Filling In for Strangers

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A sister's botched sexual escapade.
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Here's one I started a long, long time ago. Just couldn't quite find my groove on it. I know readers of Incest set a high bar, but I hope it entertains you well enough. It's brother/sister, oral action only. A small tale of discovery, about a sister in need. Input is always appreciated, even on these one-offs.

*****

"Ali, you're telling me you've never sucked a cock in your life?"

"Not so loud, Keith" replied my sister, blushing.

We were in a busy Italian restaurant. Ali and I weren't especially close growing up. She was six years older than me, so perhaps the difference in age influenced the distance in the relationship. None of our family members are particularly close, though. Sure, we shared holidays together, and called Mom and Dad every month or so, but it seemed like it was over formalities, rather than genuine love.

As for my memory, I can't recall engaging in a conversation about sex with any of my siblings, but this was special circumstances. I was more amused and bewildered, than grossed out.

***

Alison was staying with me for the week. It was originally going to be three days, but the plans changed. She told me she wanted to visit the big city. Since I live in it, it made sense to house her, saving on hotel bills. As I said, we weren't particularly close, but she's family and I'm happy to have her around for a few days. The truth of her visit came out when she came knocking back on my door, after she had supposedly left town.

"I thought you were going home," I said.

She dropped her bags and huffed. "Okay, I came here to meet a guy. I didn't want to say anything to you, Keith, because-"

"You don't have to say why. I get it."

My sisters and I don't like sharing our relationship statuses with our siblings or parents. To them, it's a competition. Ali was 28 and single, while Lauren and Lillith, the twins who are two years younger than Ali, were both married and living in Baltimore. Our brother, Phil, lived on the west coast.

Ali was the one stuck in the small town where we were raised, working Mom and Dad's "Candles and Curiosities" shop. It was quaint, but afforded them a decent lifestyle. Lots of tourists in the area.

"So you were meeting someone for sex?" I asked.

"Well... kinda..."

Ali didn't give me the details until we were seated at the restaurant, but she did inform me that she discovered the man she came to meet was married. Apparently, as things were heating up between them, the wife barged in.

"It was so awkward and terrible. I told her I had no idea he was married, but she didn't care! She screamed at me over and over."

I let Ali get it all out, with tears beading up in her eyes. Finally, I asked, "Why come all the way here for a random sexual encounter?"

My sister stayed quiet for a while, gathering up the nerve to confess. "It's so humiliating. You'll think it's weird."

"Oh, come on," I said. "You don't know me that well. Weird can be fun."

"Okay, so you know I was with Dan for four years. Everyone thought we were going to get married."

"Yeah? What about him?"

"I haven't dated anyone since he and I split."

I was shocked, because Ali is hot, and that was like two years ago when they broke up. My sister has a firm build, and a fairly sizable chest, paired with a small ass and narrow hips. Some guys like that. Some guys like more curves down below. Regardless, she's easy on the eyes.

"Dan and I had a vanilla sex life, putting it nicely" huffed Ali. "We uh.. didn't experiment much." My sister's cheeks were turning pink. "Well, I watch things. Videos online. I want to try things. A couple months back I found this website where people can hook up for blowjobs, and nothing else."

I had been drinking my soft drink and almost spit it up. Somehow, I maintained my composure and just nodded, saying, "Okay, this is getting interesting."

"I posted that I wanted to meet a nice man to give my first blowjob."

***

This is when I barked out that question that turned so many heads in the restaurant. "Ali, you're telling me you've never sucked a cock in your life?" After my sister insisted I quiet down, I leaned forward, whispering, "Really? Not once?"

Ali was shaking her head, both affirming my question, and because she was genuinely embarrassed. Quite a few tables were focused on us. Giggling from other guests could be heard. I leaned in further more, ensuring no one could hear us now. "You mean, you flew all the way out here just to give someone a blowjob?"

"Well," she whispered back. "I wanted it to be with a stranger. Someone I don't know. Someone who wouldn't expect a relationship."

I was shaking my head and snickering, yet conjured up some sobering advice. "Of all the things, that is the worst you could do. You don't want a stranger on your first time. Not with something like this. You want someone who will take their time, guide you, and care about your side of it. Random sex? Reserve that for when you're experienced."

Alison sat up in the chair. "Oh, maybe I didn't think of that."

