Kelly's Diary 177 - Cockteaser - Cover

Kelly's Diary 177 - Cockteaser

Copyright© 2025 by Kelly85

Chapter 7: Tony’s Girlfriend Heidi

Erotica Sex Story: Chapter 7: Tony’s Girlfriend Heidi - Flirt, lush, tramp, slut, cockteaser, bitch, even whore... I've been called them all. I guess it comes with the territory when you love sex and live by a "if you got it, flaunt it" attitude. I'm not afraid to admit I LOVE to tease. It's fun to see what a man will do using nothing more than the offer of your body for incentive. People ask me if I've ever NOT gotten what I wanted from a guy, at least sexually speaking. Well, my best friend's brother was one of my greatest challenges.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Ma/ft   Fa/Fa   Consensual   True Story   Masturbation   Oral Sex  

That afternoon, when I had returned home and was laying on the couch watching TV, I couldn’t help but think about Tony and how wonderful it had been to suck his dick the night before. I could almost taste the cum in my mouth again! That night I went out with a friend I’d met at a party a while back. We ended up at his apartment (I never bring them back to mine), and as he was fucking me, I caught myself imagining it was Tony fucking me instead. Indeed, at one point I almost called out his name! Now THAT would have been a bit embarrassing, to say the least. As good as it felt to finally get laid again, I came home later that night feeling a bit unsatisfied, as if something had been missing.

For the next few days, it was a constant nagging in the back of my head. All I could think about was Tony’s cock; how it tasted, how it felt while it was growing, the smell of him, the way his cum felt as it shot into my mouth. I lost count of how many times I masturbated thinking of him fucking me in his bed while his sister and parents slept. To be sure, I didn’t feel anything for him, I mean I wasn’t in love with him nor had I any desire to be his girlfriend or even a close friend. Instead, it was more like I was seeking the Holy Grail, or the Fountain of Youth, or anything else that fixated someone on a goal, a quest that they feel drawn to or even compelled to finish.

It was killing me that I had been so close, that I had his dick IN MY MOUTH and yet hadn’t been fucked. Sure, there had been plenty of guys I’d sucked and not allowed to fuck me, but it was ME that made that decision. I couldn’t remember any other time in my life when I’d had my mouth on a guy and wanted to get laid by him that I had NOT ultimately gotten what I wanted. It was frustrating as hell, to say the least. It didn’t help he was the brother of my best friend. Well, that didn’t really matter, it was that she didn’t want him to fuck me that was the problem. How the hell could I get him to do me without her finding out?

Well, the Bible says that no temptation will be made on you that you cannot overcome so I shouldn’t have doubted that sooner or later, a solution would be found. Who was it that said, “The Lord works in mysterious ways.”? Well, they didn’t know the half of it!

The key was Heidi ... Tony’s plain, but well endowed, girlfriend.

It was a slow weekend for me. Right after New year’s the demand for parties was at rock bottom and I supposed it would be a few weeks before things picked back up to normal again. Thus I had a lot of free time on my hands but still, a girl can only masturbate so much - even me! As it turned out, I was over at Beth’s house, more to just have company than anything specific, when Tony came in, closely trailed by his girlfriend,

“Hey Heidi,” Beth welcomed her.

Come to think of it, that was the first time I’d heard her refer to her brother’s girlfriend by name, it had always been “my brother’s girlfriend” or “his girlfriend” (or something nastier).

I looked at Heidi a little closer and once again had to shake my head a bit. Sheesh, what did he see in her? A hunk like him should have had his pick of any babe around but instead he was going out with dumpy Heidi. To be fair, she was a sweet girl and “had a nice personality” as they say, but a low-carb diet and some exercise would have certainly been a nice New Year’s resolution for her. Of course, it was hard not to notice what he DID see in her, or should I say ON her - the most massive boobs for a girl her size I’d ever seen outside one of my dad’s porn DVDs. Heidi was not really a BIG girl, not by any means. Sure, she had a fat ass and was overall a little chubby, but she wasn’t truly obese and she was pretty short as well. But her boobs ... OMG her boobs! The only way to describe them is they were simply massive. It was a miracle she didn’t walk all hunched over from the sheer weight of them. When Beth said her brother was a “boob guy”, she wasn’t kidding.

