Day Five

We didn’t watch another video. I think I fell asleep the instant my head hit the pillow. I woke up a few times when Kaylee smacked me in the face. I wasn’t sure if the aches and pains in the morning were from overusing my muscles or Kaylee thrashing around at night. Either way, I needed a break.

After breakfast, I informed everyone that I needed a day to rest and recover. I needed it, and I wanted Kaylee and her dad to be free of me for a day. I was holding them back at this point and I hated that they were lowering themselves to my level. Kaylee tried to talk me into letting her hang out with me for the day, but I wouldn’t have it. So after her and her dad headed out for the slopes, I went down to the lounge of the hotel we were at and claimed one of their plush couches for myself. With a giant fireplace crackling and heating me, I got comfortable and tried to catch up on things.

Paige and my parents had texted me a few times asking how my trip was going, so I finally got around to responding. The parents responded as one would expect, telling me to have fun. Paige immediately responded with, “You bang her yet?” I didn’t respond to that.

I sent a few texts to Liam to see how he was doing, figuring his test was coming up soon. That was when he broke the news that he was running a slight fever and felt like shit. The worst part, when he told the doctors, they canceled his test over fears that this was virus related. We didn’t talk long since he didn’t want to ruin my vacation with his problems. I didn’t mind, but he was insistent that we would have plenty of things to talk about once I got back.

About that time, the staff brought out a big thing of hot chocolate. Sipping my free hot chocolate, I curled up with my tablet and tried to catch up on some reading. Tried being the operative word. It didn’t take long for the harassment to begin. First, I thought it was people being friendly. Some of the girls who were in the lounge with me eventually came over to strike up a conversation. It was a bit weird at first until their intentions started to come out when they invited me up to their rooms. I turned them down as politely as I could. I wasn’t sure if it was because I was attractive, or that I looked available, but the range of women who came up to me in the three or so hours was astounding. I had women twice my age hit on me, girls about my age, and everywhere between. Some were subtle in their approach, others were straight to the point. The vast majority was interested in one-on-one, but a few couples asked if I was interested in threesomes. The worst was a group of college students. The five girls had me surrounded and didn’t seem to want to take no for an answer. They offered all sorts of promises. I could take them one at a time, or all together. Whatever number I was comfortable with was fine, just so long as I got to all of them.

I escaped by purposefully spilling the rest of my hot chocolate—which was now lukewarm chocolate—on my pants and rushing off to the restroom. I immediately got on the elevator and headed back to the room. Using the key Kaylee and me shared, I went inside to change my pants. The door clicked closed behind me. The moment I reached my suitcase, I realized that I wasn’t alone in the room. Mrs. Webb was in the bedroom section atop a man who was not Mr. Webb. I was too stunned to move, my eyes automatically taking in everything I was seeing. Her ample breasts were a touch heavy, but not to the extent they should be for a woman her age. My eyes seemed to follow them as they bounced and jiggled from the **** of her movements. Her blond hair was up in a sloppy bun. It gave her head a crown effect, and she certainly looked like a queen. She was the picture of a woman in absolute control. Mrs. Webb was enjoying herself, but she didn’t let her pleasure overwhelm her. It was a stunning sight to behold. A queen out for a ride atop her young and strong stallion.

Our eyes met, and I saw a brief moment of surprise. “Scott! I didn’t hear you come in.”

“S-s-sorry,” I managed to spit out, scrambling away from my open suitcase. “I’ll come back—”

“Nonsense,” she said, taking everything in stride. Not once did she break pace, continuing to ride the man. Only instead of focusing on a point in front of her, she was looking at me while she did it. “This is actually a good time. I’ve been wanting to speak with you. Just give me a moment to finish up here…” She did… something... because the guy was suddenly crying and sputtering as he came. I was shocked to see the guys reaction. It looked like he was having the greatest orgasm in the world. He practically collapsed on the bed under her.

With seductive grace, she lifted herself off the man and I watched the cum trail from her. “You can leave now,” she told the exhausted man. “Hurry up then.”

