I watched Hailey's back slowly rise and fall with each breath. I had been awake for a while now but I did not want to disturb Hailey's slumber. She had one leg draped over me, her head rested on my bare chest. Her long brown hair lay sprawled out behind her.
I need to tell her.
I had been feeling guilty. Even more guilty than usual about the affair I had been having with Hailey's mother, Ms. Jackson. And now there was even the encounter with Hailey's sisters that was weighing on my conscience. Hailey's methodical breaths altered for a brief moment and her head stirred. She rested her chin on my chest and looked up at me with her blue eyes. I tucked a few strands of her hair behind her ear.
"Good morning gorgeous." I said.
"Morning." She responded, her voice slightly raspy from just waking up. "We better pack. My Mom will want to leave as soon as my sisters get here. And when we get back we can start moving out of this basement!"
She quickly jumped up and did a couple bounces on the bed in her excitement. Then she jumped to the floor, pulled a wedgie from her panties out of her ass cheeks and began rummaging in her dresser drawers.
We had found a house to move into and Hailey was anxious to leave her Mother's basement. I didn't blame her. The house was small, but it was a good fit for us. And it wasn't far from Ms. Jackson's home. Only a few minutes' drive... Ms. Jackson had reminded me of this several times since we had started looking at it. However, as excited as Hailey was to move in we had decided not to start moving until after the vacation that Ms. Jackson had planned for all of us.
She had rented a large beach house in California for the week. That was the part I was looking forward to. The part I wasn't looking forward to was the drive. We were driving, which would take more than several hours. And worse, we were expected to all pile into Ms. Jacksons suburban. With Ms. Jackson, Leah, Her twin Rachel, Rachel's husband Jacob, their baby boy, Hailey, Me and all our luggage I had a feeling it was going to be crowded.
"I'm already packed. I'm only bringing a few things." I told her. By now Hailey had slipped a pair of tight jeans on and a T-shirt and was shoving bikinis into a suitcase. "Look Hailey, I've been meaning to talk to you about something."
She stopped what she was doing and looked up at me. I struggled for a few moments to find the words, then we heard a commotion from upstairs followed by "Hey everybody! Let's hit the road!". I recognize it as Leah's voice. Hailey jumped to her feet.
"It will have to wait babe." She said and then ran out the door to greet her older sister.
By the time I had showered and gotten dressed Rachel and her family had also arrived. I carried my bag along with Hailey's bags out to the driveway. Everyone else's luggage was already loaded. I managed to squeeze our bags in so that the entire back was full as well as most of the back seat.
"Shotgun!" Leah called as she exited the house. She opened the passenger door and hopped into her seat. Then she stuffed headphones into her ears, leaned the seat back and rested her feet on the dash. Her long legs stretched out, which you could see most of since she was wearing a short cotton skirt.
"We'll have to put the car seat in the middle." Rachel said as she came out the front door of the house. Jacob dutifully began assembling the car seat on the middle row of the suburban. Ms. Jackson was next to exit and she took the drivers seat. Hailey shut the front door behind her.
"I'm guessing we've got the back seat?" I asked her.
"Come on. It won't be that bad." She told me.
I climb into the back seat and Hailey climbs in after me. Jacob and Rachel take seats on either side of their child. The strange thought occurs to me that my penis has been in the mouth and vagina of every female in this vehicle.
"And we're off." Ms. Jackson says as she backs out of the driveway. "This is going to be so much fun. I am so glad you could all make it."
The back seat is crowded. Because of the luggage there isn't enough room for both Hailey and I to have a seat to ourselves. Hailey has to drape one leg over me and kind of rest in the small space between me and the side of the car. I didn't mind.
It isn't long before we are on the freeway heading west.
"Was it difficult to get work off to come Jacob?" Ms. Jackson asks from the front seat.
"Eh." Jacob responds. He never talks much.
"Yes, it was. He'll probably be on his laptop for the entire trip." Rachel adds for him.
"Tell us about the house we're staying in Mom." Leah changes the subject.
"Okay. It's right on the beach, you step out the back door into sand."
"Awesome." Hailey exclaims.
"And it's big. There's four stories, everyone will get their own bedroom. And I'm pretty sure there's a hot tub on the roof."
"Sweet." Leah says.
"So, what are we going to do the days we're there?" Rachel asks.
"There's nothing planned. We can do whatever we want. But there's an outlet near the house that has lots of good shops."
"I am so there." Hailey says.
"Swim, snorkel and surf in the day. Play games and sit in the hot tub at night. I plan on finishing my book. There will be lots of time for leisure." Ms. Jackson says.
I had to agree with the girls, it did sound nice. Even if I had to endure the car ride to get there. I resolved that I would tell Hailey about my unfaithfulness sometime before the trip was over. She deserved to know and I couldn't keep lying to her.
The next hour or so of the drive passes by slowly. Hailey and I discuss plans about moving into our place when we arrive home. Jacob plays games on his phone. The twins chatt and Ms. Jackson sings along to her 80's play list.
"Does anyone else have to pee?" Hailey asks from the back.
"I could go." The twins say in unison.
"Alright I'll pull off at the next exit." Ms. Jackson announces.
When we pull off the freeway I get out to stretch my legs. The three girls run to the bathroom. Jacob stays in the car playing his games and Ms. Jackson fills up the tank with gas.
"You don't look so good. Are you feeling okay?" I ask Hailey upon the girls return.
"I feel kind of car sick to be honest." Hailey admitts.
"Why don't you sit in the front seat? It won't be so bad up there." Ms. Jackson suggests.
"Hello. What about me?" Leah asks.
"You can sit in the back." Ms. Jackson says matter of factly.
"It's pretty cramped back there." I add.
"You two can squeeze. She's family, it's not a big deal." Hailey says.
"Whatever." Leah says as she climbs into the back seat.
I give Hailey a look. She merely smiles at me and hops into the passenger seat. Rachel waits for me as I climbed in after Leah. Once we are all in we pull back onto the freeway and we're off again.
In the back seat, there is zero room between Leah and I. Our legs are pressed together and our sides are touching. She slides her shoes off and pushes them under the seat. Her toenails are painted pink to match her fingernails.
Her short grey skirt reveals most of her long smooth legs. She wears a midriff shirt that shows off her flat stomach. The neck line is cut ridiculously wide so that one shoulder is bare, exposing a pink bra strap. Her shirt is also loose enough that any time she leans forward at all you can easily peek down to see the tops of her small round breasts, resting in her push up bra. I do my best not to look.
Her blond hair which had traces of pink highlights in it is up in a small bun. We are close enough that all I can smell her peach lotion.
"So, how have things been?" she asks.
"Fine."
"I'm guessing that you never told Hailey about our little encounter?" she says quietly so only I can hear.
"No."
"That's probably for the best." She says with a smile. "Do you ever think about it?"
"Think about what?"
"That day obviously. When we fucked like animals." She whispers.
Do I think about it? Of course, it was amazing. My dick starts stirring just at the reminder.
"No. I don't." I lie.
"Oh, I don't believe you." She says. And she takes her right hand and places it on my crotch. I take her hand and return it to her own lap.
"I felt it. You're getting hard for me already and I haven't even done anything yet." She smiles. Then she tugs on her shirt so that it comes down even further on her right shoulder showing more skin and making it even easier to see her chest. My eyes automatically glance at them.
"I saw that." She whispers.
"We are not having this conversation right now."
"I agree. I'm done talking." And with that she places her hand back onto my lap.
I look out the window. We are driving through farm country. Fields of corn and pastures of cows whizz by.
"Are you out of your mind? We're in a car full of your family." I say.
"I know, that's what makes it so much fun. I'm seriously turned on right now." She says and begins gently moving her hand around the outline of my swelling member. I place my hand on hers, stopping her motion.
"Don't try and stop me or I'll make the rest of this car ride extremely awkward." She says and glances to the front of the car at Hailey. "Besides, don't act like you don't want it."
She was right. About both things. I remove my hand from hers. She smiles a devious smile at me and then slowly slides her hand up to my waistline. She skillfully unbuttons my jeans using only one hand and then slowly undoes my zipper. Next, she curls her fingers underneath the elastic on my underwear and slides her small had inside. Once in, she wraps her cold fingers around my half-swollen shaft.
Oh my God that feels good.
Next, she pulls her prize out of my pants. I lift my butt off the seat an inch or two and slide my pants and underwear down a couple inches so that she can have access to my entire shaft. Her hand makes its way up and down my semi swollen shaft. Her movements are made difficult by friction.
She lets go of me and quickly spits into her right hand. She quickly brings it back and now lubed with her saliva her hand begins sliding more easily along the length of my shaft. Within seconds my cock is fully erect.
