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Staying With Stepmom

Staying With Stepmom

by sftopbottom
19 min read
4.38 (45300 views)
adultfiction
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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."

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"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.

I slowly slid from underneath her. Putting a couch pillow under her head. The blanket on the back of the couch would keep her warm tonight. I turned off the music and the lights, and headed upstairs.

I was drunk and tired, too tired to even jack off, despite my leaking cock. I crawled under the covers and quickly fell asleep. When I awakened in the morning, a leg was wrapped around me and a body pressed against my back.

Oh no! I feared the worst, then realized I was still in my underwear. Mom had on her robe, mostly. I groaned and made to get out of bed. Mom groaned too, and hugged me tight with her entire body. Jesus, she is not making this easy, I thought.

She slowly awakened and I heard, "Oh!' as Mom untangled her arms and legs. "Hmmm. I must have crawled into bed with you last night somehow."

"Good morning, Mom. I left you on the couch last night with a blanket. Next thing I know, I woke up with you coiled around me," I said as I made my way to the bathroom.

"You should feel lucky. I don't just crawl into any man's bed, you know," I heard through the bathroom door. After I pissed, my dick got hard and just would not go down. Now? I eventually grabbed a towel, wrapped it around myself, and left the bathroom.

Mom was asleep in my bed. At least that spared me the embarrassment of her seeing my hardon! She heard me rustling around, saw me with the towel, and murmured, "Remember to leave the door open, baby," She added. "For the steam."

Baby? Since when? She had turned back over and slept. I figured, a shower won't hurt, and maybe I should pound one out to relieve some of my tension.

I showered and although my dick was hard as hell, I was too worried about the open bathroom door. Would she see me? What if she walked in? I didn't want to be creepy and have her hate me. I definitely should not have worried about that.

I turned off the water, stepped onto the shower rug, and grabbed my towel. I dried my head, then my back. "You still want to go underwear shopping today, baby?" She was on my bed, belly down, elbows bent, her chin propped up by her hands, just looking at me and my swollen swinging dick.

"Woah! Mom!" I quickly covered myself and turned away.

"Nice buns, honey!" She laughed. "Geez, baby. Lighten up!"

I wrapped the towel around my lower half, and walked into the bedroom. Mom had turned onto her back and was gently giggling and kicking the mattress. Her robe had parted a little and her panties were fully in view. She was killing me.

I rummaged for some clothes, half looking at Mom as her finger circled her navel. "I'll get cleaned up and make us some breakfast. How's that sound, baby?" Said Mom, as she rolled over and sat up. I at least had my underwear on before she wolf-whistled and laughed hysterically.

"Military issue indeed," I heard as she laughingly walked past me and into the bathroom. I heard her raise the toilet lid, then I heard Mom's pee splashing loudly into the toilet.

"Uh, Mom, hot as you are, I don't think you're generating so much steam that you need to leave the door open when you pee!"

"Oh, Michael! You're right, baby. I'm just usually all alone in this big old house. I'll have to remember there's a man lurking about. And thank you for saying I'm hot."

"For the record, I was not lurking. You just have no modesty." I added, "Not that there's anything wrong with that. And I meant it. You are seriously hot."

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I added, "Now, just get ready so we can go see my new apartment. Then I can get out of your hair and you can dance naked to rockabilly, with your belly full of wine, all you want."

"My dear, you can get up in my hair as much as you want," she yelled from the toilet. I heard a flush and she walked into her room without her robe. "And I already told you I'll dance naked in my own home whenever I damn well please, sexy Stepson in the house or not," I heard as her door closed.

We ate breakfast and went to look at the apartment. It was nice, a bit basic, but super cheap and in a great neighborhood. I hugged my Mom, "Oh, Mom! I can't believe how good you are to me," I still held her. "How can I repay you? I know! Let me cook dinner for you tonight."

"Settle down. This is nothing," said Mom. "My top floor tenant will move out in a couple of months, then you can have the best unit in the building. It has a great view."

Mom added, "This is the old superintendent's place and I'll renovate it once you move upstairs. It'll do for the moment, unless you want to stay with me for a little while longer, despite all of my entangling hair." She giggled.

"No, Mom. I've been living with other people all of my life. I feel like I need to get my own place. I love you, but, boundaries, you know?"

"I do, totally. Now, let's go buy you some new underwear," She laughed and I rolled my eyes.

