“No, silly, that’s crazy! But it got me really hot and wet. I came so fast when I masturbated to it.”
“To it?”
“After I left your office, I went down the customer restroom. I sat on that toilet and frigged myself to the most amazing orgasm! This old lady was in the stall next door. I don’t know if she heard me, but I didn’t care. I came so hard my teeth were tingling. Then I went to the mall, and did the same thing in the ladies’ room at Dillards. Ryan, I ended up masturbating four more times this afternoon. One of them I did standing up in the foreign film section at Blockbuster.”
“Jesus, are you kidding?”
“It’s crazy, I know. But the feeling of that hot sticky cum between my tits, it’s like some crazy aphrodisiac. And when it dried, and got all hard and crusty, oh man. I could feel it flake off and collect in the bottom of my bra. Stop looking at me like that!”
I realized I had been staring at her like she was criminally insane. And indeed, this was some strange fantasy she was living out, and telling me about.
“I’m sorry, Helen, but you have to admit just how fucking weird this is.”
“I KNOW,” she sighed in apparent agony. “But I desperately wanted to try it, and I didn’t trust anyone else to understand.”
“Why did you figure you could trust me?” I queried with a certain smugness.
Helen thought a moment. “Well, I did let you pee in my hand when you were 12.”
My smugness vanished in horror as I remembered some of the humiliatingly childish things we’d done together. She watched my satisfaction disappear, and she grinned with her own smug smile.
“Ok, you got me there. But Helen, we’re in our twenties now. We’re not kids anymore. I’m sure you want a boyfriend, and I certainly wouldn’t mind a girlfriend eventually.”
“Ryan, what I want is to try out some things I’ve been thinking about for a long time. I’ve always had an active mind for fantasies, Ryan, you know that much about me.”
“That’s true,” I conceded.
“I trust you, Ryan, because it was with you that I discovered my sexual side. At the time, neither of us was equipped or trained to truly satisfy the other. You’re right, we were kids. But I’m not anymore. I want to try some things, and maybe let you try some things.”
“Um, like fuck buddies?” I asked, unsure of how this would turn out.
“That’s putting it crudely, but I guess so, yes.”
I considered that a moment. It was almost perfect, in a way. For one, it was almost unlimited free sex. Two, it was someone I already knew and loved. Three, it was almost like hooking up with an ex-girlfriend, someone with whom I already had a modicum of sexual history.
Then again, she was my sister, and she was almost certainly cracked.
And then yet again, I could probably keep jacking off into her tits, which, bizarre as it was, was actually kind of cool.
“Okay,” I sighed, as if only caving in as a favor to her. “Let’s give this a try.”
She exhaled a loud sigh of relief, while simultaneously whipping off her t-shirt in a single motion.
“Awesome. Now fucking jack off into my tits again. Now!”
She plopped down onto the couch and unhooked her bra. For the second time in a day, I found myself staring down into Helen’s impossibly sexy bare breasts.
“Now? Are you fucking kidding me?”
She ignored the question and unbuckled my pants. I let her do the work, and her warm hands on my flaccid cock caused it to harden instantly. The head was swollen, almost a lurid purple, and she wrapped her fingers around it. I prayed she would pop it into her mouth, but after a moment of tender adoration, she released it.
“Start stroking, dude. I can’t tell you how excited I am for this!”
I laughed aloud at her childish enthusiasm, and took my length in my own hand. Two things had changed since the first time this happened: I finally understood a little bit, and I was no longer at work. I decided to take my time and enjoy this.
I stroked on, using long, measured pulls designed to excite me but not get me off prematurely. I assumed, despite her clear obsession with the resultant ejaculation and its requisite destination, that she also enjoyed watching me masturbate. I hoped it was true. I turned out to be right, as she cooed and moaned, egging me on. She often put her half-opened lips near the tip, threatening to fellate me. But then her lips would curl into a smile and she’d back away.
“Do you want me to play with my tits again, the way I did today? It seemed to turn you on…”
I grunted agreeably. She commenced her caresses, cascading her hands over her full breasts, lingering on her large nipples. She pressed them together again, pushing her cleavage up toward me. The curves, the smoothness of her skin, the angle of her neck and she leaned back to watch me jack off. I felt it happening. My balls tightened, and I nearly lost my balance.
“Whoa, buddy, don’t go anywhere!” Helen put a hand on my bare ass and pulled me toward her. “Just put the tip of your cock right against my tits. I want to feel it come out.”
