Jack and Jill and Mom Ch. 01

"Jack, I need you to do me a favor."

I looked up. My sister Jill stood in the doorway to my bedroom. Jill is 20 and a junior in college, I am a senior. She has brown hair, an athletic build and larger than average breasts. Not a total knockout, but not bad to look at either.

Yes, our mother Janet named us Jack and Jill. Our dad, John -- left years ago. We still see him less and less as we get older. The emphasis on the letter J in our family runs deep: We have an aunt Julie and sister-cousins Josie and Jenny. More on them next time.

"Jack?"

"What," I looked up again. I shifted to sit up on my bed from where I was doing some homework. I pushed the books aside giving her room to sit on the edge of the bed.

"Mom has been super cranky and irritable lately."

"So, what does that have to do with me?"

"We need to get her laid, and soon."

"What?" I asked incredulously.

"I don't think she has had sex since dad left. That's more than 4 years ago."

I looked at her and thought about this. "She needs a boyfriend. Seems like you can help her with that more than I can."

"Long term, yes. But dating can be hit or miss, and she may not find someone at all." She thought about it quietly. "I don't think she has had a date, or even wants to date. She is so stressed at work and with taking care of us and the house, she doesn't give herself any time for a personal life anymore."

I nodded in agreement. "Still, why are you so concerned with our mom's sex life? And why the urgency?"

"Her 40^th is coming up, and I'm concerned about her stress. Plus it's a milestone age, some people get depressed when they are alone."

"Uh-huh," I replied, questioning her still. "This doesn't have anything to do with you wanting to go on a Caribbean cruise with your friends after the school year wraps, does it?"

"What? How did you know that," she laughed and absent-mindedly played with her hair.

"My friend Derek said his sister Amy asked their parents over dinner last night."

Realizing the gig was up, she changed her tone. "Please! You have to help. I think it would help relieve a lot of stress. And people make better decisions when they are happy. It's win-win."

"For you two, perhaps. Why am I involved in this discussion?"

"Don't you want mom to be happy?"

"Sure, as much as anyone." Then after a moment, "Look, I really don't know anyone in her age group. Nobody I would think is a good candidate to set up on a date anyway. And that says nothing of getting laid. Can't you get her a new vibrator or something?" I asked, somewhat serious.

"Not the same. That only works so long. At some point, you need the real thing, you know."

"I'm sure I don't want to know."

"The thing is, I think she needs a younger guy. It doesn't need to be a long-term thing. Just some personal attention, to help her feel good about herself. And to give her an orgasm or two."

"You're not asking much," I said. "The guys I know are all our age. If anything, they are looking to hook up with college girls." I paused, then added, "Guys typically want someone younger than them, not older. Or older to them means just a couple years older."

"I can't believe that there isn't one amongst them that wouldn't like to sleep with a beautiful, athletic older woman with no strings attached." She was right, our mom was attractive and slender in an athletic way, too. Her breasts were Ds but the looked bigger because of her petite frame.

"And how do you know there are no strings?"

"I mean, she isn't going to be looking for marriage or to get pregnant, right?"

"Ugh," I shook my head. "I can't believe I'm listening to this." I leaned forward to get up.

"Wait," She put her hand out, blocking me and prompting me to sit back down on the bed, leaning up against the headboard. "All you need to do is ask them."

"That simple? Ask my college buddies which one would like to fuck our mom... Are you kidding?"

"No, that's what she needs." She was serious. "Don't you guys talk about women?"

"Generally, our moms don't come up in conversation. That would be crossing the line. Look, I don't like the idea of any of them having their way with mom."

"I guess I thought most guys have a friend whose mom they would like to fuck," she pondered. "Isn't that what a MILF is?"

"Sure. It's like this: sometimes we see a mom at Starbucks or the market, that we find attractive enough to have sex with," I replied. "But what you're asking is that the son to get involved and set that up."

"All I'm asking for is to help mom get her groove on. Get a man back in her life. Who can say if it will result in a relationship or just a casual hookup."

"Well," I stammered. I really preferred to extract myself from this.

"And she needs to get it this weekend."

"Wait, what?"

"OK so you were right. The group is buying tickets Monday. I can't be left out," she stressed the last part.

"Now you're really asking a lot." I turned and grabbed my coke from the desk near my bed.

