Dating Dennis

Literotic asexstories – Dating Dennis by PanWhoWrites,PanWhoWrites Dating Dennis

by Pan

Chapter 1:

I’m not going to lie – I thought it would be funny. I mean, he’s two years older than me, but Dennis is such a nerd…he’s never had a girlfriend, and he’s…well, let’s just say that he’s not exactly been “lucky” in the looks department.

Of course, if I’d known where it was going to lead, I never would have done it.

My name’s Tammy – I’m eighteen, but people always tell me I look younger. And, unlike Dennis, I’ve had a couple of boyfriends. I was one of the first girls in our grade to get boobs (probs because I was the last to lose my puppy fat) and so I got plenty of attention. I’m not a slut or anything, but I’ve fooled around with a few guys, and yeah, I’ve always enjoyed myself.

I wasn’t dating anyone when I decided to prank my brother. That’s how I came up with the idea, actually – we were on the same dating site. His profile came up, and I couldn’t resist – I quickly made a new profile, and sent him a couple of messages. He replied (of course he replied – I googled “hot girl”, and used the picture that had the most clothes on as the profile pic) and soon, Dennis and “Madeline” were going on a date.

Madeline never showed up, and at first, I was going to leave it at that. I figured that I’d had my laugh, I’d tell him what I’d done. Not to be a bitch, just because…well, okay, a little bit to be a bitch. But like I said – it was funny!

But to my surprise, he kept on messaging her. And so…well…

I couldn’t resist.

Seriously, what would you have done in my place?

Madeline stood Dennis up 3 more times before I finally admitted what I’d done. I guess I knew at that point he wasn’t going to find it funny, but when I told him, I swear I almost peed myself. I laughed and laughed and laughed at his face. He was so…okay, I guess it was pretty mean, but still. I couldn’t help myself!

I sort of expected retaliation, but instead, he just came into my room, and asked if we could talk.

###

“Hey Dennis…”

“Hey, Tammy. Would you mind sitting down? There’s something I really need to talk to you about.”

“Dennis, is this about the prank? Because I swear, I didn’t mean anything by it – it was just a joke. It just sort of…got out of hand.”

“Yeah, it’s about the prank. No, don’t look like that – I’m not going to hurt you. I just need…we just need to have a chat.”

“Okay…”

“So listen, I don’t know if you realise what you did…”

“I know I hurt your feelings, and I’m sorry. I’m super sorry. I swear, it won’t happen again…”

“Well, it’s not just that…”

“What is it?”

“It’s just…look, you’re younger than me, so maybe you don’t know these things. But when I thought I was going to be going out with Madeline, I…Tammy, are you listening?”

“Oh, sorry. Your necklace is just so…is that new?”

“Yeah, it’s nice, isn’t it?”

“Mmm…”

“Anyway, what I was saying was just that you made me think I had a date. Didn’t you, sis?”

“Mmmm hmmm…”

“And so when you stood me up, well, that’s not really fair, is it?”

“Not…fair…”

“So the fair and reasonable thing to do is to make it up to me. Do you want to make it up to me, Tammy?”

“Want to…make it…up…”

“So if Madeline stood me up four times, what does that mean?”

“Hmmm?”

“Madeline stood me up for four dates, right?”

“Uh huh…”

“And so how many dates do you owe me, Tammy?”

“I guess…four?”

“That’s right. So I want you to go and get dressed, like you would for a nice date, and then come back here. I’m going to take you out to dinner and a film, exactly like my first date with Madeline.”

“Okay…”

“Meet me back here in ten minutes, Tammy.”

“Ten…minutes…”

“Oh, and Tammy?”

“Yeah, Dennis?”

“Wear something slutty.”

###

And so that’s how I ended up sitting in the passenger seat of Dennis’s car, as he drove me to a restaurant.

Obviously if I’d had any idea that I’d owe him dates afterwards, I would never have set him up – it was just meant to be a prank. I didn’t want to be dating my brother. (ew!) But I’m not going to lie, I had a pretty good time. He picked a nice restaurant, we saw a movie that I’d been wanting to see for a while, and he was a perfect gentleman the whole time.

