HEADS I WIN, TAILS YOU LOSE
I could never do that.
It’s five simple words and I absolutely hate them. What people usually mean when they say that is that they really, really don’t want to do whatever it is they say they can’t do, but you know damned well that most of the time, if they really had to, they could do it.
The queen of I-Could-Never-Do-That is my neighbor Bella. Bella’s only eighteen years old but like her mother, Bella thinks she knows a lot more than she actually does and Bella loves to tell me, “I could never do that.”
I usually run into Bella when I’m getting my mail. She’ll ask me how I’ve been and I’ll tell her about my most recent sexual exploits because it amuses me and because I know Bella doesn’t really care about anyone else but Bella. After hearing about my latest exploits, Bella will invariably say those five little words. “I could never do that.”
My response is always the same. “I’ll bet you could.”
That’s the trigger and it’s also the challenge.
A few weeks ago, I told Bella I was studying hypnosis. Bella’s response, of course, was, “I could never do that.”
“Why,” I’d asked.
“Because, I don’t know. It seems so weird. It seems so controlling.”
“I’ll bet I could control you,” I’d told her.
She’d laughed at that. “Oh, you could never do that,” she’d said and yet even as she’d said it, I thought I’d seen just a momentary gasp and it was right then and there that I decided I wanted to try.
I didn’t press too hard. “Suit yourself,” I’d told her and I’d let it hang but from that point onward, I’d kid her about it whenever we’d meet. “You ready to be hypnotized,” I’d ask.
She’d always laugh. “I could never do that.”
One night, she called me up. “Hey, Mike,” she’d said.
“Bella? What’s up, Bella?”
“I’m bored,” she’d said.
I had the feeling that wasn’t the only reason she was calling me. She was a good looking girl and there were plenty of people more her age who I was sure she could call and I told her so.
“Don’t you like me, Mike?”
Now, where the hell had that come from. “I like you just fine,” I told her. “Now, come on, Bella. Out with it. Why are you calling me?”
“I told you. I’m bored.”
“Uh huh. We’ve been over that. I don’t believe you, Bella, so if you don’t tell me why you called, I’m going to hang up.”
I waited but she said nothing.
“All right. I’m hanging up.”
“No wait.”
“Yes?”
“I really am bored,” she’d said with a pout, “but mom says I can’t call my friends.”
“And why is that, Bella?”
There was a long pause. “It was nothing,” she said. “It was just a little marijuana, and it wasn’t like I’d ever smoked it before. I just wanted to try.”
“And?”
“And the vice principal caught me. He sent a letter home to mom and mom said I was grounded for the whole month and I really am bored.”
“Yeah, so why are you calling me?”
“Mom’s working late and she’s not going to be home until late. She said I couldn’t call my friends but she said I could call you.”
“Yeah, so?”
“So I’m calling you?”
That was about the lamest excuse I’d ever heard. I mean the marijuana part was right. Marcia, Bella’s mom, had called me and had told me about it. She’d said she was going to be working late this week and she’d asked me if since I lived only a few doors down, could I keep an eye on Bella. But the rest of it was trash. I had no idea what the girl was up to.
“Mike?”
“Yeah, Bella?”
“Could you come over?”
“Why?”
“Because.”
Okay, I just want to make it clear up front that I am not stupid. I knew Bella had something up her sleeve, but I was just curious enough to wonder just what the heck it was and I was just dumb enough to say I’d go.
When I got there, Bella was in her nightie ... and nothing else.
“Bella,” I said. “What the hell are you doing?”
“I just wanted to see if you were interested in me.”
“Bella, you’re just a kid.”
“I am not. I’m eighteen.”
“Then you ought to be old enough to know better.”
“Come on, Mike.”
“No.”
“Come on. Mom’s not going to be home until late.”
“No.”
“Please.”
“No. Now go put some clothes on so we can talk.”
“I’ve got some clothes on.”
“Put some different clothes on.”
“Come on, Mike.”
“Now,” I told her.
She huffed and she puffed but she did what I told her and she went back into her bedroom and she came out a little while later in jeans and a t-shirt. “Better,” she asked with a pout.
“Yeah. Now, Bella, what the hell were you trying to do?”
“I was trying to seduce you.”
“I could see that but why?”
