The summer after high school graduation my friend Greg invited me to spend a week with him down at the family's beach timeshare. I wasn't too crazy about the scene there, and my friend had a horndog approach to nightlife that could be exhausting for his wingman. But in daytime, it was unquestionably a chill scene: Lots of good food, Greg's cute sister, Jenna, in that blue-and-yellow bandeau bikini, and Dawn, Greg's amazing mother.
Dawn had just divorced Greg's father; the alcoholism and gambling had finally gone too far. From what I remember, Dawn got just about everything in the divorce settlement, and Greg's dad bolted, plainly humiliated by it all. It was a very sad and uncertain time for her, especially with a college bill coming for her son, but she reflected little of the crisis and seemed always to show up with pizza and a movie whenever I was over on a Friday night.
If ever there was a Cool Mom, it was Dawn, who knew how far to look the other way when Greg and I drank; who knew how to ask me about girls and who I liked in a way that made me confident; who climbed into the jacuzzi with us with an unquestionable elan, and who accused me of checking her out as she adjusted her swimsuit, in a way that flattered us both and absolutely skewered Greg.
Shamefully, I admit I spied on her when she took her shower before bed, and Greg was watching a movie or playing Doom. There was a full-length mirror in the bedroom on the far wall that reflected the in-suite master bathroom, and just a murky glimpse of her big-boobed figure through the fiberglass shower door was enough to tent my shorts. So when I said sure to Greg's plan to go to the beach, Dawn was reason No. 1. A week with her, doing anything, would be pleasurable.
Dawn was an R.N. and because of her shift schedule that week, Greg and I were told to drive down with his sister first and she would meet up with us the next day. That was pretty cool. It was our first road trip and it felt very adult to be driving ourselves to the beach instead of riding with a parent.
When we got there, we checked in at the gatehouse like we owned the place and headed to the house. After a quick visit to the grocery, Jenna made us all spaghetti and then he and I sat on the deck and smoked pot. The weed made us sleepy, and there wasn't anything else going on, so we decided to turn in.
In our stupor, we kind of fucked up the room arrangement. There was a room with two twin beds, that was supposed to be for me and Greg. Jenna instead decided to sleep there. The other bedroom had a queen-sized bed, and then the master bedroom had the king size.
Greg didn't want to sleep in the master bedroom as that's where his mom would be when she got down the next day. So I ended up there. Fine. Everybody showered and brushed their teeth and went to bed. I climbed into Dawn's bed, totally nude and aroused, trying to pass into sleep.
After about ninety minutes of tossing and turning my urges got the better of me and I humped one of the pillows, thinking hard about girls from school, pictures I'd seen in porn magazines, and finally, fuck it, Dawn. I tried to imagine what her pussy looked like, whether she had a big bush all around or if she trimmed it, with a patch up above and smooth, pink, cotton-candy pussy lips below.
The thought Dawn might be a sex kitten who shaves her pussy sent me over the edge, and I pumped a steamy load of pure teenage lust into the pillow, wiped my cockhead on it, then tossed it aside and collapsed, feeling like I might finally get to sleep now.
Almost immediately, I heard the front door open. What the fuck? Light from the kitchen ringed the frame of the master bedroom door. Now there were car keys on the counter and the sound of a rollaboard suitcase over the kitchen linoleum.
I got out of bed and fumbled around where I thought I tossed my gym trunks but found nothing. Shit, that's right, I dropped them back at the vanity — and just then the harsh overhead bedroom light flicked on, giving Dawn a full view of my naked pink ass. My hands shot for the sky like I was being stopped by the cops. I had a totally guilty look on my face because of the masturbation, despite the fact I had a perfect right to be where I was, even naked.
"Oh my God!" Dawn blurted. I turned and put my finger to my lips, not wanting Greg or Jenna to hear a word of this. In hindsight, I must have looked like the Coppertone girl covering her mouth in embarrassment as the doggie tugged at her bikini bottom.
"I'm sorry! I'm so sorry!" I whispered. "What the fuck is going on?" Dawn demanded, also whispering, as I tried to cover myself, but I looked at a full-length mirror on the bedroom wall and realized Dawn could see everything I had, the same way I spied on her in the shower back at the home.
"Please put on some fucking pants!" Dawn hissed.
I hurried around the room, cursing and forgetting where I'd tossed my shorts, balls, and dick bobbing as I scampered. Finally, I found my shorts in the foyer leading to the vanity and the master bathroom. I heaved a big sigh. Dawn wanted to know why I was in her bed, naked.
"We divided up the rooms, we didn't think you'd be down here til tomorrow!" I explained, still in a stage-whisper voice. Why would I sleep on the couch with a perfectly good bed here, I reasoned. Dawn said that when she got off work earlier that day she decided, the hell with it, that she'd make the late-night drive and sleep late into the next morning so she could be here with us all of the first weekend. This was in the early 1990s, before text messaging and mobile phones; Dawn said she called the beach house line but got no answer, and there was no voice mail or answering machine at the time there either.
We accepted each other's explanations, but Dawn seemed a little crestfallen by how, well, reasonable mine was, given the state in which she'd found me. She wanted to push it, actually.
"Didn't expect to get here and find a nude boy in my bedroom," she said. The way she said "nude boy" and "bedroom," like I was a plaything for her, put a jolt into my penis. I stood there for a long moment, completely off guard and unsure of what to do as my cock stirred my shorts leg. My gut said she was coming on to me but the situation was way too explosive to be wrong about that, especially after what just took place.
Dawn's tone changed, as if she had added it up and reconsidered. "I'm sorry but ..." Dawn said and I knew it was the couch for me.
I wasn't going to sleep with Greg and for sure I was not to be in Jenna's room. "OK," I said. I went back to the bed and grabbed my pillow. Dawn handed me a sheet from the linen closet and patted me on the shoulder. "We'll laugh about this," she said.
"No we fucking won't," I said. "Greg doesn't hear a word of this."
"He's fine," Dawn said. "He sleeps with a fan on, it'll be OK. He didn't hear anything."
In the den I collapsed on a sectional and listened to the crashing ocean in the distance, praying for the sea breeze on my hot face. Dawn's bedroom door closed with a soft click. The harsh overhead light coming underneath the door crack was replaced by the softer light of a bedside lamp. I heard Dawn going back and forth in the bedroom, brushing her teeth at the vanity sink, closing a closet door, and then two footfalls. I entertained the idea it was Dawn stepping out of her panties. Then there was a heavy sound as she got into bed and fluf…
Oh, fuck.
Oh, FUCK, the fucking PILLOW.
I heard Dawn gasp.
Oh FUCK, now I really was in trouble.
My mouth went dry. Dawn opened the door and I saw her standing there, in a sleep shirt, holding the pillow I'd cum all over in her left hand by her side. She walked over to me. "I think this is your pillow," she growled. She dropped it on my face and I felt the cold, clammy dampness of my cum on my cheek and crinkled my nose at its unmistakable musty aroma. She jerked the pillow I was sleeping on out from under my head and my arm, flailing for balance, went between her knees and hooked around her smooth, voluptuous thigh.