"Ali, you should date. Just go to a club or public event. Say hello to people. I promise you'll have no problems finding someone."

"I guess. It's just I have been so busy, and I really don't want a relationship right now."

Our food arrived and we continued talking about her old relationship with Dan, and how managing the store and our parents kept her so busy. "It's probably time you flew the coup, Ali. I know you love the shop and all, but maybe it's too much responsibility for someone our age."

"You know that would really hurt Mom and Dad."

"They'll get over it. One thing they taught us was self-sufficiency."

On the drive home, I asked Ali how long she intended to stay.

"I'm really sorry I lied about my visit. I was going to stay with Peter - the man I'd met online - for three days. I guess his wife was going to visit her parents or something, and it got cancelled. That's how he got busted. I swear I had no idea he was married."

"It's too bad he lied to you and his wife. Scumbag." I could see the look of disappointment on Alison's face. "Be glad his wife came home. You wouldn't have been proud you went through with it, if you discovered that after the fact."

"I know. It's just... just..."

"What?"

"I dunno... embarrassing... disappointing. Everything. It took a lot of nerve to get the courage to do this... thing... this one wild thing. And it got totally fucked up by that asshole."

I laughed, "If it's anything to ya, it's been over a year since my last booty call. I think it's our curse. We're attractive people who can't get laid."

Making light of the situation seemed to brighten Ali's mood. "So you don't mind me staying for a few more days? I promise I'll stay out of your hair like I have been."

Since she first arrived, Ali would jet off to visit shops in the city, while I worked during the day. We'd catch up in the evenings, and so far, we had enjoyed each other's company. We probably spoke more to each other the past few days, than we had all the time growing up.

"I don't mind. Tomorrow's Saturday. There's always something interesting going on, if you wanna hang together."

"That big community festival is this weekend. Peter, the asshole, had mentioned it. Groland Park, I think he said."

"That's downtown. Big hippie festival."

"Sounds fun," said Alison.

"Maybe," I said. I couldn't help myself. I had to jab just a little. "Maybe not as much fun as a blowjob, but still fun."

Alison and I erupted in laughter. "You're never gonna let me live this down, are you?" she asked. I admitted I likely wouldn't. We were almost halfway home now, and I went to turn on the radio when Alison stopped me. "You know, come to think of it..."

"What?" I asked.

"I came out here, far from home, for two reasons. One, to see the city - and you, of course - for a few days. Two, to get that blowjob. To get it from someone who I knew wouldn't create drama at home, or who would want a long term relationship."

"One out of two ain't bad," I joked.

"But why not?"

"Why not what?"

"Why can't I get that blowjob?"

"So you want to find some random stranger after all?" I asked.

"No, Keith. Are you dense? I'm talking about you."

I almost swallowed my tongue. "ME? Are you insane?"

"Come on? Rationalize this with me. I came out here specifically to commit fellatio. Nothing more. I've never done it and I want to. You and I barely know each other. We're siblings, but we certainly don't behave like it."

"Uh... okay? How are siblings supposed to behave?"

"You know what I mean. We barely crossed each others' paths growing up. I was out of the house by the time I was seventeen. The point is, I don't feel bonded to you like a sister. I barely do with the twins, to be honest, and I'm closer to them than anyone in the family."

I knew what Alison meant, but it didn't negate the fact we were still siblings, flesh and blood.

"I can't get pregnant sucking cock, Keith. There's no risk of that. And you haven't gotten laid in a year. I mean, on the surface, the whole thing sounds crazy, but think about it: I get what I want, I suspect you could get something out of it, too... while genuinely doing what you described earlier. Guiding me. Helping me."

Already, my sister's talk was arousing me. I tried not to let it be known.

She continued, "You know me well enough to do that, right? To be honest with me? To guide? And it wouldn't be with some random stranger. Here's the cherry. When we're completely finished, I still get what I came for, with no commitments. No risk of someone wanting more out of the relationship, than just this experience."

"You're right about no commitments. I'd take this to my grave if you sucked my dick."

"Then take it to your grave! Come on, Keith, what do you say? Please?"

I couldn't believe my older sister was literally begging me to let her suck my cock. "This really is important to you, isn't it?"

"Yes."

There was a lengthy pause, before I responded. "I'll say one thing. You'll probably turn out great doing this."

"Hah! You have no idea how nervous I am."

