Fetish

Living with Step-Mother

Army veteran resumes living with his stepmother.

Spankmasters
May 10, 2024
15 min read
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Staying with Stepmom
Staying with Stepmom

Living with Step-Mother

I had recently returned to Portland, Oregon after spending three years in Germany and leaving the military. My stepmom, Diane, worked in the real estate industry and I thought she could assist me in finding a suitable rental within my budget.

Diane had been a significant presence in my life for roughly ten years. She divorced my dad when I was fourteen, but we maintained contact through Christmas cards and occasional lunches where I sought her counsel on girl issues.

In my youth, she took on the role of a second mother, with whom I shared intimate conversations about various aspects of my life. I often referred to her as 'Mom' due to our closeness.

Diane was not only strikingly gorgeous but also charismatic, nearly winning the title of Miss Oregon. After she finished her degree in business and entered the real estate field, she began building a massive brokerage company with numerous associates working under her.

Upon my arrival in Portland, I phoned Diane immediately. She did, in fact, possess a few rental properties, so she could certainly aid me in my search. She even extended an offer for me to reside at her place, which had plenty of vacant beds.

Diane's new home was situated in the West Hills of Portland. The gigantic house appeared more like a mansion to me, and she explained that the breathtaking views and serene environment justified the high cost. She had also obtained the property at a bargain price.

I inquired if she ever felt lonely. She responded that she occasionally rented rooms to young men but usually abandoned them either when they tired of her or when she caught them stealing her undergarments. Unbelievable!

"Is this the time where we discuss a few house rules since I'll be residing here?" I joked, likely not concealing my blushing cheeks.

"Fear not," she instantly remarked. "I won't subject your innocent soul to any unnecessary harm. I'm confident you're now less susceptible to shocking experiences, my intrepid world traveler."

"I'm almost twenty-one, so I'm practically ancient," I joked.

"Okay, dear, I'll extend a proposition. I'll keep my apparel on, and you'll ensure your apparel is not pushed aside on the floor."

"Deal," I agreed. "Which room belongs to me, Your Highness?"

As I followed Diane up the stairs, she explained how her luxurious apartment downtown, fitness-equipped with a furnished bedroom, offered tremendous potential. She couldn't wait to show it to me the following morning.

Diane's smile was contagious. "I'm simply thrilled to see you!" She grasped my arm, leaning into me as we strolled. "Here we are!"

She guided me into the room, accommodating a sizable bathroom that flowed flawlessly into a separate sleeping area. "Here's my bedroom. I've got a pool table in the primary bedroom, and this one boasts a beautiful balcony for morning sun exposure," she remarked.

"Cool," I said. "Let's get settled, and then we'll grab some lunch."

We relished a delightful meal and I regaled her with stories of my monotonous life in Germany. Mom leaned in and attentively listened before exclaiming, "You're so young and accomplished, yet you've done so much already." Shaking my head, she confirmed, "I spent my entire life in one city."

She then shared, "Your father could not settle down, and I had no interest in tagging along, so we decided to part ways." Mom added, "I married an older gentleman, expecting him to become more settled, but alas, not Dad..."

"I'm sorry that your marriage didn't work out," I expressed. "I'm certain he regrets his actions now."

"Mom, you've achieved so much," I asserted. "You're one of the most successful brokers in the area, possess a beautiful home, and remain stunningly attractive. You radiate warmth in every room you enter, and everyone wants to collaborate with you."

"Flattery will go a long way," Mom commented. "Indeed, my life is quite satisfying. I work diligently and set ambitious objectives."

"Well, your body guru undoubtedly deserves a substantial tip because he does an exceptional job," I quipped, wonderstruck at her stunning appearance, even compared to when I was a teenager.

"Well, I prioritize my health and physique," she clarified. "However, are you insinuating that I was not attractive when you were a teenager?" her face turned pink.

"Hey there, Mom! It's pretty awkward, right?" I uttered. "I'll admit it - I found you attractive back then. So did every other teenager in my school. They nicknamed you Miss America with much admiration. It was a bit bothersome, if I'm being honest." I chuckled while rolling my eyes. "And you're still stunning to me, Mrs. Robinson."