Well, almost the whole time. When I came back to his room and he saw what I was wearing, he really ogled me. Super gross. But hey, he’d told me to dress slutty – because, I’m assuming, that’s what Madeline would have done – and so I had to do it. I picked out these super short shorts that I know guys like – they make my ass look amazing. And to top it off, I have this shirt that’s like half-shirt, half-poncho – it shows my midriff, which can sometimes make me a bit self-conscious, but it’s exactly the kind of thing that I’d wear on a first date.

If I liked the guy, that is.

His eyes practically boggled out of his head, and whenever we were walking – from the car to the restaurant, or the restaurant to the cinema or whatever – his hand would slip down and grab my ass.

Part of me wanted to slap him, but I remembered that I was on a date, so I just grimaced and put up with it.

During the movie, and I thought this was actually pretty sweet, he reached over and held my hand. I got that nervous thrill that you get when you’re not sure whether or not a guy likes you, and I just reached back and held his hand as well. It was really nice.

When we were heading home, he asked (jokingly, I hope) if I wanted to go somewhere and neck. If it had been a real date, I would have slapped him (well…depending on how much I liked him, that is) but since he was my brother, I just gave him a death-stare, rolled my eyes, and told him that we were going straight home.

On a real first date, we wouldn’t have gone back into the house together of course, but other than that, it was a really nice first date.

Oh, the only other thing was when he parked the car outside. He looked at me, and I looked at him, and I remembered why I was doing this – I’d deprived my brother of a date, and so I owed him. If this had been for real, I definitely would have given him a kiss, so I shut my eyes, tried to get into character, and gave him a kiss.

He was pretty good, especially for someone who had never really dated much before, so I sort of lost track of what I was doing, and we made out for a bit. Not for long, just a few minutes – which was, apparently, enough time for Dennis to get his hand up my poncho and onto my breast.

(Thank goodness I was wearing a bra!)

Anyway, after maybe five minutes of making out, we stopped, I told him what a nice time I’d had, gave him a peck on the lips, and we went inside.

One date down…three to go!

###

“Hey Dennis, you ready for our date?”

“Oh yeah, I was meaning to talk to you about that.”

“What’s up? If you want to cancel, I am so into that…”

“No, it’s not that. It’s just…hang on. Let me…there you go.”

“Oh, that’s the necklace that you…”

“…”

“…”

“…Tammy?”

“Mmm?”

“I just wanted to talk to you about this date.”

“Mmm?”

“Well, it’s just…the last one went really well, didn’t it?”

“Mmm…”

“And I was thinking about Madeline…”

“Madeline…”

“If Madeline had a date like that, she’d really want to impress the guy for the next date, wouldn’t she?”

“Mmm…impress…”

“So maybe wear something even sluttier than you did last time.”

“Even…sluttier…”

“After all, things are going to get pretty hot and heavy this time, aren’t they?”

“Hot…and heavy…”

“I bet you’re horny just thinking about our date, aren’t you?”

“Mmm…”

“So you’re going to be turned on the whole time, yeah?”

“Yeah…”

“Okay. Well, why don’t you go get changed, and meet me back here in…let’s say 15?”

“Okay…Dennis…”

###

I’m really glad our parents weren’t home that night. Dennis told me they were staying at a hotel…he didn’t really explain why, but I didn’t really ask. In any case, they were out, and so I didn’t have to be embarrassed when I stepped into the hallway, dressed in my sluttiest outfit.

I’d forgotten that I even owned it, to be honest. It’s the sort of thing you buy after you’ve been dumped, and you want to feel sexy – it’s not the sort of thing you’d ever wear out in public.

Unless you owe your brother a hot date, I suppose.

It’s technically a dress, but only just – it’s black, and it goes from just above my nipples to just below my pussy. I swear, if you bend over in this thing, you fall out from both ends. And as if that weren’t bad enough, it came with these fishnet thigh-highs. The shoes that came with it are a pair of pumps – they’re, like, 5 inches, and half of that is platforms.

Though I have to admit – I got the outfit to feel sexy, and I did. From the second I left Dennis’s room to get changed, I felt warm. Appreciated, I guess. Sexy.

…maybe even a little bit turned on.

