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 40th 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.But then I felt her release. My little sister was under me, and she continued to buck and heave as I fingered her. I slowed my pace but kept at her as her body spasmed. Eventually she relaxed into the bed. I could see white sticky cum on my fingers and licked it off. Then I stuck my tongue into her juicy pussy for a moment, as far as I could go. My mouth was engulfing her vagina, and my tongue tasted her intimately.
"Holy shit" then she twisted and turned, getting out of the path of my attack. "It's sensitive right after."
Smiling, I collapsed back onto the bed, and she curled up into me. I pulled her in with my arm, and we lay there for a minute, just enjoying the moment.
"Fuck, that was awesome," she broke the silence.
"I've wanted to do that for a long, long time," I said.
"Me too. I've never come that hard," she said, "or that long."
"I didn't realize you would pee."
"Oh shit, I thought I was just imagining that." She replied. "When you put a finger in my ass, I guess I just let it all go. That was the best orgasm anyone has ever given me." Then she turned and said, "I'm sorry if that grossed you out..."
"No, no... not a problem" I interrupted. "I was just surprised a little, that's all. You could have let me know, just so I could have been prepared. It's a mess to wash out," I winked at her.
"Fair enough," she said. Then after a moment, "But if you knew going in, would you have still done that?'
I thought about it a second. "I might have positioned my face differently. Either way, I wasn't about to stop, that's for sure."
"If you had I would have been disappointed."
"Actually I'm quite flattered."
"That I peed on you?"
"Well, you did say that was the best orgasm you've ever had. I suppose if you let go, it meant you were really at the height of pleasure."
"You can do that to me anytime you want."
"I can?" I asked seriously.
"Yup. You have good moves. I approve." She winked at me.
"Thanks," I replied. "Speaking of which," I looked over at her. "Where did you learn your moves?"
She giggled. "Mom of course."
"Wait, what?"
"She said to use hands, tits or mouth. Pussy too easily leads to pregnancy of course. And giving up your ass leads to becoming a slut."
"Well, whatever she said, you have good moves. I approve." I winked back at her.
"But seriously now," she changed her tone. "Let's not forget the master plan. Is that what you are going to do to mom? She'll definitely say yes..."
"What master plan? Do what to mom and say yes to what?" Our mom's voice rang out like a gong. She had just rounded the corner in the hall and came into view. We had totally not heard her come home, nor had we thought to even close my bedroom door.
"Holy shit! What the fuck is going on here?" She was looking at the two of us, naked and in bed. Our hair was messed and we looked like we just worked out. The smell of sex permeated the room.
"Mom, I can explain" we both said at the same time.
"I sure hope so."
"I... I..." I was trying to think of something to say. Nothing was coming that had any chance of getting us out of this mess.
Jill chimed in. "OK, you caught me."
"I'd say," she replied sternly.
"I was going to ask you for something big," she went on. "And I needed you to be relaxed and happy, so that' you would say 'yes'. And the best chance of that was getting you laid."
Mom jerked her head. "And this is what you came up with?" She said, pointing back and forth between the two of us.
"Well, no. I wanted one of his classmates, but there wasn't the time."
"So," she said unconvinced. "You slept with your brother? How does that make me relaxed and happy exactly?"
"Well," Jill tried her best to answer every query. "In the end I was going to have him seduce you. I just needed to see if he had the right moves or not."
Interesting, I thought -- she didn't mention this as a payment.
"And I take it you 'approve' if I heard that correctly." It was part question, part statement. Oh shit, I thought, how long had she been listening?
"Yes, as a matter of fact," Jill answered happily.
"And you thought he would and could seduce his mom?" She asked.
"Well, there was also going to be alcohol involved."
"Well of course," she said. "Seems like you had this all planned out." It was part question.
"Full-service dinner, clean up. Bottle of wine, relaxing music, back-rub by the fire...touching leads to more..."
"I see," mom surprisingly seemed to ease her tone. "That sounds nice, under normal circumstances."
"And you," she looked over at me and pointed a finger. "You agreed to go along with all this?"
"Um, I..." I stammered, not able to come up with any response.
"Uh-huh," she looked on, still waiting for an answer.
"OK. The fact is," I started, "all summer you two have been lounging by the pool, even sun-bathing on occasion."
"Right, so..."
"So, Jill has been teasing me. I swear her thong goes farther up her bottom each time I come deliver you two drinks by the pool."
"Glad you noticed," Jill replied out loud and gave me a wink.
"And mom," she turned back towards me. "you lay down topless and I see side boob all the time. I even get occasional glimpses of your full chest."
"Glad you noticed", mom replied and gave Jill a wink.
"Truth is, I've been seeing tits and ass in my sleep. You both have nice bodies... I've had to rub one out on a few occasions..." Shit, had I said too much? I didn't care, I mean I was caught sleeping with my sister already.
"Well," my mom expressed in a half-joking tone. "I'm flattered."
"Anyway, when Jill came to me with this plan, and we couldn't find a way to get one of my guys recruited by this weekend," my voice trailed off.
"This weekend? Why the urgency?" Mom asked, looking over at Jill. "Does this have anything to do with a trip to the Caribbean?"
"What?" She cried out. "Well, yes. But how did you know about that?"
