The MILF Resort and the Pool Ropes Pt. 02: Training

Day one at the resort was... well... interesting. But it really wasn't until day 2 that I understood what was really going on. After Mom, Jennifer, John and I finished up our little poolside session, we spent most of the night talking and drinking with them. I knew that mom liked to drink, but she really let go here. It was strange. On our way back up to our rooms for the night Jennifer pulled me aside and asked if I wanted to join her for a shot at "redemption". While I wasn't exactly sure what she meant, I think I got the drift. I politely declined as I really was tired, and quite drunk at the time. I really just wanted to sleep off the day. As we split she said "That's ok, I'll get what I need tomorrow anyways. G'night hun."

That line really stuck with me. I don't know that I've ever felt like I was being prayed on before. But I certainly felt like I was now. This woman was a sexual predator, and I felt like I was walking home alone at night. At the same time, she was gorgeous! I'd be lying if I said I didn't jerk off that night to her. I could still feel her warmth as I pushed into her as hard as I could, and feeling the peak of climax while looking down at her sexy slim body with obviously enhanced breasts. It was a strange feeling to be afraid and scared at the same time.

After two orgasms that day, and a number of drinks, I slept really well. Mom eventually got me up at about 9:30 and insisted that I hurry or we'd miss the workshops. After a quick shower and continental breakfast I found myself entering the hotel ballroom to see a screen with the words "Overcoming your sexual dysfunction!" written on a powerpoint.

"Mom what the fuck!" I yelled at her as I pulled her back into the hallway. "Is this what this is really about? You think that I have a sexual dysfunction?!"

"Ssshhhhh sweetie no. Listen, after our episode at home I realized that you maybe need a little help with... stamina." And then after a scolding look she added, "And I was talking with some women on a messaging board who mentioned that this is a great place for women who are interested in younger men. This seemed like it was a good fit for us... Please honey, no. Don't walk away. Your father and I have made your life very easy. I know he and I aren't getting along, but you've got a car at home in the driveway, your college is already paid for, and you're set. Just do this one little week for me, and then you can go off to college this fall and live your own life. Plus, once you get into college these things could really help you."

I knew she was right. And yes, I've been... taken care of. Not spoiled, but very well taken care of. "Fine" I said with a tone of finality. It was a one word agreement.

After a brief introduction and a couple of breakout sessions, mom pressed me to attend one certain afternoon session. "This one's a game, sweetie. You like games, right?" The speaker introduced a game that would be played in "diads", which I had to ask, it meant groups of two. She motioned to a group of high walled cubicles. Each diad would step into a "workspace". Upon entering, the female of the diad would be tasked with seducing the male. If the female successfully seduces him and brings him to ejaculation, the female was to ring a bell placed in each workspace, after which, judges would come to verify the emission. Simply put, there were prizes for women who "rang" first, and for the boys who resisted the longest. The explanation seemed both scientifically dull and erotic at the same time.

As we moved into pairs I saw her approaching. Jennifer. She and John walked up to mom and I and declared us as "diads". On the way to the workspace I realized that Jennifer looked very different than yesterday. Yesterday it was all swimsuit and sun hat... but today... Today she was dressed in professional attire. She wore a crisp white button down shirt with an oversized and deep cut collar. She had on a pencil skirt that perfectly hugged all the right places, and might have even bunched just below the curve of her ass. She had tall black heels with red bottoms that I could only see as she walked in front of me. The bottoms of her heels matched some bright red lipstick that curled her lips to a point. I worried that even as we were walking to a workspace that I was already losing.

The moment we got into our cubicle she turned quickly on her black heels and pulled me close. She leaned in to my ear and whispered "I want you to fuck me just like you did yesterday." and even gave a slight gasping moan. I had to steel my nerve as I felt my body give in to hers. She took one step back and started unbuttoning her top. "Won't you please help me with these?" and she moved my hands to her buttons to take each one down, revealing a black lacy bra that framed her breasts perfectly. She peeled off her shirt and pressed her body close to mine, pushing her tits against me like she had the day before at the pool. Her hands ran down my sides and stopped at each of my hips, visually tenting my pants. "I know just what you'll like." She hiked up her shirt and moved the single chair to bend over the half table provided in the workspace. She showed me her full ass with just the thinnest of G-strings running down her crack. "Can I... Throw it back for you?" She asked. And then, to my complete surprise, she started twerking. Like... What the fuck?

