I had just spent three years in Germany, exited the Army, and was back home in Portland, Oregon. My Dad's ex-wife, Diane, was in the Portland real estate business and I thought she could help me find just the right rental in my price range.
Diane had been in my life for about ten years. She dumped Dad when I was fourteen. We kept in touch and sent Christmas cards and stuff. Occasionally we went to lunch, usually when I needed advice about girls.
Growing up, she was like a second mom that I could talk to about anything and everything. In fact, I called her Mom most of the time. She was that involved in my life.
Diane was also a rare beauty, with the kind of personality that just lit up a room. She almost won Miss Oregon once, and modeled while finishing her business degree and going into real estate. Mom built a huge brokerage firm and had dozens of agents working for her.
When I got to Portland I called Mom right away. It turned out that she owned a few rental properties too and most definitely could help me. She even offered to let me stay at her place, where she had plenty of spare beds.
Mom's new place was up in the West Hills of Portland. The house was huge for a single woman, but she said the view and peace and quiet were worth it. She had gotten a great deal on the property, too. It looked like a mansion to me.
I asked her if she ever got lonely. She said she had rented a room to "the occasional boy" until she either grew tired of them, or caught another one of them stealing her panties. What?
"Mostly, I just like my solitude," she said. "I can run around naked, drink wine, and listen to loud rock anytime I want, and nobody is going to say a thing."
"Is this where we maybe talk about some house rules while I'm staying here?" I said lightheartedly, my laughter probably not hiding my blushing cheeks.
"Oh don't worry. I won't do anything to scar your tender soul," she said. "I'll bet you're not too easily shocked now though, are you, mister man of the world?"
"I uh, sure. I am almost twenty one, after all...practically an old man." I rolled my eyes.
Mom said, "Okay, old man, I'll make you a deal. I'll keep my clothes on and you keep your clothes off the floor."
"Deal," I said. "Which room is mine, M'lady?"
As I followed Mom upstairs, she told me all about a furnished apartment she had right downtown that she could make me a deal on. She was very excited about showing it to me the next morning.
Mom's smile was infectious. "I'm so happy to see you!" She hung from my arm, leaning into me as we walked. "Here we are!"
She showed me into the room, which had a large bathroom that joined to another bedroom. "This other room is mine. I have a pool table in the main bedroom, and this room has a nice balcony, so it just made sense to wake up here every day."
"Cool," I said. "Why don't I get settled and we'll grab lunch?"
We had a great lunch and I filled her in on all of my non-adventures in Germany. I was stationed there during peacetime and it was relatively calm. Mom leaned forward and listened to me raptly, like I was some great explorer. "You're so young and you've already done so much," She exclaimed. "I stayed in the same city my whole life."
She added, "Your Dad wouldn't settle down, and I didn't want to follow him everywhere, so we split up." She went on, "I married an older man thinking he would mellow out, but oh no, not your Dad...perpetual wanderlust."
"I'm sorry that it didn't work out for you guys," I said. "I bet he's kicking himself in the ass now though. Just look at you!" It was her turn to blush.
I said, "You are one of the top brokers in the area, have a killer house, and look like a million bucks. You light up every room you walk into, Mom, and everyone wants to work with you. You are at the top of your game. You just seem to have everything."
"Flattery will get you everywhere," said Mom. "Yes, my life is pretty great, I have to admit. But I work hard and set big goals. You can thank my trainer and my health spa for the rest of it."
"Well, I hope you tip your trainer very well, because he seriously knows what he's doing. How can you look better now than you did when I was a teenager?"
"Well, I make my body a priority. Wait, what? You didn't think I was attractive when you were a teenager?"
"Hey, M-O-M. Awkward much?" I said. "Of course I thought you were attractive. So did every other teenage boy, and girl, in my school. They all called you Miss America, and they said it with admiration. It was kind of annoying, to be honest." I laughed, rolling my eyes. "Seriously, though, you were a total babe in my young eyes. Still are, Mrs. Robinson."
After the awkward silence, I said. "My Dad's a dumbass sometimes. I couldn't believe it when I heard you were divorcing. If you were my wife you could have welded a ball and chain around my ankle and kept me in the basement. I'd still be here years later, right at your feet whenever you wanted me."
"Wow. Um, that certainly paints a mental picture for me," said Mom. "I had no idea you were into being tied down, Michael." Mom poked me in the ribs. "It's so easy to get a rise out of you." Yep, guilty.
