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Chapter 5 (Strangers and other lovers)
“Hey guys, what’s a MILF?”
Curt’s hands had stopped making their random rubbing motions across the front of Shelley’s body when she’d asked that question. I’d stopped in mid-sip of my drink, and Kelly and Amber both lifted their heads from their quiet conversation, waiting to see how this would be answered.
“No, really.” Shelley continued, noticing that everyone was looking at her. “I’ve heard the term from Brad and his friends before today, but I’ve never known what it meant. Alex said it today about me though.”
So… what’s a MILF?”
“You’ve heard Brad, our Brad, our son Brad, using the word?” asked Curt.
“Well, yeah.” Shelley replied, “I hear him and his friends use it all the time when they get together. I’ve heard them say it after I go through whatever room they’re in, when they think I can’t hear them. What does it mean? Is it bad?”
She turned around to look at Curt, and he just looked back at her blankly. Turning to me, she said “Jack? Could you please tell me what it means?”
I opened my mouth, trying to think of how to word this, when Kelly suddenly piped in. “Mom, it means ‘Mother I’d Love to Fuck.'”
Shelley’s face turned white, as her daughter asked her, “You’ve actually heard Brad refer to you that way? That’s funny!”
I could tell that Shelley was now sorry she had put out this question. “Yeah. At least I think so. I mean, I’d bring something to the rec room, then after I left I’d hear somebody say something like ‘Nice MILF Brad’, and he’d say something like “Yeah, no kidding”, and then it gets real quiet. Do you think Brad wants to… you know?”
Once again, Kelly answered her mother’s question. “If there’s one thing I’m the expert on right here and now, its teenage boys. Brad’s sixteen, and he and his friends are just big walking bags of horny right now.”
“If his friends are saying that” she went on, “I can guarantee you that his friends mean it. Brad may not know if he means it or not, he could just be saying it to fit in.”
“How would I know?” asked Shelley. “This is kind of a weird thing to be thinking about.”
Of all people that I was expecting to talk next, it was not Amber, but talk she did.
“I have big brothers and I have little brothers, and I’m kind of an expert on horny teenage boys. So, have you two ever had your underwear or bras disappear for a week or two, only to have them just show up one day in the laundry, maybe even with odd stains on them?”
Both Shelley and Kelly nodded and said “Yeah!” at the same time, and then looked at each other with shocked looks on their faces.
Horrified, Shelley stammered “Do you think that Brad’s doing ‘things’ with our underwear?”
“Well, duh.” Amber said. “And people think that I’m the dumb one. My brothers do that, or they suddenly have to pee really bad while I’m taking a shower, then they try to startle me when I’ve only got a towel on, so that it falls off.
“Oh. And they always walk behind me when I’m climbing stairs in shorts or a skirt. It’s normal. It makes me feel kind of special, like I’ve got a power over them.”
Once again, mother and daughter had the same thought at the same time, saying, “I thought you were borrowing my stuff…”, and looking at each other in horror. Shelley spoke first. “What are we going to do about this?”
“If you stop thinking about just who this one person is for a minute,” I piped in, “and remember your original question, you should feel pretty good.”
“Good!? Good?!” shouted Shelley, “You think that I should feel good that my son wants to, uh, you know with me?!”
“No.” I said very carefully. “I think that you should feel good that both Alex and Kyle, and that apparently all of your son’s friends, and yes, maybe even your own son, think that.”
“Yesterday” I went on, “you were upset and worried when you thought that I didn’t want to be with you. Today, you’re worried because someone else does.”
“But these are kids!” Shelley spat back at me.
“Not so much, Mom. Not anymore.” her daughter replied, earning a shocked look from her mother. “I mean, I’m really not too wild about having Brad beating off into my panties… Eww!” she shuddered, “…but they are healthy, growing sixteen year old boys, with lots of healthy, growing sixteen year old girls to be thinking about, and they like us.”
“Besides.” she went on. “I would think that it’s better to dream about us, than to actually do something with the girls their own age. They could get into some real trouble there.”
Shelley opened her mouth to talk, but it was at about that point that we all heard banging noises and the sounds of screaming coming from the deck above. The conversation suddenly forgotten for the moment, we all rushed out the door and up the back stairs to see what had happened topside. Each of us was presented with the same view, as we came up the ladder onto the flybridge. Still screaming loudly, but apparently in pleasure, not in pain, we saw Heather.
