might join in.”
They both looked at me as if I was mad but could tell that I meant it. Mom hesitantly moved towards her boyfriend. Ken took her arm and pulled her onto his lap before gluing his mouth to hers and kissing her passionately. I retrieved my wine and at down to watch the action.
His hand went up her skirt almost instantly but he didn’t grab her crotch right away but stroked her thighs. Her hands were on his head, running through his hair as she returned his kisses.
It should’ve been weird watching my Mom like that, but it made me feel good. I moved my own hand up the inside of my thigh. I’d watched plenty of internet porno with Phil but this was different, this was live, with people I knew. I saw my Mom gyrate her butt on Ken’s crotch and tried to imagine his big cock getting harder. He’d pulled her tits out of her top and was nuzzling her tits and nipples and she’d thrown her head back and was moaning. Ken pushed Mom’s skirt up and I saw that she was wearing hold-up stockings, the dirty bitch. But that was unfair, I knew what older guys liked, and if I’d have thought about it I would have dressed like a hooker too.
Even though his head was buried between my Mom’s big boobies I could see Ken’s eyes flash up now and again to check me out. I’d spread my legs to allow myself access and was gently tapping my fingertips against my crotch, which was probably giving him something of a show too. It was the method of masturbation I’d perfected to pass the boring hours in school. Just enough to keep you hot, but not strong enough to make you scream out with a come.
Ken pulled my Mom’s panties off, making a big play of peeling them down her thighs and calves so she could kick them off. Her pussy smelled of musky sex and the odour soon filled the room. Immediately his hand went between her legs and he started working her pussy, which made her groan even louder. She had a big hairy bush totally unlike my own little waxed treasure.
“Enjoying the show?” Ken shouted over to me.
I spread my legs wider in answer which made him grin.
“I gotta suck your cock,” my Mom announced.
“You don’t have to ask twice,” her lover answered, bouncing her off his lap onto the couch. He stood up, unzipped his pants and pulled them down. He wasn’t wearing any shorts and his cock reared up like a stallion.
“Oh my God!” I said involuntarily, “It’s enormous!”
“I warned you,” Mom answered, getting down on her knees.
It was indeed massive, curving up from his groin almost to his belly button with a bulbous red head at the top of it. Mom took it in both her hands and ran them up and down the shaft possessively. Then she pulled it down and licked the glowing head with long sweeps of her wet tongue. I pulled the gusset of my panties aside and inserted a finger into my pussy. Unsurprisingly I was soaking.
Ken grabbed Mom’s head and it was obvious by the thrusts of his hips that he wanted her to take him in his mouth, but she persisted in teasing him with licks along the shaft, on the head and round his hairy, hanging balls. They were as impressive as his cock, dangling heavy between his legs.
“Suck on it, baby,” Ken begged.
She finally relented and took the head of the lethal looking thing into her mouth, a look of utter bliss on her face as she chewed on his thick cock. Ken stood with his hands on his hips, the star of his very own porno as he fucked my Mom’s face.
He turned towards me. “Wanna piece, honey?”
Mom spat his cock out. “She is not
sucking your dick, Ken!”
“Her eyes says she wants to.”
My Mom looked over at me and I blushed and turned away. I didn’t know what I wanted. I was incredibly turned on, watching them and my pussy was sopping, but I didn’t know if I was ready to participate.
“Do you want to suck Ken’s cock, baby?” my Mom asked me.
Almost robotically I dropped to my knees and shuffled over to her side. “Just let me taste it,” I whispered.
Mom held it out to me and I licked at it tentatively with my tongue. It was burning hot but not unpleasant. “You can suck it if you want,” Mom conceded.
I took a hold of the monster and opening my mouth wide inserted it in there. Ken had put his hands onto my head and the minute I closed my jaws he began thrusting into my mouth almost choking me.
“Easy, Ken,” my Mom warned, grabbing his wrists, “She’s probably never had anything that big in her mouth before.”
“You like my cock, Lisa” Ken asked.
I nodded and grabbed for his big balls. They were about twice the size of Phil’s and writhed in my hand as if they were alive.
Mom stripped off the rest of her clothes and lay back on the sofa, diddling herself with her fingers. Ken reached over and groped her boobies, his cock still between my teeth. I liked sucking it but I couldn’t believe such a big thing was ever going to get up my butt. Maybe Mom had been right and I’d bitten off more than my ass could chew.
“Ready to fuck me, Ken?” Mom asked, spreading her legs wider.
“I thought I was supposed to fuck Junior’s ass.”
“Oh, give Momma a little piece first, honey.”
My Mom’s pussy was obviously a better prospect than my tiny mouth so Ken pulled out of me and lowered himself onto my mother. They were obviously familiar lovers, knowing each other’s bodies and slotting together comfortably.
Mom let out a loud satisfied sigh as Ken embedded himself into her hot pussy. She pulled her knees back and her lover started pounding into her with loud squelching sounds. She pulled me up from the floor to be beside her on the sofa.
“Is that good, Mom?”
“Oh yeah, Ken’s the best. Aint ya, baby?”
Ken grinned. “I try to please.”
