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.”
“Oh.”
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.