"Wow, you're just as big as I remember." She whispers.
Hailey and Ms. Jackson are talking about decorating our new house in the front seat. Jacob has put his headphones in and is no doubt listening to some boring podcast. Leah slides her left hand underneath her skirt and starts playing with herself while she strokes me. Her hardening nipples push at the thin fabric of her shirt.
"Leah what are you two..." Rachel begins to say as she turns around. Rachel's eyes widen with shock as she witnesses what is happening in the back seat. "Are you serious?" she mouths to Leah and I. Leah stops playing with herself long enough to lift a finger to her lips in a 'shushing' motion. Motioning for Rachel to keep quiet.
Rachel glances quickly up front to make sure that Hailey and Ms. Jackson have not noticed anything, then at her Husband who is oblivious to the situation. Then her attention turns back to us, Leah continuing to stroke my hardening cock.
"Do you two really think this is the best time or place for this?" She whispers.
"No. Probably not." Leah laughs quietly.
"Rachel, please. Please don't say anything." I beg. Rachel looks at Leah and then she looks at me. And then Rachel looks at my Cock, glistening with her sister's saliva. For several moments, I watch her eyes travel up and down my member, in pacing with Leah's hand. Finally, she turns back around.
"Mother," she says. "Could you turn up the music please?"
"Sure, thing dear." Ms. Jackson replies and she turns the song up a few hits. Janet Jackson's 'Nasty' helps to cover the sound of our fornicating.
Leah lets go of my cock. She pulls herself up and motions for me to scoot over.
"What are you doing?" I whisper.
"Just do it." She instructs me. I do as she says. Next, she pushes my legs together so my knees are touching and steps over me with her right leg so that her ass is right in front of my face. Then she hikes her skirt up, revealing the bottom of her firm ass cheeks and soaked panties. She reaches between her legs and pulls her panties to the side, exposing her smooth pussy.
She grabs my cock and teases her slit with my bulbous head. Then she lowers herself onto my cock until I am fully inside of her and her ass cheeks are on my lap.
Oh my God!
Leah's tight pussy squeezes my cock as it marinates in her juices. Rachel turns around to look at us.
"You have got to be kidding me!" She whispers. Leah simply motions for her to keep her eyes forward and then she slowly starts rocking her pelvis back and forth, then side to side and finally all around.
This girl is crazy!
I look up into the rearview mirror and make eye contact with Hailey. She turns to look back at us, the seat in front of us shields the fact that I am completely penetrating Leah from her view. But she can still see that Leah is sitting in my lap.
"You two doing okay back there?" Hailey asks.
"Oh yeah. I was just starting to get a dead leg so I asked your boyfriend if I could sit on his lap. You don't mind, do you?" Leah asks.
"Oh no, it's not a big deal. You okay babe?" She asks me. "I'd totally switch you spots but I'm still feeling kind of car sick."
"Don't even worry about it. We're just fine back here."
"So anyway Mom, what was I saying?" Hailey's attention went back to the front seat.
As soon as she looks away Leah begins her gyrating again. Not daring to raise my hands to her chest or shoulders I grab onto Leah's waist and grind my pelvis into hers as she rocks back and forth.
"Ooohhh" Leah moans softly.
"Keep it down!" Rachel hisses.
"I'm sorry sister. I just can't help it, you know me. And you remember how big he is." Leah whispered back.
Leah grabs the seat in front of us for extra leverage. She stops her rocking motion and lifts her ass up and then lowers it back down again before my cock is fully exposed. She does this several times but when I see Hailey glance at us in the mirror I decide this is too risky. I grab her by the waist again and hold her down, balls deep inside of her.
Leah leans back and licks my ear, "Let me go." She whispers.
"No. You're way too obvious."
"Alright, fine. Have it your way." She says.
Then she tries her best to slide up my shaft, she succeeds in sliding a couple inches but I pull her back down. She tries again with the same result. On and on we go. Leah working all the legs in her muscles attempting to twerk on my cock while I use all the muscles in my arms to hold her down. Like she was a bucking bronco and I am attempting to tame her. Leah's ass clapping against my stomach and my cock quickly pounding her pussy makes a little bit of noise.
"Uh, Mother. Could you turn it up a little more?" Rachel asks.
"Are you deaf?" Ms. Jackson asks.
"I just like this song." Rachel says. Ms. Jackson turns the dial further to the right. Janet's brother, Michael is singing now, 'Beat it'.
Leah is really going crazy now. I could sense she was close to climaxing. She twerks up and down, then gyrates back and forth, grinding into me in a circular motion and then attempts to twerk again. This random humping and pacing continues until my balls begin to churn.
"I'm close." I warn her.
"Good, keep fucking me." Leah whispers back.
Leah continues twerking on my cock and I allow her to slide up another inch or two just for the climax. I let go of her waist and lift the back of her skirt up even further to grab two handfuls of her tight little ass. Just then my ball sack clenches as I shoot my warm load into her tight pussy. Feeling my release, she impales herself on the entirety of my shaft and slowly grinds her ass into me back and forth. Milking all the jizz out of my cock as I pump a couple more loads into her. Then she goes still as our combined juices stream out her slit and run down in-between my thighs, onto the car seat.
Oh yes.
"You two don't look so good. You're not getting car sick yourselves, are you?" Hailey asks. She was looking directly at us.
"No. I feel great actually." Leah responds.
"I'm feeling a little better. Do you want to switch seats now?" Hailey asks.
"No, I'm okay. You stay up there. At least until the next stop." Leah answers.
Leah remains on top of me, my cock inside of her for the next ten miles or so. Eventually all the liquid from our dirty deed dries up. It leaves a slight scent but Rachel rolls down her window briefly, which helps. And finally, after some time I can feel my dick is slowly starting to deflate. Leah lifted herself off me and lets my semi flaccid cock shlurp free. I quickly pull my pants up around my waist.
Leah pulls her skirt back down and squeezes herself in next to me, draping her legs over my lap.
"You're welcome." She whispers to me.
"You are seriously insane."
"I know." She said with a smile. And I couldn't help it, I smile back. Rachel gives us both a scolding look.
"Oh shut up, you're just jealous it's not you sitting back here." Leah says.
We drive for another hour or so before everyone agrees that we are hungry enough to stop for some dinner. Ms. Jackson pulls off the freeway and into a hole in the wall burger joint. The girls all normally eat healthy but they decide they can let loose since we are on vacation.
We all order a burger and get two large orders of sweet potato fries, then we cram into a booth.
"Everyone doing okay?" Ms. Jackson asks the table. Everyone nods. Even I have to agree that the drive has not been as bad so far as I had imagined it being. A huge part of that obviously has to do with Leah. I still can't believe we had gotten away with it undetected by everyone but Rachel.
I wonder if what Leah had said in the suburban is true. Is Rachel really jealous that it was not her in the back seat? Rachel had no doubt enjoyed our sexual encounter a few weeks prior, but I had assumed that was more of a one time thing. I also still was not sure who knew what. Hailey wasn't aware of anything that had happened, I still needed to tell her the truth. The twins knew about Ms. Jackson. But did Ms. Jackson know about her daughters and I? I had never dared ask her in case they hadn't said anything to her.
"What were you listening to Jacob?" Hailey asks.
"A podcast on Python."
"Like the snake?" Leah asks.
"No. It's a coding program." Jacob rolled his eyes.
"Oh, well excuse me." Leah shot back. Everyone laughed but Jacob.
We talk excitedly about what we all want to do first once we get to the beach house. Finally, our food comes and the conversation is put on hold as we eat. We were all starving.
"So, we're about half way there." Ms. Jackson says once we start slowing down on the large meal. "We can either drive through the night and get there late, or stay at a hotel and leave in the morning."
Everyone except Jacob votes that we keep driving and just get it over with.
"That's easy for you all to say. I'm the one driving." Ms. Jackson says. "Are you sure you don't want to take a break?"
"You don't have to drive the whole way Mom. Someone else could take a turn." Hailey suggests.
Ms. Jackson looks around the booth. There is an awkward silence. No one wants to drive.
"Yeah, I could drive the rest of the way. Why don't you take a break?" I offer. Hailey smiles at me, proud of my apparent sacrifice. And it really is a sacrifice, I was hoping that maybe Leah and I could have a round two in the back seat for the second half of the drive. Guess not.
"Are you sure you don't mind?" Ms. Jackson asks me.
"Of course not." I assure her.
Once we are certain we cannot eat a single more sweet potato fry we clear our table and head back to the suburban. Ms. Jackson hands me the keys. I get in the driver's seat and adjust it a couple inches back. I turn the key in the ignition and the engine comes to life. The passenger door opens and closes. I look to my right to see Ms. Jackson sitting in it.
