Here I am at one of the classiest places in town having dinner with my sister. I can barely afford it, but... well it was her choice and there was no fucking way I was saying no after what happened earlier. That was insanely hot and if there is any way it can happen again, I will do anything to help in the matter.
We finish up our meal and just chat...
"What's wrong with you? You've barely said a word since we got here," she says as I stare at my glass of water barely blinking, replaying today's events over and over in my head.
"Um... yeah sorry Jen. I was just..."
"You were just thinking about earlier, weren't you?"
"Yes," I say reluctantly, glancing up at her for a quick second then back down.
"Hahaha! You're so cute. You can't even look me in the eyes. Did I fuck you up THAT much after today? C'mon, Matt!" she says, then lowers her voice a little, "It was fun. And yes, it will happen again."
I glance up with wide eyes, glancing quickly down to her incredible cleavage.
"Yeah, you like that, don't you?" she continues in a soft tone to be sure no one around us can hear our conversation, "You better believe I was damn serious about what I said. Don't forget. You will only jerk that little dick under my supervision, got me?"
Those last words were gut wrenching, but such a huge turn on. Who knows what devious plans she has going on in that mind of hers...
"So..." I stumble on my words a bit, "how... how often are we talking here?"
"How often?" she says sounding puzzled, but you can tell she knows exactly what I'm asking.
"Yeah, you know..." glancing down quickly at her cleavage again, hoping she doesn't notice, "how often am I going to be able to jerk off?"
"As often as I fucking say. How about that?"
"..." I stay silent. 'Fucking hell' is all I can think.
"Hehe! I'm just fucking with you. How often do you do it now?"
"I dunno... Like 2 or 3 times a day maybe."
"Holy shit! Are you kidding??" she raises her voice in shock, but quickly catches herself and brings back that soft sexy tone she has... "And you wonder why you have stamina issues and cum so quickly? Matt, jesus christ. No. Fuck no. You'll be lucky if you get to cum a couple times a week with me. Seriously, we need to fix you and I really think this will help," she can't help but let out a little smirk at the end of that sentence, but quickly wipes it away by hiding it with a sip of her water.
She puts her glass down and catches me, for probably the fourth or fifth time since we sat down, getting a glance at her beautiful tits in that revealing shirt she is wearing. And then I feel it... her foot... slowly sliding up my leg. I look up at her and she's fucking grinning at me.
"What's wrong, Matt?" she says in a soft evil tone while her foot makes contact with my already hard cock.
She makes a little fake gasping noise.
"Matt... now now," she begins softly stroking my cock with her foot through my pants, "my oh my, look at you. I guess you're all charged up to shoot another one of your tiny loads? Hmm? It's been about an hour, so I would hope so. You see," she begins stroking a little harder and a little faster with her foot, "in my experience, when real men, who have real man sized cocks and actual stamina, fuck a woman, they are usually ready to go for another round just minutes after cumming AND they can do it at least a few times to keep their woman satisfied, but no... not you. Guys with little dicks like yours and no stamina can only hope to even please their lady on the first round and any round after that? Yeah right. The girl is either gone or past out and most importantly, disappointed."
I'm looking at her. Deep into her eyes. Yet I am only half listening. My eyes every now again glancing down at her tits and her neck and arms... any skin she has showing, I'm imagining myself touching it, caressing it, kissing it, licking it... I want her so bad. I want to fuck my sister.
"Mmmm yes, how you doin over there?" she continues to stroke and I continue to get closer to the edge. "You're not getting close, are you? Because you know you're not allowed. You know what," she slows down her pace on my cock a bit, "I'm thinking once week is actually a good schedule. What do you think, pussyboy?"
"Huh, what?" I know what she said, but the 'pussyboy' caught me way off guard.
"Pussyboy. That's my new nickname for you. Do you like it?" she picks up the pace on my cock a bit and I let out a little moan.
"Mmm yes. Yes I love it," I say softly, even though I fucking hate it, but I really don't fucking care right now.
"Good," she says as she takes another sip of her water. "So as I was saying. Once a week. That's how often you will cum for me."
"But.. Jen.. I..."
"Quiet," she picks up the pace and pressure even more on my cock, "Once a week. Got it? Or did you want to make it twice a month?"
"Yes, okay... once a week, please!" I just blurt out without any hesitation, my mind focusing only on one thing right now.
"Good boy. It's all you really need anyway. I mean, 2 or 3 times a day? That's way too much. Maybe for a guy with a real sized cock. Sure, no problem. They can do whatever they want. But tiny dicks? Haha, no way."
I just nod in agreement, getting closer to cumming by the second.
"Hehehe," she snickers softly, "this is so fucking easy. I wonder what else I can make you do..."
"Excuse me," a low voice comes from the next table several feet away and I completely snap out of it looking over to him as he gets up and walks towards us. Jen stops stroking, but her foot remains resting softly on my cock as she looks over to the jerk who just interrupted us, "Are you Matt?"
"Oh...hey man, how's it going?" My asshole neighbour from the apartment next door. Must be out on another one of his dates as he is sitting across from yet another incredibly hot woman. His name is James. He's probably about my age, maybe a couple years older, African American, very short black hair, pretty tall.. I'd say about 6 and a half feet probably. Built like a brick house. He's one of those single guys who has a regular job by day and hits the gym every evening.
"Aren't you going to introduce me?" completely side-stepping my question as if he has no care in the world.
"Yeah, sorry. This is my sister, Jen."
"Sister?! Hahaha, that explains it! I don't think I've ever seen you out on a date, especially with a girl as beautiful as you," he looks over in Jen's direction, "Nice to meet you, Jen." His date seems unimpressed that his eyes and attention are no longer on her, especially after that comment towards Jen's looks.
"Well it's nice to meet you, too!" They shake hands. Great.. that's all I need. My sister becoming friends with the obnoxious ass living next door to me.
"Well, I'll let you two get back to it," he says as he turns back towards his table, "I guess I'll be seeing a lot more of you, Jen. Are you staying in town for a while?"
Is he... hitting on her?
"Sure am," Jen doesn't even hesitate as I catch her checking him out while he walks back to his seat, "I'm actually living with Matt now. At least for the foreseeable future."
"Oh yeah? Well that's awesome. I will definitely be seeing you then. Have a good night!"
Why is he being such a nice guy? He's usually a fucking dick. I guess when you have two beautiful women in the room, that can really change things.
"Wow, it's a good thing they have long covers on their table here, huh? That could have been awkward." She says as she puts her foot down. "He seems nice. I thought you said he was a dick?"