"Amy's mom called earlier. Amy asked her straight out over dinner last night." She looked disapprovingly. "I guess Amy doesn't need to bribe her mom."
"Wait," Jill retorted. "Don't think of it like that. It's more like an offering."
"Offering?"
"When subjects would go to the King or Queen and ask for their generosity, appeal for their help... they would offer up whatever they had, some product or service. It was part payment, part respect. If the offering was accepted, the request was approved."
"A sign of respect," she queried.
"It's more like, we appreciate you. Working hard, tired at the end of the long week. Time to unwind, get a drink, relax and get a back rub..."
"And eventually sex?"
"Well, that was the idea. It has been a long time for you, so I thought, what better way to show you we love you..."
"Don't," she interjected. "I know you too well, little lady." She looked at her sternly. "Always looking out for #1. I bet Jack thinks he got the better of you. But all along this was part of your plan."
What? I thought. I was confused.
"Well, I can't blame you for trying. And I'm happy to learn Jack appears to know how to please a woman, if the sounds coming from this room were any indication..."
"Wait, what?" Oh shit, she had been there longer than we realized.
"Uh-huh," she said and clicked her tongue. "Well, we've had dinner already. But I wouldn't mind a few drinks and a back-rub by the fire while I consider your appeal."
"Really?" Jill and I both replied at the same time.
"Well, who wouldn't want to be pampered like a Queen," she smiled.
"Jill, you get the wine. Jack, be a good boy and start us a fire? I'll go get changed into something more comfortable."
"What?" was all I could say, quietly as mom left back down the hall.
Jill was smiling to herself. Her evil plan might work out after all.
I put a couple of logs in the fireplace and turned on the gas. Tons of things were going through my mind, not the least of which was trying to determine how far this would go.
A back-rub was innocent enough. But was I actually going to try and put the moves on my mom? And would she be receptive to that? Instead of a scheme that had to play out, everything was sort of out in the open. Mom had caught us, my sister and I, laying in bed exhausted after just having finished an oral exchange.
Caught, Jill then laid out her plan, and mom seemed to take it in stride. Now that I went back over the talk in my mind, she had not consented to anything sexual, but neither had she denied it outright which one might expect. In fact she seemed to have side-stepped around it. Or was that just wishful thinking, that she might actually play along?
The wood started to crackle as the fire caught. I closed the fireplace screen and turned on the stereo to light music. Then I turned down the overhead lights to a dim setting.
Just then Jill came in with drinks. She had a bottle of wine with two wine glasses already filled. Plus a bottle of whiskey and two shot glasses. I looked at her and she back at me. "Just in case anyone needs something stronger," she said lightly. "Liquid encouragement."
Mom came in wearing her bath robe. She looked at the tray with drinks, noticing pairs. "Seems like you're short a glass."
Jill answered, "Well, I thought this would be enough for the two of you."
"This is your plan," mom replied. "I expect service from you too," she said as she took a glass of wine and took a long pull, eventually finishing in quick order.
"From me?" Jill questioned.
"While Jack gives me a back-massage," she now dis-robed, revealing a nightie underneath. "You can start on my feet." She offered the empty glass which Jill now refilled. Mom took it and sat down on the sofa, then put her feet up on the coffee table.
I downed a shot of whiskey. Jill re-filled it, then took the other and took her own shot. I walked around behind the sofa. Jill sat on the low table, next to mom's feet. We looked at each other. The room was warm from the fire. The ambience was soft and romantic, light music played and firelight flickered on the far wall.
There was a moment of silence, of anticipation, of what might happen.
I looked down from above and behind her, this lovely woman with a slender body in her night-gown, waiting for me. My mom was waiting for me to give her a massage. I gently placed my hands and began to work her neck and shoulders. Her chest exhaled; she must have been holding her breath too.
It could have been a simple backrub, but it was so much more than that. It was erotic and romantic. Time might have slowed, or I was just caught up in it. It wasn't just that I was touching her skin. I was feeling her essence with my fingers, my hands. I kneaded her shoulders and upper back, to occasional oohs and aahs while Jill worked on her feet and toes.
After about 15 minutes, I leaned over and looked down, noticing the tops of her breasts from my vantage point. I could see her hard nipples pointing out against the sheer fabric of the nightie. I imagined caressing them and squeezing her soft breasts, maybe even while putting her nipple in my mouth, gently biting...
"See something you like," mom asked. I was caught staring at her chest! Had she seen the look of lust on my face?
But instead of pressing the issue, she changed the topic. "That was lovely, but it's time for a different position." She stood, taking another drink from her glass of wine. Then she removed her arms out of the nightie, but still held the fabric to her chest. She laid face-down on the sofa, her bare back exposed. She crossed her arms under her head and rested on them.
"You may resume now," she instructed.
I walked around the sofa, stopping to take another shot. I leaned down to touch her back. I couldn't get much pressure and the angle wasn't right. Mom noticed the dilemma I was trying to solve.
"You can straddle my hips, if the weight is evenly distributed it won't be too much."
I gently placed my leg over and sat down on her, with only the sheer nightie between us. I thought I felt her squeeze her buns, and a tingle went through me. But I sure if that was intentional or just a response to my weight.
