The Milf Resort and the Pool Ropes

"MOOOOOooooom. Stahp!" I whined probably more than I should. But I hate it when she tries to fix my shirt. Of course it's wrinkly, we just flew to another country to a.... oh god. Do I dare admit it? We just flew to a resort that we're staying at for a week. I'll leave it at that.

"Sweetie, will you stop by the bar and get mommy a glass of moscato? You can get something for yourself too."

"Mom, I'm not 21, I like, just turned 18."

"Doesn't matter in the Caribbean. Quickly hun."

Wait, did mom know that I've drank before? I don't think we've ever actually talked about it, but I'm sure that she's noticed over the years. It was never much, but looking back it was probably noticeable. Then again there has been a lot that we haven't talked about until recently. But maybe we are now, and maybe that's why we're here.

While waiting at the bar I started to notice some of the other guests. Most seemed like normal people, lots of young men my age, and lots of older women. Most of these women were still relatively young, 30's or 40's maybe. And thankfully most took care of themselves pretty well so the pool scene wasn't bad. A couple of passing women even eyed me up and down..... but like.... pretty blatantly.

After getting back to a couple of lounge chairs, I quickly went into incognito mode and tried to lay low. Not gunna lie, I'm still trying to figure this all out. Mom gave me shit for ordering a pina colada, but I didn't really know what else to order. Mom kept a pretty keen eye out though, like someone was watching her. She REALLY seemed to notice the other pool patrons.

Maybe it was the warm sun on my half naked body, or the second boozy drink settling into my stomach, but I was jolted awake right as I was drifting off by someone bumping into my drink and almost knocking it over. After quick reflexes I glanced up to see a woman settling into the lounge chairs next to me. She apologized and asked if I was saving that chair for someone. "No ma'am, it's all yours." I responded without thinking. "Ooooohhhhh such manners!" the woman coo'd giving a glance at my mother in the next chair. Of course mom started a conversation: "Well Avery's father, my ex, was in the military and we were stationed in the south for a while. Glad to see that ....." And I checked out. Well, I checked her out. She was .... really attractive. She had long blonde hair, long ass legs and a high cut bikini that was fashionable for girls my age, but looked even better on her. I could trace a line all the way from her knee up past the crease in her hip....

"Oh my god, I think he's getting an erection" snaps me back to my senses. Oh shit. My face instantly flushes red and I shuffle to hide my erection through my board shorts. Both women have a giggle at my expense. Oh.My.God.

"Your mom says your name is Avery? I'm Jennifer, and let me introduce my son John. In fact, John and I want to show you two something we found on the other side of the pool. Join us?"

On the way over John slides up beside me. We exchange very superficial hello's but I'm still reeling from the embarrassment. "Hey man, it's ok." He says. "A lot of guys have that reaction to my mom, and to be fair, I couldn't help but glance at yours.... She's a MILF for sure!"

Come to find out they led us to... a ropes course? There was a super intricate system of pulleys, ropes, and straps. I assumed it was some sort team building exercise until I realized that the straps were made to go around a thigh, or an arm, or a waist. "Victoria let me show you how, are you game?" Asked Jennifer. "Sure!" She was almost too quick to respond. "Uh.... but...." Mom moved in close to Jennifer's ear to ask a hushed question. After a moment of conversation Jennifer asked "John sweetie? Remember our conversation we had? Do you think that Victoria could help with.... that issue we talked about?"

I glanced at my new friend, not knowing that he somehow knew what was going on, but I didn't. "Yeah, that'd be cool." He responded. After that mom slipped two thumbs into her bikini bottoms and shoved them to the ground walking to the edge of the ropes. Her naked legs brushing past John on the way with a coy look. "MAAAAHHMMMM what're you doing?" I hissed. Jennifer was quick to grab me. "Hey Avery, I will need your help too on this." She redirected my attention to one of the first harnesses. She slipped one end around mom's neck and gave me the rope that pulled the strap up. She then quickly hooked the rest in place, and before 2 minutes was up, mom was suspended in air, face down and forward, with her pussy exposed on the back end, with John there, staring, his boner getting bigger with every minute.

"Sweetie? " Mom said. "I need something to suck on while I'm here." And somehow my dick sprung to life. I dropped my swim shorts and moved the head of my thickening cock to her lips. Just like we'd done before in my house before all this started. "Good boy" Mom said before taking my dick as far into her throat as she could. Jennifer came up behind me, pressing her breasts into my back and moving her lips just to the rim of my ear. "Do you like that?" She asked. "Do you like seeing mommy sucking on your big dick? I can't wait to get that inside of me as well." Her promptings ran a shiver down my back that only engorged me even more. "Remember sweetie, mommy doesn't always like a good boy." Her hand moved on top of mine which reminded me that I held a rope in my hand. She helped me give a slight tug on the collar, which pulled mom's neck up causing her to choke and gag on my dick. "Oh fuck yes!" mom said.

A small group of young men and mothers congregated at a distance. The look on the boys faces shifted from mine to John's, while the young mothers looked on with jealousy. The glances reminded me that I wasn't the only player in this game. I glanced over to find John with his dick in hand walking up to mom's back end. "Present yourself Victoria" Jennifer pressed. Mom arched her back and groaned even louder as John slapped his dick on mom's pussy mound. I'd seen that in a couple porno's but I never knew what it was for.

Jennifer pulled over a bench from the exercise area and placed it beneath Victoria. She could lie flat on her back on the bench and Victoria was still suspended about a foot above her. She wiggled her way towards Jonathan and quickly shoved his dick in her mouth. Her spit allowed Jonathan to penetrate my mom easier. Mom let out a gagged moan into my dick when he first pushed inside her. After lubing up her son, Jennifer started to lick mom's pussy while her son was penetrating her.

Mom stopped for just a second when I pulled out for a brief minute, and she pointed with her eyes to Jennifer's groin. "Common, son. Do it. It'll feel amazing, trust me." I reached down and pulled the exercise bench toward me with Jennifer on top of it still. She let out a shocked giggle and then looked down at me encouraging. I gave her a questioning look while I glanced down to her pussy which had a wet spot on the outside of the cloth, my dick just inches away. "Yes please!" she begged. I ripped off her bikini bottoms as quickly as I could.

I positioned the tip of my dick right at her opening and slowly pushed my way into her. Her eyes rolled back in her head and and she let out a quick "Yes Avery". The wave of sensation spread through me much quicker than I anticipated. I pumped and pumped and pumped as my balls slapped into her. I realized that I had to pull out once to make sure that I didn't finish within the first minute. As soon as I got back into her I used both hands to grab around her waist and with every ounce of effort I had I pulled that MILF into my dick as hard as I could. The sensation pulled me quickly to climax but I got nervous right as I was about to finish inside her. I pulled out quickly and Jennifer only needed a second to see what was happening. She spun around on the bench and asked me to put in on her face. My cum exploded out of me and she lapped up every bit that she could.

As I was coming down I realized that I probably only lasted about 4 minutes. Shame circled in on me, and I could see a couple of the other boys laughing and the mothers looked.... disappointed.

"It's ok sweetie," Jennifer said. "That's what John and I are here to work on. "Luckily we have all week!"