It took the guy a lot of effort to roll off the bed. He managed to dress quickly before stumbling for the door. As he passed me with an embarrassed smile, I noticed he was staff here at the hotel. The scary part was he didn’t look much older than I was.

“Just what I needed to start the afternoon,” she said, stretching. She was still naked, facing me. Not only did I look, but my gaze was also transfixed on the cum that slowly rolled down her inner leg. “Scott.” Her amused tone shook me out of my daze. My eyes quickly shot up to meet hers. She took a few steps toward me. One foot in front of the other in the most seductive way I’d ever seen. “The way you're looking at me is hardly appropriate for being my daughter’s boyfriend.”

My eyes were instantly to the floor. My words twisted and sputtered out as I tried to apologize.

Her light laugh filled the room. “I understand why my daughter likes you. You are so fun to tease.”

She walked away and I breathed a sigh of relief as she grabbed a robe and threw it on. “I’m going to clean up a bit. Perhaps you want to take care of that—” She looked straight at my erection and I quickly covered myself. “—before it stains.”

My face reddened as I realized she had been talking about the hot chocolate I’d spilled on myself to escape the girls. Or had she? The way she smiled made me doubt both.

As she disappeared into the bathroom, I quickly changed into a fresh pair of pants. Using the sink in the kitchen area, I did my best to rinse and scrub the spot. When I was finished, Mrs. Webb was waiting for me. Thankfully, she had put on actual clothes, even if it was just a hoodie and sweats. She settled comfortably onto the couch, gesturing for me to take a seat on the chair.

“Have you eaten?” she asked as she held up the room service menu. I shook my head. “What do you want? I find myself craving something spicy after a good workout.” She considered that a workout? I wonder if Mr. Webb knew. That was a stupid question. Of course he did. I ended up ordering a burger. After she set down the phone, she gave me a teasing smile that instantly reminded me of Kaylee. “Calm down, Scott. I’m not going to jump you. Unless that’s what you want.” I think my blood pressure instantly spiked at the wink she gave me. Again, she laughed lightly, holding the back of her hand over her mouth. “Oh, Scott. The look on your face. Relax. While I normally have no qualms poaching Kaylee’s conquests for myself from time to time, I can tell the way she feels for you is different. I would never do that to her.” My jaw dropped. She had casually admitted to sleeping with the same guys Kaylee did. Did Kaylee know that? Her randomly forcing me to promise to never sleep with her mom made a lot more sense now.

I had run from the hyenas downstairs only to escape into the lair of the lioness.

“By the look on your face, I see she hadn’t told you that little fact yet. No matter. It’s no secret that I enjoy younger men and Kaylee has excellent tastes. Rest assured, I never sleep with anyone she currently is with—no matter how fun that might be.” At my terrified look, she smiled. “A joke.”

What was the joke? Nothing she said was a joking matter. Besides, what was the joke? That she didn’t sleep with guys Kaylee was with, or the bit about it being fun.

Her expression shifted and I could tell the fun and games were over. Reaching over to the table, she grabbed a bottle of water and opened it. She drank a quarter of it before focusing on me. “While it’s a bit embarrassing to admit, I find I don’t know too much about you, Scott. I know you’ve been friends with my daughter since the start of high school, but we haven’t had much interaction until recently.” Oh shit. Was this a, ‘Are you worthy of dating my daughter?’ conversation? I was not ready for that. Especially not with her. She seemed to pick up on my panic—because of course she did—and smiled. “Relax, Scott. This is just a friendly conversation. My husband speaks highly of you, and he is an excellent judge of character. If he believes you can make my precious little girl happy, I believe it.” Her lips pressed against the water bottle again. “Of course, I always live my life by the phrase, ‘Trust, but verify.’”

Shit. This was a, ‘Are you worthy of dating my daughter?’ conversation.

She finished drinking more of the water. “What are your plans after high school, Scott?”