The pumps are really tricky to walk on, so I needed to lean on Dennis for support. For some reason he insisted on parking, like, a million miles away from wherever we were going, so we needed to walk right down the main street of our town. I swear I saw at least a dozen people that I know, but what could I say? I was on a date with my brother.

All those eyes staring at me was really doing something to me though, and by the time we got to the restaurant, I was so turned on that I had to excuse myself. When I was in the bathroom, I did something that I’ve never done before (at least not in public) – I got myself off.

Twice.

It didn’t take long – all I had to do was think about all those men staring at me, wanting to fuck me, and how sexy I looked in my little black dress, and how obviously I was on a hot date. No…how obviously I was a hot date. My panties were practically soaked, and I didn’t even move them aside – I rubbed my clit through the damp fabric, and I was cumming in a few seconds.

Unbelievable as it sounds, though, it didn’t seem to help at all – I was still just as turned on. Well, obviously I couldn’t go back to the table with my big brother this horny, so I pulled my panties down until they were sitting around my ankles, and I shoved three fingers into my pussy, pumping them in and out while my other hand rubbed at my clit.

To help me along, I imagined I was getting fucked. I pretended that some guy had seen me in the little black “fuck me” dress, and had been unable to resist, had bent me over and fucked me.

I came, imagining that I was getting fucked by my date, fucked by the man who was taking my ass out to dinner.

It was only as I was crying out in my second orgasm that I realised what I’d just done – I’d just cum, imagining being fucked by my date. Being fucked by…

My brother.

And, most annoyingly of all, it hadn’t quenched my desire in the slightest. I was still feeling hot all over – my nipples were hard points, and the stall was filled with the smell of my pussy. Glancing at my phone, I noticed that I’d been in the stall for almost ten minutes now – if I didn’t get back to my date…to my brother…he’d start to wonder what was happening.

Dating Dennis

by Pan

Chapter 2:

I was distracted all dinner. Dennis was, once more, a perfect gentleman. He didn’t comment on my squirming, or the way that I blushed every time he offered me food that even remotely looked like a cock. He didn’t question where I’d disappeared to for ten minutes, or even seem to notice the way that I kept getting lost in his eyes.

Before then, I’d never noticed how…sexy my brother was. I was having all these weird thoughts – if we hadn’t been on a date, they would have been hugely inappropriate. If we hadn’t been on a date, it would have been sick, thinking about fucking him, or imagining what his cock would taste like.

But in context, it was totally fine.

After dinner, we went on another parade of the city – I asked him if we were going to see a movie, and he just answered, with a grin, “Sort of”.

I’m by no means large, but I’ve got an ample bust and an ass to match it – I’m curvy, and Dennis is tall and thin. So I was impressed by how well he managed to keep me supported as we walked – the guys staring at me were distracting the hell out of me, and I’m not used to walking on heels at the best of times.

I must have stumbled and fallen onto him at least half a dozen times…and when he started grabbing my ass and breasts to hold me up, another dozen times after that.

Finally, we arrived, and to my shock, it wasn’t the movie theatre we’d gone to last week. It was a porn theatre.

“Dennis!” I cried, trying to ignore the small part of my brain that wanted to check it out. “What the hell do you think you’re doing? What kind of a date is this?”

“Keep it down,” he said, and I nodded obediently. “You’re filling in for Madeline, remember? And Madeline’s profile specifically said how much she liked porno theatres, so that’s where we’re going.”

That shut me up. I’d made Madeline’s profile in ten minutes flat, trying to come up with stuff that would get Dennis interested. A porn theatre sounded exactly like the kind of thing I would write, and Dennis had obviously spent way more time poring over the profile than I’d spent writing it.

I decided to let go, and just sink into the date. I was filling in for Madeline, and Madeline liked porn theatres. Fine.

We went in, and I had this weird mix of emotions. On one hand, I was disgusted – the place stunk, it didn’t feel like anyone had ever cleaned the seats or floor, and I was here with my brother.

On the other hand…when you’re turned on, the more perverse something is, the hotter it is, and I couldn’t help finding the fact that this was where men got off was kind of…erotic. I was standing where dozens, hundreds, thousands of men had brought themselves off.