It was the last straw. Her dirty mind and strange fascination with my cum tipped the scale, and my spunk erupted against her skin. I leaned into her, and my cockhead almost disappeared between her breasts. The cum curled around my sunken tip and ran down the ravine of her cleavage. Helen purred.
“Fuck, Ryan, that is the hottest thing I have ever experienced. Oh God, I can feel it oozing under my tits. Jesus, that’s amazing. God, my pussy is just soaked. I gotta frig!”
I stumbled back and dropped onto the coffee table. My sister pulled down her shorts and stuffed her hand into her lacy pink panties.
“Oh Christ, this is gonna be a good one!”
“Well, fuckin’ let me watch, Helen!”
“Oh, right, I suppose that’s only fair,” she said nonchalantly, and pulled aside the crotch of her panties. A gentle patch of dark brown hair appeared, but clearly visible through the tangle was the glistening slit of her sopping vagina. Her fingers quickly found their target, and she easily ran her fingertips up and down the well-lubricated gash.
Helen wasted little time teasing, and got right to the business of intense pleasuring. With her left hand she rubbed at her beefy clit, and with her right she pumped two fingers into her slippery hole. I could only stare in disbelief as my sister drove herself to a violent and intense orgasm. I could see rivulets of my ejaculate running down her stomach. She yelped loudly when her orgasm landed, and her hips pumped involuntarily, thrusting her open crotch at me. I felt my cock stir as I watched my dear, sexy, slightly perverted sister awash with climax.
We kept things more or less at this level for a few months. I think part of it was a fear of escalating things too quickly. I think she was also still enjoying the novelty of the cum-in-the-tits activity. For that matter, I had learned to enjoy it almost as much as she. I made her suck me off a couple of times, just to break up the action, but even then she spat out the cum and let it dribble down into her cleavage. I also talked her into let me eat her out to bring her to orgasm, at least some of the time. Her pussy was spicy and intoxicating, and I soon discovered my own fantasies and fetishes centered on her delicious snatch.
Then, one day in the fall, things got very weird again. This is where you joined the story.
“Ryan, I want to you help me get a bunch of guys to all jack off into my tits at the same time.”
“You want to do what?” Her request was so bizarre I had to hear it again.
“Please? I have been obsessing over this idea for months! Can’t you please help me make it happen?”
I looked Helen over from head to toe. She was a strangely built woman, but attractive nonetheless, at least to me. She had a very round head, and a preposterously oversized chest for her height. Her waist was surprisingly slender, but her rounded hips and full backside gave her an irresistibly womanly shape.
“You want me to find a bunch of guys to cum on your tits at the same time? Like a gangbang without the bang?”
“Quit looking at me like I’m crazy. I’m just exploring.”
“Am I not good enough anymore?” I wasn’t sure if I was jealous or just confused.
“No, that’s not it, Ryan. It’s just an extension of the same fantasy. If one load of jizz feels this good, I can’t imagine what five or six would be like.” She almost shuddered at the thought of it.
“Where would I find five or six guys? I can’t ask anybody from work. They all know you, and they know you’re my sister.”
Helen frowned at that. “Can’t you think of something?”
“Helen, don’t you think this is a little weird? And maybe even more than a little dangerous? What if somebody recognizes you? Omaha isn’t that big of a city.”
“We’ll just do it one time. Then it’ll be out of my system. I swear.”
I sighed. “Fine, I’ll see what I can do.”
I finally cooked up a scheme that might work. Since I was a reasonably well-qualified bookkeeper, I decided to get a part-time job over the holidays. I found a machine shop whose bookkeeper was out on maternity leave. I told them I’d get them through the first of the year, but that someone else would have to do their year-end books. They agreed.
The machine shop was perfect. For one, it was in a part of town that was totally unfamiliar, so the odds of seeing anyone we’d know were low. Second, it was filled with robust young men (and a few rusty old ones), several of whom were reasonably handsome and potentially trustworthy. She was, after all, my dear sister.
The fall and early winter passed quickly. Helen moved in with me in October, ostensibly to save money on rent. In truth, we fooled around at every likely opportunity, though never involving penetration, just foreplay and occasional oral sex.
Eventually I got along well enough with some of the machine shop guys that I felt comfortable even mentioning the scheme. I sat with one of the guys, Chris, while he had a cigarette break.
“Hey Chris, does this place have a Christmas party?”
“Yeah, they always put on a little thing with dinner and drinks. Nothing special. We usually go get wasted afterward. Why?”
“Oh, I’ve got an idea for how to make this year’s party a little more interesting.”
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