"Oh, hey Ms. Jackson." Sometimes, when it was just the two of us alone I would call her by her first name, Katherine, but she insisted I remain more formal in public.
"You seem surprised." She says. I am. I had expected Hailey to sit next to me for the rest of the drive. But I suppose that would have forced Ms. Jackson into the very back seat since Rachel and her family had filled the middle.
I look in the rearview mirror. Jacob, the baby and Rachel are all buckled into their seats. Hailey and Leah are snuggled up in the very back. With everyone inside I put the vehicle in drive and exit the parking lot.
"Thanks again." Ms. Jackson says to me. Then she wedges a pillow against the window and rests her head against it.
The free-way is much less crowded now. The suburban is quiet. The sun is starting to sink below the horizon. Streaks of pink and orange spread like fingers across the desert sky.
Free of distractions my mind begins to focus on the pit of guilt that has been growing deep in my gut. I glance up at Hailey in the rearview mirror. What will she say when I tell her what I've done? Will she forgive me for my weakness? Will she believe me that I don't love her any less? Or that what has happened between her Mother, her sisters and I is purely physical? I doubt she'd believe that. I don't even believe that myself. It's what I told myself at the beginning but I've come to realize that it's not true. I have feelings for all of these women. Not the same kind of feelings I have for Hailey. I love Hailey and I want to spend the rest of my life with her. But I can't deny that there is something there with the rest of the women riding in this suburban.
These are the thoughts that fill my head as I drive down the nearly abandoned road towards our supposed vacation. The headlights traveling the opposite direction begin to blur slightly. I can feel my eyelids starting to grow heavy.
"Hey, are you getting tired?"
I look over to see that Ms. Jackson is awake and looking at me.
"Oh, I'm okay. But I was starting to get a little drowsy." I admit. The sun is now gone and the only light illuminating Ms. Jackson's face is from the dashboard and a half moon in the sky.
Damn she is beautiful.
Despite her age Ms. Jackson's face is almost free of wrinkles. I'm sure botox has something to do with it. Although Ms. Jackson has also allowed herself to age gracefully. There's no doubt been some surgical intervention, ie. A boob job, but she is free from the 'plastic' look that some suburban Moms have who are so youth hungry.
"You're not the only one." She says, and motions to the back seat. I do a quick turn around and see that everyone is fast asleep. Jacob is drooling and Hailey and Leah are leaning against one another.
"But I'm up. I'll keep you company." She says, and she flashes that gorgeous smile of hers.
"Thanks." I say. "I've actually been meaning to talk to you."
"Oh, you have?" We're speaking in hushed tones, not wanting to disturb anyone's slumber.
"I know you already know this. But I love your daughter." I say.
"Yes, I know."
"And I want to ask her to marry me." I say. Ms. Jackon's eyes widen at this.
"But I didn't want to without your blessing."
"Of course you have it." She says.
"And, I also didn't want to ask her without first telling her the truth... about us." I say. Ms. Jackson sighs.
"I wish you wouldn't." She says. "But I understand. And I respect your decision."
"So as much as I love what we have. I think it would probably be best if it stopped." I say and I half regret it as soon as the words are out of my mouth.
She looks at me, her eyes wide in surprise for a second time. "Okay. Fine." I can tell she is hurt. She undoes her seat belt and leans across to me. "But you will let me at least say goodbye to our little relationship in a proper way."
And what exactly would a proper goodbye be?
She turns my face towards hers and plants a kiss on my lips before I quickly return my attention back to the road. Then she sucks my right earlobe into her mouth. "One last taste of your beautiful cock." She whispers.
"What? Now?"
"They're exhausted. And I'll be silent. Promise." She assures me as she reaches across the middle and undoes the fly on my jeans.
Ms. Jackson places her pillow on the middle console. Next, she lifts her legs and gets into a comfortable kneeling position. Her knees on her seat, her elbows cushioned on her pillow resting on the middle console. She pulls my jeans and underwear down my thighs a couple inches for better access. She reaches between my thighs and takes hold of my flaccid dick in her hand.
"Wow. This is a first. You're usually rock solid or at least growing by the time I get your pants off." She says, and I can hear some genuine disappoint in her voice. As if she is worried her sex appeal is wearing off or something. I decide against telling her the real reason. That I am most likely still coming out of my refractory period from fucking her daughter just a few hours previously in the back seat.
She leans back on her feet and shrugs her light hoodie off and lets it fall to the floor of the suburban. Thus, revealing her tight shirt which accentuates her huge round breasts. Cleavage spills out from the low-cut neck line. Then she rests her elbows back on the center console, this time over-arching her back so that her ripe ass, hugged tightly by her jeans, is high in the air. I can begin to feel my heart pumping blood away from vital organs and to my flaccid member.
"Hmm. Still soft." She says as she wraps her thin fingers around my dick once again.
She purses her lips together and gives the head of my penis a delicate, slow kiss. Then she smacks it against her plump lips. She sticks her tongue out, makes it broad and flat and smacks my rubbery cock against her tongue, making a quiet 'smacking' sound, looking up at me the whole time.
Giving in to her wishes I take my foot off the gas and put it in cruise control, then I lean my seat back a little to give her more room to work. Finally taking her eyes off of me she opens her mouth wide and easily fits all of my soft dick inside her mouth. Next, she seals her soft lips around the base of my shaft as tightly as she can. Inside her mouth her tongue is working furiously, flicking my tip and wrapping around my shaft like a boa constrictor until my malleable member is sopping wet with her saliva.
She's done it, she's flipped the switch, I can feel myself slowly began to expand inside of her mouth. As my circumference widens she is forced to expand her tight lips to accommodate. And as I grow I feel the tip of my cock pushing against the back of her throat. She gags and is eventually forced to retreat upward until her mouth is no longer at the base of my shaft but much higher now. Just a few seconds' prior she easily had her lips pressed against my stomach, now her lips are at least six inches away from my stomach and she still finds herself with more than a mouthful of firm cock.
She uses her left hand to brush her hair to one side of her face so I can see her better. She looks up at me and smiles with my cock still in her mouth, I feel her teeth against my tender skin. Then she looks back at the job she has ahead of her, the smile fades away, her lips form a seal again around my shaft and she goes to work. Working the top few inches of my colossal cock with her loving mouth.
"Aahh..." I can't help a quiet gasp of pleasure escaping from my lips. She lifts her left hand to my mouth and places a finger over my lips to shush me. Then she wraps the same hand around the base of my shaft and begins twisting it while she works the top with her mouth.
I check the rearview mirror, everyone is still fast asleep.
Thank goodness.
While Ms. Jackson is doing her thing, I turn my eyes back to the road. The road is clear except for a semi in the lane next to me and back a few yards. As the semi pulls next to me I look up at the driver. He looks at me, back at the road and then does a double take back at me, or more specifically at the blond bobbing head in my lap. I quickly lower my speed several miles per hour by knocking the cruise control switch a couple times. The semi pulls ahead and I change lanes, positioning the suburban behind him.
"Everything okay?" Ms. Jackson asks me, coming up for air.
"Yeah, fine. Don't stop." I tell her. And she doesn't have to be told twice. She checks for herself to make sure everyone is still asleep and then goes right back to my massive cock. She gets into a good rhythm and keeps it. As we drive through the dark desert on cruise control Ms. Jackson makes love to me with her mouth on cruise control. Her head going up and down, her hand stroking me in time.
God this feels amazing!
For twenty miles or more I fuck her mouth like this. I keep my left hand on the wheel but I let my right wander. I run my fingers through her blond hair. I rest my hand on the back of her head and gently push it down with each bob. She gets the message and takes even more of me into her mouth with each bob.
My hand leaves her head and travels down her back. I lift her shirt up halfway just so I can feel the skin of her lower back as its arched. I stretch, traveling further onto her firm ass. Her jeans are too tight, and her butt is so flexed in this position that it's impossible for me to really hold on to anything.
I let my hand travel slowly back up to the back of her head and repeat this process several times. I let my eyes shift as rapidly as possible from the road, to the rear-view mirror, to the incredible site of Ms. Jackson sucking my cock.
As we pass mile marker 178 Ms. Jackson begins to pick up the pace. Bobbing quicker, stroking me faster and faster. The incredible feeling causes the involuntary thrusting forward of my hips. This spurs her on even more. I check the rear view, Hailey is stirring slightly and a pair of headlights is not far behind us. Ms. Jackson sucks harder and faster.