We sat down, and a new film started. I tried to get into it, but the low quality of the plot was only beaten by the acting.

Get to the tits, I silently chanted, and must have jumped two feet off my chair when I felt Dennis’s hand reaching between my legs.

“Dennis,” I hissed, “what the hell do you think you’re doing?”

“This is a date, remember?” he said.

“Yes, but I am not that kind of girl!”

He turned to face me, and I saw that he had one eyebrow raised.

“Tammy,” he said, “if you were out with a girl dressed like this, smelling like cunt, sitting in a porno theatre…what would you expect?”

I looked down at my clothes…well, from my angle, I could only see my prominently displayed tits…

Maybe he had a point.

Besides, I was horny…and it was a date…

###

“Heya Tammy – ready for date number three?”

“Oh yeah, I’ve been meaning to talk to you about that.”

“What’s up?”

“I dunno, I’m just starting to feel really uncomfortable about some of the stuff we did…”

“Like what?”

“Well, I mean, you fingered me for like half an hour…”

“Yeah…”

“And then I went down on you what, three times?”

“You went down on me twice – the last time I just came on your tits.”

“Yeah, exactly. Don’t you feel a little weird about that?”

“No…it was a date.”

“I know, but…you’re still my brother.”

“So what’s bothering you?”

“Well, it’s not like what happens on a date doesn’t happen…”

“I know…”

“So didn’t we…y’know, commit incest? Is that even legal?”

“Oh, I think I know what’s bothering you! Here, look at this.”

“That necklace? Where did you get that, anyway?”

“Don’t worry about it, sis.”

“Don’t…worry…”

“Now look, I know why you’re feeling uncomfortable. It’s because the lines have blurred – you’re not sure when to act like brother and sister, and when to act like we’re on a date. Is that right?”

“That’s…right…”

“So why don’t we make it simpler? Even though we’re always brother and sister, let’s always act like we’re on a date. Around the house, in public – no matter where we are, just act like we’re on a date, okay?”

“Always…on a date?”

“That’s right. Always on a date. Repeat it back…”

“Always…on…a…date…”

“Good girl. Now, when we’re on a date, you’re super turned on, aren’t you?”

“Mmm hmmm…”

“So if we’re always on a date, you’re always turned on, yeah?”

“Always…turned…on…”

“And when we’re on a date, it’s okay to give me a blow-job, isn’t it?”

“Mmm…”

“So how about we do that right now? Come on over here, and put that mouth of yours to work…”

“Okay…Dennis…”

“And don’t worry about our third date. We’ll schedule that for another time.”

###

I don’t know why it took so long for us to eventually go on our third date, but I was excited. I’d had a few more chats to Dennis (mostly after blowing him) and he’d made it pretty clear what expectations he had for a third date.

It had taken me a while to pick the outfit that I was going to wear – I’d exhausted my own wardrobe, so I had to do some online shopping. But when I saw it, I knew it was perfect.

Technically, it was a top and a skirt…but if you called it lingerie, it would be hard for anyone to correct you. The top was a strip of fabric that covered my boobs and nothing else – I’d considered getting something that just hid the nipples, but there’s something to be said for the allure of mystery, y’know?

The skirt was the best part though. It was like a triangle of black material at the front and back – every time I put a leg forward, it showed off everything. Everything. If I hadn’t been wearing a thong, you’d have been able to see my nicely shaved pussy in all its glory.

I’d started wearing platform heels most of the time these days, so it was no effort to wear the 6-inch pumps that go so well with the dress. Of course, even though I could walk, I still made sure to rely on Dennis for support – I love the way he gropes my butt in public, just to show everyone that I belong to him.

We skipped the restaurant this time – thank god! I’ve been looking forward to this night for so long – I feel like I’ve just been constantly turned on for, like, weeks now. No matter how often I blow Dennis or get myself off (or, quite often, both at once) it never seems to scratch my itch, but I just know that after tonight, I’ll finally be satisfied.

Dennis took me right into the middle of town – we could have driven, but he knows how much it turns me on to show off in front of everyone. I love it when we run into someone I know, and I can just present myself…and show them that yeah, I’m Dennis’s property now. He found the cheapest motel he could, booked a room, and a few minutes later we were in the elevator.