She bahçeşehir escort was naked once again, and Alex was beneath her on one of the fold-down seats, his impressive cock buried deeply inside of her. His fingers were both up on her small tits, pinching and twisting her bouncing nipples, hanging onto them for dear life.
Heather’s body was being driven up and down onto Alex’s cock by the forces being applied to her from Kyle’s huge monster, which was buried up in her ass all the way to its base.
Kyle’s hands held tightly onto Heather’s hips, pulling her quickly back with his hips and onto Alex’s member every time he pulled himself backward. Each time that he did this, we would hear another scream, gasp, or moan emitted from Heather’s lips. For his part, Alex wasn’t just laying there letting Heather’s wet cunt fall on him as it might, he was thrusting up with a great deal of power, grunting loudly each time that he drove his cock deeply into Heather’s dropping body.
Heather’s eyes were wide open but un-seeing in concentration, and the look on her face was one of pure, animal lust. None of the three noticed us as we all burst onto the upper deck, not even as we drew around their bucking forms in a half-circle. On and on Kyle and Alex continued pounding themselves into Heather’s two holes, and on and on she rode the two thrusting men, the rest of us watching in fascination as we witnessed not one, or two, but three huge orgasms take her entire body over in their awesome power. Each time, she would shudder and shake, letting out another long scream like the one that had drawn us all up to watch.
As Heather was being wracked with her third orgasm, Alex shouted out that he too was cumming, blasting her overworked fuck tunnel with his hot seed, shuddering and groaning from his release. After this, he stopped driving himself into my tiny girlfriend, allowing her limp and sweaty body to come to rest at last on top of his own, her tiny tits being crushed into his chest.
He wrapped his strong arms around her in comfort and support as her dripping body continued to be driven across his by the force of Kyle’s big jackhammer striking her from behind.
Kyle’s monster continued to thrust deeply within her for another few minutes, but by this time she was just too tired to push back onto him. Each time he would drive himself into her depths, she would let out a small noise like that of a mewling kitten. With her body being held still beneath him instead of on him as it had been before, Kyle was now feeling the full sensation of moving within her. Letting out his own final cry, he sent himself deep into her asshole one last time, sending out so much cum with so much force that it shot back at him in a thin spray, out of her hole and around his huge cock. Finally, he too stopped his motions, pulling out of Heather’s abused rear entrance and collapsing exhausted onto a seat behind him.
The five spectators stood in silence, and then Kelly began clapping in earnest and making a hooting sound. The rest of the group just looked at her, and she stopped. With Alex still buried deep inside her, Heather lifted her head, looking at the ring of friends around her and smiling.
“Who’s next?” she croaked, her head dropping back to Alex’s chest, falling instantly asleep in exhaustion.
I wasn’t quite sure if her question was asking who was next to ride her, or who might be up next with Alex and Kyle. I avoided the question by walking up, lifting her limp form off of Alex, and carrying her in my arms down the front stairs and into my main sleeping cabin below. She slept right through all of this, but the movement of her tiny breasts against my chest and the heavy smell of sex that was pouring out of every opening she had caused my cock to grow until it was a steel bar.
I suddenly remembered about the man named Chris from the wedding and from the pool area. It had finally occurred to me that in a company where people had random sex at all hours in the office, having someone like Chris to clean up messes such as this might be a requirement. Perhaps that was his job title, it seemed to be what he liked to do best, and it would certainly save on upholstery cleaning bills. If I saw him back at the house again later, I would have to ask him about that.
After standing above Heather’s sleeping form for what seemed like many long minutes, I made my decision, lowering my head between her legs and starting to clean her up.
It appeared that Heather had been well fucked today, probably by Curt at least once as well as by the two young studs above. While she slept on the bed, I continued to lick her clean. I took my time, starting with the skin stretched across the area where her legs ended and her body began. Finding and tasting sweat and cum everywhere my tongue went, I lapped her skin and pussy lips like a cat cleaning itself.