In one swift motion, she lets my cock spring free from her mouth and takes hold of it with both hands, pumping furiously, her saliva removing any friction. She lifts her face to mine, kisses my mouth and shoves her tongue down my throat. I can feel it. She's coaxing it right of me.
There are no cars in front of us but I'm still worried about swerving, plus I'm about to bust and I don't want to jizz all over the steering wheel so I pull Ms. Jackson off of my face. Then I push her head down into my lap. She doesn't need any more guidance. Keeping both hands on my fat cock she takes the rest of it back into her mouth.
"Ooohh..." I struggle to keep another gasp of pleasure in as my muscles spasm and send a hot load of cum up my shaft and into Ms. Jackson's mouth. She Looks up at me, milking my cock with her hands while swallowing every drop of cum with her mouth. I see her throat muscles contract as she sucks my cock like a straw, sucking me dry.
Finally, I am empty. She releases me and sits back in her seat. Leaving my cock standing tall, still pulsing.
"Ahhh." She smacks her lips. "That was delicious."
I manage to tuck my dick between my legs and pull my pants up just as the car behind us makes a pass. It's a mini-van. Parents in the front seat, children in the back seat, watching an animated movie. The father makes eye contact with me and gives me a slight nod as they drive by.
"That was fun." Ms. Jackson whispers. I roll my eyes.
She's just as crazy as her daughter.
As we pass mile marker 195 I hear a disturbance in the back seat.
"How close are we?" Hailey asks through a yawn.
"Not much further." Her mother answers. "The ocean is actually on the horizon. It's just hard to see since it's so dark."
Ms. Jackson is right. She's soon telling me what exit to take, and an hour later I pull up to a thin house that is on a street where all the houses are equally thin and stacked close together. The Rest of the suburban wakes and we trudge our bags inside.
Inside the house is exquisite, Ms. Jackson spared no expense when she booked it. The main floor has a large kitchen, soft sofas facing a fireplace and large flat screen, a dining table large enough to seat us all, sliding glass door leading to a balcony. There's one bedroom on this floor, Ms. Jackson claims it.
Leah immediately heads downstairs to her room for the night. Rachel and her family go up one level and retire to bed. Hailey and I get stuck with the floor above that one, but when we reach the top of the stairs I am grateful for it. The very top floor is nothing but a large bedroom. A giant bed lays against the wall, facing the opposite wall which is made entirely out of glass, which in the morning will give us a perfect view of the ocean. Beyond the glass wall is a spacious deck.
Hailey and I organize our things in the bathroom. We are both eager to start our vacation, but we are more eager to get into the comfortable looking king sized bed and snuggle up underneath the satin sheets. My head hits the pillow and I have the thought to open the patio door a crack so I can fall asleep to the sound of the ocean. But it's too late... I'm already drifting into unconsciousness.
I awake the next morning feeling well rested. I'm in the bed alone. Hailey must be up already. Our room faces the west but it is already filled with sunlight. I look out and admire the breathtaking view. I slip out of the bed and walk out onto our private patio.
Wow. Ms. Jackson could not have picked a better house for the week. I look down to see that our back door opens right up onto the beach. From our back door, there's twenty or so yards of sand, then water. It's early but there are already several surfers in the water. A Jogger runs by. A couple holding hands strolls by going the opposite way.
"Good morning sleepy head!" I hear from below me. I look down to see that Hailey has just stepped out of the basement door onto the sand. I wave and tell her I'll be down soon. I turn to head back in and notice that from our patio there is a set of stairs that ascends onto the roof.
When I reach the main floor, I find it empty. There's a note on the kitchen counter, it's from Ms. Jackson. It reads:
Went to get Groceries. Be back soon. – Mom
I head down to the basement and then out the back door. I stop for a moment to savor the feel of the sand between my toes and then I jog to where Hailey and the rest of the gang have set up their chairs.
"Hey babe. Nice of you to join us." Hailey greets me.
I give her body a quick scan. She's wearing the new bikini she bought specifically for this trip. Her dark hair is tied up in a loose bun. Large sunglasses obscure most of her face. Her average sized breasts fill the top of her flower-patterned bikini nicely. Her stomach is flat and hard. Her hips flare out slightly. A small triangle of fabric covers the smooth surface between her legs. And her legs, they're slender, stretched out straight. Her skin is already fairly tan, but by the time we leave for home she'll be black no doubt. She tans so easily.
"Like what you see." She teases, catching me staring.
"I do." I admit. And Hailey isn't the only good thing to look at.
Leah is laying in the chair next to her. And compared to Leah, Hailey's swimwear looks ultra conservative. Leah is wearing what I want to call a tube top. Though it's more like a shoelace top it's so thin. And her bottoms are little more than a thong.
In fact, is that a thong?
Leah rolls over to sun her back and confirms that she is definitely wearing some kind of thong. Her perky round ass cheeks are completely exposed. Her lack of attire shows off all of her tattoos. My eyes are glued on Leah's backside when I hear laughter behind me.
I turn to see Rachel...
Oh my.
She's wearing a black one piece. The design comes to a V between her legs, cut high on her hips, revealing her legs. The sides have ovals cut out, showing her skin underneath and accentuating her hourglass figure. The tight suit struggles to repress her humongous tits. The neckline is modest but you can still see a large valley of cleavage. The sunlight shines through her blond hair. A genuine laugh shows on her face.
If she were running in slow motion this would be straight out of Baywatch.
Her young son clasps onto one hand, Jacob holds him by the other and they playfully dip his feet in the water as the waves roll in. Jacob looks as though he is already developing a sun burn.
I pull my shirt over my head and toss it under Hailey's chair. It's moments like these that I am thankful for the hours I put in at the gym. I don't have an insane physique but I feel comfortable with my shirt off. I look at Jacob and make a mental note to myself never to allow my body to become like that. Small spaghetti arms. Pot gut forming, soft with ice cream, fast food and too much leisure.
"Get your own boyfriend to ogle at." Hailey says to Leah and playfully hits her with a rolled-up magazine. Although it doesn't deter Leah. She keeps staring at me, in fact she gives me a wink. Hailey's not really upset. She takes the fact that I am in a good enough shape to 'ogle' as a compliment to herself.
I look back to Rachel and catch her eyes traveling up and down my body, but she quickly looks away. Rachel is much more subtle than Leah.
"What a beautiful day!" We all turn to see Ms. Jackson has returned. She's walking towards us carrying two large bags. One is full of food and one is full of beach toys. Her feet are bare. She's wearing loose tan colored capris and a baggy poncho type thing over her shirt. They do a could job concealing her curvy figure, but she still looks beautiful. A large sun hat provides shade for her face.
The girls dive into the food bag and start dividing it out. It's mostly fruit. Once they have their fair share in hand they all retire to a lounge chair and begin chatting and laughing with one another. I watch as Hailey presses a ripe strawberry to her lips, savoring the sweetness before she puts it in her mouth. Leah catches me watching and when she thinks no one else is watching she slides a peeled banana into her mouth as if she's deep throating it.
"I saw that Leah. You deviant." Ms. Jackson says. They all laugh because they know it's true. I decide I can't take anymore of watching the girls eat phallic shaped foods. I check the second bag and find a football.
"Hey Jacob, you wanna toss the ball around?" I ask him. Surprisingly he says sure.
The tide is low and we jog to the sand that is still wet and start tossing the ball back and forth to one another. The beach is more crowded now. Kids splash in the waves. Families build castles in the sand. Lots of joggers and casual strollers go by. Without fail everyone that goes by us slows and looks at the girls lounging in their chairs. Their heads turn to stare as they jog, or walk past our spot on the beach until if they wanted to keep looking they'd have to walk backwards, at which point they finally tear their eyes away. Men and Women both. I don't blame them though. The girls all look like goddesses that could have walked out of the sea like Aphrodite.
We spend several more hours at the beach. The girls soak up the rays for the most part. But occasionally when they are feeling too hot they spring from their chair and run and dive into the cool ocean. I always make sure to stop whatever it is I'm doing at the time and watch them as they do this, especially Rachel, her immense breasts bouncing up and down as she runs. And I'm not alone, all the beach goers around us stop to watch them too. I even see an annoyed lady smack the back of the head of the guy next to her who watches Hailey while making no attempt to hide it. A wife disciplining her husband no doubt.
Ms. Jackson stays in her chair though, reading. She must not want to get too much sun the first day because she keeps her capris, shawl and sun hat on the whole time.
Eventually all the fruit is gone and we begin to get hungry again. So, we pack up our stuff and head inside. Even though we have a fridge full of groceries the girls decide they want to eat out. We all slip on sandals. Everyone keeps their swimsuit on. Hailey puts on a pair of denim shorts over her bottoms. Leah does the same but with running shorts. Rachel pulls a long flowy skirt on and a thin jacket.