Well, I just couldn’t wait – as we started going up, I started going down. I just wanted to make sure that he was hard and ready for when we got to our hotel room (although considering what I was wearing, there wasn’t really much of a risk that he’d be soft…)

He didn’t even bother zipping back up when we got to the floor, just walked down the hall with his dick out. God my brother is sexy.

When we got to the hotel room, he tried to pick me up, but when that didn’t work, just pointed where he wanted me to go, and I threw myself onto the bed. He lifted up the triangle, pulled my thong down, and without any further ado, slid his cock into me.

A tiny part of my brain wondered if we should be wearing a condom, but then I became aware of his cock sliding inside me, and my mind turned off entirely.

I don’t think I’d ever been so wet in my life – despite the fact that Dennis was my first, he slid in with no resistance, and I started cumming almost immediately. My mouth was right in his ear, and he said later that he was worried that I was going to burst his ear-drum: I started screaming and screaming, and my pussy started convulsing around his cock. His eyes rolled back in pleasure, and pretty quickly, he was cumming.

Now, what kind of a date would I be if we’d stopped there? I took his cock in my mouth, and played with his balls until he was hard again. Every now and again, I’d pull it out and start talking to him – I don’t even remember most of what I said, it was just a stream of consciousness kind of thing.

“You like that, Dennis? You like watching your little slut of a sister suck you off? I can taste my pussy on your cock…mmm, I love the taste of your cum so much. I’m going to fuck you all day every day from now on, you know that? And when I’m done, I’m going to suck you clean and let you fuck me again…”

Within no time, he was hard, and round two began.

I could go on about that night all day, but to put it simply, it was the greatest night of my life. We fucked, and I sucked him, and then we fucked some more. He’d had the foresight to bring some lube, and he even took my ass – it was the hottest, sexiest date that anyone had ever had, and the sun was coming up by the time we stopped.

He fell asleep almost straight away, but I just sat there, playing with my pussy, watching him. Finally, I curled up next to him, and hoped that even in sleep, he’d enjoy the feeling of his sister’s naked body up against his.

I missed school the next morning – after waking Dennis up with my tits in his face, he just had to fuck them (something that we’d never done before) and one thing led to another…

The hotel’s late checkout fee was pretty steep, but after a few minutes of conversation with the manager, Dennis got out of it in return for letting him see my tits. I felt a tiny bit uncomfortable with that, but I didn’t want to cost Dennis any money.

We’d shared a shower that morning, but after washing all the cum off, Dennis had wanted to “mark” me – he said that any time I couldn’t just have my tits out, he wanted to make sure I could feel him on them. I don’t think the manager was expecting that, and he seemed quite excited by the sight of Dennis’s glistening cum on my huge tits.

When we got home, I was already horny again – the feeling of his cum sloshing around inside of me, as well as the knowledge that my tits were literally coated in it…fortunately Mom and Dad didn’t seem to notice as we snuck past them and fucked on my bed.

I got the feeling we’d be doing that a lot from now on.

###

“Hey sis.”

“God you look sexy in that, Dennis…”

“These are just my pyjamas, Tammy…”

“Yeah, I know. I’m just imagining what’s underneath.”

“Well, this necklace is underneath…”

“Mmm…”

“So I was thinking about our fourth date…”

“Me too…”

“And it seems to me that we don’t really need it, do we?”

“Don’t…we…?”

“Well, once you move in with someone, you don’t exactly keep on dating. And you and me…we live together, and we fuck all the time.”

“Fuck…all…the time…”

“And that’s pretty much living together, right?”

“I guess…”

“But, well…you still owe me one more date, don’t you Tammy?”

“One…more date…”

“And so I was thinking that to “pay off your debt”, so to speak, maybe you could organise a blind date with one of your friends.”

“O…kay…”

“Like…what’s that friend of yours with the big tits? Always has a lollipop in her mouth?”

“Ellen…”

“Yeah, Ellen. Can you organise a blind date with me and Ellen?”

“She’s got a…boyfriend.”

“Oh, well…it’s just one date. Maybe tell her it’s just a favor, and it doesn’t mean anything. I’ll take care of the rest…”