At some point, another head joined mine between Heather’s legs, and I glanced over, surprised bakırköy escort to see Shelley’s face next to mine. For some reason I had expected Curt. While my tongue and lips worked on the areas outside of Heather’s dripping hole, Shelley drove hers right up between Heather’s extended lips, sucking huge quantities of mixed male and female juices from within, having to swallow repeatedly in order to remove the mess. When I moved closer in to get my own share of these juices, Shelley moved up Heather’s body, licking more cum and sweat, suckling on her tiny tits and puffy nipples until those shrank into themselves and became hard.
Once we had completed cleaning Heather up as well as we could, Shelley turned her body around, concentrating her lips, teeth, and tongue back down on Heather’s clit. When she did this, her own bottom ended up next to Heather’s face.
Whether she had slept through all of the previous attention or not, Heather was awake now. Pulling the fabric of Shelley’s bikini bottoms aside, she drove her tongue between the lips of the older woman’s cunt hovering in front of her. Shelley let out a long sigh when Heather found the spots we had learned about in the hot tub the previous night, and began to sway her hips back and forth across Heather’s face rubbing her soggy cunt over the face below her, while the younger woman tried to concentrate on her now moving target.
I watched the two women enjoying each other’s attentions for a while, when suddenly I realized that every man on this boat had been inside of my girlfriend today except me. Deciding to rectify this situation, I stepped out of my trunks and moved up, lifting Heather’s legs alongside each of Shelley’s ears, positioning myself at her well-used hole, and pushing my cock past Shelley’s tongue and into Heather’s already well lubricated depths.
I began with a gentle swaying motion in and out to savor the feeling. Shelley began to alternate her tongue between circling the line where my cock and Heather’s lips met, and licking and sucking on Heather’s clit. She must have been having an effect on Heather, because I could see that familiar shaking begin all over her slim body. I continued to ease myself in and out of the familiar pussy before me, when suddenly Shelley’s body was hit with one of the patented orgasms women seemed to get when they received Curt’s special licking method.
Just as Shelley calmed down, I began to feel the pressure building within my loins, I was about to cum as well. Since we had just spent a great deal of time cleaning Heather’s pussy out, it seemed a shame to fill it up again.
As soon as I pulled myself out of Heather, Shelley grabbed my cock, surrounding its shaft with her lips, driving her mouth up and down along its length. The sudden change in textures caused the pressure to build up then to the point of no return, and I came quickly into the warm mouth that was covering my cock. Shelley swallowed every drop, without having even a single drop of my cum leak onto her face. After all of this action, we all were tired, and the three of us cuddled together as a single mass on the bed, each falling asleep in the other’s arms.
We were awakened by an alarm coming from the auto-pilot, which I had set before we left the island. It was telling me that we were within five miles of the marina, and that it was time for me to take control of the boat back. Quickly getting dressed and walking up to the flybridge, I saw Kyle and Alex looking perplexed at the boat’s control panel, trying to figure out what the alarm was and how to make it stop. As soon as they saw me, I received a chorus of “We didn’t do anything!”
“It’s OK guys,’ I told them, “it’s just the boat telling me that it’s my turn to drive.
“You may want to get below and get everyone straightened up though, we’ll be docking in just a little while.”
Taking over the wheel, I shut the autopilot off, and began the process to bring the big boat into the marina. It had been a smooth trip back from the island, and I had no problems getting lined up for the dock. Heather was MIA just then, so I had Kyle go over and start getting us tied up. Of course, I would be finishing the job, but he didn’t really need to know that right then.
Once we were docked, I told everyone they could go on up to the house, that I would finish up down here. I watched them all go down the dock as a rowdy group, then went below and finished getting the boat back into shape, stowing various items and collecting all of our garbage for disposal. Once I was satisfied, I headed on up myself, passing through the courtyard once again on my way to the room.
There seemed to be the usual array of semi and undressed people around the pool, but my eye was drawn to a particularly striking young lady who was conversing animatedly with a group of young men. She was wearing a very tiny black bikini, but not one that just presented everything to the world, rather one that suggested only hints başakşehir escort of what might lay beneath.
She was wearing sunglasses and a floppy hat, but had an all-over tan so I figured that she must not wear that hat all of the time. Her thick black hair reached slightly above her shoulders, with a butt that was just the right shape. Her well-contoured breasts stayed high up on her frame, and were some of the finest I had seen in a long time.