All I could see was the length of his cock thrusting in and out of Mom’s thick bush, but from the noises she started making it was obvious that he was pleasing her. Before long her sighs and moans turned into grunts and she pulled Ken down onto her so I couldn’t see anything but her nails raking his back. She was nibbling on his ear lobe when her orgasm hit her and it must have come on suddenly as she nearly bit if off causing him to wince. I had my hands down my panties again by this time and came in concert with my mother though not as loudly and dramatically. Her hooting and shouting would have woken the dead. As she came down from her high she turned and whispered to me, “Take your panties off, sweetie, I think it’s time you got what you wanted.”
She pushed Ken off her and dived down to his cock. “I’ll get your cock wetter and you lick her ass to lube her with your tongue,” she ordered, trying to take command of the situation again.
With Mom busy between his legs Ken stole a kiss of my lips and a suck at my tiny boobies before pushing me onto my back and lifting my legs. His thick tongue lingered briefly at my juicy little crack but he didn’t seem too unhappy about moving back to my little poo hole and inserting his tongue there. It felt weird and ticklish but I felt myself opening as he probed at me, forcing his saliva into my anus, before his fingers started stretching me too.
“You have the sweetest little asshole, Lisa,” he cooed at me and I wondered if Phil would ever be brave enough to stick his tongue up my so-called shitty ass. I pulled my knees back so he could get his tongue and fingers in even further and what had been ticklish started becoming very arousing.
“Oh, Ken, that is just so great,” I croaked, suddenly realising that having your ass penetrated could be good and not just because it was extra dirty.
“She ready?” Mom asked her lover.
Ken raised his face from my pooper. “As ready as I can get her.”
“Okay, honey, here it comes. Get ready.”
I bounced up and assumed the doggy position, spreading my ass cheeks with my hands.
“Whoa, she wants it bad,” Ken snorted.
“Not that way, honey,” my Mom advised, “For your first time it would be better if you were on top so you can control the action.”
She pulled me up and allowed Ken to lie in my place. His great cock swayed like a flagpole in the breeze till my Mom grabbed it and held it steady.
“Climb on top of it, sweety, and just lower yourself onto it at your own pace.”
I straddled Ken gingerly, facing away from him, and almost automatically my pussy tried to engulf his cock. Even there it felt big but Mom wasn’t having it anyway and pulled it out before even the tip was all in.
She manoeuvred it until my puckered little hole was just hovering over his bulbous head. “Just take your time and if it hurts, just stop,” she instructed.
I lowered myself a little more and Ken’s cock touched my ring. I froze, almost instinctively, and wiggled my ass onto the head of his cock.
“There you go,” Mom breathed as the first inch pushed its way into my butt. Now that my ass was gripping his cock she let go of it and used her hands to spread my cheeks. I wiggled some more and a bit more slipped in.
“That’s my girl, the head’s in.”
It wasn’t sore, it wasn’t uncomfortable, it was weird, like I needed to take a huge dump. Mom seemed to be reading my mind.
“You’ll feel like pushing out because that’s what your ass is designed to do principally. You have to overcome that feeling and let the cock inside you.”
I lowered my weight onto Ken’s cock and thought I must have at least half of it up me. Of course I’d been ignoring what he was feeling totally, but should have known that his instinct was to thrust into me. He reminded me of that with a brief jerk which, because it was unexpected, made me jump a little.
“Easy, tiger,” my Mom scolded him.
“It’s okay, Mom, I can take it. Go ahead, Ken, fuck it into me.”
He didn’t need any second telling but grabbed my hips and pulled me fully down on him while thrusting upwards with all his might. I let out a loud groan, part pleasure, part pain, but with the good far outweighing the bad. I’d done it! I had a man’s cock up my ass! I’d lost my anal cherry!
“Good girl,” my Mom cooed, stroking my face. “My big brave girl, took Ken’s cock without a squeak. Is it good, honey?”
“Oh yeah,” I breathed, wriggling my butt to make myself more comfortable, “It’s fucking great.”
“Language, young lady!”
We reached something of a conflict at this point. Ken wanted to bounce me up and down on his cock, but I liked the fullness of him inside me and wanted to grind down on him, to lift his balls and rub them against my pussy and clit. Somehow we managed to get things moving and I felt a come building up. It wasn’t one like I was used to, but something strange and deep, like a fire in my belly. Giving up on the grinding I started moving up and down on Ken’s pole, feeling it thrusting in and out of my stretched butt hole. I leaned forward like a jockey, grabbing at his balls like they were reins.
“Oh God, Mom, I’m gonna come!” I announced hoarsely.
That seemed to spur Ken on and he started to really pound me hard, holding my hips and moving me on top of him like a tiny doll.
My orgasm came crashing over me suddenly like a wave, making me howl triumphantly, and I did something I’d never done before. I squirted. An absolute flood, all over Ken's balls. The warmth of my juice set him off and his cock swelled some more and he shot a good thick load of cock juice up my ass.
I staggered off his cock and dropped to the floor, well and truly ass fucked.
“Oh my God, Oh my god, that was just so awesome.”
I lay there, trying to drag air back into my lungs and saw my Mom licking her lover’s cock clean. She was doing ass-to-mouth and I realised that no matter how far I went my Mom would always top me.
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<a href="https://www.lushstories.com/stories/anal/my-moms-man.aspx">My Mom's Man</a>