Dating Dennis Ch. 01

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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 18, but people always tell me I look younger. And, unlike Dennis, I’ve dated. 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 with 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.”


“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 Avrupa Yakası Escort new?”

“Yeah. It’s nice, isn’t it?”


“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?”


“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?”


“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.”


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


“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, Avrupa Yakası Bayan 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 great 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…”





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


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


“And I was thinking about Madeline…”


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


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


“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?”


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


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



I’m really glad our parents weren’t home that night. Dennis told me they were staying at a hotel…he didn’t 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, Escort Avrupa Yakası 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.

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.


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.

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