I tried to focus, so I leaned in and massaged her shoulders again, working on her upper back. "Mmmmm, that's nice, your hands are so warm," she cooed. After some time, she gave me more direction. "You can reach my lower back nicely in this position too."
I worked my hands down and in circular patterns. Occasionally I would gently then firmly use my knuckles to need into her, as I worked into the middle and then lower back.
I got as low on her back as I could, nearly at my own legs. Any more and I would be touching her butt directly. That's when I thought about it - I was sitting on her, and my groin was the sensory input sending information to my head about her soft, warm ass. I tried to block it out, but that only made me think about it more. I shifted my hips and the feeling of her bum under me made me excited.
I continued the lower back massage, but I was obsessing with her bottom now. Periodically I would move enough to put pressure on her, to angle into her, to rub against her. And periodically she would push back in response. After a few minutes of this, I risked more, and shifted my hips so my penis lined up between her ass cheeks. I leaned in, presumably to reach her shoulders, resulting in me pressing my manhood into her bum through my shorts.
She squeezed her buns again -- it was unmistakable this time. And my cock was hard enough to be recognized for what it was. I imagined what it would be like to slide it into her warm pussy, to move in with long strokes, with her ass against my groin. Would it be heaven as I imagined it.
"Seems like someone is enjoying this a little too much," she replied with a wicked smile. But did she mean her or me? "That's a different kind of massage," she said as her body shifted and I lifted up, not sure if I had gone too far. She raised to finish her third glass of wine, then laid back down.
"You may use your hands."
Did she mean just use my hands on her back? Or did she just give permission for me to massage her bum as long as I only used my hands? I was clearly grinding on her, so it seemed vague -- was she side stepping the issue, or was it wishful thinking again?
I had to test the theory. I scooted back slightly, off her bottom and sat on her legs, then resumed. She stretched out and I could feel her body relax underneath me. I worked her lower back in a circular pattern. On each pass, I went a couple inches lower. Eventually I was touching her bum, and I decided to stop trying to be accidental about it entirely. Either she would stop it and the massage would be over, or she enjoyed it and I could proceed.
I lifted myself up enough to pull her nightie down further. She lifted her side and allowed me to remove it! She was fully naked now underneath me. I placed my hands on her bottom, softly then firmly as she pushed back and moaned. I kneaded her buns, carefully waiting for any sign that I had gone too far. I scooted back further, now alternating between massaging her legs, her thighs, from the top and sides, then on the inside and up as high as I could still be on her legs. She opened her legs slightly, just enough to permit this amount of massaging. But the response was unmistakable, she was into this and I could continue.
I returned to her bum, grabbing and spreading her cheeks as I worked her bottom with my hands and fingers. I could smell her, and then I reached between her legs and touched her pussy for the first time. It was soft and moist; she was clearly aroused by all this.
"Yes," she moaned and shifted as I rubbed around her mound. At first I used my hand, my palm, then I inserted a finger into her warmth. She arched, raising up to meet me, inviting me in, then impatiently she pushed back against my hand.
Here was this beautiful woman, a sexy creature, writhing under me. She had needs and I had worked up her body, gradually building and increasing the intensity. I massaged her legs and ass with one hand and fingered her pussy with the other.
"That's it," she moaned, "make me come with your hands."
I was excited, hard and horny. But I resolved to focus my attention on her. I reached down with one hand to grab a cheek and with my thumb rub her clit. With my other I fingered her pussy relentlessly, two fingers then three as I pushed all the way in. My other thumb rested on her asshole, and she began to grunt as she rocked with the motion.
I looked over to see what Jill was doing. She sat quietly in the lounge opposite, her legs spread on the ottoman and she fingered herself while she watched us. When she saw me, she used her fingers and stuck her tongue through, telling me what to do next.
But I didn't want to leave her out either. I motioned for her to come join us on the sofa. She came over and sat down on the other side of me, turning towards us and spreading her legs as she reclined. I reached down and rubbed Jill's pussy, then managed to get a finger in her pussy. But I didn't have any angle and couldn't twist more, so I failed to really finger her strongly. Realizing the limitation, but also that she was so horny and so close, she grabbed my arm with both hands. Now she was rubbing up against my wrist, causing the fingers to move up and down as her pelvic bone grinded on me, controlling the motion of my fingers.
It was hot, and I momentarily released mom so I could finish Jill off with my tongue. Just a few licks and a strong fistful of fingering, and she bucked against me.
"Fuck me, I'm coming!" She cried out, causing mom to look up at us. Jill convulsed and juices squirted from her pussy and onto my hand.
When it was clear she got off, I returned to mom, not wanting to lose the momentum. I lowered my head to her pussy again. I licked lower and lower, eventually reaching her soft bum. I licked her butthole, flicking across the rosebud. Then I spread her ass wide with my alternate hand and stuck my tongue in as far as her ass would allow.
"Oh yes!" She moaned. I fingered her hard, rubbed her clit, and tongue her ass, moving in and out.
"That's it! You know what I like!" she exclaimed loudly, grabbing the arm rest with both hands as her body tensed and she pushed back against me.
"Your pussy is tight!" I exclaimed between breaths. "But I've wanted your ass for so long!" Then I dove back in to lick her butt.
"Finger-fuck me!!" She cried out. "I'm going to come!"