Bella looked shy. “It’s um ... it’s because ... you know, it’s because you’ve got experience and I ... I wanted to see what you could do.”
“So you wanted me to teach you about sex?”
“Pretty much.”
Okay, I was flattered. Not flattered enough to take her up on it, but I was flattered. “So, why this sudden interest in sex?”
The girl didn’t answer.
“Bella, why the interest?”
She shook her head.
“Bella!”
“It’s Ryan Matthews.”
“Who the hell is Ryan Matthews?”
“I think he’s going to ask me out to the prom and Ryan’s like totally experienced and I don’t want to look like a dork.”
“You’re doing all this for some boy.”
“Yeah, sure.”
I remember shaking my head. Kids. I wondered if I was like that when I was a kid, but then I knew I didn’t have to wonder. I knew I was worse.
And that still didn’t mean I was going to fuck Bella. Legal or not, she was still my neighbor and I didn’t want Bella’s mom riding my ass because I banged her daughter, but then that gave me an idea. “I’ll tell you what, Bella. You let me hypnotize you and afterwards, if you want, I’ll teach you some of what I know in bed.”
“You’re serious?”
“Sure. It’ll be fun.”
“I could never do that.”
So here was the plan. Hypnotize Bella, then make her not want to have sex with me, then wake her, and I’d be off the hook. Easy, huh, only little Miss I-Could-Never-Do-That had to open her big, fat mouth, and even as I was putting her under, I was changing the plan.
Oh, by the time she woke up, she no longer had any desire to fuck me or anyone else, but there was something else there, too. Whenever she said, “I could never do that”, if the next thing she heard was me saying, “I’ll bet you could,” it would start a friendly, little wager. For the next 24 hours, she would be consumed with the thought of doing just what I said she could and as the hours wore on, those feelings would grow more and more intense. If she gave in, I’d win, but if after 24 hours, she didn’t give in, then she would win and the words “I’ll bet you could” would no longer have any effect on her.
So far since that night, I’ve always won that bet.
The first bet came a couple days after I’d hypnotized her. I was picking up my mail and there was Bella.
“Hey, Mike. How’s it going?”
“Not bad. You?”
“Not too bad. Mom finally said I could call some friends, but I’m still grounded like for forever.”
“Yeah.”
“Yeah, so what you been up to?”
To tell the truth, I wasn’t even thinking about the bet. I was leafing through the assorted mail, making a small pile of things I might actually want and a much larger pile of junk mail I wanted to toss. “My girlfriend came over and she sucked my cock, Bella.”
“Oh, I could never do that.”
That got my attention. I looked at her. “I’ll bet you could,” I said.
I don’t know what I expected to see her do. I mean, I didn’t expect her to suddenly drop down and suck my cock off right there in front of the mail boxes and fortunately for me, that wasn’t what she did. That would have been hard to explain.
Like I said, that wasn’t what happened. Bella just laughed. “I could never do that,” she said again.
So much for that, I thought. Well, it was worth a try. I told Bella, “Good bye,” and then I was on my way to my apartment.
It wasn’t until later that evening that I got the call.
“Mike?”
“Bella,” I said. “What’s up, Bella?”
“I’m bored.”
“I thought you said your mom said you could call your friends.”
“She did, but I wanted to talk with you.”
Okay, so I’ll admit it. I was a bit dense but when the bet didn’t show any immediate results, I’d kind of written it off as a failed experiment. I mean, no one was ever going to find out about it, so if it didn’t work, it was no harm, no foul, right?
I should have known better. “Why’d you want to talk with me?”
“I don’t know. I just did.”
I could sense that wasn’t the real reason. “Bella?”
“What,” she said petulantly.
“Something’s bothering you. What’s up?”
“I want to ask you something.”
“Sure. Go ahead. Ask.”
“No. I ... um ... it’s kind of personal. Can I ask you in person?”
Okay, so maybe I was a little stupid but I just didn’t think about the bet. “Look, Bella, I’m just about to go to bed. Can this wait until tomorrow?”
There was just the slightest of pauses. “I could come to you,” she said. “It won’t take any time at all.”
Okay, getting ready for bed was just an excuse but she’d called my bluff. “Okay sure,” I told her. “You can come over but only for a moment, okay?”
She sounded almost giddy. “I’ll be there in an instant,” she said. “Okay, bye.”