We walk to a casual sit down restaurant on the corner and have a big lunch. After we walk around the small shops on the street, mostly tourist type places. The girls all buy wraps to wear at the beach. Finally, we walk back home as the sun is beginning to set in the west.
It's getting dark but the air is still warm, these are the best kinds of nights. The air also smells and tastes of salt. We are all a shade darker, except for Ms. Jackson, and Jacob who is a shade redder. The girl's hair all have that wavy beach look from the salt water.
Once home we gather around the dining table and play a few card games. Hailey wins both rounds of Crazy Eights. She's weirdly good at things like that. We all laugh and have a good time, but eventually the energy in the room starts to die down.
"Can't believe I'm saying this, but I think I'm going to call it a night." Leah says.
"That sun really drains you." Ms. Jackson said.
"Mother, didn't you say they have a hot tub?" Rachel asked.
"Yeah, it's up on the roof." Hailey says. "There are stairs leading to it from the patio on our level."
"Anyone up for hot tubbing?" Rachel asks. Leah merely groans. She's already pushed her chair away from the table and is heading downstairs to her room.
"I think I'm going to retire for the night too." Ms. Jackson says. "But you can go."
"Let's sit in the hot tub for a bit with them before bed." Hailey says to me.
"Okay, sure." I say.
We clean up the card game and head up the stairs. Rachel and Jacob stop on their floor to check on the baby briefly. Hailey and I reach the hot tub first. I figure out the controls to turn it on and remove the cover.
"Does it have jets?" Hailey asks.
I check the control panel again and press a button. The water in the hot tub bubbles to life. Hailey hops in.
"It's already a little warmer. Should be hot in no time." She says.
I jump in next to her. Hailey gives me a kiss on the cheek. "I'm so glad we came. This place is amazing." She says. "Oh my God, look at the ocean."
I look out at the ocean. The last sliver of the sun is dipping below the Horizon and the effect is magical. Just as the Sun disappears Rachel and Jacob come up the stairs. Jacob sheds his shirt and I can't help thinking of an eggplant.
"How is it?" Rachel asks.
"It's nice and warm. Come in." Hailey tells her.
Jacob steps in and the water raises a couple inches. Rachel slips her jacket off and pulls the flowy skirt down her legs. Then she gracefully steps over the edge and into the tub. The water raises again but not nearly as much.
It's a good thing the whole gang didn't come, the four of us sit comfortably but it would have been crowded with even one more person. Hailey sits to my left, Rachel to my right, Jacob directly in front of me.
Hailey has her long hair pulled up to keep it out of the water. Rachel has let hers down. Strands of her blond hair float on the bubbling surface. Her vast chest also seems to float slightly, pushing her breasts up creating even more cleavage then before.
"I didn't know you could throw a football so good Jacob." Hailey says.
"Thanks." He says. I can't tell if he's blushing because his cheeks are already red.
"Yeah, it was a surprise to me too." Rachel teases.
I've noticed that Rachel starts off very formal, but when you get to know her she loosens up a little.
"And you looked like a natural out there." Rachel says to me. "You play?"
"I played some sports in high school. But I wasn't really good enough to do anything after that." I say.
"What did you all think of Leah'sswimsuit?" Hailey asks. Rachel laughs.
"I know every guy on the beach loved it. They couldn't stop staring at her." Rachel says.
"That's true. But they were looking at you just as much." I say. "And you too Hailey. You girls are all gorgeous. Even your Mom."
"Thanks. You're too sweet." Rachel says.
"He's right you know. Mom is a total milf." Hailey says.
"What's a milf?" Jacob asks. We all laugh.
"I guess we should thank her. We get our genes from her right?" Rachel says.
"Seriously, what's a milf?"
"It's an acronym honey. You figure it out." Rachel says. Jacobs forehead wrinkles in thought.
"Milk is liquid food?" He suggests. This earns a big laugh from all of us all. We spend the next several minutes talking about how nice the house is, making plans for tomorrow, and other things. Jacob periodically attempts another guess at what Milf stands for. All wrong.
"I'm ready to get out." Hailey says. She stands, steam coming from her skin. She steps out and I begin to follow her. But then I feel a hand on my lap. It grabs a fist full of my swim trunks and holds me down in the water. I look forward. Both Jacobs arms are draped over the side. Rachel's arms are hidden under the bubbling surface but her face makes no indication of what she is doing.
"Aren't you coming babe?" Hailey asks me while she wraps a towel around herself.
"Uhm, yeah. In a few minutes." I say. The hand underneath the water releases me.
Hailey disappears down the stairs and we hear the sliding door open and close. I look at Rachel but she is looking up at the stars. I look up at the stars as well. There are millions of them glistening in the black sky. Suddenly I feel something rubbing against my leg.
I look down. Rachel is still not looking at me. Her head now rests on her husband's shoulder. By logical deduction I know that it must be Rachel's foot rubbing against my leg but neither of us say anything.
What is she doing?
"So, you got a job lined up now that you've graduated?" Jacob asks me.
"Uhm, yeah." I answer. For the next few minutes Jacob makes small talk with me while his wife rubs her foot further and further up my leg.
"This water is getting a little hot for me. I think it's time for me to get out." Jacob says.
"I'll be down a little later." Rachel tells him as he steps out. The water level sinks, and like boats on the ocean Rachel's breasts sink a little lower as well. Before I can even think about following Jacob, Rachel's hand is back on my lap, signaling me to stay.
"See you tomorrow man." Jacob says to me.
"Yeah, goodnight Jacob." I say as he heads down the stairs. Rachel and I look at each other in silence until we hear the sliding door close behind her husband. "What's going on?"
"I just wanted a few minutes alone with you in the hot tub." Rachel responds innocently. And her face is so innocent that I almost believe her. If it wasn't for her smooth leg rubbing up against mine.
"Are you as crazy as your sister? This house is full of people and Hailey is one floor below us. I doubt she is even asleep yet."
"In some ways, I think I'm more crazy." Rachel says. "You see what I sleep next to each night. And trust me, it's rare that we ever do anything more than just sleep. You can't give me what you gave me and then expect me to never want it again."
I can't think of anything to say. I'd be lying if I said I wasn't aching for her body every bit as much as she must be aching for mine. And as if she can read my mind she says, "I know this desire is not one sided. I still see how you look at me."
And with that she begins moving closer to me. She rests her knees on either side of me on the seat, straddling me. Water droplets run down into the chasm created by her colossal breasts. She reaches back to pull all the hair away from her face, in doing so she thrusts her chest into mine. My hands instinctively hold her thin waist. Her lips part and she leans in to kiss me.
I kiss her back, hard. She runs her fingers through my damp hair. I pull her body in close, smashing her against me as she smashes her plump lips into mine. She begins to grind her pelvis into me. She pulls her face away from mine and moves to my ear.
"I want you to make love to me." She whispers. That's all she has to say and I am total goner. The way her soft voice hits my ears. She's not telling me what to do, she's genuinely pleading. Sincerely asking me to make love to her. The stars twinkle above us. The dark ocean to my right, the city lights to my left. And even though everyone is in the house just below us it feels like we are the only two people in the universe, up alone on this roof.
"I will." I tell her. "I will make love to you."
She leans back, her posture straight. My eyes go to the voluptuous mounds of flesh directly in front of my face. Then I look up at her, she has been watching me. She simply smiles and slides one strap of her suit over her shoulder, then the other. She raises both her arms and shakes gently back and forth, her suit falls an inch or two but there's no way it's going to make its way around her enormous breasts without some help.
I reach up, out of the water and loop my fingers around the straps of her suit. Next I gently begin to pull downwards. Inch by inch her magnificent chest is revealed. I pull the suit down, around the curvature of her breasts, exposing her slightly larger than average nipples, which are already hard. Finally, I have her suit pulled down to her mid torso, every inch of her body above the water is fully nude. Her heavy breasts hang like two giant ripe cantaloupes, waiting to be picked.
I take one breast in each hand, a single breast is much too large for even both hands but I do my best to massage them. Soft tit flesh oozes between my fingers. I roll her hard nipples between my thumbs and pointer fingers. There are still some stray grains of sand from the beach trapped in the valley of her large breasts.
"Ooohhh, that feels good." She moans as she thrusts her chest forward and begins grinding her pelvis into me again. We kiss passionately while I press her whopping tits together and she grinds into me. But then she freezes.
"What is it?" I ask. She shushes me. I hear the sliding glass door.