After an uncomfortable silence, I proceeded. "Dads can be dumb sometimes. I was shocked to hear you were getting divorced. You could've chained me up in the basement, and I'd still be there, waiting for you."

"Interesting visual scenario," Mom stated, poking me in the ribs. "I've never realized you enjoyed being tied down so much."

We kept chatting and laughing well into the night, eating a pizza, and sharing a couple of wine bottles. She inquired about my love life, while I discussed hers. "Yeah, there are some young fellas who stay here occasionally. They can be quite the handful."

"How old are these chaps, Ma'am?" I asked.

"The same age as you, actually," Mom replied, sitting face-to-face with me on the couch. I won't lie; there was a moment of silence.

"Oh dear, I hope I don't know any of these guys!" I worried.

"I don't think so, but keeping track is rather difficult," she said mock-seriously and started counting her fingers.

My eyes likely widened in shock - pure horror. She burst into laughter, almost knocking off her wine glass. "Wow, did that catch you off guard!"

"Yes, absolutely," I replied, taken aback.

I decided it was time to change out of my jeans and headed to my room. I pulled off the pants, and just as I prepared to remove my leg, the bathroom door flew open into my room.

Startled and with my pants halfway off, I turned, stumbled, and plopped onto my behind. Mom giggled and said, "Careful, Big Fella." My heart raced - exposed ankles up and legs tangled in my pants - not my most glamorous moment.

"Great, Mom, thanks for the reminder about bathing suit bottoms," I muttered.

"Hilarious, funny guy," Mom laughed until tears formed in her eyes, almost causing her bathrobe to unfasten. "Let's get a move on. I need to wash up." She rushed into the bathroom.

I headed back to my room, deciding it was best to change. I removed the jeans and was about to take off my leg when the bathroom door opened into my room.

Surprised and caught off guard, I turned, tripped, and fell on my ass. Mom burst out laughing, stating, "Be careful there, buddy!"

I extricated my leg from my pants and stood, quickly covering myself. "Thanks, Mom. My underwear is pretty basic."

"Alright, shy boy, settle down," she said, the laughter finally subsiding. "Two things: One, keep the door open when you shower to let the steam out. Two, we'll have to go shopping for underwear tomorrow. I'm serious."

As I stood in the doorway, she turned on the shower, stepped out of view, and disrobed. Mom started showering. Was she messing with me? My arousal didn't care. I wanted to come in and join her. Instead, I changed into relaxed shorts and a tank top before heading downstairs.

I opened another bottle of wine, poured, and turned on some mellow jazz before finding a rolled-up joint in Mom's not-so-secret stash.

"Do I smell what I think I do?" I heard upstairs. "It's not fair that you take that joint without sharing!" Mom walked in, Still laughing. "Do you always sneak around smoking?"

"I promise I didn't mean to steal," I reassured her. "Here, help yourself," I offered. She quickly took it and inhaled before flopping onto the couch. "T','H','I',''S'..."

I joined her on the couch, and we shared a blunt. "Gimme!" she said, holding out her hand. I passed it to her, glad for the distraction. We sipped our wines. Mom sat cross-legged with her legs tucked underneath her, pulling at her robe to cover herself. It felt strange - important - to wear something so revealing when someone else was around.

"Sorry about the nighty, Michael," she said. "It's not usual for me to have company in the evening, so I wasn't prepared."

"And you don't need to worry about that, Mom. You should always be comfortable in your own skin, no matter what you wear," I replied.

"Okay, Michael! Don't worry about me! I'm not there for modeling - I'm there for my son," Mom countered, jumping up and pulling her robe tighter. "Ready to dance with your old Mom?"

She grabbed my hands, guiding me into a dance, our bodies swaying together. "I've never danced with you before, Mom!"

"I don't doubt that, sweetheart," she said. "Good thing we have this moment now."

My hips distanced from her, but her embrace made that challenging. Fuck, I thought, A pile of deceased puppies. A stack of deceased puppies. A heap of deceased puppies. It didn't succeed.