The line went dead and moments later, there was a knock at my door. I opened it up and there was Bella.
She looked almost disappointed to find that I was still dressed. “I thought you said you were about to go to bed,” she said.
“In a few minutes.”
“Oh.”
“So you said you had a question to ask me.”
“What?”
“You said you had a question to ask,” I reminded her.
“Oh yeah. Well, it’s really more of a favor, really.
“Okay, what’s the favor?”
I should have known something was up because suddenly Bella was getting all shy on me. “It’s kind of something you said earlier,” she finally said.
“Okay, what did I say.”
“You were talking about your girlfriend.”
“Which one?”
She shook her head. “I don’t know which one but you were talking about your girlfriend.”
“Okay, so what did I say about her?”
“Well, um—”
“Yeah?”
Okay, even as dense as I might have been, I couldn’t help but miss the fact that she was staring at my crotch.
“Come on, Bella,” I said. “Out with it. What is it you wanted to know?”
“It’s just that, um, I was just wondering—”
“Bella!”
“I was just wondering if you’d let me suck your cock.”
“What?”
It was clear that Bella wasn’t really looking at me anymore or to be more precise, it was clear that there was only one part of me which had her attention. “Come on, Mike. I want to know what it’s like to suck your cock.”
“No.”
“But why not?”
“Because you’re just a girl—”
“I’m eighteen,” she reminded me.
“—and because your mom would kill me.”
“Mom doesn’t have to know. This would just be between you and me.”
I’d already decided I was going to let her do it. I just wanted to see how far she was willing to go. “You’re sure about this,” I asked.
Her hand was sliding down the front of my jeans. “Come on,” she begged. “Who’s going to know?”
“Geez, Bella.”
“Come on, Mike. I want to do it. Let me suck your cock.”
“I don’t know. I mean, what if your mom—”
Her hand squeezed my cock through my jeans. “Come on, Mike. Mom’s not here and I am.”
I didn’t say anything but then I didn’t have to. Her hand slid my zipper down and then she pushed her hand inside my jeans. Her hand found my cock.
“Come on, Mike,” she purred.
I didn’t say anything.
Her hands worked at my belt and then she had my jeans open. She pushed my jeans down over my hips and then she pushed my underwear down. Once again, she wrapped a hand around my cock and she gave it a few good strokes. “Come on, Mike,” she said.
She wasn’t waiting for an answer from me. She dropped down to her knees and her hand stroked me again.
Her mouth slipped down around my cock and then she took my cock in her mouth.
I couldn’t help it. I moaned.
She looked up at me and grinned. “You liked that, didn’t you,” she said. “Am I doing this as good as your girlfriend?”
“Oh yeah,” I said.
That apparently was all she needed to hear because once again, her mouth was on my cock.
After that, I pretty much shut the hell up except of course for the occasional moan. God damn, for someone who “could never do that”, that girl sure did know how to suck a cock.
And she wasn’t stopping. Her mouth kept moving up and down on my cock. If she didn’t watch out, she was going to get a mouth full of cum.
I moaned again. If she knew what she was about to get, she showed no indication of it.
Her mouth moved up and down and I moaned again. Up and down. Up and down. Up and down.
I groaned again and my cock surged.
I could tell she was surprised when I came inside her. She paused if only for a moment but then whe went right back to sucking me off and to my surprise, she swallowed everything I had to give her.
It wasn’t until she’d sucked me dry that she finally pulled her mouth free. She gave my cock a few last minute licks and then she smiled up at me. “I guess I could do that,” she said.
Hell yeah, I thought.
And just like that, she got up and she licked her lips. “I hope I did better than your girlfriend,” she said and then she walked out of my apartment.
You know, something like that happens and there’s a part of you that just can’t believe it really happened. I woke up the next morning thinking that it really couldn’t have happened, that somehow, I really hadn’t had the neighbor girl come over and suck off my cock, but as much as I tried to tell myself it couldn’t really have happened, I knew it had and right then and there, I resolved myself to see if I could make it happen again.
I didn’t see Bella that day or the next one either but I saw her the day after that. “Hey, Mike,” she said.
“Hey, Bella. How’s it going?”
“Not bad. Got a lot of schoolwork to do though.”
“That’s too bad.”
“Yeah, but I got to do it, you know. So what you been up to?”