"The first key ingredient, to a woman giving great head, is her desire to give it. You've got that covered."

Ali and I chuckled some more, as I pulled into the neighborhood. Already, I was shaking. Ali reached over and touched my hand. "Thank you, Keith. I mean it. We'll do it this once and there's no obligation for more. I promise things won't get weird."

"I'm not worried about that, Ali. More concerned I won't last that long. It's been a while for me."

"How about we shower when we get home? We'll get used to each other. Then, we'll go to the living room couch and take it from there."

"You got it, sis."

"Yeah, you better call me Ali, or Alison, for now," she cracked. I agreed with her sentiment, though.

Once inside, Ali took the lead. "No point procrastinating. You have to forgive me, Keith. I'm eager."

"I can tell."

I knew Alison was attractive, but she looked better naked than with clothes on. Stunning. A lithe, athletic frame, with full breasts. A small, but tight ass. I'm considered a good-looking guy, and I've dated some pretty girls. Ali had them all beat.

"Wow, you're packing a whopper," said Ali, as I stepped in the shower with her.

"You're quite a package, too," I said. Ali giggled and spun around for me. I suspected she was never really shy about showing off that body. At least, in the right circumstances.

"So how is it you haven't dated anyone in over a year?" asked Ali.

"I don't know. Same reasons as you. Honestly, after my last girlfriend, I needed a break. It's just been extended longer than I expected."

"Was she a crazy ex-girlfriend type?"

"You could say that. She was emotionally exhausting. Fantastic in bed. Chaos everywhere else."

"Dan was just the opposite. Fantastic with everything, but the sex. Tell me, Keith. Did you used to get a lot of blowjobs?"

"Jo-Anne did it all the time. Sometimes in the most inappropriate of times." I winked. "She was a freak."

"Oh, I might like her."

I scoffed. "Even you wouldn't put up with her, though."

"I always wished Dan would have been more adventurous. It was hard to admit, I had to end that relationship solely due to the sex."

"That bad?"

"Meh... come to find out, Dan was gay. He needed the kick."

"Explains a lot."

Alison picked up the soap and lathered her hands. "Can I?" she asked.

"What?"

"Wash it. Let me touch it."

"Go ahead." I wasn't shaking anymore, but I was still nervous. She moaned the moment she touched it. Never had I witnessed such craving. She dropped to one knee and rubbed her hands up and down, circling my shaft. It responded by ticking up a notch or two. Alison sighed heavier.

"You gonna be okay?" I asked.

"Oh, yes. I can't wait."

"Do something for me."

Alison looked up, cock in hand. "What? Anything." She hesitated and smiled. "Well, almost anything."

"Masturbate for me. Here. Now. It will excite me."

"Will it?"

"Yes." As I said the word, Ali was already reaching down with her right hand, reaching her clit. She continued to wash and rinse my cock with her left hand as she slowly dug two fingers inside with her other.

"It won't take me long," she whispered.

"I know."

Ali put her face closer to my half-erect cock. I could see her right arm picking up pace as she worked her pussy. "That's going to be in my mouth," she said. I could feel her breathing on it.

"Soon," I replied.

Ali moaned hard and began pumping faster still. "Yes... oh, yes... I'm going to cum, Keith."

"Cum for me, Ali. Cum for me now. After you swallow my seed, I'll make you cum again."

Ali screamed in ecstasy as my words of encouragement reached her ears. Finally, she fell back in the tub, the water pouring over top of her. She was quivering. "Are you really going to make me swallow?" she managed to ask.

"Alison, I'm sure there are women out there who are outliers to the rule, but typically, the more a woman is willing to swallow, the better she gives head. In my experience, anyway."

"What's it taste like?"

"It's an acquired taste, Ali. You won't love it at first."

I have to admit. I was getting into the grove. Showering with Ali, watching her masturbate, talking, teasing. It was turning me on, and the sexually assertive creature in me was waking up. I wanted to push Ali. Do crazy things with her, much like I used to with Jo-Anne. Jo loved it when I talked dirty to her while she sucked my cock.

"But you're going to do it, anyway, Ali. You're going to swallow all of it. If you want me to teach you, you're going to be a fast learner, got it?"

Ali picked herself up. "Alright, Keith. I'll try. Whatever you say."

"You told me you watched porn movies? Of girls giving head?"

"Yeah... you know... I get off on it." Alison was somewhat hesitant to reveal more details.