It's not that she was bad at it, or that it wasn't sexy, but the way she spoke those words seemed so mechanical. She maybe saw too many tik toks before she came, and thought that would be a sure turn on. To be fair, this moment of humor was a welcome break. When she glanced back and saw a half smirk on my face, she instantly changed. There came a ravenous look on her face and she became ultra-competitive.

She darted over and nearly ripped my pants open. She pulled my boxers down enough to pull me out. Before I could protest she had my growing manhood in her mouth, and was raking her tongue along the veiny underside. "Wait, can't we just... Stop? Or talk?" I asked, even though I knew I wouldn't want to even if she offered. She paused and pulled me out if her mouth with a thick gag. "Yeah? Want me to?" She asked as she slowly stroked my cock with both hands. I knew I did. I knew I wanted to win a couple of those prizes. I knew I wanted to build stamina and that I should slow down. But then I looked down at this woman, on her knees with eyes looking up at me, pleading with me to continue. *Ding*

A bell rung out in the near distance indicating the first female winner and the first male loser. "Fuck it, I need you."

She stood up straight with a pleased look on her face and slipped one hand behind her back to unclasp her bra. It sprung off her chest and she rolled it down her wrists revealing her voluptuous breasts. She also quickly pulled her underwear off and skirt before sitting on the table, and slowly leaning back and opening her legs. Like a magnet my hips were drawn forward until I was an inch away from penetrating her. Jennifer arched her back and took both breasts in her hands toying with her nipples. She moaned a soft plea. I can do this, I can be under control. Go slow. Stop if it's too much.

I plunged myself into her and a sharp gasp escaped us both. I slowly undulated in and out of her while moving my hands along her thighs or abdomen. I felt myself engorging even more as her cunt voraciously lapped at me. She throbbed with the thrill of her younger man. I tilted my head back with pleasure, and tried focusing on the lights to keep myself grounded. My hips slowed a little, and Jennifer could tell I was starting to check out in my mind so she took decisive action. She pushed me back with her thighs and quickly stood. I heard a ding in the background. She grabbed my shoulders and removed what little clothes I had left. She shoved me onto the table and climbed on top of me. Her quick hands wasted no time in guiding my dick into her warm pussy. She started to ride me... and oh god. I tried to last as long as I could, but there was nothing else to focus on. There was a gorgeous blonde on top of me, her hips rolling back and forth, her eyes slid back into her head with every forceful thrust. Another ding. She grabbed my hands and slowly moved them to her bouncing breasts. She leaned into my arms and slid her hands past my elbows to feel the muscles while I kneaded her firm breasts. Her pace quickened, which worried me. Dings intermittently sounded around me. She rode faster and faster, and I couldn't distract any more. Every inch of blood seemed to course through my dick which stood at full mast to receive her. My breaths turned to gasps, which quickly turned to moans. I need to hold on. More bells sounded around me. I need to last. From seemingly another world a voice rose out of my chest, a moan that turned into a primal howl. I was no longer in control of my body, it was like my eyes turned red and all I could think of cumming inside this woman. My hips rose to match hers and we hit a perfect sync. Just as I felt I couldn't hold on any longer she started to be more vocal as well. "Yes yes yes yes, YES YES YES!!!" she cried as she rode me to her climax. My semen exploded out of me and into her. My sticky warmth filling her up and dripping out the side of her pussy as she continued to finish on top of me. At the last minute she arched her hips high to let me roll out and she started to squirt. Her sweet juice pulsed out of her and onto my veined member. She could barely reach up to the wall to hit the bell. *DING.*

She convulsed into a puddle of sensation on top of me. Our bodies pressed together and the sensation of skin and fluid slid between us. We breathlessly held each other as the judges opened the door and went about their inspection. She nuzzled deep into my neck and whispered "I'm so proud of you. I haven't been fucked that well in a LONG time." We talked and laughed for a few minutes, the judges leaving without me noticing.

I was perfectly enthralled with this woman. I was under her spell. Her scent was intoxicating and her voice a sirens.

As we walked back to join the others, a small crowd had gathered again. This time the looks and whispers were not about me finishing early. I ended up winning a prize, and Jennifer got the fucking of week that day. I could see it in the eyes of the other women. They now wanted me. They wanted what I had. And fuck me if I wasn't going to enjoy the rest of my week.