Miss Universe, a drunk Miss Universe, had her nearly naked flesh bound to mine with her head on my shoulder...and she was my mother.

Diane's breath scratched my neck. Her pelvis located an erect penis that shoved into my shorts, yearning to stand upright and breach through my clothing. She bent her leg and rubbed her groin against my dick. I believe we ended the dancing there.

Mom got enveloped in her bubble, humming and rubbing against me so tenderly. Is this how she dances, I pondered? My penis didn't care, and my mind churned.

"Alright. I think I've consumed too much alcohol, Mom," I said as I separated myself from her wriggling body. Where I discovered the fortitude to do so, I'll never know.

Mom turned into a pouty mess and was clearly inebriated. What was I going to do, have sex with my stepmother while she was intoxicated? It would've been enjoyable, but I wasn't that intoxicated myself. "Let's sit on the couch, Mom."

She cuddled up against me and rubbed her head. It wasn't long until she was snoring gently, her head in my lap. I observed the jumbled fringe of wet blonde hair confined to her head, wondering what my father had been thinking to ditch her.

My penis joyed in the warm tap of head snoring vibrations. What a delectable delight. I possessed a devil on one shoulder and an angel on the other. The angel triumphed.

I slinked from underneath her. I stacked a pillow beneath her head. The blanket on the couch's back would keep her warm tonight. I shut off the music and the bulbs, and went upstairs.

I was intoxicated and weary, too fatigued to even engage in self-pleasuring, despite my erect penis. I plunged beneath the covers and swiftly dozed off. When I awoke in the morning, a limb was encircling me and a body was pressed against my back.

Oh no! I feared the worst, then realized I was still in my underwear. Mom wore her dressing gown, mostly. I cringed and attempted to leave the bed. Mom grunted too, and clutched me narrowly with her entire body. Damn, she's not making this simple, I thought.

She progressively awakened and I heard, "Ugh!" as Mom disentangled her arms and legs. "I must have inadvertently pranced into your bed last night somehow."

"Hello, Mom. I left you on the couch last night beneath a blanket." I said as I made my way to the bathroom.

"You should feel fortunate. I don't just clutch into any man's bed, you know," she said through the bathroom door. After I peed, my penis was sturdy and wouldn't deflate. Then? I retrieved a towel, wrapped it around myself, and left the bathroom.

Mom was sleeping in my bed. At least that alleviated the humiliation of her witnessing my arousal! She heard me fumbling around, saw me with the towel, and murmured, "Be sure to leave the door ajar, sweetheart," She adjoined. "For the steam."

Baby? Since when? She had flipped around and snoozed. I pondered, a shower won't hurt, and perhaps I ought to relieve some of this tension.

I showered and although my penis remained hard as can be, I was overly preoccupied about the open bathroom door. Would she witness me? What if she unexpectedly walked in? I disliked the idea of causing unease and hatred. I actually needn't have fretted about that.

I shut the water off, stepped onto the shower mat, and perceivably grabbed a towel. I dried my head, then my back. "You still want to go underwear shopping today, sweetheart?" She was on my bed, stomach down, elbows bent, her chin supported by her palms, simply staring at me and my stiff vexed member.

"Holy smoke! Mom!" I quickly covered myself and averted.

"Nice behind, honey!" She giggled. "Geez, child. Ease up!"

I wrapped the towel around my lower portion, and negotiated the bedroom. Mom had reclined onto her back and was quietly chirking while kicking the mattress. Her robe has slightly parted, and her panties were fully observable. She was piercing me.

I rummaged for clothes, half viewing Mom as her finger circled her navel. "I'll get washed up and concoct us some breakfast. How's that sound, sweetheart?" Said Mom, as she swiveled over and sat upright. I at most had my boxers on before she howled with laughter.

"Military-issue, indeed," I heard as she joyfully strolled past me and into the restroom. I heard her raise the toilet lid, then I heard Mom's pee splashing loudly into the porcelain.

"Um, Mom, hot as you are, I don't think you're creating sufficient steam to need to leave the door open when you urinate!"