"Some ones coming." She whispers. And she gets off my lap, moving to the middle of the tub she sinks low in the water so that only her head is above. We hear steps coming up the stairs and we look at each other wide eyed.
Rachel sinks even further, completely submerging herself underwater just as Hailey's head breaches the top step.
"Who were you talking to?" She asks.
"Myself." I lie. Rachel's black swimsuit floats up to the surface.
She's totally naked down there!
I quickly pull it under the bubbling water before Hailey has a chance to see it.
"Rachel and Jacob go to bed?" She asks.
"Yeah." I lie again. Now Rachel is tugging on my swim trunks, yanking them down to my ankles.
"Why don't you come to bed?" Hailey asks me. Underneath the water, Rachel's mouth has found my rigid cock.
"Just a few more minutes. It's... ah... peaceful out here." I say.
"Okay. Don't be too long." She says. And after a brief pause she turns, heads down the stairs and closes the sliding door behind her.
Rachel surfaces, gasping for air. "I was beginning to think I was going to drown down there." She says once she catches her breath.
"Maybe you'd be able to hold your breath longer if you weren't exerting so much energy." I tell her. She just smiles, runs her finger through her wet hair and gives her head a couple shakes so that her wet hair is not flat against her head.
She stands up, her full breasts resurface. Beads of hot water slide down them and continue down her flat stomach, or drip back into the tub from her erect nipples or off the sides of her breasts. Just then the timer on the jets must run out because the bubbles stop and the water becomes still. We can now easily see beneath the surface of the water, removing any mystery. Rachel is fully nude and so am I, my lengthy cock standing tall, almost breaching the surface. The reflection of the water makes it appear even larger than it actually is.
With the jets off it is much quieter now. I can hear our neighbors in the back, talking and laughing. I can't see them but I can smell the marshmallows roasting over a fire pit. It reminds me that We are not truly alone in the universe, despite the feeling earlier. I also hear the methodical crashing of waves against the shore.
Rachel straddles me again, this time I feel her bare skin against my thighs, my cock against her stomach. Her hulking breasts press up against my chest. We kiss again, underneath the water one of her hands explores my straight shaft. She works her way slowly up, rubbing the head and then slowly back down the other side. Her fingers are not able to close around the entire girth.
"I've thought about this monster of a cock every day since I first laid eyes upon it." She says to me in a hushed tone.
"It's thought about you too." I respond, also in a hushed town.
"Be gentle with me." Something about her whisper is incredibly sexy.
She raises herself up enough to hover over my eager prick. She rests her left hand on my shoulder while the other hand guides me to the opening of her slit. She pushes the head in and then stops, her eyes close in pain. I wait patiently as she tries to accustom her narrow opening for my hungry cock.
"Aahhh..." she gasps as she lowers herself another inch. I hold her steady at the waist, not wanting to rush her.
"Aaahhh..." she takes in another inch, her eyes still shut. "Ooohhh..." She forces herself down a third time. She must be getting used to me because she opens her eyes now and looks down. "Oh, my God! I still have so much to go!" She looks up and smiles at me, then back down. She doesn't sound disheartened, if anything she is excited that there is still more of me to shove inside her.
She keeps her eyes open from now on and slowly continues to slide down my pole, "Aaahhh..." They are moans of pleasure now, the pain completely gone from her voice. Finally, her bare ass cheeks hit my bare skin and I am fully inside of her. As warm as the water is, inside of her is even warmer. My sensitive member burns with pleasure.
Rachel lifts her left hand out of the water now and interlocks fingers with herself behind my neck. She arches her back, lets her head fall back, her wet blonde hair dangles behind her as she looks up into the night sky, "Aaaahhh God yes..." She raises her head and looks back into my eyes. "Your strong cock feels so marvelous inside of me. Is it good for you?"
"You have no idea." I answer.
"I could stay like this forever." She tells me, and then leans in to kiss me.
I wrap my arms easily around her thin waist and pull her tight as we kiss. For a while we don't even move, we simply kiss, her soft breasts smashed up against me, my pulsing cock soaking in her warm pussy. I wonder if Rachel really meant it, if she really could remain like this forever. I know I can't. My hips are itching to move and eventually I give in to the urge.
Rachel's lips release mine as a moan of pleasure escapes from them. She begins to once again grind her pelvis into me, pushing against my own hip thrusts.
"Oh...yes.." she moans and then she starts kissing me hard, moving to my neck, my earlobes, back to my mouth. Kissing me furiously as she goes.
The grinding feels nice but I want a little more thrust. So, with my arms wrapped around her I lift her body up slightly and then let gravity pull her back down. I do this several times until She gets the message. She forces her strong tongue into my mouth one more time, then she retreats and breaks our kiss. Next, she places her knees more securely on the hot tub bench so that she can more easily slide up and down my throbbing shaft. I want it fast but she takes her time, moving slowly. I remember that she wants to make love, not necessarily fuck and I let her choose the pace.
I move my hands back to her waist and help guide her as she slides up, and then back down my thick shaft. "Do you like that?" She asks me.
"Oh yes, keep going." Despite being sexually deprived herself, she seems more concerned about making sure I am pleased.
Eventually her movements have created a mini wave pool inside the hot tub. The water laps at the sides of the tub, almost in rhythm with the crashing of the waves against the shore. Beads of water from the hot tub cause moonlight to shimmer off of her naked body, as well as illuminate her blonde hair. The whole scene almost looks surreal.
Like a race horse trapped behind the gate I desperately want to be let loose, but I continue to allow Rachel to stuff her pussy with my cock at her own tempo. She closes her eyes as I feel her muscles constrict against my cock, then release then constrict again in rapid intervals.
"Oh, my goodness." She exclaims, opening her eyes again.
"Did you just climax?" I ask.
"The slow riding of your firm cock was more than enough to make me orgasm." Despite having orgasmed she continues to ride me. "But I'm not done yet."
Man, if only I could have multiple orgasms like that.
Thankfully she begins to increase the tempo. She slides further up my pole and slams herself down rather than just letting gravity do the work.
"Aaahhh." She moans. I start thrusting into her as well. I move my hands from her waist to her heart shaped ass. Grabbing onto each of her ass cheeks I help raise her up and slam her back down, spreading her cheeks as I do so.
"Oh, God yes. Drive that solid cock deep." She moans. Her tremendous breasts begin to rise and fall with our motions.
"Please don't stop." She tells me. Her hands leave the back of my neck and grab onto the side of the hot tub. She arches her back and leans forward, giving herself the most leverage possible as she begins to ride my hard cock even faster. Rising a little bit further up my shaft and not sliding up again until her firm ass cheeks have slammed against my flexed thighs.
"Ooohhh yes...Aahhh yeah...." She moans. Her heavy breasts are bouncing up and down even more now, right in front of my face. They slap loudly against the water each time she comes down, splashing water everywhere, causing a constant drizzling of hot water droplets around her tremendous tits.
"Aahhh...Aahhhh...Ahhhh..." She moans loudly, a little too loudly. The neighbors have stopped talking at their fire and I wonder if they can hear us. But Rachel keeps riding, oblivious to anything else. The small wave pool in the hot tub has really grown now. Large waves lap at the sides of the tub and spill over the edges splashing onto the roof.
"Ooohhhhh I love your massive cock!" She risks letting go of the side of the tub with one hand just long enough to cup one of her own bouncing breasts. She tugs on the nipple, then lifts it to my mouth in a similar way I imagine she lifts a breast to her baby boy. I take it into my mouth and suck, flipping the nipple with the tip of my tongue.
"Oh, God yes!" She moans as she continues to ride me, I move my mouth from one bouncing breast to the other. I can no longer tell if the water is even warm anymore as it splashes around us. She arches her back again and lets her head fall backwards, the ends of her blond hair reaching the water. Like a mountain climber ascending upwards I can tell I am almost to the peak. I feel the familiar contracting and releasing of Rachel's pussy.
"Get off, I can't hold it any longer." I warn her.
"Good, I want you to cum inside of me!" She moans, without even bothering to raise her head, as if she doesn't have the strength to do so. Even if I tried to pull out, I wouldn't have the time now.
I lean back in order to get one last good look at Rachel as she continues to slide up and down my erupting cock. Her copious breasts bouncing up and down, slapping against the water. Water drizzling down her smooth skin, reflecting the moon light and also sloshing over the sides. I slam her ass down extra hard as I shoot my first load deep into her pussy, then another and another, each lessening in pressure until I am spent.
We slow to a stop. She lifts her head and slides off of me. My cum makes the water a little murkier as it dissipates. I stand and look around us, making sure we are still on the roof alone. A large ring of pavement stained with water surrounds the hot tub. Rachel stands as well and wraps a hand around my still hard cock. I turn back to her, with one hand still grasping my cock she wraps the other arm and me and pulls me in for a long deep kiss. Her wet naked body feels good next to mine.