I shoved my face into her pussy now. I licked her clit then inserted my tongue into her pussy alongside my fingers. She squeezed her legs against my head. Her body jolted, white fluid mixing with pussy juice on my fingers and face. She convulsed, and collapsed into the sofa, both relieved and spent.
Softly, I rubbed her back and she lay quietly, face down still. A few minutes passed.
"Mom?" I spoke, breaking the silence.
"I needed that," she said, raising her body and reaching out to caress my face. "Apparently we both did." She looked at Jill too. Then she regained herself and found her nightie wedged in the sofa cushion.
"Mom?" I asked, needing some response, some validation.
She stood to leave, "I'm going to take a shower." She gathered her robe. "Round two starts in 30 minutes."
"Round two?" Jill asked, sitting up and joining the conversation.
"I know what you want," she replied. "And you can have everything you want, both of you". She looked at Jill then back at me. "Three times. That is my price."
"Wait, both of us?" Jill asked.
"You want something, so does your brother."
"What?"
"Can't you tell? Eventually he's going to want to come too," she turned, reaching down to grab my crotch through my shorts. "But" she licked her lips, "I'm just not sure where."
"Mom," there was no reason to keep it to myself anymore. "There's so much I want to do to you, with you, for you" I said, reaching out to her. Then I continued, "I don't know where to begin."
She looked at my lovingly, "In 30 minutes, I'll show you." And with that, she went to shower.
Jill and I had a couple more drinks, and at first we didn't talk. We both knew what had just happened, and that there was still something more that had to happen.
"Jill, I..." I started.
"Don't" she cut me off.
"Wait, don't get mad at me now. You said I might get some too."
"Yea, but I didn't think you would like it this much."
"Jealous now?"
"Actually, I thought we might have something."
"We still could," I replied.
Jill thought about it. She looked at me, pained by what she was about to say.
"I just didn't think I would..."
Just them mom returned and cut her off. "You didn't think you would get off that easy, did you?"
"Mom!" Jill replied, standing up.
Mom was back, wearing her bathrobe, her hair was washed and still damp. She turned a wicked smile. "Not to mean you didn't just get off easy. I watched you playing with yourself."
"Can you blame me? That was so fucking hot, I got all worked up," Jill admitted, sheepishly. "I was so horny, I needed him to finish me off."
"Jack certainly knows what he's doing, I'll give him that." Mom was impressed.
"Jill, refresh our drinks," mom said -- lifting a now empty bottle.
"Jack, stoke the fire." I did as she asked. Jill went to the kitchen to get another bottle of wine and refilled all our drinks.
"Will that be all?" She asked, turning to leave.
"You're not going anywhere," she responded.
"What?"
"Time for round two -- time for both of you two to make mom happy."
"What?" Jill asked again, her hands down and stretched outward in gesture of a question. She was clearly not prepared for this.
"What, you didn't think you're the only one calling the shots, did you?" Undeterred, mom undid her robe, exposing her nakedness underneath. Her breasts poked out. She lay down on the sofa, facing up. She placed a small pillow under her head and reclined in total relaxation.
"Time to pay the price. Jack, you start," she laid back and closed her eyes.
"Jack?" She asked, waking me from my daydream. I took another shot of whiskey and approached her by the side of the sofa. Her beautiful breasts pointed out and begged to be touched. I caressed them, massaged them, squeezed them. They were as lovely as I had imagined so many times before, as she lay out by the pool. Only now she was face up, exposed, and offering herself up to me.
I fondled her breasts, and she arched her back, pushing them into me. I massaged her chest, her abdomen, down her sides. I caressed her neck and ended back on her tits again. I reached down and took a nipple in my mouth, biting gently.
"Mmmm, that's nice."
I walked around the back of the sofa, standing over her head. I continued massaging her tits, but she must have noticed the position change. She reached up to grab my dick through my shorts. She fondled me, getting me harder than I've been in a long time.
After a couple nice squeezes, she let go. "Remember, you need to get me off three times before you get what you want."
"Yes, mom," I sighed. Man, this was going to be tough to resist. But it was moving along, so I decided to pull back for now. I walked back around the sofa and knelt down beside her. I lifted one leg up, putting it over my back. Then I reached in to rub her pussy.
"Jill, time for you to help out."
"Yes momma," she replied, walking over.
"Stand here," mom instructed, and Jill obliged.
"Massage," she commanded.
"What?" Jill asked.
"While Jack fingers me, I find that my breasts still need attention."
Jill reached over and started to cup her breasts, and mom sighed. I slipped a digit into her pussy and slowly, tantalizingly fingered her.
"Squeeze and pinch them." Jill paused, then contemplated her options. Eventually she did as asked. She rolled her fingers and pinched one nipple, and with her other hand squeezed the other breast firmly.
"That's nice," she cooed. I continued to work at her pussy, marveling that now my sister was getting in on the action.
"Now, grab my ankles," she told her as she lifted her legs back and above her head.
Jill reached for her ankles and gently held them above mom's head. Her pussy was now fully exposed, and I dove in. I fingered her pussy and licked on her clit.
"Pull them back all the way," mom instructed, "so Jack can lick me good."