"What about Derek?" She prodded on, un-deterred.

"He has a girlfriend."

"So?"

"So," I replied back, "he's not looking to score with someone else. And I'm not going to ruin their relationship for your benefit."

"What about your friend Steven, he seems mature for his age."

"He's in Florida for visiting his dad."

"Hmmm..." she said, biting her lip.

"Colin?"

"No way, he wouldn't treat her right. And he would brag about it," I replied.

"Yea, no good," she agreed with me. "But there has to be a way. You have to think of someone."

"Nobody comes to mind." Then I turned it on her. "Look, this is your plan," I countered. "I'm not the one that wants this."

She looked at me like trying to solve a puzzle. "Don't you though?"

"What?"

"Think about it. Mom gets lucky, she's happy -- makes all our lives easier. I get what I want, I am happy -- makes all our lives easier." I could tell she was formulating a plan in her head. "Plus, I would owe you big time for this favor."

"Ummm," I was curious now. "Like how?"

"What if I could get you hooked up with Stacy?" This was intriguing. Stacy was cute and stacked.

"I wouldn't mind that at all. But I don't see how that helps -- I don't have a guy in the wings waiting to do this. It would take careful planning and plenty of time."

"Yea," she relented. Then a thought hit her and a devilish grin came over her face.

"When was the last time you had sex?"

"It's been nearly a year since I broke up with Shelly. But I don't see what that has to do with this."

"You could do it."

"Pfft," I nearly choked and put down my coke. "What?"

"You could take care of mom." She was getting excited now.

"I'm not screwing mom so you can go on a trip."

"You might not have to."

"You've lost me."

"You could, you know, use your hands, your mouth, whatever it takes. She might be so pent up and ready, I'm betting it doesn't take much."

"To get mom off."

"Yes. To relieve her stress, give her what she needs." My sister was playing the angle. "You might even get to get some, too." She was trying to sell it now.

"I'm not sure you're thinking clearly. Even if I wanted to, she would never go for it. Not with her son!"

"Hmmm," she was working things out in her head. "Maybe, that might take more time." She had an evil look on her face, but then it changed again, and she had another idea.

"How about this, we make her dinner, full setup, basically do everything -- treat her like a queen. Then there's a bottle of wine, music by the fire... I leave to do dishes. You remain, give her a slow back rub that turns into something more..."

"What if she doesn't go along with your evil plan?"

"Leave that to me. You just do your part."

"What if she doesn't like my moves?" Did I just say that? I can't believe I'm saying this. Am I really thinking of going along with this?

"True, you could test out your back-rub skills on me."

"Wait, that's not what I meant."

"What are you worried about? Trust me, I will orchestrate the evening. If you try, she will melt in your hands, I promise."

"Look, I am not looking to take advantage of mom. I don't think of her that way," I had to say it, but it wasn't entirely true. Ever since my sister and mom had become sun-bathing partners, I had snuck peeks from the upstairs bedroom window. At first I had fantasized about Jill. And I was sure she would pull her bikini bottoms to expose more when she knew I was looking. Occasionally I noticed mom too, when she would take off her bikini top and show side-boob as she would lay down on the lounge. Or when she would go topless while applying lotion.

"Don't think of it like that," she answered, bringing me back from my daydream.

"Oh no?"

"Think of this as, doing us both a favor. And getting rewarded for your efforts," she added.

"Rewarded?" I inquired.

"Stacy likes you, she told me so. I think I can work in a blow job. She is really good at oral, or so I've been told," her voice trailed off.

"Not nearly enough," I answered. "Maybe to set mom up on a date. But not for me to do anything myself...."

"I realize this is asking a lot." She looked at me, the wheels still turning in her head. "So," Jill asked coyly as she scooted close enough to me on the bed. "What do you want, big brother?" She touched my gently as she looked up with soft, wanting eyes. She always knew how to work me, like she had done many times before.

"Are we negotiating now?" I looked at her. My arm was tingling, but I was aware she was distracting me, using her assets to her advantage.

"Yes. What will this take to seal the deal?" This time the stakes were higher. She brushed her breasts up against my arm. Was she serious or just playing with me?

"This is unlike anything you've asked before." I said sternly. "But" I concluded, "I think you know."