Hey, Michael! You've got a point, hun. Most of the time, it's just me alone in this massive household. Gotta remember there's a guy hovering around. And thanks for the compliment about me being attractive.

"I wasn't lurking, just saying. Also, you don't have much modesty there," I responded jokingly. "And believe me, you definitely are a hot babe."

I continued, "Now, hurry up and prepare yourself. Then we can go take a peek at my brand-new place. Once I've moved, I'll be able to prance around naked while listening to some rockabilly music, gorging on wine whenever I please."

She yelled back from the bathroom, "I could get up in your hair as much as I want, dear. Plus, I've already informed you that I'll dance naked in my own house, no matter if any family members are around." Door shutting and her exiting the room.

We had breakfast andjourneyed to see the apartment. It was neat but simple, rather affordable, and situated in a fantastic area. I hugged my Mom, "Wow, Mom! I am astounded by how caring you've been. How do I ever repay you? Here's an idea. I'll cook dinner for you tonight."

"Chill now. This is just a little favor. In a few months, your top-floor tenant will leave, and you can move into the best apartment in the building. It's got a stunning view." She joked.

Mom confessed, "It used to be the superintendent's residence, and when you move upstairs, I'll transform it. It'll do as a temporary residence, unless you'd rather stay here a little longer. You know, in spite of all my frizzy hair." She snickered.

"No, Mom. I've been crashing with other folks my entire life. I feel like I need to have my own space. You're amazing, but, personal space, you dig?"

"Yeah, I do. Now let's go find you some underpants," She chuckled.

She locked the door after handing me the keys. "It's all yours now darlin'!" She kissed my cheek and we headed off shopping.

"Do you want me to try them on?" I inquired. "I simply go and grab what I want without trying them on."

Mom responded, "You should try some. Those military-style briefs are not doing a great job displaying your peachy derriere." The female attendant in the men's section giggled. I was mortified.

"I can envision it now," I expressed. "I'll ask girls if they like my underwear, and brag that my Mom purchased them for me. I'll hear the door slamming as my new neighbors flee from my place."

The store employee said, "You'd be surprised how many moms escort their sons to purchase such items." She slipped three pairs of underpants onto hangers. "Trust your mother. She knows which style suits you the most."

Despite feeling embarrassed, I selected the garments and walked into the private dressing cabin. There was a small staircase with three mirrors at the top. I climbed them, pulled aside the curtain, and stepped inside.

I donned the first pair. I couldn't deny--they looked great. I yearned to see myself in the mirror, so I exited the alcove and stood in front of the mirrors. My buttocks were a charming shape, and the running had definitely sculpted them.

"One whistle and I'm out!" I jested.

The store staffer remarked, "It's a safe space here, son."

My Mom said, "The front of those look fantastic. Lift your shirt to see how they fit around the waist." I obliged.

"I'm more into boxers," I shared. "These seem a touch constricting." She emerged with an alternative pack.

"Try these out," she suggested. "These are designed for individuals with a little more in the groin department."

Mom was having a grand old time teasing me.

"One of these will do," I resolved. I retreated to the changing area and slid out of those briefs. They were adhered to my crotch. Geez, we'd need to purchase those as well.

I put on the silver briefs. They felt really nice...really great, in fact. My dick was bigger, and my dangly bits were filled and sensitive. The fabric seamlessly stretched to accommodate my equipment and it was so comfortable, as if I wore nothing at all. They were more like briefs compared to boxers, hugging my bottom in a way other pairs didn't. Shining in the mirror, I turned.

"Yep, that's the one. Fabulous, darling," Mom applauded.

"I concur with your mother. How are they feeling?" replied the shopkeeper.

My penis was feeling pretty content as I said, "These are so comfortable." My back was facing the females. The shopkeeper repositioned the unstable band around my hips. My penis became completely rigid.

I could sense my penis stretching across my leg, stuck between the briefs. Drips of liquid leaked out. The two women beside me observed my rapidly increasing hardon and the expanding stain where my tip pulsed.

I darted away to hide behind the curtain. "Just wear them on the way home, my boy." I heard Diane say.