Jill pulled her ankles behind her head, and mom's hips lifted off the sofa. I grabbed her ass with my open hand and squeezed her butt and spread her cheek. She moaned and writhed.
I leaned in to lick her butthole. I used two hands to spread her cheeks, then inserted my tongue deep into her ass. Then I used one hand to finger her and rub her clit again. She was squirming wildly at this point. I rimmed her deeply, my tongue sliding in and out of her ass.
It was time to get her over the edge, so I inserted a finger into her smooth, wet bum. I fingered her pussy, licked her clit. I was about to enter a 2nd finger, but mom must have realized.
"Jack, I brought something," mom said. She reached into the robe pocket and produced a small tube of KY lubricant. I took it from her and squirted a dollop on my fingers.
I spread her cheeks wide again and put my index finger deep into her butt.
"It's been a while, son." She was anxious.
"I'll see how much you can take," I said with concern, "one finger at a time."
"You're such a good lover," she replied. "I want you so bad." Then, after she had adapted to my finger in her ass, she continued. "Give me another."
So I slide a second finger up mom's petite asshole.
"Ugh," mom replied. "Fill me up and make me come!"
I pulled out long enough to line up two fingers in her pussy, and two more in her ass. It was the double shocker. I began to push in and out in rhythm. When I got the chance, I licked and bit on her pussy lips and clit again.
"Fuck, that's hot," Jill exclaimed. I looked up, and Jill was still holding mom's legs back, but she was standing next to us, looking down into the action. She had her other hand between her legs, rubbing her pussy. I motioned for her to put one leg up on the arm rest of the sofa. When she did, I grabbed her bottom from behind. I tried to reach her pussy from behind her, but it was too far. Jill turned slightly, and I switched the arm angle and reached up and between her legs.
I was working blind, as my face was in mom's groin again. But I found Jill's pussy, and pushed up and into her with two, then three fingers. Again she grabbed my arm with both hands. Only this time she impaled herself on me. She was wet and my fingers went further up into her.
"Fuck that's good, you really know how to work my pussy." Jill said and mom looked up at her.
"Geez, do you have your entire fist in her" Mom asked.
I paused just long enough to say, "Not sure if that would fit."
"One way to find out," Jill replied. She stepped off, then took the KY and squirted some on my fingers. She squeezed them together, showing me the shape to use. Then she raised her leg back onto the arm rest of the sofa and guided me to her waiting pussy.
The tips of my fingers went into her wetness between her legs. She wiggled her body to encourage me to go deeper. I could feel the entirety of my wrist at her opening, the bulge of my thumb being the last part. She spread her legs farther. I pushed up, and she pushed down, impaling herself and my whole hand slipped into her wet cavern.
"Holy shit," she said. "My pussy is so full!"
I pushed up and tried to turn my fist, the fingers touching different parts of the inside of her vagina. Once again I briefly released from mom, and reached up to lick Jill's pussy. I bit her clit and squeezed her ass with my other hand, the one not fully up inside her pussy.
She moaned and cried out. "Fist me mother fucker!" She was horny and wild. With her squeezing her legs and muscles, combined with me twisting and turning my first up into her, the sensations were all too much. Jill came again, fast and hard. It wasn't as long as before, since she just came an hour ago. But sure enough, she squirted out and juices ran down my wrist and arm. She bucked wildly for a few seconds, then calmed down.
"You liked?" I asked.
"Fuck yeah," she replied.
"Did you call me mother fucker?" I almost laughed.
"Sorry," she apologized. "Wait," she then thought about it. "You are!"
"Sorry to interrupt you two," mom chimed in.
"Yea, sorry." I turned my head back towards the other woman needing my attention. I re-engaged my hands on mom's body. I found her pussy and did the double shocker again, two in her pussy and two in her ass. My other hand freed from Jill, I reached under mom and pulled her ass cheek wide, opening her anus so I could go knuckles deep in her.
Jill resumed pinching and squeezing her breasts. I clamped down on her clit with my mouth. Rapidly I fingered her intensely. The two of us working her, mom bucked wildly and started to cum.
"Oh fuck! I'm cumming!" She squeezed my head between her legs and her hips thrust up and out.
I was furiously sucking her pussy lips, rubbing my chin against her clit. I took a mouthful of liquid before I realized what was happening. But she was in the throes of orgasm, and I was not about to stop. The realization made it more intense, and I locked down hard and pushed in with all fingers again.
"Aaahhhh" she cried out, "I'm cumming again!" She bucked and lifted her hips up high and jammed into my face. Juices came from her pussy, running down my fingers and arm. I licked her furiously until she squirmed in sensitivity.
"Oh my god!" she exclaimed. "Oh my god, oh my god," she panted. Jill released her legs, and she collapsed down onto the sofa again.
Then after a minute, "I've never cum that hard!"
"I'm glad you liked it," I said with confidence.
"Not many men will do that," mom said.
"What?"
"Continue through all that."
"You mean..."
"Yes, when it got wet" she said somewhat embarrassed. "But pushing through and during, it makes the orgasm grow stronger and last longer."
"Well, my pleasure," I added.
"No, it was mine," she smiled back at me, touching my face again. "You keep that up, and you will definitely make women very happy." She laid back and put her hands on her face.