I smiled to myself. I’d been waiting for her to say that. “My girlfriend came over and sucked my cock,” I said.
Bella just looked at me and then she gave me a knowing smile. “That’s nice,” she said and then she turned and she walked away.
That totally sucked. I’d fully expected her to say ... well, you know what I expected her to say, and to tell the truth, I kind of felt a little cheated. I went back to my apartment in a foul mood.
I didn’t see Bella the next day out by the mail boxes but I saw her the day after that.
“Hey, Mike,” she said.
“How’s it going?”
“Not bad.”
“So you get all that schoolwork done?”
“What? Oh yeah, I got it done. Thanks. So how’s it going with you?”
I’d meant to say my girlfriend had sucked my cock again because I still wanted to see if I could get Bella to do that again but that’s not what came out. What I said instead was that I’d just fucked my girlfriend up the ass.
Bella groaned. “Ewww. That’s gross. I could never do that.”
And before I could stop myself, I just said, “I’ll bet you could.”
She just laughed and shook her head. “I don’t think so, Mike. Not that one.”
I laughed with her even as I was wondering why I’d done that. Okay, I had to admit from what I could tell, Bella had a great ass. That day, she’d been wearing some jeans that really showed off her butt, but I’d never, ever done that before. In fact, I hadn’t even really thought of doing it before so why had I just given her the trigger to make her want me to fuck her in the ass.
There was a part of me that was hoping she wasn’t going to do it. I mean, sure, giving someone a blow job, that was one thing, but getting fucked in the ass, that was a whole other thing.
I should have known better. It wasn’t even 8:00 when Bella called.
I knew it was her. I didn’t want to fuck Bella in the ass. I almost didn’t answer but that would have been mean. After all, I’d started this so now I was going to have to finish it.
“Hey, Mike.”
“Hey, Bella. What’s up?”
“Whatya doin?”
“Watching TV,” I lied.
“I’m bored. Can I come down and hang with you?”
I knew her mom had taken her off of suspension. “Don’t you have some friends you can hang out with,” I said.
“Yeah, but I want to hang out with you instead.”
Okay, I was starting to get just a little bit desperate. I mean, as cute as she was and all that, I didn’t really want to fuck her in the ass, or at least that’s what I thought, but the next thing I knew, I was telling her to come on over.
It only took her a couple of minutes to knock on my door.
The first thing I noticed was that she’d changed out of her jeans and she was now wearing a short, little skirt that showed off her little, round ass even better.
Damn!
“Hey, Mike.”
“Bella.”
It was awkward. I mean, I knew why she was there and she knew why she was there only she didn’t know what I knew, and I wasn’t going to make it easy on her because I was still trying to think of a way to get out of it.
We made small talk but that quickly petered out and I could tell Bella was getting antsy. “Mike,” she asked.
“Yeah, Bella.”
“I want to ask you a question.”
“Go ahead, Bella.”
“Do you think I’m pretty.”
“What? Yeah sure,” I told her. “I think you’re pretty.”
“What do you think is my best part?”
“Huh?”
“What’s my best feature?”
“I like a lot of stuff.”
“Like what?”
“Like I don’t know. Like you got a nice face, nice eyes.”
“Just my face,” she said. “Nothing else.”
This was getting fucking weird. I mean, what the hell did the girl want. She lived two doors down from me. I wasn’t going to fucking undress her with my eyes.
And that, of course, was exactly what she did want me to do.
“Just my face,” she asked again. “Nothing else.”
“You got a nice body.”
That perked her up. “Oh yeah? What do you like about my body?”
“It looks good,” I said.
“Like what exactly.”
“Geez, Bella. What do you want me to say?”
“I just want to know what you like. What looks good on me?”
“Geez, Bella. You’re practically my next door neighbor.”
“Then you must have had plenty of chances to see me so I’m just asking, what looks good on me?”
“It all looks good.”
“Like what?”
“Like your tits,” I said. “I like your tits.”
“Just my tits,” she said. “Nothing else?”
I knew what she wanted me to say.
“Just my tits,” she asked again. “Nothing else?”
Still, I didn’t say anything.
“How about my ass,” she prompted. “Do you like my ass?”
“Sure, I guess.”
“You guess? You’re not sure, Mike. I don’t know. Maybe you need a better look. What do you think, Mike?”