She purchased different shades, including the ones I had checked out. Mother shoved the miniature red briefs into her handbag. Remaining ones were stuffed in a stylish container.

As we left for home, she suggested visiting a lingerie store. I said "No thanks, Mom." She was still chuckling.

"Too simple," she stated.“ It’s awesome to see you having fun." She remained calm, and I found her laughter endearing. I couldn't get upset with her no matter what.

"Thanks for the briefs, Mom."

"You're welcomed, sweetie. How do you like them now?"

"Very pleasing, Mom. They don't gather when I sit. They're perfect."

She was checking the various models she had picked. She drew out the briefs from her purse and inspected the area where my penis had expelled onto the fabric. "This piece was attractive, but if it didn't cradle my part just correctly, fuck that." She turned the window down, detached the briefs using two hands, and pressed it upwards. I gaped at the window as the wind took the object carrying my drip away.

"Hey, Michael?" Mother asked a few minutes later. "What did you do with the army undies you wore to the shop?"

"I discarded those old-timey briefs! Would you like to throw those out too?"

"Kinda," she answered. We both shared a laugh as I parked in her driveway.

That evening after preparing a divine feast for us, Mom recommended a film. We cuddled on the long couch section. In my lap, I had a large, fluffy pillow, which she settled against and reclined on my chest. She wore her small silky nightgown.

I barely appreciated the show. There was a lesbian sex scene that was intriguing, then a bunch of breast shots. However, those were the only things that drew my focus away in my erection. Mom appeared uncomfortable, fidgeting on the couch, seeking a blanket, and kicking off her socks.

Suddenly, she raised her head, withdrew the pillow from my groin area, and placed a smaller one on my erect penis. My head rested on the pillow, and it seemed she got comfy.

Mom was fetally situated with her head on my lap. This circumstance didn't help with the bulge in my lap. She would go to bed soon when I decided to leave.

She made a slight commotion, shifted a bit, and swayed rhythmically below the covers. I could barely contain my excitement. Did my mother really touch herself while watching this movie? Was she ejaculating in front of me?

Mom released her grip on the pillow. The range of activity in the film intensified, along with the background music. I could see her raise her head and bite the pillow, in rhythm with her hard convulsions. I was completely dumbstruck. Was my mom engaging in sexual activity on top of my penis?

Mom freed her jaw from the pillow covering my member. The scene finished, and the noise became more subdued. I was still frozen in place. Mom stretched a bit, lifted her hands from under blankets. Not only the blanket, but the air around was filled with her scent. It induced desire within me.

"I'm almost asleep, honey," Mother stated. "I'll go now too." She turned off the TV and ascended the stairs. I remained seated on the couch. When I finally took the tiny pillow away, my penis had soiled the briefs. I stayed a wet mess.

Mom came back to embrace me. Her naked thigh massaged my groin. "Oh, you're soaked, baby," she murmured. "Just keep these.I'll wash them tomorrow."

I was jolted awake during the night. The faint unpleasant noises of Diane could be heard. Curious, I made my way towards her room to check on her. As I arrived, she was lying on her back, thrashing around in slumber. I gently placed my hand on her shoulder to calm her down. "Mom?" I whispered.

However, upon closer inspection, I realized that she was completely undressed except for her soaked panties that revealed her vagina. Her wild dreams, as she often claims, had claimed another casualty - her nightgown.

The evil voices in my head were suddenly all too loud. They showed me clear images of her ample breasts, gleaming in the dim light. Her secret crevice ached for my touch. I told myself to enjoy the view for a while, but the pull was too strong. Must resist... Want to touch them... Fuck! This was complete madness.

Stepping back a few steps, Diane rolled onto her stomach, a strange sound emerging from her that could only be described as a 'harumph'. Her left hand suddenly went underneath her body, and she began massaging her wet panties. My eyes were fixated on her losing herself in her actions. Watching her cum while she screamed into her pillow, the room was filled with her moaning, and her body went limp as she fell back into her sleep, loudly snoring. I wandered back to my room, bewildered by the mind-blowing scenario I had just witnessed.

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