Then she continued, "Kids, I want to tell you something. Your father would never do that. That's one of the reasons we're no longer together. Our sex life became nonexistent."
"Really," I asked. "I thought I overheard him once talking to a friend, that the sex was hot and heavy, and as often as he wanted..." It was part question.
"With his secretary, I'm sure it was" she retorted.
"Wait, really?" Jill asked.
"Before kids when we were younger... I used to give him everything he asked for. Oral, anal, even a threesome," she said.
"Wait, there is so much to get into here," Jill spoke excitedly, but mom went on.
"Yea, all guys want that," she looked over at me, smiled and then continued. "He was even hot for his secretary, so we got together for a birthday present. For him."
"Wait, hold on," Jull tried to interject, but to no avail.
"Years later, during an oral session for me... I peed on him, once. From then he never went down on me again," she thought back in time. "Then the sex became so little, it was down to once a month, then anniversary and birthdays. For him, mind you. I hadn't had an orgasm in years when we divorced."
"I caught him with his secretary after that. He had been banging her regularly. He didn't deny it, just said that he needed to be with someone more in tune to what he needed, and that wasn't so dirty. That arrogant bastard," she finished the story.
"Ugh, sorry mom," Jill replied. At first she was sad. But then a smile came over her again. "So, you really did need this, more than we realized."
"Well, yes," mom replied. "I guess I did."
"So, about the request," Jill asked.
"You'll both get what you want," she looked at us in turn, "but only after you get me off a third time."
"Mom?" Jill asked, confused.
"Yes honey," she looked up at her daughter.
"You said giving up your ass makes you a slut."
"Dear," mom answered, "I told you that because I didn't want you doing everything a boy wanted right off the start."
"Oh," Jill replied.
"You have to make them work for it," and with that she looked at me with a naughty smile.
Then she continued, "When you find the man you want to give it all too, and he turns out to be a kind and considerate lover," she nodded her approval to me, "then it's fine to give him your ass."
Wait, I thought to myself. Was she indicating to me that I would get her ass, or that it was OK for Jill to give it up to me?
"In fact, orgasms can be the best with ass play."
"Oh, something to look forward to!" Jill was excited with anticipation.
"Yes," mom replied. "As in, meet me in my room in 30 minutes. I need another shower."Jill and I walked into our mother's room, finding her sitting on the edge of the bed near her nightstand.
She was fully naked this time, sitting on a towel as she had just finished the shower.
"Jack, come here."
Curious, I walked over to where she was. I hoped she would start sucking my cock, but she had other ideas. She opened the nightstand drawer, pulling out a large dildo.
"Let me see your cock," she pointed at the bulge growing in my shorts. I dropped my shorts to the ground, and she reached for my stiffening member. With a few pulls and squeezes, she could tell it was fully erect. She put the dildo next, comparing it.
"Mom, what are you doing," Jill asked.
"If he wants to stick his cock somewhere," she was getting more forward with each session, "I want to be sure it will fit nicely."
I was getting really excited now. I reached for it, and asked "so, you want me to get you off a third time, using the dildo?"
She held it back and replied, "No. I want Jill to do it."
"Wait a minute..." Jill replied, incredulously.
"I've already decided that Jack is worthy, he will get whatever he wants," our mother replied matter-of-factly.
"What?" Jill could not believe it.
"Well, he got us both off twice, and even took pee the face without complaint. It was clear my pleasure, our pleasure, was the most important thing," she said lovingly to me. "He's also resisted simply fucking either of us, which must be hard since we've both come twice, and he hasn't."
"But" she turned to Jill, "you still need to convince me how badly you want it." She said the last part, handing out the dildo for Jill to take.
"Wait," she stammered, but ultimately, she took the large flesh colored rubber cock in her hand. She had held one before, masturbating with it when required. But now her mom was asking her to use it on her.
"You've been planning all along to get your brother to do your bidding," it was part question, part accusation. "And it wasn't really hard to accomplish that part of your plan."
I looked at Jill, who wasn't denying anything. Was her silence an admission? This only made me more confused.
"It's not that hard, I admit. And I don't blame him, or you. He's a horny stud, and you're a sexy young woman, and we've both been teasing him for months." Was I hearing this correctly?
"Bottom line, I'm the Queen. Time for you to submit to me."
"Mom," Jill tried to counter, "this wasn't part of the plan."
"Yours or mine?" What? I'm so confused listening to them, but I knew better than to interrupt.
"All your scheming and manipulating, it comes with a price to get what you want."
"Mom please."
"Two can play this game." She commanded and demanded. "You will get me off as I instruct, or no deal."
"That's not what we agreed," Jill said. That is so hot, I thought. Wait, what?
"That Jack would get me off three times? He will," she said, grabbing my cock and looking into my eyes. "He wants something bad, and he knows I will give it to him if he does what I ask." I nodded my approval. Was I that transparent?
"I don't need you for that."
"But mom, you agreed" Jill begged.
"I said you'd both get what you want if you both do as you're told."
Jill looked on, realizing her mistake, her dilemma.
"Now I am telling you how. Time for you to show me how much you really want it," and with that, mom climbed unto the bed, flipped on her back, and spread her legs exposing her pussy.
"Come service your Queen," mom said seductively. "And not gentle like before!"