The mystery woman waved to someone in my direction, but I couldn’t tell who might be near me. With such a large group of men around her, I decided not to be just another face in that crowd. I would look for her again at dinner tonight, if so, I could quietly invite her to come out on the boat tomorrow. I would need to find Freddie too, to tell her that I would be requiring her piloting services.
I turned away from this lovely vision, making my way once again up to the suite. On my way up the stairs towards the room I came across Kyle, Kelly, Alex, Amber, and Heather coming loudly down it towards me, wearing shorts and light shirts and carrying some bottles of champagne that had probably come from the room.
Heather seemed to have recovered well from her earlier exhaustion. “Hey Jack!” they all shouted. “We’re going to a beach party! Want to come along?”
I shook my head no, and they all started past me. Heather stopped on the landing to talk to me, saying “I’m sorry baby, I know I’m leaving you alone for dinner, but this sounds like fun. It might go really late though, so I’m just gonna stay in one of the dorms with these guys. Is that all right with you?”
“Sure.” I said, lying just a little bit. “You go out and have fun, I’ll see you in the morning.”
She gave me a long kiss and a tight hug, rubbing her body against mine like a cat, quietly saying “Thank you for taking such good care of me today. I know it’s been a busy weekend, and we haven’t been with each other very much. I really did enjoy that though, so much!”
Then she reached down and began rubbing my cock through my pants, looking up and deeply into my eyes. Sighing, she reluctantly turned away, hurrying downstairs to join her new friends.
Sporting yet another erection that had been created by Heather, I opened the door to our empty room, letting myself in. I really needed a shower, as it had in fact been a pretty long day already. Stripping out of my clothes, I headed naked into the bathroom, forgetting for a minute that it was a shared place. It didn’t really matter though, as Curt and Shelley and I had all become quite close in our short time together so far.
I didn’t expect to walk into what I did though. As I came into the common area of the bathroom, I saw Shelley leaning down over the counter on her elbows, her heavy breasts being crushed down on the surface. Her husband was standing behind her, repeatedly thrusting himself into her. Both were gasping and moaning loudly, so intent on what they were doing that they hadn’t even noticed my intrusion. As I stood there watching the two of them rutting, my already stiff cock grew even harder than it had already been.
Quietly backing out of the bathroom, I returned to sit on my bed, waiting for them to finish, suddenly missing the possibility of replicating their actions on Heather. I could hear their mixed cries for another few minutes as the lovemaking continued on, until I finally heard the sounds stop, which I took to mean that they were done. Waiting a minute more, I once more strolled naked into the bathroom toward the shower.
They were locked in an embrace, out of breath and covered in sweat. Curt noticed me coming in this time, giving me a greeting of “Hey Jack! We were wondering when you’d show up.”
“Hey yourself.” I replied. “I ran into the other guys out in the hall. I guess I’m on my own for dinner tonight, unless you want to join me. Right now though, I’m badly in need of a shower.”
“Do you mind if we join you?” asked Shelley, with a sparkle in her eyes. “I could use some cleaning up myself.”
“Hey, there’s room for as many people as you want.” I replied, “I think we’ve proven that more than once the past few days.”
“Tell me about it.” she said, looking down at my very obvious hard-on. “Those five all went at each other in there just as soon as we got to the room. I swear, those kids do nothing but fuck!”
“I think Curt has a thing for Amber though.” she continued, leaning in as if only I could hear her. “Curt was on the phone while everybody was in here getting ready earlier. You know how you can see in here if you’re in just the right spot? He must have been right there, because he completely lost track of what he was saying on the phone twice whenever she came around.
“Kelly could’ve told about it you too, but she was busy both times. The first time, she had dropped something under the bed, and all you could see was her bare ass in the air, the second time she had one of her knees lifted up between her face and the door while she was shaving her legs with Curt’s little electric razor.”
“And you saw him on the boat,” she went on, “I don’t know where his mind was then, but he was so into whatever fantasy he was having that when we walked in, he didn’t even notice us. It wasn’t until Kelly started talking that he came out of his trance, and then he only went at it harder with that poor little girl.”
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