“I… uh… Haven’t thought much… on that…” The way the woman’s eyebrow twitched upward slightly wasn’t a good sign. First question and engines two and four were already on fire and the tail section of the plane was gone.

With deliberate movements, Mrs. Webb set the water bottle on the table. “I’m sure you realize that Kaylee is going to college.” I nodded as she continued. “Beyond whatever she does for herself, she will have access to somewhat significant assets I have set aside for her. Enough to ensure her family can live in relative comfort until she is able to properly support them herself. What she does with such money is her business of course, but I can’t help but fear some may try to take advantage of her rather…gentle…nature.”

It sounded like she was suggesting I was dating Kaylee for her money. I suppose that would be a concern for some, but she had to know be better than that. Right?

“I can assure you, Mrs. Webb—”

“Lisa.”

“I—”

“If you are serious about my daughter, you will start calling me by my name.”

I shifted nervously. “Okay… Lisa.”

She smiled. “Good.” Even in a baggy hoodie and sweats, there was an impossibly alluring way she relaxed against the couch. “I am curious. How far are you intending to take this with Kaylee?”

I twisted my fingers anxiously in my lap. Cold sweat was already forming beads on my forehead. The pressure was overwhelming. “As far as she wants.”

“Excellent answer. It’s nice to have goals, but one must be realistic when it comes to the future. I expect college to be an eye-opening experience for my daughter, as it was me.” I wondered what she meant by that. It was certainly ominous. She gave me a studying look. “Have you had many lovers, Scott?”

“A-A few,” I sputtered out.

She sighed. “Has she asked you to refrain from taking other women as lovers?”

“N-no.” Why couldn’t I speak normally around her? Her presence alone was causing a mess of me without the conversation topic.

“Good. While you are in this dating period, I suggest you get as much experience as you can. Kaylee has a lot of her father in her, but she is still my daughter and she has needs. Trust me, Scott. You will need to run to ensure your place by her side. If you fall behind, she will leave you behind.”

I didn’t believe that. There was no way Kaylee would do that… right? The little voice that lived in the back of my head wondered how many other guys thought that before they got too clingy for her. Even if we were dating, I shouldn’t be relying on our status to grow complacent.

“Are you comfortable with sleeping with older women?” Warning bells went off as I stared at her. This wasn’t the teasing fun she’d had earlier.

“Never… thought about it before.”

“Perhaps you should. Toby and I host swinger parties with a few close friends every month or so. Now that you are in a relationship with Kaylee, you might consider joining us every so often. It’s a great way to pick up on some things you’d never have thought of before. Of course, I will be off-limits, but several other women are excellent in bed who would be more than willing to teach you.”

I sputtered out something that I hoped sounded like, ‘I’ll think about it.’ She had actually invited me to a swinger party… She did know that Kaylee would be there too? Was this normal? I couldn’t base it off my family for obvious reasons. They were as abnormal as I was.

She was about to ask me another question when there was a knock at the door. Saved by room service.

Getting off the couch, the way her hips swayed as she walked to the door…

I needed to get a grip. Mrs. Webb—Lisa—was dangerous to be alone with.

The man came in and set the food on the table for us. My burger looked delicious. Now I had something I could use to buy time during her questioning.

“Anything else I can do for you at the moment?”

Lisa looked him up and down. I knew that look. It was the same way the women in the lounge looked at me. “Actually, yes. I find need to work up an appetite.” The man’s gaze instantly turned to me. “Oh, don’t worry about him. He’s my daughter’s boyfriend and won’t be joining us.”

He didn’t resist as she pulled him towards the bedroom. I mean, in his position I probably wouldn’t resist either. Her hoodie was off before she reached the doorway separating the two rooms. There was nothing on underneath.

“Enjoy your food, Scott.” She gave me a wide smile before pulling the willing man into the room after her. She didn’t close the door. The implications were clear to me. This meal came with a show.

It took everything I could not to watch. The moment my food was gone, I bolted, leaving her to enjoy her second afternoon snack.

The lounge was safer than a siren’s lair.