I looked at my sister, holding the dildo. At first, I was about to feel sorry for her. But then she had a devilish smile. Wait, what did mom mean, before?
Jill took climbed onto the bed on her knees. She knelt before our mother's waiting pussy. She lowered her head and mom began to moan.
I was about to lose my mind. My sister was eating out my mom, and then she put the dildo in her pussy!
My head was spinning with all the new information. But not wanting to be left out, I positioned myself behind my sister. I tugged at her shorts. When she realized what was happening, she lifted one leg then the other so I could remove them, without her having to disengage from her task of servicing mom.
"That's it, my loving daughter," mom replied. "lick my clit and fuck me with that massive cock!"
I could tell mom was enjoying herself. I started to finger my sister again, and she moaned.
"I see Jack is trying to be useful still," mom said as she leaned on her elbows to get a view. I was fingering Jill from behind and rubbed her clit. I began to lick her ass, and she didn't object.
My view was awesome too. Mom was getting eaten by a girl, my sister no less. And the dildo being pushed in and out was making her wet and hornier with every thrust. I was thinking it might be time to slip my cock into her from behind, but just then I was interrupted.
"Jack," mom commanded. "You'll get your just reward in good time. For now, it's time both of you to finish off what you started."
"Yes, mom," we replied in unison.
"Jill, turn around, I want to play with your pussy."
Jill got up, turning herself around. Mom slid down the end of the bed, her legs dangled off the edge. Jill straddled her, then backed up until her hips were over her head.
"Jack, pull my legs back so Jill can lock them in place with her arms."
I did so, watching them get into a tight 69 position, their faces meshed into each other's groin. Jill needed all her arm strength to hold mom's legs back, so she couldn't manage to finger her or use the dildo, she had no leverage. Then she got distracted as mom apparently started licking and fingering her pussy. Jill closed her eyes and moaned her appreciation, arching her back and lifting her head up in delight.
Then Jill opened her eyes, and with an evil grin said, "Caribbean here I come." She lowered her head and completed the circle as she licked our mom's pussy.
At first I gazed in amazement. Two beautiful, sexy women, that I had been watching and obsessing about by the poolside... Here they were, engaged in oral sex, with each other!
But then I realized I didn't want to be left out. I could be part of this tryst. So I knelt down by the edge of the bed. Mom's hips were raised, her pussy angled up and easy to access. I reached down and began to rub and play with her pussy.
I noticed the dildo laying on the bed, so I grabbed it and playfully toyed with it at her pussy opening.
I slipped the dildo in, and Jill continued to lick her clit.
"That's it, that's what I want!" Mom encouraged us.
The site of the two of them was amazing. The musty smell of sex and sweat filled the room. Our moans were the only noise as we focused on each other.
I was so focused on using the dildo on mom, I didn't realize how close Jill's head was to mine. When she took a brief break from licking, she looked up at me. She had desire and need all over her face. She moaned again.
"Is she fingering your pussy?" I whispered to Jill.
"Yes," she looked at me with desperation. "I'm so fucking horny, but I need something more." She had come twice and was at the point however where she needed more to get over the edge.
"Ready for the big finish?"
"I'll do anything you want," she said quietly.
"Be careful what you say, I'll hold you to that," I replied. She looked down, embarrassed that she had gone this far, that her needs were so nasty.
"Fuck me now," she begged.
I stood up and walked around the bed. I positioned myself behind Jill, standing above mom's head.
I presented my cock to our mom, and she took it in her mouth. I just needed a few licks, then pulled out and positioned it at the opening of Jill's pussy.
"Give it to her," mom encouraged.
I grabbed Jill's hips, and mom grabbed my cock to slide it into Jill's open pussy. She was warm and wet, aching to be relieved. Mom grabbed her bottom and spread her cheeks, and I rammed into Jill a few times.
"Fuck me Jack! I love your cock!"
I banged away at her pussy, holding onto her hips and standing above mom that continued to lick the outside of her pussy. I put my thumb down to my mom's mouth, and she instinctively knew what to do. She sucked and licked it, leaving my thumb wet and lubricated.
I raised up and slipped my thumb deep into my little sister's tight butt. God that felt so good to me, but my sister loved it even more. I pushed my cock deep into her, and my abdomen pushed my hand and thumb further up her ass.
Jill started to cum, spasms ripping at her. She came on my cock, and combined with her warmth and tightness, I shot my load into my little sister.
"Holy shit I'm coming!" A few more thrusts, and I pushed in deep, relishing in the feeling, the moment. Her sphincter contracted around my thumb with each spasm.
I pulled out slowly, jizz covering my rod. I lowered myself to let my mom suck it off me.
"Fuck that's hot!" I exclaimed.
When she finished, she licked her lips and looked up at me. "My turn, son. Get me off one more time then have your way with me."
I reached down and gave her a long, passionate kiss.
I walked back around the other side of the bed. Jill had her head down between mom's legs, she was exhausted and spent.
"Jill, I need you to do something for me," I said to my new lover, my sister.
"After that, I will do anything you want. I will give myself to you unconditionally."
"I know," I replied softly. "But this is for mom," I said.
"Understood. What do you need me to do?"
"I need you to lick her clit like nothing else matters."