I looked down into her, my own needs and desires coming into focus. "I think you've known for a long time what I really want from you. What I need from you."

She looked back at me, the thought hitting her hard. Not because it was necessarily new. We had danced around this for years. Play fighting that led to innocent and then not-so-innocent touching, flirting, brushing-against, even the occasional groping. Once in the pool we were rough-housing, and I full on grabbed ass, but played it off like it was part of the game. She didn't complain, but neither did it go anywhere.

No, it was now a thing because it was finally said out loud, with clear meaning and in proper context.

I reached for her. She turned towards me, raising up on her knees. She leaned in for a hug, her breasts just barely touched my chest.

She reached down to my crotch and whispered in my ear. "You want me to suck your cock, is that your price big brother?" She said it as seductively as she could, and it had the desired effect. A second seemed like an hour, the feeling of her touching me unmistakable. She rubbed into and on me, now her chest rubbed firmly into my arm.

"Yes and no," I replied, coming back to life.

She pulled back, looking at me part questioning, part disappointed.

"No, the price for this is that you're going to give yourself to me," I looked deep into her eyes. "Fully and unconditionally."

"What?" She asked in a surprised tone. But I knew that was a ruse, she had already come to the same conclusion. She just didn't want to make the first move.

"I get you in my bed, all weekend, anything I want."

"What?" She was trying to process and come up with a response. I wasn't sure if I had played my cards right, but I wasn't stopping now.

"Sucking my cock," I continued as I stood up next to her and pulled down my shorts, "will just be the down payment to know you're really serious."

---------

It was only a few seconds, but the silence was tense as I waited for her response.

I had stepped out of my shorts and stood in front of her, offering her my cock which was level with her mouth.

Jill looked at my now rock-hard member, then to my face and back down again. But then she smiled as she reached for it, grasping and squeezing it in her hand. "Well, I didn't think you had the guts to go this far."

I gave a sigh of relief and anticipation. She leaned in and started to lick my shaft, and then used her soft lips to kiss the head. Her fingers squeezed gently at the base, and she put the head into her mouth.

After a moment, she re-positioned herself at the edge of the bed, grabbing my ass and pulling me in tighter. My cock was super hard, and her mouth was super warm. She pumped my shaft as she bobbed up and down.

At this point, I reached down and cupped her right breast, causing a slight whimper of pleasure. I had thought about them a lot over the years. More recently since the sun-bathing had resulted in her being in a bikini out by the pool regularly and often. But now I was feeling her up, squeezing and exploring.

"I want to fuck your tits."

"What? Sure." She was game now, and we both were hungry with passion and lust. She stopped long enough to remove her top, then squeezed in her arms at her side to press her tits in and up. Then she leaned into me again.

But I had other plans. "No, lay back on the bed."

"I like where you're going with this." She found a comfortable position and again squeezed her arms in to push them together. I took off my shirt, then climbed into bed. I straddled her, offering my cock again up at her mouth first. She instinctively knew, sloppily and purposefully leaving my cock wet. Then she did something that surprised me a little. She spat on her hand and rubbed extra saliva in her cleavage. She had clearly done this before.

I had been gazing in awe and this beautiful creature, my little sister. She had short shorts on, and topless she lay on my bed, waiting for me. Just then it hit me -- she was waiting for me. She looked up with sexy gaze and naughty smile. "Don't you want to come on my tits?" She rocked her arms causing her chest to move, ensuring I was fixated on them.

"I do. But I want to do so many things to you, I can't do them all in one day." It was true, there were 100 different things I wanted to do. "Today I'm coming in your mouth for sure."

"I love it. Give it to me, big boy."

I placed my cock in between her tits, and she squeezed with her hands over the top, interlacing her fingers just enough to create a tunnel for me.

"Let me know before you cum, okay?"

"Why" I asked.

"Just so I can be prepared. I don't want any to get in my hair, it's a mess to wash out." she said with a wink and a smile. "I assume you want me to swallow it all?" She asked naughtily.

"Yea, uh, of course!" Man, this was turning out good.

I began to move my hips, thrusting my cock between her breasts. They were average in size, but they looked great. And as I had my cock between them and they were wet and soft, they escalated in status to awesome. I pumped some more, and she encouraged me. "Fuck my titties with your big cock."