Maybe I actually could orgasm again. Anything is possible when you've got her body to work with.
"Rachel, I busted in you." I break our kiss, remembering what just happened. She smiles.
"It's okay. I'm at my least fertile right now. And we're in a hot tub remember? I doubt if any of your little swimmers are still alive. I think we'll be okay." She says.
I know she's probably right, but It still worries me.
"As much as I would love to turn the jets back on and keep going, it's late. We should probably call it a night." She says.
She holds on to my cock as long as possible, almost in reverent awe, but then she releases me and we get dressed. We hold hands as we tip toe down the stairs, I slide the patio door open first and poke my head in. It's dark but I can see that Hailey is asleep in our bed. I slide the door open further and let Rachel slip past me. She stops, turns, gives me a quick kiss and whispers, "Thanks stud." And then she slips out the room and down the stairs to her own bedroom.
I hardly get any sleep that night. The euphoric feeling I had with Rachel in the hot tub remains, but that guilty feeling I've had in the pit of my stomach has mixed with it. Tainting it in a way. The next morning I wake up and slip out of the bed quietly, trying not to disturb Hailey in her peaceful slumber.
I tread lightly downstairs to the main floor, it's empty. It appears I am the first one up in the house. I crack some eggs and start making breakfast, enough for anyone who wants some. Outside is overcast, the waves are larger than they were yesterday and there are not as many beachgoers.
Rachel is the first one to join me in the kitchen.
"I thought I smelled something good." She says as she dishes herself some scrambled eggs and places some bread in the toaster.
"Rachel, about last night..." I start.
"I know, it was amazing. Meet on the roof again tonight?"
"You're right, it was." I admit. "But it can't happen again."
A frown appears on Rachel's face, the first one I've seen. She looks genuinely disappointed and is about to say something when Jacob walks into the kitchen next. That pang of guilt grows a little. Not only am I dating Rachel's little sister, but she's a married woman. And while Jacob and I are not exactly buddies, he's not such a bad guy.
Leah walks up the stairs next. She's wearing a baggy iron maiden T shirt, it's clear she doesn't have a bra on. She opts for cold cereal. Ms. Jackson and Hailey enter about the same time.
"Thanks for making breakfast." She says and kisses me on the cheek. "I didn't wake up when you came to bed last night, how late did you stay in the tub?" Rachel and I make eye contact and quickly look away.
"Uh, I'm not sure. I lost track of time." I say. Jacob seemed to be thinking, his forehead scrunched the same way it was last night in the hot tub.
"You know, I don't remember You coming to bed either..." he starts.
"Woh, look outside!" Rachel changes the subject. The entire kitchens attention shifts to look outside. It's pouring rain. The few beach goers that were braving the wind have cleared out now.
"Not beach weather, is it?" Ms. Jackson says.
The morning is a slow one. We lounge around the main room for a while. Ms. Jackson puts away the dishes. Jacob plays on his laptop and the rest of us sit on the couches, watching rain pelt against the windows.
Ms. Jackson makes Leah put pants on when she realizes that the only other thing she has on besides her iron maiden t shirt are panties. When she comes back we play a couple rounds of crazy eights. Hailey wins, again.
After that Rachel retires to her room to feed the baby, Jacob returns to his laptop. It's still raining and I decide to start the book that I brought with me. So, I go upstairs, get comfortable on the king sized bed and crack my book open. I'm several chapters in when Hailey walks in.
"What's up?" I greet her. She jumps onto the bed next to me. And even though I'm getting to a good part I put my book down to give her my full attention.
"So, me and the girls were talking." She starts.
"Yeah." I think I have an idea where this is headed.
"And since it doesn't look like the sun is coming out today."
"Yeah."
"We decided that we're going to go shopping at the outlets." She smiles at me. I knew it. "But don't worry. You don't have to come."
"And I won't be in trouble later for not coming?" I ask, suspiciously.
"No, I promise. It's a vacation, you should do what you want. And I know you don't want to come."
"Thank you. That's why I love you." I tell her.
"Have fun with your book. Maybe I'll get some new lingerie and surprise you when I get back." She winks.
"And that's why I really love you." I say as she leaves.
After several more chapters I reach a good stopping point. Go downstairs for a snack. I'm surprised to find Ms. Jackson there.
"Hello." She says, she's drinking a glass of wine.
"Hi. I just came down to get a snack." I explain. "You didn't go shopping with the rest of the girls?"
"No. I didn't feel like shopping." She says. I get bread out for a sandwich.
"I'm guessing Jacob didn't go either."
"No. He's probably in his room." She says. "I was thinking of watching a movie, care to join me?"
"Sorry, I'm at a really good part in my book." I say as I take my sandwich and start moving towards the stairs. She raises out of her seat and places her hand on my chest, stopping me.
"We don't have to watch a movie. We could do something... else."
"Ms. Jackson, I'm sorry. I told you, I can't anymore." I say. The fact that I don't use her first name, despite being in private shows that I am serious. She allows her hand to slide off of me.
"You know where to find me if you change your mind." She says and then she leaves the kitchen, entering her room and closing the door softly behind her.
I turn towards the door, debating on entering. I fight the urge and sit down at the counter. But I continue to stare at the door as I eat my sandwich. Finished. Now do I go back upstairs or into her room where I am sure she is waiting for me?
Eventually I go upstairs and pick up my book. But I can't seem to focus on it. I stand up and pace the room, like a caged tiger. Once I even go halfway down the stairs before I stop and turn back. For what seems like days I wrestle with my desire for Ms. Jackson over my desire to be true to Hailey.
Finally, I can hear the steps in the main room downstairs and voices echoing up the hallways. The girls are back from shopping. Part of me is grateful they've returned while the other half of me is cursing myself for not seizing the opportunity while it was there. I decide to take a cold shower.
Hailey is back in the room when I dry off. "Hey, want to see what I got. I think you'll like it." She says with a devious smile that tells me she is talking about lingerie.
"Surprisingly, I don't think I'm up for it. Tomorrow?" I say. My balls ache from all the pressure and lack of release. They are so sensitive that I don't think I could handle any fooling around just now.
"Sure. I guess it is kind of late. I can show you tomorrow. That way we'll both be fresh." I look at the clock. She's right, it's almost midnight.
We both get ready for bed and then snuggle up next to one another. Hailey falls asleep almost instantly and once again I am left alone with my thoughts.
The sound of waves wakes me. I stretch and allow my eyes to adjust to the light. Hailey is standing out on the patio, leaning against the railing, her long dark hair blowing in the wind.
Thank goodness, the sun's out today.
Everyone scarfs down breakfast quickly and heads to the beach. I grab a boogie board and spend the first hour or two of the day catching waves. Once my body is exhausted I head in and collapse in the sand. Jacob has a shirt on today, apparently not wanting to worsen his burn. The girls are all in their chairs.
Rachel is wearing a one piece again, only this time it is red and only has a strap on one shoulder. Her breasts look massive as ever. Hailey is wearing a bikini I have never seen before, she must have gotten it yesterday. It's orange with frills on the top piece, the neon color makes her look even more tan. Leah is wearing a halter top today, so a little more modest. With similar bottoms as last time, a thong. Ms. Jackson has swimwear on today but she is still covered up with a large shawl, with a wide sun heat on her head. She's reading a Virginia Wolf novel.
"You ladies want to do anything other than sit there today?" I tease them once the hot sun has dried me.
"What do you suggest?" Hailey asks without opening her eyes.
"How about a friendly game of touch football?" I recommend.
"Sounds fun." Hailey says.
"I'm in." Leah adds.
"I'll play." Rachel says. "You playing Mother?" Ms. Jackson looks up from her book.
"Ah what the hell. Sure." Ms. Jackson says to my surprise. Jacob would really look wimpy now if her refused to play so he agrees as well.
Ms. Jackson sets her book down and removes her hat, her blond hair falls down around her shoulders. Next, she pulls off her shawl and drops it to the chair.
Damn
I instantly regret denying her the night before. She is looking fit as ever. Few women can actually make a bikini look good, especially ones her age. But she looks like she fell right out of a magazine, touched up and everything. I'm reminded again where the girls get their amazing genes from.
Her bikini is dark blue with white polka-dots. The string holding her top up and holding her large round breasts in is tied around her neck, taut with tension. The triangle shaped fabric of her top is cut large but you can still see the curvature of her breasts protruding out the sides. Her waist is trim, her stomach flat and hard. Her bottoms are small enough that if she had any pubic hair you would know it. Her butt is round and firm with muscle. Her legs lean, long and smooth. Not a trace of cellulite anywhere.