"You're so naughty," she whispered. I noticed she didn't complain or object.
"And if she starts to pee," I added, "you might feel your face being pushed in even more. Whatever happens, cover or close your mouth, just don't stop until we're all done," I said with all seriousness. "All of us."
She nodded, understanding fully now.
I knelt down again and resumed a slow methodical motion with the dildo. Jill started to rub mom's clit again, then began to use her tongue, playing with her labia and then nibbling on her bud.
When we reached the rhythm and I had the dildo going in deep, I used some more KY, and slipped two fingers into mom's ass again.
"Ugh," she replied. "That feels so good. I haven't been fucked like this in so long!"
I pushed the dildo nearly all the way to the hilt. Mom pushed back, and Jill continued playing with her clit.
I inserted a third finger now into her butt. It was tight, but at this point well lubricated and massaged, so fingers slid in and out easily. After a few more thrusts, I decided to go farther. I pulled my fingers out, and then slowly pulled the dildo from her pussy. Then I lubed it up as well and positioned it at her ass. She had followed along; she knew exactly what was coming.
I pushed in slowly, but only part way. "Ugh, that's big" she exclaimed.
"Too much?" I asked, hoping for only one answer.
"No," she paused. "I need it. You need it. Fill me up," she pleaded.
I spread her ass cheeks and pushed the rubber cock into her fully.
"Umph! Oh shit that's big!"
But I wasn't going to stop now. I met eyes with Jill, and she knew it was time. She locked down on mom's pussy, on her clit. I inserted two fingers into her pussy, finding her g-spot at the back and top of her vagina.
I fucked her ass with the dildo, giving her all it was worth.
"Ugh, oh, give it to me!" she couldn't decide if it was too much or not enough, or both.
"I'm cumming!"
We knew what was next, and that was OK. She started to pee, and Jill freaked, trying to pull away.
But mom grabbed Jill's head with her hand and pushed her face into her groin. She clamped her legs on her daughter's head that was feverishly working on her pussy and wouldn't let her up. Mom arched her back, and the spasms started. She was too deep into the orgasm to turn back, to let up, to allow anyone to stop.
"Fuck me hard, both of you!" She knew both of her kids were working her, and it had to be that way.
I thrusted the dildo in a few more times and had my fingers deep in her pussy now. Sex juices got all over the place.
Her body wracked and writhed as she convulsed.
"Argh! Oh! Oh! Oh shit! "Ughhhhhh! Fuck that's so good!"
She was exhausted, "oh my lucky stars!" mom exclaimed. "Third time!"
Not needing any more incentive or permission, I put my arms under her legs, and pulled her further towards the end of the bed.
"Pull back on her ankles again," I instructed Jill. She did, her eyes wide open with anticipation.
First I slipped my cock into her warm vagina. A few times in and out was all I needed to lube my cock with her pussy juices and cum.
Then I put my cock head against her anus, and gently but firmly slipped it into her tight ass.
"Oh shit! You're not waiting any longer are you!"
"Ugh, your ass is so tight!"
"Give it to me good, son!"
I reached down with both hands, grabbing her ass cheeks and spreading them apart. Then I put my hands on her thighs and leaned in.
"Oh fuck!" I exclaimed. The sides of her anus engulfed my cock, and the warmth, tightness and naughtiness were more than I could have hoped for. I pushed in until my abdomen touched her butt, into the hilt.
"Your cock is so big and wonderful. It fits just right!"
"I can't believe I'm this deep in your ass. This is heaven," I called out. I pulled out slowly, then re-inserted back into her. The feeling if that insertion as her ass opens and receives me was total bliss.
Then I started to pound into her.
"Oh lord, fuck me good!"
I motioned towards Jill. "Rub her pussy,"
She had raised up, but now reached back down and fingered moms clit, pinching it with two fingers.
"Right there, you got it!" she encouraged Jill.
"Fuck me harder, both of you -- fuck fuck fuck!"
"Now lick her pussy," I instructed my sister.
She leaned in, using her upper body to hold mom's legs back. She flicked her tongue over mom's pussy and clit.
"Holy shit - I'm gonna come again!"
I pounded away at her back side. Thrust after thrust, her tight hole wrapped around my hard cock. I came hard, deep in my mom's ass. I don't know if it was another orgasm, or a continuation of the previous, but she started again. Her pussy juices ran down her leg.
"Umph! Fucking god!"
I pushed in farther, enjoying the moment. There was the feeling of my mom's tight ass swallowing my hard cock. But there was also the visual. Her ass was beautiful and spread open for me. Jill held her legs back with her torso, letting me get the optimal angle. And she was participating in getting our mother off.
Orgasmic convulsions caused mom to tighten her ass around my cock, and it was more than I could handle. I shot my load as I was deep in her rectum.
"Holy shit -- I'm cumming hard!" I pounded a few lasts time, spewing my cum up inside her.
We all collapsed on the bed and lay quietly for a moment.
I looked over at Jill, her expression was of concern. "You OK?"
She looked up at me, "I want to come hard like that, too. And I want to give you everything you desire," she said as she bit her lip. "But I'm not sure my ass is ready for that. I've never had anything like that in me."
"I understand. We'll work up to that," I replied.
"We will?"
"One finger at a time."