I wasn't particularly well endowed, a modest 7 inches. I figured she just wanted to talk dirty to help me get off faster. I didn't mind, because hey I'm fucking my sister's tits. But then I appreciated her more for it -- after all, she has her own needs and desires. She was fully into it now, pushing out to give me maximum friction against her chest. I decided to give her something in return.

I reached down and behind me, exploring between her legs with my right hand. She adjusted enough to let me find her pussy. At first I was rubbing over her shorts, and I could feel the wetness and warmth. Then I slipped my finger around the side and under, touching her skin. It seemed to tickle but then she gasped as I slid at first one then two fingers into her waiting pussy. She was so wet, and pushed her hips up to angle better, enough to engulf my fingers. I felt her pubic bone then pulled back and thrust in again.

"Oh my god," she exclaimed. We rocked in unison. I was trying my best to fuck her tits and finger her pussy at the same time. But it was behind me and a bit awkward. It became increasingly hard to do both as I eagerly wanted to get her off. She must have realized the predicament. "One at a time may be best."

I was about to relent, but then had a better idea. I raised up straight then lifted my leg and hopped off to the side but still on the bed.

"Are we done?" she asked, quizzically.

"Not by a long shot," I replied. I prompted her to lift her waist, and I removed her shorts. She was now totally naked. "You are beautiful," I said. And I meant it.

"Thanks, but you probably say that to every girl that is about to suck you off." She winked again, fully into it now.

"That doesn't make it less true, but I haven't had many girls." I turned around, and straddled her again above her chest, but this time facing away from her head. "Press your boobs together again." She interlaced her fingers and I leaned in to line up my cock again at her tit-tunnel.

After a few thrusts, I leaned forward and put my left arm down to brace. It was inside her left leg, and I pushed out my elbow. She realized what I was doing at this point and pulled her leg back and over my arm. I leaned forward and down, and now I held her leg in position with my torso. With her pelvic area exposed and slightly raised, with my right hand I reached in and easily found her pussy.

"I've wanted you to play with my pussy for a long time."

With a slight shift in angle, I was able to easily finger her again. Her pussy was wet and warm, her nectar smelled lovely and sex filled the room. I thrust against her chest. She held the tunnel right with one hand. With her other hand she began pinching and rubbing the head of my cock with her fingers as often as it came to her hand.

"I'm gonna cum!" I lifted my waist up and back, positioning my cock over her face.

I released her leg, and then she was able to reach up with her head to find my cock with her lips. Then she grabbed my ass and pulled me hard into her face. I came hard and shot my load into her warm mouth. Four, five, six bursts of cum and she swallowed it all.

I was in heaven: the sexual release brought about by great physical contact combined with naughty behavior. Spent, I was about to collapse on the side. But I realize I had left her hanging. She didn't necessarily demand anything, but I felt it was the right thing to do. I wanted to please her, to give her what she gave me. Any good lover would do the same, and that's what I wanted to be to her.

So I leaned back down and quickly re-acquired the position with her left leg over my arm and her foot resting on my back. With my left arm bracing me, I reached her soft ass with my left hand and pulled her cheek out slightly. With my right hand, I slipped two fingers back into her pussy, and my thumb searched for her clit. I rubbed a minute and thrust in and out as I finger-banged my hot little sister.

Then I decided to go all out. I lowered my face fully into her pussy and licked her clit, occasionally nibbling on her labia. I pulled back farther on her leg, raising her hips up more. I thrust my fingers deep into her, searching for the spot.

"Oh shit," she replied, arching her back and forcing her hips into my head. "That's it - lick my pussy! Make me cum Jack!"

With enthusiasm I found her clit and alternated between biting her and licking with my tongue all over her outer lips. Now I had 3 fingers in her pussy, quickly pounding her tight snatch. I twisted and turned my fingers occasionally to find new spots on the inside of her. My pinky finger rubbed up against the outside of her anus, and I pressed it in to the first knuckle.

"Fuck!" She gripped my leg with one hand, digging into my skin with her nails. Het butt tightened around my little finger as she convulsed. "Fuck me!!! I'm cumming!!!" she shouted in joyful bliss. Her hips bucked and she squeezed my head between her legs. Just then wet liquid splashed my face, and it smelled funny. After a moment I realized she had peed on me.