I knew I was losing control of the situation.
“I think you need a better look.”
She pulled up her skirt and wouldn’t you know it, she wasn’t wearing any panties.
“So what do you think,” she asked. “See anything you like?”
I was staring at her ass and yeah, it really was very nice and round and tight, just the way I liked it and yeah, my cock was pretty damned hard.
“So you haven’t said anything,” she said. “Do you like this ass?”
I looked at Bella’s butt. “Yeah,” I told her. “I like your butt.”
She was rubbing her hand over the front of my jeans. “Oh yeah, Mike, I can tell just how much you like it.”
It wasn’t that long before she had my belt open and my pants down. Her hand was wrapped around my cock. She gave my cock a little squeeze. “I think you know what I want you to do with this,” she said.
Okay, I knew I was losing control of the situation and to a frisky, little eighteen-year-old no less, but I liked it. Besides, I wanted to hear her tell me what she wanted me to do. “What do you want me to do,” I asked.
“I want you to put this,” and here she gave my cock another squeeze, “in here,” she directed even as she slid a hand between her cute, little cheeks.
I grinned at her. “Well, if that’s what you think we need, I think we’re going to need to get it lubricated first before we make that happen.”
Bella grinned back at me. “You leave that to me,” she told me.
She was right and I was about to find out that there was more than one way to go down on my cock.
I couldn’t help but let out a groan. Fuck, if she didn’t watch what she was doing, I was going to be in no condition to stick my cock where she wanted it.
She pulled my mouth up off of my cock and she looked up at me. “Is this what you wanted,” she asked. “Is this what your girlfriend does for you?”
I groaned. “My girlfriend? What ... oh yeah, I don’t know. Oh yeah, my girlfriend, yeah she does it.”
“I’ll bet she does,” Bella said, “because when you get a cock as big as this one, it would hurt if you tried to put it in your ass when it wasn’t lubricated, it would hurt, but are you ready to fuck me now?”
“Yeah,” I said.
I bent her down over a chair and I pushed in behind her. I slid my cock in behind her and I pushed my cock in between her cheeks.
I heard the girl moan as she felt my cock slide between her cheeks and then I pressed my cock against her hole.
The girl stared straight ahead. “Fuck me, Mike,” she moaned. “Fuck me.”
My cock was wedged right up against her tight, little hole. “You want this, don’t you.”
“Come on, Mike,” the girl moaned. “Don’t make me wait. Fuck me. Fuck me.”
I didn’t make her wait. I pressed forward and I heard Bella groan even as my cock worked its way even deeper inside her ass.
“Oh yeah,” she moaned. “Oh yeah. Fuck me. Fuck me.”
I couldn’t help but groan as I slid inside her.
Bella was looking back at me even as my cock moved inside her butt. “Oh yeah,” she groaned. “Oh yeah, this is what I want. This is what I want. This is what I fucking want.”
“Yeah, you like this, don’t you?”
“Oh yeah,” the girl moaned. “Oh yeah. This is what I want.”
“Little, fucking slut.”
Bella moaned again. “Oh fuck. Is this ... is this ... oh shit, is this what you do for your girlfriend?”
“My girlfriend?” Then I remembered what I’d told Bella out by the mailboxes. “Yeah,” I said. “This is what I do.” Bella didn’t have to know there was no way, no how, that my girlfriend would ever let me do this to her ass. On the other hand, the way Bella was responding to my cock, I was thinking of getting a new girlfriend.
“Oh fuck,” I moaned.
“What?”
“I’m going to cum,” I told her.
The girl moaned. “I want you to do it, Mike. I want you to do it. I want you to cum in my butt.”
That’s all I had to hear. I groaned as my cock surged and all of the sudden, Bella was getting just what she wanted.
Since then, I’ve had Bella so many different ways. It’s always the same old bet and Bella loses every time although to tell the truth, I think if you’d ask her, she’d probably say she was winning. The only problem is that with all I’ve made her do, she doesn’t say those five little words near as much as she used to anymore and that’s too bad because I miss fucking her.
So, Bella, if you’re reading this, when it comes to your mouth on my cock, it’s heads I win, and when it comes to my cock in your ass, it’s tails you lose, so you know what, Bella, yeah, you really could do that.