She handed me the keys after she locked the front door. "It's all yours, baby!" She kissed me on the cheek and we headed off to go shopping.

"You want me to try them on?" I asked. "I usually just grab a pack from the shelf and call it a day."

"Yep, and those Army-issue skivvies are doing absolutely nothing for those tight buns," said Mom. "How do you expect to get laid wearing those things?" The sales woman in the men's store giggled. I was mortified.

"Oh, right, I can hear it now. I'll ask women if they like my underwear, and say that my Mom bought them for me. Then I'll hear the door slamming as they run from my new apartment."

The shop lady said, "You'd be surprised to know just how many moms bring their sons here to shop for intimate apparel." She handed me three pairs of underwear on fancy hangers. "Trust your mother, young man. Who else knows what looks the best on you other than your own mom?"

I grabbed the garments and turned toward the dressing area. There were two steps with three mirrors at the top. I climbed up onto what was basically a tiny stage, opened the curtain to the left, and stepped inside.

I put on the first pair. I had to admit that they looked great. I needed to see them in the mirror, so I cautiously stepped through the curtain and out in front of the mirrors. I could see my backside easily. The running has been paying off, I thought. My ass looked beefy and solid in the tight red bikini.

"The first whistle and I'm out!" I said.

"Don't worry. This is a safe space, boy," said the shopkeeper.

Mom said, "The front of those look great. Turn around, baby." I slowly spun. "Take off your shirt, so I can see how they fit at the waist." I complied.

"I'm more of a boxer-briefs kind of guy, Mom." I turned around. "These are kind of restrictive." The shopkeeper brought me three more pairs.

"Try these," she said. "They are designed for those with more generous packages."

Mom was having way too much fun at my expense, covering her mouth as she swallowed her laughter.

"Alright, I'll try on one of these and that's it." I went behind the curtain and peeled the briefs from my groin. They were sticky from my penis. Damnit. I guess we'll be buying those, I thought.

I pulled on the silver underwear. They felt good...great actually. My dick had swollen a bit and my balls were full and tender. The material expanded easily to support my goods and it felt like I wore nothing. They were more brief than boxers, and they hugged my buns in a way other pairs didn't. I stepped out to look in the mirror.

"Yes, baby. Those are the ones," said my mom.

"I agree with your mother. How do they feel?" said the shopkeeper.

"They're very comfortable," my dick was getting a little hard. "It's like wearing nothing at all." I had my back to the ladies. The shopkeeper came and adjusted the crooked band around my waist. I became fully hard.

My dick arched across my thigh, trapped by the briefs. I leaked. Over the shoulder of my reflection, my Mom and the sales lady stared at my rapidly swelling hardon and the growing dark spot where my head pulsed to its own beat.

Betrayed by my wayward dick, I turned quickly and dashed behind the curtain. "Just wear them home, son." I heard Diane say.

She bought several colors including the ones I had tried on (she was planning to buy everything I had worn, as a store policy). Mom shoved the tiny red pair into her purse. The rest went into a pretty bag.

As I drove us home she asked me to go with her to the lingerie store. I said firmly, "No, Mom. Come on!" She was laughing so hard.

"Too damn easy, baby," said Mom. She was being cool about it, and I loved to see her laugh. It was impossible to be mad at her in any way.

"Thank you for the underwear, Mom."

"You're welcome, baby. How do they feel now?"

"Really good, Mom. They don't bunch up when I sit. They're great."

She was going through the other pairs she had bought, holding up each one. She pulled the bikini briefs from her purse and held them in front of her face. The crotch was clearly stained where my dick had oozed onto the lining. I watched her feel the area with her thumb. "This pair looked great, but if they dodn't cradle your package just right, fuck that." She rolled down the window, stuck the bikini out with two fingers, and let the freeway wind take them away. Holy shit!

"Hey, Michael?" mom said a few minutes later. "What happened to those Army issue underwear you had on when we went to the store?"

"I tossed those grandpa panties into the trash! Why? Did you want to throw those out the window too?"

"Kind of," she said. We both laughed as I pulled onto her street.

That night after I made a delicious dinner Mom suggested a movie. We snuggled on the long sectional couch. I had a big fluffy pillow in my lap, which she sat against and laid back with her head on my chest. She wore her tiny satin nightgown again.

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