"So you know what to expect," I said. "And something else you should know, I cum a lot. Not being arrogant or cocky. Just warning you." I pulled Alison out of the shower and tossed her a towel. "No sense getting dressed, right?"

She smiled and minutes later, I was laying on the couch, with my naked sister on the other end, leaning down with my cock inches from her face. "Thank you, Keith," she said, her eyes locked on my shaft, as she teased herself near it.

"Hopefully, I'll be thanking you soon."

"Can you make it last?"

"Put it in your mouth already."

It's hard to describe the sensation of lips over your cock, when it's been more than a year since last experiencing it. Harder, when the person doing it has lips of pearl. If this was Alison's first time sucking cock, I absolutely had to have it again, once she is experienced. "Jesus, Alison. You say you've never done this before?"

As she rhythmically worked my head and shaft, she shook her head, moaning, stuffing her face, getting into the grove.

"But you've worked this out in your head for some time then, haven't you?" I asked.

She giggled while circling her tongue on my shaft, before pulling away to speak, "I fantasize about sucking cock every night, Keith. I do. It's been like this for months."

I wanted to know more. "Why exactly this fantasy?"

"Oh, I guess I can tell you. I stumbled over some random amateur video one evening. A wife, sucking her husband's cock. And I don't know... just the way she did it. It was so beautiful. It turned me on, and I kept going back to it."

"You might have to show me this video," I chuckled.

Ali kept stroking me, while talking, "Yeah, I should. I mean, I've watched other videos, too, since then. I went exploring after I discovered that video, for sure. But it's the best. She just... how to explain... it's like she is simultaneously the most selfless woman in the world, while also being the most selfish, in that moment. Selfless, in that her singular goal is sacrificing herself to her husband. Pleasing him in every way. And yet so selfish because you can SEE it in her eyes and her expression. How much she needs him to cum, so that she can cum, too."

"Okay, now you absolutely have to show me this video," I laughed. My cock was raging hard, both by Ali's actions and her talk. She wrapped her mouth around the head again, taking it in. "Ali, you're a natural. You could work on taking it deeper, as you find your rhythm."

Ali was moaning, and she kicked her left leg over mine, so her crotch was now digging into my shin. It was soaking. She softly swayed her clit against my skin as she took my cock deeper into her throat.

"You are far better than I expected," I admitted, while Ali continued working. "So listen, we're going to have to do this twice. Maybe three times." Ali stopped. With my cock far into her mouth, she awkwardly tilted up, her eyes questioning me. I explained, "Yeah, I won't last. You're too good. So I'm going to cum soon. But give me a few minutes to rest, and we can do it again. How does that sound?"

Ali's eyes went wide with anticipation, and I felt even more dampness down below. She eagerly went back to servicing my shaft. I reached down, firmly grabbing the back of her head, while being gentle enough to guide her, rather than force her. Time seemed to slow, but it was perhaps second later that my first load erupted into her mouth.

"Swallow, Ali. Swallow fast, so it doesn't gag you!"

But the warning didn't help much. As Ali struggled to swallow while being blasted with a second and third deposit, she spit up a hefty amount, cum splattering across my stomach and pouring down her chin. She tried to keep her mouth closed over the head of my cock, but failed to finish me off entirely. My last rope of cum hit her right cheek.

"Oh my god. That was so much!" she exclaimed.

"It's been a few days since I masturbated. Been busy."

Truth be told, I am more boastful about my semen count, than my penis size. Every girl I've dated has commented on my surprisingly heavy loads. I suppose there are sillier things to be proud about, but I definitely won the genetic lottery on that trait. Ali started giggling, and maybe even blushing again. I couldn't tell.

"What are you laughing about?"

"That tastes absolutely awful."

"Hah, I told you it's an acquired one."

"I'm not sure I will ever like the taste of that."

"That's too bad, becau-"

"I didn't say I didn't love doing it. Oh my god, that was so fucking hot. Of course I loved it. Please tell me you will cum in my mouth again."

"That's the kinky girl I want to know," I said, beaming. "She hates the taste of cum, but still insists on taking it."

"Fuck yes, I will. I am so glad you promised to do it more than once." Ali was still folded at her knees, her face near my cock. She was touching bits of cum, rubbing it between her thumb and forefinger. "Can you really do it again? So soon?"

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