"Rachel, Jacob and I vs You, Hailey and Leah." Ms. Jackson says and she takes the ball from my hands.
The tide is still high so we have to play on the soft uneven sand. We trace lines in the sand for end zones with our feet and line up. I allow the other team to start with the ball.
"No first downs. You can rush after six seconds." I say. They probably have no idea what that means but they'll figure it out.
Ms. Jackson plays quarter back, I guard Jacob and Hailey guard's Rachel. Ms. Jackson yells hike and her wide receivers run random routes. Ms. Jackson tosses the ball into the air. Jacob trips, falls into the sand and I easily snatch the ball out of the air. Then I begin running towards the end zone. WHAM. Ms. Jackson slams into me, wraps her arms around me and we go down.
"Didn't you hear me say touch football?" I say after I spit out some sand while Ms. Jackson's body is draped over mine.
"We're tough. We can handle tackle. Unless you're saying you can't handle tackle." Ms. Jackson teases as she gets off me. I look up to see that Hailey is laughing hysterically.
"Okay, tackle it is." I say.
The girls elect me as quarterback and Leah insists on snapping it to me. She squats down and arches her back, her bare butt cheeks are a little sandy. If there had been a ref he would have called delay of game on me for sure. I pass it to Hailey and we score.
People were ogling the girls before, but they have really drawn a crowd now that they are running around in swimsuits and tackling one another. The girls either don't notice or pretend not to notice. Except for Leah. She seems to enjoy the attention. She makes sure to bend at the waist any time she picks up the football. Positioning her ass to give spectators a good view. Our neighbors even come out on their deck to watch us, at one point they begin cheering for us when we score.
Some highlights include Hailey taking Jacob out at the legs and Rachel and Ms. Jackson wrapping themselves around me in an effort to tackle me as I powered into the end zone, Leah jumped onto my back for some reason, finally bringing me down, even though we were on the same team. The girls all played surprisingly aggressively but eventually we all run out of steam and decide to head inside for a late lunch.
"We should make it a formal lunch." Hailey suggests.
"I like that idea." Ms. Jackson says.
"You just want an excuse to wear your new clothes." I say to Hailey.
"Nothing wrong with that." Ms. Jackson defends. "Everyone meet on the main floor in a half hour for supper. Formal wear required."
There are two showers on each floor. Enough for everyone to have their own. For that reason, I take a long shower. The hot water feels good on my sore muscles. I scrub thoroughly to make sure I remove all the stubborn sand. When I return to our room Hailey is still in the bathroom doing her hair. I put on a pair of slacks and a white button up dress shirt. I consider putting on a tie but then realize I didn't pack one.
I decide that Hailey's idea for a formal dinner wasn't a bad idea after all. I feel kind of nice, like I'm going somewhere fancy to eat. I head downstairs and see that Jacob is already waiting at the table. He's also wearing dress clothes except he had thought to pack a tie. His tie is a little thick in my opinion but he looks nice. Even his little baby boy is dressed in a button up shirt.
The table is already set, the lighting is set to dim, like it would be in a fancy restaurant. Rolls rest on the table with steam coming off them and it looks like something else is in the oven as well. Ms. Jackson must have set everything up and then left to get ready.
I sit at the table with Jacob and we each snack on rolls, waiting for the girls to arrive. My stomach growls. I'm starting to get hungry and impatient. But when the girls finally do arrive my patience is more than rewarded. It must be a sister thing because Hailey, Leah and Rachel all enter at the same time. They look stunning.
They are all wearing black high heels and black cocktail dresses. The dresses are similar but with some differences in design that seem to fit their individual personalities. Hailey's is down to her knees in length. It is form fitting which shows off her slender figure and curves. The top half of the chest is made of a lacey see through design, its got tight sleeves that go down to her wrists, also made from the same see through lace material. Her lips are red with lipstick, her mascara makes her blue eyes pop. Her long dark hair is straight and shiny.
Rachel's drees is an inch or two shorter than Hailey's, ending before the knee. But while hers was also tight up top it was looser starting at the waist. The end frilled out, the type that would flare out if she twirled. It had short sleeves and went all the way up to her throat. Her blond hair was up in an elegant braid, which showed off her superb neckline and perfectly chiseled bone structure. Her plump lips were also adorned with red lipstick. The large diamond in her wedding ring sparkled even brighter when held against her black dress.
Despite having the smallest chest out of the three, Leah's dress showed the most cleavage. It was sleeveless with two thin straps going over her shoulders. The back las cut low and the front was cut even lower. Like Hailey's it was pretty much skin tight, unlike Hailey's it stopped well before the knees. It was easily the shortest dress of the three. Her shorter blond hair with pink highlights in it was down, cut at the same angle as her sharp jaw line. She wore red lipstick also, although hers was a shade or two lighter, almost pink.
They all walked elegantly to the table, their heels clicking and clacking against the wooden floor. Hailey's dress looks especially difficult to maneuver in but she made it look easy. She takes the seat next to me. Leah takes the other seat next to me and Rachel sits next to her husband.
"Wow, you all look beautiful." I tell them.
The door in the hallway opens up and Ms. Jackson steps out.
Holly...Hell...
I would never say this out loud, but for the second time today Ms. Jackson rivals her younger daughters, possibly even outshines them.
She too is wearing black high heels and a black cocktail dress. Her dress is long and flowing. The Front opens up for her legs, allowing her to walk, but the back is long enough that it drags across the floor. The dress appears as if someone drizzled dark chocolate all over her body and then let it harden, showing her hour glass figure. The neckline is not too low, but low enough to reveal the tops of her round breasts and the valley they create. Her long blonde hair is down in soft waves. She wears thin black gloves that extend almost to her elbows. Around her wrist is a pearl bracelet, a matching pearl necklace around her neck. Wrapped around once tightly around her neck, and a second time loosely. So loose that it trails down her front and disappears into the deep valley created by her succulent breasts.
I've seen those pearls before. She was wearing them the first time we fucked. She refers to it as the first time we had sex, but I refer to it as the first time she seduced me. Her hips swish from side to side as she walks to the oven and retrieves our meal. It's one of her healthy vegetarian experiments.
For some reason when she sits at the table I feel much younger. Like a little boy again.
"I think this was a great idea Hailey." Ms. Jackson says. "We all look excellent."
Ms. Jackson calls on Jacob to say a blessing on the food and we dish up. Wearing fancy clothes improves our table manners as well, we keep our elbows off the table and ask politely for things to be passed to us rather than reaching across the table for them.
"Thank you so much for planning this trip Mother. It's been amazing so far." Rachel says. We all agree with her.
"Don't mention it. I'm just glad you could all make it."
"Mom, what ever happened to that mystery guy you were seeing? I was half expecting you to bring him." Hailey aks.
"It didn't work out between us."
"What? You seemed so happy." Hailey says.
"Yeah. But we both knew it could never be anything serious. So, he broke it off."
"His loss." Hailey said. I hoped my recent tan was dark enough to cover my blush. "Seriously Mom, you are hot stuff. Don't you think so?" Hailey directed the question at me.
"What?" I choke.
"Wouldn't you date my Mom? She's freaken sexy right?" Hailey asks.
"Uhm..yeah. Your Mother is a very pretty lady." I say.
"That's not what I asked. Seriously, all of you girls are gorgeous. You're already dating me, but wouldn't you date any one of the girls at this table if you could?" Hailey asks me.
"I've never really thought about it." I lie.
"Well, would you? Yes or no?"
"I..uh..I suppose so." I stammer.
Hailey smiles, as if her point was made. I try to busy myself with the meal. It actually doesn't taste bad. Not filling at all, but not bad. "Can you imagine? You with one of my sisters? Or my Mom?! Ha, that would be crazy."
I choke on my food momentarily. Luckily Jacob says something.
"Rachel, do we have any more of these? He loves them." Jacob's referring to some kind of mashed up baby food.
"No. That's our last one." She responds.
Thank goodness that changes the topic of discussion to Rachel's baby for a while. Then Hailey and I are pestered for some time about when we are going to get pregnant. After, we speculate if Leah will ever settle down and have kids. We stray from topic to topic and I hope that the incredibly awkward one before has been forgotten. Ms. Jackson asks if anyone wants dessert. We all say no, besides Hailey has been rubbing my thigh underneath the table for the last five minutes. I think she has another type of dessert planned for the night and I owe it to her. We haven't even fooled around once since we've been here. I hadn't really noticed since I had been busy, but I'm sure Hailey is wondering what happened to my usually over active libido.