We chatted and laughed well into the evening, devoured a pizza, and shared a couple of bottles of wine. She asked me about my love life. I asked about hers. "Well, I mentioned those boys who stay here for a spell. They can be quite a handful."
"Seriously?" I poured more wine. "Just how old were these youngsters, Maam?"
"Exactly your age, actually," said Mom, over her wine glass as we sat facing each other on the couch. Talk about a pregnant pause.
"Oh, God, Mom. Please tell me I don't know any of the guys!"
"No, I don't think so, but it's kind of hard to keep track," she said seriously and started to count her fingers.
My eyes must have been bugging out of my head. She laughed so hard, spilling wine all over her shirt. "Oh, crap!" she screamed and jumped up. "It's time to change into some night clothes, anyway. I'm just going to rinse off real quick," She darted up the stairs.
I decided it was time to ditch the jeans as well and went up to my room. I dropped my pants, and just as I was about to take my leg out of the jeans, the bathroom door opened into my room.
Surprised and compromised, I turned, stumbled, and fell onto my ass. Mom laughed and said, "Careful there, um, Big Fella." Jesus, I was ankles up, on the floor, with my feet stuck in my pants!
"Nice brown undies, buddy.!" She was hysterical now. Her bathrobe almost came undone, and from where I lay briefly, I swear I saw a flash of pubic hair.
I pulled off the pants and stood, covering my privates. "Thanks, Mom. Military issue skivvies."
"Okay, shy-boy. Settle down, I'm not here to perv." She had finally stopped laughing. "Two things: One; keep this door open when you shower, so the steam doesn't build up too much. And, two; let's take you underwear shopping tomorrow. For fucks sake." And she turned into the bathroom laughing.
With her back to me, Mom started the shower, disrobed, and stepped out of view. Was she fucking with my head? My dick didn't care. I was hard. I wanted to stand right there until she got out of the shower. I wanted to walk in there and join her. Instead, I dressed in my loose cotton shorts and a tank top, and went downstairs.
I opened another bottle of wine and poured two fresh glasses. Turning on the stereo, I found some mellow jazz and pulled out a joint from Mom's not so secret stash.
"Do I smell what I think I do?" I heard from upstairs. "Don't bogart that joint, young man. I'll be right down." And she was, running past me in a flurry and leaping onto the couch. "Gimme!" she said, holding out her hand.
We smoked and drank our wine. She sat cross legged from me in a short satin robe, legs tucked underneath her body. It seemed like she was trying to be demure and modest the way she tugged at her robe to stay covered. I thought, why wear such a short robe in the first place?
"Sorry about the nighty, Michael," she finally said. "I'm not used to having someone here at night and I don't really have anything less revealing."
Wasn't she wearing a fluffy bathrobe upstairs? "Oh, as I said, it's your house. I need you to be comfortable in your own skin Mom. Stop worrying about it, seriously."
"Okay, Michael, as you wish." She jumped to her feet, "Wanna dance with your old Mom?" She held out her hands, her breasts jiggling, nipples tenting her thin robe.
I stood and we swayed together. "Have we ever danced?" she said.
"No, I'm quite sure I'd remember holding you in my arms like this," I said.
"Damn right you'd remember," Mom giggled and moved in, holding me closer as we enjoyed the rhythm.
I had been holding my hips away from her a bit, but her hug made that impossible. Shit, I thought, Dead puppies. Dead puppies. Dead puppies. It didn't work.
Miss America, a drunk Miss America, had her nearly naked body pressed against me with her head on my shoulder...and she was my mom.
Diane's breath tickled my neck. Her pelvis found a hard penis that was pointing down, achingly trying to break through my shorts and stand upright. She bent her leg and rubbed her crotch against my shaft. I think we stopped dancing at that point.
Mom seemed to get lost in her world, humming and grinding on me oh so gently. Is this just how she dances, I thought? My dick didn't care, and my brain was spinning.
"Okay. I think I've had too much wine, Mom," I said as I peeled myself away from her squirming body. Where I found the willpower I'll never know.
Mom was suddenly all pouty and clearly very drunk. What was I going to do, have sex with my stepmom while she was out of her mind? Fun as it might have been, I wasn't THAT drunk. "Let's sit on the couch, Mom."
She snuggled up against me and stroked her head. It wasn't long before she was snoring gently, her head in my lap. I looked down at her tangled nest of damp blonde hair, wondering what my dad had been thinking to cast her aside.
My dick enjoyed the warm shower-moist head snoring vibrations. Oh, man, what a delicious thrill. I had a devil on one shoulder and an angel on the other. The angel won.