The two of them quickly made their way to his bedroom, the door shutting tightly behind them. I guess at nineteen nobody could tell him that he had to keep his bedroom door open when a girl was with him although noticed that Beth didn’t seem entirely pleased with it. We soon forgot about them and spent the rest of the morning just hanging around, not doing much of anything, when Beth’s mom called. Beth answered her cell phone and I could see from the sagging of her shoulders she was frustrated - and a little pissed.

“What? ... Now?” she whined into the phone, “Oh mom ... can’t it wait until later?”

Whatever “it” was, evidently couldn’t wait as she slapped the phone shut rather hard.

“I don’t fucking believe this,” she griped as I waited patiently for her to continue, “My mom ordered this fucking cake and I have to fucking pick it up before they fucking close.”

She must have REALLY been pissed. Beth didn’t have exactly the cleanest mouth but still, she usually didn’t manage to sprinkle so many “F” words in one sentence. She looked at me and evidently the question in my eyes was all she needed to know what I was thinking. “Down at that shop on the Strip. Look, you just hang out and I’ll be back in 45 minutes or so, OK? No need for both of us to bundle up and freeze our fucking asses off.”

She stormed off to her room to get her shoes and coat, mumbling all the way in and then all the way out. “Catch you in a bit,” she called out as she went into the garage.

I’d spent plenty of time in her house alone before, just as she had in mine herself at times when I was running late or needed to go out myself for a bit. I’d been coming here almost all my life so it was like a second home to me in some ways. Thus I didn’t feel guilty raiding the frig or making myself at home so I went to the kitchen, grabbed a can of Diet Coke, and settled into the couch in the family room to watch some TV. I was a little tired so I was starting to drift off when my privacy was disturbed by Heidi and Tony. Something didn’t seem right, you could tell from the body language that the two of them weren’t exactly hitting it off at the moment. Heidi spoke first, actually the first time she’d ever spoken directly to me come to think of it.

“Kelly, are you really a slut and is your sister really a whore?”

Whoa! Now THAT was right out of the blue. I have to admit, give me a thousand guesses as to what she might ask me and I’d of never gotten that one right.

“Sorry,” she continued, as if nothing was odd about her questions, “Tony here called you a slut and your sister a whore ... so I was just a little curious.”

There was more to it than that, THAT was obvious, but I figured what the hell, why not play along and see where this train wreck was heading. I just shrugged my shoulders and answered simply, “Sure ... you have some sort of problem with that?”

Heidi quickly waved her hands and shook her head. “Oh no, I didn’t mean it that way. He calls me a slut too, you know, “she confided in a conspiratorial tone as if he wasn’t right next to her listening to every word. There was an awkward silence so I decided to probe a little and see if I could figure out for myself what was going on.

“And he told you all this because...?”

Heidi actually seemed to blush for a moment and she looked at Tony as if expecting home to support her. No luck there. She finally took a breath, her monstrous boobs heaving up and then down again as she released it slowly.

“Well, I’ve been teasing Tony about us having a 3-some lately with his sister but can you believe it - he won’t even talk about it!”

I couldn’t help but smile - my kind of girl. It didn’t surprise me that she’d gotten that reaction from him. If there was one thing I was certain of in this world, it was that Beth and her brother would never have sex together. It’s not like I hadn’t suggested it but her reaction was always the same; a look of sheer disgust and a loud “Ewwwww!”. It followed that Tony would feel the same way about his sister, even if she DID have big boobs that I knew he looked at now and then - although nowhere near the scale of Heidi’s rack.

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